Getting caught as a young crossdresser.
Late in the summer of 1985 my older sister went away to college at Ohio state. I didn’t go back to school for another 2 weeks so I finally had the house to myself to do what I want. I wasn’t allowed to have freinds come over but I was able to go over their homes. My mom and dad worked 730-530 so I had the whole house to myself. I had been going through my moms drawers for the last 4 years anytime she’d go grocery shopping, etc, and I would put her satin white slips on and walk around the house feeling like a little girl. Now I was able to go through my sister bras, panties, and clothes so I was beyond happy with my oppurtunities.
On Monday morning I woke up around 10 am, went into my sister room and put on one of her white bras, blue floral satin panties, her dark blue mini skirt and white off the shoulder shirt. I put my socks in the bra to give myself perky little titties. Her clothes fit me perfectly. I was about 5’5 125 libs with thin long legs and a skinny waist. I was very feminine shaped. I hated it and loved it at the same time.
I always wanted to put on makeup but never had the opportunity to do it. So I decided today was the day. I went into my moms bathroom and put on her red lipstick, I then put on eyeliner, and put some of her lipstick on my upper cheeks. Looking in the mirror, I looked like a girl! I was so excited I went into my moms room and adored myself in her full body mirror. I looked so cute! I went back to my sisters room and put on a pair of her pink jelly shoes and went down stairs I laid on the couch in the living room and reached under my mini skirt and started masterbating
I had my right hand on my stiff cock and my left hand squeezing my fake little boobies. I was about to cum when I heard a noise in the foyer. I stopped touching myself and listened. The front door opened and someone walked in. I immediately jumped off the couch and hid behind the couch. I heard whoever it was go down the stairs into the basement. My heart was pounding. I was scared. Was it my mom or dad? Couldn’t be my sister. I then heard whoever it was coming up the stairs and went back outside. I then went to the front window and saw my moms freind Cheryl unloading chairs from her trunk. She had borrowed them for a party and was returning them. I knew a had a chance to run through the foyer and to the stairs to go to my room. As she was closing the trunk I quickly scampered to the foyer to get to the stairs I noticed the door was cracked open and hoped she didn’t hear or see me. It was then I noticed out of the corner of my eye something else. I had one foot on the stairs and my hand on the rail when I turned and saw Cheryl’s husband Rich staring at me. I looked right at him and he said “hi Mandy! “ I turned away and ran up the stairs just as Cheryl came back in. I went into my sister’s room. Now my heart was pounding fast, I wanted to cry.
As I sat on the floor in my sisters room shaking and ashamed I realized that Rich thought I was my sister Mandy. I thought to myself this is awesome. He had no clue it was me. I then heard Cheryl and Rich talking. She asked him who he was talking to and he said Mandy came through here and went upstairs. Cheryl said “Mandy’s away at college, her brother is home though”. He just said “Oh”. I heard her go downstairs and a few seconds later our house phone rang. It went to the answering machine and I heard my moms voice saying for me not to be startled but Cheryl is bringing the chairs back that she borrowed. I then heard Cheryl pick up the phone as the machine kept going.. she told my mom that she was there now and took the chairs down, then my mom asked if I was around and Cheryl said no but Rich thought he saw Mandy. My mom said Mandy is away at college so it must have been me. I gotta admit now I was worried. Would Ruch tell his wife what he saw? Would my mom find out? I was a nervous wreck. I undressed, showered, and just stayed home the rest of the day. Gotta admit I had trouble sleeping that night as my mind was racing with worries..
The next day I woke up hopped on my bike and met my friends for a game of basketball. Afterwards I raced home. I jumped in the shower, dried off and went into my sisters room I started going through her drawers, put on a pair of her white cotton panties and black bra. I then put on this white pajama Chemise that my sister would sleep in I went into my moms bathroom and was going to put on makeup again. Before I got started the phone rang. It was my mom checking on me and making sure I was ok. After I hung up the phone I started going back to the bathroom when the phone rang again. I was sure it was my mom calling back. I picked up the phone and said hello? There was a pause and then a mans voice asked “is this E——?” I didn’t recognize the voice. I said “yes who is this”?. He said it was Rich. I was silent and he asked how I was doing today? I told him I was good. He then asked me if it was me who he saw yesterday in the foyer. I paused and didn’t want to answer. He then said he was sorry he thought I was my sister Mandy. I told him that was ok. He then asked me what I was doing now. (I didn’t want to tell him I was dressed in a white nightie with bra and panties about to put makeup on.. lol). I told him I was just watching TV. He then said something that totally shocked me. He said he was going on his break from work at ford and wanted to know if I wanted something to eat. I told him no thank you and he then pressed the issue and I asked him where was he going. He said he’d go anywhere I told him. I told him I could go for a cheeseburger and milkshake from McDonald’s. He said ok then he said something I will never forget. He told me “you looked really cute yesterday and I can’t stop thinking about you. I know your mom and my wife are freinds but I just want to see you. I know there there is an age difference, but you looked so beautiful yesterday all dressed up and made up”. I remember saying “Ok, thank you..” I was completely caught off guard by everything he told me. He then said“ I hope I’m not being too forward or scaring you, but I really want to see you like that again.” After about 5 seconds of silence I collected my thoughts. How could I possibly respond to this??
