"Sugarbabies" / "Arrangements" Amateurs or Not?

I am beyond frustrated tonight. I have been messaging a petite, light skinned 19 yo College Pot (HollywoodGuy, she was right up your alley) I found on SA for several days. She is into being submissive (I make it clear in my profile and initial messages I am a Dom), and some of our emails had been pretty explicit about what we were going to do when we met. She was down for the FC immediately, *never* brought up money or a M&G, and seemed to be focused primarily on the dirty talk (and anticipated activity). She was engaging during our emails / texts, seemed very intelligent, and was down with being obedient or being disciplined if she wasn't (and she knew I have a sadistic streak). I did my due diligence (I have sources at her school I can discretely verify things with, and her FB profile had no security whatsoever), and she was definitely for real.

Monday we were planning to meet, and that morning she informed me that her visitor had arrived, and she also woke up with a sore throat (she is a nanny on the side, so that is plausible). She assured me her visitor only stayed for a couple or three days at a time, so we planned to meet tonight (if everything "cleared up".

Everything looked good this morning, she's raring to meet, and I tell her 6 pm and at which hotel I will be (as well as what will happen if she is late, in explicit detail). She says she understands very clearly, and might be a few minutes late just to be punished. I get to the hotel, set up the room, text her the room number at 5:55.

I text her again 10 minutes later, and she says she is on her way but her roommate just got home (apparently they share a car), and she is still 15-20 minutes out because it is her turn to buy gas. (This girl lives less than a mile from the hotel).

I send her a text asking her to tell me why I shouldn't leave the hotel and block her number. She is, to put it mildly, shocked, and says that she couldn't help it that her roommate was late.

I explain that she can't help when her period is, or whether she picks up a bug from a kid she is sitting for, but she can lace up her shoes and walk a mile once she realizes she is going to be late.

She gets an attitude, saying that is not fair and it's only 30 minutes. At this point, I am steaming. I pack up the room and leave. I only had 2 hours, and if she's this flaky the first time we meet, how much of my time will she waste down the line when she's more "comfortable" with me?

15 minutes later, I get a text from her saying she is downstairs and asking for the room number again. I text back that she needs to check her email.

I sent her an email (already composed) explaining that most SD's are married, and it can be a challenge getting away from the SO, so time is very valuable to us. In addition, many of us have careers that are not salary based, so time literally is money. I encouraged her to be more respectful of her Daddy's (and Dom's, since she's really into that) time the next time she tries to start an arrangement, because being late or not respecting his time is expensive.

I attached a picture of 5 crisp, brand new Benjamins laying on the hotel bed. I wasn't going to give her that much ($ or $. 5 at most), but I wanted the message to sink in. I also wanted her to regret fucking this up when she is with her next Daddy (who will not give her anywhere near that, because the market in my area doesn't require it).

OK, I feel *much* better now.

The Doctor has left the building.

[QUOTE=FotoGuy1970;2072468]A different local girl finally logged on to SA and replied to a message I sent her a couple weeks ago. We decided to meet up that evening. She was very attractive, petite blonde, girl next door. Smart, funny, personable. My kind of SB. As soon as we got in my car, she wanted to kiss and we had a hot, over the clothes make out session right there in the parking ramp. We drove around looking for someplace with a little more privacy but didn't really find a place and she had to be up too early to check into a hotel. She seemed very interested in meeting with me as soon as possible and she said she'd make it a priority. As I dropped her off, she asked if I could help her with some money. All I had on me was a twenty, and she seemed appreciative. I was on Cloud Nine the rest of the night, I thought I'd finally found my new SB.

Sure enough, the next day she's not responding to my texts. Doesn't respond to a text on the day after, either. I'm actually concerned about her well being, but I'm also suspecting something else is going on. So I purchase a Hushed number and text her from that, pretending to be some random person texting her. Of course she responds to that text. So now I'm assuming that my "ideal SB" was playing me for as much money as she could get out of me on Saturday without having to do as much of the work as possible. Too bad for her, I would have given her a generous allowance based on her overall quality that night. What are some of these girls thinking?[/QUOTE]That was back in April. A couple of weeks ago, I saw that she had logged onto SA again, so I dropped her a message saying I was still open to seeing her. We exchanged a couple of texts, but nothing came of it and I figured she had flaked out again. Then earlier today, she texts me again wanting to see me. I actually had three girls who all wanted to see me tonight (this girl, my SDT SB, and then a POT from CL who answered my ad today). I put my SDT SB and the POT on standby while I made arrangements with the flake from SA. I wanted to grab her before she flaked out again.

