I posted an ad a few years ago on Craiglist in the casual encounters section. And a few hours later got an email from a woman so seemed real, We emailed a few times then exchanged numbers and started texting and set up a time to meet the next day. She was really cute. Mid 40s, tight body- 4’11 and less than 100 pounds, so i was hoping she had a pussy to match and she did.
I met her at a Denny’s, so that we could meet and make sure neither of us were crazy. We sat down and I ordered coffee and we awkwardly made small talk for a few minutes. I got the sense that she didn’t really want to talk and we both knew that we were going to a hotel afterwards so I just asked her if she wanted to get out of here. She eagerly said “yes” and said that she knew as soon as she saw me get out of the car, haha. I threw a few bucks on the table, not wanting to wait for the server to come back and ask for the bill, etc and we were off. We drove separately to the hotel we had discussed previously and I booked a room on my phone during the drive other there.
As soon as we got into the room and put our things down, I grabbed her and started kissing her, starting to feel her up as out clothes started coming off. Once I had her naked I started sucking on her tits before I started to go down on her, hearing her moan and say “oh yes”. That was her phrase and she said it a lot during our first meeting. After she came on my mouth and fingers, I laid back in the bed and had her suck my cock. She was really giving it 100% and it felt great and looked amazing seeing my hard brown cock, going in and out of her pretty little face.
I was ready to fuck her so I shifted and got on top of her. We should have talked about protection but we were both too horny and I just slid inside her. And as hoped…her pussy was as tight as her tiny little frame would have you imagine. I was in heaven fucking this tiny little woman, her pusssy sucking and milking my cock as I pounded the shit out of her.
After a minute she said she was going to cum and came all over my cock, I could feel her pussy twitching. She came more easily than any woman I’ve been with since or before. And even few minutes she would have another orgasm. Wish I could do that for all women, haha.
We fucked on and off for 3 hours that day. In every position I could think of. I came 3 times that afternoon and all of my cum went deep in her pussy. After the second time I came, I had her suck my clean and told her how much I liked that, so everytime we had sex over the next few years so knew how to clean off my cock and I never had to ask her again, which made it even hotter…like she just wanted to serve me.
After a few months she started to get clingy and I started to have other FWB so we kinda drifted apart as I didn’t want to hang out with her much. But every so often I would get the urge to fuck this petite little MILF so I’d text her and she was always happy to hear from me and would usually come over the same or next day and get a nice pounding and a load of cum in her pussy and mouth before she’d go home. Not to sound like a douche, but she liked her so much she would cheat on her boyfriends with me. They were older and just couldn’t fuck her hard like I would so I didn’t have to convince her, just some flirty messaging and asking if she’d like to come over sometime. The first time I saw her after a long absence and she let me film it. There’s a part at the beginning where we are making out and I’m almost naked but she’s fully dressed at this point and she says to me “I didn’t think you’d ever ask me to come over here and fuck you again”, then I push down on her shoulders and she gets on her knees to start sucking my already hard cock. The side shot of this petite little MILF on her knees servicing my cock so she can get fucked by it. One of my favorite memories.
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Source: reddit.com/r/gonewildstories/comments/i312lz/my_petite_milf_forever_mf