An Very Embarrassing Evening

This is a true story about something that happened to me, after, as many embarrassing stories do, having consumed way too much alcohol.

I'm a gay man in my mid-60s and both the characters in this story are well over the age of 18.

I'm posting this story in the "First Time" category in Literotica as it describes an incident that was very much a first for me. It could easily have been entered in the "Non-Consent/Reluctance" category, but I decided afterwards that, as I'd really had many opportunities to stop what happened, a description of my First Time is more appropriate.

There is no gay sex in this story.

I confessed this story to a close and long-standing work colleague of mine after he noticed one morning that I was not looking, or feeling, my usual chipper self. I swore him to secrecy and described to him the 'incident' that had left me hugely embarrassed and decidedly under the weather. He found the tale both funny and erotic and suggested I could share it more widely!

After a trip away for work, I had woken up after a night in a hotel where I had consumed way too much alcohol and couldn't believe what had happened the night before.

In my life, I can think of only two times when I've made a fool of myself by consuming too much alcohol and both times involved an excess of champagne! The first time was at an awards ceremony for work in the Waldorf Hotel in London and the second time was...

I was away from home for work and it was the first time in a while post the covid pandemic lockdowns. I was staying a couple of nights in a hotel and what happened was most out of character for me. I wouldn't normally drink heavily on a "school night" but it was one of those situations where everything was very relaxed - lubricated by way too much champagne - and it just happened as though it was natural and happened frequently. When in fact it was nothing but and a first (and probably last!).

The hotel was quite an up-market one. I'd arrived early evening and decided to go out for something to eat rather than stay in the hotel. Something I do not normally do as I hate eating out alone. I'd got back to the hotel around 9 o'clock, having already had a couple of beers with the meal, and decided as I wasn't yet tired and didn't have any work to do that night and that my first meeting the following morning wasn't until 10, to have a G&T in the bar.

I was the only person in the hotel bar, so I sat on a stool at the bar and was enjoying my drink whilst flipping through emails and other trivial stuff on my phone when I noticed, in the corner of my eye, someone else come into the bar.

She sat about a couple of seats along from me and ordered a glass of champagne. I don't normally pay much attention to other women, but I happened to glance up as she looked at me and smiled. I acknowledged the smile, but my head went back down to my phone.

After a while, I heard her order another glass and I looked up again. She looked about my age (60's), not overweight, but quite a big woman, very smartly dressed and prettily made up. She opened a conversation with; "do you mind if I ask you something?"

I replied, "sure, fire away".

"Are you gay?"

That's not a question I get very often and normally in public or with people I don't know well I wouldn't even acknowledge or answer it, but after a couple of beers and a large G&T and with no one around I was at least curious to learn why she even thought that, so replied.

"How can you tell?"

She explained that she thought that over the years with many other gay friends, both male and female, she'd developed a good gaydar and that she was rarely wrong! She explained that she was not gay but had a vast collection of friends, many of whom were gay or lesbian.

I didn't pursue that conversation further, but we got chatting about why we were there, and it turns out we had quite a lot in common and, before I knew it, we had been chatting about work and work-related matters for almost an hour. Her glass was empty, and I didn't really want to prolong the evening by offering to buy her another drink but when I returned from the loo, I discovered that she had taken the liberty of ordering another glass of champagne including one for me. I didn't know that she had ordered a bottle at the time.

The conversation continued, lubricated by the champagne and we were getting along famously -- we had so much in common -- at least through work.

We were still the only customers in the bar other than the bartender who was discreetly keeping out of hearing distance.

The conversation got a little more personal as we each enquired of each other about family. She was married, had kids that had left home, and it sounded as though she was more than happy with every aspect of her home life.

She then asked me the question that I hate, and wouldn't normally entertain with an answer "so, who's the man and who's the woman?". I hoped my facial expression would show her how distasteful I found the question, but she pushed further and as she was such a lovely woman, and we were having such an enjoyable evening I eventually did answer; "predominantly I'm top, my partner is bottom but very occasionally I've been known to switch", was my response.

The conversation continued for a while until we both decided to call it a night and head to our respective rooms. Remember I'd had a couple of bottles of beer, a large G&T and half a bottle of champagne by this time. I'd no idea how much she had drunk but it was at least half a bottle of champagne -- possibly more.

We made our way up to rooms discovering we were both on the same floor. As we walked/staggered along the corridor, we got to her room first...

All the way up from the bar to our rooms we continued our conversation, mainly about work, IT, and technology. It just seemed like we'd known each other for ages, had so much in common and the chat flowed easily.

At her room door, she thanked me for a lovely evening and for helping to pass the time. I said similar and said normally I hate evenings like this - alone and away from home. As I said good night and turned to head along the corridor, she surprised me by saying she still had a half-opened bottle of champagne in her room that needed finishing off!

