Seeking Arrangements

[Steve 9696]

While the sex was decidedly mediocre, this experience was such a sweet slice of life. Taking a newbie down the path to mutual enjoyment. Think this is the forth or fifth SA girl I've taken from shy reluctance to a satisfying conclusion. And there is something distinctly satisfying about that, but in a different way than just a fabulous bedroom experience. Here's how it went down with my latest Seeking virgin (others were three or four years ago — rare to find a stone cold newbie these days but such fun).

As usual on Seeking I started probably earlier than advisable just because I enjoy browsing. But sometimes that works out great because you hit a quality girl and things click and you can stay in touch 6-8 weeks in anticipation. Also guarantees they are a real girl not a hooker because hookers have no time for that.

So Marina and I connected about 7 weeks ago and had a lovely chat. Her English is very good so we mostly chatted in English. Her pics were solid if not exceptional and she was super sweet. We stayed in touch daily the last few days and she showed up right on time.

She is a very pretty girl, much prettier than her pictures and thic in the true sense, but not fat. She exercises and is well toned.

Dinner is a little slow and awkward to start but we both get Gin and Tonic doubles and things smooth out quickly. Her English is positively amazing and so it's quite easy. The food is absolutely awesome and 1. 5 hrs flies by.

I can sense she is really new to the game. She says she went on one seeking date before but the guy looked nothing like his picture and they parted after dinner. I feel like she likes me and is DTF but I want to be respectful because she's new. So I ask her if I should get a car and she says yes.

I can tell both walking to the car and in the car she is nervous about affection. But we walk to my room and head in no problem and sit on the bed. We are positioned about two feet apart and I touch her lightly and lean forward for a possible kiss but she doesn't really lean in and I know she is def feeling awkward.

She confesses she's never been back to the room before on a seeking date but that she really likes me so she wanted to. I tell her I don't want to do anything she doesn't want to and suggest I give her a massage. She says ok and takes off her jacket and lies on her stomach still fully clothed.

I give her a pretty great massage because I do that a lot w my girl back home. And after maybe ten minutes I decide to untie the bow on the back of her blouse. I guess the massage is working it's magic (I am lightly grinding plus I moved to massaging her ass cheeks) because she says let me roll over and finishes untying and then takes off her blouse. Super nice firm be cups and my mouth is on them in seconds.

Some tit circles and sucking and she is def worked up because when I go to kiss her it is deep and passionate and urgent. Ok it's on for sure now. She just needed to relax and lean into the situation.

Once on a roll it's quite good and passionate. I start by licking her tits down to her waistline and then pull back her waistband and go as low as I can go. She is def ready to rumble because when I get her pants off she is wet as a fountain and I dive right in with tongue and fingers.

She never has a huge shattering pussy clamping O but is def having a good time. Time to get me in the game. Here's where the curveball comes — as I take off my pants she says "I don't like to do blowjobs". Ouch.

In my head I think "well that def going to limit your options in life!" But nice guy that I am I say OK and finger her a bit more but kneeling cock out not far from her face. She has her hands over her head but I take her right hand and put it on my cock (these babes in the woods!) and she starts a fairly lame attempt at jacking me to get hard.

The kinda fun part of this is she is not playing a game. She is just a girl trying to figure it out and very inexperienced in bed. Now that we have moved from scared awkward girl to naked buddies I make it my mission to improve her sexual skills!

Her jacking isn't doing much for me so I move her hand to my balls and say to just stroke and squeeze lightly. She does this and it feels great. As part of my mission I tell her that working balls makes a guy horny and it's working for me.

At some point she says "I am ready" and she def is. Super wet. We go for the condom option tho I am 90% sure she would have gone bare if I just slipped it in. But my Sagami 02's (high recommend) are damn good and she feels great.

We fuck for a super long time because of no pre-game warmup. But she doesn't seem to mind and is def enjoying herself. Initially in mish for a long time and with passionate kissing. Then the Steve. Back to mish where she has a small orgasm tightening her limbs and pussy around me. Some doggie.

