Sugar Dating Experience

[FunInToronto2023]

seems very much like the norm in Toronto, at least on Seeking

I'd say paying anything over 500 is too much, especially if you're decent looking, fit and have great hygiene.
I'm normally very busy so can only see someone for about an hour each time, although I have had three or four good times in hotels - only one full sleepover in a hotel that was incredible. Blonde about 5'11", late 20s, room service and went at it making each other cum like 5 times each. But I couldn't have sex with her in the shower because she's a lot taller than me and was so tight we needed lube. We were both laughing it was pretty funny, so we hopped out and jumped back into bed.

It's funny because I always thought that taller girls would have slightly larger pussies but it all just depends on the girl. I can immediately think of 4 girls (actually more) who were several inches taller than me and they were really tight. But then I've been with shorter girls and they must masturbate with huge dildos or something because they're really not tight in the least (trying to stay polite but lots of people will know what I mean).

 

[Hipjdog]

I've dabbled with Seeking Arrangements but have never pulled the trigger as I'm worried about getting scammed.
The girls I have talked to, though, are very tempting, almost too good to be true.

Some questions for experienced guys:

• How does the first meeting generally go? Does she come to your place and just...straight to the bedroom? How long does she stay for?
• Is intimacy generally assumed each time you meet or do you sometimes just go out to dinner or whatever?

 

[FunInToronto2023]

I've dabbled with Seeking Arrangements but have never pulled the trigger as I'm worried about getting scammed.
The girls I have talked to, though, are very tempting, almost too good to be true.

Some questions for experienced guys:

• How does the first meeting generally go? Does she come to your place and just...straight to the bedroom? How long does she stay for?
• Is intimacy generally assumed each time you meet or do you sometimes just go out to dinner or whatever?

I've had to keep all of my encounters very discrete because of my SO and situation.
They message their expectations and you tell them yours.
First meetings for me have almost all involved intimacy right away except for maybe 2, which turned into intimacy the next time we met.
I usually message back and forth off the site, we flirt for a bit and trade normal pics (sometimes nude).
When messaging off the site, I feel like you get a better inclination of what they're into, if they're really real or not, etc.
And yes, to your point, there is definitely too good to be true out there - as in scammers.

I had one bad experience that went way past my better judgment but I won't get into it in the public forum. It was my fault for going along with it but I felt so stupid and it was almost a very dangerous situation. Actually it was dangerous.

Rule #1: If they only have one photo, no matter how real or attractive, do not engage.

 

[chaychay]

I'm really fascinated by this. I've always been doubtful I'd ever be able to participate - as a man of modest finances. As such, I never really researched it much. But when you mention $200, that doesn't seem out of reach for me.

You've got me thinking... I'm not un-attractive. I'm kind. I'm polite. I enjoy being with women, and complimenting them, celebrating them. I certainly enjoy making out with them! (I can't say I'd want to have sex, that might be a line I don't want to cross for personal reasons).

So you connect with a lady via one those websites. You share your number. You text for a while... then you... then what?

Would you guys mind painting more of a picture for the totally uninitiated? Pardon my naïve ignorance.

At what point does handing over $200 to a beautiful lady really happen?

EDIT to mention: I see you've kinda answered some of my questions in the time I was composing this post!

 

[Daddy2021]

I’m curious if you guys that have been with SB’s have SO’s.

Probably , you just won’t know about it. Just like you won’t be the only sugar daddy. If they say there is one another then consider 3 or 4 more. They figure they come off as being honest if they say one more so Incase they get cought…”oh that’s the one I told you about”

 

[johnd5050]

I’m curious if you guys that have been with SB’s have SO’s.

Glad you asked. I will add what is the risk factor ?

 

[FunInToronto2023]

Glad you asked. I will add what is the risk factor ?

For me the risk factor is actually huge. The downfall would be horrible and I don't recommend doing it in the first place.
It's a stupid thing to be doing, it's wrong but I basically don't get intimacy if I don't do it.
And with disposable income and the excitement factor, it's a difficult habit to stop.

 

[Mrboobs]

Glad you asked. I will add what is the risk factor ?

