Macho To Sissy

This happened when I was about 15 years old, so I was really good at football and matt (my best friend) mum was friends with my mum and matt had a sister called Julie. Anyway one day wen I was home alone I found a bright pink underwear set of my mums and put it on with black pantyhose and a red dress I was also wearing a blond wig and red lipstick. Wat I didn't know was my mum had told Julie she could borrow her blonde wig for a school show and I left the door ajar so while I'm posing in the mirror I hear julie behind me say "ooh someone looks pretty dave!" I turned round and yelled "don't look at me" and "what the Hell are you doing here". She replied "well I had come to borrow that wig but since it looks so great on you ile hav to show your mum how good it looks". "No please I beg u she will think I'm a sissy". "You ARE a sissy! But ile tell you wat since your always bragging about how good you are a football if u can beat me thw. I will keep your secret but if you loose you have to do wat I say for am entire day". I agreed and she blew me a kiss as she walked laughing out of the house. A week later I got a cal from Julie saying "my mum and brother are out for the day (her dad didn't see them anymore) so why dont you come over for a match but remember i get to decide ALL the rules". "Fine" I said and set off for her house in my football kit and boots. When I got there she opened the door and looked horrified. "Wat is it?" I said. "This is all wrong, go sit down and I will find something more appropriate for you to wear". I went and sat down and heard her walk into the hallway and yell "GIRLS!! SISSY'S HERE!!". When she came back there was four girls with her all carrying bags. Julie said "since I get to decide wat the rules are I can decide wat you have to wear and I've chosen this..." She held up a French maids outfit and red panties bra and garter belt with flowery black pantyhose and a brunette wig. She then said "girls get to work!" And they pulled down my shorts and boxers and took of my boots and shirt and began dressing me up. Thats when Julie pulled a white container from her bag and pulled down my panties. I asked wat it was and she said itching powder then poured it all over my crotch. I then screamed in pain on the sofa as they covered my lips in lipstick and applied eyeshadow and mascara. Then came the dress which was several sizes to small and I could barely stand in it. Finally they put on red high heels and the wig and they carried me outside. They then handcuffed my feet together and my arms behind my back. Then Julie read out the rules they were; davina has to always keep her lips pouted, she cannot take off any of her clothes, i can have as many players as I want and davina has to play by herself, and we are allowed to do anything we want to do to davina and she has to take it like the sissy ***** she is. The punishments for breaking any of these rules were; davina has to wear a sign around her neck with her boy name and address on it, she has to eat a whole tube of lipstick for each rule broken and their favourite was to **** on a pair of panties then make me keep them in my mouth. As soon as we started it was obvious I was going to loose, it was first to five goals but everytime I ran for the ball I would trip over in the heels. Halfway through two boys from next door came to the fence to ask who I was and Julie told them "well she used to be a boy but she's been a very naughty girl so why don't you two go tell everyone in the neighbourhood that Dave sanders is a crossdressing, boy *******, **** sucking sissy or we will put you two in dresses as well. Before long I lost and the girls stood over me and said "uh oh it looks like are teasing and cross-dressing has made poor little davina get her dress all sticky!" And it was true I had exploded all over the outfit. They took lots of pictures of the *** stained dress and took me inside they sat me down and set up a video camera and I had to describe what I had been wearing when I was caught and how happy I was to have become a sexy girl. Then they took of the dress but left the underwear on and then removed the last thing from the bag and I felt so scared. It was Julie's mums wedding dress, they came towards me and I tried to run but two girls grabbed my arms and held me still. I said please no anything but that but Julie just said "fine you don't have to wear it if you don't mind your pictures apperaing In the school newspaper and delivered to your mum and friends. I started crying as they put on the heavy silk petticoats and laced up the corset. They also swapped my heels for white ones to match the dress and put the veil on my head. Once they had finished they took so many pictures of the beautiful bride. That's when Julie suddenly started kissing me full on the mouth and pushing me back towards the sofa, she lay on top of me and kept kissing me but then suddenly shouted "NOW!" And the girls grabbed my arms and legs and tied them to the sofa. Once I was tied up Julie stood up and said "I can't believe you fell for that you really think I would go for a perverted sissy who wears a wedding dress and dresses up as a French maid! Now I doubt this will taste as nice as me but oh well" she thrust a her mums vibrator into my mouth and switched it on then taped it up so I couldn't spit it out. Then they all teased me by saying "we know you love sucking that cocky and well done u sick sissy boy. So there I was tied to a sofa in a wedding dress and sucking on a vibrato when the front door opens and Matt and his mum walk in. They stared at me for what seemed like years then burst into hysterics and I couldn't get the ***** out my mouth to beg them to stop laughing. after at least 15 minutes Matt's mum turned to matt and said I don't know why your laughing beacuse Julie told me about davina's little hobbie and I thought it sounded like a great idea so while you were off buying football kit I did a little shopping for you. From one of her bags she pulled out a naughty little policewoman outfit and a bright pink set of underwear. His mum held him down as the girls tore off his clothes and put him in the outfit and did his hair and makeup. Once he was done they untied me and pushed us together then made us kiss on the mouth non stop for at least 10
Minutes and the whole time they were taking photos. They then had their favourite idea which was to put keys on rings at the base of our dicks and said if we could get the key off the other ones **** then we could get changed. They teased as we fought to give each other blow jobs to try and get the key but neither of us managed it and they took the keys away. The they said that they would get rid off all the photographs and videos if we bummed each other but we ended up having to do it twice because matts mum had to pick up things for dinner. They finally let us change back to our old clothes and matts mum dropped me home. When I got there my mum was in and I shouted hi as I went upto my bedroom. I opened the door and almost cried, the pictures of me were all over my room and my mum came ul behind me and said "a certain mum dropped these round and I hear you've been wearing a few of my things but u won't hav to now, look in your wardrobe. I did and it was completely full of dresses. I checked every draw for my trousers and t shirts but thefe was only bras and panties. "Yes that's right you never have to be a boy again now get changed into that lovely pink dress and come downstairs, I think its time you see Matt again....
petticoatedsissy petticoatedsissy
18-21, M
9 Responses Mar 19, 2012

your mom is a ***** and so is matts sis and mum

hi ! nice !

What happened next?

these girls are geniuses!! my red lipsticked lips can't stop laughing about how sick u are! did his **** taste nice? did ur best friends **** taste nice? I bet u licked up every last drop of his *** didn't you! you should thank everyone of those girls beacause they showed u what a freak u are and how you will always be in the power of your feminine masters! and when I say feminine I don't mean the gross version of feminine you try to be, I mean breasts and vagina not tiny ****

if this all happened to me i would have rather just died. seriously im not joking about that

wow you couldn't overpower 2 girls?

well they were a year older than me and I was already wearing pantyhose, panties and a bra so I couldn't run outside


i just *** all over myself , running out of my thongs crotch and down my shiny pantyhosed legs , mmmmmm great story

Dear, can you contact me? I cannot message you at all. Thanks! j

Hiah u asked me to message u :)

i bet you liked it though! i gave mine up willingly and LOVED IT and still do but i will always remember my first!!!!

bet matt has some fun with her