Telling Mom I m A Cross Dresser part 18 Missy s Halloween Party
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I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It was only a few days away and Mom and I decided to go costume shopping both online and in the local stores to...
Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up...
CrossdressingOnly 1 chapter left after this installment....I hope you are still enjoying Sandy's adventures Chapter 19: Last Day in Vegas The next morning Tanya left for her house after exchanging numbers with us and promising to visit Peggy in Phoenix next month. The hotel had arranged a car to take Peggy to the airport for her 9:00 flight. I was sad to see them go, but at the same time, I knew I had work to do and I wanted to have some time to myself. I had to go to two accounts and I finished by noon....
CrossdressingChapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a...
CrossdressingMark was a shy guy who had always found it difficult chatting up girls. There was always some reason. He didn’t like their hair, or their body, or their look, or their personality, or his family would not approve. His upbringing was very conservative, old fashioned and his stoically minded, overbearing, controlling parents, forced their ideology on him. This had left its mark on him and he was a nervous, timid person. Any idea of an alternative life style was just not something he could do or...
First TimeHi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire. On one weekend, I went to my aunt’s place...
Cross DresserThe Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeksChapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...
CrossdressingHere are the next two chapters of Sandy’s adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan and Bob were perfect examples, they wanted to fuck a girl or at least get a blow job. They were so happy they...
Here are the next two chapters of Sandy's adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan and Bob were perfect examples, they wanted to fuck a girl or at least get a blow job. They were so happy they...
Crossdressing“Merry Christmas. How do you feel?” She yawns and stretches but replaces her hand on my cock. “Like I drank all night and had a lot of sex with a room full of women.” “Oh, me too!” She busts up laughing. “I’m not sure how any of that happened, but I’m sure if I live to be a hundred it will never happen again.” “I thought you were in college?” My turn to laugh. “It reminded me of the free love days back in the early seventies.” “I’m glad you could relive another memory.” More...
“Jake, I can’t believe you went to all this trouble!” Tanya Nolan said as her son took his hands from her eyes. The 18-year old had led her into the family dining room with his hands covering her eyes, making sure she enjoyed the surprise.“Anything for you, Mom, especially at Christmas.” It was Christmas Eve, and the two of them were alone. Tanya’s husband, Warren, had left just a few days before on business, overseeing an important project for his company in China. He’d been home for close to...
Friday December 23 Brook bailed on me when I had to go to the Love Letters set. She and the moms decided to go shopping one last time before the ‘rents flew out. I’d pointed out that there was shopping in Malibu, not only in the trendy areas of LA. How they’d missed the Country Market totally mystified me. I had planned to take Brook there, but when her parents had their problems, we’d all gotten distracted. Kitty Ellis had told me last night at the premiere that she wanted me to come in...
I never gave incest any thought, I mean sure I have had passing thoughts occasionally but I am not some kind of freak. Yes my mom is young, and I guess I always knew she was attractive from the way my friends acted around her. But until I saw her naked, I really never thought about fucking her. After that day I stopped thinking of her as my mom, and in my mind started calling her by her name Susan. If I had never found those old magazines in the attic, things might have been very different, and...
The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...
“Honey, Grandma wants to know if you can come home this weekend. She has early Christmas presents for each of us that apparently can’t wait until Christmas” Mom texted. “I have finals next week, then I’m off until the New Year, but if she needs me too, I’ll come home.” I respond. “That would be great. I’ll get your room ready. Not that you will be spending much time there. ;-).” She actually used a wink emoji, my mom has come a long way, I guess I should be glad she didn’t use the...
You may think of me as Fiona, and I am a cross-dresser.A story by Erica inspired me to pen my saga of cross-dressing. I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent. Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my...
I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...
Gay Male“Good morning... what time is it? It's almost seven o’clock on day three of your cruise. I have to go to work. You can sleep here some more or go to your own room four doors down. Either way I have to go. The whole time she is talking she is getting dressed. I sit up and she kisses me goodbye. “You were as good as the girls said you were. I’d love to do it again... when it’s my turn again.” She walks out the door and I listen. I hear hair dryers running, giggling from the passageway,...
