dahoochman
TMF Expert
- Joined
- Sep 16, 2002
- Messages
- 496
- Points
- 63
The Milf and Younger Guy – Part 1
Jen sat at her desk looking out her window at the rainy Northeast weather. It was 4:15 on a Friday afternoon, and her thoughts were consumed with the upcoming Marketing Conference in Orlando she was attending the following week. It was early April, yet the weather felt like February. She was looking forward to the warm Orlando weather. Plus, with no events planned for Friday night, she was free to go out in Orlando and do what she pleased.
The petite 43-year-old was the Manager of Marketing for a large hospitality company. The 5-foot 2 brunette was divorced for 2 years, and her only child was away at college, leaving her to be an empty nester. Since her divorce she rarely dated, choosing instead to focus on her career.
As she sat and pondered what to pack, her co-worker Renee walked in. “Hey Jen” said Renee, taking a seat in a chair on the opposite side of Jen’s desk.
“Hey Renee!” Jen replied.
“Looking forward to the trip next week?” Renee asked.
“God Yes” replied Jen. “I can’t wait to get out of this crappy weather! I’m flying out Monday at noon, and I’m staying a few extra days so I’m coming back Sunday. Got a great rate on the room so I figure why not!”
“I’m not going this time.” Said Renee. “Jason has a game on Friday night that I don’t want to miss.”
“Oh no!” replied Jen. “Who am I going to hang out with? I was really looking forward to us hanging out!” said Jen, dejected. “Besides, it’s no fun being there alone! None of those people know how to hang!”
“I’m sorry sweetie!” replied Renee. “But hey, maybe you’ll meet a hot guy and get lucky! You need to get laid girl!”
“Yeah, right!” said Jen sarcastically. “Meet who? The 60-year-olds with big beer bellies that smoke those stinky cigars and are full of themselves? Or the 25-year-old interns? Most of them are gay anyway!”
“Oh Jen! Be positive! You never know, maybe you’ll meet some cute guy? Anyway, I gotta run, I have to pick up Jason from Football practice! But have a good weekend! I’ll see you next Monday when you get back!” With that, Renee got up, smiled, waved and walked down the hallway.
Jen left shortly after, the typical 25-minute drive took close to an hour due to the lousy weather. Jen spent her Friday night at home as she typically did. Divorced since 2022, Jen had avoided dating, but with her daughter away at college she thought it might be a good time to try to meet someone. “Maybe when I get back.” She said to herself.
On Sunday she pulled her suitcase out of the closet and started to pack for the trip. For the plane ride down, she would wear capri pants and a loose blouse. For the first day of the conference, she packed her “power suit” as she called it: a navy-blue skirt suit with a white blouse, and nude nylons. For Wednesday it was her red pant suit. Another pant suit for Thursday, and a colorful floral dress for Friday. She packed a few pairs of jeans, one for the plane ride home and 1 for if she decided to go wandering at night after convention. Then, she thought about the free weekend she would have in Orlando and decided to pack something sexy in case she decided to go out. She grabbed a short black skirt, black nylons, black sling back heels, and a sheer lacey blouse.
The conference went the same as the many she had attended before: lots of long boring presentations, lots of older arrogant executive men staring at her, and lots of younger female Marketing people dressed wildly inappropriately. Jen had a great time people watching, but there was no one at the conference that interested her.
Friday came, and the conference ended at 4:30, and Jen retreated to her room to change for dinner. She slipped on Jeans, her sling back heels, and a blouse and went to the main dining area. After dinner she walked to the Hotel bar, where the usual groups were gathered to chat. Sitting at the bar she had 2 glasses of wine and sat and watched as the room emptied. Most people attending the conference were flying out that night or early the next day. By 9:30 the bar was almost empty.
With her 2nd glass almost empty the bartender came over. “Another round?” he asked.
“Yes” replied Jen, “But I have a question. Where is the action at? This place is dead! Is there any place near the hotel in walking distance”
“Well,” he replied. “There are some good places to hang in the city, but that’s a 15 to 20-minute Uber ride, not walking distance. There are a few bars about 2 to 3 blocks from here, but this a college town so it might not be your type of crowd.”
