Wife and Friend

The questionnaire was asking me about my extremes.

 

I’m a conservative professional guy.

And I have a wonderful Wife key holder and an approved friend/no sex playmate.  Keyholder as is she hold the key to a chastity device which I am intermittently required to wear.  Part of our play is me getting locked up and threatened.  Threats of public humiliations, particularly in front of her girls friends are a huge turn on for me, when we go that route.  

 

Susan, I met on a train to NY.  She was a professor.  This acquaintance became a friend through professional occasional contact.  Drinks were had 1-2x a year over several yrs. One time things turned sexy talkative. Another time.  The friend is an academic / NY gallery owner Ph.D.  One holiday season, plenty of cocktails and her tales of sexual awakenings in the attic. I was taken to a book store and Toni Bentley's Surrender was pointed out. No play but nice sharing.

Another drink meeting, more comfort sharing.   Another half calendar turn and she told of fantasy of dominating associate's girlfriend post multiple chardonnay.  Another time, quite well served,  we left and I took her to Christopher St. and Chelsea sex shops. It was her jaw-dropping "excellent adventure".  Litterally, I had to reach out a couple of times and just close her mouth.  She bought duel vibrating eggs. Oh my!  We talked about me meeting her at the gallery before other staff came in and me giving her a spanking.  Wife as always being told all.  Wife is aware of prior extremes in my life, including bdsm humiliation. Our relationship had been more mild there, certainly private with the exception of one time when we both visited a prodom I had seen before, up until this event.

 

Along comes the CB 3000 male chastity device. We talk, I get one. Months pass and there's intermittent play.

 

"Did you ever meet Susan and spank her?" my wife asks one evening post play, considerable boundary-stretching submissive play on my part.

 

"No, I think that was a fun passing comment. I'd have to be the one to continue to press the issue. She would never bring it up.  Since meeting each other is so infrequent, I think we'd need to have drinks again to warm up the topic." I said.  Susan would never email or call on her own.  I maintain the contact.

 

"Oh" she said.

 

Months went by. Vacation plans came up and Wifey wanted to go to Europe with her sister. Being her typical sweet generous self, she asked if I wanted to go to a tennis camp, or make skiing plans, or or or .  I said I was fine, and I was. 

 

"Do you want to go see a Mistress?" she asks with a couple of drinks in both of us.

 

Boing!!  That got my attention.

 

"Yes, please!" in my best imitation of Mike Myers responding to Lorne Michaels when asked if he wanted to make Austin Powers a movie.

 

"You can go three times, but on one condition" she said. 

 

"What's that?"  I  naturally asked.

 

"I don't know" she said, indicating to me she knew perfectly well and I had to tease it out of her and it could take some time. 

 

A plan was hatched.  The premise of the condition was that she was never hot on the idea of Susan getting a spanking from me, certainly without her permission.  The condition was dictated to me that evening post play in a memorandum to Susan...... it's title was "To Receive You Have To Give".  My mission was to warm up the spanking idea with Susan, make plans to execute it CB 3000 encased,  one Saturday morning, and when I got there give her the memorandum from Wifey. 

 

The memorandum was very cute, very clever and very directed for Susan to mark me 10x on each side of my rear with a favorite slapper of ours. Wifey wanted to be able to count each mark. No room for hesitant work. Susan was instructed to step up to the plate and do it right or it would be done for her.  If I were successful, I could have my 3 Mistress visits and Susan could have her otk spanking when ever she wanted it.  The memorandum made note of the fact that Susan should inspect my locked up state and be aware that I would always be in that state from now on when ever she saw me.

 

Well.  Now for the warming up Susan part.

 

I took my time easing in multiple emails, calls and occasional suggestive remarks with so so results.  So one time upon calling I said "look, darling, I'm in the mood for a liquid-ish lunch, some good food, and some great conversation with a friend, are you my friend and when can we do it?".  Bingo, it was 3 PM-ish, she hadn't eaten and the timing was right. I called Wifey to let her know.  Table cloth in SoHo, white burgundies and the memorandum came out. Weeeeeeeeelllllll, the best thing that can be said is I will never never never forget the rush of blood and blush to her entire chest, face and being. Never.  That was pretty f__king adorable.  She was flabbergasted. I had to walk a tight rope from keeping from disintegrating.  I told her how beautiful her blush was over and over. She lightened up, laughed embarrassingly and we were having fun again and stayed mostly on point. I could tell she was intrigued but this was a big big step for Ph D darling. I'd have to ease her through it.  Waiter, more wine please. 

