Sexual Education With Mr Silver

Whenever I met Mr Silver, it was always at his house. We would arrange to meet on my days off, since he worked from home most days. He would pick me up, drive me to his place, we would have sex in the morning, have a bite to eat, have sex again in the afternoon, shower, and he would drop me back in the city.

Sounds good, and on the surface it was. But there was a problem, I couldn't cum when I had sex with him. I have mentioned before how when I had sex with a guy, I had to really concentrate to reach orgasm. That problem continued when I was with Mr Silver. I didn't mind though. I could easily get off when I returned home, when I was on my own, I could replay the sex we had that day in my mind and reach a ball busting orgasm.

I had sex with Mr Silver to feel the weight of another body on mine, to kiss his lips, get my mouth around his cock, to suck on his balls, and to have those things done to me, even though my erogenous zones were still extra sensitive. I would smile and laugh with glee as he explored my body with his mouth. I was like an eager puppy and my tail was always wagging.

He certainly enjoyed my body. Loved the size and feel of my cock, which always seemed to be in a state of permanent arousal. At first, the fact that I couldn't cum bothered him. I told him that not ejaculating didn't upset me, I loved the sex we had together, and loved exploring my sexuality with him. In contrast, every time we met up for sex, he came.

Over our time together we indulged in many forms of sex. He was the first guy to rim me. The feeling of being rimmed was intense. Pure pleasure overload. I would squirm and gasp and hope it would never stop.

He was the first man I fucked. Sticking my cock up his ass was another odd sensation when I first attempted it. We were always safe, so I guess wearing a condom was part of it. He wasn't the tightest down there, but once I got used to the sensation, it felt good. Doggy style was a favourite of mine, and still is.

He had a bit of a leather fetish. He liked me to fuck him while I wore my leather jacket, loved it when I hadn't shaved in a few days, as he had this fantasy of being roughly fucked by a hoodlum, forced to take a cock up his ass, a fantasy I obliged.

Once I gave him a blowjob as he drove his car. We were on route to his house, driving down a quiet country lane. Often when he drove, I would sit with my legs spread wide, and his hand would wonder over my groin. He loved looking over to see my erection straining against my jeans, and at times my hands would fondle his groin too.

On this occasion, I had unzipped his fly, and he was going commando so his cock head poked out of the fly of his trousers. There were no other cars around, so I hooked my seatbelt around the hand rest of my seat, leaned over and gave him head. I know, totally stupid as we were in a moving car, being a horny youth is my only defence.

He loved it when I would give him a prostate massage. The first time was a surprise for him. I brought a medical latex glove from home, and when we were naked on his bed I reached over into my backpack, put on the glove and presented my sheathed fingers to him. He wondered what I was up too, and I soon showed him. I lubed up my fingers and put my middle finger up to his hole. I applied gentle pressure and my finger slipped in easily. I finger fucked his hole for the best part of an hour, time and again rubbing up against his prostate, edging him until he shot a torrent of cum. After that he made sure there were fresh latex gloves in the drawer where he kept his lube, condoms and poppers.

We had sex in most rooms of his house, I would give him blowjobs on his couch, and once on the stairs. We had shower sex, and once after sharing a bath together I fucked him in the tub. One of our most memorable encounters was when we tried bondage.

The May To December Encounter

This is how I met Mr Silver.

There was a gap of four months between loosing my virginity to Guy #1 and having sex again. By that time Guy #1 and I were no longer in contact, which was mostly my doing. Guy #1, was bisexual, married, and had a kid. By his own admission, his wife had no idea of his extra-marital activities, and there were many of those. Guy #1 was a player.

In contrast, I wanted a relationship. Something I wanted for a long time, ever since experiencing the first pangs of love whilst in university. Guy #1 couldn't give me that, so I had to look elsewhere.

When I first met Mr Silver on the gay chatline, he told me he was in his early 40's. It was only later in the relationship that I discovered he had knocked 10 years off his age, putting him in his 50's and making him the same age as my father. The age difference didn't bother me, rather the fact he lied and kept up the pretence for so long. I felt like a fool for believing him so readily.

We met when I was 23, and still a novice when it came to men. After trading text messages for a while we had agreed to meet up. The venue was outside a theatre, located near the centre of the city. He had parked near the entrance. As I walked towards the theatre, my cell phone rang. He had called to see if I was the guy walking towards his car. I said yes and he flashed his lights to indicate which vehicle was his. I rang off, walked over to his car, opened the door and got inside.

He was handsome, with silver hair cut short and spikey, hence the name Mr Silver. He had a few laughter lines around his eyes and mouth when he smiled. We said hi, talked for a while, and he asked if I wanted to go to his place for a "coffee". I suggested this first meeting to see if we liked each other, so I thought "coffee" would involve a caffeinated beverage of some kind. Hey, I did say I was a novice when it came to these things. I buckled up and off we drove.

