Caught Crossdressing

You don't hear about these sorts of things actually happening, but they do, Caught by a pervy in my wife's panties and bra. Oh No!

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  • 12 Min Read

Looking for kink

You don't see many of these situations on-line on porn sites. No videos anyway. I'm always looking. I have a memory of this happening to me. Some days I remember it like it was a dream. Other times I know it was real. It changed me. I'm always checking to see if it was a real thing. Why doesn't anyone make a film or a video about it? Is it that boys in girl's clothing is so disgusting? Is it the curse of the weird and demented? I know almost every guy has tried on a pair of panties at some point in their life. Or at least felt them against their skin when they jerk off. Everyone does. I certainly did. But after this, it has more meaning for me.

As I mentioned, at first I'll put on a pair of my wife's tight little thong back panties from time to time. Then later on I'd put on a bra, too. And then her silky nighty.  Sometimes I'd even wear some of her pantyhose or thigh high stockings, if I was feeling especially frisky. Seems my jerk off sessions would be much more erotic and my orgasms deeper, when wearing her things. 

After some time thinking of her, which is how it starts, drifted from my mind. At first, I felt closer to her when wearing her sexy under clothes. But after some time, visions of being the woman, the submissive worshiper of man and his cock, like a woman should, began to creep into my thoughts. Better, deeper orgasms followed. After that I gave in to these weird, faggot thoughts. It's just in my mind, so no harm done. Right?

Stimulation

Of course the next step is to give into the desires that seem to follow. Pinching my nipples was a very good thing to do. And then, without any input, I felt like I should have something penetrating me too. A man has two places for that. His mouth and his ass. My ass seemed to be begging for it. But what do you use? A rubber dildo? A plastic vibrator? Some sort of naughty butt plug I've seen in porn videos? I wasn't sure. My wife has a couple of simple vibrators. We don't use them in sex anymore. They just sit there, hidden in the back of her nightstand drawer. Waiting for me to revive their purpose? I wonder.

The other place a man can have something shoved into him is his wet, drooling mouth. Sucking on a big rubber dildo didn't seem so exciting to me. So what? It's funny how these things progress from simple, innocent thoughts, then into actual plans and real experiences. But they do. They did with me.

After some research on-line, I realized how many different mouth things there are to play with. Mostly, if not completely, mouth gags used for bondage and discipline play. I've kissed a pair of my wife's panties and rubbed her bra in my face before. I even sucked on the panties a little until I came on the bra. I think that is pretty usual conduct for a horny, married man. With having something in my mouth for erotica, I shoved a couple pairs f her dirty panties in my mouth like I was gagging myself, unable to speak, or moan. It was wonderful!

Gags

Later I would stuff as many panties as possible in my mouth and use her bra to tie them tightly in. I'm helpless. I'm at the mercy of whoever might be gagging me and using me as a sex toy. I liked that. Did the bra I used as a binding still have my cum on it from before? Probably not. But I could do something even better. I jerked off dreaming of being manhandled and forced to suck cock by a bad man. I came all over her red and black lace panties. I put them away until the next day. That night I jerked off in another pair. Her white lace and silk Victoria's Secret ones. Now I have two pairs waiting for tomorrow. 

As you can tell, I seem to have a lot of time to myself. our schedules haven't matched up for some time. I'm home alone a lot. 

First results

So the next day slipped on a pair of her lace thong back panties, a tight push up bra, some tan with lace tops thigh high stockings, and a leather collar from our dog. I wasn't sure where the dog collar idea came from, but I liked it. Finally, I pushed the still cum soaked panties into my hesitant mouth. It took a minute. I washed them around in my mouth, mixing the taste of the silk and lace panties, the cum from yesterday, and my saliva together. It was wonderful. I used another one for her bras again to tie everything in. I was forced to experience the taste whether I wanted to or not. That's was I was after. Forced. Helpless. At someone's mercy. I blew a huge load like never before, filling the inside of another pair of her panties more that I ever had before. 

I wasn't sure what was causing the huge increase of orgasmic enjoyment. But I wanted more. I'd satisfied myself that having my mouth stuffed was very erotic. So, anal stimulation would be next. But her small vibrators wouldn't do the trick. For the first time, I searched for something specific for me. Something secret, taboo, under the radar. A dildo.

