The Older Woman Part 2
I arrived at the pub and saw Carol sitting at a small table by the window. She looked amazing, she was dressed head to toe in black. A tight black top that really showed her fine pair of tits, her hair was up and she was wearing glasses, which made her look even sexier.
Her bottom half was a shorter than normal skirt, black opaque nylons and a pair of very high heeled ankle boots.
We said hello and I offered to get her a drink, she said she already had one so I went to the bar and noticed that although the pub wasn’t busy, it was mainly men on their break from the office and a few builders and tradesman, and they were all glancing at Carol.
I went and sat opposite her and we began to chat, about work to start with and the people in her office, she told me some gossip and we laughed.
Carol then steered the conversation to her footwear and she asked if I liked her boots, I said that I did but asked her how did she mange to drive wearing such high heels.
She laughed and said that she always kept at least one other pair of shoes in her car, which were more practical.
She then said “You have a thing about shoes don’t you”
I was about to brush it off but she followed up with “Its ok to like shoes, why do you think woman wear such sexy shoes when they aren’t easy to walk in”
I started to mumble a reply, when she got straight to the point. “I’ve seen the way you look at my shoes and the other ladies in the office have noticed as well, they say you have no idea what their faces look like but you can tell their shoe size”
“We talk about you over coffee and one lady in accounts claims you have a shoe fetish”
“Is she right?”
At that moment I didn’t know what a fetish was, so again I started to mumble an answer, but again Carol cut me short. “If you have, its ok, I love shoes and perhaps we can help each other”
I asked how and she replied, “You can start by cleaning my shoes, the ones under my desk and every single pair I have, when do you want to start?”
I replied “Now”
Carol said “Good, walk me to my car then follow me home in yours”
I got in my car and followed her, I couldn’t concentrate or process what I was doing or what was going to happen.
After 10 minutes carol pulled into a long driveway which led to a nice house, quite big and obviously worth a lot of money.
I pulled up next to her and she beckoned me to follow her.
She could tell I was nervous, so she said “Relax we are alone”
It was then that I noticed that she had changed from her boots into a pair of black patent court shoes. Carol saw me looking at them and said “I think you do have a shoe fetish” and laughed as she walked into the lounge.
We sat on the sofa and I could not stop staring at her legs and heels.
Carol then said “ I am too old for you but you are nice young man and a lot of the younger ladies in the office wouldn’t hesitate to go out with you, the lady in accounts who thinks you have a shoe fetish really fancies you and she knows we are meeting today”
“What shall I tell her. You do have a shoe thing or you just like them?”
I replied “Not sure, what do you think?”
She replied “ Let’s find out”
I was shaking with nerves and excitement, here I was in a room with a very sexy lady who was about to explore my passion for ladies shoes.
Carol told me to kneel down before her and to take a close look at her shoes, I did as I was told. Carol crossed one of her legs over the other so her shoe was directly in front of my face.
“Get closer, get close enough to be able to kiss them”
I leant forward and as I did I discovered that her black opaque nylons were in fact stockings.
I could feel my cock straining inside my trousers.
Carol then said “Lick the point of my shoe”
I did as I was told, and was so turned on that I thought I was about to cum.
“Now suck the heel, make sure it is spotless”
I must have been on my knees for about 10 minutes but it seemed to go by in seconds.
While I was licking and sucking, I could hear Carol saying “Good boy, well done, make sure you lick every part of my shoe, including the sole”
I was then told to stop.
I leaned back, red faced and almost squirming with the massive erection inside my pants.
“How did that feel?” Said Carol
“Amazing” I replied.
“So if I change my shoes or give you another pair to clean you will know exactly how to do it and how good it feels”
I nodded.
Carol looked at my erection and said “What are you going to do about that?”
I decided to take a chance, “Fuck you with it”
Carol smiled and said “I have already told you I am too old for you but I am sure we can think of something else to do with it”
“Let me show you the rest of my shoes and boots, follow me”
Carol led me to her bedroom, which as expected was large and luxurious.
She opened a door, which I assumed was the ensuite but was a walk in wardrobe.
There were rows of dresses, coats and tops and lower to the ground were more shoes and boots than I had ever seen in one place.
“What do you think”?
I replied “Incredible, have you worn them all”
“Every pair at least once, some for nights out, even some for nights in”
She asked me my shoe size, I told her I was an eight.
