Telling Mom I'm A Crossdresser Part 3: Missy's Weekend free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in.

After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of what was to happen. She told me that I was to live with a couple this weekend and do everything they say. As she spoke I couldn’t help but smile and blush at being at the command of 2 strangers.

Friday came and I got dressed a little slutty and like a hooker as per the request of the couple. I wore a black tube top that read sex object on the front over the breastforms I had underneath. I also wore a red miniskirt that barely covered my ass and panties as I walked and finished my outfit with some fishnets and 6 inch heels and my blonde wig.

My mother then drove me to their house that night as she kissed me goodbye and told me she would pick me up on Sunday night. I walked to the door feeling my heels click all the way up as I gave my ass a good wiggle just in case my new master or mistress were looking.

I knocked on the door and a tall, very tanned, muscular male opened the door. He seemed to have been in his 40’s with short hair and if I could guess, I bet he would have been a body builder.

He told me to enter and called his wife. She was not as tall as him however she had what I bet was a good 40DD chest and 38 hip size with a slender waist. She seemed a little younger, Maybe in her late 30's as they both came to the door in towels and were now leading me to the living room where they both had put on some of their underwear. I just looked at them as my eyes kept going back and forth between the woman’s beautiful tits, ass and pussy and the man’s hot abs and 8 inch cock. They introduced themselves as John and Jamie. I introduced myself as Missy and that I would be the one to serve them this weekend as I curtseyed but soon dropped it as I forgot my miniskirt was very short.

They smiled and giggled a little as they walked closer and started feeling up my body and my sexy clothing. Jamie had gotten in front of me and started to kiss me as she massaged my tits and my cock while John watched. Then she broke our kiss, turned me around and smacked my ass hard.

“Mmm You’re a cute one, my husband and I will have lots of fun with you,” she said with a playful voice, rubbing her pussy and my ass.

I just moaned as I looked up at John who was starting to rub his cock in his pants and smile.

“Get your bags and go upstairs you little whore,” he commanded.

I turned around and bent over showing them my ass as I picked them up and wiggled my hips again as I made my way up the stairs. As I did they told me to put on my new uniform that was in my room to the left. I proceeded up to my room and found a sexy maid's uniform with a skirt that went to my thighs and I recognized as a ditzie micro maid dress that I had seen in some tranny clothes and role play catalogs. I put on the dress and then waited.

A few minutes later, Jamie came in wearing a pair of sexy white lace panties and bra with matching stockings. I looked at her and she looked at me before she pounced on me and started grinding her soaking wet pussy onto my crotch. I grabbed her tits and started massaging them as gently pinched her nipples and rubbed all over her body again.

Jamie leaned forward and told me to start licking and sucking her nipples as she took off her panties which I happily did. I lapped all around them, kissing and gently nibbling each one with tender loving care as I felt her slip her panties off from her body. As I continued to suck her hard delicious nipples, I felt my panties were coming down as well allowing my cock to spring free. Then I felt it, her warm pussy wrapped itself around my cock as she started to ride me hard thrusting down on me like she hadn’t had a good fuck in ages. She moaned and screamed wildly as was I for another 10 minutes before we changed positions and she bent over the bed. I shoved my cock right back into her and thrusted into her hard as I felt her warm juices and wonderful tight pussy clamp down on me hard. We continued to fuck for another 15 minutes before she stopped me to change positions again.

She sat on the bed before falling backwards over the edge so that her back was propped up against the side of the bed with her knees to her shoulders and her legs spread wide open.

“Come here you little whore, I want to feel that big tranny cock in my dripping wet cunt,” she said in a lustful and demanding tone.

I didn’t hesitate to comply as I made my way over and started pile driving her with my dick. She moaned wildly and begged for more saying everything she could to get me to keep fucking her.

“Oh god yes baby fuck me, fuck me hard. Oh yeah just like that. Keep going. Don’t stop, keep fucking my hot pussy until we cum.”

Hearing her say that made me so horny I fucked her even harder for another 30 minutes before we both exploded into a huge orgasm. I pulled out my cock and shot her load onto her tits while she squirted like a geyser completely soaking me in her pussy juice. We laid on the floor panting like tired dogs as I then felt a hand grab me by my wig so deep even my real hair was being pulled on. I looked up to find John naked and semi hard.

