Once Upon a (First) Time

If you are gay study hard. You really want to go to college. Preferably far away from home. And to do that you need good scores on your SATs, some advanced courses, projects under your belt. Good references from your high school teachers. And it helps if you play an instrument or can paint or dance or play a sport. Although I never had trouble at home, high school was tough but I got excellent grades and made it to my first choice of college. As a gay kid and a bottom this was my chance to explore. I'd never had sex till then but had known from my early teens that I was gay. I was never flamboyantly so as I came from a small town.

So one day at college I was headed back to the library when I walked past one of the grounds. And there was this stunner doing training for track. I couldn't help but stop and watch him train. He was tall, square features, a light beard, and had strong muscular arms and legs. The next few days I walked by the grounds and sure enough he'd be there training. I'd slow down to enjoy the view. By the time I'd return from the library the training was over so I normally only saw him once a day.

One day as I walked to the library he wasn't training. I wondered why and continued on my way. As I entered the library I saw him standing by the reference section looking dumbfounded. I mustered up the courage and walked up to him and said something cheesy like "Hey, the grounds are that way! I see you training every day." He just grinned and said "I got this political philosophy assignment due. Do you know something about the ancient Greeks?"

You see he was there on a sports scholarship and needed to maintain a passable average to keep it. While I didn't know much about the ancient Greeks, I did know a lot more than he did. And knowing how a library worked I took him to the right section. Helped him pick out a few books. And we went through them a bit and got an outline for his paper ready. He really wasn't a 'dumb jock'. He picked up on ideas super fast once he had some context. We exchanged numbers and he thanked me for my help.

A few days later I got a snap from him. He had gotten a B+ on his pol philosophy assignment. That's the most he had ever gotten. On any assignment. Ever. After that we starting messaging regularly and started becoming friends.

He came from a small town as I did but that's where the similarities ended. My parents were white collar professionals. His dad drove a cab and did odd jobs while his mom was a store clerk. My parents were agnostic when it came to religion. His were pretty keen on the big G. He was the first person in his extended family to go to college - pretty much all my family were college educated. I was one of two kids - he had five siblings all younger than him. One thing I did pick up on was that he never mentioned girlfriends. He also didn't seem to have one now. This was odd for a sportsman at college.

After several weeks my college roommate was going out of town. So I ask my friend over for a study session. We'd gotten really close to each other and I felt like telling him how I felt.

When he came over I was in my usual shorts and a sleeveless T. He could see that I was smooth and shaved. He greeted me and we sat down on the bed. I was thinking of how to move this in the direction I wanted when he casually grabbed my hand and squeezed it. When I didn't pull away, he looked straight into my eyes and kissed me on the lips. I kissed him back and we began making out on the bed. He was a hunky 6 feet tall guy and I was slender and five inches shorter than him so soon he was on top of me. I could feel his bulge through his jeans.

I reached around him and pulled his shirt up. He broke our embrace for just a second to get his shirt off. He took off my shirt and soon were rolling around the bed in each other's arms. I took my shorts off to be fully naked under him and he unbuckled his belt and allowed me to push his pants down. He then got up for a second and took everything off.

I was simply mesmerised by his cock. It was so much thicker than mine and longer too. You can watch lots of porn but it doesn't prepare you for the first time you actually have a cock in front of you. It was the most beautiful thing I had ever seen.

He sat back onto the bed and I dropped to the floor on my knees. I tried to take his cock in my mouth but it wasn't easy and I worried about hurting him with my teeth. So after some virgin fumbling I settled on sucking the tip of his cock while holding his shaft and gently stroking it with my hands.

He started to really enjoy this and caressed the back of my head and neck as I tried my best to give a real blow job for the first time. Sure, I had practiced on condom covered cucumbers before but an actual penis is so much warmer and more alive. The penetration is so much more enjoyable when it is a real cock in your mouth.

After some time my jaws started to hurt and it didn't look like I would be able to make him cum through oral. He noticed my discomfort and gently told me to lie on the bed. I lay down on my stomach while he put on a condom and lubed up.

I had done a decent amount of anal masturbation and it was my go-to method for cumming. But I had never had something so big inside me. The thickness worried me. But I was eager for him to fuck my ass. I asked him to be gentle since this was my first time for real.

He took a lot of lube and rubbed it into my crack. He then stuck one finger inside. Then two. Then three. After getting me ready he climbed on top of me and spread my legs. I arched a bit to give him better access. And then he began to enter me.

The head went in easily. So did the first few inches. But after than the thickness of his cock made it painful. The walls of my boy pussy strained to accommodate him. He slowed down and gave me time to adjust. Even so it hurt for several minutes. I moaned and he kissed and caressed me and comforted me. As the pain slowly decreased I started to relax and nodded. He now pushed the rest of his cock steadily into me. I gasped and moaned as now he didn't pause but kept going till he was all in. I felt his balls against my ass cheeks and realised he was fully inside me.

This was the start of the fucking I was to receive. He gradually pulled out and pushed all the way in. Now my hole gave way easily. And so he started to increase his pace. I felt a bit of a burning sensation as he thrust rapidly and a dull pain. At the same time I felt full and complete and my prostate was getting pounded, which was extremely pleasurable. I wanted it to be over but I also wanted it to continue.

As he got closer to orgasm he began moaning and tensed up. Then he groaned as he came and his body relaxed as he covered me like a blanket. He lay there on top of my for several minutes as his cock lost its hardness and eased out of my aching hole. I whimpered and moaned underneath him completely helpless and submissive.

After lying together in this way, he rolled over the side and I embraced him putting my head on his chest as his arm went around my shoulders. My ass was sore and I hadn't cum. But I felt happy and content. I had lost my virginity and made another man cum. We didn't say anything to each other and both fell asleep. When I work up an hour later he was still asleep. So I climbed out of bed and went to clean myself up. As I wiped my ass to clean out the lube I noticed a small amount of pink - it seems I had bled a little from the penetration. So I truly felt deflowered.