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Growing up Cuckold, Story 1

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jasonwr1975

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Hello.

As a 32 year old white male with a lot of experience as a cuckold, I have held off on writing about my stories, perhaps thinking I would be able to grow out of the cuckold life or find a different identity. But it seems that like other cuckolds on this board, this life is kind of in my DNA. I might be able to escape into a vanilla relationship for a while (as I am in now), but sooner or later, it seems to be my good (and bad) luck to always find myself in cuckolding type of circumstances. I say "good and bad" because I believe that most real cuckolds would own up to the reality that as hot as this lifestyle can be, it also comes with a good share of pain.

One thing I have come to believe is that there are many different kinds of cuckolds. And while I permisterally do enjoy some of the offense and teasing and find it very erotic, I would differ with those who label cuckolds as categorially weak or inferior as men. In my mind, the real weak man is the control freak little dick guy who bosses and beats women around and clings to status symbols. And while I respect "bulls" with big cocks who know how to please women, I'm not sure it isn't a bigger accomplishment to reach a point of self-acceptance where you know that your woman deserves more pleasure than you have to offer. It would have been a lot easier to learn how to fuck a girl properly with a big cock than it has been to figure out how to be sexually compelling with a small one.

My best cuckolding experiences have come from women who saw me not as less of a man because I was willing to be cuckolded, but as more of a man. Of course, that doesn't mean that the sexual dynamic doesn't change when you bring a sexually superior third party into the relationship. I guess all I'm saying is that I have met real suicidal/depressed type cuckold men who should realize that what they are doing takes guts and humility, and that the ultimate definition of a man comes back to conviction, courage, and the ability to care and protect those you love. Cuckolds can do that as well as anyone, and many do. Being a cuckold and being a passive man without core values are two different things. And there is a difference between intentional presentation and pathetic weakness.

End of intro. Thx for letting me get that off my chest.

Now, onto my first story. I'm going to start with true stories, as real and hot as I can remember them, and perhaps occasionally I will write fantasies to go along with them. But for now, I'll focus on true accounts since I find those hotter. The more encouragement I get, the more I will write.

Growing up Cuckold, Story 1 (true story): high school sweetie (part one)

Like many (but not all) cuckolds, I grew up feeling that my penis was on the small side. This made me shy with girls in sexual situations. At 17, I was attractive, athletic, and still a virgin. I had been told that size did not matter by sex educators and by the hippie health guides lying around my house, but I wondered. The high school I went to was half black/half white. Changing clothes in the gym locker room was a real reality check.

I was not teased by the other guys but definitely felt small. Some of the guys were bigger soft than I was hard (five inches). No, not all of the black guys were hung big, but some of them certainly were. What I found interesting was that most of the guys in the locker room who had the biggest cocks tended to have the hottest girlfriends and seemed to be the most cocky, some of them were real jerks. This was my first real doubt about the idea that size didn't matter. Why would girls have wasted time with some of those fools otherwise?

Since I was told that girls liked guys who were smart, kind, and athletic that's what I focused on, and I did get some dates and fooled around a bit with some girls. I was mostly distracted, however, by Lisa. Lisa was very sexually experienced and active at 16 and was my closest friend. She was just built for sex, like a young colt or something, and had a very hot way of getting whatever she wanted from whatever man she wanted. Her breasts weren't large, but they were shapely, and her ass was just phenomenal, in fact, I think she was nominated as "the best ass in school" by some fool as a joke.

The strangest thing was that Lisa's parents were really conservative. Her dad was a lawyer and Republican lobbyist. Yet the first time I visited Lisa at home, I noticed she had a copy of the Horny Teenagers Guide to Sex right on her shelf. Another time she was talking to a friend about being sexually active and it was clear that she had her conservative parent's permission to do it. Perhaps it had something to do with learning lesmisters raising her two older sisters, I don't know. What I do know is that it turned me on greatly to know that her parents approved of her sexual activity. She seemed like a truly free spirit who made her own sexual decisions.

I was pretty much in love with Lisa from the first time I met her and she loved me too. But pretty early on in our friendship, I got that sinking feeling that I am so used to in years since: that of an alpha female who adores me but does not see me as sexually compelling. Deep down I knew that Lisa and I would never be more than friends, but I couldn't think about any other girls.

Of course, I was confused by these things at the time and knew nothing of cuckolding. One thing that was very common in my high school was that the girls who were sexually active would make a point of doing most of their fucking with guys from other schools. This way they wouldn't be dogged by so many rumors that they were sluts, which was still going on a lot at that time. Lisa seemed to be the same way. I would see her out at the mall with a pretty steady stream of guys from other schools. She was actually one of the few white cheerleaders at our school, but the only white girls at our school that "dated black" were pretty much exiled, so Lisa never dated a black guy in my high school that I know of. But she certainly dated lots of guys from other schools. Some of those guys seemed like real jerks, and most of them were hulking jocks that I felt nothing in common with and wondered why she liked.

Lisa's family had a pool with a small brown poolhouse/changing room that was to figure prominently in my early sexual education. The first time it did was at a party that was taking place at Lisa's while her parents were out of town (her older sister was loosely supervising). There was this jerky guy named Paul there who was throwing people into the pool with their clothes on. I had changed into my suit earlier so I avoided Paul's idiocy. Later that night, I remember realizing I had left my pants in the pool room when changing, and needed my pants and car keys to go home. Lisa was not around. I opened the pool room door, and straight ahead of me, 20 feet away on a bench, Lisa was kneeling down in front of Paul. Paul was seated on the bench, and Lisa was jacking his cock with both hands and licking his head.

At the time, Paul's cock seemed enormous to me. I've seen a lot larger ones since then, I would guess Paul's was around 7, but it was very thick. Paul said something like "get out of here dude!" but all I can really remember was Lisa's head as she turned around. (She was in her legendary two piece swimsuit). She had this teasing little smile on her face. Later in my life, I would come to know this face as "I hope you understand, sweety, but a girl like me needs a nice big cock like this sometimes." At the time, I was just surprised and tongue-tied. I grabbed my pants from the hook and left. I went home that night and had one of the best orgasms of my life jerking off to the scene I had just watched. It was very vanilla compared to some of the things I've experienced since then, yet it was seared in my memory.

Some more interesting things would happen with Lisa which I will try to write about soon as I have time. For now, what I would note is that while this encounter with Lisa was brief, I think in that moment she sensed a way in which she could be attracted to me sexually by making me somehow submissive to her. She was more attracted to me realizing how excited I was by her power. This theme was to get more intense later in our friendship, as she would realize how much it turned us both on that I was sexually unable to fully satisfy her no matter how hard I might try.

- to be continued -
(sorry for the long intro, I'll get right into the story next time)
cuckhsbnd

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this is very interesting psychologically. please do consider. very thoughtful and articulate.
geocleaner

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#3 · Edited by: geocleaner
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0000000.
jasonwr1975

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#4 · Edited by: jasonwr1975
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Thanks for the good words on the first installment. I shall continue on.

Growing up Cuckold, Story 1 (true story): high school sweetie (part two)

After I saw Lisa with Paul, I didn't see her alone for a couple of days. I ran into her with friends a couple times and she did have a cute smile for me. She was definitely not bothered by what happened.

The middle of the school week, we ended up having our lunch behind the stadium together, which we would do from time to time. Before I continue, I want to say that Lisa was not what you would think of as a classic Alpha female. She had more of an open-hearted, hippy chick kind of vibe, without as much of an Alpha female edge as most of the women who cuckolded me later on had. I tend to be more attracted to the edgier Alphas - Lisa was a little more "go with the flow." But, she was very confident, and she had a pretty unexplored Alpha side that seemed to come out around me in this situations. The first time it ever happend was that day, when she said, "How's my peeper doing?"

This led to a good-natured argument about whether I was peeping or not. I protested that I was just getting my pants and keys, but Lisa countered that I had lingered and stared for a while. I didn't think I had, but looking back, I don't know. Maybe I did. Lisa asked me not to tell anyone. "I'm seen as enough of a slut already, so can you just not tell anyone about this?" Part of the problem is that she was looking ahead to a dance and trying to get back together with an ex-boyfriend who would not have been happy to hear about things in the poolhouse with Paul.

I told Lisa I would never talk smack about her and we moved onto other things. For the next year, nothing really happened between us sexually. We remained friends. There was one small incident that seems important now. We were at a party and a bunch of us were standing around a keg talking about what an asshole Paul was. (Paul had pissed in the pool of a friend of ours before a big high school game between the schools). I remember going off on Paul, everyone was laughing, including Lisa. I remember saying, "Paul has nothing to offer." Lisa then said, "Jamister, Paul does have one thing to offer. You of all people should know that." Everyone cracked up, thinking she was making a crack about some homo erotic thing between me and Paul. I blushed a bit, and got a bit hot as I looked at Lisa's teasing facial expression. The look she was giving me was one that I have recognized in years since as the "I know you know that I love big cocks, and I know it makes you hot" look.

Aside from that one incident, Lisa and I were strictly friends. I still was in love with her and wanted to make passes at her and we even kissed a couple of times. But I was already intimidated by her and even moreso having seen her with such a stud. I didn't know how she would respond if she saw my little cock instead, but I was too mortified to find out. I never made a move on her.

