"New York, New York" by sissy Claire
He’d never been to America so moving to New York was a big step. He just wanted to get away from everything for a few years. His family understood, he was under a lot of pressure with work and caring for family wasn’t easy for him either.
Josh had just finished taking the last box into his flat when the lady that lived opposite him was putting the keys in her front door. She was quite slim but not thin. Her hear was blonde and flowed just past her shoulders and to the top of her noticeable bust. Her face was smooth and welcoming and she had a natural smile. Josh tapped her on the shoulder and said ‘Hey, I’m your new neighbour, Josh.’ He smiled at her and she smiled back.
‘Hey, I’m Christy. The accent, English?’ she asked, tilting her head slightly.
He nodded his head. ‘Yep, first day out here! Never even been to America before but I wanted to start anew.’
She smiled again and hugged him ‘Welcome to Sisstine Block!’ Josh blushed slightly as he felt her nipples through her tight yellow crop top. She gave a slight grin as she felt it to.
‘I was going to grab some lunch in a second. Would you like to come with? I don’t really know where anything is.’ He replied after taking control of himself.
‘As in, like a date?’ Christy asked. ‘It’s just I’m a transsexual so most guys freak out after that so I don’t date much.’ After a moments shock, Josh regained his senses and looked at her and laughed.
‘Well then they’re idiots.’ He said. ‘If we’re going to be honest like that, I used to have a sissification fantasy so if that scares you off then so be it!’ He hadn’t thought about it for a few years but he wanted to make her feel at ease by making a joke out of it.
She smiled, thought for a second and then agreed. ‘I’ll just put this shopping down and I’ll come knock for you.’ She went in, blushing a little. Josh quickly put the last of the empty boxes in the bin and grabbed a clean shirt from his cupboard.
When Christy knocked on the door, she had traded her crop top and mini skirt for a floral summer dress and some sandals. She was stunning. Josh grabbed his wallet and they set out for the nearest coffee shop.
They both decided they didn’t want much to eat so they shared a muffin and each had a cup of coffee. They chatted about what everything from jobs to family to old flames. They loved spending time with each other. They had a lot in common too. They hadn’t dated anyone for years. Despite both being VERY adventurous neither of them had had sex. Christy had been left a small fortune by an uncle but had put most of it into savings. She owned two of the flats on the floor but had made them into one big one. She wasn’t working at the moment but volunteered a lot. Josh told her about his work as a paramedic and that he’d come into a little money which had brought him here.
It was closing time in the coffee house when they were finished. They wandered around the streets and ended up in central park. The sun was setting and they were sat atop a rock by a running stream. ‘I’ve had a really lovely afternoon Josh’ Christy said nuzzling into his shoulder. ‘You’re not like other guys, you’re sweet.’
‘I feel the same about you Christy.’ They looked at each other and Josh leant into kiss her beautiful lips. Christy kissed back and they shared a brief moment of bliss. Her pink-glossed lips touched his as he placed a hand on her cheek and pulled her closer. She slipped her tongue into his mouth and wrapped her arms around his neck and kissed him more forcefully. They were the only ones around and so Christy slid on top of Josh and straddled him. They continued kissing for a while, linking tongues as they held each other closely. After about fifteen of kissing they laid there staring at the sunset just breathing next to each other. It was a beautiful moment.
‘Should we head home? It’s almost 9:00 now.’ Josh said as he checked his watch. He didn’t want to leave. Her hair smelt amazing and feeling her resting against him was an amazing start to his new life. But it was night in a city he didn’t know and had no idea of how to get home.
‘I guess we should’ She sighed. ‘Do you want to come back to mine for dinner? I only have some random ingredients but we might find something.’
‘Sounds like a plan!’ Josh replied, helping her to her feet and pulling her close wrapping an arm around her. He swept her off her feet and carried her off the rock and out of the park. As he put her down she giggled and gave him a kiss on the cheek.
They walked back to the flats hand in hand just chatting some more about life. They stopped occasionally to look at shop windows. It was a lovely walk home. Christy slipped her hand into the back pocket of Josh’s jeans and gave it a gentle stroke as they got to their building. They walked up the stairs laughing and joking.
Christy took out her key and opened the door. The apartment wasn’t what Josh had expected. This part seemed identical to his with an open lounge-diner and kitchen area. The furniture was interesting though. There was a huge TV on the wall with a bright pink leather sofa facing it. The floor was laminate boards with a massive pink fluffy rug around the couch and two equally fluffy chairs. He liked it, it was pretty. There were pictures on the wall of some old magazine covers on with models on them.
The kitchen had an oven, hob and grill on one wall and then worktops on the other wall leading into a breakfast bar that stuck out the other side, fencing off the rest of the flat. There was a staircase leading up to the landing bedroom and bathroom like in his apartment. From the bedroom you could look down at the rest of the place. There was a door under the stair case that Josh’s place didn’t have which he assumed was access to the other flat.
She saw him looking around. ‘Don’t mention the furniture! ‘ She giggled. ‘It’s pretty and I love it!’ Josh nodded his agreement and went red for the hundredth time that day. ‘That door leads to the other apartment. I use it for storage upstairs but there are…toys…downstairs. Being a single transsexual is a bit lonely sometimes.’ She went a little colon forward slash so Josh walked over to her, lifted up her chin and passionately kissed her. He ran his fingers through her long blonde hair as she wrapped her arms around his neck pulling him close to her.
Their lips parted and they stared into each other’s eyes smiling until he pulled her into a hug. ‘Thank you Josh. I’ve never met anyone like you before. You’re special.’
‘I haven’t met anyone like you either. You’re perfect.’ Josh said, taking a deep breath, taking in her scent.
‘It doesn’t bother you that I’ve got a…you know…?’ She asked.
‘Not at all. I don’t care if you had nothing down there. You’re an amazing, lovely, sweet, kind and obviously caring person. Plus, if I’m being honest, the idea kind of turns me on a little.’ A smile escaped both of them as they looked at each other. They laughed, cuddled again and then went into the kitchen. ‘So we’ve got some onions, a pack of bacon, some frozen chicken and rice?’ Josh asked as he looked in the fridge. Christy nodded with a cheeky grin. ‘Well let’s see what we can do then!’
Forty minutes later they were sat at the breakfast bar and with the help of some spices, Josh had made a pretty tasty meal. Christy had chosen a bottle of wine and dimmed the lights. As they were finishing off Christy looked up. ‘I want you to stay the night. I know you only just moved in but I feel we have a connection. I’m not asking you for sex, I just don’t want you to leave.’ She looked down at her plate feeling embarrassed.
‘I want that too. I’d love that.’ Josh replied. She looked up beaming and practically jumped across the table to hug him. Another kiss on the cheek. This time she sat on his lap, a leg either side of the chair and kissed him again.
It was so intense; Josh started getting hard and started to feel Christy doing the same against his chest. It made the moment so much hotter. They ended up making out on the leather couch for a while and then just laid there like they did in the park. It was about 11:30 by the time Christy took him by the hand to the bedroom.
‘So how do you want this to go? All of my clothes are at my place in boxes.’ Josh said.
‘Oh damn. You could sleep in just your boxers if you like, or you could were one of my t-shirts and more masculine shorts.’ She replied with a wink, already rummaging through her drawers to find something. She pulled out some loose fitting jersey exercise shorts and a pink crop top. ‘Go on, wear these!’ She pleaded. As he’d decided he’d done too much exercise today to wear the boxers and too tired to find anything in his own place, he reluctantly took the clothes. ‘Maybe one day I’LL be the one to sissify you’ She said, walking into the bathroom to get changed.
Josh got into the bed, feeling a little bit kinky but decided the top was too much and took it off. He was of slight build but tall. If he was wearing a dress, his silhouette would be that of a woman with short hair. He folded up the top and was placing it on the chair when Christy came out. She was wearing a white satin nightie with her hair tied up in a bun. She was gorgeous. She got into the bed and beckoned to the space next to her.
