5 comments/ 18414 views/ 11 favorites A Journey to Womanhood By: brendachaplin2000 John always knew he was different to the other guys in his sixth form class, though he managed to put on a good front to convince them he was a warm blooded 18 year old guy. He dated several girls and even bedded a couple, but deep down he knew he wanted to be one rather than date on. Only one other person knew of John's desire and that was Kathy. She has been one of his best friends since primary school and were closer that siblings. Most people assumed that they would one day be a couple. From a young age John had a desire to be a pilot. Both He and Kathy had joined the air cadets and were working in the sixth form towards their goals of a pilot and engineer. Since turning 17 they had both switched to a supervisor role of their local squadron until they finished the school and moved to university. John was 16 when he confided in Kathy of his other desire and shortly after their 17th birthdays (they were born only 4 days apart) Kathy had helped John transform in to Samantha for the first time. When dressed as Sam, John felt complete. They'd hang out at Kathy's whilst her folks were at work. They had even ventured out into town on a couple of occasions. So now at 18 and a half years old John could easily transform himself in to Sam without Kathy's assistance. One Saturday every month John would catch the bus to town and head to a disabled toilet and transform himself to Sam and go shopping. Several times they went clubbing as Kathy and Sam. They had turned a few male heads, but Sam was scared so rebuffed most male attention. She did have a drunken snog with one college guy, but Kathy got Sam out before she went too far. These little excursions as Sam help subdue the desire to be a woman for John but he knew deep inside that he really was Sam and John was just a mask she wore for the world. His parents were middle class liberals and he had an older brother at university. He was scared to reveal himself in case they rejected him. The life of John was about to take an unexpected turn of events. One Saturday he was out clubbing with Kathy dancing the night away as Sam when she felt a tap on the shoulder and a voice ask "John is that you" panic and horror shot across her face as she turned to see Jeff one of her brothers best friends. Jeff could see he had caught her as a deer in some headlights. Sam welds up and ran. Jeff and Kathy caught up with Sam and Jeff apologised for surprising her. That when in a small quiet bar with secluded lighting. Jeff got some drinks in and they sat around a table chatting. Sam explained her situation and Jeff said he was cool with it and promised not to tell anyone and if she was in trouble just give him a shout. For the next hour or so that just had a normal chat about life, school and other things in general. It was clear to Sam that there was a lot of flirting between Jeff and Kathy so she decided to call it a night around 9pm. As she stepped outside, she closed her eyes and took a deep breath and relaxed with the joy of having good understanding friends. Just then there was a tap on her shoulder and another familiar voice called her name. John, John Knolls? Mark Harris was an English teacher at the school John Knolls attended. He was 28 years old and been teaching for 5 years. During a lads weekend to the Manchester Mark discovered tgirls and when he had the chance he went back alone to cruise the bars. He managed to pick up tgirls regularly and enjoyed his sexual encounters with them. In his 5th visit he hooked up with another girl who thought it would fun to dress him up for sex. Some Mark had need transformed into a tgirl and was christened Maria. That night she lost her virginity and from that time on, every time she returned to Manchester she would stay at her "aunts" and spend the weekend as Maria. They would cruise the bars and pick up guys. Mark still slept with really girls, but he also loved to be taken as one. He had noticed John around school, but when Jeff Thompson and Kathy Turner sat down at the table next to his with a mystery blond he could not help but overhear the conversation. He was more shocked to hear that the beautiful blonde was John Knolls. When John or Sam as he discovered his female name was getting up to leave, he just had to follow her out. Outside for the second time that night Johns heart dropped in horror at being recognised for the second time that evening. Mark said he would like to talk to John and he hailed a taxi down. In a daze Sam got into the cab and Mark told the driver his address. Sam sat in silence as the cab made its way out of the town centre to a suburban area not far from John's house. The taxi pulled up outside a semi detached house on a quiet street. Mark paid the driver and opened the door for Sam. Once inside Mark offered her a seat and headed to the kitchen a returned with a bottle of red wine and two glasses. She poured a glass and offered it to Sam and sat at the other end of the sofa. He turned to and could see she was frightened. Mark gave a reassuring smile and told her not to worry, he just wanted to talk. Sam has a sheepish smile. Mark decided the best way to help her relax was for Sam to meet Maria. He excused himself and head up to his room. Sam thought she was in deep trouble and took out her phone. But who to call? The police, her folks or Kathy. Mr Harris had technically not done nothing wrong, he did not force her into the cab and she could just get up and leave but something told her to stay. She thought she might be dressed as a girl but she could defend herself if need be. After 10 minutes the living room door opened and a woman walked in. She had long brunette hair, light makeup and was wearing a red dress and matching heels. She held her hand out and introduced herself as Maria. Sam stood now understanding Mr Harris's interest. She