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jasonwr1975
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# Posted: 2 May 2007 08:02:42
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Taking a break from the story writing tonight, a little tired, so thought I would add a couple of pictures that help to illustrate the scenes I am describing here. Here is a pic that reminds me more of my early cuckolding than almost any other. Lisa was a bit fuller in build than this woman, not as skinny, but the teasing look captures the experience I had well, and the small cock is not unlike my own, maybe a bit smaller but same teasing ballpark. I love how she looks totally in control and totally unintimidated. I am very used to this kind of erotic "I'm in control" smile as I sure many cuckolds on this forum are.
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jasonwr1975
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46
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# Posted: 2 May 2007 08:08:13
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This picture goes earlier in the story actually, but this is not unlike the view I had when I was watching Lisa mount Frank's big cock cowgirl. This guy's cock looks to be about Frank's thickness and length. Lisa's legs were maybe shorter and her butt a bit rounder, but this is a pretty good likeness of her too. The real similarity is the happy smile on her face as she looks forward to this big penetration. I had a chance to see this with her a few times and like this girl, she could not contain her excitement.
a happy big dick mounting
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jasonwr1975
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46
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# Posted: 6 May 2007 10:18:32
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Moving right along….
Growing up Cuckold, Story 1 (true story): high school sweetie (part nine)
The next few days were kind of a blur to me. I was in a state of pretty big sexual confusion. I had tried to fuck the shit out of Lisa and had been only moderately successful. In the end, she had told me that I just wasn’t big enough to make her come on my cock. I couldn’t believe how much it turned me on to hear the truth after suspecting for a long time that my cock was not big enough to give a girl maximum pleasure. At the same time, I was in a bind – I didn’t know about true cuckolding and the option it would give me to share my girl but still have the love and sexual fulfillment I wanted and dreamed of (as well as the hot teasing that I couldn’t help but love).
So I felt a lot of teenage despair during those next days, and I also jacked off a lot. I didn’t see much of Lisa, I was out of the house a lot, riding my bike to hang out with pals, play music, just forget about it for a while. I would have had no way of telling my friends what I was into. It felt crazy. But I was too turned on to be utterly discouraged. Confusion was the best way to describe it.
And for Lisa, while she had enjoyed our scene, it had left her more horny than satisfied. So, we just kind of avoided each other. The girl I was really awkward around was Lisa’s sister Elizabeth. I thought she would think of me as a total freak, and I think partly she did. But I think she also saw the affection that flowed between me and Lisa and respected that. Some of Elizabeth’s boyfriends were kind of jerks and it seemed like Elizabeth respected how kind I was to Lisa and how well I treated her. I tried not to run into Elizabeth in the mornings before she went to work but we did have our run ins. At one point, Elizabeth smiled at me while we were both in the kitchen, and she said, “it’s sure been noisy around here lately at night.” That was her way of saying that she had heard me screaming to Lisa, begging her to “make my little dick come!” Elizabeth knew about how Lisa was teasing me then.
Elizabeth was pretty intimidating, I was a little tongue tied around her, and she didn’t seem to be that interested in the details – though I later found out that she and Lisa talked about it some. If this situation had presented it in recent years, I would have had the confidence to try to pull Elizabeth into it too. But at that time I just slinked around it, but I played that situation over and over again in my mind when I jacked off, either reliving that day Elizabeth walked in on me jerking my cock or that she was maybe lying in her bed masturbating, listening to Lisa make my little cock come while I yelled out.
There’s not a whole lot of new things to share about my first experience with cuckolding, and as I said, it wasn’t real cuckolding but a couple of kids finding their natural roles without real education on it. However, there were some more hot scenes before I moved out. They weren’t too different than the ones I’ve already described, but it may be worth it to write about one more.
What happened was about four nights went by, and finally Lisa visited me in my bed again. After curling up next to me and just talking about other stuff, she finally said,
“Do you want to watch me have sex with Frank again?”
I think I said “yes” before I could really think about it.
“I was thinking about it,” said Lisa, “and the first time you watched me with Frank I didn’t know you were watching. I really want to know what it’s like to fuck while you are watching me.”
Of course, it didn’t occur to Lisa to ask Frank if it would be ok for me to be there, or even watch. I’m sure she figured another man would not be ok with him. So, she suggested that we have a replay of the other scene. It had been a rainy week but it was supposed to clear up that weekend. Elizabeth was planning to be out of town, so it seemed an ideal time for Frank and Lisa to fuck in the backyard. I could watch from behind the curtain again.
“I would love to think about the look on your face, watching me get fucked so well. Would that turn you on too?” Lisa asked me with that total confidence she was perfecting around me.
“Yes.”
“What would you do while you were watching us?” (she knew, but she wanted me to say it).
“I’d be jacking myself off,” I said, kind of dodging the point.
“Well, that’s true,” Lisa said and kind of giggled. “You’d be jacking that little cock off so hard.”
I didn’t say anything. I loved this kind of talk but still didn’t know quite what to say sometimes.
“Wouldn’t you?” she pressed.
“Yes.” I said helplessly.
“Yes what?” she asked, more forcefully this time, not smiling.
“Yes, I’d be jacking my little cock off, jacking it off like crazy,” I added.
My submission made her smile. She loved that control.
“Would you be jealous?”
“Yes.”
“Why?”
“Because he is so much bigger than me.”
“And…..”
(I swallowed hard and admitted it)
“He is so much better than me at fucking you.”
“Yeah, Jason,” she said. “I’m afraid that’s true. Frank makes this pussy come so hard.”
When she said that, she lifted the sheet. I could see her fingering her pussy through her shorts, and a stain on the crotch was growing. It was so fucking hot. This girl was just torturing me with her hotness.
“Look at this pussy,” Lisa said. “Don’t you wish you had a big cock like Frank’s to fill it up with?”
“Oh yes….” I was off and running now, my ego was gone and my dick was so hard.
Lisa shifted her pussy rubbing to her left hand, taking her wet right hand and slapping it around my cock.
“Oh, that little dick is so hard for me. That adorable little penis loves this pussy but can’t fill it. It’s so cute.”
Lisa was jerking me under the sheets while she said that. I couldn’t even think straight. She ended up jacking me off again. This time she was nice enough not to make me yell, which would have been really embarrassing because her sister had a couple of friends over. In retrospect I wish she had made me yell but at the time it was nice to avoid the embarrassment.
That was the end of that scene, but we agreed to set it up so I would watch them fuck again from my bedroom while they were outside.
This was to be an important scene for me in terms of my own small penis acceptance. Before I could accept total cuckolding, I needed to accept my small penis. I was getting closer to that total small penis acceptance, I was maybe 80 percent there. It was going to take a little while longer. A part of me couldn’t quite remember, or didn’t want to remember, just how different she had been with Frank than me. But now that I had fucked her myself, I would watch her with Frank very carefully. And Lisa had some special treats planned for that time that I was not expecting. One thing we did agree on: if she was facing me and Frank couldn’t see me, she wanted me to open the curtain.
“I want to see the look on your face while you’re jacking that little cock and watching me ride him,” she said teasingly. “But don’t keep the curtain open for long, I don’t want him to see you there.”
In the final installment in this first story series, I’ll share that scene watching them outside. Then I think I’ll fast forward to my next cuckolding a few years later, which was a true cuckolding that I probably wouldn’t have been ready for without this “dress rehearsal.” In some ways, the true cuckolding was more intense than this warm up round, but at the same time, I guess you always have special feelings about your first. 
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inferno_reprise
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2
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# Posted: 6 May 2007 21:14:42
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Nice story, please continue!
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jasonwr1975
Member
46
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# Posted: 28 May 2007 11:07:04
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Before I continue with this story of a defining sexual experience in my life, I want to comment on a couple of emails I have received. I also want to apologize for the delay, I've run into some health problems and am having some trouble shaking them, though I seem to be improving. I hope to get back into the writing more shortly, so bear with me.
A couple of the emails I received pertained to cock size and cuckolding. One person pointed out, rightly, that size is not the only reason to get into cuckolding. That's true, I have run into some large cocked cuckolds online, and they have the same submissive tendencies and desires as some of us smaller guys. Obviously having a smaller dick leads more naturally into exploring submission, but just about anyone can wind up wanting to explore that side of themselves. That is understood.
However, I feel that if I had a larger cock, I would have been much more dominant in the bedroom as a youth. That's not to say I never would have been submissive, but I was forced into looking at that side of myself earlier and sooner due to women who were not satisfied with my size. This does not mean all women would feel that way, just my experience. And my experience is that the majority of the girls I dated were not satisfied with the size, though that majority has increased in number as I’ve gotten older and run into women who have had babies and/or more experience with bigger guys and toys.
There is also the matter that some folks emailed me regarding that five inches is not necessarily small. Having an argument on what is small and what is not is not worth it, obviously there are many factors. I can only say what I've concluded through my several cuckolding experiences and a couple cheating girlfriends as well: five inches may or may not be small compared to other men, but in my experience, it feels small inside most pussies that have had larger and thicker cocks in them. So when I say "small," that's where I'm coming from.