Josh hadn’t felt so close and comfortable with someone like this before. He liked it. He slid under the silk sheet and wrapped an arm around her and tucked in close. ‘Sleep tight beautiful. I’ve had the greatest day ever’. They drifted to sleep and slept soundly until morning.
Josh woke first. He looked at the clock and saw it was just past 8:00. After gently retrieving his arm from beneath Christy, he picked up his clothes and got dressed. He went down stairs and found some bread and eggs. He put some toast in and cracked some eggs into a saucepan so he could make some eggy bread. He found a plate and left the toast to soak up the egg. After tidying up the dinner stuff from last night, he made a pot of coffee and took her up breakfast in bed.
She was just waking up as he came up the stairs. He helped he get comfy and then placed the tray on her legs. She thanked him and pulled him into a kiss. Josh brushed a hair from her cheek and went down to get his own cup of coffee.
When he was walking back up the hard wood stairs, she was waiting for him at the top in her nightie. ‘Thank you so much for breakfast, it was delicious.’ As Josh came to the top of the stairs she kissed his forehead and pulled him onto the bed where they snuggled with cups of coffee and each other. ‘I suppose we should get up and showered then!’ Christy got up put on a dressing gown to match the white silk nightie she wore. Her figure was an amazing hour glass with long legs to compliment it.
As she tied it Josh got up. ‘I’ll head home and shower. I have loads of clothes to sort out and I have to buy some stuff for the apartment. I don’t suppose you’d like to go shopping would you?’
‘Shopping with a hot guy like you? Sure I would! Shall I knock when I’m ready?’ She asked.’
‘Don’t worry about knocking, I might be upstairs, just come in, I’ll leave the door open’ He wandered down the stairs and back into his own apartment. He went into his own bathroom to shower but when he got out, he realised that he hadn’t unpacked any towels. They were in a box downstairs.
He let himself dry of naturally for a little while before running downstairs. He got the box that he was looking for and as he opened it the door behind did the same. He was stood there naked in front of Christy. His body was smooth and hairless from when he used to experiment with cross-dressing and he wasn’t the muscliest of guys. She quickly shut the door behind her. She was wearing a denim mini skirt with black leggings and a pink tube top. Her hair was down and she gaped as Josh spun around completely naked.
‘I’m so sorry! I was in the shower and I’d left the towels down here and…’ She cut him off before he could say anything else.
‘It’s fine!’ she cooed at him. She walked up and pecked him on the lips. ‘It’s just…I’ve never seen a man’s cock up close before.’ She gently ran a perfectly painted pink nail down his chest to the base of his now erect penis. ‘I don’t want to rush things though.’ She said letting go as if awakened from a trance. ‘Dry off, get dressed and we’ll empty the rest of these boxes.’
As Josh turned around Christy couldn’t contain herself. She crept up behind him, placed her hands on his waist and kissed his neck sensuously. He stopped searching for a towel and let her spin him around as she pulled him into a French kiss. She knelt and wrapped a hand around his now fully hard cock and started to stroke it. Josh stumbled back as pure pleasure ran through his body. She put her lips to the head and gently ran her tongue over it. He ran his hands through her hair and used all his will power to pull her up to his level. ‘Is this what you want? We’ve only just met.’
‘I know, I just wanted to try it.’ She blushed slightly and turned away. Josh pulled her back around and hugged her before taking her upstairs. He towelled off and slung on some boxers. ‘Can you wear just those whilst we’re inside?’ She giggled. Josh thought for a moment. He was still very hard from her tongue and it was very noticeable. ‘I’ll do the same.’ And with that she was sliding out of her tube top and skirt. All that was left was a pair of pink ruffle knickers and a matching bra. The knickers were home to a penis that was just as hard as Josh’s but a bit longer, straining to get out.
After they’d fooled around a little, rubbing the other through the fabric of their clothes, they unpacked the remaining boxes. They chatted as they did so. Christy was asking if Josh had liked the shorts he slept in. He had to confess that they were much comfier than the men’s shorts he was used to. Then came a rapid fire of questions about his sissy fantasies. When it started, what he liked, what he didn’t like, if he had any clothes and whether he’d like to do it someday.
It had started when he was about 14 and experimenting with wigs and pretty skirts but hadn’t done anything like it for three years. He loved pretty much anything about it except for forced bi. He didn’t want some guy coming in acting like he was his bitch. The clothes he’d ever had he had thrown out for fear of being discovered and he’d love to do it some time.
She listened intently, it was evident she was interested. ‘So you never had anyone help you or spoke to anyone about it?’
‘Nope, you’re the first person I ever told.’ He replied.
She thought for a moment and then had an almost evil grin on her face. ‘We should get dressed and get some basics for you!’ They both got dressed and walked out the building hand in hand. Josh wanted to get some food and new kitchen gear. So Christy took him to a few shops in the local area and showed him the way around the city. He loved it here. There was always something going on. Street performers or parades, just something. They got to know each other even more. They kept clicking together and just loved spending time with the other. Truth be told, they were both starting to love the other. It was a relationship they dreamed of. After a bite of lunch they walked back through the park again.
When they got back, they put everything in its place and sat down on Josh’s couch to watch some TV. The credits were rolling on an episode of friends when Christy spoke. Her head was resting on Josh’s chest and a hand was by her face. ‘I’m falling in love with you Josh. I know it sounds stupid but you’re perfect.’ She nuzzled into his neck.
‘I was worried you didn’t feel the same as me. I’m falling in love with you too. I have not once in my life felt so happy.’ They kissed and they took each other’s tops off and threw them on the floor. Next thing they were on the floor unbuttoning their denim. They rubbed each other through the fabric until they were both fit to burst.
‘I want you inside me.’ Christy said as her neck was being kissed. She undid the back of her bra and released two huge breasts. They were pert and firm and she guided Josh’s lips towards a nipple and he sucked and licked and bit at it until she was moaning with pleasure. She rolled over and pulled down her panties revealing her eight inch cock and ass. She pulled down his boxers and spat into her hand. Rubbing her saliva all over is cock she directed it to her ass. ‘Stuff me Josh. I want to feel your hard cock pushing into me!’ She moaned as his head penetrated her. It was tight but clearly had been loosened by the ‘toys’ she kept. He started off slowly but built up a strong steady pace.
‘That’s it baby, pound my ass!’ She screamed as Josh kept going. Christy spun round onto her back so she could see him as his cock slid in and out of her. Josh had only ever masturbated and never used a flesh-light let alone a woman. This felt amazing. He kept going for what felt like seconds but must have been ten minutes. As he thrust he felt her cock banging against his abdomen which drove him even crazier.
‘Oh God! I think I’m going to cum!’ He groaned as he approached orgasm. He didn’t stop but just kept going. He shot the biggest load right in her tight ass. She groaned as she felt the warmth fill her up.
‘Oh baby. That feels so good!’ She closed her eyes and gently moved herself slowly up and down the shaft. ‘Have you ever taken something up the ass before? Like this big cock?’ Josh shook his head, a little nervous as to what would happen next. ‘In that case I won’t start you off with this.’ She said tapping the head against him and smiling. ‘But I’d like to cum too’ She ran a hand on his cheek. She slid him out of her and sat on the couch so that her cock was just below his face. She placed her hands behind his head and guided him towards the shiny pre-cum that had emerged.
