Growing up Cuckold, Story 1

Growing up Cuckold, Story 2, Part 7

Hello readers. When I started this section of the story, I wasn’t clear that I was going to get into the story of Bethany’s history in so much detail, but I realize it was worth doing, first because I think it is hot and interesting, and second because I think it will offer a better context for what played out once she and I met after she was out of college.

The next couple installments in this story will take us from where Bethany was at in college during the “summer of Nick” to where she was at when she and I met. The transitional installments may not be quite as intense to read in terms of sexual detail, but I hope they are still entertaining and I think you will enjoy where this tale leads once she and I meet. Onward…back to the day after she had that ill-fated threesome with David and Nick…

Bethany was at a strange point in her sexual evolution. She had just been fucked better than she ever had been in her life, and come harder than she ever had. It was an amazing feeling, one that she would not trade for anything – or would she?

Bethany didn’t hear from David for a couple of days, and in that time, she went back and forth in her mind, in a state of confusion. There were times where she missed David so much, and other times where she masturbated her sore pussy to another intense orgasm thinking about Nick’s big cock and how good it felt inside her. The biggest come always came when she imagined looking over at David jerking his little cock off while she was getting stuffed and filled by a bigger one, getting satisfied in way that he was physically incapable of. But why did that turn her on so much? And why couldn’t that have actually happened instead of what did happen?

As our readers know, Bethany was facing a common female dilemma: emotional attachment/connection to one partner, sexual hunger for a different one. In her own intuitive way, Bethany had attempted to resolve that dilemma through a cuckolding scene but that had not gone well. What had come over her? Why had she said such things to David? Did she really say them?

A couple days later, she and Nick fucked again. She found out later that David had come by then and heard them having sex and left without knocking. Eventually, later that week, she and David ended up talking, but it was only a conversation long enough for David to break up with her. David felt disrespected by what had happened, especially when the condom broke and Bethany wouldn’t stop fucking Nick. As we have discussed, David was not good cuckold material. Other girls in campus had crushes on David and he felt no need to go through any kind of psychic offense at Bethany’s hands. During the breakup conversation he ended up calling her a “slutty bitch” and that was pretty much a deal-breaking moment for both of them.

So David and Bethany went their separate ways. Bethany was a little upset but only in a distant way. She was having too much fun fucking Nick. They were having sex all the time, Bethany had never felt such an urge to fuck before. One thing that was a big surprise to her was some of the new positions she could enjoy with a cock of that size. Nick had enough length that they could fuck standing up, fuck with her leaning on a counter with her leg up in a “scissors” position, and they could fuck in that “spooning” position that guys with cocks my size tend to struggle with. Nick’s big cock was a novelty and for several weeks, fucking was all that mattered really. She even squirted a bit from her pussy a few times when he was fucking her and she came. That had never occurred before.

But as always happens in life, eventually thing shift into the question of emotions. Bethany attempted to form a relationship with Nick as a way of resolving the emotional/sexual dilemma but she knew deep down it wasn’t going to work emotionally. They just didn’t click. Outside of bed they weren’t really interested in the same things. Nick was big on fantasy gaming and chess and things like that. He wasn’t very outgoing socially and as much as she worshipped him sexually, Bethany couldn’t make those feeling carry over as much as she wanted.

Bethany also knew deep down that Nick wasn’t monogamous. Nick was enjoying his newfound sexual power and he knew, like guys with big cocks who know how to fuck do, that many women will date them even if they are not always faithful, putting up with things they would never put up with if they weren’t getting fucked so well. Nick had a margin of error and he played it to the hilt.

On a certain level, it turned Bethany on to know that she was dating someone who could fuck so well that women who would otherwise make better decisions couldn’t help themselves around him, but on the other hand it went against her desire to feel a deeper bond with her boyfriend. Nick had a habit of not calling her back sometimes for a day or two and that was the kind of thing Bethany wasn’t used to. She knew inside herself that he was fucking other women during those times though she never asked him because she didn’t really want to know. She was used to being the princess and having control and guys doting on her. And Nick sure wasn’t a doter.

Bethany had fun with Nick that summer, but it wasn’t going anywhere after that. She never let Nick fuck her without a condom again. With all that come he put so deeply inside her, Bethany felt lucky she hadn’t gotten pregnant and no way was she taking that chance. One thing that bothered Bethany is that Nick seemed to be spending a lot of time with one student from the math camp.

She was a little buxom hottie, anything but your typical math camp geek student, and she always seemed to have a blushy flirty feeling around Nick. Nick wrote the whole thing off and explained she was just getting some extra tutoring, but it didn’t feel right to Bethany. Nick could have gotten in a lot of trouble relaxing with a student, and she didn’t think he would risk it, but Bethany was still a little skeptical when she would seem them having lunch together.

On the last week of math camp, Nick seemed less interested in having sex with Bethany than usual. He wrote it off as being too wrapped up in the job, but Bethany felt suspicious. One day she thought she saw Nick and the girl from math camp (who was of legal age for the purposes of posting a story that is legal to post here) heading onto a trail that led into the woods around campus, but she wasn’t sure. Was she just getting paranoid? Seeing things?

Finally she got fed up and one morning before work she went by Nick’s room on the other side of campus. She knocked on the door and no one answered. She was about to leave when she saw a small shadow underneath the door. She bent down and could make out the shape of something on the ground. It looked like a note of some kind. The corner of it was near the door. Bethany looked up and down the hallway and then without thinking about what she was going, she pulled the paper out.

It *was* a note, folded in the shape of a heart. Bethany could hear someone coming so she stuffed it in her purse and went to the women’s bathroom down the hall. She shut herself in a stall and with her heart pounding, she unwrapped the note. It was a goodbye note from Stacy, the “extra tutoring time” girl from math camp. Before I share the contents of the note, I want to explain how Bethany felt opening it up. Bethany was sure that this note would be full of “I love you Nick!” schoolgirl crush type of thoughts. But it was anything but that.

The fact that the note was folded into a heart was the only gushy schoolgirl thing about it. The contents and tone of the note itself were almost clinical….Bethany never forgot that note and she told me of its contents. I’m sure I don’t have it word for word, but I think I can recreate it.

“Dear Nick,

I want to thank you for fulfilling my fantasy and confirming my theories. I realize we could get in trouble for what we have done, but you should know I won’t be telling anyone. You will probably want to destroy this note but I did want you to know just what it meant to me to be with you.

Before I was with you, I had never had much fun with sex. The ‘jockers’ at my school are such idiots. The only guys I had sex with were geeky shy guys. The last guy I had sex with was the science club president. I wish I had a laboratory to send his little pencil dick to so they could study it.

He wanted to please me so bad, and I think he could tell it wasn’t happening for me, and when I finally couldn’t take it anymore and had to ask him, “are you in yet?” he started crying and I spent the rest of our date comforting him like he was a little girl.

Lying in bed that night I started thinking about my problem mathematically. I've had three guys inside of me. They all felt small, but the bigger of them did feel better. So what would something really big feel like? If they felt better when they were bigger, just how big could they get?

And then I met you. I didn’t think of you as a sex guy at first, I put you in the “small dicked math geek” category from day one. But as you I both know, you are not that! Thank you for putting your huge cock inside of me. It took a lot of persuading on my part and a lot of work on your part, but my pussy wants to thank you for making it so happy. No more pencil dicks for my little coochie! Thank you for showing me everything I knew I was missing.

Goodbye Nick.”

What the heck? Coochie? What kind of girl would write a note like that? It was so cold in a way, so shallow. “Thank you for putting your huge cock inside me.” Wow. Bethany was mortified and angry and her hands tremred as she tried to fold the note back into the shape of a heart. She realized she had started crying – why? And in her frustration folding the note back up, she almost ripped it up. But finally she figured out the folds in the note to make it a heart shape again, and she shoved it back under Nick’s door. And then she went home and masturbated until her clit was sore – she knew exactly what Stacy had been lucky enough to feel. And she was familiar with the crazy lengths a girl would go to feel that way. God that was so hot!

