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Like most anonymous relationships this one started on line on one of the usual websites for D/s hook ups and we did the usual on line chat room stuff to ease everyone ones suspicions on who was real . Staged pics were obtained, nothing x-rated and video chat was short and to the point but ultimately proving we were all who we said we were.
Jenny and Pete were fairly new to the D/s scene with Jenny wanting Pete to be the take charge Dominant side of the relationship but he just didn’t have the ability to be anything other than in love with his wife and she knew it . It always felt like he was just “acting” and there was always something missing during their play and was driving both of them crazy. Crazy enough to seek out professional help from someone with experience which ultimately led them to my door and a chance to have a look at what it could really be.
We chatted for a few weeks about boundaries, expectations, likes and dislikes before settling on a date and place to meet with instructions to call the day before for final instructions on what was expected of the both of them for preparation for the day.
The night before I had them video call with instructions to be polite, submissive and respectful from this point on if they expected to serve without disappointment. Both were sat side by side looking quite apprehensive as I ran through my expectations for them based around their own wish list.
Pete was to take on a more voyeuristic role, as well as preparing his wife and releasing her into my control on their service days. Jenny wanted the full submission package without boundaries and with the added bonus of having her husband watch how she could really serve someone who wouldn’t let her get away with disrespect and inattentive behavior.
For the next day I would have Pete bathe and shave his wife , she was asked to wear a black , above the knee skirt, a white button up blouse, black 4” heels, red nail polish and lipstick. Hair would be in a high ponytail, panties would be small, white and lacy and she would not be allowed to wear a bra.Pete would have black pants and shoes, a white shirt and no underwear on. Nothing too unusual so they would not stand out in the small, intimate restaurant we were meeting in. A restaurant with secluded booths, poor lighting and good food. Perfect for nervousness on a first night with high expectations.
An hour before the meeting they called me for a final confirmation that they were about to set out and for their first instruction prior to arrival.
Pete was told to get on his knees in front of his wife and Jenny was told to pull up her skirt and wait for me to have Pete put his phone on speaker.
“Yes Sir” she replied, a good start and I then instructed Pete to start licking his wife towards orgasm.
“Begin”, I could hear Jenny gasp as his tongue connect and i informed her that she was to ask permission to come before she did so.
“Yes Sir”. I then told Pete he had 5 minutes to make his slut wife come or he wouldn’t be given the opportunity to watch her come for me. I also told Jenny that if she didn’t come quickly then her husband would watch her being spanked by me instead.
“Is that clear “ they both answered with a “yes sir”.
The excitement of the forthcoming meeting was obviously setting the pace and Jenny was already gasping heavily as her orgasm raced towards her. I told Pete to suck on her clit as hard as he could and Jenny then exploded with a shrieking “please may I come Sir” to which I said “ come now”, and she shuddered to a finish gasping a “thank you sir” through clenched teeth.
Pete was told to stand up and kiss his wife so she could taste her come on his lips then he was told to take his cock out to show his wife how hard she’d made him. I asked Jenny if she approved of her work?
“Yes sir”, i then asked if he was leaking because of it, again “yes sir”. Now i had her lick him clean and put it back in his pants before getting in the car to drive to the restaurant. My final instructions before they hung up the phone was for Jenny to sit with her leg spread open and to keep playing with herself throughout the journey in full view of her husband and anyone else that may see her should they have to stop at any traffic signals. Under no circumstances was she to come but she was to make sure she stayed swollen and wet and that her husband stayed hard.
“Do you understand?” ,
“Yes Sir”
I got to the restaurant 15 minutes early to settle into a quiet booth in a dark corner where I could arrange the seating to ensure Jenny had her back to the room facing both me and her husband across the table. They called, right on the hour, as arranged to inform me they had arrived. I let them know where I was and watched them walk over , Jenny red faced and flustered now that she realized why she wasn’t allowed to wear a bra and her heightened sexual state had left her nipples angrily seeking attention and Pete walking awkwardly behind his wife as he tried to hide his obvious erection . I enjoyed their discomfort as I ushered them to their seats , made all the more uncomfortable when they realized that they wouldn’t be sitting together but opposite each other.
I ordered drinks and informed the waitress that we’d just be having a few drinks and a chat, apologized and assured her I wouldn’t hold her table too long and I’d make sure my tip compensated for her time. She smiled and five minutes later a bottle of wine and three glasses were sat in front of us and she left us to our evening.
I complemented them both on their attire and ability to follow instructions from me. In hushed voices they both said “thank you Sir”.
“Now , do you want to proceed or is this too much?”
