I was probably between the age of 8 and 10 when it started, my friend Ollie were close but not best friends, in fact his best friend was the same person as my best friend and thats really the only reason we knew each other and became kind of friends. We would have sleep overs but it was usually all three of us, we would sleep over in Ollies lounge and watch rubbish horror films and then when we knew his parents were asleep we would flick over to the adult channels and look at the previews, our friend would fall asleep but me and Ollie would always be the last two standing and found ourselves looking at each other instead of the TV.
I was always interested in Ollie in a wierd way because he used to wet the bed so had to wear a nappy to sleep in, I wasn't interested in an attractive way but I was always just a bit curious. Our friend was on holiday and me and Ollie were at the park together, we were playing around and having a great time, we went into the woods because we both needed to pee. Ollie asked if we could pee together and wanted to see me and me to see him, I thought nothing of it and we peed together and had a bit of a sword fight with our streams.
Later that afternoon we went back to Ollies house and played a game where we built a castle each and created catapolts with boulders to destroy eachothers castles, it was so much fun! I stayed for tea and Ollie asked if I wanted to sleep over, I wanted to play more of this game so without hestiation I said yes please.
Normally we would sleep in the lounge on a blow up double bed but as it was just me and Ollie so his mum said we should sleep in his room and share his bed top and tail. We went up to bed and played on the playstation for a little while. Ollie asked me if I wanted to wear a nappy too so he didn't feel wierd, I said no thank you so he didn't want to wear his anymore, he took it off infront of me without thinking and as I looked up I saw him totally naked. He got back into bed and didn't put any of his clothes back on and asked me to be naked under the covers with him, I felt a bit uncomfortable but after seeing him naked I felt okay. We were talking about what girl we liked and suddenly I felt his hand on my cock. I was a bit shocked as no one had ever touched me there before and I liked girls, he asked if I wanted to touch his and for some reason I really did want to.
We lay there for a few minutes just holding onto each others cocks and he asked if he could kiss me, I was a bit unsure because I liked girls but he said it will be good practice for when we get to kiss the girls we like, so we kissed for a while and I remember his cock getting hard. I remember watching this in sex eduction and if it gets hard its because you want to have sex, so when I said this to Ollie we both said we should have sex but I don't have a girls parts so how can we, he said I should suck his cock and he should suck mine and give eachother a 69er. We did this for ages and I remember thinking it was great, we went to sleep like this.
Morning came and his mum opened the door to wake us up, came in and opened the curtains, luckily we were under the covers and got away with it. She asked Ollie why his nappy was on the floor and he said he didn't need it anymore and didn't want to be different. In fairness to him the bed was dry in the morning.
We did this every sleep over for a year or so, when he used to sleep over at my house I shared a room with my younger brother, so we set up a tent in our bedroom and me and Ollie slept in there, that way we could wait for my brother to be asleep and then we could start to play and play we did. In the tent we didn't top and tail so we would get naked, cuddle, kiss, toss and suck this is all we knew about and it was great.
In summer 2001 I remember we both got a bit sad because we were could to different form groups in our senior school so we wouldn't get to see each other at school and we wouldn't get to share classes together. Naturally through senior school we drifted apart. Fast foward to 2008... I was old enough to drink and go clubbing. I hadn't thought about Ollie for years, infact we hadn't really spoken since summer 2001. I was out clubbing with some friends we were all very drunk and having a great time, we ended up bumping into a group of old friends from school who we hadn't seen for a couple of years. We were all chatting away when Ollie walks over from the bar.
Thinking nothing but wow I haven't seen you in ages we chatted for a while as a group and carried on with our night out. A few hours later I needed to pee, and while I was at the urnial Ollie walked in and started peeing too, I think this may have brought back old memories because when I looked over to say hey again, his eyes were looking down and it was clear to me what he was looking at, I got his attention and looked down at his, it was safe to say we had both grown up but I think we had the same curiousities. We finished up and shaked off the last few drips and tried to put our cocks away only to realise we both had semi's.
As we got out the toilet we went to the bar and started chatting again. We exchanged numbers and said we should hang out or go to the casino or something, which sounded great and it would be great to be friends again. Two nights later I got a text from Ollie saying "I have a free house if you want to bring your tent over like old times". I read the text in my room but as I read it I instantly got nervous and felt like someone could see me, I looked up and all around just to check, even though I knew I was alone the whole time. My stomache felt a little shaky and my hands were shaking as I trying to start typing my reply.
