My First Time

I'm like most average nineteen-year-old guys. Struggling to find a job, trying to get into school, that sort of thing. I also suffer from Bipolar Disorder, and when on and off my meds for varying degrees and reasons, I tend to get extremely horny. This eventually eclipsed over one weekend until, eventually, I could take it no more. I was jacking off three times a day and getting no relief, so when my roommates decided to take a post-wedding honeymoon trip and were leaving me alone for nearly a week, I decided to take the opportunity to try something I'd never tried before.

Online hookups.

I was a bit nervous about the whole thing. Being a virgin, but being extremely horny and with little chance of getting laid by the guy whom I'd met at the club, I decided to venture forth and leave my lesser inhibitions behind. I was horny, REALLY horny, and with my roommates gone it gave me the chance to experiment without having to worry about getting negative or one-sided attention from them.

With that being said, I started pursuing Adam4Adam and a few other sites with the intention of getting laid. I had a few things arranged, but all fell through because the guys didn't show up. One even didn't want to fuck me because I was a virgin, and at that point I was getting so sexually frustrated that I was reaching out to guys who normally bottomed to top.

Come Wednesday the tenth, however, things changed.

I got messaged by a guy who asked the general 'how things were going. 'Things eventually escalated from there. He asked what I wanted to do, I said I wanted to get plowed, he said he wanted me to suck his dick and turn me around and fuck my ass, and in little more than a half-hour I had a hookup arranged. After all this time, I was finally going to get what I wanted—a nice big dick in my mouth and one up my ass.

After getting ready for the sex, which included cleaning and stretching myself out, I got in my car and drove to the dude's house.

I wasn't sure what to expect.

I sure wasn't expecting him to be so forward.

Upon entering the house, he immediately led me to his office after asking if I was horny, where things had already been prepared and ready. A blanket was spread out on the floor, a box of sex toys and instruments was in the corner, and porn was playing on the computer. Stroking his cock through his pants, giving me the eye, I instantaneously knew things were going to go fast. That was when he asked me to get on my knees.

I was ready for this.

Online, he listed his cock as seven-and-a-half inches, and being the virgin and as inexperienced as I was, I wasn't sure what to expect. However, when the guy lifted his shorts up his one leg and pulled his cock out, I was instantly sure that he'd misjudged his size because it seemed A LOT bigger than seven-and-a-half inches. It was thick, too, and the sight of it alone was enough to stir my cock in my pants.

I needed no encouragement.

I went down.

His cock tasted amazing. Thick, salty, and more than a mouthful, I concentrated on sucking the head and the first few inches of it while he continued to watch porn above me. I stroked his massive dick below my mouth as he set his hand on my shoulder and started to massage my shoulderblade. I was instantly turned on not only by the length in my mouth, but by his attentiveness, so I continued to bob up and down on it as though my life depended on it. Eventually, after a while, he tilted my head to one side and pushed the head of his cock to the side of my cheek. At this point, I ran my tongue along the underside and around the thick mushroom head and started slurping up and down on it, using as much spit as possible and awaiting further instruction from the man I was waiting to dominate me.

After about five minutes, he slipped his shirt off his head, then stood, pulled his shorts down, and shoved his cock in my mouth. He then began to facefuck me, going slow at first, then speeding up before he sat back down in his office chair. I followed him all the way, sucking the head and going down on the length, before he asked me to deepthroat him.

I tried my best and failed to do it.

He helped me by shoving my head down on his dick.

I managed to get all seven-and-a-half/eight inches into my throat, but was gagging a little bit because I'd never done anything like this before. He took this as a sign and let me go slow, taking my time, and I eventually began to deepthroat him again on my own. He started to fuck my mouth, pumping his hips up and down off the chair, for about two minutes before he leaned forward and started stroking my cock. At this point, I was sucking on the head, running my tongue along the shaft as he continued to fondle and stroke my cock.

At this point, he asked me to take my clothes off.

I complied.

He crossed the room, pulled a collar from his chest, and put it around my neck before he tied a rope contraption around my balls and dick.

At his mercy, I went back down on his cock.

The deep-throating, sucking went on for several more minutes before he leaned forward, grabbed his lube and started to massage it into my hole, which immediately started to pulse as his fingers were there.

Apparently, after he got a feel of my virgin ass, he had enough of the sucking.

He asked me to get on the blanket spread out along the floor and spread my legs.

I said I had condoms.

He said he had them instead—which was probably a good thing, considering mine probably wouldn't have fit his cock.

He got behind me, slid a condom over his massive cock, and slid what I assumed were a few fingers into my ass. I groaned, surprised at the thickness and length, then moaned, 'Fuck.' After a moment, I realized something.

