Is this even doable?

[1sttimepop]

Hi everyone! 

I hope everyone is great. I’m a first-time poster and I wanna apologize in advance If this post violates any norms, rules, or is otherwise against the spirit of the sight.  

I’ll keep this as short as I can.  
I’m about 44-year-old, previously considered heterosexual, recently divorced male. I’ve always dated women and have exclusively had sexual contact with women.

 

However, when I was 13, before I ever touched a woman, I sucked a friend’s cock. A couple of timew.  And he sucked mine. But he only did me because I think he felt obligated. I like, really liked sucking his.  And I kind of bugged him, a couple times, to keep letting me do it.
 

Thing is though, and maybe this sounds weird and maybe I’m just repressed, but I’ve always really really loved cocks the idea of them, watching them ejaculate, the idea of sucking one… But I’ve never particularly liked men, or the whole, I don’t know, idea of gayness. Besides the fucking. And the sucking. Especially the sucking.  And, God, the fucking sounds divine. 
 

I joke, but not really, because after doing the fucking for 30 years, the idea of kicking back my feet and being the fuckee for once sounds really nice you know?

 

So that went on for a while, and it kinda repressed to during my marriage, occasionally masturbated to gay porn, but that was the extent of it. Then after my separation, I began getting high, more than I used to, and I discovered 2 things: the urge to suck cock had become nearly impressible, especially when I smoke, and it was not with a really dirty fantasy of getting fucked raw by a huge, thick, uncut, cock.

 

Yeah, pretty specific for a straight dude huh? I know  

 

For the record guys, I am not a troll acting out some idea of a stray guy goes gay fantasy.  Real dude here, with a real question that’s been troubling me for some time. 
 

Bottom, line, I wanna get laid. But what I don’t want I don’t think I can get in a bar, or even on Grindr or Scruff.

 

Basically, I’m picky as fuck. I’m a pretty good looking guy, 6”3’, all my teeth and shit, but 25 pounds are so bigger around the waist than I could be.

Also, I’m old as fuck did you see that?   44. I mean, if I’m being honest I’d love some 27 year-old to fuck me.  
 

 

And what my fantasy is is this:

Height doesn’t matter so much, but I definitely want to a gym body, a real stud you know? Not too big on the muscles but cut as fuck.  Lemgth I could truly care less about, but I want a girthy, thick cock, uncut with a mushroom head if possible, and while we’re fantasizing, they kind of cock that drips precum as soon as it gets hard; kinda dom, but not too dome, maybe into getting high too, but not a dealbreaker, Willing to be patient with/or even willing to fuck a virgin

 

Note: This one might not matter, because of my lifelong request to achieve the perfect prostate orgasm, I can now stick an unlubricated fire hydrant up my ass without grimacing.
 

Most of all — and I’m more than willing to show my very recent, full panel, all clean STI test — I also want somebody clean, somebody provably on prep, with mega mega bonus points if they know somebody who can slip me a dose or two of prep, aaaaaaaaaand — willing to fuck me raw. And cum inside me. And leave pretty much right after they cum inside me and not kiss me goodbye, … that’s about it. As far as requirements go, anyway.

 

Too much? Too much for Grindr anyway, right?  That’s why I came here. Do you guys think I could find an escort who would fit the bill?
 

Any advice, suggestions, or thoughts you had would really be appreciated!

[Luv2play]

Talk about going off the deep end. I think you need some advice but not sure you will get it here. Maybe I’m wrong. I’ll let someone else say. 

[Walt]

Pick the most important qualities to you. Simplify what you are looking for to a VERY concise list eliminating all the narrative and history. Go through the descriptions of possible providers, pick one, contact him and ask! If he says no, move on to the next one. If he says yes, either meet -- or come back to CoM for questions about that one specific guy.

The simpler the question the better the answer you will get on CoM.

 

[pubic_assistance]

2 hours ago, 1sttimepop said:

Too much for Grindr anyway, right?  That’s why I came here.

Definitely too much for a hook up.

Finding a patient 27 year old escort might be a challenge.

Might want to start with someone a little more seasoned ( over 30 ) with the maturity to guide you through a first time bottoming.

[+ jeezopete]

2 hours ago, 1sttimepop said:

Also, I’m old as fuck did you see that?   44.

Yeah, all of us too......  😜

[edinbrooklyn]

Yes, very doable. You might add to your list connecting with the guy at some fun level, even if it’s a mechanical hire. You can learn a lot from someone you might never see again.  In fact, it can be easier to open up knowing that’s the base case. 
 

Best of luck!

[Luv2play]

I saw 44 in the last century.😳

[SirBillybob]

Quietly and discreetly return the missing ‘hood fire hydrant to its rightful place and no charges will be laid.