stood and shook Maria's hand and introduced herself as Samantha, Sam to her friends. They sat down and the conversation was relaxed and free. Maria asked Sam about her life. How long she had been dressing, did she like boys or girls and had she done anything with either. Sam answered honestly that she had been dressing since she was 16, she had dated girls as John but was still confused as Sam. And that she had slept with two of John's girlfriends and only kissed one guy whilst drunk. Sam asked Maria her story. She had been dressing since she was 13. When she went to university, she purged all her female attire and for 3 years live totally as a man. The desire was always there but she managed to suppress the feelings. After a lads weekend away to Manchester she saw the TV scene was large and the next weekend she went back alone and cruised the bars and picked up a tgirl for the first time. Maria then went through a phase of dating tgirls but one asked if she wanted to dress and without too much pushing found herself back in woman's attire. The tgirl was a little older and Maria called her "aunty" whilst aunty tutored her in hair and makeup and they hit the bars together while dolled up. She explained as Mark she was a heterosexual man who had sex with girls. Even those with a little extra but always the Dom and the top. As Maria she was a submissive bottom. Maria only comes out to play whilst at home in private or hitting the clubs with her tgirlfriends. Sam listened with amazement. Maria said that Mark would love to take her to bed, but Maria wanted to be her friend and guide. Sam was flattered and a little scared and thanked Maria. The hour was getting late, so Sam excused herself and headed to the bathroom 10 minutes later, John returned dressed in his male clothes. John sat down to finish his wine and he felt the heat from Maria's bare leg next to his. Maria could see the lust in the boy's eyes and leaned in and kissed her. Locked in an erotic embrace Maria rubbed John's cock through his black jeans. Soon she fished it out and took him into her mouth. John's head was in a spin from the wine and the sensations from his cock as Maria expertly bobbed on his cock. Maria pulled off his cock and stood up. She lifted her dress and John noticed she was not wearing any underwear. Her hard cock was pinned to her chest by her garter belt. She straddled John and lowered herself onto his erect member. John was surprised that he slid into her so easily. Maria whispered I lubed myself up when I changed just in case. As they kissed Maria rode John's cock slowly picking up the pace until she blew all over her stomach. The set John off and fire 4 good loads into her bowels. After Maria regained her composure, she climbed off of John's lap. She smiled and said sorry, could not resist. John said no apology needed she was the sexiest woman. Maria help clean up John's lap And fastened his jeans. Maria told him he could hang out with her house as Sam anytime and he did not have to feel an obligation to let Mark have his way with Sam though John was always welcome for good times with Maria. John thanked her with a kiss and left the house for the 10 minute walk home. On the way John wondered what life was going to be like now, two others knew his secret. The house was quiet as he got home. He stashed his bag under his bed, stripped off his boys clothes and his girlie undies and put on his Pj's. As he drifted off to sleep, he wondered what it would be like to taken by a man. Maria certainly enjoyed it. The following Monday John caught up with Kathy and they discussed the events of Saturday night. After Sam had left Kathy and Jeff chatted and he escorted her home. He took her out on the Sunday and ended up with a kiss at the end of the evening. John explained his adventures with Mr Harris and his alter ego. Kathy was surprised. John went to Mark's office during a free period. At first Mark seemed nervous as the gravity of the events hit home. John gave him a reassuring smile and said he had enjoyed Maria's company and hoped the next time she went to Manchester Sam could go to. Mark beamed a big smile and said that would be great. That evening John and Kathy were decked out in their RAF cadet uniforms for roles as officers at the local air cadets. After Jeff picked up Kathy and John started to walk home. He noticed he was not far from Mark's house so texted to see if he was in. Mark replied that he was and John was free to pop round. John knocked on Marks door and was greeted by Maria. She let him in and said she always loved a man in uniform. Maria took John's chin in her hand as she removed his peak cap and moved into brush her ruby red lips to his she broke the kiss and lead him by the hand to her bedroom. She pushed him onto the bed and tore at his royal blue uniform trousers. She reached in and pulled out his cock and sucked the length, expertly into her throat as she bobbed on his shaft her hand massaged, is balls and she slid a sly finger into his ass. This pushed him over the edge and he shot 5 ropes of cum down her throat. He went dizzy for the intensity of his orgasm. Maria climbed on top of him and joined her mouth to his spit balling his seed between them. As they lay side by side, resting Maria stroked John back to life. She told him to take her and climbed onto her hands and knees and presented her arse to him. He discarded his uniform tunic and trousers and loosened his tie before lining up at Maria's hole and pushed his cock into her accepting sphincter. Soon he was balls deep within her and started to fuck her long and slow. She turned and told him to fuck her harder. John picked his pace up to a face assault on Maria's rosebud causing her to pant with excitement. After a few minutes John pulled out and turned Maria on to her back and feed his cock back into her with her legs on his shoulders, his assault was almost brutal