Seeking arrangements success!

[+ Coolwave35]

3 hours ago, MscleLovr said:

what an error!
 

 I wonder what you felt you might achieve by doing this?

In short I fucked up. All 3 of us wound up in the same city the same weekend and stupid me thought it would be fun to all hang out. It was really good until it wasn’t. Head SB has since left the country and is quite well and well off and we remain friends and travel partners. That isn’t the relationship that terminated, it was the Paris boy that did.  I realize my bad use of pronouns may have caused some confusion. 

2 hours ago, pubic_assistance said:

"Head Sugar Baby" ? Am I naive or does this seem like a formula for hurt feelings ? I have more experience dating women, than I do men, but I'm pretty sure that jealousy runs through everyone is varying proportions. Bad move.

Agreed. I just fucked this one up. I also learned a valuable lesson from this ordeal. I do have some great photos to remember the night by, but I wish I still had the boy. 

[pubic_assistance]

9 minutes ago, Coolwave35 said:

I also learned a valuable lesson from this ordeal.

The term "head sugar baby" is the equivalent of your mom saying your brother is "her favorite" .☹️

[+ Coolwave35]

44 minutes ago, pubic_assistance said:

The term "head sugar baby" is the equivalent of your mom saying your brother is "her favorite" .☹️

My brother is her favorite, by a mile. He gave her grandchildren and I gave her an ex son in law.

It’s a funny term, but head sugar baby got all of the initial invitations to travel, that’s really the only thing that was different.  When he couldn’t make a trip it passed to the next available guy.  

Edited November 1, 2022 by Coolwave35

[MscleLovr]

2 hours ago, Coolwave35 said:

I wish I still had the boy. 

Are you referring to the Paris boy (aka the “exact” boy @Jnich desires)?
 

If so, have you considered phoning him and simply saying ‘I fucked up that last time. I’d really like to see you again. Let’s go on a trip together’? I think that sometimes young men just don’t know what to say when something misfires. He may respond very well to your openness and desire to retrieve and rebuild a friendship. 

[+ Coolwave35]

1 hour ago, MscleLovr said:

Are you referring to the Paris boy (aka the “exact” boy @Jnich desires)?
 

If so, have you considered phoning him and simply saying ‘I fucked up that last time. I’d really like to see you again. Let’s go on a trip together’? I think that sometimes young men just don’t know what to say when something misfires. He may respond very well to your openness and desire to retrieve and rebuild a friendship. 

I am referring to him yeah. I messaged him around Labor Day saying I missed him and would be open to a trip this fall if he’d like to join me. He said he would and he’d let me know when he was back in my city from school. 
 

He did invite me to a catch up meal but then cancelled. I’m afraid he got nervous. He’s on the left. 

[+ DrownedBoy]

Oh man. I refer to the regular I hire the most as my "main regular" and "my first choice," and he seems to like that. Different places, different relationships.

On 10/31/2022 at 6:12 PM, fedssocr1 said:

So, I guess what I'm saying is, a lot of guys on the site have issues. Be prepared for that.

Absolutely.

Some guys are looking for relationships with younger men. Others just want house boys. Neither is wrong, as long as both parties are mentally and psychologically prepared.

[pubic_assistance]

7 hours ago, Coolwave35 said:

My brother is her favorite, by a mile.

Which makes it even MORE bizarre that you aren't aware of how much that hurts the one who's NOT "the favorite".

[+ Coolwave35]

2 minutes ago, pubic_assistance said:

Which makes it even MORE bizarre that you aren't aware of how much that hurts the one who's NOT "the favorite".

🤔

[pubic_assistance]

1 minute ago, Coolwave35 said:

🤔

Jeezus. You really are lost, aren't you ?

Now I understand why you got yourself in this pickle. 

[+ Coolwave35]

1 minute ago, pubic_assistance said:

Jeezus. You really are lost, aren't you ?

Now I understand why you got yourself in this pickle. 

No. I’m saying you’ve given me something to think about. The problem didn’t arise with jealousy amongst the two guys. They hit it off really well. I don’t recall introducing him as the favorite. I think, if memory serves, I introduced him as the boy I typically travel with. They were excited to meet each other. That wasn’t the conflict. 