Pete hesitated waiting for Jenny, but she rushed out a very breathless “proceed please sir”
I turned to Pete. Jenny said “go on, remember what we said”, and Pete replied with “Please use my wife Sir”
“Thank you”, I looked across to Jenny, “spread your legs so I can see your panties “. She looked around but did as she was told. I settled her nerves by telling her no one can see but us and eventually, with training it won’t matter if they do. She blushed but kept her legs spread.
“Pete your slut wife is very swollen, those panties are barely covering her. Why is that?” I asked
“I made her come for you Sir and she’s played with herself all the way here Sir” he replied . I then asked Jenny if she’d been a good girl on the ride over?.
“Yes Sir I didn’t come again “ I then told her that she was to ask permission for every orgasm she has from now on , even if I was not there using her. “Do you understand?”,
“Yes Sir”
I had them sit there finishing the wine as I fired very intimate questions at them as I gauged how quickly their training could proceed. Asking how many times they masterbated, had sex, preferences for achieving orgasm, externally or internally, I asked about their experience with oral anal, voyeurism, toys, . All designed to make them uncomfortable but incredibly turned on because they had to give answers whilst sat with the hands on the table. Jenny still with her legs spread and Pete with a now very ,very obvious erection, which at point he tried to cover but was told to keep his hands on the table.
Once tha last of the wine was gone I ushered the waitress back over to pay her and let my two submissive friends sit there mortified as she gave each a cursory glance at their predicament.
I congratulated them both on passing their final test on how serious they were about serving and let them know I was impressed with their dedication to instruction no matter the situation.
“Now , shall we proceed to getting you home to conclude your service today with your presentation to me”
They looked a little confused, so I continued. “I know you were just expecting an interview and a little teaser on what it is to serve but you’ve done so well that I feel you are ready for your presentation “
I told them to take their hands off the table and make themselves comfortable, to which Jenny closed her legs and Pete place his hands in his lap before they asked what a “presentation” involved.
“Well Jenny will get her first inspection to show me how well you’ve prepared her” I told Pete.
“Jenny , you will show me how you come and afterwards you will get your first spanking in front of your husband “
I then informed her she will get to watch her husband come in front of her and he’ll get to rub it onto her newly reddened ass.
I let them know that the decision was ultimately there’s and if they needed time to think before committing, then I was fine with that too.
It was Pete who spoke, which was a surprise because I had the impression he was along for his wife’s fantasy journey and he said they’d like to talk things through before setting another date. But assured me that he definitely wanted another date and then quickly looked over to his wife who nodded. He then said he wanted Jenny to ride home to their house with me as a show of good faith that they were serious. This statement bought a gasp from Jenny and a smile from me.
“Ok , well then I see no reason why you should not continue to serve right up until Jenny gets home then “ I said
“Do you not agree?” Which got an avid “yes sir” from the both of them.
“Jenny go to the bathroom and bring me back those wet panties of yours “ , I instructed. Then verb watched her disappear into the back, only to return five minutes later with a tight wad of panties bunched up in her right hand . Once at the table and sat down I asked her for the panties which she hurried parceled into my hand, then watched as I rubbed the sticky wetness between my fingers before licking my fingers clean.
“Hands on the table and spread your legs” , Jenny complied. This time her husband and myself could see her swollen gaping pussy in all its glory, still glistening from all the abuse she’d given it.
I now turned to Pete and handed him his wife’s panties. “Go to the bathroom and put these on” I told Jenny to go with him and make sure he was wearing them to her satisfaction. Then come back to the table and wait for my next instructions.
They were gone a while and I did think they’d sneaked out the back and changed their mind but , no, they eventually stood in front of the table as instructed awaiting their final assignment.
I asked about the delay and Jenny informed that Pete was so hard she struggled to get the panties on and every time she touched him he leaked more precome and pleaded to be milked.
I asked if she did?
“No Sir” was her reply. I asked why and she replied that she hadn’t been given instruction to do that and didn’t want to be punished. I told her she was a good girl and her face lit up. Pete’s however did not, “I’m sorry sir” was all he could manage. “”
“Well I can see someone will be getting a cock cage for future training if I can’t trust you “ I told him, to which I got another “I’m sorry sir”
Final instructions for the ride home I continued.
“We will be walking out of here together, jenny will take my hand and you , Pete, will walk behind us in your wife’s wet panties” .
I then informed them that Jenny would be getting into the back of my car and Pete would be standing by the window until I tell him to go get his own car. I would then follow him home and deliver his wife back to him.
Pete took the humiliating walk out of the restaurant, probably grateful to be able to hide his erection behind us but I did notice the waitress smile and give a cheeky wave on the way out. Jenny walked, staring straight ahead trying not to think about her erect nipples still showing for all to see and just focusing on getting out into the dark parking lot and some semblance of modesty away from prying eyes.
