Letter From Ithaca

Dear Shoeblossom,

When I was in graduate school, I rented a room from a woman who was a retired dominatrix--Miss Elspeth. When Miss Elspeth discovered that I was a devotee of BDSM sites, she immediately took over my life. I left her care after getting my degree, but recently moved back to New York State and moved back in with her...I am a true submissive, though sometimes I wish she'd let me have some "normal" nights as a real guy.

For instance, my butt is still stinging from the other night, when I got home late from work. "Leland, where have you been?" Miss Elspeth asked me. She is a striking woman, and once won the Cayuga County Joan Collins look-alike contest.

"Miss Elspeth, the bus was late...I wish you'd let me get a driver's license." Really. I'm thirty-three years old, Shoeblossom, and Miss Elspeth won't let me drive yet.

Miss Elspeth took out her old-fashioned gold pocket watch and inspected it. "That's ridiculous, Leland. You leave the office at five-thirty, and it takes you 20 minutes to get home. We went over that when you took over Daddy's firm. We took the bus, and timed it together."

Miss Elspeth shook her head, and looked at me with dagger eyes. "It is now seven ten. You have an hour and a half to account for. What have you been doing, Leland?"

Miss Elspeth sighed impatiently, and inadvertently, I watched her considerable bosom shift under her pearl lined sweater. I knew I had to stand up to her.

"Miss Elspeth, I did stop for a drink with some co-workers, just briefly--"

"A drink, Leland?" Miss Elspeth's eyebrows rose. "You had an alcoholic--"

"A Shirley Temple--"I protested. "It was just a Shirley Temple, with ginger ale and grenadine."

But Miss Elspeth is very strict, and when I moved in with her back when getting my MBA, she immediately curtailed my outside activities. To school and back home, or else! I was in my twenties, but she didn't care!

I can remember sneaking off to try and play ball with a local men's softball league, and of course they just made fun of me...just for approaching them...you see Miss Elspeth had thrown out all my normal clothing...me, an adult!

Miss Elspeth had me dressed in Donald Duck like sailor suits and then sometimes Swiss lederhosen. (Miss Elspeth was a big fan of the children's uniforms in "Sound of Music")

Once,I thought Miss Elspeth was out shopping, and I sneaked away from the house when I was supposed to be studying Latin.

Although it wasn't in my major,Miss Elspeth had me construing Virgilius Maro for her pleasure, but I figured I could get an hour to play a little football in the street.

But when I got to the field, the men saw me in the new outfit Miss Elspeth had gotten me--an Edwardian purple velvet suit with ruffles and lace, and patent leather buckle shoes and stockings.

Miss Elspeth also had me wear my hair long, with ringlet curls that she curled herself! I was truly a Little Lord Fauntleroy look-a-like, but my protests had never gone well with Miss Elspeth, who didn't brook dissent well.

So there I was, trotting over to the field. It was weird being out of the yard, except for medical appointments, but I knew where it was, as the boys often threw things at me when I trotted by for my violin lesson.

When I got to the field, the men, blue collar types were playing football, dressed in torn T-shirts, jeans and motorcycle boots, some wore sneakers, of course.

Miss Elspeth always said that wearing tennis shoes was a good way to get a cold!

As the men threw the football back and forth, tackling each other three girls mimed cheerleading. When the football landed in one guy's arms, the girls would chant something like

"Tommy, Tommy, he's our man, if he can't do it..."

Then when the ball went to someone else, they finished "Alvin can!"

The girls were really hot, and had big boobs and cut-off shorts. One of them, Bonnie, I knew slightly because she sometimes came over to iron for Miss Elspeth.

I'd given her hesitant looks, peeking in at her as she ran the iron back and forth, her bosom bouncing in a tight green halter, until of course, Miss Elspeth would drag me away by the ear, goading me back to my studies!

But she'd always looked sympathetic, and when I came up to the field that day, Bonnie had smiled and waved. "Hi, Leland!" The other girls paused and lit cigarettes, which Miss Elspeth always said was bad for you.

The game stopped briefly, and a biker type, a ruffian with a Mohawk, looked over at me. "What're you doin' here, faggot?" The others laughed, and I'm afraid even Bonnie smiled.

I protested that I was just coming to play ball, and they all laughed at this, and I was feeling quite embarrassed...how could it be worse?

But it did get worse. There was a beeping of a horn, and I turned around, and Miss Elspeth's 1976 Mercedes-Benz 250 had just pulled up.

Miss Elspeth popped out of the car and strode over. "What are you doing here, Leland?"

