Caught and compromised

by BillyBoy

11 Sep 2021 5186 readers Score 8.8 (20 votes) PDF Mobi ePub Txt


George lives in the apartment next door. He is older than me, but I don't see him often. I don't see most anyone here at the apartment complex. That's the way I like it. Moving here after my divorce, I just want some quiet time. I want some time to explore my new found obsession with wearing my w wife's and my mom's old underwear, for self sexual pleasure.

I played in moms palytex girdles and panties when I was young. Then in my wife's panties and nylons. I even stole some of our neighbour's underwear several times while visiting. She was a married, big tit tramp who had lots of naughty, sexy bedroom lingerie. My wife and I regularly visited the couple for drinks and other casual events. But mostly, I was looking forward to being alone in their bathroom/ laundry room. I'd always leave with some sexy pair of large panties or a nice DD bra.

One afternoon while visiting, I noticed a small pile of asserted shiny black undies tucked back in the corner of the laundry linen closet. To my surprise they weren't underwear. They were some sort of kinky bondage harness a woman would wear. Straps and buckles and a wide belt of leather and vinyl with wrist cuffs buckled to it. Finally under all that was a thick, heavy black leather and silver buckle dog collar and a really naughty red rubber ball gag. This began my infatuation with bondage and discipline.

The next day I was jerking off in her panties and bra while dreaming of how she must have been bound and gagged for her husband's dirty pleasure. Her drooling mouth stuffed full of the ball, moaning like a captive kidnap victim, barely able to cry out for it all to stop. Mmmmmm... I came all over myself.

I didn't dare cart off any of the really 'fun' stuff. So I ordered some online and waited for it arrive. But, alas, my wife received it, then found my stash of panties and bra's. We were a little rocky anyway. Next thing I know, I'm out on my ass. So I felt like a new start was in order. I got a new job in Seattle, and I'm here.

Now I get to dress in all the stuff she didn't find. And I have a lot. I really love mom's old vintage girdles and long line bra's. I ordered some more bondage gear to try out. I like some it, some it I don't care for. But I tried a lot of it. After a while I've got two boxes of kinky handcuffs, ankle restraints, spreader bars, knee pads, discipline collars, and the best stuff of all, mouth gags.

I never really imagined who might be cuffing and gagging me. I suppose I imagined the big titted neighbour doing it to me. But in my most honest, deepest dreams, I realized I was actually thinking of her large hairy husband using me like he must have used her.

This brings us back to George. A 40 something loner with a bit of a beer gut and plenty of hair sticking out under his shirt everywhere. One evening just after I'd had a long, intense dress up, bound up, jack off session, he knocks on my door. I'm thinking to myself I'm sure glad he didn't stop by a half hour ago. That would have been awkward.

He quietly asks if I'd like to stop by sometime to catch a football game. NFL had just started for the season and he said he was a big Seahawks fan. He noticed I was too, and was hoping he could have someone to watch the games with. I said sure. But we didn't make any specific plans. I realized later he didn't give a shit about football.

I'm standing in my bedroom a few days later, dressed in a red open bottom girdle and matching red pantyhose that had previously been the property of my old neighbour. I've got black leather ankle cuffs on, hooked out to the ends of a 3 foot wide spreader bar. It's all I can do to stand. It's perfect. My hands are cuffed in front of me, locked to a ring on the front of a dog collar buckled tightly around my neck. I've got 4 pairs of her worn panties stuffed in my mouth, filling it up completely. Taped in with extra sticky, four inch wide, black Gorilla tape that I wrapped all the way around my mouth and back of my head 3 or 4 times. My mouth is filled up with the taste of her used satin, lace and cotton panties, and closed up extra tight.

I try to let out a little scream for help. Nothing. I try another, more desperate cry for help. Nothing. Mummph... just right. I carefully twist the small control in my hand. As advertised, the fat little butt plug I'd inserted and hour ago begins to hummmm. I play with the control making it pulse, then wiggle, then all three. Nearly helpless, with my rock hard cock trying to pop out from under the lace panties, I'm dreaming of how I'd be ravaged like a whore if her husband was here.

