I'm a hairy, small dick, morbidly obese, semi-virgin 35 year old guy.
Between my crippling social anxiety, zero self esteem, and OCD-ish fear that if I am near cum I'll get AIDS and die... I've only had a single sexual partner my entire life.
When I was 25 I was a 100% never been kissed virgin. I lost 75 lbs (315 to 240, currently 355), felt way better about myself, and sort of had a casual thing with a coworker where with lots of jerking and sucking, but no butt stuff because I was a scaredy cat. Then that guy moved away. I thought that he was the jumping off point to being normal, but I went back into my shell (and gained all my weight back).
I'm 35 now, certainly not getting any younger.
I finally have a real deal big boy job making adequate money.
I was thinking... Why don't I get my HPV vaccine, Hep A/C vaccine, PreP, and some Bluechew and just hire a prostitute so that I can get fucked by a human instead of a piece of plastic I sometimes stick up my butt while masturbating? I won't care what he thinks about my body because I'm literally paying him.
Then I thought - where do you even find a prostitute? There are escort sites, but they all seem to be in the city (I live in the suburbs about 25 miles away). What if I get caught and it's like the police? Do I need to rent a hotel room or have them come over my house? Can I just find a local, muscular, hot, college boy on Grindr and offer him like $500?
Maybe I should just lower my physical expectations and try to go on an actual date with someone in my age and league? How will I hide how incredibly anxious and awkward and inexperienced I am? I literally wouldn't fuck me.
Maybe I should just go to the 50+ year old guy on Grindr that's like 3000 ft away that has a bio that says he'll suck anybody. I wonder what kinds of STDs you can get from sucking dozens or hundreds of dicks?
Maybe I should get on Ozempic?
All that I know for sure is I want to do something.
I have paid for escorts before when I was insecure about being gay, my body, sex, etc. Usually they are very strict in regards to protection, so I didnt get any STD from them. I dont regret the times I did it, for me it was money well spent. I didnt do it a lot. Usually masturbation and self-play would be enough for me, but there were some times where I really needed to have some body contact. I would say, if you have the money to do it and it is something you really want to do, then just try it once. Maybe youll love it or maybe youll hate it.
On the other hand, you are being to harsh in yourself!! You have to learn to love yourself and work on the things that can be worked. I know its hard as F, but start small and keep doing it!
For me I don't even think the sex would be important, just having someone to touch me or even just cuddle.