"Sugarbabies" / "Arrangements" Amateurs or Not?

[QUOTE=IluvSmellyFish;2320796]I would bring over a few bottles of wine, the willingness to listen to her tales in person, and a very upbeat attitude about how you are going to help her get put of trouble (if the tales of woe get too depressing, you might end up as her shoulder to cry on or spend an evening in the friend zone). A more experienced brother correctly posted that wine helps bring folks together in ways that coffee simply cannot.[/QUOTE]I would just say something like "I have helped out a few girls with their problems over the years, even financial ones, but we were dating. I,m not saying that's what you had in mind, but I just wanted to put it out there.

If that seems a little too forward, lets just have a look at those bills and see if we can prioritize them in a way that's not so scary. But I'm interested if you are".

And then shut up.

Sounds like something a little too close to civi dating and I doubt I could pull this off. But the cut to the chase approach works a good percentage of the time.

Holidays were tough for me as no alone time and its hard to string several pots along for a few weeks trying to keep their interest while offering nothing.

So this week I was hopefully but looking grim.

18 year old who I have visited twice and only got as far as pussy licking seems to never be available to meet. She used to be available all the time. But doesn't stop her from talking money woes.

23 year old. We have talked for months. Great personality, I think we click great. Schedules never mesh up. This week they do but she is saying lets have a couple of public dates first. Ugh. I just don't think this will ever happen.

24 year old. Sexy, nice, sweet, no transportation. Thought this week might work out though. But she informed she has another suitor offering serious dollars but he sort of makes her feel like a prostitute. So nice guy me might win out but I worry about taking her to he FC.

22 year old. Very pretty, 10 in my book. Seems mentally all over the place. She clearly is seeking help but she also is struggling with what that means. Seriously doubt she ever sees me.

34 year old petite MILF, see 22 year old above. Chats are always sporadic and random but always indicates a willingness to meet but never responds to a specific request.

31 year old MILF see the two above.

25 year old who I have hooked up twice. Very hopeful but she is coming off the flu. May not feel well enough to get together which is a shame because she is an adventurous sort in bed.

I would sip a little wine -but make sure you take some Cash with you. Ask her if she has ever heard of an SD, that will open the door for a convo and an offer. Depending on what she says you can tell her you are one and you are "in between " Sugarbabies at the moment and could make an arrangement that will discretely help you both out. If she reacts negatively then drink up and get the heck out of there.

[QUOTE=Zauriel;2320773]Seeking advice here:

A social media "friend" (I have never met her) posts all the time about being broke and how close to financial ruin she is in. She is also hot and does some pinup / nude modeling for female photographers. I opened the floodgates via PM and asked about her troubles and the deluge of her tales of woe began. Sensing an opportunity, I told her "I bet we could find some way to get her some money" to which she replied "I would be eternally grateful!

Now I am going over to her crappy apartment to talk about "my ideas" for her. I don't want to misstep and have several scenarios loosely in mind.

What would your next step be?[/QUOTE]

[QUOTE=Zauriel;2320773]Seeking advice here:

A social media "friend" (I have never met her) posts all the time about being broke and how close to financial ruin she is in. She is also hot and does some pinup / nude modeling for female photographers. I opened the floodgates via PM and asked about her troubles and the deluge of her tales of woe began. Sensing an opportunity, I told her "I bet we could find some way to get her some money" to which she replied "I would be eternally grateful!

Now I am going over to her crappy apartment to talk about "my ideas" for her. I don't want to misstep and have several scenarios loosely in mind.

What would your next step be?[/QUOTE]This is just one mans view, but going over to her apartment during the day would be an unusual situation for me, so I'm trying to imagine what I would do based on what you've said so far. I say that because taking her out for drinks to discuss is usually a much more sure thing -- not really because the effects of alcohol directly, just the evening atmosphere and the fact that the mere smell of alcohol starts making them feel licensed to let their hair down a bit.

But, since nights aren't an option for you -- I would ask her why she's only done nude modeling for female photographers? It's one of those questions where her response (regardless of what it is) is either going to fling the door open for you and make things easy, or raise a red flag so that you don't waste any more time than necessary. Even if she says something like "I wouldn't be comfortable with a male photographer" you say "what if he's not really a photographer" or "what if I don't own a camera" or something like that to try to lighten the mood. But like Hollywood said, I'd get right to the point however you do it, especially if you're under watch.

The one thing I'd be aware of is if her answers indicate she a lesbian (as opposed to bi). It's likely not her reason for female photographers but the thought came to mind when I read that. If you do get that vibe, I'd just avoid her altogether. There are some SBs out there who have girlfriends and don't even like cock, but put themselves out there anyway as an income source. I personally don't feel they are worth 5 minutes of your time.

Have an interesting weekend coming up.

SB#1 I will see on Friday night. Treating her to a spa day and then dinner and some fun. It is her birthday. I average about 2 visits a month with her because I only see her when I travel. She recently got a boyfriend and I thought that might be the end of it, but she says that she keeps these parts of her life separate. She recently got her own apartment but I am not sure I want to venture there for fear of her boyfriend stopping by. She is a full time college student and works 25 hours a week. She was thrilled when I told her about the spa day.

