My night with Jan and her two kinky men

The personals ad read as follows:

“Mid 30’s couple looking for open minded crossdressers for kinky and unusual scenarios. We provide the costumes and a full makeover. Email for details with a picture. If we think you are a good candidate, we will reply with a phone number.”

Since I had no plans for the evening, I emailed the anonymous address including a photo of me and shortly after received a reply with a phone number from a woman named Jan.

When I called Jan, she asked me about my experiences, specifically any crossdressing I’ve done and if that involved play or sex? I told her I had dressed in private many times but have wanted to experience sex with a man when I’m completely transformed into a woman. This seemed to get her excited and she started telling me how her husband enjoys fucking men that she (his wife) fully transforms into women. They have various scenes and scenarios but those are a surprise because her husband never decides until a few hours before. Jan usually shoots video. We talked some more and she talked about how nothing excites her husband more than a virgin he can deflower.

Jan said she would love to have me come over. The only requirement is that I am completely shaven. She would take care of everything else.

I arrived at their house, parked my car as instructed and rang the doorbell. Jan opened the door wearing extremely tight jeans with heels and a very low cut tight white t-shirt. She took me through the master bedroom and into a large bathroom connected to a huge closet of all sorts of women’s clothes.

Jan said she had been thinking about how to transform me and decided to do a classy hooker dressed in white. She told me strip and recommended I let her insert an anal plug since her husband was well hung and he sometimes likes to just ram it in. Wow, this might be an intense night I thought to myself. She lubed a medium plug and told me to squat. She slowly pushed it in while caressing my cock. It was so hot I almost shot my load.

Jan went an picked out my outfit and laid it out on the bed. She said we would get dressed and then do makeup. First she had me put on some white thigh high stockings, not fishnets, but they did have nice lace on top. Next came a tightly fitting white corset that had a see through halter top. She connected the garters to the thigh highs and then filled the corset with breast forms. I was getting really turned on and had a raging hard on. She said that would be a problem since I needed to look feminine and wear panties. She kneeled down and started sucking me off. At one point, she removed the anal plug and started fingering me. It felt so good but I couldn’t hold out anymore and shot my load in her mouth. She swallowed every drop and then reinserted the anal plug.

At that point, she helped me into some silky crotchless white panties with a special band that would wrap around my cock and pull it between my legs so that I would not get a hard on unless her husband removed it. The heels she picked out were gorgeous white sandals with a 4″ heel. She then got a text message on her phone saying that her husband had invited a friend over and that they would like to start the evening doing some gloryhole play in their basement.