Later that night, without bringing up the note, she confronted Nick with more confidence and he gave in and shrugged his shoulders and admitted he had fooled around with other girls, though he said nothing about Stacy and neither did Bethany. Then something happened Bethany didn’t expect. After Nick shrugged his shoulders, he gave her this arrogant smile that implied something along the lines of, “with a big fat cock like this, and so many girls putting up with small, skinny ones, can you really blame me?” And Bethany realized that on a certain level she couldn’t blame him. This made her really pissed off, really angry, and….really turned on.

The smaller percentage of bigger guys on this cuckold forum probably know what kind of sex happened next – the kind of sex small dicked guys never get: “I fucking hate you, and I’m gonna break up with you soon…you don’t deserve this pussy, you unfaithful jerk, but in the meantime, fuck me one more time with that beautiful cock, make my pussy come!”

This would be the last time Bethany fucked Nick, and it was a fuck for the ages….at one point Bethany was taunting Nick as he was pounding her, and she called out to him, “Is this the best pussy you’ve had? Is this the best pussy, you slut?” “Oh fuck yes! It’s the best!” Nick yelled out as he came inside her. For some reamister it made Bethany feel good and powerful for him to at least admit she was the best of the summer pussy he had gotten. She loved being such a wanton servant for his cock. Even though Nick had his condom on, she could feel the tip of that condom expanding like a small balloon inside her as it filled up with his biggest load ever. It was a weird feeling but a hot one.

Bethany was kind of relieved when the math camp portion of the summer ended and Nick left. She wasn’t sure she could stop fucking him if he was around, and yet she knew she had to – it was eating away at her dignity. “You deserve this,” she would scold herself. “This is how you made David feel.” Later I told her that she wasn’t quite right about that – what she made David feel was a little more intense than that.

Anyhow, it was pretty busy getting ready for the new school year so Bethany threw herself into her work, moving into a new dorm, etc. It felt good to keep busy. During one of those days, she saw David walking hand in hand with a new girl. She felt a flash of jealousy and sadness, and then swept into a wave of happiness for him. “Good,” she thought to herself – “I didn’t damage his sexual confidence.”

There was one day right at the end of the summer that was memorable. She went back to her old dorm room one more time to get her hair dryer which she had left in the dresser, the rest of the room was empty. Looking around the empty room, she could feel all the memories flooding back. For a moment, she had a lusty flash remembering that scene with Nick and David. (“this was the bed where you really got fucked for the first time!”) But most of the memories were sad ones – memories of her great relationship with David. The love she felt for David started rushing back, and before she knew it, the tears were rolling.

As she sobbed on the bed, she wasn’t just sobbing for David. She sobbed because of the bad decisions she had made, the lust that had gotten so out of control. For the first time, she felt like the slutty whore David had accused her of being. And what would she do now? Could she ever find love again? She had more to learn about that in the next couple of years, and once we get through that part, we will reach the point where I finally enter the story.

- to be continued -

Thanks for the update! I'd love to read more.

Thanks eet...there's more to tell for sure. I am hoping to get another installment done and posted by end of weekend. Appreciate the good words, they always motivate me to get pen to paper.

wow... omg, the David in that story is so me. Jamister let me tell you, your actually lucky you were just a bit small enough to have no choice but to confront all this younger.

I'm that near Alpha, In my prime around 7' and now in my 30's being a smoker and such just under 6'. I have been Alpha at points, with women who lacking experience came and enjoyed me... only over time to lose that capacity for them.

A complicated story with alot of ups and downs and lots of time thinking I was an Alpha and then getting smashed back down...

That David in your story, very similar to me...

I mean it's hard to even relate, I should have known because My first Cuck experiences started well before HS, but my life back and forth with always some new or a new girl convincing me I was Alpha again and the last girl was a sicko lol...

Had a few women that if I could have just understood and accepted myself... I could have been with forever... I was periodically so very lucky with it... fortunately I now know myself and can enjoy my sexuality

very interesting Damian, thanks for your honest point of view. I have always felt bad for David for some of the reamisters you've described and I've wondered how he fared as he got older. As you pointed out, women do become more discerning about size I think as they get more experience. So David's chance to be an Alpha probably got undermined more as he got older...who knows how he ended up but I'm sure it was a challenge to work through that - either that or he just got married and never looked back. But we know from all the married folks on this board how rare that is.

Just curious, are you saying that the women that you could have been with forever if you had accepted yourself - did you mean they would have cuckolded you if you had been willing to go that road or suggest it?

Thanks for the good comments and I'm hoping to get another part of this written soon, weekend got away from me.

Yes exactly jamister I was actually introduced to this by one woman in particular in my early 20's and ran from it after a couple months of play...

best post on this site. Please post more

thanks Supafly1.

I appreciate the good words. I'm really hoping I'll have time for another installment this weekend. It's always good to hear from readers!

Growing up Cuckold, Story 3, Part 1

Hey folks…sorry for the delay getting back to this.

Without further holdups, we are going to begin the third story, though I suppose we are still wrapping up the second story – the third one truly begins when Bethany and I meet. Let me see if I can get us there soon.

So last time we left Bethany, she had just finished a fun but difficult summer that featured her discovery of big dicks but also the failure of her special relationship with David. It’s interesting to remember Bethany was only 19 then, going on 20, still a couple years away from graduating.

Bethany was unlike most girls her age, in that she not only had some exposure to cuckolding in her family, but she had attempted to try it in real life. However, it had not worked. Obviously, those of us with more positive cuckolding experiences can see the obvious problems in what Bethany tried, but in her mind at the time, she had tried cuckolding and it hadn’t worked. As a result, Bethany put the option of cuckolding aside. I think when you are a young, hot alpha female, cuckolding has less usefulness anyhow - unless you are truly turned on by the dominant aspects of it.

Another way of putting it: if you are young, hot, female, and single, with no family responsibilities, and Bethany was all of these things – then why not just fuck big cocks? Why get involved in the complications of cuckolding? Yes, you might miss out on some emotional closeness by focusing on quality of sexual intercourse and not on finding the best relationship, but you can get emotional closeness from your female friends and male platonic friends. At least that’s how Bethany looked at it.

So that’s kind of what Bethany did. For her junior year, she pretty much stayed uninvolved romantically and just had some fuck buddies. Bethany mostly fucked big cocks that year. She got pretty good at figuring out who was hung. She hadn’t reached the point of asking guys outright, but she was better at bringing up size in her conversations with her female friends. Now bringing the subject up often, she was surprised to learn how many of her friends preferred size. True, some didn’t like the huge ones, but virtually all of her friends who had tried bigger than average cocks preferred them. It was only a matter of how strong the preference was.

The other way Bethany figured out who was big was that tried-and-true dance floor method. She would get a guy out on the dance floor and do some slow grinding. There was really no way you could miss the bigger guys that way, or figure out the guys who didn’t measure up. As a funny aside, the biggest guy she fucked that year she met while dancing to the misterg “Wannabe” by the Spice Girls…this guy was longer than Nick, more like nine inches, though he wasn’t as thick as Nick. Oh, and the guy was Chinese, so there go your racial stereotypes, at least this time around. He was small and skinny, so his cock looked absolutely gargantuan on his tiny frame. He loved surprising white girls with his big dick.

Bethany didn’t have a problem taking nine inches like a lot of girls do, but after taking nine inches inside her, she didn’t think she could take much more than nine comfortably, he was hitting bottom a lot. But she still wanted to find out for sure someday. Looking back on that year, Bethany still thought of Nick’s super thick eight inches as the best cock she had tried so far.

Towards the end of the year, she ended up running into David and having a very friendly talk with him. He was still dating the girl she had seen him with, and he seemed really happy. After talking to David, Bethany found herself crying in her dorm room. For all her sexual confidence, she hadn’t really solved that relationship riddle after all. Bethany decided she really needed to find a real boyfriend again.

I should mention that during this year, Bethany did try having sex with a few smaller-to- average guys again, just by basis of comparimister. The first guy was about six inches, and she was struck by how less fulfilling he was than David had once been. She had definitely gotten spoiled. She didn’t tell this guy his cock was too small, they just kind of had sex a couple of times and drifted away.