At some point I think I am never going to blow a stack like this. Got to convince her to BJ. So I pull out and flop on my back and say let's do a little BJ. You don't have to take it in your mouth or deep. Just lick my balls. And she tentatively acquiesces.

She starts soft licking and it feels nice. I tell her she can lightly suck them and it's clear this never occurred her but she does it nice and gently. This is def working and she starts to move up the shaft a little. I show her how to do harmonica and that feels great. She's getting the hang of this and maybe understanding that a BJ is not just jamming it in and out.

When she reaches the tip she takes it in her mouth and starts pumping the first third in and out at a nice slow pace. Feels nice. I can feel the build in the distance. So I put her back on balls and do a sloppy self handy while she sucks away. I fucking love that and shoot out a hot load.

We cuddle for a good half hour but then I call her an uber. A truly sweet girl. A true newbie. And honestly a lot of fun to break her in. Maybe her future boyfriends will thank me!

[Steve 9696]

Interesting. I live in a part of LA with a sometimes shocking amount of money. One girl I know came from a rich family and married a guy from a richer family. When they got married the dads got together and bought them a beautiful house, paid off, in a tony part of an already nice area. I remember thinking these people must be so happy not having the stresses that mere mortals have, paying off mortgages and student loans and saving for retirement.

They divorced 3 years and 1 baby later. I was shocked. What problems could they possibly have had? I mean they liked each other enough to get married didn't they? Can't they just live nice lives basking in their privilege and comfort?

But then I realize that's not how life and humans work. It's just like Seeking. Every new girl I do repeats with (a minority) at some point become stale. And then there's that one last visit where I just feel like maybe she's phoning it in, or maybe I am, or both, and I walk away thinking well that's the last time we'll probably see each other again. It's just easier with Seeking because it's an arrangement.

That's the beauty of Seeking. Even if you totally ignore the compensation part (not starting that again!) the best part is that both parties know it's temporary. No drama around "is he / she the one". Enjoy your time together whether 1 day or one year and then next next. It's truly beautiful.

[AmericanPi]

Seems like I say this a lot but there are just as many situations as there are girls. Everybody has different motivations and it's hard to generalize. A family member very close to me is very successful, was married to a guy nowhere near as but his family had real money. He was expected to provide her with a monthly allowance. It was a cultural thing, she didn't need it and he didn't care because it was dad's money. She was very particular, wanted the best of everything and deserved it in her mind because she's intelligent, works really hard and can afford it with ot without him. Marriage didn't work because he wanted a simpler life or didn't have the ambition, didn't want the bells and whistles and 5 star whatever. I don't think she considers herself a victim and I haven't had this particular conversation with her but I suspect she realizes she's made some personal decisions that have affected her overall happiness. Almost too old to have a kid now and I know she wanted one. No one to vacation with and come home (to her beautiful home) to. In many ways our lives are parallel but I never wanted kids and my house is a panty dropper. That is until the day comes that no amount of tangible pluses overcome my lack of physical / mental appeal. Age will always catch up with us sooner or later. Dowrys are also still very common, from man to woman, so for an average guy to bag a legitimately successful woman can be very difficult in my particular example.

Interesting. I live in a part of LA with a sometimes shocking amount of money. One girl I know came from a rich family and married a guy from a richer family. When they got married the dads got together and bought them a beautiful house, paid off, in a tony part of an already nice area. I remember thinking these people must be so happy not having the stresses that mere mortals have, paying off mortgages and student loans and saving for retirement.

They divorced 3 years and 1 baby later. I was shocked. What problems could they possibly have had? I mean they liked each other enough to get married didn't they? Can't they just live nice lives basking in their privilege and comfort?

But then I realize that's not how life and humans work. It's just like Seeking. Every new girl I do repeats with (a minority) at some point become stale. And then there's that one last visit where I just feel like maybe she's phoning it in, or maybe I am, or both, and I walk away thinking well that's the last time we'll probably see each other again. It's just easier with Seeking because it's an arrangement.

