Letter from Toledo

My penis was now getting smaller, and it hurt.

Sybil's face became concerned.

"Oh, darling, I hope I didn't hurt you!"

Sybil rubbed my penis with her fingers.

Soon it was again really stiff.

"You--why you're hard again, Henreid. This is impertinence!"

Sybil reached between my legs and squeezed my balls, and I almost fainted.

Sybil then grabbed me by the ear and dragged me across her lap.

I swore, humiliated as I was that I wouldn't cry in front of Phyllis. But I'd forgotten what a formidable spanker my wife was.

Captain of the Temple River Country Club tennis team and of course Sybil also taught racquetball and squash as a volunteer to inner city kids!

What a forearm she had!

By the fifth swat of that evil hairbrush I was screaming at the top of my lungs.

Sybil had my right arm twisted behind my back and I flailed my legs tot he point that my pants and shoes came off.

But Sybil grimly continued swatting my bare cheeks until Phyllis intervened.

"Yes, I suppose that's enough."

After this, the ladies ordered me to undress completely.

Sybil's full lips were smirking at my discomfort, and her boobs shook in the tight sundress as I became fully naked. My rear was in horrific shape, and as I was ordered to kneel on the hardwood floor before them, I was careful not to let my welted buttocks rest on my thighs.

"You were so hard on him, with the whipping" Phyllis said, with a sympathetic grin.

"He needs it, he's a manipulative little bitch" Sybil said, laughing.

"Trust me, his ass has had worse. I've used the strap on and had to find bigger and bigger phalluses. His anus is wider than the Grand Canyon now."

And of course I was absolutely humiliated by this casual revelation.

Sybil smiled. "Don't touch your wee-wee yet, Perv-boy"

Sybil turned to Phyllis. "You know, Phyllis, Henreid is all excited about being allowed to jerk himself off, so the meat beating should last a while, so he can get full enjoyment before he is locked back up and sent back to another week of chastity."

Phyllis snickered. "Yeah, Henreid, take your time."

Sybil smiled evilly at me. "That's right. Try to remember the training I've already given you, sweetheart."

I was upset now, I had thought that I would be teased manually, but apparently not,

oh well.

Sybil read my mind. "No, no one wants to touch that ugly thing of yours. We don't have a microscope handy, anyhow."

Phyllis laughed so hard she almost shot beer through her nose.

I began toying with my penis slowly, and the girls sat and watched, sipping beer.

"You learn a lot about the Beta male here, Phyllis." Sybil said.

Phyllis was not as well versed as Sybil, and looked a little puzzled.

"You know, the Alpha males are the ones with five girlfriends who stand you up, and the Betas make good husbands, but don't really make you all that wet...you must've had a bit of both."

Sybil paused as she thought about it. "You know, I loved Henreid in my own way, but I married him because he was far more stable than the guy I was shtupping at the time, and brought home a paycheck. Jamal was hot, but terminally unemployed."

I remembered Jamal, the guy at the car wash. How disgusting. Jamal worked at the car wash twice a week, and Sybil had managed the car wash, and then Jamal had quit, but apparently had never quit Sybil.

Now Sybil reached into her sundress and casually pulled out one of her full beautiful boobs...smooth pink nipples...oh God. 36DD.

Sybil held it up to her mouth and began licking the nipple.

Sybil knew that this would get me even more excited. She'd denied me access to her breasts some years back, but often when she'd allowed me supervised masturbation, she'd play with them in my presence...

Since most of the other times, she kept them covered...though I was kept naked around the house.

And God, were they beautiful breasts.

Phyllis reached into Sybil's dress and pulled out the other breast and began licking that nipple.

As you can imagine, I was getting way too excited and began playing with my dick a bit faster.

And it had been some time since I'd cum, and I felt it all about to shoot.

Sybil calculated about the time I was on the verge of cumming, and using her softball trained pitching arm, threw her Schlitz beer can at my dick.

It passed my dick, as I was kneeling upright, so not to hurt my bottom, and slammed right into my testicles. Yes, and as I had my cock pulled up to my stomach, it was a clean shot to the scrotum.

I screamed, but Sybil laughed.

"I told you not to play with them too fast. Too bad I'm not wearing my nice spike heels...remember how I used to bang the tip of your cock to slow you down when you were jerking it?"

I regretfully remembered.

But Phyllis felt badly, and she beckoned to me.

