"Sugarbabies" / "Arrangements" Amateurs or Not?

[QUOTE=FredMoore;2062921]If you have read the entire thread you will recognize your early SB as a classic Nando 1 .[/QUOTE]Yes, she was definitely a Nando 1, It's unfortunate, but I learned and moved on.

As for more recent pursuits:

1. In October, I was trying to get over a relationship, so I was looking around on craigslist. I answered an ad that was primarily talking about being a submissive in a dom / sub relationship, but she tacked on at the end something about looking for a SD as well. I told her that I had no dom / sub experience, but I was open to figuring that out, and I was open to helping her out if she needed. She e-mailed me back shortly after, then we started texting, and after a couple of days we met for a late dinner. She looked just like her pictures: petite, blonde hair with glasses, 28 years old, divorced, no kids, and had a full-time job (but it didn't pay a whole lot). And it was just very normal hanging out with her. We alluded to the SD / SB thing but didn't talk about money, and at the end of the night there was a lot of passionate kissing. I couldn't wait to get her into bed then, and even more so after she had sent me a bunch of pictures of herself while we were texting late the following night. A couple of nights later we met up, and it was great. There was no sugar mentioned or exchanged.

She and I met about once a week, and it became more like a friends with benefits kind of thing -- we would start out hanging out and talking, watching tv, etc., then we would head to the bedroom. About a month after we met, she asked me for help paying her student loans, which were a ridiculous amount per month (especially considering the school / degree she received). So I told her what I could give her, and she was appreciative for that. I gave her sugar the following month too, but not again after that. The cost per visit ended up very reasonable. She brought no drama or other major issues. However, in February she received a promotion that required her to move to another state, so our time together had to end. We always knew that it was going to be a temporary thing, but I still miss her.

Nevertheless, I renewed my profile on SD4 me in February. (They double charged me using two different website names, so I had to dispute that. Definitely take the advice to use disposable gift cards, which I had done before but the little head made the decision first). I sent messages to a bunch of potential babies, got responses from most of them, but only three were anything.

2. Redhead medical assistant. She actually contacted me first. There was not an instant attraction based on her profile and pics, but I decided to continue talking with her, and we ended up texting then an impromptu meet-and-greet during my lunch one day. She claimed to be 26 (a later internet search gave me reason to doubt that), and she said that she had a job at a local doctor's office but had her hours cut significantly. She quickly jumped right into the money discussion. I told her what I was willing to help her out with and how often, and she said that would be fine. She told me about a previous SD who she had in college who would give her 3 k / month, and I wondered who she suckered into doing that. Anyway, after lunch she and I went outside to talk a little bit more. She was wearing a very low-cut shirt, and I had to check her out a little bit. But it didn't get any further, not the least because I had to return to work. She asked me for some sugar after giving me a story about a car title loan she had to make payments on. I figured it would be an advance of our first meeting in the FC that evening, so I just went ahead and gave her the money. After work, I texted her and she gave me some excuse about why she couldn't meet up.

It wasn't until the weekend (a couple of days later) that she asked me if she wanted to meet up. She texted me in the morning and gave the impression that she was basically ready to go and could meet up within an hour or so. That worked for me, so I got myself ready, then I waited. And waited. And waited. I texted her several times to find out what was going on, and when I got an answer much later it was nothing more than something like "I'm on my way." Never mind that I had things to do besides her. Oh, and she also asked if I was able to help her with the amount that we had discussed previously. Ugh. About six hours later she finally arrived and gave me a story about why she couldn't leave immediately, and she said she got lost. But she was there. So I led her into the FC, and we got comfortable. However, all I could think about was how annoyed I had been that she had been late, and that I had other things to do after she left. Then she asked to turn all the lights off. I obliged, but I like being able to see what I'm doing, so that was another negative. And the whole experience was just eh. The next week I told her that I didn't know when I would be able to see her, and she texted me a few more times but I didn't respond. I didn't want to deal with it.

But just this past week, another member here posted to offer information about this same girl to others as a UTR escort (with pictures). I assume that she approved of it, but I guess the sugar world alone wasn't enough for her. I may have dodged a bullet. Although as an escort, she would probably be great.

