The woman who took my anal virginityIt’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 canlı bahis 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 lube that she had used earlier. So I was hugely shocked when she came back up holding a bright blue plastic dildo in her hand!I started to rise and nearly bolted bahis siteleri for the door at that point, but she gently pushed me back down and used some calming words that were spoken with a gentle voice to let me know that nothing would happen that I didn’t want.She had originally been giving me a massage after we had finished having sex and, as her hands began to spend an increasing amount of time on my buttocks, she had asked if she could to use her fingers to play with my ass. It had taken a little bit of persuasion to talk me around but I had agreed, thinking that was all that would be happening, so the sudden surprise appearance of sex toys was a bit worrying. However, having experienced what she had done with her fingers so far, I guess that curiosity must have overcome my fear, because I laid back on the bed with my face down and I opened my legs for her without saying a word.She began to slowly work the dildo into my ass, taking her time to gently slip a little more inside me with each stroke until its full length was being repeatedly inserted right up to the hilt!I couldn’t believe what was happening or how good it felt, so I began to lift my rear up and pushed back against the dildo in her hand for deeper penetration. Her other hand closed around my erection as I did this and she began to wank me off from behind as she slid the dildo in and out of me. The feeling was amazing and when I came it was a pulsing orgasm that made my sphincter clench in uncontrollable spasms and grip the shaft of the dildo that had been pushed in me as far us as it would go and was now being held there!I was quickly güvenilir bahis filled with huge feeling guilt and embarrassment after cumming with a sex toy up my ass, so I started to pull away to hide my naked shame under the bed sheets. However, with a tight grip on my now shrinking genitals and the dildo that was still being held quite firmly inside me, my girlfriend kept me held in position, kneeling naked and exposed in front of her.The dildo was now feeling uncomfortable in my ass and I started to squirm, but it was apparent that my girlfriend was just as turned on by what was happening now than anything that had happened before. Realizing this and the fact that my only real discomfort was a massive feeling embarrassment, I decided to play along, because I couldn’t deny her pleasure after the incredible orgasm she had just given me.Letting go of my genitals, but with the dildo still in my ass, she got me to turn over and lie on my back. She turned her own back and straddled me in a 69 position, with her ass to my face and looking down at my naked body from above. Using my hands to part her buttocks, I started to lick her anus as she took a firm hold of my limp genitals once again and started to ram the dildo in and out of my ass. I felt her juices covering me as she pushed her clitoris into my mouth and when she came, the dildo was pushed home so hard that it hurt and made me let out a cry that was silenced by her vagina.After having her orgasm, she took hold of my hand and guided it down between my own legs to take hold of the dildo that she had kept in my ass. I was then ordered to head off to the bathroom to remove it myself. I shuffled out of the room with little steps and feeling totally ashamed to be naked and holding dildo up my own ass in full view of my girlfriend who was now laughing at my embarrassment!