getting this MILF to put out - advice please

[Scormus]

Guys,

I met this 40 year old MILF online, she is divorced with 3 kids (yes I know, "wtf are you doing, pump and dump her, etc.").

She has amazing looks and is a former model, even at her age she still rates 8/10 on the hotness scale, great face and sexy body.

We went on the first date last weekend, she'd booked a hotel for herself. We started at around 3 PM, did some bar hopping and took her to dinner that started late (the restaurant didn't have tables any earlier than 9).

After dinner and before the dessert I stood up, leaned down to her as she sat, and went in for the first kiss (easily 20 seconds, working my lips onto hers, long and lingering and bordering on making out). A long enough first kiss that I knew I was in.

Didn't think I would be able to get her back to mines for some action that night as she had paid for her hotel room after all, so I took the cab back with her to her hotel (about 15 minutes walk from my home).

Took her to the door and 2nd kiss again long and lingering and pretty much a make out session but without the embrace, I had my hand on the back of her neck.

We agreed to meet in the morning and I thought was going to get her back to mines and get some action then.

But she dropped the bomb she had to leave at lunchtime (stayed till about 1 PM).

I walked her to her car, we embraced and made out passionately, for about 5-10 minutes, before she said she really had to go. I was kissing and biting her neck and ear and she was kissing my neck back but not as hard as I was. Was getting some tongue in on the mouth to mouth kissing as well.

What bothered me was when I said, "I get it, we need to leave something for next time", after she said she really had to go, and she said, "This is the next time." I think what she meant was she wasn't putting out next date and this is the same physicality we would have the next date.

Via text messages after:

We agree to have the 2nd date this weekend, she says she is driving over to my city again (about 40 minutes away) with a friend who is seeing her own guy. I ask if she is staying over at mines, she says she is booking a hotel again. I ask if its her friend's first date with the guy, she says no its been an ongoing relationship. I say it makes no sense if she ends up alone in the hotel room and that she should stay at mines, its more romantic and practical. She says she feels we don't know each other well enough yet to stay over this weekend, but that she does look forward to the time when we do so.

What's the right play here guys? How do I get laid? I'm afraid this gets ridiculous and she pulls crap like not staying over again for the 3rd date.

I'll obviously try to get her to come to mines, even if she won't stay over, I do have her making out with me already so I should be able to heat her up and get her to come up.

Thanks in advance for any help guys.

 

[jjacob]

Girls that I've dealt with usually don't like you overtly planning for a situation to get laid unless you've already had sex a number of times. She can tell you have your feelers out trying to figure out whether or not she wants to have sex with you.. probably re-enabling her ASD when you were already knocking it down. Honestly I would do things that make it appear like I wasn't even thinking about the logistics of getting her alone. I've purposely not brought a phone charger and a change of clothes when it's already obvious I'm staying the night, puts the hamster into overdrive, just sit back and pay attention to signals she'll be throwing towards the end of the night and pounce.

 

[Greasy Pig]

Yeah, you need to be more subtle. Your desperation is assaulting every one of her senses and you run the risk of turning her off.
Just chill out, fill her full of booze and be at your coolest, funniest and ****iest.
I'd recommend you don't even try for the kiss this time.
That'll throw her hamster into overdrive.
Show her you like her in other ways (kino, take a keen interest in things she talks about) but at most, give her a quick peck on the cheek and walk.
Hopefully she'll think your losing interest and that invitation to her room will come a date earlier than she planned.

 

[ecko280]

I don't know about you, but when i am making out with a girl it is because we are about to f**k. I don't understand why guys make out so much and nothing happens. That is a lot like high school. Two kids making out all night.

What i recommend is to kiss for a few seconds. This will show her that you are not desperate and she will want to kiss you more because you gave her a little taste of it.

What i recommend now is to play it cool and don't call or text her for a few days. After a few days pass, cal her and invite her out for drinks.

 

[Warrior74]

Didn't think I would be able to get her back to mines for some action that night as she had paid for her hotel room after all, so I took the cab back with her to her hotel (about 15 minutes walk from my home).

Took her to the door and 2nd kiss again long and lingering and pretty much a make out session but without the embrace, I had my hand on the back of her neck.

We agreed to meet in the morning and I thought was going to get her back to mines and get some action then.

So...let me get this straight. Chic books a hotel room you make out at the door and you GO HOME? WHAT? She ain't brand new to the rodeo son. She's got three kids and she knows her puss can take a pounding and really needs one. She was willing to spend her money on a room and you didn't even ask to come in? When I hear the words "We agreed" I hear either 'she told me'; or 'I wussed out', which one is it?

"I get it, we need to leave something for next time", after she said she really had to go, and she said, "This is the next time."

A. Why are you assuming that? Did she say that? Or did you think she's a "nice girl" who would want to hear that?

B. She gave you a window of opportunity and you pssyfooted around. This is next time, because next time she will be with a man who knows what to do with a 40 year old milf who books her own hotel room. Which is why you got this handed to you.

