Role Reversal for My 50th Pt. 03

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Continuation of our birthday trip to New York.
4.5k words
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Part 3 of the 4 part series

Updated 06/09/2023
Created 05/25/2019
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Once we had both cleaned ourselves up, we realized we would need a good meal before heading out on our adventures for the night. As had been the case through the whole trip, Gwyn picked out my clothes and laid them on the bed while I was in the shower. I'd removed the inflatable plug from my rear before getting in the shower, and was feeling a little empty and not sure how I felt about that at the moment. I was completely naked, and fully clean inside and out when I returned to the room.

The clothes laid on the bed were my own, casual pants and a dress shirt, with my own boxers and socks. There was nothing to suggest any of the activities of the rest of the trip. Gwyn was wearing a conservative pair of work pants and a nice shirt, with jewellery to match. She gave me a quick direction to get dressed as we needed to get moving to make our dinner reservation. I followed her directions and shortly we were walking out the door on the way to dinner at a nice Thai restaurant just down the street from the hotel.

When we were seated, and our order placed, Gwyn looked me in the eye and started the conversation that we both knew was in the air.

"I wanted you dressed comfortably for this" She said. "I need you to know that you can go back to normal anytime, and that I love you no matter what. I've had a lot of fun for the past couple of days, and I know that you have too, but fantasy and reality can blur together and get to be a problem if we are unwilling to talk things through. I think that tonight could be very intense, and out of both of our comfort zones, so I wanted you very comfortable to make decisions now about how far we are willing to go in our 'alternative' roles. We can stop anytime. I don't want to yet, but I need for you to know that if either of us wants to back out or slow down with any of this, it is not just OK, it is necessary. I know that you will back down for me, and that you will do almost anything I ask you to do, but I will do the same for you."

She continued, "Here's the thing though - and it 's a bit of a surprise to me. I like this. I like being sexual with you as much as I want, and it's way more than I thought would ever be the case. I like being in charge of how and when both of us express our sexuality. I've always liked being fucked by you, and enjoyed our sex life immensely, but I REALLY like fucking you and having you under my control in that way. I don't want everything in our lives to change, and I would rather dial back to normal sex, and keep the rest of our lives as partners like we always have, than keep up the kinky sex life and not have you as my equal partner through the other parts of our lives. I want both, but sometimes that might not be possible."

Gwyn took a breath - and looked at me with love, not lust in her eyes.

"I just wanted you to know that as much fun as this trip has been, absolutely nothing has changed about how much I love you and believe in you and value everything that you are"

I looked at Gwyn - and smiled, again thinking to myself how lucky I was to find her and be with her. I thought for a moment about how to respond, and I agreed with everything that she had said, but I wanted to make clear to her that nothing would ever change the way that I felt about her.

"Everything on this trip has made our lives better, more complete, more full" I stated. "I don't know where this all takes us, but every new day for the past 20 years has been a new adventure, so I realize that we will never be able to know what is coming, but I want it all. I want to the be the friend and partner that I have always been. I want you to be able to trust me and count on me to agree or disagree with you based on who I am, not out of any fear or misplaced obedience. I will always be honest with you, and when it comes to this week - I have loved every minute of it. I want you to know that I will be your slave any moment you ask it, but that I will still give you my honesty and my love if that is what is needed. I will obey you in all things sexual, but still disagree about life things because that is who we are. I want everything we've always had, and I want you to tie me up and fuck me whenever you please. This trip adds extra dimensions to our lives but does not have to change anything that we have always had, and tonight is just another adventure that I want to go on with you."

Gwyn leaned across the table and kissed me lightly on the lips. "Wonderful. I'm glad we could both be really clear on that, and I'm glad you wore your normal clothes and nothing unusual. I trust the conversation more because of that. Now - I have a small gift for you that I'd like to give you in preparation for this evening." She handed me a box out of her purse and told me to open it.

In the box was the collar that Amy had given Gwyn earlier, the one that had 'Taken' on it. It was black leather with an adjustable sizer, and about an inch and a half wide. There was also a pair of backless black thong panties with straps so that my ass would be completely exposed. The last thing was a small pink silicone butt plug with a wide base and the words 'Ride Me' imprinted on it, and a little package of lube.

