Becoming Melissa’s Cuckold Pt. 01

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Ağu 4, 2022 // By:analsex // No Comment

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This will be a multipart series that chronicles my descent into the cuckolding lifestyle with a girl named Melissa. Everything in these stories is absolutely true. These are my real life experiences covering my late teens and early twenties. Because these events took place over a two year period, rather than provide a strict narrative of events I will instead highlight key events during that time that symbolize turning points that lead me further down the path to cuckoldhood.


My name is Grey, I’ll withhold my last name for reasons that will become obvious as my story unfolds. I was a bit of a nerd in high school. I wasn’t really picked on or anything like that, but I was shy, kept to myself and didn’t have a lot of friends. In my graduating year I became close friends with a girl named Melissa. She grew up in the city, but her parents were going through a separation and they’d sent her to live with an aunt in the suburbs while they sorted things out. Melissa wasn’t just from the city, she was the epitome of a “big city” girl. She was mature way beyond her years, very cultured and far ahead of the rest of us in the suburbs. She was into things like art and fashion and knew about all sorts of cool underground music that none of us had ever heard of before.

Needless to say, Melissa stood out like a sore thumb in our quiet suburb and intimidated pretty much everyone. Some of the popular jock guys at school tried to pick her up, but she shot them down in a hurry. Her downtown friends were the in-crowd trendsetters, they were artists or in bands and hung out at the type of clubs that no one else could get into. There was no way that some high school football player was ever going to impress her. Melissa and I bonded over the most simple thing – people were too afraid to talk to her, and no one bothered to talk to me. We were loners for different reasons, but managed to find a connection because of that.

We became very close over during our senior year. Of course I was madly in love with her, but I knew that she was way out of my league. I was a decent looking guy, but didn’t have the confidence to match so I always considered myself to be average in every respect. Melissa was a stunner. She was petite, had blond hair and an hourglass figure topped off by breasts that only a girl that age could have and the most perfect ass I’ve ever seen in my life. I wanted more from her but knew that was never going to happen between us. I felt lucky just to be her friend.

As the school year came to an end, we started talking about the future. By then her parents had divorced and Melissa was preparing to move back to the city. She didn’t want to live with either parent and was thinking of getting a place of her own, but to make it work she’d need a roommate. I wasn’t sure what my plans were. I wanted to go to college, but I was one credit short of graduating high school. Melissa convinced me to move in with her and laid out a plan for me. She knew of an alternative school where I could go part time and get the credit that I needed to graduate and one of her friends was willing to hire me on at a printing press that he owned. She created a budget for me that showed even after paying rent and other expenses I’d have enough money for my first year of college as soon as I got the last credit that I needed. I didn’t realize it at the time, but this was an early sign of Melissa’s controlling ways when it came to me.

The first few months that we lived together was a blur for me. I got to know all of Melissa’s friends and started hanging out at all of the cool clubs. The high school nerd that I was just months ago was now walking to the front of the line at the most exclusive clubs in the city. I’ll never forget the first time that I walked passed a group of football players and cheerleaders from my high school who couldn’t get into the club that I was now a regular at. I just passed them by as I went to the front of the line and got waved in by the bouncer. The looks on their faces was priceless!

As much as I felt accepted for the first time in my life, there was always a bit of a feeling that these were Melissa’s friends – that I was who I was because of her. I was having too much fun to really be bothered by it, and I figured over time I’d make my own friends in this same circle and find my own way, while always being grateful to Melissa. I’d changed almost everything about myself – new clothes, new escort ankara haircut, new confidence and I knew I owed it all to Melissa. I’d spent my whole life feeling ‘average’ and suddenly I felt like I was somebody. I left the old version of me behind in the suburbs and discovered a new me in the city.

As much as I learned about myself during that time, I learned even more about Melissa. She was far more wild than I ever could have imagined! I knew that she liked to party, but I had no idea to what extent! She was sex, drugs and rock’n’roll personified. I’d still been holding out hope that maybe I’d have a chance with her somehow, but it became more clear than ever that was never going to happen. I didn’t judge her at all for it at all, but Melissa had a lot of men in her life. I don’t want to sidetrack from my own story, but two members of Metallica came to blows over Melissa! That’s the type of girl she was. She’d often bring guys back to our place and I’d listen to her marathon sex sessions through the thin wall that separated our bedrooms. I knew that there was no way that I could ever compete with these guys.

Which brings me to my next point. I was 19 and still a virgin. I was really embarrassed about it and kept it a secret. None of my new friends were virgins. They were as wild as Melissa was, most of them had lost their virginities long ago. And that was my problem. I’d had opportunities to get with some of the girls that I’d met through Melissa, but I was too intimidated to do anything with them. They all seemed so mature and so experienced. Literally hearing how guys fucked Melissa and hearing similar stories about our other friends, I was not only afraid that I’d be a disappointment – I was also afraid that I’d lose part of the cool new image that I’d built up for myself.