‘I want you to suck my cock. Will you do that for me?’ Josh practically leapt at the chance, gently licking up the cum that was already oozing. He’d watched plenty of porn in his life so knew how to give as much pleasure as he could. He gently ran his lips to the base and tickled her balls with one hand whilst squeezing a nipple with the other. As soon as he started Christy couldn’t manage words and all that came out were gasps and moans as he sucked at her huge hard cock. He worked the shaft with his hand as his tongue played with the head. Though he’d never admit it, the taste of her juice was delicious. He’d experimented with CEI before but it had never tasted this good. He lapped it up like a little cat and stared at her beautiful face twisting as shivers went up her body.
He worked it hard and fast and she came closer to the edge until she burst. A deep moan was let out as her cum filled his mouth. She leant backwards, breathing heavily. She lifted his chin and ordered him to open his mouth so she could see her juice. He obliged and she dipped a finger into her massive load. She pulled him into a kiss and the cream flowed between their mouths in an intense moment of passion. ‘Bottoms up!’ She smiled and let it all drop back into his mouth. He gulped it down. It was warm on the back of his throat but he drank the whole load and kissed the head of her cock as he rose and sat next to her. ‘That…was amazing.’ They kissed again sharing the salty taste whilst holding each other closely.
Josh took Christy’s hand and led her to the bathroom where they shared a shower. They rubbed oil onto each other. Kissed and caressed. When they were done they both dried off. ‘Want to come over to mine for the evening? We can order some food in if you like.’ She offered.
‘Sounds like a plan! What time?’ He asked.
‘Now silly! I have something I want to show you.’ She smiled and slid her tube top back on. And buttoned up her skirt. ‘So what do you say?’
He’d seen the city and knew his way around close enough for the two days he’d been there. He knew no one else and he’d just had sex with the one he loved. He was not going to miss one second with her. ‘I wouldn’t miss it for the world.’ They Eskimo kissed and they went back across to her apartment.
Josh sat one of the fluffy chairs in the lounge as Christy told him to whilst she went next door. She came back with a small box and a big smile on her face. ‘Now I could tell by the way you talked about it that you still wanted to be a sissy so I’m going to help you! I still want us to be together as a couple no matter what and I thought it would be fun! So strip bare and let me see you!’ Josh stripped down and revealed yet another erection. ‘To start with I want to be able to make you feel as good as you made me feel earlier so that means training your ass to take a big cock like mine. So I have this.’ She pulled a thin but long black butt-plug out of the box. ‘You know what this is, don’t you?’ She said seductively. A bottle of lube was produced next and Josh was pulled across the coffee table as Christy started lubing up his tight sissy hole. She gently eased the plug in. ‘How does that feel sweetie?’
‘Really…uh…good!’ He groaned as the end was pushed through.
‘We’ll work you up to bigger ones gradually! I’m so excited! I thought you might like to cover it in these.’ She pulled out a pair of ruffle knickers like hers earlier but these had a slit at the front. She slid them up his legs and they felt so good. ‘That’s right your sissy clit goes through there.’ She put his longing cock through the hole and gently rubbed it. She gently spanked him once and then pulled up his jeans and buttoned them, rubbing his hard cock through the zip.
Christy phoned up a Chinese take-out and ordered a wide selection of dishes. They sat down and watched a repeat of Friends in each other’s arms. The doorbell rang and Josh stood up, feeling the plug move slightly inside him, answered the door and set out the food on the table. They split it onto two plates and sat down to eat. They chatted and laughed, they joked and flirted. It was like they were meant to be together.
‘I want to make you a full on sissy. Just for tonight!’ It came out of nowhere and Josh went bright red. ‘I really want to try it!’ She gave him a seductive smile and gently ran her bare foot up his leg and rubbed it against his knicker clad crotch.
‘I’d like to try that too.’ Josh replied.
Christy jumped up like a school girl and ran upstairs. She came back with a big metal case that she placed on the floor and opened it out. It looked like a corner cupboard and inside one half was coated in small slim draws and the other had two doors on it with shelves behind them. The lining was red velvet with a slight red fur trim. The draws were filled to the brim with make-up of all colours and varieties. There was everything from eye-liner to lip gloss. There was glitter in some, others were more gothic style. ‘To start with, I’m going to ask you to strip except for the pretty panties. We’re going to make you so hot!’
She started by opening the cupboards and took out a razor and some cream. She pulled the knickers down and sprayed some foam onto his pubic hair. She pushed him against a wall and ran her tongue around the head of his cock. She took the razor and gently moulded his pubic region. When she was finished a neat little heart was there right above his sissy clit. She then went back and exchanged the razor for a tube of pink liquid. She squeezed some onto her hand and gently massaged it into the heart. The light brown hair quickly turned into a pretty neon pink fur. ‘There! Already a mark to show that you are my little sissy boy!’ She tickled his balls a little and tongued him again. ‘No other hair either! You were born for this sweetie.’ She held his chin and kissed him. ‘If you’re going to be my sissy though, you need a sissy name! How about…Victoria? No! Tori! That’s perfect! My little Tori Heart!’ She gave a giggle and pulled the panties back up.
She told him to stay there whilst she dragged over a stool and the case. She started with some foundation and then spent about twenty minutes on her eyes. Everything had to be pink. She thought as it was the first time this sissy would be here, it should be in style. Then eyebrows got plucked and thinned and then a little bit of blusher on the cheeks.
Finally came the lips. She selected a bright pink that would match his dyed hair and added generous amounts of gloss to make them absolutely irresistible. Christy held out a tissue and made him lip bite onto it which left a pink lipstick mark that for some reason made Josh’s cock harden in his lacy sexy knickers.
‘There we go! You look just amazing my little sissy slut!’ She returned the shelves and boxes of make-up to the case and returned with a blonde wig. It was very long and rested about three inches above the back of the frilly knickers and as he swayed his head, the hair shook out and tickled the lower back. ‘Oh wow! You even shake your hair out like a girl!’ Christy chuckled. ‘I think we’re going to start off in some casual clothes so follow me up to the bedroom Tori!’ a subtle wink followed the instruction and they walked up the stairs to the balcony bedroom.
When she walked, Tori could feel the plug moving around, occasionally brushing past her prostate. With the knickers covering her clit, you couldn’t tell that she was actually a he. When they reached the top of the stairs Christy flung open a cupboard door and revealed a massive selection of female clothes. ‘I think your body would look good in these!’ A pair of jeggings were taken out and handed to Tori who put them on, adjusting them slightly over her knickers. ‘Hmm, I think a pink top is definitely needed. How about trying this on?’ She picked up a pink knitted top that had no shoulders and hung at the sides of the arms. It was slightly too shot to reach the top of the jeggings which gave the whole outfit a little bit of a slutty side.
Tori flicked her hair out the back of her top and shook it out which made Christy very horny very quickly. Whilst Tori admired herself in the long mirror on the cupboard door Christy started rubbing her own cock through the denim of her skirt. Tori turned and saw the horny transsexual and wondered over to her. She knelt at her feet and unzipped the denim skirt. The erect cock fell down and knocked Tori’s nose. With her new pink lips she kissed the base of Christy’s cock and left her lip marks. Christy ran her hands through the long blonde hair and directed the same pink lips to the head of the cock. ‘We’ll have to touch up your lips up after this, you’d best get the whole load in your mouth or we’ll have to start everything all over again.’
Tori took her advice and used her tongue and lips to work the head whilst both of her hands worked the big she-cock shaft. Tori’s hands could feel the cum building up as orgasm approached and teased her for as long as possible. Eventually there was no way of teasing the cock without sending her over the edge so Tori went frantically up and down the cock with as much speed and force as she could manage. The beautiful t-girl sprayed a massive load in her sissy’s mouth and, like earlier, kissed her deeply so that they could share the taste. Then Tori greedily gulped down the load and kissed each of Christy’s balls which made her shiver and thrust into her pets face a little bit. Whilst Christy recovered herself Tori slid her frilly knickers back up and did the denim skirt back up.