I pick her up and drive us to the FC. On the way there she apologizes for what happened before, that she just got really busy with school and work and such. On one hand, I understand that everyone gets busy, but on the other hand some simple communication would have gone a long way. So we get to the FC and we get right down to business. She becomes very sexual and affectionate, borderline submissive. Her pussy is one of the tightest I've been in. With a pussy that tight, I didn't last long. We laid in bed for a bit, while she talked up a storm. She promises that this will be a regular thing, and that I can take her with me on a couple of weekend getaways I've been considering going on. I'm taking every single word she says with a grain of salt. I already have trust issues and she fucked up once before. Now my guard is higher than normal with her.

She's definitely a good fuck and decent companionship, but with her tendency to flake out, who knows if or when I'll see her again. I slipped some sugar into her purse when her back was turned. As it turns out, she had a bit of a financial crisis and I suspect that it was what prompted her to contact me in the first place: She needed some cash and needed it fast. She asked me if I could help her out and I told her there was a gift for her in her purse. She seemed appreciative, but who knows.

In the meantime, tomorrow evening I have my first FC date with the roomie of my SDT SB and it's an overnight. This one I'm really looking forward to!

[QUOTE=FotoGuy1970;2127374]
She's definitely a good fuck and decent companionship, but with her tendency to flake out, who knows if or when I'll see her again. I slipped some sugar into her purse when her back was turned. As it turns out, she had a bit of a financial crisis and I suspect that it was what prompted her to contact me in the first place: She needed some cash and needed it fast. She asked me if I could help her out and I told her there was a gift for her in her purse. She seemed appreciative, but who knows.
[/QUOTE]My CL Teacher SB who is now my long-term ATF, started out as a high frequency flake. But when we were together, we had a genuine rapport. So after sticking with it and demonstrating a few kind acts (ie. One time when she wasn't feeling well, I said it was okay to skip the FC activities that day), the flaking frequency gradually got lower because she began to value the arrangement more and knew I wasn't an asshole.

I also recently found out the primary reason she was flaking was because she had a boyfriend. She pretty much goes radio silent everytime her boyfriend is in town or when she visits him. Initially these blackout periods seemed completely random, but once I found the boyfriend's FB page (he's pretty active), I was able to matchup her radio silences with his visits. So while she still goes radio silent on me for days at a time, she doesn't flake on our dates like she did before.

Point is, if she's a good fuck and a good companion, then it might be worth sticking through her BS initially even if she has a high tendency to flake. She might end up being a semi-regular eventually. Just always have a backup or two so you don't get disappointed when she does flake. And if things never improve with her reliability, then just drop her until she knows if she really wants to have an arrangement or not.

FotoGuy mentioned in his report about slipping money into the SB's purse. Quite a few other guys here have also successfully done this.

I think it's a pretty smooth and slick move. I've thought about doing it myself, however the main reason I've avoided it is because I don't want the girl to feel uncomfortable that I might have been looking through her purse. I wouldn't want her going through my wallet even if she was slipping me naked photos. Also the other problem is that the girl may leave thinking you were a cheapskate and not realize you actually put something in her purse. Some girls are more organized than others and may not quickly notice an envelope or extra cash until much later.

Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.

[QUOTE=Golfcart;2127057]She'll return with the same old song and dance because this is important to her. Confidentiality is important to KingGreg as it should be. KingGreg needs to move on to someone else.

The bottom line is things must be a natural fit or there is no fit.[/QUOTE]Well, I was wrong. ! My POT SB did compromise and travelled to see me. Friends. She is like 9. 5/10 for me. Ohh my. Nervous start. Cleared the water for 30-45 minutes. ! Oh lord. Best time of my life. Though only 1 goal was allowed. But enjoyed every bit of it. So you never know. This was a pure luck. But sugar is little high but getting quality.