3. AA new to area. This one was supposedly a 23 year old mother who said she had moved to the area a month ago. Her profile was pretty well written, and she said she was looking for a close friendship and not just a transactional thing. Ok with me. In talking some more, she claimed to need money for daycare for her child so she could look for a job. It seemed a reasonable amount, so ok. Then one evening we were texting, and she asked if I wanted to talk on Skype. We talked for an hour. She apparently had her child in the same room, so it was kind of awkward. Before she moved to this area, she said she had been a webcam girl. Her profile on Skype also listed her age as 10 years older than what she had told me, and she did look old for 23. So there were some red flags. A few days later, she asked me when we would be able to meet up. I told her I didn't know, and we haven't talked again since. I am comfortable with it.

4. College baby. A 21 year old college student. She kept remarking about how normal I seemed to be when I contacted her. Apparently a lot of other guys on there are very offputting. After exchanging messages through the site a few times, we started texting. A couple of weeks later, we met for dinner / drinks. She said she had never done anything like that before and was worried that I was going to expect to sleep with her on the first date. I told her that this was just going to be dinner. She was about a 6 or 7 in looks, but I thought definitely cute. She is a full time student and works as a waitress on weekends and some other nights. We ended up spending a few hours together just talking, and I definitely want to see her again so we can advance things toward the FC. However, getting to see her again has proven to be a challenge to say the least. A couple of times we have made tentative plans only to have her back out at the last minute. Right now I've decided to cool things off, and if she wants to come to me, then we can talk.

That's pretty much it for me. Hopefully there will be more possibilities in the near future, but the bowl doesn't get replenished around here as often as some areas.

Pregnancy update. She sent me an official looking statement that detailed the abortion costs and everything. I'm just waiting on confirmation from her two week checkup that she's no longer pregnant before I send the money for it. I'll pay $400 to keep from paying for 18 years, but I don't think I'm ever going to meet with her again.

On another note, I met a potential SB for frozen yogurt. I thought we were meeting for just yogurt, but she suggested we go get a room after we were finished. We did and I received the most amazing BJ that I have ever had (I don't really want to have sex after that scare). It was a pornstar BJ with deep throating and a little gagging. She was really hot. Nursing major, 5'9 with see cups. Everything went downhill after I finished and asked for another one 10 minutes later. She said she was really tired and she put a lot work into that. I asked again and she got really offended. We hung out in the hotel room and watched a movie. She left and I never heard back from her again. She went radio silent. Disappointing, but that was amazing head.

I have two more potentials. A 5'10 stunner who's auditioning to be an NFL Cheerleader and a sexy Alabama girl that graduated college last December.

[QUOTE=Donwhite;2063165]Pregnancy update. She sent me an official looking statement that detailed the abortion costs and everything. I'm just waiting on confirmation from her two week checkup that she's no longer pregnant before I send the money for it. I'll pay $400 to keep from paying for 18 years, but I don't think I'm ever going to meet with her again.

On another note, I met a potential SB for frozen yogurt. I thought we were meeting for just yogurt, but she suggested we go get a room after we were finished. We did and I received the most amazing BJ that I have ever had (I don't really want to have sex after that scare). It was a pornstar BJ with deep throating and a little gagging. She was really hot. Nursing major, 5'9 with see cups. Everything went downhill after I finished and asked for another one 10 minutes later. She said she was really tired and she put a lot work into that. I asked again and she got really offended. We hung out in the hotel room and watched a movie. She left and I never heard back from her again. She went radio silent. Disappointing, but that was amazing head.

I have two more potentials. A 5'10 stunner who's auditioning to be an NFL Cheerleader and a sexy Alabama girl that graduated college last December.[/QUOTE]As good as some of them are in the BJ dept, I only have one that can last a decent length of time (and she is so proud of it). When they say they are tired I just tell em to suck my balls. Never been turned down yet. But any girl that gets offended is not someone you really want to see again.

I'm envious of you guys who are satisfied by a finely crafted BJ. Unfortunately I cannot get off with one and only fucking will do it for me. I have to have the whole package including eating some sweet pussy. The latter is a good way to evaluate the girl's vaginal health because I examine her manually and visually for bumps, blisters, and stinky discharge. If they pass the taste and smell test then I am deep diving with little Fred.

[QUOTE=Donwhite;2063165]Pregnancy update. She sent me an official looking statement that detailed the abortion costs and everything. I'm just waiting on confirmation from her two week checkup that she's no longer pregnant before I send the money for it. I'll pay $400 to keep from paying for 18 years, but I don't think I'm ever going to meet with her again.