Coming to terms with my small cock was a gradual process and these stories shed some insight into it. I know I have used the phrase "sexual inferiority" in these stories but in some ways I think "sexual handicap" might be a better phrase. Only because inferiority seems permanent whereas "handicap" implies something that to some degree can be overcome or even in some cases not be an issue at all. Of course, in other situations, size can become so important that some solution (toys, other lovers, less penetrative sex) has to be decided upon for the woman's satisfaction. Some might say the defining aspect is casual versus serious relationships, but I don't agree. Size can become an issue in every kind of relationship, short or long term. "Handicap" might be the better term to accomodate all these possible situations. But, inferiority is a loaded term that can be fun to use sometimes for effect. OK, Emails answered.
Now, back to the story.
Growing up Cuckold, Story 1 (true story): high school
sweetie (part ten)
So Lisa and I had agreed to set up a scene where I could watch her with Frank with her knowing that I would be watching.
In the days before the scene, I fell back a bit into denial about my situation. I convinced myself that I had made Lisa come well also, and that I could treat her a lot better than Frank as well. Maybe I wasn’t such bad “boyfriend material” after all. As if to reinforce that, she and Frank got into a fight that was primarily based on him being an idiot and getting drunk with friends and not calling her back. For a couple of days, I thought the scene was off. I was both disappointed and also happy, glad that Frank had shot himself in the foot. I did not yet realize that guys with big cocks who know how to fuck can get away with a lot of misbehavior and still get back into good graces.
The weekend came, and I didn’t expect much to happen. Elizabeth went out of town as planned, so it was just Lisa and myself. Saturday afternoon, Lisa was out and I was reading a Stephen King book of short stories. The phone rang and I almost let the answering machine get it, but then I wondered if maybe it was my manager
calling (I was sometimes called in on weekends), so I picked it up. It was Lisa…
“Jason!”
“Yeah,” I said a bit groggy from being such a slacker reading in bed.
“We’re coming over soon, Frank and I…get ready! I gotta go.”
She hung up before I could say anything. The next minutes went by in a blur. I quickly rinsed my dishes and took my work out clothes from the living room and got rid of any evidence I was hanging around that day. Then I shut the bedroom door and turned out the light in there, closing the curtain almost all the way, but making sure I could peer out from the crack. I left the window up a crack as well so I could hear them.
I waited, trying to pass the time by reading my short stories.
Eventually I heard voices in the house and knew it was the two of them. Whatever they had been fighting about was over now, I could hear them joking and laughing. I peered out of the curtain and saw them walking outside in the distance through the main glass door. They were both fully clothed at that point. They started kissing and rubbing each other. This wasn’t so great for my view because they were on the left and pretty far away. But I knew Lisa wanted to be watched, so I was hoping she would move the action over closer. It was also really cloudy so it was a bit harder to see than last time.
Frank pulled her t-shirt off and she took his off. I was a bit jealous as she rubbed her hands on his chest, which was well built and manly as she rubbed him. They were kissing and she was rubbing her crotch on his. Even far away I could see a bit of a bulge starting to tent up his jeans. Lisa pulled them down and he kicked them off. He was wearing tight fitting bike shorts and you could see the bulge a bit clearer,
but then they were kissing again and I couldn’t see anything. He had his hands under her jeans caressing her beautiful ass and she was rubbing his bulge through his bike shorts. Then she pulled the shorts down and his large cock flopped out, already half hard. It looked so fucking arrogant and strong flapping in front of him and you could see his cocky face as she grabbed his cock in a state of lust.
Just then, I got some bad luck. It started to rain. Frank put his hands up to see how hard it was raining, then he grabbed her and she grabbed her purse and he led her into the poolside room. This was not a good development for watching at all! He went into the pool room first and I thought I saw her looking over at me as she went inside, as if to apologize, but I could barely see her from that angle as the pool house was well across from my bedroom with the pool in between us, basically diagonal to my viewpoint.
It was raining really hard now, and I realized I had been rubbing my pants and then stopped, trying to listen for them. I thought I could hear some noises, voices from the pool house, but the rain was beating down hard. The only good thing was that it had that “summer thunderstorm” feeling and I was hoping it would pass soon. It rained hard for a while, and I just waited there, pretty jealous and disappointed. I couldn’t believe she would pay so much attention to Frank after he had blown her off all week. But I guess that is the definition of sexual power. If you have it, you can control people. And Frank had much more sexual power than I did – something I would accept much more in retrospect than I did at the time. It was a very painful truth, all the more frustrating knowing he was kind of a jerk and I worked so hard to be a good guy that women said they wanted.
The rain stopped and I definitely heard some sex noises now, mostly Lisa, but couldn't really make it out. I was thinking about coming out of the bedroom and sneaking up by the pool shed to listen, but that was a really risky move as I wouldn't be able to hide very well if they came back outside. I really didn’t want to miss it. But I remember I promised Lisa not to listen/watch her fuck without permission, and maybe this crossed that line. So, I just lay there and rubbed myself a little. Suddenly I heard the voices louder and a door opened.
Lisa was walking out of the pool room wearing nothing at all. I was surprised to see she was a bit hairier in her pussy than usual, I guess maybe she hadn’t shaved down there since the last time I saw her naked, but she looked amazing in the sunlight. Frank was walking behind her, and a condom was still mostly on his cock. His mostly hard dick was glistening with her juices and standing out firmly from his body. He
looked like a porn star and I was hating him.
--- As a quick aside: Lisa had already decided that she didn't want Frank to know she was being watched, but knowing my kinks and hers as well as she now did, there was one thing I did not know as I was watching this scene unfold: Lisa had told Frank in the poolhouse that she had recently fucked a guy with a small cock and was really missing his. Now that this is known the scene will make more sense.
So, Lisa pushed Frank down on the diving board with his cock sticking straight up in the air, tall and thick. She straightened out his condom with her beautiful ass in the air towards me. But this time, when she sat down on his dick, she was facing me.
I watched her pussy slowly lower down on his meaty cock. It was amazing to watch the look of pleasure on her face, and more amazing to see her pussy stretched almost obscenely around his thick shaft, slowly sliding down. She groaned as she sunk all the way down on it. I couldn't help but think back to when Lisa and I had fucked, and how easily she had slid down on my cock. Taking Frank's cock was hard work, even with her weight bearing down on it. Still, she had it all inside her when she let out a satisfied grown and started to raise up and down on it slowly, the muscles in her tanned legs flexing on each side of him.
"Oh my God." Lisa said...."I love that cock so much."
"Yeah you do," said Frank. "I told you not to waste time with little dicks."
"Oh yeah," Lisa said. "Your dick is so much better."
I wondered how much Lisa had told Frank. I also noticed that she was being a bit submissive with him, which she never was with me. Frank knew how to make her pussy come, perhaps even when she didn’t want to come, and that was the power he wielded over her.
As I watched through the crack in the curtain, I could see Lisa's eyes staring straight at me, a look of lust in her eyes. Watching this girl that I adored, who had such an incredible body and appetite for sex, riding another guy's cock, was downright humiliating. So close, so far. But it was fucking hot and I couldn't help but start jerking, starting towards my own come.
Frank egged her on.....
"Tell me how good this cock feels..."
"Oh, so good, so fucking good," Lisa said, starting to move up and down a bit faster.
"So much better than that other cock you were stupid enough to fuck, right?"
"Oh yes, Frank."
"Tell me, or I won't make you come. Tell me."
Lisa knew what he wanted to hear.
"God, your big fat cock is filling me up so good. I could barely feel his little cock."
"Do you want me to make this pussy come? Come like you couldn't with his little one?"
"Oh god yes," Lisa said. The next lines almost ripped me apart and made me come at the same time...."Please Frank, make me come with your big cock, come like his tiny little cock can't do....."
On the next upstroke, Frank pulled out, and Lisa let out a gasp of disappointment. The excitement of knowing she was being watched and all the hot talk must have been intense for her too this first time…she didn’t’ want it to stop.
"Oh....Frank, Please let me put it back in, please put it back in, I need to come so bad!!!!"
Lisa's hips were bucking as she said this, looking for his cock which was just out of reach. She could have reached for it with her hands but I guess she was enjoying this submissive game.
"I don't know," teased Frank. "I don't know if you deserve this big cock after being such a slut."
"Oh Frank, don't tease me, I'm so close, I need to come so bad."
"What's the matter, little dick guy didn't make you come?"
"Oh, he did," Lisa admitted, "with his tongue." Frank laughed. It was all I could to not run out there and punch him. "But that was just a small come, and then he fucked me and tickled my pussy but didn't really fuck it, because of his tiny little one." Lisa stared right at the curtains when she said this, and throughout this part in her scene, she had more of a mean lusty look on her face than the teasing smile. I guess she needed to come too much to smile right now.
--- one more aside: even years later, it always bugged me that Lisa called my cock “tiny.” It was small, sure, but it wasn’t tiny. It wasn’t until years later that I discovered the concept of “cock volume” and did some math. Turns out Frank’s cock was about five times larger than mine in volume, and with some work, she could take all of Frank’s cock. No wonder my cock felt tiny to her. That also explained the massive difference in sensation. I might have been just a bit under average compared to other men, but to her pussy, my cock truly was tiny. And her pussy wasn’t worried about hurting my feelings, it was concerned with the primal need to come and take sperm deep inside of it. --
"So you've got a come all ready for me, and you need this big cock to give it to you!" teased Frank.
"Oh yes, Frank," she said.
"Ok, I'll make you come, on one condition."
"Yes, anything!"
