"Sugarbabies" / "Arrangements" Amateurs or Not?

**CantWinLosin** · 04-17-11 12:58

I second Literal's request about how to find the small-town escorts. That would be great knowledge to have. PM if you prefer. Thanks!

I'm finding that it's hard to get ladies to respond on SD4Me. I'm honest about my age and stats so that may be part of it, but I think a fair number don't really know what they want. All of the SB's that I had success with, I found on CL before they got rid of the "adult jobs" section. Sigh.

**Literal2** · 04-17-11 11:40

Originally Posted by Coolhand2 [View Original Post]

There has been a discovery (at least for me) that I have made as a result of SB no-shows. That is the small town provider. Not a provider that lives in a small town who tours, but a women who supplements her income by escorting. This is not unlike what the SB does. I have had two such experiences in the last month. One was a early thirties 5'7 spinner type with great skills. The other was a 22 yr old coed. 5'8, breasts to die for, toned, with gorgeous long hair and super tight.

There were a couple of common traits. Just by the fact of where they live I would be shocked if they had three dates a week, not multiple per day. The definition of low volume. Time did not seem to be a issue at all. I spent almost three hours with the coed and all but about 15 minutes was spent with me between her legs or she between mine (or both.) She too had great skills. Both women were highly orgasmic and the coed came so much I thought I was going to have to get a towel. I believe they aim to please because they need repeat customers. New ones are not coming along everyday. I will definitely see both again.

From a financial stand point it was pretty much the same as with a SB. The envelope was the same as I have provided (or intended to provide) SB's. I had to get a room because neither could host and did not provide in-call. That too was a cost I expected to pay with potential SB's. This may just be the same as the semi-pro SB but it had a different feel to it. I'm not giving up on the SB's but it seems to be a potential middle ground with out all the work that SB's take.

This is interesting. The only small town sb's I've checked out have been dogs. Way too skinny or way too fat or way too old. Dumb as rocks. Probably I've had bad luck, they can't all be like that. Maybe it's different with small town escorts. If you care to say, Cool, how would you suggest finding these honeys?

**Literal2** · 04-17-11 11:35

SB12 showed up on time wearing a cute sun dress, hair all shiny and clean, She said she'd been up and down all night worrying whether the alarm clock would go off for our early morning session. During our many prefuck emails over more than a month she repeatedly said she didn't want to fuck more than one guy. She's 39 and recently divorced. She said our first session was the first sex she'd had in months. Her body is tan, smooth and slim but of course not as firm as the 27-28 year olds. But I'll tell you this, she knows how to make a man cum. I've told her I'm not a long term deal and she says she is ok with that.

**Coolhand2** · 04-17-11 02:16

There has been a discovery (at least for me) that I have made as a result of SB no-shows. That is the small town provider. Not a provider that lives in a small town who tours, but a women who supplements her income by escorting. This is not unlike what the SB does. I have had two such experiences in the last month. One was a early thirties 5'7 spinner type with great skills. The other was a 22 yr old coed. 5'8, breasts to die for, toned, with gorgeous long hair and super tight.

There were a couple of common traits. Just by the fact of where they live I would be shocked if they had three dates a week, not multiple per day. The definition of low volume. Time did not seem to be a issue at all. I spent almost three hours with the coed and all but about 15 minutes was spent with me between her legs or she between mine (or both.) She too had great skills. Both women were highly orgasmic and the coed came so much I thought I was going to have to get a towel. I believe they aim to please because they need repeat customers. New ones are not coming along everyday. I will definitely see both again.

From a financial stand point it was pretty much the same as with a SB. The envelope was the same as I have provided (or intended to provide) SB's. I had to get a room because neither could host and did not provide in-call. That too was a cost I expected to pay with potential SB's. This may just be the same as the semi-pro SB but it had a different feel to it. I'm not giving up on the SB's but it seems to be a potential middle ground with out all the work that SB's take.

**Coolhand2** · 04-17-11 01:28

Originally Posted by Literal2 [View Original Post]

SB9 showed up at my hotel, right on time. She insists she's 28, so I believe her. She asked me my age and I told her the truth. She seemed surprised but didn't freak out. She claims I'm the only one she's fucking. Like SB12, she has horror stories about weirdo guys she's met on the sb website. For some reason she begged me during intercourse to fuck her especially hard today."Please, please, fuck me hard, fuck me hard," is what she said. I think it soothes her anxieties or something to have my dick tear up her pussy. Anyway I made her cum twice just to show her who's boss.

