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Crossdresser Masturbation Tips

Butt plugger
I love to rub my nipples and put a vibrating butt plug up my ass when I masturbate -- intense orgasm.

Wall banger
Lie with you legs up over you body (a wall is good to keep you propped up). Insert a dildo or something good for pleasuring your anus, and use the wall to push it in with the beat of your jerking hand, with your free hand pressing very hard behind you balls (between your balls and ass). It will feel intensely good. When you start to cum, press as hard as you can and push the dildo as far as it will go. You won't be able to control the pleasure you feel.

Stop 'n' go
Get yourself really hot and hard, and start having a good JO session. Lube your butt and a dildo up at the same time. Slowly work the dildo up your ass till it finds your prostate and start to massage it. Work your butt and your cock till you get to ""that point,"" then back off. Keep this up as long as you can...the stop and start method, and you will eventually explode with cum flying all over the place.

Girlfriend's panties do the trick
First, I get horny by reading stories just like these and looking at amateur pics. I then like to squeeze my nipples and sometimes put clothespins on them. I then begin to stroke my cock and apply lube to my ass. When I've relaxed I put a dildo into my ass. I like to look at nude and dirty photos of transsexuals and push the dildo further into my ass. My cock is now very big and red and I wank my cock while fucking my ass with the dildo and then cum into a pair of my girlfriend's panties.

Home alone
When I'm horny I go into my room and get naked, make sure no one is home, and get my dildo and put it up my ass and jack off. I like to swallow my cum as it shoots into my mouth.

Transsexual Conquest

A Transgender rocked my Sissy Butt

Then at some point she took off the condom and just started rubbing her dick on my hole. I started getting worked up and my body language must have sent her the signal that I did not mind bare backing. After a while, she had slid her raw, slick monster in my ass and started fucking me. I can honestly tell you that this was the best fuck of my life. I felt like I was in heaven. The huge piece of meat ramming my guts out. 

After a while she pulled it out and asked if I wanted to suck her. I told her not to wipe off her dick and immediately put my mouth on it. I sucked her for a few more minutes until she got rock hard and slid it up my ass again. She fucked me for a while ... then she whispered the sentence that I so desperately wanted to hear ... "Do you want to get bred by a tranny you slut?" Oh yeah, oh yeah, oh yeah I moaned in ecstasy. I wanted her cum deep down inside me. "Do you want it on your ass or inside, slut?" ... "Deep, as deep as you can get my mistress!" ... 

And then I felt her giant monster get even bigger and thicker as it swelled up inside my ass ... the walls of my inside were stretched to the limit and the sound of her balls slapping against my hot hole was driving both of us crazy. Finally, she shot a huge load inside me! It was so big that although she came deep inside my guts, it was still oozing out of my hole.