20 year old's first fuck

[Jaegar]

Hey guys. Long time lurker; first time poster. I never really thought I'd have a story to post here..

I woke up horny this morning. It was just one of those days, you know? I was constantly checking my hookup apps on my phone while doing typical Saturday stuff. I wasn't really planning on getting any action, but it was still fun flirting with the cute guys in the area. I'm a slender white kid who just turned 20, with well-kept light brown hair, and deep blue eyes. Not to mention a respectable 7.5" endowment. I didn't have any shortage of guys who would play the flirting game with me. Eventually, though, I had a 27 year old dude send me a quick series of messages that managed to amuse me, intrigue me, and turn me on.

"Hi!"

"Omigosh, you're so hot.."

"Can I suck you, please?"

"Seriously, I'll pay you.."

Flattered, and feeling a bit bad for the smaller, feminine guy of slight frame that I saw in his pictures, I responded that I was interested. I figured that he just hadn't gotten any in awhile, and just needed a bit of dick to take the edge off his hunger. Besides, he wasn't too bad looking, and I like femmes pretty well. Not seriously entertaining the thought of taking his money, I accepted his initial offer ($50) without argument.

We kept on talking, and made our arrangements. He asked me to meet him at his apartment in the next town over an hour later, to which I agreed. I got showered, combed my hair out, put on a tight fitting shirt, shorts, and Steve Madden's over my ankle socks, and got in my car to drive over. While on the road, I made a note to remember to bring a condom inside when I got there. I had plans to "save myself" for when I wanted to mount that special boy, but better safe than sorry, right?

I got there in about 15 minutes or so, and parked my car. While walking to his apartment's entrance, I called up as he had asked, and he said he would be right down. I waited patiently, shooting the shit with a Domino's delivery guy who was also waiting to be let in. Within a few minutes, the dude came down, and it was one of those "aw fuck, he posted his flattering pictures" moments. The thing about times like those is you have to make a judgement call real quick. Do you want to go through the awkward moment of calling it off, and making some kind of excuse? Are you horny enough that it's not too big a deal? Are you disappointed, but don't want to have come all that way for nothing? I went with the latter option, and greeted the guy while trying to mask a bit of disappointment.

We headed back to the elevators, and up to his room, introducing ourselves in person for the first time. He had both of his roommates out for the evening, so we had the place to ourselves. He offered me water, asked if the temperature was fine, and asked if I wanted to watch anything on the TV in his room (including porn). He seemed a bit nervous, but was obviously trying to be a good host, which I appreciated. We watched one of the world cup games in his room for a bit, with him at his desk and me lounging on his bed. We talked about the area, weather, general small stuff. Then we turned to talk of cocks, guys, etc. We discussed sexual positions as well. He said that he was pretty much a bottom, but didn't expect he could take a cock like mine. Nodding, I said I was inexperienced, but knew I'd end up topping. He nodded, too. He admitted to being very horny, and I hadn't gotten off all day, so we were both ready to begin.

I kicked off my shoes, while he slipped off his flip flops. I undid my shorts, and slid off my socks while he dropped his shorts. I quickly rolled over then, to put my keys, phone, and condom on his side table. With me lying on the bed, he grabbed the bottom hems of my shorts and pulled them off my shaved-smooth legs. He began to heft and feel my sizable package through my boxer briefs then, while I slid my t-shirt off over my head. He quickly rolled over to my side for a moment then, and shimmied out of his boxers, then taking his tank top off, throwing them both off the side of the bed. He then went to straddle my legs, and peeled my tight underwear back, allowing my seven inches to spring free, then flop against my stomach. Fixated on my sizable length, he quickly pulled my underwear down to my ankles and off my feet.

With both of us naked on his bed, then, I began to appreciate the size difference between us. I weighed a good 150lbs, while this guy might be 100 sopping wet. I stood at 5'11", and he must be around 10 inches below that. Finally, while my turgid member had several inches in length, I'd be surprised if his was more than 5".

At the base of his bed, he slightly spread my legs then, so that he could crawl between them and begin to lap on my cock a bit. It had been a good while since I'd gotten a BJ, and I lightly gasped at the sweet sensations. As he began to engulf more of my cock in his mouth, I began to get more into it. I lightly caressed and rubbed his sides and shoulders, physically encouraging his efforts. He moved further down my dick then, and moved his body further between my smooth thighs to give himself leverage. Enjoying the sensual body-to-body contact, I brought my legs in around his, enjoying feeling my calves on his, my feet on his. With the setting sun shining through the window onto his bed and our intertwined naked bodies, I had the brief thought of "thank goodness I'm gay."

He came up for air after a solid effort with my member, and we engaged in lighter foreplay. He tweaked my nipples, and rubbed my pecs, while I ran my hands up and down his back. We both brought our faces closer then, and shared a very wet kiss. I noticed when we pulled away, that he had moved his hands to my thighs, and was pushing them apart quite firmly. I could now feel the tip of his cock prodding at my crack as well. Before I could continue to process this he brought his mouth back down over my cock, resuming his efforts.

