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1.
Three penises or objects that exemplify penises, such as dildos, in one anus.

It is physically possible to achieve naturally ( without the use of toys ) but has rarely been attempted in pornography, certainly not in the mainstream.

However, triple anal penetration with the use of two penises and one dildo has been done, notably by female porn star Sandra Romain, twice.
Cindy tried triple anal with her boyfriend and two dildos

Samantha had Frank and Derek sexually penetrate her anus at the same time, and also added a dildo into the mix

Somehow, some way, Jessica got three men to fit their erect penises into her anus all at once.
by Bill Abnovsky July 03, 2008
 
2.
The insertion of three penises or dildos, or either combined, into the anus simultaneously.

Has been performed once successfully on mainstream pornography by Sandra Romain in the hardcore flick "Tournante" aka Tournament of Sex. The camera angle is somewhat off, however for the brief period of time, it is one very hot position. mmm 3 cocks in 1 ass!
That whore of a bitch sandra romain did triple anal successfully!
by The Horny Guy October 03, 2009
 
3.
The term "Triple Anal" was originated in Birmingham, AL. When a sorry ass excuse of a guy that does web sites for t-shirts and beer swears that he caught his ex-wife in bed with 3 well-endowed african-american men. Yet after further research, it was discovered that in fact, HE was the one taking on the 3 african-american men and his wife discovered him in the comprising position. From that point on, it is permissible to insult somebody by saying that they enjoy "Triple Anal". Please refer to douche bag for more info.
Mike rather enjoys the partaking of the Triple Anal.
by Brad Reed March 16, 2007