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.

Momentos Of My Other Life

I have two cell phones. One is for day to day activities, the number of which I give out to my family and friends. The one where people from work can reach me. Its the one I use to book taxis, order takeout, and hundreds of other little telephonic chores.

The other is the one I use to hook up with guys.

It's the number I give out to potential hookups. The one that contains my body and cock pics, so I can send them via text to interested guys. The one that contains the cock and body pics guys have to sent me as well as a load of saucy texts telling me what they would like to do to me, or what they want me to do to them.

The contact list is made up of potential hookups and the men I've slept with, well at least those who were more than a one night stand, or the occasional one nighter who I may like to fuck again.

I still have the number of the first guy I slept with, the number of my almost boyfriend fuckbuddy, and the number of the last guy I slept with (who was the guy I fucked bare).

These are the momentos of my other life, my sordid little sex life which I share in this blog.

On Show

I performed on webcam today, the first time this year.

It started this morning when I was chatting to a friend on MSN. We did our usual ritual of flirting back and forth. He tried to show me his body on cam, but it wouldn't connect, so went offline for a few minutes.

All the flirting had got me feeling horny, so while he was offline I removed my clothes and when he returned I was ready to show him just how horny I was. However the messenger had other ideas, and try as I might, it wouldn't let me show him my cam.

So, frustrated, I started surfing the usual gay cruising sites, looking for a little daytime action.

I ended up on one site where people can view webcams, and since I was already in the mood to cam, I published my webcam, got into position in front of it and started to jerk off.

It wasn't long before I had a list of viewers, and messages coming in about how sexy I am, how nice my body is, and how hot my cock is. Lets just say my ego was being stroked as much as my cock was.

Along with the messages came the requests:

"Stroke faster"

"Show me a close up of your cock"

"Can I see your ass?"

I tried to oblige as much as I could. While showing off my ass and hole at the request of one guy, another wanted me to stick something inside there. Something large. Which was not going to happen. Well, nothing larger than a finger or tongue.

The show lasted the best part of an hour. One guy wanted me to tell him about my first time with a guy, so I had to manage typing with one hand while continuing to jerk off with the other.

Eventually requests came in for me to produce, in porn terms, the money shot. Someone requested that I move as close to the camera as possible and shoot, however I wasn't about to ruin my keyboard with cum, and told him so. Instead I turned slightly to the side, and leaned back slightly too. I held my cock so it pointed up towards the ceiling and jerked faster, feeling the pressure build up behind my balls, and shot my load over my torso.

The first volley struck my cheek, more cum splattered my arm, my chest and my abdomen. The sticky white fluid turned cold and began to run down my body.

Show over, I disconnected my cam, and walked over to the bathroom, where I ran a bath and soaked my cum splattered body in the warm water.

Dare To Bare - Part 3

Follow the links for parts 1 and 2.

I continued to rub my hard on between his asscheeks, teasing him with it while I decided whether or not to enter him bareback like he had asked. Despite shooting my load over his ass earlier, I was feeling very horny, the thought of entering him raw is very taboo which made it all the more alluring.

I decided to go for it, moving back slightly to position the head against his hole. His ass was loose and still slick from the lube from our previous fucks, so sliding the head in was no problem. He pushed his ass back onto my hard on, and he accepted my raw cock into himself.

It felt fantastic. I could feel the walls of his ass around my cock, the slightest movement of my hips was thrilling. I can see how barebacking can become addictive, you feel so much more when fucking raw.

I had to fuck him slowly at first, to give my cock time to relish the new sensations. I almost felt like I could shoot right there and then, it was so good. My cock was the hardest it had been throughout our session, and I think he could tell too. Instead of the porn dialogue, he was moaning deeply, enjoying it as much as I was.

I pumped a little faster, and could feel the pressure increasing behind my balls and my balls beginning to rise, I was about to shoot. I slowed down my thrusting, and tried to squeeze my pc muscle to delay ejaculating. It seemed to work, and I didn't shoot.

I began nibbling on his ear as I increased thrusting. Delaying my orgasm had made me want to shoot more, and his ass felt so good. I lost myself in the moment and shot my second load of the day inside him.

This was my first experience of going raw, and it did feel good. I'm unsure if I would do it again, it would depend on the situation (how horny I feel at the time), however I have been jerking off to the memory of it ever since.

Dare To Bare - Part 2

Part one of this post can be found here.

