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Letting Go

Category: Gay Male
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At 31 I was at the top of my game when all of this took place. I wasn’t making a mint but it was steadily getting closer to it so when I won five hundred bucks as “account manager of the year, it was just found money.

With not a little bit of influence from my fellow managers, I decided to take three hundred of it to celebrate at Venus, a local gentlemen’s club that I frequent about twice a month because I almost never failed to score there and not with the pros. At the last minute, I invited a rep named Jay that was visiting from Australia to join us.

As usual, it was a good show and even the early show was excellent. God, how those girls could move and those bodies…oh my god. Awesome.

After about four or five routines and several rounds, I had to piss so I slipped away, not realizing that Jay was right behind me. 

I guess that at this point I should reveal a weakness of mine. When I’m taking a whiz, I always try to check out the cocks on either side of me, which is why I try to get the urinal in the center. I’m as straight as an arrow but I’ve always had a fascination with other men’s cocks, maybe because mine is just so damned average. 

So, when Jay moved up to the one on my left, I glanced over to see if I could check out his package. I have to admit it was an impressive 8-1/2 or 9 inches of solid, thick manhood. Subconsciously, I turned away so he couldn’t see mine.

He was staying at the Bellwood, an upscale long term residential hotel, not far from there, so when no one had scored except the dancers, who had quickly spotted us as gullible cash cows, he invited us over for a few more drinks, like we needed them, and food, which we did. 

One by one, we all crashed in the guest room, or on the couch, or on the floor, wherever our bodies were when they refused to go on. I was one of the last to go down, since I hadn’t been drinking much at all. I was trying to decide where to crash when he offered to share his room with me. I was in no position to argue so when he stripped down to his briefs, so did I before crawling into the king-sized bed.

I’m not sure how long I’d slept when I became aware that he was touching my ass, not just a casual touch, but between the cheeks and down near my balls. I rolled onto my back, thinking it would discourage him but instead, it quickly became apparent that it was exactly what he’d expected.

Eventually, I went back to sleep, but then I felt him touching my cock. I tried hard to keep him from realizing that I was aware of what he was doing but it was hard because I know now that I actually wanted him to touch me. Why? Hell, I don’t know, I just did, so it was no surprise when he pulled it free of my briefs and began to fondle it. Of course, it only took seconds for it to come to full erection and it felt so damned good the way he touched me, caressed me and the slow strokes over it. Oh my god, I was so hard it hurt. I was not, however, prepare for him to kiss it and when he did, I almost lost it. 

It was more than I could stand and I let my eyes open slightly just in time to see my cock slowly disappear into the depths of his warm, wet mouth until it touched the back of his throat. I heard a loud moan and realized it came from me, followed by another when his tongue began moving against the knob and the puffy base of it. Without thinking about it, I pulled back just from the sharp sensation of pleasure but now he knew that I was awake and that I wasn’t trying to stop him.

He looked directly into my eyes as he slowly slid up and down, hesitating at the top of each stroke to suck on the knob and slide his tongue under it, caressing that tender, sensitive tissue there.

I was fisting the sheets to keep from screaming out in pure joy. Of all the women who had gone down on me. Not one could compare to the sensations he was giving me.

He stopped for a few seconds to slip my briefs off before returning to suck and stroke while he fondled my balls and seconds later, his finger slipped into my ass, probing deeper and deeper until I felt his knuckles against my balls. It only took a second for him to find my prostate and massage it but just as I felt the climax approach, he stopped completely to shift on the bed. 

He got up and stripped off his briefs, revealing that long, thick cock that was standing erect from his body before lying down again with his face near my cock and his cock level with my face.

I never hesitated for a second to take him in my lips to start sucking on him just as he was doing to me, although I couldn’t reach his ass well so just the tip of my finger slid into him but he groaned so it was getting the job done.

Already primed and ready, it wasn’t long before I shot a wad deep in his throat but he didn’t stop at all, swallowing every drop and sucking me dry. In fact, his finger got more aggressive in my ass and against my prostate as he continued to suck me back to erection again.

I never even gave a thought to the probability that he was going to come in my mouth so I wasn’t prepared when the first shot came, causing me to gag and choke. He quickly pulled out though to spray my face with thick cum but almost immediately his cock was back in my mouth and I was sucking wildly to keep him hard.