“Really?” she replied. “OK well maybe I’ll take a chance. Can you give me directions?”
“Sure, go out the main entrance, turn right, walk to the corner, turn right, and go down 2 blocks. There is one bar on the counter called The Cantina, and across the street is The Hangout.”
“Thanks!” said Jen, as she chugged her wine. “I’ll take the check.”
Jen paid for her check and went back to her room, turning on the TV. After a few minutes she decided it was time to do something. “Screw this” she said to herself. “I can sit home alone any Friday night. I’m gonna have some fun!” She turned off the TV and went to the closet, where she had hung her clothes, grabbing the black skirt and blouse.
Jen got dressed and looked in the mirror. It had been years since she wore something so provocative. Then sitting on the bed, she slipped the sling back heels on her stockinged feet. Glancing one last time in the mirror, she made her way to the door.
Once in the Hotel lobby, she stopped at the front desk and asked one more time if there were any good bars nearby. The clerk pointed her to the same 2 bars that the bartender mentioned. She thanked him and started walking to the door. As she walked she glanced back, and caught the young clerk staring at her as she walked away. “Still go it!” she thought to herself.
Jen walked the 2+ blocks toward the bars, enduring a wolf whistle from some young guys in a passing car, and finally arriving at the corner where the 2 bars were. The Cantina looked dead. But The Hangout seemed to be hopping, with a band playing loud rock music. And then there was the cute guy working the door.
His name was Brian. He was 24, and had graduated from the local University in 2023, where he played Football. He was tall, at least 6’4, and had short brown hair. During the day he took classes working toward his Masters Degree, and at night he worked at the bar. In his spare time he enjoyed video games, sports, and as Jen would find out, had a huge fetish for ladies in nylons and tickling.
As Jen approached, she noticed Brian looking her up and down, with his gaze lingering on her legs and shoes. They made eye contact.
“Can I see your ID please?”
“Oh my god” said Jen, “do I not look over 21?
Looking at her ID, Brian replied. “No, I know you’re over 21, I just wanted to see your name and where such a lovely woman was from, OK Jennifer?” He then flashed a smile, and handed Jen back her ID. “You’re a long way from New Jersey! You must be here for the conference.”
“Very smooth” Jen smiled back. Looking Brian up and down she replied “I think I like it here better!” And with a big smile she began making her way to the bar.
Brian’s eyes followed Jen to the bar, where she climbed on a bar stool and sat, legs crossed. He found himself starting obsessively at her legs. He was smitten.
The bartender approached Jen, and she ordered another glass of wine. The band broke into a Guns and Roses song, and Jen found herself bopping to the beat. As she sat, she looked around the room and realized there were no other women there, just her, with several of the young men at the bar staring at her, and a feeling on uneasiness came across her. Then, turned her gaze back toward the door, she noticed Brian staring at her, and she smiled at him. With that, he walked over to her.
“Don’t worry, they’re harmless” he said, as he sat next to Jen on a bar stool.
“Oh, I’m not worried. If anyone bothers me, I’ll take off this heel and beat them with it.” Jen said with a smile.
Looking down at Jen’s feet, Brian replied. “Well, some of us might like that!”
“Oh my God, you’re too funny!” said Jen, finishing her wine, and shaking her foot nervously as Brian stared.
“Hey, can I get you a drink?” said Brian. “I’m working right now so I can’t drink but I would love to buy you one.”
“Sure!” replied Jen. Brian called the bartender over.
“Hey Billy, give this pretty lady another one, on me. And make it special!” he said with a smile. The bartender smiled back at Brian, nodded yes, and turned to get Jen’s drink.
Brian turned back to Jen and smiled, and as he did Jen recrossed her legs, now left over right, smiling. As she did, the heel strap from her left sling back slipped down over her heel, and her shoe started dangling from her toes. Brian’s eyes stared intently.
“You’ve got to stop doing that!” he said.
“Why?” asked Jen.
“Because that is so fucking sexy! You’re killing me!”
“Oh please, look at you! You must have all of those young sexy college girls after you!” said Jen.
“Yeah, but they’re not sexy, they’re slutty. There’s a huge difference!” said Brian. “I love how you look! The shoes, the skirt, the stockings. The girls my age don’t dress like that.”
