Weekend with Judy Pt. 01

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Judy's husband lets her live out yet another fantasy.
6.8k words
4.61
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Part 1 of the 2 part series

Updated 06/07/2023
Created 02/12/2016
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This is the next story involving Judy from my story "Jim & Judy."

*****

Just before bedtime Wednesday night I emailed Jim & Judy, it would have to be Friday of next week. I would take Judy until midday Sunday. She wanted a Doctor's office scene which she would get, and in return, I'd get a scene or two I wanted to put her in.

If you've read my story entitled "Jim & Judy", then you already know Judy is a mid forties housewife, who has recently become sexually adventurous and Jim needs help acting out the fantasies she shared with him. She is 5 feet 6 inches short, with nice curves, especially her butt, which she likes to have spanked.

This time I wanted Jim to bring her to my place. Last time had worked out well, so I thought he'd like to see where she'd be spending the weekend. In the email I'd told them my address and to plan to arrive around 7-ish and Judy should bring her toiletries, and two sets of comfortable clothes, plus a sexy lingerie set.

Eight days later I had set up my basement to fit the weekend's festivities. I have a pseudo dungeon of furniture I've made. This time she wants to play out a doctor's office scene so I dragged my examination table into the center of the room. I got it at a government auction. It was the real deal, metal with stirrups and the drop shelf and step at the end, drawers along the side. I added some bright floor lamps aimed toward the business end and "presto."

Next to prepare was my newest creation. It was a medieval set of stocks, only it works differently. This one was made with one large padded hole in the center, almost waist high, and two smaller holes above that one. The "victim" is bent at the waist through the big hole and her hands are then pulled up and back through the two smaller holes. Better than the traditional style, it provides full access to her breasts. It is made from two upright columns so that the center boards are slats that slid downward into place, each with a half-circle hole sandwiching the victim between the cutouts in the boards. I couldn't wait to try it. Since Judy is 5' 6" I had to put the bottom slat into its lowest position.

On Friday night they arrived around 6:45. I invited them in. Jim was carrying Judy's overnight bag. Judy walked straight up to me and gave me a big hug and a kiss on the cheek. She was much more outgoing and confident compared to the first time I'd met her, not that meek, mousy person staring mostly at the floor. I took in her perfume; it was that Black Opium again.

I offered them each a drink, they each accepted water. We moved to the living room where they sat closely on the sofa, their legs touching and holding each other's hand. Judy was much chattier compared to before, talking all about the weather and other small talk.

"We both want to thank you, so much" she said. "Jim and I have had such a wonderful week since you had me here."

Jim was intently watching her speak, then he piped right in. "I can't really believe it. I had some concerns, and I was a worried mess while she was with you two weeks ago. But now, wow, I never imagined..." he searched for his words. "She has such a sexual appetite; I can't believe the fun we've had. Hell, she gave me a blowjob as soon as we got home that night. She's rarely done that over the years, but this week, I've lost count."

She was grinning sheepishly, maybe a little embarrassed. She said "Aw, Jim I just like making you happy."

Jim looked at her then he turned to me. "I'm not sure what you did, but it rekindled something with us. I still support her on this if she wants to do this again, as long as she's safe and especially if she comes home like she did last time."

"OK" I said, "Jim, would you like to see some of the things Judy will be experiencing this weekend?"

Jim only nodded.

I said. "Alright Judy, I want you to take your overnight bag and neatly lay out all the contents here on the floor while I give Jim a quick tour. When you're finished have a seat and wait here for us to return."

She looked like she wanted to ask something, but I just gave her a stoic look and Jim & I stood and headed out of the room.

Jim followed me to the kitchen. When we got there in a hushed voice I told him he didn't need to see the basement if he didn't want to, the main thing was to leave Judy alone for a short while to spread out her things. He said he would like to, so we headed to the basement. When I turned on the lights he was immediately drawn to the center of the room. There was the exam table and a sheet-covered item near it.

He said, "That's a medical exam table?"

"Yes" I replied.

"That's what she said she really wants to do" he said absently. "What's that, under the sheet?"

I walked over and pulled off the sheet, it was the medieval stocks. Jim just stood there silently. I gave him a moment to absorb its sight.