Thanks for the nice feedback I received for this series about a cross dresser. If not for them, I might have discontinued this as I was making progress at an agonizingly slow pace. Apologies for the delay in the update. I am sending the next part, so for the first time, I sending two parts together. I also have some plans for another 2-3 parts of Rakhi’s journey and her slow conversion into a whore. I will start right from where we left off. Please read part three and parts before that to find...
Gay MaleCROSS DRESSER ENSLAVED A Fictional Account Of A Cross Dresser’s FantasiesPROLOGUEI am a cross dresser and a slave to my wife and her friends. Let me tell you how I got this way. Since I was a little boy, I liked being tied up. I had always had a petite, almost feminine body. When I was 15 years old I started dressing in my mother’s lingerie and fucking myself with whatever I could fit inside my ass. I also gave my first blow job to one of my friends. This was my only sexual experience with a...
This is the second part of my previous story. I will write about how I had rough Cross dresser Sex with him. Please continue to read the story, I know it’s a bit long story but I wanted to put in all details of my Gay experience. Ok, let’s move on to the story. We reached his place by a Cab. As we entered, he locked the door and grabbed me by surprise and pulled me closer. He planted his lips on mine, and I gave in too as we kissed deeply. He parted lips and walked me to his...
GayPart 3 of Book #1. Chapters 5 and 6. Please review and let me know if you want moreChapter 5: Da’ Place Adventures Sunday that week was definitely going to be a day of rest. After all my adventures on Saturday including a coast to coast airplane flight, I was exhausted. Collette called me and asked me if I wanted to get together tonight and I asked her for a rain check. I ran some errands during the day and late afternoon I spent watching a football game on my television and around 6 PM when...
CrossdressingWhen I came home from college for Christmas break during my freshman year, the first thing that struck me was how beautiful my Mom had become while I was away. Of course, she really hadn't changed at all--it was just that I was really looking at her after those 3 months, not just taking her for granted. I had seen quite a few pretty girls at college, and I had even managed to score with a couple of really hot chicks. But when I saw that big smile of welcome on Mom's face as my family met me...
Hey, I'm Corey and I'm in my final year of uni. As we all know, college is great. It's been sex (if your lucky like me), partying, and more sex these past 4 years. And yet the most erotic experience of my life by a long shot, was with my mother. My caring, erratic, devilishly seductive mother. Picture this: a buxom brunette, 37 years old, with perfect smooth tanned skin and big, loving brown eyes. That's my mom. She exudes sexiness out of every pore. It's something I've had to accept over my...
IncestYoung Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...
I had a thought the other day, my hockey equipment has a number of striking similarities to lingerie!To set the stage, I am a cross dresser. Like most of us, I love everything about ladies undergarments. I like seeing lingerie in stores, on models, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being "underdressed", that is wearing lots of lingerie under your manly clothes, when I go to work. I especially...
Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy’s adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...
Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy's adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...
CrossdressingThe New Christmas Mommy (written Dec 17-28) "Ok, I can do this," the lady spoke softly to herself as she stood at the entrance of big townhouse in the middle of the city. She crossed her arms together, tapping a gloved finger against her slim body. The flimsy wood sign next to the door read "Southside Street Orphanage" and the lady knew that, of course. Being an upper class middle class housewife, she didn't have much to do around the holiday season besides indulging in shopping sprees...
MY FIRST TIME OUT AS A CROSS DRESSER A true storyIt was 14 years ago and I had been married to a beautiful petite woman she had long Cole black shiny hair with green eyes.. We had been married about a year and one night I came out playing around in a pair of her sexy blue panties and a sexy blue Teddy and started rubbing on her and having fun it made her so hot we both had the best sex we ever had in our lives.. The next Friday when I got home there was a bag on the table she told me to open...
“Um... I’m not alone. Could you maybe eat with your mom?” I fake a surprised look and she slaps me on the arm. “Grandma... Good for you. Okay, I’ll eat with Mom and see you later. Say Noon at the pool?” She nods yes then goes back into her room. I make my way over to the other side of the ship, and drop down a floor to Mom’s room, and knock. It seems to take her a few minutes to answer. She also steps into the passageway in her robe. “Honey, um... Bill is still here. I don’t suppose...