I replied quickly saying no thanks. It's getting late and we've both got work in the morning. Whilst saying that I glanced at my watch, which she noted and said, "see it's not even midnight, and besides, you said yourself that your first meeting tomorrow wasn't until 10 am".

Desperately trying to think of excuses to get out of it I said, "what would your husband say, inviting strange men back to your room for drinks?"

For a weird moment, as she opened the door and I saw the light and TV on, I thought she was going to say it's okay he's here, but my mind was off on completely the wrong track!

"What's he got to worry about? What harm can come from work chat about IT between a gay man and a married woman? Come on, one glass each should empty the bottle."

I gave in.

Once in the room she switched off the TV and went to pour the champagne. It was a typical hotel room with only one chair beside a desk, so I sat on the bed, and she sat at the desk.

We picked up and continued the conversation from before until nearing the end of the glass she took the conversation back to the "who's the man and who's the woman in your relationship" question. I tried to explain, unsuccessfully to her why I thought that question was offensive. But it continued with a discussion about sex in the early stages of a relationship and how much it changed as the relationship lengthens and matures. I wasn't sure where this was heading or if she was steering it in a particular way but again, we found common ground; she had much more oral than penetrative sex now and thinking of my own relationship that was probably true too.

She said that her husband now preferred fellatio and she boasted about how good she was, or rather how good he told her she was.

Stupidly (with hindsight) I asked her if she knew if he'd ever had a blow job from a man? She quite angrily answered that he'd never been with a man in his life and anyway why do you ask, to which I replied "it's my view that only a man can give another man the best blow job. A man knows how it feels, where to focus, when to go slow, speed up. It stands to reason he would always create the better sensations."

As the conversation continued, I realised that I'd said the wrong thing to a woman who was so dominant, in charge and competitive.

I finished my glass and got up to leave but it was obvious she didn't consider the discussion finished.

Things were still very amicable between us when she said, "I'll bet you that unopened bottle of Dom Perignon there that I can give you a better blow job than your husband can?" WTF!

My response was that I'm a gay man I doubt you'd even get me hard! Well, that was a red rag to a bull!

This is where it all gets very embarrassing, and I know in this age of consent and 'no means no' this should never have happened but before I knew she had pushed me back on the bed and was unbuttoning my trousers. "I'll prove you so wrong."

Thinking this over many times afterwards I still don't know why I didn't stop her. Was it the drink? Did I want it? Did I want to prove her wrong? I'll never know.

As she cupped my groin, she said, "see he's hard already" to which I responded, "'fraid not that's just little old me" (I was wearing tight briefs that cupped and emphasized my junk).

She soon had my trousers and briefs down around my thighs and my -- completely flaccid -- cock in her mouth. She was working her tongue around it big style and to my horror, after a while, I did start to harden.

"See I told you so!" as she continued to work my penis in her mouth.

I tried everything to think of other mundane things to take my mind off what was happening.

She went at it for what seemed like ages until -- success! I started to go limp. She said that must be the drink. I went to say "no, it's because you're not very good and I'm gay" but stopped myself and said, "yes, sorry". I'm too nice!

So, there I am lying on my back on the bed, feet on the floor, trousers at my knees with this woman I only met a few hours ago on her knees in between my legs, when she says, "so do you also believe then that only a woman can give another woman the best cunnilingus?"

At that, I dug another hole for myself when I said, "I have no idea but I guess that must be true. I wouldn't know because the only time my mouth has been near a vagina would have been at birth!"

Before I knew it, she was up on the bed, knees on either side of my head and I was staring up at a completely hairless pussy. "let's sort that! Get licking."

This is where the night for me turned into a nightmare. I was clueless. Obviously, I knew where my tongue should be but after a short period of licking and exploring it was obvious that I wasn't doing it right for her as she started to use my nose to rub her clitoris and increase the excitement. I just lay there frozen and let her get on with it. She started moaning so loudly that eventually there were thumps on the wall followed by shouts coming from the room next door to keep the noise down, I'm trying to sleep!

I've no idea if she finished or if that put her off but she removed herself, flopping down on the bed beside me saying "a woman has never touched me there, so I'll never know if that's true."

I lay there not knowing what to do next. She spoke first. "I don't think you can claim the bottle of Dom Perignon but thanks for a very entertaining night".

I made myself decent and rather sheepishly made my way back to my room and ordered room service breakfast so I would never see her again!

I've put the evening down to experience and moved on. I'll also never go back to that particular hotel even though I will have to go back to that city for work.

I'll also never touch champagne again (not sure I can keep that promise though).

Malcy