[pubic_assistance]

12 hours ago, Coolwave35 said:

I don’t recall introducing him as the favorite.

Oh ? Well that's not the impression you gave me. Maybe that's not the impression you had given this young man  (who wasn't the favorite).

Maybe you'd like to share more details about the problem as it occurred ?

Edited November 2, 2022 by pubic_assistance
grammar

[+ Coolwave35]

39 minutes ago, pubic_assistance said:

Maybe you'd like to share more details about the problem as it occurred ?

Sure. Paris boy and I had this beautiful hotel room in Manhattan overlooking the park. I got a text from head boy that he was in town unexpectedly. I said “hey paris, I know you were curious about meeting (used his name). He happens to be in town, would you like him to join us for dinner”. He said that would be great. 
 

This is me paraphrasing. Head boy met us at the hotel and we chit chatted. Paris boy said I understand the attraction whoah. I said isn’t he great. Head boy said is this the bottom I’ve heard so much about?  I said yes. He said I bet Coolwaves always wanted to double penetrate. I said I couldn’t possibly. Paris boy said let’s do it. I laid on my back. Paris boy was on all 4s over me. Head boy fucked him from behind with my dick stationary inside.  It was a very aggressive pounding. When head boy finished and pulled out, there was an oopsie.  Head boy is huge and runs into this all the time. This isn’t bottoms first time in this predicament either. I’m embarrassed for bottom but bottom isn’t embarrassed at all. Bottom goes to one shower. Top and I go to the other. He raves about how hot he is, and wants to make sure I’m not in danger of being taken advantage of. He said can we hang out and talk a bit before dinner? I said of course. I go join bottom in his shower to make sure he’s ok with plan. He asks to hang in room and get dine in room service. He said something along the lines of this happens to the best of us and as long as you won’t bottom because you’re afraid of this, you’re denying yourself a world of pleasure. It’s a thing that happens and you move on. Both guys were super sweet and compassionate and I felt honored and privileged to be with them.

So after the shower we all laid on the couch in robes. That’s when the picture was taken. Head boy said “so what do you like to do for fun”. Bottom answered that he really enjoyed fire island over the summer, nyc clubs, his D1 sports team, technology and music etc. head boy said I went to fire island and it was a little cliquey for me. It was clear to me that I wasn’t in.

That’s when my world came crashing down. 
 

bottom said, and this is not paraphrasing.  “oh it’s easy. You let a couple of old rich guys fuck you until they let you use their house when it’s vacant some weekend. Then you become the hot 21 year old with his own share house.  You spring board that reputation into being the guy to invite to all the parties.  It worked for me. I used a couple of grandpas in June and then got fucked by 10’s from Independence Day til I met coolwave. I’m glad I don’t have to do that again(implying I’d get us a share house the following summer)”

I’ve analyzed this left right and sideways. I know he was talking to a peer. I know he was showboating and puffing to be desired because he just shit on us. I know I was paying him so what should I expect. I get that I intentionally brought him into a world of luxury that he coveted but that he wasn’t ready for, exploiting my power. I get all the angles. It still cut me to my core.
 

After that weekend I told him that I was really hurt by what he said and disinvited him to my Christmas trip to LA. We had a 2 week January vacation planned during his school break that I pulled the plug on. He apologized and tried to say that he didn’t think of me like he thought about those grandpas and that I should have known that. He also copped to there being some show boating to impress head boy.

none of it made me feel better.

6 months later with no contact I called and wished him a happy birthday in the spring and said I’d give him $50 for every trivia question he answered correctly about our Paris trip. He got every single one right. He remembered all the inside jokes, places we visited, people we met, boys we fucked etc. I got to feel like at least that part may have been two dudes genuinely enjoying each other. Who knows. He periodically texted me through out the summer some inside joke or thing that reminded me of him.  Labor Day I said I missed him and he offered a plan when he was home on break. He said no money, just friendship. And then he canceled, and it hurt all over again.

Im too experienced at hiring to succumb to these types of pitfalls. These are the pitfalls I warn others about. 
 

