The time I (accidentally) kept a crossdresser in chastity for over 50 days [M27, T23]

This story took place in June, July and August 2015. It was between myself and a crossdresser I’ve been meeting for a few years. She’s called Kyla – and I might as well shout out to her as she’ll be reading this story. If you have any questions for her, post below and I’ll try my best to get an answer. Kyla is 23 in this story and crossdresses only part time, really as an outlet. We’ve had a few deep meaningful conversations over the years and I’ve learnt that Kyla would transition but for the good things she’s got going in her life. She lives as a male, has a good job, a good family and good prospects. She doesn’t want to rock the boat too much.

I don’t think I could really say I “live” in the UK. I’m usually travelling with work so only spend perhaps ten days per month in England, and sometimes that time is in London hotels as I stopover. I do have a nice house though that I enjoy returning to when I’ve got time. When I return home I also enjoy getting Kyla to come over for a good, lengthy, overnight session. She’ll come already dolled up, will bring an overnight bag and we’ll eat, fuck and sleep until the next morning.

Kyla is, as I mentioned, 23. She’s a tall girl at almost 6’0”, very slim and feminine. She really carries herself like a woman. She wears minimal makeup, but her face is always totally smooth when I meet her. She always looks great in her cute brunette wig that really compliments her face. Underneath she keeps herself totally smooth, including her long legs. Hidden away under her panties you’ll find a very cute cock when it’s soft. It’s just a little nub, maybe 1 ½ inches, but this girl is a show-er. It rises to about 6 inches erect.

For the past few months, Kyla had introduced me to her kink. She liked her cock being caged. She’d bought a CB-3000 chastity device and we had started playing with it. On this night in question, I’d watched Kyla put the cage on her own cock as soon as she’d arrived at my house. Imagine if you’d built up to get off for over a week, and when the opportunity arises you’re already commanded to lock your cock away? It wasn’t something I was totally into, but I grew to enjoy the control it allowed me to exert. I immediately had Kyla suck me off. Very few words were exchanged.

She sucks like a good girl. Totally obedient and always does what I say. It’s easy to get Kyla to gag – and let’s be honest, that’s hot. She’s down on her knees and I’m standing over her. She’s whimpering now and again. I knew her cock was straining in the cage. Kyla was always a bit of a slut. I could fuck her for half an hour and neither of us would touch her dick and it would remain totally hard. This is why I know being in the chastity cage is really, really difficult for her. She’s a horny girl. After a while I cum right into Kyla’s mouth, and like a good girl she swallowed immediately. No screwed up face, no “ugh” noise, just a girl swallowing what I provided for her.

Kyla was looking sexy. Not in a over the top sort of way. More in a girlfriend experience way. She was wearing a grey skater dress – tight at the top showing off her great breast forms – going down to a more pleated bottom. It was quite short, but not obscenely so. She was wearing black tights with little bows all over them. I’ve got a serious thing for tights and always have done, and fuck was this pattern hot. On her feet she wore beige flat ballerina type shoes with a sheer side.

I made us spaghetti carbonara for dinner. I’m not much a cook, but get by in the kitchen. We settled down to watch a movie. If I recall correctly it was The Last King of Scotland. Kyla was cuddled up to me on the sofa and I began holding her cock and stroking it through her tights and the cage. I told Kyla I was going to give her a chance to cum tonight, and it would be her last orgasm for over two weeks as I was heading off to Vietnam. I think she was slightly taken aback. Most of the times she’d been caged had only been overnight at my house, or I think there had been a couple of occasions where it had been for 3 or 4 days, but never this length of time.

I could tell she was a bit hesitant, but I told her if she came tonight she was being locked up until I came back. She agreed. After the movie I took the cage off Kyla and got her to kneel down in front of me. I told her to begin stroking her cock. I whispered in her ear.

 

“How is it going to feel to be locked away for 2 weeks?”

 

“You’ll hardly feel like a man, will you?”

 

“You’ll be wearing panties for me the whole time.”

 

“I want you to document the experience and read it to me when I’m back.”

 

“Maybe I’ll never let your cock out. Would you like that?”

 

“What if this is the last time you ever cum?”

 

This obviously sent her over the edge. She put her hand out in front of her cock and told me she was cumming. I whispered, “good girl,” and she began shooting little dollops of thick cum into her hand. The moaning was hot – little girlish whimpers as she unloaded her cock onto her hand as I watched. I could feel my cock twitch. I got her to lick her cum off her hand and said for her to go and get cleaned up and meet me in my bedroom.

Once upstairs I caged her cock away and told her to say goodbye to her cock for a couple of weeks. I told her that she’d best be well behaved, and if she was we could take the cage off for a week or two when I got home. I took her shoes off and placed my hardened cock between her nylon feet. She was well versed in this and began gently rocking her feet back and forth on my cock. We talked about the next couple of weeks throughout the footjob. It felt fantastic. The smooth nylon was contrasted by the slightly coarse bows on the tights. I flipped her over onto her front and jacked my cock over her cute soles. The tights were slightly crinkled under here, and fuck was it hot. I shot a lesser load than earlier, but still impressive enough, all over her soles and the back of her legs.