Get caught and a 19 year old going crazy on you then getting caught.

 

[GeeBee]

I've dabbled with Seeking Arrangements but have never pulled the trigger as I'm worried about getting scammed.
The girls I have talked to, though, are very tempting, almost too good to be true.

Some questions for experienced guys:

• How does the first meeting generally go? Does she come to your place and just...straight to the bedroom? How long does she stay for?
• Is intimacy generally assumed each time you meet or do you sometimes just go out to dinner or whatever?

In all but two cases I’ve met the girls for coffee or a drink to make sure she’s real and we seem to have some kind of vibe. (Most legitimate SB’s are fine with this and from their perspective it gives them a chance to scope me out and make sure I’m not an ogre. This is the main difference from the world of escorts, try suggesting to a LL girl that you’d like to meet first just to see how you vibe) Always somewhere discreet, I’ve often found that the girl wants to be just as discreet as I do.

In most cases, once the arrangement has been agreed upon intimacy is assumed on each date, but consent is always a must for a boat load of reasons. I’ve been in longer term arrangements where it doesn’t always happen, her period surprises her for instance on the day. But I’ve found that it goes a long way to keep the date, just have a nice evening at her place, make her tea and give her a massage, and she is truly impressed by how much of a gentleman you are. Whenever this happens the next date is without fail fucking memorable

One point to add. I’m a much better lover after seeing escorts for all these years and getting their feedback on what they like and don‘t like. I guarantee I’ve got more experience eating pussy than any of the college boys most younger SB’s have dated. And I’m awesome at it apparently

 

[probyn]

One point to add. I’m a much better lover after seeing escorts for all these years and getting their feedback on what they like and don‘t like. I guarantee I’ve got more experience eating pussy than any of the college boys most younger SB’s have dated. And I’m awesome at it apparently

Good for you, but aren't you worried about getting herpes on your lips and having occasional bouts of that being visible to people?

 

[GeeBee]

Good for you, but aren't you worried about getting herpes on your lips and having occasional bouts of that being visible to people?

The relationship between an SD and an SB is a pretty open one, if you’re serious about it ask her to get tested. You can get a pretty good idea of how careful she is about her sexual health with a conversation. In my experience most are very careful and raise the subject before I do. Remember this is much more of a negotiation than dealing with SP’s, questions can be asked over a drink to make sure you’re both comfortable.

 

[GeeBee]

Good for you, but aren't you worried about getting herpes on your lips and having occasional bouts of that being visible to people?

One other thing

There has been a debate about whether an SB is just a SP by another name, and while I’d agree that both are on the spectrum of sex work, there are a couple of huge differences.

First is the meet for a coffee or a drink before and talk about the arrangement. If she wants to meet first she’s definitely not an SP.

Second, and this is just an observation and I’d like to know if any one else has noticed this. I have never had an SP expect me to put the condom on. They’re experts at doing it seamlessly, and also want to make sure it’s done right.

On the other hand SB’s always want me to do it, like I have way more experience than they do.

Any one else have the same experience?

 

[Leimonis]

Good for you, but aren't you worried about getting herpes on your lips and having occasional bouts of that being visible to people?

Yes let’s be virgins! Jesus…

 

[johnd5050]

Good for you, but aren't you worried about getting herpes on your lips and having occasional bouts of that being visible to people?

If you are so paranoid stay far away from this hobby.
BTW what are you doing on this site ??

 

[Hipjdog]

One other thing

There has been a debate about whether an SB is just a SP by another name, and while I’d agree that both are on the spectrum of sex work, there are a couple of huge differences.

First is the meet for a coffee or a drink before and talk about the arrangement. If she wants to meet first she’s definitely not an SP.

Second, and this is just an observation and I’d like to know if any one else has noticed this. I have never had an SP expect me to put the condom on. They’re experts at doing it seamlessly, and also want to make sure it’s done right.

On the other hand SB’s always want me to do it, like I have way more experience than they do.

Any one else have the same experience?

Yeah, it's the same with civilian girls. They want you to put it on because they aren't that experienced.

