Married Crossdressing Fun Ch. 2 free porn video

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Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause.

Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of the financial year to recognise the great job she was doing.

I had my own financial planning business that I ran from home. To my clients I was Mikki, a financial wizard who helped every client she had in all sorts of ways. To Caz she was Mikki who used to be known as Michael. He was her husband but Mikki was her cross-dressing slut lover.

They had shared many male lovers and were both hoping for that to continue. Because they moved to a new town for Caz’s job they were being really careful about how they went about finding someone new.

One morning Mikki had an appointment with a new client. When the client arrived she was surprised to find two extremely large, extremely handsome black men. They introduced themselves as Jamaal and Ishmael. They were part of a male stripping group whose career had taken off really quickly. They needed someone to help them with their increased income and to ensure that they weren’t being ripped off. They also wanted to ensure they had money saved. They made plenty and wanted to ensure their futures were secure.

Mikki was happy to help and over the course of the morning she outlined a number of ideas she had to help them achieve their goals. The boys were impressed. Mikki told them that she would need to meet with the entire group to get signatures and discuss any personal preferences they may have.

They organised a time in the next week for Mikki to meet with them. When they left she was immediately on the phone to Caz.

“Caz, I’ve just met the answer to our prayers,” she exclaimed.

“What are you talking about, Mikki?”

“I’ve just met two members of an all-male strip group. They are gorgeous and they might be exactly what we are looking for in the bedroom.”

Caz said, “Sounds intriguing. I can’t wait to meet them.”

“I’ve arranged to meet with the entire group next Friday evening. Maybe you can take an early mark and be here too.”

“Maybe I will,” said Caz.

And so it was organised. Mikki confirmed the meeting with the strippers for the following Friday afternoon and Caz organised to leave work early to be there too.

Over the next week our excitement levels rose and rose. We knew that these men might not even want what we wanted but if they did it was going to be great. That’s why we were excited. It was the possibility of getting back to what we had been doing before we moved.

Our sex that week was amazing. We were all over each other. We knew that we loved each other unconditionally but we were excited for the variety of new sexual partners would bring. Caz had her large dildo out permanently now and used it often on my ass.

We decided that we would both dress sexily, but not slutty, to meet the strippers. We both got out sexy lingerie. I wore a shelf bra and matching knickers and suspender belt under a sheer cream blouse and short black skirt. I put on nude coloured stockings and wore black four inch stiletto heels. Caz put on a pretty blue bra and knickers that she wore under a white blouse and short, tight blue skirt. She wore blue stockings and blue stilettos.

We took our time with our make up. I was now quite good at doing my own, so we sat side by side in front of our vanity mirror in our bedroom. Together we made up our faces. I finished off with a dark red lipstick with dark, smoky eyes. Caz went for a sparkly blue on her eyes and bright pink lips.

We both looked good and felt good too. I had on my honey coloured wig. Caz and I both put our hair up into a casual bun and held it together with a clip. It was a simple way to put hair up but looked really good. It would be really easy to let down if the situation warranted it.

We were excited as the appointment time grew near. Then, suddenly, there was a knock at the door. I opened it to see a group of twelve gorgeous black men waiting to come in. I recognised Jamaal and Ishmael and they greeted me like a long lost friend.

We went into the office where Caz sat casually on a lounge. I introduced her as my wife.

Jamaal looked surprised and said, “But that’s not even legal.”

I simply replied, “It’s a little more involved than it looks, Jamaal.”

“That sounds like a story, right there, Mikki.”

“Yes, but not for now. We need to get down to business. Caz can help because she knows the industry really well,” I said.

We introduced ourselves to the rest of the group and spent the next hour or so discussing various options. We decided that I would put together a package and each of the guys could add or take away elements as they chose. There were a couple of elements that were for the entire group, which were agreed upon but individually they had many, more options.

As business was coming to an end, Caz offered the guys a drink in our living room. Unfortunately eight of them had to go to a performance so couldn’t stay, but four could. Jamaal and Ishmael both stayed, and so did Tony and James.

They were lovely men, and Caz and I flirted mercilessly with them. They loved it. As men who were used to female attention they were quite relaxed about the whole thing.

Then Caz took Jamaal into the kitchen for a drink. A minute or so later I got up to see what was going on. Sure enough Caz and Jamaal were all over each other. They were swapping saliva and their hands roamed everywhere.

I heard Caz say, “Jamaal, this can turn into something fun for all of us but I need to invite Mikki to join in, and I would like the other guys to join in as well.”

Jamaal said okay and went in to tell the others what was going on. I walked to Caz, kissed her passionately and said, “I think this might be what we’re looking for, Caz.”

She agreed and we went back into the living room. The guys had huge grins on their faces.

“Now, guys. You know how we said that our marriage was a little complicated? Well, that’s because Mikki here is really a male dressed up as a sexy woman.”

“What? No way,” said Ishmael. “I know some trannies and Mikki is nothing like them.”

With that I began to strip. I took off my blouse and skirt. That was when the guys saw what was down below. I was hard as a rock.

“I don’t want to fuck any of you guys,” I said. “But I want you to fuck me.”

Caz was also taking her clothes off. So did the guys. Before long, we were both on our knees with a delicious long black cock in our mouths. We both got onto all fours and invited the others to fuck us. Caz has Jamaal in her mouth and Tony fucking her. I was blowing Ishmael and James was up my ass. It was heavenly. Caz and I had really missed live cocks fucking us.

We sucked and fucked until all four guys had both fucked us and been blown by us. They had all cum more than once, and so had Caz.

We were into our recovery when the guys said that they had a late performance to go to. So they left Caz and me by ourselves. We had both thoroughly enjoyed our evening and fell into each other’s arms. Caz mounted my mouth so I could clean out her cunt. She came again while I did so. Then she squirmed her way down my body until my cock was inside her. We made slow, tender love while kissing each other. I couldn’t last very long, but as we made our way to bed I said, “I hope you’re ready to keep going because I don’t intend to sleep tonight. I’m going to fuck you all night long.”

She just looked at me and said, “Bring it on, baby, bring it on.”

We eventually expanded our little group to include the other strippers from the ‘Man Oh Man’ strippers. In between sex we organised their personal financial packages. They made lots of money and Caz and I invested it for them. We made a lot of money too, but more importantly, we loved getting together with any or all of them for a night of amazing sex.

Caz and I grew more deeply in love over this time. She had some ideas for Mikki, but she kept me in the dark. I hoped it included becoming more feminine in the shape of my body. Eventually we acted upon some of her ideas, but that’s another story.

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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
2 years ago
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Mother and Crossdressing Son Fantasy

Mother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...

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
3 years ago
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Wifes Crossdressing Fantasy

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...

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...

2 years ago
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Crossdressing Charlie Episode 3 Relinquishment

CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...

2 years ago
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Crossdressing Charlie Episode 4 Lust

CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...

4 years ago
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Crossdressing Charlie Episode 5 Rachels Date

CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...

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