Cyd_StVincent

I met with a virgin, although he was a little older than you, a while ago. He didn't tell me that that was what was going on but I could tell he was nervous. Turns out I was the first person to suck his dick, ride his cock, and put anything up his ass ever! It definitely seemed like an important and positive experience for him, I think not knowing me and knowing he wasn't in an environment where I was going to judge his skill level took off the anxiety that had been impeding him in his 30 some years of life.
 
I would suggest that you let your escort know before hand for sure, not everyone is going to be down for that kind of experience, and you want to have someone without hang ups. Also when you are doing anything for the first time, let the other person take control at first and then try to follow their lead. A lot of newbies to kissing will just go all out with the tongue action, enjoy the pleasure of being kissed and having your mouth opened, and then when you are more relaxed you can return in kind. Gentle and slow is always preferable to frantic and fast IMHO.

I would love to hear more about this from other escorts. I have quite a sizable twitter audience, something I put a lot of work into cultivating - but while it has been positive in directing people to my porn I don't get a lot of proposals for hires. It's possible they all go to rentmen and communicate from there, but I'm interested to hear what other escorts experiences have been. My porn persona is a little different and more extreme seeming than my escorting life, so I wonder if that creates a disconnect.

I met with a virgin, although he was a little older than you, a while ago. He didn't tell me that that was what was going on but I could tell he was nervous. Turns out I was the first person to suck his dick, ride his cock, and put anything up his ass ever! It definitely seemed like an important and positive experience for him, I think not knowing me and knowing he wasn't in an environment where I was going to judge his skill level took off the anxiety that had been impeding him in his 30 some years of life.
 
I would suggest that you let your escort know before hand for sure, not everyone is going to be down for that kind of experience, and you want to have someone without hang ups. Also when you are doing anything for the first time, let the other person take control at first and then try to follow their lead. A lot of newbies to kissing will just go all out with the tongue action, enjoy the pleasure of being kissed and having your mouth opened, and then when you are more relaxed you can return in kind. Gentle and slow is always preferable to frantic and fast IMHO.

Thanks for your input. I've actually found an escort who knows my entire situation. He is also highly reviewed. I think he will give me an amazing experience. I just have to wait for a good time to make an appointment with him.

Agreed, topping or bottoming aint for everyone, and Gays shouldnt be "shamed" for not liking or indulging in one or the other. Recently I've just discovered FTM Luke Hudson (not in the biblical sense) . I would be in heaven just sucking on his "cock" for hours...

I second the advice to book an extended date. Consider something that's part social and part sexual too. It's a guaranteed thing and might help you build the experience and confidence to transition from social settings to sexual settings in your personal life too moving forward. Plus it will probably help calm your nervousness and feel more natural.

Lol I'm so confused by the discrepancy between the title and the clarifying question in the OP. I can only guess that it makes no difference whether the escort in question is truly into older guys or is simply a good actor?
 

 
It confuses me why this question would be in the "as an escort" section then. Are you asking us to judge our own acting abilities? Why ask us if you don't care about whether we would TRULY rather be playing with older guys or not?
 
I'm not an older guy who's met with dozens of younger escorts, so I'm in no place to judge who "appears to be really happy" with older clients. But as an escort I can say for sure- older guys come in every shape, size, smell, and personality type just like everyone else. Even tho I'm someone who has zero hangups about sleeping with older men, it's completely impossible to state that I'd truly enjoy being with ANY older man. Chemistry determines that just like with anyone else.
 
But when chemistry fails... I'm a good actor too. Why? Because everyone (who treats me with respect) deserves to feel like the sexiest guy in my world when we are together.
 
I guess I'm in a unique position right now due to my FTM transition and hormone treatment where I look almost a decade younger than I am. Hence I'm able to provide a "young teen" (18? 19?) type of fantasy experience while maintaining the experience and wisdom of my 28 years. I'd say that's been going over very well so far... guess I'd better enjoy it while it lasts!

I'd much rather have a client over 50 than under 30. My partner is 56, so needless to say, I prefer the company of older men.

I am 55. All the guys I have recommended made me feel like they enjoyed my company.
 
Caveat: I am irresistibly charming.
http://25.media.tumblr.com/dc0c40c5a5aaa2b230aef3154d12d902/tumblr_mnauolZEig1re0f60o1_500.gif

I know this subject has been discussed before, with clients saying they are not really "that old", and escorts saying they love everybody (most likely to ensure business). But , as a matter of common sense, neither of these statements is always true. I have reached an age and "physical type" where a number of younger non-professional guys indicate they are interested in me---most of whom are sweet, but have few sexual skills. So, I am not asking which escorts really and truly would rather be playing with older guys, but which ones appear to be really happy with us, and leave us delighted with this particular older/younger experience.

Saw Dixon Wednesday night and would repeat. The other chat string has the details which I won't repeat here. https://www.masseurfinder.com/members/dixon33.shtml

There is a post on the next page, "411 on Big Black Muscles in NYC." You might start there. Or start looking in Masseurfinder or M4M. Of course, you should go with a recommendation here, and you're right to ask here.

https://www.companyofmen.org/threads/massage-by-m-nyc.127675/#post-1420236

Two things:
1) Put a condom in your wallet and leave it there for those moments when things "occur" with spontaneity. You'll never again have to say, we can't have sex because we don't have a condom. Most men that I know, have one with them permanently in their wallet.
 
