Seeking Arrangements

[Midwestern]

I guess those are my two key points to other married guys:

1. Consider how bad it would be if it all went south. Is it really that bad? Set your risk tolerance around this.

2. Engineer your opportunities and plan your cover story meticulously.

Totally agree with you. My only small caveat is to be prepared if you do get caught. I have several friends that thought they'd never get caught and when they did get caught, they were totally unprepared for it. For me, I accept it's possible (and maybe even likely) that I'll get caught. But I pretty much know what I will do, and how I will live, in case I am caught.

Many years ago, I had a friend who was mongering all the time. He was happily married and loved his kids. And so I asked him, "What if your wife finds out?" he then just asked me, "What if YOUR wife finds out?" I simply said that I was prepared for that to happen, and that we cannot do the crime unless we can do the time. " he just looked at me in shock and disbelief. He said he could NEVER lose his family, and so his wife finding out would never be a possibility. But he didn't even hide his mongering that well. He was so open about it. Anyway, he got caught. It was a huge scandal because he was always viewed as the perfect loving and caring husband and father. He also somehow lost his job too. I know someone else that lost his job after he got caught. I'm not sure why these guys lost their jobs, but I do know that they were unprepared for getting caught, and that probably played some role.

[Steve 9696]

Been trying to decide whether to write this up or not because it probably just sounds like gloating and in some ways it is. But I love YOUR stories and live vicariously through them. I read Medellin and So Paulo and a few other forums just because I love this shit. I love reading a good field report. And who else am I going to spill my guts to besides you guys! So here goes.

To put this in context, you guys know I have coin but I got a ridiculous bonus year end so even the frugal side of me was just stomped out of existence which made it twice as fun. Plus some of these activities aren't as unaffordable as you might think. I've included prices. Of course Shayla was just in girlfriend mode so no costs there.

Of course for those just catching up Shayla is my SB from January whos become more like my girlfriend. She lives in an apt I own and the rest is just BFGF. Despite our 35 year age difference we get on like a house on fire. Just adore each other and try to spend as much time together as we can.

We flew into Miami and took an Uber to our beachside hotel because the cars we wanted don't hold luggage. LOL. So our first night we were car free. We got in around noon and had some sushi by the beach. Super good and so nice to be with my girl with no time limits! We did this once before with a mountains vacation and this even topped that.

Honestly tho our first day was def not the best of the lot. We had a fun time kicking around and walking on the beach but spent a fair amount of time figuring where we were going to get weed since it's illegal in Florida. Managed to score some finally. And had a lovely steak dinner at a high end steak house. Wagyu filet and cap ribeye. Wow. And wow on the bill too - $350. Worth it? Yea but just barely.

Oddly despite a couple advances sex never happened. This was a bit disconcerting but part of things being a bit more BFGF and not just someone I'm paying to suck my dick. But we fixed this totally the next day and beyond. Crashed like big dogs and slept in.

Got the car delivered to the hotel at 11 AM. A BMW I8 with suicide doors and all in metallic bright blue. Total head turner and great fun. Had it two days. $560 including delivery to our doorstep. Felt pretty badass. Had a nice lunch but had to keep it brief as we decided to book Parasailing at 1.

If you haven't parasailed you need to. Wow. That is something. We were up 400 feet in a tandem rig and drove right along the beach. It's pretty nerve wracking but amazing st the same time. High recommend. $300. Followed this up with Thai couples massage at 4 PM. Also high recommend on Thai massage. They really work and stretch you. Fixed a couple joint / back problems Shayla had. She was over the moon.

Can't recall exactly when but I brought up the fact that we didn't have sex day one and it was disappointing and I'the tried to initiate twice. Again now we are in BFGF land. She was really nice about it and said she didn't know I was trying to initiate and she is such a nerd she doesn't know how to handle these things but rest assured she always wants to have sex with me and just let her know and it's on.

So I made it a lot more clear when I was initiating after massage and before dinner and wow did we have some great sex. Not as good as nights two and three (stay tuned) but amazing nonetheless. Amazing dinner at an Asian fusion place by the water. $250. And a night in of smoking drinking and cuddling.

Third day we discovered the sixth floor dining and pool area. Duh why didn't we find this before! We ate breakfast at the restaurant there and it was mostly comped because she's a diamond member which was sweet. But the pool area overlooking a panoramic beach was priceless. Went to the beach first and had a glorious time. She loves the beach. Got super sandy but had fun. Then spent the remainder of the day in a poolside cabana now THAT is my style. Def king of the world.