"I'll be round in 5" was my reply, he sent back "bring condoms." Instantly my cock was hard, luckily I had a few condoms around, I was a virgin but I was also 18 so you never know. I remember parking my car up and looking at his house, it brought back so many memories that I couldn't wait to get inside. He opened the door as I was walking towards the house and I walked in.
He was stood there in jogging bottoms with a plain t-shirt, not only was his boner clearly visible but he had a little wet patch of pre-cum through his underwear into his jogging bottoms. He said shall we go to my room or into the lounge, the fire was lit so we went into the lounge. He asked what I wanted to do and I said everything. Within seconds his toungue was in my mouth and his hands were down my trousers grabbing my ass cheeks. I could feel his hard cock rubbing against mine through our trousers and I pulled his trousers down, he grabbed my belt and started to undo it and bring my trousers down, we stopped kissing and took our own t-shirts off so we didn't make a mess and pulled our boxers down.
It was a total in the moment kind of situtaion, we were both virgins with girls let alone boys so we had no idea what we were doing. He sat on the sofa and asked if I had any condoms, I handed him one and he put it on his cock and said come here. I walked over facing him and sat on his lap I felt his cock rub against my hole and we started kissing again. While we were kissing away I lifted my butt up a bit and positioned his cock at my hole, he had a really fat cock so it felt like it would be impossible, I grabbed all the precum from the head of my cock and used it as lube along with lots of spit, Ollie spat all over his condom covered cock and rubbed it all around, back into position I tried to lower myself down. I felt his head slip in as it it was nothing, I couldn't tell you if I moaned because I was so nervous it was all a bit of a blur. All I remember was Ollie's face, his head went back as if he was in a lot of pleasure, he grabbed my cock and started rubbing up and down, he tried to kiss me but I think I was focussing to much on getting him inside me.
He started to push in and out and I could feel it go further and further inside me with each thrust, eventually I felt my balls on his pubes, he was all the way in. It took a bit of getting used to but soon felt incredible. We stayed like this for probably 5-10 minutes just taking it all in and not wanting to cum and it all be over. As we were kissing we felt it get more and more passionate and it all got very intense, I could feel myself relaxing and watching his face as he thrust his cock in and out, we slowed down a couple of times so that he didn't cum but not for long as we couldn't resist but to get back to it. The combination of kissing him and feeling his balls slap against my ass was incredible, its funny how worried we were about being secretive as there is no chance his neighbours couldn't hear us, we were both in bliss moaning and calling out each others name with a "fuck me", "oh you like my cock in your ass" and "oh I'm balls deep in you". Eventually he said he was close and within seconds thrust deeper than ever with a huge moan/sigh, this was it he was cumming inside me I could feel his cock pulsing, I went to grab my cock to wank myself to climax but he beat me to it and the second he touched me I shot my cum further than I've ever seen it shoot before, Ollie was covered and we were both exhausted. As soon as we caught our breathes we kind of realised what had just happened and within the blink of an eye we were cleaned up and fully clothed. We could barely look at eachother and I couldn't get out the door quickly enough.
We didn't talk for a few weeks and I really didn't know how to feel... I'm not gay, I don't find men attractive why did I do that. I was feeling all kinds of crazy emotions and wondered if Ollie was feeling the same. After a few weeks I was finishing up at work and went to my locker to collect my phone ready to go home, I had 1 unread text message... Ollie, "I have a free house this weekend do you want to come over again?". I was so confused maybe he wasn't feeling the same as me, maybe Ollie was gay. All I knew was that I couldn't go round as I knew for certain that I wasn't gay. While my head was processing this, I had already replied and was parked outside his house again walking to the door as he opened it in the same joggers with his boner on show.
Before we got started he asked if I wanted to stay the night, then I explain I don't think I could because when I cum I seem to go completely straight and act disgusted at myself for what we've done, he said he felt the same but then it passed and he didn't feel that way anymore and just knew he wanted me again. His sister and parents were out for the weekend so he had all of the house to himself. We didn't get straight into the sex but we did walk around naked for a few hours, the temptation to just jump on him was incredible but I held off.
