First Anal with a MAN by DougsLair

Without a further word between us, we both, now embarrassed, walked out of the store.

In the parking lot, Gary looked a bit sheepish, I was just flat out embarrassed.

“I apologize for taking you into my mouth…” I started.

“No, no, no apologies needed, I enjoyed it, Thank you.” He replied with a smile.

We talked for a few minutes, I’d asked if we could do this again, and found out, he only lived in the housing development over from me. We kept meeting, on a irregular basis for almost three years until he stopped wanting to meet with me, no explanation given. We continued to meet, as I said, me giving him hand jobs, sucking him, he did surprise me, when, without warning, he took my cock into his mouth and sucked on me briefly, but never did anything else.

I tried a few more times to find someone to pursue my sucking and swallowing, but never could find anyone I was comfortable with taking into my mouth, or even stroking.

A year or so later, on a whim, I went to Craig’s List, and spotted an ad, “MWM, need stress relief, tired of jerking off, would like someone to come to me and provide stress relief. I can host”

I sent a response to him, and was surprised to receive an almost instant reply from him. He was married, worked from home, clean, no diseases, just wanted to get sucked off, without having to blow me.

I was good with that, we passed a few emails back and forth, he would shower while I drove to him, I would suck and swallow his cum. He told me he wasn’t too good looking, I replied that it didn’t matter, I wasn’t looking for love, just a mouthful of cum.

He responded enthusiastically, gave me directions, and I got ready to drive to him.

It took me about 10 minutes to freshen up, and another 15 minutes to drive to his house.

He answered the door, hair still damp, and a towel around his waist. He was correct, if I had been a woman, I would have passed him by. He was in fairly good shape, maybe like a hockey player build, muscular, not much fat, but he was right, not the best looking guy, but, who was I to judge.

I followed him inside, we shook hands, introduced ourselves and I followed him upstairs to the bedroom.

Children’s toys were scattered around, kids in school.

I followed him into the bedroom, where I began to get undressed. Tee Shirt and shorts were all I wore. It was a nicety about homosexual sex, there was no trying to impress, no false airs, we knew what I was there for, it was simply two guys together, to enjoy ourselves.

Fred dropped his towel, exposing himself to me, as I turned to toss my tee shirt and shorts on a chair.

Fred sat on the edge of the bed as I came around to him.

He slid back a bit, when I first took a look at him.

I was, I’m embarrassed to admit, a bit shook up, when, looking at his crotch, all I saw was a rather unattractive pile of loose skin.

Fortunately, before I had a chance to embarrass myself, I recognized that what I was looking at, was an uncircumcised cock!

The HOLY GRAIN was my next thought. You see, I’d developed a bit of a fetish for uncut cock. Never in my life, in the showers after gym class, in the showers at the university where I worked out, had I ever seen a real, live uncut cock. I’d seen a few on videos, but they were semi-erect, this was one in its dormant state.

I dropped to my knees, between Fred’s legs, and stared. Moved closer, getting a good look at it.

“I’m a grower, not a shower” Fred said

“It’s fine” I said. I know I was licking my lips in anticipation.

I leaned forward, touching my tongue to Fred’s cockhead. Or, rather, the skin covering it. I gently retracted the skin, uncovering his head. I noticed his pee hole was quite large, compared to mine, Gary’s and the ones I’d seen in videos.

I enjoyed myself, playing with my new toy. I was quite taken by the different feel, texture, and movement of the uncut skin.

With a start, I thought I should get going, Fred needed relief.

I was going to enjoy this.

My shoulders between his legs, I held his soft cock more or less upright between my thumb and forefinger, and leaned in to run my tongue inside his foreskin, across his pee hole. Some guys don’t like that, Fred let me know, with a long moan, he did. “Yessss” was what I heard.

I applied suction, and made my tongue more active. I felt a stirring in his shaft, I’d noted nothing special, he seemed normal in size, except for a lot of loose skin.

I started slowly moving the skin an inch or so each way, as I worked on his cock with my tongue. Gradually, I felt him thicken and harden. As it became firmer, and no longer necessary for me to hold, I removed my fingers from the shaft to caress and somewhat tickle his balls, playing with them in his sack.

His shaft continued to harden, I continued to enjoy myself. As it lengthened, I had to kneel up straighter, that’s when Fred asked me to get up on the bed so we could 69. As I’d said earlier, I love getting sucked, but I find that when doing a sixty-nine, it distracts me from the job at hand, so to speak. None the less, it was our first time together, I acquiesced, I slid on top of him, and as he took me in his mouth, I now had a good look at his cock.

“Fuck”, I said, “that thing is getting big” It was, WAY bigger than I’d thought it would get.

“Oh, it’ll get bigger”, Fred said.

I moved my head back, it was about seven inches long now, a distinct curve in the shaft, and getting thicker. I noticed that the foreskin had not fully retracted from the head.

“Damn”, I said, “I wonder how that’d feel in my ass, I’d enjoy getting stretched by something like that.”

Fred replied “Probably not. No one will ever let me try to put it in their ass, once they see it.”

“Not even your wife?” I asked.

“Oh no, she won’t let me even get close to her” he said.

“Well, if you ever want to try it in mine, I’m willing,” I stated “Even though I’m virgin, I want the experience of being fucked like a girl.”

“It’ll hurt too much” was all he said.

“I expect it’ll hurt” I said, “but it’s kind of an erotic thing with me. Girls get their cherry popped, it hurts them, I have to experience pain, my first fuck”

“I’ve only done anal with one guy in my life”, Fred said, “and he was hard core Gay, had been all his life. I put on a condom, and slid right in. He was first, last, and the only person, male or female, to let me try.”

“Well”, I said, as I felt him getting thicker in my hand, “I’m still willing to try. If you’ll go slow, and use lots of lube…”

“I need a magnum condom” he said

That was the end of conversation, as I put the head of Fred’s cock back into my mouth. I immediately noticed it was thicker. A lot thicker. I pulled my face back, the fore skin was retracted from the head. I needed to reassess the situation here.

I continued mouthing that thick cock. It continued to grow. People always exaggerate cock size, boob size, but we know, in the real world, huge cocks and huge breasts are augmented, photo shopped, yes, really big ones do exist, but rarely.

Fred was huge. My fingers didn’t meet, holding him around the shaft. Sure, I could squeeze, and they’d meet, but loosely, nope. The cock, base to tip of the head, probably at least eight inches. Measured on TOP of the shaft, not underneath. The head was good sized, I noted that the shaft got noticeably thicker at the base, than at the head.

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