He bobbed up and down more fervently now, running his tongue quickly up and down my shaft. I let out light moans of appreciation for his surprising expertise, spreading my thighs ever further to grant him better access. He interpreted this differently, however, and while continuing to suck me, brought one hand down below my balls to tease the smooth entrance to my now-exposed hole. Somewhat uneasy now, but still enjoying the oral attentions, I allowed him to continue. I quickly began to enjoy it, to be honest, and gently bucked my hips against his hand. He shifted his body then, and began giving me a handjob, while he sat upright between my wide open legs. He stopped teasing my hole with his hand then, and instead used it to gently rub his cock head up and down my crack.

He continued that way for awhile, and he smirked at me as I continued to gently buck my hips, now against the probing head of his cock. The developments of my situation were certainly not lost on me. I hadn't expected this smaller, stereotypically sissy fellow to make a play like this. He had desperately wanted to suck my dick, even offering money to do so, and even said he was a bottom. Pretty much. What confused me more was that I was enjoying his attentions. Wasn't I supposed to be a top? Something he said interrupted my train of thought.

"Huh?" I asked, not hearing what he said.

"I asked if you wanted me to fuck you." He stated confidently, still smirking, still pumping my cock and probing my hole, a mischievous look in his eyes.

"Please." I simply stated, and I knew I said it with a note of pleading in my voice and a blush on my cheeks.

Without another word, he climbed from between my legs to his night stand, looking for his lube in the drawer there. Thoughts drifted through my head of "this is your virginity," and "really? him?" But I knew what I wanted, and I wasn't turning back. I also noticed he hadn't retrieved a condom from his drawer, and while glancing over at mine resting on top of the table, I somehow didn't think to ask him to wear mine.

He returned between my legs then, purposefully spreading my thighs once more. I timidly watched as he squirted some lube into his hand, which he rubbed up and down my crack, and around my hole. While I gasped at the cool feeling of the foreign fluid, he squirted a bit more into his hand, which he rubbed up and down his modest length. He then used his hand to guide his cock to my tight, virgin pucker, and looked me in the eyes, that mischievous look still present.

"Ready?" He asked.

I nodded.

He shoved.

After a few seconds of firm pressure, his head gained entry, soon followed by the firm few inches of his shaft, until he had wholly penetrated me. My face flushed at the new sensations, and I gasped lightly as I felt his member begin to gently pulse within me. I could feel him so well. The tip of his cock on my inner walls, his balls resting against my crack, his stomach and mine sandwiching my now-neglected cock between them, my arms gently dangling from around his neck, and our legs still intertwined.

"You okay?" He asked, looking down into my eyes.

"Uh-huh." I affirmed, looking meekly up into his.

He began to smirk again then, and resumed bucking his hips once more, now his length pumping in and out of me. He was good, and he lasted a good while. Time and again he managed to make me gently coo with pleasure as his cock reached my sweet spot. I gently bucked my hips in time with his movements, coming to enjoy my more abstract role. I rubbed his shoulders encouragingly, and wrapped my legs around his waist, bringing them in in-time with his thrusts. As he pumped away, I began to ponder my budding role as a bottom. I thought of the defeated Kings of old, sodomized in front of their former subjects, so as to make women of them. I thought of the Greek and Roman youths pursued by the aristocracy, and young British sailors, subjected to the attentions of the senior Seamen. As he continued to buck and thrust, and I let light moans of approval escape my lips, I decided that I was quite happy to be among history's ranks of penetrated men.

Soon enough, his breaths became more heavy, and he began to pump in and out of my ass quicker and quicker. Suddenly, he seized up, and gave out a low moan. I could feel his cum slowly dripping out between his softening cock and the edge of my hole. He rolled off to the side of me then, and gave me a calm, confident look.

"I came inside you." He stated with purpose.

"I know." I nodded once more.

We lazed around naked on his bed for awhile longer, engaging in a bit of pillow talk. His lust sated, he talked about his job, asked about my job, what I was going to school for, other such things. I was happy to contribute to the conversation, but gave a light frown while glancing down at my fading erection, which had never been allowed to climax. He invited me out to dinner, but having already eaten I politely declined.

As we both stood up to get dressed, he opened his wallet, and with a grin tossed $55 to my side of the bed. I sheepishly returned his grin, and his money. Surprised, he accepted it back, but asked why I didn't take it. I shrugged, and explained I was just into the fantasy of it. He seemed to nod with understanding as he saw me out the door, wishing me a "Happy Pride" as he saw me off.

I walked back to my car, then. A noticeable twinge felt between my legs as I walked.

[tomsawyer]

I know this is old but I just saw this post for the first time and it's really hot.  Thanks for sharing your virginity with us.

[slowfuck]

Superbly written account. Just how it happens (happened) and carried the 20-year-old me along for the ride in my mind too. I especially loved the bit: "I came inside you." He stated with purpose. "I know." I nodded once more. Clearly you turned him on so much and he was proud of his bottom-becomes-top achievement! Have fun, Jaegar.

[Chipperoo9]

Wow that was hot!!