Ryan, Debbie and Debbie's Pantyhose Vol 1 F/M

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COOChob
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Ryan, Debbie and Debbie's Pantyhose Vol 1 F/M

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I have known my friend Ryan since we were 5 or 6 years old, we are now 47. Ryan came to visit me and my wife over this past holiday break. While he was here, he told me about his relationship with his Dad's 2nd Wife Debbie and I was absolutely blown away with what he told me.

To give you a background and a visual on this, Ryan was and still is a small lean guy. He's only 5'-4", has always been extremely lean has a little bit of muscle and is very proportionate. When we were younger, he didn't wear normal underwear, it was mostly stripper underwear. He has an enormous unit; he would strip down to his underwear at parties and in public all the time. Most of his underwear was animal print, some of them were thong. For the most part people thought he was funny, but he was really doing it so girls would see his package. I believe this helped him tremendously with the ladies considering his height challenges. His Dad 's 2nd marriage was to a woman named Debbie who was an inch or two taller than Ryan, probably weighed in around. 125, had short blond hair. Debbie was attractive, but the thing I loved most about Debbie was the fact that she always wore tan pantyhose. They had a pool and on occasion she would come outside and sunbathe, this was the only time I ever saw her when she wasn't wearing them. They lived in a really nice house with white carpet and there was a no shoes rule, so I got to see Debbie's stocking feet a lot in my formative years, and I loved it. Ryan's Dad and Debbie separated our Senior Year in High School not long after Ryan's 18th Birthday and his Dad moved out. Instead of going with his Dad or moving in with his Mom, Ryan elected to stay in their house with Debbie. I noticed some weird things that took place after his Dad moved out but didn't realize what was going on. Ryan started doing things to "get in trouble" and there was some sort of weird vibe between them. I thought it was weird how an 18-year-old would still get punished by a woman that wasn't even related to him anymore and how they used to have these devious smiles on their faces. As soon as I turned 18, Debbie would say weird things to me that had mild sexual innuendos, like "you're a bad boy" type stuff, I couldn't fathom that she meant to be sexual at the time. Ryan used to beat off nonstop and clean up with a hand towel he hid under his bed, he and Debbie had a cat and mouse game going on with that too. He would tell me she found it and he got in trouble, but he would just get another towel and do it again and put it in the same spot, I always thought that was weird.

Fast forward 28 years, Ryan came into town on Dec 26th to stay with us through New Years. Me, my Wife and Ryan were drinking at the bar in our kitchen when my Wife busted me out for my stockings and bondage fetish. This was the 1st time Ryan stayed with us and she does it to try and embarrass me in front of my friends the 1st time they stay. Shelly went to bed around 10:30, Ryan and I went out into the garage to continue drinking and he asked me about the bondage. I didn't go into great detail; I just told him that we used to tie up girls in the neighborhood and then a few girls I dated after were into it including Shelly my wife. He then told me he used to love getting tied up and that when his Dad moved out, Debbie started tying him up for punishment. I told him that it sounded hot, that I always thought Debbie was hot and that I liked her stocking feet with the hopes that the mutual kink would get him to tell me more and it worked.

He told me that he was into pantyhose and stockings too, I think it's a very common kink for guys our age because tan hose were a staple of the female wardrobe when we were growing up. He told me after his Dad moved out, Debbie started getting kind of flirty when he would do minor things that she didn't think were appropriate, it all started on a weekend when Debbie's daughter (from a previous marriage not related to Ryan) was staying over at her Dad's. Debbie unexpectedly came home early on a Friday afternoon, Ryan decided to rub one out while he had the house to himself. He said he had collected pictures that he used to beat off to. Some of them were pornographic and some of them were fully clothed women that were wearing short skirts, pantyhose and high heels. He had stolen a pair of Debbie's pantyhose and that he would wrap around his cock to beat off. He was naked, kneeling in the floor of his room with a picture of a woman fully dressed sitting on the bottom drawer jerking off with Debbie's pantyhose wrapped around his cock. He was right next to the bedroom door and the door was barely open, he noticed that the door moved a little but didn't know why. It was Debbie coming in the side garage door and the air pressure moved it and shortly thereafter, she turned into his bedroom and caught him jerking off to a picture of a full clothed woman, her pantyhose and dirty talking out loud. His life flashed before his eyes, he was horrified, completely embarrassed and immediately figured she was going to tell his Mom and Dad and force him to move out. He also thought she would tell her daughter who was only a couple of years behind us in school and she would tell everyone at school.

