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My Sissy Boyfriend

My Sissy Boyfriend

Content quality: 22.0 of 25
Content quantity: 13.0 of 25
Design and usability: 7.0 of 10
Originality: 19.0 of 20
Reviewer's rating: 19.0 of 20

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Site Details:

My Sissy Boyfriend

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If by sissy boyfriend you understand those guys who love to wear ladies undies, stockings, bras and other accessories, then you already know what My Sissy Boyfriend is all about. Many women and many men love this. You must have an open mind for this niche and if you do you’ll surely find great satisfaction with this website. Perhaps the word sissy is harsh for some people but truth is, these guys are whinny, needy and they lack confidence, on top of it all they love to suck it and take it up the ass so I can’t think of a better use for this word. If you thought guys like these were just a few, think again!

Main idea:

My Sissy Boyfriend is made for ladies who don’t mind fucking their boyfriends and enjoy watching their faces as they suck their sex toys. Men who like to have their asses fucked while wearing women underwear, or maybe are just curious about it will also find this place entertaining. The tour is great and pleasant to the eye in terms of looks. Three pages packed with preview trailers and screenshots make me be pretty sure that once inside the content will be awesome and red hot!

Member's area:

Lots of black and red in the color palette is always a sure sign that we’re going to find a lot of kinky stuff. The main page of a site always offers the different areas to which you can access, this time there are 6 areas. They are the regular updates where you can find the latest 20, in this case it seems an update consists of a video and a picture set of the same scene, the picture and video areas, support and 2 more bonus areas. The site looks new and so far it has perfectly maintained its weekly dose of new content so there are no reasons to think the updates are going to slow their pace anytime soon.

In order to navigate the website you have a menu bar that makes it really simple to go through the different areas so you won’t get lost or find any difficulties in that point. The picture sets have an incredible flash player that enables you to do zoom, watch the set as a slide show or move through it manually, the movie section also has a flash video player that makes the whole viewing experience thing pleasant and comfortable.

The bonus zone offers 12 niches packed with huge picture sets that unfortunately can’t be downloaded in zip format so if you wanted them in your hard drive you have no choice but to download one image at a time. So far this area offers no bonus video at all but it seems that it will in the near future. With your membership you will have gained access to three more sites, all with the same nice look and feel. The place has clearly gained some points in easy navigation and presentation.


First thing you won’t like about the website is that it has very little content, only 14 picture sets. While it is true that the sets have descriptions and that they let you know the name of the actresses and even allow you to download the whole picture set in zip format, these guys can’t hide the fact that there are only 14 sets to watch. Maybe way too little for a site that costs $29,95 a month. Regarding videos the numbers go a little higher, but don’t get too excited just yet ‘because there are only 28 scenes.

It is in content quality and good looks that this site earns some points. The videos can be streamed n 3 qualities, Low, High and Ultra. The latter two are awesome and the sound is great too. All the scenes have at least a small plot and one thing that I think isn’t minor is the fact that these guys have taken the job of subtitling all the scenes. You will only be able to view the subtitles if you watch the scenes in High or Ultra Quality. It is really sad that they don’t let you download the movies, many users may find this point reason enough not to sign up. The content is completely exclusive, probably the main reason why they don’t allow video downloads and your membership is good for 3 bonus sites.

Despite all the negative things about the site, it really pulls off its fantasy. The videos are very well staged and the performances are great. There is nothing left to the imagination so if you like the stuff but are not convinced yet, I must say that I’m pretty sure you will have a very hard time trying to find something as good as this within the niche. Not only because of the models themselves who are all teens and smoking hot but also because there aren’t many sites offering this type of adult material out there.

Cons and pros:


  • Exclusive Content;
  • High picture and video quality;
  • Weekly updates.


  • Small Collection;
  • Stream-only Videos;
  • Bonus picture sets can’t be downloaded in zip format.

My Sissy Boyfriend offers you the chance to look at young teen babes whose boyfriends let them use make up and wigs on them and also fuck their asses with strap on dildos. All the pictures have excellent resolution and the movie galleries are of great quality. Presentation and navigation are the strong points of an exclusive content site that lacks the possibility of video downloads and which content whereas great is very little and leaves you wanting more. If they keep up with the updates and so far I’ve found no reasons to think otherwise, a one month’s membership for $29.95 looks like just the right price for this place.

Featured comments:

They claim they have good reasons not to let you download the videos but I simply find it unfair that a user would have to pay this much money and not be able to watch the videos from his hard drive.

It seems to me these guys are charging a little too much for the amount of content they are offering. I know it’s hard to put out stuff like this and that the guys behind this idea have made a great effort to present this material in a clear manner and within a site that looks great. But for the amount of content they have, I don’t feel like spending this much money in it is worth it, a little less would have done more justice.

Content exclusivity, ease of navigation and nice looks don’t come cheap. You want all that, you’re going to have to pay for it. The videos and the pictures are excellent so I recommend the site to anyone who likes the niche. I’m a happy member and I can say that my money’s been well spent and that I’ve no regrets at all.

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Last Update: 22 Sep, 2015

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