Can you help me? I’m a good-looking man in my late 50s living in a small provincial town in Thailand. A few months after I was left alone, I decided to spend a few weeks at what is now my summer home on the East Coast. On the way there, I stopped at the local shop to buy some treats to enjoy during my stay. I quickly lit the wood stove and carried the groceries and my small suitcase inside. The house was not very big, but it was very cozy. We had had many good summers and weekends, but unfortunately that time was over, and I fiddled around a bit, trying to figure out what changes needed to be made. I threw a few more knots in the stove and put my coat back on to go for a walk while it warmed up.

The area where my cottage is located has quite a few “permanent residents” and a really beautiful natural setting with many paths and trails, and I knew most of the residents from various work weekends, birthdays, and so on. After half an hour I turned to go home and when I was almost home I saw Sasha standing with her head down in the engine compartment of her little car.

Hi Sasha I called out and she looked up and said can you help me. Of course, I wanted to help her. Unfortunately, I couldn’t fix the problem with her car, it probably needed more expert help. This annoyed Sasha because she had to go into town to do some shopping. I offered Sasha to borrow my car to get what she needed and if she wanted, I would prepare a piece of bread for her when she got home. She accepted both and figured she would probably need about three hours of her time. Fine by me, then I could take a shower and it would be nice and warm when she showed up. Sasha picked up the car and asked if there was anything she needed to bring me. If you’re going to the pharmacy, please pick up a tube of Voltaren, I left it at home.

Sasha is a 23-year-old Asian trans lady who has been single the entire time she has lived in the summer cottage area. She is a webcam trans. I have often seen her visiting gentlemen and once I caught a glimpse of her getting into her car dressed in a short skirt, long white knee socks and a very low cut blouse, well filled out by her breasts. The rear end is also quite nice from what I had seen. I went to work in the kitchen, boiled eggs, prepared herring, shrimp, smoked salmon, rib roast, and a few different sliced cold cuts. Cheese and grapes were also prepared. Then I set the table with wine, beer and liquor glasses and candles. Once that was done, I took a shower and after getting dressed, I was ready for it all. I sat down to watch some English football to kill time until Sasha arrived. Three and a half hours after she left, Sasha pulled into the driveway and I slipped out and let her in. Imagine my surprise when she walked through the door wearing the aforementioned “costume,” long hair in pigtails, and a bright red, very fragrant mouth. I just stood there staring at her with my mouth open and my polyps. You have seen me in this outfit before and I remember that your eyes were about to roll out of your head, she said, so I thought I would be nice to you now that you have lent me your car.

A little nervous, I took Sasha into the living room and asked her if she wanted something to drink before we got something to eat. Sasha was starving, so we went straight to the table, I was busy putting food on the table. We agreed to have red wine with dinner, as we were both afraid that beer and liquor would make us too drunk. The conversation continued and soon we were at cheese and the second bottle of red wine. I commented on her outfit and Sasha told me that despite her flaws, she needed male attention from time to time and that she had met some guys on a dating site who were turned on by her acting like a little schoolgirl. Does that turn you on too, she asked. I thought she looked good but wasn’t turned on by the little girl thing, but said I thought she looked nice and had a great body and that was probably what turned me on. I cleared the food away and we sat down on the sofa to enjoy the rest of the wine.

“What’s that over there?” she asked, pointing. “It’s my massage table that I used to make life a little more bearable for my wife, but now it’s unused. Where have you been giving her massages, Sasha asked. I didn’t want to go into details about my late wife, so I just said it was a full body massage. That sounds lovely, Sasha said, couldn’t I persuade you to give me a good one? Yes, I can, but you should know that I’m not a trained masseuse and I’m a little afraid that you’ll go crazy if I touch you where you don’t expect it. I don’t want the word to get around that I’m an old pig. I guarantee you that won’t happen and you can massage me anywhere and I hope I get a lot out of it because I asked you earlier “can you help me” and I meant it. I rolled down the curtains and set up massage tables in the middle of the floor so I had free access all around. I put a clean sheet on the table and laid out a towel, then with the comment that she could undress and lie on her stomach, I went into the bedroom to put on sweatpants.

When I came back into the living room, Sasha was lying on the massage table with the towel over her bottom, but I could clearly see that she didn’t have a stitch on her body. I asked her if she wanted me to put Voltaren on the painful/sore spots before I started the actual massage. Yes please, she said, it’s in the net I brought with me when I arrived, sorry I didn’t give it to you already. I found the net and wanted to give it to her as I didn’t want to go through her things, but she said you can take it. When I looked down in the net, I saw not only the box of Voltaren, but also another tube and some dildos. Sasha looked up at me as I unpacked the Voltaren and asked me if I was okay with what I had seen, to which I replied that I was fine and that I was looking forward to helping her out. Sasha told me that her knees, lower back and shoulders were the worst affected. Since I didn’t want to numb my hands and fingers while applying the Voltaren, I grabbed a pair of nitrile gloves from the kitchen drawer and put them on.