The rest of high school would be pretty familiar to the other cuckolds on this forum. I had some occasional sexual adventures but remained a virgin. I wanted the hot girls that never saw me as more than a shoulder to lean on. I cursed my fate and hated that they were attracted to jerks that they knew on some level were inferior to me. Lisa always told her I treated her so much better than whoever she was dating. At the time, I was insecure. But true enough, when I got older I did realize that on many levels these jerks were inferior to me. But there was one level in which most of them were superior. As much as I condemned these young ladies' men as jerks, I feared deep down that they had a talent for fucking that was as much a part of their appeal as the jerkier aspects. Perhaps some of these guys were just faking it. But some of them, like Paul, were in a well endowed position and were arrogantly taking advantage of it. I learned this a couple of years later when Lisa told me more about her sex life.

So, high school came and went and I left for college confused, I think, about what women really wanted from men. I was told women wanted thoughtful, smart, fun and athletic guys, yet I was not getting many women. I wasn't the most confident guy in the world but I was not social klutz either. So I was definitely on some level confused about what women wanted. I suppose on seem deep *** level I had this gut feeling that women loved getting well fucked by men with big cocks that knew how to use them, but I had no real evidence to support this. Perhaps I could have asked Lisa but I was too shy and maybe didn't want to hear the truth. I was about to find out the truth anyway.

Looking back at myself at the time, I see my sexual identity problem differently. I realize that I was trying to be a dominant Alpha male but didn't have the equipment to fully justify it. I think you can be pretty dominant in life regardless of gender and cock size, but now I realize that almost all of the true, no bullcuckolds brownie alpha males in my life had the equipment to back it up, to fuck a woman to orgasm even when they didn't like them or didn't want to come. I've never had that power and I understand that now. We all have unique combinations of sexual characteristics. I have a dominant side, but also have a strong submissive side, which I attribute mainly to my small penis as well as my sexual experiences related to that growing up. I know there are some large penis cuckolds out there, but for men, there's no question that small penises often lead to submissive experiences.

So, being confused about my identity, I wasn't too sexually active. College was still great though, and I did lose my virginity that year in a couple of forgettable encounters. Those forgettable encounters made me realize that I would avoid flings and look for situations where I felt a real bond...like I did with Lisa.

Speaking of Lisa, she and I stayed in touch. When she invited me to stay with her for two weeks when I got home for the summer before I found my own place, I felt butterflies in my stomach. Yet I did not know how much that visit would forever change my sexual identity.

Lisa's parents were out of town the first month of that summer. It was Lisa and her older sister Elizabeth (25 years old) living in the home, with their older brother stopping by to check on them from time to time. Elizabeth was very hot also. More conventional than Lisa, but very sexually self-assured also, with longer blond hair (Lisa's hair was never too long).

The first few days, we would all hang out at night, watching movies and stuff. But then things got busy. Lisa got a job waiting tables at night, and I got a job working in a small factory during the day for the dad of a high school buddy. I would bike to the factory from Lisa's since it was only five miles or so. I remember coming home one night and seeing Lisa get dropped off by this hunky looking guy, whose name was Frank, and he worked at the restaurant, as it turns out. Lisa told her Susan that his nickname at work was "beef." They laughed hard at that one and I did too. Seemed like a meathead and I discounted him as too dumb for my Lisa.

About a week later, I got off at noon when someone spilled some chemicals at the factory. So, I biked home early. Lisa's sister, Susan, was also out working, but I had a key. Lisa worked nights so I thought maybe we'd go get some lunch. I didn't see her in the house, so I walked to the patio door to see if she was sunbathing. Before I got too close, I saw her and "beef" standing in an embrace by the pool. She was rotating her hips and rubbing up against his crotch, dirty dancing style. Turns out Frank was not very tall, he was shorter than me and I was short. He was maybe 5 foot 5. Lisa was a good three inches taller, leaning down on him while kissing him.

Remembering that "peeper" comment, I didn't want her to see me standing there. I went to my room instead. I sat down on the bed for a moment, feeling really horny. Then I looked over at the sliding door that led out the pool area also. It was covered by curtains. I thought to myself, "you shouldn't do this," but I couldn't help myself. I turned off the room light, closed the door, and lay down on the carpet along the curtains, pulling a pillow for my head. I opened the curtain just a crack, not sure how well Lisa would be able to see the window. They were maybe 15 feet away, so not very far at all. But the sun was shining bright and maybe the glare made it hard to see inside. They didn't seem to notice me. I couldn't hear too well, but the screen was open just a crack so I could hear faintly their moans and sighs as they kissed and fondled.

All of a sudden, Lisa kneeled to the ground, and pulled Frank's workout shorts down. A large, nearly-hard cock flopped out. I heard Lisa say, "Wow! Now I know why they call you Beef! It's bigger than I thought."

I couldn't believe what I was seeing. I was rubbing myself a bit now on the outside of my pants. Was I about to see my hot Lisa fuck somebody? The answer was yes.

-to be continued-
randyadrian

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jamisterwr1975
Prey continue!
cuckhsbnd

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Your story is well written and well appreciated. Please do continue when you can. Your story describes cuckold emotions and thoughts that remisterate.
andreasss

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hei continue!!!
g
sexual_tyrannosaurus

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THANK YOU for the long intro, it actually brings things forward that I have believed for a while, but could never put it into words as well as you did.

I have simular thoughts on my high school to yours but with differences of course.

Love the story too, thanks and please continue!!!
prissy

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very, very nice jamister, please keep going. thank you
jjs23jjs

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wow - you are good at this man! - I like when you describe those "looks" the girls give you. They make me crazy too. Keep going buddy, ur one of the best!!
-jjs
jasonwr1975

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Thanks for the kind comments so far. I'm glad other readers are getting something out of this also. It's interesting to work through this in writing, and I'll continue regardless now that I've started, but the good words certainly add more urgency to continuing along.

For the true stories, I really will stick with the truth, so that may make them less hot in some moments, but overall, I think the truth of cuckolding is hotter than fiction. I will change some smaller things, for example I'm not going to call Frank "beef" too much more, even though they often called him that, as that's just silly, but otherwise the tweaks are all smaller things like that.

You will probably notice that sorting out sexual identity is a theme in the story. Hopefully you can bear with me on this theme because I think it will lead us to some insights we don't always see, or at least that I don't, when reading this stuff online. Onward...

Growing up Cuckold, Story 1 (true story): high school sweetie (part three)

From where I was watching Lisa and Frank, I couldn't really see Frank's cock well as Lisa was giving him a blowjob with her back pretty much turned to me. It looked like she had her left hand between her legs, running her fingers through her swimsuit, while she was jerking him with her right and blowing him. I was frustrated not to be able to see Frank's cock. Especially because she commented on it a few times with enthusiasm, at one point I did hear her say, "wow, Frank, you have an awesome cock!" I remember it well because "awesome" is a word not heard as much now but it was a common one back then where I'm from.

I started to quietly unbuckle and unbutton my pants so that I could rub myself while I watched. I was rock hard and my cock sprang out from the crotchhole of my boxers without taking them off. I started slowly rubbing while I was watching, not wanting to come too soon. That was not generally a problem for me, one of the stereotypes about cuckolds that was never true of me was being a 'quick cummer." Even back then, I had a lot of control over my cums but I sure didn't want to lose this one too soon.

I found myself wondering if Lisa really was going to fuck him right there in the backyard. They had a pretty tall brown fence around their backyard, but there was at least one house that had a second story that could have seen down there. But Lisa was not really the self-conscious type. Frank pushed her mouth away, telling her something like "baby, easy now, I don't want to come yet." Lisa kept jerking him with one hand while rubbing herself. She was talking soft to him and I couldn't make out her words. I thought maybe she said, "do you want to fuck this pussy?" but I wasn't sure. Then I heard them arguing about something for a minute. I was worried that they wouldn't go through with it. She said something like "Where are they?"

Turns out they were arguing about using a condom. She insisted on condoms evidently, because Lisa said, "You're not fucking me without a condom." Frank pointed reluctantly to his backpack, Lisa was too hot for him to resist. Lisa walked over to Frank's backpack and rummaged around in the pocket, looking for condoms.

At that point, I had a full frontal view of Frank. I saw his cock hanging down on his body and it looked just fucking enormous. It was hanging down half hard, twitching a bit, looking heavy and confident. I realize now that Frank wasn't as huge as I remember, because I have realized in later years that big cocks look much bigger on short guys than tall guys. I thought he was like a foot long but I think he was more like a bit over eight inches, with thickness. It was still the largest cock I had seen in a half-hard to hard state. He had his shirt off and he looked really built too (he was on the wrestling team at his school). He just looked like one of those guys who was probably only good at a few things, but sex was definitely one of them.

Thinking back, I remember realizing deep down that Lisa was taking a tone with him that she didn't with me. I realize now that the tone was that of sexual respect. Lisa was used to being in sexual control around men at all times. I think she rarely felt like she was around a sexual peer. No question she felt like a peer around Frank, and little did she know but he was about to conquer her and activate her submissive side, a side of her that I had NEVER seen. At the time, all that did not occur to me, it was all wadded up in a feeling of confused, turned-on jealousy.