Later that spring, Bethany had sex with a guy about my size, five inches. This guy was really cocky and a big athlete at the school on the swim team. He had not been brought down to size by any girls yet and so was very aggressive in his seduction tactics. He was a great athlete, and he would pump away at Bethany so hard, just pounding at her. But Bethany wasn’t too turned on by him, and she remembered being almost vaguely amused at the all-out effort he was making and the comparative lack of sensation she was feeling. She would fake her orgasm to get him to stop, and he was surprisingly good at eating pussy so that was a bonus.

This was a guy who had been really sweet to her at first, before he got her into bed, but had then started being kind of cocky and inconsiderate, not returning phone calls, hitting on her friends. The last time they had sex, he was about to put his cock into her, and as Bethany looked at him about to try to fuck her brains out, her first thought was, “God, you are tiny – way too small for this job!”

She didn’t say anything out loud, though, and she went ahead and faked her orgasm again and went through the motions. Then, to add insult to injury, this guy did relax with one of her friends and he and Bethany ended up breaking up over it, though they had never really gone out. Bethany swore that was the last time she would hold back about her sexual satisfaction – at least around jerky guys with small equipment.

Her last guy of the year who wasn’t big was actually more than six inches, he was almost seven, but he was really thin, to the day I met her, the thinnest cock Bethany has had inside of her, though I wasn’t too far behind. Bethany told me it felt more like a medical exam, being poked and prodded, than actually having sex. She could feel him, but not really in a good way. This guy was actually the first guy who was open with her about his size. After they had had sex a couple of times, he had the guts to ask her, “Am I too small for you?”

Bethany felt a lot of relief being able to just tell him, “Yes, I guess I am kind of spoiled. I really need a thick cock to come…I’m sorry.” Bethany was still at the point where if the guy wasn’t a jerk, she would feel apologetic about this kind of honesty. One more thing happened with this guy – after they had sex for the last time and had this conversation, he ended up taking a shower while she was finishing a paper.

Later that night, she thought she found some sticky sperm traces on the walls of the shower, that’s sure what it looked like. She thought back to their conversation, and how this guy had looked instantly hurt, but maybe a little excited, when she said what she did. Did this turn him on to be told he was too small? Evidently so, based on the trail of evidence in the shower. “Are there guys who get turned on when you call them small?” It was a question Bethany honestly wondered about, her curiosity had been peaked.

Anyhow, for her senior year and the year after graduating from college, Bethany didn’t find out, because she had a serious boyfriend again. She had had her eye on this guy for a while, we’ll call him Tom. Tom had been dating a real beautiful girl his whole time on campus. He was notoriously monogamous. Other girls had hit on him to no effect. Bethany was intrigued by his monogamy, and also by his big dick.

Unlike most big guys still getting comfortable sexually, Tom was not hesitant about showing off his package. He was on the school’s football team, and he had a habit of wearing stupid looking mesh t shirts and ridiculously tight shorts and throwing the football around the dormitory quad. His big cock jutted out obscenely, just bulging out the front of his entire shorts. It looked like his cock roped around like a curved sausage all through his crotch. He looked absolutely massive. Bethany had not had a massive cock yet and was very curious.

But Tom was monogamous. He liked to flirt but that was it. The girls all talked about him and Bethany still remembers one night when four girls admitted during a takesen truth or dare game that they had all masturbated thinking about Tom’s huge cock inside them. The two guys in the truth or dare game seemed really uncomfortable. Bethany remembered thinking that she should be more honest in front of guys about size, and how much it turned her on to do it.

Tom and his girlfriend were almost like the homecoming queen and king or something, and when they broke up early senior year, it was big campus news. All the girls descended on Tom but even with Tom being single, they couldn’t get to him. Finally, one girl Bethany knew who was a tall supermodel type who did some modeling after college finally got to him at a party.

Bethany found a way to talk to the girl the next day and she had no problem telling Bethany all about it. “God, he has a such a huge cock! He really knows how to fuck!” She told Bethany it was the best fuck she had ever had, and on and on about Tom’s cock.

This intrigued Bethany more than ever, she had never been with a truly massive guy, now might be her chance. And Bethany being the amazing hottie that she was, managed to get Tom alone a couple weeks later. She couldn’t believe her excitement when she first got him alone, but here was the surprise: when she pulled Tom’s shorts down, his cock plopped out huge, but as she worked it and got it hard, it didn’t get much bigger. He was still almost eight inches and fairly thick, but he turned out to be a fair bit smaller than Nick.

This was Bethany’s first realization that girls don’t always relay accurate information on size as they may not have the same basis of comparimister. And this was also Bethany’s first experience with a “shower.” Tom was more than six inches long soft, thus the massive bulge in his shorts, and she said his dick looked amazing flopping down his thigh when he walked around naked, but he didn’t get as big as you would think. She said the size of his soft cock made her think he would be ten or twelve inches, but he was not as long as Nick.

The other strange thing was that his balls weren’t that big like a lot of big guys. Tom sometimes came a lot the first time he orgasmed, but for the most part, he wasn’t a real big cummer either. Bethany was almost a little amused by how small his perfectly normal balls looked underneath his big cock. Unlike with Nick, she couldn’t feel Tom’s balls slapping against her when they fucked doggy style.

Tom was surprised that Bethany wasn’t more surprised about his size, he was used to a fair amount of size worship. But it was still a great fuck for Bethany, and she could definitely feel him inside her much better than the “poker” and the smaller guys. And more than that, Bethany found she had feelings for Tom. They ended up dating for two years.

The first of the two years was probably the happiest in Bethany’s sexual life to date. She was in love with Tom, he was definitely big enough to satisfy her, and she had resolved her sexual/emotional dilemma by finding someone who could meet all her needs. Cuckolding was no longer an option to grapple with. Bethany continued to get more confident in herself, and sometimes she would see herself as more dominant and verbally aggressive in and out of bed. This turned her on, she was starting to get a bit of that “older woman confidence” so many of us on this board are hooked on.

But relationships change, and Bethany soon discovered the problem when you center your life around someone who is first and foremost good in bed: as you become aware of their flaws outside of the bedroom, it starts to impact the chemistry inside the bedroom. Bethany and Tom moved in with each other in New York City. He got a job in the insurance industry and Bethany was not inspired by this corporate insurance version of Tom – it was not nearly as hot as the sexy athlete throwing footballs in the quad. Tom liked to come home and take beer and watch college football games he had taped on the weekend – good times! Well, maybe to Tom, but not to her. Bethany started to realize something: Tom was boring.

No, Tom did not have the fatal flaw of infidelity, and Bethany felt lucky for that. Tom was still as good looking as ever, and Bethany knew that most girls would in her position would never break up from a trophy husband like Tom. It’s hard enough to find a guy with a big cock who knows how to use it, but to find one who is not only professionally successful but seriously monogamous and not prone to cheating with all the women who hit on him – well, that was a true find!

When Bethany broke up with Tom and moved to Boston, none of her female friends could understand her leaving a catch like him. But Bethany just wasn’t emotionally fulfilled and she just couldn’t see herself growing old with Tom. He just wasn’t unconventional and adventurous enough for her. He was full of duty but not full of bold passion. I don’t think we talk enough about this on our cuckold board, but emotional needs are a big big part of what makes a relationship work for the long term.

Bethany remembered that drive to Boston and really doubting herself – what had she done? Learning about the importance of size hadn’t necessarily helped her in her relationships. She had had some great sex, but so much of it felt empty looking back. Had she dated the wrong people? Should she have been more open-minded about smaller guys who were really compatible with her emotionally? Maybe tried some larger sex toys with them?

No doubt about it, prioritizing big dicks had gotten her in trouble in her relationships. This was another version of smart women, foolish choices, but with a penis size twist. As she drove to Boston, she remembered crying to herself a bit about the problems she was having. I think this matters to our story in this way: because the sum of all Bethany’s experiences gave her strong opinions and preferences, but her difficulty finding a perfect situation had given her an open mind. She hadn’t found the answer yet, so she would be open to the different options that presented themselves to her. Soon, that option would be me.

