BondageDating

Caught by My Drunk Mother-in-Law Diane

Caught by Drunk Diane I'm sitting here rock hard thinking about what happened over the weekend It couldn't have worked out any better, I had to stop by my…

member_8d89772085 30 Aug 2026 #1

Caught by Drunk Diane I’m sitting here rock hard thinking about what happened over the weekend It couldn’t have worked out any better, I had to stop by my in-laws on my way home from work around five o’clock to drop off a few things. I knocked on the door but did not get an answer; it looked like nobody was home. I went around to the garage to find the hidden key and let myself in. As I opened the front door, the phone was ringing. I checked the caller ID and noticed that my wife was calling from our house. Answering only to discover that my mother-in-law must have just left about five minutes ago, while my father-in-law would be staying at grandma’s until at least tomorrow. I couldn’t believe my luck; I was going to be alone at my in-laws for at least four hours, and I always wanted to check out Diane’s closet for her shoes. I’ve noticed that Diane had worn nylons most of the time I saw Her, getting hard knowing that I could look through the closet without being caught. I had seen most of her shoes on one occasion or another. As I opened the closet door, I caught the scent of leather in the air. Most of Her shoes were still in their original boxes; it was like Christmas. I had to open them one at a time to identify the styles. I was looking for two different pairs: the first were tan flats, and the second were modest black pumps. I looked through about ten different boxes until I found my prize. First, I took off my pants and decided to borrow a pair of Diane’s grey nylons; I just love how they feel on my legs. I was rock hard after wiggling into them and couldn’t wait to use her shoes. I knelt by the door, pulled a shoe out of each box, and took turns fucking and smelling them. After about five minutes, I had to shoot my load while fucking Diane’s black pump; I came in waves because knowing what I was doing felt different from how most people do it. I calmed down and went to the bathroom to get a washcloth to clean up the mess inside the shoe. That’s when I noticed that the insole of the pump was cloth, not leather. It took a little longer to clean than I thought; I had to soak it slightly to get everything out. Feeling pressed for time, I just put both pairs of shoes back, got dressed, and hit the road. I left in such a hurry that I didn’t realize I was still wearing Diane’s nylons. How surprised she would have been knowing I was inside her nylons as I walked into my own house. Diane greeted me as I entered. I got into the house and out of those nylons without my wife or mother-in-law finding out. I stashed them in a bag with my own nylons and high heels. Still feeling a little shocked at seeing Diane while wearing her nylons, I couldn’t stop thinking about how much fun I had. One nice thing about my job is that I have Mondays off. When my wife works and the kid goes to school, I sometimes like to put on some nylons and high heels for selfbondage. On those days, I get out of bed, wake myself up, and dig out my box of play things with all my nylons, high heels, rope, and handcuffs; just getting the box out starts to get me hard. Because of the thanksgiving holiday, I had an extra day off. With no one home at noon, I decided to have some fun. First, I dug out Diane’s nylons that I was wearing yesterday and put them back on. Next came my red 4-inch high heels; instantly, I became rock hard again. This time, I wanted pictures of my bondage setup, so I got the tripod ready for my Canon XTi camera. I also brought my laptop into the room to plug in the camera and use the capture software, which can be set to take a picture at any interval. Today, I figured twenty seconds would work. First thing was going into the freezer to get out my chunk of ice with the string frozen inside it. There were about six feet of string within the ice, with about a foot sticking out each side of the cube. An eyehook hung in the ceiling just above where my right hand will be tied, so I could tie the key and a bell to one end of the string and loop the other end to the hook. The bell is on the string so I can hear when the drop happens because I’ll be gagged and blindfolded. Now that the camera is running and my release mechanism is set, I can get myself tied up good and tight. First thing I do is loop a rope around each of the legs of my bed frame; I tie each ankle tightly with it overhanging the edge by about six inches. Then I add a second rope to bind my ankles together at two points so they can hardly move at all. I like having my cock tied up too, taking a thin rope to wrap around my waist for a crotch strap, then looping it around the base of my cock and balls before wrapping them nice and tight. With only my hands left, I pull a nylon knee-high over my head and grab some duct tape to cover my eyes. The tightness around my head intensifies everything. My handcuffs are already on each wrist; all that’s left is closing the cuff loops onto the rope strands at just the right length from each corner of the bed. Cuffing my left hand first, I take my right hand and stroke my cock until seconds from cumming, then quickly stop to cuff the right wrist. Now tied tight until the ice melts. I always love the feeling after tying myself up; it’s usually almost enough to push me over the edge into an early climax—happened a couple of times in the past—and when it does, my time tied seems to double. Another thing is that being blindfolded makes your other senses much more acute and active; you start hearing and smelling things normally ignored. I must have been tied up for about forty-five minutes. My arms and legs were getting stiff from lack of movement. The camera shutter had such a constant rhythm, so when I heard a car door shut, it seemed very loud and close. It made me jump even though I knew I wasn’t going anywhere being tethered to the bed like this. I started calculating how long until the ice melted when I heard the screen door open; my heart raced at a hundred miles an hour hoping it was just some delivery. I really panicked hearing the key go into the lock and someone trying the handle. Hoping that staying still would let me get loose before anyone noticed, “Hello, anybody home? Hello! I brought some mail over,” the voice cried out—it was my mother-in-law Diane. Knowing she’d see me in this unusual state meant super humiliation; her only saving grace might be dropping off mail, but luck wasn’t on my side. Wishing I had dead-bolted the door since no one usually comes by. “I guess no one is here,” Diane said aloud as she walked inside. By the sound of clicking on the hardwood floor, I knew she was wearing high heels. “I knew I shouldn’t have had that fourth Mike’s Hard Lemonade so early in the afternoon; I need to use the bathroom again.” She kept talking while I waited for her to find me; she must really need to go because the heel clicks were fast. Then it hit me like a ton of bricks: the camera. The camera is still clicking away! Diane probably didn’t hear it over the sound of her heels on the floor. “Hello, are you off work today? I thought you only had Mondays off? I guess I should have knocked instead of just letting myself in,” Diane said as I heard her shut off the water and open the bathroom door. She must have assumed the camera was me when she heard it clicking.

