Shoesession

nsagaa wrote: Tue Feb 21, 2023 1:53 am When I was in my late teens, I took some risks to fuck a friend’s sister’s shoes a few times. Never ever did I get an easy chance at her shoes. She was the hottest woman I knew back then, fit, brunette, beautiful face and body, sexy dressing sense but a total bitch to anyone I saw her interact with. Total bratty bitch living with her rich parents till she was 19. Out of all the risky moments, 1 nearly gave me a heart attack.

Me and 4 other friends stay the night at this friend’s pace to play video games when we were 16-17. At around 1am we decide to go to bed. My friend puts 6 mattresses in an empty room in his house so that all of us are in one place and can brainstorm some money making ideas. Pretty soon, the doorbell rings. His parents and sister come back from a party. We all go outside to greet his parents. Nobody every talked to his sister cuz she was a dick to everyone. But as soon as I see her my jaw drops. She is wearing a black glittery dress with silver single strap high heel sandals with a thin ankle strap. Black nail polish on her juicy toes and amazing high arches on her size 5 feet. My dick literally got hard. Fast forward 2 hours, everyone fall asleep (atleast I think). I quietly get up without any plan in mind and walk to her room. Her door is shut. With my heart absolutely racing, I try the knob. Not locked. My penis brain keeps telling me that she is asleep since she is tired. I can go in. But my real brain tells me to go to bed. This is unexplainable if I get caught. Even her parents are home. So I open the door . Her face is staring right at the door. She sees me but as I look carefully to make sure if I need to run away or not, I realize that her eyes are close. She is snoring. In deep sleep. I see the heels and the dress on the damn floor. I go in and pick up the heels and get out. I’m not thinking about how I will put them back. I’m just thinking about fucking her heels. Now I need to find a place where I can fuck them. The restroom is in the room where everyone is sleeping but I can’t go in there. So I start fucking the heels in the hallway hiding behind the couch. I cum so hard and make a big mess in her heels but as soon as I do that I hear a door creek. It’s my friend. He fucking sits on the couch I’m hiding behind and starts talking to his gf. I am so fucked. Fortunately, he gets up in the longest 10 mins and goes to the kitchen. That’s my chance to get out of there. But I can’t go to his sister’s room to put the heels back. The only place I can go is the room where everyone is sleeping. But I have the heels with me. I just freak out and go to the room where everyone’s sleeping. It’s pitch dark so I guess nobody knows I was away. I hide the heels under the cover and wait for my friend to come back and fall asleep so I can put his sister’s heels back. Almost an hour passes by before he comes back. I wait and wait but his phone light is still on. He is texting. Another hour or so passes. Another friend wakes up and they start talking, which wakes up everyone. At this point I’ve put the heels in my backpack. I am so fucked. I tell them that I am feeling sick so I am going to try and sleep it off so be quite or get out of the room lol. They go sit in the hallway. A couple of them leave and then everyone else leaves. In the meantime I had nothing to do and my dick somehow got hard again with the thought of her heels so I fucked them again in the bathroom this time since nobody was there. I cleaned them up even though I wanted to leave some for here. I am so tired and sleepy by now but I know that I can’t leave before putting the heels back. I just crash for a couple hours. Big mistake. Thinking back, I should have just put the heels in the hallway and hoped that she thought she took them off outside last night maybe. Anyways, when I wake up, I see a message on my phone from my friend that he had to leave and I can just leave whenever I want as his parents are at home. I go outside and his mom is in the kitchen. She insisted that I eat breakfast before I leave. So I eat breakfast with my friend’s parents and his sister. Nothing tells me that she noticed that her heels are gone yet. So I do have a chance still. But she just finishes off her food and tells her mom that she needs to get ready for her friend’s birthday party now and leaves. I am so fucked lol. At this point, I am ready to just leave the heels on a shoe rack near the entrance door and hope for the best. All of a sudden his sister comes out of the room and starts frantically looking around the house. I have a clear view of this from the dining table. Her mom says, “what are you looking for?”. She says, “I need to take the shoes I wore last night for tonight’s party but I don’t remember where I took them off.”. Her mom tells her to look in her room and she says they are not there even though she thought she took them off there. I was having a heart attack. I just say, “I can help you look for them. What do they look like?”. She explains which turns my so ON while I am having a heart attack at the same time. Super weird feeling. I tell them I will look in the common area, and tell her to look in her room again since at this point she clearly isn’t super sure that she took them off in her room. I quickly take them out of my backpack when nobody is looking and go to her room. “Are these the ones?”. “Oh my god, yes. Where were they?”. “Near the shoe rack by the entrance”. “Ah I thought I took them off in my room. Anyways, thanks”. I hand them to her and leave. Thank god I cleaned them.

