"Sugarbabies" / "Arrangements" Amateurs or Not?

Ok, so met my 19 yo UTR who wanted me to go unprotected. On the one hand, I know it's a stupid request fraught with peril but the more I thought about it, I don't think it was a pregnancy trap. I hadn't seen her in a couple months, she could have easily told me she had started the pill, got the depo shot, or IUD. But she didn't say any of that. So, I sort of obliged, went hat practically the whole time, took it off, and ultimately left everything (hopefully) on her back. Can't say I felt great about it afterwards but not overall worried about it. Strangely enough, the whole thing just sort of took some of the fun out of it. I probably will see her again at some point because she is convenient and I like her body a lot, but my feelings toward her have changed a bit.

So I was hoping for another opportunity on Friday but alas, too much crap to do. Sometimes being a responsible adult holds us back. So turned my concentration to Sunday, Monday, Tuesday.

Sunday, tried to line up with 31 MILF. She texts back but when I lay out my proposal to get together, silence for like 6 hours. Then she says she is going thru a lot and maybe Monday is better. Now this chick knows how hard it is for me to see her, and she fails to seize the opportunities when given. I have not responded because of other POTs.

So I turn attention to stripper turn SB, says she is 19, mixed, but most would think she was white if saw her out. Cute enough, body decent but not as good as you would think a stripper should have. Maybe that is why is having to go SB route. So text her for Sunday. She lacks transportation so make more work and time for me so maybe I lack enthusiasm. She asks what time can I pick her up. I say 830. She texts back some surprised remark that I didn't understand and asked for clarification. She takes another hour to text back. Which was her loss and my game because.

While figuring out what the girl above is meaning, I text 20 yo white girl who I have talked to sporadically over the last few months. Seem super sweet, almost too nice that I question whether it's just an act. Her pics are so so, sort of a quirky girl which I usually like, not sure of what body is laying underneath. So after a few texts, she agrees to drive out to me, about 40 miles, all she asks for is some gas money. I assure I will give her gas money and then some. SHe is a little late leaving to come to me, I worry that she is going to flake. But no worries, arrives at designated meeting area, and the kicker is she was much cuter in person than her pics. Body was ok, not fat, maybe a few extra pounds, but overall I liked her look (but granted probably on lot on this board would not rate as high as me, but I like girls who are different).

And it turns out she is as nice in person as on the phone. We talk easily, eat, chit chat some more. Then I ask if I can kiss her. She says yes, and I really wasn't intending to get down to fornication just then, but she seemed like she was ready. So we did, and then we did again, and again. This girl was really into it and seems a little bit kinky. Overall, she spent over 3 hours with me, probably 2 hours of that time either naked or just in panties. It was quite a good time and exceeded all expectations.

So far Monday, I thought I had this 24 yo AA girl who I have talked to forever, but we never get together. Thought she was on board for Monday, in fact she said "I am down for it". But when I try to pinpoint a time, she suddenly goes silent. When she resurfaces, she says she can't stay too late. Well, ok, ,what time do you want picked up and dropped back off. No reply. Then she once again reiterates her commitment to Monday. I say great, what time? Then she says her phone goes off at midnight. I am so tired of this bullshit, so I don't respond.

But all is not lost for Monday, my 19 who I met last Summer originally said she was good to come see me on Tuesday. Now she has lofty expectations and she also suggested there might be limited physical possibilities. I told that was ok because I have a soft spot for this chick and she is extremely hot in my book so I am pretty cool just hanging and making out, see where it leads. She doesn't really have any type of permanent family structure, I just sort of feel bad for her. But anyway, she tells me today she thought we agreed to meet pretty far away from me to take her shopping. I said no, I thought she was coming to me, I could still take her to do a little shopping. She seems a little argumentive about it, so I just aks her, do you not want to end up at my house because you think I might expect too much from you. She texts back that I already told her that I don't want to be like that with her. I say, to be honest, I do, but of course if she doesn't, I totally respect that and won't push it. She then seems to suggest that as she gets what she wants, I will get what I want, but I am not totally clear on that. But I will see it through either way because I like this chic and I don't mind giving her some money. I know, not a "smart" financial move, but I like interesting memories. But anyway, she may come see me on Monday instead.

So a I see a new profile from an 18 year old Hawaiian spinner. She just posted yesterday. And she just graduated H.S. a month or so ago. She claimed her rich parents said she could come to L.A. just to see if she liked it and are shipping her car over shortly. Some quick messaging on line and I finally start txtin her. After 2 non stop hours she says lets just have a talking date. I say OK and another hour of txting gets to maybe we could just have oral. Finally another hour plus goes by and she says to come get her. By the time we get to my place its 10.30. No reason to waste time and we get right to the fun. As we just get naked in bed she says "BTW I,m a virgin for real". I'm like ok because with your insanely fresh and perfect body I could give a shit. She claimed she had never even been fingered before by a guy.

