Not Everything Was As It Seemed

Unique sexual experiences can be the most fun

I’m one of those people who is incredibly open to new possibilities and seeing where the adventure of life takes me, so when combined with the volume of travel I’ve done, it’s obvious that I’ve had more than my share of fun and unusual experiences.

As I previously mentioned, my superpower is listening to women and being very empathetic… plus I love sex.

You can see how this has probably played out over the years.

Traveling Regularly is Isolating

An interesting fact about me, I don’t drink alcohol, but I love hotel bars.

In large international cities, the bars at five-star hotels are like this nexus of interesting, lonely people who are just looking to find someone to talk to and share their story.

Without a doubt, some of the most enlightening and deep conversations I’ve ever had in my life have occurred with random people I’ve met at 11pm in a hotel bar overlooking some major metropolis.

People who travel internationally on a regular basis tend to be stoic for the most part, but there’s also something about them that’s a bit lonely.

Humans need to share their stories and communicate with each other, and for international travelers, that can be incredibly difficult.

Here’s an oddity: the loneliest people I’ve ever met in my life are airline attendants.

You’d think that being on long haul flights and talking to all these people would be the opposite, but I once had a lady tell me that she battled severe depression because her job basically consisted of her being a maid and waitress while making small talk with people she didn’t know.

She and I had really aggressive sex that evening after she mentioned that.

I have had sex with a lot of airline attendants over the years, but that’s a story for another time.

One Night In Singapore

This one time I was sitting in the bar atop one of the great highrise hotels in Singapore where I was staying for a couple of days for work.

It was early evening, my dinner consisted of a Chicken BLT that I ate a table in the bar while watching CNBC Asia without sound.

This incredible blonde woman walked into the bar in a very tight dress, sat at a table a few feet away from me, pulled out her phone and started typing away.

I have to be honest, I thought for sure that she was “working”, so after I subtly stared at her as she made her way to the seat, I turned my attention back to my sandwich and CNBC Asia because the Hang Seng was taking a beating which was important for my meeting the next day.

After a few minutes, this tall, lithe blonde lady was standing next to me, staring down.

I was pretty certain at this point she was “working” and I thought she was coming over to the lonely guy who was watching the muted financial news and eating a sandwich to make her pitch by offering some “companionship.”

She said in a very posh English accent, “I’m starving, that sandwich looks great, how is it?”

“It’s pretty good for hotel bar food. At least the chicken is tender.”

She thanked me, said that helped make her mind up about dinner, and she sashayed back to her table.

I again watched her nice, round little ass make it’s way back to her table. I turned my gaze back to the TV before she sat down and noticed I was staring, I couldn’t help wonder if she was trying to pitch me for “services” or not.

Taking Your Shot

After a few minutes, her own Chicken BLT came out along with a glass of red wine and she tucked into her sandwich while tapping away at her phone.

My brain was having trouble processing what had gone on — she essentially only wanted sandwich advice, but I guess she was also just another traveler looking for some kind of verbal communication with another person.

I continued to watch the panel discussion on CNBC Asia (they looked they were discussing ghost towns in China) but kept an eye on my blonde fellow traveler.

She was scrolling through Instagram, had gotten through a few fries and half her sandwich when she hit the bottom of her wine glass.

This was my chance.

I called the waiter over, ordered myself sparkling water and told him to refill the lady’s glass on my tab.

A few minutes later, another glass of wine appeared at her table, she discussed something with the waiter, smiled at me, raised her glass (I did the same) and took a mouthful.

Then… nothing.

She went back to Instagram and eating her sandwich while I decided to pull out my iPad and see what craziness was taking place on Twitter.

I lost track of time and hadn’t noticed, but my blonde friend had made her way over, wine glass in hand and was standing next to my table.

“Please, have a seat,” I said in my most friendly voice.

My gamble had paid off!

Getting To Know People Quickly

In situations like this where I’ve met someone, I’m keen to see where it goes and time is of the essence, so I turn my attention to detail up as high as it can go so that I collect all of the snippets information the other person is dropping in casual conversation.

Having said that, there was nothing that would prepare me for what I would later come to learn… But we’ll get to that.

Her name was Brianne, she was a corporate trainer for a large investment bank and she was in Singapore for a couple of days to do some training for staff in the local branch.

She told me she traveled a lot, three weeks out of the month, but because she was single and had no kids or commitments, it was easy for her at this point in her life.

