"Sugarbabies" / "Arrangements" Amateurs or Not?

I think the arrangements site asks "How much allowance are you willing to pay per month?" or something like that, which makes the relationship sound more long term. One of the earlier comments here (Thud maybe) said he tells them $1k per month based on multiple visits.

In my case I don't usually have any amount agreed to but I do hope that if we like each other it won't just be a one time thing. I try to leave them happy both by a gift and sexually so I don't have a problem telling them in advance I don't want to talk specifics but I expect they will be happy. I've cut off several possibilities after progressing to the date setting discussion because the girl became too demanding. I want the initial meet to be highly anticipated and exciting for both of us. When distrust creeps in at this early stage of a relationship it can turn everything sour.

As we've said I don't think chasing sb's or amateurs is for everybody. When you want a sure thing you sometimes really have to get it or you will feel ill and unable to think of anything else. But for me, chasing sb's is a lot like hunting or fishing. Sure you can go into the grocery store and buy whatever you want to eat off the shelf. But it just doesn't taste as good as something you've stalked for hours and landed all by yourself.

There are always more females out there if one doesn't come through.

I hope Cool lets us know what happens Monday, one way or the other.

[QUOTE=Literal2;1150638]I hope Cool lets us know what happens Monday, one way or the other.[/QUOTE]For sure. Still havn't heard from CSB2 since my answer on the allowance.

Had my meeting today with CSB2. First of all she wanted me to arrange a meeting place but I told her since she knew the town better that I would leave that up to her. I wanted to see where she would pick since I thought it would give me some indication on where her head was. I called her when my business was finished and she texted me an address as to where to meet her. It was only when I got there that I found out it was a motel with a bar. I thought this was good sign. Met her in the bar and had a drink. She was in her early thirties, kind of cute with a decent rack. She seem determined to have the "first date" kind of conversation that I really wasn't into. Not having tons of time (the warden keeps a good eye on the clock) I pressed to move things along. The "allowance" issue did not come up at all. As it turned out she had already got a room (an even better sign) so we proceeded on up. Didn't take long to get her out of her clothes and as it turned out her body was nicer then CSB1. We then spent a nice couple of hours between the sheets. She was attentive, passionate and very willing. She got wet easily and came several times with out to much effort. (At my age that's important) Here's the thing; even with all her effort and willingness, she did not have the skills of my CSB1 housewife! CSB1 really knows what to do with a dick in her mouth and provides a trip to the islands. Just because of what she did with the hotel room I'm placing her between the amateur and the semi-pro category. I put the allowance in her purse as I was leaving so I don't know her reaction yet. I'm currently in communication with two more potentials, both single moms. Another home run makes it a good day.

Sounds like a good time, Cool. Congratulations. I've never had a non-pro get a hotel room. Very unusual, especially for a first date. Who paid for the room and if she did, did you increase the amount of her gift? Just curious.

I find different girls have different sexual skills too. Sometimes oral skills are lacking in the hottest girls. Maybe they just feel they don't have to work so hard because they're cute. On the other hand, some girls just seem obsessed with getting their mouth on your dick. It would be great to find some way to predict this, just like it would be great to be able to predict what a girl's pussy looks like from her external appearance. What I like is a pussy that starts out neat and tidy and then gets messed up as you go along.

Are you planning to loop back and do csb1 again? Or will she be backup while you go for the next two potentials?

As for me, I haven't worked the sd website (contacts and emails to new girls) at all for about two weeks. I have my atf sb4 coming up again this weekend, and supposedly sb9 who I met with briefly in a bar over a week ago. SB9 is a student / artist and very curvy and flirty and has been out of town for a week on vacation. Before she left she said she was eager to move on to penetration but we shall see. It would be my luck for her to run into some dudes on vacation who have been fucking her brains out to her total satisfaction. I hope not. She has the potential to become another fave and it would be just great to have her as well as sb4 whenever I want. Meanwhile other possibles keep replying to my sd website emails from weeks ago and one or more of these may develop into something, especially if sb9 doesn't come through for me.

[QUOTE=Literal2; 1152398]Sounds like a good time, Cool. Congratulations. I've never had a non-pro get a hotel room. Very unusual, especially for a first date. Who paid for the room and if she did, did you increase the amount of her gift? Just curious.

