Dear Shoeblossom:
I really enjoyed "Letter from Los Angeles: Ms. Scunthorpe's Rebuttal" and also the story from the Time-Lock computer Mistress in "Letter from Greater Ponsonby ."
I also have a paid key holder, Phyllis.
I grew up in a strict Evangelical family, here in Ohio, and our parents were very primitive, sexually...
Masturbation and copulation were considered shameful.
Of the five boys, Llewllyn, Hycel, Gottfried, Henreid, (that's me) and Tolliver, none came out very normal. Lew was shot to death by a jealous husband, Hycel was the husband...
Gottfried went into the seminary, and spent his life as a bishop in weird scandals, and Tolly ran away from home to be a male prostitute right after high school...
And I have always been a habitual masturbator...and the battle never seems to end!
I've been in chastity on and off since the early 90's. It's difficult to find women to hold the keys to my chastity tube...
Especially in a small town like Temple River, to say nothing of the tea party-Red state this town is located in.
Phyllis is an attractive woman in her late thirties, a MILF of sorts.
She's a curvy sort with frosted blonde hair, given to wearing snug tank tops, tiny denim cut-offs with fishnet stockings and heels, long nails, bright lipstick.
Phyl is the kind of girl you notice immediately in a bar.
Phyllis offers massage services in the local weekly to guys in our area. She isn't exactly a call girl, but you can generally work something out with her.
One of my buddies told me about her seventy-five dollar blowjobs, and I did that once or twice. But essentially, I'm a submissive.
I was married to a sweet woman who held my chastity tube key even after our divorce. I'd stay locked up for weeks and weeks...
And then drop by and give Sybil, my ex, her alimony plus a few dollars more, and she'd unlock me, order me to kneel naked and jerk off while getting to stare at Sybil's long legs in their high spiked heels.
There's nothing like it, Sybil would be wearing a tight little pink low-cut minidress, sitting with her long, beautiful legs crossed, and telling me what a pitiful tiny-penis fag I was, and why she'd never had an orgasm from me...and I'd jerk off to a little squirtie, before being locked up again.
This arrangement had worked out quite well for several years. Sometimes when I came by to give Sybil her check, I'd confess to drinking too much, or I'd curse in front of her or look a little slovenly, and then, after getting her check, Sybil would strip me naked and whip me with her big hairbrush.
And then sometimes Sybil would decide, despite my begging, not to unlock me for that month, especially if she was in a sour mood.
Imagine...I'd drive all the way from Temple River to where Syb was living in Ethansville...and all the way back, HORNY.
She'd send me home in tears, forced to wait another thirty days...(or sentence me to another sixty, and just tell me to mail next month's money)...
Other times, Sybil would order me to service her orally, which we both liked very much...but if she also didn't want to let me cum, I went home REALLY horny.
Still, it was what I needed. Being locked up was an ordeal...
Think of it, pretty girls passed me by all the time anyway, because I was basically a schlub... and I didn't even have the satisfaction of jerking off when I got home!
Still, I was more focused at work, and I spent more time on hobbies and volunteer work for my church, since I wasn't jerking off to porn constantly. Though I still looked at dirty flicks, but it was even more torture, since I couldn't get into my belt.
Sometimes Sybil would decide I was a little too fat during one of the visits, and she'd demand that I lose five pounds, not an unreasonable amount, before I got to jerk off...
I loved snacking, but Sybil's dictum meant I had to throw all the Twinkies out of the house and do some serious running. I really wanted to jerk off the following month!
Did being in chastity and only seeing my ex once a month get in the way of my dating life?
Well, I didn't date a whole lot, geek that I was. Being a nerd most of my life had meant I was alone much of the time...
I'd met Sybil and gotten into her shorts when she was on the rebound from breaking up with one of my more attractive male friends.
Sybil and I had been married for sixteen years before our break-up.
The last fourteen or so I had basically been Sybil's submissive. Sybil had liked this because she didn't want to fuck me...but if I jerked off, I became less devoted to her.
Having me in the chastity tube meant she could fuck her friends, I'd do the house work, fully financially support her, and lick the cum out of her ass when she'd fuck my various male friends.
But at some point, Sybil and I had divorced, of course, and then we had this key holder thing going with the alimony arrangement, though often Sybil urged me to go into therapy.
I continued to give Sybil alimony for years longer than the judge ordered, just for the monthly masturbation sessions.
It was kind of exciting, being locked up and dreaming of when I'd get to jerk off in front of her...
And listening to her remind me that other men were getting to fuck her every night. Sometimes Sybil would actually call me at home, when I was sitting there, lonely and chaste, and tell me what a sad little wimp I was...
But then two things happened. Sybil married again, and became a born-again Christian. She told me that I could have my keys back and she wanted no more money from me.