- to be continued -

Growing Up Cuckold, Story 3, Part 2

Hey folks…I’m sorry the last installment did not have too much action. It was more of a transitional section than I expected. I don’t always know what details I should include until I start. But the good news is…I wrote some more “bonus material” I have now polished up for you. Bethany and I aren’t going to meet yet, that will finally happen in the next installment, but this one will bring you up to speed from where we left off on my life many installments ago. And this section should have some good action in it as we bring us to the point of meeting up. I think you will enjoy this one, it’s one of my favorites I have written so far.

The year Bethany moved to Boston was the fall of 2000. She was 23 then, and as fate would have it, I was also living in Boston, where I had moved at the age of 24 to the Harvard Square area. I was 25 actually when she and I met.

We’ve had quite a detour in our story filling in on Bethany’s background, longer than I expected. So let’s remember where I was at. I had just finished having that devastating little encounter with that older woman Pat, the first woman to openly call my cock inadequate for her sexual pleasure. It turned me on so much, and I got a lot of hot masturbation sessions out of that experience with Pat.

But it also made me sad – was I destined to a life of lonely masturbation? How far I had traveled from that point where size didn’t matter and my whole sexual history was still optimistically in front of me. How would I find a way out of this?

I was still a few months away from meeting Bethany. I resolved to solve my size insecurities by projecting an air of confidence, but focusing more on women who seemed to like to bond emotionally first, or who didn’t seem to have as much sexual experience.

I soon met one such woman, we’ll call her Cheryl. Cheryl might have been my last best chance to put my size insecurities behind me. She was not promiscuous, and was all about emotional bonding before sex – or so she told me. She was really fun, sexy, and outgoing, and an aerobics instructor and yoga teacher. We became fast friends. I was worried about the moment we might have to confront my size, but we were still very comfortable in the “friend zone” and sex didn’t really come up between us. All in good time, I thought, all in good time. Let her get to know “the real me” first.

Mostly we spent time alone, going to movies and sometimes to plays. But every now and then, she and I used to go to these “hippie hot tub parties.” The parties always made me nervous because most people took off their suits in the hot tub, and those that kept their suits on always seemed like squares. The parties secretly turned me on and I went to a few of them, with and without Cheryl. But I tried to stay out of the hot tub. There was usually music and card games inside, so you could kind of avoid the hot tub if you wanted.

Anyhow, there was this one guy who seemed to get a lot of girls who was often at these parties. He was this arrogant DJ and I really thought he was a jerk. I was jealous of him too of course for all the action he was getting. Either he was big or he didn’t have my insecurities.

I hated my insecurities because I felt they affected my natural confidence, but I couldn’t go back in time and erase them. Unlike Bethany’s ex David, I couldn’t put cuckolding memories behind me. I could never pull off the “alpha dog” anymore and it bothered me when I met guys that could, because I knew not all of those guys had big cocks, in fact, many were probably overcompensating. Jeremy was one of those naturally cocky guys. I hated him.

I was really relieved one night hanging out with Cheryl when she started making fun of Jeremy and talking about what a shallow poser he was. This was one more sign to me that Cheryl and I might have a sexual future together. If she found guys like Jeremy repugnant, I definitely had a shot.

But then Cheryl said something that took me by surprise: “And you know what else? I can’t believe he gets all these girls to buy into his hype! I’ve seen his cock at the hot tub parties! And he’s really pretty small!” This conversation was really turning me on – I had only heard the penis size discussion so openly a couple of times at this point. On the other hand, I was also nervous – just how small is small? And would I be too small for Cheryl? And she claimed to be interested in emotional bonding more than physical attributes. So why had she brought up size? Did she really care about it, or was she just using it to make fun of a guy she didn’t like?

I was too nervous to ask her but I jacked off like heck afterwards.

Then came a pretty fateful night in my sexual history. I ended up at a hot tub party where all three of us, Jeremy, myself, and Cheryl, were in attendance. At one point, I noticed Jeremy in the hot tub, so I got up my courage and took my shorts off and went out there. I just had to know how big he was, or actually, how small Cheryl thought he was. We were both sitting out there with a couple other people.

Then Cheryl came out there. I had never seen her naked before. It was amazing. Maybe not everyone on this board is turned on by muscular women. Cheryl worked out obsessively and you could see the muscles ripping through her abs, arms, and legs. It wasn’t my ideal woman, I tend to like a little curvature, but it was sure hot to see her body in the nude. She looked like a panther. For a moment, I imagined the idea of trying to please such an athletic amazon (she was 5-9) with my little cock, but I put the idea out of my head quickly so as not to get an erection.

Right then, Jeremy asked me to come smoke some pot with him, and since I wanted to see what he looked like naked, I agreed. When he got out of the hot tub, I was relieved. His cock was almost as small as mine! I wasn’t that big soft and he wasn’t much bigger. Of course, I was also a little nervous. If Cheryl thought his cock was small, what would she think of mine? Jeremy and I went to a table around the corner in the dark to smoke. At one point, a light went on for a moment in the bedroom and flashed on us. I remember sneaking one more peek at his crotch, and once again, I felt a sigh of relief, he was definitely not big. I do remember thinking there was something strangely substantial about his small soft cock, but thought nothing of it.

I felt much better about myself walking back towards the hot tub. Even if Cheryl thought I was small, Jeremy got lots of hot women, maybe I could too. Hope springs eternal. Jeremy went back inside and soon it was just Cheryl and I in the hot tub. She looked like she had something on her mind, so I asked her what was up. She said, “I’m confused.”

“Why?” I asked her. “Well,” she said. “I was talking with Sarah about Jeremy.” (Sarah was a hot looking blonde hippie chick who kept herself in pretty good shape through hoola-hooping…she always intimidated me due to her honest natural confidence. Sarah had a real open and upfront view of sexuality you often run into in hippie circles). “I was making fun of him, comparing his big ego and his small cock,” Cheryl continued… “Then Sarah said to me..’Cheryl, you need to lay off Jeremy a bit. Maybe you don’t like him, but I can tell you two things: he’s fucking great in bed, and he doesn’t have a small cock at all. I promise you: if you give him a try, you won’t feel like making fun of him anymore.”

I felt my little cock twitch at this story, which was not a good thing as I was in a hot tub.

I didn’t know what to say, I felt shy and turned on and also confused that Cheryl had told me this story. “Anyhow,” Cheryl said. “He’s still a jerk. And you saw his cock…it isn’t really any bigger than….” Cheryl was about to say “yours,” I just knew she was, but she caught herself. My little cock twitched almost to full erection in the water. Fortunately, you couldn’t see into the water.

Looking back now, I regret not taking this scene with Cheryl further, but at the time, I was paralyzed almost, mortified and excited and not sure what to do. I feel pretty certain if I had placed her hand on my cock she would have jerked me off, and who knows what would have happened then? But I wasn’t ready. I wasn’t the confident cuckold who knew his sexual place without apology or shyness. I was the insecure small dicked guy. There’s a huge difference.

Anyhow, the moment passed. We talked about something else, though I couldn’t pay attention well, which was too bad because we always had the best conversations. Cheryl seemed a bit distracted also. At some point a little while later, Cheryl got out of the hot tub and asked me to come inside also and get cold takes with her. I got out a bit reluctantly, as I was still a bit aroused, but I was also happy because I knew I would appear a bit larger this way.

As we got out of the hot tub, there was no question she took a good look at my cock. Then she walked in ahead of me, and I could have sworn she smiled. I have always wondered what her thought was that day, what made her smile that way. Later I masturbated about it, and of course I pretended that she was thinking, “wow, his little cock must have gotten hard when I called attention to it,” but of course, I’ll never know. I kick myself now for not pursuing it.

A little while later, the party slowed down and it was just about eight of us playing cards in the living room. Jeremy was still there, so was Cheryl, and so was Sarah. It was not unusual for folks to skip rounds to play guitar or take a piss or smoke break or whatever. I couldn’t help but notice that Jeremy and Cheryl were sitting next to each other, and for claiming not to like him, she seemed almost flirty and shy and smiley with him.

Of course, those of us who know this lifestyle know exactly what was going on and what that change in Cheryl’s attitude was about. I didn’t realize it then, but Cheryl was giving Jeremy the old, “now that I know you have a big dick and can fuck so good, that changes everything” face.

