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This is a true story of my first time with a guy. I've not been with many guys (just three) and I've only allowed one to penetrate me (the first one), although I've masturbated for and with several other guys without any touching or reciprocative acts. My first time sticks in my mind because, for me, it represented something completely new, kinky and highly erotic.
This happened in 2011. I'd been living with a US-Iranian girl (Iranian father, immigrant to US, and American mother), but had never really trusted her. She'd been involved in some pretty bad things prior to us meeting, and just before I met her I'd gone through a rough and sudden separation from my wife, Aimee, so for me it was very much a rebound relationship. Anyway, she'd moved out of my apartment and was living with some friends, and although we texted most days and still talked, the relationship was all but over (it would be rekindled later, but that's a different story).
When I wasn't at work, I found myself getting increasingly horny. I'd masturbate all day, trawl the internet looking at porn and trying to find girls to hook up with. I had moderate success - a threesome with a couple in a nearby town, $60 for sex with my first black woman, and some phone sex with some strangers, some of whom I think were men pretending to be women. One day, however, I stumbled upon some gay porn, and was surprised at how much it turned me on. I was mesmerized by what seemed to be a straight guy being seduced in a van by a gay porn star, being tricked into getting his dick sucked and then liking it so much that he ended up fucking the guy even though he seemed pissed when he found out it was all a trick. Probably staged, I know, but it made me really horny.
I'd had fantasies about guys before, but had never acted on any of them. Coming from a very strict, conservative background, stuff like that was frowned up and condemned. However, I now found that my fantasies were getting kinkier, and I was becoming increasingly desperate to experiment and try new things.
I decided that Craigslist would be my best bet - I'd looked for women on there (without success, other than the aforementioned black girl whom I had to pay for), but had never thought about looking for a man, although I was aware there was a "men seeking men" section. When I finally posted on Craigslist, I didn't want to actually have sex with a guy - I was more interested in getting naked, maybe touching his penis, and jerking off together. I got several responses (one, oddly enough, from someone I knew, to whom I regrettably did not respond as I was afraid of being found out), but no one I was really interested in. Some of the guys seemed too hairy or too fat, and it quickly became clear that I didn't know what I was looking for exactly. So I decided to repost my ad, but with some very honest and specific details, so I altered it to basically state that I was a bicurious male, recently separated, and looking to experiment with a guy. I made it clear I'd never done anything like this before.
Again, I got several responses, but one caught my eye. It was from a guy who said his name was Greg. He said he was local to me, very discreet and clean, and that he'd love to help me explore my fantasies. He also said that he'd be respectful and would not do or expect anything I didn't want to do. We messaged back and forth for a while, and then I finally agreed to let him come over to my apartment late one afternoon.
I was nervous as the time approached. I was very horny, and it was all I could do to stop jerking off. I knew if I did, I wouldn't stop. I took a cold shower, scrubbed every inch of myself, brushed my teeth, and waited for Greg to arrive. A few minutes before 4pm, I heard a vehicle outside. I went to the window, and peaking through the blinds I saw a black SUV pull up into the parking space beside my car. My phone beeped a few seconds later - it was Greg, and the message just said "here". I responded, "come on up, apt 214", and watched as an athletic man got out of the SUV, well dressed (shirt and tie), clean shaven, salt and pepper hair, and head towards the stairs.
My heart began to pound out of my chest, and I was really shaking. Could I really go through with this? I thought to myself. I was wearing nothing but the towel from my shower, and was having serious second thoughts, when I heard a light tapping on the door.
"Crap", I muttered to myself.
Shaking, I went towards the door. I could feel my dick hardening under the towel, despite the nerves and second thoughts. I looked through the peep hole and hesitated. I really wanted to do this, but I was scared I wouldn't like it or would really regret it later on. Honestly, I was at a crossroads and wanted to both let Greg in and ignore him as well. I heard another tap at the door. In that instant, I made my mind up - I would let him in. Shaking, and heart still pounding, I reached for the door handle, turned it, and opened the door slightly. Keeping my body behind the door, I peered through the crack. Greg raised his hand and said "Hi". I opened the door wider to let him in, still hiding my body behind the door, and he slipped inside. I shut and locked the door behind him.
The door opened straight into my living room. My voice shook as I asked Greg if he wanted a drink - he asked for water. I walked to the kitchen area (open plan apartment) and retrieved a bottle of cold water from the fridge, then walked back and handed it to him.
"You're shaking," Greg observed.
"Yes - I'm nervous," I replied.
Greg took a long swig of the water. "Don't be," he said when he was done. "We'll take it slow and we'll just do what you feel comfortable with."
