I Was The Fun Baby Sitter, Twenty Some Years Later I Am Worried.

I have been a stay at home mom for most of their childhood and now have been back to work for about a year and the thought of a sitter crossed my mind. I then had a flash back of the two boys I sat for during summers, not at the same time though separate houses over three summers. The second one had the attitude at first that he was too old to be looked after, his plan was to ride his bike all day and be gone, asked his mother if going to the beach would be okay with her and she told me he would love it. I put my bikini in the bag hoping that would keep his attention for me, it worked great and when we got back home I stayed in it for a bit just wearing some shorts over the bottoms.
He was constantly around me, I was getting a little worked up with all the attention, I thought maybe changing back into my clothes would be better than his mother coming home to me in a bikini top and he said Oh, Man really, you have to change? I teased him saying Why, you like me wearing this top? and even jiggled them for him. He was beside completely beside himself, his mind was racing and I could see it, I looked at him and said Do you promise not to tell if I let you help me? Help you what he said and repeated telling me he promised a dozen times.
We went to his bedroom, I had about half an hour for sure, closer to forty five minutes, I turned around and told him to untie it back there then I bent way over and told him to take it off over my head. I thought he was going to hyperventilate when I told him he could touch them also and his hands were shaking as he did it. I told him after a few minutes Okay, my bottoms are next and I undid my jean shorts and had him pull them down while I shimmed out of them. He reached up grabbing the top of my bikini bottoms with his wide and I said Yeah, go ahead and he slowly pulled them down staring at my ass the whole time, I turned around a few times like a ballerina then told him to get my underwear out of the bag.
He was down on his knees holding them for me to step into, he was happier than ever to help out as he pulled them up letting his hands run over my legs all the way to my my hips.
He stood there just staring at my breasts, I said go ahead, touch them if you want but we need to hurry it up. I told him bra was next and he was really struggling with that one, got him straightened out and he managed it in the back also. We finished dressing me and he said I was best sitter he ever had, I told him Yeah, and we still have a lot of summer left together.
I stood there years later staring at my son and thinking What would I do if some hot teenage sitter was letting him do the same thing, you cannot change the past and just hope for the best. I sat him down and we talked about getting a sitter instead of daycare. He told me Oh, that would be fun instead of going to that prison, I was like Prison? really, kid you get more attention given to you than you even realize.
One of the women who should up was older and large, I hired her on the spot.

Comments

Anonymous

by Anonymous on Jul 11, 2025 at 12:50 PM

You were a naughty girl Sherri. Imnsure that kid remembers it all well and still jerks his dick to the memories.

Did you ever give him a hand job, bj or let him finger, lick or fuck your naughty teen c unt?

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Anonymous

by Anonymous on Jul 11, 2025 at 12:50 PM

I can't comment on your own son because his age is unclear and it's probably way too early to think of such things in his case, but as for the guy you babysat...I see nothing wrong...he was just being a normal, helpful person. Hundreds of years ago you would have had your own chambermaid to help you undress, but in these tough times, we have to make do. Also, you did a great job of showing him that there's no reason to be ashamed about the human body. Changing is a practical, not sexual, act. I'm sure he felt much more comfortable when he later had to change for gym class, or with his sports team, or on overnight trips. Any boy would have been lucky to have a pragmatic, open-minded sitter like you.

Out of curiosity, do you have an age maximum? I'm 47 and might need someone to look after me some evenings.

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Anonymous

by Anonymous on Jul 11, 2025 at 1:58 PM

I was a bad sitter too, but...I was into the dads, not the young guys.

Especially the dads who would drive me home afterward. I felt so protected and safe.

It's funny when I look back on it. There were dads who didn't want to. I think they were secretly gay and had married because it was expected back then. There were dads who wanted to but were too scared. These always seemed unhappy. And then there were dads who appreciated a cute babysitter who pretended to be innocent and a virgin.

Interestingly, all the dads who did stuff to me paid me. Not one of them understood that I would have done it for free because they turned me on and I liked them.

I too had to do the socially appropriate thing and marry a guy in my own age bracket. My husband always accuses me of flirting with hot guys. He's got it all wrong. The guys I like are much, much older and not hot in the classical sense.

Hubby has no idea that I'm in an ongoing relationship with a 76-year-old widower, or that he, not hubs, fathered two of our kids.

Wives - monitor your husbands around babysitters!

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Anonymous

by Anonymous on Jul 12, 2025 at 9:26 AM

I would have loved older and large. My mother was a bbw and I have that fetish to this day.

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Anonymous

by Anonymous on Jul 12, 2025 at 12:05 PM

Yeah, I've always wondered what pervvy sitters see in small dicks, when they can enjoy big, man-sized, hairy ones by fucking the dads.

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