On another note, I met a potential SB for frozen yogurt. I thought we were meeting for just yogurt, but she suggested we go get a room after we were finished. We did and I received the most amazing BJ that I have ever had (I don't really want to have sex after that scare). It was a pornstar BJ with deep throating and a little gagging. She was really hot. Nursing major, 5'9 with see cups. Everything went downhill after I finished and asked for another one 10 minutes later. She said she was really tired and she put a lot work into that. I asked again and she got really offended. We hung out in the hotel room and watched a movie. She left and I never heard back from her again. She went radio silent. Disappointing, but that was amazing head.

I have two more potentials. A 5'10 stunner who's auditioning to be an NFL Cheerleader and a sexy Alabama girl that graduated college last December.[/QUOTE]Having been through the pregnancy scare scam a couple of times, they do a sonogram of the fetus which there should be documentation of. Ask her for proof. And go with her to the clinic and wait inside to make sure. A girl I used to mess with tried to get me for $600 saying she was pregnant and she wanted me to just drop her off at the clinic with $600. I insisted on going in with her. Well it turns out she wasn't pregnant and I saved a few hundred bucks and got the satisfaction of showing her she couldn't run that scam on me.

[QUOTE=Zman429;2058439]Interesting site, what do you mean if a message is not sent, ie they wink first or can they send you an email not sure what you mean thanks.

Oh on SA you can sure by location, which seems to semi sort by login date now finally, or by near me and sort by login date also they have a good intro price[/QUOTE]I mean you do not have to spend money (credits) to access the POTs email if they have not sent a message. I only accept dates if they send a message with the acceptance of my offer. Seems to weed out a lot of flakes.

So I had a really busy week last week, I saw my young regular, but I could not make my schedule work with my Columbian cutie and it was her birthday week. On her birthday I managed to arrange to see her before work to give her a little gift. She comes back out and tells me that her boss has given her the afternoon off and we can meet for a drink. So on to the neighborhood Chilies where though out the conversation she is sliding her foot up and rubbing my crotch. Finally I was so hot we paid the tab and moved my SUV over to the Lowes parking lot to "make out a little" She was in a short skirt, so next thing you know we are in the back seat and my face was buried between her knees giving her another birthday gift. Then she whips me out and returns the favor, eventually climbing on in reverse doggie and banging the shit out of me.

All of this in broad daylight in a busy parking lot with cars driving by.. I have to be careful with this one, I might end up on the news. That latin blood, thought I would share a little with you guys [ATTACH=CONFIG]313517[/ATTACH].

[QUOTE=FredMoore;2063391]I'm envious of you guys who are satisfied by a finely crafted BJ. Unfortunately I cannot get off with one and only fucking will do it for me. I have to have the whole package including eating some sweet pussy. The latter is a good way to evaluate the girl's vaginal health because I examine her manually and visually for bumps, blisters, and stinky discharge. If they pass the taste and smell test then I am deep diving with little Fred.[/QUOTE]I've never, ever been able to get off with oral either.

[QUOTE=FredMoore;2063391]I'm envious of you guys who are satisfied by a finely crafted BJ. Unfortunately I cannot get off with one and only fucking will do it for me. I have to have the whole package including eating some sweet pussy. The latter is a good way to evaluate the girl's vaginal health because I examine her manually and visually for bumps, blisters, and stinky discharge. If they pass the taste and smell test then I am deep diving with little Fred.[/QUOTE]I guess I make three. BJs are great, but they are always a precursor to the main event, never the whole show. This has been something of an issue with SO's in the past. They feel like they aren't doing something right because they can't make me cum. The upside is that they try REALLY hard to get me there.

The visual vaginal health exam is one of the reasons I don't trust a girl who wants to turn off the lights. Hell, I don't even want "mood" lighting. If she is sexy enough that I want to take her clothes off, then I want to see her in all of her glory. Not some shaded, shadowy figure.

Just got this response to my CL ad:

"I'm XXXXXX and I am interested in marrying you. Why have a Sugar baby and you can have someone to spend the rest of your life with. I will give you sex weekly and all you have to do is take care of me. I want kids so we can try for them next year. My pussy is tight so it might take a while for me to warm up to you. Text me at XXXXXXXXX if interested".

She didn't attach pics with this response, but she's responded to my ads before with pics attached, and she is not at all attractive. I didn't want her as my SB, let alone my wife. SMH..

