BondageDating

A Self-Bondage Marathon of Events

Alright everyone, I realize I’ve been sharing quite a bit lately, but there’s a solid reason for it: the last week has essentially been an amazing…

member_d7939186d5 24 Aug 2026 #1

Alright everyone, I realize I’ve been sharing quite a bit lately, but there’s a solid reason for it: the last week has essentially been an amazing self-bondage marathon. Perhaps “decathlon” is more accurate since it was a series of distinct events spread over several days. With the house to myself for roughly nine days, I packed in as much SB as possible during every spare moment.

To give you some examples, I achieved first-time experiences in forced urine drinking (which I’ve already shared here under “True Stories”), outdoor bondage, self-bondage with a real risk of being discovered, and even cross-dressing while shopping. There are wonderful details to follow for each event.

Cross-Dressing: I’d had a pair of 5-inch heels for ages; they’re comfortable enough to wear all day as long as I’m not standing or walking the entire time. I usually slip them on whenever possible, especially during SB scenes. I can manage four or five hours of standing/walking before needing rest, and I can endure at least two hours in a strict standing position with very little movement—though that really tires out my feet and legs.

This week, however, I finally gave in and ordered a super-sexy maid’s outfit from Pierre Silber, along with a wig and satin gloves. You can be sure I strutted around in it for hours and took plenty of photos if anyone cares to see them. I also did quite a bit of SB while wearing the outfit, including the urine-drinking part.

But before all that happened, I knew I needed a bra to complete the look. The problem? I didn’t know my size. Since I needed to buy one before the house stopped being exclusively mine, I had to go out and get it measured in person. So, I concocted a story about starring in a play where all the male actors were dressing up for female roles, followed by a dance scene—meaning simply stuffing paper down my dress wouldn’t suffice.

Armed with this tale, I headed into a women’s store that sells lingerie. The first assistant who came over was naturally about half my age. When I told her I needed to buy a bra—not for my girlfriend (in which case I’d either know the size or just steal a glance at a label) but for me—I expected her to have a heart attack or call the police immediately.

In reality, neither happened. In fact, she got quite excited because, as she explained, this was her first time ever doing a fitting! This also meant she thought it proper to summon the manager just in case. I reassured her that if her recommendations weren’t perfect, it wouldn’t be catastrophic compared to messing up with someone who actually needed significant natural support!

I started off hoping to stay low-profile, of course, but with a teeny-bopper helping me and now yelling across the store for the manager’s assistance.

The girl wasn’t really my type (a bit big-boned), though she was friendly and reasonably cute. The manager was also fairly attractive. If either had guessed at my true reason for buying and been turned on by it, I would have gladly let them dominate me, or dominated them, or both—ideally.

But I digress.

We measured, fitted, and chatted. They determined a 38C was right for me, then asked what color I needed to match (or not clash with) whatever costume I’d be wearing for the “role.” Knowing I wasn’t really playing any specific role but wanted something black, I said a black dress, so that’s what we went with.

I tell this story because, for all you newbies out there who wondered how to go about buying items without knowing your size: my observation was that maybe I got lucky, but these ladies simply didn’t care why I was buying the bra. If they suspected I was cross-dressing, they certainly didn’t show it. Maybe they liked the idea of a man playing the part of a woman in a play, or perhaps enjoyed imagining dressing one up.

Question to the women on the board: Is there something about feminizing a man that turns some women on? The point is, you can make up the exact same story and own it. It doesn’t matter if someone doubts you; they might not believe even true stories. If you know it’s true in your mind, then it is. Just go for it.

For what it’s worth, I pulled a similar stunt at another store two days later. After wearing the maid outfit (even driving around in it!), I realized I wanted a dress too. A bit of online research based on my bra size suggested I might be a 14 or 16. So I went to the shop, picked out two dresses in those sizes, and asked at the register if “my girlfriend could return whichever one didn’t fit.” Of course she could, they said.

It struck me that when men look at women’s clothing, the first impression is usually that we’re buying for a significant other. And who says your SO might not be a large woman—just as big or bigger than you? Sure, it helps that I’m of normal height and build, so a woman my size wouldn’t seem like an outlier. But if you’re in the same boat, just go in there and buy the damned things. Take them home, try them on, and return what doesn’t work.

Now I know I’m roughly a 14. And I think I look pretty good as a chick, mostly thanks to my legs and arse—not even mentioning makeup! That might be stretching it for now, but man, what a rush…

This leads nicely into the tale of calculated risk regarding discovery in SB. I am actually selling the house, so realtors are scheduling visits here and there. One was coming at a specific time. Having had great fun earlier in the week with a standing spread-eagle (where the safety release oil can fell on me for no reason—see “Backup Release with a Mind of Its Own” in “True Stories”) and brimming with confidence from how good I felt in my maid outfit, I came up with a doozy: instead of leaving during the visit, I would lock myself into that same standing spread-eagle, still in the maid’s outfit, right here in the basement garage while people were touring the house!

By “calculated risk,” I mean I wasn’t just standing there exposed. I put up a tarp dividing the garage into two halves, but only stretching halfway across. Viewed from above, the two-car garage looked like a box with a line running straight from one side to the middle. The doorway was on one side of this line/tarp; I, locked in my exercise equipment, would be on the other.

