A Journey to Womanhood Pt. 04

Story Info
Sam's long weekend continues.
2.8k words
4.62
17.7k
10

Part 4 of the 5 part series

Updated 06/07/2023
Created 11/10/2015
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Sam awoke with the sun beating through the window. It was 8.30am. She rose and hit the shower. After drying off, she dressed and did her makeup. She wore a tight pink t-shirt and short denim skirt. When she got downstairs there was a man in his 50's sat at the dining table sipping a coffee, he had on a white shirt and grey trousers clearly the remains of his school disco uniform. They both stared at each other for a few moments when Liz entered, wearing her dressing gown. She introduced her friend Ron and asked Sam what she wanted for breakfast. After accepting the offer of a full English she sat at the table and started to read on of the fashion magazines that were there.

Liz brought to plates and joined them. They chatted in general, and Liz asked about the previous night. Sam told them about Phillip and suspected he was more of a t-girl than he cared to admit. Liz joked that they could help him get the inner girl out of him.

Just then Mark entered, he was wearing Maria's school blouse but had borrowed a pair of jeans and a hold all for the rest of her outfit. Mark grabbed a quick cup of coffee and head upstairs. Liz headed to the kitchen to fix Mark some food and cleared away the dirty dishes. 20 minutes later Maria came down fully made up and wearing blue wrap around dress. She clearly knew Ron and chatted like old friends.

Ron left soon after lunch, and Sam received a text message from Phil. He wanted to know if she was free for lunch. Sam checked with Liz and Maria to see if they had any plans. Liz told her they had no plans, so Sam text back that she would meet him in town around 12pm. After a lazy morning, Sam retired to her room and redid her makeup and hair in a little more formal fashion and changed into a cream strapless dress with a black belt. She accessorised this with a half-length black jacket, 2-inch open toe heels, and a black satin clutch purse. She put her money, cards, phone and ID into the purse and headed out to meet Phil.

When Sam reached the bar Phil was already waiting for her. He had ordered a couple of large glasses of red wine. Phil stood and greeted Sam with a quick hug and kiss on each cheek. Phil seemed a little nervous to Sam as they spoke about their activates the previous night. Phil mentioned that Sam's comment about trying to play the girl during sex has got him thinking. He certainly loved being fucked and now considers himself fully bisexual. But was also now open to exploring his feminine side. Sam smiled and said with a little work he could pass easily. Phil was not so sure, so Sam took her phone out and found a picture of her as John. Phil was amazed at the transformation, John looked like any normal guy. Sam proposed that if Phil was willing she would help turn him into a girl and they could hit the Transgender clubs that night. Phil had been to enough t-girl clubs to know he would be safe and readily agreed. After finishing their drinks Sam took Phil dress shopping.

After their trip, they returned to Phil's room and the university. Sam ordered Phil into the shower with the hair removal products they purchased. As Phil showered Sam called Maria and filled her in. They agreed to meet up later at a club in town. Phil returned with a towel wrapped around his waist, he looked nervous. Sam gave a reassuring smile and whipped the towel away leaving Phil to cover is modesty with his hands. Sam joked she had seen it all before, Phil laughed and let go of his groin. Sam handed him the panties and bra they brought and with a little help he put them on. Sam stuffed his bra cups with some socks to give him a modest C cup breast. Sam instructed him to sit at his desk, as she went to work on his face and hair. First, she applied the hair net to keep Phil's hair out of the way. She expertly applied his makeup, just the right amount for a girl of his age out clubbing. She finished it off with blond wig they got from the carnival shop. It was a little fancy dress but by the time Sam was done teasing it, it did not look half bad. Sam held the cream Greek style dress out for Phil and he stepped into it. After she closed the zip on the back she turned Phil round to look at the full-length mirror on the back of the door. Phil was amazed at his transformation. He commented that he looked like his younger sister. For the next hour, Sam tutored Phil in the fine art of acting like a girl. Phil was a quick learner, and as 7pm rolled around Sam was convinced he was ready. There was only one thing left to do, every t-girl needs a name. Sam suggested Penny, but Phil looked again at his image in the mirror and declared her name as Natalie. Sam was pleased to met Natalie. And they loaded her handbag with her essentials and head back to town.

Sam noticed that Natalie was nervous at first being out in public, but as they took their seats on the bus she finally relaxed since no one screamed faggot at her as they left the campus. Sam text Maria to say they were on their way to town, Maria replied which club she and Liz were waiting in.

