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Nicks Professional Jackinchatter

1356 posts since 2012-06-23
47 year old heterosexual from Just ask
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My wife is the hot one out of the two so I have no desire to even fantasies about her sister.
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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I've posted this before, but my sister-in-law remains my ultimate fantasy.

My wife is super sexy, and quite hot. Her sister is about 10 percent higher on both counts. I would love to do some really dirty things with her, given the opportunity.

SIL is three years younger than my wife, and she's just like a newer, sleeker model of my gorgeous wife.

At our wedding rehearsal, the SIL showed up wearing a low-cut white blouse, a knee-length leather skirt and black 5" stilettos with bare legs. I remember standing there, next to the priest and my soon-to-be betrothed, looking at the SIL and thinking, "I'm marrying the wrong fucking sister."

In the end, of course, married the right girl. But, damn, SIL had me reconsidering my station in life for a brief period of time.

She knows what she does to me. She lives out of state, and whenever I do see her, the hugs are very tight and the kiss (always on the lips) is just a bit too long. Even my wife has noticed that. Fortunately, she says it's just her "dopey kid sister."

What my wife doesn't know is that we went to a family wedding a few years ago, and "dopey kid sister" arranged to sit next to me and made it a point to show off her stocking tops and panties for me, often. Her napkin fell out of her lap, and I bent down to pick it up. With my face within 12 inches of her pussy, she hitched up her short dress to show off her lacy things.

I banged the hell out of my wife later that night. She wondered why I was so enthusiastic. Never have told her why.

SIL also shares a name with my unattainable crush, Melissa, so there's that working in her favor. But I love my wife, and I just keep my lurid thoughts in my brain. She's the smile my wife doesn't understand. grin
Open to interesting ideas
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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
32 year old curious male from USA
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deleting to clean up post history.
Skype: syntheticdreams2077
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Chris41 Amateur Jackinchatter

289 posts since 2017-04-27
46 year old
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I've secretly perv to my wife's sister for over 10 yrs. Its more about the taboo, forbidden fruit, and something I def should not be doing that excites it for me.

I creep pics of her when I'm around her, and save pics when she posts on social media. I jerk to her pics 2-3 times a week.
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I have had a crush on my wife's older sister for a ridiculous ammount of years. We never see eye to eye alot of the time, we even lived together for a few years and those were a strange mix of clashing egos and lust.

As much as we clashed, we bonded alot to the point where we crossed the line more times than we really should have, we never had full sex but more close calls than should have happened.

We both respect where we are in life and who we are with. But those early days still plague me and also fill my wank fantasies.
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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
32 year old curious male from USA
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deleting to clean up post history.
Skype: syntheticdreams2077
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My wife has two younger sisters, one that is a year younger and the other is nearly ten years younger. I have stroked to each of them many times over the years.

Once early in our marriage, the next younger sister stayed at our apartment one night. We only had one bed and so she slept on the couch. It was a small apartment and the couch was only about six feet away from the door to our bedroom.

The talk was interesting before we went to bed, especially since my sister-in-law happened to find one of out Penthouse magazines in the magazine stand after we had dinner. She was paging through it when suddenly my wife realized what she was looking at. My wife ran over and grabbed it from her and took it into our bedroom. We laughed about it and SIL asked why we had it and I told her that I like to read the letters in the Forum section.

Later, when we went to bed my SIL made a comment about us doing some light reading before we turned off the lights! My wife hit me on the shoulder when I said we might.

Once in the bedroom I was horny as hell after all of the talk, but my wife was acting mad. When we got into bed, I tried to kiss her and getting something going, but she was not having any of it. She said her sister could hear us. So I turned and grabbed the Penthouse and started reading the Forum section and pulled down the covers and my PJ's and started jacking off.

My wife told me to stop, but I did not. After a couple of minutes she rolled over and started watching me, then asked me if I was jacking off to the story I was reading or to her sister in the other room. I guess my sly smile told her the answer without me saying anything. She just smiled and watched me finish.
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DirkM22 Professional Jackinchatter

1475 posts since 2019-01-29
26 year old bisexual male
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snu said:
Just got back from holiday last week with my wife and sister in law. Spent hours pretedning to read my kindle admiring her topless body, both her and my wife have nice tits, my wifes smaller than hers but I like that, and both have perfect asses. My cock is so had just thinking of her hard nipples on her sweaty tits.

