First anal

I have been bi since i was a young teen. Started out with a friend after a dare to streak across a park one night. We did that, that broke the ice, and from there we went on to masturbate in front of each other, to each other, to me giving him blowjobs. I ended up playing with a couple of other school friends as well. One tried to fuck me, but we both had no idea what we were doing, so it did not happen. 

Once we all left school it stopped. After a couple of years maybe longer I was sent out of town for some on the job training to a much bigger city.  One Friday night I got talking to an older man. He walked me to a local park, I knew what he wanted, I was ok with that. We got to the park and it was a bit awkward as we both stood there not saying anything, so i laid down and then he laid down next to me and started to rub my cock thru my trousers. 

I then did the same to him, he then decided we needed to go back further into the park. He actually wanted to take me back to his house but i was too nervous to do that. We took our trousers off and he soon had me on my stomach and tried to fuck me, but I had no idea how to relax and we had no lube. I ended up fucking him, then giving him a blow job. 

I actually felt very guilty after as i walked off back to my accommodation. A couple of days later I decided it felt good so why stop, and I went to a gay sauna for the first time. I was nervous at first. I had a walk around the place and it was not long before a guy came onto me and took me to a private stall. Again he wanted to fuck me, and while he did have lube, there was no way my arse was going to let a cock in, so we ended up masturbating each other. Over the years this same thing happened. 

One day I was due to go out of town over night for a training course. Before I headed down there i looked at a gay site and found a top with a very small cock, about 4 inches. He agreed to meet me at the motel. He turned up with wine and some amyl. We drunk the wine then we got started. I got onto my knees and too out his cock. After a short time he had me get on the bed, lubed me up, gave me the amyl and then put his cock in. Even though it was a very small cock, it still hurt quite a bit, it was all over pretty quick. he asked if i wanted him to cum on me, i said yes so he pulled off the condom and cum over my balls and cock. That was probably the best part. 

Once i was home i decided i needed to learn how to relax and take things anally. I brought a butt plug set and a vibrating butt plug, along with lots of lube. I started with the smallest one, and soon moved to the middle one. That one was not quite so easy to get in, but i learnt how too relax and take it. 

After a short time it was too easy to get in, so moved to the bigger one. That took a bit of an effort but soon was all i used, then I tried the larger vibrating one. That took a few goes to get in, but what an orgasm I had when it did.  The training set ones would stick to the shower wall and I would use them often. Sadly I lost them and my sexy G String.  

Many many years went by. I met a few guys but never tried anal sex with them. One day i signed up for grindr and advertised I was keen to try being a bottom. I was messaged by a guy who was visiting from out of town and was keen to meet. He was in his camper van not far from where i lived, so off I went and met him. 

I was excited and nervous at the same time. We soon got naked and I  started sucking his quite big cock, he then sucked mine, before I pushed him back onto the bed so i could suck him, by now i was starting to become very aroused. I decided that i was going to suck his nipples, I dont normally kiss guys, but as i moved up to suck his nipples I looked at him and had this huge desire to kiss him and thats what we did. 

We broke apart for a few seconds before kissing again, this time as we kissed he took his cock and rubbed it up against my arse, as he did that i pushed back, he then got up, got the lube and lubed his cock and me. At first there was no way his cock was going in, so i used my fingers to try and open myself up, after doing that we tried again, this time he managed to get the head of his cock in, he was so good, gentle and slow. 

Slowly but surely he got his cock into me. He then had me lay on my back and started to fuck me, it was quite painful at first, but soon the pain was replaced with an amazing physical and emotional feeling, he knew i was loving it and told me so, my rock hard cock may have also given it away. After several minutes of this he had me roll over and then started to fuck me harder, he then asked me where i wanted him to cum, so i said in me, with that he then started to fuck me hard and it was not long before he started thrusting and moaning. 

Sadly I did not feel him actually ejaculate in me, but it still felt amazing. As he cleaned himself up, i laid on the bed and masturbated. I then went home, feeling a bit sore, but also feeling aroused and excited. I was horny for days after. I had constant erections, constantly leaked precum, and lots of it. I had to masturbate several times a day to give my self some relief. I then wished I had known how good it felt to get a proper fucking, and now know thats what I want to experience more of. Sadly covid has prevented me from repeating that experience, but i cant wait to do it again.