Mary Becomes a Whore

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went on dates but couldn't get a girlfriend, he was always depressed by the rejections and constantly blamed his lack of manliness for it. To relieve his sexual frustration he saw a lot of porn and got too by the size of dicks of the porn stars. Slowly he developed a liking for cock and he turned towards watching crossdresser and Trans porn. He felt desires within himself about being feminine and fucked by a guy with a big dick. He started practising by using sex toys to prepare himself for the big day.

Mark knew that he would need someone to teach him how to dress up properly and guide him with lessons in being feminine. He started looking online on various websites to find someone who is a feminine crossdresser. On one of those websites, he came across Tasha's profile. Tasha was a beautiful crossdresser who was very sweet and feminine. She was as passable as any other natural born female. Mark instantly liked her and sent her a long message of appreciation and requested her to train him.

Next day Mark was surprised to receive a response from Tasha, he started having conversations with her and they immediately connected with each other. After chatting for a while they decided to meet at Tasha's apartment in the afternoon where Mark would undergo training to become Mary. It was Tasha who renamed Mark as Mary and he instantly liked it. It was going to be a new beginning in Mark's life as he was now looking forward to fulfilling his desires.

Tasha's home was a modern apartment with enough space for playing and experimenting. She had a lot of BDSM tools and kinky stuff like toys, hooks, whips. Tasha was an experienced crossdresser who indulged in fetishism and kinky sex and also helped newcomers like Mary to discover the sissy within them.

Mark greeted Tasha and they sat on couch and had a small conversation. It was then Tasha asked, "Are you ready to finally be the sissy you wanted to be?"

"Yes Ma'am," said Mark.

"Are you ready to be Mary?"

"Yes Ma'am"

"Then let's go for it."

Mark took off his clothes and showed off his newly shaved body. His fair body was looked milky white after removing all his body hair. Tasha couldn't resist but touch and check out his body. She playfully rubbed her hand on Mark's tiny dick and his shaved pubic area around it. She grabbed his ass cheeks and pulled it to his shaved asshole.

"It's ready for guests," she said.

Mark joined Tasha in the shower for a little fun session between the two before the makeover. Tasha had a really tiny dick that would look just like a small piece of dough. They kissed each other in the shower. Mark held Tasha's head and proceeded to rub his hands all over her body. He pinched her fluffy nipples and rubbed her ass. Slowly he put one finger inside her ass while giving her a deep kiss. He fingered her and she being to moan. He started licking her nipples and sucked them. Tasha didn't have boobs as she didn't take hormones yet she was so elegant and feminine that she didn't need them. Tasha bent down and started sucking Mark's dick. It was so wonderful for him and he had never experienced such a wonderful blowjob. She was skilled at giving blowjobs and perfectly rubbed his balls giving him a never before experienced pleasure. It was too good for him as he came in her mouth soon. Watching cum drip off from Tasha's mouth excited him and he kissed her. The taste of cum was something new to him so he spit it out soon however Tasha was playing with cum and soon spit it out.

It was time to be Mary now. Tasha's bought a white coloured lacy bra and panty that looked really sexy. As soon as Mark wore it a new rush of energy and kink ran through his body. He was finally Mary now. Tasha bought a tight black coloured dress and he wore it happily. It took an hour of makeup and a wig to completely transform him. It felt so good that he hugged Tasha and started kissing her. Mark now realised his feminine side and it was a magical moment. The feeling of the tight silky dress on her body was kinky but yet marvellous.

"Call me Mary!" said Mark as he was really excited.

"Yes, from now on you are Mary, lets show the world what you got," said Tasha.

Mary had finally ready to hit the streets. It was for the first time that Mary had went out in public dressed in sexy feminine clothing. Tasha was used to getting stares but not Mary. It was awkward for her initially but Tasha kept comforting her. She thought to herself that this is a new beginning so she should keep going.

The evening had begun and there was some crowd on the streets. While walking through a crowded street Mary felt like some hands rubbing her ass. Those rough hands felt good and she giggled. Tasha noticed that and said, "You have arrived Mary."

They went to a local diner and decided to have some dinner. While ordering food, the staff was smiling at Mary and Tasha and suggested them to try out some of the special dishes there. They started having their dinner and meanwhile Tasha had an idea.

"Have you thought about being a whore?" asked Tasha.

Mary was stunned to hear that but was equally excited. The prospect of getting fucked ushered like a dream to her and that too getting paid for it.