[QUOTE=JohnGSmith;2127513]
Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.[/QUOTE]This is my preferred technique. If it is a first time maybe I hand it to her, but generally I just put it in her purse. We may be talking at the time and she may see me do it, but nothing is verbalized.

[QUOTE=JohnGSmith;2127513]FotoGuy mentioned in his report about slipping money into the SB's purse. Quite a few other guys here have also successfully done this.

I think it's a pretty smooth and slick move. I've thought about doing it myself, however the main reason I've avoided it is because I don't want the girl to feel uncomfortable that I might have been looking through her purse. I wouldn't want her going through my wallet even if she was slipping me naked photos. Also the other problem is that the girl may leave thinking you were a cheapskate and not realize you actually put something in her purse. Some girls are more organized than others and may not quickly notice an envelope or extra cash until much later.

Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.[/QUOTE]I have never understood this exactly. I really like the hand off as it sort of sets the boundaries. With my ATF there is no direct exchange but that's only because I am paying for a bunch of stuff that all adds up to what it would be anyway.

And since I always talk about the money prior to the M & G there is no real mystery.

[QUOTE=JohnGSmith;2127513]FotoGuy mentioned in his report about slipping money into the SB's purse. Quite a few other guys here have also successfully done this.

I think it's a pretty smooth and slick move. I've thought about doing it myself, however the main reason I've avoided it is because I don't want the girl to feel uncomfortable that I might have been looking through her purse. I wouldn't want her going through my wallet even if she was slipping me naked photos. Also the other problem is that the girl may leave thinking you were a cheapskate and not realize you actually put something in her purse. Some girls are more organized than others and may not quickly notice an envelope or extra cash until much later.

Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.[/QUOTE]Back pocket while you are fondling her ass works well too. But a little tough in the summer if she is wearing a dress. And I always provide a "full tank" for their car so they know where that is coming from too.

[QUOTE=JohnGSmith;2127513]FotoGuy mentioned in his report about slipping money into the SB's purse. Quite a few other guys here have also successfully done this.

I think it's a pretty smooth and slick move. I've thought about doing it myself, however the main reason I've avoided it is because I don't want the girl to feel uncomfortable that I might have been looking through her purse. I wouldn't want her going through my wallet even if she was slipping me naked photos. Also the other problem is that the girl may leave thinking you were a cheapskate and not realize you actually put something in her purse. Some girls are more organized than others and may not quickly notice an envelope or extra cash until much later.

Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.[/QUOTE]One of the SBs I was seeing last year mentioned to me that when I just handed her the sugar it made her feel like a prostitute. So since then I slip an envelope with a SBs sugar inside of it just inside her purse, usually with a 1/4 of it sticking out of the top of her purse so she is sure to notice it, but it also is a clear indicator that I just slipped the envelope there without going through her belongings or anything like that. It seems to work for the girls I've used that technique with.

[QUOTE=Graham111;2127841]Back pocket while you are fondling her ass works well too. But a little tough in the summer if she is wearing a dress. And I always provide a "full tank" for their car so they know where that is coming from too.[/QUOTE]Here is one to try. So after finishing up, just as she was getting ready to get dressed I told her I had gotten her a surprise and I handed her a small bag. I had picked up a little Roxy sundress for her and of course she had to try it on. That lead to a discussion about how free it feels to wear a dress with no undies, which of course leads to me commenting on how nice it is to be with a woman not wearing panties under her dress. How you can just pull it up and do it, bent over a desk, in the car in a parking lot whatever.

That of course leads to us starting all over with her bent over the desk in the hotel room, then on the sofa then back in bed. I" filled her tank" if you know what I mean. So a $50 dress got me another hour of really sweaty sex with a hot looking woman (who of course had never had a man figure out her size much less buy her a dress, including her husband).

[QUOTE=JohnGSmith;2127513]FotoGuy mentioned in his report about slipping money into the SB's purse. Quite a few other guys here have also successfully done this.

I think it's a pretty smooth and slick move. I've thought about doing it myself, however the main reason I've avoided it is because I don't want the girl to feel uncomfortable that I might have been looking through her purse. I wouldn't want her going through my wallet even if she was slipping me naked photos. Also the other problem is that the girl may leave thinking you were a cheapskate and not realize you actually put something in her purse. Some girls are more organized than others and may not quickly notice an envelope or extra cash until much later.

