The woman who took my anal virginity - Sex Stories

The woman who took my anal virginity

It's been a few years since a girlfriend first talked me into letting her take my anal virginity... convincing me to lay face-down on her bed with my legs spread apart, so that she could get between them and have her way with me. It was obvious that she was really turned on by doing this kind of thing and that I was not the first guy that she had done it with, because what started out as a gentle probing with a single finger gradually turned into a vigorous ass fucking with a good sized dildo that she brought out from a box of toys that was hidden under her bed. She began things quite slowly by using her finger to apply some lube and gently stroke around my anus, which was quivering nervously, but also finding the special attention and new sensations to be very pleasurable. I tightened noticeably when she slipped her finger tip inside me because, even though I was expecting it, the actual feeling of being penetrated for the first time came as a surprise. It was kind of embarrassing and I felt very exposed lying naked on the bed as a woman that I hadn't really known for too long put her fingers in my ass. However, it also felt pretty good and I started to relax as her fingers slipped in and out of me, gradually going faster and deeper as she alternated between using different fingers and finally inserted a thumb. With the tip of her thumb inside my hole and her fingers fanned out palm-down over my buttock, she gripped my ass with a pincer action, trying to bring her thumb ...

... and fingers together. Gripping me tightly, she pushed her thumb as deep as it would go and, when it was all the way inside, she continued to push hard against my ass in a rhythmic pumping action. After a short while, she shifted position from lying beside me and moved to kneel upright between my legs with one thumb still inside me. Placing her second hand on my other buttock, she then used both hands to spread my ass cheeks apart with her palms and I felt her begin to stroke my stretched anus with her second thumb. She started to work her second thumb inside me, alongside the first, and used both hand to pull my cheeks further apart, as if she were opening me up to get a better view and look inside. However, this was too much and hurt me, making me wince with pain for the first time so that I missed properly hearing something that she said about wanting to give my little virgin ass a special treat. She pulled out very quickly and lay back down beside me, running her hand over my buttocks, between the cleft and gently stroking my sore anus with soothing fingers. As the pain began to subside I kissed her and felt her fingers slowly being pushed inside me once again. The initial penetration hurt me a little, but it wasn't too bad and I didn't protest, so she continued going deeper and becoming more vigorous until the only thing I could feel in my ass was pleasure! Pulling out of me once again, she rolled over to reach down beneath her bed and I thought she was getting more of the ...