“Well, you are very sweet!” Jen replied, smiling and raising the drink Brian got for her. “But I’m almost old enough to be your mother!” replied Jen.
“OK, I know, I’m young. But I’m really a nice guy! So, If you want someone to talk to, I’ll be right over there.” Said Brian, pointing to his stool by the front door.
“Sure thing!” said Jen, smiling. As Brian walked back to his stool, the band started playing a Bon Jovi song, one of Jen’s favorites, and she started dancing in her stool. Brian sat down, staring at Jen as she smiled and shuffled in her seat, the shoe dangling precariously from her toe as her foot bounced up and down, when it happened. The shoe dropped off her toe to the floor with a thud. Brian’s eyes opened wide, and his heart fluttered.
For her part, Jen looked down at the shoe, and then continued bopping in her seat, happy to have her nylon encased left foot exposed. After being in shoes all day, it actually felt good. It was then she noticed Brian next to her, bending down to grab her shoe. On one knee, with the shoe in his left hand, he extended his right hand. “May I?” he asked.
Jen smiled, extending her left foot. Brian grasped her left ankle with his right hand, and looking up at Jen gave her a wicked smile, putting the shoe down on the floor, and with his left hand he quickly traced his fingers over the sole of Jen’s left foot. “Tickle tickle!” he said with a huge smile, running his fingers back and forth over the bottom of her foot.
Jen’s reaction was immediate. She squealed and pulled her left leg toward her. “Hey!!!” she said, big smile on her face, as Brian held on to her left ankle.
“I’m sorry, I couldn’t help myself!” Brian said with a big grin. “But wow, are you ticklish!” he said, now grabbing the shoe with his free hand.
“Oh my god, yes I am very ticklish!” said Jen, now nervously watching as Brian slipped her shoe on. “It’s been a long time since anyone tickled me.” She said.
“Well I’m glad I did, because you have a gorgeous smile and a great laugh!” said Brian, now rising to his feet. Smiling, he returned to his seat at the door.
Jen sat on her stool with a big smile, sipping her drink. Brian’s hands on her legs and feet had actually turned her on a little bit, it had been a long time since a man had touched her, and she could feel the drinks kicking in. She looked at the clock on the wall and it was late, nearly 1:00 am now.
At exactly 1:00 the bar turned on the lights, it was closing time. Brian walked over to Jen. “Take your time, finish your drink, we have to clean up so no rush to leave.”
“I’m fine” said Jen, chugging her drink. “Besides it is getting late, and I should get back to my hotel. As she said that, Jen stood up, but when she went to take a step felt dizzy and unsteady. “Whoah, that’s weird”. Said Jen.
“Are you ok?” asked Brian, grabbing Jen’s arm.
“Yeah, I’m fine, just felt a little off balance.” she said.
Here, sit down for a minute.” said Brian “hey Billy” he called to the bartender. “Bring the lady a glass of water please.”
Smiling the bartender replied. “Sure Brian.” He then poured a glass of water for Jen and put it on the bar.
Brian handed Jen the water. “Here, drink some water, you probably drank too much and it’s hitting you.”
Jen took a sip of the water and put it down. “I’m fine. I didn’t drink that much, not sure why I feel like this? “as she stood up again on unsteady legs.
“OK, slow down, I’ll walk you back to your hotel” said Brian, taking Jen by the arm. “Hey Billy, I’m going to walk her back to her hotel. She doesn’t feel well.”
Billy rolled his eyes and nodded as cleaned glasses at the bar sink. Brian led Jen to the door, and down the sidewalk. “I’m so embarrassed.” Said Jen. “I swear I’m not drunk!”
“Hey, it’s fine.” said Brian. “It happens to the best of us.” The reached the Hotel lobby to find the entry door locked. “Hey, I need your room key to unlock the door.” Said Brian.
Jen reached into her pocket and produced the key. Brian opened the door and led Jen into the lobby and towards the elevators. “What floor are you on?” he asked.
