It has been several weeks since i have been allowed to orgasm, and i knew it didn’t bode well when Princessa bade me attend Her at the studio, properly dressed under my male costume and made up…and with the chastity on.
In the soft room i stripped to pretty lingerie, nipple clamps immediately on and She put me under. i think it was a long session of hypnotraining, and when She brought me back out of trance, i was on my back, legs spread, mouth open, playing with my breasts, which were still (severly) clamped.
Princessa was in a no-nonsense mood, and made me put on high heels and my collar (yes, the one with the disco doggy bone) and mince into the hard room behind her.
On the floor, i was lying on absorbent sheets when Princessa ordered my hands in the air, so She could slide latex gloves onto my hands, laughing at my confused look. She then made me cup my hands and poured lube onto them, told me to lie back with my legs spread and in the air, and when She had seated Herself on Her throne, ordered me to fuck myself with my own fingers.
Overcome with humiliation, i meekly slid my fingers, first one, then two then several from each hand into my pussy, and started fucking myself fo Her. She then ordered me to remove one hand and fuck my mouth, which was a pretty disgusting experience, what with the lube and… all.
Then onto the bench, legs spread, and She fucked me long and hard while i was made to pull at the clips to hurt myslef for Her, and to make my breasts and nipples bigger. Finally She ordered me to play with my clitty, laughing when my fingers encountered the chastity. For a moment i stroked the chastity as though it were a cock, and She laughed harder at that, saying the chastity must have made me forget i didn’t have a cock.
Princess Natasha kept at my pussy, and encouraged me to try to get sensation from rubbing the spot on the chastity right above where i rub my clitty when She lets me cum. Of course, it was to no avail and my frustration pleased Princessa tremendously.
She gave me a final two minutes, and when i couldn’t cum (of course not) She stopped fucking me, pulled and i mean pulled the clamps off and ordered me to shower, get into my male costume, over my lingerie, and leave. That was it. Two hours of being dispassionately fucked mentally and physically, with no sense of pleasure for me whatsover, and i was sent away.
Princessa said i had made Her happy and that made it worth it, but i felt truely used…like the whore She says She is turning me into. And i know She knows it excited me in a strange way both to feel that way for Her and to know She really wants to change me, and is enjoying doing it.
But that’s not all folks, no, no…
The next day She calls in the early afternoon to say She requires me to attend Her at the Slick Fetish Ball, at around 10 PM that night. i had no idea what that was, but She said to put on my make up at home so i could get it as perfect as possible, and put on my usual lingerie, with a half bra and Her spaghetti strapped Kitten with a Whip cami, and the pink boa. She said it was a shame i didn’t have a skirt, and, i stupid sandra, said that, well, of course i did. Wear it, She ordered, and hung up.
i was wearing the faux pearl (BIG faux pearl) necklace with the big pink bow, feather earrings and makeup when i got to the Ball space on Barneveld in the outer Mission and went to will-call. The adorable girl there took my money, dimpled and said she liked my makeup and directed me to the bathroom where she said i could “change into something more comfortable?”
Off with the jeans and on with the very short skirt which barely reached the tops of my hose, and on with the high heels. i checked my bag at the hat check, having put my valuables in my Hello Kitty purse, and strode, if one can stride in 4″ heels, to the bar for a quick cosmo or two, and girl, did i need those!
There were numerous interestingly dressed men and women around, and there was wonderful ballroom dancing going on, truely excellent dancers in pretty much all kinds of dress, although i suspect this event had its beginnings in the goth movement, since many of the couples were dressed in noir regalia.
There was no one so quite out there as i was, but at around 6’6″ in my heels i didn’t have to worry about standing out in the crowd. Everyone was very cool, although no one started to chat me up.
Then Princessa called, said they were just coming in and to have two drinks, stoly on the rocks and a cosmo, i think, ready for them.
There they were, She and Her partner, looking so elegant. Princessa’s partner was wearing a tux, looking so thirties stylish, and Princessa was wearing a very memorable pair of red chaps. Goddess, She has a glorious ass! and of course the tight bodice. i was smitten all over again.
We watched shows, chatted, i bought them drinks and attended.
Somewhere around 11PM i think, i suggested it may be time for me to go. Princessa said i hadn’t even met Miss Selina yet, and Miss Gina and her little pet were coming, and the ever gorgeous Nova and her partner Atticus were coming. Surely i wanted to see them? i melted and acquiesced under those batting eyelashes, and found myself serving more drinks as these gorgeous people showed up. Miss Selina and Nova particularly made much of me, complimenting me on how i had dressed, how slutty i looked and wasn’t i glad to make Princessa so happy with my training?
Lots more shows, some of which i saw from the floor as i knelt behind Princessa and her freinds.
Somewhere around 1 AM, i think, although things were getting a little confusing, i suggested to Princessa that perhaps it was time to leave. She said, What? batting her eyelashes. We haven’t even played yet. Play, i thought? Here?
Yup. Third floor, bear left, there is a hallway, get your face into the floor and your ass up NOW sandra, you whore, and there i was, in front of all the Mistresses and one Master in our group and who knows how many strangers, spanked hard in the “fuck me please” position, just to clear the cobwebs. i was put in trance for a bit, then found myself worshipping the feet of various and sundry, and cocksucking the stilletto heels of the ladies. At some point i seem to recall several heels in my mouth at the same time, each vying to hit the ‘g’ spot in my throat my Princessa has ordered that i shall have…and that shall become one of the few sources of sexual pleasure She is willing i should have.