Lisa came back and rolled the condom on his cock. I was glad that Frank had not seen me while she was gone, he had a good view of where I was. I think the glare from the sun must have spared me. Lisa jerked him off a bit to get him even harder, and again, I couldn't see much, but it was so hot to watch her rotate her hips and sway in lust while she jerked him.

Then came the moment I had long dreamed about. Lisa stood up, and seductively stripped off her bathing suit top and bottom. Perhaps I can find a picture online of a girl that resembles her. Her body was just perfect, it looked to me like she had shaved her pussy a bit but it was pretty full and brown and just perfectly centered between her wide, athletic hips. She even had some tan on her breasts and pussy, so she definitely sunbathed nude sometimes. She grabbed Frank by the cock and led him around me to the diving board. The diving board was a bit further away, maybe 20 feet, but it was a straight shot from the window where I was peeking out.

Lisa grabbed the edge of the diving board and stuck her round ass in the air, moving it around a bit like she was in heat. She motioned Frank forward, and told him something I couldn't hear well, but I think it was something like, "go easy at first Frank, you have a big cock." The big cock part I heard. Frank spit on his hand, rubbed the spit on his cock, and inserted his head into her. His head was a bit smaller than his shaft, so his head went in easily. Then he shoved in a bit more, maybe three or four inches. "Oh!!!!" was what I remember next from Lisa. "Oh." "Oh." Frank started moving his cock a bit faster. I was really surprised Lisa could take his cock, I assumed she was a typical tight teenage girl, but I later learned that she had been with at least 10 guys, if not more, before him, so she was not all that inexperienced.

Still, Frank was an impatient dude and maybe not the most sophisticated male lover of all time, and he got sick of the half-strokes and just grabbed her shoulders and thrust all the way in. A good eight inches of thick cock pounded into Lisa. "owww!!!!!" she said loud enough to be heard outside of the yard. "Frank, that fucking hurts! I told you to go slow."

That was when something happened I wasn't expecting. For the first time I had ever witnessed, a man ignored Lisa's sexual wishes. "If you want this cock, you're gonna get all of this cock!" Frank said. He pounded into her hard, grabbed her hair even with his right hand, and just started pounding her. "Owww! Oww! Oww!" Lisa cried out. "Stop it Frank, that fucking hurts!"

"I'm fucking you baby, fucking you good!" was all Frank shouted, he kept on pounding her mercilessly. "Dammit, Ow!" Lisa said again. "Fucking stop it!" she yelled. It sounded like Lisa was in a lot of pain, and for a crazy moment I thought about slipping my pants on and jumping out there and defending Lisa somehow.

"Stop it!" Lisa kept screaming. "Stop fucking me so deep!" she said, but suddenly I noticed that she seemed to be pushing her hips back against him. "Stop fuckking me!" Lisa said again, but for the last time. The next time, without skipping a beat, she said, "Don't stop fucking me!" "It hurts, but it hurts so good!"

Frank started talking really mean to her, in a way I would never have dreamed of. "Yeah, you love it, you fucking slut!" "Fuck this cock!" I coudn't believe he called her a slut and it didn't bother her. She hated when someone called her that and I would never have ever done that. "Damn! Oh My God!" Lisa said, as she backed her ass to Frank and he pounded her so hard. "Frank, it's starting to feel good, fuck me harder, fuck me!" Frank ate it up and egged her on. "Yeah, you love it, you bitch! Tell me how much you love this cock!" "Oh yeah, Frank," Lisa said, "I love your big fucking cock so much!"

I'll never forget that line, because I had been looking for evidence on whether or not size mattered to girls. There it was. She loved his big cock. What really shocked me was the sounds. Frank's thick cock was making these nasty plunging and sloshing sounds as it rammed in and out of her pussy. It was so dirty sounding, like he was really plumbing deep in her wetness, really pounding her. In years since, I've never been able to make a pussy sound like that, though I came close a couple of times using big dildos. At the time, I just thought it was the sound of a nasty doggy style fucking. But it was actually the sound that only a big cock fucking a pussy hard and deep can make.

"Damn it Frank, my pussy's gonna come! Keep fucking it, I'm gonna come all over your cock!" Lisa was screaming now and she even seemed to have some spit on her face from calling out. She looked around at him and I could see some sweat glistening on her back as he pounded her. Suddenly, I saw her body tremble all over, and she almost lost her balance but then gripped each side of the board hard. Then she just had a full body spasm and hollered out some gibberish and she came all over his cock. It was the most beautiful sight I had ever seen, and to my disappointment I was unable to stop myself from coming either. I came in big frantic spurts, one splashing all the way up to my face and one on the carpet I would have to clean later. The rest went all over my t shirt. I was pissed I had been unable to hold off but it was an amazing come.

After Lisa came, Frank took his cock out of her pussy and laid it on top of her ass. She continued to rotate her hips back and forth slowly as his cock rubbed up and down on her ass. She smiled at him and said something quietly, I think she said, "You really know how to fuck," or "you really know what you're doing" or something like that. Frank's cock look so smug and swollen and confident lying there on top of the Alpha girl pussy he had conquered.

I had all kinds of conflicting emotions inside me. I can interpret them much better in retrospect. I realize now that I had an awesome respect for this guy who had the cock and the hard edge to power her into an orgasm she didn't at first want to have. I was amazed at how submissive Lisa would be in that situation and the words she allowed him to say to her, and some of the dirty things that came out of her mouth also. I realized later that she would only let someone call her those things when they were conquering her pussy. And she loved - but also hated - the guys who could do that to her. Maybe she even feared the loss of control she had in that moment, as she was so used to controlling men. She looked back on Frank with a kind of awe that I never would ever cause her to do.

It might seem like it would have said, "with a kind of awe that I never caused a woman to have" but I'm glad to say that's not entirely true. I have had the good fortune to have a couple of girlfriends who viewed me with that kind of sexual awe. I can only imagine what I could have done to them to deepen that awe with a cock like Frank's.

And I realize now that sexual identity becomes a complicated problem for women like Lisa also. After all, emotionally she felt more connected to me. But for fucking, she needed a nice big cock like Frank's. Neither type of man is very easy to find. One solution is to find a man who has all those qualities. But those kinds of men are not easy to find, which is why I think she sometimes called Frank a "big dicked bastard" when she fucked him - perhaps because she hated that the pleasure he gave her came with the strings attached of dealing with him outside of the bedroom. Of course, cuckolding provides a great solution to this, by allowing a woman like Lisa to divide and conquer and find sophisticated emotional nurturing from one kind of guy and deep, high quality fucking from another.

But cuckolding is an unconventional lifestyle and many are not aware of it or know how to make it work. Like men, all women in this situation handle it differently. I point this out only to say that Alpha females don't always have it made either. I've known several of them who ended up in pretty unhappy marriages with big dick studs who maned some kids with them and ended up being bad partners in a lot of ways. So it's not easy for either women or men, regardless of their sexual attributes, to get everything they want - even if they are near the top of the sexual pecking order as Lisa was. But I'm certain that Lisa was a lot less confused in that moment than I was, lying with come from my little dick on my shirt, jealous beyond belief yet ecstatic about the orgasm I had just experienced. Perhaps I had been thrown a scrap from the table, but it was one hell of a juicy scrap.

Since I had come, I almost got up, figuring that I should quit while I hadn't been caught. But I couldn't look away from them, and they clearly weren't done. Frank's condom was still on, and Lisa was now sitting up and talking dirty to him, saying things I could not hear.

At any rate, they just talked and she jerked him for a few minutes, but then I saw her kind of swaying her hips a little bit and I realized she wasn't done fucking yet either. She pushed him back on the board so that his cock was standing straight up, his feet towards me, and started to climb on him. I was pretty disappointed that she was climbing on him with her back towards me, as I really wanted to see her face. But that's how things go sometimes with the real encounters.

Rubbing myself, I found that I was getting hard again and had another orgasm inside me as well. However, this one was to turn out very different than the last.

- to be continued -
jasonwr1975

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I thought you might enjoy if I could find some photo likenesses to go with my story. Attached is a photo likeness of Lisa, she was a bit skinnier, her hair was shorter and browner, and her face was maybe prettier, but this will give you some idea. I hope the photo upload works, have not done this before.
like lisa
like lisa
faraday5

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#13
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Great Story! Nice pic too. Please continue.
jasonwr1975

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#14
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Thanks for the good words. I will continue soon, putting some work projects to bed but I'll be back. It's interesting how intense it still is to write about these things. The next part will involve working through some pretty primal memories I haven't powerd myself to live through in a while, but its should be interesting and I'm glad folks are enjoying it.
wifedateshubwaits

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#15
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Quoting: jamisterwr1975
Of course, cuckolding provides a great solution to this, by allowing a woman like Lisa to divide and conquer and find sophisticated emotional nurturing from one kind of guy and deep, high quality fucking from another.


This is exactly why cuckolding works for us and has made our marriage stronger and happier.
jasonwr1975

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#16
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Hey folks....sorry it took me a little while to post again. I've been tied up working, and as I mentioned, the next few parts of this story are going to be a little bit intense to relive. However, I am finding the writing to be a good release so I will definitely keep going. Thanks for reading.

