JourneysEnd

For guys breaking norms (and laws and in many cases marriage oaths) by hiring escorts many of you are — dare I say — awfully narrow minded and judgmental. 
 
@coriolis888that same woman speaking to her husband would have a few choice words to say to her husband about your activities, I imagine, if she only knew. Try and be a little more open minded, I invite you. 

Blacklists still exist, a few of them as invite only message boards. 
Mr Number has so little detailed info that I wouldn't consider it much of a resource. There's talk the app developer is going to change that in the next few updates. 
Bottom line, if you're screwing escorts over (or.worse), there are more than enough well-connected people on social media to warn others and pass along information. 
The last thing anyone wants is having their personal info put onto a feed that has 100k followers. 

I have mixed feeling about this topic. On one hand, I always wonder what my Mr. Number says about me, if anything at all. On the other hand, I have no reasons to believe that there might be anything negative said about me. I am for real, responsible, clean, a good tipper, respectful and punctual, so for all practical purposes I shouldn't need to worry about bad things said about me. The only less than ideal experiences I've had have been on the provider side's, mostly shady practices, like unprofessional behavior, inadequate facilities and being recorded without my permission.
Overall, if one is a good client, one should expect to have a good reputation.

There is no comprehensive, widely used, purpose-built platform. Mr Number is one of the closest things you will find and it’s dodgy, at best. Anything else we use we keep close to the vest, and for good reason. If you knew about it, it would defeat the purpose. Next topic.

Yeah, we’ve all been there. It’s a scam. 
In that situation I abruptly cut the appointment short and pay a prorated fee for the time used.
The provider is shown the door and then blacklisted in my book. 

I think a lot of these guys are petty and mean spirited. I’ve connected with Jason many times. Not only is he look better than his pictures but he is an amazing. Don’t listen to the petty reviews here. Spend time with Jason. You won’t regret it. 

Advice is usually free and frequently untaken.  Once cash comes into play, most people begin to see the end game.  No harm in warning people about scams but as long as all they are asking for I advice, I don't mind participating.  Curious bye nature, sorry if I mistook your post as advising him to be absolutely sure.  

I don't usually care about getting trolled in these cases. The poster may be fucking with us but the question and concerns are legit. If anything, there are dozens of lurkers on here who read this post and are in the exact same situation and the advice we all have posted help someone else. That's why I love these forums. 

I do not play a doctor on TV but I am one in real life..   If you want to be totally safe, continue to be abstinent.  If you want to be as safe as you can reasonably expect to be, start Prep for at least two weeks and be faithful about taking it.  Do not start it until you are sure you are going to proceed as there is no reason to subject yourself to potential side effects if you are not committed.  
As to finding a man, go to RentMen and go to the listings for your area or the largest area within a reasonable travel for a weekend.  Look at each of the photos and read the comments.  Once you have narrowed down the field, come here with a list and ask for recommendation.  I suggest looking at all the ads as you never know what might strike your fancy and if you use the checklist, that man may have been passed over. 
As to the event itself, the first time I met with a man, my story was very similar to yours.  It is not a unique tale, n fact, it is common enough to be considered mundane.  So once, I got to the hotel and the escort arrived,. it took a bit of encouragement to start to do anything and once I got started it took all the willpower I had to stop.  Did not get to anal on my first encounter, nor my second encounter, which took place the next night nor my third encounter, which came two days later.  I then arranged an overnight while I was away on a trip and I finally had the time and was relaxed enough to try anal, as a top.   Many many men later, I decided to try bottoming and found it was not for me.  It took about 5 encounters to even get to the point where I was actually entered.  Word to the wise, do not become inpatient and just blurt out "just push the fucking thing in". I got what I requested but not what I wanted when I did that.      
You may have very specific requirements for the men you want to see at this time, but that will change and broaden as time goes by.  So consider being a bit less specific about what the man looks like and more about what kind of person he is.  For most of us here, the intellectual connection more than compensates for any perceive physical traits that the person may be missing from you checklist.  
My best advice, as opposed to Curious ByNature, do not wait for the perfect man and the perfect time or you may find that there is no perfect man nor perfect time.  But once you start to appreciate and accept your desires, almost any time can be the perfect time and you just need to allow your partner to be the perfect man.  If not, move on to the next one.  

