Advice on setting up some dates / escalation

[ray_zorse]

Question one C1

The first date I have to setup I'll call her C1, I cold approached her in the city and she was soon joined by her friend (C2... has a very similar name) and we went on insta date for some clubbing, it was very fun and there were a lot of laughs as we were daring each other to do crazy shit (see my journal) until they unexpectedly bailed whilst I was at the bar. Apparently C2 was not feeling well... the following text exchange ensued.

Sunday
00:17 Her: Hello!
00:17 Her:
00:17 Her: Sorry
00:18 Me: just finished my long island iced tea feel a bit shitfaced. dont think i can drink another 2
00:35 Her: C2 wasn't feeling well 1 she wanted to leave. sorry. Enjoy!
00:37 Me: thatok we can meet up another day. she probably wouldnt have been down for 3o in any case
00:48 Her: Yuck - her and I are both not into that sort of thing.
00:49 Me: i still have 2 or 3 dares left iirc
00:56 Her: What's my dare?
01:09 Me: u have to have 3some with C2...u can choose one of my pool partners (note: we'd previously dared C2 to ask one of the dudes I was playing pool with, this also as a result of a dare, for a dance. she did it!)
01:15 Her: I'm not really into the 3 things.
01:20 Me: haha well im in a crowded club. just met someone i dated 3mth ago, kinda interesting she has a bf now allthough he sounds like a typical boring nice guy, anyway i'll hold u to your dare later just lemme know when u are in city and ill duck out & meet u.xx
Monday
11:18 Me: hey C1 lets grab a bite to eat or drink in the coming days, so we can pick up where we abruptly left off last time, how does your schedule look before nye?
12:02 Her: Hi Ray, I'm really sorry but I've gone down to the beach for the week and won't be back until the 5th January.
12:30 Me: Thatok what beach is it? i'll be doing something similar around 4th jan so we might just miss each other unless we happen to be in same area
12:32 Her: I'm in NSW, where are you heading to? Maybe give me a call when you're back and we can take it from there.
12:37 Me: sure i'll be in barwon heads from about 4th to 14th however i will be around briefly on 7th and/or 8th so ill let u know when ive worked things out exactly. have fun & don't be naughty (much) hahaha
12:46 Her: Thanks, you too!

So she seems pretty keen, I remember having my arm around her at some stage and getting some cuddles, caressed her cheek a little... and we've invested a fair bit in the text convo so far. Now it turns out I am free on Wednesday night (only) but I'll have my kids with me... so I want to try for easy date, just put the kids to bed earlyish and then cook food and watch videos with C1... just a tiny bit worried about activating the ASD... my questions
(1) should I go for easy date or will it make her feel cheap? (I think I should go for it)
(2) would it be better to continue trying to organize babysitter, my regular babysitter is busy but I could try a commercial one... or ask some student friend etc... (but then I'll have to take C1 on a regular date which is a big deal)
(3) should I tell her about my babysitting issue when I offer insta date? (I think I should... she doesn't know I have kids... downside of not saying is, if she refuses easy date it will be hard to get her to change her mind by giving my reasons)
(4) how to escalate on easy date? I will have to warm her up a bit... so I think the 10 minute rule doesn't apply here or maybe I'll just go for a kiss / makeout, quickly break it off, and then we'll make food and then I'll hit her hard on the couch?

Question two R2

Here's another interesting situation, I invited my friend R1 (again this pair of women has similar names haha) (R1 is a PhD student at my uni from Indonesia, married to a husband who is working in Indonesia, and has a child the same age as my youngest) for a weekend away at the family beach house, she accepts... I also told her to invite her former housemate R2 who is young and hot. I met R2 when I took R1 and a mutual friend (visiting from Japan) out for some drinks a month or so back... after mutual friend went back to Japan I had R1 and her son over for a playdate and also met R1 and son again since then... I remember setting up some flirting and strong EC with R2 when I first met her, she seemed to respond to me pretty well... I got out a few chase frames IIRC... she was disappointed she couldn't come out with us. I asked R2 to my house with R1 but she had to work at that time. Anyway so here is the recent text convo with R1

