My First Time Dressing With Someone free porn video

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

I was 14 at the time, I had a girlfriend at school. Parents agreed to let me stay over as long as we didn't stay in the same room. She had a sister a couple of years older, I stayed in her room and she stayed with my gf. I'd already been interested in dressing, so when I was left alone for the night I went through her clothes. She was messy so there was used knickers on the floor and stuff. I put together an outfit, wearing a bra, skirt, tight tshirt, black tights, and a thong.

When I was dressed, I started looking in her cupboard to see what else she had. I must of been too loud, her dad came to check what it was. I was like a rabbit in headlights, frozen still with my ass in the air and my head in the bottom of the cupboard. I didn't know what to do or say so I just stayed still. I waited hoping he'd just leave, then I heard the door close. I sighed in relief, then i realised he'd shut the door behind him!

He came over and placed one hand on my waist, lent down and then the other hand around my mouth. I didn’t know what to do. I looked up him and saw him smiling, I then felt the press of something against my face. It was his hard cock through boxers. I look back up at him and realise he’s loving it. I smile and pull down his boxers. His already hard cock springs out and slaps me in the face. I try not to laugh, he pulls his hand away from my mouth. I grab his cock with one hand and place the tip on my lips. I’d seen some porn videos so I kinda knew what to do. But I’d never even had a bj myself yet. I started sucking him, with each thrust getting deeper.

I started gagging as he got deeper. Luckily I’d practiced on ice lollies all my life, I just didn’t know what for. I have no idea how long it was going on for, but I was loving her minute. Eventually he pulled back, I thought I'd done something wrong. He grabbed me by my neck and pulled me up, pushed me onto the bed. I couldn't believe it, he wanted to fuck me! I was so excited I was close to cumming in my girlfriend's sister's thong. He rolled me onto my front, pulled up the skirt and across the thong. I tried to spread my legs to open my ass as much as possible, I knew this was going to hurt. He pushed the tip gently in, then out, then in, then out. I loved it! I wanted him deeper, so the next time he pushed in I pushed back against him. Next thing I know I can feel his manly balls slapping against me as he fucked me, one hand on my waist and the other over my mouth. Just as he's about to cum, he pulls out, rolls me over onto my back, pushes my legs up in the air. He grabs his cock and rests the tip on my ass. He puts one finger into my ass to spread it, and then shoots his load into me. I'd never seen anything like it, I was trying my best not to moan. He pulled the thong back across, pulled down my skirt. He looked down at me, smiled, and then left without a word.

I’d not expected any of that. Breakfast the next morning was a bit awkward, he offered to give me a lift home. I got in the car and as we started driving back, he asked if last night was ok. I lent forward to show I was still wearing the thong from last night, as I got out the car I said “see you soon hopefully”. Later that night my girlfriend text me saying her parents liked me and I could stay whenever.

Over the next few months the same thing happened. Every time it was the same, sometimes he'd ask me to wear certain things, like what his daughter had been wearing and he'd call me her name. I didn't mind, I was a good girl :) It wasn't until my girlfriend and I turned 16 that we stopped. Now me and her were sharing a bed, and I had no time to see her dad.

0
0

08.05.2020
14
0

Same as My first time dressing with someone Videos

The Amazing Mr Mortimer

THE AMAZING MR. MORTIMER My girlfriend Rachel and I had decided to take a two week vacation to PuertoRico. I had first come across the girl on the streets of San Juan. She cameup to me and begged me for some money. At first I was going to say no. ThenI noticed how beautiful this young girl was and I was intrigued. I startedto reach into my purse to get her something, and she smiled at me. She hada very beautiful smile. It was in fact an entrancing smile. I kept her close to me with small bribes...

Mortimer and Myrtle A Love Story

Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

First time dressing

I do not claim to be a grammar expert and as such you will find some grammatical errors in this story. The errors can be the switching of tense, spelling errors, or typos. I ask if you find an error please send me an email so I can correct and make the story enjoyable for others.WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are u******e Eighteen, PLEASE DELETE THIS FILE NOW!!!!II did not know I had a disorder did...

Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

Lesbian

FaceTime with Ann Next Door

I never FaceTime. I'm not a adolescent girl. I don't need to see your face when a simple text will do. Call me an old bastard, get-off-my-lawn type, but that's the way it is. (By the way, I'm not that old).So when that mechanical beeping emanates from my phone that someone wants to FaceTime me, it's definitely out of the ordinary. Especially when it's 10:30 on a Tuesday night. I got to my phone and it said "Ann FaceTime video."Well, this was different. Ann Next Door and I been fooling around on...

Daytime friends nightime lovers

She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½ feet. Dark red… it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the crystals were so thick it turned everything pastel. Breaking it apart just enough to smoke easy, she arranged the weed in...

Daytime friends nightime lovers

Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...

Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

First time dressing with Mrs H

So carrying on from where I left off..... I regularly went round to my friends Mum ...Mrs H ....strategically when he was out an d he seemed to be packed off to his grandparents more than he ever had been...now I realise why ! LolI wa slaways welcomed by Mrs h clad in nylons and heels and sexy undies, more ofthen than not an obg in black to match her stockings and heels and she was always in artistic harming points ...at that time they were still freely available which started my passion for...

Consequences of Cross Dressing

Consequences of Cross Dressing by Cindy Johnson ([email protected]) My dilemma was that I masturbated all over mother's gown and nylons and I frantically tried to clean everything up as fast as possible. I was frightened that it would leave a stain and I didn't know what to do but after twenty minutes of cleaning everything with soap and water, I felt like I was in the clear. I put everything back where it I found them and ran to my room reflecting on what had just happened. I...

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...

Going Nova ch 3 The Dressing Room

The knocking persisted and Hazel croaked sleepily, “Honey, will you go see who that is?” Warrick sighed, sat up in bed, and stretched. He knew full well who it was. He rubbed his hand lightly on his wife’s naked back for a moment, thinking fondly about the previous night, and then got up to put on his bathrobe. He smoothed his bedhead over as he descended the stairs to the door. When he opened it, Elsie burst inside. “Hey Warrick! Is Brie awake yet?” she asked brightly. “Elsie, it’s far too...

Pleasures at Dressing Manor part 7

Pleasures at Dressing Manor - by PRIM The story so far: Young teacher Miles Johnson has tried his best to rescue his pupil, Lyndon Blonding, 18, from the sissifying plans of his spiteful stepmother, Vera Hidebotham, who aims to turn her stepson into a girl. His Headmistress, Alison Forceman, accompanied the young teacher to the boy's home, Dressing Manor, outwardly to help him but secretly in league with Vera. The two males have been fed the feminizing drug Fem-Agra,...

Dressing Phase 1 A Holiday in Venice

DRESSING: PHASE 1 - A HOLIDAY IN VENICE Barry Robbins and I have been best friends since we were three years old and met in the Reception Class at Nursery School. Naturally as two active, competitive little boys we had our moments and our spats, but it soon became clear to our parents and teachers that we functioned better together than apart. As we grew up it was apparent that our talents and personalities complemented each other. Barry was the imaginative one; I could come up with...

Halftime Stranger

It was a warm October night and I was at a college football game with a few buddies. Throughout the first half of the game, I looked to my right and there was this hot sexy bald guy 3 sections to my right. He had huge arms and was wearing a black wife-beater and jeans. We kept looking at each other and at each time, he would show that bright smile of his.At halftime, I went to the restroom and used one of the stalls, luckily I was the only one in the bathroom. As I opened the stall, he was...

Brittany in the Dressing Room

She didn't understand what she was doing here, in JC Penny on a Wednesday afternoon. Her long distance fucktoy, Jordan lived on the east coast. She had, of course, sent him dirty pictures from dressing rooms while she shopped before; usually Victoria Secret dressing rooms. And she had even played with herself in a dressing room while he watched via Facetime. But every one of those times was in a store of her choosing; he had never before specified where she should go. What the fuck was going...

Toys

First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

Dressing Room

"Honey, how does this skirt look on me?" Dee asked as she swung open the door to the dressing room and stepped out of the dressing area. She spun around in the waiting area, causing the dress lift off her legs, revealing her bare legs and ass. Dee rarely wore underwear and never missed a chance to "accidentally" expose herself in public, particularly when I was watching. "I like this one better than the green one" I said as I stood from the small couch in the waiting area and approached...

Pleasures at Dressing Manor 5

Pleasures at Dressing Manor - part 5 of 7 by PRIM The story so far: Young teacher Miles Johnson receives a letter from his pupil, Lyndon Blonding, 18, telling how his spiteful stepmother is keeping him prisoner and dressing him childishly. He takes the letter to his Headmistress, Alison Forceman, who secretly feeds Miles the feminizing drug Fem-Agra, so that he becomes addicted to girls' clothing and suffers embarrassing changes to his body, before accompanying him in his bid to...

The Dressing Room

My boyfriend and I had a date coming up. Lately our dates had been ending up with steamy sex, so I wanted to buy a sexy outfit and some new lingerie for our date. I had visited several stores, before I finally found a few things I liked. I wanted something sexy and just a little bit slutty. It had to be just right. I dressed with sex in mind when I left the house. I’m not a stick thin model. I have curves. Maybe more than most men would like, but my boyfriend loves having something to grab onto...

Quickie Sex

Dressing room

It was a month after my first sexual encounter with Manisha – a lot has happened. We had the kingdom to ourselves cause we shared a dorm room, she was my roommate, my lover, my sex toy, my everything at that moment. We had sex almost every day, and today was not going to be any different. I don’t know why, but that day I was extremely horny. The kind of horniness I was experiencing was the kind you don’t experience often in your life. It’s the kind you just need to satisfy as soon as possible,...

Lesbian

Dressing Room

It was a month after my first sexual encounter with Sarah - a lot has happened. We had the kingdom to ourselves cause we shared a dorm room, she was my roommate, my lover, my sex toy, my everything at that moment. We had sex almost every day, and today was not going to be any different. I don't know why, but that day I was extremely horny. The kind of horniness I was experiencing was the kind you don't experience often in your life. It's the kind you just need to satisfy as soon as possible,...

Summertime In Colorado

Summertime In Colorado I absolutely love summertime. The hotter it is the less the girls wear. Instead of long jeans they wear short shorts. Instead of full blouses they wear skimpy tops. Coats are strictly out of the question too. Bikinis are popular even if it is just the top half with a micro mini skirt. Like I said I absolutely love summertime. Girls of all ages are wonderful to look at. Touching them might be a different story but looking at them is still legal. The problem...

Summertime Blues

Summertime Blues Author's Note: This is an old story of mine which I self-edited using the great suggestions I been receiving. I will go back and edit it more. I want to see how well I could implement the suggestions which I got. Also, I want to give a thanks to all the people who had help me in my writing. It was a bright sunny Saturday afternoon in July yet it was raining in Joe's mind. This was for Joe was having a run of the mill bad day so he headed to the bar for a drink. He...

Pleasures at Dressing Manor

Pleasures at Dressing Manor - part 1 of 7 Chapter 1: Who can help poor Lyndon Blonding? Dear Mr Johnson, I am writing this letter to tell you about my stepmother, Vera, and how she has kept me away from school for the past two weeks. I am not allowed out of the house; in fact I am imprisoned in my bedroom with the door and windows locked. Not only that, sir, but my stepmother has taken away all my clothes. I have to wear a little short sleeved white shirt and pale green...

Pleasures at Dressing Manor

Pleasures at Dressing Manor - part 6 of 7 The story so far: Young teacher Miles Johnson receives a letter from his pupil, Lyndon Blonding, 18, telling how his spiteful stepmother is keeping him prisoner and dressing him childishly. He takes the letter to his Headmistress, Alison Forceman, who secretly feeds Miles the feminizing drug Fem-Agra, so that he becomes addicted to girls' clothing and suffers embarrassing changes to his body, before accompanying him in his bid to rescue the...

Sex in dressing room

Friday night my wife and I decided to join friends at a rugby club as one of her collogues were playing in a friendly game for the club. We went and sat on the pavilion next to our friends and I went to the bar to get us something to drink. I saw my wife walked to the field to talk to her collogue who was taking a 5min break. As she was walking there, the guys from the dressing room were making comments to her and whistled at her and telling her how sexy she looked. I returned with the drinks...

Group Sex

Dressing room encounter

‘Babe, can you come here and help me with this?’ I walk back into the dressing room as your open the door. I’m greeted by your long bare legs as my eyes begin to travel up your body. As you giggle you say, ‘here sweetie…my eyes are here.’ My eyes finally meet yours and you can’t help but notice that wickedness that you’ve seen before. After a brief moment, you lightly grasp my cock through my shorts and give it a quick squeeze. ‘Behave,’ you lightly whisper so the other customers don’t hear...

Dressing room encounter

"Babe, can you come here and help me with this?" I walk back into the dressing room as your open the door. I'm greeted by your long bare legs as my eyes begin to travel up your body. As you giggle you say, "here sweetie...my eyes are here." My eyes finally meet yours and you can't help but notice that wickedness that you've seen before. After a brief moment, you lightly grasp my cock through my shorts and give it a quick squeeze. "Behave," you lightly whisper so the other customers don't hear...

Love Stories

Dressing Room Curtain

I walked a few paces behind my wife as we strolled through clothing store after clothing store. She wasn't looking for anything in particular like I would have if I had gone shopping. If I needed a pair of black pants, I'd go to my usual store, grab one in my size, sometimes even try it on, and buy it. I'd do anything to get it over with as quickly as possible. But for her, the search was the fun part. So I tagged along. The only saving grace, other than making my wife happy, was that she...

Mrs T The Sales Girl and Me Dressing Room

Upon Mrs. T requestI read her this story as she stroked my cockshe did not let any leak out her sexy red lipsI love to shop. It always better to go shopping with someone else. There is nothing more fun then going shopping with Mrs. T. We always seem to have fun. On some occasion we have a little too much fun. I usually buy her what ever she wants. On most shopping trips she buys everything with her husband credit card or cash. She likes to make a game out of shopping sometimes. She likes to...

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age,...

Pleasures at Dressing Manor 4

Pleasures at Dressing Manor The story so far: Miles Johnson, a newly qualified teacher, receives a letter from his pupil, Lyndon Blonding, 18, telling how his father has eloped and his stepmother is venting her fury on him, keeping him prisoner at Dressing Manor, dressing him childishly and punishing him severely. He takes the letter to his Headmistress, Alison Forceman, who has Miles visiting her study every afternoon as a result, where he becomes addicted to the feminizing drug...

Reese Witherspoon dommed

any of the actresses mentioned below. This story is written down for enjoyment purposes only. Reese witherspoon woke up with a headache. She didn't know where she was. All she could feel that she was blindfolded. Not only that, she was tied to the bed with duct tape, unable to move her hands and legs. She also noticed that she was nude. A duct tape covered her mouth so that she shouldn't shout. All she remembered was going to a producer's home for some script reading of a film they were...

The dressing room

This is a true experience I had a few years ago,Several years ago, at the request of some friends, I was asked to help a girl with her portfolio. She wanted to get into modelingand knew no photographers & was afraid they were all perverts, only wanting to get them naked. At first I suggested a few women I knew that would help her to relax & get some good shots. Instead she enlisted our mutual friends to as ke to do it. She was the first"model" I had ever worked with & fortunately it...

How I started Cross Dressing and other first times

I love to cross-dress! I love everything about it!Like most of us cross dressers, I love everything about ladies undergarments. I like seeing lingerie in ads, in stores, on models, on TV, 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”, which is wearing lots of lingerie under your manly clothes, when I go to work. I especially love the incredible horniness and lack of all boundaries...

FaceTime surprise

I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

Showtime for Teri

Showtime for Teri By Teri Franken Chapter 1 My name is Teri and I am 28 years old. I have been a closet sissy for as long as I can remember. My parents knew that I was not your typical child and they let me live how I wanted to and did not judge me, they just loved me unconditionally. I grew up loving everything that a little boy typically doesn't like, such as dresses and dolls. My parents were concerned that I would be a target for bullies, so I was home schooled, took my GED...

In her Dressingroom

With a make-up wipe I took the orange glaze, the white glitter and the sweat of my face. It was always such a satisfying moment. After the show was done, my muscles sore, I would take off the sweaty costume of the Sugarplum fairy, but before I jumped into the shower of my private dressing room I first took the make-up off my face. Seeing the Sugarplum fairy disappear and my own face reappear. A moment of self care. A moment off calm, no sounds, no music, just the soft rumbling of the...

intro to the world of cross dressing1

My family was middle class mutt of a family. My mom brought two daughters and one son, Tammy, Lilly, and Teddy, or “Tee” as we call him, into the marriage; she had with my dad, and they had two, my brother and me. My full brother’s name is Ken, and I’m Sam. My dad was an accountant and a part-time college professor at the local community college, and my mom stayed at home as a housewife. We were all dragged to church every Sunday and when we became of age we were allowed to choose whether or...

Lisa Lee Xdressing Adventures

I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it! I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I do have the opportunity I tend to get pretty wild, like I did a few weeks ago….

xdressing school fucked by black teacher

This is a kinky sexual fantasy about my university teacher .Well it all started the first day my new teacher walked in the door .Six foot, very good looking black man .He was 15 years older than me very smooth with the girls.I just turned 21 and am three years into my transformation from male to female i have DD cup boobs. After 2 months of fantasizing and flirting with him i decided to make my move i needed that black cock inside me .I decided to wear the sluttiest school uniform i had it was...

Sidedressing

Sidedressing By Tyrone Slothrop Older sisters can be a boy's good friend and most effective torturer. Bernadette, charged with watching her little brother, was getting bored and decided to see how far she could manipulate him. Nothing nasty just keeping her hand in. Practice makes perfect. "Ralphie, come here, I want to try a new game." Ralph heard his sister and put down his videogame. He wandered into her room. At thirteen he was fairly average in height, about five feet...

The Halloween Crosdressing Mistake

The Halloween Crossdressing Mistake My wife Stacy and I were standing in a room with about 30 other people. The room, was one of those fancy ballrooms that you only find in old universities, or houses that were owned by people with entirely too much money. I mean really, who has the extra money just lying around to build a ballroom!? You can use these things what, four times a year if you are lucky? Well, I digress. So we are standing there in this ballroom, at what is...

Lisa Lee Xdressing Adventures

I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it! I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I do have the opportunity I tend to get pretty wild, like I did a few weeks ago…. My wife went...

Crossdressing

True tales of submission and crossdressing Chapter Two William

Introduction ------------ Following on from my first instalment, here is another true story. As before, I have tried to remember events as accurately as I can, but of course all speech is paraphrased. I hope there are people out there who enjoy reading this, and perhaps it will inspire people to go ahead and indulge their fantasies. Whatever your kink, there's probably someone out there who will be into it too, and it's not a crime to enjoy life! Curiosity... ------------ So...

Ultimate fetish dressing

0. She was sitting on the edge of her bathtub completely naked looking out into her bedroom with a kind of thill of anticipation. She had had a full bath and had just finished shaving her body except for her beautiful dark hair. She also had been given several huge cleansing enemas, until what she expelled was as clear as water. She wasn't a perfect girl, she new, slightly smaller than usual with her 163 cm, and she wasn't as thin as some of her friends, but she had full breasts and an inviting...

Eagle in the Sunset 2019Chapter 29 Summertime for Us All

October 17th, 1995, 7:30 AM PT, Metro Plaza Hotel, Los Angeles, CA Miriam had been tossing and turning all night; she spent time just sitting in the chair in the corner of the room to try and let Baruch sleep. She was so upset she was oblivious to the fact that Baruch couldn’t sleep either, which was not in her nature. She was usually fully aware of what was going on with her husband. They thought together almost telepathically, and yesterday had been one of the first times in decades when...

Timeless Beauty

TIMELESS BEAUTY BY PAUL G. JUTRAS Sam walked in the dorm house, looked at the lock and then in the dorm mistress's room. The plus size woman was dress in a black blouse and flats, black with white palm tree design jacket and skirt with dark brown nylons. She new there was only a half hour before she made her rounds and called lights out. Upstairs, roommates Chris and Alex waited on their beds. Like their friend Sam, both guys were petite and lovely looking. Being transsexuals who...

First Time Sex With My Longtime Bestie

Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali. We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department. She had a sexy shape, which gave me a...

Younger Than Springtime

The door was open. I had no reason to have it closed. We were all in this together. So I was sitting in the large chair as my nurse prepared to access my port to begin the first liter of Cisplatin. The cancer center had been busy today and I glanced out the doorway as several people passed by. Then I noticed a woman pausing as one of the nurses escorted her somewhere.It was Katherine. I recognized her at once even though it had been so many years ago. Then I heard her laugh as her companion...

College Sex

First Time Dressing

My first time didn't actually start out as a 'solo' experimentation as it seems like so many other girls' first times. It didn't start out as raiding the laundry basket of a mother, sister, neighbor, or girl down the street; finding a pair of pantyhose in some trash container; or even reading about crossdressing in some stashed away porn magazine. In fact... my first time was actually like something out of a fantasy story somewhere... you know, those stories you read where boy meets...

Dressing For Melissa

DRESSING FOR MELISSA - by: Cissy Gale It was the early 1970's, the height of the glam-rock era, when I let a girl named Kim dress me up in drag. The events of that evening spiraled hopelessly out of my control when I was publicly humiliated by Kim, then locked out of her house still in drag. This led to her friend Angela seeing me in my ridiculous outfit, an event Angela confessed she hoped to see repeated. Kim had already promised to dress me up again to surprise and amuse...

Cross Dressing Lover

The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all...

Gay Male

Old lady fucks her cross dressing friend

Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. She wanted more – a lot more – sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open minded seeks new experiences, fun and frolics. I am 5’ 4”, dress size 18 with 36D bust and welcome either gender and any age.She was amazed that it attracted a few older cross-dressing men, which surprised her greatly...

Old lady fucks her cross dressing friend

Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. She wanted more – a lot more – sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open minded seeks new experiences, fun and frolics. I am 5’ 4”, dress size 18 with 36D bust and welcome either gender and any age.She was amazed that it attracted a few older cross-dressing men, which surprised her greatly...

Porn Trends