Dear Shoeblossom:
Gillian often awakens me by kissing my inner thighs. Feeling her full lips moistly kissing around my crotch area, sometimes with playful tiny bites, is really a sensual experience. After Gillian has perceived that my eyes are open, she pushes her little body up to my face, her big soft breasts grazing my hard cock until she rests her chin on my chest.
Gillian is not allowed to speak without permission, but I know from certain hand signals that she's asking me "Would you like me to service your cock, Master? A blowjob? Or should I go to directly making your breakfast?" Often then I stick my tongue out at her.
When I'm in a churlish mood, I grab Gillian by her long mane and pull her off the bed, and then I arise and put on my slippers, gently kicking her out of the way. Gillian's big house is so much nicer than my cramped apartment—I saunter across the bedroom, heading for her private bath—but then Gillian will crawl ahead of me on hands and knees, blocking the bathroom door.
She wants me to pee in her mouth—the commode is an insult to Gillian's swallowing abilities. When I tap my ass, though...she lets me in, she's too hygienic for copraphilia, apparently.
We're working on that, though...I am making Gillian drink a tiny blot of my shit with a glass of milk every day, and it seems that soon enough she will be able to get lots of my poo poo down. We just need to work on it, right?
So then we adjourn to the living room, so I can pee in her mouth, generally starting off at about two feet away from her chin. Gillian has perfect poise—she is able to kneel with her mouth open, and then I begin peeing in an arc across her expensive Oriental rug.
At first, my urine shoots powerfully out, the result of too many Amstels the night before and Gillian juts her chin out, opening her mouth to catch it all! But then, as my shoot begins to falter, Gillian is able to scoot closer and closer, still on her knees, never missing a drop. For if she does, and a single driblet hits that rug, I will give her a vicious whipping with the cut off garden hose that I keep by the door.
Finally, when I'm almost done, Gillian crawls right to my penis, taking it directly in her mouth, and slurping up the last of the urine, quite lovingly. The old adage goes, "No matter how you jump or how you dance, a few drops remain in your pants" but not with my Gillian...she makes sure I am dry and comfortable, actually bathing my cock with tongue and warm breath, before it is returned to my pajama bottoms.
Then I generally return to my bed and Gillian brings my breakfast. The maid actually makes it...Gillian is one shitty housekeeper, but the maid has been in Gillian's employ for some years, and is used to her employer coming into the kitchen, naked except for pierced hoops through her nipples, picking up the tray and running back to the bedroom!
Breakfast is always excellent, and I let Gillian spoon feed me and refill my coffee...generally though, I find some imaginary fault with burnt toast or cold coffee, and then, after Gillian puts the tray aside, I slap her hard, until her teeth jiggle, my hand crashing back and forth across her small chin. No matter how hard I smack, she never complains!
Think of it, Shoeblossom, a little one hundred and five pound girl (albeit with big boobs and a round bubble butt) taking my big, meaty hand whacking her face back and forth in a bitch-slap, and she never murmurs complaint, not even when there's a trickle of claret from her dainty, aristocratic little nose.
If we have the day off, I instruct Gillian to put her hands on her head in the bedroom, or sometimes the parlor (The maid just ignores us, as she dusts around) and then I fun stuff like attach little spiked weights to Gillian's clit lips, watching them grotesquely hang down, cruelly snapped on with heavy chains...
Or I attach rat-traps to Gillian's full pink breasts and knock them off, laughing as Gillian bursts into wet tears. Or I put a chain through her ringed nipples and drag her around the apartment on her knees, which makes her cry harder...in silence of course, for she's not allowed to speak. Her nipples are quite tender, she tells me. But again, she never complains.
It's just the most kick-ass way to live, man!
I used to be a copy editor for a mortgage banking newsletter, and then we were shut down thanks to George W. Bush's recession...I had little training at anything else, but then I got a temp job at Knout magazine, one of the bigger BDSM journals in this part of the country.
This was incredibly lucky, as I was pushing forty, and was in that horrible position you get in when you've depended your whole life on a career, and it's pulled out from under you!
How I met Gillian Federman, the twenty-six year old publisher of this strange periodical, is a remarkable story. She owns about five different magazines, and was fairly well off. I of course was just doing drudge work, but I had to bring her some copy to review, and I was quite taken with her. Gillian has sandy hair and wide green eyes, and a healthy chest. "Irv, is it? We're glad to have you here at Knout...it's probably not what you're used to!"