Growing up Cuckold, Story 1 (true story): high school sweetie (part four)


I had already watched Lisa and her boytoy Frank through their first fucking. Like I said, after I came I had a chance to break away and call it a day and be glad I wasn't caught.

But they were still acting dirty and clearly weren't done fucking, and like I said, after watching Lisa jack his cock and talk dirty to him, I couldn't stop myself, I was now getting hard again also. Even though I couldn't hear much of what she said to him during this period, that cock worship look on her face was so hot to me, and so piercing at the same time. I wanted so much for her to look at me that way someday. But that was not to be.

Anyhow, picking up where we left off last time, Lisa started to mount Frank. Unfortunately, she chose to mount him with her back to me, so I was unable to see her facial expressions and she lowered herself down on her cock. I could see the sweat running down her back in gorgeous streams now (it was probably 90 degrees out there) and it was so hot to see that huge cock moving slowly inside her. From this angle, I could see her pussy lips getting tugged almost inside out as Frank's thick cock pulled its way slowly in and out. She would later tell me just how good this felt. I could only imagine, but I could hear her soft whimpers and moans as I rubbed myself.

What really impressed me was that at first she was not able to take all of his cock in that position. It was like she was impaled on it. I found myself wondering if my cock was big enough to make it hard for a woman to sit down on it. I would later find out much to my horny ridiculous insane jealousy and inadequacy that it was not.

In all the years since, I have not had a woman have any trouble taking me from a cowgirl position when she sat down on me. In a sense, Frank at 17 was already more man than I would ever be, and he was just learning how to use this dick. I felt that intensely erotic shame without fully understanding it, but it did make me rock hard again as I slowly jacked my cock up and down, not wanting to come too soon.

I can't remember exactly what Lisa said, but her dirty talk got louder as she started riding up and down with more intensity. Mostly she was talking nasty about how good his big cock felt inside her pussy. As if she could read my mind and knew I was watching, she made a point of emphasizing his cock size and how damn good it felt in her pussy. Of course, that was also her way of reminding herself that she would not be spending time with this dude at all if he wasn't such a good fucker.

In this position, Frank was making her do most of the work, and she was rubbing up and down faster now. She seemed to be taking all but about an inch of his cock. Like I said earlier, I realize now it was about an eight inch cock - about the size to give most girls a bit of a challenge but to eventually get it all the way inside them.

Frank seemed to sense this too, and he surprised her with a vicious upward thrust. I remember it clearly because I could see his entire cock jammed into her as he pushed her upward. "Oh cuckolds brownie!" she said. "Oh my god!" At that point, I wanted to hear more dirty talk but they were both too into the naturalistic fucking.

Frank was moving his body up and down from underneath her, pulling his cock all the way and jamming it up quickly. She was bucking harder too. He was fucking her so hard he even fell out a couple of times but she quickly powerd him back in. Those deep plunging sloshing sounds returned, and I heard her screaming, "I'm gonna cum again!" I remember this well because I was fascinated with what made girls come. As the girls of my dreams tremred and spasmed on that big cock, I found myself jerking myself faster and faster. I couldn't wait for another orgasm, it was coming on fast.

But it was at that point that the door to the bedroom opened and a light switched on. "Oh my God!" said a girl's voice, pretty loudly. Turns out it was Lisa's older sister Elizabeth. The official explanation Elizabeth had always given for stepping into that room was to get her hair dryer back from the bathroom adjoining the two bedrooms. I have always felt that Elizabeth went into this room because she wanted to watch her sister get laid from behind the curtain just as I did. She never admitted it though. What I do know for sure is that Elizabeth did not expect me to be home from work, lying on the floor jerking my cock off.

I shut the curtain and looked over at Elizabeth. I wanted to roll over but my dick was too far on the way to a cum to stop, so I just spurted over myself while she watched. It all happened so fast but it seemed like an eternity at the time. I felt embarassed as I was coming, like Elizabeth had intruded on me just as I had on Lisa. And I was feeling pretty insecure about my size at that moment and not that happy that a sexy mid-20s woman was getting a good chance to size me up. Elizabeth had a stern librarian look in her eye but a bit of a hint of a smile too. She slammed the door but she had definitely waited an extra second or two to watch me come helplessly on myself.

I was in a state of shock and denial. Cautiously I peeked out of the curtain but Lisa and Frank were gone. Turns out they had heard Elizabeth's voice and decided to go into the poolhouse to finish their fuck in there. I was alone and not sure what to do.

It's hard to go back in time and imagine my confusion and embarassment and even terror (would Elizabeth tell my lady, or her parents? Surely she would tell Lisa). If something like this happened to me now, I would know how to use it to my advantage, in that I have realized that whatever turns you on in sex you can use as material to share fantasies and perhaps live out adventures. But at the time I just felt like a desperate creep that had given up way too much in a greedy search for one more come after already having had an amazing one. And maybe I had cost myself a chance to be with Lisa, a girl I was still dreaming about dating despite what I had just seen. Denial was all I had to fall back on to make sense of my love for her.

No, I had no idea what to do with this information. I left a note on the kitchen board saying I was going out to meet with friends. Fortunately, no one was around when I did that. I left and went on a long bike ride down the river. Ended up playing in a pick up soccer game, then staying out late at a waterpark, and not coming back until I knew everyone would be arelax. I made a point of getting up extra early and actually avoided seeing anyone on the homefront for another full day. But I knew I wouldn't be able to hide from the situation forever, and a part of me was looking forward, in a naughty way I would later think of as a cuckold way, to seeing the girls and facing them. Yet I was also dreading it and hoping not to get kicked out yet, I didn't have a backup plan in place if they did. I decided I needed to find someone else to roommate with as soon as possible so I wouldn't get stuck without a place to crash.

But then came the moment that was to change everything. I was lying in bed, about to fall arelax, when I heard my door open. Lisa called out my name and hopped into bed next to me under the covers. I couldn't see what she was wearing, I thought for an incredible moment she was naked, but turns out she was wearing a bra and panties.

Lisa hopped into bed with me because she wanted to talk to me about my peeping. It turns out she was as curious about my desires and her own complicated feelings for me as I was in understanding her. My sexual education was about to accelerate.

- to be continued -
wifedateshubwaits

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#17
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Wonderful story and in some way it mirrors my early experiences. Thank you!
crazyinvt

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#18 · Edited by: crazyinvt
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ccc v
jasonwr1975

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#19 · Edited by: jasonwr1975
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continuing on...thx for the continued kind words, glad others are enjoying as much as I am recalling....


Growing up Cuckold, Story 1 (true story): high school sweetie (part five)

So here I am in bed with the girl of my dreams up until this point in my life. I had never even gone on a date with her, never even kissed her, and she's lying next to me. Of course, this scene is not exactly how I had originally fantasized it. I thought I would win her heart and be lucky enough to seduce her. Instead, she is in my bed a couple nights after I watched her fucking another man and got caught by her older sister. I'm thinking I might get kicked out of her house, and her I am in bed with Lisa instead.

Before I go on, I want to describe briefly Lisa's permisterality. Lisa didn't know much about cuckolding. But like most alpha females, she took pretty naturally to these themes once she discovered them. When I talk about alpha females, I'm not talking necessarily about good looks. Many of the real alpha girls I have know have been attractive, but not all. And I've known some very pretty girls who were not at all comfortable with the dominant alpha girl attitude. Nice girls to the core.

When we talk about alpha females, more than anything I would say that sexual confidence is the common factor. The confidence to get what she wants sexually is a theme that alpha females tend to have in common. I think many of them took naturally to this alpha role from the beginning of their sexual life, as Lisa did, but not all.

I would categorize Alpha women into three categories when it comes to cuckolding. One group is simply not turned on at all by dominating or humiliating guys they perceive as sexually inferior. They simply go about the business of choosing the best sex partners for themselves and rejecting all those who don't qualify. These kinds of Alpha women can be very frustrating for those of us guys who get into being cuckolded - they simply don't have any patience or interest in dealing with us sexually. I have found this to be the most common breed of Alpha girls, though of course some of them can get into cuckolding if they encounter it during swinging sessions, etc.

Of course, selecting sexually superior partners does not necessarily mean that all Alpha women are size queens. I have met Alpha women who didn't bother with men at all and dated only women. But generally speaking, I think it's fair to say that Alpha women who are into heterosexual sex have had enough experience to develop pretty strong size preferences. In most cases, this leads to a preference for big cocks, and in some cases, huge ones (the real size queens). Rarely do Alpha women put up with small cocks when they are looking solely for a great fucking, though it's true that some women are just not as interested in pentetration as others, and this can impact size preferences also.

Beyond that first type of Alpha woman that has no interest in cuckolding, I have run into two types that do have a natural inclination towards it. Both find sexual satisfaction not just in submitting to a great fucking but dominating those that they find inferior. One group of these Alphas tends to prefer the domination/presentation side and isn't too interested in, or turned on, by the sexual needs of the cuckold. They would just as soon lock the cuckold's useless cock away and fuck who they want to fuck.

But there's another group of Alpha women I've run into that very much is turned on by how much the cuckold man is turned on. For lack of a better term, I guess you could call this "sensual domination." This type of Alpha woman is my permisteral favorite for cuckolding because I like to be included in scenes where my own sexual pleasure is also important and relevant. Not all cuckolds feel the same. We are all different, these are just generalizations.