I’ll admit I’m bound tight to the bed, clad in nylons and high heels with a massive erection resulting from all that activity.

I hear her start walking again; her heels make that lovely clicking sound against the hardwood floor before she stops. “Oh my god, what happened? Why didn’t you call out for help when I walked in? Who did this to you? Are you okay? Oh my god, let me get you out of this contraption.” I was almost hyperventilating; I couldn’t believe she thought someone else had done this. I hoped I could pull off the lie.

“I guess I’ll have to take that ballgag out of your mouth before you can tell me anything,” Diane said as she unbuckled it. “I’ll explain how this happened: I forgot to get Kelly a birthday card on her actual birthday, and she told me the only way to make amends was to let her tie me to the bed in some nylons and high heels and wait here until she gets home,” I said as Diane sat on the edge of the bed, touching my wrist looking for a way to remove the handcuffs. I was glad I remained blindfolded because I felt my face getting red from all the attention.

“I can’t believe she would leave you like this; doesn’t she realize how unsafe it is? What if there was a fire or something? And why did she wrap that rope around your penis that way? It could really be damaging. I don’t think it can get any harder given the look of it.” Diane said, and as I heard a little ding from the bell on the rope, I realized the key must have dropped slightly.

“What is this? I’m starting to think Kelly didn’t do this to you; you did it yourself, didn’t you? I was wondering what kind of kinky daughter I raised, but I guess it wasn’t her after all.” Diane told me with an evil tone in her voice as I felt her hand move away from my wrist and place it just above my waist. “I think I might have had a little too much to drink, but the way I look at it, I can do whatever I want because you’re never going to tell anyone; your story would have to start with ‘I had myself tied to the bed wearing nylons and high heels when Diane came over and found me.’ I don’t think you’re going there, are you?” Diane said, and I knew trouble was coming.

“It’s been a long time since I had a younger man at my disposal to do anything I want with. Any strange thoughts I might have in my head that I’m afraid to share with anyone else, I guess I just found the perfect person to share them with. Before I get started, I’m going to copy all those pictures from your camera and keep them in case I ever need any favors or anything else I can imagine,” Diane told me as I heard her open the camera, take out the memory card, and walk into the other room.

I am pulling and tugging with all my might, doing whatever I can to get loose but without success. I’m working up quite a sweat and getting tired from all my struggling. One thing that doesn’t tire is my rock-hard dick; it’s almost like it has its own mind. In fact, I can tell it’s just about ready to cum, so I have to try to calm myself down before making a mess and really embarrassing myself. I decide to slow down and take whatever Diane dishes out.

“I hope you didn’t think I forgot about you; I now have everything copied nicely and put into my car for safekeeping. Now what should I do with you? Or should I say to you?” Diane said as I felt her drag her nails from my lips to right above my cock. I strained and tugged, doing what I thought would help me get off. “Oh, I just love how hard your cock is; it’s wiggling so much with you trying to get loose. I wonder how much harder it can get? Maybe if I can get you to wiggle some more, it might get even harder.” Diane said as I felt her finger work its way into my side. I pulled away as far as I could to try to escape the tickling; I tugged and began to beg. “Pleeaassseee! Stop! Ha ha ha ha, you have to stop! It tickles way too much!” I said as I tried with all my might to get loose but had tied myself well.