Melissa was the only one of our friends who knew that I was a virgin, and felt sorry for me. When she found out that I had a crush on her friend Victoria she hatched a plan to get the two of us together.

Victoria was a little more modest than the rest of our group and seemed a little less experienced too, she at least spoke less about the men in her life than the others did. Maybe that’s why I liked her so much, but it didn’t hurt that she was absolutely gorgeous too. Victoria was tall, brunette and had a slender model-like figure, which worked out well for her because she was a model. Before I’d met her or even knew that she as from the same city as I was, I’d seen her on billboards and poster sized ads in the subway. I couldn’t believe it when I met her – it felt like I was meeting a celebrity – and really couldn’t believe that she was more beautiful in person than she was in print. I was incredibly intimidated by Victoria, but she was a really nice girl and because of that the most approachable of Melissa’s friends. I figured that maybe her looks scared other men away or something. When we went out as a group she’d often find her way over to me and we spent a fair amount of time together and had quite a lot in common. For one thing, she was a bit of a late bloomer too.

Melissa’s plan to hook us up was pretty simple – she’d talk me up to Victoria and open her up to the idea of dating me, while also coaching me up and give me the skills that I’d need to impress Victoria.

Knowing that I was a virgin, one of Melissa’s first bits of advice was to try to control myself when I masturbated. I was at an age when I still denied that I masturbated, but Melissa was having none of that. “I bet you jerk off every time you hear me getting fucked!” Although I didn’t admit it, she was right. She taught me about ‘edging’ – masturbating to the point of orgasming, but stopping before there was a release. She told me that if I ever got with Victoria, I couldn’t be a “two pump chump” and needed to learn how to control myself. It made sense to me, and I had a tendency to do whatever Melissa told me to do anyway.

It was very embarrassing for me at the time, but for the next few weeks Melissa spent a lot of her time focused on my masturbation habits. She wanted to know when I masturbated, how often I masturbated and how long I was able to delay my orgasms for. I’ll be honest, I was a 19 year old virgin living with an overly sexual beautiful woman so I masturbated a lot! I was doing my best to work on prolonging myself, but orgasm control wasn’t the easiest thing for me to learn. Melissa kept a chart of my habits, but escort mersin I lied to her. I wasn’t honest about how many times I jerked off and I exaggerated how long I could control myself for.

During this time, Melissa was subtly warming Victoria up to the idea of going on a date with me. She didn’t come right out and say it, but was always sure to say something nice about me to her and pointed out how I wasn’t like the other guys who’d let her down in the past. We continued to go out socially as a group and I made sure to talk to Victoria, make her laugh and feel comfortable around me – all tips from Melissa’s coaching.

After a few weeks, Melissa convinced me that Victoria would say yes if I asked her out. It was the first time that I’d ever asked a girl out on a date and I was incredibly nervous. There was a band coming to town that I knew Victoria liked. I got a pair of tickets and casually mentioned to her that my ‘friend’ backed out and I needed to find someone else to go with. “I’ll go!” she said with excitement, maybe more for the band than me but it was a yes and that’s all I wanted to hear!

In the days leading up to our date, Melissa was drilling me with advice – what to do, what not to do, how to act, how not to act, where to go before the show, where to take her afterwards. It was like a crash course in dating. While I was absorbing everything that she was saying, it was also a bit of a reminder of how little I knew about dating.

As the day of our date approached, Melissa brought up the subject of orgasm control again.

“Your chart says that you can jerk it for 45 minutes without cumming now” – which was a lie – “that’s a huge improvement from when you first started”

“I’ve been focusing on getting better” – a semi lie, I’d been trying but was nowhere near that successful.

“Before I let you go out with Victoria, I need to know. I can’t let you embarrass me – or yourself for that matter.”

“Know? Know what?”

“How long you can last.”

“You do know – look at the chart, 45 minutes”

“No, I need to see it for myself”

“Are you saying that you want me to jerk off for you?”

“Yes, it’s for your own good. Even if you can wank it for 45 minutes – and we’ll see about that – you’ve never seen a naked woman before, never touched a girl, never shown anyone your dick before. All of your training is going to go out the window if you’re all nervous. Pull it out for me, show me what you can do with a woman in the room.”

“Melissa, I’m not going to do this.” I was trying hard to cover up the fact that her frank talk was giving me an erection.

“If you’re not going to do this, you’re not going out with Victoria. It’s as simple as that Grey. Don’t think I can’t call the whole thing off.”

I knew that she could.

“We’re going on a first date Melissa, we’re not going to have sex.”

“Yeah, but with everything that I’ve taught you this one date will lead to two, then three. It will happen faster than you think. I’m not going to let this get off the ground unless I’m sure that you won’t make a fool of me by cumming in your pants as soon as she touches you.”