I was weeping, and my lower lip was trembling. I was a lifetime teetotaler, and thus was a disdainer of beer, but it was all over me.

"Look at the little baby cry." Sybil said, laughing.

"I used to put him in adult diapers when he threw fits like this."

Phyllis smiled. "Come over and sit next to me, precious."

I was now sobbing openly, like an exhausted two year old. but I went and sat next to Phyllis on the couch.

"Now sit on your hands, I don't want any help from you...Phyllis's going to give you a nice wee-wee massage."

I obeyed, and Phyllis played with my cock, expertly rubbing the tip with a long nail, and then tickling the underside...

She kissed my ear and my neck, and giggled as I gazed into her cleavage, hypnotized.

"I love you, Miss Phyllis..." I mumbled.

But I smiled at Sybil, who was now disconsolately smoking. Sybil had more than once stabbed my erection with one of her Marlboros, but she was being so good now, and she was a gorgeous woman.

"I love you too, Sybil. And I appreciate you helping Phyllis with my training."

Sybil smiled, and moved closer, dropping one of her shoes off. She began rubbing the underside of my cock with her toes as Phyllis toyed more with the tip.

"Now ask permission before you cum." Sybil warned.

"C-can I now, I'm on the edge." I begged.

"No, not yet. Please don't make me kick you in the balls, sweetie."

"Sybil you're being so mean." Phyllis protested.

"You just don't know our little faggot. He will get over on you. Remember, spare the rod spoil the husband, all that."

I held back as the gorgeous fingers and toes continued to stimulate my now quite growing member....

I was so close and trying desperately to hold back.

Finally Phyllis nodded and I began moaning. Phyllis jerked a little faster and Sybil rubbed her toes a little more, and I shot into the air, much of it falling on Phyllis's palm.

Sybil smirked as Phyllis went and washed her hands.

"Think, I'd make you lick it up...I'd make you shoot on my full ashtray and lick it up."

Sybil was truly a martinet. But she was leaving town, and I would miss her.

We had been married for eleven years, eight of them that I'd been her chaste slave...

But I was confident that Phyllis would pick up the slack, though it would be expensive.

Now Phyllis came back. "We have to lock you up again honey."

Phyllis had brought the clean chastity tube over and she put it on my now quite small organ once more.

I gave Phyllis a huge tip over the $250, and left, feeling somewhat satisfied.

By that night, of course, my erection was once again raging against the tube, and I didn't help things by watching some femdom porn.

The next week, I saw Phyllis, and she jerked me off...much sweeter without Sybil!

And then it went on for several weeks.

Then I began running short of money, as I still owed child support to an earlier wife, and other stuff had been going on.

Phyllis had laughed when I'd explained this on the phone. "Well, you can stay locked up till you see me, or you can drop by and get the key."

"I'll stay locked and try to save money."

And I did, I got a cheaper car, and a smaller apartment. I began to be able to see Phyllis once every two weeks, and although this was harder on my chastity, I had a good thing going.

Then an interesting complication occurred. I ended up going for lunch with a girl from work, her name was Lonni.

We had such a good time, that we went to the movies the following night, and then again the next week.

Lonni was sweet and she was driving me around (I had sold my car to have money for Phyllis) and when she brought me home from dinner, we began necking in her car.

My cock was now raging in the little chastity device.

"Do you want to come upstairs?" Lonni asked...

God, she had a nice figure, and my hands were all over her tits.

"I don't mean to be forward but I give a mean blowjob."

I told Lonni that I was tired. A blowjob. Oh how hot that would've been.

I jumped in the shower, and cooled off.

Lonni called me, apologizing for being so forward.

"No, Lonni, I'm very attracted to you. I just want to enjoy the uh, process."

This of course was a complete lie. I was ready to jump her bones, but I couldn't do it all locked up.

It had now been nearly eight months since I'd been seeing Phyllis , and my penis had been locked except for the washing and teasing Phyllis gave me when I could afford it.

A couple of days later, I showed up at Phyllis's place.

Phyllis tossed her long, thick curls and smiled, and of course my heart and my cock went thump-thump.

Sitting next to Phyllis, breathing in her glorious scent, I told her about my dates with Lonni.

"Do you want me to give you the key?" Phyllis asked, concerned.

"We could take a break on this training, you know." Phyllis was smiling.

She was very grateful to have learned about the key holding service thing, and that I'd shown her a lot about it, (to say nothing of Sybil's valuable instruction"

Phyllis had other clients now--one fellow, Seymour came in only once a month, would bow to her, strip, and get unlocked...