"I want you to go to the bathroom right away. Take the box with you and don't bring it back. Throw away your boxers and the box, and show me the collar when you return. It should hide under the collar of your shirt for the time being, but it doesn't matter - no one here knows us. I want you back her in less than 10 minutes - food should be here by then."

I stood up and walked around the table and leaned in to kiss her before I left for the bathroom. I leaned into her and put my hand in her lap while we kissed. She moaned into my mouth as I pressed my fingers hard against her clit through her dress, and said quietly, "Yes Mistress" - and then away I went to the bathroom, back in Gwyn's control.

It is difficult to be subtle and quiet while changing in a bathroom stall and inserting an anal toy, but I tried my best to be quick and quiet. No one else entered the bathroom, so I managed to change without causing any kind of commotion, and the plug slid in without any difficulty as it was smaller than what had been in there recently. I put the collar around my neck and pulled my shirt up around it. When I stepped out of the stall, I threw away my boxers and all the garbage and then took a moment to look at myself in the mirror. I checked out my ass to see if the panty line was showing, but there was no sign that I was wearing anything unusual. The collar was showing just slightly under my shirt, and I was feeling a little daring, so I opened up an extra button which made it so that the word 'Taken' was very obvious around my neck. When I returned to the table, the server had just left and Gwyn looked at me and smiled.

"I have a feeling this is going to be a very interesting night" she said cryptically.

We ate a wonderful meal, mostly without conversation, and although the server looked at the collar a little funny, most everyone else either did not notice, or just ignored it. We left the restaurant and walked back towards the hotel. As we were walking, we passed a lingerie shop, and while I was trying to subtly admire the outfits in the window display, Gwyn just walked in. I was standing on the street by myself for just a moment when I felt my ass start vibrating. I realized that the small plug had a remote control, and that Gwyn was, in a most pleasing way, calling me to her. I entered the store, and Gwyn found me and grabbed my ass and quickly kissed my neck and whispered in my ear, "If you feel that again, find me immediately."

We looked around for a couple of minutes, when a saleswoman approached as and asked if she could help. Gwyn responded that she was looking for something sexy for my birthday celebration. The saleswoman looked us over and appeared to consider the meaning of my collar and asked, "For you, or him". I think Gwyn was enjoying all this process as much as I was and said, "Possibly both, but for the moment start with him.

She sized us up in an instant, and suggested we go to the back and sit while she brought us a few options. Gwyn followed her, and I trailed behind slowly, until the plug started buzzing again - that sped me up a little.

We sat in the back of the store while Patricia, the saleswoman, went off to find some outfits for us. She returned with two things on hangers. The first was a very skimpy strappy black satin and lace teddy, there was hardly anything to it, and I tried to imagine either Gwyn or I wearing something so frail and it didn't fit either my fantasies or my imagination. The other was a white and sheer merrywidow top with lace over the breast. It had clips all the way up the back, and there was also a pair of white satin panties with ruffles to go with it.

Gwyn looked at both and asked if I could try on the white outfit. Patricia said yes, and they looked at me to start stripping. For the second time to day I was about to strip in front someone other than my wife.

"Just the shirt", Gwyn stated. "You don't need to go any lower than that.

As I stood in the middle of the small room with just the collar and pants on, Gwyn took the outfit off the hanger and reached it around me. She connected all the clasps on the back, and when it was all done up, she muttered something to Patricia about the same thing in black, but with a bra. I looked silly with the garter straps hanging over my pants, but as I looked in the mirror, I could see how submissive the outfit and the collar made me appear. I was getting hard again, when I noticed Gwyn press a button on her phone, and the plug started vibrating again. It was in a random pattern, fast, slow, off, picking up speed and then dying off again. I didn't know what it was going to do, but every change kept me thinking about it and made me feel sexy right to my core.

Gwyn made arrangements and purchased both outfits, but just had me put my shirt back on over top of the lingerie. It seemed to me that the shoulder straps were visible and screaming to everyone around that I was my wife's slave - but because we were so far from home, I had no fear of being caught out, and was just turned on by the whole experience of being out in public, underdressed beside my dominant wife, with a toy vibrating in my rear, and marked as hers by the collar around my neck. We left the store and I carried the bag from the lingerie store as we walked down the street towards the hotel, through the lobby, and up once again to our room.