Christy sat on the foot of the bed and lay back panting. She glanced over at Tori ‘I didn’t think you could beat last time but my God, that was good. I’m impressed as well. You managed to give a blow job without ruining your make up! Well done!’ She beckoned for Tori to join her on the bed. The sissy lay next to her lover and rested her blonde hair on her shoulder. Christy placed an arm around her new toy and placed her chin on the wig. It was strange, they’d only known each other for two days but neither had ever felt closer to someone in their lives.
‘I think I love you Josh.’ these were two words that Christy had never thought to come out of her mouth. ‘I know it sounds ridiculous but you’re the perfect level of kinky and submissive, you’re sweet and kind and I just love you.’
Josh had only said that to one other girl but this was different. ‘I love you too. I’m not saying I’m in love with you but you’re amazing.’ He looked up at her and rested his chin on her chest. ‘I think you’re lovely and generous. You’ve guided me into a world I never have gone into on my own, you’re always teaching me new things and most importantly, you’ve got huge breasts and a massive cock!’ The last part was a joke and they both giggled and pulled into a lovers hug.
They stayed in bed, both looking slightly slutty, and fell asleep. It was a perfect night’s sleep and they stayed in each other’s arms until dawn came. Tori woke first and lay next to Christy just staring at her natural beauty. She sat up and saw herself in the mirror with, amazingly, still perfect make-up and hair. The long blonde locks were very realistic and when she ran a hand through it she looked like a porn-star. She walked over and knelt with her legs spread slightly. Her cock started getting hard and the jeggings framed it nicely producing a long tube underneath the material.
With one hand Tori ran a hand through her hair and with the other she rubbed her cock through the material like a woman would. The hand in her hair slid underneath the pink top and started playing with a nipple. After ten minutes of pinching at nipples and rubbing her stick, she stopped and admired herself in the mirror. Add some fake breasts and there was a real woman there. Tori hadn’t noticed but Christy was up and staring at her. Naturally, Tori blushed heavily when she saw her lover looking at her as she was trying to be a sexy little girl. Christy broke out into a smile, stood up, and took Tori’s hand downstairs.
They sat at the breakfast bar and tucked into some croissants as they discussed the day ahead. ‘I thought we could go out today. Maybe see a movie or something?’ Christy asked as she took a bite of delicious pastry. ‘I have a few girlfriends I’ve been meaning to catch up with. The way you look and walk I really think you could pass for one of the girls! If you want to that is?’
She couldn’t believe it herself but there was absolutely no trace of Josh left to look at. Tori really did look like one of the girls. Putting on a slightly more feminine voice she said ‘I’d love to. That would be great.’
Christy looked shocked at the voice that she had just heard but then smiled and pulled Tori into a hug. ‘Yay! We’ll pick you out a lovely outfit! I’m thinking maybe a plaid skirt and a white sweater top? We’re going to be the hottest couple around!’
They finished their breakfast and they sat on the couch together. ‘Sweetie, you know that plug I put in yesterday? Well it came with this.’ She pulled out a rubber tube and pump from the side of the cushion. ‘Can you get on all fours and stick your perky little ass up for me?’ Tori obeyed and rested her forearms on the floor and pushed her sissy hole in the air. She really did look like a slut.
Christy pulled down the jeggings and knickers to reveal the plug. There was a screw connection that the tube connected to so she screwed it in. ‘This pump will expand the plug and make your ass hole bigger. That means that if you take it well, you could be getting my cock in there soon!’
‘Oh God, really? I would love that!’ Before she had even finished the sentence Christy was pumping furiously filling the plug with air. Tori gasped as, for the first time, her ass was filled completely and then some. After a few moans caused by the new sensation, and a few minutes of pumping, the process was complete.
‘How does that feel? Good?’ Tori nodded, biting back the urge to yell out in pleasure and a little pain. ‘I just want to work it in a little more’. Christy started shaking the ass and gently spanking it causing more pleasurable noises. The plug was now about four times the size it was earlier and Tori was doing remarkably well considering her virgin ass. ‘I’m going to leave it in there for a few hours and then we’ll see how you feel, OK pet?’ she stroked the sissy hair and kissed her cheek. She then helped her up and sat her down on the couch again.
After a little adjustment and fidgeting Tori was able to find a comfortable position that she could happily cuddle up next to Christy. They spent the day relaxing and watching TV, occasionally kissing and fooling around. All the while Tori’s ass was stretching out.
Eventually, Christy removed the plug and at about five in the evening Christy took Tori upstairs and got her dressed in a pink plaid skirt with white tights on and a white sweater top. She handed her a pair of pink patent flats as well but when Christy observed she knew something was missing. After a moment’s thought she clicked and realised that the hair didn’t quite gel with the outfit. She tied it back in a long ponytail and clipped a flower of the same pink as the skirt to the side of her hair. She looked like a she. It was unbelievable.
Christy had decided to don a pair of skinny jeans and a pink tube top that complimented the darker pink of Tori’s skirt. A pair of heels was taken from the bottom of a cupboard that was the same pink patent that Tori wore. When they stood next to each other, Christy was about three inches taller than Tori.
They headed out and met Christy’s friends outside the theatre and after introductions; they headed inside and watched a romantic comedy that had just been released. About thirty minutes into the film Christy reached a hand over and started rubbing the sissy cock through the skirt as a sex scene came on. The man was muscly and handsome and very powerful and the woman was a blonde bending over and let him fuck her really hard.
Tori glanced over her lover and could see she was very turned on. Christy’s two friends were making out next to them too. Tori hadn’t realised they were lesbians. As the sex scene got more intense Christy rubbed harder and faster. Now that she was so horny, she wanted to repay Christy for the attention he was getting. They were on the back row of the cinema and they were on the earliest showing so the place was pretty much empty except for a couple on the front row.
Tori mounted Christy and kissed her deeply ‘I want to do something wild!’ she whispered. With that, she unbuttoned Christy’s skinny jeans and pulled her knickers across to let the hard cock ping up. Christy was even hornier now and started biting at her neck and running hands up her top to pinch at the nipples. Tori hoist up her skirt and slid the tights and knickers down. There was a copious amount of pre-cum on the tip of the aroused shemale cock. This was used by Tori to rub around the rim of her sissy hole to lube it up a little.
It was just under two inches in diameter and a little larger at the head which was now popped inside the hole. If Christy’s tongue hadn’t been gagging her, Tori would’ve yelped as she was stretched properly. Still lip-locked, Tori slowly lowered herself onto the cock. The feeling was amazing, the butt plug was nothing compared to this. The head pushed against her button and she slowly started to raise herself up and down.
Christy’s two friends had stopped kissing and stared at the real sex scene as they slid their hands down their partners skirt and started massaging the others pussy. Seeing this completely hormonal scene caused a feeling in Tori that ignored any pain she may have felt and replaced it with pleasure. She bounced up and down on the cock loving every second of it watching her own smaller dick bounce up and down.
Christy’s friends reached orgasm for the first time as Christy took hold of the bouncing stick and started vigorously working it with both hands. Tori came close long before Christy, because her movements were slower, but Christy just kept edging her cock closer and then leaving her for a moment to calm down before continuing.
Tori kept pushing down on the cock until eventually Christy’s body went into spasm and she tightened her grip on her girlfriend’s cock and worked it until she blew a load too. Tori sprayed all over her own chest as she felt Christy’s sweet jizz fill her tight ass. The warm liquid was completely new feeling. It was perfect and she never wanted it to stop. Tori used her fingers and cleaned up the cum on her chest. She licked of a little herself, savouring the taste of it in her mouth and the feel of it in her ass, and then gave some to Christy.
Christy pulled out and helped Tori clench to keep all the cum up there. Tori collapsed between the legs of the one she loved. ‘There’s no turning back now my sweet.’ Christy whispered to her. ‘You’re going to only crave cock from now on.’ It was true. All she could think about was doing it again.