And then Seymour would face the wall and jerk off...

How low maintenance was that?

Phyllis grinned. "You know, Henreid, we have a nice thing, but wouldn't you like to meet a girl and settle down? Maybe you could get her to do this, or you could get therapy and just be normal."

I shook my head. "I love you, Phyllis. And I like this girl, but I don't think I want to give up the training. I'm more focused at work, and I'm exercising more so I don't think about sex as much."

And of course it drove me sexually crazy that this hot girl kept me from jerking off...wow!

Phyllis smiled and gave me a big, long, kiss. It must've been terribly flattering to this former waitress that this guy was giving up all hopes of a normal sex life to do this weird tube thing.

Phyllis took me by the hand to her bed, and instructed me to undress. She was clad in an aquamarine colored tee shirt, very snug, that showed her belly. And of course tight jean shorts.

God I loved girls with the cut-off shorts! In school, I'd always dreamed of dating them, but I was a Student Council, Mathlete type...those girls preferred to smoke with the guys from Shop class.

Finally I undressed. I looked inquiringly at Phyllis.

"You know I'm not going to take off my clothes for you, honey."

Phyllis smiled as she began tying me, spread-eagled to the bed.

"I was undressing to my bra and panties for a little while, but little boys shouldn't see Mommy nude."

This of course was humiliating and arousing at the same time...

Phyllis finished tying me to the bedposts and unlocked my chastity tube.

She went to put it in the dishwasher and returned..

God she was hot in her sexy white-trash girl clothes!

Phyllis sat down on the bed next to my crotch and she bathed the accumulated sweat and dirt of two weeks (alas, that long) from my penis.

Oh, those long hot-pink nails!

"Yes, one of my regular clients was here and he fucked my mouth and my ass good on this bed this morning, and then my boyfriend came by and did the same thing...

I was naked as a jaybird most of the day! But you're a little slave-boy, and I can't give you those privileges anymore."

I was so humiliated, but again, quite aroused.

Phyllis finally got some lube and began rubbing my penis, concentrating on the crown and then the delicate area below on the underside of my cock...the frenulum.

Phyllis snickered to herself, and let go of my cock so I was humping air. She went to the kitchen and brought back a cutting board, a sort of flat piece of wood.

She put the cutting board under my scrotum (remember my legs were spread wide)

Then Phyllis took one of her heels off. Oh, I'd had this game before...

"I am a little jealous that you're seeing other women."

WHACK! Phyllis stabbed my penis with the board and I screamed.

Then Phyllis began rubbing again in quite a loving way...

"Sweetie, you know I care about you. I want you to have a good social life. I know you sit at home reading science fiction and playing with your stamp collection...

It must be lonely. Especially since you can't jerk off for weeks at a time."

This was true. I'd even given up my cable channel and all my porn subscriptions so I'd have more money to see Phyllis. Hell, when Lonni and I went out, we had to go Dutch.

Phyllis lifted the spike heel and this time slammed it on my scrotum, which was lying on the cutting board.

I screamed again, and burst into tears.

"P-please, Phyllis, I love you. If you want me to break up with Lonni I will."

What was I saying? I'm forty-two years old, am I just going to spend my life dedicated to this crazy blonde? Thinking of it my cock grew harder.

Phyllis smiled, and put her heel back on.

"Henreid, I think we should wait till next time for you to have a cum, honey."

God, that accent...what did she say?

"Why, Miss Phyllis?"

"Sybil sent me an e-mail. She says I shouldn't let you cum every time, that you just expect it every time you come here...."

Phyllis began rubbing my cock and her boobs were shaking in the cute little top.

Phyllis's long legs were crossed and tan...the previous time I'd visited, she'd let me rub oil on them and how fun that was!

"I also think you should give me three hundred dollars a visit instead of just two-fifty with an occasional twenty-five dollar tip. I think you'll value me more."

It's unbelievable...I did it. She offered to take off the device and let me pursue Lonni, but I need Phyllis more.

I did show Lonni the device, and she told me I was an evil perv, and wanted nothing to do with me.

I still see Phyllis...she's incredible, but I average about five orgasms a year, and only can afford to see her about nine times a year.

I have lost all hope of a normal relationship...but I need Phyllis more!

Best,

Henreid.

Dear Henreid...

Your life, not mine, thank God.

Best,

Shoeblossom