I’m writing this from my hotel in Thailand. I arrived during the rise of Omicron, so unfortunately the first two weeks of my work trip were spent in quarantine. Admittedly the time in my hotel wasn’t as bad as it could have been, but it’s impossible for a hotel to be 5 stars when you can only leave your room to go get tested, and eventually go to the pool area where masks still had to be worn. Only jobs like mine were bothering to waste money on sending people to a long paid quarantine, and I’m in a male dominated field, so the pool chairs are all covered in men…
Knowing that I don’t have to stay in quarantine forever, I turn to Tinder. There are thousands upon thousands of profiles to scroll through, but it becomes quite annoying when it repeats every five profiles. One is a ladyboy, one is a prostitute, one writes nothing about them, and then the last two scream about how they don’t want to talk to anybody looking for fun or a one night stand, only marriage.
After swiping right on all of the blank profiles that are somewhat attractive, I end up with a few dozen matches in my two weeks of quarantine. My profile pictures are decent, but my profile is in English. It is very clear that I am just passing through, and only looking for fun activities. I enjoy massage, erotic photography, and of course hookups if a woman is interested. Unfortunately nearly every match didn’t bother to read, or translate before matching with me. It’s just more of the same, only interested in long term relationships.
The few that would actually be interested in a hookup end up being flakes, making plans and then just ghosting when it is time to play. What are my other options? I’m not interested in a brothel or a spa for a massage with a happy ending. Even if I wanted to pay, if the two guys I am traveling with send word back to headquarters, I’m out of a good job without them batting an eye. It happened last year to one of the more disgusting coworkers we had.
I stuck with looking online and browsing the surrounding city once I moved out of quarantine. The other apps didn’t really have any better ***********ion than Tinder. I was bored in the hotel room, being burned out on movies and binge watching TV for the last two weeks. I went back through the messages I had received from women that hadn’t read my words earlier. I sent a quick “Hi’ to some of the women that appeared to be fitting. I love mature women, and chubby girls, but in Thailand, all the “fat” or “chubby” women are really just average body types by American standards.
A few wrote back in Thai, wanting to know if I would take them to the States, or go shopping, or just asking if I am looking for a relationship and staying in Bangkok. More annoying conversations that could have been avoided with a translator app. The only one that didn’t seem to come begging for purses or marriage was Tanaa (for short). She was 48, and chubby by her own de***********ion. She was new to an online dating app, and didn’t really understand that people on here weren’t all looking for the same thing.
It wasn’t a big deal. I would get a message, translate it, put some generic conversation back in the translator and send it back to her. To my surprise, she kept writing, even though she knew by now that I wasn’t what she was looking for. I found out that she was a widow for the last nine years, and had a daughter and grandchild living with her.
I was running out of options for sex, so I figured I would take a shot at getting a little bit of fun out of the situation. I told her that I do massage, and I was looking to get a massage for myself while I’m in Thailand, since I rarely get them in the States. She said she had a friend that did massage at a spa, but unfortunately it wasn’t close to my hotel. She said she could show me where. I’m sure there was some miscommunication through the back and forth translating, but I got a message saying it would be the two of them doing massage on me at the friend’s spa. Unfortunately not…
When I wrote back to confirm if she said I was going to get two women massaging me, she said “I don’t know how to massage. Can you teach me?” Yes, yes I can! This is my normal way in for many of my erotic evenings, involving sex or not. We wrote back and forth more to confirm what she wanted. I only wrote about the massage topic for a few hours with her. She was at work at one of the many malls in the area, but had time to text with me. She wanted to come over after her shift, late that evening. I wanted to be completely sure that I wasn’t going to get caught bringing a prostitute out of the hotel. Since we were only talking about massage, I didn’t want to insult her by asking if she was looking for money for sex. I wrote to her that I wanted to make sure I didn’t make her uncomfortable when we meet, since we can’t speak to each other. Are you only interested in massage, or are you considering sex tonight?