“Now that Jamie has had her fun, you now have to serve my needs you little maid whore. Get on your knees and suck my cock to make me hard.” John said as he pushed me to my knees right in front of his cock.

I began by kissing his tip and slowly licking up and down his shaft before stroking him a little and sucking his balls. His smell was intense and very manly the same as his wife but with a more womanly fragrance. I continued to lick all over and play with his cock until he was hard as steel before putting him in my mouth. I bobbed my head for 10 minutes before he pushed me off and told me to get on the bed.

“Yes master.” I replied

As I laid face down on the bed with my legs spread wide open I felt him apply lube to my ass before shoving 2 fingers inside and smacking me on my ass and calling me a whore.

“Mmm, yes, master, I will do what you tell me. I am your little whore and I will do everything you and mistress tells me.” I moaned as he fingered deep into my ass and twisted.

He then got on top of me in a laying down doggy position and started to fuck me. His cock was too big for my ass as he forced it in little by little while I held onto the pillow and sheets while screamed in pain but then turned to pleasure. He started to pound me as I turned and saw his wife was licking up my cum and rubbing her pussy with 6 inch dildo which I can assume was suppose to be my cock.

“Take it whore, ahhh yea you like that don’t you? Uhh you got a nice tight ass, I will enjoy fucking you all weekend,” he grunted and groaned while fucking me hard and deep.

“Yes oh fuck yes your cock is amazing master! I love your big cock and thank you for giving it to me, it feels so good and my mistress's pussy is so hot and soft and wet. It makes my clitty cock feel good. Thank you for making me your toy this weekend.” I screamed in ecstasy.

He continued to fuck me for another 30 minutes before finally cumming deep in my ass. I looked over and what I said must have sent Jamie over the edge as well as she let out a large moan and came with her dildo inside her as well with my cum still glistening on her face and tits. We all laid on the bed with me in the middle as we all fell asleep to rest for the next day.

Over the course of the weekend, we continued to fuck, suck and lick each other to orgasm over and over only for me to clean the house and change my clothes for them in between.We tried all kinds of different kinks from BDSM where the wife and I took turns being spanked and used while the other watch, to erotic roleplays where I was a tranny patient getting my dose of cum and pussy juice from my sexy nurse and doctor. However I think my favorite parts were when I got my 50cc's of cum and pussy juice obtained orally and anally. I also think I enjoyed watching Jamie getting tied up and told to fuck her pussy and mouth while she was helpless and John stroked his cock before fucking her ass as well.

Finally Sunday night came and my mom called my cell phone to say she was going to pick me up. When my mom had gotten to the house, she came in and asked what we did over the weekend. I told her in great detail as she smiled at me then at them. I could tell she loved the idea as her nipples got hard through her shirt. She was definitely not wearing a bra.

Then she walked up to the couple and asked for $3000 dollars. My jaw dropped when I heard that price but the couple just smiled and wrote her a cheque.

“Worth every penny,” they said with a grin.

My ass and cock were still sore from the weekend as I walked towards the door. However, before I could they stopped me and handed me the maid dress I had worn for them.

“We thought you might enjoy keeping your uniform since you seemed to have a lot of fun it in. Maybe others can have fun with you in it as well.” Jamie said with a wink and a giggle. I smiled and thanked them as we left and got into the vehicle to drive home.

My mom looked at me and asked how my weekend went.

“It was good, I have never felt the best of both world before but this weekend was amazing.”

“Mmm, well I am glad that you enjoyed your weekend, however we need to be getting home,” she said with a grin and rubbing her nipples.

“Why is that mom?” I questioned with a puzzled look on my face.

“Do you remember Missy’s first client that came to our house when I went to the org… I mean bridal shower? Well his name is Stan and he wants to see you again.”

My eyes lit up and I smiled. “Missy needs to take a shower and find something sexy otherwise she will be ready.”

To be concluded. (Maybe )

Same as Telling Mom I'm A Crossdresser Part 3: Missy's Weekend Videos

2 years ago
  • 0
  • 33
  • 0

Telling Mom Im a Crossdresser Part 9 A New First for Missy

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...

Incest
3 years ago
  • 0
  • 33
  • 0

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
3 years ago
  • 0
  • 21
  • 0

Telling Mom Im A Cross Dresser part 18 Missys Halloween Party

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...

