Letter from Lythgoe Heights

Dear Shoeblossom:

I want to tell you about my male master, Emil. He is Austrian, and although I am, I think a heterosexual male, not really bisexual, or maybe a bit now...

But Emil is a find!

Just this morning I was being tutored in how to edge without cumming. When I got close, kneeling in front of Emil, he reached down and tweaked the mousetrap on my right nipple, and whaddya know?

It's great self-control training! I heard about Emil when I read "LETTER FROM SKOKIE" which I thought meant he was Chicago based.

The letter told of Emil's work with Morrow O'Malley, a depressed anchorman for an NBC affiliate, and, how after he got hard-core training from Emil...

Morrow became Margot, and gave up his two packs of Old Gold Straights and his fifth of vodka, and turned into an enchanting weather girl.

I found this incredibly inspiring. It was so obvious that Margot was much happier, even though she became a full time pain slut to a variety of perverted men...her butt was branded with her new husband's initials, and most of her personality was seriously fragmented.

From time to time I have hired a black hustler, Ace...to dominate me. One night I told Ace about my Emil fetish, as he whipped my rear as I was tied, uncomfortably, and quite naked on a carpenter's wooden horse.

Ace laughed, as his ebony muscular arm, tight in the tank top swung a cut piece of fiberglass against my trembling cheeks.

"Whut choo want, a Nazi fantasy, Cosmo, you little bitch?" WHACK! WHACK! "This nigga not good enough for you. Not hard enough?"

Ace had then reached under my legs and pulled my hard cock out, lying it flat behind me.

"N-no please Master Ace don't...not my-"

WHACK! The cruel switch landed sharply on my bulbous glans. I shrieked.

Ace gave a belly laugh. "You dumb bitch. You ain't goin' t'get any better whippin' from some Hun, some Kraut, then you get from yo' man Ace!"

Ace tenderly thumbed my shriveled sore penis back into bulging tumescence, before landing the fiberglass again, sharply.

And it was true, I'd mused as I jerked off onto Ace's military boots before licking my semen and handing him his five bills.

Twenty painful minutes later, Ace had my ears in his big black hands, and was skull-fucking my face into four or five orgasms, shooting his spermy loads into the back of my head.

After I could not get Ace hard a sixth time, he'd given me one more harsh whipping, as he snickered, thinking about my fruitless hunt for a German replacement.

Ace was a tough guy. He'd been in and out of prison, and a professional kick boxer, and he had me cowed much of the time, but it wasn't enough...

Sure, when I'd had a fantasy about being fist-fucked, Ace was there. He'd used a cut barbed wire on my ass and made me squeal like a pig. He was a tough Dom.

It wasn't force, but IMAGINATION. I knew that Emil had more imagination and creativity, although Ace was, indeed, a handful, so to speak.

So I had to search! Finally, I emailed Emil in Austria.

His rates? Very expensive...

But, I have three inheritances and run my own hedge fund, so I was able to offer Emil, after nine months of service, a five year contract. He has simplified my life in so many ways!

I jerk a little faster, and Emil kicks me lightly in the balls. His boot is at penis level as he is standing over me, fully clothed in his smart black pants and turtleneck, as I wiggle my wee-wee, nude and exposed.

"Must I put you back in ze chastity device, Cosmo?"

Not unkindly, Emil clicks his tongue against his cheek.

I remain silent. I don't want to begin begging Emil to let me keep playing with my cock. I have my pride, after all. I'm not a child.

But Emil reaches down and tweaks my left ear till I squeal.

"I am talking to you, Cosmo. Ja, you want me to lock you up now?"

Biting my lip, I look up at him. Emil is so handsome! A blond crew cut, and a firm jaw.

"Its...up to you, Emil." I pause. I will not give in.

"I vant you to learn how to masturbate slowly-to edge. It is a nice way to give yourself some pleasure and learn self control, without having an orgasm, ja?"

I nod silently.

I can't believe how rock hard I am. This may have started after I was ejected from Princeton, and went to live with an older cousin in Secaucus, New Jersey.

Hank tutored me and got me back up academically, and when I seemed to be flagging, he'd take my jeans down and whip me with a leather belt-or sometimes, if I sassed him, I got a thorny switch from his rose garden.