I nodded, and tried to smile. "Well, you know, a job's a job, right? I probably should've taken my dad's advice and majored in engineering like my brothers did.. But I'm really grateful for the temporary position here, Ms. Federman. I can adjust to anything, even these wild pictures, really I can."
Gillian had smiled, and it was a dazzling event, that smile. "Well, it's up to me whether or not it's a temporary position, Irv. Perhaps we'll have permanent use for you." Then we went over some of the pictures and articles.
I admitted to her that it was really startling to see what these models would go through—being hung by their breasts, and having the whip hit their butts, leaving serious damage—to a Pentecostal boy from the Bible Belt, it was heady stuff."
"Well you know Irv" Gillian said, looking straight at me, "Some of the models just have rouge on their butts where the whip supposedly hit them...there are some very talented makeup artists that do this sort of thing, but you're right—you can't really fake nipple torture. The girl must like it, don't you think? I mean, we don't pay THAT much."
I had looked at her. "The nipple is so sensitive though, Ms. Federman...it's hard enough getting that kind of pain...shit, my sister's friend once just flicked my nipple playfully, and I almost cried. And this girl is hanging from her nipples!"
Gillian had tossed her pretty sandy hair and laughed. "Well, Irv—and by the way you can call me Gillian—maybe she likes it. After all, someone must, to publish these magazines, right? I'm a millionaire, after all."
"Sure, but it's probably perverted old men, not the women that go through this" I protested. Gillian was edging just a little closer to me, and I smelled her perfume, it was something else. "Girls can't possibly enjoy this. I mean—but on the other hand, the Story of O was supposedly written by a woman, so maybe I'm wrong."
And then Gillian invited me to dinner. And she paid for it, too. Good thing, since I didn't have much in the way of greenbacks.
We went back to her place, which was a nice Colonial house on the better side of town, and began making out on her couch...and then she unzipped my pants and gave me a long, sloppy blowjob, followed by a really excellent massage on her Princess bed. I wanted to reciprocate, but she would have none of it.
"I like serving a man" Gillian had said, shyly. I was totally grooving on her beautiful body. Round pink breasts, long legs, it was just incredible. "I actually started my magazine chain because I have a strong interest in female submissiveness, when I was about nineteen, and now I have a bunch of them...but it's what I love, you know?"
"But you're a heartless businesswoman" I said playfully, as I caressed her left breast. "How does that figure in with being a slave girl?"
"Don't be silly, Irv." Gillian said, grinning. "How many old businessmen do you think are getting whipped by dominatrixes? Probably quite a few, they buy my male slave books from me at quite a rate. I am a powerful, bitchy woman in public life, but here at home, I just want to find a man who will you know, direct me."
There were a few more dates, and every time, Gillian insisted on performing fellatio on me, and having me lie back and enjoy it. The massages were incredible. When I insisted I wanted to fuck her, she bent over so I could do it doggy style. "Or if you like, you can invade my anal area, Irv...I've been sodomized many a time."
"Is that really what you want then?" I asked later, as we were sharing a joint and idly watching Conan O'Brien. "To be pushed around and humiliated?" In a way it was kind of a turn on, thinking about it. I'd been shat on by so many women, and was now supporting two ungrateful ex-wives and five bratty kids through my efforts to find a little love...
"It's not a matter of being pushed around, Irv." Gillian said sincerely. "You couldn't really push me around, I've got an IQ of 150 and megabucks. I want you to be my Master, but really, it's my choice and I'm controlling it, I think."
"Think so?"I felt a bit annoyed. "You and your IQ of 150." This hit a nerve because it was true, I wasn't super-bright. And I was sensitive about it. "Get up, you whore." I pulled Gillian up and took one of her slippers off her foot, jerking her over my knee. Gillian was wearing a shortie nightgown and panties, and I dragged them down and began whipping her with her own slipper, hard.
I was angry...angry that my life had turned out so badly. Angry that I was temping for this little bitch who was nearly fifteen years younger than I...who'd had more luck in business. I whipped her harder and harder with the slipper, and Gillian stayed silent, and I hit her even harder, until the slipper broke.
Then I dragged the still silent Gillian by her left nipple, through the flimsy nightgown into the bedroom, and threw her across the bed, and took my belt off and began whacking it against her round, full bottom. WHACK! THWACK! SMACK CRACK! Finally she began sobbing slightly, and I realized I might be going a little too far.