on Maria's arse but she loved every second of it. Soon she reached her own climax shooting cum onto her belly. This sent John to the brink and he deposited his second load of the evening into Maria. John withdrew his spent cock and licked Maria's seed from her belly and shared it with a passionate kiss. After a quick cuddle Maria help John redress. As they headed back downstairs, John said that Sam would love to try that with Mark soon. Maria winked and said that she and Mark had a thing for uniforms. John smiled and said that could be arranged. With that they shared a quick peek on the cheek and John headed home. A Journey to Womanhood Pt. 02 John had a normal week at school and was pleased to hear Jeff and Kathy were getting serious as a couple. John had not visited Maria since the Monday night after cadets. By mid-week, he had decided to pay Mark a visit as Sam and texted him that she would come round and visit on Friday night but she could not promise him anything as she was still nervous. Over lunch on Thursday John and Kathy chatted about their weekend plans. Jeff was taken Kathy out clubbing Saturday night and Sam was welcome to join them. John thanked her but declined the offer and told her his own plans. He mentioned that Mark liked a girl in uniform and asked if he could borrow her old school uniform. As sixth formers, they were only required to dress smart. Kathy with a show of concern asked if he was sure he was ready for that big a step. John assured her that Sam was not going round to Mark's house dressed as a schoolgirl but if events lead to some bedroom action then he wanted to have a little surprise in his bag. Kathy agreed to let him have her old uniform and asked him to just be careful. After school, they headed back to Kathy's to hang out together since Kathy's mum worked late and her dad left them years earlier. As was traditional in these hangouts Kathy made some food whilst John headed up to her room to change into Sam. Kathy did not mind sharing her wardrobe with Sam though they had purchased Sam her own underwear. When Sam came down to join Kathy in the kitchen she surprised Kathy by wearing her full air cadet uniform. Kathy giggles as she was used to seeing John wearing a similar male version of this outfit but never imagined seeing Sam in it. Sam got all serious and said she would love to be able to actually wear this in the service. Sam always felt like a dirty little secret that had to be hidden in order to protect John's dreams of becoming a pilot in the RAF. Kathy gave a reassuring smile and said that maybe society would be more accepting. Sam then popped back upstairs and returned in a more causal skirt and T-shirt combo. Kathy had alway noticed the differences between John and Sam. As John, he was one of the lads but she knew him well enough that it was a strained act. Only when Sam appeared did the true person come out. At this stage in their friendship, John did not need to have a dress on to be Sam around Kathy. They could chat for hours about things girls their age chatted about and as soon as someone else entered the room Sam would disappear. Kathy hoped one day John could be Sam full time. On Friday John went straight home after school and stripped off his suit, shirt and tie and hit the shower. He kept himself hair free except for a neatly trimmed bush above his penis. He had done some research on how best to prepare himself should he go all the way with Mark tonight. He had purchased a bottle of love lube from the supermarket and fashioned an improvised enema kit from an old pop bottle and some old hose. He filled the bottle with some warm soapy water and lubed up the end of the hose. He put it to one side and lubed up his finger and started to work one into his virgin rosebud. To date, he had never played with his butthole and never inserted anything up there except the occasional finger. After several minutes of stretching, he slowly feeds the hose into himself. When he had several inches within himself he upturned the bottle and squeezed the contents down the hose and into his bowels. He felt the warm liquid fill him. When he felt full he removed the hose and fought the urge to let the water out. He dance around the bathroom for several minutes both to help the water clean his insides buts also he need to evacuate his bowels was becoming intense. He sat on the bowl and with several un-lady like noise filled the pan with brown water and chunks of shit. For good measure, he repeated the process and he felt his back passage was clean as it would ever be. He went to his room and his secret stash of Sam's clothes and picked out his outfit for the evening. He chooses an above the knee sleeveless Sumer dress and lemon yellow half cardigan with 1" yellow heels. He folded the outfit carefully and placed it in his rucksack along with Kathy's school uniform. He painted his toenails red and put his makeup back inside his rucksack. He threw on some boy clothes and head out to the brush land near his home. There he stashed his bag in his secret hiding place ready for later. He returned home and did his homework and watched some TV his folks were home around 6 and he left home at 6.30 to get changed and be at Mark's for 7 pm. Returning to his hiding spot, John grabbed up his belongings and headed to the local toilets. He managed to get hold of a radar key that lets him into any disabled toilet in the country and slipped inside unnoticed he locked the door and hung his dress on be back of the door so the creases could fall out. He then stripped off his boy clothes till he was left in only his panties. He slipped on his bra and stuffed the cups with his breast forms and pulled a full slip over his body. He loved the silky feeling as it cascaded down his body. He lifted the hem of his slip and pulled his Panties down so he could tuck his manhood back and away. The first time he pushed his