The men became silent. Miss Elspeth was wearing a short red skirt, matching red pumps and a snug white sweater that showed off her full bosom.

That day she came right up to me, pointing a scarlet nail in my face. "How dare you leave the house without my permission, associating with these...barbarians."

I tried to make an excuse, but of course my knees were knocking, and my hands were wringing.

Miss Elspeth went over to a nearby rose bush and, using her pearl handled penknife, cut a branch, trimming off SOME of the thorns and leaving others.

"Now then, Leland" Miss Elspeth said, tapping the long branch against her skirt, "I instructed you to stay home and construe two hundred lines of Virgil, and apparently you decided to gallivant...with these juvenile delinquents."

The bikers were silent, though...some were staring at Miss Elspeth's boobs and the others were just terrified of her!

"N-nuh-no, Miss Elspeth." I said. "I-I didn't mean to--I just went out for a little while." After all, I was twenty years old!

But Miss Elspeth would have none of it. "Take down your breeches, Leland, I'm going to show you how to comport yourself when I am not present."

"C-can't we do this at home?" I blubbered.

Miss Elspeth smiled grimly and slapped the switch against her knee. She shook her head.

Biting my lip, I unzipped my pants and pulled them down, sparking a hoot from the boys as they saw my underwear, Miss Elspeth made me wear ladies panties covered as they were with little hearts.

Miss Elspeth felt that it was a waste of money to buy individual underwear for the various sexes in our household, as she could get all the ladies undies she wanted from a wholesaler!

"Now take down your panties too, you know the rules." And I did. Miss Elspeth had been whipping my bare bottom since I was old enough to walk...she never left my behind covered.

I looked over at Bonnie and her friends. They were giggling, blowing gum bubbles and smoking their Marlboros. The guys were staring slack jawed at me.

But I knew that Miss Elspeth would make things worse for me at home if I didn't obey.

"After all, Leland, if you act like a baby, you should be treated like one--so bare your bottom." Miss Elspeth smiled cruelly.

"Come up, girls, watch this rebellious baby get his punishment."

And the three hot girls came up, Bonnie in the lead...they stared as I rolled my panties down to my knees, and bent over, grabbing my ankles.

I'd never gotten a thorny whipping before, and the first smack of the branch ripped skin off my chubby buttocks.

Bonnie's girlfriend, who had a pierced navel under her crop top had gasped, watching me get my correction!

Miss Elspeth whipped me with the thorny branch until I was on the ground sobbing as if my heart would break. The bikers and girls laughed until they were sick, watching my humiliation.

"Now get up, Leland" Miss Elspeth said afterwards. "No, don't pull up your pants yet."

"You see girls...he just has a little wee-wee...oh, what's this?"

Sadly, my penis, small as it was when I was fourteen, was hardening, mostly because I was staring through tear blurred eyes at Bonnie's ample chest...

THWACK! Miss Elspeth's rose branch slammed against my hard cock five times until, covered in thorns, it wilted.

"You are much too young to be having such impudent thoughts, Leland...let this be a lesson to you!"

Then she chased me back to the car whacking my bare buttocks as I stumbled with my pants around my knees, finally falling in the back seat.

Another time, Miss Elspeth trumped up an offense I was supposed to conjugate the Latin verb "iuvo, iuvare - to help" in present, imperfect, and future tenses, and she claimed I did it wrong, and gave me a bare-bottom slipper whipping RIGHT IN FRONT of Bonnie!

"You see, Bonnie" Miss Elspeth shouted above my wails, as the slipper slapped again and again against my purple bottom "What I must put up with? He's like a pathetic child, isn't he...what a crybaby!"

As punishment for being a crybaby, Miss Elspeth had then painted my nails and put me in a frilly tutu, and made me serve Miss Elspeth and Bonnie tea, and curtsy!

Bonnie was almost falling over herself in giggles while this was going on, unfortunately!

Miss Elspeth called me "Leila" instead of "Leland" throughout the afternoon!

Later, when I whispered to Bonnie that I'd like to sneak out and take her to the movies, Bonnie giggled "Don't you think Mummy might smack your bare butt, Leila?"

Oh, God, Shoeblossom, I was so humiliated!

Another time, I said "darn" in front of Miss Elspeth, and with Bonnie watching, I was forced to eat an entire bar of old fashioned yellow laundry soap, the kind manufactured from animal fats, olive or palm-kernel oils and caustic soda.

It was so bitter!

And on that day, to remind me I was just a wimp, Miss Elspeth had shaved my pubic hair off while Bonnie had looked on, interestedly.

