A lovely Surprise in Thailand

Story Info
Older man finds happiness with a trans woman.
4.5k words
4.62
22.9k
28
0
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
Afterhours22
Afterhours22
1,129 Followers

I needed a nice long vacation after my retirement. At 50 years old, I had worked my ass off for most of my adult life to provide stability and security for my family. Raised two beautiful girls that were now off making their own lives now.

Shortly after the youngest left the nest, my wife of 27 years decided that she did not want to be married to me anymore because she could not stand the fact that I still wanted sex from her. She had become a member of the latest cult church and now believed that sex was for procreation only, not for pleasure.

So, two years later, divorced and still living the bachelor life, I did not have time for the dating scene, not to mention the dating pool for guys my age was not particularly good as I was not looking for another family to raise and I did not want some young headache either. Work kept me busy along with going to the gym but now work was done, and I needed a break.

I decided to take a trip abroad and I had always wanted to tour the Pacific Asian countries and after many suggestions, chose to start with Thailand. Friends said that you get way more bang for your buck there with great condo locations being some of the lowest priced in the foreign market. So, I rented a beach front condo for a month in the Hua Hin District of Thailand.

The beaches there were gorgeous, white sand and crystal-clear blue waters made my choice the best I could have made. The people there, both native and tourists were genuinely nice to be around, never giving me the feeling of being in a tourist trap like some of the beaches in the US.

After being there a couple of weeks and getting to know the area better, I wanted a night out in the bar district. As I walked down through one of the streets, there were all the usual places, with girls out front, wanting you to come in and buy them a drink at this certain bar. I politely declined most of them, but not before being nice and chatting with them a bit before moving on.

There was a small bar on the corner that looked quiet with only about 7 or 8 people inside and no one outside trying to draw people in. That was where I stopped. No pressure to come in, just sat down at the bar, ordered a drink, and began to relax.

After about two drinks, and just about to order a third, a woman, looking to be in her early 30's if that, came in and sat down about 2 seats away. She was extremely attractive, looked to be about 5'5" tall, wavy raven colored hair, down a little past her shoulders, on the thin side, but perfectly proportioned in her short yellow and floral spaghetti strapped dress.

I got my drink, smiled at her and tipped it to her as she looked my way, nodding and smiling in return. The place was quiet enough to strike up a conversation with her and I was pleasantly surprised at how well she spoke English. Her name was Apinya and she told me that she had spent four years in the US going to university to become a software programmer.

Given how well our conversation was going, I thought it would be okay that I sat closer to her, so I moved to the seat next to her. She smiled in approval which gave me the feeling that she was as attracted to me as I was her. As I had said previously, I never gave it much thought to dating a younger woman, but Apinya seemed very mature and well-spoken so where this would go from here would be an open book.

Her being attracted to me, well that was not a given. I did work out and was in surprisingly good shape for my age. I could still go without a shirt on the beach without scaring women and children away, so that was a plus. We had briefly talked about our ages, her being 31 and me telling her how old I was did not send her running for the hills.

She just continued to smile while we chatted, sipping our drinks, and just enjoying each other's company. Well, the evening turned late, and I asked Apinya if I could have her phone number to call her to go out for dinner sometime. She shocked me by not only giving me her number but asking me if it would be okay that she came to my place tonight.

I was blown away by her request, not expecting her to be so forward, but after pausing for a brief few seconds, I smiled and agreed. I paid our bar tab as we got up to go, Apinya looping her arm through mine when we went out the front of the bar and into the street. We walked as if we were a couple on our first date as we slowly made our way to my condo.

We got into my place and as I went to make us a couple of drinks, she sat down on the sofa in the living room. I brought our drinks in and sat down beside her as we chatted some more, as I got more and more mesmerized by her seductive beauty. I threw caution to the wind after another drink and leaned in to kiss her.

Apinya readily accepted my pass and returned my kiss with such gentle softness, sending shivers down my spine. It had been so long since I had tasted a kiss so sweet that I had forgotten what it felt like. Our kiss turned deeper and more passionate as our hands began to explore each other.