"You don't fuck that little cock ever again! It makes you too frustrated and I have to clean up the mess!"
"Oh yes, Frank, whatever you want, I won't fuck that little dick again, just pleeese make my pussy come!" (it didn’t make me too sad to hear that because I wasn’t sure I wanted the humiliation of trying to fuck Lisa again anyway. I also learned later that girls say things in these heated moments they don’t totally mean…cuckolds know what I mean by that.)
"You asked for it!" He said..."put my cock inside you!"
Lisa then reached for his big cock and put it back inside her. Her body literally jolted with a bolt of electricity when she put it back in. This time, Frank took control of the thrusts and starting really pounding her, bucking his hips up and driving her into the air. It was so fucking violent, and you could hear that wet plunging sound that only a big cock inside a very wet pussy can make. I realized later this was one of the great secrets of big cocks: he could pull out halfway and ram back in, getting lots of power without ever taking his cock really out of her pussy.
I started rubbing my own small cock also, because I could see from the look on Lisa's face that she was heading for a come, and it turned me on so much. I looked for her to see if she would put her hands on her clit to help make her come, but I knew deep down that she was getting so much sensation from being stretched and filled that it wouldn't be necessary. Instead, she had her hands on both of Frank's legs for support while he pushed into her so hard.
There wasn't any more dirty talk at this point, there were screams and moans and stuff but nothing I could make out. Suddenly I saw Lisa start trembling, a shake that started in her legs, and I knew it was happening.
"Oh shit...I'm gonna come! I'm gonna come!!!!!!"
Lisa's eyes literally rolled back in her head as her entire body trembled and her hips shook as she sat all the way down on his cock and just let that huge come rip through her body. Cuckolds on this list probably know what I am talking about here, that there is nothing more beautiful than seeing the girl you love come so deeply, in the way that she deserves, getting an itch scratched that you couldn't scratch. It wasn't my fault I couldn't scratch that itch, and it wasn't Lisa's either. But I knew that I would never deprive her, or any woman, of that kind of pleasure. Yes, I had made Lisa come. But not like that. Not screaming so loud the neighbors must have heard. Not sweating so hard that she was just drenched. Not making her pussy so wet that juice was just rolling down her legs. Yes, my cock was too small to make her come like that. It was a fact, not a sick/hot fantasy. And that fact made my little dick come harder than I ever had in my life, come on my hands, on the curtain, on the carpet, everywhere.
Lisa came to rest on his cock after she came, and he was still mostly hard inside her. She had a big happy smile on her face, and I could see her smiling finally as she looked towards the curtains. She would tell me later that this was the best come that she had ever had. Knowing that while she was getting her pussy filled, that the man who loved her most was watching her helplessly, stroking his little cock and likely coming and in awe of her beauty and power, that put her over the top. Yes, she would have come on his big cock without me there, nothing could stop that from happening, but the intensity of the come was heightened even more by my presence...and maybe that's why cuckolding is so hot for everyone.
I'll finish this scene and the likely the wrap of the "Lisa era" in the next installment.
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Geronimo Samson
Member
415
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# Posted: 28 May 2007 14:59:11
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good work mate...hope ur health s fine now...
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jasonwr1975
Member
46
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# Posted: 13 Jun 2007 09:38:54
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Growing up Cuckold, Transition from Story 1 to Story 2
Hey folks...sorry for the delay adding to my story. I do intend to continue to tell about my early cuckolding experiences. I have had a series of health and work problems and I'm not in the clear yet, but I will keep writing whenever I can. Thx to those of you who have emailed me encouragement from time to time, that is always good to know that folks are reading. This is not the easiest story to write, partially because I am not as much of a natural cuckold, I'm someone who felt a bit forced into it due to my underendowment. Of course, over time I have found much to embrace in the lifestyle, but it's not always easy for me to revisit these stories.
I want to end the early story with Lisa and move onto the next cuckolding encounter. This is going to require a bit of transition that isn't too sexual in nature, so if you don't want to read that, just bear with me or skip this part, I'll get back to the sexual scenes soon. Those of you who like to read more context in a story may enjoy the transition and setup of the next thing, I don't know.
Looking back, I definitely have regrets about my experiences with Lisa. The biggest regret is that I ran away and she would have probably continued it at least the rest of that summer. I guess I took for granted that kind of situation, it turns out to be kind of hard to find as many of you cuckolds on this board know.
I have talked before about how for me, small penis acceptance and cuckolding are very connected. The situation with Lisa pushed me from denial of my small cock to maybe a 90 percent level of acceptance. But I still held out for that last 10 percent, and maybe that's why I bailed out on the situation. I did end up watching Lisa have sex a couple more times, and listened to her once from a closet too, and we had similar kind of teasing play afterwards as I've described here. She loved being dominant with me and I don't think she would have tired of this kind of play, but I was secretly feeling pretty lost and confused about my sexual identity. I refused to believe that my dick size could play such a defining role in my life. I was too young and arrogant to fully accept cuckolding...maybe some of you can relate to that.
I guess you could say I was looking for an opportunity to move on, and one came mid-summer when my mother asked me to come to Florida and help her take care of her sick mother and paint her new place for money. So I ended up leaving. I knew I would miss Lisa, but as much as I loved her, the one thing I did accept is that I wouldn't ever be able to fully sexually satisfy her. I was holding out hope, I guess, that other women would be different, that Lisa was the exception.
A part of me wants to go into some fantasies I have had about what that summer would have been like if I knew what I knew now about cuckolding and the roles you can play. I would have been a lot more willing to involve Lisa's sister Elizabeth, and I would have been more willing to expose my small cock for teasing and fun. But that wasn't me then, and that's not what happened. Maybe when I'm done with my real experiences I can come back and fill in a few fantasies.
So I left, and I kind of lost track of Lisa. We never spoke about that summer's sexual experiences, as she was mostly involved in serious relationships after that and it just didn't come up. I do feel pretty sure she never went further with cuckolding than what she did with me. She ended up living a pretty conventional life – nothing wrong with that. She has two kids now and I'm sure she's still really beautiful, as her beauty was always so natural and comfortable. I have no real doubt in my mind that her husband is well endowed because she seems so happy and I have spoken with him a couple of times and he seems about as confident and naturally dominant as anyone I have ever spoken with. But I guess you never know.
So I left for Florida. After that point in my life, I really made a point of avoiding casual sex. I guess on some level I guessed, I believe in retrospect correctly, that I had a better chance of avoiding sexual rejection in the guise of a real relationship as opposed to a performance-based one night stand. I had some trouble finding a girlfriend the next couple of years, but did end up finishing college and taking a teaching job. It was on that teaching job that I met Amanda. Amanda and I fell in love.
Looking back, I never realized how fateful our relationship was. We only dated for two years, but we talked marriage all the time. We were very passionate for each other. She actually thought my five inch cock was kind of big. She had two other lovers before me, and they were about the same size, maybe a bit larger, but I could last a lot longer so I was a real stud to her. I really loved being a stud like that and wanted it to go on and on. She was a beautiful girl inside and out, an athlete with an angular, dark complexion, and to this day, one of the most memorable girls I have ever met. Unfortunately while our relationship was passionate it was also volatile. We broke up in one of those breakups you can't even remember why it happened, it just did.
As sad as I was about losing Amanda – in some ways I'm not sure I ever got over that emotionally – I also left that relationship with a kind of arrogance that I would find other women that loved my sexual abilities and everything I brought to the table as a man. I was starting to believe that Lisa was more an exception, more a crazy size queen, and that I had a chance in the sexual marketplace as a studly, dominant guy.
Of course, that expectation was unrealistic. I realize now that there are many guys like me who have had a harder time satisfying women as they get older. As women get older, they tend to get more sexual partners and clearer preferences. For example, I am certain that a girl as beautiful as Amanda has now had a number of cocks bigger than my own. Would I still have a chance with her? Who knows. But she wouldn't think of my cock as big anymore. Not to mention that after women give birth, I have found their standards about size tend to increase also. But that is another story.
My confidence was bolstered even more a year later when I had a torrid passionate fling with a single mother whose children were at the school where I worked. She was coming off a bad marriage and she really seemed to appreciate my young athletic body and my staying power in bed. She had lived two decades with an indifferent, often-drunk workaholic husband, so in her desperation for affection I was an amazing lover to her. But looking back, there were signs. For example, her pussy was very loose from childbirth and I never made her come from intercourse alone. I made her come hardest with my fingers. But still, the sex was amazing and I was a legend in that school for getting this woman in bed with me. However, she fell for me pretty hard and I was arrogant enough to think I could get other women like this and wasn't ready for deep commitment. So, for the sake of everyone involved, I moved on.
At this point, I was 24, and I had put my cuckolding experience with Lisa behind me. I thought in my mind I was headed for many powerful, studly relationships. But that was about to change. My next three girlfriends were all hot women that I had some trouble satisfying. We never talked about size – I didn't want to go there – but all three of them cheated on me at various points, effectively ending the relationship. They all had quite a lot of sexual experience – the inexperienced ones were getting harder to find. The third one of the three did cheat on me with someone I know was pretty well hung because I had played on his basketball team and seen his big dick swinging in the locker room. These cheating experiences left me a little more discouraged but I just thought I needed to find the right girl. I was still pretty confident.
