I was 22 at the time and I was at the height of my MILF fever. I was travelling around Asia and my last stop was Hong Kong, great city! For a few years prior I would use this dating site called Tagged (I don’t recommend it now it’s become overrun by fake profiles and scammers) and I’d shoot my shot at all the attractive older women I could possibly find. North American women weren’t too keen on me, probably thought I looked too young and was immature (I was) so I would set my search options to other countries and check to see if the women there might be interested. I set mine to Hong Kong and found a lot of beautiful older women and they were very open and friendly to me. I remember when I first laid eyes on this one woman though holy fuck she was perfect. She was 42, Filipina, mom of 4 (her kids back in the Philippines), and judging by her photos she really liked to show off her beautiful body by wearing short tight dresses and high heels. She lived and worked in Hong Kong as a caregiver. I was head over heels gushing like a school boy when she responded to my message and gave me her number so we conversed on WhatsApp for a while and sent each other photos back and forth, I lied about my age on my profile though and said I was 26. Finally I was in Hong Kong and luckily on a Sunday because that’s when all the caregivers get the day off from work, go out with their friends and have fun (Other nationalities who live there would refer to Sunday as “Filipino day”). I texted this woman and surprised her when I said I was in Hong Kong, asked her out for a drink that night and she agreed last minute. She was much sexier in person and a lot of fun to drink with. She wore a long sleeve black shirt, short black denim skirt and these funky platform high heels. We first grabbed food at, you guessed it, Burger King 🤣 got a good feel of each other so we went to some bar, she leaned in for a kiss and I asked her if she wanted to join me in my room for some more kissing time. So I paid the bill and we were on our way, I was over the moon going back there with her and I had such a hard time holding back how horny I was feeling, even once we got in the elevator I went in for another few kisses and put my hand up her skirt. After we each showered I told her to keep her high heels on during sex and she dove straight to my dick giving me the best blow job I think I ever had. She had a way of putting my balls in her mouth and tickling them with her tongue which was a sensation I’ll never forget. We fucked but I didn’t last too long 😅 she said I was her first time with a much younger guy, felt honoured to be honest. Then she spots my passport and sees my birth year then confronts me about my actual age, I come clean to her. She didn’t seem that angry (at least I wasn’t a minor) but she started joking about how she should be thrown in jail for fucking me and I kinda liked it, turned me on. She’s putting her clothes back on because her caregiver family is wondering where she is but I’m getting hard again 😈 she was standing near the door on the phone and I’m on the floor still naked feeling her legs up, I needed another round with this woman because I wasn’t sure if I’d get the chance to see her again. She finishes her phone call and says to me “I have a daughter who would kill me if she found out I just had sex with you” her daughter was just 3 years younger than I was. She grabs me by the earlobe and pushes me back on the bed, lifts up her skirt and sticks my cock through her panties and rides me while she’s fully clothed, this time I’m lasting a lot longer. She’s shaking the bed, her jewellery is rattling and she’s making a lot more noise now, she’s gone totally wild screaming her head off! At one point she yells “Oh Harry Styles!” (I didn’t look like him, don’t know why she screamed this 😅 this was back when One Direction was the talk of the town) and BAM there I go filling up this naughty MILF with more of my cum. What a night to remember! I put some clothes on so I could walk her out, told her that I’ll be back in HK again hopefully and we could see each other. I did end up going back a year later and arranged a date with her but she cancelled on it last minute sadly. Not in touch with her anymore but I’ve creeped her FB and I see she’s found a man her age or older, good I hope she’s happy. I still have all the pics she sent me though so every now and then I’ll jack off to her sluttiest photos and remember the awesome night we had together. I wonder if she had sex with anymore younger guys after me or if I was just a one-off.
Source: reddit.com/r/Erotica/comments/sxefkd/that_one_time_i_hooked_up_with_a_milf_in_hong_kong