Lucky Break

THE LUCKY BREAK

Part 1

My name is Lucy. Im a thick 6"2 white boi. As far back as I can remember ive been into crossdressing. I would sneak into my single mums room when i was home alone and go through her pantys and lingerie. Id try it on and just be so turned on by the look and feel of the sexy womens clothes. My mum had a few sexy teddys and stuff, but mostly i liked wearing her white satin panties, skin colored pantyhose and satin slips. I never got caught in the act but i had a few close calls over the years and though i never fully stopped, it had been a while for me when my desire to crossdress resurfaced.

Id just started my first job after school as a electrical apprentise. When my mum got the promotion as an exectutive she'd been working towards, when she told me we'd have to move for her job. I told my best freind this while i was over at his place on friday night hangout smoking weed and playing xbox. I was up getting some beers out of the kitchen when i bumped into his mum Joanne. I told her what was going on and she said "not to get my hopes up, but if Matt my mates dad said it was ok I could stay with them until i found another company to work for in mums new city". I should mention Joanne was a short chubby freakled readhead with big tits and was so sexy in that full figured woman way. Over the years id perved on her so much, she'd always been flirty with me, teasing me with skirts and panthose and would always have her cleavage on display. She new what i wanted. I was so obvious, my freind and his dad would make jokes of about it. Once she even caught me sniffing her dirty panties in the laudry. She said "there's a spare room since Bianca, my freinds older sister, had moved out with a freind".

When Mathew got home it was agreed id stay. So i went home asked my mum. She agreed and we packed my things the nextday and was dropped at my new home. This is were my crossdressing urge came back. While I was unpacking I realised Bianca still had clothes in the draws. We'd always been a similar size. Joane said to "leave them there just incase she needs them one day". That night i went through everything she'd left. Not only was there silk panties and slips and teddys, there was all sorts of lingerie, pantyhose and stockings and a pair white heels. Id packed a 6 inch vibrator and i new i was going to need it now. OMG, im at my freinds place and ive got the biggest collection of gurl clothes ever. I was so excited i was shaking at one point and was so horney i came in 1 of her colorfull onepeice swimsuit id always loved and went to sleep.

The next day i couldnt think straight at work. All i could think about was what to wear late that night when everyones asleep. Straight after work i rushed to my room which had its own small bathroom and started shaving smooth. Id bought a bottle of nair and waisted no time lathering up. Everything accept my face, id use a razor for that. I'd only gone smooth a few times before and i new feeling would shocked me. I would be beyond horney. About half an hour later i was totally smooth and hanging out in the lounge with my freind in sweatpants and a jumper. After a few drinks i relaxed as we hungout in the lounge while everyone came home. We soon herd "dinner" and went to eat. Joanne and Mat welcomed me and asked if i needed anything. I said "no i had everything i needed" thinking about later. I couldnt help but have a very slight smirk when i answered. Then i noticed matt glance at Joanne with his own smirk. He looked at me with a smile and said "oh were gona have fun trust me". Now, Matts a hansome guy, 6" who's been really good to me over the years. Once i accidently saw his cock when swimming and was shocked how big it was. This was the first time a male/man had ever made me aroused. I looked at joanne who had her ass sticking out of the fridge and smiled and said "sounds good to me". She had a very short loose white dress on and i could see her whole ass. He looked at what i was looking at and laught a little. When she came back he smacked her ass as she bent over the table. It was hard and loud, she love it. Then she sat on his lap lend back and gave him a kiss while he feels her tits. It was so arkward but i couldnt stop watching, i could see up her dress. She sat back in her seat and we chatted over dinner. Mostly about my mums sex life or mine. {none].I stared at her tits the whole time which were barely held in by her dress. I felt so comfortable with them and noticed Matt was really flirty. After this my freind said he was going to bed and so i took this chance to leave as well.

I locked my bedroom door and found some lingerie that I could hide quickly if someone knocked. Just a light blue nighty. The feeling of it on my smooth body was itself gona make me cum. When i put it on i herd the sound of a bed hitting the wall. I was rubbing my cock on the silk nightie and all i could think was matt and joanne were fucking. I got up and put my ear to the wall and thought i could hear joanne moaning. I couldnt beleive how sexualised my stay here was turning out to be. I got my vibrater out and started pumping my ass until i came on the nightie. Exhausted, i fell asleep in girls lingerie for the first time.

