03 Aug 2018
My first anal experience or fantasy there of
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I had never experienced anal sex before, until this night. We were a group of about six or seven sitting having a drink one evening after work when the discussion changed to sex. The topic then went onto blue movies we had seen and what we liked and disliked. The one guy mentioned how he had seen this huge black dude pound this girl’s arse. The discussion then turned into a debate about if anal sex was nice or if people just did it to be different and to shock. This one girl, Jenny, who was sitting across the table from me, then said out of the blue, that she enjoyed anal sex. Well the table just went quiet for a while. Soon we sat drinking and chatting again until people started to leave. Not much later it was just Jenny, a friend of hers and I left. When her friend went to get another drink Jenny asked if I was shocked at what she had said earlier. She then asked if I had ever had anal sex or thought about it. I told her was surprised and that I had never tried it but had thought about it. She then asked if I would like to “Try it!” with her. Jenny was good looking. Not a model, just the girl next-door type, my type of girl actually. I said I would after thinking about it for a nano second. Her friend came back and excused herself and left. I’m still not sure if the two of them were in cahoots or not. We had something to eat and left a while later.
I was to follow her home but had to stop at a café or pharmacy on the way. She led the way and I followed like a lamb to slaughter, stopping to buy condoms on the way. I nearly lost her at a couple of robots but found her waiting at the other side. We parked in front of a huge block of flats and went inside. She stayed about half way up and had a stunning view of the city. Inside she took out a bottle of wine and handed it to me to open while she got glasses. We stood on the balcony looking at the view and chatting. I was starting to feel a little awkward, who was going to make the first move, when she announced she was going for a shower and that I must make myself useful and put on some music so I won’t hear her singing in the shower. I heard her singing and she was not that good.
When she came out she was wearing a towelling robe and asked if I wanted to shower. Handing me a towel she told me to hang my clothes over the back of the chair in the room. I climbed in and had a good thorough wash from behind the ears to under my balls to the tip of my toes. All I had to cover myself with afterwards was the large fluffy towel. She was on the balcony sipping her wine when I came out and approached her from behind. Commenting on how beautiful the evening was I placed my hands on her shoulders and gently rubbed her back. I could feel her relax and enjoy the rubbing and she gently lent back into me. That was when I first realised I was sporting a huge hard-on and the towel was not covering it very well. She wriggled her bottom against me and that just fuelled my desire. We stood like that for a while growing accustomed to each other getting in tune for our evening together. Reaching behind she took hold of my towel and headed for the bedroom. Standing stark naked on her balcony I raced in after her. With the bedroom lights off, the room was getting a soft light from the bathroom. Dropping her robe on the chair I caught my first glimpse of her body. Her shoulders were smooth and divided by tan lines. Her waist was soft and her hip curved. Her bottom was pale and her legs tanned. Crawling onto the bed I got a glimpse of her shaven pussy and arse but when she turned around her pubes were dark and curly but stopped just short of her lips. Her breasts were large and soft and swayed as she moved about and her nipples were hard.
I climbed onto the bed next to her and started to tickle and caress her with my fingers. Soon we were kissing and things heated up. I remember how she squeezed her breasts with both hands offering the nipple for me to suck and gently bite. She loved having her boobs held. Soon I was holding one breast in both hands and was sucking on the nipple while her hands, now free, explored my body. One was holding my hard cock while the other was caressing my balls. With little effort she turned and soon had my dick in her mouth and was sucking me as hard as I had sucked her. Her hand was holding the base of my dick while the other went from my balls to my rather apprehensive arse. I had fingered my own arse before during self exploration and enjoyed it, (I’ve not told anyone that before.) but having someone else caress me there was quite something. I was getting quite worked up so I grudgingly extracted my over excited and wet cock from her hot mouth and gently rolled her onto her back. I moved down her body and once my intentions were clear she spread her legs wide and lifted her knees. My tongue parted her puffy and dry lips only to open the floodgates of desire. Her pussy was so wet inside that the juices literally flowed from her parted lips. With fingers and tongue I pleasured her. She liked her clit sucked like her nipples and even asked me to bite around it gently. I think I over did it because she suddenly clamped her legs closed and grabbed my head. Coming up for a breath I saw she had a condom open and ready. Kneeling on the bed next to her she rolled it down my length. Moving between her open legs I eased my cock into her eager pussy. She felt so hot and tight. We got into an easy rhythm. With one hand she worked on her clit and the other went between her boobs. Stopping for a short while she went onto her hands and knees. Taking my cock she drew me into her pussy and met my every thrust. Slowly she lowered her head to the pillow and reached back with both hands and spread her arse. In the dim light I could see her arse and my cock slipping in and out of her juicy pussy. I took some love juice and spread it over arse and she seemed to tense and thrust back hard at me. The more I played the more she gyrated. With one hand she reached into the night stand and produced a tube of “Anal Lube” and handed it to me.
I removed the cap and squeezed some onto her arse, which made her jump because it was so cold. Using her own finger she probed her arse with first one and then two fingers. I was so mesmerised I stopped thrusting and just looked on in awe. I had to join her. Soon I was fingering her arse. With two fingers in her I pushed deep into her and heard her moan. After putting lube in the palm of her hand she reached back and covered my rock hard cock from tip to balls. It felt incredibly smooth and sensual as she wanked me off. Lifting herself up she parted her arse cheeks with one hand and guide me into her arse with the other. Pushing gently I inched into her. I was amazed at how tight she felt. Changing angles we tried again and this time went in a little deeper. Every inch made her moan or cry out but she kept on pushing back. She moved forward on her hands and was soon lying on the bed with me on top of her. This seemed to be the easiest for her as she asked me to move a little deeper and faster. Looking between our bodies I could get a faint glimpse of my cock sliding in and out of her arse. She was moaning encouragement and lifting her bum to meet me. Asking me to move off she rolled on her back and moved to the end of the bed. Putting a pillow under her arse she lifted her legs again and drew me closer. Asking me to go slowly at first she spread her butt cheeks and waited. Standing between her legs like that, with her exposed to a relative stranger, a calm came over me. Nudging my cock at her arse hole I move forward and my cock slid into her with little effort. I could clearly see my cock spread her arse and stretched her skin tight around my dick. Pushing her legs against her tits I started to move in her. I changed between short quick stokes to long deep thrusting. In this position I could easily look down and see my cock sliding in and out of her. She was playing with her pussy and rubbing her clit. Not once did I think to help her or caress her in any way. I had her legs in my hands and it was going to stay that way until I came. She was close to cumming but I was a lot closer. Looking back I have no idea how I lasted so long. My long hard thrusts alerted her to my pending ejaculation. I remember she wanted me to look into her eyes when I came. I wanted to look at my pulsing shuddering cock and at her yielding yet receptive arse but I did what I was told. When my eyes weren’t closed that is. Having cum inside her I stood looking down at her while her frigged her self to orgasm. I tried to help but she just moved my hand to one side and continued on her own. I felt her orgasm before I saw it in her face. I could feel her arse gripping my now softening cock and her whole body turned pink. Juices bubbled out of her pussy as she pressed her clit with both hands. Her legs closed and finally my cock slipped out of her. I lay down beside her on the bed and pulled the sheet over us.
When we woke it was getting light. I phoned my boss and told him I was going to be late. We got up, had a shower and drank coffee on her balcony while watching the city wake up. Jenny and I went out for about two months but things did not work out. Our lives were too different in too many ways. We stayed in touch though and spent the odd evening together but soon she met someone and we decided to part.