Helicopter ride at 3:30. This was absolutely one of the best experiences of my life. Never done it before. It was epic. Just indescribable. And with my girl. Highlight of the trip. $700. Save your pennies and put this on your bucket list!

Had some amazing sex after the helicopter and I mean best so far particularly for her. She musta cum at leave five times maybe more. She literally couldn't walk after. Just a great time. Went for barbecue and the Casino after that where we lost a tidy pile of cash but she had fun. Not my fave. Great fun driving the I8 tho. Crashed hard again not even late really.

Last day was mostly poolside. Just lounging together and her in that bikini. Fuck she looks good. She pretty much initiated sex at some point when we were back in the room. Musta been morning because we checked out at 1. She straddled me on the chair and started kissing me and of course it was on after that. She dominated me a little bit from on top and I rather liked it. We got those skinny jeans off and I fingered her while we made out. Then Asian cowgirl in the chair. Wowza! After a while we moved to the bed — I literally carried her with dick in pussy and legs wrapped around like a movie or something and it totally worked! Started in mish from there obviously then Steve 2. Steve. Mish. Doggie. Cowgirl. BJ. And a couple rounds of that. Finally finished CIM in Steve 2. Once again she had multiple Os some that were mind bending. She was an absolute floppy wet dishrag after we finished. Just done for. But a smile size of Texas. And then more pool time. LOL.

So it was a packed 3. 5 days but we made it count. Epic car. Parasailing. Helicopter ride. Just a dream really. As I say I wasn't counting pennies this trip but as you see above some of these things are affordable if you save up and only do them once. I would def do both parasailing and heli again in a heartbeat. And oh have epic sex also. 😋. Thanks for tolerating my rambling. Hope some of u enjoyed it!

[The Cane]

I guess those are my two key points to other married guys:

1. Consider how bad it would be if it all went south. Is it really that bad? Set your risk tolerance around this.

2. Engineer your opportunities and plan your cover story meticulously.

Or maybe I'm just fucking lucky. LOL.

Just stay single and free to leave at any time! No way in hell I could have the patience for all of that. No way no how!

[Steve 9696]

Hi Steve, having read your stuff for a long time and conversed with you directly it would seem you have a lot of flexibility in your marriage. Not to get too personal, but based on your posts it seems like don't ask, don't tell.

In any event, your travels are amazing and the envy of most of us here. You have many opportunities to work your SD magic in many USA Cities and several countries.

You are right. I am living the time of my life right now. But no it's not exactly a flexible don't ask don't tell relationship. A couple things here that other marrieds might cobsider:

1. At first I was paralyzed that she might find out. But the more I thought about it I realized I'the be happier single than married at this stage. I want to keep things together "for the kids" for a couple more years. And she NEEDS me. She's very dependent on me. If things went south she's be waaaaay more fucked than I would. So it's kinda funny. I keep it private for HER sake not for mine. She's a smart girl tho. She prob knows something is up and too smart to push to hard because she knows she needs me more than I need her.

2. I work very hard to ensure all details are covered. If I say I am going out to dinner I make sure that place is open. I know the menu and "what I had". It's all made up. But she asks sometimes. Likewise I recently went in a trip and didn't actually go where she thinks I did. I took Shayla to Miami instead. But I had itinerary and hotel reservations for my pseudo location. Texted take off and landing at appropriate time zone adjusted times etc. It was a fuck load of work and very dicey at times! But totally worth the meticulous planning.

I guess those are my two key points to other married guys:

1. Consider how bad it would be if it all went south. Is it really that bad? Set your risk tolerance around this.

2. Engineer your opportunities and plan your cover story meticulously.

Or maybe I'm just fucking lucky. LOL.

[WyattEarp]

It's def challenging but I was able to progress beyond the "couple of meetups". I started with a night or two when traveling in the US. And that was amazing. Then I flew Alexa to Miami (not my home) for a couple days and that was AMAZING. I started doing discreet hometown quickies like just dinner and room. Maybe 2-2. 5 hours. Then settled in on a hometown girl and did that on and off for a year. Then I met Shayla and we have progressed from that. Now she lives in an apt I own and we are like a real couple. Mind blowing. Recently flew together to Miami. Off the charts. More on that soon.

Hi Steve, having read your stuff for a long time and conversed with you directly it would seem you have a lot of flexibility in your marriage. Not to get too personal, but based on your posts it seems like don't ask, don't tell.

