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"My Story: But NOT My First Time!"

This was by no means my first time, but it's an experience that I'll always remember, as the story has an interesting twist. I was in my mid-forties at the time, and recently divorced. Needless to say, I was making the most of the opportunities to lick, suck and fuck as much as I could, whenever the chance came up.

I had been chatting with this young guy named Tim on a bi-men's IRC chatroom, who lived in the same city as I. He had been after me to hook up for a while now, as he loved being a bottom for older guys like me (Tim was 23 at the time). Tim also had an interesting bit of kink to him, in that he loved wearing pantyhose, which he did all the time.

One Saturday morning I ran into Tim in the chatroom, and he almost immediately invited me over to see him. He was at work, and had the office all to himself, and was really hot to trot. It turned out his office was just a few minutes away from where I lived, so I agreed and went right over.

This was my first time to see Tim face to face. He was short and stocky, but to me at least was cute, with a nice round bottom. He had sent me a pic of himself in pantyhose, showing a short fat little cock that I was eager to suck (a size queen I'm not).

But Tim didn't want me to suck his cock, nor was he interested in sucking mine, or kissing, tit play or any of the other things I love doing when I'm with a man. All he wanted was for me to bend him over his desk and fuck his ass good and hard.

At first I was reluctant, as this was a bit odd in my experience at that time, but he starts rubbing my crotch and begging me to fuck him like a bitch in heat. That got the juices flowing, so I stepped back a pace and said "OK, bitch. Then get those pants off now".

Tim instantly complied, and sure enough he was wearing pantyhose, with his cock bent off to one side, hard as a rock and leaking lots of precum. Damn, I wanted to taste his cock so bad, but I had met submissive bottom sluts like Tim before, and pretty much knew what he really wanted.

As soon as he got his pants off, Tim turned around bent over his desk with a moan. "Now" he said in a surprisingly fem voice "Do me now".

His pantyhose still covered his wide ass, so I got my pocketknife out, telling him to be still, and cut a slit in the back, from just behind his balls up to the elastic around his waist. The sound of my knife cutting the material sent a shiver up his spine.

I put my hands under the material of the pantyhose, and massaged his wide, smooth cheeks, spreading them so I could see his ass. You can always tells a good, experienced bottom by how clean they keep themselves, and Tim was no exception. And his pucker was twitching in anticipation.

"Damn, you are a hot little bitch, aren't you?" I said. His only reply was a whispered "Fuck me. Please fuck me".

I slipped on a condom and squirted some lube between his cheeks. At first I grabbed my cock and ran the head up and down over his ass. Mmmm. Very warm, and this just made me hotter. I lined up on his hole and pushed in slowly. The head of my cock popped in past his pucker and he let loose a loud "Owwww".

I held still, massaging his back and ass. "Just relax, baby. I'm going to go slow to start"

Tim just moaned in reply. I waited a bit until his ass relaxed, then slowly rocked my hips back and forth, pushing in a little bit more each time. Tim started moaning again as my cock probed deeper and deeper into him, until I bottomed out, leaning into his warm asscheeks.

"Like that, baby? Feel that dick inside you?"

"Yes--yes" Tim whimpered. "Oh God, give it to me".

I grabbed Tim's hips and started pumping into him slowly. Damn, this guy had the hottest, tightest ass I'd fucked in a while, and I knew I would not last long. Grabbing his shoulders, I started pounding into him hard.

Our bodies slapping together in lust, he pushed into me as I rammed into him. The way Tim was moaning and whimpering, it almost sounded like he was crying, but I was way past caring one way or the other. All I knew was that I was humping a wonderfully hot tight ass, and was getting a better fuck than any cunt that ever lived.

Tim was on a short fuse, too, as he suddenly all but screamed, arched his back and his hot ass clamped down on my thrusting cock, telling me he was filling his pantyhose with spunk.

The extra tightness set me off, and with a loud roar I also came, so hard that I saw stars and felt as though the top of my head was coming off. It was one of the most intense orgasms I'd ever had.

After a few more spasmodic thrusts to empty the cum from my balls, I shakily stood up and pulled out. Tim slowly turned over and I was amazed at how much cum he had released. Half of the front of his pantyhose was soaked, and the cum was already halfway down his left thigh.

Tim and I just stood there panting for a minute, looking at each other. I leaned over and patted his belly, and said breathlessly but fervently "Thank you".

Tim gave a little laugh and said "Thank You!"

We got cleaned up and chatted for a bit before I left. And here is where the twist comes in. Even though I prefer sex with guys most of the time, I am bi, and do enjoy sex with women now and then. Only thing is, the only kind of women that attract me are big ones, especially with big asses. For this reason, I also hung out on another IRC chatroom where a lot of the local "BBWs" (Big Beautiful Women) hung out.

As we talked, Tim starts telling me about his girlfriend, a fat little twenty-one year old named Stacy. The more he talked, the more I tried to put my poker face on. Because it suddenly hit me that I knew his girlfriend Stacy very well.

I first met Stacy on that IRC BBW chatroom about a month and a half before this. In fact, it was a Saturday evening when I first started chatting with her, and she was knocking on my door only a couple of hours later, at 2 am. Within ten minutes, I had her naked and on her knees sucking my cock. I sent her home later at 4am, with my cum oozing from both her cunt and ass (Stacy especially liked being fucked up her big soft ass). Since that time Stacy had been showing up at my apartment once a week or so to fucked.

I asked a few casual questions about Tim's girlfriend, and sure enough, his girlfriend Stacy and the Stacy I'd been pumping full of cum for the past month were one and the same. In fact, the very night before I had fucked Stacy's bottom in the exact same way that I had just fucked Tim's, and she'd loved it just as much (only Tim was a much better fuck than his girlfriend). Talk about coincidences!!!

That was the only time I saw Tim, and I only say Stacy once more after that. I'd gone out of town on business for a few weeks, and when I got back they had pretty much disappeared from the chatrooms, and I heard later they got married.


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