[M][F]A Craigslist encounter in Bangkok with a MILF (M24)(F57)

This is my first post on reddit. So please go easy on me:)

A decade ago in my mid 20s, I was in Bangkok for extended holidays and was feeling lonely. This led me to search online to meet women. I would respond to all the W4M advertisements under the Casual encounters section. Sadly, most of them were either spam or paid sex offers. After a few weeks of attempts, I responded to a non-spam looking post and got a response asking for my pictures. I sent a few, but didn’t have any hopes from it, as I considered myself as an average looking young man. I was 6’0″ tall, on the thinner & athletic side due to regularly playing football and the long hair garnered a few looks.

So to my surprise, I got a happy response with a few of her own pictures. She introduced herself as ‘Emma’. In the pictures, seemed to be in her mid-50s and in average shape. She wore summer dresses and her green eyes complemented her dark blonde flowing hair. I couldn’t tell much more from them, but I found her attractive and her appearance somewhat reminded me of Lorraine Kelly’s face and the body of Barbara Schöneberger. We emailed back and forth for two weeks before her arrival from Boston. She insisted on meeting for a movie and ‘The Dark Knight’ was running in the multiplexes. I suggested a late afternoon show at a popular shopping mall.

The morning finally arrived and she sent a message from her phone that she has arrived and would take a short nap due to jet lag. I was incredibly excited and nervous as to how the evening would unfold. An hour before the meeting time, I made my way into the city and arrived at the Multiplex lounge a few minutes earlier. Just a mere minutes later, I saw a tall woman in a black blouse and black skirt walk past me and sit down a few meters ahead of me. I was in the process of getting up to approach her, but she was quicker. She turned around and called my name. Emma looked better than the pictures and absolutely crushed with me with a very tight hug. That’s when I felt how massive her breasts were! She stood tall at 5’9″ and had dark blonde hair with a few grey strands. Her figure matched with the photos- not thin, not chubby but on the bigger side.

We hardly had time to socialise and exchange pleasantries, as we still needed to buy tickets and find our spots in the theatre. The theatre was humongous and only around 20% capacity. Additionally, there was no one in our row and in the immediate vicinity. The film started and a few minutes later, she made the first move by holding my hand. We were rolling our thumbs and fingers around for a bit before I signalled intention to wrap my arm around her hips. She happily moved forward to accommodate me. The game was on. Soon, I moved my hands underneath her dress. She shuddered and moaned a bit as my hands were a bit cold and said, “Ooh, someone is feeling naughty.”

Now, I was emboldened. I was running my fingers through her hair, massaged her neck a bit and gathered courage to play with her breasts. From the outside, I was running circles around her nipples with my fingers. Emma’s breathing got heavier and I began kneading her breasts from inside her blouse. She then took the initiative of kissing me. We were groping each other like raging teenagers. Time had flown by, and the movie had come to an end. That was three hours of foreplay, groping and kissing! Lights had come on and we exchanged naughty looks. Downstairs at the lobby, we contemplate on what to do next- small dinner or go elsewhere. I didn’t want to lose the momentum so I suggested that we go back to her guest house. After teasing me for my directness, we get into the back of the taxi and we fondle each other discreetly. I definitely didn’t want to attract the taxi driver’s attention. Twenty minutes later, we arrive at the guest house.

The lift ride to the third floor seemed like an eternity. As soon as she opened the door, we took off our footwear and plopped on the two seater sofa. I continued where we left off- more kissing and groping, interspersed with some conversation. Now, I’m figuring out on how to take her top off but couldn’t for the life of me remove the blouse tightly tucked into her skirt. Emma wasn’t too enthusiastic at my attempt. What else were we going to do apart from fondling each other? Eventually she unzipped the side of the skirt and took off her top. Out popped her breasts in her bra. Goodness me! I haven’t seen such huge breasts in my life before and since then. There were so big that I didn’t know what to do with them! I groped around a bit while she giggled at my awkwardness. My hands go around the neck and pull down her straps. It’s the clasps that need to be undone. No fumbling this time around. I finally get her topless and what a sight to behold. Immediately, I buried my face into her breasts and set upon kissing and licking her nipples.. one after the other. That got her moaning a bit. I couldn’t contain my excitement and curiosity at this moment. While kneading, I had to ask how big they were? 36D came the reply. More breast worship followed.

I was truly lost in her breasts and had to snap myself out of it. On I went southwards- licking, kissing and planted some soft bites on her belly. Next step was to get the skirt off. Emma understood the intention and dropped her skirt. She then led me to the bed and got on top of me. Another round of kissing continued until her phone rang.

Off she went to attend the call while I was sauntering around the room observing the furnishings. It didn’t take too long for her to end the call. Emma held my face in her hands softly and planted more kisses. As we were of similar height, this felt soo good. I returned the favour after she was done. It was rather challenging to simultaneously squeeze her breasts and nibble on her neck/shoulder. After a bit of back and forth chat, we finally got out of our underpants. Emma went back to the bed and I stood by her bed side table. She began to stroke my penis softly, as if it were her first time. I was enjoying the moment and then she asked if I shaved my private bits just for her. I had a beaming smile and said yes. We both chuckled at that moment. Being considerate, I sat on her chest so that she could stroke my penis comfortably. Which she did happily. The sight of her stroking my penis over her huge breasts turned me on. I grabbed both boobs and began toying with them. Then I had the idea of tittyfucking. I took back control and began thrusting my penis through her boobs. I was expecting her to hold the boobs for me, but didn’t. No problem. I held them on tightly to savour the moment. After a few minutes of pumping, I attempted to lick her pussy. It was then she revealed that she hadn’t had sex for over a year but didn’t want to have sex or engage in oral sex on the first date. However, she conceded that this was the furthest she had gone on a first meeting. Of course, I was disappointed at the news of no sex, but consent is important and the last thing to do is ruin a good moment. We ended the night by mutually masturbating each other and kissed each other goodbye.

Emma and I agreed to meet in a few days’ time for another meeting. However, on the day of meeting I had a huge fallout with my family and couldn’t commit to the meeting and attempted to reschedule for the next day. Sadly, the next date never happened. She carried on with her travels and flew back to Boston. I went homebound too. We tried our hardest to make it happen, a few months later I got cockblocked again by my family as they flew down for a wedding. Emma had planned to visit me and was willing to have sex this time as she revealed later on.

We did manage to meet again three years later. But life had moved on. She now had a boyfriend and also accidentally revealed her real name. I pressed her on that and it had to do with stalkers on Craigslist. Our contact gradually receded with time and we have never seen each other since. I did message her once during the pandemic to see if everything was fine with her, but got an unenthusiastic answer. So I’ll just let it be. Although a part of me does hope we’ll meet each other again one day.

Do I have regrets? Absolutely. It was a huge missed opportunity combined with terrible luck and I still think about it from time to time. But, the very next year I managed to find two older FWBs via OkCupid. So, it wasn’t all that bad :p I’ll publish those stories in due time.

That’s it for now. It was interesting to relive some pre-pandemic old memories :)

Source: reddit.com/r/gonewildstories/comments/oot7gu/mfa_craigslist_encounter_in_bangkok_with_a_milf