I got out of there ASAP and didn’t go back for a couple of months lol.

nsagaa wrote: Tue Feb 21, 2023 1:53 am When I was in my late teens, I took some risks to fuck a friend’s sister’s shoes a few times. Never ever did I get an easy chance at her shoes. She was the hottest woman I knew back then, fit, brunette, beautiful face and body, sexy dressing sense but a total bitch to anyone I saw her interact with. Total bratty bitch living with her rich parents till she was 19. Out of all the risky moments, 1 nearly gave me a heart attack.

Me and 4 other friends stay the night at this friend’s pace to play video games when we were 16-17. At around 1am we decide to go to bed. My friend puts 6 mattresses in an empty room in his house so that all of us are in one place and can brainstorm some money making ideas. Pretty soon, the doorbell rings. His parents and sister come back from a party. We all go outside to greet his parents. Nobody every talked to his sister cuz she was a dick to everyone. But as soon as I see her my jaw drops. She is wearing a black glittery dress with silver single strap high heel sandals with a thin ankle strap. Black nail polish on her juicy toes and amazing high arches on her size 5 feet. My dick literally got hard. Fast forward 2 hours, everyone fall asleep (atleast I think). I quietly get up without any plan in mind and walk to her room. Her door is shut. With my heart absolutely racing, I try the knob. Not locked. My penis brain keeps telling me that she is asleep since she is tired. I can go in. But my real brain tells me to go to bed. This is unexplainable if I get caught. Even her parents are home. So I open the door . Her face is staring right at the door. She sees me but as I look carefully to make sure if I need to run away or not, I realize that her eyes are close. She is snoring. In deep sleep. I see the heels and the dress on the damn floor. I go in and pick up the heels and get out. I’m not thinking about how I will put them back. I’m just thinking about fucking her heels. Now I need to find a place where I can fuck them. The restroom is in the room where everyone is sleeping but I can’t go in there. So I start fucking the heels in the hallway hiding behind the couch. I cum so hard and make a big mess in her heels but as soon as I do that I hear a door creek. It’s my friend. He fucking sits on the couch I’m hiding behind and starts talking to his gf. I am so fucked. Fortunately, he gets up in the longest 10 mins and goes to the kitchen. That’s my chance to get out of there. But I can’t go to his sister’s room to put the heels back. The only place I can go is the room where everyone is sleeping. But I have the heels with me. I just freak out and go to the room where everyone’s sleeping. It’s pitch dark so I guess nobody knows I was away. I hide the heels under the cover and wait for my friend to come back and fall asleep so I can put his sister’s heels back. Almost an hour passes by before he comes back. I wait and wait but his phone light is still on. He is texting. Another hour or so passes. Another friend wakes up and they start talking, which wakes up everyone. At this point I’ve put the heels in my backpack. I am so fucked. I tell them that I am feeling sick so I am going to try and sleep it off so be quite or get out of the room lol. They go sit in the hallway. A couple of them leave and then everyone else leaves. In the meantime I had nothing to do and my dick somehow got hard again with the thought of her heels so I fucked them again in the bathroom this time since nobody was there. I cleaned them up even though I wanted to leave some for here. I am so tired and sleepy by now but I know that I can’t leave before putting the heels back. I just crash for a couple hours. Big mistake. Thinking back, I should have just put the heels in the hallway and hoped that she thought she took them off outside last night maybe. Anyways, when I wake up, I see a message on my phone from my friend that he had to leave and I can just leave whenever I want as his parents are at home. I go outside and his mom is in the kitchen. She insisted that I eat breakfast before I leave. So I eat breakfast with my friend’s parents and his sister. Nothing tells me that she noticed that her heels are gone yet. So I do have a chance still. But she just finishes off her food and tells her mom that she needs to get ready for her friend’s birthday party now and leaves. I am so fucked lol. At this point, I am ready to just leave the heels on a shoe rack near the entrance door and hope for the best. All of a sudden his sister comes out of the room and starts frantically looking around the house. I have a clear view of this from the dining table. Her mom says, “what are you looking for?”. She says, “I need to take the shoes I wore last night for tonight’s party but I don’t remember where I took them off.”. Her mom tells her to look in her room and she says they are not there even though she thought she took them off there. I was having a heart attack. I just say, “I can help you look for them. What do they look like?”. She explains which turns my so ON while I am having a heart attack at the same time. Super weird feeling. I tell them I will look in the common area, and tell her to look in her room again since at this point she clearly isn’t super sure that she took them off in her room. I quickly take them out of my backpack when nobody is looking and go to her room. “Are these the ones?”. “Oh my god, yes. Where were they?”. “Near the shoe rack by the entrance”. “Ah I thought I took them off in my room. Anyways, thanks”. I hand them to her and leave. Thank god I cleaned them.

