Becoming Bernard's Wife
This is somewhat a true story….
I put an ad on Adult Friend Finder, thinking I'm never going to meet anyone here but was I wrong.
I am in my 30's, tall and slender, long brown hair and practically hairless everywhere else on my body. I was looking for whatever and was very curious. Just out of a relationship with a woman for 8 years. I moved to Europe and discretely started to experiment with guys and transexuals. It was one tranny who I was fucking occasionally said, next time, "I will dress you like a girl and fuck your hole." Sure enough, the next time we had a booty call, she kept her promised, dressed me with her clothes, make-up and banged me into a brand new sissy. Shortly after, I started building up a stash of girlie clothes, lingerie, stockings, shoes, make-up and would parade at home stuffing and training my sissy hole with some toys.
Time goes by exchanging messages with trolls and cretins until I get one message. A closeted bi dude looking for a little discrete and occasional kinky fun. His name was Bernard, a widowed black man in his mid-50's living with his teenage daughter. He is a choreographer at the local art academy in his town. He is tall, with long dread hair pulled back and a smoothly shaven hairless ripped body so chiseled that every muscle are just picture perfect. Then there was his ebony Adonis of a cut cock! Long, almost as thick as a beer can, full of veins, slight curve to the right, no hair and one thick mushroom head that I wanted to pop it's way inside me and mush up my sexy silky sissy hole of fun. He had big full balls like a black bull. I imagined how much seed can be in there and what it would taste like. I would get horny, hard and wet chatting dirty with him and lusting after his profile photo album. We exchanged a few emails for a couple of weeks and then exchanged phone numbers. After another week of talking and 'getting to know each other' we decided to meet up.
He invited me to his home as he planned for his daughter to be away for the weekend leaving the house free to us. After work Friday evening, I went home, showered, shaved what little hair I may have and douched my sissy hole squeaky clean. I packed my girlie clothes, make-up and a change of regular clothes. Grabbed my bag of grass, bottle of poppers, stuffed that also in the duffle. I pack a double-ended dildo i have along with two large bottles of lube. I fill my plastic anal syringe with some J-Lube and squeeze into my sissy hole two nice fillings of the thick slippery goo. I cap it off with a long, soft and flexible butt plug to keep all the goo inside and to loosen up my hole cause I knew I was gonna need it. I put on the tightest underwear I have to resist the plug from naturally popping out, get dressed and out the door I went with my duffle of naughties.
The train ride was only 20 mins but it seemed forever, especially with my sissy hole full of lube and the butt plug happily keeping everything in. I was thinking, 'what if the cops came on board and wanted to peek in my bag or frisk me?' The thought of it was making me hard I had to try real hard not to cum in my underwear. Every time I moved, every jolt and turn the train would make, the plug would rub my prostate to the point of ecstasy. I get to my destination and there he was with his car as he said he would pick me up. I thought to myself in the car ride while he spoke, 'he has no idea I have a butt plug in my sissy-hole, does he.'
After a five minute car ride we pull into his driveway and within a few mins inside his cozy looking warm home. He asked me to sit on the couch and as if he read my mind, went to get a bottle of wine and a couple of beers. He said he needed a glass or two to loosen up a bit cause he was nervous. I agreed and started with a beer. Even though we've communicated for almost two months we were still strangers and certainly not well seasoned swingers. I twist up a joint and we smoke, drink and talk. He told me about his wife's passing but he was over it and ready to move onwards. He still has a few things he hasn't gotten rid of.
Like me, he was experimenting with guys and he was very intrigued of my encounters with transexuals, admitting that he would love to try with one. He also admitted that he loved my cross-dressed photos from my profile and that he would wank off to those pictures. I told him that I brought some girl clothes with me but he said not to worry, that it was taken care of already. Wasn't sure what he meant by that.
After a few beers, two bottles of wine and some more grass, Bernard says I got a surprise and he leads me upstairs. Thinking to myself I need to get to the bathroom first and take this plug out of my sissy hole before we start to fool around, besides I need to pee really bad. We walk into his warm bedroom with a nice large bed, a window looking out to the garden and a ladies' vanity full of make-up, which I found odd but I guess this is what he meant by of the things he hans't gotten rid of. He asked me to open the closet door and to my amazement, a woman's wardrobe! Gowns, dresses, skirts, leggings, heels, boots… ohhh a Gucci bag!!
He said I can pick out anything I want and use to the vanity. He told me to take my time because he wanted me to look beautiful. He walked out the room, closed the door behind him and went to watch TV, patiently waiting for me downstairs.
I looked back at all the clothes, the shoes and the make-up… I unloaded one huge cum shot in my underwear.
… to be continued