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 Jenna’s 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 don’t 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 5’4”, probably around 130 pounds. She had a tone body from lacrosse, but wasn’t super skinny, either. I never really noticed her boobs or butt before because our relationship just wasn’t like that, but she had normal C-cups and a toned ass. I was 5’6”, 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 Jenna’s best friends, Joanna, was having her birthday party downtown. Jenna’s brother wasn’t 21, so he couldn’t 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 Joanna’s boyfriend, Jeff (so many people with J names!).

The party was fun, but overall, not very memorable. To be honest, I don’t 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, let’s 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, that’s for sure.

As we were walking home, she said, “you can crash at my place if you want.”

I didn’t think anything of the invite. It was a frigid December night so the walk was freezing. I hadn’t 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 I’d 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 they’d welcome me.

“Ya, sure, good idea,” I said. “It’s fucking freezing.”

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 it’ll be warmer and more comfortable than the couch. Again, I said yes, still not thinking anything of it. After all, this is Jenna, we’re talking about. She’s basically my best friend, I’m not even attracted to her physically, i’ve 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 don’t know how long, but the next thing I know, we’re both naked and I’m on top of her, fingering the shit out of her. I don’t 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, “Oh fuck, Ian, omg. Don’t stop.”

“Oh, I won’t,” I obliged. “Trust me.”

“Oh, thank God,” she whispered. “Just like that, right there.”

I continued playing with her tight, wet pussy, listening to her moans, still not totally sure how I got here, but also not caring.

“Oh, fuck, that feels so good, please don’t stop, just like that. Yes,” she continued moaning. “I’m getting so close, please don’t stop. Fuck. Don’t stop. Fuck.”

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. I’m not going to sit here and lie to y’all and say I have some 9” dick like every other guy on this subreddit has. My dick is completely average, 6”, and I have never had a single complaint, so that’s good enough for me. I never in a million years (ok, actually just 1 year) thought I’d 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 couldn’t 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 don’t 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 didn’t 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 didn’t care. She started squirming so hard my fingers came dislodged from her clenching pussy just as she was whispering loudly, “oh fuck, I’m cumming!”

Like I couldn’t 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, “thank you” 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.

“You are very welcome,” I replied, kissing her back, gently. “I take it you liked it?” I inquired, just to boost my self-esteem.

“It was amazing,” she struggled to get out between breaths. “Now your turn.”

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.

“Ugh, stop teasing me,” I groaned.

“Hehe,” 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.

“You tease,” I tried to say, but I don’t 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.”I guess you like that?”

“Fuck ya!” I said, not hiding my enthusiasm.

“Good,” she said as she looked up at me and winked.

I’m 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 couldn’t 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 that’s exactly how I preferred it. I’m 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 it’s as if she read my mind, because that’s 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 lord’s work.

I’d love to sit here and tell you that she sucked my dick for the next hour before I finally fucked her, but I’d 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 wouldn’t last long.

I started getting so close, so right before I was about to cum, begging her “please don’t stop, please don’t stop, God I’m close, please don’t stop,” 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 didn’t 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.

I’m sure I said something to the effect of, “oh my God, that was amazing,” 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 don’t know why, but I don't remember it being awkward.

Later that morning she texted me, “um…did we hook up last night? Lol”

“Yup lol,” I replied, giddily. I was still in a bit of denial and shock about what had happened, but at least things weren’t awkward. To this day I still don’t 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.