Preface I'm a brown guy in my mid twenties around 6'1, body in shape but around 20-22% body fat probably because of bulk. A bit above average overall. Working but living with family. I currently have 1 LTR (21 years old) and 1 plate (19 years old pushing for exclusivity recently) so it's busy managing time for other dates on the side.
These are within the past few weeks. Met them all through dating apps.
-
28 year old hb 7 - Met for drinks. She lives with her parents and I also live with my parents. Met her near her house. Flirting and minimal touch during the date. Went for a walk in the park after drinks. Sat on bench and kino, held hands, arm around her. Went back to my car to "warm up" and listen to songs. Heavy makeout + touching -> LMR when I put my hand between her thighs.
-
44 year old hb 7 milf - Met for drinks. She lives alone but I was in another country when I met her so I suggested a bar near my hotel. Flirting + kino at bar, commented on her ass as a part of a joke. Suggested we go back to my place for a few more drinks on my balcony. Uber back. Makeout and f close. Fingered her ass and she came during the sex (just a bonus because I normally am very dominant recently and lead the girl to do things for my pleasure). And dirty talking throughout sex.
- 24 year old hb 8 - Met for drinks near her place, she lives with her parents. Drinks + flirting. Kino but not much reciprocation at the bar. Went out for a walk. Cold so I suggested let's go to my car. Listened to music. She was reciprocating touch now. escalated to heavy makeout. After first makeout then i pull back, she says she should really be going now. I say ok, and continue talking then escalate again to another makeout, touching around her body, she's also feeling my chest. I repark in a darker spot. She has a bit of LMR. Makeout again, feeling boobs, she put her hand on my thigh, I do the same. After a minute she removes my hand from between her thighs. Says she should be going and thanks for the drinks, I say ok and tell her I had fun.
First and third girls had similar logistics. Maybe my escalation was too much for the location because it can't go much more. I've also heard some guys saying to go to the back seat and make an excuse to strip slowly first before even trying to put your hand near her pussy because this causes heavy LMR. Then she will be more likely to give a blowjob with the right escalation. If there's anything that seems obviously wrong with my escalation let me know.
Unrelated question: How to escalate from finger or two in the ass to anal sex? I've had anal sex before with an ex LTR but didn't warm up properly to it. My current plate and the milf enjoy having a finger in the ass during sex. Is there a way to warm them up to it with just fingers and no butt plug? I'm using adequate lube on my fingers but maybe I need to use much more. With my current plate after a lot of anal play with fingers it becomes too overwhelming so I need to balance the length of anal foreplay with the right time for penetration with my dick.
Durek_The_Bald 5h ago
1/3 women will be strictly no anal. 1/3 will do it reluctantly just to keep you interested (which isn't a lot of fun). And then there's the last 3rd, who'll really get into it. But even they mostly need to be horned up first.
If she's enjoying a finger or two up the a-hole, you're probably good to go for it. But yeah, don't do that for too long. Fingers are more painful than cock in the long run, because your cock - although bigger (hopefully) - doesn't have nails and bones.
"Show, don't tell". When women do slutty stuff, they mostly want be able to hamster it away after-the-fact as something that "just happened". ASL (anti slut defence) is still working in the background, even as you have your dick in her ass. Don't take that away from them by talking too much - unless you already have that sort of rapport with her.
Press your thump against her a-hole, whip it with your dick etc., and see what kind of reaction you get. If it's a positive reaction, it means proceed. If she asks: "You want something?", it means she wants it too, and you both know what that "something" is - she just doesn't want to say it, and probably don't want you to spell it out either.
Fuck her good first, but don't let her cum. Women have post nut clarity too, just like us. The hornier she is, the more relaxed and up for dirty business she's going to be. And if you want to do it again some other time, best make sure that post nut clarity, anti slut defence doesn't do a number on her. A bit of aftercare goes a long way, positive association with the whole thing.
universitythrowaway Should i (x1) 5h ago
Solid advice. About my plate, I don’t try to plan for it to avoid her ASD, mostly just lick my finger and rub her asshole during sex which she loves. One finger in during sex is also enjoyable for her she says the feeling is very filling. Two fingers in and there’s more tension and it starts to go towards me dominating her and her submitting to whatever I want.
When I’ve tried to insert myself in she’s agreed but then stopped after there was too much pressure during insertion. When she’s enjoying my finger in her ass during sex she’s normally riding me. The current way I’ve been trying to penetrate with my dick is in missionary position with her legs over my shoulders. If there’s an easier position that allows for more comfortable initial penetration I’d like to know.
No-Stress-Cat 33m ago
Try trimming your fingernails and file them smooth. You'll both appreciate it. ;)
mattyanon Admin 1d ago
So probably 25%.... look my dude, that's way too fat.
First date. Fair enough. Needs longer.
okay
again..... first date.... fast...... needs more time.
Can you get them to your place rather than car?
as everything else..... one step at a time.
yes
this will vary depending on her experience.
universitythrowaway Should i (x1) 1d ago
Haha don’t worry I know how to estimate correctly, not one of those people that think that bodybuilders have sub 5% bodyfat. I agree with you though. Going to go on a cut soon. My build has a lot of muscle so it doesn’t appear too fat but could definitely help with a leaner look.
Currently living with my family so this isn’t possible. I can get a hotel or escalate in the car which isn’t ideal.
I don’t mind if sex doesn’t happen on the first date. However, I don’t want to try to escalate things to that point on the first date and have that be the reason why there’s no second date.
[deleted]