With ever step Natalie's confidence grew, and Sam could tell she was enjoying the female experience. They arrived at the club and after flashing ID's they were in.

The grabbed a couple of vodka and cokes and met Liz and Maria. Sam made the introductions, and Natalie was welcomed to the group. With added alcoholic bravery Natalie was now fully embracing her new persona. At the second club, she was asked to dance by a guy in his late 20's. She got nervous and blurted out that she was not a real girl, he smiled and said I know but you look beautiful. Natalie blushed and accepted his invitation. Sam was also approached by several guys, but she did not fancy any of them and politely declined.

The moved onto a third club and Natalie's new friend Neil joined them. After about an hour Sam heard another voice offering her a drink. She was turned her head towards him to decline when she was stopped in her tracks. Stood before her was a hunk of a man in his 20's, wearing an RAF uniform. A shiver went down her spine, and she accepted his offer. She joined Chris as he introduced himself at a private table. When he returned with the drinks he sat down, Sam could tell he was nervous. Sam asked if he was ok, he replied that he had never chatted to a girl like her before but seeing her from across the room he would regret it if he did not. Sam rested her hand on his for reassurance.

As they chatted he relaxed more. He was on leave from German, and he was a chopper pilot. Sam hung on his every word about the service. She told him of her dreams, and he confirmed that though the discipline can be a pain, it was fantastic that he got to fly nearly every day. Chris had his career path mapped out, and when he retired from the service in his mid 30's he would become either a police or air ambulance pilot. Sam has not really thought passes the RAF, but guessed she would assume a civil aviation job.

After a few drinks, they started to flirt more. Sam placed her hand on the thigh of his dress blue trousers and gently stroked it. She had made her mind up, tonight this guy was hers. She noticed Natalie talking to Liz and Maria. Liz gave Natalie her number, and Natalie left arm in arm with Neil. Good for her Sam thought and turned her attention back to her own man. Chris leaned over and their lips met, and they shared a long slow sensual kiss. Sam broke the kiss and suggested they go for a walk. Chris did not need asking twice. Sam said her goodbyes to Liz and Maria, and she joined Chris by the door. Being the perfect gentleman he held his arm for her, and she dutifully slipped hers around his. They took a slow walk down by the canal, Sam could tell he was getting nervous again. She stopped them and took his hands in hers and kissed him. She reassured him that he had nothing to be nervous about, he was defiantly going to get his way with her. He confessed he had never been with a girl like her. And she laughed that he was in for a surprise. She told him to take her back to his place, so he hailed a cab.

5 minutes later they entered his hotel room. Sam took the lead and sat Chris on the edge of the bed. She gave him a quick kiss and she unbuckled his belt and opened his dress blue trousers. She sunk to her knees and fished out his half erect 6" cock. She gently stroked several times, and then leaned over taking him fully into her mouth. Chris closed his eyes as he enjoyed Sam's services. Sam reached up and pulled Chris's trouser and pants to his ankles. Without taking his cock from her mouth, she removed all his clothing below the waist. She looked up and the site of this hot man, half in uniform. He was panting and she fondled his balls, whilst deep throating him. After several minutes, she stood up and turned her back to him. She slipped off her half jacket and then seductively unzipped her dress. Chris's eyes were on stalks as she let the dress slip off her curved body. Turning around she stood before him in her underwear. She leaned forward and grabbed his tie pulling him to his feet. As she kissed him she undid his tunic, loosened his tie and unbuttoned his shirt. She ran her hands over his toned body, and she encouraged him to do the same. Chris suddenly turned the tables and pick Sam up and through her on the bed. He slipped off his remaining clothes and climb atop of Sam. Sam saw the passion in his eyes as he leaned down and kissed her. Chris flipped Sam onto her front and pulled her panties down. His strong hands pulled her knees beneath her, raising her bum into the air. Without warning, he buried his face into her crack and ate her arse out. Sam's clit rose to full erectness as her lover lashed her bottom with his tongue. Sam reached behind her pulling his face off her. She pleaded with him to fuck her. She grabbed her purse and pulled out some lube and a condom. She rolled it onto his cock and smeared it with lube. She leaned over presenting her rosebud to Chris. Chris need no further encouragement as he inserted his cock passed her sphincter. Soon he was balls deep in her body, he began to make love to her as he felt she deserved. Sam purred as Chris slowly fucked her arse, at this moments she forgot about John, and was truly a woman. After several minutes of slow love, sensual love making Chris pulled out and flipped Sam onto her back. He lifted her legs over his shoulders and fed his rod back into her. She had a look of desperation as she need to feel his cock within her. Again slowly he worked his member within her, slow deliberate strokes. Sam had never been fucked so tenderly, Chris locked his mouth to hers as he thrust. As the time went on Sam's need for release started to grow to the point she was desperate. Every nerve in her body was alive. She whispered to Chris to fuck her hard, and without a word, Chris increased his pace. A wave of euphoria washed over Sam as she fired her load over Chris's chest. His grunts signalled he was close, he fucked her mercilessly as his own orgasm approached. Sam nearly faint when she came again, this put Chris over the edge as he emptied his balls into the condom.