Then I met another older woman, just around my 25th birthday. She actually formerly had a daughter at the school where I had taught and had my hot relationship. She was a friend of this other woman's (Susan was the first mother's name) and had heard about the relationship. This new woman's name was Pat and she was a real get-what-you-want alpha female. Pat ran into me at local fundraiser and basically asked me out to drink and made a pass at me. She was taller than me, leggy and brunette, a bit intimidating but she seemed very hot for me, really in lust for me, so that took the edge off her dominant attitude. So, I took her back to my place and made an exception about the casual sex part.
Pat was the first woman to ever laugh at me when I pulled my pants down. "God I had no idea you had such a small cock!" I tried to explain that it got bigger when hard, so Pat did jack me off but remained very unimpressed. I guess Pat just assumed because I had made it with this hot older woman that I must be some kind of big-dicked stud. Pat wasn't one of those alphas who gets off on dominating men with small cocks. She just avoids them. So she pulled her pants back over her tight ass and said to me, "sorry, but I just don't fuck small cocks anymore. I'm used to a much bigger cock. I wouldn't be able to feel you and it's really not worth it for either one of us."
After Pat left, I cried for a while, cursing my small cocked fate. Keep in mind that while I had been cuckolded in a sense, I really had never experienced a loving cuckold relationship and didn't know that was even an option. I felt alone and isolated and not a part of the sexual drama. Of course, after I finished crying I jacked off until my dick was sore. The hottest thing was imagining myself putting my little cock inside of Pat's experienced, demanding pussy, looking down at her athletic legs and long, animalistic body, and then finally up at her expectant face as she waited to feel something from the friction of my penetration. And then Pat would dare me to fuck her hard, dare me to make her feel something, and I would pound and pound and she would laugh and dare me to make her come, and then give up and just tell me to move aside and watch a real man take care of her. Or maybe I would come with my little dick buried inside her as she urged my little dick to come so she could get me off of her and get a big dick inside her.
These fantasies felt so hot, but also hopeless and hopelessly twisted. As it turns out, I was ripe for a real cuckolding experience. What I did not know was that it was only a few months around the corner. I was about to experience total small penis acceptance.
- to be continued -
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faraday5
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35
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# Posted: 13 Jun 2007 12:51:52
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Don't leave us hanging. These anecdotes are great. And I hope you do get around to filling in the fantasies with Lisa's sister Elizabeth...
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more2202
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9
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# Posted: 13 Jun 2007 20:13:28
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this story is awesome
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dirtyman
Member
4
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# Posted: 14 Jun 2007 03:24:55
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I love this story. Your story reminds me of how I became a cuckold. There is nothing better than a sexy woman that needs more than you can offer and teases you about it.
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jasonwr1975
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46
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# Posted: 15 Jun 2007 08:22:51
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Hey folks...thanks for the good words, glad people are enjoying the story. I will definitely continue and have no intention of leaving people hanging between installments. I've made a commitment to telling this story and I will. Having said that, real life does interfere and I have some issues right now. But, bear with me and I'll get these installments down. I appreciate the encouraging words. I'm planning on writing either way, but an enthusiastic readership definitely motivates me to fight to find the time to write this stuff down.
More soon!
- Jason -
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jasonwr1975
Member
46
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# Posted: 24 Jun 2007 09:46:49
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Growing up Cuckold, Story 2: Small Penis Acceptance, part 1
OK, thanks for the patience those who have been reading faithfully. I've already explained some of the reasons for why it has taken me a while to write this so I won't bore you with that again.
Before I go into this story, I want to provide a bit of a background on the woman I met who changed my sexual life and confirmed my cuckolding identity. I am changing her name to Bethany because I know she has read cuckolding stuff online before and I've lost touch with her and don't know if she'd care or not, so changing her name to respect her possible desire not to have this public in her name.
It's important to understand a couple of things about this story: most women, as you know, are not well versed in cuckolding by the age of 25, which was how old Bethany was when I met her. So, I want to tell a bit about her backstory so her behavior when I met her will make sense.
Bethany was the daughter of a woman I'll call Alexis. Alex was an actress and model in her younger years. She was off broadway for a while before abandoning that career and becoming a high power banking executive. I think it's hot to point out celebrity resemblances to characters in stories. In this case, Alex was sometimes compared to Lauren Hutton. Lauren Hutton was about Alex's age and was a pretty famous model/actress in the 70s and 80s. I'll post a picture or two of her at some point. I eventually did meet Alex and I saw her pictures a couple of times and she did look a fair amount like Lauren, though not maybe quite as striking and maybe a little curvier.
Anyhow, Alex had a bit of a strange sexual history. She was in her early 20s in the early 70s, and as some of you know that was a very swinging time. Alex was an actress and pretty promiscuous sexually. She experimented with some BDSM stuff and got to know some of those folks, and through some swinging parties did get involved in some cuckolding type scenes, so she knew about cuckolding as a pretty young woman. Now, there are those on this board who I know think of cuckolding as only something that can happen between man and wife. For the sake of my stories, I'm defining cuckolding in a broader way, in situations where the woman has either taken or been given sexual control to find satisfaction from another sexual partner. So, bear with me on this broader definition.
However, Alex gave birth to Bethany in 1973 as a single mother and that was when she decided to settle down and "straighten up" her act. She didn't become a banker overnight. In fact it took her a while, but when Bethany was eight Alex married and they moved in with a man who was not Bethany's father biologically, but played the role of a loving father and helped Alex through business school and all that. It was a happy time in the family life.
In the early years of marriage, Alex was probably not so much focused on her sexual fulfillment as she was on getting her family stabilized and getting her career off the ground. Alex was a free spirit but first and foremost she was a good mother. But, interestingly enough, when Alex got out of business school and started to have major professional success, she started to feel more dominant in her relationship and more critical of the sexual aspects that weren't fulfilling. Bethany knew nothing about this, of course. And Alex didn't want to confuse or concern her daughter so she kept her sexual frustrations on the back burner for a while.
But eventually, Alex ended up cheating on her husband while on a business trip and remembering how good sex could be. After that, she could not really control that part of herself and so sat down with her husband and laid down the terms of the relationship. She knew he would be a willing cuckold based on his behavior and insecurities and so it was. At the time the cuckolding began Bethany was 14. At first, they were careful to do the cuckolding scenes when they knew Bethany was in school. After a couple of years of not getting caught, I guess they got a little careless and forgot about a school day that was cut short for parent-teacher conferences.
So, Bethany, who was 16 and just beginning to experiment with sex, got home from school early on Friday, and heard her mother screaming from the bedroom. She instinctively ran to help her, thinking something was terribly wrong. She flung the door open before realizing that the screams might have been screams of pleasure – Bethany had never heard screams like that before from her mom. The scene on the bed was one Bethany wouldn't forget: A large, very tall, very well muscled man who had an "all over tan" was on top of his mother, banging away between her thighs. Alex saw Bethany at the door but Bethany slammed the door and ran from the house, she could hear her mother calling out to her.
Bethany left in tears and went to stay at her best friend's house. She was really upset because she loved her new family and her father and couldn't believe her mother betrayed the family like that. She wouldn't even talk to her mother for two days, but finally she got on the phone and heard her mother say, "it's not what you think Bethany!" before Bethany hung up on her.
The next morning Bethany came by early to get some clothes, and she saw her parents happily having breakfast in the kitchen. This only upset Bethany more, figuring her father didn't know, but on her way out the door, Alex stopped her and whispered to her, "Bethany, it's ok, he knows! He knows about what happened and he doesn't mind at all!" Bethany didn't know what to say and went off to school. But she eventually did come back home to find out more. She asked her father point blank if she knew that her mother had a lover and he said, "yes, honey, and I don't mind. Your mother and I have an understanding." They both promised Bethany not to ever do that in the house again, and that was really it. Alex told Bethany when she was a little older she would explain more, once Bethany was 18.
Bethany didn't have too much sex those years but she had lost her virginity her 17th year. After she graduated from high school she was set to attend a summer program. It was time for Alex and Bethany to have their talk. Alex had given this a lot of thought the last couple of years. She didn't want to diminish her husband in Bethany's eyes but she also wanted Bethany to be fully aware of her own sexual options and choices.
So Alex explained to Bethany that while she respected her husband deeply as a provider, her was not adequate for her sexually. She felt terrible about the time she cheated on him but realized she wanted that freedom within the relationship. So, she explained to her husband that she needed more sexual satisfaction than he could give her and that she wanted to explore cuckolding with him. Afraid to lose her and fully aware of his own inadequacies, he agreed, and ended up loving the arrangement. Alex was an intimidating woman, I guess he felt some relief not having the pressure to please her fully. He found that he loved watching a big stud with a big cock fucking his wife deeply and to huge orgasms right in front of him.
Bethany didn't understand cuckolding at first when her mother used the term. "Cuckolding means different things to different people," Alex told her. "For me, it means that I needed a man to take care of me sexually in a way that my husband cannot." Bethany was always a confident girl, not afraid to get to the bottom of conversations, so she pressed her mother on this subject.
"What do you mean he couldn't take care of you sexually? Did that mean he wouldn't eat you down there?" Bethany asked, thinking of a couple of her boyfriends that didn't want anything to do with oral sex on her, and one that was really pretty good at it.
