Step-Auntie Josephine Finds You Sifting Through Her Panties POV Josephine 03/15/2022You were just rifling through Josephine's used panties and bras when your Step-Auntie Josephine walks in and catches you! After some admonishment, she's finding holes and stains and puts the pieces together of what you've been doing with her underwear, and admits that she understands your obsession given...
Visiting Step-Auntie Josephine Turns Into Jerk Off Instruction Josephine 02/25/2022On a visit with your Step-Auntie Josephine, she's on the couch in a sweater, a short skirt, thigh high stockings with garter belt, and black high heels. She starts by trying to motivate you to focus on your studies and work, and is shocked by your discussions of "naughty parties" you've been going to,...
Housewife Josephine Strips & Masturbates on the Couch Josephine 02/16/2022Check out Josephine in her tight navy blue dress and black high heels, chilling in the living room and sitting on the couch and opening her legs to flash her tiny lacy pink panties before ditching the dress entirely and showing of her matching pink bra and a light blue garter belt. After teasing you...
Josephine Masturbates by the Fireplace in Robe & Lingerie Josephine 02/09/2022Josephine is in her living room by the fire, relaxing on the floor in her silky red robe and matching lacy red lingerie, with thigh high black stockings & garter belt, along with black high heels. After caressing herself all over, she kicks off her heels and warms her feet before slipping off her stockings...
Housewife Josephine Stripping & Standing Masturbation Josephine 01/31/2022Check out housewife Josephine in her blue dress, thigh high black stockings, and black high heels. At first, she teases you by pulling her dress down a bit to show off her epic cleavage and intricate bra, and also by turning and lifting her dress to flash her curvy ass at you, but then loses the dress...
Josephine Recounts Her Evening, Fantasizes and Masturbates Josephine 01/24/2022Josephine is home after a night out at a party, still dressed up in her silky pink dress, strappy high heels, thigh high stockings, and long black velvet gloves. As she recounts her lovely evening, her mind wanders to a young gentleman that was at her table, the highlight of her evening. As she describes...
Josephine Elegant Stockings, Garter, and Heels Josephine 01/15/2022Josephine is near the fireplace in an elegant red dress, black silky gloves, thigh high stockings, a garter belt, and shiny & strappy black high heels. Welcoming you in, she immediately turns and bends over and flashes her curvy ass and black thong panties at you before turning to face you and flashing...
Josephine Turns Working Late into a Stripping & Pussy Play Session Josephine 01/08/2022Josephine, ever the hard worker, is burning the midnight oil when she gets a series of texts that get her gears moving. Dressed in a black button-up top, short plaid skirt, thigh high lacy red & black stockings, and black high heels, she decides to take a break to focus on herself and her needs. After...
The Legendary Josephine James is Back! Happy New Year! Josephine 01/01/2022The Legendary Josephine James is Back! As a New Year treat, Busty brunette MILF Josephine is here in a short black and gold dress, slowly unzipping it to reveal her sheer strappy black bra and bustling cleavage. Once the dress is off, she tugs at her light blue panties and flashes her nicely trimmed...
Auntie Josephine POV Blowjob Josephine 09/21/2020You've come by to spend some time with your busty & curvy Auntie Josephine. She asks about school and, especially, about girls at your school. She can see you fixating on her ample cleavage, and tries to dissuade you from staring. Eventually, she relents a bit and unbuttons her blouse just enough to...
Josephine Lingerie & Silk Robe Pussy Play Josephine 09/16/2020Curvy brunette MILF Josephine is all done up with her silk robe, barely hiding her elegant lacy black and green lingerie, thigh high black stockings, garter belt, and black high heel shoes. Smiling and stripping out of the robe, she teases you with her ass and slips the panties to the side for a quick...
Seduced by Auntie Josephine JOI Josephine 09/11/2020You dropped in to see your Auntie Josephine, and she's excited to see you - her favorite nephew. She asks you about school and any parties you've been going to. She can tell by your smile you've been looking down the girls' shirts, and she invites you to look down her shirt. Seeing the effect that's...
Josephine Elegant Chaise Lounge Masturbation Josephine 09/06/2020Curvy brunette Josephine is decked out in an elegant green dress, thigh-high black stockings, fiery red high heels, and a lacy black panties. Relaxing on her tufted chaise lounge, Josephine is in the mood to put on a show for you, leaning back to reveal a flash upskirt of her lacy panties, then bending...
Josephine Seduces You After A Bath Josephine 09/01/2020Josephine just finished her bath, but now she needs to moisturize, and she invites you to help as she opens her silky bathrobe and lets her massive MILF tits hang out. She lotions up her curvy thighs and calves, before lying back on the floor and opening her robe and moisturizing her tits thoroughly...
Josephine Strips & Masturbates in Her Garden Josephine 08/27/2020Busty & curvy brunette Josephine is in her garden, enjoying the weather and the view, and decides to put on a little show for you in her short skirt and high heels. Lifting up her skirt to flash her bright red panties, garter belt, and a hint of her thigh-high stockings. She takes the bench and removes...
Josephine Masturbates at the Gym Josephine 08/21/2020Josephine is at the gym, working those machines, working up a sweat in her skintight gym clothes. Now that the workout is over, she massages her giant MILF tits, lifting her top and letting them fall while she gropes and tugs and massages them. Now turned on and needing more, she whips off her leggings...
Equestrian Josephine Masturbates in the Barn Josephine 08/16/2020Equestrian Josephine is all decked out in her riding gear, but she's got something else on her mind. Sneaking off to the barn, she unbuttons her blouse to flash her massive MILF cleavage, bends over to shake her curvy ass, then takes the blouse off completely. She lets her bra straps fall, and pulls...
Josephine Office Strip & Masturbation Josephine 08/09/2020Josephine is at the office, waiting on a call. She hates waiting. Her mind starts to wander to who she's waiting for. She decides she has "a couple of minutes" to let her mind wander and her hands to wander her body as well. She unbuttons her blouse and rubs her hands all over her huge mature tits, before...
52yo Buxom British Legend Josephine makes her glorious return to AJ after 10yrs! Josephine 08/04/202052yo Buxom British Legend Josephine makes her glorious return to AJ after 10yrs! Looking elegant as ever in her long black & flowery dress, she strips in the hallway and shows off her huge natural MILF tits, her big bold areolas, and her pierced shaved smooth mature pussy, which she spreads and fingers...
Filthy Phillip 12/22/2021 Not too many pairs of massive real mature tits better than Josephine's on the web. Glorious big nipples and aerolias. Love watching her knead them with one hand and plunging the fingers of the other into her hot cunt. Special mention of her JOI video - love being told to wank my cock by this beautiful fully bodied lady.
8inchjim 01/01/2023 my favourite milf im glad i finally found what pay site she is on!
12/22/2021
Not too many pairs of massive real mature tits better than Josephine's on the web. Glorious big nipples and aerolias. Love watching her knead them with one hand and plunging the fingers of the other into her hot cunt. Special mention of her JOI video - love being told to wank my cock by this beautiful fully bodied lady.