Transgender, Adult Youth, oral anal, m/Trans
This story is a work of fiction and contains descriptions of explicit sexual acts between a consenting youth and adult Transgender. If this type of content offends you or you are under the age of 18 do not read it.
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Copyright 2024 Jan, all rights reserved.
You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
Trans Neighbor
By
Wolf
David got excited when he saw the beautiful brunette moving into the nice little bungalow on the crest of the hill at the end of the cul-de-sac a few houses north of his parent's upper middleclass neighborhood. To a horny 14-year-old seeing an attractive single woman moving into the neighborhood aroused his curiosity and libido in equal measures. He had to find out more about her.
She was supervising the two men from the moving company unloading the truck full of household furniture. She was telling them where to take each item and the boxes. David was impressed by the number of wardrobe boxes there were. He approached the woman and said: "Hi, my name is David Wright, I want to welcome you to the neighborhood! If I can help you get settled in, just ask!"
The beauty looked at the youth appraisingly: "Thank you Hon, my name Lisbeth Larson, thank you for welcoming me to the neighborhood. It's sweet of you to offer to help, I think we can handle it."
"Lizbeth is an uncommon name. What does it mean?"
She smiled: "It is a common name in Sweden and is an old Hebrew name meaning 'God is my Oath.' The English version is Elisabeth.
He was full of curiosity and dying to ask her a million questions. He asked her why her husband wasn't there to help. Lizbeth told him that she was not married. He wanted to know how she could afford to buy a home in this neighborhood, and what she did for a living. She told him that she had inherited a portion of family money, but she owned a florist shop that she kept busy with. David began to feel as if he was in the way and told her again: "If you need any help just let me know.
With that said, he returned home to tell his mother all about their new neighbor. He raved about their new neighbor looking so much like the actress Morena Baccarin and went on to describe what she looked like in detail. His mother listened patiently and realized that he had a teenage crush on the new neighbor.
David kept an eye on Lizbeth's house hoping to catch a glimpse of her. It took a couple of days for her to move in several more loads of boxes before she was happy with the location of the furniture. Then came the task of unpacking all of the boxes. David came by and offered to help when he saw the empty boxes and paper scattered around. She accepted his offer and had him take the items out of the boxes and hand them to her as she put them into cupboards and drawers. Room by room. He was thinking that it was good that there was a wall-in closet because of all the clothes and shoes. They worked well into the evening. She offered to order pizza delivery for them. He was thrilled to accept.
While they were eating David continued asking questions in an effort to learn more about her. Lizbeth wasn't evasive, she just didn't volunteer additional information. David was curious why she was up so early every day. Lizbeth told him that fresh flowers were delivered to the flower market at the central market early every morning. Florists buy flowers from 3:00 am to 5:00am and by 7:00am the flower market is almost empty. As soon as she got back to the shop, she started making floral arrangements for display and fulfilling orders for delivery that day. My shop is in the downtown business district and my business time is when office workers are leaving for home and remembering at the last minute that they forgot an anniversary. I close up shop by 6:00 pm. My partner and I alternate making the trip to the flower market. I do enjoy working in my own flower beds when I get home. David told her he was on Easter holiday that week, and if he could go with her to the flower market some time. She said: "Sure if you can meet me at the truck by 2:30am in the morning."
David was dressed and standing by the van when Lizbeth exited her front door. They arrived at the flower market while the big rigs were almost finished unloading their cargo. Lizbeth was greeted by name by the Japanese and Mexican owners of stalls. She quickly moved among the stalls selecting the bundles of flowers and exchanging money and putting her selections in five-gallon cans with some water in them. They were on the road for a short amount of time. Everything moved fast, as soon a van left another one was pulling in. They stopped at a 24-hour diner that was close to the flower market. There were truck drivers there at that hour having breakfast. Some of them knew Lizbeth and greeted her as they joined them at the counters to have breakfast. A couple of the drivers jokingly asked if she was into jail bait. She smiled and told them that he was a nephew, to shut them up.
As soon as they arrived at the florist shop, they unloaded the truck. There were some flowers that had to go into the refrigerator immediately. Lizbeth taught him how to trim the stems and put them in containers with water that had aspirins in the containers to help prolong the freshness of the cut flowers, while she went about arranging standard FTD floral bouquets and putting them in the fridge. Then she made bouquets that were ordered for delivery that day. Her partner arrived before the 8:00am opening and got busy filling orders too. Lisbeth mentioned that they needed to order some of the standard FTD ceramics. They worked a few hours before Lizbeth noticed that Dave was nodding when he sat down, so she told her partner she needed to take him home.