[FilthyBeaver]

Quid pro quo is the ante / entry free. Anything that happens after that depends on the two people involved. It's impossible to generalize. I've had one night stands, platonic dinner dates, multi month "flings" that were basically relationships and I currently see a girl that doesn't want to go out in public but will spend hours chatting, having sex and leaving. They've all worked for me at one point or another or I wouldn't have participated in them. I've taken pics with them but don't have social media so I post nothing and I'd politely ask that they not post pics of me on their sm. Not because I'm embarrassed, rather because as I as small an online presence as possible including pics of any kind of me.

The important thing is you get what you want, preferably without hurting (emotionally or otherwise) someone, and they get something they want in exchange. Two consenting adults, blah, blah, blah.

I am not willing to get into this debate / discussion / opinion. Whatever you may call it.

I am 200% certain seeking is quid pro quo as far as I am concerned. It could mean something else for someone else but that's his prerogative. I have no issues with that. Neither should I have an opinion about it. His life, his money, his sugar babes. Let him do whatever he wants. Unless someone asks for advice, I don't offer that.

Me saying "I thought. " doesn't mean that I really think so. It's a polite way of reminding the girl while leaving the door open for her to respond with what she thinks. To me, my politeness has given me more pussy than my wallet.

But, as you can see, I can stand firm when it counts. Including this response.

[FilthyBeaver]

Seems like I say this a lot but there are just as many situations as there are girls. Everybody has different motivations and it's hard to generalize. A family member very close to me is very successful, was married to a guy nowhere near as but his family had real money. He was expected to provide her with a monthly allowance. It was a cultural thing, she didn't need it and he didn't care because it was dad's money. She was very particular, wanted the best of everything and deserved it in her mind because she's intelligent, works really hard and can afford it with ot without him. Marriage didn't work because he wanted a simpler life or didn't have the ambition, didn't want the bells and whistles and 5 star whatever. I don't think she considers herself a victim and I haven't had this particular conversation with her but I suspect she realizes she's made some personal decisions that have affected her overall happiness. Almost too old to have a kid now and I know she wanted one. No one to vacation with and come home (to her beautiful home) to. In many ways our lives are parallel but I never wanted kids and my house is a panty dropper. That is until the day comes that no amount of tangible pluses overcome my lack of physical / mental appeal. Age will always catch up with us sooner or later. Dowrys are also still very common, from man to woman, so for an average guy to bag a legitimately successful woman can be very difficult in my particular example. He needs to prove he's worthy even though the vast majority of unions are purely symbolic, the dowry needs to be displayed in public to save face even though it's generally just given back to the couple by the woman's family.

I have another theory. How's this? It's the story they need to tell themselves to explain their existence.

A girl who says she's unhappily single approaching middle age because she squandered her youth and looks, and is simply no longer as attractive to guys her age is a girl who is being honest. But damn that's a hard hard reality and life story chapter to confront daily.

Enter the narrative. No, she's single because she's strong and powerful and most men just can't handle a strong powerful woman like her. She's gets to play the role of noble victim in this story.

Think that might be it?

[Gfefan]

I am not willing to get into this debate / discussion / opinion. Whatever you may call it.

I am 200% certain seeking is quid pro quo as far as I am concerned. It could mean something else for someone else but that's his prerogative. I have no issues with that. Neither should I have an opinion about it. His life, his money, his sugar babes. Let him do whatever he wants. Unless someone asks for advice, I don't offer that.

Me saying "I thought. " doesn't mean that I really think so. It's a polite way of reminding the girl while leaving the door open for her to respond with what she thinks. To me, my politeness has given me more pussy than my wallet.

But, as you can see, I can stand firm when it counts. Including this response.

I really do not have an ax to grind on this topic. It's just a minor topic for me. But it's germane to the discussion.

This is an almost perfect example of the point I've been making about the intersection of delusion and desire on both sides. The words "I thought that we" are the hallmark of so many conversations recounted here.

