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“I love you,” I whispered to him before we kissed.“How was your evening?” Doug asked cautiously.“I went through with it as you asked. I had sex with Jim.” I figured now was not the time to give him the details. “How was your night? Was it all you thought it would be?”Doug was freer with the details of his night. It sounded as if Rachel was a little more aggressive than he had expected. They were naked in her bed within minutes of arriving at their house. Doug told me that they did a 69 with Rachel swallowing his cum. I figured he told me that because I have never allowed him to cum in my mouth.I asked him again it if was all he thought it would be. “It was okay.” Doug seemed a little disappointed when he described how they fucked. He said he came inside her and Rachel rolled over falling asleep. He didn’t say it, but I think he expected more. I was more convinced that I was not going to tell him how many times Jim’s cock was inside me or how many times Jim made me orgasm.We didn’t. That was until one day I got chatting via a gay dating website with Brian a 58yr old guy who as it turned out wanted to purely pleasure me, he wanted to be sucked and wanked but he did not want me to fuck him. This seemed reasonable to me, and after a few more chats we agreed to meet, we arranged for him to come to my place and fuck me there. It was during one of our chats that brian asked me something that no one else had ever asked before, he requested that I crossdress for him if would be comfortable with it. Now personally I had never contemplated crossdressing before, yes I had fucked cd's on occasions and have very much enjoyed the experience but to do it myself felt daunting. After some consideration I decided that I would indulge brians fantasy, but not go the whole distance, I settled on wearing some sexy knickers a bra and some hold up stockings and heels, but not getting fully dressed up with wig and all that.I had three weeks to prepare myself for the arranged meeting, so.
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