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Cuckysitter?

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littlecrissydoll

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Posts: 9
#1
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Has anyone ever had their wife or girlfriend hire or arrange a 'cuckysitter' to stay and babysit you while she goes out and does her thing? If so, who was it? Did she get one of her friends or did she hire someone? What was that experience like? How long did she babysit you, how did she treat you, etc? Was she sweet, was she mean, did she treat you like a young or an equal? What prompted your wife/gf to get a cuckysitter for you?
My girlfriend, who definitely sees me as more of a young than a man (but still loves me very much), goes out on dates and there's nothing I can do to stop it. One time, out of frustration, I masturbated into her panty drawer, which didn't leave much of a mess since I don't cum a lot, but she still noticed it. I guess I did it out of my desire to get even with her for doing other guys when she won't give me any sex, and has basically forbidden me to play with myself. Not sure why I thought that would make me feel better or feel like I got even with her, but I was really frustrated. When she came home and discovered what I had done, she flipped out, firstly because I played with myself without permission, and second because I did it in her panty drawer. Anyway, she did give me a hard paddling with her hairbrush and threatened me that if she catches me behaving this way again, that she might have to hire a cuckysitter to watch me while she's out to make sure I behave. On the one hand, I think that would be completely humiliating and I don't know what she would be like or how she would treat me, but on the other hand I am so desperate for female 'attention'. Do you think there's a chance that if I did get a cuckysitter that she might sympathize with me and.. you know, help me out. Or am I being unrealistic? I know if I do it again, I'll surely get another spanking (which is kinda exciting, but definitely hurts and she doesn't stop until I am blubbering and sobbing real tears), but I don't know if she'll actually hire someone to watch me - and if she does, if it will be a good thing or just bring embarrassment.
I absolutely love my girlfriend and she loves me, but she just doesn't see me as a man and treats me like a young, and I'm desperate just to have the chance to be around a woman with the idea that maybe something could happen. She has forbidden me to even attempt to look for another woman (and has assured me while she thinks I'm "cute" - not hot, but cute - that I don't have the 'attributes' that women need), even though she has no problem relaxing with other men. I wonder if this is a possible way to be around a woman and not get into trouble, since she would be the one that hired her. My mind is racing.
What do you think?
ware_simon

Member


Posts: 108
#2
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This is one of my fantasies - imagine your wife or girlfriend taunting you whilst she prepares for her date. The door bell rings and you are told to answer it in your sissy attire. It is your "cucksitter". Maybe you know her but you weren't aware she knew of your sissy cuckold status - may be she is a total stranger. You have to listen quietly whilst your wife/girlfriend gives the sitter the instructions as to what you have done, need to be done, bedtime, food, punishment, etc. Then there is the peck on the forhead from your wife/girlfriend with a "better be good" comment before you are left alone with the sitter and there is that awful awkward embarrassing feeling.
Great! would love to hear thoughts and or experiences.
stinky

Member

Posts: 167
#3
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sounds like heaven! i'd love to have an older woman (ma'am) who leaves me with a sitter while she goes on dates with black men. they would be left with strict instructions to tease and deny or completely milk me, with their choice of not letting me cum at all, keeping me on the edge, or multiple ruined orgasms with lots of post orgasm *** and i'd have to provide any oral services they required.
of course i would be embarrassed at having to lick up my precum and my cummies as well as any messies ma'am brings home.
sissycindylynn

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Posts: 333 Pictures: 4 
#4 · Edited by: sissycindylynn
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My ex wife used to have her lady friend, ****** or her sister come over while she went out. I later found out they knew I was a sissy and wore panties but nothing that way happened, unfortunately.
dilatateur

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Posts: 1171
#5 
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nice post
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Cuckysitter?
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