In any event, your travels are amazing and the envy of most of us here. You have many opportunities to work your SD magic in many USA Cities and several countries.

[Steve 9696]

That's so interesting. I have never done SD that way. It's only ever been one night in town, maybe 2.

I'm married so I don't think I could get away with hiding a long term in town SB. But it sounds amazing.

It's def challenging but I was able to progress beyond the "couple of meetups". I started with a night or two when traveling in the US. And that was amazing. Then I flew Alexa to Miami (not my home) for a couple days and that was AMAZING. I started doing discreet hometown quickies — like just dinner and room. Maybe 2-2. 5 hours. Then settled in on a hometown girl and did that on and off for a year. Then I met Shayla and we have progressed from that. Now she lives in an apt I own and we are like a real couple. Mind blowing. Recently flew together to Miami. Off the charts. More on that soon.

But yeah it can progress and progress and progress. Always another layer!

[AmericanPi]

That's so interesting. I have never done SD that way. It's only ever been one night in town, maybe 2.

I'm married so I don't think I could get away with hiding a long term in town SB. But it sounds amazing.

Obviously, because she liked his company and trusted his judgement. I have had SBs where I talked to them about their BFs all the time. Hell, with some, I would expect their wanting me to meet their BF and see if I approved. That is the daddy part of being a sugar daddy.

I was with a married SB and listened to her marital problems. Her husband would cum in < 20 seconds. She was a stunner, and I thought about pursuing more than a sugar relationship with her, but it became obvious to me that she loved him but was not sexually satisfied and so I was cool with just being her SD.

With another, she would hang out with these losers and I would listen to her talk about them. Thing is she was less good in bed when she was with them because she was not as horny, but I chastised her not on that but dating all these losers. She had super model type looks and still gave the best head I have ever gotten. Still, when she found the right guy, I kind of felt guilty seeing her and eventually broke it off. The whole point of being a SD is really doing what is best for your SB and having more than just a sexual relationship with them.

So when Luminous says his gal wanted to meet with him and not have sex, that tells me he is doing it right. He has more than just a P4 P relationship with his gal.

[Ucgdx]

Good job UCG! That is my kind of gal. And you are fishing in California? Is that right?

Yep, NorCal, where there's too many rich guys and not enough cute college girls. That's why it takes so many messages to land one good arrangement.

Attaching a pic of another former 2022 SB; she had just immigrated to the US earlier this year, so I picked her up on her first week on SA.

[KeviKev68]

My experience has been the same, in the same geographical area. I'm not overweight, but short, so maybe that all balances out in the looks department.
I find that I have to message 100 girls to get 40 in-app responses, which becomes only 13 off-app contacts. Yep, I also found that a blue bubble (iPhone) means a higher chance of success. From those 13 contacts, only 3 become meets, and about 1 BBFS hookup, usually paid but sometimes free.

I usually end up paying 500-600 / meet. I'm pretty picky about the girls I reach out to, and willing to pay a premium to get what I want. I always check ID for age too.

Arrangements end up lasting anywhere between 1 meet and a year. In my current arrangement, we went CFS for the first two sessions, but they were also unpaid besides some non-cash gifts. In the 4th session, I showed her my recent test results, and she agreed to go BB since then. We also agreed to an allowance with the understanding that it would be more times some weeks, and zero times other weeks. So far so good!

I'm attaching a pic of a previous 19 YO SB, 5'3, 105, sizeBcups, former track athlete, perfect body.

My arrangements usually last a year but I have some that are semi-regular that are still on going for the past 3 years. These are a couple of arrangements I've had.

[Elvis 2008]

My experience has been the same, in the same geographical area. I'm not overweight, but short, so maybe that all balances out in the looks department.

I find that I have to message 100 girls to get 40 in-app responses, which becomes only 13 off-app contacts. Yep, I also found that a blue bubble (iPhone) means a higher chance of success. From those 13 contacts, only 3 become meets, and about 1 BBFS hookup, usually paid but sometimes free.

I usually end up paying 500-600 / meet. I'm pretty picky about the girls I reach out to, and willing to pay a premium to get what I want. I always check ID for age too.

Arrangements end up lasting anywhere between 1 meet and a year. In my current arrangement, we went CFS for the first two sessions, but they were also unpaid besides some non-cash gifts. In the 4th session, I showed her my recent test results, and she agreed to go BB since then. We also agreed to an allowance with the understanding that it would be more times some weeks, and zero times other weeks. So far so good!

I'm attaching a pic of a previous 19 YO SB, 5'3, 105, sizeBcups, former track athlete, perfect body.