4 years ago
  • 0
  • 19
  • 0

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...

3 years ago
  • 0
  • 39
  • 0

Telling Mom Im A Crossdresser Part 16 Hot talk With Mom

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...

Lesbian
2 years ago
  • 0
  • 21
  • 0

Missys First Job Chapter Two

Chapter Two Missy was enjoying getting dressed today and she got ready for the big interview with Auntie's friend Beatrice. Beatrice was a part owner of Belle du Jour Lingerie Company and was the company Auntie Veronique did most of her design work for. She stood in front of the same full length mirror in her bedroom that she had stood before that first night at Auntie's place some 6 years earlier. Her sandy blonde hair was perfectly coiffed in a retro style. She considered...

4 years ago
  • 0
  • 37
  • 0

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
2 years ago
  • 0
  • 38
  • 0

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
2 years ago
  • 0
  • 27
  • 0

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
3 years ago
  • 0
  • 32
  • 0

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
3 years ago
  • 0
  • 53
  • 0

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
2 years ago
  • 0
  • 33
  • 0

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
3 years ago
  • 0
  • 43
  • 0

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
4 years ago
  • 0
  • 28
  • 0

Telling Mom Im A Crossdresser part 10 Another Day With Mom

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...

Incest
4 years ago
  • 0
  • 22
  • 0

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
  • 0
  • 35
  • 0

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
4 years ago
  • 0
  • 40
  • 0

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
3 years ago
  • 0
  • 51
  • 0

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
2 years ago
  • 0
  • 40
  • 0

Telling Mom Im A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

Crossdressing
2 years ago
  • 0
  • 35
  • 0

Telling Mom Im A Crossdresser part 135 Missy Brings Home A Stud

I 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...

4 years ago
  • 0
  • 31
  • 0

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
2 years ago
  • 0
  • 46
  • 0

Telling Mom Im A Crossdresser Part 4 Repeat Business and Roleplays

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again.Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

Crossdressing
4 years ago
  • 0
  • 22
  • 0

Missys Naughty Night Out Part 2

Ethan walks over to me and I roll my hips again while looking ahead to the pillows. I notice a stray hair of mine on the pillow and smile. That must be from our rougher antics the other night, which I would quite like a repeat of that later on. A slap on my buttock jolts me back to the present as my cheek stings from his strike. My pussy instantly clenches and I give a light moan as Ethan clasps my hips in his large, strong hands. His fingers hook onto my hipbones and he presses his denim clad...

2 years ago
  • 0
  • 23
  • 0

Roommates Part 4 Missys Magic Wand

It came as a big surprise the following Friday when my girlfriend Jane and I came in late and heard some moaning from both Missy and her date when we came home the following Friday night. Missy was our roommate. She was a petite little redhead, with a cute round face, small, lovely breasts and a bottom which set a standard for female backsides everywhere. Cute as button, and hot as a firecracker Missy had a date anytime she wanted. But for all her dating she hadn’t ever brought a guy home...

2 years ago
  • 0
  • 17
  • 0

Missys time alone

Missy arrived home earlier than her brother or parents and this thrilled her. She opened the front door, threw her books to the bench beside the door and rushed to her room. Inside she walked to the large mirror covering her bathroom door and stopped. She admired her body in the mirror. It was beautiful. She was beautiful. She didn’t feel she was cocky in thinking this because it hadn’t always been so. At one time she had been odd looking. The daughter of mixed races, part Native American, part...

2 years ago
  • 0
  • 38
  • 0

Telling Mom Im A Crossdresser Part 25 My New Toy

It was a few days later after my night with mom at the adult shop, and my ass was still sore and I could still remember the taste of the cum in my mouth from that man. I could also still feel the pain in my ass from having to walk all the way home with my mom’s dildo in my ass.My mind wandered as I thought about how my mom reacted to getting her dildo and how horny she got just by looking at it and me during that night. After we got home, my mom told me to have a bath and go to bed because it...

Incest
4 years ago
  • 0
  • 34
  • 0

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

Part 14: Back to the spa I’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...

4 years ago
  • 0
  • 32
  • 0

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...