Just wanted to get others opinion on the Purse Slip technique. I like the idea because money is not only never mentioned but not even exchanged, so there's no awkward moments with the hand-off. I'm just concerned that if it's not done properly, the girl will think you stiffed them or might get pissed that you might have been looking through their purse.[/QUOTE]With my only long-term SB (a few years ago) I just left it on her kitchen counter in an obvious place. Not in an envelope. She continued to see me after our first encounter, so I guess it was enough for her. We actually never discussed money, not even once! I left a suitable amount, given that I went to her place and never needed a room, and that we spent several hours (an entire Sunday afternoon) together. I had four or five pops which I probably can't do any more at my current age. It was amazing and sensual. Over about 4-6 hours. That became the standard amount I gave her every time, even when we progressed into overnights. And yes, the first time we met she just had me come directly to her apartment! To say I was nervous about doing that would be an understatement! And for those of you who think she might have been a pro, I can assure you she was not. I found her on FB, and she was exactly who and what she claimed to be with a full time (but low paying job).

Norm!

This tiny 4'9" and 85 lb spinner responded to my CL ad. She just breezed into town a few days a go. So I went to her room in hollywood. I very quickly got to kissin and getting her top off and started sucking her titties. I got naked, and she played with my dick for a few minutes and then said, "this is going too fast. ".

I was like, hey, I thought you wanted to make some money?. She said she would rather get to know me first. So we walked across the street and got a bite, and then hung out at her room for a couple hours. I am supposed to pick her up tomorrow morning for the day (and night?) Will update later. Total cost for the date was 10 bucks.

She is utr, but some girls like to hang out. I thought she was the typical, I am desperate in hollywood, but I guess not.

[QUOTE=KingGreg;2126841]Or will she still try to investigate based on hotel room detail / info? I will try to use different name on my bookind.[/QUOTE]Depending on where you book, be careful about the info the hotel has. There's been discussions before in past pages about one brother using the real name with the spelling slightly off.

Depending on how nice of a place, it can get tricky.

I took a SB to a nice room at a hilton for an overnight (I like a nice room for overnights and I booked it for next to nothing). I'm in the habit of checking in and taking a look at the room and then picking up my SB. Good thing I did because when I walked in, the tv was on and on the screen was a personalized welcome message with my first and last name. I changed the channel and left it there before bringing the SB in.

And on the topic of handing over the sugar, I've learned the utr/undercover pro's will always count the money in front of me as soon as it's in their hands. I usually like to slip it into a pocket, but I like the idea of slipping it into the back pocket. Wish I had heard of that sooner. Not sure what I'll do now that it's dress season. Maybe I'll slip it down the front.

Hotel anonymity -- if there's a way to do it please let me know. I've never tried walking up to these places with cash and a handshake, but pretty much every hotel I've been in with a true SB is on average a $150-200/ night place, sometimes half the average depending on season and where. I don't think any of the girls I've been with would follow me to one of those little roadside trucker bedbug farms, although I really like the idea as long for its sheer raunchiness, as long I didn't take home any "unexpected guests" on my clothes or luggage which is usually not good for popularity back home.

Every hotel I've been to in recent years wants a drivers license and credit card. Curious what you guys are finding.

I'm wondering if there's a market for a commericial, mobile sugardaddy RV fuck truck that has a driver, is bookable by the hour through a smartphone app. Maybe an especially long one (long truck that is, not a long app.. lol).

Like a mobile phallic symbol, painted speckled pink, the front cab could be crafted to look like a penis head maybe. Ok I'm having a little too much fun with that one but do hotels really just let you show up anonymously without I-D and let you just pay in cash?

I had a very interesting week that's worth giving an update for. My CL Teacher SB is on one of her radio silence again, so the last several days I had been going through my backlog looking for BCs or short-term SBs.

