Let me start by saying that I have been a closet crossdresser since I was quite young. I have kept it a close secret for over 20 years now. I consider myself to be a semi-normal straight heterosexual married male with a liking for the softer side. I let my wife discover my secret about 3 years ago, after over 7 years of marriage. She was very supportive of my dressing and even encourages it. Our sex life has never been better. We get more daring and less inhibited with each session.
I tried for years to convince her to try a lesbian sexual encounter, always without any success. That is until I started dressing for her before we had sex. When dressed in her lingerie, she felt like she was with another woman. I become more gentle and caring during sex when I am dressed as a woman. I usually eat her until she is ready to pass out and can’t take it anymore.
A young lady named Stephanie started working with my wife about a year ago. She is VERY beautiful and so damn hot. She has been making sexual jokes about wanting my wife for her lover. We never really took her seriously. My wife and Stephanie did become very good friends. They shared secrets and discussed their sex lives. Needless to say, this made me very nervous. My wife assures me that she has kept my secret.
Well our new adventure began about a month before last Halloween. (2003 ). One of my wife’s co-workers was having a costume party at her house on Halloween Night. She invited most of her co-workers as well as their spouses and significant others. I thought about what costume to wear for about a week when my wife made a request. She asked me to dress as a hooker and she would be my pimp. I wasn’t keen about others seeing me dressed as a woman, but she informed me that Stephanie had talked her boyfriend into dressing as a hooker and she was going to be his pimp. Stephanie told my wife that she had caught her boyfriend Dave wearing a pair of her panties and blackmailed him into the agreement.
I thought about it for about a week and decided what the hell I could always say it was only for Halloween. I informed my wife that I agreed to participate as long as she agreed to have lesbian sex with Stephanie in front of both Dave and I later that night. She talked it over with Stephanie with agreed but with a condition. We (Dave & I) had to agree to act as hookers until 12:00 midnight and do whatever our pimps told us to do. We agreed, figuring what the hell, it couldn’t be that bad.
On the night of the party, Dave and Stephanie showed up at our house to get ready for the party. The girls did our make-up, hair, nails, etc. Dave and Stephanie went to our guest room to get dressed for the party. My wife helped me into my favorite outfitmy black leather corset and matching panties. This was followed by a pair of black fishnet stockings and leather garter belt. Then came the black leather mini skirt and matching vest. This was topped with my pair of silicon breasts and my 4″ black patent strappy pumps. I have to admit that I never looked better.
We went to the living room to meet Dave and Stephanie, where we saw Dave wearing a floor length red formal dress with a slit up each side all the way to the top. I could easily see the panties that he was wearing along with the strapless bra, which we found out later was filled with water balloons. Amy (my wife) and Stephanie went to our bedroom and closed the door. About a half an hour later,they returned to the living room and were ready to go.
We all got into our car and left for the party with my wife driving, since she was the man at the moment. The ride took about 20 minutes to arrive at the party. After the initial laughter, we started having a good time. Our pimps ordered us to fetch them drinks, which we did. After several hours of the same thing, we decided that it was time to go. That was just before 11:00 pm. When we arrived home, we were informed that we were still their hookers until 12:00 midnight which was still 40 minutes away. We agreed and they ordered us to service each other’s pimp. We thought that that was kinda weird until we saw what they had in mind. They ordered us to remove the others pimps pants and then boxers. We readily agreed to this. That’s when we got one hell of a shock. Both of our ladies were wearing strap-on dildos that were quite impressive. We were ordered to suck them and service them like the “bitches” that we were.
We looked at each other, then at our ladies (pimps). Then we proceeded to give them our best blowjobs. After about 10 minutes of this they pushed us away and ordered us to turn around on all fours and get ready for a good fuck. We looked at them but did as told. Amy lifted Dave’s dress and removed his panties. Stephanie did the same to me. That’s when we felt the lubricant being applied to our asses and realized that they were serious. Boy were theythey pounded our asses for what seemed like hours. It was only about 10 minutes, but felt much longer.
The ladies informed us that if we wanted them to have lesbian sex that we had to agree to do one last thing. We said what the hellwe were almost there, we might as well finish. The ladies informed us that we were to eat each other out. Since we wanted lezbo sex out of them, they wanted us to demonstrate what we expected to see.
Now this was going too far. That is until Dave grabbed my dick and began sucking it. I was quite surprised and didn’t really know how to handle it. That’s when the ladies removed their strap-ons and began kissing and caressing each other. They stopped long enough to swing Dave’s legs around so that we were in the 69 position. There hanging above me was the dick of another guy, and I was supposed to suck it.
My wife then grabbed his dick and brought it to my mouth. I reluctantly opened and accepted it. It wasn’t as bad as I thought it would be. I started enjoying it and put the same effort as I was receiving. Before long we exploded in each others mouths and cleaned each other up. It tasted weird but not all that bad. After resting for awhile, we joined the ladies who were across the floor eating each other.
We watched the show until we were both hard again and then proceeded to fuck each other’s ladies for all we were worth. I had the hots for Stephanie since the first time that I saw her.
After we all finished, we all retired to the master bedroom were we have a king size bed. We rested for about an hour or so when the ladies sucked us hard again. They wanted to see us fuck each other. Since it was already one hell of a weird night, we agreed and did.
Even I have to admit that it felt good and that we all enjoyed it. Since that night we have had several repeat performances. Since Dave and Stephanie want to move out of their parents’ houses. We suggested that they move into our spare room and we can continue the fun. They just moved in and we all walk around the house wearing lingerie and fucking and sucking ALL the time.
Does life get any better than this???
By the way – I would like to thank Kerri for having the party that made it all possible.