My First Ever Gay Date…

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Here is the deal. Last week I went on my first ever date with another man and since that night I have just been bursting to tell someone, anyone about it.

So, first about me. I am 48 and divorced. I was married for 15 years and although most of it was good (well, until she started sleeping with her boss) I always fantasised about being with a man. When I jerked off, that was what was on my mind. When I needed to get myself to climax when I was having sex with my wife, I would sometimes remember my only ever kiss and fumble with a friend at school and his delight as I gasped and the wet patch started to spread on my jeans. I was embarrassed then, and I always felt shame when I used that memory when making love with my wife. For fuck sake man, what is wrong with you? Anyway, I always thought that Demi Moore was smoking hot, so there was absolutely no way I could be gay, right? Also, my wife shared her drunken lesbian for an afternoon high school story, but I kept quiet and she is definitely straight. Her boss knows that for sure.

I kept myself in good shape and still am, so wanted to get out on the dating scene after the divorce. Frankly, I hated it. Online dating was a nightmare and I just didn’t really fancy any of the women or feel that “click”. Dated a couple for a while, and had some fun sex, but something was missing. After a while I realised that what was missing was a cock, and now that I was free, couldn’t I go and discover this whole new sexuality? I was terrified. So, I kept dating and kept jerking off thinking of a lover with a hairy chest and an erect moist penis, rather than great tits and a wet pussy. I knew I had to do something.

The Pleasuredome sauna in London was my answer. I went for the first time on a business trip to the city. Got slightly drunk with colleagues and in an adrenaline fuelled, hand shaking moment I looked up “gay sauna” found it was very near to where I was at that precise moment and before I could allow my self any second thoughts I’d paid my money and was standing in the changing area with a towel. I was exhilarated and terrified. That was my first trip and after two more I learned some things about me and my gay sex life.

The first thing I already knew. I was and am a great kisser. My first girlfriend said it and I have heard the same compliment in a private, smelly, sweaty room in Pleasuredome. Also, I didn’t think I would, but I like kissing men. Actually, the truth is I like them kissing me. I like the weight of the mouth on mine, and I like that his tongue explores my mouth first. I like the hot breathlessness and eagerness of a horny man’s face on mine.

I also sort of knew the second. I have a great ass. I’ve always liked it. Yes, it is bigger than most guys’ butts and I played rugby, so I have seen a lot of hairy arses. Yes, it is also smooth, so not really all that manly. That bothered me a bit in my rugby days, but I grew to admire its curve and frankly, its peachiness. I had a university girlfriend once who took a picture of my bum with her camera (back in the days before mobile phones existed) as she said her gay friends would love it. I went along with the idea for a laugh – after all my face wasn’t it the picture, so it could be anyone. It turned out some of them really did love it and I remember a flush of arousal at that revelation.

My bum hasn’t changed that much through time and although I knew it was nice, the real certainty I got was from a very hot, younger, good looking complete stranger in the sauna, who whispered that I had an awesome ass, as he slide his finger slowly in and out of my hole. Shortly after that he was on the receiving end of a great blowjob.

That leads me to my first completely new discovery about my gay self. Turns out, I give great blowjobs and I love to give them. I get so turned on at a cock stiffening in my mouth. I relish rolling my tongue around the tip, my lips grab the shaft with the right level of firmness, and imagine my surprise as I can overcome my gag reflex and take even a good size cock almost the whole way into my mouth. As for the cum, I want it in my mouth so much, and I think the owner of each cock can sense that and it brings them off even more quickly. I satisfy my anonymous lovers completely with my mouth and I feel strangely proud of this.

My final two discoveries are about anal sex. So, if you haven’t already figured it out, when it comes to sex, I am the receiver. The bottom. The girl, if you want. I don’t particularly mind whatever the label is but after most of a lifetime doing the fucking, I now just want to get fucked. I feel so sexy, and so overpoweringly erotic to have my legs apart, a cock inside my ass and a tongue in my mouth. What I equally like is to be on all fours with some stud (always a stud in my mind, even if it is a slightly overweight middle-aged guy behind me). That I am a bottom, isn’t a discovery, however. One discovery is that the simple male penis, of which I have seen hundreds when soft and cold after rugby matches (and I now know that I was always trying to get a glimpse Beylikdüzü Escort Bayan of certain naked teammates) is a multitude of lengths and girths when erect, and big ones really hurt, if the owner is too horny to look after your needs. The second, is that it turns out I am quite the moaner and talker when I am being fucked. I can’t help it, I gasp and grunt with every thrust, and am likely to beg for fucking in the heat of it. Like all my favourite girls when I was providing the thrusting, I am a squealer and I couldn’t stop it if I wanted.