I was totally fucking spent. We were both really tired, so I got Kyla to put on her sexy chiffon nightdress and get into bed with me.

The next morning we both had to head off. I whispered to Kyla about the cage and asked her if she genuinely was committing to the 2 or 3 weeks. She was totally resolute in her position and said yes. Kyla headed off back to real life caged, padlocked in her panties, hidden under her trousers. This was so fucking hot. I loved the thought that she wouldn’t be cumming, she wouldn’t get an erection, she wouldn’t fuck a girl for over 2 weeks. Kyla had become a true and total pussy.

Later that day I flew off Emirates to Seoul, South Korea for a couple of days and then on to Saigon. I can’t recall which Korean airline I flew to Vietnam on, but they were absolutely shit. Avoid if you can. The announcements weren’t in English, the food was rancid, there was little to no legroom. This was the unglamorous side to travel. When I arrived in Vietnam I checked my “play” email account and found an email from Kyla saying, “I am horny =(“. I sent back a picture of me stroking my cock and told her that I would be cumming thinking of her locked in her cage. I’m sure she wasn’t happy.

The weeks passed fairly quickly. Kyla and I exchanged some emails, but it turned out her grandmother had taken very ill and understandably I think she’d become preoccupied. I got home as planned, emailed Kyla, but got no reply. This wasn’t a great situation, as I was only home for 3 days and 2 nights before flying back out to Asia… for over a month. At this stage Kyla’s cock had already been caged for over 2 ½ weeks. By the time I would get back from Thailand it would be over 7. I genuinely felt a bit concerned at this prospect. Overnight, it’s sexual. A few days it’s sexual. A couple of weeks it’s arguably sexual. Over 7 weeks straight not being let out of a chastity cage is sexual to some, but I was concerned it wasn’t what Kyla had in mind when we started this sort of play.

I emailed Kyla again and said that I would be leaving for Thailand the following afternoon and wouldn’t be back until the middle of August. She wrote back and said her grandmother had passed away and she was attending the funeral in South Shields. Shit. That was at least 200 miles from my house. I wrote back and expressed my condolences and said that she would have to be a good girl and stay locked up until I got back. She wrote back and said, “=|”. The smiley said it all.

I knew this was a very long stretch, so I put the key in a tub and put in a note that said, “I trust you to use this once and put the key back. I trust you.” I hid the tub behind my garden shed. The idea was that if the length of time genuinely became too much for Kyla, I’d tell her where the key was and she could release herself. I was actually slightly concerned about the implications of being caged for over 50 days.

My trip to Thailand was part business, part play. I would be working in Bangkok for a couple of weeks, then flying down to Phuket to meet a friend who’d moved out there and was working as a teacher. I’d stay with him for a further couple of weeks, before flying back to reality. I’m not going to dwell on this trip, as I’ve got quite a few stories arising from it. I fucked an ambassador’s daughter – you’ll enjoy that one, I fucked a California lawyer, I got more than one happy ending massage, I fucked a ladyboy for money, I fucked a ladyboy for no money. I’m not going to lie, it was a pretty debauched trip. It didn’t help that my friend turned out to be a bit of a deviant himself, and was fucking the mother of one of his students. Yeah, Thailand is an odd place, and Phuket is an even odder part of an odd place.

Throughout my trip I was getting emails from Kyla and we kept a conversation going back and forth. It was clear as I retold stories of my exploits that she was getting tired of being locked up. I nearly caved at one point and told her the location of the key. I got her to send me a few pictures of her wearing panties at work. She was doing well, but as you can imagine, it was not without difficulty. We counted down the last few days.

I was arriving home mid-afternoon to London. Kyla literally wanted to meet me straight away. Unfortunately for Kyla, that first afternoon/evening I was meeting up with my parents, as I hadn’t seen them in a couple of months. The next morning I emailed Kyla and told her I was free all day. She was over in an hour. Kyla didn’t disappoint. She was dressed casually again, wearing a cute red floaty skirt, with brown brogues and a sexy skintight top I would later find out was a leotard. I invited her in and could tell she was giddy with excitement.

I stripped her off down to her panties and bra. She was wearing a matching Calvin Klein set, in a metallic light grey. The panties felt incredible. I told her I would let her out of the cage, but first I wanted her to jerk me off while she told me about being caged for so long. I was a total tease. She told me all about the difficulties she had at work. She said her trousers never quite sat right with the cage, and said everywhere she went and in everything she did she was self-aware of being in the chastity cage. My cock was fully hard. Kyla was gently stroking the full length with one of her hands. I was laying on my bed, eyes closed. She told me about going out to a club and pulling a girl. Each time the girl moved her hand anywhere near his crotch, he had to move it away. Fuck this was hot. I managed to cockblock this little slut from Thailand. Needless to say, the girl in the club eventually gave up. Kyla told me about waking up in the morning in extreme pain as her cock stretched the device to capacity.