“Twelve” Jen replied. “1218”
The elevator arrived on the 12th floor, and Brian followed the room number sign on the wall to 1218. Opening the door, he guided Jen inside. Once inside Jen walked directly to the bed, a queen size bed with nightstands on both sides, and lie down on her stomach. Brian looked down at the 43-year-old as she lie there in her clothes, her legs dangling off the bed from her calves down, shoes still on. Not sure what do, he sat in the chair at the desk by the foot of the bed. As he looked around the room Jen mumbled “I’m cold.”
Brian stood up and looked around the room. In the closet by the front door, he noticed 2 extra pillows and an extra blanket, so he grabbed the blanket and walked back to the bed, covering Jen with the blanket from her shoulders to her knees. He stared at her nylon encased lower legs as they poked out from under the blanket. Jen wrapped herself in the blanket, twisting and turning, and then sighed.
“Hey, let’s get you comfortable” said Brian, as he sat on the foot of the bed next to Jen’s legs. He reached for Jen’s left leg, lifting her foot slightly, and slipped the strap from the sling back shoe over Jen’s heel and then pulled the shoe off. He then did the same thing for the right foot. Each time, Jen moaned softly. “That’s better, isn’t it?” Brian asked. Jen just moaned, she was falling asleep.
Brian sat on the foot of the bed to the left of Jen’s lower legs, looking down at them. Her feet and legs looked so good in the very sheer barely black nylons she had on. Her gold ankle bracelet contrasted with black nylon material. Her smooth soles pressing against the material as it hugged her foot. She had small feet, maybe size 5.
After a few minutes, he could not control himself. He reached over with his left hand and slowly ran the tip of his pointer finger up the sole of Jen’s left foot.
[/url
]
She reacted immediately, lifting her foot and making an audible moan. He waited for her to put her foot down and did it again, this time a little faster with more pressure, and she squealed.
Jen’s reaction was music to his ears. He reached over to her left foot, leaning over her right, and teased the bottom. Her reaction was immediate, kicking her foot, this time saying “nooooooo”.
Now leaning with his body lying across her legs, resting on his left arm, he used his right hand to start tickling the bottoms of Jen’s feet. With his torso lying across her legs she could not kick, but that did not stop her from trying. Feeling her legs moving under him, Brian used his weight to hold her legs down as he tickled faster. Jen was now squealing, in between saying “noooooo” and “stop!” Her feet were very ticklish, and Brian loved it.
Brian’s left arm was starting to get uncomfortable, so he sat up. But he was not done with Jen’s ticklish feet. Before Jen could move her legs, he climbed on the bed, and throwing his left leg over Jen’s legs he straddled her lower legs facing her feet. Gently lowering his weight on to Jen’s lower legs he sat, effectively pinning her down. Looking down at her helpless soles, he started to stretch his fingers. He was going to tickle the fuck out of her.
Feeling Brian now sitting on her, Jen protested. “Brian, what are you doing?”
[url=https://ibb.co/vCwBS5Bs]
Brian answered with his fingers. Using both hands, he attacked the bottom of both feet, scratching his fingernails from both hands up and down the bottom of both feet. Jen’s reaction went from squeals to hysterical laughter. Brian squeezed his legs together, forcing Jen’s lower legs closer together, making it easier to ticklee both of Jen’s feet, and harder for her to avoid his tickling finger.
Brian was living a fantasy. He had always dreamed of this day: having a sexy Milf with extremely ticklish feet pinned down and helpless. His cock was throbbing in his jeans. The more Jen laughed, the more Brian wanted to tickle her.
After about 2 minutes Brian decided to give Jen a break. He stopped tickling her feet and just sat there, staring down at her lower legs and feet. Jen, who had been thrashing on the bed, collapsed on to her stomach, repeatedly saying “Oh my god, oh my god.” Brian reached for Jen’s lower legs, slowly caressing her silky ankles and calves.
Brian turned around looking at Jen. She was flat on her tummy, head on the side resting on the pillow, breathing heavy. “”Jen?” he said. “Jen?”
With Jen not replying, Brian stood up and walked to the top of the bed and looked at Jen’s face. Her eyes were closed, and she was snoring. “Aww, poor baby.” He thought to himself.
Brian walked over to the desk, grabbed the tiny Marriott writing pad and pen they leave for the customers, and scribbled a quick note. Writing his name and cell number on the paper, he wrote “Had a great time, see you tomorrow? Brian.” He left the note on the desk and left.
