Where it happened: His house
Well I had already had sex with two guys – one of them was still my boyfriend – so this is the story of my first time at anal sex. I had met this guy who was a friend of my best girl friend… I knew that they had been sexual together, but I still kinda had a crush on him, even though I was living with my boyfriend. So this made it difficult – and also, this guy was married, so that made it even less likely that anything would happen. Anyway, we got to chatting on msn one day, and it turned out that he was alone for the weekend and kinda bored. My bf was out at work, and I got quite flirty and suggested that we get together for some drinks and movies at his place. He agreed, and that evening he picked me up. We got out a few horror dvds and went back to his place to watch them on the big screen. We also bought some of my fave bourbon to drink. Anyway during the first movie, we drank a fair bit and I was getting brave, so I cuddled up to him and he put his arms around me – just like I hoped! Before long we were kissing and our hands were all over each other’s bodies. I was pretty scared about what he would think of my body because my breasts are not real big, and my pussy has never really grown much hair (even though I was 19)… But he was really really into it. I let him take off my top and he teasingly licked and sucked my nipples, which I LOVED! I took off his top and loved his bare chest pressed against me. When he took off my g-string I was so worried about what he would think so I tried to cover myself up, but he pushed my hands away and he said that girls would pay to have a hairless pussy like mine – he couldn’t believe it was natural! So then I felt more comfortable. He said he wanted to lick me until I orgasmed so I told him to go ahead! It felt so good and before long I was moaning with pleasure. I also sucked on his lovely cock – but I felt really self-conscious, because I haven’t really done that much before.
Anyway, after a while, he begged to see me bent over with my cheeks spread apart. I was embarrassed about him seeing my arse like that so I put it off… but after a few drinks I eventually gave in and I bent over and spread my cheeks to let him have a close look at my arsehole, like he wanted. To my surprise, he held my hips and started licking my arsehole up and down. He only stopped to tell me how perfect it was – I was surprised and didn’t really know what to think but in the end I just relaxed and let him lick me there – it actually was feeling pretty good. He was soooo hard so I just had to grab his dick and rub it a bit while this was happening – it’s hard to describe the position we were in, but he was licking my arse as I felt his erection. After a while, we moved onto the couch, and he started massaging my back. It felt so so lovely having his strong hands massaging my shoulders – it relaxed me so much. Every now and then I would feel his hard cock rub up and down my arse crack. To my surprise this turned me on – I must have been so wet! So I let him keep doing this, and I pushed my arse out a bit to give him better access… Then a minute or two later I suddenly realised that now his cock was inside my arse, pushing the whole way in and then withdrawing almost the whole way out. He seemed to be in ecstasy, moaning my name and telling me how perfect it was. Maybe it was because I was relaxed but it didn’t hurt at all. He paused and asked me if it was okay for him to be doing this. I told him I’d been wanting him in the front, but that I was quite enjoying myself, so he kept going and I rubbed my clit while I pumped his beautiful dick in my arse until he came deep within me. He sounded so hot when this happened!!
Well next we had a sensual shower together, and it wasn’t long before he was hard again – and I was still horny as hell! So right there in the shower I lay down and he fucked me in my pussy so hard… ohhh it’s hard to describe just how good it felt having this hot guy deep in my aching pussy. We both orgasmed and just sat there under the water kissing. After a few minutes I just started playing with his soft cock, enjoying its feel between my fingers… I have to admit that although I had cum, I still needed more satisfying. We made it to the hallway with me feeling him and then he sunk to the ground, pulling me down on top of him. This made me really worried because my boyfriend once told me I am no good on top, so I have hardly ever been on top before – but now it seemed okay, and he kept telling me I was great, so I let my wet pussy sink down on his hard cock and I just let myself go… I wished it could last forever – it was so good having his hands on my breasts and occasionally move a finger to my arse as I rode him. After a while I could see he was going to cum so I let myself cum as well and then we just collapsed, exhausted.
We did a lot more kissing and stuff that night, and then at about 2am, he dropped me back home. When I got home, my boyfriend was waiting for me. I didn’t tell him where I’d been, but I could tell he was horny. He started kissing my neck, which is my secret thing that I always give into – and he couldn’t believe how wet I was when he put his hand up my skirt. I didn’t tell him that it included another guy’s cum! Anyway, then we went to bed and I let him fuck me. It wasn’t as good as earlier that night, but it was a lovely way to finish the evening!!
Anyway, I later found out that I had got pregnant, and I don’t know who was the father, but I never told my boyfriend that it might not be him. I am now the happy mum of a gorgeous girl, and my boyfriend is still with me…
But I still fantasise about the time I let a hot guy take me up the arse!!