I had always fantasized about being with an older woman while dressed, have her treat me like a daughter, to be extra loving and touch me in all the right places. More recently I had started thinking about older men.. dressing like a cute little slut, doing whatever he tells me to do. I now was in a position to make one of those fantasies happen. Rich seemed very sincere, and I trusted him, He had a wife, good job, two k**s. In other words a lot to loose. Obviously this would stay between he and I. I decided to go for it and see what happens. My legs were now shaking, and my voice trembled I asked Rich how long before he would be over. He said about 20 minutes. I told him ok. He then asked if I would be able to dress up and put makeup on.. I told him I was already dressed and was about to put some make up on. He said “thank you baby”. And hung up.
I put my make up on, wet my hair and sprayed it. I had a cute little pixie look going..I remember waiting nervously on the couch. Lips red, eyeliner on, I even put some of my moms liquid Clinique makeup on as foundation.
at about 1230 there was a knock at the door. I opened the door and there stood Rich. He was about 6 foot, 170 lbs, nice looking with light brown hair.. I stood there with my flowing white nightie, perky little bra covered tits, and my smooth creamy legs. He walked into the foyer, handed me my food and I walked him into the den. He also gave me a little plastic bag and asked me if I would wear this for him.. I placed my milkshake and food down and opened the plastic bag. There was a blue teddy/cami in the bag. He walked over to me and put his hand in my cheek and told me that I was the cutest thing he had ever seen. I walked into the other room, took off my white teddy and put on the blue, clingy teddy. I kept my Black bra on, and loved the way the two little bumps on my chest looked in the teddy. When I walked nervously back into to room rich was sitting on the couch leaning forward. He told me I looked perfect... the teddy fit perfectly, if was snug at the wait, tight around my boobies, and went down to just above my mid thigh. I now walked confidently towards rich and stood right in front of him. He told me I looked like a princess and if his wife knew I was wearing her teddy she would kill us both lol..he took his hands and place them on my waist. He then felt up my little A cup tits and smiled. He asked me to turn around and he lifted the blue teddy and began caressig my tiny ass. He commented that my ass was perfect. I now had a nice hard girl clitty poking out of my panties. Rich then asked me if he could see what I have under my panties. I slowly pulled my white cotton panties down and my 4 solid inches of clitty was exposed..Rich looked at my hard raw clit, looked up at me and smiled...
After admiring my young exposed clitty, Rich said “I want you to play with yourself for daddy”. I grabbed my little cock and started stroking it. Rich just sat there watching me stroke, then he started telling me what a bad little girl I am and that mommy would be ashamed if she saw me wearing her nightie..he told me next time he comes over he’s going to teach me how to be a big girl, and suck on daddy’s dick.. after about 2 minutes of stroking. I could feel my orgasm about to explode... “I’m about to cum daddy”.. I blurted out... “you are such a dirty little girl!, I’m gonna tell mommy everything you’ve done!” I started shaking and shuddering as quick streams of white goo shot out my girly cock into the carpet. Rich then stood up, lifted his wife’s blue teddy off me and put it back in the plastic bag. I stood there still quivering my sisters white panties now around my ankle, black bra still hooked on. My erect clitty was now back to its original cute size. Rich thanked me and said he had to get back to work. He told me next time he’s going to teach his girl how to suck cock. After that he left as quickly as he came by.
I stood there in the den basically naked trying to fathom what just happened.. this was by far my best sexual experience so far in my young life. (Actually first time I ejaculated in front of anyone make or female.) I felt kinda guilty, and dirty. But at the same time couldn’t wait to play again. Rich never touched my penis, never showed me his or exposed himself. I was kinda disappointed..I was prepared to at least touch his manhood, and may have at least kissed or put it in my mouth. But nevertheless I had my first sexual experience. I cleaned up the carpet, got the clothes together and showered myself off.
