Getting Caught Wearing High Heels Again
We moved when I was 15 to a new town a new house a new school. I knew no one and it seemed no one wanted to know me. I had lunch alone walked home alone and did everything alone. My sisters were away at college. I don’t know what my mother did but she was never home.
One day at lunch a girl sat down at my table and the two of us talked and we became friends. Not boyfriend girlfriend, but friends, we lived close to each other and we would walk to and from school together. She invited me to her house once and I went it was big and it had a swimming pool. This was a upper middle class neighborhood and she came from money.
She and her mom and dad went to visit her uncle and aunt and their new baby twins once or twice a month, which was a couple hundred miles away. Her mom and dad said once she turned 16 they would trust her to stay at home alone Friday and Saturday night while they go on and visit the babies. One day while walking home she announced she was home alone and that I should come by, we could get a pizza, watch TV and just hang out, so I did, I showed up and we sat down and turned on the TV and started to watch a movie, she said that I should spend the night. I didn’t know exactly what she meant by that but she was quick to point out that we could just stay up all night and talk and watch TV and have fun. I said I’d run home and leave a note for my mom. I did so and I gave my mom her phone number. My friend Carol said that if she called she would tell my mom I was outside playing with her brother named Alex. This was perfect except she didn’t have a brother but my mother didn’t have to know that so that was to be the story. So I get back to Carol‘s house we sit down and she opens up a beer, we split it. It’s the first alcohol I ever had had in my life and I start to feel a buzz.
In the corner of this family room on the floor were two pairs of her mother’s shoes. They were beautiful high heeled pumps. Both classic pointed toe high stiletto heel maybe 5 inches tall. I knew at some point I was going to have to try them on. Whenever I saw a beautiful pair of shoes I always created a situation where I could try them on alone somehow. My thought was I would just wake up in the middle of the night if she fell asleep and try them on. This was first and foremost on my mind, wearing those high heels. At about 8 o’clock the phone rang Carol said it was her mom checking in She jumped up turned off the TV and ran upstairs to take the call. she told me to be quiet. I could hear her on the phone at the top of the stairs so I took the opportunity being already barefoot to go over to the corner and try on her Mother’s high heels.
They were a perfect fit, I knew what size I wore. I wore an eight. They were bright yellow sling backs with green pipping and a bow on the tow. I stood there for a minute with them on looking at my feet in various poses all the time keeping an ear open for her and her phone call. I took them off, and put on the brown suede pumps these were my favorite of the two,, the toe was such a sharp point, they were a deep brown suede high, high heel. I kept these on until I heard her ending the call. When I heard her saying goodbye I put them back carefully and went back to the couch.
She came downstairs got another beer opened it poured it into our two glasses, and we drank and talked after about an hour when she said, I saw you. I said you saw me what? She said she saw me try on her mother’s high heels, I told her she was crazy why would I do that. I would never do that, why would I want to try on a pair of high heels? She insisted I did and she saw me and I insisted I didn't therefore she didn't see what didn't happen. After many minutes of this she stood up and reached out for my hand, she took me upstairs and said, sit down on the top step and look downstairs. I did. I asked her why I was doing this and she said look at that mirror above the table on the left and when I did, I saw that it reflected the pair of shoes in the corner of the room with absolute clarity. She did see me and there was no doubt about it. She saw me roll up my pants, put on her Mom's high heels and pose to look at my feet in such pretty and sexy shoes. She saw me get hard and put my hand down my pants to rub myself, She saw unzip my pants and take my hard cock out and quickly stroke it a couple time before putting it back and zipping up.
I was speechless and embarrassed I didn’t know what to say, we went downstairs we sat down on the couch and she said that she loved wearing her mother's high heels too. She went over and picked up the two pairs asked me which one was my favorite. Very sheepishly I said the brown, she handed me the suede pumps and said put them on. She quickly sat down and put on the yellow sling backs looked at me and said again, put them on, so I did and of course I got hard as a rock. She saw the tent and asked if she could see it, so I took it out. I couldn't help but stroke it a little. After a bit, she said, we need dresses, come on and up stairs we went. We went into her room and she went through her closet and announced that she didn't have anything sexy enough, so we went to her mother's closet. She found a dress she liked and held it up in front of me and said oh yeah, it's this one for you, but you're going to need a bra to fill it out. She went trough her mother's drawers and started throwing tings at me, a bra, panties, stockings, a garter belt, and a slip. She told me to go to the bathroom and change and return for the dress and high heels.
When I came out from the bathroom, I didn't think, but she knew right away that I had given my self away. She commented and how fast I changed and how straight my seems on the stocking were and how I knew how to hook up a garter belt and put on a bra with no help, supposedly for the first time ever. She asked if this was the first time I'd ever worn women's clothes. I told the truth and said no, it wasn't. I told her this was something I did every time I was alone at home.