I find different girls have different sexual skills too. Sometimes oral skills are lacking in the hottest girls. Maybe they just feel they don't have to work so hard because they're cute. On the other hand, some girls just seem obsessed with getting their mouth on your dick. It would be great to find some way to predict this, just like it would be great to be able to predict what a girl's pussy looks like from her external appearance. What I like is a pussy that starts out neat and tidy and then gets messed up as you go along.

Are you planning to loop back and do csb1 again? Or will she be backup while you go for the next two potentials?

As for me, I haven't worked the sd website (contacts and emails to new girls) at all for about two weeks. I have my atf sb4 coming up again this weekend, and supposedly sb9 who I met with briefly in a bar over a week ago. SB9 is a student / artist and very curvy and flirty and has been out of town for a week on vacation. Before she left she said she was eager to move on to penetration but we shall see. It would be my luck for her to run into some dudes on vacation who have been fucking her brains out to her total satisfaction. I hope not. She has the potential to become another fave and it would be just great to have her as well as sb4 whenever I want. Meanwhile other possibles keep replying to my sd website emails from weeks ago and one or more of these may develop into something, especially if sb9 doesn't come through for me. [/QUOTE]Her getting the hotel room was the reason I placed her in the amateur / semi-pro category. I wasn't quite sure what to make of it. She did pay for the room so being the gentleman that I am, I did increase the amount of her gift. In retrospect that could be a problem since she doesn't know that's what I did and made create an expectation that I won't meet. I haven't decided yet if there will be another meeting with her (CSB2) so it may not matter. It may depend on how things go with the two new potentials I mentioned. There's still the five that say they are ready to meet so I have to decide something there.

If you're able to figure out a way to predict what a girls sexual skill sets are sign me up quick. That's why I would not see a provider who did not have reviews that gave me some idea of what I was paying for. With the Sugar Babies it's a total crap shoot. I may have been spoiled by the great skills that CSB1 has. Which is why, in answer to your question, I'm trying to set up a meeting with her next week. I figure why I try to sort out what I'm going to do about the other SB's I shouldn't let such talent go to waste. (Men are such dogs!)

Good luck with SB9. Even if there were some dudes fucking her brains out, vacation is over and it's time to come back to reality. I bet that what ever her financial issues were that brought her to the SD site in the first place are still there and still need to be addressed. Besides, a sore pussy will get better, unpaid bills won't!

I've been emailing SB9 for more than a month, first through the sb website and then by our own emails. One meeting was put off because of her period. When I first asked her to meet me in a hotel she said,"I don't even know you!" So we set up a get acquainted meeting to which she was so late I could only spend five minutes with her. She was sorry and said she'd be on time next time, so I set another date for a hotel. This time she said,"I've never done this before but its the only place we can meet I guess." She says she's 27 and looks like it, nice body from what I could see, very cheerful, pretty. I've been waiting to fuck her for a long while and I think it's finally going to happen Saturday. She is definitely a non-pro. She could be a keeper if I can manage the relationship correctly. I've told her it will be a couple times a month and has to be discreet and she's ok with that. Meanwhile on Sunday I have a three-peat scheduled with SB4. That girl is so hot but she is also so hard for me to get to. Plus now she wants more money. I'll have to see how things go Sunday. This may be my last time with SB4. But I want to have a harem of hot 20-something girls to fuck when I feel like it and I can't do it if I don't hold on to the ones I like the best.

She didn't contact me for more than 30 hours before our scheduled meeting so I thought it was 50-50 SB9 was going to stand me up. That would have made it 3 wasted hotel rooms in three months. But it turned out SB9 was on time, very sexy, very elegantly dressed. I love that. We met in an upscale hotel because I wanted to put her at ease when she arrived. I even left the curtains open so she could see in to the sitting room from outside when she first arrived. We had some drinks on the sofa as we talked and got acquainted. I caressed her back, arms and legs and kissed her occasionally to warm her up while we made small talk for about half an hour.

