Busting a Cherry

He claimed to be bisexual, but whether he was or not wasn't for me to suggest. Upon my only phone conversations, he sounded like one of those soft-spoken, overly sensitive guys girls just loved to date.

He'd e-mailed me once before, but it was this e-mail that finally got me to call him:

Hello,

I have called you a few times :) and I am not sure what you think at this point but I really want an experienced top to fuck me. I can leave my work at 11:30 and be in your town in 10 to 15 mins. I am serious that I really want to take me and fuck me until you get off. All I ask is that you start slow (as this would be my first time) everything else I would leave to you.

He included the photograph of him sucking a cock.

I'd taken a look back at the history to find the only other photo of him had been him fucking a girl. His earlier e-mail had read:

I have not bottomed before but I have to admit that I have had your number in my phone for a couple of weeks. I am 6' tall 36yo white male, 180lbs nice-looking in pretty good shape. I have a nice ass. The only question I have is, can you do me without killing me? 7 inches may be a little large. I may have to work up to a pounding. Can I call you? Are you available over lunch hours? after work? 5-15 ish? Saturday mornings? 

It's always a little sketchy to fuck a virgin, especially one around here in the boondocks. I get more fiftysomething men saying they waited until their kids were grown or their wife was dried up to try it. Fuck that. Let them hire a call guy.

But something told me this guy was a little different. I always go with my gut. So I called him up.

Funny talking to someone who sounded more nutty-crunchy-West Coast than Southern, but I gave him the invite and lickity split if he didn't show up in 15 minutes, as promised.

A tall six feet and beefy, he sported a thin, trimmed Abe Lincoln beard that turned out to be adorable. He stripped down and sucked me just enough to get me hard and then laid flat on his stomach.

With younger, inexperienced bottoms, I might ease into the fucking. But he practically begged for it. I got the lube instead of eating his ass, not sure of the hygiene situation anyway. I lubed my cock, I lubed his hole.

When I touched the pucker, it reacted immediately, relaxing and opening. I slid a finger just inside to feel him already relaxing. I didn't bother with any other digit play and went to lay on top of him.

I poised my raw cockhead at the hole and pushed just a bit. My head is flared and larger than the shaft, so it took a second for it to push past the first sphincter. It did with a grunt.

"How's that feel?" I asked, resisting the urge to bury my cock.

"Pull out for a sec," he said.

I did, and let him adjust to the sensation. When I entered him the second time a few moments later, the first sphincter offered no resistance, but the second did. I pushed past it and slowly, with a little at the time... He grunted and breathed hard.

"Does it hurt?" I asked.

"Yea," he said. "But keep going."

I did. And then it was all the way in. I relaxed on top of him and rotated my hips so my bare cock buried into his virgin hole.

"That's all of it," I said. "You've got a full cock in your ass."

"It hurts," he said. "But it feels good. Please fuck me."

I began thrusting, just with my hips at first. As I did, his hands reached around my arms to grab hold. His grunts became more groans.

"Oh man," he started to chant as I picked up the pace.

I really began to pound, lifting into a push-up position and letting my hips drop into his ass, my cock plunging deeper as my thighs slapped into his butt cheeks.

"I knew it would feel this good," he said.

"Why don't you sit on it and take it deeper?" I said.

We switched over, him taking a seat. Now I had access to his chest with gigantic nipples. I'd rarely seen nipples so large — two inches in diameter easily. His moderately hairy chest with a lovely treasure trail down to a very hairy bush. His cock had retreated into the unkempt bush, almost invisible except for the copious amount of precum pouring forth.

He rode my cock like a champ.

And then I positioned him on his back and fucked his legs in the air.

I pounded him some, but kept it to a minimum, knowing just how sore he'd be the next few days. I put him back on his stomach for the breeding and got the man to beg for my load in his ass before unleashing a torrent of DNA into his tight, no-longer-cherry hole.

He seemed relieved as I pulled out and rolled off. Not relieved it was over. Relieved like he'd shot a load. But he didn't. As he stood up, his precum-soaked bush never hinted his cock ever escaped its tangle.

"Damn, that felt better than I thought it would be," he said.

"So you'll come back for more?"

He nodded and smiled with a goofy grin.