Rather than finding one on the internet where I might be discovered, I stopped in the local Adan and Eve store, paid cash, and that was that. I really didn't take much time in the store. I tried to just grab something appropriate and get out of there. Once I was home I realized what I had done. Only a part of the full length of this thing was visible in the cardboard package. It said what it was on the box, but I didn't read the box. It turn out the thing I expected to push up my butt was a bit larger than i was expecting. If you've ever bought a fairly large cucumber, you get the idea. As bog around as a golf ball is round, and as long as a one foot ruler. So, yes, a 12 inch long, fat, pink with purple veins dildo. This one even had a pair of balls at the base with a suction cup on the bottom to hold it in place on a smooth wall or on the floor or somewhere. It was flexible, but pretty firm, too. "Ouch" I thought to myself. But I was pleasantly surprised to see it also came with a little bottle of lube. A marketing sample. This is perfect! I'll give it a try.

The story

As you can tell, if you're still with me, this setup could be going somewhere. It's important to understand this whole process took several years to develop. I never thought of myself as gay. But those thought began creeping into my mind after several years of boring life and little or no sexual satisfaction. So, I'll blame all of this on her. 

Like I mentioned at the top of the story, I search the internet for porn stories and videos that interest and excite me. I kept seeing gay and trans people all dolled up jerking themselves off on camera. For some reason I found these videos very erotic. I realized after a while I was placing myself in those videos, feeling like it was me in lingerie, a plug in my ass, jerking off for a loving and appreciative fan base.

I've looked in the mirror before, watching myself in her lingerie with my hand pulling at my dick. The thought of someone else watching me, a stranger, and enjoying seeing me like that, made me feel warm, sexy and horny. It's crazy! I'm not the most fem sort. But I decided if I was going to stick my toe in that pond, I'd somehow hide my face anyway. 

One long sleepy afternoon, I went for it. I wore my wife's wedding lingerie, which has been hidden away in the closet for 10 years. Yes, it was a little tight, but I liked that. It was the typical white lace corset, girdle style bottom, garters, white lace top thigh highs, etc. I felt silly wearing it all. But then, I looked in the mirror. Standing there in front of me was a tall, sexy bride, waiting to be fucked like a whore by her new husband. Or at least, that's what I saw. LOL.

We had a few leftover Pandemic masks. One was a white medical type with little strings that pulled back behind my ears.  I was a little disappointed that I wouldn't be able to show off my panty gagged mouth, but keeping myself hidden was pretty important. I actually waited to try the big nasty dildo until my first broadcast. I thought my reaction to it stuffing me for the first time might be priceless. I would be right.

I thought I had a good look going. I liked what I saw. I was getting horny just thinking about when I'd actually try this. 

The broadcast

The broadcast took a while to set up. I chose a 'Chaterbate' kind of website. You can broadcast yourself after some identity confirmation. That took a few days to figure out. Finally, I had everything I needed to run a live broadcast. I was live and a few people were already watching. On these sites you can set up a token place for tips. I wasn't trying to make money here. I just wanted to know what it would feel like to share my perverted fantasies. 

I waited until I had a whole evening free. She had a overnight business meeting in Seattle. Perfect. 

I fired up the website and started getting dressed. I was off camera, using my laptop camera, while I was carefully slipping into the lingerie. I heard a few comments ring in. then more. I'd explained what I was going to do on the webpage. I already had 20 interested perverts. Some of them, and eventually all of them, wanted me to dress in front of the camera. At the time I checked the comments I was in the white lace panties, the white lace top thigh highs and the matching white lace open top bra. My nipples were exposed because the bra was just a tight bottom thing that pressed the chest up in a quite snug push-up fashion. The corset would go over it in a minute. But for now, the bra made me look like I actually had some nice puffy B or C cup tits. The website went crazy. They loved me in my skimpy bra and panties. I'd forgotten to cover my face at this point, not remembering the camera was right there. But all was good. 

I posed in a couple of different poses and then left for the rest of my outfit. The website kept ringing. I'd received over $100 in tips already. I took my time finishing with the outfit. I was wearing the mask now so gagging myself seemed pointless. But the group had other ideas. They wanted to see me take those wet panties and stuff them in. I nodded to the camera and decided I'd do their bidding. After a half hour or so of dressing up, I produced the panties in question to the applause of the group, which had grown to over 50. I had a white lace bra for tying them in, shoved them into my mouth, close up, and wrapped the bra around and tied it.

