Bailey Chastity

Hey guys! I’m Bailey Chastity or Bailey N Chastity! Just your average 20 something total bottom, cock slave sissy faggot! I love chastity, femininity and being roughed up by strong tops! I don’t get to dress often, but when I do I really get into it! I am also very active on fetlife! Check me out! All pics posted are of me!

[baileychastity]

Moving

I will be moving all my content back to other sites;

Xhamster: sammiecdboi

Pornhub: Bailey Chastity

BDSMLR: Bailey Chastity

Fetlife: Bailey Chastity

[baileychastity]

Now that tumblr has decided to be jerks and purge NSFW content, are you going to try other social platforms? I ask because I love your blog and would love to learn a little from you.

I think I will move to xhamster, pornhub, and I’m on fetlife

[baileychastity]

Hi Bailey, I love the blog. You really inspire me. Anyway, I’ve got 2 questions. I’m a bubble butt anal slut who loves showing off her curves but has a college roommate who comes and goes erratically and I don’t want him to know. What should I do? I also have a 7 inch clit and I’m finding it difficult to get a cage. Is there any place I should start? Thanks. Love you 😘

Hey girl! Well for starters I understand the need for privacy. One suggestion I have is to find some girls like you that have their own place to have fun, or some top men that can host. When I was in a situation like that, I would seek out older men 35-50, because they almost always have their own place. This was fun because I could go over there, dress up and sometimes we would have a little photoshoot lol.

As for chastity, I would say try to use ice packs to dampen the excitement. Put the ring on then go do any other task and catch your clitty off guard and cage it up while it’s limp! 😂😘💕

[baileychastity]

The much awaited sissy BBC gangbang! I was forced to serve the superior race by BBCSlut4Sissies (fetlife profile) and it was the best experience of my sissy life. She made me beg for the BBC and then forced me to take it and serve like the sissy slut I am.

I hope all you little sissies understand this is what you are mean to do. Stop stalling and serve BBC. I can’t get enough now 😍😍💕🎀

[baileychastity]

6K

Just hit 6K followers! Thank you for all the love, reblogs and support! Stay tuned for some really hot content 😘🎀🎉

[baileychastity]

Ok girls listen up! On Friday, I had an amazing experience at The Trans Spa, in Harve de Grace, MD! This place specializes is transforming CD,TG,TS and anyone else into stunning feminine form😍.

The whole experience was amazing, Darryl the make up artist has over 20 years experience and did a great job. I started by telling them I wanted to look more passable and “natural,” as opposed to a drag look.

The spa is very private and the atmosphere is amazing! I did the Full Transformation and I am so glad I did. As you can see the spa has 100’s of wigs, of which I tried on dozens trying to find the right one! I also got some very realistic breast forms and some cute outfits!

They made me look the best I ever have! As I was driving home, I went through a toll. The older cute black gentleman was stunned when he saw me lol. He just let out a “wow,” as I handed him exact change and drove off. I saw him looking as I drove away lol.

I highly recommend this place to everyone! It was one of the best experiences I’ve ever had. Check them out!

https://youtu.be/yn0KGJtGEng

Www.Transspa.com

P.S. I was in chastity the whole time in preparation for my BBC gangbang later that night 😉

[baileychastity]

Hi pretty, i'm a little confused. I'm a 25yo male, good looking with a fit body and a 18x6 cm dick that make a lot of hot girls cum but, I have a strong urge to dress myself as a sissy slut and please big dicked man, I don't wanna be locked in chastity because my dick would shrink and the girls I fuck could notice. What should I do? Wear it only when i'm the submissive or embrace my sissy whore side fully?

Why not both?! Honestly it won’t shrink if you only do it when you are dressing. Shrinking comes from prolonged usage like me. Shrinking is my goal lol. Dress while you are still smoking hot lol

[baileychastity]

How often do you fuck big alpha cock?

I try to every few days while I’m locked in chastity. If I don’t I get cranky and irritable lol. I feel the need to be forced back into submission by a real Alfa male using my pathetic fem beta body 😁😘

[baileychastity]

Do you smoke?

Only the pole lol 😘🍆

[baileychastity]

I want to start locking myself in chasity but I have no way of getting a device. Any way I can substitute one?

Um not that I know of. I would say go to the post office and open a P.O box. They are cheap and are very private. Then you can send anything to there without anyone knowing. If the package is too big for the small box, they just hold it in the back. 😘😘

[baileychastity]

Heyy I love your blog so much, I’m 17 and love dressing, and I’m definitely ready to play with a daddy but I don’t know how to go about it, I’ve met a few online but they can’t come over and I don’t know what I should tell my family about why I’m out for so long I’m weird part of the city

Well being a young sissy requires some deception. You will have to create a plausible excuse as to where you are going and for so long. In the beginning I would bring a bag and dress at their place or at a hotel.Hope this helps!

[baileychastity]

What would you suggest to a young sissy/CD who still lives at home? I think you’re incredible x

Hey girl! I would say to continue to pursue our fetish! Sometimes it can be hard to hide all of our sissy ‘gear’ but don’t purge it! I would always take my duffle bag of girly stuff over to older men’s house and dress there! So much fun! Also, if you are trying to get stuff sent you you, a P.O box from the post office is easy and cheap! 😘😘👍🏻💋

[baileychastity]

I wanna fuck you

Get in line lol

[baileychastity]

When did you discover you were a girly little sissy slut?

Well, I first dressed in my little sisters clothes when I was around 10. I continue through my teen years and when I was about 15/16, I started to seek out older daddies to play with. I lost my virginity with a 40yo guy when I was 15. I found him online and wanted to dress up while he fucked me. The rest is history lol

[baileychastity]

Embrace your feminine side! Buy make up and cute outfits online, watch YouTube makeup tutorials and explore the cute side of yourself! 💋💅🏻🎀💓👠👗🍆🍑👛👙💕🌸

[baileychastity]

After reading your blog i so want to become that beta male and start my sissification!!!! How to begin?

Continue to surf sites with sissification fetishes like tumblr, hypnotube and fetlife. Make a profile and start taking with men. Buy toys and makeup from amazon and watch makeup tutorials. Submit to alpha men.

[baileychastity]

Probably the most influential substance of my sissy existence: POPPERS & ETHYL CHLORIDE Poppers: a must have for a true sissy slut. They make you feel so warm and slutty. Great for loosening your body and assisting in taking cock. You sniff them for short periods of time. Ethyl Chloride: similar to poppers, you spray the liquid into a plastic bag and inhale. Much stronger and more intense than poppers. Some good/reliable websites to get this from are popperslosangeles.com and aromaboy.com Thank me later 💋💅🏻🎀