I was twenty years old then, a bit old for correction, but my parents had gotten sick of my shenanigans, as I'd been kicked out of five high schools and two colleges. And, within a year, my aching butt and I were back in Princeton, making the dean's list.

Hank also gave me merciless thrashings for masturbation, as he was a very religious man. Sometimes he would suspend me from the high beams of his barn and whip my naked cock with a cut off garden hose until I screamed...

This had left me with, of course, an intense desire for chastity training and discipline.

My first wife, Haley, took to this like a duck to water, and kept me in a Prince Albert hooked in to a metal sheath for months at a time. After we split, I met Katie...

I had to explain what I was into. "I need to be kept in check."

Finally, it was humiliating, I had to ask Haley to come and show Katie, which was difficult, as Haley and I had not had a civil parting. Kneeling naked and mortified, I'd had to wait as Haley showed Katie the holes that were in my foreskin...

"Why didn't you keep your piercing in, Cosmo? These holes will have to be re-drilled, I think."

Although Haley's teasing fingers were dexterous, and she could handle a whip, she was in a wheelchair, and rolled over my toes as she went back and forth..

"You really should have maintained this, Cosmo."

"I thought maybe I was over the kinky thing." I'd muttered.

"That's a laugh" Haley had sneered, and she and Katie had bent over in giggles.

But Katie didn't work out in the end, either. And I needed someone who really knew the whole business of being a dominant.

For one thing, being impaled by a strap-on dildo, no matter how long and invasive, pushed by a woman's relatively weak hips, is nothing next to that of being sodomized by a large, thick cock.

One that I could lick my shit off and suck to a second orgasm afterwards!

Discovering Emil was really something.

Sometimes Emil would time me, and see if I could get him to cum in my mouth within three minutes, using blowjob tips from women's magazines...

"Ah, four minutes again, Cosmo. Go fetch me de razor strop."

I've learned such control under Emil. One day he had me stand, after a vicious caning, and he took a box of sewing needles and slowly inserted at least seventy of them in different parts of my butt.

"Zis will keep de memory of your correction for a bit, no? Now to the corner, and zink about your errors, Cosmo."

And finally I got to meet Margot, who told me of her miserable life as a cocaine-dependent Morrow O'Malley.

"It was hell, even when I was getting laid constantly as Morrow." the beautifully coiffed woman told me as she sat on my couch. "Now I have my cock locked down eleven months out of the year, and take it in the ass every night from my husband, who is a parking lot attendant at the TV station in Skokie."

And Margo was very happy and content, and had been sober for several years. He/She was so grateful to Emil for all the work that had been done, and indeed begged Emil to let him/her service the German's cock, but Emil politely refused.

"I have Cosmo here, put on his pink lipstick and panties and he gives me quite a good time, Margot." Emil smiled. "I am going to have him go down to the bus station and even to the pier to find more men to practice on."

I had confessed to Emil recently that I wanted to become "Cosima" and enjoy being a ladyboy. I understood that Morrow/Margot was eventually going to have the testicles frozen and removed, which I was not up to, but I did want to be a servicing sissy-boi. I wanted it badly. But I was scared.

"It's rigorous training" Margot told me. "As Morrow, I weighed a buck-ninety, and had to diet my way down to one-twenty-five to be a more attractive woman, and Emil put me through extensive exercise. And then he pierced my tongue."

"Why?" I was astounded.

"Well, he attached the piercing to a large plastic dildo which I kept in my mouth while sleeping and several hours during the day. It helped me refrain from eating-I was on a smoothie diet-and trained my mouth to loosen up for blowjobs."

Emil and Margot laughed, as I sat there, somewhat revolted.

"Margot has a large, loose mouth now." Emil explained. "She got collagen surgically put in lips, so they are plumper and more sexy, and can take large Negro dick now."

I remembered that there had been an expose when Morrow O'Malley had been in the news, that he had relatives in the Ku Klux Klan...and of course was very conservative.

Margo read my thoughts. "Yes, it's changed. My husband is an enormous half Hispanic, and half African-American. I've never gotten surgery to remove my dick, but between sleeping with the pierced dildo on my tongue, and having an enormous cucumber up the south side, I've got two holes to keep the largest black man quite happy."

