Encounter of the First Kind

Story Info
First ladyboy experience.
1.4k words
4.23
54k
19
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
gendidi
gendidi
31 Followers

I'm a married man in my mid forties. I have an older disabled wife. We don't have any children. We have been married for a decade. Ever since she was disabled, we stopped having sex. She gets depressed occasionally and has been taking happy pills for years. Maybe that's why she lost her sex drive and I don't blame her.

We never discussed about sex. I assume she minds me having sex outside (every woman does), but I still have needs. So I steal a little fun as and when I have the chance, with total discretion. I can sense that I get her green light as long as our marriage remains the same status.

I do travel outstations for work sometimes. This is when I get to satisfy my sexual needs. I will go for a body massage when I get a happy ending, hire an escort, find a sex date online etc. I also have a little fun when I travel back to Southeast Asia when I visit my family. Massage is a must have when we visit Bangkok.

One year, my dad passed away suddenly and I flew back alone to attend his funeral on the next available flight. It was long and miserable, both the flight and the extended funeral.

When it was over, I contacted a senior of mine whom I hadn't met for years. He told me that he was actually organising a farewell trip to Bangkok for a uni friend who had cancer, final stage and asked me whether I would like to join them. I jumped at the chance and joined them in Bangkok for a few days.

They were a friendly bunch, some even brought their teenage daughters. There was lots of food, shopping and of course massages. In the end, I decided to stay a few extra days on my own. I chose a different hotel far from the red light district, closer to a local housing district. The next day, I wandered around exploring the area by foot. I came across a few massage parlours near my hotel. As I was getting a bit tired under the scorching hot sun of Bangkok, I decided to treat myself with a massage. I simply walked into a massage parlour and I was greeted with a Thai woman. I told her that I would like a body massage. She then sat me down and took off my shoes and offered me a cup of tea, as she took an album out asking me to choose my masseur. In that album, they were a mixture of men and women to choose from. I flipped through the whole album and decided on a woman in her late 30s.

After that, I was led to a room with a shower upstairs with double bed. I was a bit surprised but didn't bother to ask why. I saw there was a shirt and shorts on the bed, so I just took off my shirt and trousers and put them on. A few minutes later, there was a knock on the door. I opened the door and there she was, my masseur in her skin-tight t-shirt and hotpants. She was quite petite, about 5'2" but busty. She greeted me the Thai way and I reciprocated.

"Hi, my name is Natti." Quite a sultry voice.

"Hi, mine is James."

"You want to put on the shorts we provide?"

As she can see that I put on the shirt they provided but not the shorts. I was naked waist down.

"I can't, because they gave me two shirts."

She gazed at my penis and smiled, "maybe we should have the massage this way."

I smiled back.

"What kind of massage do you want?"

"I would like to try the herbal massage and then Thai massage."

She then closed the door, asking me to take off my shirt. I was a bit embarrassed because I was totally naked in front of her. She checked out my naked body with a sweet smile. As if she agreed with what she saw. I guess years of dieting and working hard at the gym finally paid off.

She placed her hand on my shoulder and asked me to lay on my stomach. Her hand was so soft and electrifying. I felt my heart skipped a beat and my cock started to react. She then put a towel on buttocks, I was a little disappointed but didn't protest.

She placed a warm bag filled with herbs all over my back, legs etc. It was quite nice and relaxing. She then asked me to turn over. By then, I had a massive hard-on. As she held the towel when I turned over, she had a good look at my throbbing cock and gave me an even bigger smile. When she out the towel on my groin, it was like a tent...

She continued with the bag of herbs on my shoulders, chest. My sensitive nipples felt so warm when she put the bag of herbs gently on them. I can't control myself any longer and grabbed her hand. By then, she could sense that I was very excited and wanted something more. I placed her hand on my lips and kissed it gently...

She put another hand of hers on my chest and massaged it gently and lovingly. I kissed her hand even more deeply. She then put the bag of herbs away and dimmed the light as she took of her tight t-shirt, exposing her glorious breasts. I sat up with my huge hard-on, admiring her beauty. She then walked slowly to me between my thighs. I gently caressed her hair and help her face in my hands. I kissed her luscious lips. Once I started, I just couldn't stopped kissing her deeper and deeper. She seemed to enjoy this attention and reciprocated. Her wet little tongue ran wild in my mouth. And so was my hands. I searched her breasts and squeezed them. When I touched her nipples, I was amazed how soft and big they were. I ran my lips down her neck and then her chest. I lowered my head so that I could suck her wonderful nipples. I had never kissed and sucked such heavenly nipples in my life! I had so much pleasure playing with them. So was her. She moaned and groaned as she wrapped her arms around my neck.

After seemed forever, she started kissing my nipples and sucked them gently which totally drove me crazy. She then did something which sent me straight to heaven by hold my cock in her mouth, sucking it greedily. She gave such wonderful blowjob. I had to stop her before I shot in her mouth.

I placed her in bed and tried to take her hotpants off only to discover that she had a cock! A tiny brown cock. Then only I realised that my masseur was a ladyboy. I knew they existed and never bothered at all but I had never thought having sex with one. I was so horny then and I wasn't going to let this put me off. After all, I had nothing against the third sex.

"Is it ok?" Natti asked.

"Not a problem."

"Have you fucked a ladyboy before?"

"Can't say I have. Maybe you can show me how. "

She sighed with relief and pressed her marvellous breasts against my chest, which was sensational. My cock was dripping hard with precum and I was dying to cum. She applied some lube on my cock and her ass. She was on her back, legs in the air. She then guided me to the gate of heaven. It was so tight and warm. I inched inside her and she sighed of great pleasure. I had never had sex with a ladyboy in my life. From the fact that I had the greatest pleasure I had never had so far. I was glad that I finally discovered this hidden guilty pleasure. I fucked her as deep and I could and we both moaned and groaned like two wild animals. As I fucked her hard and furiously, she wrapped her legs around my waist and her hands played with my nipples. I had never experienced such intense sex and after a few minutes, I shot the biggest load of my life inside her. I was totally exhausted and rested on her for a few minutes.

When we recovered, we showered together and got dressed. I paid her a handsome tips. We exchanged numbers and I promised to contact her next time.

gendidi
gendidi
31 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousover 2 years ago

Sucked his nipples but still didn't realise it was a dude lol wtf

robin48robin48over 7 years ago
nice

get her booty

AnonymousAnonymousabout 8 years ago
Love it

My first experience in Thailand I was drunk after the bar got on the back of what I thought was an Asian hooker got to her place started getting to it she was amazing at sucking my cock better than my girlfriend at the time lol. But after stripping down came to realize it was a ladyboy!! Same thing it was such a horny and hot moment she laid me down flipped over me and we started to 69 I couldn't help but suck on her cock after a bit we she rolled over and I fucked her ass until I came flopped down on the bed thinking that was it... She got up slapped some lube on my virgin hole and slowly pushed her cock in me. It was such a rush of pleasure, shock and amazement she fucked me until she same. We both had a cold shower I paid her then went back to the hostel my girlfriend was sleeping at. I suggest visiting Thailand

AnonymousAnonymousabout 8 years ago
EEEEwwwwww.

Enough said.

Share this Story

Similar Stories

Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Addicted to Pream's Cream A man's first TS encounter at a massage parlor.in Transgender & Crossdressers
Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Meat A man takes home the waitress from his favorite steak house.in Transgender & Crossdressers
More Stories