To be continued……
Jen sat at her desk looking out her window at the rainy Northeast weather. It was 4:15 on a Friday afternoon, and her thoughts were consumed with the upcoming Marketing Conference in Orlando she was attending the following week. It was early April, yet the weather felt like February. She was looking forward to the warm Orlando weather. Plus, with no events planned for Friday night, she was free to go out in Orlando and do what she pleased.
The petite 43-year-old was the Manager of Marketing for a large hospitality company. The 5-foot 2 brunette was divorced for 2 years, and her only child was away at college, leaving her to be an empty nester. Since her divorce she rarely dated, choosing instead to focus on her career.
As she sat and pondered what to pack, her co-worker Renee walked in. “Hey Jen” said Renee, taking a seat in a chair on the opposite side of Jen’s desk.
“Hey Renee!” Jen replied.
“Looking forward to the trip next week?” Renee asked.
“God Yes” replied Jen. “I can’t wait to get out of this crappy weather! I’m flying out Monday at noon, and I’m staying a few extra days so I’m coming back Sunday. Got a great rate on the room so I figure why not!”
“I’m not going this time.” Said Renee. “Jason has a game on Friday night that I don’t want to miss.”
“Oh no!” replied Jen. “Who am I going to hang out with? I was really looking forward to us hanging out!” said Jen, dejected. “Besides, it’s no fun being there alone! None of those people know how to hang!”
“I’m sorry sweetie!” replied Renee. “But hey, maybe you’ll meet a hot guy and get lucky! You need to get laid girl!”
“Yeah, right!” said Jen sarcastically. “Meet who? The 60-year-olds with big beer bellies that smoke those stinky cigars and are full of themselves? Or the 25-year-old interns? Most of them are gay anyway!”
“Oh Jen! Be positive! You never know, maybe you’ll meet some cute guy? Anyway, I gotta run, I have to pick up Jason from Football practice! But have a good weekend! I’ll see you next Monday when you get back!” With that, Renee got up, smiled, waved and walked down the hallway.
Jen left shortly after, the typical 25-minute drive took close to an hour due to the lousy weather. Jen spent her Friday night at home as she typically did. Divorced since 2022, Jen had avoided dating, but with her daughter away at college she thought it might be a good time to try to meet someone. “Maybe when I get back.” She said to herself.
On Sunday she pulled her suitcase out of the closet and started to pack for the trip. For the plane ride down, she would wear capri pants and a loose blouse. For the first day of the conference, she packed her “power suit” as she called it: a navy-blue skirt suit with a white blouse, and nude nylons. For Wednesday it was her red pant suit. Another pant suit for Thursday, and a colorful floral dress for Friday. She packed a few pairs of jeans, one for the plane ride home and 1 for if she decided to go wandering at night after convention. Then, she thought about the free weekend she would have in Orlando and decided to pack something sexy in case she decided to go out. She grabbed a short black skirt, black nylons, black sling back heels, and a sheer lacey blouse.
The conference went the same as the many she had attended before: lots of long boring presentations, lots of older arrogant executive men staring at her, and lots of younger female Marketing people dressed wildly inappropriately. Jen had a great time people watching, but there was no one at the conference that interested her.
Friday came, and the conference ended at 4:30, and Jen retreated to her room to change for dinner. She slipped on Jeans, her sling back heels, and a blouse and went to the main dining area. After dinner she walked to the Hotel bar, where the usual groups were gathered to chat. Sitting at the bar she had 2 glasses of wine and sat and watched as the room emptied. Most people attending the conference were flying out that night or early the next day. By 9:30 the bar was almost empty.
With her 2nd glass almost empty the bartender came over. “Another round?” he asked.
“Yes” replied Jen, “But I have a question. Where is the action at? This place is dead! Is there any place near the hotel in walking distance”
“Well,” he replied. “There are some good places to hang in the city, but that’s a 15 to 20-minute Uber ride, not walking distance. There are a few bars about 2 to 3 blocks from here, but this a college town so it might not be your type of crowd.”
“Really?” she replied. “OK well maybe I’ll take a chance. Can you give me directions?”