I asked, 'Is that your cock?'

The guy groaned, 'Yes.'

My ass immediately contracted along his thick length.

He took it slow, realizing I was new to the anal play, and slid in and out in slow, gentle strokes, the head and length of his cock sliding along my prostate and stimulating my cock. After a while, he started to increase his pace, which, so early on in the fucking, was discomforting.

I asked him to slow down.

He asked me to get on my back.

I complied.

After lifting my legs into the air and propping them on his shoulders, he slid his cock back into me and began to fuck me with the same gentle pace. At this point, I was starting to get used to his cock and asked him to speed up, which he immediately complied to by leaning forward, pressing out chests together, and lifting my ass into the air to meet his hips as he began his harder, faster thrusts.

Moaning and obviously enjoyed it, he asked me to jerk off.

While he fucked me, and while I jerked off, he commented that I was leaking like a fire hose and laughed just as he went down and started dragging his teeth along my nipple. I had no idea how good this could feel, so while he did this, I started moaning like mad and jerking my cock like crazy. I knew if I didn't let up I'd come before he was done.

After letting go of my cock, he leaned back, propped my up on his upper legs and started to fuck me with just his hips, not moving his torso at all. We rocked back and forth, me to the tune of his thrusts, his to mine, until he pulled out and got on his back.

He told me to ride him.

I'd had experience with this before with my own anal experimentation, so when I immediately got down on his dick, I knew what to do. While bouncing on top of him, I stabilized my hands on his chest and went to down, going to town on his dick as hard as I could while trying my best to be gentle and not hurt him as at that point I was extremely horny. He started to moan and said, 'Yeah baby.' I then sunk all the way down on his dick and started to gyrate my hips, moving them in circular motions, while I rode him.

At this point, the dude seemed to have enough.

He asked me to get back on my back again.

Now more than prepared for what was to come, I immediately got on my back, raised my legs, and propped them up on his shoulders.

He went to down and began drilling me.

At this point, I was so horny and liking what he was doing that I was moaning uncontrollably. He was thrusting, pressing our chests together, fucking my ass at this point as hard as he could, and he seemed to know that I was going to blow soon, as he asked me to start jerking off.

I did as asked.

He told me to tell him when I was going to come.

It didn't take too long for that to happen.

Just as I was about to come, I moaned, 'Fuck!' and let loose, spraying all over my chest.

The dude pulled his condom off and asked me to suck his dick some more.

Still horny, I did as he asked and proceeded to try and deep-throat him as much as possible, though it was hard to do considering I was worn out and completely out of breath. After about five minutes of going to town on his dick, slurping up and down like it was an ice cream come and trying my best to fulfill his desires. he coaxed me on, asking me to jerk him off, and I continued to suck him as he began to fuck my mouth again.

He rolled over onto his side and asked me to suck him like that.

With the new angle, I bobbed his dick up and down in my mouth until he got directly on top of me and started feeding it to me from overhead. I did my best to suck like this, and even managed to do it a few times with his encouragement to 'take is slow,' but soon after he said he was going to come.

He pulled his cock out of my mouth and asked me to lick his balls.

I ran my tongue along his sack, thinking he meant softly.

He asked me to do it harder.

I started gnawing on them.

With the smell of his amazing ass in my face, his ballsack in my mouth and him jerking off directly overhead, I was in complete heaven.

After he asked where I wanted him to come, I said on my chest.

He leaned forward, grunted, and fired a load all over my stomach.

In the moments afterward, where he offered to let me shower so I could clean myself off, I was so tired from all the sex that I laid there for about five minutes and took slow, clean breaths as he cleaned his come off me with the towel he had lying in the distance for wipe up.

After I recovered, I wandered into the bathroom.

Guess what I discovered?

Rug burns.

On my knees.

Apparently, he'd been fucking me so hard while we were doggystyling that I got rug burns that bled.

I didn't stick around for long, as he was tired and had been up since six AM, but we did talk for a few minutes, get to know each other, then I departed and went to my car. He did, however, question whether I was truly a virgin, and when he said I was, 'Tight, but not too tight' and asked what I did to prepare, I said I just used my fingers. He seemed particularly pleased.

Three hours later (while writing this,) my lip is still numb from when he'd been facefucking me and my ass feels as stretched and awesome as ever. I've had to resist blowing my load the whole time writing this because it was so fucking hot.

So... that was the story of how I lost my virginity. It was hot, awesome, and I had an incredibly sexy and compassionate guy to lose it to, which made it even better. I'm still surprised I could partially-deepthroat and take a near eight-inch dick. Guess I didn't know the lengths of my abilities (but I sure do now!)