I was the first to come again and after milking me down, he let my cock slip out so he could shift positions, locking his long legs around my head to fuck wildly into my face until he pulled me to him with his hands, forcing his cock deep in my throat and holding it there as he filled me with cum, forcing me to swallow even though it gagged me to do so. 

. II

We lay together that way for quite a while, not speaking as our bodies continued to pulse with sexual pleasure, our balls empty and my ass throbbing from the aggressive attack as he dug for more depth. 

When we heard someone stirring in the next room, we both jumped up to grab our briefs but when I started pulling mine on, he grabbed them and pushed me toward the shower. I heard the soft click of the door locking just before he joined me in the shower. As we bathed each other, I expected him to want more, but instead, he whispered to me to dress and leave, explaining to anyone that saw me that I had an early appointment or something. He said he’d call me on my cell after everyone else had left.

I went to a bargain store nearby to get a toothbrush, toothpaste and mouthwash and I thought of getting a change of clothing, but then I realized that if I wound up going back, we’d both be naked so it didn’t make any sense. 

As I sat in a small café, sipping on coffee, I realized that I could still taste him and feel him in my mouth and ass. I also took some time to give some thought to what had happened and why I was in no hurry for it to end. After all those years of cock watching for what I thought was no reason at all I now knew for sure that I was a confirmed bi-sexual. It was somewhat disturbing to realize that I’d probably missed out on many opportunities to explore that side of my life.

The other realization was that I was prepared, at least mentally, to give myself to him completely, wherever that might lead. I’d have to work on the deep throat aspect and swallowing his cum which I really wanted to do for some strange reason. 

The one thing we hadn’t done, I wasn’t sure of. I knew he wanted to fuck me in the ass and that sort of bothered me. I’d heard from some of the women that it hurt like hell at first but that it was very satisfying in the end. (Poor choice of words, I suppose.)

I couldn’t get the size of his cock out of my head, fantasizing about how it would feel going in and once he was deep inside of me. How aggressive would he be? Would he take it slow, at least for the first time? Could that big cock fit all the way into me or would he have to be careful not to go too deep? Would he come in my ass? Would he use a condom? So many questions.

I jumped at the sound of my phone but quickly dug it out of my pocket to flip it open. He said to wait fifteen or twenty minutes before returning and that he would have breakfast waiting.

“If you’d rather not, I’ll understand,” he said. “Just tell me so I won’t expect you.”

“I’ll be there,” I said. 

I took a deep breath and headed for the car, knowing that I had committed to going all the way and I felt somehow relieved to be able to say tha even if I was just talking to myself.

When I reached his room, the door was not locked so I slipped in, locking it behind me. He was waiting for me, wearing a white robe with his cock protruding from the front, inviting me to take him deep. Instead, he smiled and led me out on the balcony where our breakfast waited. 

“You can’t eat in this restaurant looking like that? he said, handing me a robe.

I started to go in to change but he held me back. “I want to watch you strip,” he said.

“Out here out here on the balcony?” I asked, amazed that he would ask for such a thing.

“Right here,” he affirmed, and I want a good show.”

I shook my head, but before he could say anything else, I walked over to stand in front of him. “If you want me naked, you’ll have to strip me,” 

He smiled and pulled me close to him. “If that’s the way you want it.” he said, as he turned me so I was facing away from him. 

Reaching around me, he loosened my belt, a simple act that might seem innocuous in itself but knowing the ultimate outcome sent my already sexually charged mind into hyper-drive. By the time my slacks dropped around my ankles, my cock was rock hard and my body was doing strange things. I felt my balls tense and, my ass hole flex as this strange feeling, like a charge of electricity moved over me . A few minutes earlier I didn’t want him to undress me where someone could watch but now I just wanted him to fuck me wherever and whenever, no matter who was watching.

That was not going to happen, however as he took his time stripping me, making sure to make frequent contact with my cock and balls. I was almost ready to scream by the time I stood in front of him, naked and wanting. I tried to take his cock in my hands but he fended me off, dropping his robe before finally sitting down. His smile was so evil but he calmly poured some juice and motioned for me to sit down and eat.

My hands shook almost uncontrollably as I forced the food down while he pointed out places from where anyone with decent eyesight could see us. I no longer cared and, in fact, I think knowing that made it even more erotic. When he finally dabbed at his lips with the napkin before sliding the chair back, I was more than just accepting, I was ready and needing him.

He motioned for me to come near him and when I got there, he put his hands on my hips and looked into my eyes.

“Robby,” he said, “we both know what I want and what I intend to do but the question is, what do you want me to do?”

