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  Not Your Typical Date: Jessie's S/M Enema Date
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Jessie, in a straitjacket, is about to get an enema with a huge, hard squeeze bulb; she later has to expel the enema into a bucket, while still tied up

Featuring : Jessie and Andre Chance

Jessie, a flirtatious, sexy blonde – with tattoos but very feminine and with large breasts – goes on a date with an S/M Master.

Sucking the guy’s cock may not be too unusual on a date, but that’s barely the beginning: next is spanking, enemas (with ass-to-mouth bottle, followed by huge squeeze bulb), bondage, suppository, nipple clamps, paddling, whipping, belting, caning, straitjacket, hot wax, breast pumps and a huge fucking machine for Jessie’s pussy and ass!

Well, not exactly your typical date!

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The entire feature-length film, split into parts
(WMV format, with no DRM)

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This clip also available on WizardClips for individual purchase.

Nipple clamps; SUPPOSITORY; breast pumps; ass finger-fucking; cum in mouth

This clip also available on WizardClips for individual purchase.

Bottle enema in straitjacket; forced ass-to-mouth bottle; finger up ass

This clip also available on WizardClips for individual purchase.

While still in straitjacket, deep-throating long, hard nozzle of large douching bulb; 4 enemas with it; bucket expulsion; vibrator masturbation during enema and during expulsion.

NOTE: These enema clips will get re-released as a FULL FEATURE film. The full-film version will include footage never shown on this site before. Furthermore, the re-release will be at MUCH HIGHER video quality than the original enema clip. Please stay tuned! (details)

(as zipped files)
This photo set, and the later ones, replace and greatly expand the old Introductory Photo Set 0

(in alphabetical order)
Erotic elements are CLICKABLE!

Bare feet
Belt Whipping
Blow Job
Breast pumps
Clothing : Completely naked
Enema - Squeeze bulb or Bottle
Fucking machine - reciprocating piston
Hot wax
Nipple clamps
Spanking : bare-hand
Whipping (flogger)
User comments

UserComment (newest at the top)
enemaholic(NEWEST COMMENT) i applaud the way you "casually slip in" suppositories, here and there, in various films :D
BadSheDevil Seeing her so helpless and restrained in the straight jacket makes me want to take control of her, and it adds a little craziness to Jessie. My favorite part was seeing the water bottle put in her ass and then her mouth. I imagined longing for water and then finally having my thirst quenched in the most fulfilling way! From both ends! And following the path of the bottle continuously from the rear to mouth, Brilliant!
squeezeI love the sounds she makes, especially on her fourth bulb enema! Hot!

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Free large thumbnail photos :

Jessie, in straitjacket
Jessie, in a straitjacket, gets an enema from a drinking squeeze bottle. Later, the bottle goes straight into her mouth (no camera cuts!)
Jessie, in a straitjacket, is about to get an enema with a huge, hard squeeze bulb; she later has to expel the enema into a bucket, while still tied up

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Detailed description of the entire film :

Jessie Jessie is a hot girl I take out on a date. She dresses sexy, in a great minidress, and is a wonderful flirt. But will she be able to handle my S/M lifestyle? After bringing her home, it's time to find out!

Jessie has many tattoos, so it's safe to assume she isn't too shy about things; still, S/M is something that can scare away even adventurous girls... So, I first make sure that she has some wine, and then broach the subject carefully.

Jessie watches with fascinated amazement as I show her thumbcuffs, and then try to slip them on her! She coyly admits that she has never playing with bondage before and that she's nervous, but she eventually allows me to lock up her thumbs in the cuffs. I make her at ease by later removing the cuffs, and by getting her aroused with caresses and flirtation, suggestive talk. Then I reach for her breasts and, after biting her nipples, I apply nipple clamps on them!

Just as the romance is heating up, Jessie spills a glass of red wine on my white rug! She nervously asks if there's anything she can do "to make it up". "Yes!" I say as I pull her by the nipple clamps: "Suck my cock!" I rub my cock on her lovely breasts while I tell her all the things I'll be doing to her next, including spanking her and giving her enemas.

I tell her that I'm going to cum in her mouth. But, first... I will stuff up her butt with a suppository! I make her peel it, and then I make her bend over. I slowly insert the suppository, teasing her butt entrance with it; then, I finally plunge it in, dipping my finger alongside.

When Jessie's nipple clamps slip off, I make her replace them with two breast pumps. I tell Jessie to remain standing bent over, with her panties halfway down. I keep two fingers up her butt and make her repeat back to me all the things I'll be doing to her next: caning, enemas, machine and straitjacket. Then I make her open her mouth and I shoot a load of cum straight there!