I wrote a note and placed it on the garage door: “Working on a project behind the tarp; respectfully ask no one to go over there.” About fifteen minutes before the realtor arrived, I was ready—dressed as a maid, prepared to cuff myself into a standing spread-eagle. Heeled, hosed, outfitted in the maid gear, ball gagged, and facing the open end of the tarped enclosure.

The bottom line: if someone ignores the sign and peeks around the end of the tarp, I’m busted.

I already had the ice release set up—and it needed to be a reasonably large cube so that melting wouldn’t cause noise at the exact moment people might stand in the garage doorway. I heard a car pull up outside; go time! Gag on, ankles cuffed apart, wrists cuffed overhead, no turning back.

Then another car pulled up—the potential buyers. Greetings all around, etc., and then I heard something that made my heart stop: running feet and children’s voices. Kids! KIDS, I thought! What would happen if they ignored the sign and opened the garage door?

and go racing in only to be greeted with the sight of me? Disaster, that’s what, and far worse than if an adult discovered me. But it was too late to do anything about that now, and since I was gagged, I wouldn’t even be able to warn them away. I heard walking around in the house above me, could make out voices, and then I heard everyone coming down the stairs. They were milling about in the hallway just outside the garage doorway. And then, finally, I heard that door open. I knew I was going to have to be absolutely silent if that door ever opened, so I don’t think I even took a breath. But that wasn’t the whole story, because if any chain moved and made a jingle, that would attract attention too. And it was one chain for each of my appendages and another which was locked to my CB-2000, pulling my hips forward. Any movement at all and that last chain would almost definitely twitch, so I made like a statue as best I could. After the door opened all the way, here’s what I heard from within the garage: FEMALE CUSTOMER: “(Realtor’s name), there’s a sign here on the door about a project behind the tarp that the owner doesn’t want upset.” REALTOR: “Yes, I saw the sign too. I guess he doesn’t want anything to happen to the project.” MALE CUSTOMER: “I wonder what it is?” REALTOR: “I don’t know. He didn’t mention it.” MALE CUSTOMER: “We could have (child’s name) take a peek under the tarp.” People, how fast do you think my heart started to beat when I heard that? Even if the guy didn’t mean it, but what if the kid took it as an “order” and did it anyway? Remember, I was gagged, so I couldn’t have warned anybody away even if I wanted to. Time stopped for me right then. It stayed stopped. It didn’t start again until I heard the customer and everyone else laugh, and then walk back into the house and close the door behind them. I don’t know if I finally moved until I was sure they were all out of the house. Of course, even then I still had to wait for the ice to melt. That took nearly two hours in total, including the longest ten seconds of my life. Do you know what the funny part is, and funny because the joke was on them? They were standing five feet from an adult male dressed in a maid’s uniform and chained to a workout apparatus, and they never even knew it. I’m calling it “Realtor Bondage”. Maybe this forum needs a new section, and since I’m the creator, I want an award! Outdoor bondage: this was kind of a light session, with reasonably little risk of discovery, but still with some time in the open and some exposure. All I did was lock myself out of the house late at night on the back deck, completely naked except for socks, the 5” heels, and a ball gag. Wrists cuffed behind. My main key was to the front door, which to reach I would have to walk down the driveway, thus triggering the motion sensor light, and walk up the front path. Plus, there was an outside door and an inside door, up one step, so it would be a tough reach with my hands behind me. My safety was the back door key, but that was in the mailbox out on the street, right below a streetlight. Much more exposure there, so I wouldn’t be doing that unless I needed to. OK, so ice release set, door lock behind me, ball gag on and hands now cuffed behind. One nice thing I realized was that at least I could scratch my face when necessary, not with my hands but with my knees if I sat down. Much of the bondage earlier in the week was with hands and legs spread out and offering no help. I alternated between sitting, crouching and standing, but I didn’t want to walk around much because it was so quiet out I thought the sound of my heels would wake up the entire neighborhood. In fact, that was the fun part when the keys finally fell: how to go down the driveway. Go fast to minimize time in the motion sensor light, and my heels make a racket on the pavement. Go slow to be quiet, and I’m standing in the light for that much longer. I chose the former, and kind of ran on the very, very front of my shoes. A good burn for the thigh muscles, that’s for sure. And when I got to the front door, yes, it was difficult to open because of the height of the keyhole, but I finally got in. Nearly an hour and forty-five minutes I was out there! It didn’t seem that long. Funny thing about this one is, if somebody saw me, would I ever even find out about it? Would they bother calling the cops to say that their neighbor just ran naked from his backyard to the front? They wouldn’t have known I was sitting out there for two hours. Would they even bother? Even though there wasn’t much to it, it was still pretty exciting to know I was locked out of the house naked, heeled, gagged and bound. So now I am scouting other, more public locations where maybe I can get away with doing the same routine for a few hours while minimizing the risk. Without a doubt this would become the biggest leap in my self-bondage portfolio, now that urine-drinking has been checked off, but I hope I can do it. And boy do I hope I don’t get caught!