Ever been propositioned unexpectedly?

Has anyone here ever been propositioned unexpectedly? You know, hit on or someone hinting they would like sex with you in a context that was surprising to you? Men and women, share your experiences.

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  • 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!

  • Yes, because I’m a woman. You will literally have to narrow your search to help me pinpoint an example

  • Have you ever been banged by a group of midgets inside a Volkswagon beetle?

  • It's "little people", you juvenile half-wit, and a gang of us fucked your mom in a Volkswagen microbus as that was the only thing that could hold her fat ass !

  • Tell us if any shorter guys have hit on you and were you disgusted at the thought?

  • Tell us about a fat ugly man, with orange skin made you an offer to see him at a big house in DC

  • Wrong guy, you're looking for Joe Biden.

  • Biden’s not fat...Trump weighs 260 or so...he’s so fat he can’t see his cock and his Eastern European whore wife can’t even fuck him csuse his belly gets in the way

  • Hmm, I didn't know your name was Trump.

  • I haven't seem my gf in weeks for some pussy. The same thing for my mom and her bf. Last weekend she asked me if I was horny and wanted to have sex with her. I said YES and fucked her like there was no tomorrow. My mom moaned like a whore the whole time and especially when she felt my semen injecting into her pussy.

  • 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.

  • When I was in my late teens early twenties my mom started giving me a hard time about not helping others in need. I passed by a woman who was trying to change a tire and for whatever reason my mother voiced popped in my head about not helping. So I pull over and help this woman. She all flirty the whole time I'm changing the tire. Then I get done and she asks how she can repay me, I tell her no need, happy to help. That's when she leaned in close to me, cupped my balls and asks if I'm sure. We fucked in the backseat of her car, and then went out separate ways.

  • 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'm a married woman in my early forties and work in a factory with mostly men. This guy in another department will often come help in my area when we need it. He always wants to work with me because most of the time he talks dirty and propositions me. He's in his late twenties I would guess, so still a kid and I don't want him to get in trouble because he really is a nice kid. He says some of the most graphic things though. Like he keeps telling me how big he is, and he is right, he showed me a picture of his thing and he is well endowed. He tells me what he would do to me if I would have sex with him. He even told me one time that we didn't have to do penitration, he would just give me oral sex until I was satisfied and he would go home and take care of himself. Obviously I keep telling him no, but that doesn't stop him from trying. To be honest I have pictured his large thing in my head a few times and found myself getting aroused. I would never cheat on my husband though.

  • You don't think your husband hasn't fucked around on you? You should be fucking that dude at work. He has a large dick and he's willing to lick your pussy without fucking? Him licking your pussy is not cheating. It's only cheating if you fuck, which obviously you want to or you wouldn't be thinking about his big dick nor would you be willing to work with him. You will fuck him, give it time.

  • Let him do it. Getting your pussy licked isn’t cheating.

  • Funny your wife told me the same thing

  • Hmm, your husband told me the same thing.

  • 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.

  • Why do women in their middle age, need to be convinced to fuck somebody in his 20's?
    I hit on my friends single mom for ever before she finally let me fuck her. She just kept asking me why I wanted to fuck her. I told her straight up it was because she was hot and it would be fun. She kept getting hung up on the age thing like we were going to date. I kept asking if she wanted to date, she said no. I then asked what's the problem? Neither one of us wanted to date, it was just sex, and it would be fun. After 4 months of asking her she finally had sex with me. FOUR months to decide to fuck? Really. I was about to give up on asking by the time she finally asked me if I wanted to fuck.

  • Right! You would think middle aged divorced women would be dying to fuck a young stud. Girls my own age are easier to hook up with than a cougar is.
    My neighbor lady is divorced. I mow her lawn wearing only shorts and no shirt. I work out and have a good tan. I'm not ripped by no means, but I'm not a scrawny pale white kid neither. I'm 18 and yes still live with my parents, but I own my own truck and have my own money. She watches me mow her yard but when I flirt with her and make suggestions, she always shuts me down and says I'm too young. I know she not 40 yet because I heard one of her friends tell her she would be over the hill soon enough. That same friend told her she would dry up if she didn't get laid, so I also know she doesn't have a man.
    She fuckin hot too, the things I would do to that woman if she said yes. Mmmm, I would lick her fucking pussy and FUCK the shit out of her. I'd smack her fucking titties around and suck on her nipples. I'd smack that ass while I fucked her doggy style. Bitch knows she wants me, she just needs to give it up. I'd lick her fuckin pussy until she begged me to fuck her.

  • When I was younger, my girlfriend and a group of friends used to go swimming in this small river. We would walk up this farmers lane to a bridge and then inter tube back to the group. We only had 2 inter tubes. So one day my girlfriends sister was a little tipsy from drinking, but she wanted to inter tube. She demanded that I be the one who take her, eventhough her boyfriend was there. I agreed and started helping her down the farmers lane for the mile walk. Along the way she stopped and said she had to pee. She stripped her bikini bottoms completely off and handed them to me. After she finished she asked if I liked watching. Then asked if I wanted to fuck her. I thought for a minute that I shouldn't, but something inside said do it. So I bent her over a log and fucked her from behind. Then we continued on. When we got back, my girlfriend was upset we took so long, I played it off as her sister was drunk. Weeks later I found out my girlfriend and her boyfriend had snuck off and had sex the same time we had done it. Somehow that little voice in my head knew and that's why it told me to fuck her sister.

  • I am a woman and during my first year of college I worked part time for this woman at her shop just doing things like stocking and cleaning. I went to her store the following year and we talked for about half an hour then she asked if I wanted to come over for dinner and I took it as a friendly invite. She hit on me after we ate dinner and I was so shocked but left feeling some what flattered.

  • You should have let her lick your pussy. Many college girls take that time to experiment, even if they know they aren't gay. My wife said she knew she wasn't gay but still let her roommate lick her pussy when she was in college. She said no man has ever licked her pussy better than her roommate, and not to brag, but I'm pretty damn good at it according to her.

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