[QUOTE=FotoGuy1970;2064054]Just got this response to my CL ad:

"I'm XXXXXX and I am interested in marrying you. Why have a Sugar baby and you can have someone to spend the rest of your life with. I will give you sex weekly and all you have to do is take care of me. I want kids so we can try for them next year. My pussy is tight so it might take a while for me to warm up to you. Text me at XXXXXXXXX if interested".

She didn't attach pics with this response, but she's responded to my ads before with pics attached, and she is not at all attractive. I didn't want her as my SB, let alone my wife. SMH..[/QUOTE]I'm going to go with likely someone pranking his buddy on that one.

[QUOTE=FotoGuy1970;2063749]I've never, ever been able to get off with oral either.[/QUOTE]CIM is my preferred way to deliver the man-yogurt, but whether or not I can do it (or maybe I should say how fast) really depends on the girl. When I was in high school I found the average GF didn't know how to do it with enough skill for me to get off, but with a little bit of mental focus I got to the point where I could.. I started just imagining it was a really skilled 25 year old slurping away. At the time I didn't really know how to coach them toward giving a better BJ but now I do. Usually if they allow themselves to get a little sloppy with it and let some saliva drip down it, and use their hand to stroke the lower part of it, it's hard to go wrong. Problem is that many of them either don't know how to do that, or they know to do it and just don't want to come across as a super skilled BJ sloot, or they just forget to do it, or they just aren't motivated to do it. So, a little coaching goes a long way.

I'll never forget this little Peruvian college baby I met in a nightclub (not an SB, I was about 35 at the time and she was about 24, just bought her a few drinks and gave her a ride home). Outside the club after closing we got in the back of my car and she said "touching only" meaning no sex. Well I went down on her, she liked that, and when it was time for her to return the favor I got a BJ I will never forget. I find most girls don't know how to use both hands effectively, but this girl pumped and sucked me dry in no time, swallowing every drop. It was such a mind blowing blow job that I stayed fully erect afterward it never went down, and after maybe 5 minutes of talk while I'm sitting there with this awkward boner and my pants still around my ankles, she proceeds to go at it again with every bit of sloppy enthusiasm as the first time, making me pop again, and swallowing again. I didn't even know I could do that on a single boner.

The problems I run into most often have more to do with willingness to take the load in the mouth than anything else. I've had a history of them saying, when asked to take the load in the mouth, "I'm okay with doing it but not on the first date", etc... In other words they know the mouth money shot is what I really want, and they feel that they are giving more than they're giving, so they are usually trying to use CIM as leverage to get a longer term commitment from me.

One of the best GFs I ever had would do it right, and consistently. We would start off with mutual fucking positions like 69, mish, doggie etc. But then, for whatever reason in order for her to cum, she always needed to be cowgirl and in control of the motion, so she would just climb aboard and do her thing. I almost never cum in that position, but I'm happy for them to ride as long as they need to. But then after she got hers, she would hop off and suck me dry. There wasn't a lot of variety in our sessions but there didn't need to be, it was consistently some of the best sex I've ever had.

I really like hjs and bjs. I find them to be very relaxing and can finish with either if the woman has skills. Two sbs that I have met were the best I've ever had. The tilted kilt baby that I saw for about 4 months was the best ever at it. I'm embarrassed to say that she got me off in a minute before. She was extremely talented.

[QUOTE=JeezLizard;2064104]I'm going to go with likely someone pranking his buddy on that one.[/QUOTE]No, this girl has replied to my ads before with pics attached and even her college transcripts! She's not even a little bit attractive and she's always come off as a bit unhinged, so I've always passed on her. But this latest reply of hers to my ad trumps all her others, which were odd to begin with.

Great to see all the new faces around here!

I just wanted to give a brief update. A few months ago, I mentioned that I let my memberships expire on the SD sites and that I found two smoking hot SBs through CL. Well I'm happy to report both those SBs are still in my rotation. Both are flaky and I'm lucky to see them 1-2 times a month, but both are hot, petite, educated normal girls who have modest financial needs that it still works out.

CL Student.

One of them is 21 AA and a full-time student and very active in her student union at her university. Because of her busy schedule she doesn't have time for real relationships and she enjoys the stress-free companionship I give her via texts and I also help her out with a few of her expenses. But she also works and lives with her parents still, so she's not hard up for money, so she has never hit me up for money. I give it to her when I feel like it. Also she has only had one boyfriend before, so she's a little bit inexperienced but a very eager learner. I don't see her often, but we text lightly almost every day. She almost feels like a long-distance girlfriend. She's genuinely attracted to me, so that's partly why money hasn't been a big part of our relationship. I would like to see her more often, but she isn't costing me anything when I don't see her and I have other girls to fill in for her, so it's cool for now.