He lived out of the city in a small town. The journey took around 40 minutes. As we drove there, the old spectre of doubt popped up in the back of my mind. I'm in a car with a total stranger, driving to an unknown location and nobody knows where I am. I know, I know, things could have gone so badly wrong. I could have ended up injured, or worse, but there is always risk in meeting someone new.

We arrived at his house, located on the main through road leading into the centre of the town. In we went through the side door of the house into his kitchen, and he asked if I wanted anything to drink. I asked for water and he poured out two glasses from a jug in the fridge.

We sat in his lounge and talked. He told me a little about himself. He was single since his partner died and was now looking to get back out there. I reciprocated with some information about myself, how I was single, that I had recently had sex with a man for the first time and wanted to explore my sexuality further.

He seemed kind and friendly, joking with me and making me feel at ease. I noticed he was staring at me intently while we talked, and he eventually asked if he was allowed to kiss me. I nodded and we kissed. He was a good kisser, and after 10 minutes of lip locking I whispered "Let's go upstairs".

I hadn't planned on this happening, certainly not to sex with a guy within two hours of meeting him, but I thought what the hell, just go with the flow and if the sex was bad I would not have to see him again. He lead me upstairs to his bedroom.

We kissed, only interrupting our make out session to shed clothes. He took his cue from me, and because I kept my underwear on, so did he. We fell onto his bed, and continued to kiss each other. Age had filled out his body a little, but he was toned (later he confessed to hiring a personal trainer to help him get fit). I enjoyed his body, and he mine. When we removed our underwear, he marveled at my hard young 7 inch cock. His was smaller, around 5 inches, but I found it was the perfect size for sucking, and suck it I did. I relished the feeling of having a cock in my mouth again. We traded blowjobs in between bouts of kissing, our hands feeling each other all the while.

We finished with him on his back and me straddling his stomach, he jerked his cock as I jerked mine. He shot his load onto my hairy butt cheek. Again I had to concentrate to reach orgasm, eventually shooting my load, the majority of which splattered onto his headboard which was three feet away. A feat he was very impressed with.

He let me take a shower to get his cum off me, and after we dressed he took me back into the city. We agreed to text each other, and we did, arranging to meet again. Meeting up with Mr Silver became a regular thing, and my sexual horizons were broadened.

The Difficult Second Relationship

I'm finding it hard to write about my second sexual relationship. The difficulty lies in trying to separate the sex we had from all the crap that went on between myself and Mr Silver. By that I mean it's easy to describe the sexual acts I performed (and enjoyed) when we were a couple, but there was also a shift in the relationship as time went on that eventually broke us apart and taints our time together.

Hindsight is a wonderful thing, and looking back I would have done things differently, but I was young, naive and horny. I didn't see things changing till they were too late. I took things at face value and believed everything he said.

But to say it was all his fault would also be naive. I changed too. It was a combination of growing up and events occurring in my life at the time. I was no longer a wide-eyed 23 year old, practically new to sex, ready to explore and experiment. Optimism had been replaced by something darker.

The relationship lasted for three years, but we didn't spend every day of those three years together. There were times when we spent months apart, breaking up then getting back together then breaking up again. I even fell head over heels in love with someone else during one of our break ups, but that new relationship never got off the ground.

An alcohol induced text message brought him back into my life, and I found myself back in the crap that caused our previous break ups. The relationship with Mr Silver ended soon after.

The First Taste

I sat in the middle of the couch, nervous as hell. It must have shown on my face, as Guy #1 told me to relax and to move closer to him. Without realising it, I had kept a gap between us earlier when I sat down next to him. I scooched over a little.

We were sitting in the family room his house. It was a little weird to think that earlier that day his family were here with him, getting ready for a day at work and school, and now we were here, about to have sex, and they would have no idea.

He stared at me as he chatted, one arm draped over the headrest of his couch. He wanted me, the lust evident in his eyes. He asked if he could kiss me, and I nodded. His arm slid down off the head of the couch, pulled me closer to him and our lips met.

We kissed, slowly at first, but the pace soon picked up as our passion increased. His tongue found its way into my mouth, and my tongue flicked around his. We kissed for ten minutes, and broke apart, hot and breathless. He asked If I enjoyed it, and yes I did, very much. The throbbing member in my pants was testament to that.

I pulled off my t-shirt, we started kissing again. His hands wondered over my naked chest as my fingers felt his still clothed torso. My skin tingled at his touch. We pulled apart again for him to remove his t-shirt, and I was presented with his smooth muscular chest.

Not gym toned muscular, but the kind developed from playing sports, predominantly football. My left hand reached out and ran along the taut skin of his abdomen. I could feel the ridges of his abs under the skin. I leaned back in and moved my mouth down and kissed his pecs and licked his nipples, just as I had fantasised. I had finally got my hands on a man and I wanted to take advantage of every opportunity.