" she feels we don't know each other well enough yet to stay over this weekend

Honestly you sound a little desperate and non agressive, a dangerous combo.
I agree with the other posters, you need to make it light and easy and fun. You need to walk her up to her room and ask to use her bathroom. You need to makeout on the bed. You need to bang her. You need to not spend the night and leave. (gotta let my dogs out, meeting in the am, whatever..) You need to keep it fun and light the next day and make her wanna come back.

 

[Scormus]

Response

Warrior,

I take your feedback on board but to clarify:

a) we were actually in the hotel lobby not the hotel room door itself, if its the latter I'm going in. The 2nd kiss wasn't a proper make out either more like 30 seconds to a minute of smooching. On the cab back to her hotel she said I could get off at mines then she gets to the hotel alone I said no I live nearby and would go with her and could walk back home. For what it's worth it was a cheap hotel just a place for her to crash. I think this signalled to me that in her mind sleeping with me on the 1st date could get her pump and dumped.
b) it looks like she made up her mind not to sleep with me that night
c) I think there is still a good chance she puts out on the 2nd date, just that she won't sleep over. These are 2 different things.
d) important thing is I am still in, interest level still seems high and from texts exchanged recently she has basically said she looks forward to staying over, just not on the 2nd date yet.

 

[Zarky]

Gotta agree with Warrior74.. she's a 40-something MILF.. there's no excuse for not banging her on the first date. Not sure what you did or did not do, but you moved too slow.

When she said "This is next time," that says to me that she wanted to bone already.

 

[cordoncordon]

I disagree with most of the posters here...based on what OP wrote, which is all we have to go by. I believe she was turned off by OP's obvious desperation, and she was not going to sleep with him no matter what because of it. In fact I believe if OP has pushed any harder, as some here are saying he should have done, I believe she would have been totally turned off and a second date would now be out of the question. OP to me you really came off as way to interested, way to desperate for sex. Stop that.

OP here is what you do. Go out with her again this weekend, and do the exact opposite of what you did the first date. Don't kiss her, don't caress her, don't sex her in any way. Don't imply anything about you staying at the hotel or her staying at your place. Don't imply anything about a third date either. Be fun, carefree, exciting...but don't push for anything. Talk about other girls you are dating. Talk about all of the fun things you are going to do in the near future and DO NOT INVITE HER ALONG. Do all of that and I can promise you that by the end of the night she will be thinking WTF? and will be the one jumping YOU, not you jumping her.

Trust me on this. Do it. And report back.

Good luck.

 

[nismo-4]

OP, the very fact that you're having trouble and asking this is a big sign of your desperation.

Judge nismo has found you guilty of displaying desperation and illegal use of a pedestal. Pay your fine of 2 blue balls and then stop chasing her. Desperation is a turn off. Shown very much here.

BTW, sex is spontaneous, not negotiation. Keep on negotiating and being desperate if you want to, just don't whine when your princess is in another castle.

Case closed. Exit stage left.

 

[Zarky]

OP, the very fact that you're having trouble and asking this is a big sign of your desperation.

I disagree, I think it's a big sign of his lack of experience in these types of situations. 40 year old MILFs really shouldn't be that difficult to game.

Judge nismo has found you guilty of displaying desperation and illegal use of a pedestal.

I didn't get "desperation" from his posts so much as "inexperience."

BTW, sex is spontaneous, not negotiation.

I disagree, I've negotiated a lot of sex. Pretty much all of my sexual exploits have been negotiated, even if not explicitly. For example, last summer I dumped a chick who wouldn't put out on the first date. 2 weeks later she called me out of the blue and suggested I come over and f*ck her that night. That was a negotiation, even if not explicit.

How and when sex happens initially is always negotiated. Even if not verbally.

Keep on negotiating and being desperate if you want to, just don't whine when your princess is in another castle.

As an aside, I don't care for that phrase, because it assumes there is a princess somewhere. There are no princesses. The sooner men realize that, the better off they are in life.

 

[Scormus]

Inexperience

Indeed it is inexperience that's going on here.

To summarise I am a late bloomer, had low confidence for a long time, and ironically online dating saved me.

I still can't hustle phone numbers in person to save my life. Though I think that will change as my online dates prove that I am more attractive than I gave myself credit for all this time.

To each his own but I find the ability to consistently get dates online very comforting. Some of them are much better quality as well, have a 30 year old doctor with no kids or baggage to see soon.

I should never have let a string of real life rejections get me down and doubting myself, I wasted a few years!

 

[visions]

Indeed it is inexperience that's going on here.

To summarise I am a late bloomer, had low confidence for a long time, and ironically online dating saved me.

I still can't hustle phone numbers in person to save my life. Though I think that will change as my online dates prove that I am more attractive than I gave myself credit for all this time.

To each his own but I find the ability to consistently get dates online very comforting. Some of them are much better quality as well, have a 30 year old doctor with no kids or baggage to see soon.

I should never have let a string of real life rejections get me down and doubting myself, I wasted a few years!

cold-approaching is a big confidence booster and improves communication