Hey everyone. I've wanted to share this story for a long time, but just haven't had the time to sit down and write it all down until recently.
At any rate, I suppose it's most accurate to say that I had my now ex-girlfriend cuckold me while we were in college. After much discussion and deliberation we decided to give it a whirl during our last year at university. We both had a kinky side we wanted to indulge, and seeing that we would likely be going separate ways after graduation, we agreed to give my wildest fantasy a try. Before I get into the meat and potatoes, I'll give you all a little background about my fantasy, myself, my ex-girlfriend, and the guy I shared her with.
My fantasy. I wanted, more than anything, to see my girlfriend have sex with another guy. And not just anyone, I wanted her to be taken by what I called an "alpha male." I always imagined her with someone taller, in better shape, and much much bigger in the pants.
I've spent a lot of time psychoanalyzing myself in hopes of understanding my desire to share my SO and watch, and I think it's the result of two things: (1) I discovered porn at a young age and (2) my very first girlfriend cheated on me with another guy and bragged to me about his size. Apparently he was much bigger than I am and the only way my brain could accept this hurtful memory was to find a way to derive pleasure out of it. Combine that with my continued consumption of porn, and you get a cuckold fantasy. At least that's my best guess.
Myself. This all happened about 3.5 years ago. I was a senior in college and had been dating my then girlfriend for a little over 2 years at this point. I'd say I was quite the nerd at the time and looked the part too - average looking, skinny, unathletic, glasses, big into video games, etc. You get the picture. I'm only about 5" down there and after literally being cuckolded once before by my very first girlfriend, I felt somewhat inferior because of my size. I felt like I wasn't good at sex and never would be.
My Girlfriend. We'll call her Hayley. Hayley is a wonderful person. She's smart, funny, has a bubbly personality, and is cute as hell. She was far too cute for me but had a nice body as you can see. Hayley was fairly vanilla in the bedroom (and so was I). She hadn't had much sexual experience before we started dating. I was the 3rd person she had sex with. Initially sex for us was missionary so we could look into each others eyes and kiss while we made love. We discovered later that she wanted nothing more than to be manhandled and roughed up a bit in bed. We experimented with everything from anal to handcuffs while we dated. It was wonderful and we fucked like rabbits the entire time we were together.
The Stud. We'll call him Sean. Sean was an acquaintance of Hayley's. The two of them had met at college orientation a few months before Hayley and I started dating. Sean was from up north and came down south for college to escape the snow. He was a pretty normal guy. He liked football, IPAs, and Call of Duty. He's 6'3 with broad shoulders, a nice beard, and a 9" dick.
Meat and Potatoes.
I'm sure you know where this is going. I watched Sean fuck Hayley several times senior year. It was both the hottest thing I have ever witnessed and the most emasculating experience of my life. Here's what happened....
I approached Hayley with my fantasy about a year before we acted on it. We had been discussing sexual fantasies one day and I reluctantly told her that I wanted to share her. She was taken aback to say the least. She felt like maybe I didn't love her if I wanted her to fuck someone else. I assured her it was quite the opposite. We discussed this topic on and off for a number of months and she never really seemed too enthused by the idea of someone new in her bed.
Finally one day I just told her that I wanted to try it. I told her this was my ultimate fantasy and I really wanted to see it realized. We had just started our last year of school and I wanted us to make the most of things before life began and we had actual responsibilities. After a long talk, she agreed to give it a try. I was thrilled. We decided that we'd start simple: we'd find a guy and she'd suck his dick while I watched.
We started talking about logistics and how we could find a guy. She was uncomfortable thinking about a stranger so we started thinking about people we knew. It was at this point I revealed something to Hayley. I told her that I didn't want to share her with just anyone - I wanted her to hook up with someone taller, in better shape, and bigger. Most definitely bigger.
That's when she mentioned Sean. I hadn't met Sean before and she had never talked about him. She told me they had a fling freshman year. Hayley was a virgin at the time and Sean was the first guy she got involved with at college. She didn't fuck him, but she almost did. Apparently she refused to have sex with him upon seeing his dick.
She thought he would hurt her, so she gave him a blowjob instead. Hearing this story from her got my mind racing. I wanted to know how big he was. Hayley didn't have a measurement for me, but she assured me "it's big."
I really wanted her to do this with someone she had some chemistry with. I wanted her to be attracted to the guy. I wanted her to want him. Sean seemed like a good candidate for that. And he was.