“Whatever you want,” I said. “All I ask is that you be patient and gentle at least at first, and that you try not to hurt me.”

“I have no intention of hurting you,” he said. “but I do intend to possess you completely.”

“I know,” I said, “and I want that too, or at least I think I do.”

He smiled and got up to lead me into the bathroom where a large plastic bag with a long tube was hanging from the shower door. Filling it with warm water he attached a long nozzle to it and motioned me into the shower.

“This may or may not be a pleasant experience for you,” he said, “but it has to happen before we go any further.”

He bent me over and pushed the nozzle completely into my ass until I felt two of his fingers inside me as well. The next thing I knew, warm water poured into me until I felt like I’d explode.

“Hold that for as long as you can,” he said, as he re-filled the bag.

When it became apparent that I desperately needed to release it, he continued to hold me down, turning me until I was almost facing the doors. 

“You can let it go now,” he said, as he turned on the shower, moving the head to where it sprayed on the back wall.

I sprayed the brown fluid over the wall, letting it run down the wall and into the tub where it poured down the drain. When I finally stopped, he put the nozzle back in and once again filled me to the brim to repeat the whole process only now the fluid was almost clear at the end.I knew it was an enema of course, but I’d never had one before.

He cleaned me up and led me to the bed where he got into a sixty-nine with me. He brought me to two very satisfying climaxes but wouldn’t let me get him close at all and I knew the reason for that. After sucking me dry, he rolled me over to push his finger deep into my ass, adding a second without slowing the deep strokes. Reaching into the bedside table, he pulled out a cone shaped toy about six inches long and three inches around, with four distinct steps in the cone. After drizzling some lube on my hole, he began working the toy into me to stretch me open before fucking me.

Holding it in, he led me onto the balcony, waddling like a pregnant goose, so the whole world could see me give my anal virginity to this man with the nine inch cock, but I could hardly wait to feel him enter me for the very first time.

I had assumed he would take me from behind, since that was the only position I’d seen gay men being fucked in, but instead, he put me on my back on top of the table, where he raised my legs high over my head before pulling the toy from my ass with his teeth. Dropping it to the floor, he licked my ass several times, then placed the head of that magnificent cock against the opening. There was a slight tinge of pain shortly after he entered me but thanks to the use of the training toy, it didn’t hurt when he first pushed it in. I grunted several times as he pressed forward, hesitated, backed out and went deeper, forcing my rectum to open to the intrusion.. I felt every inch of him inside me and wanted him deeper. Eventually, his balls pressed against my ass cheeks and I knew he was completely in. 

Starting with long, slow strokes he slowly picked up speed with shorter strokes, slowing occasionally to allow for longer strokes. As my body became used to him fucking me, the experience got better and better and the feelings became more and more desirable. As he drew nearer his climax, he became more aggressive, driving harder and deeper into me with every stroke until, with a series of body slamming strokes, he exploded deep in my ass. For the first time in my life I’d had a gay lover take me to the limit.

He took me into the bathroom then and flushed me out to cool my rectum and remove his cum, which he said could leak out hour hours if we didn’t do that. I was hoping he would take me again but instead, he took me to the bed where he went down on me again. 

We made love again a few hours later and went down on each other twice, Each time, I tried to swallow his cum and finally choked most of it down on the second try. I had to leave then but it was hard to stop and all the way home, I had my cock in my hand, stroking it until I’d almost come, then waiting for it to recover before bringing it back over and over. I needed something in my ass though and I made up my mind to take care of that problem as soon as possible. If I’d known someone I could trust to be discrete, I would have been on the phone before I even got home.


The next morning, he came into the office just before noon to pick up some paperwork. I tried not to look at him but found myself staring at his crotch every chance I got. Just before he left, he put a folder on my desk, explaining that it was an account he would be working with that had an American office. He wanted me to work with him to keep both offices happy.

I shoved it into my drawer but when I left that night, the folder went with me. As soon as I got into the car, I opened it to find a hand-written note 

“Be back In three weeks,’ he wrote. “In the meantime make sure your passport is current so you can call on this customer in Australia in the very near future.”

I detoured to the adult store and picked up several toys and a video to keep me happy in the meantime and headed for home to test them. Three weeks isn’t that long, I convinced myself as the first toy slid into my ass. It might give me the time to learn to swallow his come and take him deeper in my throat, which is why I’d bought the video about cock sucking techniques.

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