I will admit even getting one finger all the way in there comfortably took about 10 minutes. Eventually I had 2 in there and that probably took about another 20 minutes. Finally she says try putting your dick in. After about another 20 minutes it might have gone all they way in and I just stopped to let her feel it. Finally she said lets break and it really hurt, but she was pretty proud of herself for getting that far.

After about a 10 minute break we spent the next hour plus on her practicing her dick, ball handling and prostate massage skills. And her proper way of speaking to me. She had pretty decent kissing skills that improved dramatically by the end. All told a full two and half hours in the FC. As a first date it was a 9 and she was an easy 8 all around. As I was dropping her off I gave her the $ and she said wasn't it $$/ She pushed for a moment but one thing for sure nobody is more clear on the compensation than me. She saw i had another twenty on me so I gave it to her.

If I was to lose her over this I would be extremely disappointed. But I don't think that's the case. I,ll know for sure by tomorrow nite. She was 5,4" about 110 at most. Tan skin and smelled great. She also said she never had an orgasm before. She said she let a few girls in H.S. try but it never happened. I didnt make it happen either. Her stated goal is to learn to cum and learn to be a good little wh*re for her Daddy. She also says she wants to hang out as well and do stuff, which is fine with me. She is way more than cute enough to hang out with and go places with even though she looks underage. So I got my fingers crossed.

There is one baby where she says in her profile that she is "420 friendly". Does anyone know what that means? The Urban dictionary only states it to refer to pot smoking with friends and meeting time. A term from the 80's I believe it said.

[QUOTE=Mike7794;2541881]There is one baby where she says in her profile that she is "420 friendly". Does anyone know what that means? The Urban dictionary only states it to refer to pot smoking with friends and meeting time. A term from the 80's I believe it said.[/QUOTE]It means that you are cool with smoking pot with her.

[QUOTE=HollywoodGuy;2541761]So a I see a new profile from an 18 year old Hawaiian spinner. She just posted yesterday. And she just graduated H.S. a month or so ago. She claimed her rich parents said she could come to L.A. just to see if she liked it and are shipping her car over shortly. Some quick messaging on line and I finally start txtin her. After 2 non stop hours she says lets just have a talking date. I say OK and another hour of txting gets to maybe we could just have oral. Finally another hour plus goes by and she says to come get her. By the time we get to my place its 10.30. No reason to waste time and we get right to the fun. As we just get naked in bed she says "BTW I,m a virgin for real". I'm like ok because with your insanely fresh and perfect body I could give a shit. She claimed she had never even been fingered before by a guy.

I will admit even getting one finger all the way in there comfortably took about 10 minutes. Eventually I had 2 in there and that probably took about another 20 minutes. Finally she says try putting your dick in. After about another 20 minutes it might have gone all they way in and I just stopped to let her feel it. Finally she said lets break and it really hurt, but she was pretty proud of herself for getting that far.

After about a 10 minute break we spent the next hour plus on her practicing her dick, ball handling and prostate massage skills. And her proper way of speaking to me. She had pretty decent kissing skills that improved dramatically by the end. All told a full two and half hours in the FC. As a first date it was a 9 and she was an easy 8 all around. As I was dropping her off I gave her the $ and she said wasn't it $$/ She pushed for a moment but one thing for sure nobody is more clear on the compensation than me. She saw i had another twenty on me so I gave it to her.

If I was to lose her over this I would be extremely disappointed. But I don't think that's the case. I,ll know for sure by tomorrow nite. She was 5,4" about 110 at most. Tan skin and smelled great. She also said she never had an orgasm before. She said she let a few girls in H.S. try but it never happened. I didnt make it happen either. Her stated goal is to learn to cum and learn to be a good little wh*re for her Daddy. She also says she wants to hang out as well and do stuff, which is fine with me. She is way more than cute enough to hang out with and go places with even though she looks underage. So I got my fingers crossed.[/QUOTE]I double-booked Sunday to avoid being flaked on, get flaked on by both girls, and you're fingering virgins. Smh, you're the man.

[QUOTE=Mike7794;2541881]There is one baby where she says in her profile that she is "420 friendly". Does anyone know what that means? The Urban dictionary only states it to refer to pot smoking with friends and meeting time. A term from the 80's I believe it said.[/QUOTE]It means she's willing to smoke marijuana with you, or is looking for someone that likes doing that as well.

