Hotel Rendezvous - Cover

Hotel Rendezvous

by tiffany58

Copyright© 2024 by tiffany58

Erotica Sex Story: I was inspired by the opening premise of Oliver Twist’s excellent “My double life as a whore,” where a surprise meeting in a hotel bar leads to many other things, to recount my own true story of my recent hotel bar adventure.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma   Consensual   Romantic   Gay   CrossDressing   True Story   Anal Sex   Analingus   Enema   Exhibitionism   Oral Sex   Public Sex   .

It was about 4.00pm when I left the tall glass tower block in central Manchester, a smile on my face and my stomach turning over with hopeful excitement, and skipped, almost girly-like, down the street.

I had just completed a very profitable meeting and had come out with a contract for some ongoing work for a new client who needed the support of the advertising agency I jointly owned with my business partner. It meant that I would be in Manchester at least once every week for the foreseeable future, which was another reason for my girlish glee. I had a hot date that night with a guy I hoped might become more than just a one-off meeting.

As I walked briskly back to my hotel, just off the main gay area of central Manchester, I thought about my planned rendezvous this evening. I had been talking for some time to an attractive man called Shane, who I had met on Tvchix, and tonight was our first opportunity to meet in real life, not just virtually. We had met on video several times and I had seen his naked body and solid looking penis, and he had seen me in my best lingerie and stockings. He was coming to my hotel for 7.30 and would come directly to my room once I sent him the room number. I was excited, and also aroused, as I had not had a proper relationship for at least a year and my last sexual experience had been a couple of months ago with an old friend who I see occasionally.

I rushed back to the hotel, where I had checked in before going to my meeting, and impatiently rode the slow elevator up to the third floor, where my room was at the end of the corridor. Once inside I rapidly stripped off all my work clothes, took my hair out of the bun that I kept it tied up in when working, and began to lay out my clothes for my romantic evening. New black lingerie with matching half cup bra, small thong, and deep waisted suspender belt with six straps, all in a combination of silk and lace, and paired the set with a new pair of Wolford black stockings. I laid my little black cocktail dress on the bed which, when worn, came to mid-thigh and fell just below my stocking tops. Finally, I put my four-inch heeled stilettos on the floor next to the bed.

Next, I took my toiletries and make up bag into the bathroom and, for the next hour or so, prepared my hair and body to impress my online admirer. I removed any minor traces of hair that had appeared below my head, gave myself a couple of thorough enemas in hope that I would be using that point of entry at some point this evening, and, after a long slow shower with lots of delicious smelling gel, used my hair dryer and straightening tongs to shape my natural brunette hair into its shoulder-length bob – my usual hairstyle when trying to impress.

Finally, I applied my make-up – foundation and rouge first, then eye shadow and mascara to my lashes, before finally applying a dark red lipstick that I know complements my black dress and heels. The preparation work was done and Tiffany was nearly ready for her visitor! Only my clothes to go on now and I would be ready, just about on time for his arrival.

I slipped the bra on to cover my natural A-cup breasts and already hard nipples, stepped into my little thong and adjusted it to sit comfortably, before fixing the suspender belt around my hips and lower stomach, the straps inside my thong. The last items to go on were the new silky black stockings. I lifted my foot on to the bed, slid the silk up my legs to my thighs, and fixed the clasps to the stocking tops, the six straps making sure that both were firmly fixed and should not slip whatever may happen tonight.

I then stepped into my dress, struggling as always to pull up the zip that sat between my shoulder blades behind my back. It was a delightful straight cut dress, with no sleeves and a V-neck that enhanced my small breasts, and it clung to my hips and bottom. It was, as I had hoped, about mid-thigh in length, and sat just below my stocking tops, although nothing was revealed unless I forgetfully bent over with straight legs – maybe I might do that later! By 7.10 pm I was almost ready, with just my jewellery to put on – a pearl bracelet, a simple pearl necklace and matching pearl stud earrings that I slid into my ears and applied the small screw to hold them in place. Now I was definitely ready! I sent him a WhatsApp to tell him the number of my room and waited for the knock on my door.

By 7.40 there had been no knock at my door and by 7.45 there had still been no word from him. I was getting annoyed and frustrated so sent him another message asking if he was alright and when would he be arriving? Finally, just before 8.00pm, my phone beeped and there was a reply from him – it merely said, “Sorry, can’t make it – another time maybe.” I was furious and deeply frustrated – I had spent hours preparing myself for him, not to mention the money I had spent on clothes and undies, and more to the point I was now left all dressed up and nowhere to go!

I let myself calm down and was thinking about taking my clothes off and removing my make up when I had a much more positive thought. When staying in hotels I rarely go to the bar because it is always a bit of a meat market with lone men staring at you, but tonight I needed a drink and not just a miniature out of the mini bar. So, I grabbed my small clutch bag, with room key and money in it, and decided to go down to the bar that I had seen just off the lobby when I checked in earlier. A s my room door clicked behind me, I suddenly felt nervous. I had not done this before and felt a mix of excitement and trepidation. Would anybody say anything to me? Would I be ogled or ignored? It seemed an endless walk to the elevator but just as I reached out to press the call button, the door opened and a man stepped out with a small trolley case and a brief case. He was tall, about late fifties in age, and nicely attractive. He smiled at me and said good evening as he held the doors open for me. I smiled back at him and then stepped in. I pressed the button for the lobby, taking a deep breath as I did so, and rode down in the slowly descending box, musing over the nice man who I had just met.

