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Jenna and I had been best friends for over a year. We had met in Italy while studying abroad and happened to be from the same college. So, after studying abroad ended, we returned to college as new best friends. I needed a roommate, so she got me in touch with her brother, who moved in. The three of us would hangout all the time. I spent a lot of time at Jennaâs house because her house was cooler than ours and so were her roommates. They had some parties and her friends were all cool, so we continued hanging out a lot. I was never attracted to Jenna as anything more than friends and I donât think she was sexually attracted to me, either. In fact, she had previously hooked me up with a few of her friends (stories for another day if this story is well-received).
Jenna was a bit shorter than I was, about 5â4â, probably around 130 pounds. She had a tone body from lacrosse, but wasnât super skinny, either. I never really noticed her boobs or butt before because our relationship just wasnât like that, but she had normal C-cups and a toned ass. I was 5â6â, about 140lbs. I was on the school track team so I was pretty skinny and fit, but not very muscular. It was hard for me to keep weight on, even when I tried back in high school during football season.
Anyway, one night one of Jennaâs best friends, Joanna, was having her birthday party downtown. Jennaâs brother wasnât 21, so he couldnât attend, but Jenna and I went to the party together. I knew most of the people there because Joanna and Jenna were on the same lacrosse team, so I had met most of them previously. I was also good friends with Joannaâs boyfriend, Jeff (so many people with J names!).
The party was fun, but overall, not very memorable. To be honest, I donât even remember that much of the party anymore, seeing as it was 15 years ago. After a while, Jenna asked if I was ready to head home and walk together, since we lived nearby each other, which was about a mile from downtown. I said sure, letâs go. I was also very drunk at this point. I don't know how much she had to drink, but neither of us were sober, thatâs for sure.
As we were walking home, she said, âyou can crash at my place if you want.â
I didnât think anything of the invite. It was a frigid December night so the walk was freezing. I hadnât stayed at her house before, but her house was closer than mine, so it did make sense, especially to get out of the cold asap. I figured Iâd just sleep on the couch, then in the morning walk home. No big deal. Her roommates liked me (one of which I had previously slept with; again, a story for another day, depending on the reception of this story), but I knew theyâd welcome me.
âYa, sure, good idea,â I said. âItâs fucking freezing.â
Once we got to her house, her roommates were asleep or out, so the house was dark and quiet. She said I could sleep in her bed if I wanted since itâll be warmer and more comfortable than the couch. Again, I said yes, still not thinking anything of it. After all, this is Jenna, weâre talking about. Sheâs basically my best friend, Iâm not even attracted to her physically, iâve slept with 3 of her friends, and her brother is my roommate. What could go wrong?
Little did I know that that night would change the next 3 years of my life.
Fast forward I donât know how long, but the next thing I know, weâre both naked and Iâm on top of her, fingering the shit out of her. I donât know how we got there, how long it took, who made the 1st move, nothing. All I know was, here we are, best friends, completely naked, going at it.
And I was not about to stop. No. Fucking. Way. I was having way too much fun.
And from her moans and soaking pussy, so was she.
Her pussy was so wet, my fingers were sliding in and out like somebody going down a waterslide at a waterpark. It was glorious.
Her moans were music to my ears, âOh fuck, Ian, omg. Donât stop.â
âOh, I wonât,â I obliged. âTrust me.â
âOh, thank God,â she whispered. âJust like that, right there.â
I continued playing with her tight, wet pussy, listening to her moans, still not totally sure how I got here, but also not caring.
âOh, fuck, that feels so good, please donât stop, just like that. Yes,â she continued moaning. âIâm getting so close, please donât stop. Fuck. Donât stop. Fuck.â
Her hips started bucking into my fingers as her right hand went to her breasts. She started squeezing and massaging her delightful C-cup boobs so tenderly at first, it was so hot to watch, my dick was as hard as a rock. Iâm not going to sit here and lie to yâall and say I have some 9â dick like every other guy on this subreddit has. My dick is completely average, 6â, and I have never had a single complaint, so thatâs good enough for me. I never in a million years (ok, actually just 1 year) thought Iâd be so turned on by Jenna, my best friend, but here I was.
Watching her grope her boobs as her head tilted back, eyes closed, mouth open was so hot to me, I couldnât wait to be inside of her. Later. For now, it was all about pleasing her.
