Dear Shoeblossom:
On my eighteenth birthday, Ms. Sandefur summoned me and forced me to perform between her legs, and came wetly on my face, telling me that she'd taught me a valuable skill. Who knows?
After I left school and started at Balloil College, part of Oxford University, I had a nice allowance, and began seeing a professional dominatrix, Moira, and got caned regularly, twice a week, either at her place or in my rooms.
Moira was the first girl to teach me about cock and ball torture. She explained to me that cock caning would take my mind off of sex so I could focus on my academics. And indeed, after her rattan had caught my balls a few times, as well as welting my penis, took my mind off getting a little fun...my tutor was quite happy with my devotion to the Classics!
Sometimes she also would cane my pudgy stomach and my nipples, and I would cry in pain and frustration...and then Moira would belittle me, telling me that she caned longshoremen who could take it with an amazing stoicism.
I begged Moira to make love to me, I felt like we had a real connection, but she'd just whip my cock, sometimes just with a rolled up magazine, and laugh as I cried bitterly. "You just don't know the meaning of a woman's body, Lord Fleamarsh...you are only good for cleaning other men's scum from my crack, you know."
And this was literal...Other men were allowed to sodomize Moira for free, and I had to pay two hundred fifty pounds for a caning and then to be allowed to lick her rectum clean, and then masturbate on the floor, on my knees in front of her! Oh, and I am an English Lord!
And then I moved to the States...would it be different here? Of course not! You can emigrate to find freedom, many have, as it says on the Statue of Liberty, but if you are only aroused by enslavement and imprisonment, I fear all is lost, and it certainly was for me...but of course I am hard-wired towards being a submissive male...
And my beloved Stella has emphasized this! She is a wonderful wife...she's taught me good habits, and broken me of bad ones!
It took Stella a long time to break me of masturbating. She'd find clues—a stained Kleenex or the manhandled Victoria's Secret catalogue in the bathroom, and I'd get a horrible whipping. Or she'd get Roger and my other friends together, and put me in my fishnets and high heels.
"Now pull your wee-wee for the folks, Edie." Tears would be coming from my eyes. Why couldn't I receive my friends in my familiar turtleneck and corduroy pants? Why did I have to be stripped like this?
"Show your friends how you can't control yourself, Edie...you bad little girl!" My eyes brimming with tears, I beg Stella to let me off, and let me put a bathrobe on. My friends are either laughing or contemptuous, Roger and Zlotnick, my Russian bartender are tossing beer cans at me and screaming "Go, faggot"
George Sutherland, my basketball buddy, no longer shoots hoops with me—he screams epithets when I go by, and only drops in to fuck my wife and watch as she humiliates me. Willis Van DeVanter and James McReynolds threw me off their bowling team, telling me that after they'd seen me in the fishnets the first time, they laughed too hard to throw a strike, and Pierce Butler, who used to throw darts with me at the Four Horsemen bar has had me banned from drinking there, because they don't want "pansies" But they all come to see me subjugate myself!
"You'd better play with your dinkie, or Momma's going to burn it with her Cigarillo" warns Stella, and I know she ain't kidding. I bite my lower lip and begin slowly playing with my penis, but the shame of the whole thing makes me unable to get hard. Really, it's almost impossible.
"C'mon!" George and Pierce start shooting rubber bands at my stockinged thighs as I wince and pull my pud, but it's almost no use. Can my friends have really turned against me?
Jim McReynolds laughs his ass off. "Jesus, you're a friggin' English Lord, but now you're just Edie the Transvestite chicken-choker." Everyone laughs at this. It is no wonder I'm not invited to Super Bowl parties any more.
Stella is so sexy, laughing at me as I fumble with my shrinking penis. She has a way of showing off a leopard skin bra through her pink top, or wearing ruffles, and pushing the swelling top of her cleavage to drive me wild!
Sometimes when I'm pounding away, trying to get excited in front of our friends, Stella will turn to Pierce or George and let them nuzzle her beautiful cleavage, which has been forbidden me for the last nine years of our marriage.
Stella has huge breasts, and just a perfectly flat stomach, and sometimes, if she really wants to reduce me to sad tears, she'll actually pull off her shirt and bra and let one of my buddies suck her boobs right in front of me!
"Do you miss it, Edie?" she asks, giggling, and of course I'm just shattered inside.
