Chessie Moore – The ultimate titfuck?

Ever since I asked “Anyone for a nice tit-wank?” in the earliest days of MyBoobSite, I’ve been in search of the pinnacle of boob sex; the champion of cleavage coitus; the master of mammary masturbation (ok, I’ll stop now). For a given example of the act to qualify for my top-notch titfuck toplist, the male participating in it would have to be brought to orgasm using the breasts alone – no handjob, no blowjob, no “cheating”. Sadly, in the ten months since I’d first blogged the exquisite art of tit-fucking, I was unable to find any examples that were taken “to completion”, as it were…until today, that is.

Earlier this month, I first blogged 44H Chessie Moore was back with a new website – ChessieXXX – and have been following its development ever since. New photo & video content is being added all the time, so I decided to take a perve at Ms. Moore in motion. And there, sandwiched between the gangbang groupsex extravaganza that is her “Hot Shots” series of videos, I happened upon my holy grail; the ultimate tit-fuck. Using only her H-cup breasts, her partner’s penis and a little baby oil for lubrication, she’s able to coax a copious cum-shot from his cock that cascades down her cleavage.

Now, THIS is what a tit-fuck should be; the ultimate pleasure to be bestowed between bountiful boobs. And so I present Chessie Moore from her all-new website, in what is by far the best example of breast sex I’ve encountered in the world of big tits porn to date:

Chessie Moore 44H from    Chessie Moore 44H from

Chessie Moore 44H from    Chessie Moore 44H from



44 thoughts on “Chessie Moore – The ultimate titfuck?”

  1. yeah thats a pretty good TF if ever there was one……is it my imagination or has chessie dropped a fair amount of weight? hard to tell in the clips.

  2. Heh heh – that looked pretty awkward but got the job done. Not sure if the oil made it too slippery for the guy. She needs to keep a scrunchie around to tie that hair back so as not to block the view of those massive tits.

    Nice vids.

    Probably would have been easier if he was on top and gave her a pearl necklace with his load. Reese – there’s gotta be tons of videos with that type of content in it. Or does that not qualify?

  3. BigBoobFan~

    If there is, I certainly haven’t found it. All of the “reasonable” titfuck vids (i.e. F-cup & up) I’ve come across thus far, even with the guy on top, still rely on a handjob or the bloke jacking himself off for the cumshot. If you’ve found any other examples of a genuine, unassisted big-tit-fuck orgasm, please let me know…as there’s always room for more contenders. ;~)

    ~Reese! :~)

  4. You’ve heard of Dawn’s place haven’t you? There is a video where she does the same, but it isn’t a very long video, sorry I don’t know the name of it since I no longer have the clip =(

    Good luck if you can be bothered finding it :P

  5. There used to be something trashy hot about her–you know, the woman mama would never let you go out with. She was hot, over the top big boobs and sexy lingerie and a desire to please you totally in ways nobody else would but then she just shot straight downhill. I don’t know why she was hot but she was. Too many boob jobs and too much culinary largess or something, not to mention a string of bad choices. Sort of feel sorry for her now. But she was hot in a clandestine way once…

  6. This woman was my DREAM GIRL back in the early-mid 1990s.

    Infact, besides Sarenna Lee, I DARE you to find a prettier face, and hotter body in all of porn. This woman had it all. Sure she is total white trash, and believe me it showed! Huge hair, poor make-up job, and not the best taste in clothing. But behind it all was one of the most attractive women in the history of the adult industry.

    In her prime, that body wsa absolutely SLAMMIN! There was one set of hers in particular where she was wearing this practically painted on, hot pink, one piece dress/skirt. Her hair and make-up wre flawless (obviously not done by her), and to this day I have yet to see a hotter photo of ANY porn star.

    Her breats were absolutely perfect. Hell, the doctor responsible for that work of art should receive a nobel prize for the job he did on her! Combine that stunning face, killer legs, and man made breasts, and you got yourself arguably (and cetainly in my opinion) the hottest porn star of the 1990s.

    She seemed to struggle with her weight as her career progressed, but I actually liked the extra padding in some of her later scenes. She was still fairly thin, and could still put herself in all those wondeful positions:

    Getting pounded in the rear while placing her legs behind her head! Classic, patented Chessie!