After being best friends for over a year, you would think that this would be weird to hear coming out of her mouth, but either it was the booze (probably) or just how natural it felt hooking up with my best friend, I just kept going. It felt so normal, so natural, like we should have been doing this the past year. How much time and orgasms have we missed out on by not doing this sooner?! And yet, I still donât know how we got here, who made the first move, how long it took from us to close the bedroom door until I came to and was fingering her. I also didnât care. Nope, not at all. This was too awesome to overthink. Just keep going, my mind said.
Right about then, Jenna started moaning so loud I thought she was going to wake up her roommates, but I also didnât care. She started squirming so hard my fingers came dislodged from her clenching pussy just as she was whispering loudly, âoh fuck, Iâm cumming!â
Like I couldnât tell. Thanks, Captain Obvious.
I crawled down off of her and lay next to her as she lay panting, struggling to catch her breath and enunciate anything other than, âthank youâ and kissed me. I let her catch her breath and gave her some water as she recuperated for a few minutes. I was very proud of the work I had just done.
âYou are very welcome,â I replied, kissing her back, gently. âI take it you liked it?â I inquired, just to boost my self-esteem.
âIt was amazing,â she struggled to get out between breaths. âNow your turn.â
I was in no position to argue.
After catching her breath, she crawled under the blankets and started slowly kissing my neck, my shoulder, my chest, my stomach, my obliques, slowly working her way south to where I hoped she was going. She kissed the outside of my hips, down my thigh, back up the inside of my thigh, getting closer to my groin.
âUgh, stop teasing me,â I groaned.
âHehe,â she giggled, pleased with the torment she was putting me through.
Her lips slowly moved further up my inner leg, just next to my balls, and up to my rock hard shaft. Instead of stopping and kissing my dick, she moved further north, bypassing it altogether like the tease she is.
âYou tease,â I tried to say, but I donât even know it was audible to her as my breath was so heavy.
She slowly worked her mouth down via kiss after kiss until finally she kissed my impatient dick. The first kiss was so gentle, like a feather, and I squirmed. My dick flinched at the light touch.
She giggled again.âI guess you like that?â
âFuck ya!â I said, not hiding my enthusiasm.
âGood,â she said as she looked up at me and winked.
Iâm not usually one turned on my eye contact during blowjobs, but that wink killed me.
She then focused all of her attention on my long-waiting dick and put the whole thing in her mouth. Slowly. Inch by inch. No rush.
The feeling of her wet, warm mouth encompassing my hard dick felt so good I couldnât help but start moaning loudly. My moans told her to keep going, so she did.
Slowly she went up, down, up down, up, down, as if she knew thatâs exactly how I preferred it. Iâm not one for the sloppy blowjob, I prefer her to just keep it in her mouth, working it up and down while slightly twisting her mouth and using her hand to make her mouth feel longer than it is. I don't know how she knew my preference, but itâs as if she read my mind, because thatâs exactly what she did. Up w and down with the twist. Up and down with the twist. Perfect.
I then noticed her other hand was playing with her clit so she started moaning into my mouth, making it feel even better. I reached down and could just grab both of her tits in my hands and start massaging them as she kept doing the lordâs work.
Iâd love to sit here and tell you that she sucked my dick for the next hour before I finally fucked her, but Iâd be lying. The truth is, after probably 5 minutes I was getting close to cumming. I had been so turned on for so long while getting her off, I knew this wouldnât last long.
I started getting so close, so right before I was about to cum, begging her âplease donât stop, please donât stop, God Iâm close, please donât stop,â I busted the biggest nut for months right into her thirsty throat.
Apparently she didn't think I was as close as I was because she seemed a bit caught off guard, especially since I didnât ask for permission. For a fraction of a second she looked terrified or that she was about to be sick, but she quickly regained composure and was able to swallow it all, every last drop, like a pro.
Iâm sure I said something to the effect of, âoh my God, that was amazing,â but I was honestly so beat that I probably just fell asleep within 15 seconds and slept like a naked baby next to my best friend.
I had to leave early the next morning, I donât know why, but I don't remember it being awkward.
Later that morning she texted me, âumâŚdid we hook up last night? Lolâ
âYup lol,â I replied, giddily. I was still in a bit of denial and shock about what had happened, but at least things werenât awkward. To this day I still donât know how things progressed from getting into her bed to sleep as friends to coming out of my blackout butt naked on top of her, but here we are. No complaints. No regrets.
This was the first of many times Jenna and I hooked up over the next 2 years.
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