Dressed In Holiday Style I free porn video

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Dressed in holiday style I

I watched the speed limit, which is unusual for me, as I pointed the car west towards the Evil City. It was about 1:30 a.m. and dark on the interstate that stretches across the prairie, so I was wearing a black mini-skirt, fish-net garter stockings and my four inch stilettos as I drove through the night. Beneath my soft cashmere sweater, I was wearing a black silk chemise and I kept the cabin of the car cool so that my nipples were erect through the silk fabric.

I usually don’t dress and drive, but it was a special occasion. I was about to lose my virginity as a gurl.

I had met Dean and Sandy online, when they had messaged me, admiring some of the pics I had posted. Through the months, we became friends, trading photographs and messages online. They lived on the west coast, far from the quiet boredom of the high plains where I reside.

Dean originally was from the plains and had family in the area in the major metropolitan area about four hours from where I live. (On the plains, we don’t measure space by miles, but by the time it takes to get somewhere.) Imagine my reaction when Dean informed me that they were planning a visit to the Evil City.

I wrangled a free-lance job to photograph the Christmas lights in the Evil City. I picked a time frame where I knew that my spouse had to work, arranging three days and two nights to do the shoot which would coincidentally coincide with Dean and Sandy’s visit.

I could hardly wait and I found that I was growing hard beneath my lacy thong as I drove through the night listening to my homemade Avenue D cd in the car.

I had been cross dressing off and on since high school. I couldn’t help it seemed after I had once slipped on that soft silky slip that I’d found in the trash. After feeling the soft sheer material on my genitals, I was hooked and my longings for being a woman, always suppressed, intensified.

I’d stop for a while but then I’d begin again in a frenzy for about three decades. After I discovered the internet, I learned that I wasn’t the only freak out there cross-dressing in the world, that I was probably cross-gendered and slowly came to terms with the fact that, since I am middle-aged, I wasn’t going to transform readily. I finally accepted my life as a closet CD.

But I also discovered that I really, really wanted to be taken as a woman at least once in my life.

Dean and Sandy were a dream come true. Dean loved cross dressers, and using his theatrical background had spent years assisting them with dressing, makeup and all other nuances of passing. He had shown me some of his work on the web and it was impressive.

I sang in my best falsetto voice with the recording as I drove carefully through the night. ‘Do you look like a slut? Un huh…shut up!’ My boi clitty became harder as I seat-danced to the song, wishing that I had boobs to undulate as I drove and danced under the clear night sky. I played with my nipples and the lace-covered cock as I drove.

I stopped at a deserted interstate safety stop shortly before entering the City, pulling off my heels and replacing them with sneakers. I pulled on the sweat shirt and hoodie that I had in the passenger seat next to me and then continued my drive to the City. I arrived at the large downtown hotel and checked into my room, a nice suite with an adjourning door to the room that Dean and Sandy had reserved. I suppressed an urge to knock on the door, as I knew that they weren’t due into the city until late the following evening.

Drawing the blinds, I slipped into a new lacey nightie and tried to sleep, but the excitement of the upcoming adventure was too much and my boi clitty was still hard as a rock, poking like a tent pole through the satin fabric.

I grabbed all the pillows on the bed and the extra ones that I had brought and made my pillow mount, tucking the clitty behind my ass as I lowered my weight on the mound, ensuring that the rolled pillow was in place where my vagina should be to hold the dick in place a push my balls behind me.

I reached behind me and found the head of my clitty and it almost leaped for my bung-hole, the pre-cum hot and slimy oozing from it’s little opening as I slide it home.

I sighed and leaned forward on my elbows, pulling my small boobs out of the shift and began to massage my nipples as I bounced on the pillows the head of my cock sliding in and of my hole, never deeply penetrating as I longed for, but filling the opening nether less. I suddered as I came, then rolling off of my pillow mound I stretched and cuddling a body pillow, fell asleep.

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My SexPacked Holiday Part Nine A Final Threesome

I awoke early on Friday morning, and lay in bed idly strumming at my clitoris. I opened my legs just far enough to let me slip a couple of fingers inside my pussy, and was pleasantly surprised to find how sloppy I already was up there. It was the last full day of my holiday, and to be honest, it hadn’t been anything like I’d expected. I’d had a hell of a lot of sex, for a start, and not just of the normal “in, out and wipe yourself clean” kind, either. Peeing, fisting, anal: I’d had my eyes...