I spent the next 2 weeks waiting for my “daddy” to call me back for my next sex lesson.. that call never came. My parents continued to hang out with Cheryl and Rich and they would come over for holidays/ parties. There was always an uncomfortable tension between Rich and I, like one of us would tell on the other.. that never happened and unfortunately we never got together again
On Monday morning I woke up around 10 am, went into my sister room and put on one of her white bras, blue floral satin panties, her dark blue mini skirt and white off the shoulder shirt. I put my socks in the bra to give myself perky little titties. Her clothes fit me perfectly. I was about 5’5 125 libs with thin long legs and a skinny waist. I was very feminine shaped. I hated it and loved it at the same time.
I always wanted to put on makeup but never had the opportunity to do it. So I decided today was the day. I went into my moms bathroom and put on her red lipstick, I then put on eyeliner, and put some of her lipstick on my upper cheeks. Looking in the mirror, I looked like a girl! I was so excited I went into my moms room and adored myself in her full body mirror. I looked so cute! I went back to my sisters room and put on a pair of her pink jelly shoes and went down stairs I laid on the couch in the living room and reached under my mini skirt and started masterbating
I had my right hand on my stiff cock and my left hand squeezing my fake little boobies. I was about to cum when I heard a noise in the foyer. I stopped touching myself and listened. The front door opened and someone walked in. I immediately jumped off the couch and hid behind the couch. I heard whoever it was go down the stairs into the basement. My heart was pounding. I was scared. Was it my mom or dad? Couldn’t be my sister. I then heard whoever it was coming up the stairs and went back outside. I then went to the front window and saw my moms freind Cheryl unloading chairs from her trunk. She had borrowed them for a party and was returning them. I knew a had a chance to run through the foyer and to the stairs to go to my room. As she was closing the trunk I quickly scampered to the foyer to get to the stairs I noticed the door was cracked open and hoped she didn’t hear or see me. It was then I noticed out of the corner of my eye something else. I had one foot on the stairs and my hand on the rail when I turned and saw Cheryl’s husband Rich staring at me. I looked right at him and he said “hi Mandy! “ I turned away and ran up the stairs just as Cheryl came back in. I went into my sister’s room. Now my heart was pounding fast, I wanted to cry.
As I sat on the floor in my sisters room shaking and ashamed I realized that Rich thought I was my sister Mandy. I thought to myself this is awesome. He had no clue it was me. I then heard Cheryl and Rich talking. She asked him who he was talking to and he said Mandy came through here and went upstairs. Cheryl said “Mandy’s away at college, her brother is home though”. He just said “Oh”. I heard her go downstairs and a few seconds later our house phone rang. It went to the answering machine and I heard my moms voice saying for me not to be startled but Cheryl is bringing the chairs back that she borrowed. I then heard Cheryl pick up the phone as the machine kept going.. she told my mom that she was there now and took the chairs down, then my mom asked if I was around and Cheryl said no but Rich thought he saw Mandy. My mom said Mandy is away at college so it must have been me. I gotta admit now I was worried. Would Ruch tell his wife what he saw? Would my mom find out? I was a nervous wreck. I undressed, showered, and just stayed home the rest of the day. Gotta admit I had trouble sleeping that night as my mind was racing with worries..
The next day I woke up hopped on my bike and met my friends for a game of basketball. Afterwards I raced home. I jumped in the shower, dried off and went into my sisters room I started going through her drawers, put on a pair of her white cotton panties and black bra. I then put on this white pajama Chemise that my sister would sleep in I went into my moms bathroom and was going to put on makeup again. Before I got started the phone rang. It was my mom checking on me and making sure I was ok. After I hung up the phone I started going back to the bathroom when the phone rang again. I was sure it was my mom calling back. I picked up the phone and said hello? There was a pause and then a mans voice asked “is this E——?” I didn’t recognize the voice. I said “yes who is this”?. He said it was Rich. I was silent and he asked how I was doing today? I told him I was good. He then asked me if it was me who he saw yesterday in the foyer. I paused and didn’t want to answer. He then said he was sorry he thought I was my sister Mandy. I told him that was ok. He then asked me what I was doing now. (I didn’t want to tell him I was dressed in a white nightie with bra and panties about to put makeup on.. lol). I told him I was just watching TV. He then said something that totally shocked me. He said he was going on his break from work at ford and wanted to know if I wanted something to eat. I told him no thank you and he then pressed the issue and I asked him where was he going. He said he’d go anywhere I told him. I told him I could go for a cheeseburger and milkshake from McDonald’s. He said ok then he said something I will never forget. He told me “you looked really cute yesterday and I can’t stop thinking about you. I know your mom and my wife are freinds but I just want to see you. I know there there is an age difference, but you looked so beautiful yesterday all dressed up and made up”. I remember saying “Ok, thank you..” I was completely caught off guard by everything he told me. He then said“ I hope I’m not being too forward or scaring you, but I really want to see you like that again.” After about 5 seconds of silence I collected my thoughts. How could I possibly respond to this??