“If your sides tickle this much, I wonder how ticklish the rest of your body is,” Diane told me in a devilish voice. She gave me a break, and I felt her sit on the edge of the bed. I was still breathing pretty hard as she took it away again; Diane lightly touched my rock-hard cock, sliding her nails up and down my shaft with just enough pressure to let me know she was there but not enough to make me cum. “Oh, do you like that? Do you think I should let you cum so quickly? I don’t think so, considering all the effort you used to tie yourself up; it would be a shame.” Diane told me as she started using her other hand to lightly play with my balls. The touch was almost enough to bring me over the edge, but when Diane noticed, she turned things into a new direction. “I think I may have to get a drink from your fridge,” said Diane. “I wouldn’t want my buzz to quit while I’m having so much fun. Do you want something to drink? You know what, that might not be a good idea right now.” Diane told me as I felt her get off the bed and walk down to the kitchen.

The clicking of her high heels was driving me crazy knowing that after all that happened she never took off her shoes. I could tell she’s coming back as she begins to speak. “I never would have guessed you for a guy who likes to wear nylons, let alone high heels; I guess you learn something new about somebody every day. Did I ever ask if your feet are ticklish? Because I think it might be time to find out after I put my drink down.” Diane told me in a playful voice as I heard her set her drink on the dresser next to the bed. “I think I will start with your left foot; it looks like it needs to be tickled,” Diane said as I felt her nail stroking the top of my foot. I tried to pull away and wiggle, but it was no use. “My my my, I would have never guessed a big strong man like you is so ticklish. I think you must really be liking it from the way your cock stays rock-hard. I wonder if I tickle both feet at once can I make you cum? Do you think that’s possible?” Diane told me as I felt her fingers working on the soles of each foot through the opening at the side of my d’Orsay pumps; it was driving me mad and making me hornier. “Please, just stop, let me go, and I will never tell anyone about what happened,” I told Diane begging and hoping she would stop. I was pulling so hard trying to get loose that I was getting lightheaded from all the straining.

I felt her move onto the bed and sit between my tightly tied legs. “I sure hope that’s not all you’ve got for trying to get loose because I’m not stopping until you get at least one limb loose, or until you cum; it’s up to you,” Diane told me as she dragged her nails up and down both legs simultaneously, digging into each sole and then stroking my cock about five times before repeating the whole process over and over. I was almost on the verge of cumming when suddenly she stops everything. Argh! I screamed as frustration drove me mad; I was nearly worn out.

Then Diane told me, “I’ve read that if you ever have sore feet you should roll them back and forth over a hard wooden pole. I have a different kind of pole to use; I wonder how well it will feel?” As I heard her start removing the straps from her shoes…

I can feel the bed moving as she takes off both shoes and wraps both of her feet around my rock-hard cock. “You know they might be right; I think my feet are feeling better already,” Diane tells me as I become lost in this surreal moment.

The smooth nylons and warm feet are about to take me over the edge as she leans back on the bed, begins to unbuckle the straps of my right shoe, and tickles my tightly tied foot without missing a beat. “I bet it won’t be long now until you cover my nylon-covered feet in your hot cum; I think I am really getting a better workout than going to the gym or walking.” It’s time for both shoes to be off and both feet

“Tickled for the grand finale,” Diane said while removing my other shoe. I was going wild, desperate to ejaculate; all my senses were heightened as Diane worked her magic, continuing to tickle my feet and stroke my cock with them.

“I think you’re getting really close now. Should I stop again, or are you ready to cum?” Diane asked me.

Yes, just ha ha ha do it already! I can’t he he he take any more please, pretty please—I’ll do anything for you—just let me cum!”, I begged as she began to slow down the rubbing of her feet. “Anything, eh? I’m going to make you an offer. I will finish my work here, but at least once a month you need to make yourself ready for me to come over and do as I please with you. I know that you have every Monday off by yourself, so you don’t have any excuses about having to find a day when nobody is home. What do you think? Do we have a deal?” Diane asked.

I didn’t need any time to answer: YES, please yes—just let me cum! “That’s great; I think this is going to be a very good deal for both of us,” Diane told me as her feet and hands went back to high speed. “I think this is it. Are you ready?” she said as I began to spurt all over her feet and legs.

I came in waves. Diane finally stopped the tickling and slowly stroked my cock with her cum-soaked feet, then turned around and started licking me clean. I was in heaven as she licked me up, even throwing in a few rib tickles while she was at it. “You know, I am thinking—how much fun would it be if Kelly comes home and finds you this way?” Diane told me. “I think I may tie your key into a knot, just out of reach of your hand, that way when Kelly gets home she’ll just think you got in trouble all by yourself.”

Diane moved off the bed and over to the table with the handcuff key, retying it so there would be no hope of me getting loose on my own. “You had enough fun, didn’t you? Why are you doing this to me?” I asked, and she just laughed.

“I have a bunch of pictures that say I can do whatever I want to you,” she said. “Besides, I think you are still wound up enough for round 2. In fact, I’m going to type a note on the computer that says ‘Tickle me a whole bunch; I’ve been a very bad boy.’ That might just be good for starters.”

“Have fun! I will be calling you soon about next time,” Diane said as she worked the ballgag back into my mouth and buckled it one hole tighter than usual. Then, while tickling my foot on her way out the door…”, “post_id”: 21593,