The Second Time Getting Caught Wearing High Heels

We moved 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 with her days and nights, but she was never home.

One day at lunch a girl named Mary sat down at my table and the two of us talked and got on 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 an upper middle-class neighborhood and she came from money.

She, 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 this 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. Mary 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, I get back to Mary ‘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 classic high heeled pumps. Both pointed toe high stiletto heel had to be 4or 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 after she fell asleep and try them on. This was first and foremost on my mind, wearing those high heels. We were walking around barefoot. My feet were clean and dry, just ready to slip into those beautiful high heels at a moment’s notice.

That moment came at about 8 o’clock. The phone rang Mary 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 stilettos. They were a perfect fit; they were a size eight. I rolled up my pants and put them on. 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 pairs, the toe was such a sharp point, they were a deep brown suede high, high heel. I could feel my dick getting hard and I was all alone after all, she was upstairs on the phone, I could hear her, so I unzipped my pants and took out my cock, it was hard as a rock, I gave it a few quick strokes, and put it back and zipped up my pants. I kept the heels on until I heard her ending the call. When I heard her saying goodbye, I put them back carefully, rolled down my pants cuffs and went back to the couch and sat down.

She came downstairs and got another beer, opened it, poured it into our two glasses, and we drank and talked. After about an hour 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 insisted she saw me and I insisted I didn't therefore she couldn’t have seen something that didn’t happen. After many minutes of this she stood up, reached out for my hand, she pulled 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 put on her mother’s high heels and there was no doubt about it. She saw me pose to look at my feet in such pretty and sexy shoes. She saw me get hard and take my stiff cock out for a few teasing strokes, and she saw me put it back and zip up.

I was speechless and so embarrassed this was all too familiar a situation, just like the first and second time I got caught wearing women’s shoes. I didn’t know what to say, we went downstairs we sat down on the couch and were very quiet for what seemed like a very long time, but was probably only a minute or two. Eventually she spoke, 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 ones, 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 again. She saw the tent and asked if she could see it, this too seemed familiar to me, 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 upstairs 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 through her mother's drawers and started throwing things 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 myself away. She commented and how fast I changed and how straight my seams of the stocking were and how I knew how to hook up a garter belt and put on a bra with no help, supposedly all 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 size D cups somehow made it looked as though I had real cleavage and a really sexy pair of tits. She said brown shoes weren't going to make it and found the pink high heels her mother would wear with this dress, again 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 than I ever though. She said oh you need a wig, 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 than 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 an adult woman, a sexy adult woman. I looked like I was maybe a female in her mid-twenties, no doubt about it. She decided I still need one thing more and handed me a rhinestone purse a little 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 touched 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 in the palm of 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. She was shocked and knew without me having to tell her I’ve eaten cum before.

We would do this every time her folks went to see the twins. She got in to it, we'd share the jizz. After a year or so she got the nerve to lick what little cum was still on my cock, and then she decided she should just put her mouth near my cock and have it shoot directly into her mouth. The first time she tried this all she got a messy facial, but I cleaned her up. The next time she just put her mouth around my cock as I beat off. Finally, she just sucked my dick. We would share the jizz with a sloppy kiss until we shallowed.

She loved having a cock in her cum in her mouth and insisted that I had to try it somehow myself.

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.

Mary 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 Seven-Eleven carry out store and buy magazines.

I was sent to boarding school, so party time was all but over. The next time I saw her, she was a senior and considered herself to be a sex expert. She told me she had given many blowjobs and loved doing it.