I had always fantasized about being with an older woman while dressed, have her treat me like a daughter, to be extra loving and touch me in all the right places. More recently I had started thinking about older men.. dressing like a cute little slut, doing whatever he tells me to do. I now was in a position to make one of those fantasies happen. Rich seemed very sincere, and I trusted him, He had a wife, good job, two k**s. In other words a lot to loose. Obviously this would stay between he and I. I decided to go for it and see what happens. My legs were now shaking, and my voice trembled I asked Rich how long before he would be over. He said about 20 minutes. I told him ok. He then asked if I would be able to dress up and put makeup on.. I told him I was already dressed and was about to put some make up on. He said “thank you baby”. And hung up.
I put my make up on, wet my hair and sprayed it. I had a cute little pixie look going..I remember waiting nervously on the couch. Lips red, eyeliner on, I even put some of my moms liquid Clinique makeup on as foundation.
at about 1230 there was a knock at the door. I opened the door and there stood Rich. He was about 6 foot, 170 lbs, nice looking with light brown hair.. I stood there with my flowing white nightie, perky little bra covered tits, and my smooth creamy legs. He walked into the foyer, handed me my food and I walked him into the den. He also gave me a little plastic bag and asked me if I would wear this for him.. I placed my milkshake and food down and opened the plastic bag. There was a blue teddy/cami in the bag. He walked over to me and put his hand in my cheek and told me that I was the cutest thing he had ever seen. I walked into the other room, took off my white teddy and put on the blue, clingy teddy. I kept my Black bra on, and loved the way the two little bumps on my chest looked in the teddy. When I walked nervously back into to room rich was sitting on the couch leaning forward. He told me I looked perfect... the teddy fit perfectly, if was snug at the wait, tight around my boobies, and went down to just above my mid thigh. I now walked confidently towards rich and stood right in front of him. He told me I looked like a princess and if his wife knew I was wearing her teddy she would kill us both lol..he took his hands and place them on my waist. He then felt up my little A cup tits and smiled. He asked me to turn around and he lifted the blue teddy and began caressig my tiny ass. He commented that my ass was perfect. I now had a nice hard girl clitty poking out of my panties. Rich then asked me if he could see what I have under my panties. I slowly pulled my white cotton panties down and my 4 solid inches of clitty was exposed..Rich looked at my hard raw clit, looked up at me and smiled...
After admiring my young exposed clitty, Rich said “I want you to play with yourself for daddy”. I grabbed my little cock and started stroking it. Rich just sat there watching me stroke, then he started telling me what a bad little girl I am and that mommy would be ashamed if she saw me wearing her nightie..he told me next time he comes over he’s going to teach me how to be a big girl, and suck on daddy’s dick.. after about 2 minutes of stroking. I could feel my orgasm about to explode... “I’m about to cum daddy”.. I blurted out... “you are such a dirty little girl!, I’m gonna tell mommy everything you’ve done!” I started shaking and shuddering as quick streams of white goo shot out my girly cock into the carpet. Rich then stood up, lifted his wife’s blue teddy off me and put it back in the plastic bag. I stood there still quivering my sisters white panties now around my ankle, black bra still hooked on. My erect clitty was now back to its original cute size. Rich thanked me and said he had to get back to work. He told me next time he’s going to teach his girl how to suck cock. After that he left as quickly as he came by.
I stood there in the den basically naked trying to fathom what just happened.. this was by far my best sexual experience so far in my young life. (Actually first time I ejaculated in front of anyone make or female.) I felt kinda guilty, and dirty. But at the same time couldn’t wait to play again. Rich never touched my penis, never showed me his or exposed himself. I was kinda disappointed..I was prepared to at least touch his manhood, and may have at least kissed or put it in my mouth. But nevertheless I had my first sexual experience. I cleaned up the carpet, got the clothes together and showered myself off.
I spent the next 2 weeks waiting for my “daddy” to call me back for my next sex lesson.. that call never came. My parents continued to hang out with Cheryl and Rich and they would come over for holidays/ parties. There was always an uncomfortable tension between Rich and I, like one of us would tell on the other.. that never happened and unfortunately we never got together again
4 years ago