It took me an hour or more to get untied, undressed and back to being a normal man. I'd experienced one of the most intense orgasms ever. I came so fucking hard and with so much force I thought my balls and my cock were going to rip apart. I laid on the couch, remembering the wonderful time I'd just had all by myself. Much better than anything I'd ever had with the x wife.

A knock on the door. What the fuck? George is back with much the same message as before. He noticed I was a Seahawks fan. Some time we should get together for a game. I didn't invite him in. Some of my dirty stuff was on the bed and of course I didn't want his seeing it. He left without another word. "Maybe next time."

I thought maybe now I should finish cleaning up the bedroom. While I'm picking up the assorted panties and stockings and leather items, I notice my Russell Wilson poster on the wall. I do like the Seahawks. I hesitate, looking around, and realize that is the only Seahawks poster, or anything, I have in my new apartment. I get dizzy and stumble to the bed. What the fuck? How did he.....?

My blinds are just wide enough to cover the window. Unless I look in from outside. The gap between the shades and the window is almost an inch on both sides. Cheap apartment fucks. I notice the parking spaces are right there. George's truck is parked right outside my window, next to my car. We walk right by on our way in. Looking in after dark the inside of my lighted room is clear as day. My bed. My dresser. My Seahawks poster. Hss he been... What the fuck?

I don't play for a while. A long while. I'm nervous as shit. Finally, I can't stand it anymore. I try a little less of a production. Panyhose, a bra, some duct tape wrapped around my ankles and knees under my covers. I rub for a few minutes but It's just not the same. I wiggle around and get a new rubber ball gag I've not used before. It barely fits in my mouth. It's extra big but really soft. I bite down on it until I get tired, then it pops back really filling my mouth all the way up. My cheeks are puffing out. It nearly gags me as it opens up all the way to the back of my throat. I strap it in really tight so it does that. This is better. Helpless and unable to cry for help. This is the feeling I'm looking for.

Not wanting to waste a good opportunity, I plug the little vibrating butt toy in as deep as it will go. I turn on the wiggle mode and toss the control off to the side. Now let's finish this up. Carefully putting the key to the police handcuffs on my night stand, I reach back behind me locking my wrists together. Now I can wiggle, struggle, squirm, hump, moan like a captive bitch, and rub out a real nice one.

Well, you probably know what happens next. George has been waiting for a long time too. He has been waiting for me to give him another show. He has been saving himself until I finally give in and play dress up again. I'm just beginning to get into it when I hear him at my front door.

I freeze in horror. I locked the door, didn't I? I'm sure I would have. He doesn't stop knocking. "Are you OK? I heard some noises and want to be sure you're OK. Can you just let me know you're OK?"

I can't get loose for a while. I begging to wiggle around to reach the handcuff key. It's a struggle. I never mean for it to be easy to get unbound.

The front door of my apartment opens. What the fuck? Footsteps. He walks right back into my bedroom. I'd never felt terror, the humiliation, the embarrassment like this before. I realized a heightened sensation of every tight wrapping of tape, the cold metal cuffs, the naughty little butt bandit in my ass, and the mouth filling gag. A wave of dizziness and euphoria came over me. I choked on the gag and gave in to the experience. I closed my eyes trying to forget he was here. My balls exploded shooting a huge load of jizz through my hard cock like never before. I was moaning and struggling. This was the craziest thing I'd ever been through. My pantyhose were warm and full of my just unloaded load. I was a mess!

"I was hoping you'd invite me over for one of your little play times. But you never did." I'm just looking over my shoulder at him. My eyes must have said it all. "Don't worry. I'm not here to bother you. I just want a little taste of what you're doing there." He reaches toward me and pulls the covers all the way off. If I can hear the plug in my ass buzzing away, I know he can too.

His hand touches my shoulder. I cringe and let out a muffled squeal. I've never been touched by a another man. He gently rolls me over on my back. We both look down at my crotch. Inside my pantyhose is a huge wet load of cum. "So, you enjoyed me walking in on you, it appears." I moan and try to bite down down on the rubber ball so can respond. My mouth is already too tired and sore.

