Tuxedo Shopping

By moc.duolci@026.slohcinottik

Published on Dec 30, 2024

Transgender

Rita and I arrived in New York City around 4 in the afternoon. She directed me to go to the Plaza Hotel, so that we could get checked in and call a car service from there. We pulled up to the Plaza, a valet let Rita out and I popped the trunk for the bell hop to grab our bags. I handed the valet my key fob and he handed me my ticket, got in and drove my car away to park.

The bell hop with our bags, escorted us in, to the front desk to check in. The door man graciously nodded to me when he opened the door to let us in. We got to the front desk and the hotel concierge was waiting, as we got there.

`Reservation for, sir?' She asked warmly.

Rita answered before I could say anything, `Felix Zimmer, for two, we booked a suite over looking the park.'

The concierge smiled, typed and said, Ah, yes here you are Mr. Zimmer, may I get your card that you used to make the reservation with.' I nodded, got my wallet from my jacket pocket and found my American Express Platinum card and handed it to her. Thank you, may I say you to look lovely. Ready for a night on the town?'

I nodded and Rita replied, `yes darling and may you call a car service for us to be here in a half hour or so, to meet us out in front. I think we would like to get freshened up a little, after our drive up from the Capitol.'

`Indeed Mrs. Zimmer.' Neither Rita or I cared to even correct her assumption. As Rita said, we wanted to get checked in and get freshened up after our drive. I hadn't gotten a chance to shower this morning before I went to Rita's and I didn't get to after our play session, so I probably smelled of sex; even with my new clothes on.

The young lady handed me my credit card and our room key. We followed the bell hop to the elevators, the doors opened and he let us go in ahead. He pressed the button for our floor, the doors closed and up we went. The bell hop made idle chit chat while we rode up to our floor, without any notion that Rita had a firm grasp on my ass and was massaging it as we went.

The elevator stopped at our floor, he cleared his throat and said. `Here we are sir and madame.' We stepped out into the hall and Rita slipped her arm under mine as we followed him to our room. We got to the door I unlooked it, had him put our bags down and gave him a tip and he exited our room.

I looked at Rita and said, `So I take it at some point you took my card out of my wallet to make this all happen?'

Rita smile, `What was that Boy, I don't think I heard you, properly!'

I got the picture, `Mistress Rita did you use my card for all of this?'

She kissed me on the forehead, nodded and winked while walking to the bed. She kicked off her heals and laid back onto the bed. `Ahh, this is luxury!'

I grinned and said, `yes, yes it is, I am glad that I am able to afford such things. I need a quick shower, I probably smell of cum and sweat. Mistress may you assist me getting out of my clothes?' She laughed at me but got up and helped me out of my clothing, stripping me all the way until I was stark naked. She slapped my ass, as I walked towards the bathroom, first thing I did was use the toilet, it had been a bit since I had peed, last; flush and the water went down.

I got into the shower after adjusting everything to get the water, just right. The hot water felt so good as it sprayed and ran down my body. I heard Rita come into the bathroom and open the toilet lid, I noticed her sit down and heard her start to relieve herself; I wasn't the only one in need of a tinkle.

Once she flushed, I said, `Mistress Rita, may you please get my dopp kit from my bag? I would like to shave once I get out and it has all my other toiletries in it, thank you!' She didn't respond but I heard her walk out and come back in a minute later.

Rita said, `your kit is on the counter darling, I hope you are enjoying your shower. By the way there is another gift for you, waiting inside your kit.'

I turned off the shower, stepped out, grabbed a towel and began to dry off. Noticing the robes hanging there I put one on and went to the lavatory to put on deodorant and shave, I could feel the stubble. I opened my kit and on top was a strange object, not sure what it was, I just set it aside and went to work shaving and getting ready.

After I was finished, feeling and smelling much better, I grabbed the object and took it out to the room with me. I said, `may I ask what is this, Mistress Rita?'

She beamed, oh that, that Boy, is your new vibrating butt plug. Come over here and I will help you get it in.' I walked to her and placed it in her waiting hand. Turn around,' she slid the robe up my back, patting my ass whilst she did, I felt a bit of pressure on my asshole as she slid the toy into me.

