jesswintersof
@jesswintersof
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@jesswintersof OnlyFans
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
mini photo shoot for y'all before i go out 😉
April 13, 2025 - 06:00:47this 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.. 😩😩😩
March 31, 2025 - 09:04:20theres nothing better than when strong men grab your hair to control your head to please his 🍆😩(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 😉)
March 29, 2025 - 09:17:15i 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 ?
March 15, 2025 - 11:09:01a little obsessed with my butterfly flat cage 😭😍
March 12, 2025 - 02:22:17she 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 . 😅
March 11, 2025 - 05:20:45she 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 ! 😤
March 4, 2025 - 08:20:45bad girl punishments vs. good girl rewards
March 3, 2025 - 06:44:20Just a lil something to let y'all know I'm back 😉 expect fun things 😍❤️
March 2, 2025 - 03:20:39Sissy in pink and white enjoys horsecock dildo 😵💫
January 18, 2025 - 15:19:36Lost pet... needs owner !
January 12, 2025 - 06:55:28Back from vacation! Here are some ol ' Christmas photos 🙂
January 10, 2025 - 00:30:43video of me putting on my full chastity belt and bra. 2025....it's going to be a year of discipline and restraint(s) 😉
January 1, 2025 - 09:49:56You never know what a regular looking girl could be hiding her normal clothes 😉 🔐
December 28, 2024 - 07:07:51I'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 😵💫
December 27, 2024 - 08:35:14Cute lil metal chastity just to go with my white outfit and sparkly panties 😉
December 22, 2024 - 04:14:30I think my girl has found a new home 🙂
December 18, 2024 - 18:09:39How bad do you wanna see how much I could be hiding under my regular clothes when I go out 😉
December 16, 2024 - 22:19:48Collared, chained, then whipped... is how I normally would wind up at the end of a date now ..
December 13, 2024 - 04:33:08Remember when I said I don't rly dom... well about that.. put your wrists in these, I wanna show you smth 😉
December 1, 2024 - 03:24:04I don't do ahegao faces often.. rare pic lol
December 1, 2024 - 02:39:56{RE} I know I look a little Dommy here but trust me I just wanna be submissive 😇
November 30, 2024 - 00:30:51Babessss I love you alllll!! Btw , got some new toys for this weekend . Can’t wait to play with them for you 😍
November 21, 2024 - 09:51:56Omfg what have I done , now what am I going to rub??
November 14, 2024 - 06:53:43Dressing up, chores, and dancing 🙂↕️
November 10, 2024 - 06:54:32Weekend is almost here. I’m going to post a good amount of hot stuff for yall soon heheh . I’m fucking horny
November 8, 2024 - 05:14:17Idc if this is sexy or not. I’m a Star Trek nerd 😭
October 31, 2024 - 15:50:26omg i cant rememebr which one is the best one.. so here just take them all!! the first one is the long one tho ;)
October 24, 2024 - 02:37:07Hey babes.. glad to be back. Enjoy these teaser photos... The Video is coming tomorrow ;) hehe, enjoy 😉
October 21, 2024 - 06:30:41Heels 🔒 Chastity 🔒 What else do you think should have a lock?
October 12, 2024 - 05:30:55Locktober day 8. Today is also my birthday !
October 8, 2024 - 20:17:18Day 5 of locktober Xxx spooky month calls for some spooky stockings
October 5, 2024 - 04:24:26Just a girl and her toys
October 3, 2024 - 00:59:00My new pfp! Now with titties 😍🖤 what do you think?
October 1, 2024 - 05:52:04Locktober isn’t till tomorrow, but I was always taught the importance of being early 🙂↕️
September 30, 2024 - 15:27:39What do you mean, “see you in a few HOURS?!”
September 29, 2024 - 08:46:53Do you like athletic trans girls? 💪 🥰
September 22, 2024 - 04:30:57Do I need a college degree for this position?
September 18, 2024 - 03:02:14Hey 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
September 17, 2024 - 02:41:34Double the machines double the fun..
September 14, 2024 - 02:26:09hey 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 ❤️❤️
September 9, 2024 - 19:02:55how to train your kitten 😉
August 13, 2024 - 06:13:02an average saturday night... just wishing i had the real thing though ;')
August 4, 2024 - 07:15:55looking for some fun baby? 💙
August 2, 2024 - 15:40:57sunday night plaps, now with more plaps in more places!
July 29, 2024 - 04:51:52people always ask me what my max is.. probably 8-9 of you guys 😉
July 25, 2024 - 05:25:53ugh, daddy, i just got home.. are you really collaring me already ?
July 25, 2024 - 05:22:18I tried on a few of my old cages 😉
July 6, 2024 - 06:53:58Im having a lot of hot fun with this little red toy.. would be hotter if it was with you though ;)
June 30, 2024 - 05:00:22OnlyFans is a registered trademark of Fenix International Limited. Fleshbot is not owned or affiliated with OnlyFans. All information is derived from public sources and operates as a data search engine.
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