A boy is blackmailed into pretending to be a girl for a whole week. If you like this then I will happily do more
I was 15 when this happened. I was quite short, 5"8. The shortest out of all my friends by far. They all joked about me being girly but I didn't mind. I knew what I was. My best friend was actually a girl, Claire Johnston, and one day when I was over her house, she left me alone in her room as she went to the toilet. I sat there for a while watching TV but then something caught my eye
One of her draws was open and there was a pair of knickers hanging out. They were pink and frilly and the most girly things I’d ever seen. I went over to them and picked them up. I rubbed them against my cheek and smelt them. They were beautiful.
I looked out onto the landing and there was no sign of CJ coming back. I quickly pulled my trousers and boxers off and put on CJ’s lovely thong. I looked outside again and upon seeing nothing decided to risk it even more. I took my shirt off and found a bra in another cupboard. It was a fair match for the thong that I was wearing and I put it on. I stuffed some tissues down it and looked at myself in the mirror.
I saw CJ in the reflection and turned around just in time for her to take a picture of me in her underwear.
“Shit, I’m so sorry” I pleaded, “Don’t tell anyone please”
CJ was laughing so hard that she had to wait a minute before announcing what she was going to do. “Hmmm”, she pondered, “Ok I won’t tell anyone, us being friends and all”
“Oh, thank you so much” I said undoing the bra.
“No, I didn’t say I was going to let you off that easy” she said, stopping me in my tracks. “If you don’t want me to tell anyone then you’ve got to let me have fun first.”
“Do you mean sex?” I couldn’t think of anything else.
“Eww, we’ve been friends forever, I don’t think of you like that. No, I have something better in store. If you want to dress up like a girl then go ahead.”
Her terms and conditions were that she was allowed to give me a complete makeover. It was school holidays and her parents would be away on a romantic break for a little while so she had the house to herself. She told me that I would have to move in with her for the next week and act as her BFF.
I pretended to agree reluctantly, but the idea of becoming a girl for a while was exciting. She took my underwear off and covered me in shaving foam, stripping all of my bodily hair. It felt weird and tingly but my skin was so smooth. She stood their looking at my penis and said, “Well, we will have to do something about you”. She got a roll of sellotape and stuck it down sideways so it went flat along my waist. She stuck my balls the other way so that they were horizontal. She pulled out some lacy, red lingerie and made me put them on. They felt so good. CJ was totally into drama and had loads of props from old shows. She just happened to have a pair of fake breasts which were the perfect size, big without being stupidly so.
I looked at myself in the mirror and instantly got a hard on. I hoped the sellotape would hold.
After looking through her wardrobe for what seemed like ages, CJ pulled out a black low-cut vest top and a pair of denim hot pants. I had seen her wear both of them before and never thought anything of it. However, the idea of me wearing them made them so much more appealing. I pulled them on and they were just the right size.
Next was my hair. Again CJ turned to her prop box and found a jet black wig which was perfect. It was a long process of dying my hair and making the extensions look right but it was perfect in the end. Then she started on my make-up. Again this seemed to take ages but eventually she announced that her work was done and she stepped back, handing me a mirror.
Again I got an immediate hard-on. My jet black hair rested on my shoulders which were exposed by my vest top. The top also left me my midriff expose which looked great. I wasn’t at all athletic so I was very slim, but I also had a naturally good physique (from my mum’s side) so I looked perfectly slender. Then the denim hot pants began, which then led on to my smooth, bare legs. If it had been a real person in front of me and not just my reflection then I would’ve fucked her right there and then.
CJ then took me through the basics of being a girl, how to talk, how to walk, things which she had taught many a boy before in drama. Then she stopped, “Shit”, I haven’t given you a name.” She said. She opened up a nearby magazine and flicked through until she found a picture of two models. She took the first name of one and the last name of another. “Nikki Daly” she announced proudly. “That is your new name.”
We sat around doing girl stuff for a couple of hours and then CJ got an idea to make me feel as awkward as possible. “Let’s have a girl’s night in.”
“Aren’t we already having one of those?”
“No. I mean a proper girl’s night in with other girls. Like a slumber party. It’ll be great”
I protested but knew that she wasn’t joking about showing everyone the pictures and so I agreed. After a while it sounded great. A night in with hot girls all snuggling up. Once CJ let it be known that her house was empty we already had five girls telling us that they would come. Most of them hot!
They turned up one by one and CJ introduced me as her cousin who was staying while her parents were away. I knew them all, but not well enough for them to recognise me in drag. As it was summer, they were all exposing plenty of skin. I had to make sure the sellotape on my cock would hold.
We had great fun doing make-up (even though I wasn’t good at it) but eventually the conversation turned to boys. Thinking that I didn’t know any of the local boys from school they showed me pictures of them on face book and asked me which one I would like to shag the most. Obviously I did know them and felt quit weird about the whole thing, some of them were my close friends. They even showed me a picture of me! I had never thought about any of the boys at my school in a sexual way before. But I settled on a picture of a boy that I didn’t know too well. His name was Jack and he was one of the sporty kids. Ripped from head to toe and with stubble on his chin.