 

Edited November 2, 2022 by Coolwave35

[GTMike]

1 hour ago, Coolwave35 said:

Sure. Paris boy and I had this beautiful hotel room in Manhattan overlooking the park. I got a text from head boy that he was in town unexpectedly. I said “hey paris, I know you were curious about meeting (used his name). He happens to be in town, would you like him to join us for dinner”. He said that would be great. 
 

This is me paraphrasing. Head boy met us at the hotel and we chit chatted. Paris boy said I understand the attraction whoah. I said isn’t he great. Head boy said is this the bottom I’ve heard so much about?  I said yes. He said I bet Coolwaves always wanted to double penetrate. I said I couldn’t possibly. Paris boy said let’s do it. I laid on my back. Paris boy was on all 4s over me. Head boy fucked him from behind with my dick stationary inside.  It was a very aggressive pounding. When head boy finished and pulled out, there was an oopsie.  Head boy is huge and runs into this all the time. This isn’t bottoms first time in this predicament either. I’m embarrassed for bottom but bottom isn’t embarrassed at all. Bottom goes to one shower. Top and I go to the other. He raves about how hot he is, and wants to make sure I’m not in danger of being taken advantage of. He said can we hang out and talk a bit before dinner? I said of course. I go join bottom in his shower to make sure he’s ok with plan. He asks to hang in room and get dine in room service. He said something along the lines of this happens to the best of us and as long as you won’t bottom because you’re afraid of this, you’re denying yourself a world of pleasure. It’s a thing that happens and you move on. Both guys were super sweet and compassionate and I felt honored and privileged to be with them.

So after the shower we all laid on the couch in robes. That’s when the picture was taken. Head boy said “so what do you like to do for fun”. Bottom answered that he really enjoyed fire island over the summer, nyc clubs, his D1 sports team, technology and music etc. head boy said I went to fire island and it was a little cliquey for me. It was clear to me that I wasn’t in.

That’s when my world came crashing down. 
 

bottom said, and this is not paraphrasing.  “oh it’s easy. You let a couple of old rich guys fuck you until they let you use their house when it’s vacant some weekend. Then you become the hot 21 year old with his own share house.  You spring board that reputation into being the guy to invite to all the parties.  It worked for me. I used a couple of grandpas in June and then got fucked by 10’s from Independence Day til I met coolwave. I’m glad I don’t have to do that again(implying I’d get us a share house the following summer)”

I’ve analyzed this left right and sideways. I know he was talking to a peer. I know he was showboating and puffing to be desired because he just shit on us. I know I was paying him so what should I expect. I get that I intentionally brought him into a world of luxury that he coveted but that he wasn’t ready for, exploiting my power. I get all the angles. It still cut me to my core.
 

After that weekend I told him that I was really hurt by what he said and disinvited him to my Christmas trip to LA. We had a 2 week January vacation planned during his school break that I pulled the plug on. He apologized and tried to say that he didn’t think of me like he thought about those grandpas and that I should have known that. He also copped to there being some show boating to impress head boy.

none of it made me feel better.

6 months later with no contact I called and wished him a happy birthday in the spring and said I’d give him $50 for every trivia question he answered correctly about our Paris trip. He got every single one right. He remembered all the inside jokes, places we visited, people we met, boys we fucked etc. I got to feel like at least that part may have been two dudes genuinely enjoying each other. Who knows. He periodically texted me through out the summer some inside joke or thing that reminded me of him.  Labor Day I said I missed him and he offered a plan when he was home on break. He said no money, just friendship. And then he canceled, and it hurt all over again.

Im too experienced at hiring to succumb to these types of pitfalls. These are the pitfalls I warn others about. 
 

 

Hmmm? I don't know @Coolwave from your original point you thought you screwed up introducing two friends and one was considered higher on the pecking order and in retrospect that was a bad idea. 

Based on all this it seems you're needlessy blaming yourself for a faux pas or bad judgement. Seems like for the most part all parties were fine and the set-up of the situation was ok and feelings weren't hurt because of that dynamic. They both knew about the other.

Just seems like in so many things in life if you spend a lot of time with someone, or situations just brings out an unfortunate aspect of a personality, and excuse the pun, but "shit happens".   

Seems to me the one guy just might have felt the need to measure up a bit and in that state may have gotten carried away, overplayed his hand, and exposed to you a calculating/user-like angle of his personality.

