For the past few years, when going on business travel, I always took the early flight and packed some of Brenda's clothes so I could crossdress as soon as I got to the Hotel. I had been a closeted crossdresser for years. Tonight was going to be a bit different.
It was going to be just another fun night. I was finishing fitting my wig and started outlining my lips with lip liner, and followed up with some Revlon red lipstick. While not great looking, I had a great pair of lips when painted with lipstick. For the past few years, when going on business travel I always took the early flight and packed some of Brenda's clothes so I could crossdress as soon as I got to the Hotel. I had been a closeted crossdresser for years. Tonight I was going to wear a very pretty red and black detailed jacket and gorgeous black dress pants. To top it off I found some great matching black dangle earrings.
To finish my outfit I put on some 3-inch heel black patent dress pumps. A sexy but not too slutty heel height. I always then liked to admire myself in the mirror for a few moments when I dressed as Brenda. I had become pretty darn good with makeup and was passable at a distance. I would then usually go and drop by the mall and walk around for a little bit. I loved the sound my pumps made on the pavement. I didn't prance around for too long as I would be outed by a few people who upon closer look could see who and what I was. In addition, not too many people dress to the hilt as I do just to go to the mall, and not many women use red nail polish and lipstick anymore. It was still a lot of fun, and I do get nice looks from men now and then who obviously approve of the way I dress.
When I got back to my room at the hotel I popped open a bottle of merlot and poured myself a glass of wine and popped out the webcam. I liked to spend an hour or so in Transgender chat rooms letting others admire how I looked. The messages I would get would be everything from insults, marriage proposals, to every offer of sex imaginable. I consider myself totally straight and never considered being with another man period but I loved letting them view me.
After my third glass of wine and fixing up my lipstick, a message popped up saying, "Hello fellow Fort Worth person."
I was in Fort Worth tonight. I replied hello back. The person said he was also a businessman on travel and was admiring me on webcam. He said he liked the outfit and it would be something he would like to see on his wife. He seemed to actually have a brain and we chatted for a few minutes mostly about sports which I liked. He gave no indication to have any sexual advances to me whatsoever. I did ask why he was talking to a crossdresser and he replied he looked up people who had sports on their profile. We chatted about sports for a while and then he said he had to get up early and signed off and said he was going to be in town all week. I didn't think much about it.
Two days later, my work day had an early ending so I was given an opportunity to dress again. I was back on webcam drinking another bottle of wine when my friend from the previous day messaged me again. We were both watching the Thursday night football game, and chatting about the plays and other sports junk. He said he was bored and asked if he could come over and watch the game. Thinking better I responded I was straight and had no interest in sex of any kind with men and meeting would not be appropriate. He responded he had no interest in anything other than drinking a beer and watching the game. He also said he would be happy to take some pictures of me posed in my outfit and heels which is something I always wanted to be done. Probably too much wine let me say ok and I gave him my hotel information and room number.
About 40 minutes later a knock on the door was heard, and my anxiety increased a million fold. I could not believe I was doing this. I was a closet crossdresser, and now some strange guy was knocking at my door. What the heck was I thinking? I did manage to open the door and sheepishly said hello. He immediately replied to not worry that things were cool were just gonna catch the game. I had known he was black from the pictures on his profile, but he was taller than I thought. I relaxed a little as he started to watch the game, and seemed more interested in that than myself. We yapped about sports and he talked about if TO was good for the Cowboys.
It was a simple conversation and I was relaxed about the whole thing. In talking, he stated he just gets lonely on the road and wants to talk to human beings when not with his family. The game went on for about another hour and a half and ended with a Cowboy's victory. He said he was going to take off and get some sleep but wanted to know if I still wanted some pictures. I said sure and gave him my camera.
At first, I did some poses standing and then some on the bed in more sexy looks. After about 15 minutes of pictures, he put down the camera and then unexpectedly started to unbutton his shirt. I immediately asked what he was doing, and he said, "Brenda, I decided I like how you look and I need you to pleasure me babe."
I responded that I was straight and no way was this happening.
After finishing taking off his shirt, he looked at me. "I don't care if you're straight, queer, or whatever, cause in a about three minutes those pretty red lips are going to be wrapped on my cock,".
He rather loudly shouted to get my ass over to him. He was extremely loud. He said he was going to make so much noise every person in the hotel was going to know what was going on in here and do I really want that. Obviously being dressed as a woman and with fellow workers in the hotel, I could not afford a scene or trouble. I asked him to quiet down and talk about it.
"Babe ain't no problem here and there isn't anything to talk about, I am horny as hell, you look hot, and you are going to be my woman for a while. In an hour it's gonna be over and we're both gonna be really happy."
Feeling trapped, I asked that if I sucked him, would he leave. He responded affirmatively. I approached him and he smiled, and said, "See it's all good in here."
I came to where he was standing and he started to unbuckle his belt and pull down his pants. He took them off and I could see the bulge in his underwear. He told me it's going to be alright and to get on my knees and pull off his underwear which I did. I was shaking as I never thought in my life I would take down another man's underwear. When done with that I could see he was well hung. He was hard and probably 7-8 inches. He grabbed me by the back of my head and said just lick it a little. Repulsed I stuck out my tongue and for the first time ever touched another man's cock. He pushed my head a little up and down.
"Good baby now open up."
From there he proceeded to insert his cock into my mouth and I closed down with my lips. At first, he moved my head back and forth as his cocked entered in and out and moaned that's how he wants it done. He took his hands off my head and I started on my own doing something I thought I would never do and suck a man's cock. Slowly I went up and down on his shaft and wrapped my lips around his cock tightly. It was a strange feeling and taste, and at first, I was hesitant. I could see I was leaving red marks of lipstick on his cock and caught another glimpse of a sight. In the long mirror of my room, I could see myself fully dressed as a woman on my knees going up and down on this large cock of a tall strong black man. It was a rather hot looking scene and I started to watch myself suck this huge man. I was getting hot seeing my lips around his cock. My cock was dripping in my panties.
In two minutes, I went from a simple crossdresser to feeling like a complete woman giving pleasure to this man. No longer resistant I was excited and eagerly sucking his cock. I now wanted his cock in my mouth, I needed it in my mouth. My hands with my long red nails went up and rubbed his body and hard ass. I could not take my eyes off the mirror. I loved sucking this man and wanted to pleasure him. He could tell the change, and responded: "I told ya babe, we were both going to like this." We went on for another few minutes when he started to jostle and said he's gonna cum. As he joined my head up and down while moaning his cock unloaded in my mouth its first batch of cum. I licked it eagerly and cleaned off the rest of his cock.
He thanked me for a good head session and put back on his pants and asked if he could relax for a minute. I said ok, and went to the bathroom and cleaned up my face and reapplied my lipstick which was a mess. When I came back he again thanked me and said he appreciated those sexy red lips and hoped maybe we could do it again someday. I said yes and cracked him a beer and said no rush to leave. I was very aroused and was surprised how attracted to him I was. I was admiring his strong frame on my bed and not really wanting him to leave. I poured a glass of wine and laid next to him on the bed.
My final surprise was how womanly I was acting towards him. My red nails were gently lovingly caressing his strong frame, hoping he would return the thought. He was just sort of looking ahead as I continued to try and seduce him. Finally, I could tell he was aroused and he turned to me and started to kiss me. I kissed him back and he commented how quickly I became his bitch. He was right, he owned me. In a minute he stopped kissing and said you know what you want......go down and get it. This time without hesitation and with great pleasure Brenda, went down and pulled off his pants and proceeded to give her second blow job.
My business will definitely be more interesting and enjoyable from here on.