On the ride home David told Lizbeth that he loved her. Lizbeth's eyes never left the road as she calmly said: "Dave, I'm flattered that you feel that way about me, but I'm sure that you would be shocked to know that I'm not the kind of woman that you should be in love with!"
Dave was puzzled by her comment, he thought she was the most beautiful woman he had ever met. He had to ask: "What do you mean? I have never met a more beautiful woman like you before!"
"Thank for the compliment, but I'm a transsexual."
Dave was confused because he didn't understand the term: "What does that mean?"
Lizbeth took a deep breath: "Honey, I was born a male and I knew that I was meant to be a girl. I went through a number of procedures that included hormone treatments to prevent me from entering male puberty. My body went through female puberty. My vocal cords changed to the timber of a female and I developed a layer of fat under my skin that gives me the figure of a woman. I even developed female breasts. I wasn't satisfied with 38-B tits so I had breast implants to give me 38-D sized breasts. The one thing I have not done is to have my penis turned inside out and made into a vagina."
It took a moment before David to processed the information and in all incense asked: "Does that mean you have a dick?"
Lizbeth smiled: "Yes Dear, I have a dick but my scrotum is very small."
"I have never seen any sign of a dick, even when I've seen you in short-shorts,"
"I tuck it between my legs and have a way of ensuring that it will not spring out, without mentioning that she tucks the head into her asshole. I legally had my name and sex changes and have a birth certificate to reflect the change."
David sat in silence for several minutes before he asked: "Can and how do you have sex?"
Lizbeth chuckled: "I can Have with males and females all I want. I can have sex with both males and females. I can do anything women can, and I don't need a dildo to fuck a woman. I can still have all the sex I want with males."
David was afraid to ask the next question. Lizbeth could tell Dave had a question unasked. "Do you want to know if I allow men to have anal sex with me?"
"Yes"
" I do have anal sex with males I really respect and feel safe with. Can I rely on your discretion not to tell anyone what I've told you, especially your parents? That's one of the reasons I had to move into a new community. When it became common knowledge that I was trans the religious assholes wanted me stoned or arrested, and there were both women and men that wanted into my panties. That led to some jealous accusations true or not.
David's head was spinning by the time he got out of the van and walked home. He needed to sleep, after he got a few hours of sleep his mother made him something to eat and asked about what he had done and what he thought of the flower business.
He told her all about what he had observed and was impressed with Lizbeth's ability to speak Japanese and Spanish, and carried on about the smell of the flower market and the cool damp morning air. Having breakfast with all of the truck drivers delivering flower and produce to market. He was overwhelmed by how busy the city was during the early morning hours. He said there are almost as many people working overnight as there are doing the day. She just didn't mention that he had found out that Lizbeth was transexual.
David's fascination with Lizbeth only increased. He was taught how to masturbate by a childhood friend and even engaged oral sex with a few guys until he learned that such activity was taboo. Now he was questioning his own sexuality.
The next opportunity he had to talk to her more about her sexual activity. Lizbeth told David that their relationship was dangerous for her because if it became known that she was trans she could be charged with corruption of a minor if his parents suspected that he was having sex with her. David objected: "Were not having sex!" That wouldn't matter, all there has to be is the suspicion that I was molesting you!
David said: "I would like to find out what sex with you would be like!"
Lizbeth said: "I was afraid of that from the day you talked to me while I was moving into the neighborhood. I did find you attractive because you reminded me of the teenage boy that introduced me to anal ex when I was 11-years-old."
David pressed her to tell him all about what happened. Lizbeth sighed before beginning her narrative of her childhood experiences. She told Dave as I told you I knew I was meant to be a girl when I was very young. I was molesting playmates of both sexes as a youngster. My father wouldn't hear of it and divorced my mother. She had me see a therapist and it was agreed that I would be happier if I were allowed to undergo the sex change. I was undergoing hormone therapy and dressing as a girl and was having my name changed from Lance to Lizbeth. That was when I met a neighborhood 15-year-old boy that was a basketball player and the high school junior varsity basketball player. He knew that I was going through the transition. He made friends with my mother and got her permission to date me. He took me to the movies and made out with me. When we got home, I sucked his cock and swallowed his cum. After several months of dating him, he broached the subject of him wanting to fuck me. I was excited about allowing him to fuck me. When Mom was visiting a friend one evening my boyfriend came over and I allowed him to fuck my asshole. I was hooked I allowed him to fuck me until he went away to play college basketball in another State. By that time, I was legally a girl.
David had a ragging boner that was stringing at his underwear and blue jeans. Lisbeth observed the effect her story had on David. She felt sorry for him and was aroused. She said: "David if I do this, you can never tell anyone or look at me with longing in front of anyone!"
