Home Alone: Day 01

Story Info
Young man loves crossdressing at home.
864 words
3.66
95.7k
12

Part 1 of the 2 part series

Updated 08/30/2017
Created 08/09/2008
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The day at work dragged in. It seemed to take an age before 5o'clock came around. When it finally did I raced to my car and sped home.

My parents, brother and sister had taken a weeks holiday and I had the whole house to myself, I couldn't wait to play out some of my fetishes. As I walked through the front door there was a note from my mum --

- There is enough food in the house for the week so you don't need to go shopping

- Remember to lock the door at night and when you leave

- There is a spare key next door in case of an emergency

- The name of the hotel and flight details are below

Basically all the boring things my mom thought she needed to tell me. After throwing the list in the bin I stripped from my male clothes and headed straight to the shower. I shaved my private parts bald and moisturised in my mom's best stuff. I then proceeded to under my bed where I pulled out a cock ring, (one of the long ones with 5 joined rings) and an 'O' gag. My next stop was my moms panty draw.

For as long as I have known I have loved to dress up in female underwear. I just love the feeling of silk and lace against my body. I found a plain black thong with a matching bra, I decided to go for plain as I had housework to do and it was only 6o'clock. After pulling out a pair of my sister's jeans and a playboy vest I tried to find a pair of shoes to fit me. As I am a size 10 and my mum is only a 4 with my sister being a 7 this was rather hard.

Eventually I came upon a pair of pink pumps which I could just fit into. Looking in my sisters mirror I though I looked like a perfect 19 year old girl ready to lounge around the house. However looking at my head there was something missing, a wig.

After rummaging around the loft I found a wig with long blonde hair. Perfect After a bit of blusher and foundation I could maybe just pass as a girl.

By 9o'clock I had finished the housework and had eaten, so I thought its time to have some more fun. After searching the internet for self bondage help I found two different ties I could try a hogtie and a full body harness. Tonight I thought I would try the hogtie. After returning the basic clothes I found a pair of pink briefs with ribbons on and a matching bra. The feeling of the silk against my cock instantly made me hard. The feeling of my cock straining against the cock ring made me more desperate to cum but I held it back. This time I went heavy on the make with pink eye-shadow and bright pink lipstick. Finally a pair of tight fighting pink stilettos finished the look off. Looking in the mirror I thought this time I look much more like a slut ready to go and fuck some cock.

I grabbed some rope and a porno DVD. I put the DVD in and set it off, on the screen a fresh 18 year old was gagging on cocks that were being thrown at her from everywhere. I tied my self as the picture I had downloaded showed. First my hands were bound together then my legs were. Finally I tied a short piece between my hands and legs and pulled tight after rolling onto my front I thought this is it I'm in my first self-bondage position. Not until this moment had I thought about how I was going to get out of this.

I lay there watching this girl getting cumshot after cumshot landing on her face trying to work out a way of getting out of this. My cock felt like it was about to explode, but I couldn't get to it too release my load.

I decided to see if I could roll to the study to try and get a pair of scissors to cut my way out. After half an hour of painful rolling I managed to get into the study and roll myself onto the chair. In the most uncomfortable position I have ever been in I started rummaging about for a pair of scissors. I had nearly given up when I finally found them. After a few snips I had cut the middle rope and could finally sit normally. After I had cut my hands and feet free I ripped the cock rings off and after only a couple of strokes deposited a massive load of cum all over the study desk.

By now it was 12 o'clock and I had to go to work the next day so I returned the stilettos and lingerie, removed the make up and set about going to bed. I found a silk nightie so put this on and went to sleep with the thoughts of the evening still fresh in my mind.

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