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Submissive tgirl, kinky.. read "more info" Chastity-locked, always horny & fantasize about living a submissive BDSM lifestyle someday Always trying to feminize myself further, & I love girly things I dress & create when I can. If there's ever a break between content it's only because I get busy like everyone else! I'm human! All support here will go toward helping me afford to feminize myself further like permanent hair removal/piercings/gym membership, and other long-term body stuff! Tips also go toward outfits & clothes for my lifestyle. If you want to buy me clothes directly, check out my Amazon Wishlist. I appreciate any generosity! I will produce receipts if requested! Whether it's a monthly sub or any tips, it all goes towards helping me make better content. I always appreciate the support through my sissy life. Please enjoy! Jessica


@jesswintersof Latest Posts

  • mini photo shoot for y'all before i go out πŸ˜‰

  • this is so hot. for over 7 minutes, i was on my knees sucking off my mistress's boyfriend, he doesn't cum quickly at all; he loves to take his time with me and likes to put his hand on my head... finally he shoots his load directly down my throat while i was deepthroating!! at the end, my mistress rewarded me with my hormone pill for being such a good girl and doing a good job.. she told me since im so good at it i have to work for it every time now.. 😩😩😩

  • theres nothing better than when strong men grab your hair to control your head to please his πŸ†πŸ˜©(ps. this is only a tiny clip of one of a bunch of much longer videos that are coming, i just wanted to post something ASAP πŸ˜‰)

  • i spit roast myself between my machine and my wall, reinforcing my cock-pleasing training! i toy myself with the one on the wall after i suck it for a while and finally (after a brief change of clothes) i make myself cum through my cage with a vibrator into a cup, and then drink it all like a good girl ! is it crazy that i still want to do more ?

  • a little obsessed with my butterfly flat cage 😭😍

  • she had me crawl around with my plug in like a pet, then told me "good girl" and to practice my bj skills on the toy she had. she was kind of gentle this time.sorry this vids a lil short we're working on making longer ones now that i have a better computer . πŸ˜…

  • she knows how much i love her tits.. i asked her if she would let me have a boob job and she said "sure.. i'm still not unlocking you though.." she's so mean ! hmph ! 😀

  • bad girl punishments vs. good girl rewards

  • Just a lil something to let y'all know I'm back πŸ˜‰ expect fun things 😍❀️

  • Sissy in pink and white enjoys horsecock dildo πŸ˜΅β€πŸ’«

  • Lost pet... needs owner !

  • Back from vacation! Here are some ol ' Christmas photos πŸ™‚

  • video of me putting on my full chastity belt and bra. 2025....it's going to be a year of discipline and restraint(s) πŸ˜‰

  • You never know what a regular looking girl could be hiding her normal clothes πŸ˜‰ πŸ”

  • I'm working so hard on trying to take the whole thing..! Used my vibrator to cum after a while cause I just couldn't take it anymore πŸ˜΅β€πŸ’«

  • Cute lil metal chastity just to go with my white outfit and sparkly panties πŸ˜‰

  • I think my girl has found a new home πŸ™‚

  • How bad do you wanna see how much I could be hiding under my regular clothes when I go out πŸ˜‰

  • Collared, chained, then whipped... is how I normally would wind up at the end of a date now ..

  • Remember when I said I don't rly dom... well about that.. put your wrists in these, I wanna show you smth πŸ˜‰

  • I don't do ahegao faces often.. rare pic lol

  • {RE} I know I look a little Dommy here but trust me I just wanna be submissive πŸ˜‡

  • Babessss I love you alllll!! Btw , got some new toys for this weekend . Can’t wait to play with them for you 😍

  • Omfg what have I done , now what am I going to rub??

  • Dressing up, chores, and dancing πŸ™‚β€β†•οΈ

  • Weekend is almost here. I’m going to post a good amount of hot stuff for yall soon heheh . I’m fucking horny

  • Idc if this is sexy or not. I’m a Star Trek nerd 😭

  • omg i cant rememebr which one is the best one.. so here just take them all!! the first one is the long one tho ;)

  • Hey babes.. glad to be back. Enjoy these teaser photos... The Video is coming tomorrow ;) hehe, enjoy πŸ˜‰

  • Heels πŸ”’ Chastity πŸ”’ What else do you think should have a lock?

  • Locktober day 8. Today is also my birthday !

  • Day 5 of locktober Xxx spooky month calls for some spooky stockings

  • Just a girl and her toys

  • My new pfp! Now with titties πŸ˜πŸ–€ what do you think?

  • Locktober isn’t till tomorrow, but I was always taught the importance of being early πŸ™‚β€β†•οΈ

  • What do you mean, β€œsee you in a few HOURS?!”

  • Do you like athletic trans girls? πŸ’ͺ πŸ₯°

  • Do I need a college degree for this position?

  • Hey everyone !! Can't wait to start sharing more posts regularly again!! I had a bit of reconstruction being done on my house (including my room) so I didn't have much to work with in terms of space but I'll be back making hot content for you all when it all settles down (will be soon!). Thanks for your patience and I appreciate all your support. If you're reading this it means you didn't leave me so I REALLY love you and thank you for being patient..! With love, Jessica

  • Double the machines double the fun..

  • hey babes (; sorry that its been such a long wait (since ive posted) but i havent abandoned my page or anything i have just been busy with my gf... speaking of which.. there will be some videos of that soon too.. stay tuned ❀️❀️

  • how to train your kitten πŸ˜‰

  • an average saturday night... just wishing i had the real thing though ;')

  • looking for some fun baby? πŸ’™

  • sunday night plaps, now with more plaps in more places!

  • people always ask me what my max is.. probably 8-9 of you guys πŸ˜‰

  • ugh, daddy, i just got home.. are you really collaring me already ?

  • I tried on a few of my old cages πŸ˜‰

  • Im having a lot of hot fun with this little red toy.. would be hotter if it was with you though ;)



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