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Crossdresser First Time Anal Advice

New crossdresser looking for advice, kink & fun
Shy, closet crossdresser, looking to experience gentle anal play for the first time.
part time crossdresser with a nice round ass looking for that special someone to take my anal cherry
funny, outgoing, intelligent, adventureous(obviously), spur of the moment couple who love to have a great time. we are very open and honest people. jorge will go out of his way help anyone in almost any situation from technical advice to relationship problems. Bella loves to listen and gives as much advice as she can to make things better. emotionally we are very happy together and very open to each other's needs.
crossdresser that enjoys top men and top women. I can perform oral and I like anal as well from both males and females. I am happy to be anally penetrated by a good man or a woman with a strapon, or even with another crossdresser that is a top.
I am a really down to earth person. I love to give advice and recieve advice.
Hello Stuck:

I see your post is from May, I am wondering if you have had your first anal encounter. WantaFirst, there are several good forum posts on this subject. One is Anal Cleansing in the Personal Advice Section. Another is Anal Hurts- Help Please ( or something along those lines) also in the Personal Advice category.

If you type Anal or Anal Advice in the search it brings up a crap load (pun badly intended) of posts about folks seeking anal. I found if you type in Lubrication, it brings up more Anal Advice topics.

I found several of the posts helpful. The concensus is to clean up, lube up, cover up (condom), ass up, relax and get to it.

Connie97 makes some great points. A water based lube is important especially if you are using a condom since petroleum based lubricants, like vasaline will disintegrate latex or other condom materials. Too much soap or too high of a concentration of vinegar will dry you out. Connie97's advice about having your partner take a piss inside is tricky if you are using a condom. I gusess you'd call that a golden enema.

There is a good deal of experience from many of the folks here and some great forum posts on the subject, but it will take a bit of search and click to find them.

Good luck and I hope you'll share your experience when it does happen.

Have fun...A
Wow!I first learned the do's and dont's of anal pleasure from sex magazine advice column, you definately have to relax at the start and if your mind isn't into it the your body doesnt want it and you will tense up,i watch a lot of anal videos,i like to watch it makes so horny,i have yet to see up close anal.my ex was my first everything so he would be my first anal,but only twice b-cause he was at least 11" and that was just to much for me,i eventually did myself after a day of self pleasure,i find that no more than 7 and half is all im willing to take.Lubrication is so helpful it actually shortens the ow! moment,also if you get really into the sex you will automatically relax,my boyfriend now is perfect so ive even learned new positions,i just have to learn not to want anal all the time(which is why i watch the videos).Enjoy,tip:if you controll the actual act you can go at your own pace.ooh!yeah!
I'm 64 and widower for 13. I was wondering if there might be someone(s) who may be interested in the same things. A m-f(s)relationship/fwb, nothing serious. I prefer caucasian or asian women. A first time m-f female(s)pegging. A first time m-m(s) friendship in which I would like to stroke, suck, maybe anal. Nice size, maybe 8+, cut white cock. I am limp. A pretty transwoman(women) with nice, cut, white cock maybe 8+. A pretty crossdresser, 8+, white, I would give oral and receive anal. A white couple with bi-male to give oral to 8+, cut. Maybe anal and giving f oral or pleasing her. Not asking too much. Right?
Had a nice time last night. Gave my husband a very intense orgasm, using a vibrating anal toy, and bj, at the same time.. First time serious anal play, for my man. His orgasm was explosive! I read through alot of the advice and tips section, among other topics, and tried to follow up on all that I'd read. I was amazed at the amount of ejaculate he spurted! Usually, he doesn't have that much, and this time, I got it thrown in my face, which was OH SO HAWT! Now, if I could play with his ass, while another woman is sucking him off, I think I'd have a gushing climax, myself! Last night, I was concentrating so much on giving him pleasure, that I ignored myself. And, that's all right too. I was all too happy to see him enjoy himself. :-D
Hey there, Ali speaking.

I got a question for all of you lovely BP people out there. Seeing as Vince has recently came out as bi, he hasn't had any real experience with another guy..... including sex. And seeing as we just bought ourselves a strap on, (it isn't here yet:(), I was wondering if anyone out there has any tips on first time anal sex. I mean, we have done it on me before, but this is also a question for when we actually do find a guy. Also, any advice for him on giving head will help too. Again, I do it, but advice from more than one person can't hurt. He has given a blow job before, but that was like 10 years ago. So like I said, any help, tips, advice, or even stories of experiences you have had will help. Thanks!

Peace Love Hugs and Kisses

Ali aka Saylenia

"If I wasn't for the gutter, my mind would be homeless."
"If you want to win the lottery, buy a ticket."
I was wondering if anyone had any advice for first time anal sex. It has been something that I quite frankly until recently have been hesitant to try. I finally let a guy rim me and omfg was it good. Not when I am really turned on I almost get an ach when I want to be fucked. Does it really hurt the first time, if so how bad? What doi need to do to prepare myself for it?
Thanks

Interests:

Anal Cream Pies
my wife doesnt like receiving anal.so the only time i get to eat anal pies is out of mens asses or when we're with a couple where the lady likes anal. and i love to be filled with cum and have it tongued and sucked from my hole
Anal Play Man And Woman
Los Angeles - San Fernando Valley - Bi - Crossdresser Seeking MMF Anal Play! Flower
Drug Sex
Very hot, extremely anal crossdresser. Looking for strictly tops that like to smoke meth & have their clocks sucked until they explode in my mouth. Then you can fuck my tight, round ass all night until you fill it with hot cum...
Anal Stretching
Wow LOVE these posts. For some reason - don't know why, I've always loved the idea of being opened up really far. The fist for me is the ultimate turn on but I have no idea how to get my ass that stretched. I'm married and my wife thinks anything anal is dirty. We used to be swingers at NW in Lynnwood and that was fantastic, she got to eat and play with girls but I was never allowed to play with the boys :( How do I convince her to let me have some cock too and how do I get her to help me get my ass open enough for her fist. (I wish) Any advice would really be appreciated. Tony
Anal Beads
My GF used a set of anal beads one time we got together and it was great!!! We have been having a lot of fun exploring anal sex.
Anal Fisting
We have suceeded in this catagory and do it on a regular bases. Maybe I had better clerify I ( Donye ) Fist Kevyn's ass on a regular basses and it is quit invigerating and I do not know how to explain it but he has suck large and numerous orgasms from that it makes also have them myself while performing this act on him. The only advice I can give any one is just take your time and use lots of lube and eventually it just happens naturally. In time your partner will learn how to relax and just open up easier and allow the process to happen quicker and with less restricions. Also to let you know if you do not succeed in say half hour or less quit and try again latter. I have found that after that amount of time has elapassed it will very discomforting to them . Not to painfull.:-D

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peregrine
Thanks for the welcome & advice on how to maximize my experience with your site, which, by the way, is pretty damn awesome & very easy to navigate.