Pot#2- found on SA. Messaged her months ago with no response. I sent her a last ditch message saying by now you have discovered that many of the guys are creeps. Give me a chance letter. She responded and we have been emailing each other. She is a full time college student and pursuing a graduate degree after this next semester. She is drop dead gorgeous and super talented- photography, piano, speaks several languages. Her posting on SA says she is seeking moderate support (up to 5000.00). I can only see her about twice a month when I travel for 2-3 hours at a time. I will shoot her 200.00 per visit and see what happens. I am taking her to lunch on Saturday. Any advice would be appreciated.

Sb#2-24 year old social worker with 1 child. Boyfriend dumped her after child was born. She is struggling to make ends meet. She does have an apartment we can use- kind of a dump, but it's ok. We skipped the m&g our first time and I brought her some Starbucks and some VS lingerie and she was thrilled. Had her clothes off in no time flat and sucking my cock within 10 minutes. Nice little body. Took direction very well. No complaining even when I deep throated her and made her gag- she was right back on it without being told. Tight little pussy. Would have never guessed she had a child. Blew my load right into her mouth and not 1 complaint. I am traveling for business and will see her on Sunday morning at my hotel. The only thing I didn't ask for was Greek and May try that this weekend.

So I have 2 for sure meetings and 1 m&g this coming weekend. If the potential starts to give me GPS would it be worthwhile to tell her that I have two 9's that accept 200 per visit??

[QUOTE=BeardedMan67;2321159]Have an interesting weekend coming up

So I have 2 for sure meetings and 1 m&g this coming weekend. If the potential starts to give me GPS would it be worthwhile to tell her that I have two 9's that accept 200 per visit??[/QUOTE]Be nice and just tell her that your budget is $200 but if she would like a good time and changes her mind you would love to see her. The dreamers usually come back when the going gets tough.

40 yr old MILF is back but demands condoms. I might go with it until I find a replacement.

Pot # 1 AA 23 yr old demands condos also -WTF? Planned Parenthood is doing too good a job. She sent a nude and her body is a 10 ,so I might go with her if she shows. She has a 2 hour drive so I doubt she will make the trip.

[QUOTE=HollywoodGuy;2320822]I would just say something like "I have helped out a few girls with their problems over the years, even financial ones, but we were dating. I,m not saying that's what you had in mind, but I just wanted to put it out there.

If that seems a little too forward, lets just have a look at those bills and see if we can prioritize them in a way that's not so scary. But I'm interested if you are".

And then shut up.

Sounds like something a little too close to civi dating and I doubt I could pull this off. But the cut to the chase approach works a good percentage of the time.[/QUOTE]Might I suggest that this is just the tight approach, but do it in the reverse order.

Get her to bring all her bills. Go through them and let her come to the conclusion that even with expert help, she has no way of getting out of the fix. Then, hit her with the "I have helped someone before, but we were dating" line.

Also, if you have her bills, you can tell the exact moment when the financial crunch time will be. Even if she declines your offer today, in a week or so when the crunch comes, you can contact her and say your offer is still open. And you will know exactly how much she needs.

You might also ease her in a bit by offering to pay her for a nude foto shoot for a lesser amount, which you can upsell on the day so she can get enough to pay the critical bill.

On SA, I sent an introductory message to this girl. She replies with the following:

"well thank you, I appreciate the time you took to write all that. And unfortunately I really don't get a lot of messages on this site. I'm looking for emotional and financial support I really need a good friend at the moment a lot of these guys are completely fake. I'm in a horrible situation as of right now. I'm living with my grandmother for a bit but I can't stay here long. Its an old folks community type thing but unfortunately I'm homeless. Back in June I decided to give another shot to my ex (I moved to florida to leave him then came back to him because I really missed him. At that point it was 31/2 years together) and I got kicked out of our apartment the landlord had enough of our arguments and since he had a job and paid to live there, he made me leave. I have no phone, because he threw that in the toilet as well (his idea, I paid for it so its mine and I can do whatever I want with it.) I don't have a car, no license, I need glasses, I need to reissue my permit and most of all I need a place to live. And I have backed child support for my daughter. ".

Wow, way to make a first impression. I'll pursue a bit for fun and see where this leads. I'm sure it'll be smooth and trouble free.

SM.

[QUOTE=RubberyMan;2321265]Might I suggest that this is just the tight approach, but do it in the reverse order.

Get her to bring all her bills. Go through them and let her come to the conclusion that even with expert help, she has no way of getting out of the fix. Then, hit her with the "I have helped someone before, but we were dating" line.

Also, if you have her bills, you can tell the exact moment when the financial crunch time will be. Even if she declines your offer today, in a week or so when the crunch comes, you can contact her and say your offer is still open. And you will know exactly how much she needs.

You might also ease her in a bit by offering to pay her for a nude foto shoot for a lesser amount, which you can upsell on the day so she can get enough to pay the critical bill.[/QUOTE]I never knew about the whole photo shoot thing till I hit this site. A couple guys in my area do that a lot.