Things haze out, but i recall there was an awful lot of laughter way above me (farther now than ever, regardless of how tall physically i may be in heels) and i recall my nipples being tortured with the nipple clamps i cleverly brought. Stupid sandra. Stupid.
Then, of course, around 2 AM, Princessa said maybe i should go, shouldn’t i, and was i okay? In what way? i dumbly wondered. Certainly don’t have an ego to worry about being bruised anymore, and i was used to having my body hurting for Princessa, and now i was used to being “sandra, toy.”
Off i went to the street concentrating fiercely on finding my car, and slid behind the wheel gratefully, where i was much more stable than stumbling down the street.
Fired the car up drove a few blocks and realized i didn’t have clue fucking one where i was. This became real white knuckles driving, in a strange part of town, outer Mission, 2 AM Sunday morning, unable even to see the street signs, and occassionally even missing the center of the road…and there, for a wonder, was 19th Ave! All i had to do was make sure i turned the right way on it and i was home free, my own internal GPS system having overcome my alcoholic haze and submissive overload . i drive this route day and night practically everyday on my way to and from the airport. i could do it blind, which was a good thing…because that was pretty much what i was doing.
The cop was very polite when he informed me i was going 60mph through Golden Gate Park on the way to the Presidio. Very polite and conservative because i bet it was closer to 75, ’cause i love that chicane through the Park, and with little traffic, and less common sense and no moral compunction, i bet i was really letting it out. i say i bet i was, because of course i don’t really remember.
Anyway, the cop and i had a nice chat, and then he went back to his car to run me on the computer and no doubt order up a paddywagon. That was going to be very bad, and then, in the bright glare of the powerful police floods behind me, i realized with a sinking feeling that it was going to get much worse, because i… hadn’t taken off the earrrings; hadn’t taken off the necklace…the cami…the bra. All those the cop easily saw. What he didn’t see was the lingerie, and the, gulp, chastity, still on. It was a wonder i had taken off the heels. Yup, i had, they were on the passenger seat right beside me, right where he had flashed his lights minutes ago. And i was wondering, as he started back toward me, how the boys in City Jail would like my perfect makeup, ’cause when i looked in the mirror, i realized that i had, as Princessa had told me often, refreshed it, including the bright red lipstick.
Officer to me: You been drinking…sir? (if he was a smoker we would both have been incinerated by the fumes coming out of my car not only from my breath, but also from the half empty (half full?) ‘Princess Natasha’ in the cup holder he must have seen beside me. A ‘Princess Natasha’ is made by pouring Belevedere vodka over ice, and then adding nectar of Princess Natash, which She had so kindly given me the day before; i had made one for the trip to the Ball). me to officer: Yes sir, a couple in Daly City. Why lie? Well, why lie too much?
The officer looked at me and i looked at him, he looked away for a moment and turned back, probably wondering if what he was about to do was going to come back and bite him on the ass… and he said he was writing me up for doing 60 in a 35. i thanked him and waited for the other (much bigger, heavier and painful) shoe to fall. “You ARE going right home, aren’t you…sir?” To which i fervently replied “i truely do hope so, officer.” “See that you do” he said. And i did. As i am here to witness, this cop made the right choice and is going to heaven, because i would be no good to anyone cornholed to death at City Jail. i have been in jail before but that was long ago when i was a different person and wasn’t dressed as a sissy whore.
If i had had only one of these adventures i would have been emotionally spent, but with these three in quick succession, well, fast times at ridgemont high don’t begin to express how i feel. i crave excitement, but, Princessa, please leave the cops out of it next time!
And then, on Sunday, She required me to go alone to the Dore Alley event called “Up Your Alley”, (a gay- guy pun which i am sure you, dear readers, get) , which is a street fair, a day of drinking and carrying on of leathermen..and many naked men, some very obviously enjoying the attention. Princessa wanted me to attend because i am not allowed to wear leather, i am not a man, and i am definietly not gay…while i wore my little spaghetti strapped cami and boa…but that is a story for another time.
Slippery slope indeed; juiced with the nectar of Princess Natasha and greased with the sweat of my abject fear.

3 responses so far ↓
1 natasha // Aug 3, 2005 at 1:14 pm
Great write up sandra! Goodness! I hadn’t heard about your trip through the park! Goodness, that would be quite the outfit to be hauled to jail in…. blue eye shadow, Princessa camisole and a chastity belt! Hahaha! But really, how many times have I told you to butch down the driving? Really sorry I couldn’t join you at Dore Alley to make sure someone took an interest in your cocksucking skills.
2 sandra // Aug 3, 2005 at 4:12 pm
Well, You have always maintained that i get myself into more trouble than You ever possibly could. Of course, the trouble i get myself into, i usually get out of. Your kind of trouble, there apparently is No way out of.
Yeah, too bad You couldn’t have put me on my knees at Up my Alley. Shame, that. Broke my heart. Maybe next millenium?
sissy sandra
3 syndi // Aug 3, 2005 at 5:46 pm
sandra, we need to start using the “Designated Sissy” system to keep you out of jail!!!!
Leave a Comment