2) You really need to understand that people with HIV are people. Real human beings. Sexy as fuck, annoying as hell, exciting, boring, but real and full of all of the same emotions as you. Maybe then, HIV won't be as terrifying, and, you can stop looking at someone and seeing the virus.
 
PrEP is a good thing and has its purposes. You and I have messaged back and forth and we've talked a lot about it, but the fear is something you should figure out how to get passed.
 
 
 

This is very unfair to him and to yourself. You have the knowledge and facts, from the CDC, from people with firsthand experience, etc... and still choose not to trust. That is very sad.

Get tested to put your mind at ease about your brief bottoming experience.
If the idea of medication side effects and long term effects concerns you, maybe drugs arent for you. Just go the condom route.
Fear is a basic human emotion. You can try to address your fear regardless of the protection method chosen.

Here's the thing, from my perspective. If you want to try again, and it sounds like you do, then you have to ask for some consideration for the unsatisfactory service from the second encounter.
 
If you don't ask, you will not be able to shrug it off and have a good time in the future with him. He may say yes or he may say no. That's his choice. His choice will lead you to your decision.
 
As for your tip on the second occasion, I gather that tip was about you, and not about him. You may have sent a confused message and that confused message is coming back to you now. Time to correct it.
 
Since he reached out to you, I'd suggest responding with a comment that says something like... "I appreciate the offer. I am a little hesitant because last time I felt we didn't connect and the session ended on a down note. I'd be open to considering another chance... make me an offer I can't refuse. *wink*"
 
That leaves it all in his court.

95% of the time I have a date, it all goes reasonably well and the agreements that we have made around payment and condom use get followed, 5% it does not. I understand all the feeling you talked about, when you work so hard to compromise with someone and make them feel like an experience is positive even when it seems like they're working against you every step of the way, and then they rip you off it kinda breaks my heart a little bit. I've been in the biz for a long time but I'm still kind of an optimist about humanity.
 
I usually write a text to them, knowing that I'm probably not going to ever see that money, and therefore just genuinely telling them how that experience made me feel and like speak my anger but also force them to see my humanity. When your job is so much about adjusting yourself to make other people feel good, being totally honest and straightforward can feel healing even if it doesn't return the cash. I wish you the best, sorry you had that experience.

As a top I've often run into a little bit of something but really, not to be crude, its about the texture of whats going on. Usually I'll just withdraw my hands, put on some gloves and no muss no fuss if its just little of something solid.
 
For myself, only like 10% of guys want to do anal and usually they let me know beforehand but if they don't sometimes I excuse myself to see what the situation is but lets be real a decent enema takes 30+ minutes and sometimes I just have to say I'm not sure about the weather and suggest we meet again.

Lol well I take comfort in knowing that trans guy sex robots will probably still be a ways down the track

95% of the time I have a date, it all goes reasonably well and the agreements that we have made around payment and condom use get followed, 5% it does not. I understand all the feeling you talked about, when you work so hard to compromise with someone and make them feel like an experience is positive even when it seems like they're working against you every step of the way, and then they rip you off it kinda breaks my heart a little bit. I've been in the biz for a long time but I'm still kind of an optimist about humanity.
 
I usually write a text to them, knowing that I'm probably not going to ever see that money, and therefore just genuinely telling them how that experience made me feel and like speak my anger but also force them to see my humanity. When your job is so much about adjusting yourself to make other people feel good, being totally honest and straightforward can feel healing even if it doesn't return the cash. I wish you the best, sorry you had that experience.

95% of the time I have a date, it all goes reasonably well and the agreements that we have made around payment and condom use get followed, 5% it does not. I understand all the feeling you talked about, when you work so hard to compromise with someone and make them feel like an experience is positive even when it seems like they're working against you every step of the way, and then they rip you off it kinda breaks my heart a little bit. I've been in the biz for a long time but I'm still kind of an optimist about humanity.
 
I usually write a text to them, knowing that I'm probably not going to ever see that money, and therefore just genuinely telling them how that experience made me feel and like speak my anger but also force them to see my humanity. When your job is so much about adjusting yourself to make other people feel good, being totally honest and straightforward can feel healing even if it doesn't return the cash. I wish you the best, sorry you had that experience.

My most difficult clients are the ones who haven't wanted to kiss, thank god its only been a few. Sometimes it has been guys that are just super shy or closeted, but often its an indicator of being dissociated in a way that leads to pretty bad sex I find. When people ask me what I'm into I always highlight kissing because if they're not into that I want them to self select themselves out.

My most difficult clients are the ones who haven't wanted to kiss, thank god its only been a few. Sometimes it has been guys that are just super shy or closeted, but often its an indicator of being dissociated in a way that leads to pretty bad sex I find. When people ask me what I'm into I always highlight kissing because if they're not into that I want them to self select themselves out.

Lol well I take comfort in knowing that trans guy sex robots will probably still be a ways down the track

I've been hired by several escorts - people who provide sexual care and attention focused on others want the opportunity to be selfish sometimes and what better way to experience than then hiring yourself?