My First Time in College

I did not, by any means, have the most exciting time in college. In particular, my freshman, junior, and senior years were characterized much more by studying and school anxiety than they were with parties, belligerence, and especially encounters with the female gender. Freshman year I lived in a 'pod' with three other guys, two of whom would go on to become some of my best friends. By the time we all left to go home for that first christmas break we had cemented ourselves as a social group that would persist (plus or minus a few people over time) through graduation.

None of us were especially 'cool' by popular standards. We enjoyed video games (FIFA), playing music together, and occasionally sneaking jack daniels into the dorms to spice up our Friday nights. By the end of freshman year we were finally beginning to break into the off-campus party scene. I don't think we really fit in with many of the others at these parties, but as a group we enjoyed playing (and often winning) at the beer pong table and then venturing off into the forest behind campus for drunken adventures. That was just what we did and we were happy with it.

Sophomore year was by far the wildest of my time in college. We started to attend off campus parties much more regularly, and our little friend group grew to include a few female members which we certainly didn't complain about. Thankfully (And I don't really know how this worked), our new female friends didn't really introduce much sexual tension into the group. Frankly we really just enjoyed hanging out together.

Now, while I was not technically a virgin when I went off to college, I had essentially zero sexual experience save for a little awkward exploring that I high school girlfriend and I had done in the summer before school before we decided to break up on the grounds of being on the opposite sides of the country. It's also worth noting that while I went on a couple dates during freshman year, I had no sexual/intimate interaction for the entirety of my first year in college. It did bug me a little at the time seeing as I pictured college as one massive orgy, but before long I sort of accepted the reality of the situation. My college experience was not going to be one massive sexcapade and I was relatively okay with that.

One of the girls that frequented our group was Jenn. She more than anyone else in the group didn't really fit in. She was on the basketball team, she was a tall, attractive brunette with a very athletic body. She had sort of a tomboy feel and often dressed like a country girl rather than typical college girl fashion. And if there was anyone that us guys in the group sort of oogled over, it was Jenn, but of course Jenn had a boyfriend who was a senior at a nearby college, and not long into sophomore year she was actually engaged. Though that didn't put an end to the oogling, it certainly stamped out any hint of sexual tension that might have otherwise existed with Jenn.

So sophomore year meandered on into winter and then early spring. Our group carried on just as we always had before, however, I was beginning to feel a little funny about my relationship with Jenn. I noticed that she started sort of hovering around me at parties, always wanting to be my partner in drinking games, sitting on the couch next to me, sometimes being a little touchy when she was drunk. She wasn't blatantly coming onto me, but there was just something in the air between us that had a hint of sexual tension. This did not go unnoticed by the guys, who of course had to tease me, but hey, we all knew it was not going to go anywhere.

Everything changed one friday or saturday night in the March or April. We were all over at one of the off-campus houses for a smaller get together. If anything it was much more of a hangout than an actual party. I vividly remember that night because Jenn was drinking more than usual and becoming more touchy with me. I think it seemed a little weird to everyone (including myself) seeing as she was engaged and to be married later on in the summer, but again, we were all friends, just hanging out.

That night I went back and forth between distancing myself from Jenn and spending time with her. I was getting a stronger feeling from her that she was interested in me, but boy did that make me feel uncomfortable. At some point we all decided to call it a night and head back to the dorms. I was certainly more sober than most of my friends as we meandered the neighborhood roads back to campus. Jenn was holding onto my arm going on about something, somebody else was trying to balance a beer bottle on their head as they walked. I herded everyone back into our pod as quietly as I could and before long most everyone was passed out in their beds or a sofa. Of course Jenn was not.

I went to brushing my teeth and getting ready for bed, wondering when Jenn was going to head back to her dorm room. I even asked her if she wanted me to walk her back.

"No, I think I'll just sleep here tonight" was her reply, which (For the sake of clarity) was not weird at all. In fact, we often had people sleep over on friday or saturday night.

But that night all the sofa space was taken.

"Do you want my sleeping pad?" I asked, thinking that Jenn could just pass out on the floor and that would be the end of an otherwise awkward night.

"Sure, that'd be great" She said as she downed a glass of water.

I dug my sleeping pad out from under my bed and inflated it for her. I brought it out to the common area along with a spare blanket and one of my pillows and set it out on the floor before going to the bathroom. When I went back to my room I saw that Jenn had relocated the sleeping bad next to my bed. She was laying there, snuggled up in the blanket just looking at me.