Suddenly my mind was flooded with images of me being his girlfriend and us making, his hand caressing my inner thigh. Then me sucking his cock until he came all over my face. I’d never tasted cum before but I imagined it to be good. My imaginary montage ended with him fucking me hard up the ass, again with cum flowing everywhere. He whispered in my ear that he loved me before climaxing and leaving both of us lying there sweaty and panting for air. My head resting on his muscular torso.
My choice seemed to satisfy the girls but I was shocked at myself. I went to the bathroom and discovered that I’d actually jizzed a little bit. After tossing off in the bathroom, partly over Jack and also over the group downstairs I wiped myself off and changed my underwear before going back down to the girls. They had ordered pizza and were playing spin the bottle as they were waiting for it to arrive. Unfortunately I sat down at just the wrong time. The bottle pointed at me immediately just as the delivery car pulled up outside. We saw the man getting out of it. He was fairly average looking; He was in his early twenties, small goatee and a forgettable face. Not ugly but he was hardly Jack.
Just as the doorbell rang one of the girls shouted “You have to snog the milk man”. I was stunned into silence and the doorbell rang again. I was pushed to the door and it was opened for me as I was still in shock. One girl took the pizzas off him while another gave me the money. I was left alone with him on the doorstep after someone whispered to me that I had to hold five seconds with him. He held his hand out waiting for the money as I stood completely still. Eventually I realised what was happening and gave it to him and smiled at him. He turned away and was about to get in his car when I was pushed out the door after him. I looked around to see the girls egging me on through the window. If it was any other day then I would’ve bailed, but now I was curious as to how I was feeling .I tapped him on the shoulder as seductively I could so he turned around.
“You forgot your tip” I said as I wrapped my arms around him and bought our mouths together. Our tongues batted each other and I had to move my hips away to disguise yet another erection. I counted to five in my head but then kept going anyway. Eventually he pulled away, and looking awkward he got into his car and drove off.
The girls made fun for a while but it was soon forgotten. Eventually it turned dark and it was time to get out the mattresses in the living room. Then, suddenly all the girls took their clothes off. Six naked girls stood before me. There was one in particular that caught my eye. Her name was Ashleigh and I had had a small crush on her for ages. Her hair was short and dyed red and she had the perfect body. I had imagined her naked many times but seeing her now was unbelievable. She was not skinny, but perfectly curvaceous. I don’t know how I felt about guys, but I was definitely still into girls. She caught me looking and I looked away. I realised that they were getting changed into their pyjamas. I was going to have to get changed in front of them too.
Luckily CJ saved me, “Oh Nikki you didn’t bring any pyjamas did you? Go borrow some from my room”. I got some pyjamas, with shorts and short sleeves and was able to change in CJ’s room. I also reapplied the sellotape.
We all got together under one mattress and put on a horror film. Luckily, I was cuddled up next Ashleigh. I pretended to be scared a few times so that I could cuddle up to her. Eventually we fell asleep all under the same blanket. I was the last one to fall asleep due to how horny I was and so was able to manoeuvre myself so that I had one of my arms resting on her tits. As we had all fell asleep in a big pile it would seem innocent enough in the morning I hoped.
I was woke up in the night by Ashleigh shaking me. I woke up and saw her gesturing for me to go into a different room with her. I hoped she hadn’t noticed me checking her out. We went into CJ’s room and sat on the bed together.
She eventually spoke, “I think that I might be bi-sexual”.
“Wow” I said, genuinely shocked.
“I can tell you because you’re not from around here, and besides, I saw you looking at me earlier.”
“Why are you telling me?”
“Well, seeing as you won’t be here long, I was wondering if you could help me experiment?”
I was shocked, I had often thought about ramming her with my cock, but now, the girl of my dreams was coming on to me: thinking I was a girl.
We made out for a while and it was magical, exceeding all my expectations. Much better than the postman. Then she stuck her hand down my pants and recoiled.
“I’m sorry, I should’ve told you sooner, but I’m a guy. Please don’t tell anyone, I want you so much.”
Eventually she recognised me and I explained CJs blackmail to her. To my surprise she laughed.
“Here I was wondering if I was a bi, and I just happened to run into someone who’s both a boy and a girl.”
She pulled my cock out and stuck it in her mouth, moving up and down. I was careful not to moan too loud and wake up the girls downstairs, but Ashleigh was incredible. Up and down she went, not too fast and not too slow. After a couple of minutes she was fitting the whole thing in her mouth and massaging it with her tongue. Then she started licking my bollocks.
I lifted her top up and began to play with her nipples which went hard extremely quickly.
“I’m going to jizz.” I said.
“Quick”, she replied pulling her pants down, “I want you to fill me with your cum”.
Without hesitation she sat on me and put my whole shaft inside her pussy, and not a moment too soon. I immediately ejaculated harder than I ever thought that I could. We stayed like that until I finished and the I began thrusting into her, harder and faster. One of my hands was still fiddling with her nipples while the other was fingering her ass. I don’t know who was having a harder orgasm.
Slowly, we ground to a halt, and with one last thrust she fell to my side on the bed.
“Did that help?” I asked.
“Well, I still don’t know if I’m bi or not so who knows, we might have to do this again sometime.”
I almost ejaculated again at the mere thought of it. We tiptoed downstairs and lay down among the other girls. I put my hand on Ashleigh’s tit again. I reached out with my other one and it landed in the crotch of another girl. I thought what the hell and stroked a little bit before falling asleep as one of the girls.