Jaq Invites Crossdresser Over free porn video

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Anyone who follows our adventures will know what type of lifestyle we lead.

A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.

All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very short dress, stockings and high heels. I was more reserved although smartly dressed in nicely tailored jeans and open-necked shirt.

At seven-thirty the doorbell rang, Kieran looked amazing when I opened the door to let him in. We all sat in the lounge and I fixed some drinks for us, Kieran told us that he liked to be known as Karen when he was dressed. The chat was getting sexier as the drinks flowed, Karen was fully dressed and made up. In short skirt, vest type top, stockings and long boots Karen looked amazing.

Jaq made the first move, with Karen across her lap she lifted her little skirt and playfully spanked her. Karen seemed to love being spanked. I looked on as Jaq continued to spank her. Karen still had her little red lacy panties on and the sight was making my cock swell. I was getting undressed as Jaq turned Karen over, lifted her top and let Karen suckle on her big erect nipples. I could see the little bulge in Karen's panties and made my move.

Karen was busy enjoying Jaq's lovely titties as I moved to the sofa. I put my hands into the legs of her panties and eased them down a little. Karen had a sweet little cock about four inches erect. In fact. it could have been a large clitty. The little cock was really hard and seeping pre-cum. Jaq watched me as I took the little cock into my mouth and gently sucked it. 

Jaq was really encouraging me as Karen became more and more vocal. Releasing Jaq's titties from her mouth, she groaned with pleasure. I worked my tongue around the little cock until I felt Karen tense up. I sucked it all in as the first jet of warm seed hit the back of my throat. I could not believe the amount of cum as Karen emptied her little balls into my willing mouth. Fully spent, Karen relaxed, sucking again on Jaq's big erect nipples.

Jaq now needed some attention> Karen sat and watched as I eased Jaq's panties down. Jaq's big wet hairy pussy seemed to excite Karen. We watched as her little cock began to show signs of life again. My cock was really swollen now. Jaq pulled Karen over and let her suck the pre-cum from my dripping member.

Jaq announced that she wanted me to fuck her as Karen watched. Positioned on her back, Karen held her legs open as I nudged my thick cock into her wet pussy. Jaq was really into this now and I was soon ploughing my cock in and out of her. Karen meanwhile was now sitting over Jaq's head having her little smooth balls licked. This was a bit too much for me and I unleashed a huge load into my dirty wife's pussy.

Jaq had not yet had an orgasm and felt a little left out. No need to worry though as Karen was soon between her legs. Karen slurped licked and sucked on Jaq's dripping pussy. Orgasm after orgasm washed over Jaq as she begged for some recovery time. 

I knew that Jaq would want to watch me and Karen together some more. Sure enough, Jaq wanted to watch me fuck Karen. Karen's panties now removed, we got her into position, still in her long boots. Jaq held her legs open. Jaq watched as I lubed up the little anal passage in front of me. Inch by inch I eased my cock into the horny little crossdresser.

Karen was very vocal as I proceeded to give her a good fucking, telling us that she was a dirty little whore who needed a good fucking. Jaq sat facing me as she held Karen"s legs wide apart, her pussy over Karen's face, being licked to yet another orgasm. It was not long before I was ready cum for the second time. I pulled out and shot my load over Karen"s pretty made-up face.

I watched as Jaq and Karen kissed and enjoyed the taste of my load. We now needed a little rest before any of us could perform again. Karen being a lot younger was soon sporting a hard-on again. It was now my turn to watch as Jaq and Karen got into the sixty-nine position. Before long, Jaq was receiving a nice mouthful of cum. It felt so right as Jaq and I enjoyed a passionate kiss, sharing Karen's cum between us.

We invited Karen to spend the night with us, she gladly accepted. Jaq wanted me to sleep with Karen and took the spare room. I fucked Karen twice more that night. The following day Jaq said that she could hear me fucking Karen, her big rubber cocks keeping her satisfied.

After breakfast the following day, we said our goodbyes. Karen messages us almost daily about getting together again soon. We have enjoyed another night together since. A story that I will write shortly.

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it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

3 years ago
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Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

3 years ago
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Cd crossdresser sissy caught by mom and dad

Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

2 years ago
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Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing
2 years ago
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Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

Gay Male
2 years ago
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My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

3 years ago
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A Crossdresser8217s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

Gay Male
2 years ago
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Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

1 year ago
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Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

1 year ago
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crossdresser violation

My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite. Like most...

2 years ago
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CD crossdresser daughterrsquos bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

3 years ago
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Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Crossdressing
1 year ago
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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

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