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Editor’s note: this story contains scenes of incest or incest content.
Dear Reader: This story is a response to a request. It’s a stretch for me to try an unfamiliar genre. Since I am not gay and have very little experience interacting with the gay lifestyle, please excuse my naive view and know I wrote from the heart. Regards, shptchr. As always, this story is fiction and any resemblance to persons living or dead is purely coincidental. Now, on with the story.
Andy Markson appears to be your average male. He is a bit shorter than average height and weight. He is handsome and has a slightly soft complexion. Women seem to flock to him like moth’s hover around a streetlight in the summer. Unfortunately, even with his good looks, high school was particularly problematic for Andy when it came to dating. His emotions were conflicted. The crowd he hung out with were much like him, outcasts from the socialites, athletes, and goth kids. Although Andy was successful academically and received a full-ride to a Division II college, he was a failure at romance. Throughout high school, he tried dating girls. His classmates bragged in the locker room about who they fondled, fingered, and fucked, but Andy could not bring himself to do so. He was scared of girls, and the thought of kissing or groping a girl at school was unnerving. Growing up in a profoundly religious home, his fire and brimstone Baptist mother put the fear of God in him.
Andy’s parents died at age 17, two days before his 18th birthday when they were killed by Tower 2 on 9-11. They were sightseeing in Manhattan when the tower collapsed and was buried under tons of debris. The loss of his parents was emotionally devastating.
In college, Andy struggled with his sexuality. Oh, he was cute all right, his physique was perfect to model underwear, but there were no agents in his Podunk Midwest farm school town who could give him a career. During his senior year, a very nice farm girl sat next to him in his Econ class. Andy liked her, and she would meet him in the commons building for lunch twice a week after class. About six weeks before graduation, Andy’s fraternity held an off-campus party celebrating the end of their schooling. Not one to be a party animal, Andy was required to be at the party because he was a sponsor of some of the freshmen pledges. He was sitting off to the side nursing a beer when the girl from his Econ class sat down next to him.
Andy hated parties, and it showed. The furrows in his brow were deep trenches as he watched the shenanigans of his frat brothers. He thought the immature people were disappointing and shameful. His mother taught him to always be the gentleman and to treat people nicely even if they may not do so to him.
“Penny for your thoughts Andy.”
“Uh, what, I’m sorry Mary, what did you say?”
Andy was in deep thought about his future. He had no home to return to because his parents did not have life insurance. The sale of the family home paid the mortgage, but it wasn’t enough to be comfortable. The sale of the house provided enough equity money to pay for his college education expenses, but he had to work part-time at the campus bookstore to make ends meet.
“I said, what are you thinking about?”
“Nothing, in particular, I was watching my idiot frat brothers making fools of themselves.”
“Andy, may I speak with you in private? It’s too loud in here. Follow me.”
Mary took Andy by the hand and walked upstairs to a bedroom where she and Andy were alone. Once inside the bedroom, she took Andy to the bed and sat down.
“Do you think I’m pretty?” Mary asked.
“Of course, I think your pretty. Mary, I think you are probably the prettiest girl at school.”
“But do you like me, Andy?”
“Yes, I like you.”
“Why then haven’t you tried to kiss me?”
Andy became very nervous. His blood pressure rose, he started to sweat, and his voice cracked as he spoke.”
“Well, ahem, I, ahem, girls and I, ahem…”
Quicker than he could realize, Mary stood up, faced Andy, put her hands on his shoulders, and pushed him onto the mattress. With her body weight on his, her mouth found his mouth, and they kissed. Mary’s tongue invaded his mouth. Andy was conflicted. On the one hand, he liked the feeling of Mary pressing against him. His dick engorged with blood as her hips ground against him. But, he was paralyzed as the sensations enveloped his brain. Mary stood up and worked to unbuckle his belt to remove his trousers. She was amazingly fast. In less than three seconds, Mary had his pants around his ankles. Andy’s eyes rolled back into his head as he felt the pleasant sensation of Mary’s mouth on his cock. Her tongue lapped at the underside on his Ahh-spot. Although Andy’s cock is longer than the average size man, his girth is typical, and Mary had only a little difficulty getting it down her throat. She was an expert cocksucker. Her hands were like that of an expensive call-girl, stroking him as she şişli bayan escort gave him head. His mind was awash with pleasure, and his climax was close at hand.
