Transsexual Babysitters in order

What happens when the babysitter shows up and she's even hotter than you dreamed... and she's looking at you like she's ready to screw? You go for it! But there's something you didn't count on: she's got a cock bigger than yours! This is a collection of films in the Transsexual Babysitters series released by Devil's Films. 29 films, 52h 54m in all, in release order.

Transsexual Babysitters
2006
What happens when the babysitter shows up and she's even hotter than you dreamed... and she's looking at you like she's ready to screw? You go for it! But there's something you didn't count on: she's got a cock bigger than yours! Don't worry, you're just in for some ball-draining tranny madness, so whip it out and get it up! We've got four of the most beautiful transsexual tramps ever, including fabulous covergirl Danielle, and they love sucking dicks almost as much as having you suck theirs. And when it cums to ass-fucking, you're in for a raunchy, jizz drenched night in Tranny Town! Maybe you can even drive her home!
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Transsexual Babysitters 2
2007
She's there to help out while you're away but what if she's not a she? What if this gorgeous chick as a dick bigger than yours and it's getting harder and harder. You know... just begging to be stoked and sucked. Would you make your excuses and try 'her' out? Would you like to see what it's like to screw (and get screwed by) a Tranny? Here's you chance to see for yourself... watch beautiful Vanity and her awesome Tranny sluts show you what it's like on the really nasty side!
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Transsexual Babysitters 3
2007 · 130 min
So the new babysitter wants you to check her out, in private! And when she shows up, dude- she's HOT! Sexy face, big tits, and a killer ass... and she WANTS IT! But before you get your dick out, she's got HERS out! Yep, you've got a tranny for the night, so get ready to get your dick sucked. Then you get to suck hers. And she'll want to slide her big cock up your tight ass, but get ready for the big screw, because she wants your big load deep inside her aching butt. Awesome, and how about tomorrow?
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Transsexual Babysitters 4
2007 · 127 min
What if a babysitter shows up and she was really fucking gorgeous? Looks like you're gonna be late for dinner, but you're also in for a surprise—because she's not a chick, this babysitter's a TRANNY! Sure you'll love fondling those big swaying tits, but when you get between her legs you're going to find a big hard cock! Go ahead dude, suck 'her' cock, because she's sure going to suck yours! And wait 'til you feel 'her' cock up your ass... Forget about dinner, you're about to enjoy a full course of the wildest sex imaginable, TRANNY BABYSITTER sex!!
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Transsexual Babysitters 5
2008 · 122 min
Now that you're getting a little bit older and wiser you should probably settle down and forget about all those crazy years when you'd fuck anything that walked... Right? WRONG!! Now is the time to get really kinky! Hell, your uptight fat ass wife isn't giving you any. So instead of getting a typical cute young girl to be your babysitter, you get a Transsexual. Now that's kinky!! So when your friends ask if you're fucking the babysitter you can say, "No, the babysitter is fucking me!"
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Transsexual Babysitters 6
2008 · 120 min
So the new babysitter shows up and she's gorgeous! Suddenly your dinner date can wait, you gotta check this chick out instead. Buddy, are you in for a BIG surprise! This is no chick- she's a hot, horny and insatiable Tranny! And she wants you as much as you want her! So pull out your stiff dick while she grabs hers. Here CUMs a nasty night on the wild side! Who knows, maybe she's better than a chick!
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Transsexual Babysitters 7
2008 · 123 min
Boy, did I get a wrong number! The babysitter I called and hired for the night had to be the cutest chick I'd ever seen - with a body that started my balls boiling. So I thought I'd better check her out... behind locked doors. That's when she whipped out a big hard cock and said, "let's fuck!" So she sucked, I sucked, we both screwed and pumped out huge loads of hot cum. Never did go out to dinner that night!
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Transsexual Babysitters 8
2008 · 122 min
So I'm sitting at home alone and I hear the doorbell. I open it and there's the babysitter. I totally forgot that I promised to pay her today. Well I'm flat out of cash so I asked this little cutie if we can work something out. She says, "I've got something you can workout!". And the next thing you know, she pushes me inside, closes the door, grabs my crotch and says, "I'll show you mine if you show me yours". Immediately we both whip out our cocks! What?! Surprise! I had no idea this little fox had a dick, not to mention a big, beautiful one. I guess we CAN work something out.
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Transsexual Babysitters 9
2009 · 109 min
I was wondering who the agency was sending as tonight's baby sitter when I heard a knock on the door and in walked the most gorgeous chick I'd ever seen. Pretty, built, great ass and a look in her eyes that said "Fuck Me!" That's when I realized I was the one who needed babysitting! Then 'fuck me' she did, with one exception... her cock was bigger than mine! Some chick, eh? And after an all night, cum pumping Tranny sex-fest all I can sat is... I need more TRANSSEXUAL BABYSITTERS!
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Transsexual Babysitters 10
2009 · 129 min
If you need a baby sitter, and you have a dark, kinky desire for Trannies, then let us help you out. What you really need is a Tranny Babysitter. They're lousy babysitters, but that have beautiful, hard cocks!! When they walk through the door you'll realize you've made the right choice. These gorgeous Trannies are NOT shy to lift up their skirts and show you their big, throbbing dicks, and even less shy to sock them deep in your mouth and let you ass fuck their clean, tight asses. You can thank us later.
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Transsexual Babysitters 11
2010 · 120 min
Like peanut butter and jelly, we've combined two of the yummiest treats, Transsexuals and Babysitters! When you call these babysitters, you'd better get ready for a serious night of hardcore cock sucking and ass fucking the way only tight and hot transsexuals can deliver. They'll do thing you've only fantasized about and after they're done with your ass, you'll be the one who needs a babysitter!
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Transsexual Babysitters 12
