Letter from Toledo

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."

"Not if I take my time...rub you for a while."

Now I was getting really hard. Would she actually take her time?

And, unlike most prostitutes, Phyllis let me kiss her...so it might be an extended necking session.

Oh, I was getting horny thinking about this!

I thought about Phyllis in her hotter moments...we'd gone out for ice cream once and she'd been wearing this little striped top and tight jeans, and then she'd poured her cone on my neck and licked it off....

And then I watched her cute little denim pockets dance on the way home!

Once I'd helped Phyllis paint her living room, and then she'd taken down my pants and sat on my legs when I was sitting on the commode, and she toyed with my penis and giggled. What a girl!

Then Phyllis's seductive voice broke into my reverie.

"And maybe I can do some spanking. Your ex-wife Sybil called me. She found my number on one of your old Amex bills. Sybil says I should charge you up the wazoo."

Oh no.

"Sybil says I should deny you for more than a week or two."

Oh, Sybil!

I began crying softly into the phone. But of course Phyllis had me over a barrel.

My penis was getting even stiffer at the idea that Phyllis had jumped her price from one-eighty to two fifty...

And that she might deny me even more!

But again, it was really too much to charge. Phyllis was a cutie pie, she wasn't one of these high priced call girls, and just advertised in the free weekly as a masseuse who could offer a "happy ending"

I had to be firm. But could I?

"I'm going to enjoy giving you a nice time, Henreid, but you're such a naughty boy..."

By Monday, when I was walking up to Phyllis's apartment door, I was more than enraged, excited and a little nuts.

I'd been watching lots of porn, BDSM stuff and the rest, without having the ability to jack my dick.

My old fantasies of my secretary mistreating me...

Which I used to pound my pud to...

had to just persecute me.

And my secretary, Ambrosia, was a stern but shapely creature, who snorted when I asked for petty cash or to use the pencil sharpener.

But now, Phyllis greeted me with a big kiss.

"Got my money?"

Numbly, I handed her the cash and Phyllis beckoned me into the other room. My God, Sybil was there!

Both women were so gorgeous, Sybil was an ash blonde, her considerable breasts snug in a yellow sundress...

Phyllis of course had wild platinum blonde hair and looked a little like a pudgy Pamela Anderson.

I wondered if we were going to have a three way.

"Now, Henreid, I'm going to help Phyllis learn how to get you in line." Sybil smiled.

"You're just lucky I'm not making you pay me as well...

Dave [Sybil's new husband] could really use a new snow blower."

It was a point of contention with Sybil that I made fun of Dave as he was not much of an earner.

"Phyllis the best part of this is" Sybil smiled...

"You don't have to take any of your clothes off if you don't want to. See, you're the boss!"

Sybil chuckled and Phyllis giggled. I was getting upset and a bit humiliated.

"Take off your clothes, Henreid, get it all off right now."

"Sybil, I don't know that I gave permission to Phyllis to include you in my fantasy session."

Sybil put a manicured hand in her big purse and pulled out the hairbrush... the big, large hairbrush!

My sister gave it to Sybil at my mom's funeral, giggling...

It had dreadful meaning to me!

"You really need to not sass me or Miss Phyllis, Henreid."

I was incredibly horny watching Sybil's red nails tapping the hairbrush, which was rubbing her short skirt...with the long legs encased in pantyhose.

It was driving me a little bit crazy.

I was not spanked until I was nineteen, but then Mom made up for it!

My mother often looked like this as well when she provided me with discipline. I was terrified, and yet quite attracted to Mother, and often she would bring down my britches and whip my bare buttocks till I screamed, then sending me to the corner to weep and snivel while my siblings snickered.

Sybil tapped the brush a bit more. Oh, God.

Now Sybil crooked a magenta nail at me, and I was so terrified.

"Come on, Henreid, take your medicine." Sybil ordered this, and her marvelous eyebrows arched.

"Please, oh please, Sybil..."

