My First Real Outfit

By Chrissy_CD_slut

Original link:

Tags: crossdressing, masturbation,

Added: 12 Nov 2009 Views: 25611 Avg Score: 4.6

My First Real Outfit

I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my mom’s pantyhose and jerking myself to incredible orgasms while wearing them or being forced to wear them from a older friend when I was young.

I loved the feeling of the silky smooth nylon on my legs and cock. I would occasionally put on one of her night gowns with the hose, the feeling of the satin touching the nylon hose would drive me nuts and I would just lay on the bed and roll around rubbing my legs against the gown.

When I went off to college I was able to explore my fondness of all things soft and silky even more. I had a roommate but he would leave every weekend to go home to Houston and I would have the whole place to myself. This is when I first really started to “dress up” and be the woman I desired to be.

I skipped class on a Friday and drove to Houston . I went to a lingerie store and bought myself some really sexy gear. I remember it like it was yesterday. I bought a red lacey “Wonder Bra”, matching thong, garter belt, and a pair of black lace top thigh highs. I found a sexy red strappy spandex type dress that was short, but not too short, maybe about 3 inches above the knee and had a sexy slit up the side.

I went to the counter to pay and the lady looked up at me and smiled. She told me that who ever I was buying this for sure would like it.

I just smiled back and said I hope so, it’s for a special night.

She sort of giggled and said that she hopes she likes it and placed it in tissue paper and then slid it in a bag for me.

I got in my car and drove off looking for a shoe store to buy some girly shoes. I went to a Famous Footwear store and went in. I browsed around trying to look inconspicuous in the women’s shoe dept., without much luck. An older lady came and ask if I needed help. I told her no I was just looking, she smiled and walked away. I looked around and found a foot scale to see what size I wore in ladies. I checked my foot and went to the size 11 section. Apparently women who wear size 11 don’t have a lot of choices for sexy shoes. I did manage to find a pair that would do. They were a pair of red velvet sandals with thin straps, a 3 inch heel and ankle strap with a buckle. I grabbed them and went to the end of the aisle and tried them on real fast, snug but they worked.

I went to the counter to pay and when the lady saw what I was buying she just grinned at me and rang me up. As I was walking out I could here her and another lady giggling at me.

I got in my car and drove to another parking lot to examine my purchase closer. I took out all my stuff and laid it out on the seat next to me so I could see it all. I took out the stockings and rubbed one on my leg. The feeling was electric! I kicked of my sandal and pulled one of the stockings up to my knee. I took one of the heels and slid my foot right in and buckled the strap. The nylon sure helped my foot glide in the shoe, and the look of that shoe on my foot was so erotic.

I tucked everything back in it’s bag and shoes in their box and drove home thinking of what laid in store for my evening.

When I got home I scanned the parking lot for my roommates car. It was nowhere to be seen so that meant that he had already left for Houston . I grabbed my stuff and ran up the stairs. I was so nervous with anticipation I could barely get the key in the door. I got in and locked the door with the deadbolt and the chain.

I went to my room and stripped to my boxers. I took all my new clothes and took the tags off and neatly laid them out on the bed.

I went to the kitchen and grabbed a beer, went back to my room and sat in a chair with a raging hard on drinking my beer and staring at the wonderful outfit laid out before me.

I drank a couple more beers and smoked a half a joint while watching some porn. Remember we are college guys so there was no shortage of booze, weed and porn around our apartment. I sat there for about an hour and finally decided it was time.

I went and took a nice hot shower, dried off and blew dry my hair. I blew my hair upwards so it would have a full look to it. (this was the 80’s and my hair was about 4 inches past my shoulders) I teased it up a bit on top and sprayed it with hair spray doing the best I could at feminine looking hair.

I walked into my room and took the bra and wrapped it around my waist, spun it around and pulled the straps over my shoulders. I walked to my dresser and got a pair of tube socks and rolled them up nice and round and placed them in the cups of the bra. It felt so good, just enough wiggle from the water in the “Wonder Bra” and the softness of the socks to feel somewhat like real tits.

I went back and sat in the chair and slid the stockings up my arm and pulled them down so they were bunched up at my hand. I put my foot in it and slowly pulled it all the way up my leg and then I did the other. I rubbed my legs together feeling the nylons against my skin.

I took the garter belt and put it around my waist. I clipped the clips to the tops of my stockings and checked in the mirror to make sure they were straight. They weren’t and I had to repeat this about 4-5 times before I got it right. I sat down and leaned over sliding my hand up my legs from the feet pulling the stockings snug and then adjusted the straps tight.