CL Teacher.

The other CL girl is 22 and a substitute elementary teacher believe it or not. Her body is a 10 and her face an 8. She's hot. And what makes it even hotter is that she's a nearby schoolteacher. I bet there a bunch of male parents (& teachers) at the school wishing they could bang her, but they can't, yet I am. Awesome feeling. She actually still lives with her parents, so her financial costs are also modest. I still can't quite figure out this girl. Sometimes she's into me and we meetup for amazing sex, and then she'll drop off the radar for a week and become distant. Then out of nowhere she's back in the saddle again. She's flaked on me several times as well. But she keeps coming back and she's so hot and easy to talk to when we're together, that I put up with it. I honestly don't know how long it will last. She thinks I'm a nice guy and likes me, but I can tell she's not 100% there. It's likely other personal issues that I can't see. I give it another month or two before she says she can't do it anymore. But I'm going to enjoy the ride while I can.

Another tactic I've been doing lately when I'm bored is browsing through escort ads and using my spidey-sense to determine which girls are low-volume / UTR and would be receptable to a SB / SD arrangement. Why target escorts who are often hardened, jaded, money-grubbing, and cold? Because sometimes you can catch that one girl who only posts an ad once every 4-5 months and then quickly disappears. They may have had some financial emergency and had a friend who convinced them to make some quick money over a couple weekends (enter, 2 girl special), but it's not something they want to do regularly or even have the time for. The appeal for me of these type of girls is that they're open-minded, generally sexually experienced, and know the laws of discretion. Often make good booty calls and can be more reliable than the typical SBs.

The challenge is figuring out which of them are still fresh to the game or too far gone. The ones that are too far gone, you'll always just be a client and things will be very business like. But with the fresh ones, it's still possible to have a more personal relationship. I've actually gotten the real Facebook pages of 3 escorts within the last two months without ever meeting them. So some of them aren't fully locked into the escort life and find the idea of a SD / SB arrangement appealing. With that in mind, I'll proceed with the second half of my update.

Escort SB 1.

I just started talking up with this one recently. She's mixed, half black / half asian, a spinner and beautiful face. She posts ads every 6 months or so. She goes to school, so that limits how much she can escort. She would prefer to have just one guy she can lean on for a few of her basic bills. We've texted a lot over the last couple of days and she's extremely personable, moreso than any escort I've talked to in recent memory. I sent her my pics and she said I was much more handsome than she expected, so I think she has a genuine attraction. We're suppose to meetup later this week and no discussion of money has been brought up yet. So actually might have the potential of being a legit SB and not just a booty call. That would be a first ever in my side-hobby of trying to convert escorts to SBs. So I'll let you guys know how the first meet goes later this week.

Former Escort SB.

This one is an interesting case. She actually used to escort a couple of years pretty heavily on Hx. She is an *extremely* hot AA, I'd say a perfect 10 in looks. Perfect hourglass frame, not too skinny, not too thick. Just perfect. The thing is, she's actually retired from escorting and has so for well over a year. Now she just does the occasional massage and gives the lucky dude a happy ending. We got along pretty well a couple of years ago, so we kept each other's number. I mentioned recently that I was in the market for a new SB and unlike a couple of years ago, now she was interested. She really doesn't want to escort again, but she's having some money problems again. So we're trying to do a "provisional" arrangement. I know her real identity and everything, and I've given her some money (not a ton though). The problem though is that she doesn't want to have sex. She'll do everything except for actual sex. I was really surprised to hear this at first, but she offered to return the allowance and said she just wasn't comfortable yet. I let her keep the money and just said we'll take things slow. Honestly, she's so hot that I don't mind spending time with her doing almost-sex. Plus she's a very nice girl and it really seems like she's trying to open up a new chapter in her life and I don't want to pull her back down. So we've been talking and I'm helping her with starting a legit massage business and getting a license.

So far this 2014 I've been taking the nontraditional route with SBs. Part of it is because I've had to tighten the belt financially, so I've had to alter my strategies and move to different fishing pools. But it's offered some very unique experiences so far.