She was very satisfying and passionate in bed. All the usual stuff: dfk, BBBJ, mish, dg, cg, etc. No DATY since she had just finished her period. She has a nice slippery little slit which she keeps shaved. She came very fast with clit and nipple play and my dick in her mouth. Her natural large boobs are extremely sensitive and I could possibly make her cum just by sucking on them. I think she's about five years older than she claimed online, which would make her early 30's. I'd rate her an 8 for looks.

She's a tall girl and her weight is about 8-10 pounds above ideal and her hair is a little thin. She's not the knockout SB4 is but she's got a great body and is very attractive. I'll see her again. This gives me three I can see anytime I want now, but SB5 is too fucked up for me, dumb as a box of rocks and too skinny so I'm not planning to see her again unless Johnson has an emergency. I'm sure I could fuck SB6 and SB8 anytime too but they are just too heavy.

I'm probably paying double for my keeper UTR's what the skilled mongers pay for pros but I'm trying to building a stable of prime young amateur females and I don't have the advantages of youth, good looks or a bachelor pad so its hard.

Tomorrow its back to SB4.

[QUOTE=Literal2; 1155023]She was very satisfying and passionate in bed. All the usual stuff: dfk, BBBJ, mish, dg, cg, etc. No DATY since she had just finished her period. She has a nice slippery little slit which she keeps shaved. She came very fast with clit and nipple play and my dick in her mouth. Her natural large boobs are extremely sensitive and I could possibly make her cum just by sucking on them. I think she's about five years older than she claimed online, which would make her early 30's. I'd rate her an 8 for looks.

She's a tall girl and her weight is about 8-10 pounds above ideal and her hair is a little thin. She's not the knockout SB4 is but she's got a great body and is very attractive. I'll see her again. This gives me three I can see anytime I want now, but SB5 is too fucked up for me, dumb as a box of rocks and too skinny so I'm not planning to see her again unless Johnson has an emergency. I'm sure I could fuck SB6 and SB8 anytime too but they are just too heavy.

I'm probably paying double for my keeper UTR's what the skilled mongers pay for pros but I'm trying to building a stable of prime young amateur females and I don't have the advantages of youth, good looks or a bachelor pad so its hard.

Tomorrow its back to SB4. [/QUOTE]Congrats Literal on SB9. To bad DATY was not available this time but looks like you'll have other opportunities. I like your idea of building up a stable of SB's. I think we're about the same age (60ish) and I have the same restrictions (don't have the advantages of youth, good looks or a bachelor pad.) I'm not sure of how many. They do take some amount of work.

I've had a interesting couple of days on the SB front. CSB2 is now out of the rotation. She sent me a text asking for money for some lame reason. This is a no-no. Text's are only to be sent on meeting days, no exceptions. (Tiger Woods rule) The pussy was good but not that good. I've been in a fast and furious round of communication with a 21 yr old. (CSB3) She said she had a previous SD who gave her $700-$900 a visit and anything less was cheap. I called her bluff, told her my allowance amount was $$, and if that was not acceptable I wished her well. Now this is a quote "well it was a nice try. 200 can be suitable." She says she has her own place so I'm going to try to set up a meet next week. I need to get to it before some one agrees to her original asking price. I'm set to meet CSB1 on Tuesday. I'm not yet ready to give up the tried and true. There are two more that say there ready to meet but CSB3 bumped them in the line. It's been a long time since I had any non-pro 21 year old pussy.

Another good session with SB4. This risks becoming a relationship.

Cool, it sounds to me like you are real disciplined with your money and I salute you for that. If you succeed with the 21-year old, I'll be envious. I haven't had a 21-year old girl since well since I was about 21. The few 19 year and 20/21 year olds I've pitched on the sb site have not come thru for me. Most of the time they just ignore me but as I reported two of them set dates and then disappeared. I did date a 23 year old stripper for a while a few years go, and now that I think of it, I dated a 20 year old stripper in Toronto a few times. The 20 year old was gorgeous, but completely insane, unpredictable and wild. She was a cutter (cut herself with razor blades). I couldn't handle her behavior. The 23 year old had a couple kids and wanted to move in. AAAARRGHHH! So my luck with the barely legal set on and on the sb site has not been real good.

I was amused by your Tiger Woods rules. I have my own version. Still trying to perfect them.

[QUOTE=Literal2; 1155482]Another good session with SB4. This risks becoming a relationship.