“Sure, go out the main entrance, turn right, walk to the corner, turn right, and go down 2 blocks. There is one bar on the counter called The Cantina, and across the street is The Hangout.”
“Thanks!” said Jen, as she chugged her wine. “I’ll take the check.”
Jen paid for her check and went back to her room, turning on the TV. After a few minutes she decided it was time to do something. “Screw this” she said to herself. “I can sit home alone any Friday night. I’m gonna have some fun!” She turned off the TV and went to the closet, where she had hung her clothes, grabbing the black skirt and blouse.
Jen got dressed and looked in the mirror. It had been years since she wore something so provocative. Then sitting on the bed, she slipped the sling back heels on her stockinged feet. Glancing one last time in the mirror, she made her way to the door.
Once in the Hotel lobby, she stopped at the front desk and asked one more time if there were any good bars nearby. The clerk pointed her to the same 2 bars that the bartender mentioned. She thanked him and started walking to the door. As she walked she glanced back, and caught the young clerk staring at her as she walked away. “Still go it!” she thought to herself.
Jen walked the 2+ blocks toward the bars, enduring a wolf whistle from some young guys in a passing car, and finally arriving at the corner where the 2 bars were. The Cantina looked dead. But The Hangout seemed to be hopping, with a band playing loud rock music. And then there was the cute guy working the door.
His name was Brian. He was 24, and had graduated from the local University in 2023, where he played Football. He was tall, at least 6’4, and had short brown hair. During the day he took classes working toward his Masters Degree, and at night he worked at the bar. In his spare time he enjoyed video games, sports, and as Jen would find out, had a huge fetish for ladies in nylons and tickling.
As Jen approached, she noticed Brian looking her up and down, with his gaze lingering on her legs and shoes. They made eye contact.
“Can I see your ID please?”
“Oh my god” said Jen, “do I not look over 21?
Looking at her ID, Brian replied. “No, I know you’re over 21, I just wanted to see your name and where such a lovely woman was from, OK Jennifer?” He then flashed a smile, and handed Jen back her ID. “You’re a long way from New Jersey! You must be here for the conference.”
“Very smooth” Jen smiled back. Looking Brian up and down she replied “I think I like it here better!” And with a big smile she began making her way to the bar.
Brian’s eyes followed Jen to the bar, where she climbed on a bar stool and sat, legs crossed. He found himself starting obsessively at her legs. He was smitten.
The bartender approached Jen, and she ordered another glass of wine. The band broke into a Guns and Roses song, and Jen found herself bopping to the beat. As she sat, she looked around the room and realized there were no other women there, just her, with several of the young men at the bar staring at her, and a feeling on uneasiness came across her. Then, turned her gaze back toward the door, she noticed Brian staring at her, and she smiled at him. With that, he walked over to her.
“Don’t worry, they’re harmless” he said, as he sat next to Jen on a bar stool.
“Oh, I’m not worried. If anyone bothers me, I’ll take off this heel and beat them with it.” Jen said with a smile.
Looking down at Jen’s feet, Brian replied. “Well, some of us might like that!”
“Oh my God, you’re too funny!” said Jen, finishing her wine, and shaking her foot nervously as Brian stared.
“Hey, can I get you a drink?” said Brian. “I’m working right now so I can’t drink but I would love to buy you one.”
“Sure!” replied Jen. Brian called the bartender over.
“Hey Billy, give this pretty lady another one, on me. And make it special!” he said with a smile. The bartender smiled back at Brian, nodded yes, and turned to get Jen’s drink.
Brian turned back to Jen and smiled, and as he did Jen recrossed her legs, now left over right, smiling. As she did, the heel strap from her left sling back slipped down over her heel, and her shoe started dangling from her toes. Brian’s eyes stared intently.
“You’ve got to stop doing that!” he said.
“Why?” asked Jen.
“Because that is so fucking sexy! You’re killing me!”
“Oh please, look at you! You must have all of those young sexy college girls after you!” said Jen.
“Yeah, but they’re not sexy, they’re slutty. There’s a huge difference!” said Brian. “I love how you look! The shoes, the skirt, the stockings. The girls my age don’t dress like that.”
