This is my first story. I have never really written anything like this that I have shared with other people. If there is enough people that like it I will continue the story. Thank you for the read.

His name was Ryan, a guy in his mid 30s. Married to a wife that was too consumed with her job and complaining to pay any attention to his needs so he was left to take care of himself.

From time to time he would look at porn sites. Watching clips and vids that caught his attention. One night he stumbled upon a video that started off with a beautiful woman. She had amazing tits and curves in all the right places. She looked amazing he thought. He found himself with his hands down his pants before she had even shown anything outside what you would see walking down the street.

Ryan continued to watch the video stroking his cock. He had a full hard on at this point. The lady started to strip off her pants and shirt leaving her in just panties and a bra. She danced for a bit like this and all he could think was that she was really good at teasing him. He found himself increasing the speed that he was stroking his cock. The lady in the video pulled the back side of her panties down flashing her perfect bubble butt. It was so smooth with a perfect tan. She quickly pulled her panties back up with a naughty look. He found this excited him even more.

She exposed her ass again then asked the viewer if they would like to fuck her ass. This put Ryan over the edge and he exploded. He so aroused by this that he decided to keep stroking. He was now using his cum for lube. There was a bit of sensitivity from cumming and continuing to stroke but that faded.

He kept watching the video his dick still hard he felt something he had never felt before. His dick was throbbing so hard he felt the throbbing on this anus. This both confused him and excited him so he continued to watch the video.

The lady in the video had taken her bra off at this point and he was marveling at her perfect breasts. The lady was now pulling down at her panties again. Ryan was getting close to cumming again. This was new to him as he had not cum twice in this short of time before.

Ryan was getting more and more excited. He wanted to see her whole body, every inch. She had teased him and he found himself slowing down his strokes so he would not finish before he saw all of her. She once again teased taking her panties off with her seductive dance. Then she turned around to smack her ass saying she had a surprise for the viewer.

She turned back around and started to pull her panties down. He thought yes this is finally what I wanted to see that sweet pu……his thought was cut off.

She pulled her panties down past a point and a cock flopped up. It continued to bounce. He was unsure what to do. He was so close to cumming a second time. Then she asked the viewer if they would like to suck it, offering they could finger her ass while they sucked kn her big clit. At that Ryan exploded so hard that he shot a bit of his cum into his mouth by accident. The buttery, sweet, and salty taste was new to him and out of reaction he spit it out.

He sat there after cleaning himself up and clearing his history thinking about what he saw. Wondering if he was gay, he decided that maybe he was bi and thought to himself who cares.

————————————————-

Over the next few weeks Ryan found himself jacking off more and more. He would find videos where it seemed like the lady might be trans. The surprise is what had him hooked. As time progressed he found himself just searching for transsexual videos. He knew he was on a path of self discovery and unsure where it would take him but he liked where it was going so far.

————————————————-

The weeks past and Ryan’s wife had not noticed any of this was happening. He noticed a text saying she had to go on a business trip out of the county. Her trips usually lasted a month but this one was going to be an extra long one, at three months.

Ryan decided since his wife was gone he would go out to get something to eat. There was a restaurant that had just opened up the street he had wanted to try, but his wife hated to go out for food. When he walked into the restaurant it was packed. The manager told him they were all booked up for the night and that he should come back another night. A lady grabbed onto his arm and said “my date canceled on me. Care to join me? My name is Julie.” Shocked at her beauty after a couple mumbles words he finally was able to spit out a yes.

She told him if it made him feel better he could consider this their first date. Shocked he said he would love that. They were soon seated. They really hit it off talking about their lives and such. Ryan was afraid to scare her off so he left out that he was married.

They finished their dinner and unsure if they wanted the night to finish she asked him to come over so they could see what happened. He followed her in his car to her house.

Upon arrival she took him to the living room. She explained “I have never done this. Bring a man I just met home, that is.”

He responded “It’s ok. Don’t feel like you have to do anything. We can just hang out.”

She responded “give me a second. I need to change and get my head straight. You have me flustered.”

He sat in the living room. It seemed like an hour. He decided to go find her. He walked through the house looking in each room. He saw a light on and went to that door. He looked into the room and saw her in the room. She was facing away from him. She was completely naked. She bent over to pick up her panties on the ground. Her ass was perfect. When she bent over he noticed something, something extra. She had balls!!!! Shock and excitement hit him all at once.

He stammered. “S s s s sorry. I didn’t know what happened to you.”