[AmericanPi]

Got a theory about this. It seems to me, around director level. Nobody tells them no. Their idea is stupid, their shit don't stink, etc. Well the wife (or husband) didn't get that memo and still expects the trash taken out, dishes washed, dog walked, whatever. That's a very big reason why their are so many affluent divorces. It's not just physical and mental changes that occur over time. There's a large social and socioeconomic factor. Power at work is very intoxicating..

I have another theory. How's this? It's the story they need to tell themselves to explain their existence.

A girl who says she's unhappily single approaching middle age because she squandered her youth and looks, and is simply no longer as attractive to guys her age is a girl who is being honest. But damn that's a hard hard reality and life story chapter to confront daily.

Enter the narrative. No, she's single because she's strong and powerful and most men just can't handle a strong powerful woman like her. She's gets to play the role of noble victim in this story.

Think that might be it?

[AmericanPi]

that means we have to rethink financials".

I responded "Ouch. I thought we both enjoyed the non-transactional nature of our arrangement last time we met. ". She goes "well, I have to come to you, commute time and whole night. It adds up, you know".

I really do not have an ax to grind on this topic. It's just a minor topic for me. But it's germane to the discussion.

This is an almost perfect example of the point I've been making about the intersection of delusion and desire on both sides. The words "I thought that we" are the hallmark of so many conversations recounted here.

[Elvis 2008]

I have no qualm with you. You're a core contributor and interlocutor here. People like you keep this thread alive and interesting. This reply is just because it's an interesting conversation. And it's ok to see things differently.

I feel the same way. There was no malice intended in my post, just a different perspective. I want everyone to get the best experiences possible out of seeking.

Where I think we see things differently is the notion you have that you can effectively suss out people's intentions with careful observation. I don't think that jibes with how duplicitous humans really can be. Half the men on here are married for gods sake. I have a whole alternate reality going on, complete with phone numbers, accounts, password protected apps, and the like. I might be further on the duplicity spectrum than most, but I assume as a baseline that most people ID meet on Seeking reside on that spectrum too. These relationships usually start with pseudonyms and google voice numbers and might become more transparent from there. But again, at the core of it, a girl selling beauty and sex for resources, and a guy giving resources for that access, are engaged in a relationship that's far more likely than not to be an exchange of fantasy and not two people living at the intersection of their respective unvarnished realities.

Okay, I see where you are coming from. Steve wrote something about "keeping the fantasy alive", and I am like I am beyond a fantasy, but when you are married, and you want to ramp up the intensity, it needs to be a fantasy.

In my case, when I was married, I only had sugar babies in the USA and I cannot recall any time getting burned trusting them. They were usually pretty hot and had other guys more than willing to step into my shoes. I guess you could say I set limits and told the women I was married and we all knew how far the relationship could be stretched and did not go beyond that. There were issues with other sugar babies I had but for some reason not with any of the women I met off of seeking.

Of course, there were the ones who showed themselves to be untrustworthy early on and when you talk places like Colombia or other countries where there are so many attractive women and so much less money, getting a well to do sugar daddy replacement is much harder. I could see being more skeptical with trusting a woman in places like that.

But I had sugar babies in other countries and for the most part, my trust was more than reciprocated, and it led to incredibly fun and intimate times.

I get it though. It is not easy to pick out what people / women to trust. I can see guys saying trust no one to protect themselves. I am just saying IMO it is not always the best way to be and certainly not the only way to be.

[FilthyBeaver]

Just a mild reminder of the quid pro quo thing. Not that I'm any more desirable or have anymore game but I've never given more than a "standard" date if they spend the night. I've willingly over paid and they're expected the same thing later but I generally move on.

Working on my upcoming schedule.

The squirter I met earlier was trying to meet me. I technically could meet her and was exploring options. I floated "Hey, how about this time I get a nice hotel with sauna and stuff and we spend the whole night?

She goes "of course. That would be nice but that means we have to rethink financials".

I responded "Ouch. I thought we both enjoyed the non-transactional nature of our arrangement last time we met. ". She goes "well, I have to come to you, commute time and whole night. It adds up, you know".

