A Journey to Womanhood

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A young man starts his journey from boy to woman.
2.3k words
4.41
64.1k
34

Part 1 of the 5 part series

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

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ColonelinguistColonelinguistabout 1 month ago

Fear not BC! Nobody in their right mind expects perfect English on these pages.

Pros: many Literotica stories are way too long! This story was perfect in this respect imo.

I suspect that many of these authors haven’t yet figured out how to “wrap it up,” and therefore their stories, though powerful for a page or two, lose their way by their mid-point. Whenever I happen upon one that’s on chapter 8, in my mind it a no-brainer; I’ll be skipping it for sure.

Pros: You illustrated quite well, the paralyzing fear that every cross dresser has of losing the love and respect of those who are the closest folks to them, especially when there coming out of the closet for the first few times. Fortunately for John, there were 3 people who had ample compassion for the person he knew he was on the inside.

As I often do, I like to find an author’s earliest submission and, if I feel something from it, move forward from there; something I attend do with your postings for sure BC!

AnonymousAnonymousover 8 years ago
get some help

as has been stated before, you need an editor. the paragraphs felt like someone with ADHD wrote them. Get some conversation going, instead of explaining who said what have them actually say it in separate paragraphs.

AnonymousAnonymousover 8 years ago
Get an editor

English is clearly not your first language, or indeed your spellchecker's first language. Your writing shows promise - do everyone a favour and get an editor.

AnonymousAnonymousover 8 years ago
Constructive criticism

Maybe Literotica needs to have a basic literacy test for authors wanting to post here because this isn't even good gibberish!

InosolanInosolanover 8 years ago
Not being snarky here...

...but is English not your first language?

Because this reads like someone writing in a language they don't naturally think i.

The basic story is good, but the expression is a bit off-kilter.

I'll be reading more when/if there IS more, though.

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