"Sugarbabies" / "Arrangements" Amateurs or Not?

[Literal2]

One of the first SB's I contacted when I went on the site seemed ready to go. There were lots of back and forth emails and I was ready for my first SB. There was no discussion of sugar at all. Finally when I tried to set the date she backed off. She said she wasn't ready for a relationship based purely on sex. (Is there any other?). She was 27 and I'm sure this was her first foray into this kind of setup. After four months, she contacted me yesterday and said she was more than ready; she was anxious to get started. I don't know what prompted this. Financial situation worsen; general horniness or what. My problem is with what I have already on my plate, I don't know when I can schedule her. The point is I left her alone and she came around in her own good time. Just don't know when I'm going to be able to take advantage of her new mindset.

Damn, Cool. You are on a roll. Come on, you can take half an hour out of your schedule to fuck this little sugarbaby.

[Literal2]

I have to disagree somewhat. As I've posted previously, I'm looking for a long-term mistress type of arrangement. I'm not looking for a girlfriend or a wife, but it's still a deeper level of connection I'm seeking. It's not all about the sex for me, I enjoy the emotional and social aspects as well. Going to dinner, taking her shopping, etc. If I wanted just the sex, I wouldn't bother with all of this, I would just call a pro. That's not intended as an insult to anyone here, I understand the joy of finding someone fresh, just a realization that we're all looking for something unique. It's what makes it a fun world!

Now, I'm guessing my situation is different from most posting here. I'm not married and I have no family to worry about. I work from my home for a few long-distance clients, so I have few points of vulnerability. But, I am careful until I get to know someone before I give out a lot of info. I do give my real name and I have a google voice number that I give out (thanks for that tip fellow forum member. I forget who it was!). But until I'm really comfortable I don't bring anyone to my home. My first SB spoiled me as much, if not more, than I spoiled her. I'm looking for that again. Don't know if I'll find it. But I'm sure trying.

Spit, I hope you find what you are looking for.

[Literal2]

I think the most important factor by far is setting expectations with the girl before the pussy is accessed. I make sure they know I'm not free and also that I won't take care of all their needs. Be explicit in a polite way. Offer directly or indirectly to back off, walk away and give up access to her pussy if she did not previously understand or cannot accept what you say. This makes it much easier later when she asks for more. Just say, sorry no. You have to do all this with a smile and with tenderness though, not as some hard ass. At least thats what I do. So far its worked ok.

Today one of the girls asked me for extra money. I said no, but I don't like this and may have to eat my words.

[Coolhand2]

Sugar in advance told Sb3 that Literal2 was not a tire kicker. Not coming to the chamber for three months after their public meeting told him she wasn't ready and needed time to take the step, but he didn't know that when they met in public. It was probably her first time. Literal2 was patient and letting her move to him was the key. He didn't push on a string. I'm betting she had many opportunities and chose him because he let her control what she chose and when she chose it. This is the only way that works.

One of the first SB's I contacted when I went on the site seemed ready to go. There were lots of back and forth emails and I was ready for my first SB. There was no discussion of sugar at all. Finally when I tried to set the date she backed off. She said she wasn't ready for a relationship based purely on sex. (Is there any other?). She was 27 and I'm sure this was her first foray into this kind of setup. After four months, she contacted me yesterday and said she was more than ready; she was anxious to get started. I don't know what prompted this. Financial situation worsen; general horniness or what. My problem is with what I have already on my plate, I don't know when I can schedule her. The point is I left her alone and she came around in her own good time. Just don't know when I'm going to be able to take advantage of her new mindset.

[Spitfire]

So, the advice is to just keep it on the surface! Stay away from getting to know these broads. They are out to get paid and you are out to get laid. When you take it deeper than that you get screwed, but not in the bed.