Good job UCG! That is my kind of gal. And you are fishing in California? Is that right?

[Elvis 2008]

The real story is she wanted to have you take her and her boyfriend to dinner and not have sex? Why would she think anyone would be ok with that?

Obviously, because she liked his company and trusted his judgement. I have had SBs where I talked to them about their BFs all the time. Hell, with some, I would expect their wanting me to meet their BF and see if I approved. That is the daddy part of being a sugar daddy.

I was with a married SB and listened to her marital problems. Her husband would cum in < 20 seconds. She was a stunner, and I thought about pursuing more than a sugar relationship with her, but it became obvious to me that she loved him but was not sexually satisfied and so I was cool with just being her SD.

With another, she would hang out with these losers and I would listen to her talk about them. Thing is she was less good in bed when she was with them because she was not as horny, but I chastised her not on that but dating all these losers. She had super model type looks and still gave the best head I have ever gotten. Still, when she found the right guy, I kind of felt guilty seeing her and eventually broke it off. The whole point of being a SD is really doing what is best for your SB and having more than just a sexual relationship with them.

So when Luminous says his gal wanted to meet with him and not have sex, that tells me he is doing it right. He has more than just a P4 P relationship with his gal.

[Luminous]

Well, sometimes you develop a connection with a person. I was not in love with her but I liked her as a person and I think she did too. I didn't think she was trying to squeeze a dinner out of me. It's like when you go to different city and meet an old friend, you go out for dinner, simple as that.

I am not saying I have not been taken advantage off, this just wasn't one of those.

The real story is she wanted to have you take her and her boyfriend to dinner and not have sex? Why would she think anyone would be ok with that?

[AmericanPi]

So true. I have SB in Medellin, few months back she found a boyfriend and told me she would love to have dinner with me but will bring her boyfriend too and no sex. I didn't make it to Medellin any so that never happened. 6 months later when I was texting her a few days back, she still has the boyfriend but is totally game to sleep with me.

The real story is she wanted to have you take her and her boyfriend to dinner and not have sex? Why would she think anyone would be ok with that?

[AmericanPi]

That is a fine piece of tang.

Good on you my man. Good on you. Living your life to the fullest.

My experience has been the same, in the same geographical area. I'm not overweight, but short, so maybe that all balances out in the looks department.

I find that I have to message 100 girls to get 40 in-app responses, which becomes only 13 off-app contacts. Yep, I also found that a blue bubble (iPhone) means a higher chance of success. From those 13 contacts, only 3 become meets, and about 1 BBFS hookup, usually paid but sometimes free.

I usually end up paying 500-600 / meet. I'm pretty picky about the girls I reach out to, and willing to pay a premium to get what I want. I always check ID for age too.

Arrangements end up lasting anywhere between 1 meet and a year. In my current arrangement, we went CFS for the first two sessions, but they were also unpaid besides some non-cash gifts. In the 4th session, I showed her my recent test results, and she agreed to go BB since then. We also agreed to an allowance with the understanding that it would be more times some weeks, and zero times other weeks. So far so good!

I'm attaching a pic of a previous 19 YO SB, 5'3, 105, sizeBcups, former track athlete, perfect body.

[Ucgdx]

... However, for the past 10 years I have been on Seeking Arrangement. I am just a 50+ overweight guy and I have had enormous success on that site.
I reside in the Nor Cal area and live a few blocks from a major university. At seems likes every year I meet a 20-22 year old junior or seniors who recently joined the site.

My experience has been the same, in the same geographical area. I'm not overweight, but short, so maybe that all balances out in the looks department.

I find that I have to message 100 girls to get 40 in-app responses, which becomes only 13 off-app contacts. Yep, I also found that a blue bubble (iPhone) means a higher chance of success. From those 13 contacts, only 3 become meets, and about 1 BBFS hookup, usually paid but sometimes free.

I usually end up paying 500-600 / meet. I'm pretty picky about the girls I reach out to, and willing to pay a premium to get what I want. I always check ID for age too.

Arrangements end up lasting anywhere between 1 meet and a year. In my current arrangement, we went CFS for the first two sessions, but they were also unpaid besides some non-cash gifts. In the 4th session, I showed her my recent test results, and she agreed to go BB since then. We also agreed to an allowance with the understanding that it would be more times some weeks, and zero times other weeks. So far so good!

I'm attaching a pic of a previous 19 YO SB, 5'3, 105, sizeBcups, former track athlete, perfect body.