Jeremy probably picked up on that vibration, and thought of a reamister to go into the bedroom and play a video game. A couple minutes later, Cheryl got up to go use the bathroom, but she didn’t return. Another round of cards went by and I couldn’t restrain myself. I got up to use the bathroom but I went into the game room/bedroom instead. The door was slightly open so I didn’t knock.

What I saw I will never forget. Jeremy was sitting on this swivel game chair, kind of facing ahead at an angle to the door. Cheryl was on her knees sucking his cock with her mouth while jacking the base of his thick cock with her right hand. She had her jeans on, no shirt, and had her left hand in her crotch. Her mouth was on his cock, and his cock was hard as a rock and really pretty damn big. I can’t say exactly how big it was, I have since seen much bigger, but it was definitely in the 7.5 range. Damn!

Cheryl was moaning and obligation on his cock head and seemed very horny and excited. I was able to shut the door back to a crack without really bothering them, Jeremy had his eyes closed, Cheryl did look over at me before I was able to shut the door and expressed surprise in her eyes, not embarrassment really, just surprise, but I was out of there before she could take her mouth off his cock. She looked like she was trying to swallow a Coke can – kind of obscene really, but kind of hot too.

I made my way back to the card game and Sarah gave me a harsh look. She had a bit of a view of the hallway from where she was sitting, and she was the kind of alpha who could look right through a guy like me and sense every devious desire, every insecurity, every bit of small penis shame. The look Sarah flashed at me was, “how dare you interrupt my homegirl when she’s trying to get fucked by a real man for once?”

But it passed, and I tried to focus on the card game and not think about what I had just seen. Then we heard some unmistakable screams from the bedroom – Cheryl. At least one permister in the group sat straight up, seeming concerned.

“Oh don’t worry about it, that’s Cheryl, she’s just getting fucked real good,” Sarah said, laughing as if it happened all the time. At her house, it probably did. Then we heard it: “Oh my God!!!!” Right then from the bedroom, right on cue, and pretty much everyone except me cracked up. Was I paranoid, or did Sarah notice I wasn’t laughing?

“Who’s back there with her?” asked this other girl, I didn’t know her name. “Jeremy,” said Sarah with a knowing smile. “Ahhhhhhhhh” said a couple of the girls, and they seemed to exchange knowing looks. “Yeah,” Sarah said – she was always pretty honest but especially times like this when she was takes – “She was making fun of Jeremy and I told her not to underestimate him until she tried him….and now she knows.” Sarah stopped short of bragging up Jeremy’s big cock in front of the guys in the group, but her point was not lost on anyone.

The fucking sounds got louder. I was kind of hoping to hear some slutty “big dick” talk from Cheryl but all you could hear were her natural screams and moans. It was clear she was coming and coming hard. Was she riding him? I could only imagine how good Cheryl’s pussy felt squeezing and massaging Jeremy’s thick pole. Sarah told us to take our card game outside and “give them some privacy – they obviously need more than one room to themselves,” she said, and everyone laughed and smiled.

I remember being torn when we were outside. A part of me wanted to go back inside and maybe jack off in the next room and listen to this girl I had a big crush on getting totally fucked by the big dick I wished so much I had. But I was worried I would get caught. I noticed Sarah looking over at me sometimes, and her look said it all. I thought if I went inside she would be onto me, and I didn’t want to get caught jacking off by her.

“Eat your heart out,” Sarah seemed to say to me with her fierce teasing looks… “Listen to this girl you liked getting fucked! Can you believe she spread her legs for Jeremy and she wouldn’t for you?”

I wanted to wait until Cheryl and Jeremy came back out and see how Cheryl would deal with me, what on earth she would say after she and I had bashed Jeremy all week, but I didn’t have the heart. I started to feel lonely and upset. So I excused myself from the game, said something about working early the next day, and went home.

After I got home, I felt pretty bad about everything, getting passed over again for another jerk like Jeremy. God knows most cucks on this board have experienced that kind of agonizing, sexual-rejection-laced loneliness. Especially us small-dicked cucks. If you haven’t ever experienced it, you are damn lucky! There are few worse feelings in this world, not just to be alone, but to feel like you have no sexual place in the world at all. But then I started getting horny, and my imagination got the better of me. I must have jacked off my little cock three times before finally going to relax that night.

I would imagine all kinds of scenes – one of my favorites was Cheryl sucking off both of us, starting off about the same size soft, but then Jeremy’s cock growing and thickening while I stayed short and skinny, and Cheryl fucking him right in front of me and telling me how good a real cock felt, and that as much as she liked me, I wouldn’t be able to fuck her because unfortunately, I had a little boy’s dick, and as much as she wanted to, she wouldn’t be able to feel me.

An even more exciting version of this scene involved Sarah walking in on us, jacking off my little cock and teasing me while Cheryl got pleased by Jeremy, and then Sarah climbing on Jeremy while Cheryl teased me and my little cock, and asked me if I wished I could feel what it was like to really fill a pussy up, and how sad it was that I couldn’t ever feel that, but how hot it was too, and how she wanted to see my little dick spurt for her hand like it never would in her pussy. Who knows, maybe I could have pleased Cheryl, but she never gave me the chance in real life. Jeremy’s “big cock reputation” got him further in a night than I had been able to get in a month.

For the next couple of months, I went through this confusing back and forth, sometimes being totally aroused by what had happened, sometimes feeling upset, feeling betrayed by Cheryl for her not being honest with me about what she liked and why. It seemed like all the women in my life said they wanted one thing sexually and then did something else. And at least in the heat of the moment, their need to get a big cock inside them was definitely more powerful than any hurt feelings I might suffer on behalf of my ill-founded hopes.

I started missing Lisa and how direct she had been with me that my cock was too small for her, and how much that turned me on and how I trusted her so much more for not hiding her true natural desires from me. I thought about calling Cheryl, but as much as I wanted her to cuckold me, I sensed she was probably, in real life, too nice, too vanilla. And I was too shy, at least with her. Somehow I couldn’t go back in time from the house of cards I had tried to build for her as the sweet Alpha male who didn’t mind taking his time. What every girl claimed they wanted until someone who could fill a pussy a lot better than me came along.

Maybe I could find a real cuckolding kind of girl again? My experience with Cheryl felt a bit like a last straw to me. Sure, a part of me would always hope to meet some nice girl who didn’t care about size, but with each experience, I felt more and more strongly that those girls were in the minority – especially amongst the cocky, outspoken and independent alpha girls I was attracted to. And deep inside, I suspected something that has proven to be alarmingly true: as I got older, the percentage of girls who would find my five inch cock fulfilling, or at least not a significant liability, would get smaller and smaller. And I was definitely right about that. It was time to face the sexual music.

I resolved that the next situation that presented itself to me, I would go ahead and also be honest about myself. After all, how could I justifiably expect honesty from the women I was trying to date if I was not honest about my own small cock shortcomings? I had seen enough now in my life to convince me that most sexually experienced women needed more than I had to offer – so why pretend otherwise?

Why not set a truthful tone from the beginning? It’s not like I was getting laid by letting the romance build anyhow, Cheryl was perfect evidence of that. Better to just be clear from the beginning. Still confident, but clear that I knew my cock was too small to make most experienced and selective pussies come. Maybe we could use toys, maybe I would just eat a lot of pussy, maybe I would let my girl be with other guys. All kinds of creative solutions might be possible.

But it was time to be honest from the get-go: my five inch cock might be nearly average by medical standards, but sex wasn’t about medical averages. In real life, my dick was way too small for almost all demanding and experienced Alpha girls. Maybe if I tried honesty from the beginning, I would get a different result.

- to be continued -

Hey folks...back in work mode, away from the story for now, but thought you might enjoy a couple of pics of a woman who has a similar build to Cheryl since her muscular body is not something you see all the time. I found some pics of a woman who looked similar, though Cheryl was taller and had shorter hair. Otherwise, a pretty good likeness.

Will try to get to another installment soon -

Jamister

Most excellent writing, Jamister. Keep up the good work. I need to go back and read in more detail.

