amandacarrol's blog post - Getting Caught

On another web page I ran across a discussion about being caught. While I have never actually been caught dressing I did come extremely close once when I was young. I posted the story there and thought I would post it here. My parents use to own a college boarding house. The house was an old Victorian style home that had been converted. As you walked in the front door there was a main staircase to the second floor. There were twenty bedrooms, a couple on the first floor and the rest on the second and third. Each bedroom was shared by two girls.. During winter break someone had to go check on things.

On one occasion I was at the house. I unlocked the first room on the first floor and went in. There in a dresser was a bra and panties. I stripped down and put them on. Leaving my clothes on the bed I headed to the second and third bedrooms. I found and put on a pair of nylons. I was in heaven prancing around, looking in the closets for laundry and poking through dressers. As I made my way back down the main stairs in just a bra panties and nylons I heard a key go into the lock. There in the side light I could see a young lady trying to open the door. In a panic I ran into the closest bedroom and hid behind the bed. It was then that I realized my shirt and jeans were in a different bedroom. What to do? Walk out naked and make some excuse? I sat there unable to move for a few minutes. Just as I had my story straight I was getting up to strip down and walk out naked the front door opened and the young lady and her friends left. My heart was pounding as I ran to the correct bedroom and grab my cloths. Before changing back I went into the bathroom closed the door and jerked off. Don't think I have ever had a better or bigger climax.

This lead to one of many fantasies I had as a young man. I would fantasize about being caught. Here is how it would go. I stood up to take off the bra panties and nylons. As I stepped out of the nylons the door to the bedroom opened. There stood a collage coed and her boyfriend. Her 5 foot 7, very slender with long dark hair and blue eyes. He was 6 foot with a very athletic build. Who the fuck are you she screamed. Her boyfriend stepped in front of her and said don't worry babe I got this little fagot. Please I begged pleases don't hurt me. Again she screamed who are you. I am the son of the owners, see I have a full set of keys to the house. I was here to make sure the heat is on. And you just put on my underwear? Yes I couldn't help myself they are so pretty. We should go call the owner and the police this little sissy fagot broke into your room who know what he took or how many times he has done this. Please I begged I will do anything you ask please don't call my parents or the police. I stood there the tears starting to run down my cheeks. Again I begged, please don't tell anyone I will do anything you ask.

It was at this moment that the young lady began to giggle. Look Tommy his little dick is getting hard in my panties. He must really like wearing them. Do you like wearing my panties she asked. Yes was all I could say. She then smiled and said, you will do anything I ask? Yes anything you want please don't tell anyone. She then leaned over and whispered something into Tommy's ear. Don't you think that makes me gay Ashley? How can that make you gay? That is not a guy it is just a little sissy girly want a be. She then walked over to the closet and opened the door. She reached in and pulled out a sheer, short baby doll nightie. Take off my bra sissy! That is my favorite nightie when you wear it. As I slipped the nightie over my head I could see Ashley undoing Tommy's pants. Come over hear sissy and get down on your knees. I knelt down and Tommy stepped closer. Ashley then lowered Tommy's boxers to expose his growing cock. You will suck Tommy's cock until he cums in your mouth and all over your sissy face or I am calling the cops and Tommy will make sure you stay dressed like you are so they can see what kind of pervert you are. With that I started to lick the head of Tommy's cock. I could taste his precum as I took the head into my mouth. As he grew hard in my mouth Ashley kept telling him to imagine it was her in the pretty sheer blue nightie. Tommy just moaned with pleasure until he blew his seed all over my face and in my mouth. As he began to relax he said good but not as good as you babe. With that they both laughed.

Not being instructed to do anything I just knelt there. What a pathetic little sissy fagot he is. Get up and take off my cloths sissy. As I stood Ashly just broke out laughing. Grabbing my hand as I went to pull off her panties she just laughed even more. Look how wet the front of my panties are. Did you cum in my panties sissy? No Ashley. Leave those on they are yours I don't want them back until you have washed them. As I got dressed Ashely looked at me and said you will be here on Friday night at 6 pm. You will be wearing my panties and this bra under your cloths. We are going to take a vote and she what the rest of the girls want to do. Tommy laughed, I think the guys are going to get a real laugh from this one. Bring the whole frat and some beer and we can have a party with a sissy to serve.