testicle back into his body it was awkward and hurt like hell, but now he was a seasoned pro and the popped back in without any problems. Smoothing out his slip, he took out a makeup bag and made up his face with a medium level of makeup. He liked the smokey eye look and had spent hours on YouTube perfecting Sam's look. He painted his nails to match his toes and sat on the loo texting Kathy reassuring her he was ok. With her nails done he slipped on his dress and slipped on his heels and put his wig onto his head and Sam had arrived. A quick touch-up on the makeup Sam put all her things away and put her money into her handbag and fired off a picture to Kathy. Kathy replied she looked stunning and wished her lucky. She threw the rucksack over her shoulder and left the toilet. The walk from the park to Mark's house as not long and Sam knew she was completely passable though she did stick to the back streets as best she could. She rang Mark's doorbell and he answered wearing a Hugo boss suit dark blue with a white shirt and matching blue tie. He compliments Sam on her outfit and she told him he looked handsome. She was surprised when she saw he had laid out a dining table and he escorted her to her seat. He gave her a glass of wine and turned on so soft smooth music. He headed to the kitchen and brought her a plate of food. Even though she had eaten and was nervous she was very hungry after the enema earlier. They chatted about general things as if this was the first date in a fancy restaurant. This was the longest Sam or John had spent time with Mark outside of school. Sam was amazed that only a few nights ago this handsome strapping man was dress as a sexy woman with John's ball slapping her arse. After dinner, they remained at the table and Mark placed his hand on top of Sam's. This sent an electric shock throughout her body. John looked deep into her eyes and softly said that he was not here to start a relationship with her, the age gap was too big for any long term thing. He was happy to have fun and be a mentor to her as she explored her female side to the fullest. He said that she was beautiful and sexy. He finished up by saying that if Sam wanted more than friends with benefits then they should not take things further. Sam said she understood and agreed that she was not ready for anything but someone to help guide her in a safe environment. Mark cleared the table and Sam sat on the sofa sipping her wine. When Mark returned he turned up the music and held out his hand for Sam to join him for a slow dance. Sam felt safe in his arms as he cuddled her close to his chest. She felt the first signs of stirrings in his trousers. She looked into his eyes and said are you trying to seduce me, Mr Harris. Mark smiled and replied is it working Miss Knoll's. Sam smiled and kissed him on the lips. As they slow danced their tongues explored each other's mouths as Mark's hand wandered down Sam's back to her bottom. Sam had made up her mind that she would give herself to this man. To let him teach her what it was to be made love to like a woman. She broke the embrace and whispered into his ear that she was going to slip into something less comfortable. And with a wink she picked up her rucksack and headed to the bathroom. Once she was locked in the bathroom Sam took out the school uniform and laid it out in the toilet lid. She slipped her dress and slip off and admired her figure in the mirror. She pulled her hair back into a ponytail and picked up the white blouse. She fastened the cuffs and buttoned the front all the way to the collar. She cursed herself for bringing her yellow heels, but she was stuck with them now. She pulled on the grey box pleat skirt and tucked the blouse into the elastic waistband. Lifting the collar she threaded the green and gold striped tie around her neck and checked it for length. Even when she had to wear the male version of this uniform she was always dressed immaculately. Guess pride in a uniforms appearance was something she learned from being an air cadet. She knotted the tie into a full Windsor and put on the green pullover with gold accents around the neck and cuffs. Finally, she slipped on the matching green blazer complete with the school's crest over her left breast and completed with the same gold trim as her pullover. Examining herself again in the mirror she straightened her tie and was surprised how young the outfit made her look. She noted that should she wear this again to go easier on the makeup. With a trembling hand, she unlocked the door and with a deep breath opened it. As Sam entered the room Mark's back was to her. She tried to pose sexy with one hand on her hip and said hello sir. Mark turned mouth gaping at the sight before him. Sam trying to get into character said she had been sent to see Mr Harris for some sex education. Sam closed the gap between them and her lips met Mark's. Mark caressed her arse under her grey school skirt. Sam pulled away and reached for Mark's tie. She broke the knot and unbuttoned his shirt. She caressed his torso as she stroked his smooth body down to the waistband of his trousers she freed his belt and unfastened the button. Looking into his eyes, she lowered the zip and pulled the trousers down to his ankles taking his boxers with them. His hard cock sprang free and Sam took it in her hand gentle stroking it. Sam lowered herself to her knees and guided Mark's cock into her mouth. It took her a few moments to take him fully in. Mark help by giving her instructions on how to swallow as she sucked. Within minutes, she was bouncing her head like a pro on his shaft. She cupped his balls and massaged them with her hand. Mark let out a long loud FUCK and flooded her mouth with his seed. Sam slowed down her pace as she swallowed all his spunk. She stood and took a swig of her wine and with a wry smile told him she was not done with him. Mark kicked off