Instead of just shutting the door and leaving him be so he could gather himself, she wanted an explanation of what he was doing. She wanted to have the discussion with him while she stood over him, this was making him even hornier and his boner wasn't going away. She told him to put on some shorts and come see her in the living room and that's what he did. When he got in there, she asked him how long he had been jerking off like that and made a comment that the woman in the picture wasn't even naked. He was too ashamed to discuss it with her and asked her not to tell his Dad. She told him that she wouldn't tell anyone, but there had to be consequences for his actions, and they needed to talk about ground rules going forward. She told him that she didn't want him walking around the house in his underwear anymore, he needed to wear shorts, she didn't want to catch him jerking off again and if she found her pantyhose or a crusty towel in his room that he would get punished. Ryan was 18 at the time, he could have moved in with his Mom or Dad, so he said he was already feeling a sexual power play vibe from Debbie and his cock was raging hard the entire time. His cock is so big, it was front and center, but Debbie didn't even acknowledge it. He agreed to follow the rules before she even told him what the punishment would be, then asked. She told him that if he couldn't keep his hand off his cock, she would tie him up so he couldn't touch it. She even went into detail telling him she was going to take him to Ace Hardware and buy some rope in front of him, he was going to have to watch them cut it off the roll in lengths specified by Debbie. He was so horny at this point, he said his balls were killing him, so he told her they had rope in the garage, she wouldn't need to take him to Ace. She told him to show her, so they went into the garage, and he showed her a box where his Dad had some cotton rope. She took it all out and untangled it to see what she had and then said, this will work for the time being, but I still want to buy some rope for you. You need your own rope that I can write your name on. She told him that she was going to keep it in her purse so if they were out somewhere and he started running his mouth, she would tie his hands behind his back and embarrass him and wouldn't care who was around. Then she told him to go to his room and clean everything up. He went back into his room and shut the door, his cock was hard the entire time and he wanted to jerk it off real quick. As soon as he got his shorts off and wrapped Debbie's pantyhose around his cock, she opened the door and was standing there with the rope in her hand and blurted out, "what the fuck are you doing you little pervert, we just talked about this, you couldn't even make it 5 minutes!" He was stunned, he figured he would be done whacking off in a few pulls, but she was right behind him. He said he got a nervous feeling because he didn't know what she was going to do to him, he thought she was really angry at this point. She told him to turn around and put his hands behind his back and he did.

She tied his hands behind his back really good, he said he had been tied up before playing games when he was younger, but he had never been tied up like this. When she was done, she picked up her pantyhose off the floor and told him he was disgusting and went on about his sick pantyhose perversions, she continued to embarrass him while his hands were behind his back and his cock was sticking straight out. She told him she had things to do and he would need to stay there while she did them and left him there. He could hear her cleaning up around the living room, he wanted to dry hump the side of his bedspread, but he knew he couldn't clean up afterwards because she tied his hands good. She came back into his room, made him lay down in the floor while she cleaned up his room. He was laying on his hard cock and he watched her feet as she moved around the room. He was trying not to move too much because he didn't want to carpet burn his junk and he didn't want to get off like that because he couldn't take that kind of embarrassment. When she was done, she shut out the light and left the room. He got himself up and moved over to the bed, his comforter was a light flannel material that was very soft, so he started dry humping it. It didn't take long before he shot a massive load all over the side. He said the comforter was dark green with a white and blue pattern and his load was so noticeable that you could probably see it from space because it hit the areas that were dark green. After the euphoria of the orgasm was over, fear of what would happen to him set in. He had no choice but to release the load, but he was now living in a world of regret.

He told me a lot more, the good part is yet to come, but I have to stop this here. I will continue this in the next couple of days.

*I'm going to continue at least the 1st part of this post in the comments section so it's easier for people reading it to track it.
Last edited by COOChob 1 year ago, edited 3 times in total.
Lost_the_keys
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Post by Lost_the_keys »

Great start!
jone123
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Post by jone123 »

great start indeed, please share more
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Tie_me_up91
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Post by Tie_me_up91 »

Great set up!
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Post by charliesmith »

Please continue. It sounds very intriguing and interesting!
Please feel free to read and comment your thoughts.
My ongoing stories:

Roadtrip of Dreams (M/F) Chapter 14 Added.
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COOChob
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I'm back, I had to go to a meeting and I've been timed out on previous posts so I thought I would post the last at a good breaking point. Before I get back into it, Ryan told me this story the 1st night he was here. He didn't tell me the stories this fluidly, I had to ask a bunch of questions to get these details but I'm writing it with the pieces filled in. Over the 5 days he was here, I shared a few of my experiences with him so that he would share more of his with me. A couple of them were boring and uneventful, but a few others were good enough to share and I will follow those up in separate posts.

When I left off, Ryan had just dry humped his comforter and released a massive load that left a stain. After the euphoria of the orgasm left his body, he got nervous. This was new and sudden, and he started to wonder if Debbie was getting off on it or if she actually thought it was punishment. In addition, the load was massive and it was all over the white carpet. Debbie was obsessed with keeping the carpet pristine, he figured even if Debbie was getting off on this, he was going to be in real trouble if there were carpet stains.

