Office MILF Penny Barber dominates her sissy in exclusive BTS video

to another one of my poorly thought out but also I'm thinking about it constantly poorly planned out overthought out rambling little vlogs it's gonna be fun I just finished shooting two different things in this little outfit, which I actually liked a lot more than I did. I got all these like little chiffon or silk or whatever the fuck they are bows now, which I love. And so I was supposed to do like a teacher thing today. It's about, this is kind of teachery, right? I always think of, I know I'm not wearing a bra. I did know that in case you thought I didn't. But, so other than that, it's pretty teachery. I mean, I know it's a crop top, but it's like it meets the short, the The skirt. It looks pretty good. I like it. I'm happy with it. I'm doing my annual like 50% off custom sale right now. So I have been shooting a lot of customs. And I keep thinking about doing vlog and then like just being so exhausted. I only shot two today. Usually I'll shoot three. And I just cannot. I just can't afterwards. My lipstick probably all messed up. That was like sucking on my little fucking machine over there. He's not much of a fucking machine. I will tell you. This is loosely. I actually got this for the sissies. Because I was like, oh, a pink fucking machine. How beautiful. But it doesn't go very hard. So mostly it's just like a dildo holder that I can like, oh, I've got it screwed in. But like I can like position it. And so that's pretty much what he is. Let's get this condom off of here. That's a bit inside of me. I don't fuck toys without condoms. I think that's actually really, really gross. Like, if it's like a stone toy or something, or if it's glass, then I'm like, eh. But if it's, if it's silicone or anything, I always do not know how these girls fuck these things. And they're like, well, I boil, or I do this, or I do that. And I just think back to, I just don't want to. Maybe it's fine. I don't know. Maybe it is fine. It could very well be fine. I don't know. I'm not a... dildo doctor except on in clips but uh yeah so that was only about two and a half minutes of me rambling uh what are my sissy fantasies my sissy fantasies i think is the topic and i have just been so disappointed with dating recently i really don't well like for example last night was the um with the monthly sissy munch that we have here in San Francisco and I always think about going. I'd like to go and then I just kind of think about like, oh, but what's gonna be there when I get there, you know, like it's gonna be not great. They did a photo shoot there one time of the sissies and most of them were not dressed super well in my opinion. I'll give you an example that's not from there so they don't like hurt someone's feelings that I might actually see someday. But I am when I went down to DomCon they had a they had this sissy pageant and if you know me I love pageants. Oh my god. They're utterly ridiculous. I love the like over-the-top femininity. I think it's so great. I especially love like cross-dresser pageants. Oh my god, you do not even know. I used to do the age play pageant, which was so much fun. I love pageants, right? So of course I was going to go to the sissy pageant at freaking DomCon. I was there with bells on. Possibly literally. I took so many pictures. But I was down there because I had this kind of friend, like acquaintance, and she was like, oh, I'm going to have a sissy in the pageant. I was like, oh, that's great. And so I went down there to get a look, and it was not good. It wasn't great. She had on this ratty old wig that was just like. Had not been combed. It looked terrible. It was really long too like long wigs require a lot of maintenance like if you are a sissy or a crossdresser and you want to look cute I strongly suggest that you go for a short wig. I know you're like oh, but long flowing hair, but it's not going to be like that it's going to be a long fucking rats nest of Extra fake looking hair. It's not good. You know you don't have You're not wearing like a real human hair wig. You're probably wearing like some cheap synthetic wig and it's going to look bad. So her wig was horrible. Her... She was wearing flats, which I was like, she was older, you know, like probably in her 60s. And so I was like, okay, well, maybe she just can't walk in heels. But, um, so she was wearing flats, which... My my sissies do not wear flats unless there's a very good reason and if they are wearing flats It's because they're doing a little girl thing and they're wearing like patent Mary Janes and this it looked like she was wearing flats because she couldn't walk in heels Which is not very impressive. Let me tell you She was wearing this ill-fitting corset that was like down over her ass instead of like up on her waist She would just her mate. It was it was she's a fucking mess and I was just like Oh my god. Like, I, I, if I was out in public with a sissy, I mean, first of all, my sissy would not look like that. If I was out in public with a sissy and they were dressed like that, I would just be like, do not tell people that you're here with me. You know, like, honestly, it's not good. Um, so what I like about sissification isn't so much, it isn't even really the taboo of, like, Boys dressing like girls. I mean, I guess maybe a little bit, but you know again, I'm a millennial and so it's not like as much the thing. It's more about feminine type of submission and don't get me wrong I really like masculine types of submission to like actually quite a bit but um I really like gender I like it I love gender I mean I'm a high high high femme and I like my sissies to be high high high high femme too and that includes you know a lot of training with knowing like different types of curtsies and which ones to do when knowing little like routines that they can do being well dressed for whatever they are. What I do not like are like the slutty sissies. You just like throw on some stuff and they're like, yeah, I know I'm a slut. And I'm like, I wouldn't fuck you. Good luck being a slut. I wouldn't touch you with a 10 foot pole. But then, you know, you get the sissies who are really feminized, who are more like slutty sissies, like crossdresser type sissies. And we know they got their legs perfectly shaved or they're wearing like layered tights and stuff so it looks really good. They're wearing heels that they know how to walk in. They're not wearing open-toed heels with pantyhose. I hate that. You know, they're wearing clothes that fit them that are very flattering to them. If they're corseted, they're corseted in a corset that fits them. You know, their hair looks good. Their makeup looks good. They've actually taken the time to cover up their beard, which... You know if you're feeling if you're a sissy you should like makeup you should like the process of being feminized you know so you shouldn't Rush through it. I don't like to rush through it. I like to take my time I like to take at least an hour at least an hour to get a sissy ready I like sissy who like to go shopping for the things that they want to get that are going to work for them and Who aren't like all humiliated and embarrassed about that and I mean like there's mm-hmm, excuse me There's like being like coy and cute and embarrassed like you know for your mistress, which I think is really really cute and then there is you know sitting in the car for two hours before you can go into the store with your head between your knees hyperventilating which I am I guess I get it, you know, I mean I suppose if you've really built it up in your head but you know also nothing's going to happen. I don't have too much patience for that and I know that a lot of sissies and crossdressers really need that kind of patience to like really get them to the point where they can go into the store and like buy panties or something. That said, I also don't like the guys who just walk in swinging their, you know, little erections around and jus