Becoming Bernard's Wife free porn video

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This is somewhat a true story….

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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

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Becoming A Sex Toy Part 3 Buying A New Bed And Chloe Visits

I consider myself to be a sexual girl. the day prior to this particular story, I’d had the ninth and tenth different cock fill me with cum. I’d had sex with the three members of my adopted family, as they sought to use me as their sex toy. The day began as any other weekend would but once my eyes were opened, seeing my step-brother Rob in a more sexual light, there was no turning back, despite resisting the urge to masturbate in front of him. My fall into the abyss really started when I went...

Exhibitionism
4 years ago
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Becoming Dee Dee

Becoming DeeDee by DeeDee Pauca Chapter One It's hard for me to believe that I lost my parents more that ten years ago. They were killed in an auto accident on June 10th - twelve days after my fourteenth birthday. Obviously, that's a day I'll never forget; to lose one's parents at such an age is traumatic. But I'll also remember the day because it became the first day in a whole new lifestyle. Mom and Dad left only one relative. My Mother's sister Bunny...

4 years ago
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Becoming A Masturbation Addict

I love to masturbate. This is the story of how I turned myself into the bad masturbating slut that I am today. It all started when I was sixteen. I was in high school and I was a good girl at the time. I had never done anything sexual before, in fact I'd never even kissed anyone. I wasn't bad looking or anything but I was very shy. I had many friends who were all far ahead of me when it came to sex.One day I was with a few of them eating lunch. We were all talking about girly stuff. The...

Masturbation
2 years ago
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Becoming Father Michael

Becoming Father Michael Pt 1 Introduction: Michael finds celibate is the last thing a Father is. Genre: Fantasy.  Becoming Father Michael is a complete fantasy and any resemblance to anyone, or any location or convent is completely unintentional.=========================================================Becoming Father Michael part 1."Have you thought of becoming a priest Michael?" Father Rafferty said after one mass when I just finished my confession."No father," I said, "I think now I've...

2 years ago
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Becoming Beth

BECOMING BETH By Betty Noone CHAPTER ONE. THE EARLY DAYS Before I married my beautiful wife of fifteen years, I confessed to her that I occasionally had the desire to dress as a woman. At the age of 24, I had my own apartment before I wed, and had just a few articles for me to dress up in. One pair of panties, a bra, and a house-dress, commonly called a duster. I used pancake concealer to hide my beard and a little lipstick. I did not have a wig, but used a cotton...

2 years ago
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Becoming a whore wife

That was just a normal night, when this is all started. I had been upstairs and came down to get a drink. My husband was with his laptop typing something. I leant over and noticed he was chatting. Kissing him on the forehead, I asked who he was talking to. “Some buddy” was reply. I went back up stairs and got back to what I was doing. After a while, I got back down stairs and found my hubby still typing away. Being very curious, I looked over his shoulder to see a picture of my ass on the...

2 years ago
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Becoming a Slut Wife

I never wanted another man other than my husband, but he's long had the fantasy of me being a little slut. It started as role playing at home and while we were fucking I'd make up stories about pretend encounters, both singular and gang bangs and what we found is we both got off on it. I never realized it until the day he pointed out that when I was talking about fucking other men, I came often and I came hard... and I mean HARD. I never failed to have 3 or 4 multiples with my husband, but...

4 years ago
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Becoming Jennifer

Becoming Jennifer By The Princess I received the shock of my life on the eve of my fortieth birthday. My name is or rather it was Mark Holms and my life at that time seemed idyllic. My wife of sixteen years, Jenny, had presented me with three wonderful sons. Our first boy was Andrew, aged fourteen. Our second lad was Doug aged twelve and our youngest was Michael aged ten. Jenny was still lovely at thirty-eight. Her five foot eight inch trim body was all woman and her looks if...

3 years ago
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Becoming WendyWhore

Emshon's Authors Note--This is an older story of mine that was posted on Crystal's Story Site (R.I.P.) back in 2001. I'm going to consolidate everything here on Fictionmania. I hope you enjoy this oldie-but-a- goodie. Becoming Wendy-Whore For those of you just joining in on this story, please allow me a moment to recuperate before I catch you up to speed on my tale. After all, so much had happened to me in the short span of just a few days, that I felt certain at times that I...

3 years ago
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Becoming A Were

This is the fourth story in my Were universe. But since I am using a new character, I thought that I would follow the example that I set in Be Were and instead of calling this Were 4, I am calling it Becoming a Were. Becoming A Were By Morpheus I scowled deeply as I leaned back on my bed, staring at the math book and homework questions that I'd been working on for the last half hour. Then with a sneer, I tossed the book onto the floor. "Who the fuck needs this shit anyway?" I...

4 years ago
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Becoming Chloe Part 2

Becoming Chloe Part 2 She felt so guilty about the incident at the bar with Ricky and wanted to make sure I wasn't hurt and explained that the only reason things went that way was because of the heightened sexual tension that was happening between her and I that night. She explained that with their sexual foreplay, all the drinks she had, things just got away from her and when Ricky showed up she wanted to tease me even more. She did admit that she enjoyed her time with Ricky but...

2 years ago
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Becoming a Sissy Maid for Mark and Rebecca Part Two Ms Rebecca Explains the Purpose of Stevies Visit Explains

Becoming a Sissy Maid for Mark & Rebecca, Part Two: Ms. Rebecca Explains the Purpose of Stevie's Visit As we sat in the living room of the new house she and Mark had bought upon their return to the Dallas/Fort Worth metroplex a few months earlier, Rebecca continued to lead our discussion as she shared her memories of the three of us in college, and more specifically how she and Mark had sometimes dominated me and forced me to serve them as their personal waitress at times. "As...

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