Saunas were not a long-term option for me. The three times I went were fun, and I really honed my oral skills in the most fun way, and had sex with three different guys. One young, cute guy with quite a small cock, who was very considerate and kept asking if I was ok, one who was very quick (slightly overweight middle-aged guy) and one who slammed his cock in and just fucked me like he was using me to wank. It felt seriously hot to be used, but it was also quite sore as he was pretty big. Penetration really hurt. I really moaned and squirmed with him on me. All good dirty fun but I wanted more.

I wanted that elongated foreplay. I wanted to know my lover’s name and him to know mine. I wanted the tension to build and I wanted a point where we both knew it was going to get hot and heavy sometime soon. I didn’t want a husband or even a relationship. That’s just a good date.

I was away in NY last week for business again and that when I decided to take gay to the next level. I set up a tinder profile on Tuesday, looking for a date on Wednesday. I sat in the bar at my hotel with a glass of wine and started swiping. It was so horny to sit there my myself with people all around as I innocently went about choosing a sexual partner. In New York on Tinder, that was not difficult. Within the hour I was in about 8 different chats and I’d already slipped to the toilets to give myself some much-needed hand relief. I was shaking with lust at the prospects.

I quickly narrowed it down to one guy. His name was Mike and he was also in town visiting. He had that he was 100% a top on his profile so that was cleared up quickly. He was about the same age as me, a lot of hair that was going grey in a sexy sort of way and he was a bit taller than me. I’m 6ft so I liked that. I also have a shaven head and look anything but feminine, so was delighted to get from him that he liked men who were, well, men. We chatted through the app for about 30 minutes and arranged to meet the next night. I finished my drink and went back to my room, where I had to jerk off again before going to bed. I was massively excited and horny.

We met in a quiet bar the next evening. He was already there when I arrived five minutes early and asked what I was drinking. I was incredibly nervous. This was more nerve wracking than undressing in a gay sauna as someone is watching with intent. I now had to have a conversation and all the build-up I had so craved now seemed difficult.

Mike made it easy. He was a really nice guy, open and honest. He was married, which made me a bit edgy, but he explained it was pretty much over and they agreed they were together for the kids. He was in town for a conference and this was something he did frequently. Really frequently. Clearly there was an experience gap. He was also much better looking than in his profile picture, which was absolutely unheard of with the females I’d met from online posts, and quite frankly I’d made my mind up that I wanted him badly very quickly. It appeared he wanted me too. To my relief as the drinks flowed, he slipped his hand on my thigh very gently under the table and squeezed. I immediately felt a firmness in my trousers, and my mouth go dry. I drank more.

The conversation turned to sex, or rather Mike turned it to sex. He asked about my experience and he was clearly delighted to find out that I well behind him in terms of partners, but he was also impressed at my admittedly quite slutty sauna adventures. I think he was turned on by that as his hand slid under the table where no one could see and this time he ventured further up by thigh to my bulge. I took another mouthful of wine.

As he ever so tenderly rubbed my erection and made me a bit breathless, I talked about my gay sex discoveries. He had asked and I wanted to tell. His rubbing was brazen and assumptive, but I didn’t want him to stop. I was entering a fuzzy state in my mind where I knew he was in charge and I wanted him to be. I wanted him to make every move and feed his desire. It was exhilarating.

He smiled at my comment about large cocks.

“You’ll be disappointed, then”. He said.


“I am well above average, and I know what average looks like. But don’t worry, it is all about patience, and I am very, very patient.” As he said this he was looking right in my eyes and he had moved round close so that his right hand was now completely cupping my balls. I wanted to kiss him right there and let him fuck me on the table, but he lingered Bahçeşehir Escort Bayan just long enough for the big tease and then moved away still holding my eye. I was feeling an absolute overload of lust for this man.

“Let’s go,” he said and then whispered in my ear “I. Want. You. Now.”