4 years ago
  • 0
  • 25
  • 0

Missys Naughty Night Out Part 1

Ethan kisses my cheek as he stands beside me at the bar. I smile up and kiss him in return. ‘Ready to go home Missy?’ ‘Is that a suggestion or a command?’ I answer with a mischievious gleam in my eye. Ethan squeezes my thigh and winks, ‘It was a question.’ He leans in and tucks a stray lock of hair behind my ear, whispering, ‘Now what is the answer little madam?’ ‘Let’s go home.’ Sipping the last of my bellini, Ethan helps me down off the bar stool and places his hand on the small of my...

1 year ago
  • 0
  • 12
  • 0

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...

3 years ago
  • 0
  • 22
  • 0

Telling Mom Im A Crossdresser Part 11 Girl time

Part 11 It 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...

3 years ago
  • 0
  • 34
  • 0

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...

2 years ago
  • 0
  • 19
  • 0

Telling Mom Im A Crossdresser Part 16 Hot talk With Mom

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...

4 years ago
  • 0
  • 21
  • 0

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...

4 years ago
  • 0
  • 21
  • 0

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

3 years ago
  • 0
  • 49
  • 0

Telling Mom Im A Crossdresser Part 4 Repeat Business and Roleplays

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also pink with white stockings and long lace gloves that went up to my shoulders. Finally the top was like satin...

4 years ago
  • 0
  • 35
  • 0

Telling Mom Im A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

2 years ago
  • 0
  • 24
  • 0

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...

3 years ago
  • 0
  • 32
  • 0

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...

3 years ago
  • 0
  • 37
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
2 years ago
  • 0
  • 19
  • 0

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

2 years ago
  • 0
  • 54
  • 0

Crossdresser porn story 1

Ray Hirsch sat at a desk filling out form after form. It was amazing, the information that an employer required before you could start working at a new job: health insurance forms, Social Security, etc., and etc. He was now filling out a questionnaire on his background which would be used to conduct a security investigation, since his work might involve working on classified government projects. He stopped for a minute at the question: List any aliases you have used. “I wonder if I should...

2 years ago
  • 0
  • 26
  • 0

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...

3 years ago
  • 0
  • 24
  • 0

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

4 years ago
  • 0
  • 23
  • 0

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...

4 years ago
  • 0
  • 17
  • 0

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...

4 years ago
  • 0
  • 22
  • 0

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...

4 years ago
  • 0
  • 20
  • 0

CD crossdresser sissy caught by mom and dad pt3

Please go back and read part 1 and 2 before reading this or nothing will make any sense. I ended part two after going to the pool with my mom and dad, having sex then coming home and showing together. That was a few days ago. Not much happened between now and yesterday but I've been wearing girls clothes when at home, basically a bra and thong, heels, and normally a dress. My mom ordered me a romper and some skirts and blouses to wear too. I've also been wearing the chastity belt all the time...

2 years ago
  • 0
  • 20
  • 0

Cd crossdresser sissy caught by mom and dad pt4

Sorry to all those waiting on another post - been busy and haven't gotten to it.So my mom, dad and I just returned from a wonderful trip to the Bahamas on our boat and we had some wonderful sex.I had totally forgotten about this trip until the day before we left when my dad brought our boat home from the place we keep it about 20 minutes from our house. My mom had rented a house on one of the islands in the bahamas with a small private beach and a place to put our boat. Well I started packing,...

3 years ago
  • 0
  • 23
  • 0

CD crossdresser sissy caught by mom and dad pt2

So I left off my true story last right when I woke up the morning after getting caught by my mom and her and my father having sex with me, go read that before you read this otherwise it wont make since.That was about a week ago now. Well that next morning I woke up naked in my parents bed at about 9:30 naked from the sex the night before, walked into my kitchen and saw my mom sitting at the table in lingerie with a coverup just wrapped around her but not hiding anything with my one of my dress...

2 years ago
  • 0
  • 27
  • 0

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
3 years ago
  • 0
  • 35
  • 0

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
3 years ago
  • 0
  • 31
  • 0

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
  • 0
  • 26
  • 0

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
2 years ago
  • 0
  • 150
  • 0

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...

2 years ago
  • 0
  • 25
  • 0

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...

2 years ago
  • 0
  • 43
  • 0

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...

3 years ago
  • 0
  • 32
  • 0

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...

Porn Trends