Her dark skin was like silk when I traced my fingers up and down her arm, then delicately touching her neck up behind her ear while we kept exploring each other's mouths. I felt her hand move slowly down my chest, across my abs and coming to rest on my now very erect cock straining to get out of my shorts. She let out a soft moan and I gasped into her mouth.

Her fingers were quick and went to work on my button and zipper, releasing my extremely hard prick into her hand and wrapping her slender fingers around me, causing yet another groan to escape my lips. She pulled away from our kiss, smiled at me then bent over, taking me into her mouth. Oh my GOD, her mouth felt incredible!

She slowly moved her lips up and down my organ, just taking a little in at a time. I could feel her tongue sliding around it as she did, sending me into another level of pleasure. I leaned back on the sofa, my eyes barely opened as I watched this gorgeous woman, make love to my cock like I had never done before. Even in my early marital days, my wife never sucked me this good, not even close.

Apinya paused to pull her dress up over her head, leaving her in just her slinky pink panties, then went back to work on my engorged hard on. I reached down and ran my hands up and down her soft back then moved around to caress her small barely A cup breast. Her nipples were like pencil erasers and when I fondled them, she groaned into my cock.

It had been so long since I had last experienced such pleasure and so I knew it would not be long as I felt my climax already building. Apinya was taking me in and out of her mouth at an increasing pace, using her hand to stroke me while she did so. I felt the first spasm begin and I let her know that I was going to cum, but she kept sucking me, not showing any signs of slowing.

I groaned then cried out as the first jet of my cum erupted from me and into her hungry mouth. I held onto her tightly as she swallowed with each pulse, moaning along with me, not letting even a drop escape her. She massaged my cock like a pro, keeping her mouth over the head, to squeeze out every bit of my seed, and as I came down from my orgasm, her hand movements slowed as she kept me firmly held inside.

She gently caressed my balls, then placed loving little kisses around my cock, pausing only briefly to catch a few leftover pearl drops that tried to escape me. I was spent and could hardly move. It had been so long, and that orgasm was so powerful, it literally left me weak from head to toe. Apinya looked up at me, smiled her sweetest smile, then moved back up and kissed me.

She was extremely passionate and sweet to the point that I was beginning to think this was all a dream, as this gorgeous deeply tanned angel of a woman, curled up beside me, kissing me with a love that I had never felt. We stayed like that for several minutes as I continued to touch her, making my way to her intimate areas, but before I could go any further, Apinya moved away from me, stood up and put her dress back on. I asked her if she wanted to stay with me, but she smiled and shook her head no.

She slipped her sandals back on, picked up her small bag then leaned over and kissed me again, whispered for me to call her and slipped out the door. I was a little put off that she left like that, but then had to regroup for a minute as this was my first experience with a Thai woman, so I should just wait and see what the next day would bring.

After starting the day with a shower, coffee, and breakfast, I pulled out my phone to find Apinya's number. I sent her a text, since that seems like the thing to do with the younger generation, saying, "Hi Apinya, this is Rick. I really enjoyed my time with you last night was hoping you would be free for lunch today?" I pushed send and hoped for a quick response since she sure seemed to like me.

I waited but got no response from her. I wondered if I had entered the right number but remembered that she entered her digits for me before asking me to come to my place. I went to the beach, did some swimming and relaxing, periodically checking my messages through the rest of that afternoon but got nothing back. I began to wonder if I had somehow done something to offend her.

I had dinner and decided that I would try going back to the bar where we met to see if by chance she would be there. I got ready to head over to the bar district and was just about to leave when I got a text message from Apinya, "Hi Rick, sorry for the late response. I will explain later, if you agree to meet me along the beach walk, at one of the benches near the rocks." I texted back telling her that I would be there.

I could not help but get a little nervous not knowing exactly what to expect as I arrived at one of the benches. The sun was just about to go down and there were people still milling around as I waited and watched for Apinya. After about 20 minutes, I saw her approach from one of the streets on the town side of the beach walk.

