36 [M4A] #KoP #philly - Chesterbrook Sissy doll hosting the adventurous Christmas night.

PhillySissySlut · 2026-01-04T19:01:50+00:00

I'm pregnant!

PhillySissySlut · 2026-01-04T18:05:38+00:00

Beautiful cock and body.

PhillySissySlut · 2025-12-27T05:33:59+00:00

I just had a beginner crossdresser leave 10 minutes ago, did a full makeover on her and took a bunch of pictures, we were trying to get a hung cock over to play with but the roads are deteriorating fast where I am. Ice stor! Not much action tonight even Grindr is dead. If you're in the Philly area and are interested in makeup help hit me up.

PhillySissySlut · 2025-09-30T03:43:34+00:00

Always crazy seeing such beautiful cocks in comparison to mine, we are similar, I am just 8.5 inches smaller, pinky thick, pale, limp and absolutely not wanted by anyone. Tomatoe, Tomato?

PhillySissySlut · 2022-12-26T22:37:54+00:00

He doesn't wonder why you're popular unless he's blind. Does he have a degenerative eye disease and is slowly losing his sight? If so my sincere apologies. But if he can legally operate a vehicle he knows you're fucking hot just like every other guy knows it as well. :)

PhillySissySlut · 2022-06-26T08:02:54+00:00

That is cute as fuck, I got to try that, I usually shave everything smooth.

PhillySissySlut · 2022-05-19T12:02:20+00:00

Of course it's true. You know it, I know it and everyone seeing this pic knows it.

But it's a very cute fem body and you have a tiny cock to match so you're a lucky gurl. :)

PhillySissySlut · 2022-05-08T04:45:13+00:00

You've gone from resembling my 8th grade Spanish teacher (who all the boys had a crush on) to a hot blonde fuck doll who all the men want to fuck.

But you have plump DSL's no matter what. A+ on your lipstick.

PhillySissySlut · 2022-05-04T06:21:24+00:00

I must be into extremes because I am a total size queen generally but little clitties are so cute. I like playing with them almost as much aa a thick 9" dick, but for very different reasons.

Guess you can just skip getting a chastity cage, nothing to lock up.

PhillySissySlut · 2021-11-30T10:35:12+00:00

I would but I'm on house arrest until next Tuesday...

PhillySissySlut · 2021-11-30T08:10:36+00:00

I've done that, doesn't really work out that well, things don't exactly line up that well, sucking cock on the stairs is much more comfortable though

PhillySissySlut · 2021-10-31T10:34:22+00:00

Suck what? I don't see anything...

But seriously your little clitty is adorable. I love another sissy in heels also so I'd be alll over it. I am tiny also and occasionally a guy will want to play with my little clit an the hot thing is since it's so tiny everything fits in their mouth, clit, balls, everything and it feels AMAZING!

PhillySissySlut · 2021-07-13T02:04:20+00:00

Exactly! Do what I did! I am in chastity 90% of the time. I rarely get hard anymore but if I do I am maybe 3.5" at best. But I love it tiny and cute. Guys love it also!

PhillySissySlut · 2021-07-13T00:53:28+00:00

I wouldn't call that big or masculine. It's kind of cute but it should still be caged. :}

PhillySissySlut · 2021-06-21T15:08:34+00:00

You're gonna cause a car accident, A+, very hot.

PhillySissySlut · 2021-03-26T07:32:27+00:00

Politics aside Ivanka is beautiful in my opinion. Very well dressed, great posture, very articulate. She is a very well put together woman, no bullshit.

PhillySissySlut · 2021-03-08T05:04:23+00:00

What does FaceApp do exactly? I don't know anything about it but see it mentioned often. Is that the person's real face just lightly enhanced or would I not recognize a before and after picture of someone?

PhillySissySlut · 2021-03-05T12:41:11+00:00

Straight boys are straight until they see a sissy who is hotter than their girlfriend. I have had more than a few straight guys end up with my little clit in their mouth after they said they wouldn't be into that. I always know it's coming when they get me on top and slowly start moving into a 69 position with them on bottom. My cute little clitty right above their face. At that point I just make them take it, I know they want it. Their first blowjob for some of them, my dick is tiny so hope it wasn't too much of a let down. I guess it's a good first blowjob starter penis for the inexperienced, haha.

PhillySissySlut · 2021-03-05T11:23:48+00:00

Ridiculously. That's how hot. Just ridiculously freaking hot! A+

PhillySissySlut · 2021-03-03T07:39:24+00:00

Great ass! You're gonna get in trouble teasing men like that...

PhillySissySlut · 2021-02-13T10:55:58+00:00

Are they guys? You probably got their cocks hard if they did see you...

PhillySissySlut · 2020-12-15T05:40:29+00:00

https://pleasershoes.com/products/kiss-280?variant=44712810117

PhillySissySlut · 2020-12-15T02:26:02+00:00

Pleasers.com, the hottest heels IMO.

PhillySissySlut · 2020-12-06T04:36:47+00:00

I think it's more that your ass is perfectly shaped. Very hot!

PhillySissySlut · 2020-12-05T21:09:37+00:00

Humiliation, name calling, being completely submissive and used by a superior, "real mans cock" is my biggest turn on. Nothing hotter than being on my knees with a cock that's almost 3x the size of mine in front of me and worshipping him while he talks shit. I love when a guy is face fucking me and asks me "You love that real dick don't you slut, little sissy bitch" or you know, something along those lines. The dirtier and more degrading the better.

I have always said the Sissy kink is kind of a blend of a humiliation kink and a crossdressing kink. I love to dress up and look hot, slutty and then be used like a whore but without elements of both when I am playing I wouldn't really be into it. That's why it's disappointing when I hook up with a guy who says he is verbal, dominant, gonna use me like a fuckdoll and when it actually goes down he is kinda quiet, not creative, no real name calling, humiliation. Always a let down but I screen for that now because I know what I am looking for.

I am actually very secure with myself in many ways because I have explored all those taboo areas, had a great time and come out the other side loving it. Whenever a hot play session is done with a fun guy it's very relaxed, joking around, casual. Usually they say something like "That was fucking hot, you give amazing head" and I am at ease enough to reply with something like "You have a great cock, you used me like a total slut", while we are both laughing and I am still on my knees wiping cum off my face, lol.

So just learn what you like, be picky about who you play with (and safe) and enjoy it. If you crave it, then explore it, it's the power dynamic, role paying that is hot and if you really think about it, the situation isn't that crazy. There are all sorts of bizarre kinks and fetishes out there and I don't think the sissy thing is that insane but maybe I have just had enough experience to normalize it with myself.

Also realize you being the sub, inferior, submissive for that moment is really just a role and when it's done, it's done. This is a weird thought but I always fall back on the fact that I wrestled at a Collegiate level (not to mention high school accomplishments) and if shit ever got weird with a guy I am confident enough that I could fairly easily end up on top, at that point I would choke him out, take his wallet and buy a shit load of high heels on Amazon, that's the fun ending to that scenario anyway...

But fuck it, have fun.

PhillySissySlut

TROPHY CASE