We hooked up his laptop to the TV and watched some gay porn together, both our cocks were leaking all over the place as we grew more and more horny, it was time to go to the bedroom. Ollie had a few toys out, I didn't know he had toys but I think they were bought for the occasion haha. One was a little but plug and the other was a small vibrator connected by a wire to a little switch that someone else could control, we went up to his room and started rubbing our cocks together, it felt great because we were both really wet with precum, Ollie got on his knees and took my cock in his mouth, this time I was a little more composed so it wasn't such a blur, infact I use the memory of this time to get myself going. Ollies mouth was really warm and wet, I remember him making a lot of slurping sounds which I didn't enjoy but it felt so good it didnt matter, getting head has never done anything for me so I just enjoyed watching Ollie enjoy tasting my precum. It was my turn now, I gave Ollie a kiss on my way down and started sucking on his cock, I remember putting my toungue between his foreskin and the head of his cock, that really made him moan and say "oh yeah, you love my cock in your mouth", "you love me fucking your mouth" I really did.
I came up for air as he said he was getting close, we got on to his bed and started to get into a 69 position I remember I was a bit shorter and was on the bottom, I was playing with his balls with my toungue and grabbed some of his precum and rubbed around his hole, this really got him going and I felt his toungue licking my ass hole, I've never felt anything like that in my life and it really got me going, that made me come close to cumming but I didn't want it all to be over and me not be able to look at him, I wanted to spend the night and sleep naked like we used to.
Ollie got off and picked up one of the toys, he grabbed the little plug looking toy and spat on it and positioned it inside himself, I loved watching his hole wink at me as he was trying to get it in, he then asked me to lift my legs as he grabbed the vibrator and put it inside me, I thought this isn't so great just give me your cock.. he then started to suck of my neck and turned the vibrator on, all I can say is wow! I've never felt such a feeling, considering at the time I thought I was straight I was overcome with pleasure and was certain that cock was everything I have ever needed.
We had been doing this for a few hours and Ollie asked if I would try fucking him, we only had one condom and he wanted to finish inside me again so he asked if I would put it in without one but just not cum in there (as if that helps). I didn't even think about it, I think I was just so horny I would have agreed to anything. Ollie laid on his chest and opened his legs making way for me to go inbetween, he had clearly shaved his ass but only the crack as he still has nice fluff around his cheeks. I pulled his cheeks apart and gave his hole a lick, not for the taste which wasn't bad but so that I could try and make it as wet as possible. He shivered and was quickly covered in goosebumps. I laid ontop of him and slowly put my cock on his wet hole, my cock was soaking wet with pre cum and his hole easily took the head of my cock, he let out a moan and i felt his hole tighten around me, I asked if he wanted me to take it out but he pushed back making sure that I couldn't, I started thrusting in slowly at first and from his moaning could tell he was enjoying it, I kept pushing in as deep as I could go and I felt my balls hit his, I pulled out and he pushed his bum up to try and stop me, as my cock came out his ass let out a little fart sound, it was so hot it made me want him to fuck me.
We swapped over and he put a condom on his already hard dripping cock, as he put it on he accidentally ripped the edge, we had nothing else but knew that I was a virgin and so we guessed we were good and clean/ safe. I jumped onto my back and sprung my legs in the air ready to take him, he put his cock up against my hole and started to push, it went in so much easier this time than it did the last time. It also instantly felt incredible, my cock started to leak with pre cum instantly, Ollie pushed all the way in and felt his balls slap my ass I couldn't hold in the pleasure and moaned like I've never moaned before. I felt an incredible fullness, desire and pleasure all in one go, it felt so much better this time, more pure by having it skin to skin inside me. Ollie started pumping in and out I could hear him getting out of breathe as he tried to kiss me. He bit my lip and knew he was close, I could feel his cock pulsing inside me, I'm pretty sure he was hitting my prostate as I started to feel like I was going to either pee or my cock was just going to explode. Suddenly I started to feel overwhelmed and while telling him how big he was, how much I love his cock inside me and how hot this was Ollie grabbed my ass cheeks and pulled them apart and let out a giant moan, seeing him like this made me reach my peak and I came all over myself, I could feel my ass hole tensing up around Ollies cock as he started to cum too.
We were both covered in sweat but to make sure I didn't feel straight or awkward Ollie kissed me, and pressed his belly and chest into mine as he laid ontop of me, I could feel my cum gluing us together. He stayed inside me for quite some time and pulled out when his cock had gone soft. I felt his cum drip out of me as he pulled out and made the decision to get up and clean myself up, I went into the toilet and gave myself a wash and came outside, Ollie asked if I had to go, I replied absolutely not, I'm happy to stay if you want me to?
This went on for a couple of years, it is now 2020 and we havent met up in about 10 years, we're both in straight relationships and avoid any contact on social media. Although I am sure one day, we will bump into each other again and who knows, maybe we wont be able to resist.