This goes back to when I was a policeman who enjoyed dressing and having sex with other men and also loved sex with women. I had two girlfriends at work, one a female detective and one a civilian employee who worked one floor up from my office. Both women knew about each other and how much I enjoyed them sucking me off from time to time, usually in my office or in the detectives car. Her, Donna, and I worked together on cases and on part time jobs, so we had sex quite often and she was very good at giving oral sex. The civilian told me her ex husband divorced her because of her lust to suck cock. I on the other hand would love to have a woman at my home who would suck others while I watched, and even would help.
Well, I had video taped the civilian (Joan) sucking me off in my office and also had, on the same tape, me sucking on a rubber dildoe. I mean really taking it deep into my mouth. I do not know why I took that video but I did. At the end was me dressed in female clothing.....all in my office.
So, one night when I was off work my partner, Don, broke into my locker and watched the video and then took it to the office where Donna worked and let her and a couple of other detectives were working watch Joan give me head to completion and me sucking on the dildo.. I never found out about this for at least a year later.
Well, one night Donna asked me to get a dildo to use on her. So I brought the dildo from my locker to her condo one night and when we made love she asked me to use it on her. I inserted it into her pussy and she loved it and took hold of it and used it herself, pushing it deep into her pussy and moaning and groaning. Then she asked me to take pictures of her with her Polaroid camera. Well, I did so and then we had five photos of her fucking herself and a couple of her sucking me. Then I fell asleep and woke up with her pushing the dildo into my mouth, ever so gently. As I woke up and felt the dildo in my mouth I got hard as she also stroked my cock. She kept up a rhythm as she fucked my mouth with the dildo. When she stopped she asked me if I liked it and I said "ooh yes". Then we started talking about the guys who worked at the hotel where we both worked security. She told me about some of the conversations she had with some of them, particularly about their gay habits.
As she talked about two of them telling her about how they had sex with each other in different places in the hotel. One would suck the other, and as she continued with the story she started rubbing my cock and got me hard and excited. Then she went down on me and sucked me for awhile and stopped to ask me if I would like to have one of the waiters from the hotel go down on me. Well, at this point I was very excited and horny and said yes. She told me she could arrange it for me.
One night when we were at work she asked me to bring the video camera with me when I visited her the next night. I thought that would be hot and I was anxious to do so and wanted to video tape her naked.
At this point I did not know about her seeing my video tape (yet) of me being blown by Joan and of me sucking the dildo. But I would soon know something. So, when I got to her place she was totally naked and hot to trot and told me she wanted to video tape us making love. OH YES I thought. So, naked we got and I set up the camera and we started kissing and her fondling me and my finger fucking her pussy. Then she said she wanted to show her sucking me deep in her mouth. Exactly as she said it, "deep into her mouth". So I face fucked her as she moaned and groaned and was soon fucking herself with the dildo. This was great and I was having an awesome time. Soon I was fucking her as she retold the story about the two hotel employees having gay sex and fucking each other at the hotel. Then she told me how she had watched, at their invitation, as they took turns fucking each other in the dining room of the hotel, at night in the dark.
Well, needless to say that got me off in no time and I filled her full of cum. As we rested she told me that she knew the story would excite me. I did not correct her. Then she told me she had asked one of the guys to meet with me and have sex. I told her I would like that and would she want to be there. She said yes, she wanted to watch.
The night, well the first time, this happened at the hotel was a summer night and we were both (Donna and I) working security at the hotel. After we closed the bar and lounge she grabbed a key to one of the hotel rooms and went there to make sure it was empty. Then she told me she would go and get Jeff, and for me to get naked. I waited for them and played on the bed naked and horny as hell.
When they enter I met Jeff for the first time. He was a young stud, maybe 20 and good looking and tall and slim. I was very turned on to having sex with him. I had never told Donna that I had previously had sex with other guys, usually having them suck me and I had sucked a few guys off before. And she never knew about my desire to crossdress (yet).
Jeff was soon naked and playing with my cock as Donna got naked too and watched it all. Jeff took my cock into his warm mouth and sucked me and I moaned and put my hand on his head. As he sucked me Donna whispered into my ear and told me she wanted to see me suck Jeff. So, I went down on Jeff and sucked his average size cock into my mouth and sucked him deep into my mouth, as Donna gave me words of encouragement. Saying, "oh honey, suck his cock and please him. Do it for me and make him feel good." Then she said to Jeff, "cum in his mouth baby and let him know what its like". So, Jeff had a hold of my head now and was fucking my lips hard, deep and rough and soon was emptying his cock into my wanton mouth. As I swallowed his cum he just kept pumping my mouth with more cum and Donna told me to save some for her. As Jeff climbed off of me, Donna told me to kiss her and share the cum. As we kissed and she goggled up the extra cum she told me that she truly enjoyed the show that me and Jeff had performed for her. Jeff was gone in no time and we played there for awhile and she soon wanted to make love and we did.
Later we talked about me having sex with other employees and she wanted to know if I would like one of them to fuck me. I told her I was not sure but would think about it. I told her that if she wanted me to that it would turn me on to do anything and everything in front of her and with her permission.
