"Sugarbabies" / "Arrangements" Amateurs or Not?

[LongLasting]

Care to share her with the rest of us? Sounds like could be a lot of fun. Thanks either way. Nice post!

Sorry, I'm in the Midwest, not the Richmond area.

[LongLasting]

Thank you. She needed financial help too but we seemed to hit it off well socially.

But I had no idea she was so horny. As soon as I went down on her, I knew she was a live one.

She was not shy at all about expressing her pleasure and the naughty places she wanted me to touch.

Extremely vocal throughout and the longer we went, the naughtier the phrases were out of her mouth. She did not.

Tell me she was a squirter beforehand but the first time she did I felt it right away. Soon I figured out that going straight in deep.

Would make her squirt on demand. She loved the release each one brought and it seemed she could not get enough. I was afraid I would dehydrate her. Each time I went in deep and hard she would never fail to squirt. I know it seems like I'm exaggerating but I know it had to be close to 15 times. I enjoyed it as much as she did. I would not have believed it myself if I hadn't experienced it first hand.

[Rdudreaming]

This may have been asked before and if so I apologize for asking. How do you get a hotel room and not use a CC or especially your I'd??

Assume for a moment that the girl is not found in the room chopped up with a chain saw, what difference does it make? Pay cash. No invoices sent to the house. Use real I'd. Clear all incidentals before you leave. Is it likely that the hotel clerk is going to mail a copy of your I'd to your SO? If it's PI paranoia, he already took pics of you going in the notel regardless of a fake name.

[John HandCock]

Do they not publish Penthouse Forum anymore?

Just another good story which seems to pop up on all sb threads. Woukd have been better.

With pics but lots of guys like creative writing.

[F Scott]

Been in the bowl a few years and met quite a few gals.

Recently had a experience like no other. Pretty but over weight MILF.

She wanted it bad and was like the energizer bunny in bed.

We did it continuously for 4 hours with a shirt break for dinner. She was a squirter and she let loose at least 15 times. Soon I learned exactly what I had to do to make her squirt on demand. She wanted it deep and hard and wasn't shy about letting me know how good it felt. She craved my hard boner and deep throated me several times, getting me rock hard every time. Then she would beg me to put it inside. A true Nympho. To finish, she stroked me til I came and licked me clean. She craved hard cock and loved sucking me to get me hard. Let's just say she wasn't the shy type. She was impressed with my stamina and it was easy staying hard knowing how horny she was.

Do they not publish Penthouse Forum anymore?

[JackOhhhh]

Been in the bowl a few years and met quite a few gals.

Recently had a experience like no other. Pretty but over weight MILF.

She wanted it bad and was like the energizer bunny in bed.

We did it continuously for 4 hours with a shirt break for dinner. She was a squirter and she let loose at least 15 times. Soon I learned exactly what I had to do to make her squirt on demand. She wanted it deep and hard and wasn't shy about letting me know how good it felt. She craved my hard boner and deep throated me several times, getting me rock hard every time. Then she would beg me to put it inside. A true Nympho. To finish, she stroked me til I came and licked me clean. She craved hard cock and loved sucking me to get me hard. Let's just say she wasn't the shy type. She was impressed with my stamina and it was easy staying hard knowing how horny she was.

Hang onto that one, they are far and few. Most are just looking for $. Sounds like you found a live wire. While I am mostly into spinners, I did date a squitter ONCE. Tot pleased al turn off for me.

[JackOhhhh]

Been in the bowl a few years and met quite a few gals.

Recently had a experience like no other. Pretty but over weight MILF.

She wanted it bad and was like the energizer bunny in bed.

We did it continuously for 4 hours with a shirt break for dinner. She was a squirter and she let loose at least 15 times. Soon I learned exactly what I had to do to make her squirt on demand. She wanted it deep and hard and wasn't shy about letting me know how good it felt. She craved my hard boner and deep throated me several times, getting me rock hard every time. Then she would beg me to put it inside. A true Nympho. To finish, she stroked me til I came and licked me clean. She craved hard cock and loved sucking me to get me hard. Let's just say she wasn't the shy type. She was impressed with my stamina and it was easy staying hard knowing how horny she was.

Care to share her with the rest of us? Sounds like could be a lot of fun. Thanks either way. Nice post!

[LongLasting]

Been in the bowl a few years and met quite a few gals.

Recently had a experience like no other. Pretty but over weight MILF.

She wanted it bad and was like the energizer bunny in bed.

We did it continuously for 4 hours with a shirt break for dinner. She was a squirter and she let loose at least 15 times. Soon I learned exactly what I had to do to make her squirt on demand. She wanted it deep and hard and wasn't shy about letting me know how good it felt. She craved my hard boner and deep throated me several times, getting me rock hard every time. Then she would beg me to put it inside. A true Nympho. To finish, she stroked me til I came and licked me clean. She craved hard cock and loved sucking me to get me hard. Let's just say she wasn't the shy type. She was impressed with my stamina and it was easy staying hard knowing how horny she was.