The date was going perfectly. It was better than my every fantasy, but would the sex match? I was worried it might hurt, I was sure there would be no mess as I had really prepared for this, but his size and my nerves and inexperience could make the next hour or so a bit of a let-down. My worry was misplaced, as I was to find out.

We went straight back to his hotel room. He had a large room with a big sofa at one end and a massive bed. I was staying I a nice hotel but this was something else.

He kissed me hard. We had just entered the room, and he slid his arms around my waist and moved his mouth smoothly to mine. It was wonderful. Lusty. He pulled me close and for the first time I could feel his bulge as well. He was pushing it in to mine as he pulled me to him. He smiled as he moved away. “You are a good kisser”. I smiled back and rubbed his crotch to feel what was there. I was worried, but I was so delighted by what my hand explored.

He moved away “Drink?” It was a question but he was already pouring.

“Please,” and then I asked something, that seemed strange in hindsight but at the time felt important. It was a warm evening, we’d been walking and I wanted to be perfect for him.

“Would it be weird if I took a shower?”

He looked at me and smiled as he took a drink.

“No, go ahead. I’ll be waiting here for you. Don’t be long…”

I showered quickly and as I was drying I noticed the hotel staff had left two bathrobes out on the pegs. Presumably a “his” and “hers”. One long, to the knee for him and one short, mid-thigh level for her. I put on the “hers” and enjoyed the soft towel material on my skin. I went back in the room. Mike was sitting on the sofa, legs crossed, arms resting on the back.

Sit with me he gestured, and I obeyed. I was now trembling as I sat beside him. He was sitting forward now leaning towards me. He was fully dressed, and I felt vulnerable and sexy as he pulled open the bathrobe towelling belt. He pushed one of the folds aside as he slipped his hand onto my naked waist. I gasped and he smiled. It was a lovely smile, I thought. My skin was hot from the shower and his hand was cold from the ice in his drink. It was thrilling.

He moved his hand slowly up my side and across to my chest, holding my eye the whole time. My mouth was open, half with the sensation of cold and half begging for his mouth, his tongue. He didn’t kiss me. Yet. He moved his hand onto my right nipple and started kneading it gently between his thumb and second finger. He pulled it softly and released. I gasped. He pulled it again. Then he kissed me, a deep slow kiss, with his tongue darting in and out as he played with my nipple and my cock stiffened completely.

“I want to do something for you” he whispered, his breath right in my ear as he just squeezed by cock. I hoped he wasn’t going to pull it or suck me as I was sure I would blow quickly. But that’s not where his mouth was headed.

He rolled me skilfully and gently round so that my knees were on the ground now and my chest was on the seat of the sofa. The bathrobe was open at the front so I could feel the sofa fabric on my hardened nipples, but it draped halfway down my thighs and I thought it felt like a skirt would. I then felt his hands underneath it pushing it up. I pushed my ass out a little and spread my legs a little apart, in anticipation of what I hoped was coming next. I wanted him to see me completely vulnerable and open for him. Open for his desire.

He pushed the robe up my back, and I was then bent over, ass in the air half dressed. He was still fully clothed and was rubbing my ass cheeks and teasingly running his finger along the crack. I just closed my eyes and murmured my enjoyment of this.

“Patience” He said, as he pressed a finger against my hole. I pushed back, but he took it away. Then with my eyes still closed and my ass pointing to the sky, I felt his touch go only to almost immediately return but softer and wet. He was softly biting and licking my cheeks and his tongue was moving closer to the central target.

It seemed like an age before he put his tongue on my hole, but that was only because wanted it so much. I moaned loudly as he did, and my moan was met with greater force from his tongue as he probed. His hands were on my ass pulling the cheeks apart and I could feel his bristle and his breath as he licked my hole with true hunger. He pushed my legs a little further apart and I felt the tongue leave and the finger return. He eased it into the moist hole to the first knuckle and started twisting it slowly inside me. I moaned again and this again encouraged him.

“Don’t move” he said and removed his finger and stood up. I looked round at him, my ass still up and he locked eyes again as he started to undress. He took off his shirt and his chest was a lovely mix of dark and grey hair, sexy, manly. He licked off his shoes and pulled off his socks. Even as I was offering my ass to the man, I was still thinking that took some balance. Then he unzipped. He slowly pulled his trousers and underpants down in one movement to expose his absolutely beautiful and pretty damn big cock, semi erect. He took his trousers right off and stood, allowing me to admire.