“I’m going to cum.” He warned.
Mary released his hard cock and crawled up straddling his legs. She lowered her naked quim onto his dick and started fucking him. The feeling of the warm tightness of her cunt on his cock was pleasurable but confusing. Andy felt the cum rising from his balls and prostate as Mary ground away. Her naked clit rubbed against his pubic hair causing her to moan. She brought his hands to her breasts and encouraged him to feel. Nature took its course, and a massive load of baby batter filled Mary’s cunt. She climaxed as she felt the hot cum coat her insides.
Breathing heavily, Mary collapsed onto Andy and spoke softly into his ear.
“God damn, that was good.”
A knock at the door startled Andy. He pushed her off him, pulled his pants up and dragged Mary into the adjoining bathroom.
“Is there anyone in there?” The voice said.
Andy opened the door to find Trevor Wilson, his frat brother standing with, make that holding up, a drunken girl. She was silly, smiling, and horny.
“Are you finished? Shelia here wants to fuck.”
“Ask your friend if he wants to join us. He’s cute.”
Without saying a word, Andy rushed out of the room, flew down the stairs, and drove back to his apartment leaving Mary far behind. He was sick to his stomach and barely made the toilet before vomiting. His mind was reeling with confusion. Mary is a nice girl. She was not drunk, she is fun to talk too, but he’s not sexually attracted to her.
For the next six-weeks, Andy avoided Mary as much as possible. When they were in class together, he was distant but cordial. When Mary tried to get Andy to go out with her to parties, Andy declined to say finals were coming soon.
Graduation came, and as he left the stage with his diploma holder, Mary found him. They had not spoken much since the party.
“Andy, I’m pregnant with your baby.”
“What? No way. How could you- “Mary cut him off mid-sentence.
“At the party. I’ve not been with anyone before or since. You are the father, Andy.”
His world collapsed in pfft of a second. His heart dropped, and his shoulders sank. Andy felt the weight of the world upon him. He turned and started walking away. Mary walked beside him and spoke:
“You can’t run away from this Andy. I’m carrying our baby, and I am NOT going to have an abortion or give it up for adoption. We are going to get married and raise our child together.”
Andy heard what Mary said, but did not process the information. His mind was in a fog of disbelief. Mary drug Andy toward where her parents were standing. Andy shuffled along barely able to walk.
“Mom, Dad, this is Andy. He’s the one I told you about.”
Mary’s father shook his hand vigorously.
“Glad to meet you son. I see you have been taking good care or our Mary.”
Her mother was next. She pulled herself close and hugged him tightly. She kissed him on the cheek and said:
“Mary has told us all about you.”
Mary had her arm through Andy’s beaming with pride. All he could do was produce a weak smile.
“Mom, Dad, Andy has asked me to marry him. We were waiting until we graduated before telling anyone.”
Both of Mary’s parents were super excited. Her mom had tons of questions to ask, and her father asked Andy about their future.
Andy started to think on his feet: “Well, we haven’t given it much thought yet. We both need to find jobs right away. Until then, we can stay in my apartment after the wedding and then decide what to do.”
Mary’s folks invited Andy to join them for lunch, and they walked toward their cars.
The wedding was a Catholic Mass. Several hundred people showed up for the combination wedding reception and the 25th anniversary of Mary’s parents. The events of the days leading up to and including the day of the wedding were a blur for Andy. He did not remember saying I do during the ceremony. It was as if Andy was dreaming a nightmare. At the wedding reception, a friend of Andy’s father-in-law offered Andy a job at his Port of Houston operations in the shipping and receiving department. He would oversee making sure cargo was loaded on ships and offloaded properly. It did not take long for Andy to become proficient at his job. He made enough money to afford a beautiful apartment in a suburb of Houston while Mary carried their baby.
Nine months to the day, Mary delivered a beautiful daughter. They named her Charity Ann Markson. When Andy first saw his daughter, it was love at first site. He had never felt this way before about anyone, and the emotions were overwhelming. From the instant first held Charity, her little hand latched on to his finger. It was as if they were meant to be together. Andy’s life started its downward spiral immediately after Charity was born. Sudden Infant Death Syndrom took Charity away from Andy when she was 8-weeks old. şişli escort After their first anniversary, Andy became a recluse and more disenchanted with marriage. Sex had become non-existent with Mary, and he was now resentful for trapping him. Andy tried hard, in the beginning, to make his marriage work. But he began to not look forward to having sex with Mary.
