Sheer black stockings, black suspenders, I looked sexy. Next, I slipped on the French cut-ruffle, ruby panties. The black and scarlet colors looked hot and sexy on me. Putting on a bra was a challenge. After a few failed tries remembered seeing, my wife put on a bra. She put it on backwards, fastening the hooks in front then twisting the bra around slipping the straps over the shoulders.
Dressed in my ruby ruffle French cut panties, I was ready to meet several men who all would be willing to treat me like a slut. I put on the black dress then looked in the mirror. I was dressed sexy and impressed with how feminine I looked with makeup. I had developed my makeup skills by reviewing many YouTube videos about transsexual putting on makeup. I had a better understanding of makeup application. For the last week, I have been taking care of the skin on my face by cleaning, toning and moisturizing. I made sure my face was clean allowing the makeup to work the best. I applied a concealer under my eyes, and around my nose. A concealer to cover up the beard was especially important. Following up, I apply a base or foundation that closely matched my skin tone. I used a powder puff to place a light dusting of powder to hold the foundation in place.
To lighten up my eyes I started with the eyeliner. Then I highlighted my eyebrows with an eyebrow pencil, filling in any bare spots, and finally apply eye shadow then mascara. I applied a light dusting of blush, working my way down to the lips. My lips had a gorgeous shimmer after application of lipstick and lip-gloss.
I place my wig snugly on my head; the wig was groomed short on the sides and long in the back, with a part in the middle. I selected this wig because it allowed some of the hair to drape over my face hiding my manly features. It took me a little over two hours to go from Roger, the straight average man to Cindy, cross-dressing, and sexy slut.
My first date was scheduled to arrive at 5 PM. I said my date because I had posted a message on Craigslist, and had several men responding they wanted to meet me. I guess my post was a little suggestive by letting everyone know that I was an easy lay. At 5 PM, my phone rang; it was Greg, a rugby player who informed me he was the lobby. I told him my room number expecting him to be knocking on my door in a minute. I had exchanged many emails with Greg, whom admitted that he considered himself straight. He told me that idea of having sex on a man made him physically ill.
Greg told me that one night in a Pub he had one too many drinks, had hit on a good looking woman who was sitting at the bar. After a few minutes they left and found an alley where she got on her knees and gave him the most wonderful blow job. He wanted to return the favor and lifted her skirt and was confused as to what he was seeing. There was a large bulged in her red panties. Greg realized that something was not right and tugged on the panties to revealing a seven inch uncut dick. Greg realized in an instant he had received the best blow job of his life from a man in a dress. He lost it and threw up. Greg said that the idea of having sex with a man made him physically sick.
Greg had told me in his email that he was undecided from having a great blow job and having it from a man. No woman he met had let him cum in their mouth and then would be willing to swallow. Greg grew very horny for a good blow job and in desperation contacted a transsexual to receive oral.
The transsexual was passable and as such when she sucked Greg, Greg did not see a man dress but a woman sucking his dick. As long as the transsexual looked like a woman he was ok, receiving oral sex from a man.
One last check, makeup, lips, yes, I was passable, in a dark room. I turned off all the lights except the one in the bathroom as there was a knock at the door. My heart rate increased; I had worked hard to dress perfect for Greg; I hoped he would approve. I opened the door, and Greg walked into my room. I only saw a picture of his dick and not a picture of his face. He was handsome, clean-shaven, square jaw, with a Kirk Douglas dimple and dark-blue eyes. He wore tight jeans and a ruby striped shirt. The rugby shirt was tight in the shoulders showing large biceps and best muscles. I gathered in Greg's looks as he walked into the room. I sat on the bed and he took a seat in one of the chairs. Sitting on the bed I could show off my stocking clad legs, my short skirt rode up my thigh, showing the top of my stocking with a suspender strap showing. I inhaled to increase my bust and tucked in my tummy.
I started the conservation by saying, "Greg it is to meet you after all our emails. I know much about you."
Greg said, "Cindy you are just like your pictures, attractive and sexy." His eyes were not looking at my eyes but my chest, as most men would.
I said, "Greg, I bet you say that to all the gurls you meet," pretending to be blushing.
I said in my best female voice, "Greg Sweetie, I have been waiting to meet you since your first email. Your picture was a turn on, and I wanted to dress up just the way you asked me to." I pulled up my skirt to show off my stockings and suspenders but not enough to show my ruffle panties. "Do you like my outfit Sweetie?" I walk towards Greg, straddle one of his legs, and slowly rub him between his. At the same time, I move my hand over my body, from my hips up to my breast then to my mouth where I suck my fingers.
