Crossdressing Encouragement Videos

Sis Helps You Crossdress, Part 2 video from Fiona Dagger

Sis Helps You Crossdress, Part 2 by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera!) It's been a couple of days since your sister accidentally walked in on you trying on a dress, and today she's got you a present! She explains that she was out shopping and there was a a sale on at a lingerie store, and she remembered that you said you wanted to try a garter belt and stockings, so she bought you a full set of bra, panties, garter belt and nude stockings to go with them! She tells you she's really happy that you're enjoying yourself experimenting, and says that she thought you looked so good when you tried on her clothes the other day. She asks if you want her to leave so you can try them on, but you tell her you're fine with her staying - and you suggest that she puts on the other set, which she'd bought for herself, so that the two of you can try your new lingerie together! Your sister seems pleased at your suggestion, and the two of you turn around and face away from each other while you get undressed and put on your new items (though of course, you do take a few sneaky peeks at your sister while she's changing...) Once you're both dressed in your new lingerie your sister helps you fasten the stockings to your garter belt, giggling as she notices how sheer your new panties are, and how visible your cock is! She gives you lots of compliments, saying that she really thinks she's going to have to get any future boyfriends to dress up in girls clothing for her, as she thinks it looks so hot! You're enjoying her admiring your body, and feel your cock starting to get hard as she watches you. Your sister notices it and does her best not to stare, but she can't seem to tear her eyes away.... She realizes that the panties she's wearing are actually crotchless, and tries to hide herself with her hands, but you tell her it's fine! She seems embarrassed but admits that she can feel herself getting wet, and that's very conflicting for her - she shouldn't be getting wet over her own little brother's cock! She says she should probably go, as this is all getting a bit weird - but you convince her to sit down on the bed and calm down, assuring her it's fine. You ask her if she really likes seeing you like this, and she tells you it's really turning her on, and in fact she's been thinking about you dressed up like this ever since the other day... You tell her you think she looks really hot too, and that you don't mind that she's turned on over you - your cock is rock hard for her right now, after all! Your sister shyly asks if you'd let her watch you stroke it; admitting that she's been fantasizing about seeing you stroking your cock whilst wearing panties... You slide your hard into your thong and start slowly jerking your cock as your sister stares, then tell her it's fine if she wants to touch herself too... You notice she's making a puddle of wetness on your bed as she opens her legs, revealing the crotchless part of her panties and her pink, wet pussy peeking through... She starts rubbing her clit shyly as she watches you stroke your cock, with both of you growing more and more confident, and confessing how much it turns you on to see each other like this... She tells you she's getting close, and asks if you really want to see your big sister cum? You tell her you do, and that you'll cum with her as well. She moans at this and tells you she so badly wants to see your cock cumming in those panties, so the two of you keep pleasuring yourself and looking into each others eyes as you make yourself cum really hard! Afterwards, your big sister tells you how much she enjoyed that, and leans in nervously, asking you if you'd like to try kissing her... TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo, bro sis, brother sister, crossdresser, crossdressing encouragement, sissification, sissy, feminization, mutual masturbation, jerk off encouragement, lingerie, fingering

^$7.00 Add to Cart

17:59

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play video from Victoria Lotus

First Time Crossdressing: Lingerie Shopping to Hotel Room JOI CEI No Humiliation Gentle Femdom Jerk Off Instructions Butt Plug Prostate Play by Victoria Lotus Hi there! This was a custom video so feel free to contact me on my profile to get in touch for ordering your very own. Here is the script: "Hey! As discussed via DM, I'd like a custom to guide me into my first crossdressing experience (thong bra, no other feminine clothing involved). In three sections (don't have to be equally long, you judge): shopping for the lingerie, putting it on and wearing it out and about, and JOI/CEI wearing that lingerie in my hotel room. I think the vid will work best if I can play part during each section, then pause it before moving on to the next (e.g. back to my hotel). The context will be: I am going to a conference and feel free to explore my fetish while I'm away, so can go into a lingerie shop and then wear my new purchases and play. The tone should be encouraging/sexy, not humiliating or too femdom (I'm ok being instructed, just not insulted). I don't want to restrict you with a script, so here's just a list of things I like or would like to try: me wearing a non-vibe glass butt plug or a vibrating one (I'll take both, you choose!), clenching my butt with the vibrating plug to stimulate my prostate, gently rubbing my nipples (I really adore edging like this), subtly flashing my lingerie (e.g. bend over to expose a thong in public), self-facial CEI, moaning when I'm turned on, repeating sexy mantras (e.g. "I'm such a cum slut for you"). I dislike: humiliation, pain, insults, being called a sissy. If possible, I'd only want to stroke my cock at the end to push myself over the edge to cum (not throughout the video). As for you, I'd love for you to wear lingerie too, really show me how to put on the bra and thong properly, put in a butt plug with me, and definitely show off your ass frequently as that's a real turn-on for me. My real name is "Shawn" for inclusion in the video. Do contact me via DM if you need more information!" #Crossdressing #Lingerie #FirstTimeCrossdressing #CrossdresserJourney #ThongBraAdventure #ShoppingForLingerie #CrossdressingConfessions #JOI #CEI #CrossdressingInLingerie #Feminization #CrossdressingFantasy #HotelRoomPlay #NaughtyLingerie #SensualCrossdressing #CrossdressingTransformation #CrossdresserLife #ExploringCrossdressing #CrossdressingDiscovery #CrossdressingExperience