“Well, you are very sweet!” Jen replied, smiling and raising the drink Brian got for her. “But I’m almost old enough to be your mother!” replied Jen.
“OK, I know, I’m young. But I’m really a nice guy! So, If you want someone to talk to, I’ll be right over there.” Said Brian, pointing to his stool by the front door.
“Sure thing!” said Jen, smiling. As Brian walked back to his stool, the band started playing a Bon Jovi song, one of Jen’s favorites, and she started dancing in her stool. Brian sat down, staring at Jen as she smiled and shuffled in her seat, the shoe dangling precariously from her toe as her foot bounced up and down, when it happened. The shoe dropped off her toe to the floor with a thud. Brian’s eyes opened wide, and his heart fluttered.
For her part, Jen looked down at the shoe, and then continued bopping in her seat, happy to have her nylon encased left foot exposed. After being in shoes all day, it actually felt good. It was then she noticed Brian next to her, bending down to grab her shoe. On one knee, with the shoe in his left hand, he extended his right hand. “May I?” he asked.
Jen smiled, extending her left foot. Brian grasped her left ankle with his right hand, and looking up at Jen gave her a wicked smile, putting the shoe down on the floor, and with his left hand he quickly traced his fingers over the sole of Jen’s left foot. “Tickle tickle!” he said with a huge smile, running his fingers back and forth over the bottom of her foot.
Jen’s reaction was immediate. She squealed and pulled her left leg toward her. “Hey!!!” she said, big smile on her face, as Brian held on to her left ankle.
“I’m sorry, I couldn’t help myself!” Brian said with a big grin. “But wow, are you ticklish!” he said, now grabbing the shoe with his free hand.
“Oh my god, yes I am very ticklish!” said Jen, now nervously watching as Brian slipped her shoe on. “It’s been a long time since anyone tickled me.” She said.
“Well I’m glad I did, because you have a gorgeous smile and a great laugh!” said Brian, now rising to his feet. Smiling, he returned to his seat at the door.
Jen sat on her stool with a big smile, sipping her drink. Brian’s hands on her legs and feet had actually turned her on a little bit, it had been a long time since a man had touched her, and she could feel the drinks kicking in. She looked at the clock on the wall and it was late, nearly 1:00 am now.
At exactly 1:00 the bar turned on the lights, it was closing time. Brian walked over to Jen. “Take your time, finish your drink, we have to clean up so no rush to leave.”
“I’m fine” said Jen, chugging her drink. “Besides it is getting late, and I should get back to my hotel. As she said that, Jen stood up, but when she went to take a step felt dizzy and unsteady. “Whoah, that’s weird”. Said Jen.
“Are you ok?” asked Brian, grabbing Jen’s arm.
“Yeah, I’m fine, just felt a little off balance.” she said.
Here, sit down for a minute.” said Brian “hey Billy” he called to the bartender. “Bring the lady a glass of water please.”
Smiling the bartender replied. “Sure Brian.” He then poured a glass of water for Jen and put it on the bar.
Brian handed Jen the water. “Here, drink some water, you probably drank too much and it’s hitting you.”
Jen took a sip of the water and put it down. “I’m fine. I didn’t drink that much, not sure why I feel like this? “as she stood up again on unsteady legs.
“OK, slow down, I’ll walk you back to your hotel” said Brian, taking Jen by the arm. “Hey Billy, I’m going to walk her back to her hotel. She doesn’t feel well.”
Billy rolled his eyes and nodded as cleaned glasses at the bar sink. Brian led Jen to the door, and down the sidewalk. “I’m so embarrassed.” Said Jen. “I swear I’m not drunk!”
“Hey, it’s fine.” said Brian. “It happens to the best of us.” The reached the Hotel lobby to find the entry door locked. “Hey, I need your room key to unlock the door.” Said Brian.
Jen reached into her pocket and produced the key. Brian opened the door and led Jen into the lobby and towards the elevators. “What floor are you on?” he asked.
“Twelve” Jen replied. “1218”
The elevator arrived on the 12th floor, and Brian followed the room number sign on the wall to 1218. Opening the door, he guided Jen inside. Once inside Jen walked directly to the bed, a queen size bed with nightstands on both sides, and lie down on her stomach. Brian looked down at the 43-year-old as she lie there in her clothes, her legs dangling off the bed from her calves down, shoes still on. Not sure what do, he sat in the chair at the desk by the foot of the bed. As he looked around the room Jen mumbled “I’m cold.”