I stood there confused, trying to think my way out of the situation.

“I can see your boner through your pants. I know that you want to jerk, just do it. Do it if you want to go on that date with Victoria. I’m going to count to 10. When I get to 10 I’m either going to see you with your dick in your hand, or I’m calling Victoria and telling her the date is off. 1…2…3…4…”

And in that moment, I made a decision that changed things forever for me. I quickly undid my pants, pulled them down and slid my hand into my boxer-shorts. I grabbed my cock and started stroking.

“Underwear too, I want to see it all.”

I was nervous, but already committed to this. I pulled down my underwear and stood naked form the waist down in front of a beautiful woman for the first time in my life. I saw a bit of a smirk and maybe a smile cross Melissa’s face as she looked at my cock – did she laugh? She looked me in the eyes and with a devilish look on her face she said “stroke”.

I stood there harder than I’d ever been and began stroking my cock with more intensity than I ever had before. I was ready to cum within seconds and struggled to distract myself. I looked down at floor knowing that if I looked at Melissa it would put me over the edge. She had no mercy.

“Look izle at me” she said and I slowly tilted my head up from the floor. Melissa was grinning ear to ear, clearly enjoying my predicament. “Tell me what you’re thinking about. Are you thinking about sliding your cock into Victoria’s tight little pussy?”

And with the image conjured up by that one sentence my cock exploded and I shot jets of cum all over the place, including on to the bottom of one of Melissa’s pant legs. I wish that I had more time to enjoy the best orgasm of my life, but I was shocked back into the moment with Melissa yelling “GET IT OFF OF ME, NOW!”

It became a bit of a comedy, me fumbling around with my pants around my ankles, hand still covered in cum trying not to touch anything and Melissa screaming at me.

“Don’t worry about your pants, get a towel and clean me the fuck up now!”

I stepped out of my jeans leaving them behind and half naked ran to the bathroom to get a towel. I came back to our living room with Melissa still standing there with a furious look on her face. I got down on my knees in front of her and began to wipe away my cum from her pants.

“The floor too, don’t let that shit stain the hardwood floors!”

With everything finally cleaned up and the towel in the wash, I sheepishly made my way back to the living room.

Melissa was now sitting on our couch with my pants and underwear at her feet. I bent over to grab them and she moved her foot on to them preventing me from picking them up. “Stand up” she said. I did, and instinctively use my hands to cover myself up.

“Do you think after a performance like that you’re ready for a woman like Victoria?”

“I hadn’t masturbated today…”, I tailed off sensing that she could tell that I was lying. “You’re making too much of this. It’s just a first date.”

“No it’s not, there’s no way you’re going out with her. I’m not going to let you embarrass me. Move your hands, I want to see your dick.”

I stood there frozen and somewhat humiliated.

“Move your fucking hands” she said with emphasis on each word.

As always, doing what she told me to do I moved my hands to my side.

“You know Victoria is a model, right?”

“Yeah…” I said not sure what she was getting at.

“I know that you’re a virgin, but I thought when you set your sights on Victoria that it meant that you had at least a decent sized cock in your pants.” Pointing at my dick, “That, that’s not enough for a woman like her. She’s not going to want that. She needs a real man’s cock, that’s a boy’s penis. Haven’t you noticed when she’s mentioned guys before that they’ve all been black?”

I hadn’t until now, but as soon as Melissa mentioned it I realized that she was right.

“I’ve spent nearly a month trying to convince her to try dating a white guy for once because I stupidly assumed that you knew what was up and had the goods. It was a challenge knowing that you were a virgin, but I was hoping that with a decent sized cock she’d have a little fun breaking you in. I can’t set her up with that” she said pointing to my penis with a sense of disgust in her voice.

All of my new found confidence that had been building up for months came crashing down around me, what was happening? I’d become aware of Melissa’s controlling side before this, but this mean streak was new to me. It was impossible to not realize that the nature of our friendship was changing in that very moment.

“Take your clothes and go to your room”

I did as I was told.

From my bedroom I heard Melissa on the phone “Hi Victoria? Good news/bad news. Grey can’t make the concert on Friday but I’ll be using his ticket. We can go together, maybe afterwards we can hit the club and pick up a couple of guys!”

I sat alone in my room trying to make sense of everything. It was a very confusing time for me. In the year or so that I’d known Melissa I went from being a suburban high school nobody to being part of the cool clique in the city. It was an incredible rebirth for me. And in the last half hour all of that felt like it had been washed away. My confidence had been replaced by insecurity – was my penis really that small? I’d never thought so but hearing it said out loud had me doubting myself. On top of that, I had no idea where my friendship with Melissa stood any more. Was she going to kick me out? Was she going to banish me from her circle of friends? Was I going to head back to the suburbs with my tail between my legs?

I barely slept that night with all of those questions running through my head, but I’d start getting answers as soon as the next day.

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