I've said it before and I'll say it again: "YOU THE MAN." I want to know what you eat for breakfast.

**Coolhand2** · 04-17-11 01:22

Originally Posted by Literal2 [View Original Post]

Cool, you were very disciplined with these ladies and I wonder if you ever loop back? I find there is something about the male-female relationship that makes girls want to say no from time to time, even if they really truly want to get laid. Usually you see this on first approach. I always expect a girl to say no the first time I ask her to be alone with me, and once she does I figure some of the pressure is off her. Then you can wait awhile and loop back. Second or third time around, she's already proved to herself she's not a prostitute because she said no before. So she can psychologically be more accepting of penetration. This may be especialy true of sb's who may be considered pro's by some but most of them don't think of themselves that way.

Now somebody who has already spread her legs for you is past that point in her mind. It could be that you just don't click with her anymore and that happens to all of us. But it could be some other dude is offering her more or is more likely to turn into a husband, you just can't tell. But I'm just wondering if you loop back.

First post as a Senior Member.

I had been considering trying CSB1 again as you suggest. What's been holding me back is the potential of wasting a pass from the Warden. They take some setup to acquire and if I cancel in less than 24 hours it has the potential of making them harder to acquire. With the luck (all bad) that I've been having in setting up new SB's, I may take the risk.

**Literal2** · 04-16-11 20:16

SB9 showed up at my hotel, right on time. She insists she's 28, so I believe her. She asked me my age and I told her the truth. She seemed surprised but didn't freak out. She claims I'm the only one she's fucking. Like SB12, she has horror stories about weirdo guys she's met on the sb website. For some reason she begged me during intercourse to fuck her especially hard today."Please, please, fuck me hard, fuck me hard," is what she said. I think it soothes her anxieties or something to have my dick tear up her pussy. Anyway I made her cum twice just to show her who's boss.

**Literal2** · 04-16-11 19:56

Originally Posted by Spitfire [View Original Post]

We'll never know how it would have worked, she never showed up. A wasted trip.

Bummer. I'm sorry for you, man.

**Spitfire** · 04-16-11 18:22

Originally Posted by Literal2 [View Original Post]

I'll be interested to hear how this works out. I'd worry that presenting the two envelopes would make her confront herself and what she is doing too directly so she would chicken out. If I got her as far as the room I think I'd just touch her hair, then her back, etc. Etc. Allowance would discreetly be delivered at the end of the meet. But maybe she's a negotiator and wants everything spelled out. Often that's what a really hot girl does. Either way, man, good luck. Five hour drive, whoa. You sound as crazy for pussy as I am.

We'll never know how it would have worked, she never showed up. A wasted trip.

**Literal2** · 04-16-11 11:09

Originally Posted by Spitfire [View Original Post]

We've had discussions where I told her that I was looking for more and to make sure she's ok with that aspect of it before meeting me again. We're meeting alone this time, first to dinner then back to my hotel. I plan to have 2 envelopes ready. I'll tell her one is for dinner and goodbye and the second, much larger envelope is for serving me dessert. It will be up to her if she goes home with both envelopes or only one.

But this is her second, and final, chance to get things right.

I'll be interested to hear how this works out. I'd worry that presenting the two envelopes would make her confront herself and what she is doing too directly so she would chicken out. If I got her as far as the room I think I'd just touch her hair, then her back, etc. Etc. Allowance would discreetly be delivered at the end of the meet. But maybe she's a negotiator and wants everything spelled out. Often that's what a really hot girl does. Either way, man, good luck. Five hour drive, whoa. You sound as crazy for pussy as I am.

**Literal2** · 04-16-11 11:03

Originally Posted by Spitfire [View Original Post]

Last night, I met my first of 2 college girls I have lined up this weekend. Not my first SB experience, but since it's the first official report on this forum, I'll call her SSB1.

As it turns out, the 'college' part was a bit of exaggeration on her part. She works at a Hooters restaurant and takes an occasional class at a community college. But she's still young, attractive and has a toned body. We met up for dinner and had nice conversation getting to know each other beyond what we had already discussed via email. She seems to be sort of a free spirit and not really sure what she wants out of life yet. But anyway, we had dinner, some laughs and proceeded back to my hotel where things progressed nicely. I'll definitely see her again.

