Ah, a subject that I can 'get into'. I too enjoy anal play, but with a twist. You see, I am also a cross dresser, strictly for sexual pleasure. What I like to do is use an ejaculating dildo and a condom. I have this setup where the dildo has a long tube attached which attaches to an enema bag. So, I lay out the clothing I wish to wear. I then place the condom onto the dildo and insert the dildo into my anus. I then dress. I first put on a tight panty, usually satin. I follow that with a pair of support or control top pantyhose (maybe two pair). I love the confining feeling I get with tight under clothing. And my cock being confined is the best.
Then I simply finish anyway I wish with a bra, dress and slip, or slacks and a top. Sometimes I put on a girdle and stockings. The tube from the dildo runs up my back and out the neck of whatever I am wearing. I then fill the enema bag with warm water and connect to the tube. I now have a seamless and leak-proof system between the bag and the condom covered dildo in my ass. When I wish to feel filled up I raise the enema bag and allow the water to flow into the condom, creating a fantastic filled up feeling.
When I lower the bag the water flows back into the bag, depleting the water in the condom. I can raise the bag again and again, filling my rectum with warm water. All the while my cock is seeping pre-cum into the satin panties making them wet and slippery. Eventually I can touch myself, moving my cock around inside the panties, getting more and more excited. Finally, with one last rise of the bag I fill myself from behind and release from the front.
What's nice is that I can take a rest and start all over again. I have done this for up to 12 hours, and four climaxes, at a time on occasion. Cleanup is not all that much. I dispose of the condom, wash the dildo, panties and pantyhose and I'm ready for the next adventure.