This is about the first time I went out in public as Brie in college. Ever since I was a teenager, I had always loved dressing up in my older sister's panties and pantyhose. Unfortunately, when she went to college she took all of her stuff with her except for a pair of white cotton string bikini panties. I decided to take them and I would wear them to bed or around the house when I was alone.
Jump ahead to freshman year at college. I'm now 5'6", blonde hair in a fairly long ponytail, 150 pounds, and a more feminine then masculine. I was finally free to do what I want except that I had a roommate... who dropped out by the third week. So now I have this whole college dorm room to myself and I decided to start wearing my panties all the time. One night I had my music blaring and I was dancing in my white string bikinis and a tight tee shirt. I guess it was too loud because I didn't hear the sound of a key turning in the door lock. What I did hear was a female voice saying "what do we have here?"
I turned to see Kate the RA from the girl's wing down the hall. Kate is gorgeous with long legs, B cup firm breasts, a tight ass, and a sexy smile. I tried to think of something to say but kept stammering and was trying to cover myself up. She quickly closed the door and told me to turn the music off. I did it and returned back to where I was standing, scared out of my mind. She told me to calm down and that it was ok, she wasn't going to tell anyone. She started to ask a bunch of questions like how long had I been a crossdresser and do I ever go out. I told her my history and how they were my sisters panties and that I had never been out.
"Well, you better get ready because we're going out tomorrow night. I want you shaved and at my room by 7:30" Kate said. "What? I can't." "Why not?" "I don't have any clothes and I just can't." "Its ok. I'll let you borrow some of my stuff as long as you wear those cute panties and I promise I won't tell anyone." She said this as she started to move closer to me and she caressed my butt through the panties. "You know, I really am a lesbian but there is something about innocent white string bikinis that really turn me on. Maybe if you are a good girl, I'll help you to become the real girl you want to be" and with that she moved her hand to my rock hard, incredibly small penis. I took the hint and told her I'd go with her tomorrow. After that she left and I was left to wonder what I had gotten myself into. I masturbated that night to the thought of Kate sucking me and me sucking her in a hot, sweaty 69.
The next day went by in a blur and I showed up exactly at 7:30. She was wearing a short black cotton skirt that stopped at her mid thigh and was wearing a spaghetti strap red tank. She had on nude pantyhose and showed me her blue sparkling thong underneath. She then handed me my outfit: nude pantyhose, a white cotton skirt just like hers, a light blue tank and a white lace bra. I was in heaven. Finally, a full outfit for me to wear. The pantyhose felt so smooth on my freshly shaven legs and my penis was at full attention. This did not go unnoticed as she turned to me and said "we can't have this in the way can we?" Then she really blew my mind as she sank to her knees, pulled out my cock and started to suck me off. I came in minutes and she swallowed it all. There is nothing like having a lesbian, a beautiful long legged, athletic, brunette lesbian sucking you off while she is on her knees.
"You owe me one for that. Not as good as a real pussy but not bad either."
On that note, we left to go to a small bar that catered to gays and lesbians. We got there and she seemed to know a lot of people and she introduced me as Brie. Everyone was really friendly, especially her lady friends. Maybe I did pass, I don't know but what I did know was that my nerves were through the roof and it was time to get my drink on. Matt was one of the bartenders and seemed to take all of my drink orders. He was about 5'10", muscular, and I guess good looking. The thing is, I'm not gay. I'm totally into girls and I'm here to better my chances with Kate. Kate pulled me onto the dance floor with all of her lesbian friends and we were really having a good time. Kate kept grinding into me while reaching under my skirt and rubbing the front of my panties. I was really getting turned on but I was also getting really drunk and really really had to pee.
I stumbled my way into the men's bathroom and made my way towards one of the stalls. It was then that I accidentally ran into Matt who was coming out of one of the stalls. He seemed surprised to see me but we both apologized and I ran into the stall. I lifted up my skirt, pulled out my cock and started to pee. Just as I was finishing I felt the stall door open and I heard Matt say "I thought bitches were supposed to sit when they pee." I was a little too drunk to understand what he meant so I shrugged it off, laughed, and tried to pass him.
