Brittany's Sexy First Time With a Man

by Brittany Moore

 

I had been crossdressing since I was 13 years old and had been making online purchases of everything from wigs and makeup to boots and lingere. I always had the desire to be with a man as a sluttly girl. I decided that it was time. It was when I was 29 years old and was weighing a nice 180 lbs and 6'2. I live alone and I decided to dress up in my favorite black thigh his stockings, my lacey garter belt, my thong black panties and a sexy sheer black bra. I put in my silicone implants. I modeled for myself and felt my ample tits as I faced the mirror. It was time for me to take out the makeup. I sat at my makeshift vanity and began to apply my foundation to my face. You could not see any part of facial hair as I put it on thick. I then proceeded to put on my black Maybelline eyeliner. Drawing a perfectly done line around my eyes. I proceeded to take out my extra length black mascara and extended my lashes very well. I completed my eye makeup by using some subtle eye shadow to complete the job. I then moved to my lips as I applied long lasting wet shine purple lipstick on my lips. I puckered my lips to taste the awesome taste of the sexy and slutty color. I then applied another coat to insure it did not come off easily. I put on a long black wig with straight hair which rested right below my shoulders. I crossed my legs like a lady and proceeded to light up a vs 120 cigarette. I sat there taking a sexy drag satifying my smoking fetish as well as my crossdressing fetish.

When I finighed smoking it I went to my closet and took out my favorite black leather skirt. It was tight and sexy and really showed the shape of my ass. I then put on a tight v-neck purple blouse. My 36 c breasts were very formidable as I was wearing it. My nipples showed through the tight blouse. I then put on my black knee hi boots and zipped up the sides. I was now feeling like a true woman. A woman with her clitty getting hard. A woman who desired a man. I poured myself a glass of wine and lit up another cigarette as I sat on my couch. Legs crossed again. I turned on my laptop and went online. I had been talking man to an older man from my area for some time now and he was online as well. I began talking to him again and told him that I was dressed and a little horny. We had spoken for about 30 more min before I decided to invite this so called "cd admirer" over to my home. After the arrangements were made I dimmed the light in my home and lit a great many candles. I knew it would take him about 10 minutes to get over to my place. I paced around smoking my cigarette thinking about how I would be during this experience. He had told me this was an unexplored fantasy of his. He insisted he was not gay but he thought he would enjoy the company of a crossdresser. I finally began to relax and sat on my couch. 5 minutes later a knock was at the door and I simply told him to come in, in my feminine voice.

He walked and rounded the corner and same me. I smile went over his face. He was in his late 30's and was wearing jeans sand a white button down shirt. He was well built and attractive man. He was glancing over at (in my opinion) a sexy, slutty looking girl sitting on the couch with a glass of red wine in front of her seductively holding a long cigarette in one hand as her crossed legs revealed the tops of her silky thigh his and the garters which supported them.. I walked over to him and he introduced himself and Jim as I introduced myself as Brittany. I invited him to sit with me and offered him a glass of wine. He accepted. We began to talk as he expressed his nervousness as did I. After a couple of minutes the talk shifted as he began to be very complimentary of outfit and look. I kept saying "thank you" in my feminine voice and reached with my left hand to touch his thigh. He moved closer to me and began to move in to give me my first kiss as a woman. His lips touched my purple lips and his tongue slowly entered into my willing mouth. The soft and sensual kiss continued as he reached to grab my tits. He pulled away for a second to say "Brittany you are so fucking hot". I responded to this by moving my tongue back into his mouth. This time the kissing was more intense. I reached my hand down to his jeans and felt his huge cock in his jeans. Jim's breathing became heavier. I got on my knees in front of him and he pulled off my blouse to reveal my pretty tits through my sheer bra. I unbuttoned his shirt and began to suck on his nipples. Light biting of them made him squirm in excitement. As I pulled away he asked me to hold on as he took off his jeans. I reapplied my lipstick. Sharing my fetish, he asked if I could light up one of my Virginia slims 120's. I obliged and began to talk dirty about his cock, saying how I wanted it in my mouth so bad and how I wanted to taste his cum. He obliged. I took a sexy drag and exhaled and then moved into his cock and put it in my mouth. Kissing the head followed by a lick up the shaft. I took it all in my mouth and began to give him a hot blow job. He was calling me a whore and slut as I sucked it and held my long cigarette, taking breaks to take a drag. After about 10 minutes he asked my to get up and turn around.

I obliged and he pulled down my skirt. He began to pull aside my thong and lick my man clit. As he licked it he spanked my ass asking me how I liked it. Of course I loved it. This went on for a short time until asked me to lay down on my back. I did and he pulled my legs back and began to fuck me. He again asked me to hold/smoke a cigarette during this as well. He fucked my pussy good even though it did hurt, but in a good way. I began talking dirty back to him asking him to make me his cum slut and to fuck me like the whore I am. He obliged. As he neared orgasm he pulled out to cum on my face and tits. He did so so well. It was awesome. My cum covered tits and face loved every second of it. Since I had not concentrated on handling my own orgasm he did me a favor at my request. He took my vibrator and used it in my pussy ass as I stroked my cock. I came shortly. After this I laid there as he gave me a cigarette and lit it for me. He also opened up the lipstick tube and as I laid there he reapplied my lipstick. Shortly after we talked some more and he left. I had completed the first erotic session as a slut. I never had anything like it. Since this time I have only been with Jim and meet with him a couple times a month. We have done other sexy things including his dressing with me, but that’s another story. I will always remember that night and believe it was the most erotic night of my life.

 

Brittany Moore

  

  

  

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