Jenna Chaste aka lockedupslut

Anonymous asked: The questions on this site (souce on google: Gendercare MF9 Test in English), you can measure your femininity ... Please answer me by saying how much was your score ....

Whoops… only 25%…

unsuspectable-crossdresser:

Unsuspectable Crossdresser

Not me, but you’ve seen me do this before. This should be the only way a sissy is allowed to cum.

(via sissyfantasy)

Anonymous asked: If you could have any 2 celebrity cocks in your ass and mouth who would you want?

Regular celebrities: Vin Diesel and Terry Crews. Porn celebrities: Erik Everhard and Lexington Steele.

Anonymous asked: You should toy your ass every time they fuck!

Oh how humiliating… nice…

Anonymous asked: Will we ever see the maid outfit set?

If I get my old figure back, yes. Need to work out..

Anonymous asked: UPDATES! You have followers that check this site almost everyday (I do) in the hope to get a few sissy pics, a video, anything. I read previously that your roommates stay home a lot which limits the time you can do things. How about late at night after they are asleep? I know you have some more outfits we haven't seen. Or like a weekly pic? Are you in chastity now? When was the last time you came? Did you eat it?

I’m glad to hear that there are still people following me ;) Well the thing is that I can’t stay up till after midnight every day and do kinky stuff, since I actually do have a job and need to make a living. But you’re right. I really should do some more. I’ve gained some weight, but maybe I’ll be able to make something nice nonetheless… A weekly pic actually do sounds realistic. Thanks for the idea. Honestly, I haven’t been locked up for a week right now. And I masturbated just yesterday. I’ve been a bad, bad sissy… But at least I jerked off to a sissy story. Since I get disgusted of this sissy stuff after I had a male orgasm, I couldn’t eat my load. But I know that one day, I will be able to…

Anonymous asked: When you hear your roomie fucking his girlfriend, do you wish the one making all of those slutty moans was you?

Sometimes, yes. I even toyed my ass once or twice while they were having loud sex. The humiliation stings, but I know it’s the right thing to do in order to rewire my sexuality and to slowly become a real bottom sissy…

whiteskinnydevil asked: Hey Jenna, long time no talk. How have things been?

Very busy. And a bit frustrating because I gained some weight and my roommate is almost always at home, so I can’t dress up as much as I’d like to. But hearing him fuck his girlfriend while I’m wearing my chastity tube can be exciting sometimes ;) 

sextaboos asked: are all the pics on your image fap site of you??? send me a pm

Yes, my galleries on imagefap all contain either pics showing me or photoshopped fakes made by me. What’s your user name?

Anonymous asked: Is there a reason why you have chosen to forcefully go from straight male to gay sissy? I mean did you ever have feelings that you were gay or is it purely fantasy driven?

I was never able to make girls cum with my dick. Sometimes I even had a hard time getting it up. One of my ex girlfriends once said “Maybe you’re gay.” That really hit me. I then stumbled upon a erotic story called “Erin gets gayed” where a girl puts her boyfriend into chastity and convinces him to become a fucktoy for men. It was the hottest thing I’ve ever read. And that’s where my fantasy began to evolve…

Anonymous asked: Jenna you have a profile on Flickr?

Nope, why? ^^ 

haversackers asked: A brief comment about your advise about refraining from ejaculation to build up pressure. Any pressure build-up in the prostate is a psychological thing (which is not a bad thing). The prostate is self draining after a very short period of denial. Prostatic fluid is released from a full prostate each time you pee. When you clench your muscles to get that last bit of piss out, you're also squeezing the prostate gland. The fluid is also re-absorbed by the body. I'm enjoying your blog!

I see. Thank you for the professional input. What I can say from personal experience is that not having orgasms for a while will make you sort of desperate for any kind of release. I can imagine that it’s mainly a psychological thing. But it works (at least for me) pretty well :) 

audreybabe4u asked: I have no clue which one it is haha

lol okay! Can we see some pics from the front then? ;) 

This looks kinda cool…

Anonymous asked: Hi there, I love your blog and I was hoping you might be able to help me. My girlfriend and I (male) have tried pegging before and I really enjoyed her being so dominate over me, but as it was our first time the it was a little physically unpleasant. We used a ton of lube so going in was easy, but we weren't really sure what to do beyond that. Do you have any tips I could pass along to her to help her find my prostate and help me get anal orgasms eventually? Thanks so much.

Well I’d tell you to explore your anus first for yourself. Practice gently how to rub your prostate. Get to know your body and see where and when it feels good. Then you can give your girlfriend some instructions. Practicing seems very unromantic, but it is mandatory. Also, you reaaally need to be very relaxed. Are you wearing a chastity device? If yes: Good! If not: Try not having an orgasm for at least 15 days. That will build up the pressure and will make prostate stimulation probably much more effective. Just remember that anal orgasms feel different. Don’t give up, if you can’t get there yet. It took me a very long time to learn how to cum from anal… I hope that helps!