"Don't be mean, Sybil" Phyllis said, listening to me babble.

"Phyllis, this wimp is just going to try and con us out of disciplining him."

Phyllis laughed uproariously as I finally shuffled over to my ex-wife.

My face became scarlet as Sybil undid my trousers.

"I can remember Henreid attempting to use flattery and four syllable words to con me into letting him cum...

Right before I was going out on a date, and poor Henreid was of course tied to the bed and talking a mile a minute. I finally shut him up by shoving a huge black dildo in his mouth, and then I left him crying, with the schlong in his mouth while I went out to fuck his old frat buddy!"

I began sobbing softly at the memory.

But I had to try to argue Sybil out of this.

"Sybil you're being a little presumptuous" I insisted as my slacks were dragged to my knees.

Both women laughed as they saw I was wearing women's panties instead of jockey shorts. I was such a little sissy!

"Really, Sybil this is between Phyllis and I, dear."

But then the panties came down as well.

Sybil clicked her nail across my chastity tube, and my penis feebly attempted to swell from within.

Phyllis tossed Sybil the key, and she unlocked my device. It was a bit hard to get it off, because I was so stiff, so Phyllis brought some frozen peas and pressed them against my crotch until my penis went down.

Then Phyllis removed the tube, and took it to the dishwasher to be cleaned, and put the frozen peas back.

"You're a saint, Phyllis" Sybil said, giggling.

"I don't wash his tube, I usually made Henreid lick his disgusting sweat and moisture off the tube with his little mouth. You spoil this boy."

The bag of frozen peas had made my penis tiny, but then Sybil went to work.

As I watched, looking down at my crotch, fascinated...

Sybil rubbed my growing penis with her long nails. My thingie had not had any tactile stimulation in almost ten days...and I began getting quite excited!

"Keep your hands behind your back, you little sissy faggot..."

Sybil snarled up at me, and I was a little freaked out.

"I can't believe I was actually married to a epicene idiot like you, Henreid...

What a pathetic creature you are!"

As Sybil murmured this, she began rubbing my penis a little faster.

Phyllis came over and tied my shirt-tail just over my belly button and walked off, giggling.

I felt tremendously humiliated, standing like this in front of the two clothed women.

This, of course made my erection even bigger in Sybil's palm.

I was also staring at Sybil's quite exposed cleavage in her sexy dress.

"You like these titties, don't you, faggot?" Sybil asked acerbically.

"I remember how you'd mow the lawn and wax the floors just so I'd get in the mood for you to slobber on them...

Or when you'd buy me something expensive like leather pants just so I'd let you suck...

And how you cried like a little bitch when I told you that I wasn't going to let you touch my honeys anymore, no matter what...

Do you remember that, Henreid?"

Tears coursed down my chubby cheeks as I nodded. It had been many years since I'd been allowed to touch my ex-wife's bosom.

I wondered if Sybil was going to let me cum first, and then spank me after the horniness was gone. She'd done this before.

This would make the punishment even more vicious, because I wasn't horny and submissive, just a guy getting a horrible spanking.

Now, Sybil let go of my cock.

"I want you to go limp. This is impertinence, Henreid."

I tried to think about sports scores, or the presentation I was doing at work tomorrow, but my cock got harder, especially as I continued to gaze at Sybil's cleavage.

Sybil lifted a pretty white hand and flicked my sensitive penis with her red nail and I howled. But still, my cock remained quite hard!

Phyllis, watching, said "Don't worry about it, Sybil. He'll limp up after the spanking. He's just horny for us, aren't you Henreid?"

I nodded miserably. I knew this would not be enough for Sybil.

Sybil leaned over and reached in her handbag.

"Sybil, not the metal ruler, please." I begged.

"I haven't cum in nearly two weeks, that's why I'm getting so excited. I promise--"

But there it was, the short metal ruler...Oh God.

WHACK!

My penis burned, and I buckled, nearly going to my knees with my pants around my ankles.