“I am a size five, nothing in here would fit you, have you ever worn heels”?
I told her I hadn’t and she replied “I think we should change that, I know a place where they stock your size”
I was intrigued and incredibly excited, my erection hadn’t gone down and Carol had noticed.
“Have you ever worn women’s clothes”?
Again I stammered over the answer but manged to say yes I had.
“Let’s dress you up, see what you look like”
Carol went to a drawer and pulled out a black suspender belt, black stockings and a black girdle.
“I bet you won’t need any help putting these on”
“Take your clothes off”
I stripped and stood there in my boxers.
“And those”
“When you are dressed, come and see me in the bedroom”
I was shaking with excitement as I put the lingerie on, I was desperate to touch myself but more desperate to see Carol.
As soon as I was ready I walked into the bedroom, Carol had removed her clothes and was sitting on the edge of the bed in he underwear, black bra, black knickers and black hold ups and she had kept her shoes on.
She looked at me and smiled, “You do look very pretty, you have great legs”
“With a bit of help, you could look like a girl”
“But that bulge between your legs isn’t helpful”
I wasn’t sure what I was supposed to do or what was going to happen next.
“Come and sit next to me”
I did as I was told.
“What shall I tell the girls at work, shall I tell them you have a shoe fetish and you like dressing in lingerie”?
I replied please don’t, I couldn’t show my face there again.
“Don’t be silly, you will be surprised how many of them would be excited by hearing that, especially the accounts lady who has a thing for you”
“You and her would get on very well, I know she can be very naughty”
Carol then said “Look at the time, I am supposed to be somewhere soon”
“You had better get changed, or shall I keep you like that”
I replied “I can put my clothes back on”
Carol said “But do you want to”?
I shook my head.
“Right, this is what we are going to do”
“You can get changed, but when you come to the office on Monday, I want you to be wearing my lingerie under your work clothes, and I will want proof”
“I might not be in Monday, they may send me somewhere else”
“You will be there Monday, I have spoken to management, you are with us for at least the next three months”
Carol leaned forward and kissed me gently and whispered “Next time, we will sort this out” and squeezed my cock.
I almost exploded, I was on the verge of collapse from sexual excitement and frustration.
Carol stood up “See you Monday” and walked to the bathroom.
Her bottom half was a shorter than normal skirt, black opaque nylons and a pair of very high heeled ankle boots.
We said hello and I offered to get her a drink, she said she already had one so I went to the bar and noticed that although the pub wasn’t busy, it was mainly men on their break from the office and a few builders and tradesman, and they were all glancing at Carol.
I went and sat opposite her and we began to chat, about work to start with and the people in her office, she told me some gossip and we laughed.
Carol then steered the conversation to her footwear and she asked if I liked her boots, I said that I did but asked her how did she mange to drive wearing such high heels.
She laughed and said that she always kept at least one other pair of shoes in her car, which were more practical.
She then said “You have a thing about shoes don’t you”
I was about to brush it off but she followed up with “Its ok to like shoes, why do you think woman wear such sexy shoes when they aren’t easy to walk in”
I started to mumble a reply, when she got straight to the point. “I’ve seen the way you look at my shoes and the other ladies in the office have noticed as well, they say you have no idea what their faces look like but you can tell their shoe size”
“We talk about you over coffee and one lady in accounts claims you have a shoe fetish”
“Is she right?”
At that moment I didn’t know what a fetish was, so again I started to mumble an answer, but again Carol cut me short. “If you have, its ok, I love shoes and perhaps we can help each other”
I asked how and she replied, “You can start by cleaning my shoes, the ones under my desk and every single pair I have, when do you want to start?”
I replied “Now”
Carol said “Good, walk me to my car then follow me home in yours”
I got in my car and followed her, I couldn’t concentrate or process what I was doing or what was going to happen.
After 10 minutes carol pulled into a long driveway which led to a nice house, quite big and obviously worth a lot of money.
I pulled up next to her and she beckoned me to follow her.
She could tell I was nervous, so she said “Relax we are alone”
It was then that I noticed that she had changed from her boots into a pair of black patent court shoes. Carol saw me looking at them and said “I think you do have a shoe fetish” and laughed as she walked into the lounge.
We sat on the sofa and I could not stop staring at her legs and heels.