I blacked out midway through the op. 
Does anyone have a Cliff's Notes version available?
But seriously... This is the emailed information you send to the escort. Keep being specific and see what/who you end up with.
Trial & error means you're going to have to learn to take the good with the bad. 
And stop focusing on trying to prove your sexual partner is on PrEP. You're a big boy: It's on YOU to take care of you.
 
Best of luck 👍
 

Lots of good advice here. I wanted to add that my understanding is that PrEP takes a couple of weeks to become fully effective for anal sex, so having someone slip you one or two won’t work. As others have mentioned, talk to a medical professional about starting PrEP. For most people it also takes some getting used to. For me it took just a few days, but others it can take a bit longer. 
I’m not a doc, though I do have a lab coat for those who are into that kind of thing.  But talk to a real medical professional to get yourself ready for your adventures. 

You guys are cool as shit. Thank you.  Surfed Grindr, but I’m so much more attracted to the guys on escort sites,  and I think it would be best to have a professional handle this kind of situation. Thank you for all your advice, guys you were super great.
thank you. 

Congratulations of your evolving sense of self and your sexuality. Enjoy the ride. LOL
There's some great advice offered on this thread, especially around focusing your specific needs, and your own health and safety. I'd add a caution not to load too many expectations on any single encounter.  Enjoying sex with male partners is a skill you need to learn, just as you had to learn to be with women.  It doesn't come fully formed, and no encounter, paid or otherwise, is going to fulfill all your fantasies.  Arrange a meet, see it through, and learn what worked and didn't.  As the cliche goes, it a journey, not a destination.

44 is not old as fuck.

I'm confused. Could you be somewhat more specific about what you're looking for?
 
Just joking, of course. Adding to the excellent advice and insight already given, look at Rentmen ads, find someone who matches most of your physical requirements, then come back with questions about the prospective provider's expertise and reliability. Then contact the provider with a much abbreviated list of wants and wishes.
Or, as an on-the-edge alternative, and already mentioned, seek the counsel of a reputable sex therapist. Remember, you're not just looking for fulfilment of a sexual fantasy, you're also transitioning to a different expression of sexual identity. Remember, the largest sex organ is the brain, and getting that in good order might help best of all.

Welcome to the Company of Men, and your new adventure!  Wanted to reinforce the notion of unprotected sex and the education and precautions you will need before going down this road.  If you do not have a gay or gay friendly doctor, see one even if it's not your PCP.  Many major cities have a health clinic that specializes in the unique issues and needs of gay sex.   These clinics are just like any other doctor's office, there is no stigma to going there.  You may also seek these services via Telemedicine if you are not comfortable going in person or these services are not available where you live.  There are a handful of vaccines you will want in addition to PREP, also be aware there are one or more STIs for which there is no prevention or cure (Herpes for one).  
I'm not intending to dissuade you from the path you are on, you are meant to be here.  Just encouraging you to go down this path fully educated and protected.
Have fun!
Jack
 
 