I got out of there ASAP and didn’t go back for a couple of months lol.

qazwsxedcrfv wrote: Wed Mar 01, 2023 9:25 am For some reason I can't upload images anymore, so hopefully just text will do. There have been plenty of chances I've taken over the years, mostly when I was in high school and college. I'd be at a party or at someone's house or have people over and they'd leave their shoes by the door. Sometimes they'd have their shoe closet adjacent to the bathroom which was the best case. Never got caught, but came close. I've gotten smarter and also had fewer opportunities for getting into trouble over the years. Hard to pick just one story. Someone posted a similar question in the bootjob forum, so I'll limit my response here to just stories with high heels.

The closest I ever came to getting caught was as a teenager at home. My sister had moved out of the house so I didn't have constant access to her heel collection anymore. She had a pair of brown pointy-toe stilettos that I loved and she would sometimes wear them over to my parent's house after church. One time the rest of the family was in the kitchen and I snuck off to the living room where she'd left her heels. My dad nearly walked in on me, but I heard him in the hallway just as I was about to cum. I couldn't bring myself to not cum on her shoes after getting to that point, so I splattered her heels and had just enough time to slide them under the couch and put my dick away before he came in. Fortunately he was just passing through the room so I grabbed her heels to put them back. It was one of the biggest loads I've ever blasted a pair of shoes with, if not the biggest. There was a big pile of cum across the toes that was dripping off onto the carpet. I was honestly surprised at how much cum I covered them with. I wiped off what I quickly could on the carpet since I didn't want to risk going off to grab a towel or something. My sister left not much later, maybe 20 or 30 minutes afterward. She didn't notice anything, but there was definitely some wet residual cum on her heels when she left the house wearing them.

Posted this story in the cabin crew forum a while back, but this was probably my highest stakes shoe cumming adventure. Just going to repost here:

I was getting on an early morning flight and by luck (didn't pick my seat) I got an aisle seat in the back by the bathrooms. This part isn't relevant to the shoe storage, but as I was boarding one of the FAs needed to squeeze by. The guy in front of me was fumbling with his luggage in the overhead bin, there were people behind me, and people already sitting on both sides of the aisle, plus I had on a backpack so I made as much room for her as I could but she bumped right into me and there were a couple of glorious seconds where she got entangled with me. She was young, cute, and wearing heels, which made it even better.

Shortly after takeoff, the same FA who bumped and kicked me earlier slid a bag under the seat across from me (see picture). I saw her wearing flats and heard a 'clunk' as she dropped them on the floor, so I knew it must be her heels in the bag. Luckily, there were a number of empty seats around me in the back and since it was an early flight a lot of people were asleep. When they started the cart service there was no crew in the back, so I just waited for a couple of people to clear out of the bathrooms, made sure the few people near me were asleep or not looking, then took my chance. I dropped my jacket on the floor as I was getting out of my seat so I'd have a reason to bend down. I quietly slipped her bag under my jacket and carried it into one of the bathrooms. Sure enough, it was the same pair of heels that she had kicked and stepped on me with earlier. I got my revenge by fucking them for about 5 mins. I was hoping to shoot a big cumload across them and slip them back in her bag to dry and leave cumstains, but with the time and space I had the best I was able to manage was a little cum that I smeared across the toes. I also wish I'd been able to piss on them, but I didn't have anything in me. I didn't want to push my luck as I knew I needed to finish before the crew made their way to the back with the carts. I put her shoes back in the bag and wrapped them up in my jacket. Fortunately, it was still quiet and nobody was in line for the bathrooms, so I quickly slipped her bag back under the seat and sat down.

One more story, this one happened with the most people around. I shared this story on a different site, so just going to copy and paste here as well:

The most epic shoe cumming experience I had at a party was at a friend's wedding. They arranged for limos to pick up guests at designated hotels, and this one particular guest was staying at the same hotel as me. She was a bit older, maybe 10 years older than me, incredibly hot, and wearing pointy stilettos. She sat next to me in the limo and, intentionally or not, kept stepping on my foot and popping her heel out of her shoe while doing it. Unfortunately she was seated at a different table than me at the reception, but I noticed on the dance floor she had taken her shoes off. Her table was all the way in the corner, so I stealthily made my way all around the tables on the way to the bathroom. As I rounded the corner, sure enough her heels were lying on the floor. I knelt down as though I needed to tie my shoe, whipped out my dick, and quickly had my way with her heels. I had the table blocking me from everyone else, but it was exhilarating masturbating with her shoes in the same room as her and everyone else. I didn't want to be too obvious about being down on the floor too long, so I spent as long as I dared and then headed to the bathroom. I just wish I'd had a way to conceal her heels and take them to the bathroom with me for a massive cumload all over them. Later that night on the way back to the hotel she sat across from me in the limo and kept kicking and stepping on me again with her heels. I had a raging boner the whole ride, and it was so sexy having her touch me with her heels while completely unaware that my cum was on them.

qazwsxedcrfv wrote: Wed Mar 01, 2023 9:25 am For some reason I can't upload images anymore, so hopefully just text will do. There have been plenty of chances I've taken over the years, mostly when I was in high school and college. I'd be at a party or at someone's house or have people over and they'd leave their shoes by the door. Sometimes they'd have their shoe closet adjacent to the bathroom which was the best case. Never got caught, but came close. I've gotten smarter and also had fewer opportunities for getting into trouble over the years. Hard to pick just one story. Someone posted a similar question in the bootjob forum, so I'll limit my response here to just stories with high heels.