My heart was calming slightly but I could still feel it pounding.
"How do we start?" I asked, feeling my voice shaking.
"Well, how about you come over here to me?" said Greg. He was standing in the middle of the living room. I walked slowly towards him, conscious that he was fully clothed and I just had a towel on. My dick started to harden, and I walked towards him. He put his hands on my shoulders, and slowly massaged them. He said, "mmmmmm, you smell nice", and slowly started to rub his hands over my neck, my back, and down my chest.
I began shaking again, but this time with anticipation. I felt his hands reach my nipples, slowly brushing across each one, which sent a shiver down my spine, and then his hands continued to slowly make their way down my body. He rubbed them round my back and across my belly, pulling me in closer, until his hands reached the top of the towel. It was tied in a knot at the side, and his left hand slowly made its way over there, pulling at the knot until it came undone. I felt the towel slowly slip away from my body, the fall delayed slightly as my cock was released and sprung to attention. I could feel the AC on my bare ass.
I inhaled sharply, turned on by the fact that I was standing in front of another man naked. I think the sensation was heightened by the fact that he was still fully clothed - I found something highly erotic about that. I could feel the towel around my feet. The next thing I know, Greg had taken a step closer and I could feel his breath on my neck. It was hot, and sent a feeling like electricity down my spine. I shivered. I felt my cock touch his clothed leg, then I felt his hands on my again, exploring my back, and slowly tracing there way once more from my neck, traveling down to my chest, then my belly. I thought he was going to grab my cock, but he didn't. Instead, he slowly traced his fingertips around my waist, and started to massage my buttocks. He kept doing this for a few moments, then I felt his lips on my neck, his hot breath and tongue teasing my skin, making me shiver even more.
Suddenly, he became a little more forceful, and I felt him spinning me around to face away from me. His left hand continued to massage my ass, while his right hand reached around and slowly teased the full length of my cock, before taking it firmly in his hand and starting to work it back and forth.
A moan escaped my lips, and I found myself grinding my ass against his hand and alternately thrusting forward into his cupped hand. I was so turned on I could barely stand it - I was being dropped and jerked off by a fully clothed man while standing naked in my living room. My breathing was coming hard and fast, and I was afraid I would cum, but before I could get there I felt Greg start to ease off, until he finally let go of me completely.
"How did that feel?" he asked.
"Incredible!" I replied.
I was desperate for more - I felt Greg's hands grasp my shoulders, tilt my head to the side, and he started to kiss my neck again, soft at first, but soon becoming more passionate and animalistic. My cock was still hard, but it wasn't being touched, it just kind of stood out straight in front of me. Without meaning to, I pushed my ass back towards Greg, and found myself grinding against his hard cock through his pants. I could feel it rubbing against my ass, teasing my crack, and knew it wanted to be uncaged.
Trembling, I broke away from Greg, turned around, got on my knees in front of him, and fumbled at his belt, finally unfastening it, unbuttoning and unzipping his pants, and slowly peeling the pants away from his body, pushing them down to his ankles. I gently felt and rubbed his cock through his underwear (briefs), before slowly peeling them away. I watched as his hard cock came into view, and exhaled sharply when it sprung to attention just inches from my face. I gazed at it, the purpose mushroom head pulsating as it invited me in. I ran my hand up the inside of his leg, and slowly reached in towards his erect member. It twitched as I touched it, and Greg let out a heavy sigh. It felt so good and so different in my hand. Not sure what to do, I started to slowly work it back and forth, hearing Greg sigh and moan and breath heavily as I did so. I watched the hole at the tip, watching the skin slide back over the mushroom head, fascinated and content to keep doing it. Greg, however, had other ideas.
"Do you want to suck it?" he asked.
I hesitated, but then slowly nodded. Greg took a small step closer, presenting his cock to me, I let go of it, started to rub his legs and ass, and leaned in towards him. I felt the tip of the cock touch my sealed lips, and pulled back quickly.
"It's ok," Greg said, "Just take it easy."
Slowly, I moved towards it, still on my knees. I looked at it for a few moments, before opening my mouth and slowly taking the tip inside me. It felt warm and tasted slightly of salt. I loved it. I teased the tip with my tongue, feeling Greg shiver and start to moan. I slowly eased my mouth over the rest of him, and before I knew it he'd buried about 6 inches of himself in my throat. My tongue began to furiously lick him up and down, and I moved my head back and forth on his erection, loving the feel of him sliding in and out. I could feel my own cock still hard, and reached down to play with myself while I continued to roughly suck him off.