She stuffed the bra with tissue and had me put on the dress, It was a pink party dress with a full skirt, sleeveless with a plunging neck line. The torpedo bra with it's size D cups Somehow made it looked as though I had real cleavage and a really nice pair of breasts. She said brown shoes weren't going to make it and found the pink high heels her Mother would wear with this dress, my favorites, pointed toe 5 inch stiletto heels, these were a d-Orsay style, so pretty! When she saw me, she said, you look so much better then I ever though, so let's get one of her wigs. She goes through her mother's wigs and comes back with one that looked just like Mary Tyler Moore's hair from The Dick Van Dyke Show. Dark, long with bangs and a flip, very feminine! She couldn't believe her work, so of course she said just a little makeup and you'll be a babe. Red lipstick, fake lashes, eye liner, mascara, rouge. She did a much better job then I had ever done, that's for sure. I looked pretty, I really did, but she wasn't done next some jewelry, earrings, necklace, bracelets and rings. She put me in front of the mirror and admired her work in turning a boy into a adult woman, a sexy adult woman. I looked like I was maybe 28 or 30 year female, no doubt about it. She decided I still need one thing more and handed me a rhinestone clutch. I don't know why but the addition of just the purse made my cock so hard it tented in the dress and she noticed. Without thinking she said there's something wrong with the dress and reached underneath to fix it. All she found was my hard cock. She had her hand around my cock. I gasped a bit. She said she was sorry, I told her to please do it again and don't let go this time. She did. She had never touch or seen a penis before and didn't know what to do, I put my hand on her and gently stroked my cock with her hand. She got the idea and I let go. She gave me a hand job, I was very careful to lift the dress and slip before I came and didn't get any jizz on anything but her hand. She was mesmerized and just looked at the cum on her soaked hand. She said a girl at school said you're supposed to eat this and held it up in front of me, so I licked her hand clean.
We did this a lot after this first time, she started to licked her hand clean, so we'd share the jizz. After a year or so she got the nerve to lick and then suck my dick. She loved doing and insisted that I had to try it somehow myself. She found a guy at school and convinced him that this would be fun.
My mother never knew I didn't have a friend named Alex. She never asked to meet him or even where he lived. I spent many weekend nights at "Alex's house" and she could have cared less which was fine with me.
Carol and I never became boyfriend girlfriend, but from the high heels we became dressing up buddies and that was the best fun ever. Once she got her driver's license we'd get dressed up and go for car rides, sometimes we'd go into a local carry out store and buy magazines.
I was sent to boarding school and we slowly lost contact. One of the last times I saw her, she was senior and considered herself to be a sex expert. She told me she gave a guy a blowjob and loved it. She wanted us to dress up, go out and find a guy we could suck off together. I never told her that I had already sucked cock, I always for some reason wanted her to think of me as a straight guy that just liked to dress up every now and then. This is part of my life long struggle with shame.
She never told anyone about our parties
One day at lunch a girl sat down at my table and the two of us talked and we became friends. Not boyfriend girlfriend, but friends, we lived close to each other and we would walk to and from school together. She invited me to her house once and I went it was big and it had a swimming pool. This was a upper middle class neighborhood and she came from money.
She and her mom and dad went to visit her uncle and aunt and their new baby twins once or twice a month, which was a couple hundred miles away. Her mom and dad said once she turned 16 they would trust her to stay at home alone Friday and Saturday night while they go on and visit the babies. One day while walking home she announced she was home alone and that I should come by, we could get a pizza, watch TV and just hang out, so I did, I showed up and we sat down and turned on the TV and started to watch a movie, she said that I should spend the night. I didn’t know exactly what she meant by that but she was quick to point out that we could just stay up all night and talk and watch TV and have fun. I said I’d run home and leave a note for my mom. I did so and I gave my mom her phone number. My friend Carol said that if she called she would tell my mom I was outside playing with her brother named Alex. This was perfect except she didn’t have a brother but my mother didn’t have to know that so that was to be the story. So I get back to Carol‘s house we sit down and she opens up a beer, we split it. It’s the first alcohol I ever had had in my life and I start to feel a buzz.
In the corner of this family room on the floor were two pairs of her mother’s shoes. They were beautiful high heeled pumps. Both classic pointed toe high stiletto heel maybe 5 inches tall. I knew at some point I was going to have to try them on. Whenever I saw a beautiful pair of shoes I always created a situation where I could try them on alone somehow. My thought was I would just wake up in the middle of the night if she fell asleep and try them on. This was first and foremost on my mind, wearing those high heels. At about 8 o’clock the phone rang Carol said it was her mom checking in She jumped up turned off the TV and ran upstairs to take the call. she told me to be quiet. I could hear her on the phone at the top of the stairs so I took the opportunity being already barefoot to go over to the corner and try on her Mother’s high heels.
They were a perfect fit, I knew what size I wore. I wore an eight. They were bright yellow sling backs with green pipping and a bow on the tow. I stood there for a minute with them on looking at my feet in various poses all the time keeping an ear open for her and her phone call. I took them off, and put on the brown suede pumps these were my favorite of the two,, the toe was such a sharp point, they were a deep brown suede high, high heel. I kept these on until I heard her ending the call. When I heard her saying goodbye I put them back carefully and went back to the couch.