Amd, I am like "Ok. It is a bit of an effort for me to divert from my path and come see you. So, do ourselves a favor Go ahead and plan your day / night without me in the picture. I will continue on my path".

Boom. Done. She could have made 300, squirtrd a ton and enjoyed all the other perks. This whole shit of "my time is valuable" is so delusional.

[FilthyBeaver]

Got a theory about this. It seems to me, around director level. Nobody tells them no. Their idea is stupid, their shit don't stink, etc. Well the wife (or husband) didn't get that memo and still expects the trash taken out, dishes washed, dog walked, whatever. That's a very big reason why their are so many affluent divorces. It's not just physical and mental changes that occur over time. There's a large social and socioeconomic factor. Power at work is very intoxicating.

I'd say 40% of the director level / business owners I know are divorced and I doubt that would change any time soon. Thank God we can trade in omfir a newer model with less miles. Much more difficult to do the same.

This really did go off on a tangent, sorry. Sometimes when you write on your phone it goes in weird places. But this is interesting.

The problem with some, not all, of the career women I know (and in my circle I know a lot) is that they've convinced themselves they're single because guys can't handle a powerful woman like them and the men are intimidated. Or they are telling themselves that and hoping men believe it. I'm telling you it's such a thin veneer. I worked in Fortune 500 with some of these ladies and have known them almost 2 decades. The problem isn't that guys are intimidated by them (I myself am married to a successful professional with an advanced degree from a top 10 university). The problem is that the whole "guys are intimidated by a stronger sau 40powerful female like me" thing is boring and there's no way to honestly coexist with someone whose core life narrative orbits around that idea. You either have to pretend to honor and celebrate it (despite seeing how thin it is, how desperate some of these women are) or you are cast as the villain in the story, a guy who just can't handle such a strong woman. You know what I do? Honestly? I pretend to honor and celebrate it. And these women love me. They are the ones asking if I have friends like me I can set them up with. But inside I have moral and cognitive dissonance because I really just want to tell them they'd be far more attractive as partners if they'd just be honest about their needs and wants, which requires some vulnerability.

Which brings us back to Seeking. I see a similar form of delusion here at times. Not from you, FB, but from some. It's true that I don't know the people here personally and there are exceptions to every rule. But let's be honest, everybody thinks they're an exception.

[Gfefan]

Working on my upcoming schedule.

The squirter I met earlier was trying to meet me. I technically could meet her and was exploring options. I floated "Hey, how about this time I get a nice hotel with sauna and stuff and we spend the whole night?

She goes "of course. That would be nice but that means we have to rethink financials".

I responded "Ouch. I thought we both enjoyed the non-transactional nature of our arrangement last time we met. ". She goes "well, I have to come to you, commute time and whole night. It adds up, you know".

Amd, I am like "Ok. It is a bit of an effort for me to divert from my path and come see you. So, do ourselves a favor Go ahead and plan your day / night without me in the picture. I will continue on my path".

Boom. Done. She could have made 300, squirtrd a ton and enjoyed all the other perks. This whole shit of "my time is valuable" is so delusional.

[AmericanPi]

AP, do you see what you are doing? You are injecting YOUR reality into people you do not even know.

Ok, but there are con men who are not on seeking too.

The issue I have with stereotyping with seeking is people say the women on seeking are all about the money. That is fine, but where is the world where women are not all about the money? Because IMO that world does not exist.

And with men with wealth, how would they get wealthy if they were not able to spot scam artists?

I have no qualm with you. You're a core contributor and interlocutor here. People like you keep this thread alive and interesting. This reply is just because it's an interesting conversation. And it's ok to see things differently.

I only kept a portion of your reply so it doesn't take up all that space. I agree with the notion that men and women all exist on some spectrum. It's an obvious point to me that you can't paint everyone with the same brush. But parsing details on a chat board is hard.