She said her parents were going to be gone Friday through Sunday and she’d be all alone. I knew what that meant and said I’ll see Friday at 4pm. When I got there, she had a few outfits on her bed already picked out. One of them, it seemed to me was what she might wear to school, a skirt and a blouse sweater set with her flats and some jewelry. I asked her about her choice and she told of a little fantasy she was having. I have this same little dream myself. The difference is I made it happen many times. The dream is that I wear exactly what my mother or my aunt or my sister was wearing. It seemed very exciting to then to see them out and about wearing that outfit again and it was my secret that I wear their clothes and shoes too. She wanted me to wear her school clothes so when she wore them on Monday, she’d know a secret that was in plain sight to everybody but no one would know. To do this right, it had to be panties, panty hose, a bra then the clothss and shoes. She was a shoe size 8 like her mom and like me. I know this is a popular on Fictionmania, to be small with long hair and be mistaken for a girl even when your dressed in your most masculine self, but it does happen. Oh, and yeah it all fit, I’m small, really small. 5 foot 4 inches, 105 pounds, narrow shoulders, small hands, small feet. It’s like I stopped growing in 7th grade. My dick gets hard and I came cum, but I think that’s about all puberty did for me. Pubic hair, but nothing on my face, chest, back. If I were my k**, I would have brought me to see a doctor to ask, what the fuck is going on here? Not my mother though, she noticed I wasn’t growing but just said I was just a late bloomer. It never happened. One thing that’s actually funny is I met this k** when I was about 17 and he was just like me, really small and for some reason I assumed that he must cross-dress too. We talked and I asked him since he has small feet does he like to wear his mother’s high heels. He said NO, what do you? I said of course not and tried to make a joke out of it, but he thought I was a freak and got up and left. Wow this is sort of steam of consciousness. I’ll get back to Mary and her school outfit, so I dress up in it and she puts a little eye shadow and lip stick, puts my hair in a high pony tail hands me her purse and a coat, and says you look so pretty, just like any high school girl, let’s go for a car ride, so we did. During the ride I started to get turned on. I did look like any teenage girl and that started to be a very hot notion. On this outing, no high heels, no big breasts, no big hair and almost no make-up. I really started to dig it and so did she. She said she can’t wait until Monday when she will wear the same panties, the same bra… the same everything, she kept saying that I looked really pretty. I loved that! We went back to her place and changed in really feminine cloths and again she had picked out one of her dresses and her 3-inch high heels, all very appropriate clothes for a 17 year old girl. She was keeping her little fantasy alive so again she gives me a purse and a dressy coat, and again she says let’s go for a car ride. She had a plan that she wasn’t telling me, she wanted us to dress up, go out and find a guy we could suck off together. She wanted to watch me suck a cock. I never told her that I had already sucked cock many times and was really good at it, 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 drives to a drive-in movie, pays and parks. Before I have even fully digested this, she’s jumps out of the car and say’s I’ll be right back, I’m going to find us a boy to play with. We’re going to suck some cock so get in the back seat and be ready. She took off, so I got in the back seat to wait.

It took her all of 5 minutes and she was back and with her was a guy that looked like he was in his twenties. I was in the back seat like I was told to be. She opened the back door and in he got, right next to me. She got in the passenger side of the front seat. She had told this guy he was get a blowjob if he came with her. He unzipped his pants pulled them and his underwear down below his knees. His cock was huge, I didn’t know what to do and finally Mary said blow him already. He took my hand and placed it on his cock. His cock was getting hard and bigger and bigger. He placed my hand around his shaft and said to me, stroke it. I started to beat him off, Mary was hanging over the front seat, she kept saying suck it, suck it I want to see it in your mouth. He put his hand behind my head and pushed it down to his crotch. His hard cock was but an inch from my mouth, he kept pushing. It was pressing against my lips, Mary said, open your mouth and give him a blowjob. I opened my mouth and in it went. I immediately went into my fag mode and started going at him, up and down, up and down. I licked and sucked his sack and balls. I was really enjoying this, I forgot Mary was even there until I felt her hand on the back of head pushing down. I was gaging, which seemed to turn her on, she was breathing heavy, she might have been playing with herself, but I couldn’t see for sure. His cock was so big and she kept pushing my head down on it, I was drooling and gagging and almost deep throating this man when he let go. It felt like he just blew a quart of jizz down my throat, Mary saw what was happening and said, don’t swallow it all bitch. I didn’t she leaned way over the seat and we kissed and swapped cum. Someone else’s cum. It tased different than mine and different from my friend Tim’s cum. I liked it… a lot. He zipped up and said, thank you ladies and got out. I said to her, go get another guy and this you suck him off in the back seat. She said, OK and jumped out. I got in the front seat and less than 5 minutes she was back with another guy, who again looked like he was in his twenties. She got in the back and he followed. Nothing was happening so I told him to pull his pants and underpants down below his knees and he did, wow another big cock. Mary was looking a little scared and wasn’t doing anything. I had to tell her to grab his dick and start pumping. She was beating him off, but not very well, I could tell she was a little freaked out I told her to swap places with me and I’d do it. I got back in the back and she was back in the front and here I was with another cock in my mouth and Mary saying over and over suck it, suck it. I did and did it very well, he came, she and I kissed, he got out and we went back to her house. She apologized for not talking to me first about her plan, I told her it was OK and that I was going to find something a bit more adult to wear.
I went to her mother’s drawers and found her bathing suits. I picked out a one piece with rigid D torpedo cups and put it on. I let my cock and nuts hang out of one of the leg openings. I put on her mother’s black high heels and came back to her. She look at me and got on her knees, she sucked me off with some skill, I was impressed, of course she didn’t swallow and we kissed one of those 10 minute cum soaked kisses.

She never told anyone about our parties
发布者 ninaloy22
3 年 前
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4
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BillyRueben2
WOW, WOW, WOW, totally fucking hot! I have to go edge now and eat my own cum! 🤪💦🍆
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Guy49007
Great to have a friend that understands your needs pitty you moved
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MPLSbiGUY : Thank you, it really means a lot to me that someone is reading these. They're my true events growing up.
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MPLSbiGUY
Wow!  These are great stories!  - Dave
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