YouKnowWho
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Posts: 201
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This will be a 4 part recollection of actual events involving one of a number of married couples I was involved with.
There are some superb writers in this forum. I don't claim to be one of them, but I did my best to edit and provide the right context.
Feel free to view my other older posts here to get a background.
Thanks to all. Special thanks to the admin for keeping this site going for so long.
The Food Court - Part 1
This happened circa 2003.
Cara and Greg. Married in 1989.
I had met Cara when contracted by a trade show company needing a series of designs and graphics for about 6 of their top clients.
At the time, I had been seeing two other women (one recently separated, one married, but on the rocks. But that's another series of stories).
She had great computer skills, an infectious sense of humor, a beautiful body and an obvious sex drive.
We became fast friends. Sexual chemistry was there from the start. At lunch, she would share things about her marriage that was a signal she was looking for more. Greg, her husband, was a successful engineer, good provider and one of the easiest people to get along with.
She and I got together one night shortly after for the first of many sessions of very un-vanilla sex, jokes and good local food. But I let her know after our first private meet that I wasn't comfortable continuing anything in secret. She responded by telling me Greg understood she had some needs he couldn't provide her.
That wasn't enough. She knew about my past by then to understand there could be no going forward until he was fully aware, informed and behind the affair. She was silent for a while. Then her sexy sense of humor bubbled up and asked, "What did you have in mind?"
"Tell him the truth. Tell him I want to meet with all three of us to hear it from him directly". To my surprise, she gave me an incredibly sultry smile and said, "DONE". Wow!
A week later we all met at their apartment. He wanted details of my experience with couples and wives, and I was happy to oblige. At that point Cara moved from her seat next to him and sat on my lap facing her husband.
"Tell him more, Greg".
"I, uh, want to see it"
"See what?", I asked.
"You both..."
"Both what?!" with an edge of impatience in my voice.
"Answer him now!!", she shouted.
That snapped him into a better place. After being clear about watching me go deep and bare in her, I decided to up the terms. "What are you willing to do if we let you watch?
" Wha..? "
I didn't answer, but explained that I'd walk out if I didn't get a response. That's when Cara snapped again."Talk!! Now!! I don't want to ruin this chance because you're too modest". I suggested a few more glasses of wine to break the ice. She told him to bring two glasses for us and water for him.
Done and relaxed a bit more, she looked at him and said, "Well??"
"Anything".
"Give me specifics", I said.
He said he loved going down on her after coming, and that he wanted to start by doing the same once I was done with pumping her full.
I could feel the heat coming from an undoubtedly wet pussy as the back and forth continued.
"And while we're f*cking too", I demanded. He froze. Cara squirmed even more at the thought of this new twist. Especially since she liked getting it in the back door as much as the front.
What followed was over a year of some of the kinkiest sex you could imagine. When not going deep in his wife, Greg and I could talk about anything as if we were just normal friends. He was good at his job and often ran construction crews at building sites.
Once, while talking about one of our mutual interests (furniture making), I told him it was time for him to become more obedient and docile. It was out of the blue, so he wasn't prepared for what came next. "You need to start dressing and acting more feminine." He had vaguely shared fantasies of similar, but wasn't ever ready to act them out. That was about to change.
One incredible transformation evolved over the next 6 weeks.
It began with him giving me regular blow jobs (in front of Cara, and occasionally with her best friend Penny there). Each time we required one new change added. Panties, shaving body hair, stockings, heals, makeup, a decent wig and mannerisms.
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Hrellir
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Posts: 120
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Great start, have subscribed waiting for more to come... - H
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YouKnowWho
Member
Posts: 201
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Hrellir
I'll put up a new chapter about every 2-3 days.
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YouKnowWho
Member
Posts: 201
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The Food Court - Part 2
What came next was planned between Cara and myself without his knowledge. I showed up on a Saturday afternoon, ready to enjoy her incredible, wet, contracting pussy. Instead, we let him go first (all dressed up). He didn't last long since he was usually cut off from any penetration. But that was part of the plan.
She ordered him to lick her clean. And as that was going on, I rolled on a condom, covered it with lube, and proceeded to quickly f*ck his shaven ass. He grunted in some real discomfort, but Cara and I didn't want him to enjoy it at all. For me, there was nothing physically satisfying in the act, but the psychological roleplay of dom/sub was incredible for her and I. His pleasure would come at the idea that he could bring us both off.
Two weeks after that, our meet up at a mall food court happened, and the story took some unexpectedly wild turns.
To start, Greg had a conference to attend out of state in the intervening weekend, Cara opted to visit her parents. So I spent an overnight with the girl with the troubled marriage, Chris (Christina). She told me her teenage ******** had learned that a mall makeover booth a few towns west of us was staffed by two males... but you would never know it, they were that good at dressing, makeup and mannerisms.
That got me thinking of Greg and Cara. So I called her and we came up with another unexpected game.
He had never been out in a public setting dressed in any hint of feminine clothing (the one exception was an adult movie theater). The plan was to visit that same mall which also had a well-known women's intimate apparel shop. We would all be dressed normally, visit the store where she'd try on a few sexy outfits, model them for me with him sitting outside the booth. When she and I were ready to buy, all 3 of us would go to check out and he would pay for them with his card. The one variant was him wearing a lacy black camisole that was partly exposed. Pretty vanilla, but it was convincing enough that he didn't suspect we had two more things in mind before the modeling and buying thing played out.
