Wife's Crossdressing Fantasy free porn video

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This is a work of fiction. Any resemblance to persons or incidents is coincidental.

My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease.

We talked about many things. He told me I was cute and that if I dressed up I would look like a very beautiful girl. I didn't say anything about that, but I did think about it and it was exciting to think about it. Nothing else happened, but the seed was planted.

Most boys begin to develop masculine features at about age sixteen. I was not one of them. I was about to graduate high school and still I was slender, small and rather fragile looking. Because of that I always felt out of place and that is why the words of the dentist impacted me so strongly.

I couldn't stop thinking about what the dentist told me, so a few days later I took a pair of red panties and a red bra off my neighbor's clothes line. I put them on and the feeling was amazing. Looking at myself in the mirror I developed a sense of pride that I could look so good in the panties and bra. The dentist told me I could look like a beautiful girl if I dressed up and he was not lying. Somehow looking myself in the mirror made me feel really excited and good inside. That was my first time dressing up in girl's clothes and it changed my life forever.

I didn't dress up again until I was an adult. I thought I had outgrown such things and didn't think about it much. Then my wife went to South America to spend some time with her daughter. One evening on the phone she told me about a fantasy of hers where I was her slutty girlfriend and she was the man. When she said that I was so turned on and excited that I could hardly breathe. All the feelings I had enjoyed as a teenager dressing up rushed back and I knew I was about to confront my destiny.

I went out and bought a pair of red satin panties, and a red bra to match. I also bought red thigh high stockings and a red garter belt to hold them up. Over that I wore a schoolgirl miniskirt and a white blouse. To finish the look I had purchased a pair of rather large breast forms and a blond wig.

Just before she got home I dressed up in my clothes and applied some of my wife's makeup. I had been practicing the week before, so I would have just the right look when she walked in. When I looked in the mirror I can't adequately describe the feelings that coursed through my body. I was so excited. It was wonderful to me to look in a mirror and see a beautiful woman staring back.

I couldn't wait for her to come home and make me her woman. When she finally walked through the door and took one look at me she dropped her bags, held me in her arms and kissed me passionately on the lips. I was in heaven. She then told me to wait a minute and went into the bedroom. After a couple of minutes she came out wearing one of my suits and we started making out again.

I didn't know it, but she had purchased an eight inch strap-on and I could feel it pressing against me as she held me tight. She told me to turn around and she pulled my dress up to reveal my red satin covered ass, then started rubbing my cheeks. I was so horny from all this foreplay that I couldn't think of anything else but turning around and banging her right there. But then I felt her cock head touch my bare asshole. I hadn't realized it, but she had pushed my panties aside so that there would be easy access to my ass.

"I'm going to fuck you with my cock," she spat. And with that I felt her press forward. The tip pressing past my opening. I could feel that she had covered her cock with a lubrication and that helped her slide it in so easily. She had gotten inside me before I had a chance to protest, then commanded again, "Spread your cheeks for me, bitch," and with that I reached back and pulled my cheeks in either direction. "Oh, you want to be fucked like the little slut you are, don't you?"

I just waited silently. She was relishing this moment, so she asked again, "Don't you, whore?"

"Yes," I said softly.

"Yes, what?" she asked.

"Yes, I want you to fuck me," I obediently stated, very turned on by her dominant nature.

She pressed further in, aided by my spreading and slowly buried her eight inches all the way to the base. "That's a good little slut," she proudly said. She held herself there for a moment, enjoying the control she had over me. Then I felt her pull back out, put her hands on my hips, then glide back in to the hilt. She continued this for what seemed like an hour.

She had both hands grabbing the bunched up mini dress that was above my ass. All the while, I was so turned on that I could feel the pre-cum from my cock starting to flow into my panties. I couldn't believe it, but I was actually enjoying being her sexual toy.

She fucked me for several minutes, but it seemed like it only lasted a minute, or two. Then I felt her slowly pull her cock out and back away. I heard her walk to her bathroom, flush the toilet, then come back. When she came back she said, "stand up slut and fix yourself up."

I did as commanded and adjusted my dress back in place as I noticed she had gotten dressed again. I was now her bitch and I didn't want it any other way. I couldn't wait to feel her cock inside me again. Since that day I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before.

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I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

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2 years ago
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An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing
2 years ago
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An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing
3 years ago
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Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

3 years ago
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A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

2 years ago
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Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing
4 years ago
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Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

3 years ago
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Wifes crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing
4 years ago
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Wifes Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing
2 years ago
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Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

3 years ago
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Kissing Crossdressing Cousins

For as long as I can remember, I have always been drawn to wearing women's clothing. When I was 4 years old, my mother would take me shopping and I would throw tantrums if my she didn't take me to look at the girls clothes too. I would try on pants but only on one condition: I got to look at the dresses when we were done!When I was 5 years old, I wanted to be Princess Leia for Halloween. My mother thought it was adorable and was more than happy to buy me the costume. The following year, I...

4 years ago
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Making Scents of Crossdressing

Making Scents of Crossdressing By Ricky I am a hi-tech person. I work and play with some of the latest computers and electronic equipment, have stereo speakers in every room of the house, and can bore you for hours with torrents of jargon on just about any subject you care to name. When I don my feminine attire I have a fondness for synthetics, those modern wonders of the laboratories of some multinational chemical giant. Who else but those hi-tech wizards could turn a barrel...

Humor
2 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

4 years ago
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Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

2 years ago
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Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

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