"If you can't behave maturely, why should you be treated like a man...profane language is infantile behavior!"

And Miss Elspeth had put me in adult diapers, Depends, I believe they're called...I looked ridiculous!

I had to go around on my hands and knees, with a frilly bonnet and the diapers...and Bonnie had been in hysterics!

Sometimes, Miss Elspeth made me wear only a pair of long johns in the house with the crotch cut out, so my penis and balls hung loose...

It became my responsibility to shave my own crotch, and Miss Elspeth would inspect me afterward, pulling neglected hairs from my crotch area with a nasty pair of tweezers!

And she would often flick my penis when I made an academic error, or talked back.

I can remember standing miserably in the living room, my penis flailing as Miss Elspeth whacked it with a spoon because I didn't polish the silver well enough!

"You are going to have to get a better attitude Mister" she said as she slapped my poor dickie..."You're going off to college like a big boy, but you can't even do an adequate job polishing the silver!"

I looked a bit ridiculous, no shirt on, my gut (even at 18, Miss Elspeth allowed little exercise) hanging out, and those ridiculous long-johns on, with the hole crotch!

Miss Elspeth flicked the tip of my penis with a sharp red nail. I jumped, howling.

As I covered my penis, Miss Elspeth reached up and tweaked one of my nipples. "Did I tell you to cover up? I know your lack of enthusiasm for polishing is related to your secret onanism habits, Leland."

Miss Elspeth's war against my masturbation was a vindictive one at the time...

She was constantly sneaking up on me in my room, trying to prove I was choking my chicken. And when she caught me, there was hell to pay.

One night, she caught me with a Fredericks of Hollywood catalogue that I'd stolen from a neighbor.

Miss Elspeth tied me down naked and showed me pictures of the women, stabbing my tender cock with a heated fireplace poker whenever it got hard!

After that, I didn't touch myself for weeks!

But anyway, Miss Elspeth had me there, all summer long, afraid to leave the house (as I was wearing this humiliating crotchless long john thing) and by the time September came, I was thoroughly cowed...she set a schedule for me at Cornell, and I had to adhere to it!

I had to be back home by four o'clock and I had to call Miss Elspeth after each class. Whenever I got less than an A on a quiz, Miss Elspeth would strip me, and bind my hands behind my back, laying me across the bed.

She would then take her two foot long, two inch wide supple leather tawse, and whip me ten times for the first point off my quiz, and one lash for every additional point.

( I remember a C- I got in an Intermediate Macroeconomic Theory Class...she nearly killed me! 74 out of 100 points, that was twenty-six lashes, and of course she poured Ben-Gay on my butt to soften it...oh God.)

Some time after this, I just realized I'd had enough, and after I graduated from Cornell, I surreptitiously joined Teach for America, a part of Clinton's Americorps program.and moved from Ithaca to Talladega, Alabama.

Thanks to Miss Elspeth's ministrations, I had graduated college summa cum laude, and so after a year with Teach for America, I was able to get a job in Los Angeles as an investment banker...and I spent five years making up for the freedom I'd missed!

Cocaine, women, parties...I had a Ferrari 430 Spider and a Harley-Davidson motorcycle, and I began having a REALLY good time.

But...I had perverse desires. For a while I dated little blond bimbos, they were everywhere, and many dropped heavy hints that I should propose. But when we went to bed, there seemed to be something missing.

And I discovered that the only time I felt complete was when I visited Miss Scunthorpe. She had an odd position in Los Angeles--Ms. Scunthorpe was a Keyholder.

I became interested in chastity sites on the Internet, and discovered Ms. Scunthorpe's program some time into my third year in LA.

Ms. Scunthorpe, a busty blonde in her mid forties, locked me in chastity, and charged me $1200 monthly for keyholding and "maintenance visits"

If I wanted more than a weekly "visit," I had to pay an extra $500 per visit...and I wanted them, because quickly Ms. Scunthorpe had me in a tough situation.

Here's an example of a typical visit: I showed up every week, and it went something like this:

I come into Ms. Scunthorpe's attractive Huntington Beach townhouse, and I'd sit down. "Well now, Leland, how have you been?" Ms Scunthorpe, dressed in a snug blue low cut gown would ask...

"Well, Ms. Scunthorpe, I've had a stressful week, it was so disappointing last week, when you told me I hadn't earned an orgasm...You teased me so much, and locked me back up!"

Ms. Scunthorpe snorted. "Don't whine to me, Leland. I suppose you're going to bitch that you went on some dates with Lala land sluts, but you couldn't go all the way, because you couldn't show them your little belt..."