Brian stood up and looked around the room. In the closet by the front door, he noticed 2 extra pillows and an extra blanket, so he grabbed the blanket and walked back to the bed, covering Jen with the blanket from her shoulders to her knees. He stared at her nylon encased lower legs as they poked out from under the blanket. Jen wrapped herself in the blanket, twisting and turning, and then sighed.
“Hey, let’s get you comfortable” said Brian, as he sat on the foot of the bed next to Jen’s legs. He reached for Jen’s left leg, lifting her foot slightly, and slipped the strap from the sling back shoe over Jen’s heel and then pulled the shoe off. He then did the same thing for the right foot. Each time, Jen moaned softly. “That’s better, isn’t it?” Brian asked. Jen just moaned, she was falling asleep.
Brian sat on the foot of the bed to the left of Jen’s lower legs, looking down at them. Her feet and legs looked so good in the very sheer barely black nylons she had on. Her gold ankle bracelet contrasted with black nylon material. Her smooth soles pressing against the material as it hugged her foot. She had small feet, maybe size 5.
After a few minutes, he could not control himself. He reached over with his left hand and slowly ran the tip of his pointer finger up the sole of Jen’s left foot.
[/url]
She reacted immediately, lifting her foot and making an audible moan. He waited for her to put her foot down and did it again, this time a little faster with more pressure, and she squealed.
Jen’s reaction was music to his ears. He reached over to her left foot, leaning over her right, and teased the bottom. Her reaction was immediate, kicking her foot, this time saying “nooooooo”.
Now leaning with his body lying across her legs, resting on his left arm, he used his right hand to start tickling the bottoms of Jen’s feet. With his torso lying across her legs she could not kick, but that did not stop her from trying. Feeling her legs moving under him, Brian used his weight to hold her legs down as he tickled faster. Jen was now squealing, in between saying “noooooo” and “stop!” Her feet were very ticklish, and Brian loved it.
Brian’s left arm was starting to get uncomfortable, so he sat up. But he was not done with Jen’s ticklish feet. Before Jen could move her legs, he climbed on the bed, and throwing his left leg over Jen’s legs he straddled her lower legs facing her feet. Gently lowering his weight on to Jen’s lower legs he sat, effectively pinning her down. Looking down at her helpless soles, he started to stretch his fingers. He was going to tickle the fuck out of her.
Feeling Brian now sitting on her, Jen protested. “Brian, what are you doing?”
[url=https://ibb.co/vCwBS5Bs]
Brian answered with his fingers. Using both hands, he attacked the bottom of both feet, scratching his fingernails from both hands up and down the bottom of both feet. Jen’s reaction went from squeals to hysterical laughter. Brian squeezed his legs together, forcing Jen’s lower legs closer together, making it easier to ticklee both of Jen’s feet, and harder for her to avoid his tickling finger.
Brian was living a fantasy. He had always dreamed of this day: having a sexy Milf with extremely ticklish feet pinned down and helpless. His cock was throbbing in his jeans. The more Jen laughed, the more Brian wanted to tickle her.
After about 2 minutes Brian decided to give Jen a break. He stopped tickling her feet and just sat there, staring down at her lower legs and feet. Jen, who had been thrashing on the bed, collapsed on to her stomach, repeatedly saying “Oh my god, oh my god.” Brian reached for Jen’s lower legs, slowly caressing her silky ankles and calves.
Brian turned around looking at Jen. She was flat on her tummy, head on the side resting on the pillow, breathing heavy. “”Jen?” he said. “Jen?”
With Jen not replying, Brian stood up and walked to the top of the bed and looked at Jen’s face. Her eyes were closed, and she was snoring. “Aww, poor baby.” He thought to himself.
Brian walked over to the desk, grabbed the tiny Marriott writing pad and pen they leave for the customers, and scribbled a quick note. Writing his name and cell number on the paper, he wrote “Had a great time, see you tomorrow? Brian.” He left the note on the desk and left.
To be continued……
