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He's not my type, but sometimes a girl's mind wanders...
She seemed nervous so I took her to my bedroom and we lay down on the bed to finish watching a wild porno of a woman being fucked up the ass by a group of inmates in a prison. She was clearly aroused by the DVD and I asked her if she had ever been fucked up the ass before. She said her husband had tried but it hurt too much and that turned her off. I explained to her that anal sex should not hurt one single bit if done right with plenty of preparation and she seemed to become more relaxed at the idea of it. I showed her my drawer filled with toys and dildos of all shapes and sizes. She had never seen so many probing instruments before and when I showed her my second drawer containing my bondage and fetish gear she became more excited and fascinated.
As she sat looking at all my toys I asked her if I could see her tits and promised her that she could see mine too. We each exposed our tits and began to feel each others nipples, pulling and kneading them for a while. I enjoyed it but was thinking of her ass all the time and knew I would have to explore it soon or I would explode. The thought of her smooth perfect skin on her gorgeous ass was making me drool as I imagined how her cute puckered asshole would look, smell, feel and taste. It was too much for me and so I told her what I wanted to do. Her eyes got bigger and she looked almost fearful but she obediently turned around and lay down on her stomach for me. I looked down on her naked back and jean-clad bottom and excitement took a hold of me.
I reached for some vanilla scented massage oil and began to rub some onto her smooth back. She began to relax more and more with each second as I rubbed and kneaded her muscles, working my way down lower and lower till I came to the waistband of her jeans. She reached down straight away and loosened the zipper so I could pull down her pants. My hands shook a little as I began exposing her luscious ass cheeks and I moaned with lust when I finally uncovered her entire ass crack enough to see the bottom of her wet velvety pussy lips peeking out from between her thighs. I told her how beautiful the sight of her like that looked to me and she moaned and pushed her ass up a little while spreading her legs even more so I could see her entire pussy...
My hands explored her ass, rubbing oil over them slowly and sensuously. She pushed up against my hands and I felt encouraged to continue and move things to the next level. I reached into my drawer and pulled out a long smooth ass probe. It was not too thick, a bit thicker than a thumb. She moaned as I pushed gently against her tight little asshole. With one hand I continued to massage her ass as I rubbed and probed her asshole. Finally the fat little head of the anal probe popped into her anus and I heard a little sound of surprise escape her mouth. She buried her face into a pillow when I began to slowly fuck her ass with the toy. Sounds of pleasure filled the room as she relaxed and let me have my way with her ass. I groaned low animal like sounds as I worked the head of the toy in and out of her ass. The sight of her beautiful bottom all oily with her perfect pussy all wet and glistening drove me wild with excitement.
I reached for my vibrating egg and held it up against her clit. She gasped loudly and began shaking violently as a powerful orgasm ripped through her body. I had trouble concentrating as I watched her body react to her very first ever orgasm but I felt so proud to be the first person to give her such a wonderful gift. For so many years now she had been missing out on so much due to lack of knowledge or concern her previous lovers had for her enjoyment. She actually broke down in tears, totally overcome with emotion at what had just happened and all I did was hug her and hold her until she was able to talk about it. She couldn't believe how much she had missed in her life.
A few minutes later she expressed a desire for more and I happily got back into my position near her ass.