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Sissy Alone for the Night

As I pulled into the car park outside the hotel, switching the engine off and stopping for a second to catch my breath, my heart beat with excitement.After a few deep breaths, I looked around, making sure I didn't recognize anyone before stepping outside to make my way to the trunk. My hands were trembling as I reached inside for my suitcase, pulling out my bag and trying to hide the guilty look painted all over my face.I composed myself, then walked inside and approached the front desk where a...

Sissy Story Chapter 05 Finale

All the stuff, some dishes, the leash, the collar, the toys, a chew bone and a ball with a bell in it, a couple of bags of training reward dog treats, and some dry dog food, were ready the next day. His dog tag and dishes with his name on them would take a couple of weeks, but I thought that was way too long for the first time in a chastity belt. I wanted him fired up, not frantic and thinking of ways out. I felt like it was most important to start having fun. Mom agreed, so I sent off...

Sissy the Redhead Making of a Slut Part I

Part I She was out mowing the lawn again. That little red head across the street. She was probably thirteen or so. Maybe fourteen, and she had long thick curls of deep red hair. The kind that looks dyed, but isn’t. Her titties were just coming in, but they were coming fast. She must be pushing a B cup by now, only she wasn’t wearing a bra that day, just a tight little baby tee that said “Candy” on it that showed off her tight, flat waist. The shorts she had on didn’t hurt in...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

Sissy Experience Episode 3 Neighbourhood Uncle

Hello All,Hope you’re all doing well!Hey Guys and Girls if you have not read my previous episodes I recommend you read those and come back to this one.In the previous episode I told you guys how the sissy part of me was evolving. I was now dressing like a complete girl whilst fingering my ass pussy and pinching my titties. My ass would get wet and my dick hard when I would dress like a girl. Whenever I was home alone I would look for sexy clothes either in my Mom’s or Sister’s cupboard and put...

Sissy masturbation and light exhibitionism

This is the backstory of the gallery "Sissy masturbation". I would like to share the thoughts and sensations behind the pictures and videos I took. Today my brother had classes in the morning and my mom was driving dad to work. I knew I had an hour to satisfy myself. I took a shower before my family left, don't want to get my last set of underwear dirty. I then retrieved the set of underwear from my secret stash. The sports bra was tight and I struggled into them. The cotton panties were so...

Sissy Fucked In Adult Book Store True Story

100% True Story.I was 19 years old and working 3rd shift at a department store and taking classes during the daytime. I had visited an Adult Bookstore about 15 minutes away a few months back and went back into the video booths. It was the first time I had even been in an adult video arcade and wasn’t really that impressed. There was a strip club next door and I had heard stories of hookers giving guys head at the bookstore video booths. I realized that turned out not to be true. I was pretty...

Sissy all dressed up at a rest area

Sissy all dressed up at a rest areaSo, i had a bit of a scary encounter recently. But it was totally worth it =]. I was driving from my home town to the town where i go to school. It is a windy little road that goes right through a big slice of nowhere, with very minimal cell service. And it was night time. I had been all dressed up and hoping to find someone at a local wildlife area that is an OK place to find guy sometimes, but no dice. I am pretty shy, and don't go to places like that much,...

Sissy Lucy meets her daddy

I’m in my late 20’s and manage a local restaurant/bar. I am 5ft 8 and slim with quite feminine features. To most people I’m just Tom, a regular guy who has occasional girlfriends, likes a beer and watching the football. To my closest friends I’m Lucy, a sissy slut who loves cock. Recently I’d found a ‘daddy’ online. He was an older more experienced man. We started off chatting and I sent him some naughty photos and video clips of Lucy playing. As we talked I revealed that I like to be...

SISSY

Looking at me now, one will have an extremely difficult timebelieving this story. But let me assure you that every word istrue. It started late one spring afternoon. The weather was typicalspring weather, windy, wet and cold. I was walking home from highschool, hoping for a ride. I had just turned 18 a couple of days before and was within two months of graduating. My options after school were causing me much concern. I was very small, looked 16 and feminine. If you're thinking that's normal...

Sissy Slave

Joanne, my wife, has for many years insisted that I wear lingerie and girly things under my male clothes when at work as part of my sissy training. At home I am a sissy slave.“Sally” she said “Today we are going to make you feel more aware of the pretty things you wear”. After years of taking hormones my breasts are a nice 38C with dark brown shades round my nipples and Joanne had arranged for me have my balls and sac removed when we went to Thailand one year. Despite this and though my cock...

Sissy Downfall

Sissy DownfallThis story is about my conversion from a cross dressing sissy to submissive transformed slut owned by Mistress Rebecca George. All characters are over 18.Having been to the beautician for a full body and face wax I check into the hotel to prepare. The suite consists of a large living room and a comfortable bedroom with a large bathroom. The bedroom has a nice dressing table with mirror and stool. A full length mirror is adjacent. The king size bed is of an older style with metal...

Sissy boy and a shave

It’s a Saturday night. I’ve been talking with this guy online for a while now trying to determine if he and I are the right fit…. and also work up the balls to meet up (…so my balls and much more can be worked over). We’d spoken about a whole bunch of things whilst chatting, his fetishes, mine, and what both of us would like to do to the other / have done to us. From this it all seemed pretty enticing so we teed up a night we were both free to dedicate to debauchery. Thankfully for me my...

Sissy

Well. That was interesting, wasn’t it? We’ll play with your little titties again tomorrow. For now, just close your eyes and rest. Did you have a good nappy? Do you need to go potty? Ok. But remember to catch the little dribbles with a tissue. You wouldn’t want to stain those cute little pink panties. Now that you’re back, I think it’s time we did something about that little tiny – it’s too small to call it a cock, don’t you agree? It’s not even a dick. Dicklet. A dicklet. That’s all it is. Not...

Sissy Tranny Annie Slutty Fantasy

I have been dressing since an early age, dressing in my mothers stockings, suspender belt, bra, panties and heels. I used to feel my smooth legs and my cock would get hard straight away. I love how my cock looks when im dressed as a sissy slut and from that early age all ive ever wanted is to have a horny guy in front of me, with his cock hard knowing that he wants to fuck me. My fantasy and dressing got a lot more sluttier when I first in with my first love. Her name was Claire and she loved...

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