We agreed to approach Sean. Well, Hayley approached him. She reached out to him on Facebook and soon they were exchanging messages and decided to meet up for lunch one day and catch up.
The plan was simple: she would bluntly proposition him, and he'd either say yes or no. Easy. Hayley did her makeup and wore a low cut top that day. She trotted off to lunch after her morning class. I told her to call me after their date. We were both so nervous.
To make a long story short, Sean agreed to join us. His girlfriend had just graduated the semester before and had moved to China to teach. He was single and not looking to get tied down for his last year in college. He wanted some simple fun and the thought of getting with Hayley again excited him. Although he did (and probably still does) think I was a weirdo for wanting this.
The three of us decided to meet for drinks a brewery down the street from Hayley's apartment not long after their lunch date. Hayley wore a nice dress. Sean walked in and I was instantly intimidated by him. He was tall and all smiles. I felt small already. We talked about this and that for the first half hour, then got down to business.
Sean asked me what I wanted to see. I told him.
"I want to watch Hayley suck your dick."
A few beers later we were all back at Hayley's apartment. She told Sean to sit on the bed and the two of us went into the bathroom for a pep talk. I was so nervous at this point. My hands were clammy and I was a little shaky. We both asked each other if we still wanted to do this, and we both said yes. Hayley put on a little more lipstick, then we went back into the bedroom.
I took a seat in a chair a few feet away from Sean. Hayley walked over to him and put her hands on his thighs. They kissed a few times and then Hayley dropped to her knees. Sean looked over at me and asked if I was sure I wanted this.
"I'm sure," I said.
Sean stood up and Hayley began unbuckling his pants. I was shaking in my seat. She pulled his jeans and boxers down slowly, revealing an absolute monster of a dick. I couldn't believe he was even real. He was completely flaccid and still put me to shame. Hayley sat there grinning. She started stroking his dick with one hand. She teased him with her lips, kissing his shaft and running her tongue along its length. She sucked on his balls and stroked with her hands.
Sean's dick grew and grew as my pretty little girlfriend pleasure him with her lips. She sucked and stroked and licked and kissed his dick all over. Sean made sure to let her know she was doing a good job.
"Just like that, baby."
I sat there in amazement for 20 minutes while Hayley sucked this giant dick right in front of me. Watching her try and deepthroat this monster was insane. She couldn't get more than 2/3 of him in her mouth, but he was so impressed with her effort and enthusiasm. She seemed to be having so much fun sucking on him. She'd smile and giggle while looking up at him with those beautiful blue eyes. I couldn't look away.
Sean would have her sucking on his balls while he rested his monster across her face.
"Fuck, look at that. So pretty baby."
Or he'd tell her to sit still while he slowly thrust his cock between her pretty little lips. She'd sit there staring up at him while he fucked her mouth.
I was sitting there harder and more aroused than ever before. But I also felt so inferior. Sure, it was just a blowjob, but seeing her pleasure Sean like that made me so jealous. I felt threatened. But it was everything I wanted.
Hayley began sucking the tip of Sean's dick while stroking his shaft with both hands. Moments later I watched his dick convulse in her hands and pump her mouth full of cum. She swallowed his load, then looked up at him and smiled. Sean fell back on the bed.
I walked Sean to the door while Hayley cleaned herself up in the bathroom. He told me I was a lucky man. Said Hayley was beautiful and gave some of the best head he's ever had. I shook his hand, we both thanked each other, and then he left. That was that.
After the door closed behind him, Hayley and I had an intense make out session that lead to some steamy sex. I was still in awe of both Sean's gigantic member and the insanely hot blowjob she had just given him. Kissing her lips moments after they had been wrapped around his dick got me off faster and harder than anything ever before.
Over the coming weeks I couldn't stop telling Hayley how amazing she was to watch. That half hour is still burned into my brain and it's a memory I love to revisit.
We were both really happy with our first experience. I got to see her handle a HUGE dick and she said it was really exciting for her and made her feel very sexy.
Fortunately, it didn't end there.
I wanted Hayley to fuck him. That was a big step though. We were both nervous despite the previous experience. What if it was too far? What if we regretted it? What if it seriously hurt our relationship? We didn't know, but all the risk and the taboo was rivaled by excitement and desire. The more we talked about it, the more we discussed the blowjob, the more appealing the next step became.