"Mary wants to be a whore tonight." she said.

"Very good, my training is paying off."

Mary giggled.

"You are going to be a street whore tonight, fix your price and I know a place where you can get some action." Tasha replied.

After completing their dinner they proceeded to walk around and after taking a few different roads they finally reached an isolated spot near a garden.

"You know what to do, bring me some good news." said Tasha.

"Yes Ma'am."

Tasha proceeded back towards her home while Mary stood there alone waiting for a customer.

Mary's tight sexy black dress was so appealing that no one could resist her. After waiting on the footpath for a while, a car stopped by. There was a guy driving that car, and he looked to be around 30 years old. He was muscular and beefed up. Mary drooled at the sight of his body and started imagining the night with him.

"How much?" asked the guy.

"120 dollars"

"Get in."

She stepped into his car and they drove off. She was feeling nervous but at the same time very excited about having sex for the first time with a guy and that too a muscular one. They drove around for a while and in the meanwhile he started making a small chat to make her feel comfortable.

"What's your name?" the guy asked.

"Mary"

"Nice, it suits you."

"And what's yours?"

"Greg, and it's my real name" he said as both of them giggled.

Mary was feeling comfortable now, with Greg and her new avatar. After a few minutes they had now reached his home. It was an apartment on the 3rd floor of an old style building. The building looked like crowded and there were some occupants. As soon as they stepped inside the lift he grabbed her and started kissing. He was so much naughty and didn't wait to get inside the house. They entered the room soon.

He gave her the money and she kept that in her pure. They continued kissing and after that she started undressing slowly. She revealed her panties. He grabbed her once again and started kissing like an animal. Mary felt like it was a heavenly experience. She was really excited and had and erection but was controlled by the careful tucking.

He removed his clothes and took out his cock. Mary's mouth opened at the sight of the cock. It was just like the porn movies. It was thick and long. She happily took it inside her mouth and started sucking it like a candy. It felt so good, the warm big cock that went straight down her throat and was choking her. She sucked it for a few good minutes until it was wet enough.

She proceeded towards the bed and climbed it. She went on her knees with her face down on the other side. Then she slowly lowered her panty slightly to reveal her asshole.

"Fuck me daddy, make me your slut," she said.

"Yeah baby!"

Greg wasted no time in getting lube and started fingering her. It was a real tight asshole and he loved it. It was going to be a wonderful time for both of them. He gave it a nice massage that made her moan with pleasure. She started breathing heavily with excitement.

It was now time for the dick. As he put his dick inside her Mary shouted.

"Oh God!"

Greg gave her a wicked smile. He began to hold her and fuck her really hard. Being held by a strong muscular man was a feeling of high and getting fucked by his big dick was a dreamy experience for Mary. She knew now how the girls in porn felt while getting fucked and realised that this experience of getting fucked is much better than fucking a girl. This was like a dream, she felt like reaching a sexual high that she wished would never end.

They changed position now. He laid down on the back while his big dick hung in the air. Mary sucked it once again to make it nice and wet, then gleefully jumped on the dick and started riding it. The joy of jumping on a big dick was something she had never imagined. After riding in this position for a few minutes she got up.

She then proceeded to lay on her back and started getting fucked. He bent down and kissed her slowly. It was so romantic and pleasurable. After kissing for a while the guy put his hand on Mary's neck and was choking her while giving a few thrusts. It was so orgasmic and kinky that Mary let out a bit of precum inside her panties.

"I want your cum daddy, give it to me," said Mary as she was having an orgasm.

Upon hearing this he took out his dick and Mary went on her knees. Mary opened her mouth wide open and let her tongue wide out. After jerking for a minute a thick load of white cum came out of the cock. It was very thick and she didn't want to waste a single drop of it. She wished if Tasha was here to see how wonderful her slut has performed. She gargled slowly and swallowed all of it. She sucked his cock for the remaining cum and licked it clean.

"Wow, you are a really naughty girl," said Greg.

"Yes daddy!"

"What are you doing this Saturday? Would you like to join me and my friends? They would love to have you around. "

Mary got really excited at hearing that; a gangbang was something straight out of dreams.

"I would love to."

"Give your number, I will call you."

Mary was shaking as she stood up and proceeded to wash herself. They kissed once again as she got dressed up and left. She could barely manage to walk after that wonderful banging but she had to go home. She took out her phone and called Tasha.

"I have some good news."