I have a round “pillow,” a foam rubber cushion covered with some kind of latex/vinyl. I asked Sasha to lift her abdomen and placed the pillow under her hips to lift her abdomen. I began rubbing Voltaren into the back of her knees and around her knees, then moved up to her head and gave her shoulders the same treatment. Now it was time for her lower back, which was probably the most damaged from the car accident she had many years ago. I moved the towel and massaged the Voltaren well into her lower back. I enjoyed the sight of her exposed buttocks and sex, which now showed me that she was a true redhead. Sasha started to make a little noise and said it felt good. I wanted to finish the Voltaren and asked Sasha to turn around so I could push her shoulders forward. At the same time, I had a clear view of a pair of beautiful breasts with nice protruding nipples. Once that was done, I put a blanket over her, gave her the wine glass, and said there would be a five-minute break to let the Voltaren take effect before we continued. Sasha said it was wonderful and that it wouldn’t be the last time she had to relieve the pain this way.

We got Sasha back on her stomach and she did not want to be covered as it was warm enough now and she also had an internal heat. I had two different massage oils from earlier, one with a lavender scent and one with a light citrus scent. Sasha chose the latter and we could finally start the actual massage after I had taken off the top of my tracksuit and was now wearing a short-sleeved undershirt. I took some oil in my hands and began to massage my neck and throat with gentle but persistent movements. Slowly I moved down to the shoulders and both arms and armpits also got a good massage while I kept adding more oil, Sasha actually had a nice body, maybe with a few extra kilos here and there but I had plenty so I shouldn’t complain. I continued down Sasha’s back, making sure to massage her sides and the parts of her breasts that were accessible. Finally, after giving her lower back and hips a good rub with both hands and elbows, I reached her lovely buttocks, which were well lifted by the pillow under her hips.

No oil was spared and when Sasha spread her legs a little more, there was a nice view of all her glory. I massaged her buttocks well and thoroughly and could clearly hear that Sasha felt great. When I let a little oil run down between her buttocks, her legs were spread further and when I let my hands slide between her buttocks and massaged out towards her inner thighs, Sasha moaned loudly and a little yes sounded from her. I now went down to her feet and lifted one of her legs and began massaging her toes and feet and up to her shin. The other leg received the same treatment. Now I had reached her thighs and Sasha had spread her legs further so that there was now a completely clear view of all the delights and I could see that her new man-made sex had begun to open up a little as her clit had grown. I continued the massage up her thighs and approached her crotch, making sure her inner thighs were well stimulated. My fingers grazed both her clit and her star in their tireless work. Sasha was now moaning loudly and begging me to give her an orgasm as she was about to burst with pleasure.

I told her that we had talked about a full body massage, so it was a bit early. Just a little one, she said, and I began stroking her clit lightly. Now Sasha became almost hysterical and demanded more action to get the expected ejaculation. I carefully opened her vagina and found that she was dripping wet. I gently inserted my middle finger inside her and quickly followed with my index finger. The third finger was also inserted into Sasha’s uterus and as my thumb began to stimulate her perineum and star, she exploded in a beautiful orgasm. After Sasha recovered a bit, I patted her bottom and told her to turn around. Thank you, she said, it was just so super wonderful, but let me just have a five minute break and a glass of wine. Sasha got off the table and went to the bathroom while I poured the wine. When Sasha came back from the bathroom, I went out to relieve myself and wash my hands.

Back in the living room, Sasha was lying on the table with a big smile on her face and announced that she was ready for the big ride. I started again at the top of her head where her rat tail made it relatively easy to avoid getting too much oil in her hair. I began with her neck and ears where there are some very active erogenous zones. Slowly I moved down her body and of course gave her breasts a good workout, finishing by rubbing her nipples until they were nice and stiff. I continued down over her stomach and approached the hard trans clitoris. Under loud protests from Sasha, I stopped here and went back down and began massaging her thighs from the knees up. I pushed a pillow under her lower back so that her crotch smiled cheekily up at me. I could see that there was still moisture around her flower and Sasha responded with some moaning as I approached her crotch. I leaned over her and took one of her nipples in my mouth and nibbled lightly on it while gently opening her womb with a finger and letting my thumb lightly massage her clit, which turned out to be the largest I’d ever seen.

A few more fingers and the thumb had to give way to my mouth and tongue. Sasha was in seventh heaven now and demanded more, screaming at me to use what’s in the net. Still with three fingers inside Sasha, I bent down and placed the net on Sasha’s belly. She quickly fished out a small, thin massager and a tube of lube. She begged me to fuck her cunt and lubricated the small device, and I also got a dab on my free hand. Furthermore, she quickly turned around and lay on her stomach again with everything straight up in the air after the poo had also come under her hips. I began to lubricate and press lightly on the star and relatively quickly a finger slid up past the sphincter. It was something Sasha could use, three fingers in the new vagina, circling over her pussy, while she demanded that my finger in her butt be replaced with the little massager.

As commanded, I did and it wasn’t long before a huge orgasm rocked Sasha. When she caught her breath, she asked me to remove my fingers and I brought them to her mouth where she eagerly licked them. Now she wanted to lubricate my hand with lube because, as she said, I had promised to help her. As said, my hand was well lubricated and she lubricated the entrance as well. I gently widened her vaginal opening, first with three fingers, then with four, and finally brought my thumb into play. Slowly and under a lot of babbling of more or less incomprehensible words from Sasha, I gently pushed my hand up into her new vagina. I couldn’t move it much, but it wasn’t necessary because Sasha exploded in a great orgasm and almost lost consciousness. I carefully removed my hand and vibrator and let Sasha come back to this world. What about you, Sasha asked. No thanks, I said, my pleasure is to please my wife, so that’s fine with me. I gave her a few slaps on her bottom and helped her down from the table and she quietly got dressed, after which I drove her home.