"Is it okay if I sleep in here?" She asked

"Uhhh sure." I said, knowing in the back of my mind that this was probably letting things go too far.

I turned off the light, took off my shirt and crawled into my bed. I remember laying there, listening to Jenn breathing on the floor below me, and I remember feeling my cock harden as I thought about Jenn.

Moments later I heard the ruffling of Jenn's blanket. I saw the silhouette of her body as she stood up and slid under my covers. My mind started running one thousand miles per hour as her body found its way against mine. I could feel that she was only wearing a shorts and a bra. My cock became painfully hard, my heart was racing, I felt incredibly nervous, almost shaky.

"Is this okay?" She whispered.

"Uhhh" I had no idea what to say now, at this point my body was sold, I wanted nothing more than to keep her in that bed, but my mind was busy fighting World War 3 over this situation. After all, she was drunk and engaged. "Yeah...its okay." I said finally.

We were facing each other. I could feel her minty breath on my face and the fabric of her bra pressing up against my chest. I knew that she could feel my hardness against her groin. She and I laid there, perfectly still as if trapped in time, and then I felt her hand brush against my waist and slide down my shorts. She gently grabbed my cock and just held it in her hand.

"Is this okay?" She whispered once more, and slid herself a little closer, pressing her chest more firmly into mine.

"Yes." I said, as I soaked in that indescribable feeling of a woman's hand wrapped around my member, something that I had only experienced one or two other times in my life.

"Just tonight." she said and then pressed her lips against mine.

I had no idea what I was doing as I kissed her back, but my body switched into auto pilot. As we made out in my bed, our tongues exploring each other's mouths, my hand feeling her side, her ass, and under her bra, her hand was so very gently caressing my hard cock. I finally worked up the courage to slid my hand down her panties where I felt a shaved, swollen, and soaked pussy. Only the second pussy that I had ever touched in my life.

My inexperienced fingers explored Jenn until I finally found the spot that made Jenn moan quietly when I touched it.

"Oh fuck" she said pulling her tongue out of my mouth, "Do you have a condom?"

"Yes." I said catching my breath, "In the top drawer of my dresser." For I did actually have the wherewithal to buy a box before heading off to school.

"Good," She said as she pulled open my drawer and found the unopened box of condoms, "Take your pants off."

I did as Jenn said, as she opened the box and slid back under the sheets. I don't think Jenn had any idea of how much of a newbie I was as she took it out of the wrapper and slid it onto my dick. Seconds later, Jenn had slipped out of her panties and had removed her bra.

"What position do you want?" She asked before kissing me passionately once more.

"Whatever you want." I replied in between kisses.

Without answering, Jenn got up onto her knees and strateled herself over my cock.

I took a deep breath as Jenn lowered herself onto down and as I truly experienced the feeling of a woman's vagina enveloping my manhood. Even though it was dark, I could see Jenn's slim figure over top of me as she worked her hips up and down on my cock. Without saying a word, she took one of my hands and brought it to her pussy.

"Touch me again." She whispered.

I did. And I wanted to stay in that moment of euphoria forever as Jenn held back her moans and I felt her warm, wet, tightness sliding up and down over my cock.

Of course, I didn't last anywhere close to long for her as I was quickly overwhelmed by the sensation on my penis. She slowed as I filled the condom, my cock twitching firmly inside of her. She moved my hand out of the way and proceeded to masturbate herself, my cock still inside of her, still shooting thick strings of cum into the condom as If I hadn't cum in a decade.

It was over just as fast as it had happened. Jenn got off of me once she gave herself an orgasm and went back to the sleeping pad on the floor.

I laid there. Enveloped in a combination of disbelief, complete bliss, and a growing sense of guilt and shame. I could smell Jenn's scent in my bed, on my pillow. I felt so good and so bad all at the same time.

"That was nice." Jenn whispered from the floor with a subtle giggle in her voice.

"Yeah it was." I answered.

The next morning was awkward to say the least. Thankfully Jenn left before anyone else was awake. There was not a word about what had happened between us that night, and I was increasingly concerned that I had made a terrible mistake by sleeping with her. I took out the half empty trash that had the used condom in it, and just prayed that nothing bad would come of my choice.

I spent the rest of the day studying and watching TV with my roomates, none of whom had any idea what had happened, and were busy recovering from their hangovers. By dinner time I was feeling a little less guilty and that's when Jenn texted me.

"I think we need to talk." was all the message said.

"Well fuck." I thought.