I said "Don't worry, she will be fine. In fact afterward she will be better than fine. Just wait and see."

His mouth was slack as he nodded his head while I placed the sheet back over the stocks.

"Remember, you contacted me because she really wants this and you just don't have it in you." I assured him again, "She'll be fine, it is a fantasy, a realistic fantasy, but a fantasy no less. Do you trust me?"

He said "Yes, I said I do, I mean that, it's just, it's just; we've been married for what, 22 years now, I never knew. You know? I don't completely understand, but yeah, I trust you to only do what you say you'll do."

I grabbed a small bag off the exam table and said "Let's head back up and check on her progress."

When we entered the living room Judy was seated back on the sofa. She had two short rows of items on the carpet. A pair of sweat pants and a sweat shirt, a t-shirt, pair of shorts, socks, and a couple of white panties and bras. In the second row were a red lacy negligee and small zippered case, plus the empty bag. I set the small bag I'd brought up on the coffee table as we re-took our seats.

"Judy, has your list of fetishes and limits changed since last time?" I asked.

She looked quickly at me "I, I don't believe so."

The list she'd filled out for me weeks ago was cemented in my brain. She was inexperienced in most everything except traditional sex, oral sex, and tickling. She wanted badly to try bondage, spanking, blindfolds, nipple torment, gagging, humiliation, hair pulling, etc. She was a little interested in whipping, slapping, biting, and maybe try some anal, but nothing big anally.

Staring into her eyes I asked, "Do you remember your safe word?"

"Vermilion" was all she said.

"Judy, walk over to your things." She did. I said "Remove your clothing."

She looked at Jim, then back at me, frozen.

"What are you waiting for?"

She said "But Jim's still here."

I said with a grin "Jim has seen you naked." Sternly I repeated "Judy, take off your clothing and put them with the rest."

Jim had been looking at me too, but now he was staring at his wife. She glanced at him, saw him looking then quickly looked down. She slowly unbuttoned her blouse, then slipped it off her shoulders, folded it and placed it onto the pile. She slipped her shoes off and undid her slacks, sliding them down her legs and off. After she folded them and placed them with the blouse she removed her socks then stood and looked at me.

"What are you waiting for young lady?" I asked.

She said "But..." I cut her off with an open hand in her direction. I snapped my finger and pointed to the pile on the floor.

She reached behind her and undid her bra, as she slipped it forward down her arms her breasts dropped into their own weight and her nipples came into our view. Jim was fixated. He's no doubt seen her naked breasts thousands of times, but not like this. Not with her looking so utterly vulnerable. He licked his lips as she held the bra in one hand and slipped her thumbs into the waistband and slipped her panties down. Her tits dangled seductively as she bent to remove her panties and placed them on the pile.

I heard a small groan from Jim as she stood upright. She pushed her long black hair from her face and moved her hands to cover herself. I shook my head at her and wagged a finger downward; she lowered her hands to her side. She was a beauty. Not the firm little cutey she probably was in her twenties; she now had rounded hips, a little sag in her breasts, stretch marks, and was maybe 15-20 pounds heavier, she was however, a real MILF. Her raven black hair was striking against her pale skin, especially that thick dark pelt between her legs. Her body colors reminded me of that Playboy cartoon girl "Femlin" from the Party Jokes pages. Judy would look absolutely delicious in long black opera gloves, black thigh highs and black heels.

"Jim would you like to kiss your wife goodbye before you head off?" I asked as I stood up. Jim was still sitting there, staring at his beautiful wife, like he'd never seen her naked before. I guess he hadn't, not like this anyway. He slowly looked my way, then, when he stood he used his hand to reposition the bulge in his trousers.

He walked around the coffee table over to Judy and gave her a hug and kissed her. I could see he was squeezing her exposed ass cheeks. She hugged him around his neck and passionately kissed him back. As he pulled away he kept his hands on her, trailing them around her midsection and then he raised them up to her breasts and he lightly pinched her nipples. She jumped when he did this and he chuckled.

I told her, "I'm going to walk Jim to the car, take the medical gown out of the bag on the coffee table and put it along with your panties."

