My First Time Crossdressing For A Friend free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
One night when i was 14 i had a friend spend the night, we talked about sex as most guys our age did, and the fact than neither one of us had ever had sex. We talked about the typ of porn we liked as we had found our parents porn stashes and would watch them every chance we got. Then it came up that he had seen a bi vid that his mom had, it was mm/mmf, with one sean involving a guy dressed like a girl and it had realy turned him on. He said that the guy looked hot as a girl, and that he was getting a hard on just thinking about it. I could see it getting hard in his shorts and i was starting to think about us doing the things he was discribing . I had played dress up with my older sister when i was younger as she didnt want a little brouther, i dressed up a few times on my own after that i loved the way i felt. I told him about playing dress up and he asked what i looked like and i told him i looked like my mom. I was tall and thin long legs and firm round ass sholder length dark broun hair and deep green eyes when im excited. the only thing i didnt have was tits, well and i had a small dick then that was tucked when i dressed up i went on telling him. I didnt know why i had the urge to tell him things i never thought i would ever tell annyone, but it just felt right some how. He told me that if i looked like my mom that i must look so hot all dressed up. The thing that realy got him is when i told him that when i dressed i dressed and ackted just like her including the way she smokes. It wasnt long and he was begging me to dress up, telling me that my parents were out of town and my older sister was staing next door. after a few min. of him pleading with me i gave in and started for moms room and got dressed up, and did my makeup. i had a black lace braw 38 dd that held two ice bags filled with warm watter that giggledas i moved. next was black stockings and guarders with a pair of 6 inch black heals, fallowed by a black short skirt and a very thin white blouse that you could see my braw threw it. When i was all done i went back to the couch where he was waighting, i light a cigarette and set next to him after doing a littel turne to let him see it all. He was speachless, then he said wow you do look just like her and that i had her act down to a t. He told me that he fantisized about doing thing with my mom when he would jerk off. Thats when i asked him like what he said like her giving him head and then fucking her. I noticed he was even harder then befor, and i asked him if he was hard for me or the idea of me looking like my mom. He answered quick mostly your mom but its still you. Buy this time he was rubbing his crotch and i said damn that thing lookes like its going to rip through your pants. he laught and said it feals like it to and it wont go away. I half joking said i bet mommy could make it go away he said realy. I didnt know what to say i had wanted to try sucking a dick but i was scared that i would be bad at it. I thought for a moment and said whipit out big boy and to my suprise he did. He was about 7 inches long and very thick. I chickend out, and he put it back in his shorts and we down on the blankets on the flor and watched tv till we fell asleep,i was still dressed.I woke a few hours later to him rubbing my tits and the sound of him jacking off as he was whispering my moms name, and saying how good it felt. I kept my eyes closed just enough for him not to know i was awake, but enough to see what he was doing. He was stroking it just a few inches awaw from my face. after a bit he used his free hand to gently open my mouth and put the head of it in my mouth and started to move it in and out slow trying not to wake me. I had never realy wanted a dick in my mouth till then. I now was so into it after a few minouts i started to suck it. he jumped back pulling it out of my mouth with a soft popping sound. I looked up and asked why he stoped and he said it wasnt right that he shouldnt have done that to me. I told him but you did it any way you had your dick in my mouth and you said you like it. He set there for a minout, and i patted the floor where he had benn, and he slowley moved back next to me on the floor. I opend my mouth and guided the head in and started to suck him. He said my name as i was sucking him and i stoped, and said call me linda dont say that outher name if you want me to keep going and he said ok. I sucked him slow and deep, after a few minouts his dick started to swell in my mouth and i knew from my own that he was going to cum. I stoped and asked him how where he wanted to cum, in my mouth or do you want to fuck me? He said bouth that he can cun 3 or 4 times a night. I smiled and said ok pleas fuck me first, and reached for my purse wich i had put my cigarettes and a tube of moms lube and a condome in it befor going into the room with him. I lit a cigarette and we set next to each outher on the couch, he told me i looked just like her and i said i am her dont think of me as looking like her think of me as being her or i cant do this just call me linda or miss riggs. I told him the more he calld me by her name the more i got into the part, he agreed that it was getting him harder then he had ever been. He then said linda i want to make love to you so bad, and ismiled and we started kissing. I had caught my mom having a few on night stands and knew what she liked and what things she would say to help get the guy off faster, so with that in mind i leand over and started sucking his dick again. he was gently pushing my head down on his dick and soon i felt his balls on my chin and knew i had all 7 inches of it in my mouth and throat.He started to cum and pushed me all the way downas i felt each of 7 hard squirts in my throat then he relaxed his grip on me and i felt 2 more squirts on my toung. It was very thich and salty, and i loved the texture as i swallowed it all down it burnt a bit but i loved my first tast of cum. I set back up and finished my cigarette, im a slut i thought to my self i just swallowed a guys cum and im haveing a cigarette just like mom after giving head.I wanted more, we talked as him and linda and the whole time i could still taste his cum in my mouth. He was still hard and soon he was kissing my neck and telling me he wanted to be inside me so bad it hurt i nodded my aproval and he started kissing me downmy sides and sliped his hands up my thighs and pushed up my skirt and slid my thong down my legs and took them off then tosed them on the floor next to the couch. i was tucked and i looked just like her with a thick patch of hair and it almost looked like lips. He got the condom and i told him what mom tells guys she wanted bear( ive had my tubes tied so you dont need that unless you want to)just to let him know it was ok with me if he wanted to cum in me bearback. I spread my legs wide and lubed my hole and he lubed his big dick then got over me.I reached down and took his hard dick in my hand and put the head right at my hole and said i want you in me, but rember you have to go slow you have a big dick. With that he leand down and sliped his toung in my mouth and pushed fowared slowly, i felt a pop and a sharp pinch as the head sliped in then we stoped for a second to let the pain go away. Then he slowly pushed till it was all the way in. I wasnt getting hard but it felt like i was on fire in my ass and my clit. He moved slowly in and out of me for about 3 minouts and i was kissing him amd telling him how amasing his big dick felt inside me and then i couldnt take it anymore i started begging him as slutty as i could pleas fuck me, fucke me hard and fast. It was a good thing we were alone as i was not whispering, i was screaming and shouting fuck me as he hammerd my ass as hard as he could. A few minouts later he finaly started swelling up and i felt him tens up as he started yelling oh fuck im cumming and my ass got real hot and slippery, as he finished cumming in me he colapsed on top of me kissing me and gasping for air. We laid there for a bit with his dick sti in me half hard and he said he loved the way my tits bounced as he fucked me. I kissed him and said i loved the way his dick felt inside me, and that i wasnt done with his dick unless he couldnt go any more. He said he wanted a lot more but didnt want to use my moms name that we need to come up with a name of my own. We set up and his dick sliped out and i stood up and got my cigarettes and set on the couch with my legs crosed as i smoked my cigarette i thought about names.iI chose deborah from a distant aunt, i took lyn from my best female friends ever and riggs is from the bestguy friend i ever had growing up. He was gay but was the only one who didnt know it lol he is still one of the best friends ive ever had.