I make these generalizations to explain that Lisa fell really into that third category of sensual domme. She was always interested in my pleasure and how it intersected, albeit somewhat vulgarly, with hers. I feel some gratitude that if I had to be cuckolded, that it was done by someone who felt as she did. Needless to say, the amount of love and affection in the cuckolding relationship is also a major factor, and in this case, there was that strong emotional connection. We both lacked for experience in how to do this and make it work, but the love and the intersecting desires were both there.

On with the story:

So, Lisa is lying in bed with me. The scene is so intense I am having a hard time thinking straight or saying anything. But I can't forget the next line:

"So, Elizabeth tells me that my little peeper is at it again."

I felt my cock twitch when she said that. Even though she wasn't necessarily referring to my cock as little, it sure seemed that way, and it was the first time a girl had ever even implied that to me. It was so intense.

"Jamister, did you watch me having sex with Frank?"

"Yes" was the only thing I could say.

"Did it turn you on?" she asked?

For some reamister, I didn't want to submit to her yet and give her a straight answer. I was new to this kind of thing and still had my adolescent macho pride. "I guess." I said kind of casually.

"Well, Elizabeth said you were pretty turned on."

I didn't even know what to say to that.

"She said when she walked in on you that you were looking out the window and tugging on your tiny penis. She said you spurted all over yourself. Is that true?"

I coudln't believe what I was hearing. It was like my hottest fantasies and worse fears were coming true at the same time. Was I really that inferior? I could feel my dick twitch again.

"Yes," I said kind of shyly. "But my cock isn't tiny!" I asserted self-consciously. I knew from my locker room that there were guys much bigger than me. But I had also seen guys who were about my size and a little larger. And while I was pretty tiny when I was soft, I had measured my cock at five inches hard and the sex books had said 5-6 inches was average and that size didn't matter anyway. I didn't want to feel that inferior.

"I'd like to be the judge of that!" said Lisa. "Let me see your cock."

She pulled at the covers but I kind of held them up, I wasn't ready for this really. Sure, I had dreamed of being in bed with her, but I wanted her to be all hot for me, kissing me, squirming under me, getting all nice and horny before she saw me naked. I certainly didn't want her to just pull the covers like this. (I was wearing underwear but it was tighty whities in those days).

"If you got to see me have sex, the least you can do is show me your cock. Now show me that tiny little cock!"

The last line pierced me. I guess Lisa was taking Elizabeth's word for my cock size. But it was more the way she said it, so powerfully. I felt powerless against it. Cuckolds here know what I'm talking about. Lisa pulled back the covers, exposing my underwear. I did not resist this time. "Off with those!" she said, and I dutifully took them off like I was programmed to follow her instructions.

Unfortunately for me, my cock had gone soft again through all this stress and it really did look tiny down there, even to me.

"Wow Jamister, that *is* a really tiny cock! No wonder you've never made a pass at me!"

(the last line will strike home for a lot of you guys growing up, as we realize that a the hot girls we were friends with suspected that our shyness around them in terms of hitting on them was due to our size insecurity).

"It gets a lot bigger when it's hard!" I said defensively. I knew that much was true, I have always been more of a grower than a shower.

"Well, Jamister, Elizabeth saw you when you were hard and she wasn't too impressed."

This last line *******ed me and I was just red-faced. I think I got a real sad look on my face, I felt sexually defeated, as if I was looking towards an adult life where no matter how cute, funny, athletic, smart, or successful I was, women would always think of me as sexually inadequate.

Lisa cared a lot for me and must have sensed on some level my growing despair. "Hmmm...well, maybe we'll get it hard and see just how big it can get."

Oh my god. Just thinking about it today is so intense. I should mention before I go further that when she rolled over the covers, Lisa also exposed herself in a white lacy bra and panties. Her gorgeous brown skin was amazing. It was like I was in bed with an Amazon goddess.

So it was that much more intense when she reached down with two fingers and grabbed my small soft shaft and started rubbing it.

"Ohhh....." I said.

The pleasure was so fucking intense, so much more intense than anything I could have done with my own fingers. Guys on this forum know exactly what I mean.

Lisa kept rubbing and my cock twitched a little bit but didn't get much harder or bigger.

"It's not getting any bigger!" Lisa said.

"It will," I said, but try as I might, I couldn't make it bigger even though the touching felt so good.

"I think I'm just nervous." I confided.

I think that was a turning point for us. When Lisa heard me confide in her like that, it kind of changed the sexual tone between us. We both felt more comfortable. We were starting to learn how to talk to each other like a cuckold and cuckoldress have to learn to talk, but of course we had no examples so we were feeling our way into our natural roles.

Lisa's role came really naturally to her. I was suprised by how powerful she could be, it was a side to her I hadn't seen, but in the context of her sexual power it made sense to me. And she kept just a dash of that nice girl side of her. No, the biggest obstacle was me and my fear of submitting and giving up my misplaced sexual pride. I didn't want to give up my macho side or lose my "rep." In fact, had we still been in high school, this probably wouldn't have happened, certainly not on my end.

But high school was over, and while I wasn't sure if Lisa would keep this all a secret, these weren't my peers in the same way they would have been seeing them in class and at my locker. So it went forward.

Lisa had some appreciation for my confession of nervousness.

"What can we do to make that cock hard?" Lisa said as she rubbed me.

I was in too much pleasure to say anything.

"What can we do to make that little cock hard?"

When she said the word 'little," my cock twitched noticeably in her hand.

I was almost hoping she didn't notice, but she did. "Oh!" she said. "Look at this! Your cock likes it when I call it little!"

I was going to deny it out of shame but it was no use, my cock twitched again. "Oh, now we know. Now we know how to get that little cock hard! Let's see how big that little penis can get," Lisa said with a wicked teasing look in her eyes, as if she had just discovered a big secret. The use of the word 'penis' here really stood out to me, because it was a clinical sounding term, not at all the same as calling my dick a "cock." It was a non-sexual term in some ways. It turned me on so much.

"That little cock is getting harder now!" Lisa said, smiling as she sensed her sexual power over me. She started moving her hand up and down and using more fingers. It felt so good. Looking over, I looked at Lisa's legs, kind of uncrossed and spread out. I could see a wet spot starting in her crotch and spreading out on her panties. This was turning her on too.

She started rubbing my cock faster to get it all the way hard. There was no looking back now, I was way turned on. Soon it was all of five inches, as hard as it had ever been.

"Well, it *is* a hard cock Jamister. And you're right, it's not tiny. It grew a lot!"

For a moment, I felt this surge of self-esteem and confidence.

"But to be honest, Jamister, it's still a small penis."

I looked at her with a mixture of hostility and sadness and probably curiosity.

She could tell I needed to hear more. "I mean, you saw me out there fucking Frank a couple of days ago. His cock is SO much bigger than yours, isn't it?"

I had no choice but to say "yes."

"And yet the whole thing fit in my pussy."

"Yeah, his cock is big," I admitted. "But mine is still average," I insisted, holding onto my old masculine sexual identify by a thread.

But Lisa had figured this scene out and knew her Alpha girl lines as if she had been taught them by heart. I don't know why she did it. Maybe it was sexual destiny, maybe it was that she was a little mad at me for peeping on her, maybe she was just turned on to exert her power in this new way. Whatever reamister she had, she was not leaving this bed without getting me to submit to her totally.

-- to be continued ---

(sorry to leave off here but I have to get some relax and I don't want to rush this part of the story. Plus I need a break from remembering this for tonight.)
jasonwr1975

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Posts: 46
#20
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I thought you might enjoy a likeness of Beth, Lisa's older sister who lived with us that part of the summer and walked in on me. Beth was also a very attractive woman, mid-twenties. To be honest, she maybe wasn't quite a hot as this picture, so a bit of fictional liberties here. But not too much! Beth had a couple of small scars on her face, but her body was similar to this, and she had the same take charge attitude you can pick up on from this picture. So, the attitude (and the tan and leggy look) is right!
Likeness of Elizabeth
Likeness of Elizabeth
wifedateshubwaits

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#21
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Keep it up! The similarities between my first experience is amazing.
jasonwr1975

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#22 · Edited by: jasonwr1975
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Thanks for your patience in between installments and for the good words. Let me see if I can pick this right up in my mind from where we were last time.

Growing up Cuckold, Story 1 (true story): high school sweetie (part six)

Where we left off, Lisa was really starting to feel her power over me as she jacked my cock off and teased me. I had just protested once more that my cock was average.

"Well, Jamister, your cock isn't average to me. It's actually small. I've been with one guy that small and he was a sweet lover but...." (and she was jerking me as she said this)..."I really couldn't feel him in my pussy. It tickled a bit but it didn't stretch me." She smiled kind of teasingly when she said this and she could feel me twitch in her hands. But she seemed to want to take the edge off, so she also said, "but I will say this: you are a LOT bigger then you were when I started touching you. And you are really hard, aren't you?"

I nodded, and she went in for the ******* I guess, testing my level of presentation.

"Does my hand feel good on your little cock?"

"Yes" I said kind of sheepishly, finally giving up the prideful front.

"Do you want me to make this little cock cum?"

"Oh God Yes." I said.

"OK," she said, "I'll make you come." Then she gave me a real teasing look. "I'll make this little dick come harder than it ever has in its whole tiny life."

