We find Jesse Martin sipping his morning coffee on the spacious back deck of his ranch house. He had just turned fifty and had retired as he was financially set for life. He admired the lush lawn and shade trees of his back acreage and smiled to himself. It cost a small fortune to have it maintained, but it was worth it.
For twenty years he had lived in a tiny two-bedroom apartment above a Chinese restaurant where he spent the bulk of his time sitting in front of his desktop researching possible investments.
A modest inheritance and his work at a small firm helped him with his plans and as time went on, his portfolio grew. Finally, the day arrived when he decided to liquidate it, this sprawling ranch house was one of his rewards. He caught movement out of the corner of his eye and saw the pretty young lady with the long brunette hair walking up his driveway, she was even earlier than promised.
His heart began to beat a little faster with desire at the sound of her high-heeled thigh-high boots as they echoed between the houses in the thin early morning sunlight, it only increased his want for her. Her short black pleated skirt bounced off the exposed portion of her nylon-covered thighs as she moved and Jesse found himself getting harder by the second.
“If you do this, there is no turning back,” he said to himself.
The girl headed to the back of his spacious ranch house and mounted the stairs to the deck where she found him waiting by the sliding glass doors. He slid open the doors. She placed a small kiss on his cheek as she entered his house.
Over the course of the first six months after he moved in he had come to know all the people in and near his house and they had come to know him, his neighbors recognized him as a polite and quiet man. When their kids went door-to-door selling candy or magazines for a school fundraiser he always made a substantial purchase.
It was the first week in May that he first saw this attractive girl on the back deck of Barclay’s house, which was behind his house and two doors down. She was clad in an almost see-through silk robe that did nothing to hide her magnificent body. She was also sipping on a cup of coffee and to Jesse everything about her was perfect.
He Jesse believed that he knew all the neighborhood girls and wondered how he had missed this one.
Now Jesse didn’t do well with his female classmates in high school, college was a little better, but it was his shyness that kept him from succeeding with the girls he met. Masturbation and online porn helped him survive these lonely times. As time passed, he became less shy and had plenty of dates but never more than one with the same girl, they all had marriage and children on their minds, and these goals were not high on Jesse’s priorities.
Jesse darted back inside and found a large piece of white cardboard from a recently delivered package. He then took a jumbo magic marker and wrote out his cellphone number in big, bold letters.
He went back outside and whistled loudly, causing the girl to look in his direction. She saw the sign that he held up and a second later she pulled a smartphone out of her robe’s pocket, a heartbeat after that his smartphone rang, it was this raven-haired beauty on the other end.
“Good morning,” he heard her say.
“And a good morning to you,” Jesse responded.
“That is a novel way to get someone’s attention,” she stated.
“Well, I wasn’t going to yell,” he informed her.
“I’m Jesse,” he informed her.
“Yes, I know. My name is Ilsa.”
Jesse complimented her on her outfit and she moved closer to the railing to give him a better look and he was overjoyed and his cock hidden under his terrycloth robe became harder by the second. When she ended the call due to her enrollment in an online university, Jesse headed back inside and extracted his throbbing manhood, and stroked himself as he recalled the image of her leaning over the railing.
Soon their conversations while on their respective decks over their morning coffee became a daily occurrence and Jesse looked forward to them as had been without female company for quite some time. Over the course of the following weeks, her attire became even more alluring. See-through babydoll nighties were often hidden under her robe and one morning she parted her robe to reveal that she was clad in the prettiest bra and panty set that he had ever seen aside from his beloved porn sites.
When he complimented her on her ensemble, she confided that she loved dressing like this and had purchased some new outfits just to wear for their morning chats and Jesse felt flattered.
“I was unaware that the Barclays had such an attractive daughter,” he told her one morning after she revealed that she had a full-length white slip under her robe.
There was a long pause on the other end before she responded.
“They don’t,” she said simply.
There was a long pause on Jesse’s end as his brain was processing what he had just been told. He was surprised that he did not lose his erection, in fact, it had become harder than normal. He blamed his condition on the porn sites that he surfed and the day he accidentally clicked on the trans section.
Jesse found himself wide-eyed at the visions before him. Here were some of the most attractive ladies dressed in the most erotic lingerie that he had ever seen. They were even more attractive than some of the college girls that he had dated. As he clicked through the images he found himself getting as stiff as steel.
He had to constantly remind himself that as sexy as they looked, these were young men dressed and made up as women and he was forced to click onto a different site in an attempt to put those images out of his head.
“Are you still there?” he heard Ilsa inquire, which brought him back to the present.
“Yes, I’m here,” Jesse replied.
“I thought that maybe you hung up on me now that you know the truth,” she confessed.
“I would never do that,” Jessie replied.
Over the course of the next hour, before her online classes began, Ilsa began to relate the story of her life. It seemed that as a young man he had become fascinated with silky lingerie. As he had no sister to borrow from and he couldn’t bring himself to borrow his mother’s clothing, he began to prowl the second-hand shops as well as order items online.
Ilsa confessed that the first time he slipped on a pair of panties, the orgasm he experienced was one of the most intense feelings he ever had.
“Soon the lingerie and nighties weren’t enough and I began to order skirts, blouses, nylons, and heels of all types,” she continued.
“I take it that your parents are unaware?” Jesse asked.
“Yes. This is not something you share with family,” she responded.
“What about your friends” Jesse inquired.
“I don’t have that many friends. I started taking online classes since junior high after the first time I was jumped and beaten up for being too girly,” she confided.
“How do you pay for all those pretty things?” Jessie asked.
“A small inheritance from my grandfather plus I work part-time from home.”
Before Jesse could ask another question Ilsa informed him that it was time for her classes to begin.
“Tomorrow?” he asked.
“Tomorrow,” she affirmed.
The moment she disappeared inside her house Jesse darted inside his and flopped on the couch. He untied his robe, lowered his silk boxers, and grabbed his erect cock. As he stroked himself the image of Ilsa was on his mind and he wound up shooting his wad in the air.
Jesse thought about Ilsa for the rest of the day. During his housework and his weightlifting regime, her pretty face, curvy body, and stunning lingerie were ever-present in his thoughts. The next morning began like most, coffee was made and he took his place on his deck as he waited for her call, he didn’t have to wait long.
They exchanged their morning pleasantries and a second later Ilsa untied her robe to reveal a black bra, garter belt, panties, and thigh-high nylons ensemble and Jessie responded by becoming hard within seconds.
“Oh baby, you look fantastic,” he told her as his cock thickened.
“Are you hard?” she asked.
“Every time you show me what’s under your robe I get hard,” Jesse admitted with a touch of embarrassment.
“I’m glad that it’s not just me that gets turned on. I get excited showing you what I’m wearing,” Ilsa admitted.
“Well, I guess you need to invite me over for coffee so we can meet face-to-face,” Ilsa informed him.
“What about your classes?”
“My grades are good, so missing a class would be no big deal,” she replied.
Jesse was silent as he pondered what she had suggested.
“I have a black pleated miniskirt and thigh-high boots that are matched with a black sweater that I have never worn,” she informed him. “You did tell me that you loved girls in short skirts and boots.”
“Yes I did,” he replied. “Would tomorrow be too soon?”.
“Tomorrow would be perfect,” she responded as the call ended.