his shoes and trousers as Sam watched on. Mark popped to the kitchen and returned with a shot glass and a bottle jäger bomb. Handing the glass to Sam, he poured her a drink. He explained that a couple of these would help her relax and loosen up for her first time. She smiled and downed the shot, Mark refilled the glass and she slung it down her throat. Sam found the warm tingly glow within her and her mind was focused on getting fucked. She took Mark's hand and led him to his bedroom and laid him on the bed. She reached under her skirt and removed her panties and seductively climbed next to Mark. She rubbed his thigh to his cock and stroked it back to its full hardness. The alcohol was giving her a good buzz and she felt like a real giggly schoolgirl. She leaned forward kissing mark on the mouth and told him to take her. Needing no further encouragement, Mark pushed her head into the pillow and lifted her arse into the air. Crawling behind her, he flipped her skirt up exposing her virgin pussy. He parted her cheeks and pushed his tongue into her aching rosebud. Sam purred and Mark assaulted her hole with his mouth whilst her own cock standing hard and proud. Mark inserted this index finger into her, the booze had helped her relax and she took his fingers easily. After pumping her with 3 fingers, Mark reached into his bedside cabinet and pulled out a bottle of lube. Pouring some down her crack, he pushed his fingers back in. Sam had never felt this good and ached for more. Mark did not disappoint as he withdrew his fingers and lined up his cock. He told her he would go slow and would stop if she wanted him to. Sam bit her lip and gave a quick nod of agreement. Mark pushed his enlarged head passed her sphincter and fed inch by inch his cock into her bowels. At first it felt like a fire had ravaged her arse but when the invader hit her prostate she gave a little moan. Mark remembered Maria's deflowering and the same moan leaving her lips. He wait a moment before pulling half way out and slowly back in. With only moans of ecstasy from Sam, Mark picked up his pace. Mark pulled out and turned Sam onto her back and lifted her legs over his shoulders. He slowly fed his cock back into her arse and resumed his rhythmic assault on her bottom her cock had grown to its full size and was lifting the skirt hem high above her groin giving Mark clear access. The sight of the prim and proper schoolgirl below him spurred him on and he knew he was close to cumming. Sam was panty and moaning with pleasure, she urged Mark to fuck her faster. She almost passed out when her orgasm hit. Without touch her cock she fired 5 long ropes of spunk into her skirt, as she clenched her arse it was enough for Mark to fire his load deep into her. Mark composed himself as he withdrew from her boy pussy and laid next to her. Sam final came down from her orgasm and turned to Mark, she said being the girl was far better than being the boy. Mark smiled and agreed. They laid together for a while and even fell asleep for a couple of hours. Sam awoke and saw Mark fast asleep next to her. She slipped out of bed and loosened her tie and opened her top button. She crept out of the room and headed to the bathroom. She turned on the shower and undressed. She took a tissue and wiped up her load from the skirt and flushed it down the loo. It was a good thing that Mark shared this bathroom with Maria since it was fully stocked with all she needed to remove her make up and assist her changing back to John. 10 minutes later John pulled closed the front door and headed home via his hiding spot where he stashed his two outfits from this evening. His folks were already in bed when he got home. He quickly changed for bed and laid there for a while replaying tonight's experience over in his mind. He defiantly wanted to be Sam full time but how to make it happen. A Journey to Womanhood Pt. 03 Two weeks had passed since Sam dressed up as a schoolgirl and was deflowered by Mark. Since then life had returned to relative normality. Since John was now deep into his final exams, Mark advised they cooled their fun as not to distract him. With the last exam passed there was a plan for an end of school party at one of the kids houses the following Saturday. John had not seen so much of Kathy since she started dating Jeff and he missed her company and arranged a night out just the two of them for Thursday night. It was also a rare occasion since John actually went out clubbing as John and not Sam. Over drinks, they chatted about their relationships and the fact that it had been over two weeks since Sam had come out to play. Kathy had sensed that John had been uptight recently but put it down to the pressures of the exams. The fact was he was in desperate need of a female release. The night with John re-enforced his desire to become Sam full time. Kathy just bluntly asked him why he did not just come out and be his real self. John dreamed of flying for the air force and did not want to jeopardise that dream. Kathy assures him that the military was more understanding these days, but John dismissed it completely as it was too risky. Kathy then said that John could come out to his family and friends and revert to boy mode for the airforce. Once his service was complete he could then have a gender reassignment and become a commercial pilot. John thought the idea through without commitment. The next day Kathy and John had agreed to enlist in the RAF. Both dressed in the dress cadet uniforms, they rode the bus into town. They spoke with the officer in charge who took them through the application process and said they would hear within two weeks if they had been successful in their applications. As they were in town they headed to a Weatherspoons pub for lunch. Over lunch, John declared that if he was turned down he would start his full-time transition into Sam. If he got in then she would remain