^$20.00 Add to Cart

13:40

Seduced By Silk - Star Nine video from Star Nine

Seduced By Silk - Star Nine by Star Nine This satin dress feels so good against my flesh and these classic black pumps accentuate my long legs. It's a shame men can't wear this sensual fabric, because our culture doesn't allow that. We should probably stop before you can only get hard from wearing women's clothing. You want to continue with the pink satin but not be a crossdresser? If we lock your cock in a chastity cage, it will prevent erections and prove that you're just indulging sensation play and not a deviant. We have to make sure you have a limp cock before we put the metal cage on. So have one last orgasm while I give a sensual jerk off encouragement. When I put your cock in the cold cage, it's another form of sensual play. I will do the keyholding so you can focus on the sensations! Includes crossdressing encouragement, sissy humiliation, joi, chastity, sensual domination KEYWORDS - sissy training sissification sissy sluts sissy training cages orgasm control orgasm denial jerk off instruction masturbation encouragement masturbation instruction cock tease dirty talking dirty female domination pov femdom pov silk & satin fetish clothing fetish clothes high heels stilettos blondes tall woman tall women kink Send your custom video request to star at starbondmedia dot com

^$18.00 Add to Cart

20:39

Sis Helps You Crossdress video from Fiona Dagger

Sis Helps You Crossdress by Fiona Dagger (This video is a bit cheaper because it's shot on my phone rather than my filming camera! There is no real sexual action in this video, it's just crossdressing encouragement, but a part 2 will be coming soon where bro and sis mutually masturbate together!) Your big sister walks into your room without knocking, about to ask you if you want to go to the gym with her - but she's shocked to find you wearing a dress and admiring yourself in front of the mirror! At first she gives you the benefit of the doubt and assumes you must have a costume party, but you fumble your excuses and she quickly realizes that you're lying! She tells you it's okay, you can tell her the truth - did you just want to know what wearing a dress felt like? You're so embarrassed but you admit that yes, you just wanted to dress up in cute girl clothes to see how it felt... Your sister tells you not to feel bad about it, and that she's happy you're experimenting - but that the dress you're wearing is really ugly, so how about she lets you try on some of her clothes, which will suit you a lot better! She fetches a few dresses for you to try on, and suggests you start with a cute pink sundress. She's very supportive of how it looks on you, telling you that you look really good, but that she can't help but giggle a little in shock as it's just so strange seeing her little brother dressed like this! The next dress you try on is a sexy, tight bodycon one, so she instructs you on how to roll it onto your body and warns you that it will be very formfitting! The dress feels so nice that you can't help but get an erection, and when your sister turns back around she immediately spots it, as the dress is so tight that she can basically see the outline of your hard cock super clearly! You're embarrassed again but she tells you it's fine, she did kind of guess that this was a sexual thing for you, and she doesn't want to shame you at all - in fact she reiterates that she thinks you look really nice, even saying that maybe in future she'll ask her boyfriend to try wearing a dress for her! She tells you she brought another dress in, but warns you it's very sexy - it's basically a babydoll nightie, with massive slits up each side so it doesn't leave much to the imagination... You put it on and your boner sticks out so much that your sister giggles even more, but she also can't seem to take her eyes away from you! She shyly suggests you try some actual lingerie, and fetches some stockings, and a bra and panties from her room. She teaches you how to put the pale pink, lace top stockings on first, and then tells you to put the red, lacy lingerie on - warning you that the panties are very small and won't cover much at all! Once you've put it all on she can't stop staring at your hard cock, barely constrained by the tiny strip of red fabric, and after giving you lots of compliments and promising that you look really good, she suggests she leave you alone so that you can take care of your boner - and tells you just to wash the lingerie before you give it back to her! As she leaves she keeps glancing at you and at your hard cock, and you wonder if she might even be going to 'take care' of herself as well... TAGS: british, english, redhead, ginger, tattoos, tattooed, solo female, roleplay, dirty talk, posh accent, pov, taboo , bro sis, brother sister, crossdressing, crossdresser, cross dressing, cross dresser, sissy, sissification, encouragement, lingerie, big sister, little brother

^$7.00 Add to Cart

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