Chris collapsed next to Sam panting. He looked at her and took in her beauty. Sam closed her eyes and basked in her post-sex feeling, she felt no trace of John within her and was truly a woman. Chris rolled her onto her side and spooned up behind her. Soon they were both asleep.

Chris awoke before Sam, as he returned from the bathroom he stopped for a moment and looked at his lover. The only give away she was not 100% a woman was her cock between her legs. He had never imagined ever sleeping with anyone with a cock but after the evening he had shared with her he did not care. He joined her back in bed and went back to sleep. Sam was woken by the first rays of sun poking beneath the curtains in the hotel room. She felt Chris sleeping behind her, she propped herself on her elbow and looked at this man. She climbed out of bed and took her clothes to the bathroom to get dressed, as she had done with Phillip the night before. Once dressed she returned to the room and just before she was to leave she decided Chris deserved more than a goodbye note. She wanted to see him again. With a wicked smile, she crawled back onto the bed and took his limp cock into her mouth. In no time he was rock hard, he also began to stir. He opened his eyes to see a gorgeous girl deep throating his cock. She looked him in the eye and smiled. Chris told him he wanted her, badly. She climb off the bed, reached under her dress and pulled her panties off. Chris grabbed the lube and a condom, Sam told him to forego the condom she wanted his load within her. She walked to the sofa and bent over the arm and lifted her dress, exposing her eager arse to him. He crossed the room and soon had several lubed fingers up her hole. She demanded that he fucked her. He replaced his fingers with his cock and thrusting his cock deep into her. This morning he was not holding back and fucked her with an urgency for release. Sam gripped the arm of the sofa as her bottom was being assaulted. Chris soon unloaded his seed into Sam and collapsed on top of her. Regain his composure he reached under Sam's dress and wrapped his hand around her cock and pumped it. With a minute, Sam fired her load over the sofa. Chris let her up and they shared a kiss and cuddle. Chris said he would love to see her again, and they exchanged numbers.

Chris offered her breakfast but she declined as she needed to get back to Liz's house, and get ready to head home. After another long lingering kiss, she left the hotel and grabbed a cab back to Liz's.

As she checked her phone she had a text from Natalie. She had spent the night with her suitor and had the best time.

When she entered the house Mark was up and preparing his bags for the journey home. Sam gave him a quick summary of her night and headed upstairs and hit the shower. Unlike Mark, she decided to redress as Sam for the journey home in a skinny t-shirt and mid-thigh skirt. Liz was up when she came down. Liz commented that she never did meet John, and Sam thanked her for letting her stay. All too soon they were in the car heading south.

Mark commented that she was quiet. Sam replied that the last three days had been the freest she had ever felt. Within a few hours, Mark pulled into his driveway and let Sam into his house. 40 minutes later John emerged and took a slow walk home. He was feeling low having to be back in boy mode. Just before he reached his home, his phone beeped with a text from Chris. He was back at his base and wanted to thank her for a great night. He said he could not wait to see her again.

Once inside his home, his mother greeted him and handed him an envelope with MOD marked on it. Tearing open the letter he unfolded the paper and read. Seconds later he whooped, he had been accepted into the RAF's pilot training program. He called Kathy to see if she had gotten in, and she had. Once in his room, the conversation turned to their respective weekends. They made plans to meet the next day.

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ColonelinguistColonelinguistabout 1 month ago

Wow! Part 5 coming up already and what began as a 3 character story now has at least three times as many. That can often lead to some confusion on the part of the readers, but you have managed things very well so far!

AnonymousAnonymousalmost 8 years ago
Won't last long

RAF has some strict rules.

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