Now it's off for a 5 hour drive in the opposite direction to meet the other young lady; hopefully it will be much smoother than the first time we met.

Now that sounds like a great evening. Think of all the Hooters customers who see her every day who wish they could get into her pants, but you're the one who found the key. Nice.

**Spitfire** · 04-16-11 10:18

Last night, I met my first of 2 college girls I have lined up this weekend. Not my first SB experience, but since it's the first official report on this forum, I'll call her SSB1.

As it turns out, the 'college' part was a bit of exaggeration on her part. She works at a Hooters restaurant and takes an occasional class at a community college. But she's still young, attractive and has a toned body. We met up for dinner and had nice conversation getting to know each other beyond what we had already discussed via email. She seems to be sort of a free spirit and not really sure what she wants out of life yet. But anyway, we had dinner, some laughs and proceeded back to my hotel where things progressed nicely. I'll definitely see her again.

Now it's off for a 5 hour drive in the opposite direction to meet the other young lady; hopefully it will be much smoother than the first time we met.

**Spitfire** · 04-16-11 10:07

Originally Posted by Literal2 [View Original Post]

Good luck to you too, Spit. Two college girls, damn. That sounds tasty.

Can I ask a question. With the girl you saw once before, what is / was your strategy for moving to penetration? Are you meeting alone this time? I remember with SB2 after a get acquainted session over cokes she emailed me saying she'd had a nice time. I replied,"So did I Sweetie, but the next time I see ya we're going to be alone and I'm going to touch ya." She said something ambiguous in response, like "I hear you," but when I got to her house she was dressed in sweatpants with no underwear and when I slipped my hand in them her pussy was boiling liquid. She turned into a squirter. I think it was the delay and her anticipation that caused her to get so hot and she knew what I was going to do to her before I arrived.

We've had discussions where I told her that I was looking for more and to make sure she's ok with that aspect of it before meeting me again. We're meeting alone this time, first to dinner then back to my hotel. I plan to have 2 envelopes ready. I'll tell her one is for dinner and goodbye and the second, much larger envelope is for serving me dessert. It will be up to her if she goes home with both envelopes or only one.

But this is her second, and final, chance to get things right.

**Literal2** · 04-16-11 09:47

Originally Posted by Spitfire [View Original Post]

Good luck with your weekend! I've got 2 girls lined up myself, but of course, both require travel and they're in opposite directions. Both of them are college students. I've met one of them before and I'm breaking my own rule about not seeing her again since there was nothing more than dinner the first time.

Good luck to you too, Spit. Two college girls, damn. That sounds tasty.

Can I ask a question. With the girl you saw once before, what is / was your strategy for moving to penetration? Are you meeting alone this time? I remember with SB2 after a get acquainted session over cokes she emailed me saying she'd had a nice time. I replied,"So did I Sweetie, but the next time I see ya we're going to be alone and I'm going to touch ya." She said something ambiguous in response, like "I hear you," but when I got to her house she was dressed in sweatpants with no underwear and when I slipped my hand in them her pussy was boiling liquid. She turned into a squirter. I think it was the delay and her anticipation that caused her to get so hot and she knew what I was going to do to her before I arrived.

**Literal2** · 04-16-11 09:27

Originally Posted by Coolhand2 [View Original Post]

I'm going to take your advice on CSB1 and totally back off for awhile. I'll see if she contacts me.

Cool, you were very disciplined with these ladies and I wonder if you ever loop back? I find there is something about the male-female relationship that makes girls want to say no from time to time, even if they really truly want to get laid. Usually you see this on first approach. I always expect a girl to say no the first time I ask her to be alone with me, and once she does I figure some of the pressure is off her. Then you can wait awhile and loop back. Second or third time around, she's already proved to herself she's not a prostitute because she said no before. So she can psychologically be more accepting of penetration. This may be especialy true of sb's who may be considered pro's by some but most of them don't think of themselves that way.

Now somebody who has already spread her legs for you is past that point in her mind. It could be that you just don't click with her anymore and that happens to all of us. But it could be some other dude is offering her more or is more likely to turn into a husband, you just can't tell. But I'm just wondering if you loop back.