Amateur

It felt so natural… I didn’t even give it a second thought when his hand trailed down to my thigh. He looked at me with that thrilling mix of anticipation, horniness, caution, and fear of rejection. The only thing I could think to do in that moment was to lean over to him and give him a gentle, tender kiss. As we kissed he found renewed confidence and his hand went straight for my crotch where it found my stiffening dick. That reaction, along with my tongue darting in and out of his mouth, gave him exactly the answer he had been yearning for.

Work had sent me to a week-long conference in Denver. I was basically holed up in one of the big, downtown hotels, attending meetings and workshops all day and then dinners and strategy sessions in the evenings after dinner. I had hit it off really well with some of the other attendees at the conference, including Martin who was from the Chicago office. By Wednesday we were eating lunch together and making snide comments at the back of the room during the more boring parts of the conference. After the evening networking session on Wednesday we both felt like sitting around and talking so we headed for the hotel lounge. We talked for nearly an hour in a dark corner of the lounge, chatting about all kinds of things.

When more personal topics came up, he hinted that he might be gay. I picked up on the hints and made cautious suggestions that I would be more than OK with that. Soon full-fledged innuendo took over and he was almost flirting with me. I felt that familiar rush of excitement and arousal and decided that Martin and I would have some fun together. That’s when his hand trailed down to my thigh and I responded by pulling him in for a gentle kiss. After a few more minutes of this horny high school-type foreplay, I broke away and said,

“It looks like you’re up for a little fun tonight. I’ve got some supplies up in my room. Let’s pay up and go upstairs.” He didn’t need any more encouragement. He smiled and slid out of the booth in the dark corner of the lounge and I followed him. We paid our tab and headed for the elevator. As we waited for the doors to open, he turned to me and said,

“I hope you don’t mind. I just felt so—I don’t know… comfortable with you? I don’t quite know what to say.”

“Don’t say anything. You felt comfortable because you could sense that I was comfortable with you. Follow your instincts.” With that, the elevator doors opened and we got inside. I punched 14 to take us up to my room and we waited while the elevator rose. Martin got close to me again and we started kissing right there in the elevator. We had to break it off abruptly when the elevator stopped on the 7th floor to take on a few more passengers. We both shot knowing glances to each other during the seemingly endless ride up to my floor.

Once we got in the door of my room we started kissing again with abandon. I ran my hands all up and down his back and ass, stopping to rub the warm globes of his ass for an extra long time. He did the same as we started grinding into each other. Our dicks were both super hard with horniness as we smashed them into each others’ abdomens. I broke away from our embrace, started unbuttoning his shirt, and said,

“I’m flexible and up for anything right now with you. What would you like?”

“It’s been ages since I’ve had a good fucking; like a really deep, passionate fucking. Do you think you could give me that?”

“Oh yes. Just feel the heat coming off my cock. It’s rock hard and ready for your ass, baby.”

“Then let’s get busy!” He turned away from me and pulled off his unbuttoned shirt, kicked off his dress shoes, and then unbuckled his belt. His pants soon slid to the floor revealing a set of boxer shorts straining to hold back his dick. As Martin undressed I did the same, stripping down completely naked, including my socks.

I excused myself to the bathroom to grab my overnight bag. I hadn’t expected sex on this trip (though I had fantasized about it) so my lube and other supplies were still packed. I grabbed the lube and a few condoms and rejoined Martin, who by that time was laid out on the bed naked with his dick curving up toward his belly. I set the lube and rubbers down on the night stand and then knelt down next to the bed.

“Let’s see what we can do about this first,” I said, as I grabbed his dick. It was smooth and firm with taut skin and a bulbous purple head. It just looked sexually delicious. I almost instinctively leaned in and started licking that delightful purple head while I slid my hand over the shaft. Martin moaned in appreciation. I kept lightly pleasuring him in hopes of getting him to relax a little bit, which he eventually did. The initial round of horniness canlı bahis şirketleri subsided and he was somewhat calmer and ready for some sweet anal loving.