Stella loves to torture me in other ways as well. She sometimes, while the gang is making fun of me, and my dick isn't working well enough to cum under pressure, will order me to kneel at her feet...and then she begins playing with my penis with her high heels!
Stella loves wearing punitively sharp spike heels, and kicking and kneading my penis with energy. And then when my dick DOES get hard from this, all my friends are convinced that this means I really am a masochistic pervert.
Roger was drunk one night when I was being manipulated with Stella's heels, and he stumbled over and kicked me in the balls with his Doc Martens. "What, don't you like that, Fleamarsh?" Of course I was dazed with pain from this assault...but I'm not complaining, I'm not really allowed to complain.
Usually during these evenings, whenever someone, male or female needs to pee, they drag me by the ear to the bathroom. When Celine McReynolds, Jim's wife, peed in my mouth, that was kind of a thrill, she is a curvy monster and has a well trimmed pubic area...but the night that Stella's sorority sister Eunice, all 270 pounds of her, sat on my face and emptied out, it was quite disgusting.
I've also been trained to take a man's urine loaded cock deep in my mouth and let them pee down my throat. I am not supposed to wince or make any faces when this disgusting thing is going on.
It is sometimes arousing for them, as along with my fishnet stockings, I am forced to wear Seventies light blue eye shadow and heavy, shiny lip gloss. (A horrible contrast with my balding pate).
Pierce always wants a blowjob after he pees in my mouth, and I've learned the quickest way to get a man to cum, so we can return to the hell in the living room, is to lock my lips at the base of his penis, suctioning them up and down the bottom half of his shaft quickly, and steadily, flattening my tongue against his frenulum, the sensitive vein under the head.
"That's good. That's a good boy" Pierce will mutter as I am pushing my tongue and lips against his rock hard penis, trying very hard not to gag as he grabs my ears and tries to skull fuck me. I have never, never realized how heterosexual I am then when I'm feeling utterly nauseated while sucking another middle aged man's penis. Generally, after Pierce cums, I vomit my dinner into the toilet. It's that bad.
Once or twice Pierce has dragged me into the bedroom (Yes, I think he's a little bi) and butt-fucked me, and then I must use my anal sphincter muscles to tighten around his big cock so he'll cum as fast as possible as well.
It's just the most revolting experience. Stella has shaved most of my body hair off me, and plucked the rest (worse than being whipped, let me tell you) and having the dick jammed up my ass over and over again is oh, so horrible. But then Pierce cums and I can get up and waddle back into the living room to resume my masturbation exercises.
Sometimes Stella decides that no matter how horny I am, no matter how long I've been denied, I have to jerk slowly, and NOT cum. This is even harder, though perhaps it's easier to be distracted when my friends are jeering at me.
"Come on, there Edie, go a little slower, you pathetic piggy" Stella will say, laughing as I gingerly stroke my erection, trying not to go over the edge. Then it's really hard, because I have to not stroke the sides of my penis, and sometimes Stella will do something like order me to only stroke the head of my cock, or just play with my balls.
When she's kept me sexually chaste for long weeks at a time, and I'm super horny, that's when she decides to have a pizza party, invite the males of the neighborhood over, as well as various women, including sometimes the members of her Ladies Church Choir group...it's just awful.
Then, Stella will let me jerk off quickly sometimes, but I'm distracted because she's got two of my male friends whacking my ass with paddle and cane, and it's almost impossible to focus on my hopeful orgasm!
Or, I'll be on the verge of cumming, and then Stella will quickly kick my nuts, or, if I'm lying on the carpet, she'll drive a sharpened spike heel into one of my nipples!
If I go through all the bullshit of the evening and have been a good submissive, sometimes Stella will let me fuck her, using a condom, and then she'll order me to drink the condom empty...I'm used to this, as I am frequently drinking her lover's condoms as well.
Since I don't wear a chastity belt, sometimes Stella will call at work and ask my secretary, Beulah, an overweight black woman, if she'll check after I get out of the bathroom to see if I've been jerking off.
It is really horrible when Beulah orders me to step before her desk, and she unzips my pants with her press-on nails and pulls my dick out, touching it and rubbing it to see if it gets hard (not that she's any visual prize, 55 years old in an ugly lemon velour pantsuit) and then she'll say into the phone "It's okay, Miz Mortlake, he still got his dick full" before letting me zip up again and go, humiliated back in my office!
Then I of course feel ridiculous when I ask Beulah to do any typing or copying for me...might as well just do it myself. Oh it's awful!