She came downstairs got another beer opened it poured it into our two glasses, and we drank and talked after about an hour when she said, I saw you. I said you saw me what? She said she saw me try on her mother’s high heels, I told her she was crazy why would I do that. I would never do that, why would I want to try on a pair of high heels? She insisted I did and she saw me and I insisted I didn't therefore she didn't see what didn't happen. After many minutes of this she stood up and reached out for my hand, she took me upstairs and said, sit down on the top step and look downstairs. I did. I asked her why I was doing this and she said look at that mirror above the table on the left and when I did, I saw that it reflected the pair of shoes in the corner of the room with absolute clarity. She did see me and there was no doubt about it. She saw me roll up my pants, put on her Mom's high heels and pose to look at my feet in such pretty and sexy shoes. She saw me get hard and put my hand down my pants to rub myself, She saw unzip my pants and take my hard cock out and quickly stroke it a couple time before putting it back and zipping up.
I was speechless and embarrassed I didn’t know what to say, we went downstairs we sat down on the couch and she said that she loved wearing her mother's high heels too. She went over and picked up the two pairs asked me which one was my favorite. Very sheepishly I said the brown, she handed me the suede pumps and said put them on. She quickly sat down and put on the yellow sling backs looked at me and said again, put them on, so I did and of course I got hard as a rock. She saw the tent and asked if she could see it, so I took it out. I couldn't help but stroke it a little. After a bit, she said, we need dresses, come on and up stairs we went. We went into her room and she went through her closet and announced that she didn't have anything sexy enough, so we went to her mother's closet. She found a dress she liked and held it up in front of me and said oh yeah, it's this one for you, but you're going to need a bra to fill it out. She went trough her mother's drawers and started throwing tings at me, a bra, panties, stockings, a garter belt, and a slip. She told me to go to the bathroom and change and return for the dress and high heels.
When I came out from the bathroom, I didn't think, but she knew right away that I had given my self away. She commented and how fast I changed and how straight my seems on the stocking were and how I knew how to hook up a garter belt and put on a bra with no help, supposedly for the first time ever. She asked if this was the first time I'd ever worn women's clothes. I told the truth and said no, it wasn't. I told her this was something I did every time I was alone at home.
She stuffed the bra with tissue and had me put on the dress, It was a pink party dress with a full skirt, sleeveless with a plunging neck line. The torpedo bra with it's size D cups Somehow made it looked as though I had real cleavage and a really nice pair of breasts. She said brown shoes weren't going to make it and found the pink high heels her Mother would wear with this dress, my favorites, pointed toe 5 inch stiletto heels, these were a d-Orsay style, so pretty! When she saw me, she said, you look so much better then I ever though, so let's get one of her wigs. She goes through her mother's wigs and comes back with one that looked just like Mary Tyler Moore's hair from The Dick Van Dyke Show. Dark, long with bangs and a flip, very feminine! She couldn't believe her work, so of course she said just a little makeup and you'll be a babe. Red lipstick, fake lashes, eye liner, mascara, rouge. She did a much better job then I had ever done, that's for sure. I looked pretty, I really did, but she wasn't done next some jewelry, earrings, necklace, bracelets and rings. She put me in front of the mirror and admired her work in turning a boy into a adult woman, a sexy adult woman. I looked like I was maybe 28 or 30 year female, no doubt about it. She decided I still need one thing more and handed me a rhinestone clutch. I don't know why but the addition of just the purse made my cock so hard it tented in the dress and she noticed. Without thinking she said there's something wrong with the dress and reached underneath to fix it. All she found was my hard cock. She had her hand around my cock. I gasped a bit. She said she was sorry, I told her to please do it again and don't let go this time. She did. She had never touch or seen a penis before and didn't know what to do, I put my hand on her and gently stroked my cock with her hand. She got the idea and I let go. She gave me a hand job, I was very careful to lift the dress and slip before I came and didn't get any jizz on anything but her hand. She was mesmerized and just looked at the cum on her soaked hand. She said a girl at school said you're supposed to eat this and held it up in front of me, so I licked her hand clean.
We did this a lot after this first time, she started to licked her hand clean, so we'd share the jizz. After a year or so she got the nerve to lick and then suck my dick. She loved doing and insisted that I had to try it somehow myself. She found a guy at school and convinced him that this would be fun.
My mother never knew I didn't have a friend named Alex. She never asked to meet him or even where he lived. I spent many weekend nights at "Alex's house" and she could have cared less which was fine with me.
Carol and I never became boyfriend girlfriend, but from the high heels we became dressing up buddies and that was the best fun ever. Once she got her driver's license we'd get dressed up and go for car rides, sometimes we'd go into a local carry out store and buy magazines.
I was sent to boarding school and we slowly lost contact. One of the last times I saw her, she was senior and considered herself to be a sex expert. She told me she gave a guy a blowjob and loved it. She wanted us to dress up, go out and find a guy we could suck off together. I never told her that I had already sucked cock, I always for some reason wanted her to think of me as a straight guy that just liked to dress up every now and then. This is part of my life long struggle with shame.
She never told anyone about our parties
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