Greg seemed impressed as his hand was resting in his lap, trying to hide his growing hardness. I leaned forward putting my hands on his shoulders and letting my lips lightly kiss his neck moving to his ears. From our emails, he told me he did not want to kiss on the lips, but the neck and ears were erogenous zones and a good place to start to turn on a man. Greg's hands reacted instantaneously and reached up to run up from my hips to my tits. My fake tits should have felt real to him. I wished they were real, so I could feel the excitement as Greg felt them. He felt the fake raised nipple and thinking they were real he to pull me close as he sucked them through my blouse. I would have loved my real nipples to have responded to his touch.
At this point, I did not think Greg was reluctant being here with me. I stood; turned around showing him my behind. He grabbed one cheek then the other. I moved my hips in a rocking motion as his hands slipped down to my legs lifting my skirt. His hand started to rub up and down the inside my legs, a turn-on for me. He pulled me backwards causing me to sit on his lap. In this position I could move my arse in circular movements giving Greg a pleasurable lap dance. I felt his hardness rubbing my thighs as we both became aroused. When with a man I liked to be obedient and need the man to decide what we are do. Greg ordered me to get on my knees. Assuming the position I knelt on my knees in front of a man, what he would do next was up to him, I give him full control.
Greg opened his legs, letting one hand to rub his bulge. I took my hands placing one on each knee. Teasingly I slid one hand up on the inside his thigh as I have reached closer to his now stiff dick. Greg reclined in the chair with his head looking up at the ceiling; I got the feeling that he wanted to get a blowjob but did not want to watch a man in drag do the deed.
My hands move to his belt, then to his zipper where I discovered that he was not wearing any underwear. I reached in letting my hand encircle his thick dick. His dick was big, warm, silky to the touch, and getting hard. Trying not to bend his erection. I freed his dick to revel an impressive example of male manhood. I have always surprised when I see a man's dick for the first time. His dick was large, uncut, thick and smooth. I tug on his pants as he lifts his legs allowing me to pull them down to his knees. He was still not looking at me. I kissed the inside his thigh, next the other thigh, moving to his balls. I held his dick in my hands as my mouth kissed one ball, next the other. My kissing turned into licking each ball and finally sucking one then the other into my mouth. When his balls were in my mouth, I let my tongue move across them, hoping that it tickles him to arousal.
Being a good dick sucker means taking your time and enjoying what you were doing. If you enjoyed sucking dick most likely so did the man who owns the dick. A good dicksucker knows how to touch a dick, slowly taking it in your mouth, letting your lips to feel like a pussy. One can kiss the tip of a dick then licking the shaft from the bottom to the top, running your tongue around the glan then back down to the balls. Having only sucked a few uncut dicks I found them to be a unique experience. I had read the foreskin was sensitive, and decided to test and see how sensitive Greg's foreskin could be. I licked his foreskin at the top of his dick; this kissed the foreskin around the tip then finished with opening my mouth allowing him to feel my warm mouth. I rubbed my tongue around his dick tip, letting my tongue find his opening to where his glan head was covered. I pulled down on his shaft with my hand, disclosing his glan head. My tongue found this hidden glan head then delighted in messaging every inch.
Greg's gave a little moan. I must have been doing something right. I kept the skin pulled back allowing his dick head to be disclosed and available to my mouth, lips and tongue. Greg starts moving hi hip as he places his hands on each side of my head. With a light but firm touch, he pushed his dick further into my mouth. I was not sure how much of his dick was in my mouth. I was going to fit willing to try. Each time a little more of his dick disappeared until my mouth touched his balls.
I could not breathe each time his dick went all the way down my throat. I had to control my breathing in rhythm with Greg's his thrusts. I looked up at Greg's face and saw him looking at me my sucking his dick, taking all of his erections in my mouth. He smiled, as I took his dick out of my mouth, gland disclosed with precum oozing out of his pee hole. I licked his sweetness then rubbed his precum on my lips. I opened my mouth wide allowing Greg to see his dick disappear. His hips moved with deeper thrusts, his hands held my head fixed for each movement. Greg says, "Oh baby, I'm cuming. Oh, suck my dick, baby. Take my load." With that my throats felt a squirt of warm fluid. I tighten my throat muscle and move my tongue to coach another spasm. I needed to breathe and pulled his dick back so now the squirts of semen were in my mouth. Swallowed his warm fluid, swirled it around my mouth, accepting his favor. When my mouth was fully open I showed him his creamy fluid. Looking up I smiled and swallowed. I licked the remaining cum from his dick then placed my head on his lap. I was satisfied; in a few minutes Greg stood up, zipped up his pants as I saw a smile on his face because of my cock sucking ability.
Greg told me," Wow Cindy that was wonderful. That was amazing; my girlfriend does not suck as well as you do." He paused, smiled and said, "You should give lessons. She spits, and you did not. I like that, makes me feel like you wanted to suck me."
We chatted for a long time with Greg relaxed in the presence of Cindy. He saw Cindy as a woman and not a man in a dress receiving pleasure from her oral pleasures better than what he was receiving at home.
That evening Cindy had several other dates but that is another story.