Josh had just finished taking the last box into his flat when the lady that lived opposite him was putting the keys in her front door. She was quite slim but not thin. Her hear was blonde and flowed just past her shoulders and to the top of her noticeable bust. Her face was smooth and welcoming and she had a natural smile. Josh tapped her on the shoulder and said ‘Hey, I’m your new neighbour, Josh.’ He smiled at her and she smiled back.
‘Hey, I’m Christy. The accent, English?’ she asked, tilting her head slightly.
He nodded his head. ‘Yep, first day out here! Never even been to America before but I wanted to start anew.’
She smiled again and hugged him ‘Welcome to Sisstine Block!’ Josh blushed slightly as he felt her nipples through her tight yellow crop top. She gave a slight grin as she felt it to.
‘I was going to grab some lunch in a second. Would you like to come with? I don’t really know where anything is.’ He replied after taking control of himself.
‘As in, like a date?’ Christy asked. ‘It’s just I’m a transsexual so most guys freak out after that so I don’t date much.’ After a moments shock, Josh regained his senses and looked at her and laughed.
‘Well then they’re idiots.’ He said. ‘If we’re going to be honest like that, I used to have a sissification fantasy so if that scares you off then so be it!’ He hadn’t thought about it for a few years but he wanted to make her feel at ease by making a joke out of it.
She smiled, thought for a second and then agreed. ‘I’ll just put this shopping down and I’ll come knock for you.’ She went in, blushing a little. Josh quickly put the last of the empty boxes in the bin and grabbed a clean shirt from his cupboard.
When Christy knocked on the door, she had traded her crop top and mini skirt for a floral summer dress and some sandals. She was stunning. Josh grabbed his wallet and they set out for the nearest coffee shop.
They both decided they didn’t want much to eat so they shared a muffin and each had a cup of coffee. They chatted about what everything from jobs to family to old flames. They loved spending time with each other. They had a lot in common too. They hadn’t dated anyone for years. Despite both being VERY adventurous neither of them had had sex. Christy had been left a small fortune by an uncle but had put most of it into savings. She owned two of the flats on the floor but had made them into one big one. She wasn’t working at the moment but volunteered a lot. Josh told her about his work as a paramedic and that he’d come into a little money which had brought him here.
It was closing time in the coffee house when they were finished. They wandered around the streets and ended up in central park. The sun was setting and they were sat atop a rock by a running stream. ‘I’ve had a really lovely afternoon Josh’ Christy said nuzzling into his shoulder. ‘You’re not like other guys, you’re sweet.’
‘I feel the same about you Christy.’ They looked at each other and Josh leant into kiss her beautiful lips. Christy kissed back and they shared a brief moment of bliss. Her pink-glossed lips touched his as he placed a hand on her cheek and pulled her closer. She slipped her tongue into his mouth and wrapped her arms around his neck and kissed him more forcefully. They were the only ones around and so Christy slid on top of Josh and straddled him. They continued kissing for a while, linking tongues as they held each other closely. After about fifteen of kissing they laid there staring at the sunset just breathing next to each other. It was a beautiful moment.
‘Should we head home? It’s almost 9:00 now.’ Josh said as he checked his watch. He didn’t want to leave. Her hair smelt amazing and feeling her resting against him was an amazing start to his new life. But it was night in a city he didn’t know and had no idea of how to get home.
‘I guess we should’ She sighed. ‘Do you want to come back to mine for dinner? I only have some random ingredients but we might find something.’
‘Sounds like a plan!’ Josh replied, helping her to her feet and pulling her close wrapping an arm around her. He swept her off her feet and carried her off the rock and out of the park. As he put her down she giggled and gave him a kiss on the cheek.
They walked back to the flats hand in hand just chatting some more about life. They stopped occasionally to look at shop windows. It was a lovely walk home. Christy slipped her hand into the back pocket of Josh’s jeans and gave it a gentle stroke as they got to their building. They walked up the stairs laughing and joking.
Christy took out her key and opened the door. The apartment wasn’t what Josh had expected. This part seemed identical to his with an open lounge-diner and kitchen area. The furniture was interesting though. There was a huge TV on the wall with a bright pink leather sofa facing it. The floor was laminate boards with a massive pink fluffy rug around the couch and two equally fluffy chairs. He liked it, it was pretty. There were pictures on the wall of some old magazine covers on with models on them.
The kitchen had an oven, hob and grill on one wall and then worktops on the other wall leading into a breakfast bar that stuck out the other side, fencing off the rest of the flat. There was a staircase leading up to the landing bedroom and bathroom like in his apartment. From the bedroom you could look down at the rest of the place. There was a door under the stair case that Josh’s place didn’t have which he assumed was access to the other flat.
She saw him looking around. ‘Don’t mention the furniture! ‘ She giggled. ‘It’s pretty and I love it!’ Josh nodded his agreement and went red for the hundredth time that day. ‘That door leads to the other apartment. I use it for storage upstairs but there are…toys…downstairs. Being a single transsexual is a bit lonely sometimes.’ She went a little colon forward slash so Josh walked over to her, lifted up her chin and passionately kissed her. He ran his fingers through her long blonde hair as she wrapped her arms around his neck pulling him close to her.
Their lips parted and they stared into each other’s eyes smiling until he pulled her into a hug. ‘Thank you Josh. I’ve never met anyone like you before. You’re special.’
‘I haven’t met anyone like you either. You’re perfect.’ Josh said, taking a deep breath, taking in her scent.
‘It doesn’t bother you that I’ve got a…you know…?’ She asked.
‘Not at all. I don’t care if you had nothing down there. You’re an amazing, lovely, sweet, kind and obviously caring person. Plus, if I’m being honest, the idea kind of turns me on a little.’ A smile escaped both of them as they looked at each other. They laughed, cuddled again and then went into the kitchen. ‘So we’ve got some onions, a pack of bacon, some frozen chicken and rice?’ Josh asked as he looked in the fridge. Christy nodded with a cheeky grin. ‘Well let’s see what we can do then!’
Forty minutes later they were sat at the breakfast bar and with the help of some spices, Josh had made a pretty tasty meal. Christy had chosen a bottle of wine and dimmed the lights. As they were finishing off Christy looked up. ‘I want you to stay the night. I know you only just moved in but I feel we have a connection. I’m not asking you for sex, I just don’t want you to leave.’ She looked down at her plate feeling embarrassed.
‘I want that too. I’d love that.’ Josh replied. She looked up beaming and practically jumped across the table to hug him. Another kiss on the cheek. This time she sat on his lap, a leg either side of the chair and kissed him again.
It was so intense; Josh started getting hard and started to feel Christy doing the same against his chest. It made the moment so much hotter. They ended up making out on the leather couch for a while and then just laid there like they did in the park. It was about 11:30 by the time Christy took him by the hand to the bedroom.
‘So how do you want this to go? All of my clothes are at my place in boxes.’ Josh said.
‘Oh damn. You could sleep in just your boxers if you like, or you could were one of my t-shirts and more masculine shorts.’ She replied with a wink, already rummaging through her drawers to find something. She pulled out some loose fitting jersey exercise shorts and a pink crop top. ‘Go on, wear these!’ She pleaded. As he’d decided he’d done too much exercise today to wear the boxers and too tired to find anything in his own place, he reluctantly took the clothes. ‘Maybe one day I’LL be the one to sissify you’ She said, walking into the bathroom to get changed.
Josh got into the bed, feeling a little bit kinky but decided the top was too much and took it off. He was of slight build but tall. If he was wearing a dress, his silhouette would be that of a woman with short hair. He folded up the top and was placing it on the chair when Christy came out. She was wearing a white satin nightie with her hair tied up in a bun. She was gorgeous. She got into the bed and beckoned to the space next to her.
