First Anal with a MAN by DougsLair

I thought.

GLORYHOLES!

What a wonderful idea. Anonymous, anyone could go, no one would know who you were, everyone was trying to hide what they were doing, seemed good. I was all ready to go, when it occurred to me, what about diseases?

More research. Seemed likely it was relatively safe, but the key was, relatively. Not good enough.

During all this, I continued to watch my favorite video. Continued to masturbate violently, and craved a mouthful of warm cum.

During this time, I’d begun fingering my asshole, trying to insert small objects into myself. I realized that the objects that I were inserting were way too small. Even soft, my own cock was way thicker.

How to do this? It suddenly dawned on me, going back years to my first blowjob, not long after, she’d asked me to fuck her ass. You can imagine how little convincing that took. I did, and after taking it slow a couple of times, she loved it. It became a regular part of our sex play. She was physically much smaller than I, and if she could take it, and enjoy it, so could I. Another girlfriend, I remembered, that I introduced to giving me blow jobs AND getting herself ass fucked loved taking me into her ass so much, that I once asked her if I was ever going to get in her pussy again. She weighed 99 pounds, when I weighed 224 pounds, and she was 5 feet 1 inch and I was 6 foot 6 inches.

With that knowledge, I sought to stretch out my hole.

Still not having touched another guys cock.

I continued buying larger and larger dildos, using lots of KY jelly, and could pretty much take it with minimal amounts of KY, and with no discomfort.

Hoping I was prepared, I looked through Craig’s List, after a couple of weeks, I found an ad from a guy, married, about my age, who only wanted a hand job.

WOW, another revelation. I shot him an email, and I stressed to him, he had to be freshly bathed, as I would be, disease free, he totally agreed, and after some back and forth, found we were both free, but neither could host. We settled upon the ABS, which for me, was about 5 miles away.

We agreed to meet in about 45 minutes, which gave me time to get ready, I was so nervous driving to meet him, I’m lucky to have not been in an accident.

I arrived before him, the parking lot had only one other vehicle, which turned out to be the old lady at the desk, inside.

Gary pulled up a few minutes later, he was as nervous as I was. We went inside, bought some tokens, and entered the booth area.

We found a couple’s booth (didn’t know they had those), fed the machine to get a video going, no idea what was playing, don’t think I ever looked, and we turned to each other. I’d told him he didn’t have to touch me; I was happy to just give him a hand job. He was shorter than me, and began to undo his pants.

I was very nervous.

He lowered his pants, and started to pull down his underwear, but I stopped him.

“Please let me.” I asked, looking at him.

Without a word, he nodded in the affirmative, and let his outer pant drop.

He was wearing black briefs, and his already firm cock was stretching horizontally towards his left hip. My first look at another cock, and it looked huge.

I paused, didn’t know if I could continue, but fuck it. I’d come this far.

I reached out, lightly tracing the bulge in his shorts.

He let out a low moan.

I continued, lightly tracing along the thick stalk, then down to his balls. After a bit of moaning, I eased his shorts down, freeing his cock.

A couple of thoughts hit me.

First, it looked very nice. God enough to eat, ha ha. But he’d asked me not to suck on him.

Second, he was quite hairy, and his balls were pretty good sized.

Lastly, he was fucking huge. For fuck’s sake, if he’d tried to fuck me, I’d ’a been ripped apart. I need to re-think my stretching, not that I intended to get fucked ever, but in case the worst happened, and I was assaulted, over powered, who knew?

Looking back at it, he wasn’t that big, much smaller than me, but it was the first I’d ever looked at besides my own, (didn’t have any interest in gym class at the showers) and the first I’d ever touched.

I gently stroked it, marveling at how the skin moved, watching it grow in my hand. A small drop of cum appeared at the pee hole, I moved my finger to play with it, smear it around a bit.

I moved my face close, inspecting the cock that I’d brought to life, now holding in my hand.

I felt quite a tingling in my own cock.

I know I’d said that I wouldn’t try to blow him, but before I knew it, I couldn’t resist. I tried, but I couldn’t help myself.

Ii leaned the last couple of inches, pressing my lips to his pee hole, the drop of cum there, coating my lips.

I pulled back, thinking he would hit me, but he didn’t.

I licked my lips.

Fuck that tasted fantastic! That’s what I was here for.

Without thinking, I plunged my face forward, my lips parted, and I sucked in the head of his cock, gently searching for another taste of his precious cum. I NEEDED it.

He moaned.

It startled me, snapping me back to reality, I pulled off him, telling him I was sorry.

“It’s okay,” he said in a low voice

I looked up at him. His eyes were closed, a slight smile on his lips.

Encouraged, I moved my head forward, my lips gently surrounding the head of his cock, my wet tongue beginning to run laps around the corona.

After several times around the head, and not being struck for disobeying our agreement not to suck, I began sliding my mouth down his cock.

As I slid him deeper into my mouth, my tongue was not idle. I kept it wet, and moving. A low murmur of satisfaction came from Gary. I began to withdraw my mouth and lips, applying a slight suction as I did.

Reaching the head, I let my lips and tongue caress all around, before I began my descent again.

I WAS A COCKSUCKER!

I began a slightly faster bobbing of my head, and to my happiness, I felt him begin to fuck my face.

I decided to see how much of him I could get in my mouth, but was met with a slight gagging sensation. Pulling back, I began methodically fucking him with my mouth.

All pretense of a hand job was gone, at this point.

I was blowing him.

I could taste his cum.

I loved it. Exactly what I’d been hoping for.

After maybe five minutes of giving head, my lips touched the base of his cock.

I’D DONE IT.

Applying a bit more suction, I began giving head in earnest.

Gary fucked my face as I sucked his cock.

All too soon, I heard him say “I’m going to cum.”

I panicked. I withdrew my mouth, and resumed the hand job that I was supposed to have been giving him.

It only took maybe a couple of strokes before he began to cum.

I held out my other hand, Gary’s cum filled my palm, and ran over onto the floor. Not because I tipped my hand, he OVERFLOWED my hand. In my life, I had never cum that much at one time, I think I was a bit mesmerized by the quantity, and thinking it was glad I’d pulled away, lest I drowned.

But, to this day, I wish I’d taken that load.

Gary pulled out some paper towels he’d had folded up in his pocket for me to wipe my hands with, I, in turn, turned my head, took his cock in my mouth, and cleaned off the few drops of cum still clinging to the tip.

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