[JackOhhhh]

Thanks LoVecchio.

IMHO, there is really no need to discuss whether it will be long-term ore a one-time thing. It's just a date after all. If you take her to a nice dinner she will know she is expected to put out if she wants to see you again. I'm not saying to "play a game". If you are from out of town, fair enough. She doesn't need to know when you will return. Most of them have several daddies, I'm sure they won't be sharing that info with you. If you treat them well, I think they will be happy. I certainly wouldn't advertise you are only looking for a one-time hook up.

Just my two cents.

So, I got back from my out-of-town trip. Thanks to all of the guys who gave advice.

I had a lot of trouble finding someone, a fact that I attribute primarily to two factors. First, I was upfront that this would probably be a one-time deal, as I did not expect to come back in town for subsequent visits. I felt that I had to say that because I did not want to mislead, but I'm sure that eliminated many women. It's one thing to tell yourself that sugaring is not escorting when it's an ongoing relationship; it's another to convince yourself that it's not escorting when it's explicitly a one-off thing. The second problem was that the city I was traveling to was relatively small (population < 250,000), with no other larger cities around for hundreds of miles). I live in a large metropolitan area, which provides a greater cloak of anonymity, and hadn't initially realized the different challenges presented by a small city.

Anyway, I sent out lots of messages, but with a relatively low level of nibbles (maybe 10% I had some conversations that looked promising but that then abruptly stopped. Two or three of the girls de-activated their profiles in the middle of our discussions (without having read my last message). Because there was nothing in the exchange, as far as I could tell, that would have prompted their withdrawal, I assume that it wasn't specifically related to me, although it might have been. A couple of conversations that seemed promising became dead-ends after they provided me enough information to investigate them on Google and find that they were not people I wanted to spend time with. Finally, after a couple of weeks of frustration, I clicked with a POT just before I left on my trip.

[HoyaSvnFgr]

Went out with older gal needing a sponsor. Lied about age (28). She's early 40's. Short, BIG ass. She had some type of waist spandex. I get her undressed and it's a belly there that's had a C-section with a machete! Personality type: Failed independent business owner, talks a lot of wealth talk and drives a clean late 90's Benz. I sensed the desperation from the constant text and open ended meeting attempts. Second date for drinks and she's ordering an appetizer described has "spices with a kick". She comments about how she needs something like that in her mouth. You know where this date is going.

I take her to my place and she gives oral for 30 minutes. Not too good, I expected more. Then I grab a condom for sex and things get weird. She grabs my junk and begs me not to use a condom. Says she can't get pregnant, no stds and really wants me to come inside her. I ignored her fought to put the condom on and had 1 minute of the dryest most rubbery ride ever.

The biggest waste of my time. The next day I noticed micro flesh colored bump on my penis tip. I assume it's from the rough oral or her grabbing my junk as I was trying to put a condom on. I couldn't imagine it being an STD. Unprotected oral. She didn't appear to be a pro or have open mouth sores. Afterwards I mention the bump, she says she's clean. Claims she hadn't had sex in a several months and she's just horney as hell and wants to be in a one-on-one relationship with bareback sex all the time. $sugar $ requirement is to treat her like a GF (dates, drinks, place to fck). Not worth my time at all. SMH.

[LoVecchio]

I have been in the bowl for the last three years and have been amazed by the new vistas it opens up. I am in my mid-60's and have to confess that I've been having the best sex of my life with women 1/3 to 1/2 my age. Because I am married, I am limited to discreet meetings in hotels and have never tried to meet a baby when I'm traveling. A few weeks from now, I'm going to be going to a far-away city where I won't be so constrained and was thinking that it would be nice to meet up with an SB with the idea (well, my idea, anyway) of taking her to a very nice restaurant and then hoping to take her back to my hotel.

I'm at a bit of a loss in figuring out how to approach girls and also which ones to approach. I can't offer more than a one-time thing, because although I occasionally go to that city, I'm generally with my wife when I do so. I assume that it would be easier if I could dangle recurrent visits, but I can't really do that in good faith. So, I have to make clear that this is a one-time thing (or at least be careful not to seem like I'm promising more than that), which makes it hard to approach someone without offending her and making it seem like I am treating her as an escort. On the other hand, I don't want her to think that I JUST want a dinner companion. So, I'm having trouble figuring out how to approach a woman.

I'm also having trouble figuring out which women to approach. The choice seems to boil down to: 1) approaching the same women I would approach if I were trying to set up a long-term arrangement. These would be women who are educated or on their way to being educated and are people I think would be interesting dinner companions but perhaps far less than sure things to take back to the FC; or 2) approaching women who might be less educated, perhaps single mothers, who even if nice people might be less than enchanting dinner companions (and perhaps out of their element at a nice restaurant) but perhaps more of a sure thing to get to the FC because they may be more highly motivated by the money.

That leads me to the next thing, which is how to make it clear (or at least clear enough) that I am offering more than just a free meal if the night goes well.

