A Journey to Womanhood Pt. 03

Story Info
A long weekend gives John the much needed time as Sam.
3.7k words
4.6
22.1k
12

Part 3 of the 5 part series

Updated 06/07/2023
Created 11/10/2015
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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.

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ColonelinguistColonelinguist19 days ago

There’s a realness to this tale of yours which pleases me Brenda. There’s a certain kind of sophistication that comes across with you English authors that I always enjoy.

AnonymousAnonymousabout 8 years ago
Theh Mark showed up with Aids.

And the real consequences started.

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