I’d parked a the back of the lot away from other cars just for a little extra privacy should it be needed and as it happened it was. I opened the rear door and let Jenny get in, leaving Pete standing by the open door waiting for instructions. I got in the front telling Pete to close the rear door. Once I heard it close I let down the rear window on Pete’s side so he could hear what I said.
“Jenny slide into the middle of the seat , take all of your clothes off except your heels and pass them to your husband”
She hesitated, “ unless you want your husband to watch me spank you before he takes you home instead “
She jump out of her uncertainty and quickly stripped as instructed. Passing the clothes to pete who quickly took them to their own car and came back.
Jenny was slim , mid 40’s with shoulder length dark hair , nice firm breasts and a plump swollen pussy, that went well with her rounded full ass . Still she was self conscious and true to hide herself by crossing her arms until I told her to put them down.
“Now Jenny reach into the pocket on the back of the seat and take out the dildo you’ll find there. Then spread your legs”
The dildo was back , around 8” long but fairly thick, thick enough to make Jenny uncomfortable holding it. I reached into the center console, took out a tube of lube and passed it back to Pete. I then told Jenny to pass the dildo to her husband, which she did.
“Pete I want you to make sure there’s enough KY on that so your wife can manage it, do you understand?”
He replied with a hasty “yes sir” tinged with relief that it was , indeed, for Jenny and not him.
“Now pass it back to your slut wife” , the now very slippery dildo was back in the hands of his naked wife
Now it was Jenny’s turn to comply.
“Jenny I want you to start fucking your self until you’re stretched enough to take it all. By the time we arrive at your home I want your husband to see how much of a slut you are with it all the way in. Do you understand?”
“Yes sir “ she replied
“Now begin” I told her and she started to slowly work the dildo into her sopping pussy. After five minutes of slowly easing it in and out she had half of it in. The length wasn’t the issue, nor was it intended to be, I wanted her husband to see how much girth she could take. After a few more minutes I told Pete to get in their car and I would follow him, I also told him to bring a decent sized coat out to his wife once I was parked on their driveway.
With that we begs the journey to their home with me occasionally looking in my rear view mirror to check that Jenny was still working her pussy.
I asked her to inform me when we were close to our destination and also informed her that this time she could come as often as she liked as long as she asked permission.
This information increased her paced and before long she was gasping out her request to come, the dildo was three quarters of the way in so I told how proud I was of her and that yes she could come. Her orgasm came in a shuddering sobbing, desperate need and she slowed her thrusting as it subsided.
“Do not stop fucking yourself” I commanded and she increased her speed
“Now work on burying that cock inside you, you do want to make your husband proud don’t you?’”
“Yes sir” she whispered. She was running out of energy so I told her she could slow down and concentrate on filling her hole ready for when she got home.
Within 10 minutes she was pointing to their street gasping “here” and I watched her husband pull into their drive and go into the house.
I turned to look at jenny. She was still working the heavy dildo in between her legs and succeeding in burying it all the way to the fingertips she needed to hold on to it. I told her to pull it all the way out until only the tip was in then plunge it back in when I said “now”.
I had her do this a half dozen times and the sudden impact of the dildo thrusting in had her pussy leaking heavily and had her whimpering every time she pulled it out to wait for the next “now” to thrust it back in.
Then she was told to hold the position with just the tip in her pussy. I told her I wanted her husband to see her gaping whore pussy and what she’d been doing to it. As the door to the house open and Pete came walking down the drive, coat in hand , I gave Jenny her final instructions before I handed her back to her husband.
“Every time you ram that dildo into your hole I want you to say”“fuck me” do you understand?”,
Too exhausted to answer she just nodded.
Pete stood by the rear door waiting, I opened my window and told him to open the rear door to take a look at his wife.
Once the door opened the interior light came on and he took in the sight of his naked wife, bathed in sweat, legs spread wide with the huge dildo set at the entrance to her swollen, throbbing pussy. I let him take it in for a minute or two then said “now “
Jenny rammed the thick dildo in to the hilt and in doing so squirted juice over the seat as she screamed “fuck me” before pulling it back out to just the tip. As the dildo sat waiting for its next mission her pussy began throbbing and Jenny asked permission to come. I gave it but told her to keep fucking herself without stopping. Her hand kept into action as her orgasm swept over her and she screamed “fuck me” 8 more times before collapsing, sobbing and spent.
“Thank you Jenny I’m very proud of you”, she smile and just lay there.
I told Pete to take the dildo from out of his wife, put the coat around her and take her into the house.
I was unsure if Jenny would have any energy left to take care of Pete but I do have a thank you message and an ask to serve again ….so
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