And with that, she stood up and peeled off her bra and panties. Then she straddled me, so that her pussy was lying on my legs and she was facing me. She gave me a real seductive look and I realized this was turning her on too. Of course, I now know why - she was turned on by my presentation. I was a pretty popular and hot guy in my high school class, people tended to look up to me and see me as in control, and now she knew all my secrets and was taking control from me. That turned her on almost as much as me I guess.

Lisa then grabbed my balls in one hand, stuck her right hand in her pussy to get it wet, and wrapped that hand around my cock. I had never felt anything quite like it...I'm sure I said "Oh my God" again.

"Oh, you like that." She said. "My little peeper likes that."She was stroking me, but not too fast. I think she wanted to savor the moment, and she was moving her hips back and forth on me.

Then she got a naughty look in her eyes again..."so, did you like watching me fuck?"

"Yes."

"Yeah....You liked watching me getting my brains fucked out like that didn't you?"

"Yes"

"Were you jealous?" (her slow stroking continued)

"Oh God Yes."

"Did you wish you were Frank?"

"Yes."

"Did you wish you had a big thick cock like his that could fill my pussy up and make me come over and over like he did?"

What could I say but "Yes."

"Did you see me jacking off his cock with both hands?"

"Yes."

"I love how it takes two hands to move up and down his cock, how big and heavy it feels...." (another very teasing look...)"But I don't need two hands now do I?"

"No."

"And why is that Jamister?"

I wasn't quite ready to say it. And Lisa was getting so horny she was rubbing her pussy up and down my legs.

"Damn!" she said. "My pussy is really dripping."

"I'm so hot right now!" She said. "I really need to get fucked! God I wish your cock was bigger!"

She let that sink in while she stroked me up and down and rubbed my balls. "Oh well..." she said. "I'll have to settle for a different kind of come. You can help me with that," she said.

I was curious what she meant by that.

"But you're not going to be much help to me until you come. Do you want to come Jamister?"

"Oh please!" I remember blurting out.

"Oh, I'll make you come," she said, with utter, fascinating confidence (you have to remember I had never seen her in such a position of power as this, as it was a huge turn on) "but you have to ask for it first." She stopped stroking.

"Please make me come." I said.

"almost...." she said.

"Please make me come, I want it so bad." I said. "You're so hot!" I added, thinking that might be what she wanted to hear. I loved how her breasts looked over me, small, firm, perfect, poised and just a little brown from nude tanning.

"I'll make you come on two conditions." she said, hands rubbing around her own pussy while she teased me.

"What's that." I said.

"First, you can't ever watch me fuck again without my permission."

I felt a flash of guilt and shame. "Ok." I said.

"And second, I want to hear you admit that you have a little cock. You saw Frank's cock. You know that you are so small compared to a big stud like him."

"Yeah, you're right." I said. I felt so relieved to finally admit it after so many years. I always felt so much pressure around girls I liked, as if when they asked me to fuck them I wouldn't be able to please them, or might not be able to. It felt like such a relief just to admit it.

I looked up at her, thinking she would start jacking me again. My cock was aching and swollen and I needed to come so bad.

"So tell me." she said. "Tell me to make your little cock come, and I will."

With that, she wrapped her hand around my cock again and stroked it slowly. "Tell me!" she said.

I gave in. "Make my little cock come," I said. I couldn't believe how edgy she had become, teasing me so vulgarly like this. But I loved it so much and the cuckolds reading this know what I mean, that this felt like a loving thing in a way to be told the truth after all those lies and excuses girls had told me in the past or simply not acknolwledged and ignored me instead.

"Say it louder," she said. "Say it louder if you want to come so hard."

"Make my little cock come," I said again, but not too loud because I thought Elizabeth was home.

"Say it louder if you want to come," said Lisa. "Say if fucking loud! Yell it!"

"But your sister might hear," I said.

"So what if she does," said Lisa, a fiery look in her eye as she stroked me slowly. "She already knows you have a tiny cock!" She said this pretty loud, Elizabeth could have heard that. I damn near came when she said that.

Finally, I couldn't take it any more. It probably sounds crazy writing it now, but I wanted to come so bad and I guess a part of me just wanted to finally accept myself and be myself instead of working so hard to put on a front. So, the heck with it.

"Make my little cock come!!!!!!!!!!" I screamed!

"Again!" she said.

"Make my little cock come!!!!!!!!" I screamed !

"One more time!" she said

"Make my little cock come!!!!!!!" I screamed even louder.

"That's it," she said. "Now we're getting somewhere." With that, she started rubbing my balls real quick and jerking my cock real fast. "I'm gonna make that little dick squirt!" Then she rolled on her side next to me, and wrapped a leg on mine, and I could feel her pussy juice on my thigh, so close to me yet in a way so far away.

She leaned over next to me and starting working my cock up and down with her right hand super fast, and then she whispered in my ear. I thought I heard some footsteps in her hallway, perhaps Elizabeth had passed by and heard something, but I was too far gone to care and it kind of made me hot anyhow, you've seen my likeness picture of Elizabeth so you know.

"Squirt for me," Beth whispered as she rubbed me. "Squirt that little cock. Let me see how much come is in that little cock."

"oh god." I said.

"what?" she said.

"your hand feels so good wrapped around my little cock." This was the first time I had volunteered that kind of expression about my dick and I could tell from the look on her face that my honesty pleased her, and it seemed to turn her on.

"Of course it does." She said comfortingly. "Now let me see how much come is in this little cock," she said, jerking very very fast. "Come for me now!" I couldn't hold back any longer, I gave in to her totally as her hand jacked up and down almost blurry with their speed. I started spurting in huge spasms and bucking my hips into the air. Come went everywhere. I had about seven thrusts in me, then I finally stopped coming. It was by far the best come of my life to that point, much better even than the one I had watching her outside with Frank.

"Wow." she said. "That little dick holds a lot of come," Lisa said, wiping some from her breasts. I didn't bother telling her that this was by far the most come I had ever ejaculated at one time. "Not as much as Frank," she said, "but a pretty nice come."

I felt a little proud about that, as if I might have a shred of masculinity to hold on to. But mostly I just felt overwhelmed. I think I was in a state of shock about how much my sexual identity had just been turned on its head. I knew for sure that I could never tame her the way I had dreamed of in my head (though I would later try a couple more times just out of idiocy). It felt so intense - in a way, my worst fears and greatest fantasy had been realized at the same time. 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.

But at that moment, my biggest confusion was how someone who loved me so much could be so mean. And yet, adding to my confusion, it had not felt mean. It had felt truthful and loving. And there was a point later where I really appreciated just how loving it is to be honest. And what I found out was that just like I badly needed that chance to be told (and to admit) I had a small cock, she needed the chance to take control of a situation like that and show me my place by showing me hers. Once that had been accomplished, a more affectionate side of her would emerge again, to compliment her ruthless sexual Darwinism, which I realized was much less ruthless than that Alpha girls who just ignored me. She wanted to include me in the way that she felt I deserved, given her feelings of love for me but her clear and accurate sense that I was not her sexual equal. And to my surprise, though she would never fantasize about fucking me after that, she would respect me more than ever for being honest.

But that's more than I have time to type tonight. Good stopping point.

- to be continued -
lurkerjoe

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Brilliant!
Kyttenpet

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#24
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very well written......
kinda reminds me of my own teen years....

i had a girl friend who would never fuck me, but she was always with the more dominate guys in the school.... including one of my best friends, whom i knew to be quite well hung (ok he had a monster in his pants)
but thats what ladies like these want, right??
thewhitecuckmaster

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we are all greatful....would like to hear of your other sluts tah
goodhusband

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Jamisterwr1975

I like your story.

GH
demonic1000

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#27
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Very good story! Can't wait for continuation
sixpacksi

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#28
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Update pleeeeaaassseeee!!!
jasonwr1975

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Hey folks....my apologies for the delay on writing this. I was caught up in a business trip and some permisteral matters on that trip that kept me away from telling my story. That was the longest trip of the year so if all goes well, I should be able to proceed more regularly from here on out. It's become important to me to tell this story so I will definitely continue, bear with me and thanks for the good comments. Since this is a true story there may be parts that are not as erotic and maybe even difficult in their honesty, but I hope it is a good read.


Growing up Cuckold, Story 1 (true story): high school sweetie (part seven)


That night was a cross between my greatest dream and my worst nightmare. Cuckolding has almost always struck me as a bit of both, and this first experience was just like that. Lisa spent the night in bed with me, and it was heavenly to feel her naked body spooned up inside of me. I could feel her ass against my limp and happy cock as we both slept through the night, my arms around her. I had dreamed of this night for so long and it had finally happened. But of course not in the way I had necessarily wanted it.

I remember the sun coming up through the window and something about that moment caused me to start crying. I don't know why, I guess I was just overwhelmed by happiness and confusion and not wanting to face the day. I had a sinking feeling inside me, like this was the only night I would ever be with Lisa. And I also still had this ill-fated desire to prove to her I could be as much of a man in bed to her as her stud Frank. But in the back of my mind, after what I had seen, doubt was starting to creep into my mind. Were the sex books that said size didn't matter really that wrong? I thought that love could conquer all. Could it really come down to a couple inches? I knew nothing about cuckolding, so I figured I was either in as Lisa's alpha dog or I would be out forever. It was too much and I was crying a bit, I'm ashamed to say.