Cool, it sounds to me like you are real disciplined with your money and I salute you for that. If you succeed with the 21-year old, I'll be envious. I haven't had a 21-year old girl since well since I was about 21. The few 19 year and 20/21 year olds I've pitched on the sb site have not come thru for me. Most of the time they just ignore me but as I reported two of them set dates and then disappeared. I did date a 23 year old stripper for a while a few years go, and now that I think of it, I dated a 20 year old stripper in Toronto a few times. The 20 year old was gorgeous, but completely insane, unpredictable and wild. She was a cutter (cut herself with razor blades). I couldn't handle her behavior. The 23 year old had a couple kids and wanted to move in. AAAARRGHHH! So my luck with the barely legal set on and on the sb site has not been real good.

I was amused by your Tiger Woods rules. I have my own version. Still trying to perfect them. [/QUOTE]Well Literal SB4 sounds like a winner. Did a increase to her allowance come up? Be careful; relationship is a dangerous word. As to the 21 year old (CSB3) , no date has been set and I have not heard from her since our little back and forth. Maybe someone did slip in there who was willing to pay her asking price. I do live in hope. As a rule I tend to stay away from the young ones because they can be such unpredictable flakes. That's why I like the ones in there 30's. Much more stable. I did dream I saw a 19 yr old pro last year who had the tightest pussy I could ever remember. She got out of the biz before I could repeat. What a lost!

I do try to be careful with my funds since they are not unlimited for the pursuit of pussy. I was taken to task on this board for what I spent on a dream even though I felt got my monies worth. (see Richmond Escort Reports post #3425) I just want to make sure I get value for the money spent. Seeing an amateur where there's an exchange of money involved is the same to me as seeing a pro with no reviews. If she has great skills I would be willing to review the financial arrangement but those skills must be demonstrated first. That's why I like my housewife (CSB1) , not the hottest but absolutely mad skills and has never asked for a price increase.

My Tiger Woods rule was instituted after his text messages caused all of his misfortune. I consider it an update to my rule set brought about by the advances in technology. My second marriage blew up over a similar incident with a pager. (shows how old I am) It led to a very messy and costly divorce. I can't afford that happening again.

[QUOTE=Coolhand2; 1155636]Well Literal SB4 sounds like a winner. Did a increase to her allowance come up?

My Tiger Woods rule was instituted after his text messages caused all of his misfortune. I consider it an update to my rule set brought about by the advances in technology. My second marriage blew up over a similar incident with a pager. (shows how old I am) It led to a very messy and costly divorce. I can't afford that happening again. [/QUOTE]Yes she's asked for more allowance. Problem is, I know she needs it. She's a single mom, daddy pays nada, the girl works as a receptionist and is trying to play the sb / sd game straight as far as I can tell, meaning: she isn't seeing other sd's. She's pretty, emotional, passionate, funny. If I were 40 or even 30 years younger. Oh well. Anyway, she's trying hard to keep it together so I'm sympathetic. But I have my limits and I can't get involved beyond those limits. I have to make a decision about her in the coming weeks. This is one of the problems with the sb / sd concept. People get involved.

As to the Tiger Woods rules. I don't take texts from girls. Also I use a dedicated cell which is off most of the time (except for voice mail) and scrub the registers every time I use it. I keep a PO Box for some billing purposes and prefer cash whenever I can. I keep sensitive data encrypted with Truecrypt. I'm always looking for new security techniques so any suggestions or alternative techniques would be appreciated.

[QUOTE=Coolhand2; 1155636]I do try to be careful with my funds since they are not unlimited for the pursuit of pussy. I was taken to task on this board for what I spent on a dream even though I felt got my monies worth. (see Richmond Escort Reports post #3425) I just want to make sure I get value for the money spent. Seeing an amateur where there's an exchange of money involved is the same to me as seeing a pro with no reviews. If she has great skills I would be willing to review the financial arrangement but those skills must be demonstrated first. That's why I like my housewife (CSB1) , not the hottest but absolutely mad skills and has never asked for a price increase.