I looked down shamefacedly. It was true, I'd met a cute little computer programmer, Thalia, who I'd necked with madly in my convertible, but when she'd said, "Baby let's go up to my place," I'd had to demur...

And then Ashleigh, a restaurant hostess from Dave Chasen's had offered me a blowjob, but I would have needed a blowtorch to get the belt off!

Then I hesitantly said "But even if I could have just had a masturbation session last week...it's been 93 days since you let me have a release."

Ms. Scunthorpe snorted. "Well, did you complete my assignment? A five thousand word essay on the meaning of obedience, one letter in pencil, the next in pen?"

But of course that had been impossible. Composing the thing was tough enough, but pen and then pencil for hours? I shook my head mournfully. "I did about seven hundred fifty-six words--"

But Miss Scunthorpe shook her head. She unbuttoned the top two buttons of her dress, showing me her marvelous cleavage.

"Leland, don't you understand? If you can't please me, then what's the point of me letting you play with yourself? What's the point of me letting you touch my breasts...which I know you want to do?"

My lip trembled. "It's...it's just too much, Ms. Scunthorpe! A few weeks ago, you made me go out in drag and make up and perform oral sex on truckers for money, and then I didn't make enough, so you rejected my plea for an orgasm...and another time you put your fist in my rectum--"

SLAP! Ms. Scunthorpe's hand hit my face and I burst into tears.

"Your whining makes me ill!" Ms. Scunthorpe said savagely. Her cleavage bounced in the pale blue dress. "Take off your clothes and lie down over my ottoman."

Crying, I undressed and lay over her footstool, and Ms. Scunthorpe bound my hands and legs. I heard her going into the other room, and she came out with her Scourge.

Ms Scunthorpe's blonde hair was piled over her head, but I looking over my shoulder, I saw her undo it and shake it around her head, and my cock swelled against the cruel little metal tube it was locked in.

Shoeblossom,you wouldn't believe how tight that little tube was! One of Ms. Scunthorpe's other slaves was a metalworker, and she'd instructed him to make an especially snug one for me, so I couldn't really get an erection, and my dick would just crush itself when I got excited...

So all week long, I was constantly in pain because of the temptations of all the hot girls in LA...gaping at them, having my cock contract and squeeze in frustrated agony as I watched some hottie's fake breasts bounce as she waltzed down Melrose Avenue...

It was quite unpleasant. and it was double-locked so there was no way I could sneak out of it!

The scourge Ms. Scunthorpe used was a Flagrum, which had been used for mortification with priests in the last century. It was a wooden stick with leather cords with metal objects interspersed through the cord, sharp little pieces, and very painful.

Ms. Scunthorpe gave me thirty with the Flagrum, until my buttocks were purple and bleeding, and finally, she helped me up, and, after toweling my butt off, and rubbing it with witch hazel (even more painful) she took me to her bed.

Ms. Scunthorpe lay me on her bed, on my back. with a pillow to prop up my head. My hands and feet were still bound, She unlocked my chastity device, as she did every week, to give me a teasing.

I watched in awe as she pulled off her dress and sitting with her lingerie bra holding her considerable breasts, began to rub and play with my hard cock, pulling and squeezing it...

"There there, darling" Ms. Scunthorpe crooned. "I'm not going to let you cum until you show some attitude adjustment...but doesn't this feel good?"

Her long French nails teased my bulging penis and soon I was on the verge of cumming.

Then, Ms. Scunthorpe went back in the living room and got the Flagrum.

"No, no please..." I begged. "Not my cock!"

"Well, go limp then, honey." Ms. Scunthorpe said soothingly. "I'll give you thirty seconds..."

But of course I couldn't...and she kept stroking my cock a bit, until I was even closer to orgasm!

"Oh...too bad." Ms. Scunthorpe shook her long hair around her neck, and swung the Flagrum viciously.

Five times across my cock and balls until they were a bloody, limp mess...and then of course Ms. Scunthorpe cleaned them off with Witch Hazel and locked me back in the chastity device!

Of course I left her home, weeping bitterly...my ass and crotch were on fire, and my cock was lengthening AGAIN, because cute high school girls were passing the house, and I had still not cum!

But this was how Ms. Scunthorpe would reel me in! Now I had to complete the essay, five thousand words, one letter ink, one pencil, and I had a new assignment, to get a picture of me rimming a gay hustler's bare ass at the Fautline, one of the notorious leather bars in L.A.

I had to pay him to eat Ex-Lax, which cost a lot, since then he had to put up with dishrag...and then I had to rim him on cam for ten minutes!