Overall though, Kyla said that the last few weeks had been less difficult as her body adjusted to absolutely no sexual sensations. She said her cock hadn’t been hard for weeks and she had very few sexual thoughts until she knew I was coming home. I got Kyla down on her knees. I could feel the telltale rush of cum building up at the base of my dick. It was held there like a cocked gun, ready to explode. I got Kyla on the floor, got her to lift up her skirt so I could see her little caged cock, and I just let loose a fucking massive load of cum all over her face. I spurted right in her eye and she welped in pain, and let the last few spurts go into her mouth.

When I was fully spent I got Kyla to lie down on the bed. I pulled her panties down slightly and began gently toying at her ass. She literally begged me to take off the cage. I did as she wished and unlocked the padlock. I slowly pulled off the shaft cover. I gently touched her cock – the first human touch in over 50 days. I stroked it slightly. The skin was so soft. I could feel it twitch a bit so I took out the middle “bolt”, then took out the clamping part. I then fully released her balls. I gave her whole cock a little squeeze. I wasn’t going to make this too easy for her. I went and got my handcuffs and cuffed her hands behind her head. I started gently stroking her cock.

It wasn’t getting hard. I was stroking it back and forth and it remained almost totally soft. I said, “this is a total sissy cock,” and said to her that it was, “useless.” I asked her who she intended to fuck with it? I said it might never get hard again. I kept stroking, and Kyla kept moaning but it wasn’t getting hard. It was unbelievably sexy. I kept looking up at her face, with cum all over it while I stroked this absolutely pathetic cock. Eventually she did start to harden, and it began to grow.

The funny thing was, when it reached full hardness I swear it was significantly shorter than before. It had previously reached a hardness of about 6”, but this couldn’t have been more than 4.5”. I stroked her fairly rapidly, whispering, “good girl,” and, “let it cum,”. She was clearly getting very worked up, but she kept saying it was so sensitive.

I eventually started saying, “will we put it back in the cage?” I said, “maybe we shouldn’t ever let you cum again, would you like that?” “How about we get it removed?” She was clearly getting very, very turned on by these comments. I told her she had ten seconds to cum or she was getting locked up for another 4 weeks.

 

“10.”

 

“Uhhh, uhhhh.”

 

“9.”

 

“8. You better fucking cum.”

 

“7.”

 

“Please, stroke faster.”

 

“6.”

 

“5. That’s half your time gone you slut.”

 

“I’m going to cum, please, please, I’m going to cum.”

 

“4.”

 

“3. If you’re going to cum, you better hurry up.”

 

“2. You’re going back in the cage soon.”

 

At 2, Kyla let out this noise and started bucking her hips. She effectively screamed that she was cumming. I let go of her cock and sat back. She whimpered and moaned loudly. She continued to buck her hips and I whispered to her that she was a complete fucking slut. She loved it. She bucked her hips one last time and lay flat and rigid. It was then that I heard her gently moaning, “uh, uh, uh, yeah, so long,” and just then I saw her cock start to dribble out cum. There was no force to it, the pathetic thing simply dribbled out cum onto her stomach.

I took the cuffs off and she cleaned up. We went and had some food and I fucked her against my kitchen island. She came on the floor. We fucked again that night and she came twice more. This girl was getting good use out of her cock after so long locked up.

It’s an experience we haven’t repeated. Honestly, I found it a little stressful. Every time I thought about Kyla being locked up for 5, 6, 7 weeks I had pangs of guilt and thought it was too much. We enjoy playing together, but I don’t want to be a complete hindrance on her life. In male-mode she wants a girlfriend, and I don’t want to get in the way. Kyla told me herself she found it a bit odd. We’ve used the cage again overnight, or for a weekend, but never again even for a short business trip.

Regardless, my cock is hard now thinking about this experience. I wouldn’t repeat it, but fuck is it a great memory. I’ve got lots of stories with Kyla from the past few years. I’d like her to post a couple from her own perspective, particular the first time we met. If anyone is interested in reading a story from Kyla, leave a comment and I’ll see if I can convince her! Unfortunately, we haven’t met since January, but that’s how it goes with us. Sometimes there will be a stretch where it’s every week for a while and then a couple of months go by. She’s a great girl though.

I intend to use this account to catalogue my many different experiences with both genetic and transgendered women from around the world. I am absolutely not an author, so please leave any feedback on how I can improve my writing for future stories.

Source: reddit.com/r/gonewildstories/comments/4c50v6/the_time_i_accidentally_kept_a_crossdresser_in