She looked beautiful, wearing a light-colored sundress, that was loose and billowy, coming down just above her knees and gently blew in the light evening breeze, and wearing the same sandals that she had on the night before. She saw me and smiled, pushing one side of her hair back behind her ear. I stood up as she drew near and greeted her with a small kiss and embrace.

We sat down on the bench and she looked at me and said in her near perfect English, "Rick, I am really sorry about leaving like I did last night. I could tell that you were confused as to why I did not accept your invitation to stay with you but let me first say that it was in no way because of you. There is something I need to tell you before we go any further." She hesitated for a few minutes looking at the ground, her smile leaving her.

I looked at her intently waiting for her to finish. I could tell that there was something she needed to get off her conscience, so I smiled and said, "Apinya, just say what you need to say, there is nothing that you could do or say that would make me run away from you."

She looked up at me and replied, "Rick, normally meeting a guy for a night would not be a problem for me but with you, it is different. In the short time we talked and spent time together, I liked you immediately and that is why I got scared and left like I did."

"Apinya, please just tell me what is going on, okay?"

She paused again then blurted out, "Rick, I was born a man."

I looked at her, not knowing what to say at first as I had to process what she just said to me. At first, I felt anger stirring up inside, but as I looked into her sweet fearful eyes, I could not help but still feel the way I felt when I saw her walking towards me. I really liked this woman and I wanted to be with her.

Her face turned to one of sadness and she looked back at the ground, "You see, this is what I was afraid of, but I had to tell you the truth." I could see a tear fall down her cheek and my heart softened even more. I put my fingers to her chin and gently turned her to face me as more tears flowed. I kissed her soft lips briefly then pulled her into a warm embrace.

I pulled back from her and picked her chin up so I could look her in the eye and said, "Apinya, I do not know what kind of life you had before, but all I see is a beautiful woman here next to me now, and that is all that I care about." She smiled and leaped into my arms giving me a crushing hug as the tears of sadness turned to happiness.

We sat there for a bit longer, hugging and drying her tear-filled eyes. Apinya was all smiles again so I stood up, took her by the hand and walked with her down the beach walk. We chatted while we walked towards my condo and when we arrived, I had her sit on the balcony as I got us some drinks.

I came back and sat down with her and she began to tell me her real story of how she knew that she had been born in the wrong body and always felt like she was a woman. Her parents did not want anything to do with her after she came out to them but thankfully, her Grandmother stayed by her side, taking her in to live with her.

Then she went on to talk about when she started HRT and that she hoped in six months to get her sex reassignment surgery if her finances came together, something she had been struggling with since she had to take care of her sick Grandmother.

Then it clicked to me why she grew so apprehensive when I began to get close to her nether region last night. I reached out to hold her hand, getting the sweetest smile from her as she told me everything. After she finished, I asked her to stand up and as she did, I pulled her into my lap and kissed her passionately. At that point, I did not care about her past, I just wanted her now.

Apinya could tell that I truly desired her and just melted into me as our lips came together and our tongues danced a sweet tango. I put my arms under her and picked her up, then carried her into my bedroom and laid her on my bed. She looked at me once more with a slight fear in her eyes, but I quickly moved down on her, kissing her deeply again.

I then moved down the front of her neck and down across the top of her chest, placing little kisses as I did. I reached down taking the hem of her dress and with some help from her, lifted it off her, exposing her entire body, except for her tiny white panties. I moved back in on her, kissing around her small breasts, sucking each nipple into my mouth as she moaned her pleasure.

I then kissed down her very firm little tummy until I reached the top of her panties pausing to look up at her. Apinya had that apprehensive look again, but I just nodded to her as I looped my fingers through the sides of her panties and gently pulled them down.

As they cleared her knees and she spread her legs ever so slightly, her sex came into full view. She had kept it hidden by tucking it and as I tossed her panties to the side of the bed, her small penis came to life in front of my eyes. I leaned in to get a closer look as I laid my head on her thigh. I reached for her flesh and she nearly jumped out of her skin when my hand touched her.