A New Christmas Mommy Part 2 (april 24, 27-28, May 1-3, 6-7, 15 2018) Tim awoke from his slumber, looking over to his alarm clock. It read 630 o'clock in the morning. Oh snap, he realized, Diana has a long day of work then an afternoon appointment to get to, so he needed to hurry. He dashed quickly over to Diana's bedroom. Making sure to close the door quietly, Tim got out the elements of his 'Diana Princeton' guise, laying them out carefully on the bed and her vanity table. Tim...
If there is an i****t goddess I was a grateful recipient of her bounty on Christmas Eve... although at first it sure didn't feel that way as I drove through a wild winter storm.I was meeting my girlfriend three hours away at her parents'... as my family wasn't celebrating Christmas until the 26th; my sister was flying in later (fares at half the ridiculous pre-Christmas level).So I was driving three hours north (or perhaps it would take far longer since I was driving through a near blizzard) to...
Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.Now I am in my late teens and at college.One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.“Not bad thanks, Dad, how about you?” I replied.“Pretty good...
Crossdressing100% fiction! This story begins 5 years ago at christmas. Christmas has always been a small affair for our family. Me 18yo, my mom dad aunt and uncle all sleep over at my grandparents house for the small family get together. Me and my aunt have always been close. I tell her about all the stuff i do good and bad. We have always flirted a little bit over the years. Mostly just patting each others butts when we walk by. I always thought my aunt was sexy. She was 45 at the time. She has a well kept...
Incest"He's an absolute asshole Aunt Bridget," were the first words I heard when I barged into the kitchen after I'd got home from football practice. "Hi mom," I said with a big smile as I reached to grab a couple of cookies from the pan that had just been pulled from the oven. It was their aroma that had drawn me unerringly to the room. After giving mom a quick kiss on the cheek I turned to Rosie and asked with a twinkle in my voice, "Got a kiss for your favorite cousin beautiful?" "No!"...
My night with Laci was amazing, It was like I could tell what she wanted and when she wanted it by instinct and she could do the same for me. All that weekend it was all I could think about as I continued on with a normal weekend. Nothing to special really just washing my normal and my Missy clothes as well as taking care of chores around the house. I went off with some friends at times to because even though I do have my Missy life I also like to keep my normal life as well.Eventually my...
Lesbianby BrettJ © 2010 As she tidied up her daughter’s room, Karen Shower was perplexed. The 38-year old blonde was at a total loss as to what she could give her daughter Crystal for Christmas. Now that she was Assistant Manager of the Bank, she could finally afford to give the 16-year old anything she wanted, but Crystal hadn’t indicated there was anything she wanted. Not yet, anyway. There had been a lot of lean years for Mother & Daughter both, as Crystal’s dad had vanished when he...
A week later Chris and I met to go cloths shopping. We met at a coffee shop in a town a hour drive from me. She greeted me with a warm hug followed by a deep kiss. Our obvious age difference drew some judgmental stares from a lot of the other patrons. Chris sensed the fact that I was uncomfortable. She whispered in my ear "If only they knew all of the cum I licked from your ass". We grabbed two coffees to go and headed out."So Eric said I needed to get something kinky to wear the...
As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie’s bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren’t for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria’s Secret. ...
As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie's bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren't for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria's Secret. ...
I still can't believe what happened to me. December 25th 1999 is a day I will never forget. That is the day my mother raped me for the first time. (Merry fucking Christmas you bitch!) I mean it was just cruel and sick and nasty. There is no excuse, no rational explanation for her behavior. It wasn't just that she raped me, it was how she did it, the utterly despicable way she went about it. I guess I'm getting ahead of myself a little. To understand you have to go back a year to the events...
I decided I'd walk over to her place. It wasn't far and it was a nice day. Once dressed I picked up the bag and headed out the door. I arrived just before 8. She answered the door in her dressing gown. "darling" she said and we kissed each other on both cheeks as I entered. I stood in the hall. The flat had high ceilings. We went to the kitchen. We discussed proceedings over tea and toast. Showers were a must. I had a lot of shaving to do. That would take some time. There was one...
I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour.Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they...
An Incident in a Cross Dresser's Life Part 4I always dressed in pantyhose while teaching class. I had on an extra tight pair of panties to hold in my butt plug. Every movement sent shivers across my nipples. The only person who knew was my fuck buddy and fellow teacher. She was the first to let me explore my cross-dressing (see previous stories). After school, we would go to the park in her van that had dark windows that no one could see in. She would sit back and I would eat her pussy until...
