This is a true story written entirely by me hoping to share some of my eritic experiences with the readers here.
I grew up a normal healthy boy in the suburbs of a large city in the Midwest. At puberty I started to feel the beginnings of sexuality. I noticed girls of course but I was attracted and fascinated by older sexy looking women. I loved to look at pictures of women with heavy make up, tight short dresses, and of course red lipstick, high heels and stockings. I was captivated to no end. I remember when I was probably 14 finding one of my moms lipsticks on the sink in the bathroom. I'll never forget that the shade was called "Bravado". I removed the cap and twisted up the phallic looking red lipstick. I looked in the mirror and as if in a trance I applied it to my lips.the feel, the smell was the most uniquely sexual experience of my young life. I felt a sensation in my penis and it instantly became erect. It felt great to touch it while I made sexy faces in the mirror. All of a sudden the room begin to spin. I seemed to loose complete control and my penis begin to grow then twitch in my hand. I shot a little white spurt of something in the sink. Although it felt good, it scared me. I had no idea at that point that I just had the very first orgasm of my life. I quickly wiped off the lipstick, wiped my cum from the sink and went outside to play. I remember the next few days trying to sort out what had happened.
After a few days I decided to see if I could repeat the experience, and as you can guess I was putting on lipstick and masturbating every chance I got. I almost got caught by my mom or my sister several times but it somehow made it even more exciting and dangerous to do. By the time I was 15, whenever my family was gone I would put on one of my moms dresses, wig, and high heels and parade around the house. I wished I was born a girl and began to wonder what it would be like to be with a boy when I was dressed as a girl. I knew I wasn't a homosexual but when I dressed as a girl I had had fantasies of sucking a cock. I knew where my dad kept his porn tapes and I watched them with great interest and practiced my budding blow job techniques on a pop bottle. I also experimented with alcohol about this time and snuck swigs of whiskey, vodka or gin from my parent's liquor cabinet. The taste was terrible but I liked the warm buzz it gave me.
At 17 my parents decided to go away for a long weekend to visit family and I talked them into letting me stay home me at home alone. My sister was away at collage and I was so excited being alone to be a girl all weekend. They asked our neighbor, Denny to look in on me from time to time. Denny was a nice guy, younger than my parents at 30 years old, and a good looking guy. All the teenage girls in the neighborhood thought he was a real dreamboat and he was always nice to me.
For weeks I fantasized about how I would dress and what I would do. I would take my time to dress sexy, watch some porn and have a few drinks, and of course masturbate the weekend away. I was so excited I was ready to burst! I did some shopping to pick up the things I couldn't "borrow" from mom and sis. I got some sexy false eyelashes, glue on red nails, a pack of menthol 100 cigarettes, panties, stockings and my own hot red lipstick. After they left I saw Denny in the driveway and told him I was just watching TV tonight and I would call him if I needed him.
I picked out a great outfit from a combination of mom and sis and laid it out on my bed along with the other things I bought. I made a vodka and seven-up and drew myself a nice hot bubble bath. I felt butterflies in anticipation of the great night ahead of me as I sipped my drink in the tub. After I dried off I applied a perfume scented powder all over than I sat at my mom's make-up table to apply my make-up. I had practiced a lot so it went very well. I love heavy sexy make-up and tonight I did it all. I put on my eye shadow (shades of grey and light purple) and lots of eyeliner and mascara. My brows were perfectly arched (and actually matched) and the false eyelashes gave me the exotic look I was after. My new creamy bright red lipstick, perfectly lined gave me the full pouty lips of a high class hooker. I about came right there just admiring my handy work.
I went down to the kitchen to make another drink and I put a porn tape in the VCR. I watched a sexy girl give a nasty blow job then went into my room to get dressed. I pulled up the black stockings and slipped on the patent leather stiletto pumps. I wondered where my mom wore these but was happy she did. Next I squeezed into a black leather miniskirt. I already had on a black lace bra that I filled with two water balloons. They bounced a little bit when I walked just like the real thing. I selected a white sheer blouse and I turned up the collar and unbuttoned it down to just below my bra. Next I put on a sexy long blonde hair wig I bought on the internet. It took me awhile to get the styling down but it looked hot after a struggle. I went back to the living room and liked the sound my stiletto heels made on the tile floor.so sexy. I took a few digital pictures then poured vodka seven. I was really in heaven with the combination of scents feelings, and vodka. As I watched the porn take I applied the finishing touch, I applied the long red nails carefully to my fingers. As I waited for the glue to dry I lit a cigarette. It looked so sexy with my red nails. My she-cock was aching for relief but I decided to tease myself and not allow myself a cum just yet. I walked back to the kitchen to fix another drink and by this time I was pretty tipsy and I liked it.