"Oh no," Alex said. "He was always good at oral sex. But there's something I have to tell you about your father, and I don't want you to think less of him because he is a great father and you should always respect how he has cared for both of us." Bethany was a little confused by this talk. "You see, your dad has a small penis, and I'm a big girl. I need a big penis inside me to feel really good. I had some big penises before I got married and loved them. I forgot how much I missed them, and I was very grateful to your father when he allowed me to try them again. If he hadn't, I honestly don't know what I would have done."
Bethany and her mother ended up having pretty detailed conversations about size at that point, Bethany never told me all of this and it's probably not relevant anyhow. Bethany wanted to understand what her Mom considered large and small, how big her lovers were, etc. To make a long story short, Bethany was surprised because she had not really had a problem enjoying sex with guys that her mom considered "small." "Well, Bethany, you're still practically a virgin and still young. When you get older and have some more experience and some bigger cocks, you'll understand how important it can be sometimes. And Bethany, after I had you, my desire and ability to take larger cocks got more intense." Bethany felt a little awkward about this conversation but she did admit to me that she masturbated about it later, thinking of this muscular, big cocked stud making her mother's pussy come while her father listened from the closet (which was what he preferred to do rather than watch or participate.)
Alex wanted to make sure Bethany understood a few things during this heart to heart talk:
One, she wanted Bethany to understand that size matters to a woman's pleasure. She felt so strongly about it that she made Bethany promise that she would try a big cock before she got married, just to make sure she knew what she was either getting or not getting in her marital situation. Second, she wanted to encourage Bethany to always be honest with her partner about all aspects of sexual needs and satisfaction, to never cheat on her partner and to always bring all problems and desires into the open where they could be discussed and addressed. "Your father almost left me when I cheated on him that first time," Alex said. "That was not the right way for me to handle my desires and you should always be honest before you run into that kind of trouble."
Alex strongly suggested that Bethany remain on the lookout for big cocked sexual partners. She said to be careful to understand that there is a difference between love and sex. "Don't fall in love with a guy just because he has a big cock and can make you come!" Alex warned. "The problem girls have is when they fall for guys who are good in bed but treat them so badly out of bed or aren't good relationship partners." So, Alex said, "get your sex where you need it, from boys that can please you," and "worry about love separate." If it all comes together in one great guy, "then marry him, no matter how young you are, because those guys are rare!" But she said, "If you end up falling in love with a smaller man, just remember that most smaller guys are turned on by watching their girls with bigger guys, if you handle it in the right way and include them and tease them." And many smaller guys, she said, "will treat you super nice and support you like your father has done for me." (overall, this seemed like pretty great advice to give a young sexually active heterosexual girl...don't you think?)
Bethany then talked more with her mother more about cuckolding and asked more questions about it, and her mother gave Bethany a lot of details. Bethany told me about this years later and we both agreed that the one thing Alex didn't do was she probably didn't tell Bethany about the more humiliating things her husband was into. She didn't want to take any chances that Bethany would respect her father less, so she didn't go into all of the details of this part of the situation, except to say that he was turned on by watching her have sex, and that he also approved of Bethany being told of this aspect of their relationship when she turned 18. I have no doubt that it turned him on to know that his daughter knew more of the story about him, I know it would turn me on in that same situation. But I also understand why they waited and why they were in the end somewhat discreet about the whole thing.
So, Bethany went into college in her 19th year with more of an open mind about the importance of penis size and more of a knowledge about cuckolding as a viable lifestyle option that most girls of her age. I'll pick up the story here next time.
- to be continued -
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alpha69male
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202
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# Posted: 24 Jun 2007 12:28:25
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great story man
Alpha
E mail me : alpha69male@yahoo.co.uk
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jasonwr1975
Member
46
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# Posted: 25 Jun 2007 10:23:40
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Growing Up Cuckold, Story 2, Part 2
I'm not going to spend a lot of time on the detail of this part of the story as I want to get back to the part where my life intersected. However, Bethany told me about her college sexual experiences in a lot of detail since we both enjoyed talking about it. So, that may be a topic to revisit down the line after I have finished telling of my own adventures. I will cover this part in brief now so we have a good understanding of Bethany's sexual outlook when I met her. I may spend some time on some parts of this college story, but I'll skip over others and come back to them maybe later.
Let me describe Bethany briefly as I haven't done that. Heading into college she was a 5 foot 6 blonde with pretty striking facial features, kind of a movie star look which she had inherited from her mother. Her breasts were on the small side but well shaped. Her ass was in my opinion her best asset, perfectly round (though by the time I met her it had gotten a little bigger). Bethany was one of those girls who was always a little frustrated by a little extra fat on her ass even though guys just loved it. She definitely oozed sex in kind of a classic "Marilyn Monroe" kind of way and had a really fun personality, more of a geek in some ways than a goddess, though she learned more how to be a controlling goddess as she got older and more experienced.
Her first year of college she pretty much ignored her Mom's advice and didn't discrimate based on penis size. She ran into some small and medium sized cocks and had fun, but all cocks pretty much felt good to her then and she was more focused on just experimenting, so she tried anal sex a few times, even had sex with a couple of girls. Her interest in sex was strong enough that she decided to include sexual health as a significant part of her college studies. She would eventually major in a pre-med health curriculum and minor in theater.
Her second year in college, Bethany got involved in a health clinic that was partially staffed by work study students. There, she met her first real boyfriend of her college years, who was also involved in sexual health as part of his goal to be a social worker. He was one of those social change types and looked back fondly on more experimental sexual times in the 70s. He prided himself on being real open-minded sexually, had been with a couple of guys even. To the point I lost track of Bethany, this guy remained number one all time pussy eater in her book, even counting the handful of girls she had been with. He had a combination of zest for the job and well-practiced technique. His cock was average at six inches or so, not real thick, but he knew a lot about female anatomy and knew how to find his way to the gspot. He was a good boyfriend and lover for her, though he pushed her to experiment so much that sometimes Bethany just wished they could be monogamous. They had a few threesomes, things like that. I'll call him David.
Things proceeded along those lines for most of her sophomore year. Then, toward the end of the spring semester, she ended up doing a counseling intake session with a girl that she knew from the dorm. This girl, Abby, was a pretty attractive, busty brunette, marketing major, a go-getter. For the past month she had been dating a pretty geeky guy that seemed to be having surprisingly good luck with the girls in the dorm. Bethany recalled thinking that he had an odd, off-key self confidence.
As an intake counselor, Bethany's job was to take a brief survey of the issue and then offer a bit of advice and refer her to a full time staff person. So Bethany sat down with this girl (Abby), and asked her what the reason for her visit was.
Abby got kind of flushed. "Well, I'm kind of embarrassed to talk about it." Bethany assured Abby this was all totally confidential.
"Well, I'm having some trouble with sex with my boyfriend David. His penis is just too big for me and I don't know what to do. I can't take it inside me and we are both frustrated."
Bethany knew the basics of this kind of thing, so she asked Abby if she was using lubrication.
"Yes, but it doesn't help much. I'm really tight and as much as I want him inside me I can't get it in. I love playing with it though!"
Bethany felt a little flushed and out of her league. Big cocks were not something she had experience with.
"Have you ever had this problem?" Abby asked Bethany hopefully.
"No, but...." Bethany felt shy talking about it. "I've never really had a big cock."
Abby looked disappointed. "But don't worry," Bethany said, "I'm sure one of the full time staffers here can help you."
Bethany thought through her mind...there were only two female doctors on the staff. One was older, near retirement age, and was helpful for some problems but probably too conservative for this one. The other female doctor, Sally, was in her mid-forties. She was one of those older women who was not as attractive as she once was but seemed to hint at a lot of sexual experience and likely was very hot when she was younger.
Bethany referred Abby to Sally, who would see her the next day. That night, Bethany woke up after David was asleep and found herself masturbating thinking about this big cock that wouldn't fit inside a pussy. She had never really had any trouble getting a cock inside her. What would that be like, to go up against your limits? What if David had a cock like that, what would it feel like inside her? Would it feel differently than his small one? This was the first time she had ever thought of David as "small," and she corrected herself in her mind. "David's fine, he's average, he feels good inside me." But the fantasy carried her and she came hard.
The next day, Bethany had a day off from the clinic but she found herself making an excuse to come by. She poked her head into Sally's office.
"So," she asked Sally, "Did you talk to Abby about her little...problem?"
"Yes I did." Said Sally, motioning to Abby to close the door of her office and step inside.
"Actually," said Sally, "Abby has kind of a 'big' problem." Then Sally made a gesture with her hands and smiled kind of wickedly.
Bethany couldn't restrain herself. "How big?" asked Bethany.
"Well," said Sally, "from what I could gather from Abby, he's about eight inches long, which is large but not exceptional. She should be able to take most or all of his penis inside him when she is aroused."
Bethany felt herself getting wet just listening to this.
"The problem here is girth," said Sally, emphasizing the word "girth" as if she loved using it. "Her boyfriend is pretty exceptionally thick. It sounds to me like he is seven inches around. That can be painful for a young woman who hasn't had a lot of sex."
"Of course," smiled Sally, "It is a really great thickness for many older women." Sally was implying that she would have no problem taking such a cock but she was careful to remain a little bit professional about it and not speak for herself.
Bethany felt a decided drip come out of her pussy and trickle down her leg, but good thing, she was wearing jeans and not shorts. She found herself feeling a little squirmy and sat down.
"So what did you tell her?" asked Bethany.