Letting the robe back down, she said, slyly, `now, anytime you are disobedient or vex me in any way, you will feel, this.' She pushed a button on a small remote and I felt the anal toy start to vibrate, it sent shivers up my spine but felt amazing. My cock pressed against its cage but found it couldn't rise further; that was another new feeling, confinement, it was a bit uncomfortable but I figured that I would get use to it.

Rita smiled as she had noticed the wince on my face, she turned off the vibe and said, `I am going to freshen up my makeup, get dressed, let me know when you need help. The front desk should be calling anytime to let us know that our car is waiting.' She was walking toward the bathroom with a makeup bag as she finished her sentence.

I took off the robe, laid it across the bed and started to get dressed back up in my new tuxedo. I put on my boxers, pants, socks, shoes and pulled the tee over my body. I noticed that the boxers and tee were both fresh and clean, as were the socks. I grabbed the robe and took it into the bathroom to hang up. Rita smiled at me in the mirror and I hung the robe on the hook and I bent down and grabbed my towel to hang up as I had let it drop on the floor once I had dried off.

I turned to Rita and said, `I am ready for your help, if it pleases you, Mistress?'

Rita nodded and said, `Just about finished and I am done, meet me out there.' As I walked out our room phone buzzed, it was the front desk, letting me know the car had just arrived. I placed the phone back down in its cradle, as Rita came behind patting my bottom and licking my ear.

`Was that the front desk?' She queried as she started to help me finish dressing. I nodded as she grabbed my dress shirt and slid a sleeve up my arm. She had helped me get all buttoned up and my tie retied and I put on my vest and jacket. I grabbed the room key, putting it in my pocket, double checked my jacket pocket to ensure my wallet was there and grabbed Rita under her arm and escorted her to the door and down the hall to the elevators.

Being alone this time, in the elevator, Rita and I made out a little but not hard enough to mess with her makeup. Though when the elevator stopped she rubbed my lip, I probably had a bit of lipstick transferred.

We walked to the door and out to the waiting town car, the door man nodding again, as the valet opened the rear passenger door for Rita. I held her hand and let her in, I walked to the driver side rear door and got in as the valet closed the door for her.

`Where to sir,' asked the driver?

Rita stopped me from answering and gave him the name of a cocktail lounge in Manhattan and a restaurant that we had a dinner reservation for. He smiled and merged into traffic. Rita with her legs crossed, had her hand on my knee while we rode through the city, in style.

We arrived at our first destination, the driver got out and let me out and I went around and took Rita by the hand to let her out. The driver handed me a card with his number on it, so I could call when we were ready to go to for our dinner reservation.

We walked into the bar, it was very nice, the man at the door checked our id's before allowing us in further. There was soft piano music playing and I saw a baby grand piano on a small stage with someone at the keyboard playing away. We walked to the bar, ordered our drinks and went to a table close to the stage.

I pulled a chair out for Rita, she sat and I gently pushed her in. I sat down and our drink order arrived, just as we got settled. The waitress said, `I am Hannah and I will be your server this evening, please let me know if you need anything. By the way, you two make a gorgeous couple!' We both smiled and nodded in thanks. Rita had a dirty martini and I had my usual Seven and 7, we toasted and sipped as we listened to the music.

We enjoyed our drinks and ordered another round. While we were waiting for our next round to come, Rita grabbed my hand to check my watch. She told me that I should pay the check once we got our drinks, our reservation for dinner was fast approaching.

When Hannah came back with our order, I asked, `may I get our check please?' Hannah smiled and handed me our bill, I smiled politely back as I hand it back to her with my card.

I will be right back with your card sir,' Hannah said as she walked to the bar to close out our tab. A few minutes later she handed me the bill to sign and I put my card back into my wallet. I took out a twenty before putting my wallet back in my jacket pocket and handed it to Hannah with the signed bill. She beamed and said, thank you, you two have a good night.'

I looked at Rita as Hannah walked away and said, `should I call the car, to meet us out front?'

