My First Time

This series of stories is something that I have compiled overtime, I started having sex with guys when I was rather young, and made a point after my first 3 or 4 sex sessions to document the meets that I thought stood out amongst all the sessions that I've had. The series is in 24 parts starting with my first time and running through to the present day. Everything you read is genuinely true and I hope you enjoy reading through them!

Chapter 1: My First Time

I had just turned 18. I was a student at Harlow college, I spent 3 days a week in Harlow attending college, and after we was dismissed in the afternoons, I'd walk over to the bus station and started to have thoughts of meeting someone completely random to have sex with. Harlow gave me that horny and anonymous feeling every day that I'd walk around the place.

One lunch break I was walking through a wooded area just outside of town and found an area next to a big tree, and on the ground were at least 5 condoms all filled with cum just lying on the floor. This got me seriously thinking to myself that I wanted to hook up with someone random and let them have their way. However, I found that it was easier to get decent chats sites that were for gay guys rather than straight. I always wanted to feel what I was like to suck a cock, and get fucked and also wondered what it would be like to swallow a random guys load.

One night I discovered squirt. The gay hook up website. I had been chatting to a guy from Norfolk but was living in Epping. It looked like he had a decent sized cock but he claimed it wasn't as big as it looked. I talked all night to him and stared and pics of his cock thinking that maybe I was going to lose my bottom virginity to him. We said that we would meet the next day.

The next day came and I went straight onto squirt to arrange my first time but couldn't get hold of the guy I was talking to the previous night. However, I soon found another guy. He was a fast responder paramedic living in Harlow. His screen name I can remember, it was 'HarlowFun'. Always remember your first timer. He said to me to come over and gave me his address. It suddenly dawned on me that I had to make a choice to go or not to go. I would have to go by bus and I wasn't old enough to drive yet. Screw it I thought, I had to find out what it was like. So, I told him I'd be about half hour and I went to get the bus. I got on the bus shaking and the trip to Harlow seem to last forever. The closest bus stop to the guys house that my bus went past, was around 1/4 mile away from him. So, I had a little power walk to his place once I got off the bus.

The guy lived at number 74 Five Acres. I found the place and knocked on the door, physically shaking. Then a guy, around age 45, opened the door and was surprised that I actually turned up as I'd taken longer than expected but was still rather happy. He led me upstairs and we laid on his bed. And started chatting. Soon he started to stroke my trousers so I returned the favour. I could feel the relatively small dick throbbing under his shorts. He suggested that I took my jeans off so I'd be more comfortable, so I did. He asked what would you like to do, so I replied let's suck it and see. He laughed and pulled his shorts down. There in front of me was my first cock. Relatively small but already quite hard. I slowly moved my face closer to it and opened my mouth. I started to suck his head rather slowly and then all the way down his cock, which wasn't that far if I'm honest.

After a short while he started to suck me off briefly and then said would you like a shag. I thought yeah sure. He laid me down on my back and started to rub his cock on my hole. I laid there thinking to myself, oh my goodness this is it, I'm about to lose my virginity to a random bloke. I braced myself. But then felt a warm sensation on my stomach, he hadn't even penetrated my ass and he had already cum all over my stomach.

Well that was a waste of time I thought.

We cleaned up and he seemed desperate for us to meet up again. I left his house and headed for the bus stop, with the thoughts of I hadn't set out to do what I wanted to do. I had sucked my first cock, but that was it. My mission was a failure.

I headed home very pissed off and I never spoke to the guy again.

The next day I got back on squirt to find my next client...