I guess my crying woke Lisa up. There was enough morning light in the room for me to see her face as she turned around to face me.

"Hey, Jamister, hey. Don't do that. Don't cry. This was a beautiful night with you. Don't be sad."

She wrapped her arms around me and for some reamister that made me cry harder, not exactly what I was going for.

lisa knew what to do to make me stop crying. She reached down and put her hands on my cock again.

"Ohhhhhh..." was all I could say.

"There we go," she said. "Don't be sad, let me make you feel good." With that, she started rubbing up and down on my cock and balls again. My cock started twitching and coming to life.

This time when Lisa jacked me off, she didn't make fun of my cock at all. She still had the look of total control on her face. But it was as if she sensed my ego couldn't take any more teasing right then. I'm ashamed to remember thinking at the moment that I wished she would tease me about my small cock again - even while desperately hoping it wasn't as small as I feared in her eyes.

I came all over the place as she jacked my cock hard.

"That's it," she cooed in my ear, "that's it."

After I came, she guided my hands in her pussy and I could feel my fingers moving in and out. I could sense her rhythm and knew I could make her come that way. It was an amazing feeling to have her hips bucking slightly and her pussy clenching at my fingers as she came.

After that, we kissed for a while and then the moment I dreaded came: we got up and moved on with the day.

Fortunately, her sister Elizabeth was gone by then, I wasn't ready to face her yet.

In retrospect, I might have done things differently, but in this case, it was real life and I didn't know quite how to behave around Lisa after this had happened. As a result, I was maybe a little cold to her and I avoided her a bit the next few days, making excuses like picking up extra shifts and staying out with friends. In my head, though, I couldn't stop thinking about what I had seen. The image of Lisa's pussy coming all over Frank's big cock was seared into my head. I sensed that this scene had big implications for my future sex life but wasn't clear yet as to why.

I remember jacking off each night before bed the next few days, jacking like crazy to that scene, waiting and hoping Lisa would come in, but she didn't. She didn't even come home a couple of those nights - at least not until well after I was arelax.

Finally four nights later I heard my door open around 3am and Lisa slipped in bed next to me.

"Jamister, are you awake?"

"Yeah," I said. The moon was bright that night and I could make out her face clearly. She was wearing this night shirt with bunny rabbits on it. I remember thinking how silly that night shirt was, but realizing that she probably had nothing on underneath.

"I'm so mad at Frank."

"Why?"

"He's out with another girl tonight. I'm so horny. He promised he would fuck me after work and he's out with that bitch Gwen instead. God, he's such a jerk to me sometimes." (as Lisa said that, I felt a flash of anger and jealousy at Frank for having such a better high school life than me. Here he was stringing the love of my life, Lisa, along, while fucking this other girl Gwen instead. Gwen was a tall bookish girl, like a smart-looking supermodel, a girl I never would have dreamed of asking out. It bothered me how easy it was for Frank to get girls.)

Lisa and I seemed to have achieved a new level of honesty, and that was proven by her honest admission that she was horny. Remembering how I had made her come the other night with my hand, I slowly slipped my hand in between her legs, thinking I'd love to make her come again. But she swatted my hand away, a little irritated.

"Not tonight Jamister. Tonight a finger isn't going to do it for me."

"Well, then I'll fuck you!" I said, trying to muster up all the bravado I could.

"Oh sweetie," she said, kindly smiling at me. "We talked about that, right?"

"Not really." I said, just playing dumb because I wanted to hear her say it.

"You're so good to me, but your little cock is too small for what my pussy needs tonight."

"Are you sure?" I said. "I know I can fuck you really good." (I'm not sure where this confidence was coming from, but I wanted to give it my best shot, and a part of me really believed I could win her over with my passion).

"Jamister, it's really sweet that you want to make me feel good, but trust me, it's just not going to work. You saw Frank's cock. That's the size I'm used to these days. I don't think I'd be able to feel you. And if I can't feel you, I can't get the kind of come I need."

I rolled over on my back, kind of crestfallen. I felt discouraged and yet mad at Lisa for not letting me try to please her. Another strange thing was that my cock was pretty hard, it was sticking up and since I was under a sheet, you could see it pointing out and making a tent.

Lisa seemed to sense my frustration and she also got a kick out of my erection. "Wow, I can see you are hot for me Jamister." Looking at me with a wicked look on her face, she said, "I'll be right back."

She left the room and came back in with a condom. She said to me, "I like your attitude Jamister. I haven't had a small cock in me for a while, but if you want to try to make my come, I'm going to let you, because I want to get fucked so bad tonight."

I was excited. This was my alpha male moment. I pulled her down on the bed aggressively. She giggled and the condom fell on the floor. For the next 15 minutes, it was just what I had always dreamed it would be. I kissed her, moved on top of her, rubbed her, made her so hot for me that her hips were swirling around me, I put my fingers in her pussy and felt the wetness, I could smell her lust. I let all my passion loose - this was my chance to make her forget all about Frank and show her that I could please her so damn good. The only thing that made me a little nervous was that my fingers did go in her pussy pretty easily, but I pushed that thought away and just concentrated on making her my girl as I had always wanted.

Finally, she jumped up, turned the lamp on, and reached around for the condom. She was done with the foreplay and ready for fucking. She ripped open the condom and I lay on my back with my dick as hard and big as it ever had been. She started sliding the condom on it.

"Oh oh." She said.

I looked down at her to see.

"We've got a problem," she said. She looked a little frustrated, but when I asked her, she started smiling in a really teasing way.

"These condoms are way too big for your little cock. See?" Lisa held the extra space in the condom up. I looked, and as much as it hurt to hear her say that, it was true. The condom was just too big.

"There's no way we can fuck with this," she said. "Frank's condom is going to slip right off your little cock."

I wished she would stop calling my cock little, it was really affecting my alpha attitude, but I was as hard as ever.

Then I remembered: I had one condom in my backpack I carried around for times like these and never used. But I made of point of replacing it frequently so it would still be good. I knew it would fit more snugly as I had bought a box of them and tried them.

I got out of bed and got it out and handed it to her.

Lisa put the condom on my cock, and the fit was much more snug. She looked almost disappointed that it fit as well as it did.

I flipped her over on her back to get ready to fuck her. The look on her face is one I have seen a lot over the years since and wish I hadn't. It was the look of a beautiful, sexy girl who was about to get fucked by me but wasn't the least bit intimidated, nervous, or excited about how my cock was going to feel.

Nevertheless, I just ignored Lisa's look and told myself I would fuck her brains out and prove to her that I could fuck well.

--- to be continued ---
jasonwr1975

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Continuing right along�

Growing up Cuckold, Story 1 (true story): high school sweetie (part eight)

My five inch cock was rock hard and ready to enter Lisa�s pussy. I was still at a point where I could not totally admit to myself that my cock was small. I still wanted to believe I could fuck a girl as well as a jerk like Frank. But looking down at my cock as it entered her, I did have this thought flash through me that my cock looked pretty small, like it was about to be swallowed up by her pussy.

But I pushed that thought out of my mind and thrust my cock hard into her pussy. Wow. It felt so good, her warmth around my shaft. I had never felt anything so good. Lisa had a curious look on her face.

�Is it all the way in yet?�

�Yes,� I said.

�I can�t feel you too well,� she said.

I didn�t want to hear that, so I pulled all the way out and slammed back hard into her.

�Aw!� She said. �I felt that!�

I slammed into her again, feeling my confidence building. �Did you feel that?�

�Yes!� she called out.

I slammed as hard as I could�.and she kept calling out �yes.� What she could really feel was the base of my cock slamming against her. Since I fit into her pussy so easily, it was not a problem to bang her and I was banging hard. For some reamister I was not coming right away, I had jacked off a lot that week and so I was not a quick cummer like I often am in a pussy I haven�t fucked before.

This was perhaps my last innocent sexual moment when I felt like a huge alpha male. Here was this girl bucking beneath me, calling out �Yes!� while I fucked her as hard as I could, savagely and with confidence. In the years since, I have never lost that attitude. As hard and as often as I have been cucked, I refuse to give up sexual pride and I hope other cucks feel the same. At the same time, I have also learned my place, and with some decisiveness. It�s that complicated mixture of �big stud attitude� and �small penis acceptance� that now defines my sexual identity.

The biggest lesmister in that regard was coming right up. I took a break from fucking Lisa and lied on top of her, panting.

�Did that feel good?� I asked Lisa confidently.

�Oh Jamister, yes, you fucked me a lot better than I thought you were going to.�

�Did you come?� I asked her.

�Oh no,� Lisa said, and then with a twinkle and a tease, she said the words I was hoping for and utterly dreading: �Your cock is much too small to do that.�

She could probably see all the conflicted emotions on my face, which included a mess of sexual excitement and wrenching disappointment. She continued: �Don�t be upset Jamister, I�ve never come on a small cock. You fucked me as well as any smalled cock guy has ever fucked me. But that�s why I love big cocks now. It feels so good to come on them.�

While she was talking to me, I was thrusting slowly in and out of her, rock hard from the hot talk. Something came over me, some last determination to prove her wrong. I started pounding her ruthlessly. And then, remembering something from a sex book, I reached down and starting trying to rub her clit. �Oh Jamister!� she said, but then she swatted my hand away. �That�s the right idea, but I�ll do the clit, you just keep fucking me hard!!!!�

I pounded her with all I had, and as she frantically rubbed her clit I could see her orgasm building. She was going to come�..! �I�m coming!!!!!� she said and she squeezed her pussy around my cock and I could almost feel a tight grip for a moment. It was amazing.