Rita sipped her drink and said, `not yet, let's finish our drinks darling.' She smiled slyly, her drink in one hand and her other hand on my knee. I felt her hand leave my knee a moment and then felt my ass vibrate, I started up, then relaxed. She smiled again, then chuckled a little, I laughed a bit and smiled back.

We finished off our drinks and I called our driver, so he could meet us at the entrance. I stood and helped Rita from her chair and she placed her arm in mine and we walked to the door, the door man opened the door for us and our driver was waiting, he got out and opened the door for Rita. This time she slid over as I helped her in and I slid in beside her, the driver closed the door behind us, got in and signaled to merge into traffic.

It was around seven when we arrived at the restaurant. It was very nice and had a covered drive, for the driver to pull up to, to let us out. He opened my door and I got out and went around for Rita, she gabbed my hand and stood. The driver and I closed the doors in sync and he again let me know to call when we were ready and he went to park.

We walked to the door and I opened the heavy door for Rita. The man at the reservation table asked for the name and I gave it to him. He called for a hostess to escort us to our table, she smiled at us and we followed her.

The hostess said, I hope this table works for you.' I nodded and smiled as I helped Rita sit in her seat. The hostess replied, your server tonight will be Stephan and will be with you momentarily, may I start you off with water and a cocktail?'

Rita said, `please bring us some sparkling water and I will have a Manhattan and he will have a Seven and 7.' The hostess smiled, nodded and walked away to give our order to the bartender. A few minutes later our drinks came.

The server said, I am Stephan, I will be serving you tonight.' As he placed our drinks on the table, Rita took a sip of sparkling water, once he had poured a glass, I did as well. I will give you two a minute to look at the menu, just put a hand up, when you are ready to order.' I nodded and took another sip of water, as he walked away with the drink tray.

Rita and I busied ourselves looking over the menu, I was famished, as I hadn't eaten a thing all day besides the coffee I had at Rita's shop and her load of girl cum. We decided to order a sample plate to for an appetizer and both found entrees to our liking.

I raised my hand and Stephan came back, pad in hand, ready for us, Rita said, `we will try the sample plate for starters, he would like a steak, rare with a side salad and baked potato and I will take the surf 'n turf also with a side salad and baked potato, my steak rare too.' Rita too, was obviously as hungry as I was.

Anything else,' Stephan asked? We both shook our heads no and he said, okay I will get your orders in and have your hors d'oeuvres out shortly. He walked away to the kitchen. I took a drink and excused myself, to the bathroom. I got up and walked to the restrooms, I went to a stall closed the door and relieved myself in the toilet. As I peed I felt my asshole vibrate and I heard a familiar chuckle outside the stall, I hadn't noticed that Rita had followed me.

She opened the stall I was in and told me not to flush, she put the seat down, dropped her thong and hovered. I heard her pee splash into the bowl as I did up my trousers. I saw the familiar look of relief come over her face. She pulled her thong back up, as she stood and flushed. We walked to the sinks and washed our hands.

Once we had dried our hands Rita grabbed me, as she leaned against the counter, time to give your Mistress a blow job before dinner.' She saw the look in my eye and said, don't worry Boy, I locked the door on my way in, no one will disturb us.'

I got on my knees, lifted her skirt and pulled her thong aside, she was already hard. I could still taste her pee from using the toilet. I licked her up and down like a lollipop and she grabbed me by my ears as I started sucking her. She pushed my head down and her soft ball sack hit my chin and she was deep in my throat.

It took no time with me bobbing and she shot her load into my mouth. I sucked her dry, moved her thong back into place and let her skirt back down. She pulled me close and kissed me and licked what little cum of hers was left on my lips.

She patted my ass and said, `good boy, unlock the door and let's go eat, I am starving!'

As we made our way back to the table we noticed that our drinks had been freshened up and our water refilled. I sat Rita down and then took my seat, just as Stephan brought us out or appetizers. I nodded in thanks and he took his leave. I served Rita first and then made a small plate for myself, we toasted, took a drink and started to eat.

Hi, I am Kit, if you are enjoying my series, please help the archive and donate, thank you. https://donate.nifty.org/

Next: Chapter 7


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