"You probably have herpes, syphilis, and mono. You should seek therapy instead of random women to swap diseases and bacteria with. You solicit yourself for $100 that's despicable and pathetic. You are trapped in a juvenile state of mind and I feel bad for you. You need professional help. What you desire is not normal and surely not healthy, but that's your risk not mine. Seek religion anything that can help you get beyond the primitive state of mind you are trapped in. No!"

[URL]http://www.sugardaddyforme.com/ALLprofile-3168942-JEl-BaldwinHills-California-SugarBaby[/URL]

[URL]http://wac.3adc.edgecastcdn.net/803ADC/sd4me/photos/83/PMB4444583_3.png[/URL]

I guess she turns heads but doesn't give any. At least not for a $. I wonder what she thinks about guys her own age that offer nothing but a 5 minute thrill ride at her expense? Never get discouraged brothers. She's just venting because it's her first day on the site. Actually after googling her image I see she is one of Tazs Angels. Guess thats not payin too well either. There are just too many unsatisfied horny women to really care. And they are the only ones I really care about.

[QUOTE=HollywoodGuy;2321706]"You probably have herpes, syphilis, and mono. You should seek therapy instead of random women to swap diseases and bacteria with. You solicit yourself for $100 that's despicable and pathetic. You are trapped in a juvenile state of mind and I feel bad for you. You need professional help. What you desire is not normal and surely not healthy, but that's your risk not mine. Seek religion anything that can help you get beyond the primitive state of mind you are trapped in. No!"

[URL]http://www.sugardaddyforme.com/ALLprofile-3168942-JEl-BaldwinHills-California-SugarBaby[/URL]

[URL]http://wac.3adc.edgecastcdn.net/803ADC/sd4me/photos/83/PMB4444583_3.png[/URL]

I guess she turns heads but doesn't give any. At least not for a $. I wonder what she thinks about guys her own age that offer nothing but a 5 minute thrill ride at her expense? Never get discouraged brothers. She's just venting because it's her first day on the site. Actually after googling her image I see she is one of Tazs Angels. Guess thats not payin too well either. There are just too many unsatisfied horny women to really care. And they are the only ones I really care about.[/QUOTE]Hollywood, is this an extreme example of "no thank you"? Curious as to what your usual, and rare, negative responses are like. In any case I appreciate your sharing some of the details of your quest.

[QUOTE=HollywoodGuy;2321576]I never knew about the whole photo shoot thing till I hit this site. A couple guys in my area do that a lot.[/QUOTE]This is a good gig and would be worth sitting in on a community college class on photography, buying some prof.

Sation starter as well. You could advertise on SA and other sites to do shoots for these girls cheap.

Well SLO MO " I don't have a car, no license, I need glasses, I need to reissue my permit and most of all I need a place to live. And I have backed child support for my.

Hter. ".

Run! This girl is a Nando 1 of the first order and you will get endless pleas for money, usually an advance because the (place disaster here) is due today at 3 PM! The pussy will not be worth it.

Question for the board:

Got a 20 yr old 10/10 in my exercise class I have chatted up. She has not come on to me and knows my SO from the Gym. She wants to save up for a graduate class which costs about $12 K. I can do that for her in a year of visits. How do I approach her about it without tipping my hand? I don't want her talking to the other girls or even worse, my SO. I know I should leave this alone but I have seen her pretty much naked and it would be a win / win for both of us. I have an anonymous facebook account. I thought about friending her and see if I can PM her without revealing my identity.

[QUOTE=FredMoore;2321941]Question for the board:

Got a 20 yr old 10/10 in my exercise class I have chatted up. She has not come on to me and knows my SO from the Gym. She wants to save up for a graduate class which costs about $12 K. I can do that for her in a year of visits. How do I approach her about it without tipping my hand? I don't want her talking to the other girls or even worse, my SO. I know I should leave this alone but I have seen her pretty much naked and it would be a win / win for both of us. I have an anonymous facebook account. I thought about friending her and see if I can PM her without revealing my identity.[/QUOTE]Yea you should leave this alone all downside.

[QUOTE=FredMoore;2321941]Question for the board:

Got a 20 yr old 10/10 in my exercise class I have chatted up. She has not come on to me and knows my SO from the Gym. She wants to save up for a graduate class which costs about $12 K. I can do that for her in a year of visits. How do I approach her about it without tipping my hand? I don't want her talking to the other girls or even worse, my SO. I know I should leave this alone but I have seen her pretty much naked and it would be a win / win for both of us. I have an anonymous facebook account. I thought about friending her and see if I can PM her without revealing my identity.[/QUOTE]You are currently at the Testosterone Crossroads. That point at which your dick is telling you to go in one direction, but the voice is so loud that it is drowning out the sound of better judgment telling you to take the other road (because she knows your SO).

Run far away from this one. Change gyms if you need to in order to resist. There is a lot of other pussy out there that does not have a direct and critical risk path to alimony.