After he looked me over for what seemed like hours, he took off his shirt and laid on the bed next to me. If I wasn't nervous before, I sure was now. He reached over, took the handcuff key and put it in his pocket. "I've been thinking of what I'd do in this situation. " I looked at him with puppy dog eyes. I moaned a little from under the nasty ball gag. Why did I pick this one for today? His hands slowly moved tward me. 

He leaned in and kissed my cheek. I moved my head away, but it didn't matter. He licked and kissed my face. His breath was hat. He was breathing hard. His tongue and llips were warm and wet. I felt one hand up under my satin and lace bra. He was groping my chest. His fingers found and pinched a nipple. I tried to bolt, but you know, I was bound pretty tight. His mouth wrapped around and covered the ball in my mouth. His lips touching mine. His other hand slipped under my ass, inside the pantyhose, grabbing a cheek. I was moaning and struggling. He stopped for a moment. Smiling and looking straight in my eyes, he says: "I like it when you try to cry out and wiggle free. You can keep doing that".

The hand under my panthose moved up and in front He took my half hard cock in it and squeezed. There was cum everywhere inside there. On his hand, On my cock. Drenching the panthose. He stroked me using the cum as a lube and he wouldn't stop. More licking and kissing. More nipple grabbing and pinching. More cock stroking. Fuck! I was gettig hard again.

He took a moment. He reached behind my head and unbuckled the ball gag's strap. The ball sprung out with a loud pop. I gasped for breath. I said something like, "Oh Fuck. Thank you!" I was releived. But even more nervous. too. His fingers wrapped around under my mouth. He leaned back in and kissed me. His tongue slipping inside. I was so tired and my mouth was so sore, I couldn't resist. I let him deep throat me with his tongue. I laid back and let him stroke me back to a full erection. My nipples were tender and sore from his relentless groping and pinching. All I could do was take it. My mind was exhausted, but racing with crazy thoughts. What was going to happen next?

"I'd be remiss if I didn't take full advantage of this opportunity." I was pulled up, sitting on the bed with my back to the headboard. He climbed on me, stradding me, kneeling in front of me. His pants unbuckled and dropped below his waist. He pulled his shorts down exposing his already hard cock. It was big. Well, it was a foot in front my face. So, it sure looked big. He reached into a pocket and showed me the handcuff key. "I'll give you this when you've finished, and when I'm done. OK? "

His hands slipped down to my pretty bra cups, grabbing my 'tits' like a a man would grab a girls. He leaned forward putting the tip of his hard on right in my face. He shuffled his legs in closer. The his cock. It was pressing againt my closed lips. I turned away. He just patiently waited. Gently rubbing and squeezing my chest. I turned back. I tried to say something. It was in my mouth. Fuck!

His hand took the back of my head and pulled me closer. His cock slipped in deeper. He pulled my head back. Then forward again. "LIke this sweetie."

What was I suppose to do? I'm cuffed and shackled and half dressed like a woman slut. I let it happen. I even sucked a little. Closing my eyes I took it in deeper with every forward thrust. He asked me to open them and look at him. He was breathing hard and smiling down at me. He pinched my nipple really hard. My mouth filled up from the tip of his hard on like a stream of whipping cream being blown out of the can. My cheeks puffed out. I gasped and a flood of cum spilled out of my mouth. I choked and tried to catch a breath. I was covered from chin to belly with warm, sticky, gooey man jizzz. 

Next to the handcuff key he wrote down his number. He told me to give him a heads up the next time I was going to dress like a whore and wanted some assistance getting tied down to my bed. He said he would be waiting for my call or text. He said if I waited too long, he would just stop in and take me by surprise again. He said maybe that was what I prefered anyway. So I should be ready whenever I play like a girl. He said he will stop over whenever he feels like it. He said he was OK with it either way. 

So now sometimes I text him. And sometimes I get all dolled up, tie myself up and wait for him to break in and take me. The more we do it, the more I feel like a slutty girl. I'm not sure if thsi was how it was suppose to go, but what else can I do?

by BillyBoy

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