Debbie walked back into the room and immediately noticed the stains on the comforter and his fresh load on the carpet. She asked him why he got up off of the floor and how he was able to get off without touching his cock. He was too ashamed to answer her, she said "If I leave you alone for 2 seconds you'll figure out a way to play with that little cock" and then abruptly left the room (he said she always referred to his dick as "little cock" since his dick is massive, it was a huge turn on for him to hear her say it). He thought she was going to get something to clean up, but she came back in holding another length of rope. He was on his knees in front of the bed, she told him to turn around and bend over the bed. Since she wasn't worried about cleaning up the floor, he realized at this point that Debbie was getting off on his punishment and his dick got hard again. Debbie made a comment about his cock getting hard and how he should be ashamed of himself for being a sick little pervert. He shuffled around and leaned up against the bed, he was too short to lean over it. Debbie tied his feet together and stood next to him, she said "I'm gonna whip you into shape if it's the last thing I do" and spanked his ass, she kept spanking him alternating ass cheeks while she verbally belittled him. He had never been spanked before in a sexual manner and he was loving it. His hard cock was rubbing the side of the comforter again and it felt really great, he was pretending to squirm away from the spanking, but he was squirming because so he could rub his cock on the soft material without blatantly dry humping the bed.

As she was spanking him and belittling him, he was starting to build up another load until she eventually told him that she was going to keep rope in her purse and if he acted up when they were out, she was going to tie his hands behind his back, tape his mouth shut, pull his pants down and spank his ass in front of everyone. He said he imagined how embarrassing that would be and started shooting the second nut all over the side of the bed. He said the load was enormous and it just kept flowing out. Debbie didn't overreact about the carpet getting cum all over it, she kept spanking him and scolding him about the fact that he was cumming while he came. Once he was done, Debbie told him she didn't want to see his little cock anymore, she helped him down to the floor and made him lay on his stomach with his head facing the bed. She told him he was not to move until she told him he could. She came back in the room with some floor cleaner a brush and some paper towels. She got down in the floor on her hands and knees to clean up his mess. She positioned her feet where they were in front of his face if he lifted his head up and continued to tell him she couldn't believe how perverted he was. At one point she told him she couldn't wait to tell her Sister Becky how sick he was. He looked up the entire time she was positioned like that so he could look at the soles of her stocking feet. When she was finished cleaning up his mess she left the room with the cleaning products and soiled paper towels and came back in a few minutes later and untied him. She was out of character when she untied him, after he was free, she left the room with the rope and didn't say anything. Ryan wasn't sure why she didn't talk, but was hoping that this wasn't a one and only play session.

He stayed in his room and watched TV for an hour or so before he ventured out into the living room where Debbie was sitting on the couch watching TV. He went out and sat down on the couch and watched TV withe Debbie in uncomfortable silence for a little while before Debbie broke the silence. She told him that tying him up and spanking him didn't seem like a punishment that was going to work for him, he obviously enjoyed it. Ryan was getting confused that Debbie didn't think they just had a very kinky twisted sexual experience. Then she told him that she felt like he didn't respect her and the only way she knew how to make him show respect was for her to control his cock. From now on she owned his cock, and he wasn't to touch it, dry hump anything or be with other women unless he had permission from Debbie. Ryan was dating a girl at the time that he eventually married but he figured he was either going to have to break up with her or he was going to use that relationship to get punishment from Debbie. Just from the single play session they just finished, he was a full-on bondage addict and who could blame him.

I was completely blindsided by this story, the fact that this was happening while I was at his house regularly made me wish I could go back in time. I would have given anything to have had Debbie strip me naked and tie me up when I was 18 years old, I can't even imagine what that was like for him. I beat off hundreds of times thinking about tying Debbie up because of the outfits she used to wear with pantyhose. Debbie worked at her Sister Becky's clothing store, and we would go by there to see here on occasion. She wore similar outfits to this, but I saw her in a sheer off white one-piece dress outfit that was real short and instead of the dress opening up at the bottom, it was shorts that were shorter than mid-thigh, the neckline was deep, and she was showing cleavage. Best of all she was wearing sheer tan pantyhose with white peep toe high heels that had a strap in the back where her pantyhose heel and the arch of her foot was visible. For years after I saw her in that particular outfit, I would fantasize about wrestling her to the ground and hogtying her in the floor of the store during my beating off sessions. Unfortunately, I had no idea I probably could have worked something out like that if I knew what I know now.

She tied Ryan up for punishment for 7 or 8 months, until she got into a car accident that messed her back up really bad. The punishments increased in kink factor, and I will share a few of the other instances he told me about in future posts, I will name them the same and just put Vol 2, Vol 3 and so on until I get them up.

I hope you enjoyed.
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Tie_me_up91
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Post by Tie_me_up91 »

Wish I Debbie in my life when I was 18!
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COOChob
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Post by COOChob »

How do you think I feel? I was at his house 5 days a week and regularly stayed the night there and had no idea it was going on.
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Tie_me_up91
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Post by Tie_me_up91 »

Must have been pure agony! Lol.
Can’t wait to hear more about it in the volumes.
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Post by dogrednuht123 »

Super hot. Thanks for sharing. Can't wait to hear more. Love it.
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Post by Tiengag5 »

Great bondage story.
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