"Well, I asked her about lubrication first," said Sally, "but I knew you already covered that. Then I asked her about foreplay. It sounds to me like her boyfriend could use some work on the foreplay, getting a girl warmed up."
"Bethany, you may find this part interesting," Sally said with a knowing smile. "But a lot of women, even older women, don't understand this part. Abby told me that they always took time for foreplay and by the time he tried to insert his big penis they were both really turned on."
Bethany felt flustered by the phrase "big penis." It seemed like Sally was trying to make this conversation as sexual as possible without being unprofessional. "But I asked her, 'have you typically come by this time?' And Abby said 'no.' Usually he licks her but then they get too excited and they want to have intercourse at that point. I told her it was very important that he make her come with his mouth or fingers first. Only at that point, after an initial orgasm, will the vagina expand enough to take that kind of girth for the first time."
There was that word girth again, emphasized again by Sally. Bethany crossed her legs and tried to ignore how warm she was getting.
"One thing I did warn Abby, however. I told her that no matter how warmed up she is, there is a good chance the first time with such a thick penis will be painful for her, at least at first. And she needs to watch the length carefully also, to make sure she can take the whole thing before she tries any deep thrusting."
"So I said, 'Abby, you have a choice. You can avoid penetration with this partner and avoid some initial pain. Or, you can try these techniques and grit your teeth a bit. If you do, from the research I have done, you should have some of the best orgasms of your life. You'll have some pain, maybe always just a little, and certainly some soreness afterwards, but there is a good chance you won't regret it. It will take some work, as this lover is probably three times as heavy in size as the biggest lover you have had previously'." (Sally seemed to have some knowledge of the important concept of cock volume, though she didn't use that phrase. It's something I've thought about a fair amount in recent years...cock volume comparisons are far more revealing than cock size comparisons when it comes to a woman's pleasure).
Sally continued with her advice but Bethany had an odd feeling she was now addressing it more to her than to Abby. "Remember, a longer, thicker penis will stimulate your orgasmic pleasure in a few different ways that smaller ones can't. First, a thicker penis will rub against the clitoral hood while thrusting, and likely pull the walls of the vagina in and out which is highly pleasurable also. Thinner penises can't generate that friction." When Sally said that last part about thinner penises, she looked at Bethany almost like she was accusing Bethany of putting up with inadequate lovers. Or maybe Bethany was just taking this too personally.
"In addition, many women will experience a massive, deeper vaginal orgasm through the sensation of being filled and rhythmically stretched throughout the vaginal cavity. And some even report a very pleasurable orgasm through contact with the cervix, though you have to be careful as penile-cervical contact is not pleasurable to all women."
Bethany felt a little tongue-tied by the honesty of this advice. She found herself dwelling on that word 'massive,' picturing a massive cock slamming in and out of her tight little pussy, making her feel pleasures she had never known before. She suddenly thought of David, pushing his little (there was that word again!) cock into her and not stretching her pussy and not tugging on her pussy walls and she thought of him banging away but not filling her up and not hitting her cervix for good or for bad.
"Bethany," Sally said with almost a wink, "I hope you remember this advice for future treatments and intakes."
Bethany had lost concentration, thanked Sally and excused herself. That night David did not sleep over, he had to cram for an exam. Sally did not need David's help that night to have a huge orgasm. She was lucky that her roommate was out of town, as she screamed extra loud while making herself come, jamming extra fingers inside a pussy that had been leaking and craving a big come all afternoon. And on her way to her orgasm, she had a very nasty image that came out of nowhere, it felt so mean it was almost satanic, but it was an image of David jacking off his little thin cock sitting on the edge of her desk while she screamed in ecstasy, her pussy clinging to a big fat cock that literally pulled her pussy inside and out, while her body dripped with sweat and contorted underneath the pounding thrusts of...Abby's boyfriend? No! That was too much, too twisted...but she had one of the best orgasms of her life in the middle of those thoughts.
- to be continued -
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jasonwr1975
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# Posted: 27 Jun 2007 08:25:27
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Hey folks...since I don't currently have time to write another installment, I thought I would take the time to track down a couple of pictures that resemble the people in the story. In the previous installment (story 2 part 1), I refer to "Alex," Bethany's Mom, and that she looked a bit like Lauren Hutton. Attached is a picture of Lauren about the age, I think, that Alex was when I ended up meeting her. Alex wasn't quite this hot but had a similar look of grace and self-confidence. I can't post a real pic of Bethany unless I track her down again and get her permission, but I'll find a likeness of her too here and post it pretty soon.
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illbyourbitch
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6
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# Posted: 30 Jun 2007 16:20:34
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hey,
just wanted to say great story! I've been enjoying it for a while, and I can't wait to hear the rest.
As a very well-endowed (almost 8" and thick) submissive cuckold I will say, that in the end cock size doesn't make the cuckold.
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jasonwr1975
Member
46
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# Posted: 1 Jul 2007 08:41:41 · Edited by: jasonwr1975
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Thanks for the good words "Ill be." Hopefully you read earlier in this long-winded story that I did acknowledge that cuckolds do come in all penis sizes. Penis size and submission are different concepts, however, I do feel that for many (though not all!!!) cuckolds they are related. For example, I think it is harder (though not impossible) to be a dominant guy with a small cock. (if you have ever been cuckolded by a guy much smaller than you, "I'll be," you should share that with this board sometime as it would make a very informative perspective on cuckolding we don't hear as much of around here).
At least some Alphagirls simply won't be dominated by a guy who is smaller in size. I have been with a number of girls who could only come vaginally on larger cocks, and for those girls, they were much more submissive in the presence of cocks that could make them come whether they were in the mood for sex or not.
But just as not all cuckolds are small, not all women are turned on by the same things or think the same way about size. This diversity is great and also means there is hope for all of us to find our right sexual "match." For me, my smaller size was my avenue into cuckoldry and also sexual submission. Mostly it's been a great ride, sometimes it's been difficult. I've already hit on both sides in this piece and will continue to.
I have a dominant side too and I have to think that if I had a bigger cock I would have explored that side of myself more easily and thoroughly. But I guess I will never know. So, I agree with your point of view, and we never want to simplify these things into saying that "all cuckolds are like this" or "all women are like that." At the same time, this is my story and I find that it's better to just tell it as I experienced it without trying too hard to incorporate all viewpoints. Since I have never run into a cuckold with a big cock in real life, it doesn't factor into my story. Anyhow, thanks for the good comment and I'm trying to get to another installment now. Back to the writing.
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jasonwr1975
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46
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# Posted: 1 Jul 2007 10:11:42
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Growing up Cuckold, Story 2, Part 3
I realize I have gotten a little caught up in this "Bethany college life" thing but I feel it's important to share this part so it will be easier to see how a 25 year old knew as much about cuckolding as she did when I met her. Plus this part of the story was always so hot to hear her tell, and I can't help but share it. Since several of you have let me know by email that you are enjoying this detour, I will keep going a bit, then bring the story back around to me.
So, Bethany wrapped up her second year of college with these nasty fantasies about Abby's boyfriend in her head. Nothing much happened with them, though. She didn't even know the guy except by sight (I'm using made-up names for this part of the story, so I'm going to call him Nick.) Anyhow, Sally would see Nick around from time to time, and she couldn't help herself from staring at his crotch a bit to get a view of his size. But Nick was geeky and shy and his clothes reflected that, he tended to wear baggier clothes. Once towards the end of the year Nick was playing guitar (not all that well) in the quad and she got a look at him wearing shorts, and for a second he uncrossed his legs and she thought she saw an enormous bulge, but then his shorts shifted and he crossed his legs the other way and that was that. She stuck around hoping to see more glimpses but nothing happened.
Meantime, she and David continued to have fun in bed and they even ended up having one threesome with another sex educator they worked with who was really open about her bi-sexuality. Her name was Becky and they had a fun time with her one night when everyone drank too much but then the school year ended.
However, Bethany and David both stuck around for the summer. They got a job doing summer landscaping and cleaning working for the college. It seemed like a good way to work a no-brainer job and not go home. They were housed next to each other in a student dorm and summer life started in. It was a pleasant summer, the kind of no-worries/Bob Marley-in-open-windows summer that you really take for granted when you are younger and long for after that. Bethany and David still had fun together sexually but perhaps they were both a little bored. There weren't that many student workers there and so there weren't as many options as usual to consider for fun exploration. They tended to find themselves kind of tired from the physical labor anyhow. Bethany still masturbated sometimes thinking of Nick and variations on Nick and her and her boyfriend, but even those fantasies seemed a little distant to her.
But then, Bethany got the surprise of her summer. One day she was carrying her tray through the dining commons and she saw, of all people, Nick walking towards her carrying a tray also. She told me that the minute she saw Nick she would never forget. She felt an electric jolt go through her whole body and wind up between her legs. She could almost her pussy screaming in joy. Nick disappeared into a meeting room with some professors having lunch, but before he went into that room, he gave her a smile and a nod of recognition. That sent a second jolt through her body and in between her legs. That was when Bethany had a really awful, bitchy thought that she told me later because it was so memorable, wrong, and nasty: she knew at that moment that whatever it took, whatever it cost her in her friendship with Abby or in her relationship with David, she was going to get Nick's big cock inside her pussy.
