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This was the first time I had done anal sex, I had always had a fetish for it, but never done it. The closest I had come was licking and fingering my girlfriends ass when we were together, but never anal sex. I fucked her for about 15 mins in multiple positions before she asked me if I wanted to have my ass fucked. I was a little unsure, but thought 'what the hell'.She started slowly with me facing down and her lying on top of me, at first it really hurt and she told me I had to relax and not resist. I tried my best to relax, but it was still hurting me, then started to feel like I was going to shit myself so I asked her to stop. I started giving her head again while she pulled me off, and finally asked me what I'd been waiting to hear all night, 'would you like to taste my sperm?' I was so excited, my biggest fantasy was to have a ladyboy cum in my mouth while I sucked her penis, and this was the main porn I watched. She had me sit with my back against the bed head and started face. It was then she reached around me and ran her hands over my tits briefly, "Yes dear" she said "Right now" and moved up right behind me as I reached down and unbuttoned my blouse. She took hold of it and pulled it down to waist area. I was very nervous at this point because my back and tits still showed some redness from the whipping I took from Joe, but that didn't seem to make any difference as she moved her hands back up my back, undid my bra and took the straps off my shoulders. My bra fell down exposing my tits to my boss when he reached up and cupped one tit in his hand, "Fuckin' nice baby" he said. His secretary reached around and cupped my tits in her hands, "Oh you're so right" she said "Nice fuckin' tits" she added and when she moved her hands back behind me, "Lean down Carmen" she ordered me and I bent down towards my boss, who moved up a bit and taking one tit in his hand, squeezed it and then stuck it in his mouth and started sucking on it. After a couple of minutes he.
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