Hello "hope to be cucked." sorry I didn't respond to your comment sooner. Thanks for the kind words, I have said it before but it really motivates me to hear from readers. I am hoping to find the time to add another installment this weekend, there is some good stuff to share if I can pull away from some social things and get on the computer.

I hope you do add another installment soon. I'm really enjoying what you've done so far. Thanks and keep it up.

Hi everyone. I just wanted to apologize for not adding a new installment for a little bit. I've been dealing with some health problems that fortunately aren't too serious but can be a challenge to deal with sometimes. I have every intention of telling the rest of my story, and the kind responses from folks like faraday and everyone else who has emailed me means a lot. Thanks.

- Jamister -

I hope you"re OK !

Thanks a lot for your story, it's nice to share it with us. I like it very much .

Get well soon Jamister. This is a great thread and its worth waiting for.

Thanks, I really appreciate the kind words. Peakmb, your patience is really appreciated and means a lot.

I'm not going to go into my health problems here but they have been a drag, and I'm not out of the woods but getting a little better. I'm pleased to report I am finally writing down the next part of my story, it feels good to put it to paper and I hope to post it soon but can't put an exact timeframe on it.

more soon -

Jamister

Hey folks….again, sorry for the delays…..I’m finally managing to find the time to get a bit more of my story done.

But before I do, I want to briefly go back to one thing since I’ve gotten a couple more emails on this. I got an email from a big-dicked cuckold who wanted to raise the point again that cuckolds come in all dick sizes. I agree with this and I won’t go into detail again as I have commented on it before. Cuckolding is ultimately a form of presentation, sometimes (though not always) involving offense, and men of all sizes can be interested in exploring their submissive side – some more intensely than others.

But here’s the thing: if I had been endowed with a big cock, I’m not sure I would have ever learned about cuckolding, except maybe as a bull. I have a pretty alpha permisterality and would have loved to have been more dominant with women if they had perceived me that way. Having a small cock kind of powerd my hand, if you will, and pushed me into cuckolding situations more often and at an earlier age. Cuckolds can come in all cock sizes, but guys with smaller dicks tend to find themselves at the “cuckold crossroads” more often and sooner. That’s not necessarily a good or bad thing, for me I would say it’s a bit of both, but what can you do but live out the hand you’ve been dealt the best you can? So for the larger cuckolds reading this, I’m not trying to exclude you, I’m just telling my story.

The other thing I want to mention is that I worry that for aspiring cuckolds, my story will give the impression that it’s easy to find cuckold relationships. I was lucky/unlucky enough to experience that early near-cuckolding in high school, and that, I think, pre-disposed me to find a couple more cuckold relationships. But they aren’t that easy to find really. I went a number of years between my first one and my second. So don’t feel bad if you find these relationships harder to find that they seem to be in this story. I will talk more about my search for cuckold relationships in a later installment.

Anyhow, continuing on…

Growing up Cuckold, Story 3, Part 3

At the time we left off, I had just had that difficult experience with Cheryl where she had fucked a bigger guy at the same party I was at, once again underscoring that what women imply they want sexually and what they really want is not always the same thing.

This part of my story is kind of hard for me to write about. It was a pretty intense time emotionally. First, there were the near-suicidal feelings I had after the thing with Cheryl. We were still friends after the party, but something had changed, at least for me. I felt us drifting apart a bit. I felt like I didn’t know where to go with my life sexually. It was easy to think of reamisters not to go on living, and when you’re young, those feelings can be pretty intense.

The next few months, I didn’t really go out much. I made a decision not to put myself out there for casual sexual situations where size was more likely to be an issue. I thought maybe in a longer term relationship I could experience the trust to be open about what I now knew was a sexual disadvantage, and I would be better appreciated for my other qualities. I had already resolved not to mislead anyone about size and to be upfront if it came to that. But I wasn’t exactly going to broadcast my size to the world either.

Bethany and I met in an odd way. My friends realized I was depressed and they encouraged me to get off the couch. I had a lot of political organizing s*******s in college, so I decided to volunteer to work on a political campaign in Boston. I’m kind of embarrassed about the naivety I had then about politics and also feel a bit self-conscious getting into detail on that part of the story here, but the bottom line is that I was getting out of the house and using my s*******s, and I soon became the leader of a small team of interns on the project.

One of the interns turned out to be Bethany. Remember that Bethany had broken up with Tom and moved to Boston to get away and start a new phase in her life. At the time I met Bethany, she was 23 and I was 25. The one thing you have to understand is that the Bethany of this part of our story was quite a bit different than the Bethany I described in her college experiences.

Bethany in college was sexually confident, but only to a point. She was reluctant to hurt people’s feelings on some level. But by 23, Bethany was very brazen sexually, extremely confident about what she wanted. Her problem, as we discussed, is that her appreciation for big dicks had made it more complicated for her to find the perfect guy. Needing “big size” along with everything else she was looking for made it hard for Bethany to find what she wanted sexually.

Bethany didn’t exactly feel the kind of despair I did at that time though. The difference between Bethany at 23 and me at 25: we were both a bit lost in terms of sex and love, but Bethany could still go out and get fucked by a big dick when she got particularly horny, whereas my little dick wasn’t getting inside of anyone. That’s how it goes sometimes for smaller guys – it’s harder to mix things up with a booty call. But Bethany decided she needed to broaden her interests beyond the club scene and that’s how she got involved in the political work.

When I got to know Bethany, she was a little heavier than she was in college and she was always a bit annoyed about that, though she was still confident in her body. I permisterally liked the way she looked, her ass was a bit bigger than she might have liked but guys often like that more rounded shape. I thought she looked amazing. We became friends from the beginning. It’s hard to put into words, but most of your readers probably know what I’m talking about when you meet someone and everything clicks, everything flows, everything is easy.

It wasn’t necessarily that we shared the same interests or anything like that. But we just had a banter from the beginning. Bethany was impressed by my confidence and she liked that I was decisive in how I led our team, but never mean to anyone. She told me later that she liked how I worked my power. I wasn’t the most powerful permister in the organization by any means, but I had that kind of young ambitious potential that she was really drawn to I guess. She told me later that she started stealing glances at my crotch to see if maybe I was the “whole package.” She never really noticed much of a bulge but didn’t rule me out at that point sexually.

But it didn’t matter, as I had already ruled Bethany out as a sex partner. She was out of my league without any doubt. I felt from the first time we talked and I heard her cocky attitude that I would have no hope of satisfying sexually. Some of you cuckolds may know what I mean. There is a certain kind of Alpha female that seems like they would only be impressed by a total stud. An actress that comes to mind who fits this bill is Jessica Biel. I think Jennifer Connelly has that, and maybe Jennifer Lopez has a bit of that also. Perhaps they are not that way in permister, but it’s hard to feel confident around that much sexual power. Bethany was like a blond Jessica Biel, and there was no way I was going to risk trying to please her sexually. The small cock experiences had accumulated at that point, denting my sexual confidence.

So I had ruled Bethany out as a lover from the beginning. That doesn’t mean I didn’t dream about fucking her. I remember one day we decided to post flyers in Harvard Square on roller skates. She wore this little white halter top that exposed her wide, perfect hips and tanned legs. I rode behind her, watching her supple legs coast confidently wherever she wanted to go. It was hardly fair. Guys would look at her and look at me jealously, assuming I was her boyfriend. And she had that way of acting really affectionate around me.

That night, I masturbated a few times, till I couldn’t come anymore. The first time I imagined fucking the hell out of her, but what really got me off was the idea of being her cuckold, watching her get dominated and totally fucked by a man who knew how to tame her and push right through her confident demeanor and make her submit totally. But I knew that was just a stupid fantasy, so after that first night I stopped reliving it – it was too painful to live just in fantasy while my celibate reality seemed to trap me further each day.

I guess my indifference to Bethany romantically made her more interested in me, I don’t know, perhaps it made me a little mysterious. That was certainly not my intention to come off as mysterious. I just didn’t know what to do with her. I did know how to be a good friend to her, and I wasn’t sure, but I felt like we were kind of falling in love. We just had a way of knowing what the other permister wanted. It wasn’t long before we were talking on the phone at night and becoming that “last permister you talk to before you go to bed” friend. I knew she was coming off a painful breakup and wasn’t really dating. At the same time, I had a hunch she would go out with her girlfriends and get fucked sometimes, because on those occasional nights she wouldn’t call me back and while she would say she went to bed early, I suspected otherwise, because I would see her friends out the next day talking about getting takes and not getting much relax.