“Swing around and put your legs over the edge of the bed, baby. It’s about time for me to start loving you deep.”

Martin did as I suggested and soon his dick was right in my face. I grabbed a little lube and swirled it on my two fingers which I then led over to his ass. I started gently rubbing around his tight little rosebud, all the while adding a little pressure as I did. I also lightly teased the head of his cock with my tongue just to heighten his arousal. Martin started squirming around and moaning and soon he was pushing his ass back onto my fingers. That was my signal to give him a little more.

“OK, baby; I’m about to slide my cock into your ass. I know you want this; I know you’ve been waiting for a big, strong man to come along and give you some asslove. Time to relax and get ready for your ass to embrace my cock.”

Martin’s head rolled back and he sighed. He could feel the intense pleasure coming from his ass while I pressed my lubed fingers in. He could barely wait for them to be replaced by my pulsing, warm cock. I pulled my hand back and then reached for a condom. I ripped it open and rolled it over the length of my hard shaft, after which I slathered on a generous amount of lube. I leaned forward over him and guided my cock into his ass slowly and carefully. I could see the look of intense pleasure as his sphincter embraced my beautiful, rubber-clad cock. I loved watching his dick twitch as I pressed more of my manhood into his receptacle. Soon I was as deep in his ass as I could possibly go; my balls were up against his ass and it felt amazing. Being balls deep in an ass, whether male or female, is an amazing feeling and one I never tire of.

I ground my hips into him in a swirling motion just to make him squirm with some more ecstasy. I loved that feeling of ultimate closeness between two men when one has accepted the other’s dick in his ass. That’s an incredibly powerful, vulnerable, close feeling. After what seemed like ages of laying there getting used to being inside of him, I started fucking him in a slow, comfortable rhythm. Given how horny I was I wanted to pound him for all I was worth and cum as quickly as possible but I somehow corralled the strength to go slowly with him, savoring every delicious stroke in and out of his ass.

After what seemed like ten minutes of slowly pleasuring his ass with my dick, I was building up to a monster orgasm. I started speeding up and after just a little more time I was going fast enough that I erupted in his ass in a torrent of orgasmic bliss. I felt like I was living my whole life through the energy pulsating in my throbbing dick inside his tight ass. I pulled out and stumbled back onto the other bed, almost delirious in pleasure. His legs dropped down to the floor as every muscle in his body released its tension.

I don’t know how long we both laid there after the act but it wasn’t more than a couple minutes. Martin eventually sat up and said,

“Wow. That… was… I don’t even know. So powerful, so fucking intense. Amazing.”

I got off my bed and walked over to him. I pulled the rubber off my dick and held it straight at his mouth for him to lick, which he did. He started tentatively swirling his tongue around the head of my soft dick. I put my hands on the back of his head and pulled him in closer and soon my whole dick was in his warm, wet mouth. He kept swirling his tongue around it until it started to stir and stiffen. Before I reached full hardness, I pulled out and asked him a question,

“What next, stud? You ready for another round or should we call it a night for now? I wouldn’t mind you fucking me. It’s been a while for me, too.”

His dick now starting to come back to life itself, he started greedily sucking on my hardening dick. That pretty much answered my question.

“How about you go lie face down on the bed and spread your legs. I’ll do the rest,” he said to me. I eagerly complied by pulling my cock out of his wonderful mouth and going over to the other bed and lying down. I spread my legs as far apart as I could for him so he could access my ass. He followed me on the bed with the bottle of lube and poured some of it on his fingers. The cool lube felt wonderful as he started pressing it into my asshole. I could feel my whole body relax with each press against my sphincter. I started to whimper like a wanton slut as he slid his second finger into me. It felt so good to have someone lubing up my hole for sex! I couldn’t help myself and I started squirming around on the bed, rubbing my dick canlı kaçak iddaa against the sheets.