Immediately, my mind started pulling a picture together because this early 30’s stunning woman wasn’t married, had no significant relationship, no kids, and traveled a lot, I needed to understand more.

I explained that I traveled a lot as well and asked her if she found the entire experience very isolating and lonely.

“I like being alone right now, I’m learning a lot about myself and this phase of my life.”

That was like gold to someone like me because I could ask several deeper questions to learn more about her so that I could understand her better.

I asked what was the thing she discovered about herself that made her the proudest of who she was.

That question caused her eyes to light up with an intense sparkle that I’d not seen before and she smiled as she told me how she realized how brave and resilient she was as a person.

That sparkle was the sign that she was now interested in me and we’d made a connection… The next three hours flew by.

Dealing With The Unexpected

It was approaching midnight and we were still talking. Brianne was an excellent conversationalist — she clearly dealt with a lot of people, so she’d learned the art of small talk.

I figured that it was probably too late for this to go anywhere, so I was happy to keep talking until she had to go to her room and sleep.

As mentioned, I have a rule about never making the first advance and Brianne was friendly, but not really “flirty”.

To my surprise at about ten past twelve, she said, “I noticed you are not drinking, so I wasn’t sure how to ask you if you wanted to come to my room for a drink without it sounding weird.”

Well, that was unexpected at this point.

I laughed and we made our way up to her room.

Interestingly, my room was better and I offered her the chance to go there, but she said hers was fine. I just assumed she felt more comfortable in her room, so I didn’t push it.

As we entered her room, she put the security latch on the door, turned around and kissed me deeply.

Brianne was strong and she probed my mouth firmly with her tongue.

It didn’t take but a second for my penis to firm up and she could feel it pressing against her.

She smiled, dropped to her knees, unbuckled my pants and took my cock into her mouth fully.

This was obviously not the first time Brianne had done this activity because she was very, VERY good at it.

If we’re being honest, I’m not a massive fan of blow jobs — I like them, it feels good, but for the most part, it’s just foreplay for me and normally, it’s not something that leads to an orgasm.

Except this time… Brianne knew what she was doing.

I felt wave after wave of pleasure as I came in her mouth — it doesn’t happen often, but when it does, it’s intense for me. My knees were literally weak.

After I had finished, Brianne stood up, kissed my cheek and told me to go get comfortable in the bed.

She went to the bathroom, dimmed the lights and had a drink of water before coming back out in nothing but a pair of silk black panties.

I had removed the rest of my clothes, collected myself and slipped into her bed under the sheets.

Sometimes Things Go Off Track

Brianne slid into bed with me, we kissed some more (she’d brushed her teeth which was a nice touch) and we rubbed up against each other.

I ran my hands over her C-cup breasts and could sense that they weren’t real, but that didn’t matter to me as I took the nipples into my mouth firmly and tongued around the areola.

Brianne’s back arched as I suckled and played with her nipples, she was enjoying it a great deal.

I slid my hand onto her stomach and started to make my way down feeling for the edge of her panties so I could slip my hand inside and explore her body more fully.

She grabbed my hand and said, “Stop for a second.”

She reached down with her free hand, lowered her panties and then gently and slowly slid my hand down over her naked pubis.

Then suddenly, I had a semi-erect penis in my hand.

Yes, Brianne was a trans-woman.

I was… surprised… For a few moments, I sat there holding Brianne’s penis.

And there was silence for what seemed like an eternity, but maybe was only five or six seconds.

I looked up at her, removing her nipple from my mouth, “That was unexpected.”

She went from having a look of slight concern to laughing out loud.

I slid back up the bed, laid on my back and laughed with her.

Brianne was apologizing and explaining that she had a few too many wines, normally she’s pretty upfront about her gender, but she really enjoyed my company and had gotten a bit carried away.

Where Do You Go From There?

I told her to not to be silly and to stop apologizing.

I even said, “Hey look, no harm, no foul” which was odd and not quite fitting the circumstance.

This made us both laugh even more.

Then Brianne leaned over to give me a peck on the cheek but I turned into it and it became a kiss on the lips… Which lingered to more deep kissing.

She started running her hands over me, I was feeling her body which was soft and smooth, while steering clear of her cock and balls.

Within a couple of seconds, she could feel my returning erection and she slid down under the sheets to do that magic with her mouth again.