2010 · 120 min
Some guys have a tit fetish, others a cock fetish, and some even have a babysitter fetish! Well we have put them all together and come up with Transsexual Babysitters!All your kinky fantasies rolled up into one unbelievable package. You're gonna be blown away at these hot, hot trannies and their ability to take care of your baby...and by baby we mean Cock!
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Transsexual Babysitters 13
2011 · 120 min
At the end of a hard wouldn't it be nice to have a beautiful Transsexual Babysitter to cum home to? They can rub your feet and beat your meat. So bring home plenty of bacon and get ready to cook all night.
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Transsexual Babysitters 14
2011 · 140 min
Hiring that transsexual babysitter was the greatest idea you've ever had. You come home after that long day at work and the babysitter helps you forget the stressful day. A little stroking, sucking, then some hardcore fucking. Unloading your cock in this hot tranny's ass is a great end to the work-day.
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Transsexual Babysitters 15
2011 · 134 min
Finding that tranny babysitter was the best idea you've ever had. You come home after that long day at work and the babysitter helps you forget the stressful day. A little stroking, sucking. then some hardcore fucking. Unloading your balls in this hot tranny's ass is a great end to a otherwise stressful day.
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Transsexual Babysitters 16
2011 · 129 min
Who knew that hiring a tranny had such extra benefits, a rock hard cock after a long day of work, some stress releasing ass thrusts and some nice oral cock massages! Man this is the best! I can't wait to cum home to my Transsexual Babysitter.
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Transsexual Babysitters 17
2011 · 120 min
I came home and the babysitter was looking extra hot! Gigantic tits and these lips that were aching for a sucking. I knew she wanted it since the day I hired her. So after all this time I got to fuck the sitter, even though she wipped out a hard cock I was ok with it and she was ok with me ramming her tight trannie Tush!
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Transsexual Babysitters 18
2011 · 121 min
It's tough searching for the right babysitter, they need to be reliable, trustworthy and most importantly... have a cock!! You need a babysitter that's going to watch your kids and then ride your fat cock until your pump your hot cum load all over their cute little Tranny face! It's the best part of watching your kids grow up!
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Transsexual Babysitters 19
2012 · 139 min
Hot and horny tranny babysitters will take care of everything. Forget about the kids, you're the one that needs attention. As soon as you get home, drop your pants, sit back and enjoy a nice, thorough cock sucking. And when you've had enough of that, you can fuck that tight tranny ass as long as you want. Hey, she works for you right?
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Transsexual Babysitters 20
2012 · 118 min
You and your wife just can't agree on a babysitter. She wants to use her friends babyistter, but you have other plans! This is your only chance to hire a Tranny Babysitter, fuck her when your wife isn't home and never tell her a thing. She would never suspect the babysitter has a dick, not to mention that you'll be fucking and sucking that Tranny cock every chance you get! And there'll be LOTS of chances!!
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Transsexual Babysitters 21
2012 · 119 min
You've decided to go ahead with your crazy plan to get a babysitter that has a cock! She'll be so cute that your wide will never suspect a thing. You'll get home early from work and you and your tranny babysitter will have a raunchy, kinky, hardcore fuck and suck session! Your only concern is... you hope your wife doesn't walk in just in time to hear you scream... "Fuck me harder!"
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Transsexual Babysitters 22
2013 · 121 min
You didn't really hire a Tranny babysitter to watch your kids, you hired her so you can feel her hard cock on your tongue and lips and watch as that big she-dick slides all the way in your puckered butthole! One of these hung tranny babysitters is all you'll ever need... until your wife finds out. Then you'll need a hung tranny lawyer!
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Transsexual Babysitters 23
2013 · 120 min
What could be better than a sexy sitter... a Trannie Babysitter! They make the best sitters, they get the kids tucked in bed on time and when I get home from a long day of overtime hours at work, she puts her rock hard cock into overdrive and earns herself a ride home!
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Transsexual Babysitters 24
2013 · 122 min
You have a Tranny fetish and you need a Babysitter! Well the perfect solution is a Transsexual Babysitter! Watch your kids for the day and drain your balls at night! And your wife thinks she's just a really nice girl!
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Transsexual Babysitters 25
2014 · 114 min
The going rate for these sexy, slutty tranny babysitters is a good hard fuck after the kids go to bed!
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Transsexual Babysitters 26
2014 · 120 min
Ever in need of a babysitter and she isn't what she seems? These babysitters are just that, hot as hell but also packing a big surprise with them, a nice juicy cock! Watch how these babysitters go the extra mile to get the job and will let you do anything you want to their hot ass bodies!
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Transsexual Babysitters 27
2015 · 103 min
These babysitters are in need of a job and will do about anything to impress. They are hiding a big secret though and aren't sure if their potential employer will like it. What are they hiding? They are hiding the fact they have a huge cock between their legs!!! Luckily for them their employers love the fact they have a nice piece of meat between their thighs and are willing enough to try it out!!
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Transsexual Babysitters 28
2016 · 112 min
The neighbors won't believe what's going on over here!
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Transsexual Babysitters 29
2022
These trans beauties are great at sitting...on cock! In their skimpy outfits that barely hide their perky tits and their growing bulges down below, these young girls turn on the charm and seduce older men into taking advantage of their special skills. They're everything a woman can be and much more!
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Frequently asked questions