Anyway, it seems that finding a Road Baby presents some different challenges from finding one close to home. If anyone has any advice, I would love to hear it.

So, I got back from my out-of-town trip. Thanks to all of the guys who gave advice.

I had a lot of trouble finding someone, a fact that I attribute primarily to two factors. First, I was upfront that this would probably be a one-time deal, as I did not expect to come back in town for subsequent visits. I felt that I had to say that because I did not want to mislead, but I'm sure that eliminated many women. It's one thing to tell yourself that sugaring is not escorting when it's an ongoing relationship; it's another to convince yourself that it's not escorting when it's explicitly a one-off thing. The second problem was that the city I was traveling to was relatively small (population < 250,000), with no other larger cities around for hundreds of miles). I live in a large metropolitan area, which provides a greater cloak of anonymity, and hadn't initially realized the different challenges presented by a small city.

Anyway, I sent out lots of messages, but with a relatively low level of nibbles (maybe 10% I had some conversations that looked promising but that then abruptly stopped. Two or three of the girls de-activated their profiles in the middle of our discussions (without having read my last message). Because there was nothing in the exchange, as far as I could tell, that would have prompted their withdrawal, I assume that it wasn't specifically related to me, although it might have been. A couple of conversations that seemed promising became dead-ends after they provided me enough information to investigate them on Google and find that they were not people I wanted to spend time with. Finally, after a couple of weeks of frustration, I clicked with a POT just before I left on my trip. She was a real person, late twenties with one child and a responsible job. We spoke on the phone before I left home and actually had a nice conversation (I often find those phone conversations to be a bit forced). Anyway, we arranged to meet at the nicest restaurant in town (which was actually amazingly nice given the size of the city). She was pretty attractive and reasonably well-built, although a little heavier than is my ideal but within the range of many people's preferences. We had a nice dinner, at which I introduced her to a couple of things she'd never tried before. She then came back to my hotel and, with little small talk, we found ourselves in bed. She stayed for a few hours, but she had to leave to relieve the babysitter.

So, I got the kind of evening I was looking for. It was the first real (well, sort of real) "date" I had been on in a long time. We've exchanged a few messages since (of the, "I hope we get to see each other again" sort, although we both know that it won't happen).

I'm not sure if presented with the same situation, I would do it again, though. It was incredibly time-consuming. Perhaps it didn't have to be, but once I had embarked on that course, I was dedicated to the goal. I suppose that if the opportunity arises again, I'll convince myself that the new opportunity is more promising than the last one, so I'll probably fail to learn from experience.

[Black Chi]

This may have been asked before and if so I apologize for asking. How do you get a hotel room and not use a CC or especially your I'd??

Look four posts down. PrePaid credit cards.

[Titleist2323]

This may have been asked before and if so I apologize for asking. How do you get a hotel room and not use a CC or especially your I'd??

[John HandCock]

Being a true dominant isn't really something you can just dabble in. It is more than just being rough or cruel. It is not about strong or weak. It is about the partner trusting you and giving you control. My best submissive partners are otherwise as confident and together as me. There is a psychological and an emotional component to it. I hear from plenty of women that many guys try and don't get it right. I'm sure I didn't at first either -- and I know I misjudged its power as well. Tread carefully and cautiously. With great power comes great responsibility.

Good post. Alot of sick fucks out there that call themselves Dom that get off just beating women. Lots of women are ruined by these guys or scared away from it. I've had numerous girls tell about guys that want to break bones or worse or how they had looked forward to a first time experience only to be published so severely they would never try again. My advice to any girl wanting to try is never be bound by someone until they have earned their trust.

[Beachesnole02]

Being a true dominant isn't really something you can just dabble in. It is more than just being rough or cruel. It is not about strong or weak. It is about the partner trusting you and giving you control. My best submissive partners are otherwise as confident and together as me. There is a psychological and an emotional component to it. I hear from plenty of women that many guys try and don't get it right. I'm sure I didn't at first either -- and I know I misjudged its power as well. Tread carefully and cautiously. With great power comes great responsibility.

Had an incredible experience with a woman today, and it was about trust. Started with a blindfold, and my tie around her neck as a leash. Moved her around the room a couple times to disorient her and while doing that used pallet wrap to pin her arms to her side, and her ankles together. My last move before wrapping the ankles was to put her back to the bed, left her standing there while I warmed the coconut oil in the sink. Without warning, I pushed her back on the bed and the games began. I started soft, blowing on her with a straw, and worked on from there. If she squirmed or moaned from a touch, she got a quick swat on the rear end. Finished in the back door before I cut her loose. She went on for the next hour during normal play about how exciting that was an how her young guys just went through the motions. Said the push caught her completely by surprise because she was helpless and was not sure where she was falling. As soon as she hit the bed was thinking about how much she wanted to touch my cock. I will say this, I spent most of the time doing things I knew she would like. Maybe not the back door part, that was for me.