In amongst thinking that she was easily one of the top two or three women I’ve ever encountered for blow jobs, I started having all of these cliches running through my brain…

“In for a penny, in for a pound. If you’re going to be a bear, be a grizzly.”

Brianne stopped and slid back up, “You seem like you’re still keen.”

I kissed her hard and she reached over into her night bag beside the bed, pulled out some condoms and lube.

She rolled a condom on, lubed us both up, and she mounted me.

She rode me for what seemed like hours, slowly and methodically and she told me that everything was perfectly lined up and rubbing against her prostate.

After a while, I couldn’t hold back and I came for a second time — I pulled her hips down as I thrusted up. I’d forgotten I was in her ass rather than a woman’s vagina and that it might have been a bit too hard and far, but afterward, when I mentioned it, she said it felt great.

May As Well Go With It

As I was recovering, she asked me if I’d ever “done anything like this before”.

I told her that I’d been in some MMF threesomes but never anything with a transwoman before. I also told her I’d done anal a fair bit with biological women but had never topped a biological man.

She asked me how I felt about it and what changed my mind.

My answer was simple, “We were having a good time, you’re incredibly attractive and I figured we were having fun, so why not just go with it.”

She laid back on her pillow with a big smile and said she was happy that I did because she’d had two amazing prostate orgasms.

We both started laughing — it was kind of one of those tension breaker laughs.

As we talked for a bit, the bedsheet was low and her breasts were just sitting there and I started getting excited again.

I was still in a “may as well go for it” kind of mood, so I leaned in, kissed her and slid my hand down onto her semi-flaccid cock.

I had never touched another person’s penis in a sexual way before, I really had no idea what I was doing, so I decided to pretend like it was my own and rub it the way I liked mine rubbed.

This surprised Brianne, as she pulled out of the kiss, leaned her head back and said, “Are you sure?”

I kissed her again and felt her smoothly shaven balls as well as her slightly growing penis.

I made my way down and sucked her tits and nipples while I gave her my attempt at a handjob, which she seemed to be appreciating from the sounds she was making.

Going Where This Man Had Never Been Before

I certainly wasn’t game to give her a blow job or bottom for her, but a handjob while sucking her tits was certainly something I was able to do.

After a few minutes, I started getting another erection and it was pressed against Brianne’s leg.

She stopped me and said, “Go stand at the edge of the bed.”

Doing as I was told, she rolled another condom on me, lubed us up and then had me enter her in a traditional butterfly position.

As I entered, she grabbed my hand and had me continue the handjob, which I happily obliged.

It was odd because I was not as focused on my own action of fucking her in so much as I was interested in delivering the handjob. I was transfixed on making her cum.

Up to this point, I hadn’t even considered that this might not be possible, but it dawned on me in that moment that because of hormones and whatnot, she might not be able to achieve an orgasm.

So, I did what any open-minded guy with his dick inside a transwoman’s ass while stroking her penis would do, I asked, “Can you cum?”

She was CLEARLY enjoying the entire experience and managed to barely get out a response between sighs and panting, “Yeah, I’m going to cum soon.”

Well, alrighty then, let’s make magic.

I lifted the pace of my handjob quite a bit and there was an almost instant reaction as Brianne’s back arched and she pressed her ass further towards me.

Within seconds, I could feel incredible contractions on my penis inside her and the familiar feeling that men get when they’re masturbating and they start to cum how their cock pulses… Except this time, it was hers and not mine.

Streams of cum started jetting out of her penis onto her stomach, deep moans and wicked contractions inside her ass.

I started sliding myself in and out of her ass faster now bringing myself to orgasm — just as her’s was subsiding, I finished inside her again… The last pulses of her orgasm milking my cock to its own climax.

Entirely Unique Experience

I was physically spent at this point, but despite it being nearly 3:30am, I was mentally wired — I could have probably figured out how to keep going.

But Brianne was finished, she’d had enough.

We talked for about 15 minutes while I was collecting my things to head back to my room, but there was no talk of doing it again.

I think we achieved everything there was to achieve.

For me, looking back on it, this was one of those random unique experiences that you can only have when you are open to possibility.

I don’t consider myself bisexual despite having had a couple more experiences with men after this. I’m not sexually or romantically attracted to men, but in certain circumstances, I’ve been free and confident enough in my own sexuality to just have a good time with whatever comes along.

Life is for living and unique experiences are the things that add the spice to an otherwise plain existence.

Author’s note: Names and places changed to protect everyone’s privacy.

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