Damn it. The virgin txted me this morning and said she was not happy with the compensation and that she wants more. She said she wasnt planning on losing her viriginty last nite, but oh well, shit happens and she wasnt sorry it happened. She says she is willing to talk about it. I don't know if I can salvage this or not. Keep you posted. And she keeps saying how she comes from a rich family and its just not enough. I may give in a few times to see if I can show her why what I pay combined with being a good guy is worth it. F ing shit.

[QUOTE=HollywoodGuy;2542196]Damn it. The virgin txted me this morning and said she was not happy with the compensation and that she wants more. She said she wasnt planning on losing her viriginty last nite, but oh well, shit happens and she wasnt sorry it happened. She says she is willing to talk about it. I don't know if I can salvage this or not. Keep you posted. And she keeps saying how she comes from a rich family and its just not enough. I may give in a few times to see if I can show her why what I pay combined with being a good guy is worth it. F ing shit.[/QUOTE]Better roll out that charm. Once one side feels like they aren't getting the level of value they want, shit starts falling apart.

HWG. You truly are an inspiration.

I know how you feel. I told myself that I would never provide more than $250 as an allowance, but my most recent blonde 19 year old blonde made me break that one. We established a much lower amount initially. And now we are at over double what was initially agreed to.

I've rewritten my rules though and for my specific situation, it has made me happier. Very recently, I upped my blonde swim instructors allowance for a variety of reasons. She really was in need of the cash, and so rather than a per date allowance, we moved to a weekly allowance. Sure, a higher allowance, but more value from my perspective.

Next, I had started to get bowl fatigue and she is my ATF baby to date. I got tired of m&gs with utr girls who were asking for per date allowances that exceeded the rates of some of the hottest pro talent in my area. Spend more for someone with less experience, for the privilege of listening to inane chatter. No thank you.

Like your Hawaiian, my blonde 19 year old swimmer is inexperienced sexually, has not been with many guys, but truly loves to please me. It really helps that she wants to spend time with me when I am free, but gives me as much space as I need, when I need it. It also helps that I have an all access pass to all lanes with her.

I released my Asian head student to make way for the higher allowance I am providing to blondie, and am keeping the low maintenance sexual dynamo 19 year old Asian in the wings for whenever I need or want something different.

Long story short, I am happier changing my rules. Even though the number of different ladies in rotation has gone down, trips to the FC has gone up and overall budget is about the same.

Have you thought about putting your Hawaiin on a weekly allowance? You may have to kick some of your lower quality babies from your rotation, but you may be happier for it in the long run, while keeping your overall budget the same.

[QUOTE=HollywoodGuy;2542196]Damn it. The virgin txted me this morning and said she was not happy with the compensation and that she wants more. She said she wasnt planning on losing her viriginty last nite, but oh well, shit happens and she wasnt sorry it happened. She says she is willing to talk about it. I don't know if I can salvage this or not. Keep you posted. And she keeps saying how she comes from a rich family and its just not enough. I may give in a few times to see if I can show her why what I pay combined with being a good guy is worth it. F ing shit.[/QUOTE]

[QUOTE=HollywoodGuy;2542196]Damn it. The virgin txted me this morning and said she was not happy with the compensation and that she wants more. She said she wasnt planning on losing her viriginty last nite, but oh well, shit happens and she wasnt sorry it happened. She says she is willing to talk about it. I don't know if I can salvage this or not. Keep you posted. And she keeps saying how she comes from a rich family and its just not enough. I may give in a few times to see if I can show her why what I pay combined with being a good guy is worth it. F ing shit.[/QUOTE]HWG I could be wrong, and I hope I am & that this turns into something good and long-term for you, but there's something about this girl's behavior and story that's got my BS detector going off like it hasn't in a long time.

If she's as rich as she says she is and her parents would do as she said they did, she does not need an SD. If she is cute enough to be an SB, she has all the opportunities for sexual experimentation laying at her feet. If she is just one of those that has a fetish for older men, the chances of her developing that fetish before her cherry is busted is less than 1 in a million.

Even assuming the virgin part of the story is confirmable via blood loss (you didn't mention so I wasn't sure), the other aspects of her story don't add up. Especially with the demands for more money, huge red flag. Money she shouldn't really need if her parents are so rich, yet she's using wealth as the reason she needs more. Whaaa?

[QUOTE=IluvSmellyFish;2542240]HWG. You truly are an inspiration.

I know how you feel. I told myself that I would never provide more than $250 as an allowance, but my most recent blonde 19 year old blonde made me break that one. We established a much lower amount initially. And now we are at over double what was initially agreed to.