This probably wasn't the smartest course of action. Walking back towards her room, almost dizzy from the thoughts, Bethany found herself hoping that Nick would go away again, wherever he had come from, and not wreak havoc on her summer.
But she ran into him again the next day getting his mail from the student post office boxes. For the first time ever, they had a conversation. Nick seemed really shy and he wasn't easy to talk to. She realized later he must have been a little intimated by her, it was only later she realized how much alpha girl power she could exert, especially wearing skimpy summer shorts and suggestive tops. But she did get out of him that he was back on campus for six weeks, as part of a mathematics camp where he was a tutor for the kids. He was also living on campus but on the other side with the tutors and professors. But they all had lunch in the dining commons it seemed, and she saw Nick again a couple of times in the next week, usually having lunch with professors. He always smiled and waved. It seemed so innocent, but her feelings were anything but.
One thing I want to say here is that Bethany eventually learned that you don't risk a good relationship for lust, no matter how intense that lust might seem in the moment. This was a good adult lesson for her to eventually learn and by the time I met her she had learned it. At the same time, she would tell me later that while risking a good relationship is not something worth doing, at the time, it certainly heightened the intensity of her sexual feelings. Thinking she might be willing to throw everything away for a chance with Nick led to some of her hottest masturbation ever, she felt like such a wanton crazy slut, a slave to her own pussy's craving to be filled. It was very intense for her sexually. But then after she came, she would feel conflicted about it all. And David really was a good boyfriend, a bit distracted sometimes by his own utopia and adventures but very thoughtful and considerate most of the time, and very committed to her.
One day, it occurred to her that she didn't necessarily need to risk her relationship with David. All she needed to do was convince the two of them to have a threesome. (Now, you may find it odd that it took her a while to realize this option was a viable one. Looking back on it much later, Bethany told me that on some level she must have known that despite David's superficial open-mindedness, that he would be very threatened by Nick's big cock. She knew on some level that this would not be an easy threesome for "free-thinking David.)
David claimed to be bisexual and open to threesomes with men, they had just never done it. I'll cut this part of the story short, but after some talk, David did agree to try a threesome with Nick. He didn't understand at this point why she wanted to give Nick of all people a shot at a threesome, but she just told him she thought he was nice and would be fun to play with. David was kind of bored with the summer sexual routine so in time he agreed.
The hard part was talking to Nick about it. They had run into each other enough times and even had some talks on the way out of the dining room, but never the kind of talks where something sexual could be brought up. Nick seemed flirty with her but he also had seen her with David and so he knew she had a serious boyfriend.
One day there was a stroke of good luck, and she found herself running along a tennis court where Nick was shooting hoop on the side. She remembered thinking that he looked kind of awkward and girlish and not much of an athlete. But he waved and they sat down on a bench together. It was just dinnertime, the campus was pretty empty and no one else was around. They talked for a while, and at one point Nick mentioned that he and Abby had broken up, but that they were still friends.
It was there that she was able to ask Nick the question. It wasn't easy for her but she was so in lust with the idea of getting him into bed that she just popped it out there straight:
"Would you like to have sex with me and David?"
Nick was shocked. He didn't say anything for a minute. Then he said, "Well, I want to have sex with you. But David?"
Bethany explained that they liked to experiment in their relationship and bring in other partners. She made it seem like they did it all the time, male and female, which wasn't true, but she wanted to put Nick at ease and not make it feel weird.
"Nick, I'm really attracted to you, but I don't want to cheat on David. This seems like a way to do that."
Nick was pretty taken aback. "I'm not bisexual!" he said kind of strongly. (Nick later told her that he had been teased a lot and called a "f**got" in junior high and high school and he was really self-conscious about being seen as girly and gay, and he thought that this is why Bethany had picked him out from the other guys that summer, because maybe he seemed more "bi" than other guys. But she didn't know that then). He seemed a little mad when he got up from the bench, and said something like "no thanks."
But Bethany couldn't hear him well, because she was distracted by the distinct hint of a big fat pipe-like bulge running down the side of Nick's leg before he turned and walked away from her. The sexy talk, as awkward as it had been, had gotten to him. Her pussy got another big jolt. She was disappointed that he didn't agree to do the scene, but she didn't get too upset. She could feel that strong electric tingle between her legs, and her pussy almost whispering to her, reassuring her to be patient, that she would get to try that big cock at some point if she was crafty enough.
Nothing happened to further this situation for a few weeks. It reached the point where there were only a couple weeks left of math camp and Nick would be leaving soon. Bethany was feeling frustrated. They still talked and flirted but didn't really speak of that day. It seemed obvious she had hurt Nick's feelings in some way despite telling him that she was attracted to him. Bethany couldn't figure out what to do about it. She began thinking about cheating on David again, but just couldn't quite bring herself to do it.
But finally, she got an opportunity to push the issue. There was some kind of student party that Friday night, a local store owner had some sympathy for them and sold them a bunch of beer even though he was not supposed to sell to the college workers and most were underage. Suddenly there was a drinking party behind the dorm's loading dock. Nick ended up showing up. David was there too. David seemed to be keeping a wary eye on Nick but Nick didn't talk to Bethany much anyway and eventually he left. David got really drunk that night and ended up heading out into the woods with a couple of pals to do some kind of weird scavenger hunt. That's when Bethany saw that Nick had wandered back into the party.
"Want to go on a walk with me"? Bethany asked him. She didn't know what she was doing, but knew she had to get him alone. They walked towards the edge of campus and sat on a rock facing the woods where they had some privacy.
"Nick, I'm sorry if what I told you upset you," she said.
"It's ok," Nick said. "It just sucks that you have a boyfriend. And I hate it when people assume that I am bi," he said.
"What?" Bethany asked? "You thought that's why we asked you?"
"Yeah," Nick said.
"Oh no...!" She said. "That's not why at all!"
"Then why?" asked Nick. (He did not yet have enough sexual experience to realize just how much sexual power he could wield in situations like this and just how much girls can talk about stuff like that between each other...so his question was honestly innocent.)
Bethany felt a flush coming to her face, but she had a bit of drink in her and was a little buzzed and verbally loose. Something came over her and she just blurted out, "because I heard you have a big cock, and I really really want to try it!"
Nick blushed incredibly. He was speechless.
Bethany was in overdrive, however. Some of you cuckolds out there know what I mean, but when a dominant woman starts feeling her power, look out. She told me later that this was one of the first times something really took over inside her, something completely confident and insatiable, devious in her ability to get exactly what she needed sexually in a way that most people can only fantasize about, including me.
Bethany pushed his back up on the rock and straddled him quickly and aggressively, looking right in his eyes. "So do you Nick? Do you have a big cock for me?"
Nick didn't know what to say, he was totally taken aback, but he did seem to have a hint of a wicked smile. Bethany felt a surge of submission inside her also, realizing that most guys would have withered after such a direct question about their cock size. Nick didn't boast, but he didn't shy away either.
Bethany reached for his belt buckle, humping her hips on him. "That's it Nick. Enough teasing. I want to see it. I want to see it right now."
She pretty much frantically pulled down his zipper and pulled his cock out. It was tough to pull it out, already half hard, and she was struck by how thick and masculine it felt in her hand.
Then with one more tug Nick's cock surged, big and swollen in the moonlight. "Oh Wow, Nick! That is one big fucking cock!" Bethany said, still stroking it, trying to get it even harder.
"Really?" Nick said. He was having more fun now and getting more comfortable, he had certainly had this reaction before and it fed his adolescent ego.
- to be continued, sorry to cut it off here, gotta run -
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colleenslittletoy
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# Posted: 1 Jul 2007 18:14:55
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I really got caught up in your story. One reason is that I had a girlfriend named Lisa who used me like your friend did.
My Lisa looks like Jennifer Love Hewitt only sexier, if you can believe that. I met her at work, I'm a manager and she's a secretary. She was going through an ugly divorce and I took advantage of the situation and offered my shoulder for her to cry on.
One thing led to another and soon she was living with me.
Like you, I suffer from an average, if not smaller appendage, but at first, Lisa didn't seem to care. Maybe she was grateful for me taking her in and paying all her bills. Our sex life was awesome, at least for me, but I soon realized that she came away frustrated usually.
Consequently, more and more often, I tried to satisfy her with my tongue and mouth. I was trained by my ex-wife, who took cheating to an art form, to appreciate a woman's body with copious oral adoration and found that I enjoyed it almost more than love-making.
Most nights found me beneath the sheets with my mouth glued to Lisa's mound trying my best to get her off. Everything seemed ok until the night she rolled over.
As an aside, I have a strong streak of masochism that runs through me and if I don't control it, it soons controls me. The end of my marriage was partly caused by my worship of my wife to the extent of getting off by mouthing her. When she taught me to kiss her ass I was doomed. By submitting to this depraved act it became easy for her to convince the both of us that cuckolding was the only solution to our marriage.
Back to Lisa. When she rolled over I was back in the situation of surendering my control to another woman. As I licked, I entered some zone of submission and soon shot all over the bed. It didn't help that Lisa was chuckling.
At work, Lisa started flirting with a warehouseman. I watched, secretly, as they flirted. Of course, I was torn between jealousy and arousal, the familiar state that my ex-wife kept me in.
I decided I should talk to the guy, thinking I could stop things from getting out of hand.
You talk about alpha women, this guy was a alpha man.