    But I consider these last few years a considerable fall from grace. Bottom line is she is happy with herself and that’s all that matters. But for me as a fan who used to worship her, the EXTREME weight gain, and big ass tattoos (especially that giant color flag on her breast… yuck) are just so unappealing.

    But, at least I have great memories… and a few classic mags and vid/DVDs!

    But no matter what, Chessie and Leanne Lovelace will always go down as my all time favs. :D

  7. What an incredible TF movie! Chessie plays the dream Mom in this flick, helping her “son” cum by fucking her awesome breasts. What makes this video so wonderful isn’t just her boobs or her boy’s big cock raming up and down, but the proud Motherly look on her face when he cums for her. All you guys out there with big titted Moms, should show her this so she’ll understand what you need.

    You know, you should run a contest page for your viewers to rank the top 10 TF vids.

  8. Oh yeah i liked Chessies Pix and Movies since the first time i saw them.
    Now she is such a dirty slut and even moore desirable!
    Keep on fuckin’ Chessie!!!
    Such a pitty that i live in Europe, loved to hug your tits.

  9. “All you guys out there with big titted Moms, should show her this so she’ll understand what you need.” — Mom Lover

    And my cock INSTANTLY shriveled up into my body. Thank you soooooo much for the incredibly disturbing post…

  10. Definitely an awkward position, but that’s what makes it fun I think. Also not a long distance thrusting event. He barely is able to move it back and forth just a little. But Reese’s Rule of 1) no hands, 2) no lips is kept and it truly is an orgasm brought on by big tits ONLY. Great clip. I once ordered a movie from S & H Prod (I think thats what it was called) entitled ‘Best of Titfucking.’ It contains 3 – 10 minute clips of some of the best scenes of the 90s (ok, some 80s too). There are a couple of scenes in there that would also qualify, but I think this is the best I’ve seen as far as the woman’s performance is concerned.

    Oh, Yes, Chessie rules. At least pre-tat Chessie. The Duchesse of Down and Dirty was one of my all time faves.

  11. “All you guys out there with big titted Moms, should show her this so she’ll understand what you need.”

    Sounds good to me. Big-tittied aunts and mother-in-laws too.

  12. Amazing video, btw. Chessie had the best titties, period.

    You should also find some good interracial titty fucking videos with black women and white men.

  13. “All you guys out there with big titted Moms, should show her this so she’ll understand what you need.”

    Thank you, K, for your support. A long time ago I came to “grips” with the fact that big titted Moms have a mission in life — to give their breasts to their sons, and anybody who wanted to be one!

    To Mad Dog, why do you think MILF’s are so popular!

    Time for to recognized BTMs!


    The whole thing with MILFs is that they are OTHER PEOPLE’S MOTHER’S!!!

    Not MY MOTHER!!!

    YUCK! Geez, now I have to take another shower… attracted to your own momma’s boobs… ACK!

    You sick, sick man! LOL! ;P

  15. I have no attraction to my own mom, but when I see women who look as good as Chessie does in this video, pleasuring their sons like this, it’s hot because of how taboo it is.

    Mom Lover, I’d like to email you at some point. If there’s anyway to get in touch with you, let me know.

  16. K understands — and so do BTMs! (BTW, K, post your email and I’ll be glad to contact you) I would have thought more of you guys who visit this blog would understand, too.

    BTMs (Big Titted Moms) are women with big tits (obviously) but more importantly, they understand the urgent, primeval, perhaps even biological need we have to suck and fuck those tits, and they are proud, loving, helpful, supportive, i.e. MOTHERLY, in offering their breasts to us.

    We all know how there are big titted women who didn’t get why us guys go crazy for their tits. But then there are those who encourage it. Like Chessie so clearly is in this video. “I think your getting the hang of it,” she tells her boy so encouragingly in video 2. Then in video 4, look at her face and smile, at how truly happy she is that her tits made him cum.

    It isn’t that BTMs are really your mother, Mad Dog, although as K notes, it is hot because it is so taboo. It is her attitude and personality in combination with her tits. A BTM wants to be your Big Titted Mother and help you like a son!

    Her ultimate satisfaction isn’t a coital orgasm — it’s helping her boy fuck her breasts and then cum on her chest! Just like Chessie!