I have to disagree somewhat. As I've posted previously, I'm looking for a long-term mistress type of arrangement. I'm not looking for a girlfriend or a wife, but it's still a deeper level of connection I'm seeking. It's not all about the sex for me, I enjoy the emotional and social aspects as well. Going to dinner, taking her shopping, etc. If I wanted just the sex, I wouldn't bother with all of this, I would just call a pro. That's not intended as an insult to anyone here, I understand the joy of finding someone fresh, just a realization that we're all looking for something unique. It's what makes it a fun world!

Now, I'm guessing my situation is different from most posting here. I'm not married and I have no family to worry about. I work from my home for a few long-distance clients, so I have few points of vulnerability. But, I am careful until I get to know someone before I give out a lot of info. I do give my real name and I have a google voice number that I give out (thanks for that tip fellow forum member. I forget who it was!). But until I'm really comfortable I don't bring anyone to my home. My first SB spoiled me as much, if not more, than I spoiled her. I'm looking for that again. Don't know if I'll find it. But I'm sure trying.

[Golfcart]

She's handing that problem to him.

Both must be happy naturally. I don't think negotiating with a woman works. If one gives in for harmony resentment will creep in and everything goes south.

[Literal2]

So, the advice is to just keep it on the surface! Stay away from getting to know these broads. They are out to get paid and you are out to get laid. When you take it deeper than that you get screwed, but not in the bed.

I know, man. I know! But when I get accustomed to penetrating a fine young female with smarts and a nice way about her, it's hard to let go. It's hard to stay objective.

[Literal2]

I think the most important factor by far is setting expectations with the girl before the pussy is accessed. I make sure they know I'm not free and also that I won't take care of all their needs. Be explicit in a polite way. Offer directly or indirectly to back off, walk away and give up access to her pussy if she did not previously understand or cannot accept what you say. This makes it much easier later when she asks for more. Just say, sorry no. You have to do all this with a smile and with tenderness though, not as some hard ass. At least thats what I do. So far its worked ok.

[Coolhand2]

Harvesting sugarbaby pussy is like mongering, there is always a level of risk. All you can do is to reduce it as much as you can but unless you give up the pussy, some risk will always remain. How to reduce risk? Well, start by setting the girl's expectations correctly, always treat her right, and make it hard for her to find you when you don't want to be found.

I've had several girls ask for extra help. One just told me I wasn't giving her enough sugar and dumped me. It wasn't a problem, I had accessed her vagina from her clit to her cervix as much as I desired and was chasing other girls anyway. A second sb always had her hand out for more. I like her and went along for a while but then just said, sorry can't do it and reset to the original deal. It didn't affect my ability to release semen inside her pussy at all. Another is really broke and trying to keep up a suburban housewife lifestyle with big car and tvs etc. I haven't seen her for months but she still occasionally asks for money. I just say no, but try to be sympathetic. In any case I've tried to keep her from knowing enough about me to cause trouble.

You guys must have had similar experiences.

Of course. It comes with the territory. When you see a escort you're not expecting to hear from her again unless you call. No texts, no emails (unless to let you know she's back in town) and for sure no requests for more sugar; but she is not fresh. If she hasn't been around the block a few times she's at least firmly headed in that direction.

The SB on the other hand has the allure of freshness. The kind of girl we would go after if we were thirty years younger and had maintained our bodies. Regardless of their age we expect them not to be jaded. That when we look in their eyes, all the lights are still on. So we spend the time in the SB fields trying to harvest (love that term) the ones that catch our attention. The emails; the phone calls; the meet and great meeting; the false starts; the will-she-won't she. And that's before you've even got the pussy; which you may not get!

After you get the pussy comes the real risk that others have talked about. Those risks are real. My CSB2, after giving up the pussy, started texting me the next day for money to go shopping. This went on for about three days. Needless to say I dropped her immediately. (Tiger rule violation) CSB6, after being happy with the sugar, wanted interim payments and sent me several emails with her requests. It comes with the territory.

I wasn't quite sure what to expect when I started down the SB path but what I found is, when it works, I love the fresh!