Josh hadn’t felt so close and comfortable with someone like this before. He liked it. He slid under the silk sheet and wrapped an arm around her and tucked in close. ‘Sleep tight beautiful. I’ve had the greatest day ever’. They drifted to sleep and slept soundly until morning.
Josh woke first. He looked at the clock and saw it was just past 8:00. After gently retrieving his arm from beneath Christy, he picked up his clothes and got dressed. He went down stairs and found some bread and eggs. He put some toast in and cracked some eggs into a saucepan so he could make some eggy bread. He found a plate and left the toast to soak up the egg. After tidying up the dinner stuff from last night, he made a pot of coffee and took her up breakfast in bed.
She was just waking up as he came up the stairs. He helped he get comfy and then placed the tray on her legs. She thanked him and pulled him into a kiss. Josh brushed a hair from her cheek and went down to get his own cup of coffee.
When he was walking back up the hard wood stairs, she was waiting for him at the top in her nightie. ‘Thank you so much for breakfast, it was delicious.’ As Josh came to the top of the stairs she kissed his forehead and pulled him onto the bed where they snuggled with cups of coffee and each other. ‘I suppose we should get up and showered then!’ Christy got up put on a dressing gown to match the white silk nightie she wore. Her figure was an amazing hour glass with long legs to compliment it.
As she tied it Josh got up. ‘I’ll head home and shower. I have loads of clothes to sort out and I have to buy some stuff for the apartment. I don’t suppose you’d like to go shopping would you?’
‘Shopping with a hot guy like you? Sure I would! Shall I knock when I’m ready?’ She asked.’
‘Don’t worry about knocking, I might be upstairs, just come in, I’ll leave the door open’ He wandered down the stairs and back into his own apartment. He went into his own bathroom to shower but when he got out, he realised that he hadn’t unpacked any towels. They were in a box downstairs.
He let himself dry of naturally for a little while before running downstairs. He got the box that he was looking for and as he opened it the door behind did the same. He was stood there naked in front of Christy. His body was smooth and hairless from when he used to experiment with cross-dressing and he wasn’t the muscliest of guys. She quickly shut the door behind her. She was wearing a denim mini skirt with black leggings and a pink tube top. Her hair was down and she gaped as Josh spun around completely naked.
‘I’m so sorry! I was in the shower and I’d left the towels down here and…’ She cut him off before he could say anything else.
‘It’s fine!’ she cooed at him. She walked up and pecked him on the lips. ‘It’s just…I’ve never seen a man’s cock up close before.’ She gently ran a perfectly painted pink nail down his chest to the base of his now erect penis. ‘I don’t want to rush things though.’ She said letting go as if awakened from a trance. ‘Dry off, get dressed and we’ll empty the rest of these boxes.’
As Josh turned around Christy couldn’t contain herself. She crept up behind him, placed her hands on his waist and kissed his neck sensuously. He stopped searching for a towel and let her spin him around as she pulled him into a French kiss. She knelt and wrapped a hand around his now fully hard cock and started to stroke it. Josh stumbled back as pure pleasure ran through his body. She put her lips to the head and gently ran her tongue over it. He ran his hands through her hair and used all his will power to pull her up to his level. ‘Is this what you want? We’ve only just met.’
‘I know, I just wanted to try it.’ She blushed slightly and turned away. Josh pulled her back around and hugged her before taking her upstairs. He towelled off and slung on some boxers. ‘Can you wear just those whilst we’re inside?’ She giggled. Josh thought for a moment. He was still very hard from her tongue and it was very noticeable. ‘I’ll do the same.’ And with that she was sliding out of her tube top and skirt. All that was left was a pair of pink ruffle knickers and a matching bra. The knickers were home to a penis that was just as hard as Josh’s but a bit longer, straining to get out.
After they’d fooled around a little, rubbing the other through the fabric of their clothes, they unpacked the remaining boxes. They chatted as they did so. Christy was asking if Josh had liked the shorts he slept in. He had to confess that they were much comfier than the men’s shorts he was used to. Then came a rapid fire of questions about his sissy fantasies. When it started, what he liked, what he didn’t like, if he had any clothes and whether he’d like to do it someday.
It had started when he was about 14 and experimenting with wigs and pretty skirts but hadn’t done anything like it for three years. He loved pretty much anything about it except for forced bi. He didn’t want some guy coming in acting like he was his bitch. The clothes he’d ever had he had thrown out for fear of being discovered and he’d love to do it some time.
She listened intently, it was evident she was interested. ‘So you never had anyone help you or spoke to anyone about it?’
‘Nope, you’re the first person I ever told.’ He replied.
She thought for a moment and then had an almost evil grin on her face. ‘We should get dressed and get some basics for you!’ They both got dressed and walked out the building hand in hand. Josh wanted to get some food and new kitchen gear. So Christy took him to a few shops in the local area and showed him the way around the city. He loved it here. There was always something going on. Street performers or parades, just something. They got to know each other even more. They kept clicking together and just loved spending time with the other. Truth be told, they were both starting to love the other. It was a relationship they dreamed of. After a bite of lunch they walked back through the park again.
When they got back, they put everything in its place and sat down on Josh’s couch to watch some TV. The credits were rolling on an episode of friends when Christy spoke. Her head was resting on Josh’s chest and a hand was by her face. ‘I’m falling in love with you Josh. I know it sounds stupid but you’re perfect.’ She nuzzled into his neck.
‘I was worried you didn’t feel the same as me. I’m falling in love with you too. I have not once in my life felt so happy.’ They kissed and they took each other’s tops off and threw them on the floor. Next thing they were on the floor unbuttoning their denim. They rubbed each other through the fabric until they were both fit to burst.
‘I want you inside me.’ Christy said as her neck was being kissed. She undid the back of her bra and released two huge breasts. They were pert and firm and she guided Josh’s lips towards a nipple and he sucked and licked and bit at it until she was moaning with pleasure. She rolled over and pulled down her panties revealing her eight inch cock and ass. She pulled down his boxers and spat into her hand. Rubbing her saliva all over is cock she directed it to her ass. ‘Stuff me Josh. I want to feel your hard cock pushing into me!’ She moaned as his head penetrated her. It was tight but clearly had been loosened by the ‘toys’ she kept. He started off slowly but built up a strong steady pace.
‘That’s it baby, pound my ass!’ She screamed as Josh kept going. Christy spun round onto her back so she could see him as his cock slid in and out of her. Josh had only ever masturbated and never used a flesh-light let alone a woman. This felt amazing. He kept going for what felt like seconds but must have been ten minutes. As he thrust he felt her cock banging against his abdomen which drove him even crazier.
‘Oh God! I think I’m going to cum!’ He groaned as he approached orgasm. He didn’t stop but just kept going. He shot the biggest load right in her tight ass. She groaned as she felt the warmth fill her up.
‘Oh baby. That feels so good!’ She closed her eyes and gently moved herself slowly up and down the shaft. ‘Have you ever taken something up the ass before? Like this big cock?’ Josh shook his head, a little nervous as to what would happen next. ‘In that case I won’t start you off with this.’ She said tapping the head against him and smiling. ‘But I’d like to cum too’ She ran a hand on his cheek. She slid him out of her and sat on the couch so that her cock was just below his face. She placed her hands behind his head and guided him towards the shiny pre-cum that had emerged.
‘I want you to suck my cock. Will you do that for me?’ Josh practically leapt at the chance, gently licking up the cum that was already oozing. He’d watched plenty of porn in his life so knew how to give as much pleasure as he could. He gently ran his lips to the base and tickled her balls with one hand whilst squeezing a nipple with the other. As soon as he started Christy couldn’t manage words and all that came out were gasps and moans as he sucked at her huge hard cock. He worked the shaft with his hand as his tongue played with the head. Though he’d never admit it, the taste of her juice was delicious. He’d experimented with CEI before but it had never tasted this good. He lapped it up like a little cat and stared at her beautiful face twisting as shivers went up her body.