One afternoon, Andy came home unexpectedly for lunch. When he entered their apartment, he heard noises coming from the bedroom. The noise sounded like Mary might be in trouble. As he approached the bedroom, from the hallway he could listen to Mary say:
“Oh, yes, your cock is so big. Fuck me, fuck me hard. Give me that meat stick. Slam my cunt.”
Andy could not believe his ears. He peeked around the corner of the open bedroom door and saw Mary on their bed with her face on the mattress and one of his co-workers Jim Landers laying pipe. Mary’s head was facing away from the door and did not see Andy move to stand in the doorway leaning against the door jamb. Both Mary and Jim were fucking like animals. After a few minutes, Andy heard Jim grunt and moan while he was filling his wife with cum. Jim pulled out of Mary and lay beside her. She flopped onto her back next to Jim. Both were oblivious to Andy’s presence and were startled as he spoke:
“Mary, I don’t understand. Why did you do this?”
Jim sat upright and started putting his clothes on. Mary, on the other hand, said nothing. She lay there with a smirk on her face. Jim pushed past Andy and left their apartment. After she heard the front door slam, she flew into a rage:
“YOU WANT TO KNOW WHY?” Pointing to the cum dripping from her snatch she said: “THIS IS WHY! DO YOU EVEN REMEMBER THE LAST TIME WE HAD SEX? DO YOU?”
Andy realized he was a failure as a husband. He had zero sexual desire for his wife and accepted the fact that she was cheating on him. Calmly, he turned around and left.
Not knowing where to go, he drove aimlessly around the city. His thoughts were scattered. Several hours after leaving, Andy decided to return to his apartment, packed his suitcase, and stopped to speak with Mary.
“You are right. Our marriage is a sham. I have never loved you and have resented you trapping me into marriage. It makes no sense to stay married to you. You can have everything. I want nothing from you.”
Their divorce was final six months later. Andy had quit his job and moved back to New York. He found work in Manhattan at an accounting firm following up on customer audits. His workday was to audit the auditors from his company. Life became boring for Andy, and he struggled with his sexuality. At home after work, he would often find himself looking at porn sites on the Internet and, when he saw a couple engaged in sex, his attention focused on the man and not the woman. Soon, he was discovering the joy of masturbation while looking at transexuals and transvestites. Something in his mind clicked, and he started ordering women’s underwear and stockings from the Internet. He would wear the garments while watching porn and jacking off.
Andy especially liked the feel of nylons on his legs and the silky feeling of a shimmering nightgown against his pantyhose clad legs. He was becoming a transvestite.
At first, he was not passable as a woman. He read many stories and realized that he was a woman trapped in a man’s body. The joy Andy felt dressed as a woman was exhilarating. Afraid to go out in public, he wore women’s clothes in private.
On weekends Andy would make his transformation right after work and stayed feminine until going to sleep Sunday night. Sometimes, he would wear a bra and panties to work. The tight feeling of the thong against his cock made him suffer from a hard-on nearly all day. On those days, he would make several restroom breaks to jack off and relieve the pressure. One night, Andy stumbled onto a website where transvestite men would meet and dress ladylike for one another. Stirring up the courage to meet a group of like-minded people, on the following Saturday afternoon, Andy packed a small suitcase with his feminine items and met two men at a gay bar. They had been chatting online for several weeks and had exchanged pictures of ordinary clothes and cross-dressing. Nervous as a long-tailed cat in a room full of rocking chairs, the meet and greet went well. They agreed to share the cost of a hotel room together. Once inside the room, the three individuals started to prepare themselves. Andy was amazed at his transformation. The other two gave him tips on makeup, how to tuck his package, and how to walk and talk feminine. Andy felt he was passable and when the others decided to go back to the bar where they met, Andy was reticent but agreed to go. They arrived at the bar in a taxi, and as they exited, the doorman commented on how lovely the ladies looked. Andy felt flush as the gaze of the big and burly doorman smiled at him. Inside, the three found a table and ordered drinks. It did not take long for handsome men to come mecidiyeköy escort to their table to talk. The other two excused themselves and left the table to go be with their male admirers. Andy was now alone.