“No”
Well, I had higher hopes, but it is what it is. She later wrote that she hadn’t had sex since her husband died. He was the only man she had ever been with. I can understand that she is shy, and if she made it to 48 years old with only one man in her entire life, some texting in an app probably won’t have her dying for an American inside of her!
We arranged a time, and I went down to the mall nearby to look for massage oil. I had no plans to do this on my trip, so I hadn’t packed it. Unfortunately the mall didn’t have a great ***********ion of stores, mostly clothes and fast food. I walked into the one pharmacy, and picked up baby oil. When I walked to the register, the condoms were right there, so better safe than sorry…
That evening came, I prepared the bed, putting down a large towel so the oil wouldn’t go everywhere. I went downstairs to pick her up out of her taxi and bring her up to the room. I’m not much for small talk, so it is actually quite convenient that we couldn’t speak to each other. I had prepared her well with our prior writing. We got inside, took our masks off, I showed her the bed was prepared, and then I walked her back to the bathroom. She went in and took a quick shower. She came out wrapped in a towel that was way too big, but she was too shy to use one of the smaller towels, let alone come out nude. I had stripped down to my boxers.
I welcomed her to lay down, but she was motioning for me to lay down first. How am I supposed to teach her massage if I don’t show her first? I laid on the bed in position to show her what to do, and then got back up. She speaks a few short phrases, clearly too shy to dive in. I wait patiently as she lays down in her giant towel. I can only see her shoulders, and the bottom half of her calves…
I gently started tugging at the towel to get it out from under her. She helped a little, letting it come out. I folded it until it was finally only covering her butt. I proceeded to do my thing, massaging her arms and shoulders first, then I moved down to her feet and started moving up. She kept her legs pinched tightly together. I got the message and just massaged the back and outside, not trying to slip my hand in between her legs. I pushed my hands up under the towel to work on her butt without her feeling too exposed.
I moved up and straddled her legs to massage her back. I made sure she could feel my semi hard cock resting on her leg through my boxers. I worked extra long on her back and shoulders to give her plenty of time to relax, and also feel my hard cock in the most respectful way possible at that time. I stood up and moved the towel back over her, telling her to turn over. I refolded it once she was on her back, to just barely cover her breasts and pussy. I started massaging her legs again, eventually moving my hands up dangerously close to her mound, brushing only a few pubic hairs when I got there. I finished by rubbing the front of her shoulders and a little bit of the top of her chest, but her C cup breasts were trying to slip out from under the towel.
I made a motion asking if she wanted me to massage her breasts, but she shook her head, and went to stand up. One of her breasts did come exposed, but she didn’t seem to notice. She wanted me to get on the bed next. I went into the bedroom and lost my boxers, grabbing a small towel. I walked back out with the towel in front of my hard cock, leaving her the option to look as I walked by if she really wanted to try. She was once again wrapped up tightly in her huge towel. I layed on my belly and tried to relax as she nervously gave me a frenzied and unskilled massage.
When she went down to my legs, she was definitely not as polite or delicate as I was. She was running her hands up as far between my legs as she could manage. I moved them apart a little more as she kept rubbing brushing her fingers against my balls multiple times. I turned over on my back with the little towel covering my hard cock laying to the side, and my balls hanging down. She had turned a little less shy, and a little more silly. Giggling little phrases I couldn’t understand as she started rubbing my hairy chest with the baby oil. The only thing I could pick up was “King Kong”.
She moved down to my legs and again worked her hands up to the top quickly, repeatedly brushing against my balls. She wasn’t doing it by accident, and I could tell she was hoping to brush against my cock too, but it was too high for her to accidentally touch. She finally gave up trying to find it, and was done massaging me. I could see through my mostly closed eyes that she was looking directly at the bulge in my towel.
