"Sugarbabies" / "Arrangements" Amateurs or Not?

[Coolhand2]

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]

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]

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]

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

Bummer. I'm sorry for you, man.

[Spitfire]

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]

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]

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]

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]

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]

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]

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.

[Literal2]

ATF SB4 opened her pussy for me again today. God I love that girl, I mean I love her body. I think I sucked her clit for a half hour while she sucked my dick. SB9 and SB12 both sent emails today confirming they will fuck on schedule tomorrow and the next day.

[Spitfire]

After emailing this lady six weeks ago or so I called it quits because of her unreasonable demands. She was actually a no show at a get acquainted meet the day I got the flat tire driving back from SB4. A few days ago I got back in touch with her, how are you doing, etc. She wanted to meet, fewer demands. It was supposed to be in a hotel bar. She actually arrived early and came straight to the room.

She's at least 39, as she said. But she is in very good shape. Beautiful ta ta's (professionally enhanced). Silky long dark hair. Slim waist, nice heart shaped ass (though a bit soft). Stretch marks show her age (like the photo of Christie I posed in another thread, very similar in appearance) and she has some flexibility issues in her joints. She looks like Minnie Driver the actress, if you remember her: dark eyes, wide mouth. A first for me: she has a stud in her clit hood. I played with it until she came and fucked her several different ways. All good.

But here's an interesting thing. She said she hadn't had sex for a while though she's been trying. She told me one dude on the sb / sd site said he was 49, promised to send a limo to drive her to him, the limo didn't show, he called to say he had problems with his private jet. She googled his digits, the guy's facebook shows he's a college student.

She said another dude gave her a bank check, she went to cash it at a bank and the check was counterfeit. She nearly got arrested.

So I guess its not just girls who are unreliable on these sites.

I'm glad I was patient with this sb. The weekend has begun well and I have a new filly in the stable if I want her.

Glad it went well, sometimes patience pays off. My lack of patience gets worse as I get older LOL. Let us know how it goes with SB4 and SB9

[Literal2]

After emailing this lady six weeks ago or so I called it quits because of her unreasonable demands. She was actually a no show at a get acquainted meet the day I got the flat tire driving back from SB4. A few days ago I got back in touch with her, how are you doing, etc. She wanted to meet, fewer demands. It was supposed to be in a hotel bar. She actually arrived early and came straight to the room.

She's at least 39, as she said. But she is in very good shape. Beautiful ta ta's (professionally enhanced). Silky long dark hair. Slim waist, nice heart shaped ass (though a bit soft). Stretch marks show her age (like the photo of Christie I posed in another thread, very similar in appearance) and she has some flexibility issues in her joints. She looks like Minnie Driver the actress, if you remember her: dark eyes, wide mouth. A first for me: she has a stud in her clit hood. I played with it until she came and fucked her several different ways. All good.

But here's an interesting thing. She said she hadn't had sex for a while though she's been trying. She told me one dude on the sb / sd site said he was 49, promised to send a limo to drive her to him, the limo didn't show, he called to say he had problems with his private jet. She googled his digits, the guy's facebook shows he's a college student.

She said another dude gave her a bank check, she went to cash it at a bank and the check was counterfeit. She nearly got arrested.

So I guess its not just girls who are unreliable on these sites.

I'm glad I was patient with this sb. The weekend has begun well and I have a new filly in the stable if I want her.

[Spitfire]

Exchanged texts yesterday with a 30yr-old from Newport News from the site (seriously hot petite blonde with major ta-tas. I suspect she's a pro or semi-pro) and set up an initial meet for tonight at a restaurant she knew. Thought we had a firm appointment, and had to be there anyway, so headed there at the appointed time. About 10 minutes before the appointed time, I got a text that she hadn't heard from me. Since I was driving I couldn't respond immediately, but when I got to a light about 10 minutes later I responded that was on my way and would be there in a minute. We were meeting at a place I'd never been before, and when I got to the address (a major intersection with stripmalls on all sides) I circled thru all the malls and couldn't find the place she had named, so I texted that I couldn't find the place and please call or text details. No response, so I called and got voicemail, left a msg, and waited. After about 10 minutes, I texted again. 20 minutes later, I got "I didn't here (sic) From you so I didn't know to meet you". Shit. So I txted no problem, sorry for the confusion, I thought we had confirmed last night, did you still want to meet or re-schedule? After another 10 minutes and not hearing anything, I headed home. An hour and a half later, still no response.

So much for her.

It's aggravating to weed through the flakes, time wasters and the 'do I really want to do this' types. I always try to call or text the day before and then follow up before I hit the road to confirm since I have to travel to most of the women I meet. It's not an easy road, but every once in a while there's a reward at the end.