thank you hoped you enjoyed reading about my first time. if you liked it let me know and ill wright more.

debby r.

Same as My first time crossdressing for a friend Videos

2 years ago
  • 0
  • 17
  • 0

Caught Crossdressing by Aunt Sharon

Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...

1 year ago
  • 0
  • 21
  • 0

My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

1 year ago
  • 0
  • 9
  • 0

My crossdressing fantasies Free Sex Stories and Adult Erotica Stories

I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...

Cross Dresser
2 years ago
  • 0
  • 10
  • 0

First time crossdressing with a friend

My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....

Crossdressing
3 years ago
  • 0
  • 10
  • 0

Crossdressing Charlie Episode 6 The Tennis Uniform

CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...

3 years ago
  • 0
  • 95
  • 0

JOANNE SLAM A LIFETIME OF CROSSDRESSINGhellipAlmost

JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...

3 years ago
  • 0
  • 13
  • 0

Crossdressing Charlie Vol 1 Episode 1 The School Uniform

CROSSDRESSING CHARLIE Volume One Episode 1 THE SCHOOL UNIFORM The thump of the car door made Charlie open his eyes. The sound of a second door slamming made him sit upright in the bed like a startled squirrel. He listened carefully. The ignition jerked several times before the engine started up. He was still as a statue as he listened to the low rumble of the car reversing out of the driveway. He scurried across the blankets, jumped off the side of the bed and stumbled over a pile...

4 years ago
  • 0
  • 20
  • 0

Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

1 year ago
  • 0
  • 15
  • 0

A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

Humor
3 years ago
  • 0
  • 31
  • 0

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

Crossdressing
2 years ago
  • 0
  • 11
  • 0

Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

3 years ago
  • 0
  • 15
  • 0

Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

2 years ago
  • 0
  • 11
  • 0

first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...

1 year ago
  • 0
  • 14
  • 0

An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

Crossdressing
2 years ago
  • 0
  • 15
  • 0

Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

Crossdressing
3 years ago
  • 0
  • 16
  • 0

Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

3 years ago
  • 0
  • 9
  • 0

First crossdressing experience 3 cocks in1 hr pa

I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...

2 years ago
  • 0
  • 12
  • 0

Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?This is a real life story of a crossdresser caught in the act!This happened around when I was 15 yrs. old.As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my...

