Dressed in holiday style I
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 f****y 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 sl**p, 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 asl**p.