in his closet. Kathy joked that when they got in she would donate her cadet uniform to Sam's wardrobe. Over lunch, John noticed some girls eyeing him up but now he had experienced sex as a girl he no longer desired them. On the bus home, he texted Mark to see if Maria fancied a visit from Sam, a girly night in. Mark replied that Maria would love that, but she was already away for the bank holiday weekend, but Sam was welcome to tag along. She would need to bring a bag for a 3-day trip as they would be visiting Maria's aunt in Manchester and returning late on Monday. John thought for a minute and replied asking what time did Sam need to be around his house. With times arranged John said his goodbyes to Kathy and they went their separate ways. Once home he filled his mum in on his enlistment and said he was going away for a couple of nights on a lads weekend away. Since he was 18 his mother did not mind. Up in his room, he packed Sam's bag and included her school uniform just in case as well as a couple of clubbing outfits. On top of this, he put his own change of clothes in for his trip home. He watched some tv before arriving at Mark's house. He was still in his work suit having just gotten home. Mark had his bag already packed and ready to go, but he needed to send a couple of work emails before they left. John took the opportunity to slip into the bathroom and change into Sam. Emerging 10 minutes later no trace of John was left as the teenage girl wearing a short floral summer dress exited the room the teenage boy had entered minutes before. When Mark came back from his home office he gave his seal of approval and took their bags to his car. Soon they were on their way north. Mark explained that they would be staying with his aunty, the t-girl who guided Maria through her early days. Whilst they drove Mark said he had been thinking and if he was to help Sam fore fill her promise of becoming a fully fledged t-girl then perhaps they should have a platonic relationship as mentor and student. Sam was sad to lose a fuck buddy but appreciated the Sentiment even more. It was passed 9 pm when Mark pulled into the driveway of a nondescript semi detached house in the suburbs of Manchester. Carrying their bags, he lead her to the front door and rang the bell. A woman in her late 40's answered the door, she wore a skirt suit with a cream Oxford blouse beneath the jacket. Once inside Mark introduced Sam to Elizabeth or Aunty Liz to Maria. The girls shared a hug and Liz showed her guests to the dining room where she had prepared a meal. Due to the lateness of the hour, Mark was not going to bother changing into Maria so close to bed time. Around 11 pm Liz showed Sam to her room, it was at this point Sam remembered that she forgotten to bring any nightwear. Liz pops to her room and returned with a short black camisole nightie the did very little to hide Sam's modesty. Sam felt sexy in the silky nightgown and was soon fast asleep. Liz went back downstairs and discussed what plan of action they would take with helping bring Sam out of her shell further. Sam awoke from a blissful slumber and notice that it was nearly 11 am. As she got out of bed she realised that though she had packed several going out outfits and one school uniform she had forgotten to bring any casual day wear. She pulled on some clean panties and head downstairs. In the living room, Liz was chatting to Maria both casually dressed in blouses and skirts. They greeted Sam and Liz popped to the kitchen and returned with a mug of coffee for Sam. Sam explained her problem and Liz said that it was a good excuse to go shopping though she thought Sam would look cute dressed as a schoolgirl around the house. Sam showered and dressed in a borrowed outfit from Maria of skinny jeans and tank top and met the other girls downstairs. Liz insisted they took the bus as parking was a nightmare and they headed to the Arndale centre. Sam wanted to go into Primark as she only had £60 in her bag, but Liz and Maria insisted on treating her to some clothes of better quality. The visited H&M, New Look and Next. By the time, they hit the food court Sam was loaded down with several bags loaded with outfits and shoes. Liz pulled out her phone and checked the events lined up in the city's transgender friendly clubs. She saw Napoleons was having a school disco night and after Sam admitting she had her uniform with her suggested they all got dressed up and attend the disco. The others thought it was a great idea and after lunch, the girls hit the department stores looking for uniforms for Liz and Maria. They managed to find a uniform similar to Sam's so they could try and match up. After the shopping centre, Liz took the girls to another part of town and knocked on the door of an end terrace house. A guy in is early 30's answered. Once inside Liz outlined that they needed some fake ID's for Sam. The guy was called Rob and took Sam upstairs to his office. He first off took some pictures of her as Sam and then threw her a shirt and tie and told her to man up. Sam was a little confused until Rob said he needed to make her ID as a man as well, so same went into the bathroom took off her wig, tank top and bra and put on the shirt and tie. Looking in the mirror, she removed her makeup and was amused that she was trapped half man half woman from the waist down. Back in Rob's office, he took some more pictures and took all John's details. Rob told her to get changed and wait downstairs for him. Sam went back into the bathroom and put her feminine outfit back on. Back downstairs Liz loaned her some makeup to fix her face. 20 minutes later Rob came down and handed Sam 4 ID's. The first two were for university of Norwich student passes one in Sam's name the other John's. The other two were Uk proof of age cards in both her names. Both cards made her out to be 22 years old. Liz slipped Rob £50 and the