Newbie here considering getting topped by a TS.  I'm considering Eva (in Chicago) but I'm a little intimidated.  Are hear that it can be painful and you could be sore for a few days.  Is that true?  Does it vary more by person or by amount of experience?

depends how queer you want to be, you might find it the best sex you've had in your life, on the other hand you might find it painful and .......your cherry will be busted,  and so may you

Lov2rim, if you do the penetration it won't hurt contrary to being penetrated.I'm a woman, I've been penetrated in that area, and I don't ever remember feeling so nervous. I prefer vaginal sex but I think it is a better orgasm for the man to insert himself in the other area.Is that why in the Koran it says a good muslim will have 10000 virgins when he dies?Do you men agree is vaginal sex second best?
   

Rhythmmanx, isn't penetration and or any kind of sex with anyone other than a man and woman queer per se. I hate to stereotype and or generalize but you made the statement.I'm just responding.

I think it all depends on your ability to relax and being with someone who will make that possible while taking things slowly.  Of course, you should also make sure that they are willing and able to top you.  Try to stick to girls who have been reviewed here.

If this is your first time with a TS, you may want to see her once and decide if you like her and see if she is able to help you relax without entering you.  Don't put too much pressure on yourself for your first TS experience.  It may be easier to relax with someone you have seen before.  Also, use an enema and shower before visiting so you won't be worried about cleanliness and any possible mess.

Many of the girls will advertise that they welcome beginners.  They will tend to be patient and take their time getting you accustomed to the new experience.  Even if they do not mention this in their ad, do tell them you are new to this, but want to try it.  

Still, relaxation is the key, specifically your sphincter muscle.  The soreness during the next few days will be minimal or non-existent if you can keep yourself from "clenching up" during the session.  When you reactively clamp down at the same moment she is stroking into you, it can be painful.  Either way, you will get over it within a few days.  You may even want to try using toys yourself to get used to it ahead of time.

Lastly, don't listen to the ignorant comment rhythmmanx made about "depends how queer you want to be".  Either he doesn't belong on the TS board because he just wants to bash someone who wants to try something new, or he does enjoy being with a TS but thinks he is different because he only tops them or performs oral with them.  What's the difference there?  It still involves a sexual act with someone who has a cock!

Enjoy and be safe!!

Soreness seems to depend on the Giver and the Givee,RELAXX is the key.When the moment arrives and you feel that cherry bust,just go into another mental 'world' and live with the fantasy.Within a few moments everything just happens naturally.Hopefully you will pick one that knows when to nail it and when to ease it.Hope it goes well for ya and do remember to let us here know how it went.

What do you mean by that?  It sounds painful and bloody.