Edited February 6 by SirBillybob

[+ azdr0710]

Hopefully, you didn't get wiped out in the divorce. Because you'll need to get ready to spend $300-500/hr on this. Definitely can be done, but stick with well-regarded providers that are 'approved' here in the forum. Don't do the Grindr thing. 

As said above, don't tell a provider any of your "how I got to this point in my life" stuff that we all just had to read(!!!). Just mention what you want discreetly, politely, and professionally. To-the-point. Stick with a pro. Decide if you want a "burner" phone for contact. Decide if you want to host or not. Read thru much of this forum for comments and cautions. 

[Guest]

29 minutes ago, azdr0710 said:

Stick with a pro.

Yep.

[Becket]

Wow you're off on an adventure for sure. I bet you can find a willing partner that will meet most of your requirements. Fair warning though. This little hobby of ours is kinda addictive. Bet you can't eat just one. Anyway, have a great time.

[CuriousByNature]

I've never met with anyone, and I'm several years older than you.  What immediately jumped out at me was the phrase "provably on PrEP" and "willing to slip (me) a dose".  I cannot stress enough that a person cannot rely 100% on another's declaration of health status or their reported use of PrEP - provable or otherwise.  Compliance with medication cannot be proven, so even if you are shown a prescription or a bottle of pills, you have NO way of knowing whether or not your partner is using the medication correctly or at all.  Your health is 100% your responsibility, and entrusting it to another is extremely risky.    But only you can decide how much risk you are willing to assume.  As for having a dose or two of PrEP slipped to you, that is also very unwise.  How would you know if you were even given PrEP?  Plus, these are medications that can have significant side effects, and should only be prescribed by a physician who can assess your compatibility with the meds.  It isn't like asking someone for an aspirin.  I cannot tell anyone what they should or should not do, but if you are not at the point where you can receive advice from your own doctor about this, I question whether or not you should be considering a meet-up, given that you've referred to the safety aspect as the most important consideration.   Not trying to be a wet blanket, but I wouldn't want you to jump into a situation you may regret afterwards without fully assessing the risks. 

[Simon Suraci]

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.

[+ JEC]

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

 

 

[Skip]

Call Axel Rodham , he works for prep, really nice guy, tell him what you want. He will deliver and fits your specs. Fly to NYC, check into a great hotel (Ritz Carlton overlooking the park) Enjoy, then take yourself to the Grill for dinner (by yourself if your insist) and reflect on what you've been missing.  

AxelRockham - Male Escort, Gay massage - New York City | Rent.Men

RENT.MEN

---

AxelRockham Gay Escort in New York City, New York, available for Gay Escorting. | Find all the best Male Escorts at Rent.Men

 

[wsc]

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.

Edited February 6 by wsc
grammer

[+ glutes]

Welcome back Kris Parr / Coolwave!

Make sure you don't have a "Disaster of an overnight".

Edited February 6 by glutes

[Your Man in Arlington]

15 hours ago, 1sttimepop said:

Also, I’m old as fuck did you see that?   44.

44 is not old as fuck.

[+ robear]

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.

[viewing ownly]

On 2/6/2024 at 2:16 AM, Skip said:

Call Axel Rodham , he works for prep, really nice guy, tell him what you want. He will deliver and fits your specs. Fly to NYC, check into a great hotel (Ritz Carlton overlooking the park) Enjoy, then take yourself to the Grill for dinner (by yourself if your insist) and reflect on what you've been missing.  

AxelRockham - Male Escort, Gay massage - New York City | Rent.Men

RENT.MEN

---

AxelRockham Gay Escort in New York City, New York, available for Gay Escorting. | Find all the best Male Escorts at Rent.Men

 

But......what are YOUR plans now going to be?!?

[1sttimepop]

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. 

[+ ThroatCummer]

Your post is awesome. Authentic and open and really well done. You came to the right place. 

What city are you in or near if you don't mind me asking? I know a lot of escorts and have a few names that could really really give you an amazing experience but hard to narrow down location wise.  The most important thing is to tell any potential escort that's what youre looking for. In fact, approach them, be respectful, don't waste their time, but ask nicely if they wouldn't mind reading this post and give them a link to it. 

Any escort worth their shit, if you approach them the right way, will spend two minutes to read this post and tell you they can help or pass. It's you being genuine and saying what you want or need -- and that's the entire point of escorts. It's a business and they can help. 

Good luck. Post back (or DM me) with your city, please. 

[nate_sf]

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. 

[+ BenjaminNicholas]

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 👍

 

Edited February 10 by BenjaminNicholas

[+ purplekow]

 

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.