[Miketastic69]

I've had exactly what you describe with one sb. The one I mentioned having some trouble getting rid of. The first 2-3 times were what we're looking for. Fun, good sex, no drama. This is also the only local sb I've seen. Then it started. Will you get me a pack of cigarettes and drop them by my house? I need to buy a book for school, I'm behind in my daycare payments but I promise I'll fuck you for free for 2 weeks all you want (which never happened of course). When I cut her off, she threatened me with blackmail basically. I took a deep breath and just told her we were done and she had to do whatever she had to do. Told her I wasn't responsible for her financial troubles and it had ceased to be fun for me. Fortunately I haven't heard from her in several months so I think I'm in the clear on that one.

It goes without saying gents, be careful out there. While some of us do have conversations with our sbs, don't give up too much information where they can find you. Use a throwaway cell phone, pay for meals in cash. More than once I've paid with a credit card and the "friendly" server when he brings the check has said "thank you and have a good day Mr. Rat". Bingo! Now they know you're name assuming you use your real first name. Probably better not to even do that. As our friend Literal said, there's always risk unless you want to give up the (strange) pussy, and I'm not ready for that as I'm currently working on harvesting 2 new sbs, and have another one I've seen a couple times that is so hot to trot it's ridiculous. The good part about that is I don't really give a shit if the other 2 work out or not as I have options. Kind of like going to a strip club for a drink and to look at naked women, knowing you're going to get some pussy in an hour or so from a sb / escort.

I learned from experience that you don't want to even start down the road of "extras." Keep it to a strict arrangment and don't slip no matter how tempted you get.

I got started because she seemed to legitimately need a few things. She was so sweet and precious that I thought,"what the hell?" Then, it became more-demanding. When I finally ended it she started with the threats. It got to a point where she saw my car parked at a store and put a note under my windshield wiper. If I had a girlfriend or wife that would have been horrific.

Luckily, she got bored or found a new fish. But for a few weeks I was pretty worried.

So, the advice is to just keep it on the surface! Stay away from getting to know these broads. They are out to get paid and you are out to get laid. When you take it deeper than that you get screwed, but not in the bed.

[Magic Rat]

I've had exactly what you describe with one sb. The one I mentioned having some trouble getting rid of. The first 2-3 times were what we're looking for. Fun, good sex, no drama. This is also the only local sb I've seen. Then it started. Will you get me a pack of cigarettes and drop them by my house? I need to buy a book for school, I'm behind in my daycare payments but I promise I'll fuck you for free for 2 weeks all you want (which never happened of course). When I cut her off, she threatened me with blackmail basically. I took a deep breath and just told her we were done and she had to do whatever she had to do. Told her I wasn't responsible for her financial troubles and it had ceased to be fun for me. Fortunately I haven't heard from her in several months so I think I'm in the clear on that one.

It goes without saying gents, be careful out there. While some of us do have conversations with our sbs, don't give up too much information where they can find you. Use a throwaway cell phone, pay for meals in cash. More than once I've paid with a credit card and the "friendly" server when he brings the check has said "thank you and have a good day Mr. Rat". Bingo! Now they know you're name assuming you use your real first name. Probably better not to even do that. As our friend Literal said, there's always risk unless you want to give up the (strange) pussy, and I'm not ready for that as I'm currently working on harvesting 2 new sbs, and have another one I've seen a couple times that is so hot to trot it's ridiculous. The good part about that is I don't really give a shit if the other 2 work out or not as I have options. Kind of like going to a strip club for a drink and to look at naked women, knowing you're going to get some pussy in an hour or so from a sb / escort.

[Literal2]

Harvesting sugarbaby pussy is like mongering, there is always a level of risk. All you can do is to reduce it as much as you can but unless you give up the pussy, some risk will always remain. How to reduce risk? Well, start by setting the girl's expectations correctly, always treat her right, and make it hard for her to find you when you don't want to be found.