I was starting to get so attracted to her and to feel so strongly about her that I almost sucked it up and asked her out. But then we ended up going to a Red Sox game with a bunch of our friends. After the game, I remember seeing her and her girlfriends at the far end of the bar laughing and having an obviously girl-to-girl conversation, and as I walked to the bathroom nearby them, I heard Bethany proposing a toast, and I was pretty sure she said, “to girth!” and the three other girls laughed and said, “to girth!”

I went along to the bathroom, hoping Bethany didn’t see me. When I came back out, I said goodbye to Bethany and told her I was tired. On a hunch, I walked by an hour later and peered in a window. I saw her all flirty and talking to this big, muscular black guy who I recognized as a bouncer from a club down the street. He was standing between her legs at the bar, and they were having the kind of relaxed conversation that old lovers have when they know they are going to be fucking each other later. I quickly went home, and assured myself that I would not be asking Bethany out. There was no way I could please her. On that night, she did not call me before bed. Later I learned what happened that night, but I’ll tell that part of the story later.

A few more months went by, and things continued to deepen as a friendship between Bethany and myself. I thought I felt this physical chemistry between us too, just a kind of power we would feel when we were together, drawing us like magnets even when other people were around. Sometimes we would get in these heated arguments about politics or even sports, and our friends would kind of back off and leave us alone as we yelled at each other. But unlike some lovers I have had, we would always work through the argument and end up in a close and sweet feeling of understanding.

One of those nights out, we started getting into this passionate argument, and this girl I’ll call Evie finally got fed up with us and yelled out, “Geez, why don’t you two just fuck already!” We both got kind of flushed in the face, but after that comment from Evie, something shifted further between us. It was one of those magical movie script nights, where we eventually found ourselves alone, a little buzzed, all our friends off into the night already. It seemed perfectly natural when Bethany said, “let’s go.”

That meant “let’s go back to my place,” something we had never done at the end of a night. I could feel my heart pound and I wondered to myself what the heck to do. I was reassured though, as her roommate Jackie would be there to keep the pressure off me from having to do anything physical with Bethany. Bethany was wearing this blue jean skirt with long brown boots halfway up her thighs, I could see her breast rising and falling confidently in her shirt as she walked next to me. She was a total goddess. What was I going to do?

Before I go further, I want to address one thing about my story so far. I have mentioned that I’ve had a series of girlfriends in this story who were all pretty hot sexually. That doesn’t meant that every girl I dated has been that classic hot type. Some of my better relationships were with women who were not stereotypically beautiful, in fact the woman I am seeing now fits that description, but she is plenty beautiful to me. But in those years, I was an up-and-coming guy professionally and pretty good looking and had some decent luck with the Alpha girls, and of course it was the Alpha girls that got me into the trouble we are interested in on this forum. I am going to try to find a picture of what Bethany looked like at 23 so you can see what kind of trouble I was in here.

Anyhow, when we got up to her apartment, we sat on her couch and Bethany went to get me a take. Bethany said something about Jackie being out of town for the weekend, and I thought, “Oh cuckolds brownie! How should I handle this totally hot girl?” When she sat back down, she put the movie “The Sixth Sense” in because one of our ridiculous arguments was at what point did Bruce Willis’ character realize he was dead. I was right about that, and she said something like, “I hate it when you are right, but it turns me on too. How right you are about so many things.”

With that, she straddled me on the couch and started kissing me. “Oh crap,” I thought to myself. “What I am going to do?”

But then came a moment that changed everything for me and for her. Suddenly she stopped kissing me and pulled back.

“Jamister, I don’t get it. I know you want me, but you haven’t made a pass at me in six months. You know I’ve been single this whole time. I know you’re not gay, at least I think you’re not. So what’s the problem? Do you have a small dick?”

This last part kept ringing in my head, it is still ringing years later as I type it tonight, it was like the world froze for a second. I couldn’t believe she said it. But that’s how Bethany was. So upfront. She meant it mostly as a joke. Mostly.

And here’s the interesting part. Something came over me, I have no idea what, and I just quickly and without hesitating blurted out the truth.

“Yes, Bethany, I do have a small dick.”

I couldn’t believe I had said it. As soon as I said it, I wanted to pull the words back in my mouth. As much as I had thought it would be a good idea to be upfront, it was another thing entirely to do it. But in a way, I felt relieved, even though I knew that it would mean the end of this makeout session.

Looking back on that night, Bethany told me later that what intrigued her was how open and almost brazen I was about the whole thing. If I had just stuttered and stammered out an indirect non-answer, the whole night probably would have turned into just a couple of friends getting takes and being flirty. But she felt some electricity jolt between her legs when I said “yes” so quickly and, in a bizarre way, so confidently.

Now, neither of us were very experienced cuckolds. But something shifted once again, at least for Bethany. I was too mortified to say much of anything.

“Well,” Bethany said, “I seriously doubt that. I’ll bet I can get it pretty big.” And with that, Bethany started unzipping my jeans and just running her hands in there. Her hands felt amazing on my dick and I started to bust out hard immediately. It wasn’t hard for her to get my cock out from my boxers and sticking out of my pants. As I looked down on my dick, I realized it was a little bigger than usual, and as hard as it has ever been. Maybe in that state it was five and a half inches, about the biggest it could get.

“Well, OK, Jamister.” Bethany said, as she continued to rub my cock. “You’re right, this is a small one. I can’t say I’m impressed by your dick,” Bethany went on with her kind but vulgar forthrightness (and it hurt a lot less to hear her say that while she was jacking it), “but I am impressed by your honesty. In fact, it kind of turns me on.”

And with that, she started kissing me again. What the fuck – I threw myself into it and did my best to assert my confidence and go with our chemistry. I was in uncharted territory now. When she stood up and took off her shirt, I thought I was going to die and go to heaven. Her breasts weren’t that big, but they were perfect looking to me.

- to be continued, sorry to stop here, but I should be able to post the real action in this scene soon. -

That was a wonderful post. Thank you for taking the time, particularly given your illness, to share. Your work is very psychological and simply more thoughtful than most of what we read on this topic.

oh man...ur cruel...u cant stop at this point...hurry up...

Thanks for the kind words Cuckhsbnd....

And sorry Geronimo, my intention is not to leave you or anyone hanging but unfortunately this is not as simple as whipping up a burger and fries. It is hard for me to get this done being sick and also trying to keep my work life going, but don't worry, I will keep this going, it will just take time sometime. Your patience is sincerely requested. I can't offer a time for sure but if you check back Thursday morning I hope to have the next installment ready by then.

Jamister,
For a fit man with time, that section was very, very good. For an ill man with no time it was just superb. Please don't ******* yourself for us, the great unwashed. This thread is just too good to risk. We can wait for you, it's good practice !!

Take your time, Jamister. This is one of the best stories out there - particularly notable for its thoughtfulness. Don't rush just to appease the impatient. Take care of your health and the story will take care of itself.

very good story. Thanks
Visit my blog:
http://www.konnio.com

Hey folks, I truly appreciate the outpouring of kind words. I’m in a struggling place with my health right now, so getting writing done on top of everything else is really difficult, but I think I’m heading in a better direction healthwise, and I want to keep sharing my story. I appreciate the patience and enthusiastic response, it really keeps me going, I won’t give up on doing this. So, without further delay…

Growing up Cuckold, Story 3, Part 4

Bethany and I started passionately making out and before you know it, there’s no clothes on between us at all. I didn’t know whether to be dom or sub with her and didn’t really care at that moment, it was all passion and desire and affection for this woman. I haven’t done enough to describe who Bethany was, but she was not a powerful woman in a mean way.

I always saw Bethany stand up to those in the wrong and she always had a kind thing to say to anyone. She saved her fiercest protection for those who were less fortunate than her. It was never strange to see her go up and talk to someone who was sitting alone and not fitting into a social situation. I admired her intensely and that made me want her all the more, made me so proud and happy that I would be the guy to tame her.