David foolishly was quick to swear that he would do anything she told him.
Lizbeth said: "I guess you're dying to get a look at me naked!" With that she stood up and turned on the FM radio to an appropriate station playing romantic music and started performing an impromptu striptease dance in front of David.
When he got his first look at her tits and she lifted them up to show them off he couldn't see any scars. She told him that the scars had healed a long time ago. Dave wanted to feel them but that would come later. When she removed her short- shorts and hip hugger panties. David thought he had been kidding about having a cock because he saw two flaps of skin dangling below the triangle of dark pubic hair. Lizbeth reached between her legs and pulled out a cock that was a respectable length. Dave asked what was that skin I saw? She told him that it was her scrotum sticking out on either side of her cock. When she lifted the cock up her scrotum looked like an empty bag of loose skin. She posed before the youth before she started to remove his clothes.
David felt foolish allowing a sexy woman with a cock to undress him, but he was still in a state of shock, so he allowed her to maneuver his body around as she removed his shirt, T- shirt, shoes and socks, blue jeans, and tidy whities underwear. She admired his youthful body, and he did physically remind her of her first lover. David had the body of an active skateboarder. He was slender but strong enough to be able to do handstands on a moving skateboard. She appreciated that for a youthful teenager that Dave was endowed with a pretty big cock and mature scrotum. There was something adorable about the fact that David's hair was changing from his youthful platinum blonde to a sandy brown and a little haggy. (As men grow old, they envy the bushy hair they had in their youth.) His skin was as smooth as a baby's. She was drawn to his sex organs. When she took hold of His cock, Dave was shocked to see how long it got. His cock had never been as long as it was at that moment. It was at least seven-inches long and harder than it had ever been before. It resisted her efforts to push it down. His pubic hair was still blonde. Lizbeth couldn't resist taking His cock into her mouth and trying to suck him off.
Dave had been masturbating at every opportunity for five years and cumming for at least four years. This was the first time he was having sex and it was with the sexiest woman he had ever seen. As much as he was enjoying the sex he was starting to suffer because he couldn't ejaculate. Lizbeth recognized the signs of his dilemma because she had experienced the same problem in her youth when her teenage lover had sucked her off. She did to Dave what her first lover had done to her. She slipped her hand under Dave's butt and stuck a long finger up his asshole. That took his mind off of his cock and he shot the biggest load of cum that he had ever had into Lizbeth's mouth. Lisbeth lay between his legs and licked the shaft of his cock clean as Dave's cock's erection subsided.
While Dave was recovering, she asked: "Do you want me to be the first love to take your virginity?"
Dave was thrilled at the idea but feared the pain and asked: "Will it hurt a lot?"
Lizbeth assured him that it would hurt a lot more if he resisted. Her best advice was to strain like he was trying to pass a big turd. She placed Dave on her bed with his butt right on the edge. She used a generous amount of Vaseline to lubricate her cock and his asshole, before she picked up his legs by the ankles and placed his feels against her tits and guided her cock to his puckered asshole. She said push at the same time she thrusted her hips forward driving her large mushroomed head into the teenager's asshole. David whined in pain but endured it. Lizbeth reached around the boys left thigh with her right hand and took hold of his cock and masturbated him while she was fucking him. Dave reached his second orgasm before Lizbeth had hers. It was little more than a trickle of clear pre-cum with a little white cum mixed in it, as it flowed down over her hand. When Lizbeth reached her orgasm, she didn't produce much in the way of cum. Her male hormones had been suppressed for years.
When she pulled out of the boy's ass, his asshole was gaping open and any attempt on Dave's part to try and pucker his asshole sent a shooting pain through his asshole. He lay there with his legs dangling over the side of the bed. He didn't want to move. Lizbeth went to the bathroom and drew a tub full of very warm water with bath oils. She went back and helped Dave sit up and walked him to the bathroom and helped him step over the rim of the tub. She helped him sit down in the tub and kissed him while she washed the sweaty body. She let him soak in the tub until the water got cold. She drained the tub and had Dave stand while she used the hand-held shower nozzle to rinse off his body before drying him off. She kept him entertained and walking around until Dave could walk without looking like he still had a cock up his ass.
Dave was eventually allowed to get dressed and walk home. Dave matured faster than most teenage boys his age. Girls seemed to recognize the maturity in him and sought him out for sex. Also, the gays that Dave met also recognized him as a kindred spirit and wanted sex with him. Even Dave's mother assumed that he was fucking the beautiful older woman. She never caught on that Lizbeth was a transsexual. Dave grew to be a bisexual and remained friends with Lizbeth for many years.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com
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