Within a few minutes of his friends leaving, Andy felt like the woman in the Jimmy Buffet song Fins. “She’s takin’ care to look for sharks, they hang out in the local bars, and they feed right after dark. You got fins to the left, fins to the right, and you’re the only bait in town.”
One by one, admirers came up to Andy and chatted. When one asked his name, he was dumbfounded. He did not have a feminine moniker. He tried to be coy and dodged the question, but the man kept pressing for a name.
Finally, he said:
“Andrea is a beautiful name for a beautiful woman.” The man took Andrea’s lace gloved hand and kissed it. Andrea’s heart fluttered.
“My name is Howard, it’s very nice to meet you Andrea.”
Howard was an average male and ruggedly handsome. He was wearing an expensive suit, but his hands were rough and calloused. Andrea learned that Howard worked overseas 18-months at a time in the oil industry and had to return stateside when his visa was up. He would be home for six months and then back overseas again. Howard had just returned from southeast Asia.
After all the years of self-abuse for not being like a normal man, Andrea felt at ease with Howard. She liked the way the man was kind to her and showed an interest in her mind. At first, she was reluctant to speak, but the alcohol soon took her inhibitions. When the gentleman suggested that they retire to his apartment for some privacy, Andrea was ready.
In the years following her divorce from Mary, Andrea had come to realize she was gay and longed for the opportunity to suck on a cock. Now, she is giddy with excitement at the prospect of fulfilling her dreams and fantasies.
Howard was an international business traveler. He hop-scotched his way around the world selling computer parts for companies in southeast Asia. When Andrea entered his apartment in mid-town Manhattan, she was awestruck at the appointments and furnishings. Erotic paintings and sculptures from contemporary artists were throughout the place. Andrea was stupefied at the beauty before her eyes. Howard pointed to the large leather sofa, she sat at one end while Howard brought out a bottle of vintage Cabernet.
Sipping the French wine, Andrea asked:
“The artwork you have is lovely. Do I see a Monet over there in the hallway?”
“Yes it is a Monet, but it’s a terrible forgery. I bought in Paris several years ago from a gallery on Champs-Élysées back in the early 90s. I paid a pretty penny for it, only to find it was fake. I keep it there to remind me of how significant provenance is when trading art.”
“It certainly is beautiful.”
As you may imagine, Howard is a strong masculine figure compared to Andrea’s demur and feminine features. His expensive Italian suit, pheromone cologne, and buff physique contrast with her simple cocktail dress, stockings, and pumps. She is trembling with desire as Howard scoots closer to her.
“You know, Andrea I find you very attractive. I sense you are out for the first time as a woman. Is this true?”
Bowing her head and looking at her folded hands in her lap she let out a barely audible: “Yes.”
Taking his bent index finger and placing it under Andrea’s chin, he lifts it gently so he can look into her eyes. Her emotions run the gamut from fear and anxiety to butterflies in her stomach and downright horniness.
“May I kiss you little dove?” Howard asks.
Andrea closed her eyes and leaned forward as he brought his face near hers. When their lips touched, it was as if a million volts of electricity was triggering every neuron in her brain. His kiss was gentle as butterfly wings. It only lasted a few seconds, and when they parted, Andrea opened her eyes and saw Howard smiling at her. She was trembling.
He held her hands in his and told her how beautiful she was. Howard leaned forward again, and their lips met. Only this time, she was the aggressor and thrust her tongue inside his mouth. Unknowingly, she parted her legs as her clit became erect. He had his hand on her thigh and moving it up toward her crotch. Andrea was focusing on his kiss and did not feel his hand. When Howard’s hand touched her clit, she let out an audible gasp. Her eyes were wide open and having a man’s hand surround his hardness was a brand new feeling. Andrea mewled as Howard’s fingers encircled him. Her hardness increased as the firmness of his grip started to slowly move up and down her clit. Their kissing increased its intensity and soon they both were clawing at one another. Her hands were under his coat around his back. He was leaning over as she slouched on the sofa. He maneuvered himself around to her side as she lay stretched out on the luxurious leather furniture. Instinctively, Andrea spread her legs as Howard continued to stroke her clit. He broke their kiss, and while looking into her eyes, he raised her dress up to her waist and pulled her thong out from under her body. Andrea’s clit was only 5-inches long, but it was standing straight up like a flag pole. Howard’s mouth began to water as she said:
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