Suddenly I was startled by the back kitchen door opening and as I looked up there was Denny looking just as surprised as me! I panicked and tried to run but Denny was standing in the doorway. I tried to get past him but when he didn't move I begin to cry and begged him to not tell anyone about catching me like this. He put his arms around me to consul me and said he would never tell anyone. As I sobbed he squeezed me tighter and gently rocked me back and forth. He told me it was OK and that I looked absolutely fantastic as a girl. I was pretty shaken up as he sat me down at the kitchen table and handed me my drink. My hands shook as I took a sip and he continued to say how sexy I was. Denny made himself a drink as we sat and talked. After several minutes I began to feel more comfortable, in fact kind of nice. It dawned on me that my make up must be all messed up from crying so I excused myself to go the bathroom to fix it. I saw him watch me as I walked away so I made sure I did that little wiggle of my ass that guys like. Once in the bathroom I saw that my make-up actually held up pretty well so I touched up a bit and applied another coat of mascara a little powder several more coats of lipstick. I pulled up my stockings and sprayed some more perfume.
When I returned Denny was sitting on the couch watching the porn tape I had playing. As I came around the couch he stood up and told me I looked fantastic and hugged me. I hugged back and told him thanks for being so understanding and as we parted we looked each other in the eyes for several long seconds. I thought he would kiss me and my heart was pounding so loud I thought he could hear it. He didn't and then sat back down on the couch and asked me to sit down next to him. He was so understanding and easy to talk to. I could tell he liked it as much as me. The electricity in the air was incredible, with the porn on the TV, the drinks flowing.
My mini skirt rode up and exposed the top of my stockings and Denny lightly rubbed his big manly hands on them ever so gently. I noticed the bulge in his jeans and ran my long red finger nails across the bulge. We continued this teasing as we watched a hot babe on the tape give a sexy blow job. We were both mesmerized until the guy shot a load in her mouth. Denny then put his arm around me and asked if I was sure I wanted to do this. I looked him in the eye and replied that I have been fantasizing about this for a long time and I was very sure. Denny stood up and started to unbuckle his belt and I pushed his hands away and told him to let me do it. We both laughed when I found how hard it was to do with long nails, but after a bit of a struggle I popped the button to his jeans, and pulled down his zipper. I reached into his underpants and grabbed the first cock I felt in my life other than mine. I pulled it out and it was beautiful. My first cock was inches from my lips and I wanted this moment to last forever. I asked him to wait a second as I reached over to the coffee table for my purse. I removed my lipstick and looked up at him as I applied it liberally until my lips felt soft and creamy. I set it down on the table and took a sip of my drink as I leaned forward and without touching his penis I engulfed the large tip between my red lips. Denny moaned and stiffened his body. I placed my hands behind his muscular legs and slowly pulled him closer and his penis deeper in my mouth. It felt so different than I imagined. It was hard yet soft at the same time. Denny told me how great it felt as I slowly and deliberately sucked the head of his cock. Ever so slowly I picked up the pace until he was fucking my mouth. I cupped his balls with one hand and placed the other on his shaft. I opened my eyes to see his shaft covered with my lipstick red tinted saliva and my long red nails working its length with a twisting motion as it went in and out of my mouth. I placed my tongue on the underside of his cock and I felt it grow even more. Suddenly it begin to twitch and he spurted his cum in my mouth. It caught me by surprise and I gagged a bit at first then sucked it deep as he fired spurt after spurt down my throat. It seemed to last forever then his cock softened slightly as I resumed sucking it. I felt his legs quiver and I released them and Denny sat down on the coffee table opposite me. As I fixed my lipstick again he told me he never had a blow job quite like that and asked where I learned to do that. I replied that I did it a thousand times in my mind and of course I was very highly motivated to pleasure him. He waited until I fixed my lipstick then I leaned over and hugged him and kissed him.
He looked me in the eye and said now what? I said looks like you have a fuck- buddy now Denny and he smiled and kissed me deeply. We made out on the couch for a long time and Denny reached under my skirt and played with my cock as I played with his. When he got hard again a told him to lay down on the floor for me and I straddled him as we kissed. I sucked him again to full attention. I asked him to hold on and I scooted into the bathroom for some baby oil. I squirted into my hand and massaged it into my crack and my ass hole then rubbed the remaining oil on Denny's hard cock. I again straddled him and guided his cock to my ass. I pushed against it and it didn't seem to fit then plop, it plunged in and surprised me and hurt just a bit. After a few seconds the feeling changed to a delightful fullness and I begin to move up and down. It felt so fabulous to get fucked! I wanted more so I got off Denny and turned on all fours with my ass facing him.
Denny fuck me I said and he got on his knees and slipped his cock in my willing ass. It slid in with no resistance and he fucked me silly for a very long time. I was literally screaming to Denny to fuck my ass and he was pounding me hard. My own cock was hard and twitching with every trust. Denny said he was cumming and I swear I felt it every spurt of cum in my tight pussy-ass. My own cock without being even touched shot its load at the same time. Exhausted I laid down and Denny lay on top of me, both of us breathing heavily. For several minutes all we could both say was Oh my gosh, Oh my gosh..
To be continued..