As the elevator ground to halt and the doors slowly opened, I walked out into the lobby, pretending to be much more confident than I was really feeling. I looked around and saw the entrance to the bar, a narrow, poorly-lit space, with the bar and stools on one side and small tables and chairs on the other. I walked in and made my way to the far end of the bar without looking to either side, and then slid my tightly-clad bottom on to the last stool.

As I crossed my legs and rested one foot on the footrest, I took my first look around the bar. Most of the little table were occupied by single men of all ages – there were probably ten or so there, all trying hard not to be seen looking at my stocking-sheathed legs. The bar man wandered over to me and asked what I would like. “A large gin and tonic with lots of ice and lemon please” I quietly replied.

I tried to ignore the eyes boring into my back as I waited for my drink to be served, and carefully uncrossed my legs to put both feet on the footrest, knees closely together, so I was less conscious of them staring at my thigh. The barman brought my drink to me and, with a leering smile, said “You have caused a stir in here tonight – they do not usually get anyone as attractive as you to stare at.” I gave a shy smile and thanked him before pretending to look at my phone to let him know I did not want to chat.

After about ten minutes I was suddenly conscious of someone standing beside me and a deep voice saying “Hi, I am glad I found you here.” I looked up and found the guy from the elevator looming over me. A quick glance told me he was tall, about 6-3, wavy grey hair, looking confident, sophisticated, and wealthy, mature, and decidedly sexy! I admit I have always had a thing about older men, ever since I lost my teenage virginity to a man 30 years older than me, at a time when I was still discovering who and what I was. He was one of my university professors in my first year and was supposed to be giving me extra tuition which he certainly did. After some tentative shy kissing which developed into enthusiastic groping and fondling, it culminated in him taking me over the back of his old leather sofa, and my love of mature men lasted ever after.

I pretended not to recognise him until he said “We nearly bumped into each other upstairs.” I smiled at him and said “Of course, nice to meet you too.” “I was hoping you would be down here – I wanted a chance to say hallo properly. Do you mind if I join you? I am John Taylor by the way” he said as he sat on the stool beside me, not waiting for an invitation to sit. “I am Tiffany Woods,” I shyly replied. “Well Tiffany, can I get you another drink?” he asked, before turning to the barman and saying “Two more gin and tonics, please” before I even had a chance to reply. The barman gave me a knowing smirk and simply said “Lots of ice and lemon again?”

“So, what brings you here, business or pleasure?” my mature companion asked, giving me a beautiful but cheeky smile as he said it. “It was supposed to be both” I replied with a pretend sad look on my face. “Oh, do tell me all about it,” he grinned.

I started by telling him about my successful business meeting and my hope that I would be visiting Manchester frequently in the future, to which he replied that he too came here at least a couple of times a month so hopefully we might see a lot more of each other. It turned out he was a Chartered Accountant and a senior partner in one of the big firms, and he had a major client in the city centre.

“That’s the business bit done, now tell me why the sad face on the pleasure front?” I could not help laughing and so told him about my hot date that had stood me up 30 minutes after we were supposed to be meeting. “My god, the man must be a complete idiot standing up a gorgeous thing like you,” he exclaimed, waving his hand in the air as he said it, before bringing his large hand down to pat me on my knee. Perhaps because I did not move or say anything he just left his hand sitting there on my knee and lower thigh, just occasionally giving the gentlest of squeezes to it.

Over the next thirty minutes or so we chatted about everything as we got to know each other. Much to my secret delight it turned out he was 58, divorced for ten years, no kids and a full partner in his firm (so rich!) I was enjoying the conversation so much that I did not really notice or, if I did, I was enjoying that too much as well, that his hand had left my knee and was now resting on my thigh, well above the hem of my dress. His index finger was gently caressing the suspender clip that was immediately under the dress at that point.

We stopped chatting for a minute and simply sat there sipping our drinks, until I looked down at his hand on my thigh and his big finger circling the bump in my dress. We looked at each other and both smiled as he said “I love the feel of suspenders on a beautiful thigh.” “I wear them all the time – I love them” I whispered as I felt his hand pressing more firmly on my thigh. He began to stroke my leg from knee to suspender and, at some point, his hand went under my dress and stroked silky stocking clad thigh.

Gradually his hand moved from top of thigh to the inside and with no real pressure eased my knees apart so his hand could stroke the inside of my thigh, gradually resuming its slow slide up my stocking until it reached the first suspender clip. As he continued to stroke my bare flesh above my stocking top, I caught the eye of the barman casually leaning against the bar, watching every move, and once more giving me a sly smirk. I was breathing deeply by now and became conscious of several of the men sitting in the bar also watching the hand gently moving under my dress. I leaned towards my man John and said “We are being watched” to which he simply replied “I know - would you like to go for a walk and maybe a drink somewhere else?” I nodded and he removed his hand.

As we both stood up, I straightened my dress and hoped that there were no visible signs of my arousal. We walked through the bar to the reception area, his hand resting on my hip and all male eyes on me, and with me giving a girlish finger-wiggle wave goodbye to the barman who blew me a kiss in return. As we left the hotel John told me the Manchester gay quarter was literally just round the corner, and suggested it might be fun to go to a bar there, which I was happy to agree to. We walked arm in arm into a street full of bars and restaurants, with me explaining I did not usually walk in the street in my high heels so needed his arm to make sure I did not stumble. He laughed and slipped his arm round my waist, pulled me close and told me he would make sure I did not fall!

 
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