I have no clue how long this went on for, but I felt Greg stiffen slightly and pull away from me.
"Slow down, tiger, I don't want to cum yet." He pulled me to my feet, and started to undress himself. His clothes came off one by one, until they were discarded on a pile on the floor of my living room. I gazed at his nakedness, drinking him in, heart pounding, sweat beginning to glisten on my body, aching for whatever came next.
Greg closed the distance between us, and I felt him take my cock in his hand. I did the same with his, and we slowly jerked each other off, enjoying each other's manliness. Greg then pushed my hand away, put his hard cock over the top of mine, and started to slowly pleasure us both. Feeling my hard cock next to his was incredible - there are no words to describe how erotic it was. I thrust forward to meet his every push, and could feel my cocking pulsating in his hand.
"Where's your bedroom?", I heard Greg say.
"Through here," I said, noting that my voice was still shaking. I led him towards my bedroom. I was very conscious that I was naked and he was looking at my ass if I walked. I felt completely exposed, but loved it. I knew that he wanted me, and that made it even better. We entered the bedroom. Unsure of what to do next, I sat on the edge of the bed. Greg then took charge, clambered on the bed beside me, pushed me down onto my back, then laid on his side. He pulled me towards him, and I turned, reaching for his cock, feeling his strong hands on my back pulling me in, and before I knew it his mouth had found my own and his tongue was inside my mouth. My tongue sought out his, and soon we were kissing passionately, pulling on each other's cocks. My body was thrusting and grinding against his. I'd not felt anything like it before this point.
Soon, our kissing broke. I was breathing so heavily I felt like I was gasping for air. Even though the kissing stopped, my body continued to grind and thrust. I felt my legs opening and knew I wanted to feel him inside me.
"If I go gently, can I fuck you?" asked Greg.
"Yes!" I said. I was nervous, frightened even, but desperate for this experience. I fumbled around in my beside table drawer and retrieved a condom and some lube - I had stipulated safe sex only. I laid on my back and played with my cock while Greg worked the condom onto his pulsating dick, then took a generous helping of lube and rubbed it up and down his shaft.
"Turn over," he said gently. I did, getting on all fours. Greg took charge again, raising my ass up and pushing my head down. I could feel my dick throbbing, but didn't know what to expect. I then felt pressure against my ass hole - I tickled around the rim, making me shiver, but then the pressure came and I knew that he was trying to slowly and gently enter me. I kept my ass up, and could slowly feel my ass opening and his dick entering. It was a slow process, and it hurt, but it also felt good at the same time.
"Is it in?" I remember asking.
"Almost, you're really tight," said Greg, breathing heavily. I felt a little thrust at that point, then a tingling electric sensation inside me. I knew he'd hit my prostate - he then slowly started to work back and forth, pushing in and out, in and out. I could feel both pain and pleasure - it's hard to describe, but I knew I didn't want him to stop. I began to push back hard against him, feeling him slide, first all the way in, then all the way out, slowly at first, then building up speed.
I began to grunt and moan - I could feel his physical mass above me, dominating and controlling me - even if I'd wanted to stop at this point, I couldn't have gotten him off me, so I was at his command. I fumbled around for my own dick, and realised it was semi-hard, but as he continued to fuck me I felt something build and build inside me, a pleasurable pressure that just wouldn't ease up and kept gaining in intensity. Greg was now fucking me hard and fast, harder and faster and faster and I was thrusting against him. I felt an odd sensation continue to build in me, my cock still only semi-hard, but within seconds I felt spurt after spurt of my own cum coming out of my dick, covering my sheets, as Greg continued to pound. I could feel him building up and then he slumped on top of me, spent, and I felt his cock twitch and spurt inside me, his cum caught by the condom.
Release was amazing - I felt physically exhausted and totally content. I laid flat on my stomach, my own cum sticking to my leg and groin, and Greg slumped on top of me, his dick still in my ass, slowly softening. When he finally pulled out, I rolled over, and watched as he took the condom off. It was fully of cum. My ass felt funny, all lubed up and sticky, and it burned slightly, but I knew that I wanted that experience again and again and again.
Greg left without saying much else, but did say he was available any time for a repeat performance.
I never saw him again - he never responded to any texts, although I did see him around once or twice with whom I can only assume were his wife and s. He was my first guy, my first top, and gave me the courage to try new things. I still think about that experience when I masturbate, and although I'm now married again, I do still occasionally get together with another man for a mutual masturbation session - I never learn their names, and only see them once. No one knows this about me - it's my dirty little secret.
This website is for sale. If you're interested, contact us. Email ID: [email protected]. Starting price: $2,000