He worked it hard and fast and she came closer to the edge until she burst. A deep moan was let out as her cum filled his mouth. She leant backwards, breathing heavily. She lifted his chin and ordered him to open his mouth so she could see her juice. He obliged and she dipped a finger into her massive load. She pulled him into a kiss and the cream flowed between their mouths in an intense moment of passion. ‘Bottoms up!’ She smiled and let it all drop back into his mouth. He gulped it down. It was warm on the back of his throat but he drank the whole load and kissed the head of her cock as he rose and sat next to her. ‘That…was amazing.’ They kissed again sharing the salty taste whilst holding each other closely.
Josh took Christy’s hand and led her to the bathroom where they shared a shower. They rubbed oil onto each other. Kissed and caressed. When they were done they both dried off. ‘Want to come over to mine for the evening? We can order some food in if you like.’ She offered.
‘Sounds like a plan! What time?’ He asked.
‘Now silly! I have something I want to show you.’ She smiled and slid her tube top back on. And buttoned up her skirt. ‘So what do you say?’
He’d seen the city and knew his way around close enough for the two days he’d been there. He knew no one else and he’d just had sex with the one he loved. He was not going to miss one second with her. ‘I wouldn’t miss it for the world.’ They Eskimo kissed and they went back across to her apartment.
Josh sat one of the fluffy chairs in the lounge as Christy told him to whilst she went next door. She came back with a small box and a big smile on her face. ‘Now I could tell by the way you talked about it that you still wanted to be a sissy so I’m going to help you! I still want us to be together as a couple no matter what and I thought it would be fun! So strip bare and let me see you!’ Josh stripped down and revealed yet another erection. ‘To start with I want to be able to make you feel as good as you made me feel earlier so that means training your ass to take a big cock like mine. So I have this.’ She pulled a thin but long black butt-plug out of the box. ‘You know what this is, don’t you?’ She said seductively. A bottle of lube was produced next and Josh was pulled across the coffee table as Christy started lubing up his tight sissy hole. She gently eased the plug in. ‘How does that feel sweetie?’
‘Really…uh…good!’ He groaned as the end was pushed through.
‘We’ll work you up to bigger ones gradually! I’m so excited! I thought you might like to cover it in these.’ She pulled out a pair of ruffle knickers like hers earlier but these had a slit at the front. She slid them up his legs and they felt so good. ‘That’s right your sissy clit goes through there.’ She put his longing cock through the hole and gently rubbed it. She gently spanked him once and then pulled up his jeans and buttoned them, rubbing his hard cock through the zip.
Christy phoned up a Chinese take-out and ordered a wide selection of dishes. They sat down and watched a repeat of Friends in each other’s arms. The doorbell rang and Josh stood up, feeling the plug move slightly inside him, answered the door and set out the food on the table. They split it onto two plates and sat down to eat. They chatted and laughed, they joked and flirted. It was like they were meant to be together.
‘I want to make you a full on sissy. Just for tonight!’ It came out of nowhere and Josh went bright red. ‘I really want to try it!’ She gave him a seductive smile and gently ran her bare foot up his leg and rubbed it against his knicker clad crotch.
‘I’d like to try that too.’ Josh replied.
Christy jumped up like a school girl and ran upstairs. She came back with a big metal case that she placed on the floor and opened it out. It looked like a corner cupboard and inside one half was coated in small slim draws and the other had two doors on it with shelves behind them. The lining was red velvet with a slight red fur trim. The draws were filled to the brim with make-up of all colours and varieties. There was everything from eye-liner to lip gloss. There was glitter in some, others were more gothic style. ‘To start with, I’m going to ask you to strip except for the pretty panties. We’re going to make you so hot!’
She started by opening the cupboards and took out a razor and some cream. She pulled the knickers down and sprayed some foam onto his pubic hair. She pushed him against a wall and ran her tongue around the head of his cock. She took the razor and gently moulded his pubic region. When she was finished a neat little heart was there right above his sissy clit. She then went back and exchanged the razor for a tube of pink liquid. She squeezed some onto her hand and gently massaged it into the heart. The light brown hair quickly turned into a pretty neon pink fur. ‘There! Already a mark to show that you are my little sissy boy!’ She tickled his balls a little and tongued him again. ‘No other hair either! You were born for this sweetie.’ She held his chin and kissed him. ‘If you’re going to be my sissy though, you need a sissy name! How about…Victoria? No! Tori! That’s perfect! My little Tori Heart!’ She gave a giggle and pulled the panties back up.
She told him to stay there whilst she dragged over a stool and the case. She started with some foundation and then spent about twenty minutes on her eyes. Everything had to be pink. She thought as it was the first time this sissy would be here, it should be in style. Then eyebrows got plucked and thinned and then a little bit of blusher on the cheeks.
Finally came the lips. She selected a bright pink that would match his dyed hair and added generous amounts of gloss to make them absolutely irresistible. Christy held out a tissue and made him lip bite onto it which left a pink lipstick mark that for some reason made Josh’s cock harden in his lacy sexy knickers.
‘There we go! You look just amazing my little sissy slut!’ She returned the shelves and boxes of make-up to the case and returned with a blonde wig. It was very long and rested about three inches above the back of the frilly knickers and as he swayed his head, the hair shook out and tickled the lower back. ‘Oh wow! You even shake your hair out like a girl!’ Christy chuckled. ‘I think we’re going to start off in some casual clothes so follow me up to the bedroom Tori!’ a subtle wink followed the instruction and they walked up the stairs to the balcony bedroom.
When she walked, Tori could feel the plug moving around, occasionally brushing past her prostate. With the knickers covering her clit, you couldn’t tell that she was actually a he. When they reached the top of the stairs Christy flung open a cupboard door and revealed a massive selection of female clothes. ‘I think your body would look good in these!’ A pair of jeggings were taken out and handed to Tori who put them on, adjusting them slightly over her knickers. ‘Hmm, I think a pink top is definitely needed. How about trying this on?’ She picked up a pink knitted top that had no shoulders and hung at the sides of the arms. It was slightly too shot to reach the top of the jeggings which gave the whole outfit a little bit of a slutty side.
Tori flicked her hair out the back of her top and shook it out which made Christy very horny very quickly. Whilst Tori admired herself in the long mirror on the cupboard door Christy started rubbing her own cock through the denim of her skirt. Tori turned and saw the horny transsexual and wondered over to her. She knelt at her feet and unzipped the denim skirt. The erect cock fell down and knocked Tori’s nose. With her new pink lips she kissed the base of Christy’s cock and left her lip marks. Christy ran her hands through the long blonde hair and directed the same pink lips to the head of the cock. ‘We’ll have to touch up your lips up after this, you’d best get the whole load in your mouth or we’ll have to start everything all over again.’
Tori took her advice and used her tongue and lips to work the head whilst both of her hands worked the big she-cock shaft. Tori’s hands could feel the cum building up as orgasm approached and teased her for as long as possible. Eventually there was no way of teasing the cock without sending her over the edge so Tori went frantically up and down the cock with as much speed and force as she could manage. The beautiful t-girl sprayed a massive load in her sissy’s mouth and, like earlier, kissed her deeply so that they could share the taste. Then Tori greedily gulped down the load and kissed each of Christy’s balls which made her shiver and thrust into her pets face a little bit. Whilst Christy recovered herself Tori slid her frilly knickers back up and did the denim skirt back up.