He had told me to not move and for that night I was all his, but this would be one a would not obey. He was happy for me not to. I moved over to him on my knees, and without touching it (yet) with my hands I pulled his cock into my mouth with my curled tongue. I looked up at him, looking down at me, as I rolled my tongue over his head and slowly moved it deeper into my mouth. It was his turn to gasp and open his mouth with pleasure. It was my turn to be encouraged to move faster and more.

It was now completely hard and it felt like it filled my whole mouth. I wrapped my hands around the shaft and felt the warm rock. I sucked and I licked the head and I treated that cock better than any that had been in my mouth before.

He pulled my hands away but allowed my mouth to keep working. His hand was on the back of my head gently pushing me onto his shaft. I loved it, but I could not take it all and gaged a little. He released the pressure and then reapplied. How dominant I thought, as I felt my own cock stiffening once more.

Mike pushed my head away and took his throbbing cock out of my mouth. He pulled me up to my feet, slipped the robe off and kissed me hard and passionately as it fell to the ground. Our bodies, now both naked pressed together and I felt giddy with that, and our hard cocks rubbed our stomachs. For the second time I was worried that I would just come, but now I just wanted to as well. Maybe Mike sensed my rising urgency because he stopped and said.

“I told you to stay put…” he was mock firm and gave me a not mock firm, slap on my left ass cheek. It would be a bit pink from that. I liked it.

Without speaking I went back to my position over the sofa. Legs fully spread this time. Ass high as possible. No robe to get in the way. My eyes closed again. Waiting.

I felt the cold lube trickle down my crack and that made me twitch. That got another slap. Another burst of pleasure and another gasp. I opened up and thrust my ass out.

I could feel his finger on my crack. It was all wet there. He was just rubbing up and down my hole, teasing and delighting. He would slide it in, but not yet.

Another slap. He knew I liked it and there would be more. Good.

The finger started to press the opening. It was tight but it slipped in.

“Patience” he whispered in my ear again, this time as he slowly moved the finger in and out. Then out and …slap. Then in. I didn’t want this pattern to stop, but I knew that this man wanted, needed to fuck. I could feel his cock still stiff against the back of my legs as he worked his finger in and out.

Pause. Then a slight pain and feeling of stretch as I guess another finger went in. The finger fucking, which had picked up pace, slowed down again. Patience, I thought. He is a patient man. Two fingers in me moving in and out a bit quicker until the feeling of stretch disappeared, and it felt so good. I was moaning now and pushing back on his hand. Slap. Gasp. Moan. Slap. Patience.

He kept on building the pace and then slowed back down and just started rotating his fingers. Then he gently pulled his fingers out and I felt open and exposed and sexy and wanting and anticipating…

“Condom” he said to explain the delay, but there was no delay before I felt his hands on my hips again. One hand left and I felt him press his head against my hole. The head was much bigger than two fingers, but it slid in easily, and slowly. No pain, but an intense feeling of being full.

His hand having done it’s guiding work returned to my hip and pulled me slowly towards him. I let him enter me at his pace, and it was the right pace. My eyes were closed and my mouth open as my breath quickened, and I felt the head hit a spot in me that made me dizzy. He was big, but I wanted him all. He had me completely and now he should fuck me completely. Just fuck.

He kept entering slowly and then when I couldn’t not take any more, he was all in and started grinding. We both moaned as the grinding quickened and he started to pull part out and slide full in. I let out a lough “Uuugg” with each thrust. I looked round to watch him fucking me and his head was back, his eyes closed and his mouth open. He looked down and pulled me up gently by the throat to kiss the side of my mouth.

“Good?” he whispered in my ear. My “Uuuugggh” as he trust answered the question.

His pace was building, and I felt his hand come round me and squeeze my cock. The feeling was beyond intense as he fucked and squeezed. I was rock hard again in no time and he was stroking me. I knew I was coming, so I took his hand away. I didn’t want the focus on my cock. His cock and my ass. He understood immediately and pulled my hips into him as deeply as he could. My orgasm would follow for sure.

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