curiousnomore

Great perspectives! And it would make a lot of sense if you were not being paid for your time.
 
To me, it seems the OP is saying...I paid for your time, I told you what I expected (sorta), and I even enhanced the experience, and yet I'm not getting what I want. With much respect to the human side of companions, if they prefer to pull out or don't like to cum in a condom, they should decline the OP bc they either can't perform it or prefer not to. Then the OP has a chance to decide if he still wants to continue booking.
 
I think it does go back to the original responses...in my opinion, either the OP is hiring the wrong companion or he is getting (consciously or unconsciously) duped by those who accept & end up pulling out. Excuses notwithstanding , it does not honor the requirement.
 
PS- is anyone else feeling a little frisky after reading nycman's response ?

I find it impossible to cum in a condom. Fucking in a condom is like kissing through a door screen.

I agree with jawjatech, you sound like a dream client...and whatever rate he offers, I'll undercut it by 10%.
 
As a hardcore top, I love feeling a bottom cum while I'm fucking him. Not exactly analogous to the feelings
you describe above, but damn close. It can be intense and amazing, and I think I understand what you're
trying to describe.
 
However, I don't enjoy coming in a condom. I play safe, but I've always hated the feeling. Fucking?
No problem, condoms don't bother me at all. Cumming? I don't just dislike it, I hate it. I always feel
like my balls aren't free to empty all the way. Worst part is, the more turned on I am and the harder
I cum, the worse the sensation gets. Sometimes, it's even a little painful. So the times I'm having the
most fun always end on a sour note if I try and cum in the condom.
 
So it's become almost routine for me to get as close to cumming as I can and then pull out, rip off the
condom and finish off by hand on the bottom's ass. At this point I'm so into it, it almost qualifies as a fetish.
 
Also, for much of my adult life, most bottoms wouldn't let you cum in their ass, even with a condom
on. That's changed significantly in the past decade, but at the time it was a big deal, and I got used to it.
 
I've noticed a few bottoms get disappointed by this. Some go as far as to blame themselves. As if their ass
wasn't good enough to get me off 100%....which of course is insane.
 
So there you have it. I'm not sure it helps. I thought it might be interesting to hear the story from the
side of a top, who is VERY committed to keeping his bottoms happy, but sometimes can't.

+1 on lrtwo's comment

Clarity: the mother of getting whatcha want. Personally, when I want something very specific, I don't add complicating layers....no dinner, no chit-chat, no worrying about my own suitability. I focus my companion on the task at hand and then reward him with all of the above (except for the self doubt bc I know I'm perfectly imperfect).
 
Now, any professionals (not necessarily clients) out there care to chime in with their view of this cum-in-my-ass dilemma?

OP, when you say it like that, people think you want it barebacking. That's what I thought until I carefully read through your whole post. The escort might think the same thing if you're not clear.

I am a total bottom and enjoy making certain the top I am with is having a really good time. The better time he has the better time I have. I enjoy having my arms around him, with him deep inside me as he cums while inside me (with a condom). I enjoy hearing the sounds from him, feeling his body spasm as he unloads inside. I don't object to him cumming on me, I just prefer in me.

I have a question, not to anyone in particular—just to the world of escorts at large:
 
Why won't you cum in my ass?
 
I play safe. I insist on a condom, either the traditional sort or a "femdom"/female condom. I don't want you to bareback me, or vice versa. I am as disease-free as one can be, having been spared all STIs (including herpes, which is nearly miraculous, it seems). I am a good-looking man, middle aged and nicely built, without curious neurotic habits that might make you go limp, and have a fine ass (if I can compliment myself without appearing to be too conceited). I am polite, respectful, and get money matters over with at the beginning. I take you to dinner, amuse you, and keep it all lightly friendly. I'm not looking for love (got that already). While I do get sex elsewhere (from my husband and boyfriend), you're my extra-special fantasy for a few hours...a bit of sexual theatre...pornography incarnate. I'm a nice guy who dresses well. (Really!) But I enjoy hearing, seeing, and feeling a guy lost in the throes of orgasm as he clutches me tight while he fucks my ass. I could make you promise to cum in my ass at the outset, but that just doesn't seem right somehow. And it has no guarantee attached.
 
So, what gives? I've set the stage for a pleasant evening or more. I've made sure my hygiene is impeccable. I give great oral, kiss like a fallen angel, and genuinely enjoy sharing our common humanity. Even my whispered suggestion, "You can cum in my ass", goes unheeded. You pull out and unload all over me. Which is great and fine, but it's not quite as exciting as hearing you grunting in ecstacy, feeling those nearly uncontrollable thrusts and shudders, and fearing—just a tiny bit—for my ribs as you try to grasp me tighter than seems humanly possible.
 
Is it barebacking? Has it become so common that cumming in a condom is impossible? Too many clients? (I usually book evenings or overnights.) Fear? Any ideas?

