3 day trial: $1.85 | 1 month: $29.99

This hilarious three-year-old site is the place where “straight guys get tricked and trannies get dicked.” It is based on everyone’s favorite surprise – the guy who lifts up a woman’s skirt to find instead a monster cock waiting for him or her. Of course at first the guy who is being tricked is reluctant and really is not into the tranny but after being convinced or wrestled down by the She Male he is sucking cock or taking it up the ass like an old gay granny.
If you like nasty sex then this is the tranny site for you. There is no soft introductory stuff or wasting of time. The video content is pure ass slamming and fisting so it is not for those who like sex with their trannies to be tender (like it might be with a real woman.) The videos on Tranny Trouble are strictly Rough Trade!
One problem with this site is that the content does seem a little slim for the price. There were less than twenty videos at the time of writing (August 2006) and also the content is not dated so it is hard to say how often it is truly updated. The exclusive photo content is equally slim but each portfolio does have about 100 photographs in it.
The videos are downloadable in both QuickTime and Windows Media Player. You can view them as a download or as streamed. You can also download the full-length version of these videos, which is usually about 35 minutes long. Each video is broken down into roughly seven minute long video clips. Just a tip - to download the movies or the videos, you will have to click to stream them first and then choose the download option if you want to save it (which is a bit of an unusual way of doing it.)
The picture opens in a separate window and you are given the option to save the video on your computer. The good news is that there is not a download limit on this material. There is also no copyright limit on it however all of the videos do contain a small watermark that does not interfere with your viewing experience.
Along with your membership to Tranny Trouble you also get access to fifteen exclusive bonus sites including Gay Hitchhiker (that features a gay guy cruising the highways for cocks to suck), Suck Me Bitch (which features slutty looking women giving blowjobs) and Latina Sex (that features Spanish hos sucking and fucking.) Surprisingly only Gay Hitchhiker is a gay site among the fifteen bonus sites. The rest cover all kinds of genres such as plus size women, foot erotica and masturbating women.
You also get over sixty other sites with non-exclusive content that are part of the RAW XXX porn site network. These bonus sites do include some tranny sites such as Transexualz and Shocking Cocks. Both of these sites have a similar premise to Tranny Trouble – basically a young man is completely surprised by the cock he finds under the gorgeous woman’s skirt. The rest of the sites are not necessarily gay but are pretty kinky. Included as part of the Raw XXX bonuses are Squirting Chicks (about women who can ejaculate a couple of feet across the room), Grande Girls (about plus size women who like to seduce skinny men) and Foot Erotica (which of course is about the love of feet.)
At times this site offers a trial membership that is easily one of the cheapest trials on the net (under two dollars) so it is worth checking back to the site every now and then to see if it is being offered. Keep in mind though that this trial membership will only offer you limited access to content.