Apinya was now hard but the skin covering her was as soft as the finest silk, as it now stood about four inches into the air. Her breathing had become erratic and I could tell that she was still a little scared. The only way I knew that she would fully relax was for me to take her into my mouth. I did not for a second consider it as being gay, I just wanted to please this beautiful, sensuous woman.

I moved up over her tender flesh, not exactly knowing what I was doing but just figured I would do what I would love done to me. I kissed the head of her small cock and she jumped again, letting out a small moan of pleasure, then I took her into my mouth.

Apinya tasted wonderful and the heat generating from her was like fire between my lips and inside me. Her sounds of pleasure as I began to suck on her, moving up and down, tasting her flesh just sent that fire all through my own body. Her hands gently caressed my head and hair, her hips beginning to move with my oral love on her.

I backed off her, pausing briefly to stroke her hardness, noticing a bead of precum started to flow from her. I dipped my tongue into it, to taste her. It had no taste but knowing it was from her just made me want more. I sucked her back into my mouth and moved up and down on her with more intensity, more sounds of pleasure coming from her as I did.

I knew she would cum soon and really was not sure how to react but since she had so readily swallowed my cum last night, I just felt like I should do the same for her.

Her hips moved faster as her head was back, and her eyes closed. She moaned out my name repeatedly telling me how wonderful I was making her feel.

Apinya then grabbed my head tight and tried to pull me off her but I was not having that as I kept my mouth on her. In the next second, she erupted into my mouth, her hips bucking and nearly driving her cock to the back of my throat. Her fluid was hot as I gagged initially from her thrusts, but then swallowed it. It was thin in consistency and it flowed more than it spurted, tasting a little salty sweet running down my throat.

Her body was shaking as her orgasm subsided while I kept her inside my mouth, just as she had done to me, I wanted every drop. I was instantly intoxicated by her heavenly nectar. When her flow ceased, I released her from my mouth. Apinya pulled me up to her face and began kissing me in the most passionate loving kiss I have ever had, showing her love and appreciation for what I had just done for her.

I wanted more of her, and my rock-hard cock agreed with me as it throbbed against her thigh during our kissing. She reached down and started massaging me, rubbing the precum flowing from me around the head, using it as a lubricant to stroke my manhood. Apinya whispered into my ear, asking me to get her bag off the table.

I went out into the kitchen, got her bag, and brought it back in to her. She set it on the nightstand and before I could lay back down with her, she grabbed my cock and engulfed it into her sweet mouth. Dear God, her lips felt so good on me as she moved my flesh in and out of them.

She then backed off me, reached into her bag and brought out a small container of lubricant, squeezed a generous amount on her hand and massaged it all over my hardness, then turned, laid on her tummy and put some on her sweet little rosebud that was now in full view as she did.

Apinya reached out and took my hand to pull me to her. I moved over her, with my erection now tucked between her cute ass cheeks. She then reached back, taking it in her hand and guided it towards her tight opening. She felt so warm and inviting as my cock began to push against her sphincter. It slowly began to give way and the head slid tightly in.

She groaned deeply into the pillow, and I paused to give her a minute to adjust to my thickness. She reached up to my hip with her hand and urging me onward as more of my cock disappeared into her very tight ass, slowly until my balls were resting against her perineum, eliciting another deep groan from her.

I laid against Apinya, feeling her fiery heat hugging my manhood as I started to move in and out of her very slowly. She felt so good, with her warm silky skinned body against me as began to build a gentle rhythm with her moving with me in perfect sync. She turned her head back towards me and I kissed her, sucking her tongue into my mouth.

I pulled out of her briefly to turn her over onto her back. I wanted to look into her beautiful eyes as I made love to her. She lifted her legs back to give me unabated access back inside her sweet ass as I sank all the way back into her. Her eyes half closed as she looked deep into mine.

Afterhours22
Afterhours22
1,129 Followers
12