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My Sissy Boyfriend

Sissies ass fucked with strapon cocks.

My Sissy Boyfriend
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Site quality3.5
Update frequency4.5
Site usability3.5
Content amount3.5
User rating *4.0
Overall rating4.0
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My Sissy Boyfriend Overview

A sissy is a little different than a shemale. A sissy is a boy dressing as a girl and not really trying to go all the way to female. The sissy likes people knowing he's a boy underneath it all. He likes dressing in the women's clothing but maintaining some of his maleness beyond his cock. Sissies are almost always submissive too. They like to bottom and they like to be humiliated. My Sissy Boyfriend is a pretty good example of this type of content as the boys are dominated, humiliated and strapon fucked.

My Sissy Boyfriend is about glamorous girls taking sissy boys, bending them over and fucking them in the ass with strapon cocks. The tour is a good resource for free pictures and videos if you want a sample. The streaming trailers are the best part of the action and they show some pretty intense and awesome sex. They also demonstrate just how sissy these boys are going to be. They're really convincing so it will be fun to watch them get hammered.

Members Area of the My Sissy Boyfriend Site

My Sissy Boyfriend adds a new content set every 1-2 weeks with most updates coming on a weekly basis. You can see the dates and the new scenes on the updates page or just go right to the pictures or videos, depending on your preference. The images are high resolution and can be downloaded in a zip file. They use a Flash browsing system for the thumbnailed galleries that I'm not fond of but that's life. There are 14 image sets. They also have 28 videos and they can only be played in browser. They come in three resolutions and the Flash player works well but there are no downloads and that's just awful.
Members area of My Sissy Boyfriend #1
members area screenshot #1
Members area of My Sissy Boyfriend #2
members area screenshot #2

There are a couple of things I really like about My Sissy Boyfriend. The girls are the first thing. Over and over I was looking through the pictures and watching the videos and noticing how they were consistently making the girls look really glamorous. I love that! It's really a mix of glam and sluttiness and that works really well. They're done with perfect hair, sexy makeup and they're usually wearing something sexy. The sissies are the other excellent part. These cute boys are slim and a little bit feminine to begin with and then they go all out to transform. They wear skirts and dresses and lingerie, they put on heavy makeup, they wear wigs and they put on high heels to make their asses look great. Most scenes have a bit of sissy transformation too.

It's the strapon sex that doesn't really work. In many scenes the guys can't take much penetration and the strapon harness is cheap so it makes thrusting hard. The girl will get the dildo in there and when she goes to thrust the harness will simply pull away from her body because the guy is so tight. That means little penetration action. It's kind of boring to watch. Given that I would recommend you join another site for strapon sex and stick with this one if you want the sissy action.

There are three bonus sites listed with My Sissy Boyfriend and two of them are currently working. One features mature chicks getting fucked by young guys and the other features mature chicks having lesbian sex with teens. The third bonus site features sissies getting fucked by guys and I assume that it will launch at some point so you can probably count on that. If you like those sites it obviously improves on the value of this one.


My Sissy Boyfriend is a hit and miss experience. The girls in the scenes are glamorous, confident and hugely sexy. The guys are turned into sissies with ease and they look convincing. It's a lot of fun to watch them get dressed and put on their makeup. The videos can't be downloaded though and it's hard to justify that in the modern world of porn where everything is downloadable. The strapon sex is largely lousy, too. There isn't much penetration and when there is they don't show you much of it. It's about the sissies here, not so much the sex. There's some value but it's hindered by the non-downloadable scenes.

PS. If you are looking for more information about My Sissy Boyfriend you can read other My Sissy Boyfriend Review

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