Where I think we see things differently is the notion you have that you can effectively suss out people's intentions with careful observation. I don't think that jibes with how duplicitous humans really can be. Half the men on here are married for gods sake. I have a whole alternate reality going on, complete with phone numbers, accounts, password protected apps, and the like. I might be further on the duplicity spectrum than most, but I assume as a baseline that most people ID meet on Seeking reside on that spectrum too. These relationships usually start with pseudonyms and google voice numbers and might become more transparent from there. But again, at the core of it, a girl selling beauty and sex for resources, and a guy giving resources for that access, are engaged in a relationship that's far more likely than not to be an exchange of fantasy and not two people living at the intersection of their respective unvarnished realities.

[AmericanPi]

Not really related to seeking but ….. It takes a a certain level of ambition, aggressiveness, bitchiness whatever you want to call it and most men's egos can't deal with it..

This really did go off on a tangent, sorry. Sometimes when you write on your phone it goes in weird places. But this is interesting.

The problem with some, not all, of the career women I know (and in my circle I know a lot) is that they've convinced themselves they're single because guys can't handle a powerful woman like them and the men are intimidated. Or they are telling themselves that and hoping men believe it. I'm telling you it's such a thin veneer. I worked in Fortune 500 with some of these ladies and have known them almost 2 decades. The problem isn't that guys are intimidated by them (I myself am married to a successful professional with an advanced degree from a top 10 university). The problem is that the whole "guys are intimidated by a strong powerful female like me" thing is boring and there's no way to honestly coexist with someone whose core life narrative orbits around that idea. You either have to pretend to honor and celebrate it (despite seeing how thin it is, how desperate some of these women are) or you are cast as the villain in the story, a guy who just can't handle such a strong woman. You know what I do? Honestly? I pretend to honor and celebrate it. And these women love me. They are the ones asking if I have friends like me I can set them up with. But inside I have moral and cognitive dissonance because I really just want to tell them they'd be far more attractive as partners if they'd just be honest about their needs and wants, which requires some vulnerability.

Which brings us back to Seeking. I see a similar form of delusion here at times. Not from you, FB, but from some. It's true that I don't know the people here personally and there are exceptions to every rule. But let's be honest, everybody thinks they're an exception.

[FilthyBeaver]

Not really related to seeking but interesting nonetheless. A successful middle aged women past her physical prime is rarely going to settle for hot stud monkey boy as a long term commitment. Any middle aged man in the same boat isn't looking for someone his own age (with very few exceptions). When I was a corporate drone I knew a few, frankly the men all had personality flaws they were able to hide from the women they connected with before she knew what she got herself into. I'm willing to bet most are divorced by now but I don't keep in touch with any and I have no clue. I know some very successful women, acquaintances and family members, but I wouldn't introduce them to anyone I know even though I want the best for my family. It takes a a certain level of ambition, aggressiveness, bitchiness whatever you want to call it and most men's egos can't deal with it. I know them well enough to know that their personality quirks are not conducive to long term relationships (at least to anybody I know). Like you, I play coy and don't get involved.

I agree with everything you wrote. And I'm quite alright with what being on Seeking means for me and the girls I bang there. I'm fully aware girls are trading their sexual appeal today because it's a fading asset. I actually admire girls who have the foresight to embrace this earlier in their lives, and bag a rich guy while doing so doesn't mean dating their dad. You know who I'm talking about. The smartest hot sorority girls in my college got linked early and hard to a guy who was clearly on the way up (Eg dad is a CEO and son will take over one day). The dumbest ones got drunk through their twenties and got desperate by 35. I am now middle aged and I have female friends who are still single at my age and it's sad. They always, always ask if I have friends for them. And I always play coy and think 2 things. First, some of my friends know about my whoring and there's no way I'm cross pollinating that into another friend group. And second, none of my friends my age want to date women their age. Some of these women spent their prime years trying to be girl bosses or whatever and talking about how they don't need a man, only to wake up at 45 desperate, unhappily childless, and with poor romantic prospects. I have no idea how I got on this tangent, but I'm writing on the phone, so I'm just going to hit upload.