Friday night arrived and I knocked on the front door promptly at 6 pm. Ashley opened the door and instructed me to follow her to the living room. There sat and or stood a dozen girls and several guys. This is the little sissy I told you about ladies. One girl spoke up from the corner of the room, and he was just standing there in your bra and panties when you walked in on him. Yes he was. Show her sissy! I took off my shoes and undid my pants. Lowering them my shirt tails continued to cover Ashley's panties. Finally I had no choice but to remove my shirt. As I stood there in her bra and panties the room broke into laughter. Such a cute bra and panty set but they look a little tight. I think I have something that may fit better. With that one of the girls left the room. I see what you mean about his little dick. It is already making your panties soaking wet. One of the girls walked over to me and pulled the panties down to expose my cock. Again laughter filled the room. That is not a cock! I can see how you would think it was a girl sucking your cock if he was in a sheer nightie. Just then the girl returned. Here take those off and put on these. She handed me a matching red lace bra and thong panty. One girl stood, rushed from the room and shouted oh my he must have my garter belt and stockings on. The next hour was filled with various outfits including the short sheer nightie I had worn on Tuesday. Finally Ashley lead me to her bedroom. You are to wait here
and do as you are told by everyone who comes to visit.

By this time I stood in a black garter belt with a matching pink thong and lace bra, After a moment the door opened and in walked one of the guys. I hear if I close my eyes you are almost as good as the real thing. I won the draw and I get you first. With that he undid his pants and lowered his boxers. Get over here on your knees I want to cum all over your face. That's right sissy suck my cock and make me cum. I dropped to my knees and began to lick the head of his cock. The delicious pre cum dripping into my mouth. As I took his cock in I could feel it swelling in my throat. After a few minutes his cock was completely hard and all 8 inches were in my mouth when he started to cum. He pulled out and shot his seed into my mouth and all over my face. As he dressed he said stay right there, don't clean a thing, just wait for the next person.

The door then open and in walked one of the young ladies. She smiled and asked if I had enjoyed her boyfriend. I could say nothing. She just giggled and instructed me to sit in the desk chair in front of the window. My god I had not noticed the currents were open and with the lights on anyone could see in. Thank god the window faced the back yard. I think you need a little make up sissy. As I sat there she applied foundation, mascara, eye liner, eye shadow and finished with a ruby red lipstick. This is important.... after you suck a cock you must refresh your lipstick for the next man. Here show me how you will do it. As I applied the lipstick she just smiled. Now my turn. She sat down on the edge of the bed and lifted her skirt to reveal her womanhood. Come sissy lick me and make me climax. I knelt down and moved my face towards the sweet smell of her pussy. This I had done many times before and I did everything I could to please. After a few minutes she shuddered with an intense climax. She sat up lowered her skirt and said now fix your lipstick sissy. As I did she giggled and said I wonder who is next.

This continued through several more people including all of the guys and a few of the women. Some had me change into different outfits some just walked in dropped their pants and pointed. The last person to come into the room was Ashly. She had me stand and bend over with my shoulders on the edge of her desk. As I stood there I felt the lube drip onto my sissy hole. Nobody was interested in fucking you tonight but I think you should know what it feels like to take a man. With that she slid a plug into my sissy hole. You are a virgin aren't you? The pain was intense as I said yes ma'am under my breath. Now kneel down in front of me. Ashley lowered her jeans to reveal her pretty panties. They were pink lace with a sheer panel in the front covering her pussy which was completely shaved smooth. Do you like that sissy? I saw a woman shaved like this in a porn movie I was watching with Tommy. He found it really hot. She then lowered her panties and sat on the edge of the bed. My turn! Once again I lowered my face to a pussy. The smell and taste were heavenly. When Ashley was finished she redressed and instructed me to follow her to the living room

Once again I was stood in the middle of the room dressed in just lingerie. One young lady who had not come to the bedroom said lets see this little cock. Pull down my panties. I lowered the panties to the top of my thighs and again the room broke into laughter. It is so small how could any one want to fuck this pathetic sissy. Your panties are so wet Lisa, he must be so horny. Let's have him jerk off like the pathetic sissy he is. Ashly said go ahead sissy jerk off show us what you have. I began to pull my cock but because I was so horny it took all of 30 seconds for me to cum. Oh my God Lisa exclaimed. Look how fast and he didn't even get hard. OK! Let's take a vote. Show of hands all those in favor of calling the cops and making a complaint raise your hand. One guy raised his hand and said my blow job was terrible I say we call the cops. Lucky for me no one else raised there hand. Ashly then walked over and said you may put on your shirt and jeans but leave the lingerie on. You will bring it back on the first Friday of the month when we will take another vote. I dressed and left. This became a regular thing on the first Friday of the month for the remainder of the school year.

I often dream that this fantasy came true and that it set me on a path to becoming a real woman. These days when I think of this fantasy I think of wearing this sheer nightie when I first suck Tommy's cock for Ashley. Hope you enjoy the reality as well as the fantasy.

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