Erotic fiction and short sex stories

New stories daily




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.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.

womanhood   journey  

Sep 11, 2018 in anal

Tags

Search