Locked in chastity by a lady of the night

[allenUnderMe]

I met her on my birthday. She rents her time out to gentlemen, and I told her how I like to be used and denied. She had never tried that before but she gave it a shot and it turned her on.


it’s been 17 days now that we met, after which I have not came, and I have a deep ache throughout my groin and into my belly.

just two days ago she finally let the soles of her feet get visibly dirty before allowing me to lick them clean, and that unexpectedly got her off.


now she wants more and can’t get enough.

when she decided to keep both keys instead of sending me home with one for emergencies, I saw the little shudder travel her whole body.


she may let me cum on Friday when I am allowed to scrub her shower clean, or she may not. Either way I will have to clean leftovers once or twice before that happens.

just today we finally communicated how to play with punishments. I don’t want to “mess up” on purpose to get punishment even if I kinda like it, so I told her she can just make stuff up to get mad about and do punishments, but I just like to know when it’s just made it up, so I can stop stressing about my own behavior and enjoy the ride.

when I see her next, tomorrow evening, maybe she will concoct some delicious misbehavior and appropriate punishment to enjoy.


She has never done anything like this before, never even thought about it. The most amazing part of this adventure, is watching her discover new things that turn her on and get her off.

with all that experience, years later and hundreds of clients, I am showing her totally new sht that is leaving her in quivering puddles. That’s what’s getting me off. She also said I have an amazing and gifted mouth and face. I always thought so, but this felt like a life affirming confirmation. She’s probably had 200 faces trying to get her off and I make the top 3? Maybe best but it’s hard to pick, she says. That got me off too.

I’ll have lots of stories. Maybe eventually pictures too. The hottest beauty is in the tiniest details not the broad strokes.


she calls me “no dick” and she says that I will never be allowed to, or able, to fuck a woman again for the rest of my life.

 

[allenUnderMe]

Clapping around like a bell, my wee willie rattled in her cage as she reached out with her foot, experimentally, to jiggle the cage. She was rewarded with a needy gasp and a low moan, and surprising herself made the exact same gasp and moan at the exact same time. I could smell that she suddenly got very wet. She jiggled the cage some more, and then grabbed with her toes and pulled my face hard into her freshly fucked cunt.

Grinding my face in and teasing with my whole face, I slid my nose slowly into her well used messy hole, she gasped and moaned again and I started licking her asshole.

She grabs my hair now, stretched and messy pussy grabbing and stroking at my nose, riding her ass up and down my tongue. “Oh yeah” she cries and cums, clenching and quivering around my nose as her asshole pulses against my tongue.

 

[Custer Laststand]

Sounds like you've found the woman of your dreams.

 

[Custer Laststand]

Clapping around like a bell, my wee willie rattled in her cage as she reached out with her foot, experimentally, to jiggle the cage. ....... She grabs my hair now, stretched and messy pussy grabbing and stroking at my nose, riding her ass up and down my tongue. “Oh yeah” she cries and cums, clenching and quivering around my nose as her asshole pulses against my tongue.

You look good in your cock cage.... very natural. Keep up your good work with your tongue, nose and lips, satisfying your Mistress by kissing her ass.

 

[allenUnderMe]

I should update this. It’s going how many others have gone for me, she has decided that she likes me too much to keep me cucked and denied, and has been making a real effort to “lift me out of” the humiliation and turn me back into a man.

Sometimes being likable is not a blessing lol

I have been able to switch from cuck to bull on the occasion, so it’s not new to me, but this an opportunity to become a LOT more familiar with the role.

She’s listed “cuckold fantasies” on her ****** profile now, and expects that most clients looking for that would want me as the bull.

Maybe this time it will stick. Lol

I know having been a humiliation cuck for 30 years, I have some perspective than can just be devastating as a bull.

I was a bit of a Goldilocks with my cage, small medium and large. Turns out I need a larger cage (so much for sph lol) so as it happens I even have three cages on hand, so if a cuck isn’t caged already they can be immediately caged. A nice value-added service for couples experimenting.