[B]Asian 18/yo BC[/B]

I mentioned a few weeks back that I was talking to a young 18 year-old petite Asian hottie who was just graduating high school. This girl could probably command 400-500 a date if she was in LA. Well we came to an agreement on allowance and sugar a few weeks ago, but I would have to drive 50-60 minutes to see her and I had quite a few things on my plate. And honestly, I've gotten spoiled by seeing local SBs that don't require me to travel more than 15-20 min or not at all. So with this Asian hottie I tried to move our date to a different day at the last minute, which she didn't like at all. She said I wasn't serious and I didn't hear from her again.

But then a few days ago, I texted her asking if she wanted to meetup that night since I would be in the area. She responded quick and was wiling and ready to meet that night since she needed the money. She lives at home, no car, and has a very tight schedule so we had to just fool around in the car. But wow, it was fantastic! She gave head like someone twice her age and had all kinds of sexy talk. She got buck naked in the car and her body was amazing. She has very small tits, but nice long legs, fantastic ass, and silky soft skin. Obviously this wasn't her first time, but given her age she wasn't a seasoned UTR or anything. But I do think she had already had a few BC SDs she met off CL. I honestly didn't care because it was worth the drive even though it was just a car thing.

Sadly, she hasn't responded to my texts since our meet that night. So it might be just a "One Hit Wonder". We got along pretty well and she liked my car and everything, so it might be that she doesn't need money right now so she's jumped back to her regular life. Who knows. I might send her another feeler in a few weeks time when my spidy sense tells me she may be in need of money.

[B]Collegiate Athlete SB[/B]

If you read my posts from over a year ago in winter, I was trying to break-in this smoking hot college athlete into the Sugar Bowl. It was one of those things where I invested in her while she wanted to "take things slow". The investment never paid off and I spent a decent amount of money on her and went on a few dates without getting more than a kiss from her. I eventually cut things off. We remained in loose contact and I could see her gradually getting acclimated to the Sugar Bowl but eventually contact stopped altogether last fall.

Flash forward 9 months later to this week, as I was going through my backlog, I decided to see what she was up to lately. I found out that she was working in a restaurant (known for hot waitresses) that was just literally a couple of minutes away from my office. After a little small talk, I suggested after her shift she should come to my office for an "extra tip". Perfect timing on my part because she was very agree-able to it. There was zero discussion of how much the tip would be and what we would do exactly. But I was just amazed at the complete change from a year ago, where she constantly asked about money and how much, this time no questions asked. She arrived at my office after her shift and she looked just as amazing as when I saw her before but this time it was a complete attitude change. She was super-friendly toward me even though I was uncharacteristically nervous because I couldn't believe what I was seeing and hearing. After a little small talk, I initiated the action and WOW. I got to say, it was worth the wait. She's AA and her body-type would be a perfect 10 by Hollywood Guy's tastes (and mine). Because she's an athlete she doesn't have an ounce of fat on her (except where it counts) but also has small bone structure so she's not bulky or anything. She really got into the kissing and exploring each other's bodies. I gave her DATY, which she enjoyed, then went through various positions BB and finished inside her (she said she was on birth control, hopefully! A complete 180 from a year ago, where she barely let me kiss her. I'm guessing some other sugar daddy managed to break her in good, but at the same time she hasn't gone all GPS or Pro SB. The "tip" I gave her was fairly modest considering what we did, but I still gave enough where it basically equaled her night in tips at the restaurant. So by seeing me after her work, she doubled her nights earnings.

I'm still in shock how I had been chasing after her for many months last year with nothing to show, only to have her literally fall into my lap now with the entire kitchen-set available. I'd like to think at least some of the work last year, paved some groundwork for this week. She always said I was a gentleman compared to the other pervs and creepers she met. It's still too early to say if she will now be a regular or it's one and done, but I'm optimistic because it's just very convenient for both us. Every now and then after her shift, I can give her a "full tank" and an extra tip, which will nearly double her night's earnings. So we'll see, though I'll try to keep things simple and have it mostly just after-work Booty Calls and not try to make her a full status SB.

Both girls I thought were lost, ended up being found. So just remember to regularly check your old contacts and your backlog. If I wasn't pro-active in contacting them again, neither of these two experiences would have happened. But just remember when you're renewing contact with someone where things may have soured, it's important to be pretty direct quickly, so you're basically conveying, "Fuck the baggage, I'm ready to go right now. Are you?