I was still living with Sue when I first met Pauline, so it had to be kept a secret. We actually met at a dance class which we were both going to and ended up fooling around a little bit in a small, dark room under the studio once the session had ended. I actually ended up fucking Pauline that very first night, a fantastic shag that immediately let me know that here was a game girl, someone who would be up for a bit of sexual adventure in her life.
And so she was. We would snatch some shag time whenever and wherever we could, enjoying the fact we were doing something really naughty, really wrong.
Then one Sunday afternoon, when I was round at Pauline’s flat, things moved on to another level. As we kissed and cuddled and fondled each other, I somehow found myself behind her and close to her bum with my erect cock. I decided to take my courage in my hands and carefully introduced it to her anus. Pauline didn’t shy away exactly, but instead stayed perfectly still. I carefully pressed forward and suddenly my cock entered her – just the head – very quickly. Pauline squealed a bit and ever muscle in her body seemed to lock up. It was obvious to me that she wasn’t enjoying the experience, so I quickly pulled out and that was that for the day. The matter simply wasn’t discussed and I felt worried that I had gone too far too quickly and maybe that I had blown my chances of making a real go of it with this undoubtedly sexy woman.
I needn’t have worried. I obviously hadn’t upset Pauline too much with my little slip, because a few months later we were living together and both enjoying life. I have got rid of Sue and was really glad I had. Pauline was a seriously sexy girl who was very adventurous in bed. Despite that, I didn’t dare explore the possibility of anal with her. Not after my ‘ failed entrance examination’ the last time! But I was more than happy with the way things were going anyway, so that didn’t upset me at all.
Pauline was a qualified masseuse and as you would expect we got into the habit of doing massages for each other. On this one particular afternoon I was giving her an all over massage, which as much a turn on for me as it was for her. She was lying on the massage table on her front. The room was nice and warm and the lemon and Patchouli that was in the oil was making the air heavy with scent. First I worked on Pauline’s back and shoulders, neck and arms, bum and thighs and moved all the way down to her feet. Then I turned her over and began to massage her front. I worked on her legs, and then went up her thighs to her tummy, paying particular attention to the little grooves where her stomach met the tops of her legs, just along the lines of her pubic hair. Pauline always loved that. Finally I moved up to her breasts, easing my fingers up slowly, then pressing in firmly as I got to her nipples, which were pink and swollen hard now. Her chest heaved as she breathed deeply, her eyes closed in ecstasy.
Pauline was totally relaxed by this point, so I asked her to turn over onto her stomach again, which she gladly did. I gave her back some gentle rubs again, smoothing her oily skin before I moved down to her buttocks. I worked and kneaded them, hearing her sighing with sighing with pleasure, loving the attention. I wondered if she might like me to explore further, so gently lifted one thigh and eased it sideways so that her legs were opened just that little bit further. Pauline slowly moved her other thigh to match. I could just see her pussy hair between her legs.
I worked more on her bum, bit by bit easing further down in-between, up and down, squeezing firmly, watching her beautiful anal opening clench and relax as I came closer and closer to it. I didn’t touch it yet, though. At one point I stopped massaging and just rested my fingertips on the inside of her cheeks. She groaned and lifted her tummy off the table, so that her anus pushed against them. I took this as a signal and began to massage all around the entrance, smoothing and easing, prodding just inside once in a while. Pauline didn’t complain, but rather sighed and gasped and even moaned a little. At that point I suspect that she would have let me do anything.
“ Can you slide down to the end of the table?” I asked. Obligingly she slid down to the foot of the table so that her upper half was still on it, but her legs were hanging off the end and her feet were on the floor. They were slightly apart and I could see between her cheeks, where the whole area was glistening with oil.
I stood at the end of the table between her feet, using my thumbs to massage her buttocks, pulling them outwards. After a while I leaned forward and pressed my tongue into her anus. She clenched her bottom and gasped. While my tongue was bust there my hands were free to unto my trousers, slipping them down and off. My cock was as hard as iron. I moved forward and let it rest between her cheeks, then began to slide it up and down, gently at first, then pushed it down more firmly. Every time my helmet slid over the entrance it caught the edge for a second and Pauline held her breath. Did she want me inside? I plucked up my courage.
“Do you think we should go for it, Pauline?” I asked. “Do you want me inside you?” She simply nodded. It was all the invitation I needed. Her bum hole was slippery and smooth, so I gripped my cock in one hand and pressed it down against her opening. With each of Pauline’s breaths I could feel her anal muscles first give slightly, then tense again. Finally they relaxed just enough and the shiny purple head of my cock slid in and disappeared. When the head was inside I stopped for a moment, then pressed on. The ring of muscles around her entrance clamped tight just under the head of my dick. The feeling was amazing. I could feel my come starting to rise in my shaft and it was all I could do to stop myself coming there and then. Pauline breathed more deeply and I inched deeper in. I asked if she was ok and she told me that I would have to put some more oil on my cock, so slipped out again. I greased myself thoroughly and gently slid back in. Pauline started to giggle. She was clearly enjoying herself more now and let out a loud, orgasmic sigh when I was finally in so far that my balls slapped against her arse cheeks. I enjoyed the feeling for a moment, and then started to thrust and retreat, thrust and retreat. I pushed in and pulled out and enjoyed the tight feeling of Pauline’s arsehole hugging my still cock. Her whole body seemed to be out of her own control now; moving, pulsing and clenching.
“Oh god, this is fantastic,” gasped Pauline. “Your cock feels so tight in my arse. Amazing.” I had never heard Pauline so turned on and listening to her as she told me to fuck her in the arse was an incredible turn-on. Again, it took all my strength not to come there and then. After a few more slow and easy strokes I knew that I wouldn’t be able to last much longer, so I started to thrust harder and faster, with shorter strokes. The faster I went, the more hoarse Pauline became. She was still gasping and crying out encouragement to me. At first I’d thought that she wouldn’t be able to turn herself on to the point of orgasm – not unless one of us could reach her clit and rub it hard anyway – but the sensation of me stroking my cock in and out of her arse actually seemed to be doing the trick on its own.
“I want you to come deep inside me,” she gasped. “Right inside me, as deep as you can go.” I pumped faster and faster, deeper and deeper, and suddenly felt the end of my cock swell up to bursting point. That was it. I would not be able to last any longer. I felt my own body tense up and I came – four or five hot jets of it- right up her lovely tight arse. The sensation of my hot come made Pauline come immediately as well and her arse pulled tight around my cock as she shuddered to her own violent climax. She squealed and squealed and I could feel her arse pulsating tight around my cock as orgasm shot through her whole body.
“Oh my god! Oh my god!” cried Pauline loudly as the final waves of ecstasy engulfed her and she finally collapsed back onto the massage table, utterly exhausted by our anal sex session.
It was absolutely, positively the most exciting sexual experience I have ever had. And when she could finally get her breath back Pauline could only agree with me.