Out of town, I broke free
So I was out of town on business, and I hadn't worn any female cloths out ever in my life, but this time I took some sexy cloths from my roommates girlfriend..and I had been chatting with this transgender girl in the city I was heading to for a few weeks, we would skype and get off together, and she would make me do things to please her..I'm a switch but for this girl I'm her sub slave. When I got to the hotel I took a shower and shaved myself..complete, then I call my Trans friend, for the sake of this story I'll call her Dana, so I called Dana, she told me to get dressed and meet her at this bar, I was so nervous, but but on these silky white panties, with garters, stockings and matching bra, black blouse and white skirt, my make up wasn't the best but I thought I did ok, I had bought this cheap red wig a while back so I wore that too..I didn't think I was passable in the bright light of the bath room, but I actually was in the bar.
I was so nervous, my smooth body covered in women's cloths, I ordered a drink at the bar and then moved to a corner table, I was so hard and could feel my precum soaking my tight little panties. I had just finished my 2nd drink when Dana walked in, she sat down, and said well done..are you ready for what I have planned? Yes Mistress I said with a trembling voice. Good now come here and kiss me, I could hardly wait I slid over a licked her supple lips and and sucked her tongue, it was so hot, she ran her hand up my skirt and teased my cock, I was already dripping cum, she fed it to me and kissed me again, I was losing my mind..she told me to take her to my hotel so she could have her way with her little whore, I didn't object. The ride back to the hotel seemed to take forever, when we got there, she sat on the bed and told me to get on my knees, I did and as she pulled her skirt up I began kissing and licking her feet all the way up to her cock, it wasn't hard when I got there, but when I took into my mouth it didn't take long and she grew to 8", it was cut and smelled like vanilla I was hypnotized, I was sucking her balls and licking her ass, she moaned and gave instructions, I was starting to rub on my cock and finger my ass..she noticed and seemed upset, told me to lay on the bed..as I did she pulled off my skirt and blouse, she cuffed my hands to the bed post, all while talking "you wanna touch yourself whore" "who the fuck do you think you are?" I would apologize, but she said too late, as she sat on my face and ordered me to eat her ass..I didn't mind one bit, she was grinding an moaning, and starting to finger my ass..I loved it, didn't take long until she was jacking me, and even less time til I came, she made me eat and swallow all of my hot cum, after that she gave me a small kiss and then fucked my face, I could swear her cock had grown as I gagged with every thrust, within minutes she exploded in my mouth and told me swallow it all like a good little whore, I moaned in agreement as I sucked her dry savoring every last drop. Dana layed down next to me kissing me sucking my lips and tongue, as I could tell she loved the taste of cum, as I lay there still cuffed to the bed, Dana went to the bathroom and came out with a ball gag, and said, "didn't think I was finished with you did you? Can't have you screaming at what comes next."
I had no control and I loved it..Dana was licking and kissing me, she worked he way down to my once again hard cock, and began to suck me off, she would only stop to lick my ass, I wasn't gonna last long and moaned as to let her know I was going to cum, so just before I did she took me in her mouth and I exploded, she kept my cum in her mouth and slowly dripped it out over the ball gag, it was dripping all over my lips and down both sides of my face, I was spent, before I knew what happened she was sticking lubbed fingers in my ass, just before her giant cock..it hurt like hell, but I couldn't do anything but squeal through the gag..she pulled my legs up and leaned into me as we locked eyes I never felt such ecstasy, I didn't even realize it, but my ass was grinding into that monster cock, she removed the gag and kissed me..I can't believe what I said, but I did.."please cum in me" she smiled and kissed me again..moments later as her nails dug into my hips and her cock launched her hot cum deep in my ass..Dana collapsed on me and kissed me..she kept her cock in my ass for at least ten minutes, I felt like a new person when she pulled it out. We fell asl**p in each others arms..best sex of my life.