Next, Martin got up on his knees behind me and slid a rubber over his cock. By this time it was fully hard again and ready for my ass. He laid down on top of me and started working his hard, slender cock into my man hole. It felt amazingly good to have a cock in me again. I *LOVE* getting fucked in the ass. It’s the most intense sexual experience and one that I crave regularly. He picked up a slow, easy fucking rhythm and I could feel his balls slapping against me as his whole body was moving on top of me. This was the pinnacle of man love: one man giving anal pleasure to another in the way that only two men can. I reveled in the delicious fucking he was giving my ass.

After what seemed like a very long time, he started to quicken his pace and then he tensed up and, with a few quick jerks of his body, he filled the condom in my ass with warm, wet cum. With his final thrusts he also hit my prostate well enough to cause me to tighten up my ass and start cumming, which in turn milked a little bit more from his dick. It was the most wonderful, luxurious feeling of the two of us cumming together in some kind of primal, male ritual.

He laid there on top of me tracing gentle lines on my cheek and nibbling at my neck for a few more minutes until his dick finally slid from my well-greased hole. I immediately felt that post-fucking void of being empty after having been so full and pleasured. He slid off me onto my side and I turned my head and we started gently kissing again. It was the most tender kiss imaginable after such a warm, tender fucking. After a little more kissing and rubbing our hands over one another, I invited him to stay the night in my room. He took me up on the offer. Shortly afterward he got dressed and went to get a few things from his room and returned.

It was a warm night so we slept just under a sheet draped across both of our freslhy-fucked bodies. It felt so good to have a man in my bed again; I loved laying against his hard chest and arm. We drifted off into blissful sleep together.

Six o’clock the next morning came far too early for us. We were a sweaty, sticky, lube-and-cum-covered mess. To save time while getting ready for the 8am conference, we decided to shower together and get cleaned up. That took a little longer than planned as we instinctively started caressing each other in the hot, soapy shower and eventually I jerked him off from behind. The hot water just kept stoking the furnace of desire between the two of us and I gave him a good hand job to get him ready for the day. The whole time he was flexing his ass cheeks which were around my hard cock.

Eventually we made it downstairs where we could grab coffee and a couple doughnuts and then dash into the day’s activities. We were in different work groups for the morning sessions but at lunch we got back together. Giddy like school kids who had just discovered sex for the first time, we couldn’t wait to get together again. Since we only had an hour for lunch and needed to eat, we grabbed a sandwich from the hotel deli and he took me up to his room, wanting to return the favor from the morning.

We went into his hotel room and he pulled me in for another sensual kiss. We kept kissing and fondling for a few minutes until he broke away and then slid his hand down to the front of my crotch. He could feel I was already good and hard. He led me over to his bed and motioned for me to lay back on my back and slip my pants down. I did as he suggested and then he came back to me with a silk scarf he had pulled out of his luggage. He slid my briefs down and let my cock spring out from the waistband. He then started to gently slide the silk scarf over the head of my penis. It was a whole new and amazing feeling. I sharply inhaled air into my nostrils as the sheer pleasure hit me. He then switched and started sliding the scarf up and down the shaft of my cock. That send even more shockwaves of pleasure through me. I don’t know how much longer he kept that up for but it must have been about five minutes. By that point I was so close to cumming I couldn’t help it. He grabbed a tissue from the night stand and gently placed it over the head of my cock with one hand and started jacking me off with the silk scarf with his other hand. It didn’t take long before I was shooting long, sticky ropes of cum into the tissue. He had driven me mad with desire and I couldn’t believe how sensual and beautiful an experience it was with the silk scarf. I asked him about it,

“Wow, babe, that was amazing! Where’d you get the idea to do that from?”

“I had a girlfriend who used to love jacking me off in different canlı kaçak bahis pairs of gloves—silk, leather, lace—you name it. Eventually I started experimenting with silk scarves and discovered this. Looks like you enjoy it as much as I do.”