As a cross dresser you feel like such a woman when you have on your sexy panties and bra, and other feminine unmentionables. Sometimes you just wear them underneath your boy clothes. But sometimes I like when you have a dress and even high heels on too. I get to look at you, a beautiful and sexy woman. You get to tease and titillate a guy like me with your sexy body. You make me so horny and hard when you prance around the house looking so pretty. You always wiggle your sweet ass when you...
Hello everyone. I am Anuradha / Sameera, a Secret Crossdresser of 29 years old from Telangana. My breast might be around 34-36 as 36 size too fits well. I love sports bras and padded bras. started in my junior college days when my friend became my boyfriend. It started with him sitting beside me. We used to stroke each other’s cocks secretly under the bench. The handjobs slowly turned into blowjobs. I also had my boobs squeezed by a few others in the class. But I was too scared to tell my...
ONE Over the next couple of weeks, I lost track of the days. At first I would return home and breathe a deep sigh of relief. Grateful I had tolerated any torment, that I had survived all I had been subjected to. And as I relaxed and wound down, I found solace in the many happy moments my day would bring; which I then used to spurn me on. Something as simple as an understanding smile from a customer would keep me on a high for hours. It gave me something to hold on to as...
A New Christmas Mommy Part 9: The Spring Dance (March 6-7, 9-11 2019) "Oh goodness, what a busy day...." Diana said wearily as she opened the door to her condo. She took a moment to take off her high heels, rubbing her stocking clad feet for a moment. Ah, Jane isn't back yet.... as she noticed no other sound coming from the condo. Ah well, she figured, I can unwind with luscious mistress of wine, as she placed her clutch purse down and walked over to the kitchen fridge. Opening it up,...
The following story is a complete work of fiction and fantasy. Any resemblance to persons living or dead is purely coincidental. Note that as opposed to most of my posted works, this is a stand-alone story, offered as a holiday thanks to all my loyal readers. Keep that in mind when reading—I hope you enjoy it. And please take the time to vote or leave a comment, the authors do appreciate it. "Jake, I can't believe you went to all this trouble!" Tanya Nolan said as her son took his hands...
It was about 11am by the time I woke up and found myself still in bed with mom. I looked over to see she was still sleeping and still in her lingerie as was I. I got out of bed carefully and as soon as I did I felt how sore my ass really was. I decided to tighten up my stance a little by putting my legs together and squeezing the muscles in my ass tight as I walked. It was a lot like my sexy walk and to be honest it gave me my morning erection as I walked to my room.Once I got there, I took off...
IncestShe had to make it good. It couldn't be just another gift wrapped cologne set, or a gift card to Ulta. She wanted this Christmas to celebrate her newfound lust with her k**s. She wanted David and Dana's presents to be fun, kinky and perverted. That's why, after a few weeks of thinking about it and a little searching, she had finally found David's gift.David had very open tastes. He was very in touch with his sexuality; he knew what he liked, and he was willing to explore new things to keep...
It was a few days later after my night with Greg and being his police bitch for the night when I found myself sitting on the couch in a pair of nylon stockings, thong, bra and of course my new brown hair wig and breast forms. That night mom had to work late so I had the house to myself. For the first half of the night, I walked around the house and watched some of my favorite zombie movies. Eventually, I got horny (as usual) and decided to try out that Sybian that mom had gotten me so many days...
IncestI told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud.Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...
CrossdressingThis happen a few years ago. And opend up things I would had never imagen possible. I lived with my mom alone. I never knew my real dad. During the years a few man lived with me and mom but they came and left. Mom is a real dificult person,she not easy to deal with. Shes always been kinda immature.Mom was 44 at that time she had a very beutiful body for her age. I never looked at her in a sexual way back then. I even was kinda use too watching her tapless around the house or hearing her having...
It is 8:35 on a warm summer morning. I hear the front door close and already the excitement is building. I hear the car start and then pull out of the drive way. I run to the front of the house and watch my mother pull up the hill and off to work. My sister left for work 5 minutes ago and Dad is gone until 2PM.I turn and walk up the green carpeted stairs. With each step I feel my heart pounding harder and harder. As I reach the top of the stairs I take one last look out the window to make...
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...
CrossdressingGrowing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature...