First Time Dressing With Mrs H free porn video

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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 ! Lol

I 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 them. She had showed me how she got dressed in her clothes, how to dress up and show off her womanly figure in a sexy way, how to walk in high heels, how to move her hips and bum to attract the attention of men and then would regularly have me , often after a minimum of 4 hours whilst she rode my cock, and never before she had had five orgasms would she let me cum....often inside her pussy, sometimes in her mouth or over her tits and stockings. She would always lick up my hot cream except when I came on her stockings, then she would share it with me telling me it was good to lick up my hot spunk off the nylon and then kiss each other deeply and passionately. So I became used to fucking her good an hard to satisfy her before being allowed to realise the pleasure of my own orgasm until one day, she welcomed me at the door, dressed as usual in ff nylons, an obg and heels but this time she was holding a brand new packet of artistic harmony points in black, an obg and heels which I had not seen before...dangling them off her sexy long fingers , the red nail polish contrasting against what she was holding.

she said she had a surprise for me which she knew I would enjoy and something that she said she had tried with her husband but he did not enjoy it but she knew I would !

firstly she took me to her bathroom where a nice warm bubble bath was waiting....I got in and she proceeded to tell me I was to wear nylons and heels to experience what it was like to rub my nyloned legs against other nylons but first she needed to shave my lightly hairy legs..... I immediately was concerned that my own mum would notice my legs were shaven but she said, it’s winter you won’t be wearing shorts for ages yet , and joked that my mum no longer saw me naked which was true! So I let her soak my legs and she explained it would get the hairs nice and soft. She then proceeded to shave my legs all the way up to my pubic hair which she also trimmed and shaved into w nice triangle just like I had seen the girls have in girlie magazines that I had wanked over. All the time she was explaining to me that the feeling if the nylon stocking against my skin would be very nice, and that it would make my cock harder for longer so she could ride it longer and take it deep inside her pussy.

once she had finished shaving me, she dried me off with a nice fluffy towel and put cream on my legs and public area, paying particular attention to my cock which was , as usual, standing very much to attention ! Lol she then proceeded to put the obg on me, it was very tight and felt great as she pulled it up my legs and around my waist. It looked great in the mirror as I posed in front of it as she told me to do, showing me how it made my waist even flatter than it was, and the cheeks of my bottom stick out slightly giving them a more feminine curve. She told me how great I looked and then she opened the packet of ff nylons and showed me how to remove them carefully from the packaging. She gave me a pair of white soft gloves to put on and then explained how to roll them up to the reinforcing of the toe, keeping the seam as straight as possible as I slipped it over my toes and along my foot.....I was trembling as I did so and she then showed me how to pull it over the heel of my foot and keep the seam straight as it started from the end of the point heel and pull them slowly and gently up my legs all the time adjusting the seam as I did so.

she then showed me how to clip the suspenders clips into the stockings, starting at the back into the finishing loop and then the other three clips around the top of my legs. She did the same instruction with the other one , and I stood before her as she sat and she smoothed the nylon up and down my legs until she was satisfied they were perfect. She then said that these nylons were always worn with high heeled stiletto shoes and she picked up the shoes she had with her. They heels looked very high, as high as the ones she often wore and were black patent with a very sharply pointed toe. She said that I was two sizes bigger than her ...she was a five and so therefore I was a seven, and that she had bought them specially for me to wear when I visited her. She said she would keep them in her special drawer for me, along with all the clothing she bought for me ove rthe next few years. Later on, I would often be allowed to take stuff home with me to wear in bed !

so she helped me put the shoes on as I sat and admired them in the mirror.....and they looked just perfect to me, the sheen of the patent fabric shining in the mirror and complementing the sheer nylon of the fully fashioned stockings. She made sure my seams were snow straight again and then she said I was to stand up very slowly and carefully.....it felt awakward for a few moments but as I looked in the mirror, something in my head clicked and I knew I was hooked on dressing up.....my cock was rock hard which she commented on, saying that I must like what I saw ? I mumbled yes and although I was a little embarrassed at what I saw, I knew it was very much a turn on.

she then showed me how to walk in the shoes, slowly at first, over the carpet and then after about ten minutes, she said I should try the stairs which were wooden. She held my hand tightly, it felt so erotic as she did so , all the while telling me how sexy I looked in my heels and nylons, how long my legs looked and how beautiful they felt as she brushed and rubbed the nylon. The sound of the heels clicking on the wooden stairs felt divine in my head...she said did I like the sound of the heels....I said yes...... very much so. Ok she said, don’t get over confident but now see how you can walk up and down the stairs holding onto the rail...do it till you feel it’s natural...so I walked up and down the stairs for then minutes, eventually managing to do so without holding on to the rail.

ok she said, you seem to have the hang of it, now let’s go for a walk downstairs around the house and I proceeded to strut around downstairs, my heels clicking faster and faster as I got more daring at walking in those sexy gorgeous six inch heels. All the time, she was watching me, looking at my cock which was still as hard as rock and she kept commenting on the effect all this was having on me and how sexy it was.

we then had a conversation about transvestism and how it turned her on....he husband had tried it a few times with her at her instigation but he did not like the way it made him feel she said..... he was a very manly man and although I think they had an ok sex life, she was I discovered very much into the kinkier side of sex than her was, and i subsequently discovered that he only used to fuck her once a week in a Saturday evening before he died and she needed so much more than that. And that was my introduction to dressing with her...needless to say we fucked like rabbits that day....and many more afterwards, all the time caressing each other’s nylons and heels, me bending her over and being instructed to lick her seams, all the way up to her legs, then her pussy and bum hole, we really did go thru the whole spectrum of nylon and heels appreciation.

more to come about the first time she really feminised me completely.

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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...

4 years ago
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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...

4 years ago
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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….

1 year ago
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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...

3 years ago
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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...

2 years ago
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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...

2 years ago
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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
3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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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...

1 year ago
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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
4 years ago
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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...

4 years ago
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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...

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