Margot also mentioned that she'd heard about Emil from an even more PREVIOUS letter to you, "Letter from Port Corcoran".

This missive, in which Emil subjugated a middle school vice principal, and before that, that educator heard about Emil from...

Incredibly- "Letter from Bullfrog Commons (back in '06!)" so apparently Emil is a big hit with your people!

Autry Cavendish, the freaky girl (actually a woman-born woman for a change) who wrote from Bullfrog Commons, liked it when Emil pushed her curling iron up her anus...Sheesh.

But yes, Emil was worth it, but still way scary.

"You want to be a beautiful woman, Cosmo, to be Cosima, and that means no more junk food (Emil pronounced it "chonk fud") in front of Sportscenter." Emil warned me.

I began getting up at four a.m. and running naked in place, as Emil urged me with a swinging bamboo cane. My ex-wife Haley, the wheelchair bound nutritionist, came by with a powder I could eat three times a day, along with eating wheatgrass and drinking tomato juice as my weight dropped dramatically.

Haley laughed, her full breasts bouncing above the arm rests of her chair, as I teetered back and forth on high heels, wearing only thigh high stockings.

"It's good you can teach him how to walk, Emil. Pile those books on his head. Cosmo's such a little bitch anyway."

"I had lunch with your second ex, Katie last week, and she thought this sex change is so hilarious, Cosmo, especially as you are always contributing to those Congressmen and Senators who are so anti transgender." Haley purred.

"Soon, Haley, I shall have Cosmo in makeup and dress going out to service tramps and hoboes behind de Lythgoe Heights Salvation Army. It will give him a marketable skill, ja?"

I stared down at my heels and my cock, hardening against the steel chastity device. It was so humiliating. Why did I have such strange desires?

After college, as a young man in my early twenties, I'd gone on a European tour and had stayed for some time with my grandmother, who was quite youthful and had a large house in Luxembourg.

Grand-Nana had seen some of my transcripts and was appalled at my study habits. "You do not deserve to wear the pants of a young man, Cosima." She had been the first to feminize my name!

Grand-Nana had had a whitish-blond crew cut and looked a bit like the busty movie star Brigitte Nielsen. After she'd discovered me masturbating into her laundry bag, she had taken control.

For the nine months that I'd stayed in Luxembourg, Grand-Nana had forced me into frilly Austrian frocks and black Mary Jane shoes with tall white socks.

For the least fraction of decorum, Grand-Nana would hike up my skirt and pull down my frilly panties and thrash my bum with a braided horsewhip, and she also, like Emil, had encouraged early risings and bedtimes.

Grand-Nana had stripped me more than once a week, stroking my hardened cock with long red nails, trying to understand my masturbatory proclivities.

"If I cane your wee-wee with a cut rose branch, perhaps it will discourage your filthy habits."

But of course Grand-Nana never broke me of them.

My drunken, athletic cousins, Tate and Taft, who'd always snickered at me for being the nerdy intellectual, came to Luxembourg to laugh at my frilly dresses, but then Grand-Nana moved in, and transformed them to Tina and Trixie...and I think they still run Grand-Nana's perfume factory...(and they got full dick-less operations...)

So, of course at some point I fled home!

Emil and Haley had listened to my stories of cruel Grand-Nana and they too agreed that it was best that I stay in chastity extensively to help me refrain from wasting time rubbing and poking at my privates.

"How's this, Cosmo?" Haley asked cheerily. "If you lose two pounds a week, at the end of the month, we'll let you jerk off. But if you don't lose, you'll get a caning every week."

I remembered an old letter to you, Shoeblossom, "Letter from Huckleberry Heath" where an obese woman was trying to lose weight, and was regularly punished by her husband and his young mistress...and sometimes there were plateaus where she just couldn't take the weight off...and she was punished very severely.

I recalled from the letter, the woman's big white body covered in long red weals and cuts as little Bambi had gone over her with a thorny rose branch.

I mentioned this, and Emil grinned. "Yes, but eventually she lost the weight, didn't she?"

I reluctantly nodded.

Haley, who often liked me to go over her knee as she sat in her wheelchair...