1 year ago
  • 0
  • 9
  • 0

The Late Crossdressing Husband

THE LATE CROSSDRESSING HUSBAND by enduringshades Edith and I had known each other since we were teenagers. We went shopping together and often met for lunch or coffee. Friday night used to be our Girls Night Out when we dressed to the nines and headed for our favourite bar. Then we got married (not to each other!) and stopped going out together. Edith was still a party girl, but I stayed at home with my wife, Betty. I never told Betty that I was a crossdresser. I missed being...

2 years ago
  • 0
  • 45
  • 0

Stefanies Crossdressing Memoirs Vol 6

I've decided to switch the category for these over from blog post to sex story, as at this point in my adventures as a gay crossdresser, I had pretty much hit my stride dressing up and finding men and other crossdressers online to have sex with. So I guess you could say my posts moving forward will be a little more "action" oriented. Plus at this point it is hard to remember all of my experiences chronologically, and for the most part that's really kind of irrelevant. If any of you are...

2 years ago
  • 0
  • 25
  • 0

Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual
1 year ago
  • 0
  • 17
  • 0

Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

3 years ago
  • 0
  • 17
  • 0

An Introduction to Crossdressing Pt 5

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...

Crossdressing
3 years ago
  • 0
  • 28
  • 0

Girlfriend Catches Me Crossdressing

At this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...

3 years ago
  • 0
  • 32
  • 0

Duped Into Being a Crossdressing Bull Part I

During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...

3 years ago
  • 0
  • 13
  • 0

The story of how i began crossdressing Part 13

Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...

3 years ago
  • 0
  • 13
  • 0

The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...

3 years ago
  • 0
  • 13
  • 0

Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

1 year ago
  • 0
  • 14
  • 0

Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

1 year ago
  • 0
  • 15
  • 0

Crossdressing Fun From A Womans Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...

Crossdressing
3 years ago
  • 0
  • 21
  • 0

Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

2 years ago
  • 0
  • 21
  • 0

Ashleys Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

Crossdressing
3 years ago
  • 0
  • 11
  • 0

Sex with a crossdressing in a public toilet

Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...

3 years ago
  • 0
  • 9
  • 0

Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

3 years ago
  • 0
  • 11
  • 0

An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

Crossdressing
2 years ago
  • 0
  • 10
  • 0

An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing
4 years ago
  • 0
  • 14
  • 0

An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing
2 years ago
  • 0
  • 9
  • 0

Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing
2 years ago
  • 0
  • 14
  • 0

Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing
2 years ago
  • 0
  • 16
  • 0

Married Crossdressing Fun Ch 2

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

Crossdressing
3 years ago
  • 0
  • 10
  • 0

Married Crossdressing Fun Ch 1

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

Crossdressing
1 year ago
  • 0
  • 19
  • 0

An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing
2 years ago
  • 0
  • 14
  • 0

An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing
2 years ago
  • 0
  • 10
  • 0

Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

2 years ago
  • 0
  • 10
  • 0

A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

2 years ago
  • 0
  • 9
  • 0

Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing
1 year ago
  • 0
  • 9
  • 0

Mother and Crossdressing Son Fantasy

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

3 years ago
  • 0
  • 17
  • 0

Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

2 years ago
  • 0
  • 7
  • 0

Wifes crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing
3 years ago
  • 0
  • 11
  • 0

Wifes Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing
3 years ago
  • 0
  • 18
  • 0

Wifes Crossdressing Fantasy

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease. We talked about many things. He told me I was cute and that...

Crossdressing
2 years ago
  • 0
  • 9
  • 0

Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

3 years ago
  • 0
  • 10
  • 0

Kissing Crossdressing Cousins

For as long as I can remember, I have always been drawn to wearing women's clothing. When I was 4 years old, my mother would take me shopping and I would throw tantrums if my she didn't take me to look at the girls clothes too. I would try on pants but only on one condition: I got to look at the dresses when we were done!When I was 5 years old, I wanted to be Princess Leia for Halloween. My mother thought it was adorable and was more than happy to buy me the costume. The following year, I...

3 years ago
  • 0
  • 10
  • 0

Making Scents of Crossdressing

Making Scents of Crossdressing By Ricky I am a hi-tech person. I work and play with some of the latest computers and electronic equipment, have stereo speakers in every room of the house, and can bore you for hours with torrents of jargon on just about any subject you care to name. When I don my feminine attire I have a fondness for synthetics, those modern wonders of the laboratories of some multinational chemical giant. Who else but those hi-tech wizards could turn a barrel...

Humor
2 years ago
  • 0
  • 14
  • 0

Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

3 years ago
  • 0
  • 9
  • 0

Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

2 years ago
  • 0
  • 11
  • 0

Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

2 years ago
  • 0
  • 7
  • 0

Crossdressing Charlie Episode 3 Relinquishment

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

Porn Trends