First we were going to visit the makeup booth, sit him down, and with his black lace garment peeking over the unbuttoned top of his shirt, give him a a full nail polish and facial work-over. Lipstick, rouge, eyeshadow, mascara. Once done, walk openly to the erotic accessories store. The last twist was having Greg also model and purchase his own intimate girly outfit.
That's about the moment another turn in events sprung up. This time from Greg.
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YouKnowWho
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Posts: 201
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The Food Court - Part 3
We all decided to get something to eat at the food court first. Cara told Greg what she wanted and then said she had to "make a call" and she'd meet us at one of the tables. She was actually going to the booth to make sure they were prepared for our plan and that they would go over the top with the makeover.
As Greg and I were waiting on line, I spoke low to him that he was going to need more practice sucking cocks and getting popped before I let him near my dick again. I mentioned that we had discussed the idea of finding him an assertive boyfriend to develop his skills with.
He went silent, and a bit pale at that. I thought I may have overstepped here, but he was finally able to pipe up once a minute had passed.
Since the Saturday encounter we had two weeks prior, we didn't bring up what happened up between us. He and Cara talked about it, but I had no reason to pry into that.
He again told me about how uncomfortable his side of getting screwed was, how used he felt and how angry he was about having his own say ignored... especially when Cara insisted on feeding him the contents of the condom I used and then thanking us both afterward.
But...
Then he said the more he thought about it, the more aroused he got. And even though he told me it 'hurt like hell', he had to have it again.
That's when he started telling me about his conference the prior weekend. Or, more to the point, the non-conference part. Instead of arriving at his hotel on Friday night, he had opted to book a different nearby place starting Thursday afternoon. Along with his work clothes, he had packed one of his existing feminine outfits, makeup, etc.
Once settled in, he went to the front desk and asked if there were any gay or bisexual clubs nearby. He got directions to a classy place, and one that was a type of gay biker bar. He opted for the latter, but said he didn't have the nerve to dress up first.
After entering and sitting, it took all of 20 minutes to be approached by a trim, tall guy in jeans and leather. After a few ******** and laughs, Greg invited him back to his room. They walked there figuring it was safer than taking this guy's motorcycle.
They had more ****** ordered from the lobby bar delivered when Greg showed him his stockings, heals and whole getup. He offered to put them on, but the guy (I think his name was Ray or Ryan) wanted him to hold off. So they spent the night together. The next day, he invited Greg on a bike tour of the suburbs and highways ending up in his own apartment. This time wanting Greg to wear his outfit. So they rode together. Him in leather. Greg in lace.
For the whole day and night Greg got a no-holds education on being a man's subm1ss1ve sex bunny. He was hooked. And the kinkier it got, the more he liked it. What he described to me was unconventional in the truest sense of the word.
Saturday was all work, but they managed to get together Sunday afternoon for a college soccer game and more sex before his evening flight home.
When he was done telling me this, I asked him what Cara thought of it all since they shared everything. I was wrong there. He tried to cover his tracks by saying she encouraged him to explore experiences with other men (never, EVER with other women), but I pointed out our agreement that there was to be NO SECRETS.
I was pissed. We took our food to the table and I told Cara Greg had something important to tell her. As he started retelling the experience (as well as apologizing multiple times) her face got darker, hurt and angry. She ripped into him especially because he did this all with a stranger, had no clue if he was STD-free and put her at risk too.
We still managed to get him made up at the booth, but we bypassed the apparel store. We went straight to her parent's house (they were on an extended vacation by then), so we had the house all to ourselves.
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YouKnowWho
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The Food Court - Part 4
Greg's constant pleas for forgiveness were getting on our nerves. We ordered him to strip, offer his hands and feet to be tied and cuffed. His mouth was stuffed with Cara's soaked panties. She told him not to take his eyes off us as we spent the next hour in every position. Her anger channeled to multiple orgasms and ***** of him for his inability to be any kind of a man.
We left him laying there while we went out to eat and dance. Getting back, he had managed to get his feet free and mouth unstuffed. We found him in the bathroom ******** water from the sink tap. As soon as she saw him, she slapped his face and and yelled "Who the f*ck told you to get up?!"
Before he could answer, I stepped in and said I have an idea to keep his mouth busy while she and I got back to f*cking.
We ended up with him on the floor with us over him. Her on her hands and knees facing his feet, me kneeling behind her in a slow, prolonged thrusting. Each time she came, I could feel her strong contractions on my cock.
Greg was treated to worshipping my ass with his tongue for most of the half hour she and I went at it. When I finally couldn't hold back, filling her up, I first had him clean me off and thank me. Then Cara moved back and rubbed her wet cummy pussy and sweaty ass all over his face, forbidding him from using his tongue or cleaning himself off until the following morning.
But this one secret became the first of many for him. Eventually they got divorced. She remarried a physically and fiscally capable lawyer while perusing a successful photography career.
Greg remarried also. To a woman who was helped him develop his feminine, bi, docile side while she had numerous boyfriends and 2 babes from them (never him). He's still a successful independent engineer and technician. And, to his credit, no longer keeps secrets.
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