  17. Absolutely superb vids. Chessie has superb tits and knows how to use them. As you say It’s rare to see an unassisted tit-fuck orgasm.
    I’d love to see some more classic Chessie along with some other greats like Tiffany Towers, Angelique and the not so often seen Dixie Bubbles.

  18. As I’ve said before, this is without a doubt, one of the best Big Titted Mommy tit-fuck videos I’ve ever seen. But you know what you need to also find for us, oh wonderful MyBooSite blogmaster? Videos showing Big Titted Moms feeding their boys suck her breasts while she jerks them off! I bet Chessie has got a good one just like that! K and I and the rest of the gang will love it and I’m sure Mad Dog will have something to complain about it.

  19. Gees he didn’t look like a blue collar worker at all! :>)

    But it was a real tit fuck. No hands, no sucking just tits and dick. And he came flowing down between her cleavage! Hmmm something to emulate I’m sure, but maybe with less oil(?)

  20. what the fuck is wrong with u mad dog Sarenna Lee do u know samantha anderson she is the number one bbw on the net right now and second one in my openion is ewa sonnet then eden then nadine but samantha is the number one check her out every one samantha anderson known as samantha 38g or busty samantha

  21. Good video. Chessie has great tits to fuck. I have titty fucked her on several occasions. Will be with her in december to do it again. Titty fucking her is better when she is on her back. That way you can cum in her face.

  22. yo mojo, does chessie…ahhh still take apointments like she used to say she did on her website? Just curious, no offense meant. She does look good in these clips. Better here than with the tattoos, but if she were offering me a ride in between them, no waay I’d refuse.

  23. Great titfucking scene, and a unique position, too! One of the better ones I’ve seen in awhile! It would have been nice if the guy in the movie did a little better job of acting like he’s actually DONE it before, but I guess I’d be nervous too, sliding my cock between Chessie’s enormous H-cups!!

    For anyone interested, there is a GREAT titfuck scene on the Bang Bros. website with Brandy Dean! The scene shows a guy sitting on a couch, and Brandy straddling his prick with her humongous knockers! The camera is situated behind his shoulder, so that it looks like it’s YOUR cock sliding up and down, between her huge tits….definetly a MUST-SEE!

    As far as my thoughts on Chessie Moore:

    Any straight, titfuck-loving guy out there would give his left nut, to have a women with Chessie Moore’s “endowments” pleasure him that way! Tell the truth now….if she gave you the chance, you’d fuck those bazookas, like your life depended on it!

    I know Chessie has picked up a LOT of weight the last few years, and I know she did some beastiality stuff, but I still think she always had a pretty face, and an incredibly dirty mind!

    I’ve been watching big-bust movies for years now, and I’ve seen some good tittyfuck scenes in my time, but in the early to mid 90’s, there wasn’t another cleavage in porn, I wanted to shaft worse!!

  24. I am also more a fan of the Chessie of old. One of my favorite scenes was watching her get it in all three holes at once…yeah it had been done by so many others, but Chessie was at the peak of her slutty and sultry ways with a killer voluptuous body. Seeing her fuck dogs was like watching Michael Jordan play baseball. No, I don’t like the flag tattoo on her breast, especially with G. Dub at the helm of our sinking ship. Would I fuck her today? Hell, yes, but I would rather have her lock her legs around her head for ol’ time’s sake and let me plow her well-used asshole until I shot my wad on those magnificent mammaries. And my favorite titfuck scene stars a then up-and-coming Rachel Love who is doing what is supposed to be a solo scene in a “buttman” type of video and she starts undressing the cameraman, stroking his cock amid his protests “Rachel, Rachel, Rachel, you can’t DO that!”,— “I’m just touching you like you were touching me”, she says innocently, then gets him off with her boobs in what looks like an unplanned, but still copious cum shot.

  25. Chessie still rocks. Not as much as she did a decade or a decade and a half ago, but if I were lucky enough to hit the lottery, she’d be one of the stops on Baz’s Big Hooter Sex tour.

    I’ve seen clips from the doggie vid, and while surely not my bag, no canines were in any way harmed in the making of that video; unless Fido’s a really good actor, pretending to enjoy it that much and all.

    The tats are very slightly bothersome, but the weight gain is okay as I’ve always liked busty BBWs.

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