I've had several girls ask for extra help. One just told me I wasn't giving her enough sugar and dumped me. It wasn't a problem, I had accessed her vagina from her clit to her cervix as much as I desired and was chasing other girls anyway. A second sb always had her hand out for more. I like her and went along for a while but then just said, sorry can't do it and reset to the original deal. It didn't affect my ability to release semen inside her pussy at all. Another is really broke and trying to keep up a suburban housewife lifestyle with big car and tvs etc. I haven't seen her for months but she still occasionally asks for money. I just say no, but try to be sympathetic. In any case I've tried to keep her from knowing enough about me to cause trouble.

You guys must have had similar experiences.

[Varoom]

With all the reports coming out of the woodwork I'm surprised someone hasn't mentioned a SB hitting one of us up for a loan / advance / whatever as in, "Honey, I'm a little short this week."

That is the biggest risk of a sb / sd entanglement that once they get some leverage, they decide to attempt to use that leverage wisely. I know some of you play several hours away from home, but lets face. That distance is a phone call away. Not far enough, in other words.

So no tales of whoa in that regard from the group, and I am surprised by this. Of course also pleased that no one has had to go there at the same time. This may speak well of how you gents play your hands with the sb's.

[Golfcart]

With all the reports coming out of the woodwork I'm surprised someone hasn't mentioned a SB hitting one of us up for a loan / advance / whatever as in, "Honey, I'm a little short this week."

[Magic Rat]

This thread keeps getting better and better. It seems we have similiar experiences with the sb's and advance sugar discussions.

I've had longer term "relationships" with 2 sbs so far, not counting my couple of stripper / sbs. I'll steal Literal's idea of a list, although mine will be in order of favorites:

SB1-this wasn't her first rodeo. We chatted a lot on the computer before meeting and absolutely knew where the process was heading. She's the only sb I've met in the hotel room first. Our chat was one of those deals where who is going to make the first move and throw out a number. I relented but gave a range for a regular meet and a higher sugar amount for an overnighter. She told me her minimum was the overnight rate I quoted. That ended up one of several overnights with her resulting in her being my atf sb. Multiorgasmic, squirter, sex freak. Most meetings took place at her house so no hotel $. Too bad she found a regular guy and got married.

SB2-we met for lunch, drinks, get to know you time. She casually made mention of a Days Inn up the street, then turned the topic to sugar. Her sugar contribution ended up being my standard amount as it turns out, although she was only the second sb I had seen at the time. After one time at the hotel, all future meetings were at her place. I saw her off and on for about a year and a half until she moved 500 miles away.

SB3-and current favorite. We met for the get acquainted meeting, where she said she had never actually done the deed with a sd. No discussion at all of sugar and we end up in a hotel room. At the end she asked if I was going to give her anything. Of course I said and gave her my standard amount for a multipop, multi hour date. I guess it worked because she texted me a few days later asking when we could meet again. This one is still in process. Could be awesome, could be over after 2 trips to the F Chamber.

SB4-met for lunch, walked out to car and she asks how I thought it went. Next thing I know her big tits are crushed up against my chest and her tongue is down my throat. End up at nearby hotel, no advance discussion of sugar. All events were quicker than my favs above so she got less sugar. Ended up she wanted an ATM more than a fuck buddy so she was dropped rather quickly, although it wasn't that easy getting rid of her.

SB5-the youngest I've met so far. Mid 20s and very pretty. Met for lunch and drinks, no discussion of sugar. Met a couple weeks later in hotel and I gave her my quickie sugar rate in her jeans pocket. We met one more time and she was expecting way more sugar than I was willing to pay or she deserved based on her service level. GPS.

All the others-4 total. Met for lunch / drinks, proceeded to hotel for fairly uneventful time, gave them all my quickie rate and never saw or contacted them again. No advance sugar discussions and put the sugar in pants pocket or open purse at the end.

I guess the point is, there is no one way this Sugarbaby deal works. My favorite mentioned sugar upfront, most of them haven't. I've only had the one disappointed in the amount of sugar and I'm not a high roller by any means. I enjoy this way more than escorts as in general I find the sbs appreciate the $ and sex more, and some are actually much wilder than escorts. Plus once you've arrived at the proper amount of sugar, the monetary aspect is quite minor to the experience.