I wasn't sure if this thing had audio, so I tried it out, letting out a loud "Mummphh!!!"

The place went wild. 

One member quickly paid me a $20 tip, demanding I "Shove that cock up my ass and jerk off like a bitch."

I guess it was time. I'd laid out a piece of plywood from a shelf in the garage. It was a foot or so square and had a slick finish on one side. The suction cup on the dildo stuck right to it. It had been in the frame of the video the whole time. Rising up like a naughty reminder of what was going to happen to me. I noticed on the screen, it looked as big as someone's arm, from the elbow to the tips of the fingers. Big, long, veined and dangerous. I'd forgotten how large it really was. I was pretty nervous. But the show must go on, I thought. So did my fans.

One of the fans suggested I complete the bondage scene for them. Everyone chimed in and agreed. A gag was just a small part of the look. They suggested I bind my ankles and even my wrists, so they could enjoy me struggling as I impaled myself with the huge dildo. I motioned to the dog collar I'd put on, but they were not having it. 

I took a break, looking for something appropriate to use to tie myself up. I returned to the show with a kitchen chair, a necktie, and a roll of duct tape. Everyone applauded. My plan was to move the dildo to the seat of the chair, then sit up and move myself over it. I couldn't bind my legs together if I was going to do this, but I could tape each of them to the outstretched legs of the chair. When I moved the rubber cock up to the chair, everyone realized my plan. I was a hit.

I quickly wrapped the tape around each ankle, spreading my legs out. I used the necktie to bind my wrists. I tied a loop in it then pulled it tight until my hands were out in front of me, bound. The room went wild. I was really getting a kick out of this. All of it!

As I was beginning to stand up a little bit, getting ready to squat over the dildo, I noticed I may have tied the necktie a bit too well. I couldn't pull it loose. I figured I would be able to remove it easily, when the deed was done. I shook it off and proceeded. I slipped my already hard cock out of the panties, rose to the height of the tip of the dildo, and moved over it. I had used half of the lube that came with the rubber dong in my ass already. I gently dribbled the rest of it over the tip of it while everyone watched. The tip jar kept ringing.

To see what I was doing, I had positioned the wall mirror behind my laptop. I finally could take a quick look at that I had created. I didn't recognize myself. Again, I saw a tall, pretty bride in her wedding lingerie. But this time she was helpless and at the mercy of a gang of perverted fuck heads. It was like I was going to gang fucked. I loved it!

I look back at the recording of me taking the dildo. My face is precious. My grimace is genuine. The sounds I made with those panties gagging me were unforgettable. I made over $400, even with the website's override, which is a lot. But what happened as I was at the peak of the broadcast, changed me forever. 

Just as I was all the way down on the dildo, my face red with a combination of pain and excitement, still trying to find a way to get the necktie to loosen up, I heard a door in my house open, then close. The look on my face then was priceless. Was my wife home? She can't be. Footsteps. "Fuck!"

The group was crying they were laughing so hard. They couldn't wait to see how this plays out. My legs were really tired. I couldn't get off the fucking dildo. I just sat there, tied, gagged and filled with a huge rubber cock, waiting for my fate.

A tall man wearing a similar mask walked right into the room. I let out another loud, nervous "Mummphh!!!"

Looking toward the laptop, he put his hand on my shoulder. "You've done a fine job with your broadcast. Now let's see what everyone would like you to do now, my bitch."

The tip jar started ringing again. My hands were not getting free. I was fucked! The man leaned in the laptop, reading the gangs requests. Then he moved back giving his attention to me. "They want you to suck my cock. I think that's a great idea. Don't you, my bitch?"

"Mummphhhhhhhhhhhhhhh!!!"

Well, you guess it. This guy was a pervert neighbor of mine. He was watching the broadcast and couldn't believe what he was seeing. He had suggested the bindings. He was waiting outside my door until the time was just right. And he was correct. His cock was warm, wet and hairy. He was really hard, too. There I was, sitting on a 12 inch dildo, tied to a chair, my head turned to the side with his cock in mouth. Everyone loved it! 

Even me.


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