I've rewritten my rules though and for my specific situation, it has made me happier. Very recently, I upped my blonde swim instructors allowance for a variety of reasons. She really was in need of the cash, and so rather than a per date allowance, we moved to a weekly allowance. Sure, a higher allowance, but more value from my perspective.

Next, I had started to get bowl fatigue and she is my ATF baby to date. I got tired of m&gs with utr girls who were asking for per date allowances that exceeded the rates of some of the hottest pro talent in my area. Spend more for someone with less experience, for the privilege of listening to inane chatter. No thank you.

Like your Hawaiian, my blonde 19 year old swimmer is inexperienced sexually, has not been with many guys, but truly loves to please me. It really helps that she wants to spend time with me when I am free, but gives me as much space as I need, when I need it. It also helps that I have an all access pass to all lanes with her.

I released my Asian head student to make way for the higher allowance I am providing to blondie, and am keeping the low maintenance sexual dynamo 19 year old Asian in the wings for whenever I need or want something different.

Long story short, I am happier changing my rules. Even though the number of different ladies in rotation has gone down, trips to the FC has gone up and overall budget is about the same.

Have you thought about putting your Hawaiin on a weekly allowance? You may have to kick some of your lower quality babies from your rotation, but you may be happier for it in the long run, while keeping your overall budget the same.[/QUOTE]I have already kicked or been kicked by everyone but my ATF who is at a straight $ a date for 10 months. I have had a lot of unexpected medical expenses so I am trying to balance it out and business sucked for the first 2 quarters this year. So its a problem. And I am weak from all the dr visits and surgeries etc. One day at a time as they say. Even now my back is killing me.

Approximately 2 months ago my sweet Asian SB ended our relationship (I reported that here) because she started a "committed" relationship with someone else. I wished her well and told her if things change to let me know. Today I get a text from her asking how I am doing. She tells me how much she misses me. Well, probably going to get together tomorrow. Life is good again.

[QUOTE=JeezLizard;2542371]HWG I could be wrong, and I hope I am & that this turns into something good and long-term for you, but there's something about this girl's behavior and story that's got my BS detector going off like it hasn't in a long time.

If she's as rich as she says she is and her parents would do as she said they did, she does not need an SD. If she is cute enough to be an SB, she has all the opportunities for sexual experimentation laying at her feet. If she is just one of those that has a fetish for older men, the chances of her developing that fetish before her cherry is busted is less than 1 in a million.

Even assuming the virgin part of the story is confirmable via blood loss (you didn't mention so I wasn't sure), the other aspects of her story don't add up. Especially with the demands for more money, huge red flag. Money she shouldn't really need if her parents are so rich, yet she's using wealth as the reason she needs more. Whaaa?[/QUOTE]We don't always agree. But you make some valid points here that had already crossed my mind. Also I did push her a little psychologically into some role play. Which she happily complied with, but it is new for a lot of girls. I remember when I first did that with my ATF she told me she was a little uncomfortable with it. Now she can't live without it. Things could be worse. Lots of POTS and pre-POTs hitting me up.

[QUOTE=HollywoodGuy;2542482]We don't always agree. But you make some valid points here that had already crossed my mind. Also I did push her a little psychologically into some role play. Which she happily complied with, but it is new for a lot of girls. I remember when I first did that with my ATF she told me she was a little uncomfortable with it. Now she can't live without it. Things could be worse. Lots of POTS and pre-POTs hitting me up.[/QUOTE]Will be great if she is what she says she is. Most women, particularly cute asians from rich families just don't give up their virginity for a hundred bucks or so. I've seen them do it for free, but for other reasons, so her upsell for higher allowance immediately afterwords is a red flag to be sure. Hopefully I'm wrong.

Need some guidance from the seniors on this one, just a post-mordem to see if I could have done anything differently. I don't think so, but a second (or eighth) set of eyes is always good.

So I sent out a batch of messages last night to new signups, I had a couple of no shows over the weekend I need to replace. One was to this 20 year old middle eastern girl, she only had a single public picture but a bunch of private ones and no profile info filled out. She'd only been on the site a few hours. I get a message back this morning and I fire up the usual line of questioning to see where it goes. As you can see below, she responds well to the entire thing, her answers are crafted to my questions and she's putting effort into it so it's definitely not a copy paste and the responses are pretty prompt so she's not wasting time. Not sure what went wrong at the end, maybe another monger beat me to her (screw you guys sometimes, LOL) with a higher offer or a girlfriend told her to upsell a bit:

Prelim messages I'm not going to copy as it had some identifying info in it, she gave me access to her pictures at this point as well. Very suggestive poses, bikini shots and some great shots of her waist+abs. This girl is smoking hot. This starts at Step 2 in HWG's 5 Steps guide:

MY MESSAGE 2.