Carol then said “ I am too old for you but you are nice young man and a lot of the younger ladies in the office wouldn’t hesitate to go out with you, the lady in accounts who thinks you have a shoe fetish really fancies you and she knows we are meeting today”
“What shall I tell her. You do have a shoe thing or you just like them?”
I replied “Not sure, what do you think?”
She replied “ Let’s find out”
I was shaking with nerves and excitement, here I was in a room with a very sexy lady who was about to explore my passion for ladies shoes.
Carol told me to kneel down before her and to take a close look at her shoes, I did as I was told. Carol crossed one of her legs over the other so her shoe was directly in front of my face.
“Get closer, get close enough to be able to kiss them”
I leant forward and as I did I discovered that her black opaque nylons were in fact stockings.
I could feel my cock straining inside my trousers.
Carol then said “Lick the point of my shoe”
I did as I was told, and was so turned on that I thought I was about to cum.
“Now suck the heel, make sure it is spotless”
I must have been on my knees for about 10 minutes but it seemed to go by in seconds.
While I was licking and sucking, I could hear Carol saying “Good boy, well done, make sure you lick every part of my shoe, including the sole”
I was then told to stop.
I leaned back, red faced and almost squirming with the massive erection inside my pants.
“How did that feel?” Said Carol
“Amazing” I replied.
“So if I change my shoes or give you another pair to clean you will know exactly how to do it and how good it feels”
I nodded.
Carol looked at my erection and said “What are you going to do about that?”
I decided to take a chance, “Fuck you with it”
Carol smiled and said “I have already told you I am too old for you but I am sure we can think of something else to do with it”
“Let me show you the rest of my shoes and boots, follow me”
Carol led me to her bedroom, which as expected was large and luxurious.
She opened a door, which I assumed was the ensuite but was a walk in wardrobe.
There were rows of dresses, coats and tops and lower to the ground were more shoes and boots than I had ever seen in one place.
“What do you think”?
I replied “Incredible, have you worn them all”
“Every pair at least once, some for nights out, even some for nights in”
She asked me my shoe size, I told her I was an eight.
“I am a size five, nothing in here would fit you, have you ever worn heels”?
I told her I hadn’t and she replied “I think we should change that, I know a place where they stock your size”
I was intrigued and incredibly excited, my erection hadn’t gone down and Carol had noticed.
“Have you ever worn women’s clothes”?
Again I stammered over the answer but manged to say yes I had.
“Let’s dress you up, see what you look like”
Carol went to a drawer and pulled out a black suspender belt, black stockings and a black girdle.
“I bet you won’t need any help putting these on”
“Take your clothes off”
I stripped and stood there in my boxers.
“And those”
“When you are dressed, come and see me in the bedroom”
I was shaking with excitement as I put the lingerie on, I was desperate to touch myself but more desperate to see Carol.
As soon as I was ready I walked into the bedroom, Carol had removed her clothes and was sitting on the edge of the bed in he underwear, black bra, black knickers and black hold ups and she had kept her shoes on.
She looked at me and smiled, “You do look very pretty, you have great legs”
“With a bit of help, you could look like a girl”
“But that bulge between your legs isn’t helpful”
I wasn’t sure what I was supposed to do or what was going to happen next.
“Come and sit next to me”
I did as I was told.
“What shall I tell the girls at work, shall I tell them you have a shoe fetish and you like dressing in lingerie”?
I replied please don’t, I couldn’t show my face there again.
“Don’t be silly, you will be surprised how many of them would be excited by hearing that, especially the accounts lady who has a thing for you”
“You and her would get on very well, I know she can be very naughty”
Carol then said “Look at the time, I am supposed to be somewhere soon”
“You had better get changed, or shall I keep you like that”
I replied “I can put my clothes back on”
Carol said “But do you want to”?
I shook my head.
“Right, this is what we are going to do”
“You can get changed, but when you come to the office on Monday, I want you to be wearing my lingerie under your work clothes, and I will want proof”
“I might not be in Monday, they may send me somewhere else”
“You will be there Monday, I have spoken to management, you are with us for at least the next three months”
Carol leaned forward and kissed me gently and whispered “Next time, we will sort this out” and squeezed my cock.
I almost exploded, I was on the verge of collapse from sexual excitement and frustration.
Carol stood up “See you Monday” and walked to the bathroom.
18 days ago