++++++++++++++++

"It's time for us to get ready for tonight", Gwyn stated. "I want you to have a shower, and make sure you are well shaved. You may remove the plug that you are wearing while you shower and use the toilet, but after the shower, you are to replace it where it belongs. When you come out into the room, make sure you are dry and ready to be dressed. I'll have your clothes laid out for you, with any accessories you might need. Do not masturbate - I know you might want to, but I will let you know when and where you are allowed to cum tonight. You wanted me in control, and now you better hope I am kind and generous if you want to have your fun. Understand?"

I nodded and headed off the shower, removing the plug and trying to keep my hands away from my cock. I was ready to explode, but I wanted to follow every command, obey every order that Gwyn gave. I knew that she was into the game thoroughly, and that she would ensure that both of our needs were attended to.

I showered and shaved, and dried thoroughly and then looked again at the plug. I cleaned it up very well, and realized that I didn't have any lube in the bathroom, so I put it into my mouth while I loosened up my hole with a little spit. Looking at myself in the mirror, with the end of the plug and the words, "Ride me' sticking out of my mouth, I could only wonder what the rest of the night might bring.

I put the plug back in my ass, and walked out of the bathroom and into a whole new world.

On the bed was my purple outfit that Gwyn purchased in the morning with Amy. Gwyn took the other bag that she had bought into the bathroom and told me to just relax after I was dressed and that she would be a while.

The tight, shiny, zippered metallic shorts and shirt left me feeling chilly, so once I was dressed I got into the bed and under the covers and turned on the TV, quickly coming across a tennis match from down the road at the US Open. I imagined being in the crowd with Gwyn, dressed for Fetish night, and the thought was enough to distract me while Gwyn got herself ready. I'd never really imagined going out in public dressed for sex, or feminized, but at this point I couldn't help but wonder what our future might hold.

Gwyn came out of the bathroom with a long coat on, and made up for a night out. She was wearing black stockings, with tall black heels on her feet. She had her hair up, and light makeup, with deep red lipstick, and long earrings. I thought about her coat and wondered what I would be wearing to travel to the club. She answered the question quickly.

"Get dressed in casual clothes, like what you were wearing earlier. I want to be prepared for anything, including just going out for a nice meal. Make it quick - we're leaving as soon as you are dressed."

I dressed and Gwyn grabbed her purse and away we went, down through the lobby and off to a Fetish club by Uber. The driver looked at us when we got in the car, and smiled to himself as he put together the clues from Gwyn's outfit and the address we were headed to. If anything, he probably thought that I was the one in charge tonight, but it's amazing how wrong he was.

We arrived at the club and stopped at the door. The doorman looked at us and rolled his eyes saying that I couldn't come in dressed like I was. Gwyn looked at me and told me to quickly take off my casual clothes. She removed her long coat leaving her in a dark green and gold satin corset dress, tight enough to highlight every curve, and with just enough coverage at the top to push up her breasts and cover her nipples. The dress came down to mid-thigh and I could see the lace top of her stockings just below the dress line. She was stunning!

Now the doorman took another look, and his expression changed entirely. We asked if there was a place to leave a bag, and he directed us to a room with lockers for our extra things and jackets. The last thing Gwyn had me do was get out of my boring black loafers and put on a pair of shoes almost identical to hers. I wobbled back to the desk, and after locking up our things and paying the admission, we were allowed to enter the club. This was the moment of truth for us. Could we handle this scene, and how would the rest of the night go for both of us?

We walked through the doors, and were greeted by something unexpected. It was fairly light, the music wasn't too loud, and although everyone was dressed sexually, there was a wide variety of outfits, crossdressers and latex, sailor and anime costumes, and hats - lots and lots of hats. It was fun to look around and just observe the space and all the variety of people that had made their way there. It was like a Halloween party, where everyone was free to be as sexual as they wanted to be. Both Gwyn and I are pretty shy at heart, and neither of us really like clubs or big parties, so we probably looked a little like deer in the headlights. I think we were both lost in the experience when Amy, from the store in the morning, walked up to us.