"Where do you think you're going?" "I'm going to go back out to the dance floor to find Kate." "I don't think so" and he spun me around while twisting my arm behind my back. I tried to struggle but I was too drunk and he was much stronger than me. "Stop it" I whimpered. "Shut up bitch, I know you want it. Why else would you dress up like a little slut." "I'm not gay." "You are tonight." I tried to struggle again but he just held on tight as he wrapped a cable tie around my hands behind my back. I tried to protest but he slapped me across the face and forced me to my knees. I started to cry knowing what was about to happen. "Have you ever sucked cock before bitch?" "No." SLAP. "No what?" "No sir" "Good, I always like to break in a virgin." He unzipped his fly and pulled out his penis. I've never been face to face with a cock. Sure I've seen them in the locker room but I've always tried to avoid them because again, I'm not gay. Now I am face to face with this throbbing, pulsing 7" piece of meat thats moving towards my mouth. "Open up and don't start until I tell you so!" I open wide and he lays the big purple head on my tongue and leaves it there. It seems hours but it was probably only seconds as lef it there. Precum dripping onto my tongue. "Close it and start sucking. No teeth or I'll knock them all out." I start to suck him off as he grabs my hair. He is gentle at first, sliding in only a little, but he soon picks up the pace and starts to push deeper into my throat. I am gagging and coughing which makes him harder and hornier as he starts face fucking me even faster. I think that he's about to cum in my mouth when he pulls out.
"Turn around." "No, I can't." SLAP SLAP "I said turn around bitch, don't make me say it again." "Yes sir." I turn around, my knees on the pee covered stall floor, realizing what is about to happen. "Please sir, don't do this. I've never done this before." "I know, thats why I am going to break you in. Just remember to relax and it won't hurt that bad." He pushed me over so my upper body was resting on the toilet. "White panties, my favorite." Matt put his cock into my ass crack, wedging the pantyhose and panties into my hole. I start to whimper and cry because I realize my situation. I'm completely helpless, hands tied behind my back, dressed like a girl, about to get pegged by this guy I just met who thinks I'm gay. He starts to hump me and I feel like he is harder than he was before. Grabbing the waistband of my pantyhose and panties, he pulls them down and off my legs. He shoves the panties in my mouth and wraps the pantyhose around my head to keep them in.
Now my ass is completely exposed to him. I hear him spit into his hand and then I feel the head start to push against my virgin ass. I renew my efforts to get away but we both know its futile so I begin to cry and whimper even harder into my panty gag. The pain is intense as his head pops in. I yelp but he doesn't stop. He gets halfway in and starts to back up only to slam it all the way inside me. I scream and he pulls my hair and tells me to shut up. I can hear him moaning as he starts to fuck my tight ass.
"I guess you really are a virgin, I can see your cherry blood." My face is completely red and I can't stop crying into my gag. He slaps my ass and begins to pick up the pace. "Do you like this bitch? Do you like dressing up for your daddy so he can fuck your cherry hole? Is his little girl enjoying this? I bet you are. You know how I know? I can feel your hard clitty." Oh no. It can't be. Do I really have a boner right now?
"It's ok baby, daddy knows that you like it rough. Don't worry, I will make it exactly how you want it." With that he really began slamming into me and I couldn't believe that I was beginning to feel a tingling spreading throughout my body. My pain was turning into ecstacy, my moans of pain into moans of pleasure. I started thrusting back to meet my daddy's thrusts.
"Fuck my pussy, I'm so close to coming Daddy. Oh daddy, fuck me. Fuck me." I yelled into my white panty gag.
"Oh baby, I'm gonna cum. Are you ready to be filled? Oh, fuck yeah. Ugh, Ugh, UGH, UGHHHHHHHHH" and I could feel shot after shut of cum filling my ass as my own orgasm caused me to shoot all over the side of the toilet. I screamed and writhed against my bonds as my body shook with pleasure. Matt rested on top of me until his cock went soft and slipped out of my ass with his cum following, dripping down my leg. He didn't say anything as he zipped his pants back up and left the stall. I was left on the dirty stall floor, still gagged with my white string bikini panties and pantyhose, my hands tied behind my back, and my ass leaking cum for the first of many times.
I hope you all enjoyed the story. It is my first so any advice would be greatly appreciated. I do like to chat, email, and discuss my dressing up and fantasies so if you would like to talk to me about them or want a story about it, please email me at sissibarbimastr@hotmail.com