She was still standing naked in the living room when I opened the front door to go outside. Her nakedness was open to the neighborhood, only for a second, but she was fully aware of it, quickly turning away, hiding her front but exposing her ass cheeks to the front door. No one was outside anyway, but it made a good parting scene for Jim as he walked through the door.

I was nice enough to close the door after Jim exited. He was hesitant when we reached his car. Again I told him not to worry, "Be back here Sunday at 1:00 in the afternoon to pick her up, no earlier. She will be fine, remember, this is her fantasy, not yours." He just nodded.

It was getting close to dusk as Jim backed out of the driveway and headed off into the western sunlight. I re-entered the house through the side door and headed to my bedroom, bypassing the living room. I quickly stripped off my street clothes and donned some light green scrubs, I even had the cap and a clipboard to go with my outfit.

When I got to the living room Judy was sitting on the sofa, her gown on. "Judith?" I said as I entered. She nodded. "So, how are you feeling today?" Without waiting for an answer, "I see you're due for your annual physical examination. Any special concerns I should be worried about?"

She replied "No doctor." Wow, she really was ready to play this out.

"I see you've had some water to drink, would you like anymore before we begin?"

"No, Doctor, thank you. But I do need to use the ladies room."

"Please follow me" I told her. I led her to the guest bathroom. She went in and closed the door. I could see her bare back and white panties as she entered. When the door re-opened I was standing right there, startled, she looked up at me and I turned to head to the basement. When we got there I stood by the exam table and looked back. She stopped a few feet short and stared at it.

I was using my best, most professional sounding voice. "Please Judith, have a seat so we can get started." She sat on the edge and I grabbed my low stool and also sat. "I see here you've been married 22 years and have two children."

"Yes Doctor, that's right.

"Please" I said "no need to be so formal. Address me as 'Sir.'"

"Yes Sir."

Looking back at my clipboard I continued, "You and your husband have an active sexual relationship?"

"Yes Sir."

"How is your sexual relationship?"

She really perked up at this point. She said "Well Jim is really great at taking care of my needs. Especially lately, we've tried many new things lately."

"Lately?" I said. "So you did return to him after your interrogation and pay him sexually for allowing your fantasy? You sucked his penis deep into your throat like you were instructed?"

"Yes Sir." She said confidently.

She was getting too comfortable, I needed get her off balance a little. "So you enjoy pleasing him orally? Do you also enjoy having him put his manhood in your rectum? Does he put other large things in your anus?"

She was stammering "Well, no, I... we, not those things. You know just the usual..."

I cut her off "Please remove your underwear and lie back on the table." The table was set to a reclining position so she would be slightly upright. After she removed her panties she settled back. The stirrups held the legs up from behind each calf, they were padded and had a nylon Velcro strap to immobilize the leg. I swung them into place and put her first leg in and strapped it tightly then did the same to her other leg. I spread her legs wide and tightened the clamps that hold them there.

She was nearly where I wanted her. I walked to her side and had her lean forward so I could undo the gown straps behind her. When she laid back I slipped her left arm through the hole but left the gown covering her. I took her arm and used the nylon Velcro straps along the side to secure her wrist and upper arm in place. Then the other side, slipping her right arm out of the gown and securing it just like her left arm.

Behind her where she couldn't see, I grabbed a bottle of rubbing alcohol I'd placed within reach and twisted off the cap. I dribbled a little on the concrete floor just below where her head was and capped the bottle. I knew it would make the basement smell more like the doctor's office.

She was now tightly secured to the examination table, legs up and spread, her gown covering her like a bed sheet. I opened the drawer of the exam table and grabbed two latex gloves. I slipped them on and made sure to snap them as I pulled them into place. She was breathing a little quicker. We were now on the threshold of her fantasy and she knew it. I flipped on the lamps, they were brightly illuminating her pelvic area from two different directions. She had to squint through the light to see me.

I pushed my stool in between her feet and lifted the hem of the gown and rolled it back. She had her head up watching me. I could easily smell her arousal. I wanted to dive in, but this was all at her request, no rushing. I said her, "I can tell you are aroused. Does this happen to you often? Are you some kind of promiscuous MILF? Are you a shameless slut?"