I opened my eyes and slid down to the end of the bed, letting the towel sort of still cover my cock as I got close to her. She had clearly said she wasn’t looking for sex tonight, but I could tell my work had swayed her thoughts now. Can I break this widow’s nine year dry spell with a mere 40 minutes of mutual massage?
Yes.
I took the baby oil out of her hand and set it on the bed. I put my hands on her hips, covered by the towel. She moved forward pushing her body against my face. I looked up as I brought a hand up and took a hold of the end of the towel that was holding it wrapped around her body. I nodded my head as I asked “okay?” She nodded her head and I let the towel drop, revealing her round and soft breasts, and a belly that looked about 5 months pregnant, not big at all for being one of the “chubby” women.
I took a breast in my hand and started to suck on her nipple. She melted immediately, pulling my head tighter onto her breast. I moved between them, back and forth for a few minutes. I let her breast fall from my mouth and I flopped back onto the bed. She reached down and removed the towel that was still barely covering me up. The look on her face when she saw my cock for the first time was priceless. I’m not huge by American standards, but I was clearly going to be the bigger of the two men that would ever be inside of her.
She used her hands to play with my cock for a little while, mostly for her own amusement. She was not skilled at intimacy, and I don’t blame her since she was the next closest thing to a virgin when it came to experience. She wasn’t stroking or anything, just flipping it back and forth to make the head hit my legs like a hammer. I decided to stand up and have her lay back on the bed, because she wasn’t going to take the lead on this.
I knelt next to her, and put my finger on her clitoris. She looked surprised that I found it, let alone so quickly. Seems like her late husband didn’t do anything with her other than make a baby. I leaned over and started sucking her nipples again as I worked on her clitoris. It couldn’t have been more than twenty seconds before she squeezed her legs onto my hand, trying to stop me as she closed her eyes and stifled her moans of her first orgasm.
I continued to suck her breasts and finger her clitoris, moving further down to get one, then two fingers into her pussy. She didn’t have huge orgasms, but she had a lot of them, every minute or two. She moved her hand to my cock and started stroking it as I continued to pleasure her. I stood up and she pulled herself over with my shaft and put her mouth on my cock for the first time. She sucked for a short time before throwing herself back on the bed to catch her breath.
I opened the nightstand drawer. I pulled out a cock ring and slid it down my rigid shaft. Then I picked up the box of condoms and showed it to her, pointing at it. I wanted to be perfectly clear that this hard cock was going inside of her, so I could be sure she wanted this. She nodded her head, so I opened a condom and put it on. I moved down to her legs and pulled them apart, kneeling in between them and getting into position. I put a little extra baby oil on the condom to be sure it was slick, and put the head at her lips. She gasped a little as I slid my hard cock inside of her. I can imagine the thoughts running through her head as she felt this big American man pushing the biggest cock she has ever had deep inside of her. I hit the bottom easily, even in missionary position.
I folded her legs up and put them on my shoulder. I couldn’t get any deeper into her tight little pussy, but I could hit the bottom harder. I could feel her engorged cervix rubbing the top of my head through the condom. She wasn’t doing a good job of keeping her orgasms quiet anymore, even though she was still trying. After a few more, I let go of her legs. She rolled over to her side, and said something I still didn’t understand. It didn’t matter, because she got on all fours in front of me with her pussy pointed right at my cock.
I took aim and took hold of her ass as I pushed deep inside of her once again. I went a little easier on her as I didn’t want her to have a ton of pain after she left the only American man she has ever had, and regret opening her legs for him. She had a few more orgasms, but seemed to be worn out. I let her collapse down onto her belly, and kept fucking through her tightly closed legs. I love this position because of the dominance, and the added feeling it gives on my cock, making her pussy feel deeper than it really was.
I held myself off, waiting for her to have another orgasm, and I finished with her, filling the condom with my cum. I waited for a moment and let her calm down before pulling out of her with my freshly filled condom.
It was again pleasant for me that we could just clean up and get dressed without any talk. She didn’t seem upset, like she had been used or anything as I took her back down to her taxi.