I agree with much of the above. I would broaden your physical criteria a bit. Is uncut a must? How important is the age? A girthy cock is fun, but if you have never taken one of any size before, it’s wise to start with a medium size, nothing really long or particularly girthy. Once you try it, it’s easier for you to gauge what you can take and will enjoy the next time around.
Maybe you can get some of your wishlist, but since this is your first time, it’s going to be more important to find the RIGHT guy for the job - someone experienced, patient, and professional. Some of the 27 year olds you mention may be hot in a photo online, but many of them have short attention spans and even shorter patience for newbie clients, especially those with zero experience with adult men. Chemistry matters a hell of a lot more than how defined an abdominal muscle is or how flawless the skin is around his eyes. A 30yo+ man will most likely be your best bet, at least for your first time. You can always seek out others later that fit your wishlist more closely. It’s just a lot to put on a 20 something…and have to tick all of your other boxes too. Trust me, it will be more fun to hire those young studs after you know what you’re doing.
My recommendation: search providers in your area on RentMen that strike your fancy, but please don’t filter on looks alone. You need someone who looks good, but more importantly, someone who will do a fantastic job for you. With your short list, search the forums in the deli section and see what info you can find on any of your guys. Take your time. Ask questions. Read reviews. Based on what you find, you will likely be able to narrow down the list to a shorter one. Find the best matches for a first time experience. Let your other criteria go for now and consider it a bonus if the right providers tick your other boxes. Be flexible when they don’t.
Once you have that done, reach out to the few you selected stating that it’s your first time bottoming and that you want him to be patient with you. Assuming he’s good with that, ask about rates and any pertinent info like incall or outcall and any questions you have. Don’t be afraid to circle back while you inquire of others and shop around. Tell them you are considering hiring and will get back to them. That approach doesn’t leave them all hanging in the meantime.
Take responsibility for your own health. Whether hiring or hooking up, it’s up to you to assess your own risk tolerance and protect yourself. Talk to your doctor about PreP and get on it. Generics are covered on all basic health insurance plans. Condoms are a good safeguard for any STI, not just HIV. If you’re willing to use one, that is another way for you to take responsibility. You can’t outsource responsibility by putting it on a provider. Not only is this impractical, but impossible, for reasons already stated. If you don’t want to get on PreP or can’t, use a condom. If you want your bareback fantasy, get squared away health wise first. Again, your first time might be with a condom and that’s not the end of the world. You can have bb sex in subsequent hires if you like. Either way, be prepared and take responsibility.
I have been the first time for many a man older and younger. I know how to treat virgins and how to be patient and respectful and sensitive, and how to make it a special, meaningful, and memorable time. But I also know when to kick it up a notch once he’s feeling emotionally and physically comfortable. You won’t find that delicate balance on Grindr, and very few 20 somethings can handle such a task with the necessary care. 
When you are ready to hire, check out the forums here that discuss douching. It makes all the difference not having to second guess and worry about hygiene. Be confident. Be ready. Enjoy.

Not, sir, for as long as you live and breathe.
Your post is an erudite and polished Apologia, as good or better as some of the best I've ever encountered.
I am sorry for the lack of consideration you've experienced from others, and hope I did not join that company in my joking -and perhaps clumsy- attempt to explain the dichotomy in reports of interactions between you and actual or would-be clients. Your expression of a personal viewpoint and perspective is welcomed and appreciated.
To echo the above poster's sentiment, Bravo!

I concur without qualification.
 

Btw, I only posted te above because he just texted me to say he’s currently in Puerta Vallarta, so if you’re there check him out!

I’ve seen him many times, in nyc & Paris. He’s classically handsome, has a great body and is very sexy. Completely vers. A real gentleman.

Based on what you've written here, the date/time hasn't occurred yet. Therefore, the escort hasn't had the opportunity to either a) honor the playdate and give you a good time or b) cancel or flake on you. This might not be easy, but my suggestion is to avoid projecting the bad experience you had with a prior escort onto this escort. 

So he has blocked you on all social media.  Might I suggest from a mental health point of view to get some closure.  Write him an old fashioned letter.  You have been to his home and so ou probably know the address.  Write out whatever it is you want to say.  After it is done.  Rip that first one up and write the second one with all the initial hurt and anger diffused.  Mail it out and forget about it and him.  He may try to contract you and at that point you can make a decision of finality but I would say don't return to the scene of this crime after the closing letter.  

Why should it matter or concern you, as long as the provider delivers the desired experience you are looking for?

This is between a man and his own penis.  
 
Full stop.