So I was getting sucked by the guy in the previous post, and from time to time I would push my cock in all the way and hold it there. This guy liked to be dominated. I tried to get him to lick my balls (another favourite) by pulling out my cock and offering my balls near his mouth, but he just wanted to suck my cock, which he did greedily.

After a while he flipped over onto his stomach, and I lay on top of him with my cock nestled in his crack. He said he loved the feeling of a man on top of him, and the feeling of my cock slowly grinding in his crack. He wanted to be fucked again.

I told him that I was no longer wearing a condom, and he said that it was up to me if I decided to put one on. Common sense won out and I got up to find another condom, rolled it onto my erect cock when I found one and rubbed some lube onto it.

I positioned myself between his legs, using my knees to move his legs apart. Gripping the base of my cock, I slid into him again. I pumped away, meanwhile his porn dialogue repertoire had resumed. I nibbled on his ear whist fucking him and the faux dialogue was replaced with some very real moaning.

I had a need to get off, so after a while I pulled out and pulled of the condom. I started jerking off. He wanted me to cum, first in his ass, which I questioned, then on his ass, so I increased my jerking and soon shot my load over his hairy cheeks.

We cleaned up, then lay back on the bed chatting, me lying on top of him, which as I mentioned before he liked. I gave him a massage, starting with his back and shoulders,but without any oils it wasn't one of my best, still he seemed to like it.

I flipped him over and lightly licked and nibbled at his nipples. I reached for his cock and jerked him off, I wanted him to cum too, but I guess he's one of those guys that gets off on making guys cum without the need to cum themselves.

He flipped himself back onto his stomach and told me to lie on his back, which I did. We chatted for a bit like that, and he could tell I was getting horny again as my hard on had returned, and was resting between his cheeks.

I began slowly grinding myself against him, slipping into his crack, and teasing the opening of his hole with my cock head. He wanted me to stick it in him, raw. I continued teasing his hole, deciding whether or not to do it.

Dare To Bare - Part 1

"Ohhh! Fuck me! Fuck me! Fuuuuuuck me!"

This guy had definitely been watching one too many porn movies, and didn't know how much of a turn off it was. He was lying naked on the bed, and I quickly stripped off my remaining clothes and joined him.

I lay on top of him and we kissed. I moved down to lick his neck, then down to suck and nibble on his tits. Tits being an accurate description as he was a little heavier than his profile picture. I made a little sawing action on his engorged nipple with my teeth which sent him into a state of bliss and he let out a sigh of pleasure.

He wanted to be fucked there and then, so went across the room to get a little kit bag containing the condoms and lube, and I rolled a condom onto my cock as he lubed up his hole.

He returned to the bed, lying on his back, legs in the air, with his ass hanging off the edge. My sheathed cock entered him, and he moaned audibly. I slowly pushed in until my cock had fully entered him then left it there for a moment. His legs had come to rest on my shoulders, and again he said what he wanted:

"Ohhh! Fuck me! Fuck me! Fuuuuuuck me!"

I obliged, pulling out slowly, before pushing back in with a little more force. I slid in easily, and again he moaned. I made a circular movement with my hips, which made his head swoon back.

He wanted it harder, and deeper, so I held his legs tighter and pulled him part way off the bed. More of his weight was now supported by my legs, and meant I could use those muscles to pump deeper into him.

His incessant porn star moaning did nothing for me, and after a few minutes I started to loose my hard on. I pulled out and jerked my cock to get it hard again. Meanwhile he had flipped over onto his front and said he wanted me to lie on top of him. I did, using my legs to push his apart, rubbing my cock between his ass cheeks before I entered him again.

A few minutes of ass pumping went by, accompanied by yet more porn dialogue, so unsexy, and again I began to loose hardness. I pulled out and turned him over on his back, using that time to jerk more blood back into my cock. Again he placed his legs on my shoulders, I entered and spent time working his tits with my mouth as I fucked him.

The fuck was doing nothing for me, and again staying hard became an issue. I pulled out of his ass for a third time, ripped the condom off my cock, and with a little bit of maneuvering aimed my cock into his mouth, which put a stop to the porn style moaning.

Much better, I grew harder in his mouth, and face fucked him. I changed position, with me standing and his head hanging off the edge of the bed. This allowed me to go in deeper.

I attempted the 69, which is one of my favourite sexual positions, but I guess he doesn't like having his cock sucked, so I had to go without that sexual favourite.

More about this latest fuck in the next post.