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tsb2b Novice Jackinchatter

30 posts since 2022-02-18
43 year old
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Another person I wank over:

1. Who is she (Family member, friend, colleague)? Friend

2 .Description of her. Cute oriental lady, around 5'4, slim, long black hair up to just below her shoulder. In good shape as she does pilates and yoga. Got married just before lock down, where her wedding dress showed quite a nice vpl.

3. Age now? 30

4. Age in fantasy or pictures used? late 20s/30

5. How often do you masturbate over her? weekly

6. What are your main source of pictures (Facebook, Instagram, personal collection etc.)? Facebook, instagram and a sneaky bridal perv shot

7. If you fantasise about her, is it purely fictitious fantasy or based on fact, tell us a bit about it. Mainly fictitious. Very sweet and attractive lady, a big hugger, and looks great in a summer dress. Have fantasies of her being slowly undressed and fondled before being taken hard. But she has mentioned she has been harassed / groped before, and that got me (secretly) hard.

8. Have you ever taken advantage of access to any of her personal items, Underwear, etc? No alas, but have seen them

9. Have yer ever told her or hinted to her that you masturbate over her, What was her reaction? No.

10. Have you had any real life sexual interaction with her? No, only the odd vpl / downblouse / upskirt she has carelessly provided.
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vc08 Amateur Jackinchatter

274 posts since 2014-03-21
29 year old curious from United Kingdom
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AussieVoyeur Novice Jackinchatter

77 posts since 2020-05-13
52 year old
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1. Who is she (Family member, friend, colleague)?
Sister in law (wife's younger sister, 9 years age gap)

2 .Description of her.
Tall thin blonde. Mother of two but her body snapped straight back to slim and fit both times

3. Age now?
39

4. Age in fantasy or pictures used?
Teens to current

5. How often do you masturbate over her?
Pretty much every time I have a social interaction with her, usually 2-3 times per week

6. What are your main source of pictures (Facebook, Instagram, personal collection etc.)?
Personal collection, family snaps and some of her private pics obtained from her phone

7. If you fantasise about her, is it purely fictitious fantasy or based on fact, tell us a bit about it.
Sometimes fantasise, sometimes just admire her body. If its a fantasy, usually involves watching her get fucked or being involved but masked so she doesn't know its me.

8. Have you ever taken advantage of access to any of her personal items, Underwear, etc?
Yes...many many times. I am the guy who is trusted to watch her house when she is away. The day I met her years ago, I came in her bra.

9. Have yer ever told her or hinted to her that you masturbate over her, What was her reaction?
No way, she would tell my wife instantly

10. Have you had any real life sexual interaction with her?
No, other than the odd peek down her tops over the years. I once heard her get fucked when on holidays with her and her kids after she got divorced.
Skype me at [email protected]
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Dirtytom Novice Jackinchatter

22 posts since 2022-01-08
62 year old heterosexual male from South U.K.
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vicarswanktoo Amateur Jackinchatter

395 posts since 2011-09-14
60 year old curious
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I have several that would fit this description but I'll start with my massage therapist, a lovely lady a few years older than me who I've become friends with over the years.


1. Who is she (Family member, friend, colleague)?
Massage Therapist (a professional LMT)

2 .Description of her.
Around 65, fit, lovely athletic curves, very pretty in an unassuming way. Gives a great massage, leans into the healing power of it all, whisking away the bad energy, that sort of thing.

3. Age now?
65 or so.

4. Age in fantasy or pictures used?
My favorite picture of her might be about 5 years old, any age really for my fantasies.

5. How often do you masturbate over her?
Every couple of months. I definitely have a wank thinking of her before I go for an appointment.

6. What are your main source of pictures (Facebook, Instagram, personal collection etc.)?
Facebook. She did let me take a picture of her hands for her profile picture in my phone. Thinking about those hands is sexy too.

7. If you fantasise about her, is it purely fictitious fantasy or based on fact, tell us a bit about it.
I fantasize about those accidental touches when she's moving the sheets around leading to a handjob or even better a 69 situation. I did have a whole fantasy story written up in my head one day but never put it to the page. Wish I had done that.

8. Have you ever taken advantage of access to any of her personal items, Underwear, etc?
No. I do shower at her house before my massage (I'm a bit of a clean freak) but the bathroom I use clearly isn't the one she uses.

9. Have yer ever told her or hinted to her that you masturbate over her, What was her reaction?
No. I'm guessing that would be a deal breaker.

10. Have you had any real life sexual interaction with her?
Not really, aside from the occasional accidental touches of my flaccid cock as she moves the sheet around. When I started with her many years ago I would jack off just before going so I wouldn't get stiff during the massage. As I got older and we became friendlier I was wishing that I hadn't trained my body to not get stiff when getting a massage; that combined with my age keeps me from getting hard while on her table. I do remember one time she didn't talk much after some initial pleasantries but then gave me a kiss on the cheek when we were done. I was surprised and should have asked her about it at the time. I thought it would be a regular thing and lead to more but it wasn't and never did. Time before last, though, I remember the room filling with the unmistakable scent of a post-menopausal woman's sexual excitement about 2/3 of the way through the massage so I feel like I may have a similar effect on her. That may have been the time I left so much pre-come behind on the sheets she could not have noticed it as she was changing them. Still thinking I might tell her next time that my arm and back are sore from my regular and vigorous jacking sessions.
Not an actual Vicar
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