Threesomes
2 years ago
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My Holiday fuck with a Chav

I guess I was always the shy kind. I was never particularly outgoing in many respects. I was the second c***d to a well brought up family. I had an older sister called Carli that was much more aware of life than me. I was in every respect a shy naive guy when I became 18. I was studious, a constant worrier and I think in many respects that is why mum decided after getting my A-level results to book a holiday in the August of 2011.She had decided to book a two week break in Ibiza. Mum knew that...

2 years ago
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My mums holiday

I usually phone my mum about once a week to see how she is. On this occasion I was quite nervous, considering what had happened between us the previous weekend (see stories: My Mum's Birthday, and parts 2 & 3). I thought she might be quite stand-offish, or even blame me for taking advantage of her when she was so drunk. But to my relief she seemed quite her normal self, and didn't even mention what had gone on over her birthday. Either she can't remember, or she's too embarrassed, I...

2 years ago
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Kinky Holiday

We’ve been in Puerto Rico for a week now, we are both very chilled out and nicely tanned, we both look healthy and fit. We’ve been on the beach for most of the day catching up on our tan’s and playing in the sand and sea, so we decide it’s time for a slow walk back to the apartment and to call in and have a couple of happy hour cocktails in a bar we like on the way back.We grab a couple of drinks in the bar, which is quite quiet as its change over time for the holiday makers, people going to...

3 years ago
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Holiday Romance

Holiday Romance by Richard-to-Rachel It was two days before our holiday to Prague that my girlfriend decided to leave me, it turned out that she'd been cheating on me for a while and had come to realise just now that she couldn't live with it on her conscience any longer. I was heartbroken, I had felt that we'd had a real connection and now I found out that she'd been deceiving me all along. I'd never really had much luck with women, I wasn't great looking and kind of shy and it had...

3 years ago
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Lizs holiday threesome

Liz was now in her early twenties. After a fairly late start to her sexual life, it started to flourish when she was in her late teens. It was a time when men came onto her from every angle, and it was difficult to turn the attention away. She did have the odd longer term boyfriend, but often this would end in disaster as she found it hard to focus on her boyfriend when men were chasing her.Basically her late teens mean't lots and lots of cock for Liz. She was a stunning blonde, large...

Group Sex
2 years ago
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Holiday Sex

Hi, my name's Lisa and I want to tell you a story about my first girls holiday abroad. At the time i was 20 years old, stood at 5ft 6 and pictures of me taken on this trip would reveal that i wouldn't look out of place in any hot list. My shoulder length brunette hair caressing my slender figure and whilst my breasts were small they were adorned by fat nipples that demonstrated when I was turned on.It was about halfway through the holiday and so far i'd been very disappointed with the sexual...

1 year ago
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Holiday break

This story was written for legal, open-minded adults only. Among other elements, it explores dangerously, the border of consensual sex.... ------------------------------------------------------------------------ If you are into stories where the first sentence cuts straight into the hardcore scene. I.e. A wife contends with an 18" penis being inserted into a selection of different orifices, with little erotic storyline and no connection to the realities of life. Then you will probably find this...

Group Sex
3 years ago
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Stuffing the Holiday Virgin

Stuffing the Holiday VirginBy Macy Alexander this story will be included in new book out this week!amazon . com / author / macyalexander I was really looking forward to going home for Christmas – I didn’t want to admit it, but I was a little homesick my freshman year at University. So, I was shocked when my mom called and told me that she and my dad were going on a cruise this year instead of hosting the holidays like they’d done every year of my life! Mom said that they had been planning this...

2 years ago
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Holiday of Fun Part 1

Holiday of fun Part 1My annual holiday had been booked months in advance, I was looking forward to chilling for 14 days in the sun, relaxing on the beach and having a few drinks at night. This year was different though as I was travelling alone, my friend had recently got engaged and would be holidaying with his fiancé. So, as I enjoy my own company I decided I would still travel but this year I could do as I pleased without having to compromise to keep my friend happy as well.It was Friday...

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