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My introduction to anal sex.I continued to go round to Tom’s whenever I could all through the summer. I was still masturbating virtually every night, sometimes several times a night, but I was always really excited when I was at Tom’s. Mostly it was just the two of us but a couple of times Brian came round to join in. Usually they watched as I stripped naked and wanked in front of them. It was a big turn on for me to see them become excited as I stroked my teenage penis in front of them until I cried out and released my sperm on the floor or over my hands.I was very comfortable with Tom and he sometimes pulled his pants down and slowly wanked as he watched me. Brian was a bit more unsure and only did that once. I sat on the floor with my legs open stroking myself up and down as they both sat on the sofa watching me. After about half an hour I said I was about to come and closed my eyes and cried out “Oh god, I’m coming Tom” and I felt my warm semen on my legs and hand. looking at Tom and Brian on the sofa they were both masturbating and then Tom stood up and leaning over me he ejaculated and I felt his sperm land on my chest and shoulders. Brian was still wanking so I shuffled over to him and he followed Tom’s lead and directed his orgasm towards me and added to my cum shower with several spurts which landed on my stomach and legs. After that I need to go and wipe myself down, the smell of all three loads iskenderun escort of spunk mixed together was quite strong and very sexy.A couple of weeks later I went to see Tom on Saturday as usual and after we both spent an hour masturbating together Tom asked if I fancied trying something else? He asked me if I knew what anal sex was and I said I wasn’t sure. He explained that instead of a woman’s vagina the man would slide his penis into a girl or boy’s bum instead. He said he’s done it a few times with his late wife and it was nice. I was worried about it hurting but he said that it was all to do with preparing properly. Thinking about it I started to tingle with nervous excitement, I’d already told Tom about using a candle in my bum when I masturbated so I was expecting him to suggest it as some point!Tom went to a cupboard in the living room and handed me a couple of things, one he explained was a douche and told me to fill it with warm water and squeeze the bulb until the water went inside then repeat after going to the loo until was clear. The other thing was, he explained, a butt plug which I needed to insert slowly so that my anus would be more relaxed. Tom seemed a bit nervous but also clearly very keen, he hadn’t come yet so I think he was saving himself. He told me to use the downstairs loo and join him in the bedroom when I was finished.I was about ten minutes getting ready and escort iskenderun although Tom gave me a jar of vaseline it took quite a while to get the plug inside, the worst bit was just at the widest part but I pushed a bit harder and it slid in and felt amazing! Completely naked and with the butt plug inside me I walked up the stairs to Tom’s bedroom, he was inside and standing by the side of the bed. He was stroking his hard penis and had rubbed vaseline on it as it looked shiny and slippery. Tom asked me to kneel on the bed and push my bum to the end, which I did with my chest on the bed. Tom eased my legs apart and I felt his legs push up against the inside of my thighs, I also felt his cock, hard and warm in the crack of my bum. He slowly eased the plug out and it felt like a relief when the widest part left my anus. I felt Tom’s fingers on my bum and he wiped more vaseline on me and slid a couple of fingers inside. I was nervous but also really excited although I was too nervous to get a full erection yet. Tom said “OK, I’ll be really slow” and I felt him pushing against me without anything happening. He changed position and I could feel his hand moving his cock into the right place, pushing a bit harder it stung at first and I winced. Tom stopped then slowly pushed further. I felt his penis entering me and after asking if I was OK he kept pushing until he was all the way in and iskenderun escort bayan I felt his stomach against my bum cheeks. After waiting a few seconds he slowly pulled out a bit and slid in again and started to get a rhythm of stroking in and out and it felt incredible. I couldn’t reach from the position I was in but I desperately wanted to wank myself as Tom was fucking me. As I became more relaxed Tom thrust a bit harder and I herd him slapping against me as he entered. He was starting to moan and I was sure he was about to come. His hands moved from my hips to near my shoulders and he leaned across my back putting almost all his weight on me as he thrusted in hard three or four times letting out a loud groan! He lay there for a little while then pushed himself up and I felt him slip out of me. I turned round and Tom was quite red in the face and smiling, his cock was starting to soften and was shiny and slippery, with a clear stream of cum hanging from the end. I touched between my legs and felt Tom’s semen dribbling out of my bum and it felt incredibly sexy. I was very turned on and my cock was not rock hard. With only two or three strokes I cried out as several spurts of cum landed on my stomach and chest.Tom asked if I liked it and I said that did and that I’d like to do it again some time. Tom was pleased and thanked me, giving me a towel and saying I could use the shower. Later that night I probed my bum, which was still slippery with the vaseline and semen still inside, with two fingers and I thought about what we’d done as I masturbated several times during the night and the morning coaxing out a further five orgasms before it was time to get ready for school.

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