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This is my story in a short form of how I became me a 22 year old black gay crossdresser. I've always had gay tendasies from as long as I can remember but at age 17 I met a guy who house I use to walk by after school and we would chat, after a while I told him about me and he said he always thought I would make a cute girl, now he was white and a bit older than me at 30.
After a couple weeks he talked me into comming in his place said he had a present for me, well what it was several girl outfits from panties to short skirts, heels and wig, I was hesitant but he said come on you know you want to see what you look like as a girl and he wanted to also.
I was nervous as I went in the other room getting dressed in a short black skirt white top, white tiny bikini panties and even the heels fit, last the wig, I didn't look that bad but was still nervous going out to see him, he was all smiles and complimentary making me feel semi relaxed, he could tell so he went and got us a couple shots of liquor, now I didn't drink but I wanted to relax drinking them they were nasty and strong but I did feel better.
He told me I needed one more thing to make my look complete getting some lipstick putting it on me, we walked over to the mirror with both of us looking at me, he was standing right behind me telling me how cute I looked and we looked good together putting his arms around my waist pulling me back to him.
I jumped and froze with him telling me to relax resting his head on my shoulders holding me tighter moving his hips on me and I could feel him getting hard on my butt, he told me don't that bump feel good on my ass, I nodded yes I had been thinking about being with a man and was wondering if this should be the time and with him.
He turned me around holding me around my waist saying do you mind if I kiss you, I nodded yes it started with a few pecks then a deep wet kiss with him putting his tongue in my mouth telling me how to kiss with him, now this was my first time kissing anyone like this and it felt so good even better when his hands went down undr the skirt feeling all over my bottom for a few minutes making me kiss him harder.

He took my hand lowered it putting it right on his cock which somehow he managed to get out his pants running my hand on it telling me what to do, I wasn't expecting this but the drinks and his touch had me so hot I just kept doing it even when he released my hand putting his back on my butt.
He stopped pulling his lips from mine taking me over sitting me on the couch standing in front on me telling me he wanted me to suck his dick, now this was another thing I had never did but fantasized about it alot so when he pulled my head forward I just opened up my mouth doing it, I wasn't very good but he coached me on telling me what to do when I was sucking it right and how to lick all around it with my tongue, the more he told me what to do the better I started liking it.
He told me to hold my lips tight on it and his hips began going really fast to my face he said he was going to cum in my mouth and swallow fast when he did, I was really nervous but excited by this and when he came i tried but he came quicker than I thought and I tasted it before I could swallow at first , it was slimmy and tasted like nothing I had before but I gulped it down swallowing it all as he paused holding it in my mouth.
Umm you did that so nice he said as he pulled back letting it come from betwen my lips pulling me up in his arms holding me saying but we are not finished yet reaching under my skirt pulling the panties down taking them off me telling me we must finish my transition turning me around getting behind me, he started putting oil on my butt hole pushing his fingers in me turning and twisting them then I felt his cock going in me at first it hurt but he really took his time putting pleanty of oil on it.
Slowly more went in until I felt he was all in me I felt stuffed, at first he just held it in me then started moving slow, my ass was so tight on him afterall this was my first, he told me to lean over on the couch as he pumped back and forth in me it didn't take him long and he stopped and I felt him cumming in me, it was unbelievable how wet and warm it felt he just held it deep in me getting it all in me then he pulled back and it seemed my hole popped.
I turned going in his arms and he held me stroking my back and butt saying guess you're no virgin anymore I just looked at him and he kissed me hard and deep again telling me we'll be doing more of this but it must be our secrete, I put my regular cloths on leaving telling him I would see him tommorow for some reason I felt so good about what I did I wanted that for such a long time smiling walking home.

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Fantasy & Sci-Fi

A Chance Encounter with Kaley Cuoco

You are sitting at home watching TV when you turn over to The Big Bang Theory and see sexy shot of Kaley Cuoco. The beauty plays Penny who lives next door to some nerds who are shy and can't really talk to women, then starts dating one of them. You love the show mainly because you can relate to the nerds and she is really hot and she wears revealing outfits. You can't remember how many times you have jizzed off thinking and looking at her massive tits and how many times you have thought about...

GAIL 2

Gail said she felt real naughty not wearing panties or a bra while we ate our meal. Many of the patrons were looking at her. I smiled and said" I guess I will have to punish you when we get home" The men were whispering to the ladies they were with. The women looked at Gail with disgust. I called a cab and requested the mini van. When It arrived I helped Gail into the van. This time I put my hand firmly on her ass. When we got to the apartment I helped her out of the van and again her skirt...

Emilys Seduction part three

There was a tapping at my library door. It had to be Emily. I had been avoiding my stepdaughter for a few days. It was something of a surprise when she had touched my turgid prick with her feet. I had not responded properly, at first. I admit that I had some rather unfortunate urges concerning Emily. She was my new wife's daughter. She was nearing seventeen years of age soon. I would need to control myself. "Come in." The door opened slowly and Emily entered. She was dressed in only her bikini...

Taboo

A Voyage Around My Mother

Once you've crossed the line, there isn't any problem. It takes a little bit of psychological adjustment and if you get that right, and you accept that you're never going to be understood by anyone on the outside, then it just becomes a world within a world.You know that most of the stuff that happens is ugly and dysfunctional and most probably non-consensual, but not all of it. And no-one wants to think that any of it is going on by choice, or even worse, to consider that it's better than...

Oregon Coast Ch 04

This one is a little personal, my father in law was a Japanese-American GI in WW2 and there are a lot of echoes of my family in Doc M’s family. The Battle of the Lost Brigade happened in October 1944. Like the Light Brigade at Balaclava, the 442d was ordered by incompetent generals to do a militarily impossible task and did it on sheer courage, at great loss to themselves. For this and many similar feats the all Japanese-American 442d became the most decorated unit in the US Army, including...

Erin visits Jake longer than expected

Erin is a 24 year old beautiful single woman. She is 5’9” tall, medium length silky blonde hair, blue eyes, and a smile that lights up a room. Her athletic build includes a tight ass that she maintains by routine workouts. Her laugh is contagious, but unfortunately, she has no close family members since her mom passed a couple of years back. Her career allows her to take time off during the year for a month or sometimes more - which she uses to enjoy recreational travel and adventures with...

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