So I'm pretty clear on what I'm looking for, what about you? Usually I find women are looking for 3 separate things:

#1. Financial help.

#2. Unmet physical needs.

#3. Emotional support.

The more of one you get, the less of the other two. I try to strike a good balance of the three, and I'm experienced enough at this to adjust as needed. I provide a safe environment where you can express what you might not express to others in your daily life. Whether that's just talking about a bad boss, a family member, or working out some physical needs on someone you don't have to face daily. I don't judge and I also don't pretend to be the perfect fit for everyone. We'll see soon if we are a good fit or not. .

So which of those 3 are you looking for?

HER MESSAGE 2.

LOL well even though financial support is something I'm looking for, it doesn't mean I won't take the time to actually see how your day is going and if you needed to talk. I'm an SD virgin (never had an SD or arrangement before) but even though you have money, you're still a human with feelings in my eyes. You're not a cash cow or opportunity to me. Out of that list, it's hard to choose honestly since all 3 are needed.

MY MESSAGE 3.

Some mixture of all 3 is normal, I throw that question out because if a woman answers nothing but #1 then we're not going to be a good fit.

I need a connection or chemistry, whatever you want to call it, for this to work for me. I've had initial meetups with drop dead gorgeous women that I walked away from because all they were interested in was an ATM. I give enough to show I'm not trying to get something for nothing, but not so much someone would stay with me only for money.

So are you looking for the highest bidder? If you're looking for top dollar, I guarantee that's not going to be me. There are some guys on here who will throw obscene amounts of cash at you. Maybe you'll need that much to stomach being around them, there are plenty of assholes and losers on here.

If you're willing to accept less from a chill guy who's reliable, interested in your well being and not just your body, and very drama / problem free we can work out. What do you think?

HER MESSAGE 3.

Not searching for the highest bidder at all. I understand that trust is needed as well as affection and genuine feelings on your part. I'm not going to fake my feelings just to get what I want. You seem like a serious and caring person with a huge heart. All I want is a friend that I can do everything with, but financially just enough to cover college expenses until I graduate. If you want me to pay you back that's fine.

MY MESSAGE 4.

Well that's good to hear, that's the type of girl I like to date. I typically start at $150 per meet up, it won't pay for college in one visit but it does add up. I generally expect to meet someone 2-4 times a month, depends on both our schedules.

I understand if that's not enough for you, like I said before I know that I won't meet every woman's needs. I just prefer to know someone is with me for more than just money. That won't outright pay for tuition, but I'm sure it would put a hurting on books and fees. If that sounds good to you let me know and we can talk about what dates will look like.

HER MESSAGE 4.

I'm interested. $150 is fine. I won't blow it on silly things knowing I have fees. That wouldn't be very smart.

MY MESSAGE 5.

I'm not going to copy / paste what I sent for this one, but I explain what few rules I have (no social media pictures, discretion, and STI tests + condoms if she isn't on birth control I can verify). I explain my sexual needs, nothing outrageous or extreme. I mainly look for a GFE, the same type of thing I bet most of you do. I just want a good looking fucktoy every weekend is all.

HER MESSAGE 5.

I like your terms. Very easy and agreeable. Sex is fine with me. I'm disease and drug free but if you would feel better if I got tested to show you proof I'm fine with that. I give oral and we can do Anal if you're into that. I'm on a birth control shot called Depo Provera but if you choose to use a condom regardless it's fine. <REDACTED AFTER THIS, PERSONAL INFORMATION .

The rest after that is just schedules and locations, I leave off with giving her my GV number and she says she's going to 'text me now'. I was busy at work, so I didn't check for a couple hours, and when I did I saw there was no text. I check the SA convo and there's no update. Now I've had a few problems with GV texts not coming through on occasion, particularly MMS if they send a picture, so I send her another message saying "hey if you texted me I haven't gotten it, sometimes my phone drops them so let me know if you're trying to send me something". I put the phone down, go back to work, check back 30 minutes later and I'm blocked on SA chat and she revoked access to her (very good looking) pictures.

Obviously this shit happens with girls selling their asses on the internet, just seeking some input on anything I might have done wrong here. Like I said up top, I think she either had another guy offer more cash, a girlfriend told her to get more, or I somehow managed to creep her out with the last message. Not sure how the last option works considering she was telling me I could blast inside her ass or pussy 4 hours prior, but hey these girls are kinda crazy sometimes. Her profile isn't deleted, so she didn't just give up on the whole idea either.