So I finally did it, went to a versatile transgendered escort. A fantasy I've had for -years-. Seriously, one thing that gets me incredibly hot in the idea of a woman with a penis boinking me hard. I don't really watch porn since I can have a woman generally do what I can watch, but with a TS... well, most TS women outside of pornography want to be women and not really use their penis, I understand as well as respect that. However, this made finding a beautiful transgendered woman to fulfill my fantasy of being topped in real life was nearly impossible.

Thus, I turned to escorts. I tried one out, and then I realized something that I'd known as common sense before but somehow had forgotten; Porn lies. One of my favorite porn sites is TSSeduction. The previews alone can rev me up nicely. However, I didn't realize that the men on that page getting plowed by those beautiful women must have had to prepare ahead of time as when I had a woman with a 7-incher mount me I felt like I was being tortured. I have a very high threshold for pain, but inside my rear-end was not exactly a place I've had more than a few fingers in before.

The kind provider suggested I get some bigger toys and, well, stretch myself out. I have used one toy before, but it was apparently way too small compared to a real penis. I'm not exactly rich, so if I want to see a versatile TS provider then I'd like to be better prepared as half of what I wanted to do was be topped. Does anyone have any suggestions for a newbie to being mounted by a beautiful woman?

Thanks,

Jim

Get a bigger toy get used to it, providers usually over advertise so someone who is advertising 7 or 6, and also invest in an enema bag, the last item is key

I kind of had a feeling as I've measured myself and I'm about 7.5 inches and she was smaller than me. Anyway, what kind of toys are good? There are so many out there.
Enema bags, eh? I was hoping I could just fast the day before, but I probably really should do an enema (they're supposed to be healthy at the least).
Thanks

PS - To clarify, I was planning on taking her suggestions. I was just hoping some people had some specific advice, like specific types of toys, or even specific toys themselves.

I tell my lovers NOT to fast the day before...you'll need your energy...haha...seriously, best not to eat a few hours prior, but to do the enema and practice your enemas...practice makes perfect...not everyone is in tune with their bodies and a proper enema should never be rushed

when it comes to toys...I say nothing bigger than 6" inches to start and not too thick...no-one wants to feel like they are throwing a hot dog down a hallway...haha...6" is good because it will train you nicely and if the TOP is bigger, it will still be hot to be "opened up" and feel your hole give into the intense pleasure of taking something that is a challenge

also try using non porous toys like silicone, glass or metal...silicone is my favorite to train my lovers' holes...most realistic feeling, doesn't burn(like some odor holding plastic/rubber/"jelly" toys) and easier to disinfect

I have vitamins and energy-types of things I can take in lieu of food that let me fast fine and actually be healthier and more energetic for the day, though doing it for more than a few days wouldn't be good, lol.

I'll make sure to do some enema work and do one the day before I meet with her next time. Should I start off with a 6" or smaller and build up to it? I also worry about damaging my exit-hole if I do things too frequently with it.

Thanks for the tips, I'll look into those types of materials now

If you really want to get into the joys of being a bottom, then get some anal plugs. Different sizes. Start out with a small one. Put it in and leave it in for as long as you can. I have one that I wear out in public. Nobody knows, of course, but the thrill of walking around and feeling it stretching your ass is awesome. Once you get used to a small one, move up to a larger one. Keep moving up in size until, you feel you are ready. I am at the point where I can handle being mounted by anyone and there is no pain at all. Just pure pleasure. Getting mounted can be addicting...

There is always the option of using toys with your GF/wife. A lot of women really enjoy pegging their guy anyway. You can use the same approach as the plugs. Start out with smaller ones and work your way up.  

I wound up going with some Aneros toys since they seem to be fun to use alone and by themselves. It's pretty easy for me to get a gal, though a gal I'd meet in a regular circumstance may not be as open to this sort of thing. I suppose I could go to a fetish escort to prepare for the versatile experience I've fantasized about. Who know, I may find a new source of fun times!

2012 was my year to take the plunge too.  It's been great - I did not experience the pain you described.
All the suggestions you've received are correct! Here has been my experience:
I started with a 5" butt plug and was surprised how quickly I got use to it. Tried 2 other larger dildos and got comfortable with those. Settled on a reasonable 6.5" dildo that I use once or twice a week.
I can't walk around with a dildo in. I get hard and stay hard with one in me.
Fleet Enemas have worked great for me. You don't need any gear and you can buy them anywhere. I usually use 2 bottles, about an hour apart. I take my time, and so far so good. Take a nice long shower after the second one.
Choose the right girl and have fun!

I went to several providers and while there was pain involved I found that the important thing is to relax and have a skilled provider.
I never used a plug. I assume sex is initially painful for all virgins but that is part of the initiation.
Now I have a provider who knows exactly how to top me and it is great.
Practice makes perfect.

So what's your idea of a well conducted enema? I use a streem master and I used to find the procedure arduous until I realized that using a slow flow of water and gradual filling worked best for me. Sitting on the john after I learned, after years of doing it wrong, was that not straining but instead just relaxing and rocking back and forth gently cleaned me out with much less effort than before.