 

I got her talking about her adolescent attic experiences which flowed freely. We segued into buzzing benwa balls, then my cock enclosure. She wasn't comfortable slipping into the bathroom to look at it but she touched it with a little help from me as I was telling her how it made me feel.

 

The bottom line was she was interested but not promising anything; still blushing blushing blushing in the most adorable way, the gallery wasn't a good place to go back to after lunch though I pressed for that multiple floors, back rooms and all; she wasn't sure she could actually strike someone. "Well, darling, you're just going to have to fucking grow up and do it" I said.  "Remember telling me about all those things you haven't done, well that bullshit's over".  I could almost feel her cum. I think my words went right to her pussy and drenched it. I was pretty shocked watching the impact my words had on her. I held her wine glass up for her to take a drink and she obeyed.  "Pretty exciting, isn't it". "Very" she said. Feeling the momentum, I said "well, Debra (Wifey) isn't going to take my word for it, if those panties are as wet as I think they are go take them off and give them to me!".  "I can do that" she said with a smile.  I almost shit.  Too adorable.  Boom, up she got. Within in 60 seconds she back, stick her hand in my blazer pocket and sits down. Coffee, but no closed deal, at least not today, maybe Saturday.  That was Susan, maybe. She was gone and I called Debra.

 

"Well why don't you have another drink there because if she's not going to redden your bottom, I will. In fact, you might have to toak up". I rarely drink and smoke, did in the good-old-and-damm-horney-whipass-bdsm-days, so the thought was both scarey and enticing.   And I was well on my way, having had a favorite ritual of lunch, wine and pisser conversation.  We bonged and played. Through tease and denial Wifey got me to beg for a multi implement reddened ass. Way harder than usual but awesomely hooch enhanced.  I was a happy guy.  Then she has me call up The Hidden Chamber, final bong hits and WE go over with food and wine.  My favorite ending is golden shower oriented, but Debra only knew of this from me saying so.  Early on, I'm teased adn denied onto my knees, large O ring in place, Susan's panties stuffed in my mouth and my wife is peeing in my mouth promising we're not leaving until I drink her dry.  On the suggestion of our Mistress, I would get my mouth filled and told to wait until a guest Mistress could come in to whip my ass while I drank. I rolled a dice for the implement and the Mistress praying one certain Mistress would not be rolled.  I could start drinking on the first stroke. I did drink her dry, and missed the most severe thrashing thankfully, but know I'd been marked for a good several weeks which hadn't occurred in years. We showered and left.

 

In the cab, Debra directs the driver to Susan's SoHo gallery. "Holy fuck, what are you going to do?????"

"You'll see."  I was in a kind of heaven having gone to such extremes with my Wifey. I was comfortable and trusted her.  "It's going to be tasteful, right".  "Yes", I was assured.

 

We browsed just like other gallery goers. When Susan spotted me, she knew immediately Debra was my wife. She strode out confidently in her own shop and extended her hand. "You must be Debra, how lovely to meet you".   My heart was pounding. Debra was completely gushing with charm.  They were like lost girls friends in a few minutes, they needed no help from me. I figure my pants are going down sometime and my probably unattractive whipped, paddled and reddened ass will my exposed to Susan in some way.  My cock was hardening with the thought of the humiliation to come. Debra was orchestrating beautifully.  "Do you feel, ok" she asked me. "Yes, I feel fine".  She lifted her hand to my face and forehead.

 

"Does Joe feel warm to you, Susan" Debra asked, and with that she grabbed the back of Susan's hand and pressed her palm for long long seconds against my ass.  "He feels warm doesn't he?" 

 

"Yes, very warm" Susan said, both women totally comfortable with the play. I thought pussy juice was going to come running down a leg.

 

"I'd better get him home. We had dinner but I insisted Joe take me by your gallery.  It's beautiful! I want to come back when we can spend more time and get to know one another. But I think he’s whipped. I think they worked him over pretty good today and he had to drink some bitter medicine.  I am so glad we met. Let's make dinner plans soon.”   She agreed and we left.

 

That's what extreme we went to.