 

[FunInToronto2023]

One other thing

There has been a debate about whether an SB is just a SP by another name, and while I’d agree that both are on the spectrum of sex work, there are a couple of huge differences.

First is the meet for a coffee or a drink before and talk about the arrangement. If she wants to meet first she’s definitely not an SP.

Second, and this is just an observation and I’d like to know if any one else has noticed this. I have never had an SP expect me to put the condom on. They’re experts at doing it seamlessly, and also want to make sure it’s done right.

On the other hand SB’s always want me to do it, like I have way more experience than they do.

Any one else have the same experience?

This is where I can admit to being legit crazy. Ok stupid. I’ve never had any STD and I’ve been intimate with at least a dozen girls from sugar dating sites. Maybe 15-20 now. I’ve only ever worn a condom twice. But we’re open and discuss STD status before doing anything.

I met an absolutely stunning 29 year old in Hamilton this past summer. Went to her place, we talked a bit on the couch and started making out. Then got up and went to her bedroom, we’re the same height so it was perfect, off came the clothes, we kept making out and I pinned her against the wall by the bed. I put her right leg up on the bed and she grabbed my thick cock and used it like a sex toy on her pussy and clit. She was super wet and when I was fucking her standing up she kissed me hard and started to cum.
We had sex three more times and it was so good but a couple of days later she called it off because there’s that mental aspect of it all. If you’re a SP I’m sure it’s the same but you’re mentally in it for a job, whereas a SB might temporarily need cash and it’s far more of a choice.

 

[Hipjdog]

Dude, wear protection. You don't know how many other guys she has arrangements with.

 

[superman12]

I've dabbled with Seeking Arrangements but have never pulled the trigger as I'm worried about getting scammed.
The girls I have talked to, though, are very tempting, almost too good to be true.

Some questions for experienced guys:

• How does the first meeting generally go? Does she come to your place and just...straight to the bedroom? How long does she stay for?
• Is intimacy generally assumed each time you meet or do you sometimes just go out to dinner or whatever?

From my experience first meetings are always in a public place like a coffee shop or a mall. I have never really had any time limit when I meet up with sb's since your usually just paying per meet up. At the first meet you get to discuss all of your expectations and what both sides are looking for in the arrangement. Intimacy is generally assumed but it's good to make it clear to the girl that's what your looking for. Most of the sb's will be ok with it anyways. Don't expect intimacy on the first date unless the sb your seeing is an escort lol. By the 2nd or 3rd date the sb is usually horned up enough to want sex. With an sb the more you pamper and spoil them the more inclined they are going to be to fuck.

 

[Hipjdog]

From my experience first meetings are always in a public place like a coffee shop or a mall. I have never really had any time limit when I meet up with sb's since your usually just paying per meet up. At the first meet you get to discuss all of your expectations and what both sides are looking for in the arrangement. Intimacy is generally assumed but it's good to make it clear to the girl that's what your looking for. Most of the sb's will be ok with it anyways. Don't expect intimacy on the first date unless the sb your seeing is an escort lol. By the 2nd or 3rd date the sb is usually horned up enough to want sex. With an sb the more you pamper and spoil them the more inclined they are going to be to fuck.

I'm hesitant to spend 500 bucks just to walk around the Eaton Centre talking or whatever. I guess if you're a high roller it's worth it. At least with escorts you know what you're getting.

 

[Daddy2021]

From my experience first meetings are always in a public place like a coffee shop or a mall. I have never really had any time limit when I meet up with sb's since your usually just paying per meet up. At the first meet you get to discuss all of your expectations and what both sides are looking for in the arrangement. Intimacy is generally assumed but it's good to make it clear to the girl that's what your looking for. Most of the sb's will be ok with it anyways. Don't expect intimacy on the first date unless the sb your seeing is an escort lol. By the 2nd or 3rd date the sb is usually horned up enough to want sex. With an sb the more you pamper and spoil them the more inclined they are going to be to fuck.

Dude take the girl to dinner as a first meet. Walk around the mall? Not unless you’re planning to use your credit card. Lol