girls left and returned to Liz's house. After a coffee, the Sam headed upstairs for a shower and a laydown. After a long hot shower, Sam wrapped in just a towel laid down on her bed and drifted off into a restful nap. When she awoke she saw it was dark outside. And looked at the time on her phone. It was 19.15 so she sprung out of bed and pulled shut the curtains and turned on the light. She dropped her towel and fished out her outfit for the evening, and laid it out on the bed. First she put on the matching white bra and panties set and complimented it with a pair of sheer black hold-up stockings. She slipped the white school blouse over her shoulders and fastened the buttons, only leaving the top one free leaving the collar open. She stepped into the grey box pleat skirt and tucked her blouse in. Sitting at the vanity table, she did her makeup for a night on the town that would be a complete contrast to her outfit. With her make done, she pulled on her wig and brushed it out and tied it back into a ponytail. She fastened her top button and lift her collar, then reached for her tie. Levelling out the tie she expertly tied it in a full Windsor knot with the V just touching the waistband of her skirt. She slipped on her 3" black heels and picked up her blazer. She put her ID's, money and phone into her inside pocket, and checked herself in the mirror. Satisfied she turned off the light and headed downstairs. In the living room, Sam was greeted by Liz and Maria, both dressed in their school outfits drink a glass of wine. Liz had gone for the full school slut look. Her skirt was barely covering her panties, and her blouse were mostly unbuttoned exposing her lacy black bra. Her tie was tied loose and scruffy, hanging low. Maria was a little more conservative, with only her top button undone and tie hanging low. She also had worn her skirt shorter than Sam but was modestly stopping mid thigh. Liz poured Sam a glass of wine and they sat down. Liz got serious for a minute and told Sam if she pulled a boy she was not to bring him back to her house. She tossed a packet of condoms at her and told her always use one of these if you are not 100% sure your lover is clean. This was a sobering thought for Sam, but Liz quickly lightened the mood with a toast to a great evening. Liz and Maria put on their blazers, and the girls headed for the bus stop. Along the way, the attracted the attention of several motorist who tooted their horns at the girls. On the bus to the city centre, Maria asked Sam why she had dressed prim and proper. Sam replied that she did not feel comfortable wear the uniform and other was. Liz commented that she looked a perfect schoolgirl slut ready for plucking. Sam laughed that it was too late for that. In town, they headed to Napoleons and after a quick ID check, the girls were in. Sam had used her male ID as it was a transvestite night at the club and she would have been scrutinised more if she tried to pass herself off as genetically female. The club was full with t-girl schoolgirls of various degrees of passability, and their schoolboy admirers. Liz and Maria said hello to a couple of t-girls they were friendly with and introduced Sam. The first was called Crystal and was the typical image of what the public thought a tranny looked like. She was in her early 50's and wore the full St Trinians gymslip uniform, complete with straw hat. Sam wondered if he was in a dead-end office job during the week. The other t-girl was called Sharon, she was in her mid 30's and was rocking the goth schoolgirl look. They both made Sam feel welcome. It was still early and they found a table and had a few round of drinks whilst the evening livened up. Around 10.30, Sam noticed a couple of slutty girls escorted by a guy walk in. What drew her attention was he, like her, was dressed neatly. His collar was buttoned with a perfectly tied tie. He looked as if he had stepped straight out of a private boys school. Sam turned her attention back to the conversation at her table, but every now and then she glanced up and noticed the guy was looking at her. After a while, it was Sam's turn to get the drinks in and headed for the bar. As she waited for her order she saw out if the corner of her eye the guy standing next to her. She turned and made eye contract and smiled. He smiled back and leaned in so she could hear him over the music that his name was Phillip, and she looked very attractive. Sam introduced herself and they had a brief chat till the barman handed Sam her drinks. Just as she was about to leave Phillip asked her to dance. Sam thought why not and lead him back to her table and handed out the drinks. She took a quick slug from her vodka and Coke and let Phillip lead her to the dance floor. The girls made whooping noises as she left, and she shot them a bashful smile. The tempo of the music was fast, and there were plenty of dancers strutting their stuff. They danced for a couple of songs and Sam moved off to the side for a quick breather. Phillip stood beside her and the chatted some more. He was 24 years old and was attending Manchester university on a science course. Sam said she was 22 and was awaiting entry into the RAF. Sam decided to bring up the subject that she was not a 100% woman. Phillip or Phil was bi-sexual but preferred t-girls to full on men. The two girls he came in with are his roommate and his girlfriend, she was a t-girl admirer and loved her boyfriend dressing up. They danced a little more until Phil offered her a drink. He returned with a fresh vodka and Coke for Sam, and JD and Coke for himself. The DJ turned the tempo down and started the slow dancing music. Phil led Sam back to the dance floor and she slipped her arms around his neck as his found her bum. As they swayed they looked into each other's eyes and their lips met. Sam felt his hardening cock push against her as they slow danced. Her own cock