The closest I ever came to getting caught was as a teenager at home. My sister had moved out of the house so I didn't have constant access to her heel collection anymore. She had a pair of brown pointy-toe stilettos that I loved and she would sometimes wear them over to my parent's house after church. One time the rest of the family was in the kitchen and I snuck off to the living room where she'd left her heels. My dad nearly walked in on me, but I heard him in the hallway just as I was about to cum. I couldn't bring myself to not cum on her shoes after getting to that point, so I splattered her heels and had just enough time to slide them under the couch and put my dick away before he came in. Fortunately he was just passing through the room so I grabbed her heels to put them back. It was one of the biggest loads I've ever blasted a pair of shoes with, if not the biggest. There was a big pile of cum across the toes that was dripping off onto the carpet. I was honestly surprised at how much cum I covered them with. I wiped off what I quickly could on the carpet since I didn't want to risk going off to grab a towel or something. My sister left not much later, maybe 20 or 30 minutes afterward. She didn't notice anything, but there was definitely some wet residual cum on her heels when she left the house wearing them.

Posted this story in the cabin crew forum a while back, but this was probably my highest stakes shoe cumming adventure. Just going to repost here:

I was getting on an early morning flight and by luck (didn't pick my seat) I got an aisle seat in the back by the bathrooms. This part isn't relevant to the shoe storage, but as I was boarding one of the FAs needed to squeeze by. The guy in front of me was fumbling with his luggage in the overhead bin, there were people behind me, and people already sitting on both sides of the aisle, plus I had on a backpack so I made as much room for her as I could but she bumped right into me and there were a couple of glorious seconds where she got entangled with me. She was young, cute, and wearing heels, which made it even better.

Shortly after takeoff, the same FA who bumped and kicked me earlier slid a bag under the seat across from me (see picture). I saw her wearing flats and heard a 'clunk' as she dropped them on the floor, so I knew it must be her heels in the bag. Luckily, there were a number of empty seats around me in the back and since it was an early flight a lot of people were asleep. When they started the cart service there was no crew in the back, so I just waited for a couple of people to clear out of the bathrooms, made sure the few people near me were asleep or not looking, then took my chance. I dropped my jacket on the floor as I was getting out of my seat so I'd have a reason to bend down. I quietly slipped her bag under my jacket and carried it into one of the bathrooms. Sure enough, it was the same pair of heels that she had kicked and stepped on me with earlier. I got my revenge by fucking them for about 5 mins. I was hoping to shoot a big cumload across them and slip them back in her bag to dry and leave cumstains, but with the time and space I had the best I was able to manage was a little cum that I smeared across the toes. I also wish I'd been able to piss on them, but I didn't have anything in me. I didn't want to push my luck as I knew I needed to finish before the crew made their way to the back with the carts. I put her shoes back in the bag and wrapped them up in my jacket. Fortunately, it was still quiet and nobody was in line for the bathrooms, so I quickly slipped her bag back under the seat and sat down.

One more story, this one happened with the most people around. I shared this story on a different site, so just going to copy and paste here as well:

The most epic shoe cumming experience I had at a party was at a friend's wedding. They arranged for limos to pick up guests at designated hotels, and this one particular guest was staying at the same hotel as me. She was a bit older, maybe 10 years older than me, incredibly hot, and wearing pointy stilettos. She sat next to me in the limo and, intentionally or not, kept stepping on my foot and popping her heel out of her shoe while doing it. Unfortunately she was seated at a different table than me at the reception, but I noticed on the dance floor she had taken her shoes off. Her table was all the way in the corner, so I stealthily made my way all around the tables on the way to the bathroom. As I rounded the corner, sure enough her heels were lying on the floor. I knelt down as though I needed to tie my shoe, whipped out my dick, and quickly had my way with her heels. I had the table blocking me from everyone else, but it was exhilarating masturbating with her shoes in the same room as her and everyone else. I didn't want to be too obvious about being down on the floor too long, so I spent as long as I dared and then headed to the bathroom. I just wish I'd had a way to conceal her heels and take them to the bathroom with me for a massive cumload all over them. Later that night on the way back to the hotel she sat across from me in the limo and kept kicking and stepping on me again with her heels. I had a raging boner the whole ride, and it was so sexy having her touch me with her heels while completely unaware that my cum was on them.