That was how everyday went until friday. That night my freind went to a party with a group of people i didnt like. Jo [we call her jo] and Matt go to a local karaoky bar every friday and are home late everytime. So i had the place to myself. When they left I waited 5 minutes to see if they'd forgoten anything and stripped naked. Then i went straight for Jo's panty draw. I was in heaven. She had so much variety of lingerie. But that wasnt what caught my attention. They had a sex swing hanging at the end of the bed. In the cupbords i found boxes with wigs and heels, others had stapons, vibrators, penis pumps and all sorts of toys. They had a double ended dildo which confused me alittle. I was shaking i was so turned on. I put on one of jo's black lace baby dolls and one of the strapons. It was hollowed out for u to put your cock in and it vibrated. I looked in there mirror and the sight of the cock i had on got me rock hard. Then i noticed they had an ipad. It had no code so i opened it up and went to the photos hopping to see some of jo. The first up was a video, i clicked it and on the screen was Jo in a green bodystocking with a strapon fucking some girl doggy style. I came right then and had to get outa there. I packed everything exactly how it was, but before leaving i sent the whole photo library to my phone, and deleted the record. I ran to my room and opened my phone. Sure enough i had a huge text from an unkown number. I layed naked in bed and went to the next video. Again it was Jo fucking this woman. This time she'd set the camera at the other end of the bed. The lights were better from this angle and it hit me. I was watching Jo pegging Matt. She was saying to him,"take it bitch, u whore, u total cock fag". Matt just moned and panted. i slowly rubbed my cock as i skipped through every picture and video. Alot were Jo being topped by Matts huge cock, some were matt dressed as a tranny posing sluty or being pegged. There were even a few picks were Matt had a real cock in his mouth and it was clear Jo was the one taking the pictures. I couldn't beleive it. I must've come 10 times that night and i still couldnt stop watch those videos. I discovered Jo liked to share the men who come round. There were videos of her being spit roasted by john and someguy. She loved choking on those cocks and even getting double dicked. The guy wore a mask so i never knew who it was. One thing was for sure I wanted it to be me. I just had to come up with a way to make happen.

The next morning i was laying in my bed wondering what the hell i was goning to do when my freind knocked on my door and said he was going away with his girlfreind interstate, i got dressed and got up to see him off. It turns out he'd be gone a month and maybe more. This was perfect. Now i could really find out what Mathews cock felt like buried in my ass. Jo and Matt got up and we all had breakfast together. jo had a million questions and agreed it was an exciting idea and so they took off leaving me alone with these two perverts hopefully to fuck our selves crazy.

A little later that day i was lounging on my bed playing xbox when i herd a faint knock then my bedroom door opened and Jo came in wearing only a tight white tshirt which her stomach poked out of and some white satin panties carrying a washing basket and asking if i had any washing for her since she was doing a load. I said sure, and she started picking up my dirty clothes bending over for me to have a perfect view of her volumptuos ass. I had sweatpants a hoody and socks on hiding the fact that i had a red see through gstring on underneathand, my toenails were painted slut red and my body was completely smooth. Luckily because my dick was getting hard. That was when everything changed. She turned around and headed out but when she passed me she grabbed my hoodie and took it off me before i could react saying "you've been wearing this all week it must need a wash" and through it in the basket. My heart was beating so fast and im sure i went pale. She then grabbed my pants at the feet and slipped off my pants and socks in one motion and threw Them in the basket. When she saw me she froze staring at me. A smile growing on her lips. "Whats going on here? " she laughed. "I turned my hips to the side to hide my hardon by this just exposed my ass in a gstring. And whack she slaps my butt laughing "mmm look at you all smooth and sexy. Your mum told us about your little secret. And she was right. you do make a good sissy boi. "Wait what? How did she know?" i said. "Oh she set up a camera to catch you a while ago. She was worried it was perverted since your dads not around. Matt and I told her not to worry and that you could stay here for a while to get a mans influence. So we came up with a plan to help you explore your sissy side and boy did you fall for it. " she laughed. Buy now she was siting on edge of the bed slowly slidding her hand up and down my leg smilling a warm understanding smile at me. Then she said" so what do u think, do u wanna explore your sissy side with Matt and I. Its not exacly what your mother wanted but i wont tell if you wont". "What did u have in mind" i said as she leand over and kissed me on the lips. I was in heaven. I kissed her back and we started sliding our toungs in and out of our mouths. I reached out with both arms and pulled her on to me so she was laying on top our legs interlocked. She was rubbing her thigh on my hard cock and i had one hand on her ass and one up her shirt playing with her big tits. Just as i was about to blow she grabbed both my wrists and pushed my arms above my head and climbed up to were her knees were either side of my head. Her pussy was right in my face. If it wasnt for her wet panties I could have been licking her clit. She started rubbing my face back and forth and said " oh no, a good sissy doesn't get to come before his mistress". And she hoped off. She could barelly keep from laughing at me. The state of insane lust shed brought me to. "Not until Matt and I have both finished using you. You stay right there sissy Ill be right back". And with that she left the room and was back in a minute or so. I couldnt tell how long it was because I was still in a state of complete arousal. I saw she brought something in i couldnt tell what it was and she walk up, pulled my panties down and grabbed my cock. Well it was more like a pinch. Before i new what had happened i was locked in cock cage. I lay there confused she said " this will make sure your willing to do any thing we want you to. Ive got the key and you can have access to that little cock when Im satisfied you have learned your place. Now go have a shower, Matts home soon and we still havent done your hair and make up". I got up and jumped in the shower. Joanne was right. I definately would have jerked off as soon as i could. Insted I could just wonder what they had in stall for me as I showered with blue balls.