was begging for release as their tongues danced between their mouths. Sam noticed Maria to her left slow dancing with her own schoolboy. After several songs Phil asked if Sam would invite him back to her place, Sam said she could not. Phil looked disappointed until Sam said he could invite her back to his. The finished their drinks, and whilst Phil said goodbye to his friends Sam told Liz she was leaving. Liz gave Sam a spare key, and told to have fun but be careful. Outside the club, Phil put his arm around her as they walked to the taxi rank. As they wait for a cab, Sam looked at Phil and confessed her real age. Phil kissed her saying that she was older than 16 and that was all that mattered. They climbed into the cab headed off into the night. The taxi dropped them outside the halls of residence for the cities university. Phil escorted her to his room. Once inside the small apartment, Sam sat on the bed as Phil fixed her a vodka and Coke. He sat next to her and they toasted to new friends and downed their drinks. Phil took Sam's face in his hand and kissed her tenderly on the lips. Soon Sam was laying on the bed whilst Phil's hand wandered up her grey skirt. He rubbed her swollen member through her panties, and she let out a long soft moan into his mouth. He removed his blazer and loosened his tie, freeing his top button. Returning his attention to Sam, he unbuttoned her blazer. He slowly unbuttoned her blouse, only loosening her tie to open her collar. He parted her blouse and lifted her bra and breast form up to reveal her natural nipple beneath. He took the nipple into his mouth and rolled it around his tongue. Sam whimpered at this new sensation. Phil slowly pulled down her skirt revealing her white panties. With the skirt discarded, he removed her knickers freeing her cock. Her took her into his mouth, and Sam almost came on the spot. Sam decided to take charge and pulled Phil off of her. She threw him into his back and wrestled with his trousers, tossing them to the floor. She took his cock into her mouth and gave him a sensual blowjob. She pulled off of him and reached into her inside blazer pocket and pulled out a condom. Phil looked disappointed, but Sam insisted. Rolling the condom over his manhood, she gave it several big spits of saliva. She straddled him and lowered herself onto his hard rod. She was relaxed and horny enough to accept his invader into her body. It was his turn to moan, as her arse swallowed him whole. As she started to ride his cock, she slid her blazer off her shoulders. Phil moved his hands under her blouse and caressed her belly. Sam loved the sight of her tie rising, and falling in unison with her strokes. Phil was memorised by the sight before him, and a sexy schoolgirl with a 6-inch cock riding him long, and slow. Sam raised her arms behind her head and stroked her neck as she started to get lost in the moment. Slowly she quickened her pace, making both of them pant as their climaxes approached. Phil fired first, filling the condom buried deep within her. Sam's own cock fired a ropey string of sperm over Phil's shirt and tie. Sam wiggled her bottom side to side, enjoying the feeling of Phil's spent cock within her. The feeling caused her own cock to raise once more. Phil's limp dick slipped out of Sam's arse and she peeled the spent condom off. She reached behind her and grabbed a fresh condom from her blazer pocket. Phil said she would need to give him a moment before using that condom. Sam had other ideas, and Phil looked on in surprise when she rolled the condom onto her own rigid cock and spat to lube the end. Stunned Phil offered no resistance as she parted his legs and push her cock head into his rosebud. His eyes widened as she fed him all 6" inches of cock into his virgin arse. As her balls slapped his arse cheeks, she gave him a minute to get used to her invader then slow withdrew. Phil clenched his teeth as Sam ripped him apart, she was now slowly fucking him. Soon his face began to relax as the pain turned to pleasure. Phil's cock betrayed any pretence to disliking Sam's treatment, as it rose to the occasion. Soon his cock was rock hard and tented his shirt. This was turning Sam on more as she increased her pace. Since she had recently come she had more staying power and raped Phil's arse with an overwhelming desire for release. Phil's whimpering turned to a moan as he fired a load of spunk under his shirt. Sam gave several fast strokes before filling the condom deep inside Phil. As she recovered she pulled out of Phil and discarded the condom. She crawled up the bed and Phil spooned her. He whispered that he had never felt so much pleasure, and was defiantly going to be fucked again. Sam smiled back that perhaps he should try it as a girl, it makes the whole experience better. Soon they drifted off to sleep. Sam awoke a little later, the room still illuminated by the bedside lamp. Phil was fast asleep, so she slowly climbed off the bed. She pulled on her knickers and fastened her blouse. She found her skirt and shoes and put them on. On the table was an A4 writing pad, and she wrote a note to Phil thanking him for a lovely evening. She wrote down her phone number as an afterthought. Looking in his mirror, she buttoned her collar and straightened her tie. She found her blazer and put it on. Quietly she left the room and headed outside. She called for a cab, after earlier noting the number of the cab that dropped them here. 20 minutes later she let herself back into Liz's house and sneaked up the stairs. Maria's door was open and the bed was empty, but there was a light on in Liz's room and Sam heard the unmistakable sound of sex coming from behind the closed door. With a feeling of slight disappointment, she peeled off her uniform and got into her night wear. She was sound asleep seconds after her head hit the pillow. She dreamed she was the sexiest girl in school.