But could I tame her? I was so hot but still confused.

She led me by the hand to her bedroom and asked me if I had a condom, I said I didn’t and she said it didn’t matter, she was on the pill and she wanted me inside her too much to worry about anything else.

As she spread her legs for me, I could see her desire in her arched hips and she was ready to thrust. She was ready to pull me inside her. She wanted me! For a minute, I felt like that stud of my early years, about to fuck some girl’s brains out, and falling in love besides.

But then Bethany said something that surprised me. “It’s going to be interesting to fuck you,” she said to me as she pulled me closer and reached her hand down to guide me in.

“I haven’t fucked a cock this small in a pretty long time. I hope I’m not too loose for you.”

Bethany told me later she could feel my cock literally twitch in her hand when she said that. This was how it was between us – downright lusty and affectionate in one moment, and in the next moment, this searing, life-changing honesty of Bethany asserting her sexual power.

“Ohhhhh…..” I moaned as I moved inside her. It felt so good inside her. I felt no real resistance as I plunged all the way in with ease, but it still felt absolutely amazing.

“Does that feel good?” She asked me as I moved into her and back out again.

“Oh God Yes.” And it did, it felt amazing to have my cock inside of this beautiful girl, watching her arch her hips and move with my rhythm underneath me. We were kissing, holding each other, loving with that passion of two people who have been longing for someone just like the other.

“C’mon!” She suddenly said. Again, it was always like that with us. Special moments of intimacy and then right back again to aggression, with her leading the way.

“Give me everything you’ve got! Fuck that pussy as good as you can!”

Almost a teasing comment, but somehow it didn’t break the mood. This first time we fucked, Bethany was pretty careful not to totally tease and humiliate me. She didn’t know how much I could take and maybe she wasn’t used to it either, though she would grow to love it. But she and I both could sense this teasing was going on under the surface, and it was turning both of us on.

As I was fucking her so hard, going all the way in easily, feeling no resistance until my pubic bone slapped into her, I couldn’t stop thinking about the big studs who had probably been inside this pussy before me, stretching it out so well. If I had known the whole truth I have already described in the previous chapters, it would have turned me on all the more.

All the same, it was still incredibly hot being inside her. Looking down at her athletic body moving in rhythm underneath me, her strong thighs clinching my cock, and with all those hot images in my head, I found myself coming after only maybe ten minutes. That wasn’t bad, I guess, but I could usually hold out longer. I was disappointed not to be able to demonstrate my best sexual attribute.

I rolled over, a little sheepishly, but soon she was lying all wrapped up in me and we were kissing and talking and having fun, and it all felt right. Being with her always felt right.

And then she switched gears again.

“Sex is weird,” Bethany said.

“Why is that?”

“Well,” she continued, “You were just fucking me so hard and you got off so good, but I didn’t get off. It felt pretty good, but I didn’t come.”

“That’s not really fair, is it?” Bethany asked me pointedly, still skirting the issue a bit but starting to come around to total directness. I think she was skirting it only because she cared for me and we hadn’t had a breakthrough on this topic yet.

“No, it’s not fair at all,” I agreed.

“But I have a solution.”

“What”?

“Eat my pussy.” And with that, she practically shoved my head between her legs. “I hope you can eat it good, I really need to come.”

The good news for me is that I was indeed pretty s*******ed at oral sex. I was even better with my fingers, but no use telling her that now with my head shoved in her crotch.

As I worked my tongue along her clit and darted it in and out, Bethany started responding, much more intensely than she did when I was fucking her. She had to hold my head down hard with her hands to avoid bucking up too hard against me.

“Oh God!” she said. “That’s it…keep doing that, just keep doing that!”

And this is where it went up one more notch, to a place I wasn’t expecting and maybe she wasn’t either.

The next part here might seem like she was being mean to me, but all I can say to you is that it didn’t feel mean at all at the time. It felt like the most truthful thing anyone had ever said to me, at least in a long time, and there was a vulgar kindness to it. You could argue that real love is as much about truth as anything. If that’s the case, perhaps that’s why what she did next ended up feeling loving for both of us, and ultimately deepening our bond.

I think it ended up being cathartic for both of us too, a real release to have, at last, a totally honest sexual interaction, but one where there was an undercurrent of trust and affection – perhaps not present in this moment, but waiting like a net underneath us to catch us softly later.

So as Bethany got closer to orgasm, she got a little more edgy, maybe it was something about her being close to coming, and pushing my head between her legs and feeling that control over me, I don’t know, but her cockiness suddenly came out….

“Yes, eat it, keep working my clit!”

Which I did.

“Oh, yeah, make me come……!”

And then….the gamechanger that I will never, ever forget:

“Make me come like you couldn’t with your little dick!”

Oh man.

I felt my cock twitch in recognition, but I ate her that much more intensely, and I could feel the ripples of orgasm starting to build as I worked her. I could feel her bucking up against my face and so I pulled my hands behind her and lifted her even closer, feeling her round ass underneath me, and soon she was coming all over me. It was the most amazing feeling to have this powerful woman coming on me like that, scratching my head and screaming out my name. “Jamister!!!!!!!!!”

Then we were lying next to each other again.

Neither one of us smoked, but if we did, that’s when the cigarette would have been lit. We just talked about a bunch of stuff, random really, just soaking up the moment, both of us in a little disbelief about everything. Eventually her head was on my chest and I could feel her breasts up against me. It was the perfect moment. I could hear her breathing level off, she was falling arelax on me and it was like some beautiful cat curled up against me.

Then she shifted up for a second…

“Jamister?” she said, turning on my chest to face me.

“I’m sorry I called your cock ‘little.’”

“That’s ok,” I said.

“It’s really not that small,” she said reassuringly.

“No, I really appreciate your honesty,” I said. “I wish I’d been more honest in my previous relationships.”

I could see her nodding in the room, which had some lighting from the street lamps outside.

I took a deep breath…it was time to continue with the risk-taking that had gotten me this far:

“And besides,” I said, “I do have a small dick. I don’t need you to sugar coat it.”

“Oh wow,” Bethany said, suddenly wide awake again and looking up at me. “That takes a lot of guts for you to say that.”

“Well, it’s true,” I said, “and I don’t feel like hiding or apologizing for it any more.”

“No!” Bethany said. “You shouldn’t apologize. Never apologize for who you are.” And then she kind of smiled a teasing look at me I hadn’t seen before. “And you’re right, it is small. It’s a small cock.” Needless to say, I could feel my dick beginning to twitch under the covers.

“This is so different,” Bethany said, pulling me tightly against her. “I’m so used to avoiding the truth in these situations, I almost did the same thing to you just now and said what I thought you wanted to hear, instead of the truth. It feels so much better this way, don’t you think?”

“Yes,” I said, feeling relieved that all this was out in the open. I felt a flash of nervousness that other people might soon know about this conversation, but I decided to cross that bridge a later on.

“You really are a man,” Bethany said. I loved the look on her face when she said that, the respect that flashed across her face. Not desire, mind you, but definitely respect. I was her first small boyfriend that was accepting of that situation but who was also honest, clear, and somehow still confident, even if I knew my sexual limits. That’s what she was thinking anyhow. “It takes a strong man to admit where he comes up short.”

I didn’t know quite how to take that. It stung and made me feel proud all at the same time. After this first conversation, I think we both felt a lot of anticipation about where these conversations might lead us in the future. But we also realized we were worn out for the night. We fell arelax in each other’s arms.

- to be continued -

cheers mate...another great chapter....

hope ur doing well healthwise

Thanks for the kind words Geronimo...I'm still not feeling too great, unfortunately, though I'm working hard to feel better. I'm doing my best to continue this piece, I want to write it as much as some folks seem to enjoy reading it. It's funny, because even though I know how the story ended in my life, I'm still kind of suspensful about writing it, I guess I'm learning about myself as I look back. Hopefully that comes across. I'm close to finishing a new installment, hope to post it by end of weekend at the latest!

- Jamister -

Yeah this is definitely the best thread in the story section right now. We're all waiting to read more!