The bluntness of the question compared to my former professional demeanor caught her off guard. Before she could reply I touched her sex, her head dropped back onto the padded rest and she responded with a moan. She began to push her mound harder into my hand. I massaged her pussy through my latex glove for a few moments. I inserted a gloved finger into her, then easily a second. Her eyes were closed and she was rocking a little, pushing up into my fingers.

I took my hand away and said "No, this just won't do." She started whimpering very quietly.

I reached into the drawer and she heard the humming. I'm sure she thought it was a vibrator. She jumped at the feel of the buzzing, cold steel. It was a small hair clipper. Again I said, "This just won't do. I can't see your pretty pussy, this dark fur has to go." I trimmed back all the hair between her legs, and then made two straight trim lines up from her pussy. Her pubic hair was dark and thick. It made a wonderful looking 2" wide landing strip above her pussy. It contrasted beautifully with her pale skin. I pulled out the shelf below her ass cheeks and left the room. She was craning her neck trying to see what I was up to.

I came back with a small bowl of warm water, razor, wash cloth, towel and can of saving cream placing all of this on the little shelf. I submerged and wrung out the cloth and laid it over her pussy and bikini area. She was mewing and rolling her hips slightly as the warmth worked its way into her shin.

When I decided she was ready, I removed the cloth and worked in the shaving cream. I wiped the lather off my gloved hands and began the shaving. I decided to start on the landing strip. Long strokes down each side and across the top, then it was on to her lips. I pushed on her thigh to make the skin taught and shaved inward to her pussy. She was breathing noticeable deeper during this. After I shaved both thigh-to-lip areas I shaved the spot above her hooded clit and created a nice little void between the hood and her new landing strip.

She jumped a little when I moved down to her puckered hole. She had some rogue hairs near her backdoor so now was the time to clean her up back there too. A few swipes with the razor and she was smooth as a whistle; front to back.

When I put the warm wet wash cloth back on her she really started rolling her hips. She was clinching her bound thighs and making her hands into fists, plus trying to get that warm cloth to provide more pressure on her pussy by twerking her hips. I put my open gloved hand on the wet cloth above her mound and applied some pressure. She really liked that. I then used the wet cloth to wipe away the little traces of shaving cream. I dried her with the towel, and put all that shaving stuff out of the way.

When I sat back on my stool I could see how aroused she was, her wetness made her whole pussy area glisten in the bright light. I reached into the drawer and grabbed a speculum. It was plastic and resembled a duck bill with a thumb lock on the side. Thanks to Amazon Prime I had it in time for Judy's session today. I tore it from its package and didn't even need to lube it since she was dripping wet from being humiliated, spread, bound and shaved.

"Just a little pressure" I told her. Yeah right, when the speculum met her entrance she pushed her pussy hard onto it. She was more than ready for this. I slid the device all the way in and then slowly clicked it, opening her up. Her legs twitched, her arm muscles flexed and her head rolled back and forth as I stretched her open. "How does that feel?" I asked when the speculum was locked fully open.

"Oh Doctor, I mean Sir, it's... I don't know, it's, please; please touch me again." Her breathing had become quick and shallow.

I slid two gloved fingers up into her and slowly messaged where her g-spot should be. Good thing she was tied down. Soon she was making the exam table shake. She made the stirrups rattle loudy with her movements. The manipulations inside her pussy were driving her crazy. Her whole body was contracting as she fought her bonds. I leaned down and put my tongue on her clit.

"Oooooh, argh!!" flew from her mouth.

I used my tongue to flick her little nub. She was rocking the whole table back and forth and gasping breaths between her deep guttural sounds. That's when she broke. It seemed too quick, too easy, but then again, her arousal had started when she stripped in front of her husband well over an hour ago.

It was a high pitched scream that filled my ears. Her orgasm made her whole body contract at once. I lifted my head and her whole body was tense. She had a sheen of sweat all over her. There was a flood of juices flowing out of her and down my glove as I removed it from her sex tunnel.

I carefully released the lock of the speculum and let it retract. She started saying "Ooo, oooo" and was twitching all over as her orgasm was subsiding.

I moved over to her head and placed my wet, sticky gloved fingers in her face. She looked up at me and opened her mouth. I inserted those two fingers in and she sucked on them, her eyes were still thin slits barely showing her dark pupils.

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