My First Crossdresser - Part Three free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

Harrah's was crowded, loud, and bright. She walked in front of me, holding my hand and leading us through the maze of people. I didn't mind being led because I could watch her walk, her ass and legs were as sexy as any I've ever seen. We made it through Harrah's, lurched onto the street and into the cool night air. The sidewalk was crowded still, but now we could walk side by side, hand in hand. I could hear giggles and whispered comments as we passed other pedestrians, but I didn't care. We crossed the strip in front of Caesars Palace and made our way to the Bellagio fountains, where she wanted to stop and linger.

We leaned against the rail and watched the fountains. I think the song playing was "Singing In The Rain", but to be honest, my head was spinning with lust and emotions so it's hard to remember. I put my arm around her and she leaned her head on my shoulder. We didn't speak. After a minute or two she turned to look at me, and when I looked back she kissed me. Soft and sweet, her lips and tongue began caressing mine. We pulled each other closer, kissing even more deeply, and I could feel her cock pushing against my leg. Just when I thought I might cum in my paints, she pulled away, tossed her hair and giggled, took my hand and led me down the strip.

We walked over the bridge from New York New York to The Excalibur. In the middle of the bridge she stopped me and we kissed again; this time she cupped my ass with her hands and pulled me tight against her. Our cocks were straining, tongues working each other, and she was moaning ever so softly. I imagine that we were making quite a scene, but didn't want to stop, I don't remember ever being so turned on. I felt like a teenager again.

We boarded the monorail at Excalibur for the short ride to Mandalay Bay. We sat tightly against each other, her head on my shoulder and holding hands. She whispered in my ear "You did very well, I can't tell you how much I loved that walk. I'm going to reward you with the best sex you've ever had." My dick has been hard ever since we met, but this makes me throb. The train stops, we walk into Mandalay Bay and find the elevators. Holding hands all the way up, off and into the hall, we walk to her room. She opens the door and we walk in. The door shuts behind us. She takes my face in here hands a begins to kiss me even more passionately than before. My head spins and my cock throbs.

To be continued...

0
0

30.10.2021
18
0

Same as My first Crossdresser - Part Three Videos

The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

Portrait of a Crossdresser as a Young Man

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time...

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

Crossdressing

AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male

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...

Jaq Invites Crossdresser Over

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...

Crossdressing

Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing

Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

A Crossdressers Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now. This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

Gay Male

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

firsts time Im seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

my life as a sissy crossdresser

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...

olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

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...

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...

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

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

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

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...

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...

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...

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...

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

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...

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing

Blackmailed Crossdresser part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier,...

First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Crossdressing

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest

CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

Simran A Crossdresser Part 3

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I went downstairs and looked through the window, and what I saw was astonishing. People were running, screaming...

Crossdressing

Telling Mom Im A Crossdresser Part 12 Tow Truck Drivers Big Score

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience.Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do with the money I am saving I just tell them I am thinking of getting a new car or something, but that’s not the...

Crossdressing

Telling Mom Im A Crossdresser Part 11 Girl time

Part 11It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended.I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got...

Crossdressing

Telling Mom Im A Crossdresser Part 8 Bus Drivers and Cops

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long.One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I was sitting at the back of the bus and saw how there wasn’t any other person on the bus besides me and the bus...

Crossdressing

Simran A Crossdresser Part 1

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible.I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a mustache and body hair which I cannot remove because of religious reasons. But it is a blessing in disguise because...

Crossdressing

Telling Mom Im A Crossdresser Part 17 Seven Days Of Sex Days 1 2

This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! It was now Monday and mom had to work. I was left home alone and I had already began a 10 day holiday with about 8 days remaining....

Crossdressing

Telling Mom Im A Crossdresser Part 75 Amateur Pole Dancers

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

Crossdressing

The Next Night Crossdresser Part 2 of 2

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. ‘I was just about to wake you up with a blow job,’ she smiled.‘Funny, I was thinking of doing the same to you!’ I laughed.Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my...

Crossdressing

Telling Mom Im A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole.I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

Crossdressing

Telling Mom Im A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

Crossdressing

Girlfriend Ne Crossdresser Bana Diya 8211 Part I

I’m ricky sharma frm delhi and now i am 25 year old. ye meri pelhi story hai agar galti hui ho to plz maaf karna aur mail bejh kar suggetion jarur dena. ye mera real life experience hai… lets start the storyMeri famly me papa-mummy chota bhai aur 2 sal badi sister hai. So story start karta hu apni cd life se. Ye stry aj se 4 sal pelhe se start hui ki kaise mein cd bana. Jab mein 21 ka tha tab meri neha naam ki gf thi. Us ka kadh lagh bagh mere jitna hi hai 5’6. Figure 34 30 32 tha ek dam...

Telling Mom Im A Crossdresser Part 85 Cops and Prostitutes

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan.“We can definitely let him have a free night in exchange for not getting a criminal record.” Mom said as she gave a sigh of relief.We started to talk about the sybian that mom had bought and some...

Crossdressing

Telling Mom Im A Crossdresser Part 7 The Spa

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy.I loved that idea and hurried upstairs to pack Missy’s bag. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

Crossdressing

Telling Mom Im A Crossdresser Part 6 Missy and Mistress Keri

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least.One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at the kitchen table. I instantly knew that Missy had been hired for another job.I sat down next to my...

Crossdressing

Confessions of a Sex Crazy Crossdresser Part 9

Hi all, hope you enjoy Sandy's adventures. Chapter 17: Viva Las Vegas Peggy and I woke up in each others arms around 5 AM and we made love again. Then at 6AM when we both had to get up we showered and made love again under the water in the shower. We were avoiding the subjects of me leaving for Las Vegas today and her having to be at work at 8:00. I drove Peg to her apartment on the Northwest section of Phoenix and we exchanged phone numbers. I told her I would call her from Las Vegas and...

Crossdressing

Confessions of a Sex Crazy Crossdresser Part 7

Chapter 13: One Hour Photo I checked in at the motel and went to my room. It was a standard motel near the freeway, two levels tall and I was on the lower level in the room farthest from the office and facing away from the freeway. I opened the door and turned on the air conditioner. It was still about 85 degrees and it was after 5:00. After a quick shower, I picked up my voice mails from home and returned a couple of calls for work and then got dressed into some nicer clothes. I knew there...

Crossdressing

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and one weekend my parents went away with some friends and I knew that this would be the perfect oppurtunity to...

Crossdressing

First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

Gay Male

Telling Mom Im A Crossdresser part 13 Missys Turn

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to “visit”...

Crossdressing

Porn Trends