Tuesday
17:58 Her: Hi Ray. Thank you for coming by yesterday. Regarding your plan to have a holiday in your grandmom's place, when will the day again? Is it saturday or sunday? And can I bring R2 as well?
18:02 Me: hiya it was fun wasn't it, i'll be in bh from 4th to 14th jan so a good time would be the weekend of 10th/11th jan, absolutely bring R2 too
Sunday
12:53 Her: Hi Ray. Happy belated new year . Wish you a better life in this year. So are u still on the plan to go to 10-11 in your grandmom place? R2 is excited and looking forward to it too
14:04 Me: awesome. im just about to pick up kids and head down there now actually. ive spoken to my mum and we are go... it will be a bit of a full house bc sisters birthday but its good u can experience the party admosphere
14:33 Her: Thank you Ray. Please let us know the address so we can find out the nearest station or bus stop from your place. Have fun with the kid.
15:29 Me: (address) but i will pick u up from (station) (v/line). trains are about every hour or so. u can check timetable online
15:48 Me: Thank you Ray. Anyway ...how old is your sister?
17:58 Me: turning 25 as it turns out, sorry late reply

Hmm so these women are keen, it's a bit hard to get a read on the sentiments of R2 as expressed by R1, maybe she just wants a weekend away, but maybe she's excited to be seeing me again? Well I think it will be a bit of a tough seduction environment, lots of people around especially R1... I may be able to setup the sleeping arrangements to get a bit of mileage, since things will be a bit squashy we might all have to sleep in one room, I was thinking of putting both the women in the double bed and taking a sleeping bag on the floor, but it would be only a hop skip and a jump to end up in bed with them... I've also been getting out a fair bit of sexual flirting with R1 just for fun... so it would be great to get some 3 way action going, but they're both pretty conservative so we'll see? How to escalate? Any tips? I was thinking of trying to get something going with R2 and if R1 objects... tell her to watch us going for it and masturbate, then she wouldn't be cheating on hubby... if this works then obviously that's not how it's going to end But I will really have to have a lot of balls and resolve to act if I'm going to get this done... it would be too easy just to let everything slip into platonic territory and I guess that's what they are expecting... probably they expect if I'm keen for R2 then I'll set up a formal date with her later on... so how to get things happening without shocking them / breaking their expectations? Lots of sexual flirting first?

cheers, Ray

 

[ray_zorse]

Thinking about this some more I'll probably call C1 tonight, try to recapture some of the good feelings with a bit of light teasing then proceed as outlined. With R2 the go seems to be to try to separate her from R1 if only briefly in order to feel out the situation. So from the time I pick them up from the station I'll give R2 a little extra attention, occasional touch, occasional strong EC, then I'll say we are going to prepare a meal for the family and have R2 accompany me to the supermarket in the next town while R1 keeps an eye on the kids. I'll order R2 to hold my hand in the car and if she's down for this maybe we park by the beach for a quick makeout, then proceed later as outlined. A lot of what if's, but I think this is a step-by-step I can follow. Any better suggestions welcome

Ray

 

[ray_zorse]

Nogo on C1 it seems...

19:17 Me (by voicemail) Hi C1! It's Raymond... just checking in. I'd imagine you're on your way back from your beach holiday... give me a call when you can. Okay, bye!
20:15 Her (by text): Hi Ray, thanks for the phone call. I hope you had a good nye. It was great to meet you but I feel l should be honest - I just split up with my long term boyfriend and I'm not ready to date anyone.

Oh well fuck it she wasn't that hot anyway, I liked her height and attitude though... and I don't often date Aussie chicks either. I have plenty of responses to this text (to effect that I could relate a similar story and that's why I don't really do formal dates anymore, just hang out, no pressure)... but I don't want to reward this crap with attention and chasing... so I might just ping her again in a few weeks if I can be bothered.

Ray