She turned shocked. Her cock was stiff and he couldn’t take his eyes off of it. It was not huge but his first thought was it was a perfect size to fit the entire thing in his mouth. Then he thought that was a weird thing to think.

She quickly covered up with a silk robe and said “shame on you. You peeked!” She got a smile on her face “well I guess you saw my secret. It’s only fair that I see you naked now.”

Ryan was a bit shy when it came to being naked. She came over and pulled his belt off. Then unbuttoned his pants. They fell to the floor. She then pulled his underwear down. Shocked at the sight of his hard cock she said “my someone is excited. Have you been with a girl like me before?”

Ryan responded “no but I have dreamed about it for a long time”

Julie responded “well then I hope I can live up to your dreams.”

She leaned in to kiss him. Her robe coming open and their cocks brushed each other. A shiver shot up Ryan’s spine, a feeling of excitement.

She pushed him to the bed and said now let’s see how tight you are. Not understanding what she meant and enthralled in the moment. She started to kiss his cock and then suck on it. Then he felt her hand reach around and the felt a pressure. And then he jumped as one of her fingers went into his ass.

After licking his cock from shaft to tip she asked him “how does that finger inside you feel?”

He responded “different but not…” She wiggled her finger around and started to massage just inside. He moaned.

She said “ok let’s see if we can fit more.” She thrust another finger inside him. “See that wasn’t so bad.”

He could feel the pressure. She went to add a third finger. He let out a scream in paid. She said “oh sorry. You are really tight. We will work on that another time. “

Relieved, Ryan was just wondering what was next. She laid beside him on the bed. Her cock right in his face and his next to her face. She looked down and said “you know what to do. “

Confused and not he wrapped his mouth around her cock. He was excited to see what it taste like and if he actually could fit it all in his mouth. He bobbing his head up and down. The taste was not much different that sucking his finger. The smell thrilled him. It was indescribable and arousing. He decided he wanted it all in his mouth. He slowly took more and more into his mouth. He was over halfway and he started to worry he couldn’t do it.

She told him, “you don’t have to take it all”

He replied with excitement “I want to. I need to! I have to!”

She said “ok go for it.”

He started to go back down on her. He got almost all the way down and he felt the head of her cock on the back of his throat. He felt like he was about to gag. He knew he wasn’t going to make it. He felt so bad and then he heard her say “want some help?” He hummed “mmm hmmm”. She pushed his head down the rest of the way. He felt head of her member slide down his throat. It was exciting. He started to raise his head and she pushed him back down while moaning. She asked him if she could finish. He didn’t answer but kept going. She took this as a yes and pushed her cock back down his throat. She started thrusting down his throat faster and faster. He could feel the head of her cock getting bigger with her moans getting louder.

He decided to do as she had done to him. He took two fingers and plunged them into her ass. She moaned with pleasure and then screamed “more!!” He obliged and put another finger in. He singled them around massaging inside her.

Suddenly she started to twitch. And he felt it happen. She shot her load right down his throat. She rolled onto her back still breathing hard saying “you are amazing at sucking cock.” He laughed a bit saying “I have never done it before. You are my first.”

She looked at him and said “ok we need to get you off. How would you like to get off. Anything except in my ass. I don’t have anal on the first date.”

He looked at her and said “you choose”

She said ok. She started to oil up her ass. He watched confused. She then told him to rub his dick between her ass cheeks. She reached around and put his cock between her cheeks. He thrust up and down.

This felt amazing he though. Looking down at her back with those sexy dimples he loved. Her ass shiny from the oil. He felt a tingle. She re adjusted as he thrust back. Upon thrusting back he felt his cock enter into a warm and inviting area. He looked down and noticed he was inside her ass. He apologized “I’m sorry I know you said not on the first date. I didn’t mean to. “. She didn’t seem frustrated. The look on her face was pure ecstasy. She didn’t respond to him in words. She just pushed her ass against him, forcing him deeper inside her. She was tight and felt amazing. He knew he wouldn’t last long.

A few thrusts later and he exploded inside her. She moaned with delight. “Oh baby yes. Keep going. Give me more!!!” Each thrust he shot more into her.

He roll off of her his cock laying on his stomach. Cum still dripping from the tip. She laid next to him. Her cock laying over his leg. She told him “you are an amazing lover. We must do this again.”

A feeling of guilt flushed over him. He said “I’m married”.

She responded “I will not tell anyone if you keep me satisfied. No one will ever know. Make up whatever story you need. I will play along. All I want is more of this. Eventually your ass will be ready for my cock. Until then your throat will have to do.”

They fell asleep in each others arms.

To be continued…..

---