Christy sat on the foot of the bed and lay back panting. She glanced over at Tori ‘I didn’t think you could beat last time but my God, that was good. I’m impressed as well. You managed to give a blow job without ruining your make up! Well done!’ She beckoned for Tori to join her on the bed. The sissy lay next to her lover and rested her blonde hair on her shoulder. Christy placed an arm around her new toy and placed her chin on the wig. It was strange, they’d only known each other for two days but neither had ever felt closer to someone in their lives.
‘I think I love you Josh.’ these were two words that Christy had never thought to come out of her mouth. ‘I know it sounds ridiculous but you’re the perfect level of kinky and submissive, you’re sweet and kind and I just love you.’
Josh had only said that to one other girl but this was different. ‘I love you too. I’m not saying I’m in love with you but you’re amazing.’ He looked up at her and rested his chin on her chest. ‘I think you’re lovely and generous. You’ve guided me into a world I never have gone into on my own, you’re always teaching me new things and most importantly, you’ve got huge breasts and a massive cock!’ The last part was a joke and they both giggled and pulled into a lovers hug.
They stayed in bed, both looking slightly slutty, and fell asleep. It was a perfect night’s sleep and they stayed in each other’s arms until dawn came. Tori woke first and lay next to Christy just staring at her natural beauty. She sat up and saw herself in the mirror with, amazingly, still perfect make-up and hair. The long blonde locks were very realistic and when she ran a hand through it she looked like a porn-star. She walked over and knelt with her legs spread slightly. Her cock started getting hard and the jeggings framed it nicely producing a long tube underneath the material.
With one hand Tori ran a hand through her hair and with the other she rubbed her cock through the material like a woman would. The hand in her hair slid underneath the pink top and started playing with a nipple. After ten minutes of pinching at nipples and rubbing her stick, she stopped and admired herself in the mirror. Add some fake breasts and there was a real woman there. Tori hadn’t noticed but Christy was up and staring at her. Naturally, Tori blushed heavily when she saw her lover looking at her as she was trying to be a sexy little girl. Christy broke out into a smile, stood up, and took Tori’s hand downstairs.
They sat at the breakfast bar and tucked into some croissants as they discussed the day ahead. ‘I thought we could go out today. Maybe see a movie or something?’ Christy asked as she took a bite of delicious pastry. ‘I have a few girlfriends I’ve been meaning to catch up with. The way you look and walk I really think you could pass for one of the girls! If you want to that is?’
She couldn’t believe it herself but there was absolutely no trace of Josh left to look at. Tori really did look like one of the girls. Putting on a slightly more feminine voice she said ‘I’d love to. That would be great.’
Christy looked shocked at the voice that she had just heard but then smiled and pulled Tori into a hug. ‘Yay! We’ll pick you out a lovely outfit! I’m thinking maybe a plaid skirt and a white sweater top? We’re going to be the hottest couple around!’
They finished their breakfast and they sat on the couch together. ‘Sweetie, you know that plug I put in yesterday? Well it came with this.’ She pulled out a rubber tube and pump from the side of the cushion. ‘Can you get on all fours and stick your perky little ass up for me?’ Tori obeyed and rested her forearms on the floor and pushed her sissy hole in the air. She really did look like a slut.
Christy pulled down the jeggings and knickers to reveal the plug. There was a screw connection that the tube connected to so she screwed it in. ‘This pump will expand the plug and make your ass hole bigger. That means that if you take it well, you could be getting my cock in there soon!’
‘Oh God, really? I would love that!’ Before she had even finished the sentence Christy was pumping furiously filling the plug with air. Tori gasped as, for the first time, her ass was filled completely and then some. After a few moans caused by the new sensation, and a few minutes of pumping, the process was complete.
‘How does that feel? Good?’ Tori nodded, biting back the urge to yell out in pleasure and a little pain. ‘I just want to work it in a little more’. Christy started shaking the ass and gently spanking it causing more pleasurable noises. The plug was now about four times the size it was earlier and Tori was doing remarkably well considering her virgin ass. ‘I’m going to leave it in there for a few hours and then we’ll see how you feel, OK pet?’ she stroked the sissy hair and kissed her cheek. She then helped her up and sat her down on the couch again.
After a little adjustment and fidgeting Tori was able to find a comfortable position that she could happily cuddle up next to Christy. They spent the day relaxing and watching TV, occasionally kissing and fooling around. All the while Tori’s ass was stretching out.
Eventually, Christy removed the plug and at about five in the evening Christy took Tori upstairs and got her dressed in a pink plaid skirt with white tights on and a white sweater top. She handed her a pair of pink patent flats as well but when Christy observed she knew something was missing. After a moment’s thought she clicked and realised that the hair didn’t quite gel with the outfit. She tied it back in a long ponytail and clipped a flower of the same pink as the skirt to the side of her hair. She looked like a she. It was unbelievable.
Christy had decided to don a pair of skinny jeans and a pink tube top that complimented the darker pink of Tori’s skirt. A pair of heels was taken from the bottom of a cupboard that was the same pink patent that Tori wore. When they stood next to each other, Christy was about three inches taller than Tori.
They headed out and met Christy’s friends outside the theatre and after introductions; they headed inside and watched a romantic comedy that had just been released. About thirty minutes into the film Christy reached a hand over and started rubbing the sissy cock through the skirt as a sex scene came on. The man was muscly and handsome and very powerful and the woman was a blonde bending over and let him fuck her really hard.
Tori glanced over her lover and could see she was very turned on. Christy’s two friends were making out next to them too. Tori hadn’t realised they were lesbians. As the sex scene got more intense Christy rubbed harder and faster. Now that she was so horny, she wanted to repay Christy for the attention he was getting. They were on the back row of the cinema and they were on the earliest showing so the place was pretty much empty except for a couple on the front row.
Tori mounted Christy and kissed her deeply ‘I want to do something wild!’ she whispered. With that, she unbuttoned Christy’s skinny jeans and pulled her knickers across to let the hard cock ping up. Christy was even hornier now and started biting at her neck and running hands up her top to pinch at the nipples. Tori hoist up her skirt and slid the tights and knickers down. There was a copious amount of pre-cum on the tip of the aroused shemale cock. This was used by Tori to rub around the rim of her sissy hole to lube it up a little.
It was just under two inches in diameter and a little larger at the head which was now popped inside the hole. If Christy’s tongue hadn’t been gagging her, Tori would’ve yelped as she was stretched properly. Still lip-locked, Tori slowly lowered herself onto the cock. The feeling was amazing, the butt plug was nothing compared to this. The head pushed against her button and she slowly started to raise herself up and down.
Christy’s two friends had stopped kissing and stared at the real sex scene as they slid their hands down their partners skirt and started massaging the others pussy. Seeing this completely hormonal scene caused a feeling in Tori that ignored any pain she may have felt and replaced it with pleasure. She bounced up and down on the cock loving every second of it watching her own smaller dick bounce up and down.
Christy’s friends reached orgasm for the first time as Christy took hold of the bouncing stick and started vigorously working it with both hands. Tori came close long before Christy, because her movements were slower, but Christy just kept edging her cock closer and then leaving her for a moment to calm down before continuing.
Tori kept pushing down on the cock until eventually Christy’s body went into spasm and she tightened her grip on her girlfriend’s cock and worked it until she blew a load too. Tori sprayed all over her own chest as she felt Christy’s sweet jizz fill her tight ass. The warm liquid was completely new feeling. It was perfect and she never wanted it to stop. Tori used her fingers and cleaned up the cum on her chest. She licked of a little herself, savouring the taste of it in her mouth and the feel of it in her ass, and then gave some to Christy.
Christy pulled out and helped Tori clench to keep all the cum up there. Tori collapsed between the legs of the one she loved. ‘There’s no turning back now my sweet.’ Christy whispered to her. ‘You’re going to only crave cock from now on.’ It was true. All she could think about was doing it again.
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This was one of my favorites to write! Thank you Goddess!
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