After Lisa came, I rolled over on my back next to her, feeling smug and satisfied. I had made her come after all, albeit with her help on the clit. But I could learn how to do that.

�So I can make you come!� I said confidently.

�Well�.� Lisa said. She knew nothing about cuckolding, but this whole game was starting to make sense to her. As much as she liked and respected me, on some deep, primal level almost beyond her control, it was becoming important for her to show me my sexual place. I don�t know why she felt a need to do it any more than I knew desperately I needed to hear it. For some reamister it all needed to be said. I�m not sure if the truth would set us free, but Lisa must have felt that I was better off in the long run with the truth. So she gave it to me.

�Yes, that was a good come, and Jamister, a pretty good little fuck. Maybe if I had never had a big cock I would think that was all I would need. But you see, there�s a different kind of come, a bigger kind of come that only a big cock can give me. It�s a filling come, like I am being turned inside out, like an itch is getting scratched so good, I just go fucking crazy.�

�You know, right?� she continued as she looked right in my eyes. �You saw me coming all over Frank�s big cock right?�

�Yes.� I said. I remembered. I wanted to believe her come with me was stronger because I knew she loved me more, but memory told me different.

�Yes, it�s such a deep come I can have with a guy like Frank, and his thick cock is pulling on my clit too, it feels soooo good. The come you gave me, it�s like a little warmup come. It feels good, just like if you ate me out that would be a great come. But it�s a warmup. You tickled and teased my pussy into a come, but it�s a hungry little pussy now and it wants more. It wants to really come HARD. And Jamister, your dick is way too small for that. �

As Lisa was lying on her back next to me telling me this, she was slowly jerking my cock with my condom still on it. I was harder than ever.

�Here, let me show you,� she said. With that she climbed on top of me and lowered her pussy onto my cock facing me. She slid down on me in one stroke, easily.

�Look how I slid right down on you,� she teased. (Everything from here on out, she said in a teasing kind of tone, without worrying herself anymore about my ego.) �Remember when I sat on Frank while you were jacking off your little cock?�

�Yes� I said kind of quietly.

�His big pole was stretching me so much I could only lower myself slowly, I couldn�t even take it all for a while. He was moving me up and down and it almost hurt, but it hurt so good, stretching me like that, giving me all this heat on the inside. From the second he gets his big dick inside me, my pussy tells me I�m going to come so hard.�

�Guess what my pussy is telling me now?� Lisa asked as she moved easily up and down on me.

�What?� I asked?

�That it has a hard little cock inside me, a little cock that wants to make her come but just can�t reach the cummy place. It�s not fair,� she said and she fucked me harder. �This pussy is plenty wet to make you come, but not nearly full enough of your dick for me to come.�

�Isn�t that right?� she asked me. �If I keep fucking you like this with my hot pussy, your little cock is gonna spunk in me, isn�t it?�

�Yes.�

�But for all that pussy fucking I do for you, I won�t come because I can barely feel you.�

�That�s not fair, is it?� she asked me.

�No.� I admitted.

�That�s why I need a big cock, right?� She said as she lifted her pussy all that way off my cock?

�Yes.�

�And what kind of cock do you have?� Lisa asked me.

�A little one,� I said.

�That�s right,� she said, as she slammed down on me, taking me easily to the bone.

Then she pulled out and got on her hands and knees.

�Come over here, I want to try something. Did you see Frank fucking me doggy?�

�Yes.� I said.

�Let�s see how you do.� She said.

I had a sinking feeling on this one, but got behind her. It took me a while to find the opening and get it inside her. While I moved in and out of her, she felt so loose to me from that position. I tried to pound her harder, to make her feel it good, to unleash my maleness on her. But I kept slipping out. It bothered me so much, seeing her beautiful round brown ass swaying up at me, daring me to fill her pussy and fuck it good. But I couldn�t.

�That�s what I thought,� she said.

�Your little tiny cock keeps slipping out of my pussy from this position.�

�Frank�s got a great cock, it�s so big and thick that he can have a lot of cock inside me and move me all around, pounding me and never falling out. He made me come so hard in doggie and I can�t even feel you.�

Lisa rolled over on her back, a little frustrated. �I want you to lick me,� she said.
We proceeded to do an oral sex session, and I licked her as well as I could with so little experience. I did remember as one sex book said to really just love it down there and put your passion into it, and I did pretty good and she had another excellent come.

Then she sat up. She looked at me and probably sensed my disappointment at how this sexual encounter was turning out. I was not yet as comfortable being submissive as she was being dominant. Lisa called me over and I sat between her legs. She reached around and grabbed my cock.

�Don�t feel bad Jamister, it�s not your fault. You�re a great catch for a girl. Lots of girls haven�t had big cocks like me, and you�ll be plenty fine for them. And I still had a lot of fun playing tonight, more than I thought I would.�

As she was saying this, she was stroking my cock. Lisa was learning how to be a cuckoldress. �Does that feel good, sweetie?� she asked me.

�Yes� was all I could say. It bothered me a little that she called me something as harmless as �sweetie,� but her powerful control over me was a huge turn on too.

�That�s nice�..does your little dick have some come for me tonight?�

�Yes.�

(this marked the first point in my sex life where I was fully ready to accept that I had a little cock � at least for any woman who had experience with larger than average. Slipping out of her frequently during doggie style, remembering how obscene her pussy looked as Frank�s big cock pounded her senselessly from that same position � it was something I could no longer deny. The difference between Frank�s huge cock and my small one must have been incredible to Lisa. I would later learn that a cock as big as Frank�s was almost five times the size of me in total volume, which helps to explain why she felt so different. So of course a woman who had such a big cock inside her would find my cock small. It didn�t matter what the sex surveys said about five inches being pretty average. How I compared to other men was not the key. What mattered was that my cock was way too small for an experienced pussy like Lisa�s, a pussy that had its choice of the cocks that it put inside of it and was able to take a cock five times the size of mine as a tight but comfortable fit. I knew that now. My journey into my submissive side had begun.).

�Does my hand feel good around your little cock?�

�Yes.�

�If you want to come, you�re going to have to ask me again.�

(this led into a scene very similar to one I described earlier, which I will not repeat here, except to say that again I did yell out �Make my little dick come!� again and again as she teased me before I spurted all over her face and my own).

And that was the end of the scene. Lisa didn�t relax with me that night, she went back to her own bedroom. I think she was a bit sexually frustrated as much as she enjoyed the encounter. Neither one of us had enough experience and no knowledge of cuckolding. As a result, we had a hot scene that was sexually a great one for me, but for her, it kind of peaked her appetite more than satisfied it. Of course, knowing what I know now, I would have made sure that a guy with a nice big cock was involved to satisfy Lisa fully after I got her hot and bothered with some warm up cums. At the least we could have tried a large toy, but I don�t think she had one and it didn�t occur to me.

So, not knowing anything more about cuckolding, this exact scene did not repeat itself as Lisa found it kinky but ultimately unsatisfying. However, we were to discover a variation on this scene that worked for us a few more times. I will describe that in the next part I write. But before I close this installment, I�d like to comment briefly on Lisa�s comment about how I would be fine if I found girls who had not had big cocks.

By and large, that is true. The best �vanilla� sex of my life has been with girls who had not had a cock much larger than mine. And I have found several over the years, though as I get into my thirties, I find that there are fewer and fewer girls that have not experienced big cocks and do not have size preferences as a result. True, there are always exceptions, but finding exceptions is not necessarily easy. Add to that the complication that women who have had youngren, in my experience, are even more demanding about cock size, and it can be tricky to find that vanilla relationship where I can be the alpha stud in that particular girl�s eyes. This is why I find myself gravitating back into cuckolding again and again, usually led by my female partner and sometimes led my me. It�s so much better to be honest about our shortcomings and honest about all aspects of sex than to drive our partners to cheat to satisfy their cravings.

That�s a long way of saying that Lisa was right, but I think her advice was really only appropriate for my teenage years and early 20s. After that, in almost every relationship I have had, my small cock has become a factor at one point or the other, even in cases of �true love.� Love can make those issues go away for a while, but sexual fulfillment always becomes an issue at some point. And if you date attractive women, they are going to be tempted by big cocks sooner rather than later. And that�s a turn on in its own way. But for me, it has turned out better to be honest than to risk breakups and cheating. Some of those later stories I will hopefully share in this forum, as they are interesting.

But at the moment, I�m back into a vanilla relationship again. I have no doubt it will eventually turn into a cuckold relationship, but since this one seems to be �for life,� I�m in no rush to push the issue, as there will be no going back once the cuckolding happens - as all of us on this forum know too well. But since I�m enjoying the vanilla phase, and warming up for the cuckolding phase, it�s a good time to look back and share stories. More soon.
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