You all of course are experts of your personal dynamics and were the one's there but  (as a hypothetical example), without #1 in town, you could've easily taken #2 to a fancy party, he might have one too many drinks and you overhear him glibly gossiping to another SB bragging about the same thing to impress.

Really just saying given everything it didn't seem like this substantially occurred because of poor judgement on your part introducing them if that makes sense?

 

 

[MscleLovr]

5 hours ago, GTMike said:

given everything it didn't seem like this substantially occurred because of poor judgement on your part

I completely agree.

 

6 hours ago, Coolwave35 said:

I intentionally brought him into a world of luxury that he coveted….exploiting my power.…It still cut me to my core.

I don’t mean to be harsh @Coolwave35 but… 
Did Bottom promise you fidelity and monogamy? Did you promise Bottom that he would be your only boy?

Did you tell Bottom that you wanted him to be exclusive? Did you promise Bottom that you would pay all his bills even when you were not together?
 

Earlier you mentioned how you admired Bottom’s drive and initiative, eg his making money trading on Amazon. How is his resourcefulness on Fire Island different?
 

It seems to me that maybe you had some romantic notions about him. Bottom is a lovely, fit young man who does what you like in bed. He wanted to enjoy the Summer and he met other guys who, like you, were happy to reward him for his company. Having successfully navigated the social whirl of Fire Island, Bottom was able to enjoy spending time with other lovely, fit young men. 
 

You’re not naive @Coolwave35 but I wonder if there isn’t some jealousy that Bottom was able to have a great time without you? When you were not there to orchestrate his activities? 
 

From what you’ve written, it doesn’t seem to me that Bottom misled you in any way. You had a thoroughly good but transactional relationship with him. I feel you overreacted in cancelling your other planned trips with him - that to me seems like “cutting your nose off to spite your face”.

I’d urge you to be the bigger, more mature man here. Call him up and tell him you really want to see him again and make a date!

 

[pubic_assistance]

11 hours ago, Coolwave35 said:

That’s when my world came crashing down. 
 

bottom said, and this is not paraphrasing.  “oh it’s easy. You let a couple of old rich guys fuck you until they let you use their house when it’s vacant some weekend. Then you become the hot 21 year old with his own share house. ......I used a couple of grandpas in June and then got fucked by 10’s from Independence Day til I met coolwave. I’m glad I don’t have to do that again

Well .....at least you're not in the" grandpa" category.

Transactional relationships can be complicated. You pay for a fantasy that isn't going to be fun when you start believing the fairy tale and then get slapped in the face with the truth. Prince Charming is an escort. He's there because you pay him. Escorts will choose the man who pays the most and annoys them the least ( until that dynamic changes ). DIS-inviting him and complaining to him turned your relationship into something different. It's no longer the easy alternative to old grandpa.

 

[+ Coolwave35]

13 hours ago, GTMike said:

Seems like for the most part all parties were fine and the set-up of the situation was ok and feelings weren't hurt because of that dynamic. They both knew about the other.

Seems to me the one guy just might have felt the need to measure up a bit and in that state may have gotten carried away, overplayed his hand, and exposed to you a calculating/user-like angle of his personality.

Really just saying given everything it didn't seem like this substantially occurred because of poor judgement on your part introducing them if that makes sense?

One of the agreements if we move into an arrangement is that it isn’t exclusive for either one of us. My seeking profile makes that abundantly clear too. I love hearing about their other arrangements. They are curious about mine. I regularly mix and mingle boys on ski trips, house parties etc. After reading your post, I definitely feel less like it was poor judgement. Still disappointed it happened, but I hear what you say that it could have happened another way too.  Thank you. 
 

8 hours ago, MscleLovr said:

Did Bottom promise you fidelity and monogamy? Did you promise Bottom that he would be your only boy?

Did you tell Bottom that you wanted him to be exclusive? Did you promise Bottom that you would pay all his bills even when you were not together?

Definitely not. Just the opposite. It’s a turn on, and inspirational, to hear about other arrangements these boys have and where I fit in from their perspective. Not all of his bills but he had far less financial worries than other kids his age. 
 