I like the occasional nature of this hobby. No strings attached.

No I haven't, for one reason. My wife has destroyed my interest in any defined relationship.

My arrangements were college boys with a built in ending. They would graduate (hopefully), move on with life, possibly re-locate, enter the work force, etc. I provided a set monthly stipend for a certain number of days/nights per month. No exclusivity. Two of them posted ads and were hired by other clients; they gave me scheduling priority. The other collegian saw no other clients (as far as I know); he was satisfied with the stipend.
 
These arrangements worked well because of the character of the young men, which I vetted through several meetings/hiring situations before terms were offered and accepted. All three of them went way beyond the minimum requirements in terms of satisfaction, scheduling, and number of meetings. Each ended amicably. They moved on to professional careers, and my interaction/communication with them ended.
 
It's a privilege to help aspirational young men.

I have. It was fun when it lasted and it inevitably came to an end. As most of these relationships do. Sugar daddy relationships don't really work because of the inherent conflict of interests. The 'son' always worries that the 'dad' can discard him at any time when somebody hotter shows up. The 'dad' worries that the 'son' is just staying in the relationship because of the money. Exclusivity issues can be problematic. Will 'dad' and 'son' live together, or separately? There will be real heart break when one party sees is as a quasi-marriage and the other party sees it as a short term arrangement. My advice: don't do it. Except if you both know/agree it is a short term thing. Or if you are really in love and are getting married.

Thanks for this thread Wolfer. I'm sure that I'm in the minority, but my first bottoming experience is still in my top three. The guy(Escort) was Hot. We had had met the night before I topped only). I woke up super-horny so I texted him and he was available, so he came over. After topping him twice (multi-hour appt), I asked him to fuck me. He took his time, prepped me, and it was amazing. Enough said.

Falling into lust (or more) for a particular person you want to bottom for is a great gateway, motivator & enabler. It pulled me into bottoming at age 46, and all I could think after was -- no idea what I'd been missing all those years!

I'll leave the detailed advice-giving to others, and will only suggest that rather than FORAY into bottoming, it is always best to SASHAY into it.

Anthony Driller
 
J D Daniels
 
Two classy men

I'm sort of an equal opportunity guy -- I like men from northern Europeans to dark black men. That said, I've met three black men I particularly enjoyed: Devin, formerly of Atlanta and now of New York. Sean Xavier, now retired I believe. And J.D. Daniels, with whom I'm meeting again this Friday evening in Atlanta. I plan to wear him out! (Or him to wear me out). We'll see who cries mercy first.

I've only met one escort that fits the criteria, JD Daniels, and he's great.

I've only met one escort that fits the criteria, JD Daniels, and he's great.

I opened my first Spanish textbook an the first day of my HS freshman year. And found a list of English to Spanish curse words and phrases that had been overlooked by the school staff. That list is all I remember.

I opened my first Spanish textbook an the first day of my HS freshman year. And found a list of English to Spanish curse words and phrases that had been overlooked by the school staff. That list is all I remember.

Yeah... I can blame him for me becoming bi-curious... haha.... wow.

OP, you're not alone

Op, you're not alone. My "Perfect Man" hasn't changed in 30 years. I went into hiring escorts looking for that guy, but all the early 20s jocks I contacted were, well, flaky. I ended up hiring a 33yo and a 37yo that first weekend. Wow!!!
 
While they met my "they're attractive" minimum threshold, I was still nervous. In person, they blew me away. Good looking And experienced? That combo beats 20s hot and self absorbed any day.
 
I'm still gonna meet Rey tho. Early 20s, hot and into Daddies is someone I can't miss out on meeting, lol.

Purplekow......Okay, most of us are into the guys i described, but that's all I'm interested in. Older men don't appeal to me. Many men can like that type of guy, but also other types. I mean, you are attracted to who you are attracted to, but I wonder if tastes for a lot of men change or evolve over the years because mine haven't. In fact, talking to one of my former escorts from 15 years ago I told him I wasn't involved with anyone, but hired a hot young escort a couple times a year. He sounded like he thought I should have moved on to older men by now. He wasn't being ignorant or anything, he just figured the type of guys i was attracted to would have changed over the years. Thickornotatall....I live in a small town outside a big city. The only gay men are closeted gay men, so you really don't know who they are. I could always head into the city bars, but I'm not into that scene. Your uncle meeting the dancer sounds so awesome. Yes, I've heard there are actually quite a few younger guys who prefer older men.

I wonder if you live in a small town or large city...That make quite a difference....My uncle lives a few streets away from me in The Village...We were taking the train uptown and a very cute young guy asked us if we are a couple......I said no.....mind you he is quite a bit older that I am....He was a dancer on Broadway for many years and is in great shape...very active...lots of energy....and almost 80!....I introduced them....The young man just turned 36 years old and is now with my uncle 2 years....Not my cup of tea....But they are out there....Someone for everyone....