Sounds like you could be talking about potential sex addiction (no judgment) which is an entirely different topic. I like bottoming because I can “top” any time I want without having to fork over roses. I like the power exchange and the physical sensation obviously. If it was cheaper or around the same price I’d also do this with cis providers who peg, but that is significantly more expensive and a lot want you to bring your own strap on as well.

As for my early bottoming adventures, the only things I regret are not doing enough research beforehand to properly enjoy it, and not taking into consideration the “size” of the girls. If you are interested learn how to properly prepare (more than just cleaning out, stretching too) and don’t go for the hung/dominant girls right out of the gate. If you go into your first bottoming experience with what you just described you will likely not enjoy it and could potentially even hurt yourself.

Yea I would say sex addiction is definitely a struggle for me, I typically don't do nothing for about a month or so till I get the itch to have a great release and when I do it definitely reignites the desire to have fun again in the following week or 2 until I fight the urge off but I'm single no kids no responsibility it's kind of a fun thing for me but then always a trap of addiction like you said the bottom part I guess is just the curiosity of reading reviews from others about the feeling they get from it

I love it. I’m heterosexual but giving in and being fucked by a TS is a turn on for me. My O is fantastic and the afterglow is excellent. The girl I see regularly also has an O. Nothing better.

Technically, the first time I "bottomed" was with a GG who was INTENSELY kinky, with a shit ton of ropes, gadgets, all sorts of equipment (TER: 138109 - I'm reasonably sure she's long retired) and when she mentioned "strapon" I kind of said, "Ummm ... okay, I'll TRY it" and it was indeed an intense experience, but I didn't think I was going to repeat it.  (I saw her again some months later, but kept it as a strictly GFE type encounter, and she was truly lovely at that.)

But the whole pegging experience lingered in my mind.  Sometime some months or years after that, I stumbled into some porn video of some fine TS lady stroking her cock - that was all, just a brief clip of some well endowed lady stroking a hardon, and it had me utterly fascinated.  The lingering thoughts slowly turned into obsession.

When I finally did get a woman with a big hard cock to do me it was yet again more of a freaky experience than one of sexual pleasure.  I walked/drove away from that encounter thinking, "Holy Shit!  What did I just DO???"  (I think maybe I would have just "liked" it more had she been of average endowment, and this gal was pretty aggressive - she clearly liked to fuck!)  

But it had me hooked.  Gradually, I started seeing fewer and fewer GGs and more and more Trans ladies.  As time has gone on, I've shifted from versatility toward being 98% bottom.  Part of that is encroaching elderliness with attendant borderline ED and impotence, but also, I like the lady I'm paying to put in most of the work ☺.

The only time ive had any regret is way back before the prep came around. Always was super worried condom would leak or something of that sort.  

If there is something in life you want to do, do it. No sense in living vicariously if you dont have to.  

Addiction is only for the weak willed. If you want to stop, you will.

Take the time to learn the terminology... "do you regret being bottomed" should read; "do you regret being topped", or "do you regret bottoming"? To ask "do you regret being bottomed" is asking if they regret topping someone who bottomed for them. By learning the terminology you will less likely cause confusion if you decide to pull the trigger. If you've never had a girl friend finger you or use a toy on you and massage your prostate, you may also want to learn the pleasures that can be obtained via the prostate... Lastly, the thought you can't miss what you never had, is not accurate, Freud said we all covet what we see... Good luck!  

... though literally opposite. Sorta like "I couldn't care less." ... "I could care less."  Posts ate often syntax FUBAR. You have to read between the lines and even then you're not sure sometimes.

Honestly, everytime I tell myself “last time” but eventually find my self craving it then making the same choices. The girl (s) I usually see are amazing even though I only go once a year or so now days. In the mean time I usually just go to parlors for cis services.