 

8 hours ago, MscleLovr said:

How is his resourcefulness on Fire Island different?

You’re not naive @Coolwave35 but I wonder if there isn’t some jealousy that Bottom was able to have a great time without you? When you were not there to orchestrate his activities?

That resourcefulness is different because it feels exploitive and usery, and if he’ll exploit and use someone else, he’ll inevitably do it to me too.

I tend not to be a jealous guy in general so I don’t think it’s that. It really was the casual cruelty he conveyed that bothered me. 

 

4 hours ago, pubic_assistance said:

Well .....at least you're not in the" grandpa" category.

Transactional relationships can be complicated. You pay for a fantasy that isn't going to be fun when you start believing the fairy tale and then get slapped in the face with the truth. Prince Charming is an escort. He's there because you pay him. Escorts will choose the man who pays the most and annoys them the least ( until that dynamic changes ). DIS-inviting him and complaining to him turned your relationship into something different. It's no longer the easy alternative to old grandpa.

Yes. I can’t disagree with you. It still sucks. 

 

 

[pubic_assistance]

37 minutes ago, Coolwave35 said:

Yes. I can’t disagree with you. It still sucks. 

I don't think it HAS TO suck.

What "crashed" is your fantasy.

Find some joy in the reality.

If you have access to enjoying the company of young attractive men in exchange for compensation, then just enjoy it and stop overthinking the emotional connections you may or may not be making.

There is always a degree in exploiting going on in a pay-4-play relationship. That's just the reality of it. Santa Claus doesn't exist. The Easter Bunny doesn't bring you a basket and Jesus Christ isn't saving you from evil. These are all fantasies meant to make you feel safe and happy. You're an adult now. YOU make yourself safe and happy and MONEY is the tool that gets you want to want and need to be happy.

Edited November 2, 2022 by pubic_assistance
spelling

[BonVivant]

In memoriam to all the failed SBs and those that just can’t make it on SA. 
 

 

Edited November 2, 2022 by BonVivant

[Harryinny]

This thread was started by @MrMiniver saying that he created a profile in the site and paid the entry fee.  Sorry to ask, but what site is that?

[pubic_assistance]

SEEKING is a Sugar Daddy site

https://www.seeking.com/

 

 

[fedssocr1]

4 hours ago, Coolwave35 said:

That resourcefulness is different because it feels exploitive and usery, and if he’ll exploit and use someone else, he’ll inevitably do it to me too.

I tend not to be a jealous guy in general so I don’t think it’s that. It really was the casual cruelty he conveyed that bothered me. 

 

 

I think that's what really jumped out at me in reading your story. Ultimately it seems sensible to enjoy things as they are and when things change for whatever reason it's natural to be left a bit off balance.

I'm not sure exactly what the point of the quiz was. Was that to find out if your relationship was more than him collecting money from you?

[+ Coolwave35]

1 hour ago, fedssocr1 said:

I'm not sure exactly what the point of the quiz was. Was that to find out if your relationship was more than him collecting money from you?

No, it’s a component of my arrangements. After the Paris trip I called him and he was out to dinner with his best friend. I asked if I could talk to her, and then quizzed her on our trip for cash. I was curious what stories he relayed to her, in what context and what the highlights were for him that he shared with her. It’s just a different way of getting money into his hands and something we’d done many times before. 

[Skip]

Wow, this is quite a thread, from just a few questions about the Seeking website. I have had several very successful arrangements including one that I am in now with a fabulous guy. A couple of observations, while you may be atttactive or in great shape, you're probably still a grandpa in their eyes . That's okay, they signed on for that. Treat them with respect and you will get the same in return. Turn the feelings of jealousy of other things they do around. Would you really want this twenty somethng guy with all the issues that go along with being that age around 24/7? Even if they are the next Jamie Dimon the issues facing that age group can be exhausting for those who have been there done that ! So if they see other guys or travel without you, be happy for them, not jealous. Don't ask questions if the truth will bother you.  You may remember the movie Saving Private Ryan, when the young soldier Matt Damon, morphs into the old man in the Normandy graveyard. We all had our turn to be Matt Damon. Now even Matt Damon is looking a little "older" . Gay men can be a petty jealous group, try to rise above that. Personally I am glad that I have the ability to hire or arrange with these guys and am not figuring out how to retire on Social Security. Four or five days every other month is plenty.  Zadun in Cabo San Lucas in February will be  lot more fun with this guy than with my peers even though they would pay !  Some people can get just way too involved. Be glad for th opportunities that modern technology and communications have brought to us. 