There was also the physical aspect that concerned us. Well, I'd say it concerned her more, as it was a serious turn on for me - Hayley is a small person and Sean is 9". She was tight, even for me, and Sean's about twice my size. She didn't think he would fit, but she was willing to try. And it's all I could think about. She even told me her best friend, Joelle, always raved about big dicks, and Hayley was curious about the hype. A month after the blowjob she got her chance to investigate. We reached out to Sean again, and asked him if he'd like to come over and take things a little further. He agreed.
Watching Sean fuck my girlfriend was...incredible.
I'm sure it's fairly obvious already, but I'll spell it out. He's tall, confident, better than average looking, has a muscular build... basically, he's never had any trouble picking up women. Hayley had described him as a bit of a player, and he was. He had been in a fraternity at our university, and had lots of experience with girls throughout his four years. So pairing him up with my very vanilla, sexually inexperienced girlfriend was sure to be exciting for all of us.
He showed up shortly after dinner on a Friday night. I had rolled up a joint for us all to share. We sat in the living room smoking and chatting for a good 15 minutes. I was even more nervous this time. Hands clammy, shivers, mind racing. It sounds scary, but it was just this insane buildup of intense excitement.
Hayley seemed calm however. We all retreated to her bedroom and closed the door behind us. I sat in the chair again and Sean sat back on the bed. He pulled Hayley in and they started kissing. He ran his hands all over her body. He kissed down her neck, pulled off her clothes, then told her to get on her knees.
Hayley pulled his pants down and started sucking his dick and Sean just sat back and enjoyed the view. Hayley was horny. I could tell because she pulled out all the tricks for him - sucking on his balls, deepthroating, spitting on his dick. I sat there with a hand down my pants, holding my little guy while she eagerly worshipped his monster. He was loving it. And Hayley really riled him up.
Sean stood up and put Hayley on the bed. She laid back and he went down on her. He was down for there maybe 30 seconds when Hayley grabbed his head, pulled him in, and said "I'm ready."
Sean stood up and put the tip of his dick up against her, then he pushed in slowly.
I just remember seeing Hayley wince while her jaw dropped.
"Oh my god," she gasped.
It took a several minutes of very slow, shallow thrusts for Sean to start opening her up. He went a little deeper every few. Hayley would gasp at first, then get used to it. He began to pick up a little speed and get into a rhythm, giving her more and more of him. He wasn't thrusting very quickly, but Hayley was turning red.
Her pale skin always gets red blotches across her chest and face when she's having sex. She seemed to be in pain though. She was wincing, and pushed her hands against Sean's stomach, telling him to stop. He did, and that's when I realized what was happening. Hayley was having an orgasm. Sean still has his dick in her while she came. After a few deep breathes, Hayley opened her eyes, looked up at Sean and said, "holy shit!"
"More?" He said with a smirk. Hayley shook her head, yes.
Over the next half hour, I watched Sean fuck Hayley every which way. They did missionary, doggy, cowgirl, spooning (which I can't do because of my small size). And in the end I watched him pound her into the mattress, then cum deep inside her. She had several orgasms throughout, which was incredible. I've made her cum from P in V sex before, but I couldn't always get her there, and it never happened more than one time. Seeing Sean get her off so easily made me feel SO fucking inadequate and inferior.
I know that size isn't everything to everyone. Some girls like smaller dicks, some like 'em bigger. Different strokes for different folks, whatever, but that day Hayley and I discovered that big dicks are her thing. It was both exciting and humiliating at the same time. So hot to see her get off like that, but I felt so pathetic for not being the one to give her that.
Anyway, Sean left her in a state I will describe as "dick drunk." She was all happy and giddy afterword, just sprawled out on the bed and laid there for a good 20 minutes after he was done.
He didn't stick around long after he finished. I walked him to the door again, but this time it was different. I felt like we both now knew who the real man was. We both recognized my inferiority. Sean knew he gave Hayley something that I've never been able to give her, and I knew it too.
We shook hands again. We both said thank you. He left.
I went back to Hayley and got in bed with her. She was still hot and sweaty, just worn out. We laid there together for a few minutes, started kissing, and had sex.
She felt completely different. I could tell immediately how much he stretched her. It made my dick so hard and I came within a minute of entering her. I rolled over next to her, we both smiled and cuddled together.
We invited Sean over several more times before graduation and I got to see some amazing things. It's been several years now, and Hayley and I are no longer together, tho we keep in touch. I'm glad I got to experience my fantasy, but I'd be lying if it didn't come at a cost.
My self esteem and confidence took a HUGE blow by the end. I definitely have some intimacy issues, but I've been in therapy for a while now and I am getting better. The size of my dick shouldn't hold me back as a person.