He is stronger, a lot more muscular, and has a condescending way about him even though I am techinically his boss.
Instead of making the situation better, it worsened because I approached him. He quickly saw how intimidated I was around him and before I knew it, he invited himself over to my house.
more later
J
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curio
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# Posted: 5 Jul 2007 18:19:55
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This was my first reading on this site. I was really blown away by this confessional. Thanks so very much. I hope you post again. You really seem to have a deep understanding of the whole cuckold/beta male thing. It's fascinating.
This quote (below), in particular, speaks for so many of us less fortunately endowed, yet intelligent individuals. I've felt this so often in the past. Have denied my "inclinations," yet it seems to be in my nature or genes. I've even hated myself for have these inclinations. But it turns me on, I can't say why. I don't want to be a "perv" yet I feel myself instantly aroused at the thought of it. Because, again and again, I recognize that women have these primal needs; it's always surprising, but undeniable. On some level, we're really beasts underneath. Females desire the bigger lion to mate with, on a primal level; I've lived long enough to recognize this, again and again. Sensitivity and PC correctness aside, they all fantasize about the big hard dick, whether they admit or not.
But here's a quote from you writing that I liked so much:
"It was sexually gratifying, but it left an emptiness in its wake and at the time, a profound confusion over how I should carry myself as a man."
This is really great. Boy, I've felt this so often. I hope you'll write more.
Thanks again for posting.
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jasonwr1975
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# Posted: 6 Jul 2007 08:16:38
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Hi Curio. I'm glad that my story struck a chord with you. My goal from the beginning of writing this story was on some level to entertain by sharing my journey but to offer more than just a good read for those who have also struggled (and continue to struggle) with aspects of the cuckold identity. The Alpha/Beta struggles of coming to terms with your masculinity in a world that is still driven by primal attraction is intense.
One thing I would say here is that I have made a commitment to seeing this story through to completion, so I will do it. Health and work problems are keeping the progress slower than I would like but I will persevere as I am working through some key things for myself while writing it. At the same time, I welcome feedback from folks like yourself because it energizes and motivates me to know that others are taking something from my work.
If this story makes people less lonely and isolated in their own sexual identity then I am really humbled by that and glad for it. I know what you mean about struggling with self-hatred and even aspects of your identity that might feel perverted. God knows I have been there before and will probably be there again. During times when I have been single, I have had huge porn addiction struggles trying to make sense of my fetishes, which have tormented me but are not something I think are ultimately healthy to deny. The goal is some kind of healthy integration.
At the same time, there are some great things about coming to terms with who we are sexually, and I think, an odd and different kind of "cuckold confidence" that can emerge from this. Now, I'll be the first to say that some cuckolds thrive on the humiliation and don't look to be sexually confident in that classic way. But while I think it's hard to have Alpha male confidence when you have a cuckold identity, there is a different kind of "cuckold swagger" you can find. It's got something to do with having faced your deepest fears, your shadow as some would say, and come out on the other side proud and unashamed, and fully accepting of one's sexual strengths and weaknesses and how to get all those needs met.
As I said in the intro to this whole story, I think it takes more strength to acknowledge our weaknesses and/or handicaps and embrace/allow them fully into our identity than to just be control freak/small dick jerks running their women into the ground, or trying to, and we all know guys like that, who take out their insecurities out on others in a secret rage about their unexpressed inadequacies. I believe our insecurities can become a source of sexual connection and power if acknowledged and celebrated. Not, no alpha male confidence and power, but power nonetheless - the power of an intelligent, unashamed, erotic mind and self-awareness. At least that's what I am shooting for! Though I'll be the first to admit that it's never going to be easy being a sexual "beta" in an Alpha type of world. Well, perhaps in this forum we can help each other through it and even inspire from time to time. And of course get some hot sexual stories out of it too!
Ok, end of thought process, will try to post another installment soon.
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curio
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# Posted: 8 Jul 2007 02:02:02
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Some incredible points:
"The Alpha/Beta struggles of coming to terms with your masculinity in a world that is still driven by primal attraction is intense."
"It's got something to do with having faced your deepest fears, your shadow as some would say, and come out on the other side proud and unashamed, and fully accepting of one's sexual strengths and weaknesses and how to get all those needs met."
Wow. You're a true artist, with the reference to a Jungian "shadow." I'll be into reading anything you write.
I'm definitely in the same psychological boat as you, it seems. I'm similarly endowed and aroused by the humiliation caused by this.
I've been called "small" directly to my face. There's something disarming about acknowledging this "fact." My inadequacies are nothing I can do anything about.
I'll always know she'll want and fantasy about someone more virile and masculine, and there's nothing I can do but accept it and eroticize it. I'll always know I'll be on beta end of the scale, instantly replaceable in the bedroom and more than likely quickly forgotten.
I'll go through periods of striving to see myself as something more ... but it always comes back to me in end. Size, but also hardness and virility is a factor. In romantic relationships, my destiny is clear; I'll always be a secondary choice, more "the friend" and never "the one." The one who takes her breath away and make her swoon.
It's almost gotten to the point where the more humiliating things are for me, the more of a turn-on it is. In many cases, it's not just about cuckolding, it's accepting (or being forced to accept) the sexless, beta-male "girlfriend" role, which is my constant fear and therefore of course what I fantasize about. The "boyfriend who moves in" scenario always blows my mind, too -- and the slippery slope effect of that, of having to accept that "role."
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jasonwr1975
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# Posted: 8 Jul 2007 08:31:04 · Edited by: jasonwr1975
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Growing up Cuckold, Story 2, Part 4
Thanks to all for the good comments of late. It's nice to know that this story is being read and enjoyed and sometimes provokes good discussion. Curio, I was going to comment more on your last post but I think I'll continue on with the story instead and get through this backstory, and as I go forward I'm sure some of the good themes you have raised will be addressed in certain ways as I tell my story.
Anyhow, picking right up...
As Bethany stroked Nick's cock to full erection, she wondered at the size of it. She would later see some longer cocks, but she never saw a cock too much thicker than his. Bethany told me later that as soon as she wrapped her hands around Nick's cock, even before she had ever tried it in her pussy, she knew instantly that all the feel-good New Age stuff she had been taught in her sex education training about how "size didn't matter" was way off. She felt so turned on stroking this big piece of meat, she felt herself involuntarily humping Nick's leg and she could literally feel her pussy starting to lube up and drip. She had never had that reaction to smaller cocks. It was primal, politically/sexually incorrect, and completely undeniable. Perhaps some girls would not be able to explore these size fantasies, but Bethany was young and in sexual control and she was going to find out one way or the other. She almost wanted to stop though, just because she was at that age where you hate it when your mother or father is right about something. But as much as she resented her mother in that moment for being right about big dicks, she was too turned on to care.
"Oh Nick, I love how your cock feels in my hands."
"Ohhhhhhhh...." was all he could say...the pleasure of seeing such a sexy girl go crazy for his cock and the feeling of her hands jerking it up and down, it must have been incredible to him, especially after a junior high school life of being shoved into lockers and picked on. Sure, junior high was a while ago at that point, but as the cucks among us know, sexual status feelings are formed early. Nick was like someone who had rose from the bottom of the sexual totem pole to near the top, and he couldn't quite believe his fortune yet and hadn't totally seized his new power.
"Wow....it takes two hands to jerk your dick off....it only takes one hand for me to jerk David," she said.
"Yeah," said Nick..."What about David?"
"I know...."Bethany said, kind of self-consciously. She felt conflicted about it, but guilty wouldn't be the right word. Some weird lusty part of her was telling her that she had a right to this cock. At the same time she was torn, but lust was taking over. She started jacking Nick's cock up and down, mostly with one hand and long strokes while she rubbed herself through her jeans.
"Oh Nick, I want to fuck you soooooooo bad."
Nick could barely speak he was in so much pleasure.
"Nick, do you want me too? Do you want to get this big dick inside me?"
"Oh god yes........."
"I'm a little worried," Bethany said, "I've never had a cock this big and I don't want it to hurt. Is it gonna hurt me Nick?"
Nick told her that his first girlfriend found it painful, she was a virgin, but after that he learned more about sex and never had a problem getting it inside a girl. It took a while to explain this as he was moaning the whole time.
"But can they take it all?" Bethany asked as she slowly rubbed his cock up and down.
"Well," Nick said, struggling to get his words out. "Most can...a few couldn't take me all the way in but we still had fun," he said, with a wicked grin on his face. Nick was starting to feel cockier, seeing how lusty Bethany was for his cock. Nick still didn't find it natural to be a "bull," but he was definitely starting to grow into that role more.
Bethany liked talking to him about his conquests while she was stroking him, so they talked about that. She asked him how many girls he had been with; he said shyly that he had lost track at about thirty. This was another one of those signals to Bethany that size maybe mattered more than she thought. David was a lot better looking than Nick and more outgoing too, and he had about ten sex partners and some of her other boyfriends had had less. Nick, meanwhile, had been with way more than thirty, including a friend of his mothers during high school (she would learn more about that later).
"Nick, I want to fuck you so bad," Bethany said. "But I don't want to cheat on my boyfriend."
"Uhhhhhhh." Nick was in such pleasure he wasn't communicating well.
"Nick, David likes to have sex with other people, threesomes..." She smiled at him and starting jerking his cock off a bit faster. "I already asked him if he would do a threeso |
