My Sissy Boyfriend

If you've ever wanted to engage in a gender role-reversal with your female lover, then check out these sissification scenes. Especially if your idea of a good time involves watching hot babes penetrating their men with strapons before having the favor returned with a real dick. Unfortunately, the site isn't very big and they're just rotating the content.

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Will Peters

Update done by Will Peters

Published Nov 16, 2009 , updated on Mar 21, 2015

Pros and Cons

  • excellent-looking videos
  • exclusive content
  • everything's well organized
  • rotating content
  • streaming-only videos
  • can't post comments

When I logged into My Sissy Boyfriend, I fully expected to be met with a bunch of scenes featuring guys getting kicked around by angry riot girls hell-bent on humiliating them. Instead, the guys on this site not only retain their masculinity while dressing as women (think Buffalo Bill from "Silence of the Lambs"), they also lead a good deal of the action in the movies.

If you're into hardcore Femdom porn, you might be a bit let down with what you'll find on MySissyBoyfriend. Aside from the guys sucking dildos, getting fucked with strapons and wearing wigs, the male/female dynamic is pretty standard and the babes strive to please.

They appear to be rotating the content, though - even if the videos are dated as if new ones are added every two weeks, the amount hasn't changed since our last visit. You'll still only find 26 movies. On top of that hopefully you won't get too attached to the material because you can only stream these videos. If you can get past that, rest assured that the Flash streams are high in quality and you won't miss one detail of the action as it unfolds.

However, you can save the 14 high-res picture sets in Zip files. They really were crazy about their concept when they made this site. When you see the quality of the photography, you'll understand what I'm talking about. Who knows? These images just might be the factor that pushes your GF into the same kind of kinky role-reversal.

For the time being there are eight bonus sites and the bonus page indicates that more are on the way. There's another sissy site in the mix (although it's gay), as well as Matures Under Boys and the lesbian-themed Matures Fuck Teens. You can also check out some additional photos and flicks that cover diverse hardcore themes.

Bonuses are nice, but the rest of the sites in the network also have small collections that appear to be rotating. They really need to consider shooting more new scenes if they want anyone to stick around for more than a month. My Sissy Boyfriend isn't very big, doesn't appear to be growing and won't let you download the videos.

Latest Update

(done on Mar 21, 2015)

Since we did our last full review of the site on Nov 16, 2009

  • The site hasn't gotten any bigger, which isn't surprising considering that they rotate the content.

Members Area Screenshots

Membership includes 6 bonus sites

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Content and Stats

(as of Mar 21, 2015)

Site Membership

    • $29.95/30 days

Other Deals

    • $44.95/60 days
    • $59.95/90 days

Rating Score

  • Content Quality 15/15
  • Usability 4/10
  • Updates 0/10
  • Content Amount 5/15
  • Value 7/10
  • Unique Content 15/15
  • Video Downloads 0/5
  • Video Streaming 5/5
  • Features 3/5
  • Other Score 7/10
  • Rabbit Score: 61%

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