I slid the thong up my legs and over the garter belt straps. This is how I saw the girls in pornos wear them so that’s what I wanted to do, be a porno slut.

I reached over and grabbed the heels and slid my foot into one and buckled the thin strap around my ankle. I looked down and admired my leg with a sexy shoe and stocking covering it. I put the other one on and stretched my legs out in front of me and stared at them. I felt so sexy and feminine; my hard on was raging and oozing pre cum into my new thong.

I stood up and walked to the full length mirror on the closet door. I stood there admiring this feminine being in front of me. I turned and looked at my ass, bent over, watching myself in the mirror the entire time. I was amazed at how sexy and girly I felt wearing this lingerie.

I practiced walking around the apartment getting used to the heels, which was quite a chore. They were only 3 inches but felt like 6. I damn near fell a dozen times before I somewhat got control of it. I went and got a beer and sat on a bar stool at the bar and smoked a cigarette with my legs crossed like a woman

I loved the look of my legs with the stockings and heels, it was so intoxicating. I finished my cig and beer and walked through the kitchen again just to hear my heels clicking on the floor. I went back to my bedroom and got my dress. I held it up in front of me looking at it in the mirror as I held it against my body. I stepped into it from the top and pulled it up my legs and slid my arms through the straps. After a few minutes of pulling and adjusting it I finally had it on right. It fit very well, snug but not so tight that it showed my bra straps or garter belt. The bottom had just a slight flare to it and a nice slit so it hung a little loose on my thighs. I stood there looking in the mirror in a total daze of how sexy I looked and felt.

I sat on the bar stool drinking beer and smoking cigs for a good hour, crossing and uncrossing my legs. I loved the way the slit in the dress showed just the lace top of my stockings and when I had my left leg over my right leg you could see the garter belt strap. It made me feel so sexy!

I had a real good buzz on so I turned my attention to the TV where I had a good hardcore porno going. I was really getting into watching the guys fuck these girls like madmen. Just watching the girls turned me on so much. I loved how they always wore their thigh highs and heels while getting fucked.

I started rubbing my cock through my dress getting myself horny as hell. I would pull my dress up and expose my thong and garter belt shaking my ass and slapping it.

I finally couldn’t handle it anymore, I had to cum. I had been all dressed up for over 2 hours sporting a hard on for almost all of it.

I took off my dress and slid my thong down freeing my aching cock. I walked to the bathroom to get a bottle of lotion while watching my cock swing up and down as I walked. I felt so slutty! I sat on the sofa with my legs spread wide open and cock sticking straight up to my face. (I have a 7” cock, cut and fairly thick that curves upward like a banana)

I pumped a couple of good drops of lotion over my cock head and this sent shivers through my body. I slowly started rubbing it all around my head, stroking and pushing it down between my legs so it looked like I had a real pussy when I closed my legs. I started stroking faster and harder while playing with my balls. I was rubbing my balls furiously when my fingers slid between my ass cheeks and I shuddered.

I took some lotion and rubbed it all around my asshole. I leaned back and spread my legs wide in the air and slowly started to finger my ass with one finger. It felt amazing when it slid inside me. I fucked myself with one finger, then 2 fingers while pumping my cock. I could feel my load brewing deep inside my balls. I pushed my 2 fingers all the way inside my tight ass and jerked my cock like mad. I felt it coming so I bucked my hips upward and shot a massive load of hot sticky cum all over me. The first shot hit my chin, the second on my neck and the rest, 5-6 more shots landed on my bra and stomach.

I pulled my fingers from my ass and slowly milked every last drop from my cock onto me. I lay there totally exhausted and covered in hot man cum. I reached down and rubbed it around with my fingers feeling the sticky cum. I scooped some up and brought my fingers to my mouth, I looked at it for a second or two, then I sucked my fingers in my mouth tasting my salty semen. I closed my eyes and moaned as I sucked my fingers clean. I took the rest of it from my chin, neck and stomach with my fingers and licked every drop from my hand.

I laid there totally exhausted but in total ecstasy from the huge orgasm I had just had.

I went to my room and slowly undressed the rest of the way. I put my lingerie on a shelf in the back of my closet and hung my dress on a hanger way in the back. I walked over and fell in my bed and went right to sleep.

When I awoke the next morning I felt like I had the best night sleep of my life. I walked to my closet and took down my lingerie and stood the staring at it. I felt the bra and smelled the crotch of my thong. It smelled so sexy. I put them back where they belonged, closed the door and went and made me some breakfast.