After six years I finally slept with [m-20]y best [f-19]riend's cousin. | 2016

I've been best friends with John since we were in the 6th grade. All throughout middle school we were inseparable. We were great friends in high school too. I was practically part of his family and he was practically part of mine. It was downright annoying how good friends we were. One of the main differences between us was that he was a serial monogamist and I was not. I don't recall a time when he didn't have a girlfriend. I'd hook up with people but I wasn't really into relationships at such a young age. John's family fed directly into our high school, and he had a cousin who was one year younger than us named Jessica. I met Jessica during our sophomore year of high school when she was a freshman. We didn't talk that much except at the occasional family gathering where I went as John's guest. I rarely saw her if at all.

Fast forward to my senior year of high school of high school- it's John's graduation party. They had rented out a nice place and John was swimming in attention and gifts (his family came from a good amount of money). Jessica is there and we hadn't spoken in two years. I almost forgot what she looked like. The short, awkward girl I was awkwardly talking to four years ago had grown up, and I immediately thought she was attractive. Still, she was my best friend's cousin. I can't do anything with this girl. I don't want to risk my friendship over a one time lay. At the end of the party she comes up and me and starts talking. Holy shit, this girl is flirting with me! She's touching my arm, laughing at my shitty jokes- it's downright obvious. The next day I get a text Hey, it's Jessica! I got your number from John. We should get coffee sometime over the summer. I agree and we set up a date for the next week.

I walk into the coffee shop I've been in a million times before and I can't find her. She had found two chairs in the corner behind a wall- talk about being weird. I order my drink, ask her if she wants anything- she doesn't- and sit down next to her. Jessica proceeds to basically profess how much she likes me and how she wants a relationship and everything. I say that I can't. I'm moving in three months, she's staying in town. Her cousin is my best friend. I know the family too well. It would be too awkward if things didn't work out. Everything told me to say no, so I did. She was sad but still understood why. She asked that we start talking just as friends- her hanging on for hope- I agreed. I don't know why I did. She was attractive, but I know I shouldn't have accepted. This got the ball rolling for what happened next.

She texted me almost every day over the summer. We met for coffee one more time before I left for college. We live in a big, east coast (American) city. I was going to a large, private school about two hours away and John was going to state school about five hours north. Still, I don't come back to town until Thanksgiving and John ends up staying up at his campus because he only had school for a week after Thanksgiving for winter break. To my surprise, I still get an invitation to John's family Thanksgiving dinner. I had gone several times before- but never by myself. I later learned this was Jessica's doing. I show up, it's a formal event, so I'm in a suit and tie. Everyone looks great. Jessica walks in and HOLY SHIT SHE IS HOT. I don't know what happened over the course of six months but she had turned form cute high school girl to stunner. She was about 5'6" (wearing a crazy pair of heels which almost made her as tall as me at 6'), 110 pounds-skinny (I have a stocky build- about 220 pounds, so nothing like her here). Long, straight, brunette hair, an average pair of perky boobs, and a body/ass that would make you sing. Her legs/ass looked spectacular in her dress and heels. I had no idea how she could be that skinny and still have those curves. I wanted to grab her and fuck her right there on the table. She could see that I liked what I saw, and guess what? Her high school crush on me was still there. Jackpot.

After dinner everyone moved to the living room to watch football and talk. I sat on the couch with Jessica and she told her parents I was telling her about college. They left us alone. Thank God John wasn't there or else this next part wouldn't have happened. We're talking and she straight up asks "do you want to have sex with me?" My jaw drops. I respond "of course I want to, but I can't. Your family and your cousin and everything. I just can't." She's disappointed. I lean in, kiss her, and then back up. She was burning inside. She wanted me so badly. And guess what? I wanted her too. I come back three weeks later for winter break and John, Jessica, and I spend some time together. There's obviously some tension between Jessica and I and John notices. He tells me when she's not there "dude, I totally think that Jessie has something for you. Isn't that hilarious?" So at this point he knows at least her side- but none of mine. I'm nonchalant about it, saying "Yeah, crazy." I go back to college and so does John. Jessica keeps texting me, and our conversations are getting racier and racier. She asks me if I want nudes- and one night I say yes. I get them and her ass looks great. Her boobs were so perky. She looks like nobody has ever touched her before: so pristine. I eventually ask if she's ever had sex before. She tells me that she broke up with her boyfriend of two years a month ago and they had sex often. I'm happy- this is a girl who probably knows what she's doing. Now I only had to make my move.

Jessica, for reasons beside me being there, applied to and was accepted to the university I attend. She organized a visit up to campus in April and would stay with me in my apartment. I totally knew that this was my shot. I told my roommate that a girl was coming over and he knew what was up. It's in the afternoon on a Friday and Jessica knocks on my door. It's a hot day so she's wearing a low cut top and tight shorts that are driving me crazy. Her legs and ass are on fire. My roommate said he was going to go study, and left us after saying hello to Jessica. I move her into my room, tell her she has the bed, and she suggests we share it. We're sitting on the bed and I say "remember what you asked me at Thanksgiving?" she responds, "How could I forget?". I say, "well, this is my real answer." I lean in and kiss her. The kiss turns into a sloppy make out. She practically tackles me and she's on top of my on the bed. I immediately become hard. I've wanted this for almost two years at this point. It's the perfect amount of forbidden. Bad enough to where I shouldn't be doing it- so it feels great. But not so bad that I feel guilty afterward. After she gets on top I start thrusting my now hard cock up so she can feel me. She pulls up and hops off, undoes my belt and my shorts, and my cock springs up and almost hits her in the face. She looks at me with her dark, blue eyes and takes me into her mouth.

In all honesty, the blowjob wasn't that great. She was going slow and not licking very much, but I didn't care. The fantasy that had built up in my mind for so long was finally happening. After two the three minutes I pulled out and said I wanted to have sex with her right here and now. She smiled and undressed completely. So did I. She said she wanted to start out on top so I lied down and she straddled me. I put on a condom and then she slowly inserted me inside of her. Oh my god she was so tight. She started grinding back and forth and it felt amazing. She wasn't very loud at all. A quiet moan or gasp was all she made every time I thrusted into her. But really, that was all that I needed. After going like that, she hopped off and I said I wanted doggy. I needed to see and feel that amazing ass I had been marveling at for so long. This was where we both lost it completely. I lasted maybe another two minutes and she started audibly moaning. I thrusted deep inside of her and shot my load into the condom. I fell down on top of her and we started making out again. This next part was mind blowing. She pulled the condom off my dick and squeezed my hot cum into her mouth. She swallowed the whole thing. Holy shit. I had no idea she would be like that. The mild mannered, rich prep girl from the nice family whom I had known since she was a middle schooler wouldn't have done that. She wanted me badly and now that she had me she would do anything. We spend the next three hours in bed. Kissing, talking, blowing me, fucking again. By the end of weekend neither of us could walk straight. She toured campus and left on Sunday, kissing me goodbye.

She ended up staying in our hometown for college, which means that I get an amazing hook up every time I go back home. John and I are still friends and because he's always at his campus he doesn't know. Jessica and I have a system of not being with each other when he's around except at formal functions where we won't have much contact anyway. If I'm being honest, through talking to her I've started to like her. I don't know what I'm going to do with those feelings but she's told me she feels the same way. For now we'll keep fucking, but I think one day we'll be in a relationship. John always joked that we'd be actual family one day, maybe this is my shot.