I was happy of course that Sybil had been good enough to hold my keys for that long.
I actually gave Sybil and her new husband the down payment for their house, and one more time Sybil whipped my cock with a belt, while her husband just looked away, very into his Bible. But then it was all over.
Sybil moved to Snydersport with her new husband, and I've not seen her since!
After this, I wasn't too sure what to do. I tried putting the keys in ice to keep me from beating off, but that didn't work well and wasn't very sexy.
I began having paid sex with Phyllis, and then eventually I told her about the key holding thing.
Phyllis thought this was hilarious. She made me model the little tube between my thighs. I'm a pudgy little man, and having this chesty blonde laughing her ass off was actually quite arousing as well as very humiliating.
"So you want me to take this tube thing off you once a week and play with your dick?"
I was feeling so ridiculous, standing there as she sat back, beautiful legs crossed, smirking at me.
Phyllis was in one of those cute denim miniskirts and the high heels. I was pudgy, naked and tubed....
"Yes, that's right, Phyllis."
"And then you make your mess and I lock you back up again?"
"Sure, and it'll give me something to look forward to so I'm not jerking off all the time."
"I bet you're quite the porn addict, Henreid."
It was very mortifying. At work I have a staff of forty, and here I am almost naked standing nervously in front of this redneck girl, who I doubt got past 9th grade!
Phyllis's breasts bounced merrily in the meager tube top she was wearing...
And my penis swelled painfully in the metal tube that I was wearing!
Phyllis took the key and sent me home, telling me to return the following Monday.
But she forgot to let me cum before I left. I thought of going back to remonstrate with her...
And of course when I called Phyllis about this she laughed.
"No no, see you in six days, horny boy."
It was really an intense experience. I got home that night and began fantasizing about the whole key holding experience.
I had of course read all about it on computer blogs and in porn lit.
And I'd seen a few films, more than a few, actually, about chastity and denial.
But I always jerked off at the end of the absurd fantasy of being locked up....it was a contrary situation!
The real thing, is so different from the fantasy...
Kind of like watching "Rambo" compared to being drafted, I guess.
I lay in my bed and fingered the metal tube between my thighs.
I thought of what it would be like to live with gorgeous Phyllis full time an d having her tie me down for hour long tease sessions four or five times a day.
For some reason in these dreams I didn't work or do anything that would distract from the teasing.
It was a little ridiculous, this dream, since Phyllis's hands wouldn't be energetic enough to play with my penis all day long...
You'd think it would bring on arthritis!
Imagine it, for two or three hour increments!
But the image of my wrists locked behind my back, or being tied spread eagle to Phyllis's Princess bed...
While my beautiful girl toyed with my empurpled member for hours...just drove me nuts.
Phyllis's long nails rubbing and tickling the foreskin...
And of course previous to the entubing, I could jerk off, and go to sleep or something.
But now all I could do was touch the tube lackadaisically.
I tried to remove the tube for one fervid wank, and of course it was securely locked!
I considered going into my toolbox and breaking the tube, but I'd spent over two hundred dollars on it, and it seemed a little ridiculous.
When Sybil and I were together and she'd locked me in chastity, at least she was around a bit...oh God.
The next day at work, when I usually punctuated my afternoon with wank trips to my private executive restroom, I was especially frustrated.
My brother Hycel dropped by. He was just out of prison for shooting my other brother during the cuckolding episode...
Hy had been President of my uncle's firm, where I work before he'd gone off to stir for shooting our other brother during the cuckolding...now Hy was starting out in the mailroom again.
Hy came by my office, looked at me, grinning.
"I bet you're spending half your time in the Executive Washroom, beating your meat."
Hy left with his little mail cart, whistling, and I blushed, though I was truly frustrated.
I LOVED my private restroom. I had recently been promoted to a job where I could have my own one-staller, and now I could no longer use it for the nefarious, but glorious purpose!
When Sybil and I had been married, sometimes she would show up at the office, and order me to drop my suit pants...
And Sybil would give me a few sexy wanks after unlocking the tube...
And then lock me back up, and spank me hard, just to take my mind off my horniness!
Then Phyllis actually called me at work!
Right as I was ruminating about the old days...
"I just wanted to see how you were doing with the chastity tube!" she giggled.
"It's not that easy, Phyllis, but I am bearing up to it."
"I wanted to tell you that I'm raising my hourly rate to two fifty, Henreid."
"What? Why, Phyllis? We're old friends. That's a call-girl rate."
"What, I'm an old hag?"
"It's so expensive, Phyllis."
"Well, my kid needs braces, and I'm going to be doing you a special service, Henreid."
"Phyllis, it's going to be easier than the old routine.. blowing me, or fucking. It's just a hand job. I'll probably be out of there in less than an hour."