I slid off the couch onto the floor.I was on my knees between his legs. It was the perfect position to be in for what I had in mind. I wanted cock, and one was practically within reach. I asked if I could see his dick. He lifted his ass off the couch so he could push down his track pants and underwear in one movement, then sat back down.

There it was, the prize I had waited a lifetime for. Resting between two muscular and lightly hairy legs, surrounded by a trimmed bush, was his cock. I wrapped my left hand around it and slid the foreskin back and forth, slowly exposing and then covering the head. My grip became slightly firmer as I jerked him off. A drop of precum appeared on the slit, my signal to take the next step. I leaned in as I stuck out my tongue, using the tip to lick at the clear drop in front of me. I savoured the taste, mentally comparing it to the flavour my own precum. I then put my lips around the cock head, careful to cover my teeth as I did so, and started gently sucking him, my hands resting on those muscular thighs.

That was it. The first taste, and I was addicted. I sucked more, taking him further into my mouth. His groans of pleasure indicated I was doing something right, and his cock grew to it's full 7 inches in my mouth. I admired its length and thickness as I licked the shaft and head, trying to emulate the actions I had seen in the gay porn film I had recently purchased. I ran my tongue down over his scrotum, licking at this balls and savouring the flavour. All traces of nervousness had disappeared, replaced by lust and horniness.

My cock was hard, throbbing and leaking precum in my underwear, and I was still in my jeans. I pulled away from his crotch, stood up, unbuckled my belt and quickly removed my jeans and underwear in record time. I tossed over to a chair, abandoning them on top of my discarded t-shirt and next to my sneakers and backpack. I stood there, hard and naked, in front of him. The head of my cock slick with precum. He slipped off the trackpants and underpants from around his ankles and then stood up.

I took his place on the couch and he took my previous position on the floor. He sucked my cock into his mouth and began to give me a blow job. The sensation was intense. My cock had only ever known the feeling of my hand, so this was new territory. I put one hand on each side of his shaved head, not to stop him or force him down onto my erection, but to lightly hold his head as he blew me.

After a while I pulled him off my cock and switched positions so I was between his legs again. Let's just say I had found out something about myself that day. I was a born cocksucker. The thing missing from my life had been placed between my lips. Sucking on his cock felt right, and I was in heaven as I blew him, licking his cock and balls with ecstatic glee.

When I shifted position so I was on my back on the floor with my legs up on the couch, he looked at me with a puzzling expression on his face, wondering what I was doing. It took a moment for him to realise what I wanted. 69.

He lowered himself onto me, one leg each side of my head. My mouth on his member as his mouth sucked on my cock. It was the perfect position, sucking on his prick took my attention away from the intense feelings of having my cock sucked, and I could enjoy the sensations of having my cock sucked while sucking on one myself.

My hands moved up and down his thighs as we blew each other. In this position I had a good view of his asshole, perfect and puckered, above me. I had the urge to finger it, but didn't want to rock the boat by doing something he may feel uncomfortable with, so I left it alone. I had lube and condoms in my backpack, just in case, but they were not used.

As he increased the thrusting motion of his hips, more of his cock disappeared down my throat. Only once did he bottom out, his full length pushed into my mouth and I gagged around his cock. Tears streamed from my eyes, but he pulled back a little, sensing my panic, and I kept right on sucking him.

He had to be at work later that day, so we didn't have long left. He got up, went out of the room and returned with a large bath towel. By the time he came back, I was sitting on the floor with my back resting on the couch, slowly jacking my spit soaked cock.

He laid the towel on the floor, and we both sat on top of it. We both began to jerk off as we watched each other and he came in a matter of moments, pointing his cock down so the fat drops of sperm fell onto the towel. He wanted me to cum too, and I was trying. This would be the first time I would cum in the presence of another person, shyness crept in and try as I might I could not get myself to the point where I could blow my load.

He moved forward, rubbing my torso and licking my nipples in an effort to make me cum quicker. It didn't work. I was not used to having someone else touch me when I jerked off, my mind had an established rhythm in the lead up to ejaculating, and his actions had the opposite effect to those he desired.

I closed my eyes and had to concentrate. I thought about what I had done that morning, that I had finally lost my virginity, finally got to feel another mans cock in my mouth and see him loose his load because of me. That this would be the first in a lifetime of man on man sex.

That was it, I worked my way to a ball busting orgasm, and shot my load onto the towel.

Well most of my load. A few drops of sperm shot beyond the towel and landed on the carpet (well, I was a horned up 22 year old, and had been known to spray my load over my shoulder and onto my headboard in my solo sessions). He wasn't best pleased. Leaving evidence like that could have blown his cover. I apologised and used a corner of the towel to wipe away the incriminating evidence. I cleaned up my cock and dressed as he left the room again to get rid of the towel. He came back into the room to dress in the clothes he had left in a pile next to the couch. Dressed, I picked up my backpack and we left his house.