Slleeping arrangements most nights were me downstairs on the sofa bed, wife and sister upstairs in the same room. The toilet was upstarirs too and no door on the bedroom.

My routine was get up early have a wank then make breakfast.
After breakfast I'd take a walk and enjoy the nudist beach and dunes. If I didnt get to shoot my load in the dunes id have a wank in the sea while admiring the view. Then a quick beer and go back.

They both just want to sunbath all dayso when I got back they'd be sprawled out just wearing their bottoms. Id spend the rest of the day perving over them and then going back to the room for a wank. Sometimes my wife would nip back for a fuck and catch me wanking, i knew who it was but was disappointed her sister did not "catch" me.

Happy times, hope she is still single next year, probably will be because apart from being hot she is high maintenance.

Anyway, its going to be 28C here and she is coming round to spend the day here.


Did your wife and sil ever have lez sex together? Watching that would make you cum.
always ready to JO
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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
32 year old curious male from USA
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deleting to clean up post history.
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Chris41 Amateur Jackinchatter

289 posts since 2017-04-27
46 year old
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I've secretly perved to my sis in law for over 10 years. I collect all pics she posts on social media. I've cum in her panties, body lotion and a few other things. I also sneak creep shots of her when we are together so I can jerk to them later.

Most of the thrill is the taboo that she is my wife's sister and how wrong it is, and how nobody knows
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Sparkie Enlightened Jackinchatter

4345 posts since 2005-08-16
53 year old heterosexual male from Kansas City
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Nicks said:
My wife is the hot one out of the two so I have no desire to even fantasies about her sister.


No hot SIL for me either and her brother's wife isn't hot either.
WTF Do you want now?
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My SIL and I have had a semi-fling for decades. Never all the way, just very risque.
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Feminine_MaleLesbian Professional Jackinchatter

1088 posts since 2015-04-17
56 year old heterosexual from Louisville, KY.
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Been quite a bit of sister-in-law posts lately.
My ex-wife had 5 sisters and I was often jacking off to 2 of them. She knew I jacked off to them and was okay with it. She said she didn't blame me because they were really hot and she knew a of guys probably jacked off to them. We stayed friends after our divorce and I also stayed friends with her family and especially with her two sisters. Unfortunately, my ex-wife passed away some time ago, but I am still close to her family and again especially with he 2 sisters, but for a while now, both of them have been quite a bit flirty, but in different ways. One seems a bit more like she wants to be closer in a more romantic way while the other has seems to be flat out saying things, like once she said she was having a rough time and I asked her if there was anything she needed and she said "yeah, I could use about 9 1/2 inches", but then says she is just kidding, but I think she is really wanting to mess around and saying things like that to gauge my reaction and then saying she is just joking just in case I may have thought it was inappropriate, which I don't. I actually think my ex-wife would approve if I got to mess around with one or both of them. I think it would be great after all these years I have been jacking off to them.
The thing is that I totally think very highly of them both and they both mean a lot more to me than just that> they are like best friends and family to me still I really thought something was going to happen a while back with one of them when we had plans on getting together to hang out, but we are in different towns, not too far away, but still a little bit of a drive and trying to coorddinate with our schedules has been tricky, but I am still hoping to get some time with them no matter if anything else happens or not. Not going to lie though, I am hoping id does.
Love stroking with the women in person, on the phone or on webcam.
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girlsorguys Amateur Jackinchatter

216 posts since 2016-02-10
42 year old curious
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Chris41 said:
I've secretly perv to my wife's sister for over 10 yrs. Its more about the taboo, forbidden fruit, and something I def should not be doing that excites it for me.

I creep pics of her when I'm around her, and save pics when she posts on social media. I jerk to her pics 2-3 times a week.


I had to double check that I didn't write that grin
Send me your pics that you would like me to cum to
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Chris41 Amateur Jackinchatter

289 posts since 2017-04-27
46 year old
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Saw my Sis-In-Law this afternoon, now I'm feverishly jerkin off to her pics
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