She was dressed in full dominatrix wear. She wore thigh high boots with at least a 4 inch heel, so she was face to face with me even in my smaller heels. She was in a red latex corset dress and shiny black tights, and her hair was curled and sparkling in the lights. She had red latex kitten ears on her head.

Amy walked up to the two of us, and brought us out of our daze. She kissed me lightly on the cheek, brushing her tongue forward and parting my lips before intensely kissing me for a few seconds. She then moved to Gwyn and skipped all the pleasantries and kissed her on the neck before grabbing her breast and pulling her nipple up and out of her dress and kissing it as well. She then looked at us, taking in our stunned expressions, and said, "Welcome to the club. I figured out from our conversation earlier that this was likely where you were headed so I thought I'd meet you here. Please join me at my table." Then she turned and walked off into the crowd.

Gwyn and I were too stunned to do anything but follow her, and she led us to a table with a bench. There was a bottle of wine and some appetizers waiting for us, and she poured all of us a glass and took the first sip, just to show that there were no drugs or anything untoward involved. All of the tables had candles lit, and were set elegantly. It seemed strange that they all would have long black tablecloths that almost hung to the floor, but it was all just part of the oddly normal décor. Everything seemed almost normal, but not quite, just like most of the people.

Amy invited us to sit, with Gwyn next to her on the bench seat and me on a chair across from her. She leaned towards Gwyn and they had a whispered conversation that made both of them smile, while I just sat quietly and sipped my wine. I was so far out of my element that I had to force myself to not turn around and stare at everyone. It was probably good that the only thing in front of me was the wall and two beautiful women who would not mind if I stared at them a little.

Gwyn and Amy finished their conversation and turned back to me. Amy was the first to speak.

"Turn around and look at the table across from us. Do you see the man in the uniform, sitting next to a woman in a leather dress? Look below them to the floor. Do you see the shoes sticking out from the bottom of the tablecloth?"

"That is where I want you right now. Under the tablecloth with your heels sticking out. I want you to please your wife with your tongue - no hands. Do you want that too?

"Absolutely" I responded.

Amy continued, "I picked out her outfit for tonight so that she could sit here and you could have easy access to her pussy from the floor right where you are sitting. I assumed I would see you tonight, and if you listen to me you may have the night of your life. Do you believe that I want you to have a great night, and that I have your interests at heart as well as my own?

"Yes, I actually do", I stated.

"Perfect. This evening you may refer to me as Mistress Amy, if you need to speak with me at all. Now, get on the floor and lick your wife to orgasm."

I pushed back the chair and got onto my hands and knees on the floor. I adjusted the tablecloth so that just my heels were showing, and moved in front of Gwyn as she spread her legs and pulled up her dress a little. She wasn't wearing any panties so there was nothing in the way as I dove between her legs and started kissing and licking her the best ways I knew how. She was already wet and I could sense that her breathing soon became a little more ragged. I'd been down on the floor for about ten minutes when I felt her first spasm and tasted the first rush of cum from her. I held my tongue on her clit as best I could through the heart of her orgasm, and then I could feel her pushing my head away from her. I was about to get out from under the table, when someone grabbed my ear to hold me in place. Gwyn sat up slowly and shifted her legs closed, and then the hand holding me dragged me gently to the left, and positioned me between Amy's legs.

My eyes widened as I was face to face with another woman's pussy for the first time since we were married. Amy had a different scent than Gwyn and her light coating of pubic hair was blond and neatly trimmed. Amy reached down and grabbed both sides of my head and pulled me towards her glistening slit. She shifted forward in her seat to give me better access to her, and although my head was spinning in all sorts of directions, I dove in action - kissing and licking her in the same way that I did for Gwyn. Amy shifted a little further forward and guided me towards her ass so I kissed and licked there. I'd been there for a few minutes when I felt a hand reach for me mouth. I took it in and wet it as best I could, and then the hand moved up to where Mistress Amy's clit would be and started playing and vibrating. I kept up my work on her ass while Gwyn played with her clit and dove her fingers into Amy's pussy. Soon Amy was clenching and cumming and she gushed all over my face. I'd never experienced anything like that before so it caught me off guard and I almost pulled away. Three hands simultaneously grabbed my head and pulled me back in between Amy's legs and I stuck my tongue out and rested there for a moment.

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