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So I have been talking to this nice older woman. She has a son, is single, and is rather nice to me. She messaged me out of the blue last night at 10 talking about how she wants a boyfriend for Christmas and that made me under the impression that she might possibly be interested in me, especially since she finished the conversation with XOXO.
If you wanted to know, yes I want to fuck milfs and I’m 18 so it’s not like I don’t want her interested in me.
Sure, older women can be much better at sex and many know how to take the lead. Message her that you want a girlfriend for Christmas followed by a wink emoji and XOXO. Keep it simple and let her make the moves.
I usually agree with most of what you say, JD, and I agree that if the OP messaged her along the lines you suggest he should let her make the _next_ move, but if he's really interested in her, he shouldn't expect her to do _all_ the pursuing.
We don't know what sort of a person she is, but we do know she's older than him, and it's possible she might be worried that he thinks she's _too_ old. So maybe she's being coy and not laying her cards on the table because she's afraid he'll reject her.
It's the usual dance, of course, but possibly complicated by the older woman-younger man thing, and all that follows from that in terms of social norms and expectations. I think OP would be wise to make sure she understands that he actually likes the fact she's older.
Get some Christmas gift-wrap. Cut a piece wide enough to cover you from the top of your pubes to just below your balls, and long enough to go around you. Wrap this around you along with a ribbon, and put a stick-on bow on your crotch. Take a picture of yourself from waist to thighs, and send it to her along with a note saying that you've heard a rumour that she might be on Santa's very naughty list.
You're aiming for something that's a little jokey, doesn't allow you be identified from the photo, and allows you both to laugh it off and retreat without either of you feeling like an idiot, but is also a definite expression that you're interested.
Hmm, I’m debating this but I’m poor and I don’t know if I should go this far to quick, not to mention I’m in a dorm so I don’t have the time to make it ATM lol
Damn! Too poor to afford a roll of Christmas wrapping paper? I guess you could recycle some after the day. 😜
Sounds suspiciously like you're wimping out, bro.
Like leggs says, you live to regret this sort of thing if you don't give it a shot. Of course, you might live to regret it if you do, but the list of things I regret _not_ doing is longer than the one of things I regret trying.
Assuming this post is real...
Sure why not go for it? She is older and more mature than silly-ass hoes your age so even if she IS being a prick teaser, it is not like she is going to act like a dipshit just because you asked her out.
Next time you two can talk in person or even over the phone, just say, "So when you said about needing a B/F, is there anyone in particular you had in mind?"
Or maybe, "...I would like to fill that role".
Not like I am so great at this. Besides at my age, if an older woman wanted me, I would puke.
ONE thing though - if she is prick-teasing and does NOT mean she wants you, try not to get too disappointed. Women have stupid ways of leading guys on sometimes. In this case it does sound like she is possibly interested in your company but you need to ask. if she says "No" well at least you tried. If she says "yes", buy condoms.
If you do not ask at all, you will regret it later. When I was younger There was a lady I might have had a chance to sleep with but of course I had other things going that seemed more important. I am not sure what would have happened. And almost 30 years later, I still look back and think "what if..."
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Just go and fuck her.
Same thing happened to me and I ended fucking her. She is gorgeous. She has a daughter of my age. I am also dating her daughter. Her daughter also knew about me and her mother. And I am just planning to fuck both of them together. Just go and fuck her.
as long as they have no active partner i dont see why not, kids are the only obstacle
a lot of assuming going on here so tell us -
How or where did you meet this woman?
If in real life, you might have a chance but if it was some dating site or one of those craigslist type sites, it probably is a prostitute or some other fake.
She said boyfriend, not fuckboy, so depends what your intentions are. She can already get laid any time she wants. You however can't, considering you're too broke to pay for it. So just keep that in mind before you assume she just wants sex.
Did you find her on craigslist? It's either a scam or she's a prostitute. No one else writes that way. I want a boyfriend for Christmas XOXO? Just leave your valuables at home if you plan on meeting her.