Laura's First Time

It was Friday afternoon about 4:30 and I was just arriving home from work. I was looking forward to a quiet evening of relaxing as my other persona, Laura. My roommate Mark had gone in on afternoons and I had the apartment to myself for the next few hours. I stripped down to my silk undies and stay up stockings that I had worn to work in anticipation of dressing tonight as Laura.

I started a bath, adding bubbles and skin softeners, and returned to my room to pick out an outfit. I chose a black pencil skirt that comes to just above my knees and a green silky blouse to wear over a matching silky black thong and bra set, a garter, black stockings and 3" pumps. I arranged my clothes on the bed and throwing a chemise on over my panties I went for my bath. Sliding out of my silky garments into a hot, bubbly and relaxing tub I lay back and let the water take me. I ran my hands over my legs and felt the stubble. I needed to shave my legs. I decided to shave my entire body as it had been a few days. I got out my razor and set about getting my self smooth. I removed all my hair except for a little strip above my penis.

I quickly washed up and got out of the tub drying off as it emptied. I returned to my room and throwing the towel aside I sat on my bed. Following my routine I fastened my garter around my waste. I slipped my arms through the bra and sliding the straps on my shoulders I reached behind me and fastened my bra. I stood in front of my mirrow and made minor adjustments. Now for the stockings. I sat again on the bed and began rolling up my stocking, as I finished I dipped my toes in the stockings and started to slowly roll them up my leg. This is a sensation that I enjoy, the feeling of silky stockings on my legs and thighs.

As I finished rolling on my stocking I stretched my leg in front of me and smoothed and straightened them. I fastened the garter clips on the top of the stockings and then put my stocking on the other leg repeating the process. Once my stockings were secure i stood again in front of the mirror and made slight adjustments. I picked up my thong, held it in front of me and stepped into the leg holes one at a time. I wiggled the thong over my thighs and pulled it into place tucking my now hardening cock in between my legs. I stood in front of the mirror admiring the sexy outfit. I ran my hands over my chest and crotch loving the feeling of the soft garments against my skin.

I had discovered dressing at the age of 12 starting with my sisters panties and nightgowns because I loved seeing my sisters in thier silky nightwear. I found myself alone at home one day and was drawn to her laundry basket where i found panties and a silky pj set. I was in heaven!! I dressed in them and slid under the sheets of my sisters bed and pretended to be my sister playing with a strange cock. I quickly ejaculated a huge load on my sisters pj's the sensation was so good..

Very early I found my self thinking of pleasuring men when I dressed. I would enjoy the sensation of the silky fabrics to the point of becoming very horny and then I would masturbate while running my hands over my body thinking of how I would want to be with a man. The thought of holding a strange cock in my hands while I was dressed was a favorite fantasy.

I soon progressed to wearing bra's with my panties and one of my sisters, bless her soul, liked to wear stockings. She had an assortment of garters and panty and bra sets. I found I loved the sensation of wearing stockings with a bra and panty. I also started to try on her full slips and half slips with a chemise over my foundation garments. I loved the silky feel of the slips and this soon became my favorite pastime when no one else was home. I was starting to build my own collection of pantie's, bra's, garters, stockings and slips.

When no one was home I would go to my room and play dress up, changing into an array of different combinations of lingerie. Once dressed I became bored of being confined to my room and decided to walk around the house dressed in my silkys. As I passed my sisters room I saw her closet was open and a recent purchase hung on the door. I had a sudden urge to try her new dress on. It was a sexy little black dress that came above my knee. I zipped up the back of the dress and looked in the mirror and I was hooked. What a feeling slipping into a slinky little number and zipping yourself in. It felt so good sliding on top of my slip and stockings and I loved the way it looked. I stood on my toes looking at my self in her mirror and then thought why not try on a pair of shoes!! On the floor in front of me was an assortment of shoes in her closet. I chose black pumps with 3" heels and slipped my feet into them. Oh my, I loved the way they looked and it dawned on me that I would no longer be happy lounging around in my lingerie. I wanted to dress as a woman, in dresses, skirts and silky blouses. I wanted to wear heels and I knew I would now want a wig.

I noticed the makeup on my sisters dresser and took a closer look. I picked up her lipstick and popped the cap off. It was a bright pink and I immediately began to apply it to my lips, followed by blush, blue eyeshadow and mascara. It was a rough job but at the time I was so excited by my apparrel and what I was doing I became extremely aroused. I lay on her bed and groped my self as I thought of being with a fantasy lover who allowed me to kiss him and touch him to arousal. I only became interested in men while dressed as a woman. I had no interest when I wasn't. As I imagined I was a woman stroking a mans cock to fruition I felt my own approaching orgasm. I feared making a mess on my sisters new dress and cupped my hand around my cock to catch my cum. I had the most intense orgasm of my life. 5 strong spurts filled my hands to over flowing and with the fear of staining my sisters new dress I began licking the cum off my hands as it started to leak between my fingers. As I lay on the bed holding my sisters dress above my waste and licking cum from my hands I felt so slutty and horny that I poured cum from my hand onto my waiting tongue. I liked the taste and now I had progressed to dressing fully in womans clothing and fantasing about pleasuring a mans cock with my mouth. This remained a fantasy as I did not have the courage to go out dressed and never actively looked for anyone.

My green blouse went on first as I stood in front of the mirror doing up the buttons in the front. I picked the pencil skirt up from the bed and held it in front of me as I stepped one leg in at a time. I slipped it over my hips, tucked in my blouse, pulled up the back zipper and fastened the button. I stepped into my 3" black pumps, I love the feeling of nylon sliding into a pump, and fastened on my ankle bracelet. I have both ears pierced which gives me lots of options for earings. Tonight I choose big gold hoops with matching chain and bracelet. I sat in front of my dresser mirror and applied false nails and painted them red. Once dry I put on my long brunette wig and headed for the bathroom with my makeup bag. I fixed my hair in front of the big mirrors and began to apply my makeup. I had a lot more experience now and a lot more makeup too!! I used a lip liner before applying bright red lipstick, blush, eyeliner and shadow, I was just touching up my mascara when a shadow crossed my light. I looked to the bathroom doorway and there stood my roommate, Mark, with a surprised look on his face. A little smile crossed his lips and he said " Well, well, and what do we have here?"