The plan was to drive me to the train station where he picked me up, but as he was running late for work, he asked if he could drop me off near a bus route that would take me into the city. I agreed. I guess in the back of his mind he was thinking he had to get back home and check that I had mopped up all the drops of spunk that had landed on the carpet, that all evidence of that mornings illicit activities had to be erased.

As he dropped me off, I told him that I had an amazing time, as did he. He couldn't believe that was my first time, and I had to assure him it was. He said he would text me later in the day, we said our goodbyes and he drove off. We texted a few times after that, but he was due to go away with his family on holiday, so meeting up again would have to wait.

It would be five years before we would meet again, and in doing so he would introduce me to the pleasures of group sex.

The Good Student

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Guy #1: The First Meeting

I was 22 when I first had sex with another man. He was a married bisexual jock in his early 30's with a shaved head, smooth torso and 7.5" uncut cock.

This is the guy I alluded to at the end of my last post. It was on my day off and I travelled by bus to a train station located roughly equidistant from where we both lived. I was more than a little nervous as I walked up the road towards the station, not least because I was meeting a complete stranger and no one knew where I was.

I spotted a man sitting on a low wooden fence and next to a car, on the side of the road I was walking on. He had given me a description of his car in our last phone conversation, but I was so nervous the information flew out of my head. As I got closer I could see that the man roughly matched the description of the guy I was meeting, and was wearing clothes similar to the clothes he said he would wear.

I slowed down as I approached him, the hint of a smile on my face. I wanted to appear friendly, but was wary in case this guy turned out not to be the man I was due to meet. I need not have worried. He said hi and used my name, I returned the greeting, we shook hands and he asked if I wanted to sit in his car with him. I agreed.

He studied me as I sat in his car, and I did the same. He was as attractive as I had imagined (this was a time before camera phones so I had no idea what he looked like before this first meeting) with hazel eyes and high cheekbones. His head was shaved smooth and his skin was tanned.

We chatted. I knew he was married and had to be discrete, as did I as I was not out. I explained to him that I was still a virgin, and apart from kissing a guy during my time at university, I had no experience with guys. He said that because of his situation he couldn't take me back to his place on that day as his wife was home, even though he wanted to, so we agreed to arrange another time to meet when he had the place to himself.

He told me how attractive I was and how much he wanted to kiss me, but as we were out in public we didn't touch. He said he definitely wanted to have sex with me. I just wanted to have sex, but I rephrased it by saying I liked him too.

I left him in his car with the promise that I would text him when I had a day off from work, so he could take some time off too. So two weeks later we met up again at the same train station. I once again got into his car and this time he drove me to his place where we had sex.

Hangin' On The Telephone

When I got my first cell phone, little did I know that it would be my passport to man on man sex.

The phone was to be a way for my parents to contact me when I was out at work, but I used it for so much more. Every Saturday I would buy a broadsheet newspaper on my way to work, inside of which was a television and local listings magazine. The magazine had a dating section and adverts for chatline services, both straight and gay. As this was my only outlet for contacting gay men I thought I would give it a try.

It took a few tries before I found one I liked, and I would often call my favourite chatline late at night and jerk off while listening to the voice profiles of the men online. I began to recognise the profiles of some of the regular users, including the profile left by guy I would loose my virginity to.

At the start my profile was pretty basic, so it was rare that I would get a response. Over the months I used the service I picked up on how men would describe themselves and the terminology they used depending on what they were into and what kind of sex they were looking for and I adapted my profile, making it more descriptive, which attracted a lot more attention.

I actually met one guy who responded to my profile. We had coffee in a shopping mall. It was so long ago that I can't remember much of the encounter, though I remember he wasn't the most attractive guy, and the conversation was a bit dull but if he had invited me back to his, I would have gone. It wasn't about the guy, it was just about having sex (which, with enough posts detailing my sexual history, you will see is a recurring theme).

Instead we parted and although we communicated by text a few times we never met again.

I went back on the chatlines, usually at night with me lying naked under the covers masturbating. One night I was on there and as I was going through the list I heard a, by now, familiar profile. The guy seemed to be online every time I was, and I had often jerked off to his description of himself. He sounded very hot, but I thought he was out of my league, so I would not contact him.

However, that night I was feeling brave and I sent him a hello message, to which he replied. We exchanged many messages that night and by the time I ended the call I had his name and his cellphone number, knew a little about him and he about me. I sent a text to him that night, so he had my cell number.

Over the next few weeks we texted back and forth and also had a few phone conversations in which we arranged a time to meet, as I put it, "to see if we liked each other". He agreed and on a cloudy Tuesday morning I found myself traveling on a bus to meet my bisexual football jock.