Afterwards, Jessie masturbates while lying back on the floor. I tell her to build up her arousal, to better handle the spanking that is coming up next... She masturbates for a while, and then I move her across my lap, right next to the wine spill -- and start spanking her.

I tell her that I'll make her butt as red as the wine stain -- and I do! Then I strip her naked and fondle her lovely, sizable breasts while I pull her dress over her head.

Next, I paddle Jessie with a leather strap while she lies down and kneels down.

I spank Jessie some more. Then I tell her that I'm going to tie her up. She appears excited at the prospect. I also show her the Black Magic Machine, "for later"...

She asks me "What are you going to do to me?" I tell her that I'll spank her really hard, and then have her fucked by the big machine! She resists the bondage, but it's clear that she's a slutty girl who's going to enjoy it...

While she's on her back, I tie up her left ankle to her left wrist and her right ankle to her right wrist. When I apply nipple clamps on her, she nervously notices a 3rd clamp -- which I apply on her clit!

For starters, I paddle her hard with a leather paddle. Then I tie her up to the bed, in a fetching position with her legs straight up.

I paddle her really hard, but she barely bats an eye! A pain slut?!

I decide to go even harder on her, but first I give her something "to make it more bearable": a vibrator. I simply leave it on top of her clit, and then proceed to strike her with a belt her all over, including on her feet and the sides of her breasts. After some hits with the belt, Jessie is no longer as unperturbed as earlier!

Next, it's time for the cane, while she lies on her side, still chained up and deliciously exposed! While she desperately holds the vibrator to her pussy, to make the pain more bearable, I repeatedly strike her with the cane and with a variety of paddles, including a leather strap, a hairbrush and a whip. I make sure to also include her breasts and her pussy.

I finally free her from the bondage, and remove the clamp on her clit. It has been there for a long time; so, it really hurts when it is unclamped.

Jessie, in straitjacket It's now time for the straitjacket!

Jessie, in a straitjacket, gets an enema from a drinking squeeze bottle. Later, the bottle goes straight into her mouth (no camera cuts!) I put Jessie into a straitjacket, and then swing her onto my lap, telling her I'm going to give her an enema straight from a drinking bottle! First, I widen up her rear entrance with a finger. Since Jessie is squirming around, I supplement the straitjacket by tying together her ankles. I widen her up shy entrance with 2, and then 3 fingers, and I manage to squeeze in the top of a plastic drinking bottle. There's no spout -- I directly insert the large bottle opening up Jessie's butt! Then I squeeze all the water up her colon. Immediately afterwards, I take the bottle straight from her ass to her mouth (no camera cuts!) and I make her take it in her mouth and drink up the last few drops -- not without a struggle, though; she resists, and I have to pinch her nose to get the bottle fully inside her lips!

She complains she's already feeling full... Understandably, since it's her very first enema. I slide a finger up her butt: I can feel the water, and even the suppository from earlier!

I give Jessie a bucket to expel in, but she doesn't let anything out. Embarrassed? The way I deal with stubborn girls like herself is to just fill them up with more water! Jessie, in a straitjacket, is about to get an enema with a huge, hard squeeze bulb; she later has to expel the enema into a bucket, while still tied up After tickling her a bit, I use a large douching bulb. First, I make her deep-throat the long, hard nozzle... Then, after giving her a "mouth enema", I shove the hard nozzle up her ass give her an enema while she kneels in the straitjacket. Afterward, I give her again an opportunity to expel into a bucket. When she doesn't, I give her another enema!

At the next opportunity to expel, only a tiny trickle comes out: I prop up a vibrator against her pussy, and give her a 3rd squeeze bulb enema. Yet again, barely drops come out into the bucket!

You can guess: I give her a 4th squeeze bulb enema! This time, I position the nozzle, pointing up, directly underneath her rear entrance, and make Jessie impale herself on it. She takes the long, hard nozzle virtually "to the hilt"...

By now, her colon is full with the contents of the drinking bottle and 4 large squeeze bulbs.

Squatting yet again on the bucket, Jessie finally lets it out, while I masturbate her with the vibrator!

Then I give her one last squeeze-bulb enema, and make her expel in the bucket again -- all along while masturbating her with the vibrator.

While Jessie is still in the straitjacket, I set up the Black Magic Machine. For starter, I make Jessie kneel in front of the machine, and rub her clit against the dildos (still outside of her.) While she does that, I cover her exposed parts (i.e. what's not in the straitjacket) in baby oil. Then I whip her and strike her with a belt!

Next, I impale her pussy on the first of the 2 dildos attached to the mechanical arm. While she rides that, I drip hot wax on her. Finally, I ease the 2nd dildo up her butt, and let the machine fuck both of her holes. When I eventually turn the machine off, and pull Jessie off it, she appears worn out but with a huge smile. Not too bad a date!

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