[/QUOTE]I looked at your post 3425 and the girl does seem unusually uninhibited. I tend more towards the shy types myself but occasionally a wild one is really a treat. I had a model out in LA once who was that way and she cost even more than 3425. In my case, it was great one time and the second time I wasn't into it. I don't know why, maybe I just like to be the dominant one in the action. My SB2, a chubby little hospital administrator, was very uninhibited, squirted all over the place, and nearly broke my damn dick off the three times I saw her. She kept trying to do anal and I kept avoiding it. Not my thing. Anyway she was riding me cg and slipped my dick up her butt without me knowing it. I put my hand way up her pussy and felt something I thought was a diaphragm. I pulled it out and it was my goddam condom! I panicked and got out, got up, washed and had her jerk me off. I waited a few weeks and went for an STD test which came back negative, thank god. It was a learning experience but I prefer the shy ones as a general rule. Skills are secondary for me. No disrespect to anyone else's preferences.

As far as money goes, every woman I've ever had has cost me money, my first wife most of all. For me it's a question of who makes me happy, not whether I'm getting a good financial deal. I'd rather fuck Princess Diana in her prime and spend $2k than fuck some old bag lady and spend a quarter. That being said, this forum is a great place to learn the going rate which is always of interest. And I love a bargain when one comes along.

I enjoy the shy ones also. Wading through all the scams, time wasters and 'want to-bes' can be a real chore, but when you find a good one, it makes it worth it.

Sorry to jump in here but I was told text messages were only stored for 24hrs then deleted. Only with a court order can they be retrieved.

[QUOTE=Literal2;1155871]As to the Tiger Woods rules. I don't take texts from girls. Also I use a dedicated cell which is off most of the time (except for voice mail) and scrub the registers every time I use it. I keep a PO Box for some billing purposes and prefer cash whenever I can. I keep sensitive data encrypted with Truecrypt. I'm always looking for new security techniques so any suggestions or alternative techniques would be appreciated.[/QUOTE]How do you manage the dedicated cell? I know if a second cell was discovered by the warden there would be hell to pay. The same with a bill for a PO Box. I've just careful to scrub the phone of texts and numbers before I come home. If she found something encrypted, she would want to know why. One has to stay on ones toes in this mongering business.

[QUOTE=Literal2;1156511]I looked at your post 3425 and the girl does seem unusually uninhibited. I tend more towards the shy types myself but occasionally a wild one is really a treat. I had a model out in LA once who was that way and she cost even more than 3425. In my case, it was great one time and the second time I wasn't into it. I don't know why, maybe I just like to be the dominant one in the action. My SB2, a chubby little hospital administrator, was very uninhibited, squirted all over the place, and nearly broke my damn dick off the three times I saw her. She kept trying to do anal and I kept avoiding it. Not my thing. Anyway she was riding me cg and slipped my dick up her butt without me knowing it. I put my hand way up her pussy and felt something I thought was a diaphragm. I pulled it out and it was my goddam condom! I panicked and got out, got up, washed and had her jerk me off. I waited a few weeks and went for an STD test which came back negative, thank god. It was a learning experience but I prefer the shy ones as a general rule. Skills are secondary for me. No disrespect to anyone else's preferences.[/QUOTE]As to the one in the post, she let me dominate by doing exactly what I wanted for as long as I wanted. I was seeing a women in California who worked in the film industry. A absolute freak but she was totally unstable. As great as her skills were, I had to cut her loose. Skills don't trump craziness. I do place a high premium on skills which is why I didn't begrudge the provider in the post the money. It was a one time thing but I'm hoping to run across a sugar baby who matches her. Maybe you should turn me on to SB2 when you're done with her.

[QUOTE=Literal2;1156511]As far as money goes, every woman I've ever had has cost me money, my first wife most of all. For me it's a question of who makes me happy, not whether I'm getting a good financial deal. I'd rather fuck Princess Diana in her prime and spend $2k than fuck some old bag lady and spend a quarter. That being said, this forum is a great place to learn the going rate which is always of interest. And I love a bargain when one comes along.[/QUOTE]I couldn't agree with you more. My second wife took me to the cleaners. It's been over 12 years and it still hurts a lot. I keep a bargain in my pocket. There's a thick ebony pro I dream about in Richmond who I call when someone cancels. $.5 and all avenues open. I usually can get her on short notice so a trip is not wasted.

You're right; this forum is great!