I’ll have to see what happens to my psyche over the next couple days. In the past I’ve tended to drop deep into subspace about 5 days before every new moon. I am in the middle of those 5 days now and I am still ideating as a bull. So, so far she’s been successful. If I end up going 3 months without getting stuck in subspace for longer than an hour or two, then I will be ****** to admit that she has succeeded in the “big flip” where many have tried and failed before.

 

[allenUnderMe]

When we met, I was so obsessed with getting turned on by being denied, that as soon as she told me she wanted me to actually fuck her, my erection just died. And then get it back and as soon as I tried to put it in it died again.

Took me three days to start fucking from a submissive place. I imagined myself a fuck-slave getting tested before being sold, where if she didn’t cum I lost my dick, and if I came I lost my balls. Once I was able to wrap fully around that idea it was on.

She was in a little bit of a different place though, and after she came 5 times, she was determined to make me cum. Which of course I did. She’s fucking amazing. The next time we fucked I tried the same thing, ultimately the same result. And then last night I managed to do the whole thing in “bull space” took her as my personal fuck-meat while we both imagined a cuck crying on her feet.

She only came once during PIV last night (several times before and after, but that’s another story) but said despite that the sex was actually better because it got her off that I was actually going for my nut instead of only focusing on making her cum over and over.

I have to admit that I understood that completely, because that’s been me the last 30 years. I got off on making the lady cum when I did not, at all. So I understand that want, which made it a lot easier for me to take it like that. Not that I ever intend to bust one without taking her over the edge first.

There’s just something incredible about feeling a pussy cum hard around my dick. Making the muscles convulse around my shaft while driving her deeper into it.

I know this isn’t what anyone expected of this thread. It’s not what I expected either. I expected to be kept in near permanent chastity and kept frustrated for months at a stretch, and to be her bottom maybe for years if not forever.

But maybe it will be edifying all the same. The chances are at the other end of this I’ll be able to switch back and forth from top to bottom a lot easier than I can now. It used to take me days to flip headspace, now it’s down to an hour. when it gets to where I can flip back and forth in the moment, she wants me to start talking to other women and couples.

I think it’s going to be a pretty amazing journey.

 

[Custer Laststand]

When we met, I was so obsessed with getting turned on by being denied, that as soon as she told me she wanted me to actually fuck her, my erection just died. And then get it back and as soon as I tried to put it in it died again.

Maybe that was caused by your Mistress keeping you for a long time in your cock cage, where whenever you felt like becoming erect, that quickly became painful — so you became soft again.

Took me three days to start fucking from a submissive place. I imagined myself a fuck-slave getting tested before being sold, where if she didn’t cum I lost my dick, and if I came I lost my balls. Once I was able to wrap fully around that idea it was on.

If that's what worked: very good. As they say: Your strongest sex organ is between your ears.

There’s just something incredible about feeling a pussy cum hard around my dick. Making the muscles convulse around my shaft while driving her deeper into it.

Excellent. You have the right idea.

But, maybe it will be edifying all the same. The chances are, at the other end of this I’ll be able to switch back and forth from top to bottom a lot easier than I can now. It used to take me days to flip headspace, now it’s down to an hour.

Congratulations. You've made great progress under the guidance of your Mistress.

When it gets to where I can flip back and forth in the moment, [my Mistress] wants me to start talking to other women and couples.

Given this, and your earlier comment:

"She’s listed 'cuckold fantasies' on her ****** profile now, and expects that most clients looking for that would want me as the bull."

You should, of course, continue doing what your Mistress tells you to do.

I think it’s going to be a pretty amazing journey.

It sounds like it. Please keep us updated.

 

[Custer Laststand]

When we met, I was so obsessed with getting turned on by being denied, that as soon as she told me she wanted me to actually fuck her, my erection just died. And then get it back and as soon as I tried to put it in it died again. ............... I think it’s going to be a pretty amazing journey.

You haven't posted since 12 Oct. 2020, AllenUnderMe. How about an update....?