[HoseMaster]

On 11/1/2022 at 7:09 PM, Coolwave35 said:

Sure. Paris boy and I had this beautiful hotel room in Manhattan overlooking the park. I got a text from head boy that he was in town unexpectedly. I said “hey paris, I know you were curious about meeting (used his name). He happens to be in town, would you like him to join us for dinner”. He said that would be great. 
 

This is me paraphrasing. Head boy met us at the hotel and we chit chatted. Paris boy said I understand the attraction whoah. I said isn’t he great. Head boy said is this the bottom I’ve heard so much about?  I said yes. He said I bet Coolwaves always wanted to double penetrate. I said I couldn’t possibly. Paris boy said let’s do it. I laid on my back. Paris boy was on all 4s over me. Head boy fucked him from behind with my dick stationary inside.  It was a very aggressive pounding. When head boy finished and pulled out, there was an oopsie.  Head boy is huge and runs into this all the time. This isn’t bottoms first time in this predicament either. I’m embarrassed for bottom but bottom isn’t embarrassed at all. Bottom goes to one shower. Top and I go to the other. He raves about how hot he is, and wants to make sure I’m not in danger of being taken advantage of. He said can we hang out and talk a bit before dinner? I said of course. I go join bottom in his shower to make sure he’s ok with plan. He asks to hang in room and get dine in room service. He said something along the lines of this happens to the best of us and as long as you won’t bottom because you’re afraid of this, you’re denying yourself a world of pleasure. It’s a thing that happens and you move on. Both guys were super sweet and compassionate and I felt honored and privileged to be with them.

So after the shower we all laid on the couch in robes. That’s when the picture was taken. Head boy said “so what do you like to do for fun”. Bottom answered that he really enjoyed fire island over the summer, nyc clubs, his D1 sports team, technology and music etc. head boy said I went to fire island and it was a little cliquey for me. It was clear to me that I wasn’t in.

That’s when my world came crashing down. 
 

bottom said, and this is not paraphrasing.  “oh it’s easy. You let a couple of old rich guys fuck you until they let you use their house when it’s vacant some weekend. Then you become the hot 21 year old with his own share house.  You spring board that reputation into being the guy to invite to all the parties.  It worked for me. I used a couple of grandpas in June and then got fucked by 10’s from Independence Day til I met coolwave. I’m glad I don’t have to do that again(implying I’d get us a share house the following summer)”

I’ve analyzed this left right and sideways. I know he was talking to a peer. I know he was showboating and puffing to be desired because he just shit on us. I know I was paying him so what should I expect. I get that I intentionally brought him into a world of luxury that he coveted but that he wasn’t ready for, exploiting my power. I get all the angles. It still cut me to my core.
 

After that weekend I told him that I was really hurt by what he said and disinvited him to my Christmas trip to LA. We had a 2 week January vacation planned during his school break that I pulled the plug on. He apologized and tried to say that he didn’t think of me like he thought about those grandpas and that I should have known that. He also copped to there being some show boating to impress head boy.

none of it made me feel better.

6 months later with no contact I called and wished him a happy birthday in the spring and said I’d give him $50 for every trivia question he answered correctly about our Paris trip. He got every single one right. He remembered all the inside jokes, places we visited, people we met, boys we fucked etc. I got to feel like at least that part may have been two dudes genuinely enjoying each other. Who knows. He periodically texted me through out the summer some inside joke or thing that reminded me of him.  Labor Day I said I missed him and he offered a plan when he was home on break. He said no money, just friendship. And then he canceled, and it hurt all over again.

Im too experienced at hiring to succumb to these types of pitfalls. These are the pitfalls I warn others about. 
 

 

Thank you Coolwave for opening up and sharing the details of your experience, as well as your pictures.

[Jon Brown]

@Coolwave35 stories are simply the best part of these forums, easily :’)