She'd grab my balls and hold them behind my legs as she whacked them with a ruler...

Often as a punishment for sneaking Twinkies, began smiling at the idea that this could be implemented for the diet!

"We can take care of this. We have to curb his appetites. The reason I'm in this damn chair is because Cosmo paralyzed me while he was driving drunk one night, we had an accident. Then he told me he'd "forgiven himself" thanks to therapy."

"Gott, that is so disgusting." Emil said as he stared daggers at my cowering, naked body.

"That's when I began really dominating Cosmo, and I was able to get him to give up drugs, and alcohol for good. But he's still a disgusting snacker. If he wants to be a real woman, he's got to be careful of his appearance. What do I have to do to break his male spirit to consume, shove a speculum up his ass"

Emil laughed at this image as I cried bitterly. It was true, I had driven drunk and destroyed Haley's lower body, although she could do really serious damage still with what she had above the waist.

I glumly agreed to the diet-and the "weight loss program"

After a year of painful diet, exercise and worst of all-ice-cold enemas, I was down to one hundred forty pounds, which looked relatively slender on my six foot five frame.

Some time after this, in full drag, my ex-wife invited my pals over and had me blow them- George Christopher Casemont, "Casey" the leader of our pack, or at least he'd always vied with me as the coolest one...the girls had always gone wild for "Casey and Cosmo" in our Princeton days-and our buddies Rod, Flynn and "The Squirrel"

Casey had enjoyed mightily seeing me kneeling naked in a pink, frilly party dress and full makeup.

Casey at one time had had a quickie affair with Haley before the accident, and I'd beaten the shit out of him, but now I was the feminine princess...and he really enjoyed skull fucking me.

The fact was, although I could kick Casey's ass, and probably Flynn and Rod's at the same time, I had been ordered by Emil and Haley to be a sweet, submissive woman, and thus, I had to let them, my old buddies, the crew-man handle me.

It was surreal, having Flynn's dick in my mouth and the Squirrel's dick in my ass at the same time, but I strangely began to enjoy it, and actually felt a sort of anal orgasm...

Emil began only allowing me to jerk off to gay porn, and then not that often.

"But Emil." I whined. "I'm really heterosexual."

"Really, Cosima?" Emil asked, smiling. "You are paying me ten thousand dollars a month plus expenses to use vicious discipline to turn you into the basic equivalent of a cocktail waitress. You need to accept the person you are now."

Then I learned something fascinating. I had never seen Emil naked, and he told me that at one time he'd been "Emily"...and had become a transman.

"I'm a man now, but all the first thirty years of my life, I was a sweet young girl. And if I can change, you can too...don't be a dummkopf!"

This really astounded me, as Emil is one of the most masculine people I've ever met!

Despite everything, I decided not to get estrogen treatments, or have a boob job. I have an on and off again career as a guy, and that's very important to me. But I can have two lives on both ends of the sexual uh, dynamic, and enjoy being a girl, and a boy, and whatever' s in the middle.

Emil told me that he had never gotten a penile implant, which is why he wouldn't let Margot "suck" him off. Sometimes Emil harkens back to his life as Emily, and I guess that's the new normal.

I've read that Caitlyn Jenner thinks occasionally about returning to being Bruce...

After all, there are advantages in both camps, right?

Well, you can probably guess where we evolved. Emily and I married, and during the day she is a devoted wife and I am a respectable businessman...and then at night, I am her sissy slut, and she is, with a strap-on dildo...Master Emil!

It's not perfect, but it works

Love, Cosima

Dear Cosima (or Cosmo) The gender-bending in my readership has gone up tremendously. Leslie tells me in her "LETTER FROM CAPE FRAYNE" that she had tits and added a real dick, and now charges very confused submissive men and women to get the works from both sexes...Connor and Alicia, a Republican and quite staid married couple wrote in "LETTER FROM PIONEER SQUARE" that they are BOTH ladies now, but also do knitting for the Log Cabin Republicans; and Wilhelm J. sent me a "LETTER FROM NORTH CROSLEY" e-mail explaining that he is not only Wilhelmina, but that he is involved with his Airedale Retriever.

So, why judge?

Best,

Shoeblossom