“Fuck yeah! That was incredible. I never knew a man could be so delicate with another man’s cock. I’m usually about the power and the hard fucking but that was just beautiful.”

“Stick around—I might have something to show you tonight as well.”

As I recovered from the strong orgasm, we ate the sandwich and got dressed to head back to the conference. To be honest, I no longer really cared about the conference and whatever we were supposed to be learning. I was all about this newfound sexual adventure with Martin.

We sat together at dinner and then next to each other at the last after-dinner breakout session of the week. We were both a mix of fear and anticipation, that heady elixir that comes from illicit pleasure. I was wondering if any of our colleagues at the conference could tell that we had been fucking the past twenty-four hours and I’m sure he was nervously wondering the same. Once the last activity of the night was wrapped up, he came over and told me to meet him in his room in about forty-five minutes. I told him that he would definitely see me there and we parted.

Precisely at the appointed time, I showed up at his door and knocked. When he answered, he was dressed in drag. He had a blonde wig, tight red blouse with fake tits, latex skirt, and high heeled shoes on. I stood there somewhat in disbelief until he held out his hand and pulled me in the room. He had some light, tasteful makeup on, including some bright red lipstick.

“Hi,” he said, “I’m Martina. I want you to love me oh so badly! Do you think you can do that, big boy?”

Instantly, I felt a rush of blood to my cock as I got super aroused. Even though we had only been together for a couple days, I grabbed him and pulled him in for a kiss as naturally as if I had been doing it for years. I held him very tight and pushed my tongue as far into his mouth as I could reach. He went a little bit weak and I held him up in my arms. After that first embrace, I released him and he pretended to blush a little bit and said,

“My, MY! Aren’t we a naughty boy. Martina doesn’t give up her secrets quite so easily. You have to treat me right to get a piece of this ass!”

He turned around and flipped up the latex skirt and showed that he had no panties on underneath.

“Come here, big boy, and see if you can get me properly aroused. Maybe then I’ll let you have a piece of this.”

I unbuckled my pants and stepped out of them as I walked forward toward Martina. I grabbed him at the waist with the skirt still flipped up around his midriff and started grinding my crotch into his ass.

“Ooooh, yeah… that’s the spirit. I want to make sure that cock is truly ready for this sweet honey ass!”

I slid down my boxers and grabbed the lube he had left out on the night table. I lubed up a couple fingers and slid them into his nice, tight hole. I moved my fingers around all over the place, rubbing on his prostate and generally getting his ass loosened up for my dick. After I felt like he was ready, I pulled my fingers out and he said,

“OK, big boy, I think Martina’s ready for a good fucking. Can you give it to me rough? Huh? Can you give it to me rough like Martina wants it?”

I assured her I could. I slid the condom onto my dick and then poured more lube on it. I pressed straight into Martina’s ass as roughly as I could. It was such a shock to him that he gasped. I took that as a sign I has giving him just what he needed and I started fucking him as hard and fast as I could. I gave him a savage pounding right there against the bed in his room. After about five minutes of that I finally tensed up and shot a huge load inside the condom in his ass.

“Oh… my… GOD!! That was fucking incredible! You’re amazing!,” Martina gasped out before she collapsed forward onto the bed. Of the entire couple days of sexual experiences with Martin, fucking his female persona Martina was the most amazing. I felt rugged and primal after that dominating fuck. I may have even started grunting after my orgasm I was feeling so manly.

Shortly afterward I collapsed on the bed beside her, completely exhausted from our two days of vigorous fucking. Twenty years ago I probably could have gone another two rounds that night but, at my age, that was enough and I was down for the count. I rolled over to face Martina, planted a tender kiss on her lips, and then got up and got dressed. I didn’t say a word as I silently slipped out the door and went back to my room on the fourteenth floor.

The next morning as we were all scrambling to get to the airport for the flights home, I caught a glimpse of Martin getting in an Uber to head out. I flashed him a knowing smile and he gave me a priceless grin in return.

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