What order should I watch Transsexual Babysitters in?

1. Transsexual Babysitters (2006), 2. Transsexual Babysitters 2 (2007), 3. Transsexual Babysitters 3 (2007), 4. Transsexual Babysitters 4 (2007), 5. Transsexual Babysitters 5 (2008), 6. Transsexual Babysitters 6 (2008), 7. Transsexual Babysitters 7 (2008), 8. Transsexual Babysitters 8 (2008), 9. Transsexual Babysitters 9 (2009), 10. Transsexual Babysitters 10 (2009), 11. Transsexual Babysitters 11 (2010), 12. Transsexual Babysitters 12 (2010), 13. Transsexual Babysitters 13 (2011), 14. Transsexual Babysitters 14 (2011), 15. Transsexual Babysitters 15 (2011), 16. Transsexual Babysitters 16 (2011), 17. Transsexual Babysitters 17 (2011), 18. Transsexual Babysitters 18 (2011), 19. Transsexual Babysitters 19 (2012), 20. Transsexual Babysitters 20 (2012), 21. Transsexual Babysitters 21 (2012), 22. Transsexual Babysitters 22 (2013), 23. Transsexual Babysitters 23 (2013), 24. Transsexual Babysitters 24 (2013), 25. Transsexual Babysitters 25 (2014), 26. Transsexual Babysitters 26 (2014), 27. Transsexual Babysitters 27 (2015), 28. Transsexual Babysitters 28 (2016), 29. Transsexual Babysitters 29 (2022).

How long does it take to watch all of Transsexual Babysitters?

About 52h 54m across 29 released films.

Do any Transsexual Babysitters films have post-credit scenes?

None are listed on TMDB.