Ever been propositioned unexpectedly?

42 single mom. Three weeks ago, while shopping at Walmart I ran into one of my daughters Ex boyfriends. Haven't seen him oh about three years. We caught up on life . Before we went our ways. He asked me out to dinner and a movie. I replied how old are you now? He said 19. I said let me think about it.

Someone walked up to me and said "Nice shoes wanna fuck" I said sure and we did..
They were just regular tennis shoes nothing fancy lol

Yes. A babysitter once hit on me. She was a good looking young adult, but she was married and I was able to resist the temptation. I later wondered if she was going to get a divorce and wanted a relationship. Who knows what life event will change the course of our lives.

A friend’s mom hit on me at a Bat Mitsvah once.

And? You tapped dat milf ass and leave a thick load in her?

Yeah, this four-eyed cock smoker in an adult bookstore asked me if I wanted to duck into a movie booth with him. It was the first time a guy ever propositioned me. I didn't take it well. Lets just say, that was most likely, his last proposition of the day.

I was making sandwiches in the kitchen once for my son and his two friends who were over. It was really awkward, but one of the friends came in and confessed that he had a crush on me. He then pulled out his hard cock. I was flabbergasted, told him thanks for the compliment but to put his cock back in his pants. He looked beautiful though. He's going to make a girl happy with that thing one day.

Two times for me that I can recall. Once while at a bar a woman came up to me and started chatting. ten minutes into the conversation she asked me if I would be interested in coming home with her to fuck. I was all in until she told me her husband would be there watching us . He wouldn't join just watch and jerk off.

The other time was while driving and a guy flagged me down who was broke down on the side of the road. He tells me he is out of gas and if I take him to the gas station and back he will suck me off.

Hi, I'm hinting in my WhatsApp messages to my sister that I would like to have sex with her. For example, suggesting films that involve incest like A Simple Favour where the main character sleeps with her brother. I tell her that she had amazing hair and that she had a great body. We both have marriages so this a delicate situation.

One of the first jobs I ever had was a census worker going door to door to have people fill out the census forms. I went to this one house and it was just a single man living there. Through the course of the poll he is looking me up and down kind of creeping me out.So all the questions are answered and he says he has a question for me. He tells me he is a sculptor and would like me to model for him, he will pay me $200.00. I was a little leery but agreed to come back. I get there the next day and he invites me in to his studio and tells me to get naked. I'm like what? he says he wants a nude model . I needed the money so I stripped off my clothes. He looks me over and says" nice, now get it hard" .He wanted me to stroke my cock until I was hard or he could help me get an erection. I told him I was straight ,he just laughed say he has gotten lots of straight dick hard and most have blown their loads with him just stroking them. As it turned out he was really paying just to play with some 18 year old cock and as I was already standing there nude I let him do his thing. I do have to say he did get me hard and made me blow my load using his mouth. As he was handing me the two hundred he offered another two hundred to me if I would let him fuck me. I took the first two hundred and got out of there!

My gf made the foolish mistake to ask if I have ever paid for sex. I have not and told her so. I then asked if she had. She laughed and said No. Then I asked if anyone had ever paid her to have sex with them. She paused and said Yes. Turns out she took $200 to suck a guys dick at a bar on spring break and up until 2 months before we met she was the paid dinner date of a man 35 years older than her. She’s 25. It took a bit of prying but she admitted that for $1000 a month she had dinner with him and sometimes (which means most or all) he would fuck her. And I mean FUCK her.

Skank. Did you find any moldy old man cum up in there?

You have no idea. Dude the guys 65, more money than he will ever know what to with in 10 life times. I took a lot more prying and drinks but he makes her dress up in a school girls uniform complete with pig tails and a sucker. After she is dressed and ready she meets him in his bedroom and kneels, takes her sucker out, opens his robe and starts to suck him to get ready. Then he makes her decide where. And I’m not talking about which room. And she can’t pick the same (gag) hole 3 weeks in a row. So 2 weeks in the pussy the next week it the ass for my girl.

At dinner she has to remind him to take his viagra by saying “Now did you take your vitamins? You wouldn’t want to disappoint your baby later would you?”

I’m a kinky fucking freak but this guy has me beat by miles.

I was on the road for business a lot, and would stop at malls to take driving breaks, eat, use the men's room, etc fairly often. Once met an absolutely gorgeous, fitness model-type, sweet, and insanely nice woman, chatted with her, and was asked to help her find boxer for her bf. She was hot, I needed the road break, and I figured..Boyfriend. No doubt. Help her anyway to get some time with this gorgeous creature, then hit the road happy.

We hit a few stores, and with each one, she got more physical and close with me. I had my arm around her a few times, too. We finally get the boxer shorts and I tell her I need to hit the road again. She pulled me in, gave me a deep, where did this come from but I'm not complaining, kiss, thanked me for keeping her company, and reminded of of the Ramada Inn in the mall parking lot.

We ended up having an afternoon and early evening of amazing sex, checked out, and that was the end of it. Nothing further, no I'll text or call you. Just simply..We met, hit it off, had sex for hours on end, and left. Best road trip I ever had. She was just so damn beautiful and fit. Above my level, to be honest. But a great time.

I work as a waitress in a somewhat upscale restaurant in NYC. A couple of years ago I served a couple who looked to be in their early 50's. I was 22. We chatted and they seemed to want to know more about me on top of taking their order. They looked nice and we chatted. I gave them their bill, picked it up, and went back to process their credit card. On the slip they not only gave me a huge tip, but added their phone number and wrote "My wife and I would like you for dessert" and included their room number for the hotel across the street. It was a little weird. If I weren't in a relationship, I might have gone over.

When I was in sixth grade, an older lady swam up to me at a hotel pool and asked if I wanted to follow her to her to her room so she could be my first.

How much older was she? Like your mom or teacher's age? Did you go through with it?

Like, early 40s, so a little older than my mom. And yes I did.

Good man. Must've felt damn good in her. That would be so hot of a confession.

Certainly hope my husband doesn't read this.

Well I’m not sure if this fits but here goes. I’ve been propositioned. Yes. I had just recently met the most wonderful man. It was our 4th date. Everything was amazing! Dinner, flowers and a gift of new pair of boots (tight to my calves and shinny black) I had had my eye on. As my bf walks to the bathroom a very handsome older man and comments on how nice my new boots are. Then he says looking towards my legs. I pull them away from him. He leans into and says “I’ll give your $2,000 but I want to see you in you in the boots and nothing else. Hmmm” just then my bf walks up. I smile nervously and go into panic mode. I try to introduce them and realize I never asked his name. He saved me and hands my bf a business card. William, William probably will be able to get any women he wanted. Then I thought that I’d never go through with it. Three days later I was at Williams $2,000 in my bag boots and I am naked I’m surprised but this money will come very handy

Wow ! How much did your husband have to pay for you ?

I had the Airways Transit guy drive me home, then he asked if anyone was home and did I want company.

I’m a doctor and had a patient hit on me several times. I never took her up on it she wasn’t my type.

I went walking in the park with a friend. We were in our 40s and average looking. Well, a couple of guys who were playing frisbee befriended us and they were like maybe early 20s. One of them asked us over to their apartment, but we weren't dumb. They wanted to fuck. We said no way, but we did take their numbers. A couple of months later we called them up and we did it.