# # #

My female babysitter/cousin and I. Learning what “playing doctor” meant at age 11 (True story)

1842 words | 4 |4.52

This is a true story about my babysitter and I.

As bullshit as this story may appear to some readers, I assure you it happened. I used the #abuse tag because although I didn’t see it as that then, and I still don’t now, I do realize that that’s certainly what it’s considered these days.

Anyway, when I (M) was 11 and my babysitter (F) was 15, my mom and dad used/hired her to be my babysitter when they were at work. This girl, R, was also my cousin. Everything went as you may expect for a couple of weeks or so but then one day she wanted me to play “doctor” with her. I had never heard that term used before and I had no idea what “playing doctor” meant, although any kid these days would. I mean they insinuate on movies and shows that it’s “something naughty”, so it would be obvious but I had never heard that at the time.

So I told her I didn’t know how to play it and she told me no problem, it was easy and all I had to do was what she told me to do. We were in my bedroom and she told me to lie on the floor near her. She was sitting on the floor at the time. So I did, face up, but she told me to turn face down, which I did. The first thing she started doing was rubbing my back. Why, I have no idea. But that’s what she did. It wasn’t long though, until she was rubbing my ass. I thought that was a little unusual but no big deal. Then her hands stopped rubbing and now she was squeezing my ass cheeks.

I know now, of course, that she was just progressing further to see at what point I was going to freak out or say I didn’t want to play anymore. After she had been squeezing and rubbing my ass cheeks for a few minutes she suddenly stopped and said it was my turn to do her. So I sat up and she lay face down. Not knowing how this “game” was to be played, I figured the safest thing to do (not wanting to look like an idiot) was simply the same thing she did. So I started rubbing her back but almost immediately she said “No, my butt.” So I did. At first I tentatively rubbed it lightly, but thought “Fuck it” and just decided to go for it and was squeezing the heck out of her ass, not believing she was letting me. Sure enough, she didn’t say stop like I was thinking she was going to.

I was really massaging her ass with all caution thrown to the wind when she said “My turn again”. I wasn’t 100% hip on giving up two handfuls of girl ass only to get my own ass rubbed again but she sat up and so I lay back down. This time she went straight to squeezing my ass and surprised me a couple of minutes later when she started to pull my shorts down in the back. I grabbed them. I thought it was some kind of trick or she was going to spank my ass or something. She said “What are you doing?” So I replied “What are YOU doing?” She then said that to play the game right I had to pull them down at least a little bit.

I wasn’t about to pull down my shorts and expose my bare ass to a girl, the thought of it was embarrassing, but if SHE did it herself…well, that was different. So I let go of them but made no move to pull them down. For a second she didn’t do anything so I just laid there. Then she told me to raise up a little, which I did, and she didn’t pull them down a little bit, she pulled them almost down to my knees. Before that surprise could sink in, I had expected her to just squeeze my bare ass, she didn’t start squeezing, she spread my butt cheeks. Then she started squeezing, spreading, squeezing, spreading…like that. Not being completely stupid, I was thinking this next phase of “playing doctor” may have something to do with a person’s butthole.

I didn’t know what she was planning on sticking in there but at that point, she said it was again my turn to do her. Holy crap. I was 11 but I definitely knew pulling down a girl’s pants was a no-no and I didn’t know if a) I’d have the nerve for it or b) she was actually going to let me if I tried. What I was nervous about happening was that she’d jump up screaming “What the hell are you doing!!” and tattle to everybody that this had all been my idea. She had just said it was my turn to pull down her pants, but I knew that didn’t seem likely to happen without somebody getting in trouble, probably me.

So I started massaging her ass again. After a minute, I was thinking to myself “If I do try to pull them down and she jumps up, I’ll just deny I did it.” I wanted to do it, but pretty nervous about it. Plus, I had on shorts but she had on jeans. She must have unsnapped her jeans the last time we switched but I didn’t see her do it. That being the case, I was surprised at the ease with which the back of her jeans came down a couple of inches when I tried it. She raised her hips exactly like she had told me to do, so again I said “Fuck it” and just pulled them down in the back like I didn’t give a single fuck.

There her bare ass was, so no use now being nervous about it, just go for it so I did. The instant I had a handful of bare ass cheek the first things I noticed were how warm it was and how soft it was. I was thinking “Holy shit! This is great!” I wasn’t sure about the ass-cheek-spreading but I did it and she didn’t stop me. I had an urge to stick my finger in her butthole or at least touch it but I didn’t dare. To this day, I don’t know if she really wanted me to grope her or whether she was letting me so that I’d have an idea what a great opportunity I was giving up should I decide to call off this “playing doctor” game. Or both. Who knows.

In any case, I was doing it and she was letting me. I had no objections to it, for sure. After a few minutes of that she told me it was her turn and I was wondering where this was going next. Probably butthole, I was pretty sure. However, if she continued with this tit-for-tat that was happening so far, she was going to have to do something pretty drastic for me to say no.

As before, she went straight to spreading my cheeks open but no squeezing or massaging this time. She must have licked her finger or something because when she did indeed touch my butthole with her finger (like I figured she was about to), it was wet. I thought maybe she was just going to touch it but she stick it in, but barely. Then a little more. She said, “Does this hurt?” I said, “No” and she immediately put in in more. Like I mentioned earlier that I threw caution to the wind, she must have done the same because she just kept pushing it in further until she could go no further. She didn’t ask me if it hurt again, which it didn’t or I would have said something, but she had her entire finger in my butt. Then she pulled it all the way out and put it all the way in again.

Then kind of an awkward moment happened because while she was doing this, I was fantasizing that, barring unforeseen circumstances, I was going to be fingering her butthole just the same way in just a minute. My pecker was hard as a rock. But it was safely under me and I knew she couldn’t see it. As things turn out sometimes though, she must have also been thinking about or wondering about my hard pecker. Whether it was or not, anyway.

She said “Raise up a second” and I thought she meant to pull my shorts the rest of the way off or something. Instead, she cupped my dick and balls with her hand and held it there. I froze. Then she moved her hand and stuck her finger back in my ass. I was hoping she wasn’t going to say anything about my dick but she said “Oooh! Seems like you like playing doctor!”. So that was the “awkward moment” part. My dick was hard because I was thinking about fingering her ass but she thought it was hard because she was fingering MY ass.

Her “turn” lasted quite a while longer than it had before. So long, in fact, that I began to think I wasn’t going to have a turn at all. That this was the end of the game. Although at that point, she hadn’t bothered to pull her jeans up, she was sitting on my floor on her bare ass. I was so relieved when she finally said the magic words and that it was my turn to do her. Also, she had told me this ass-fingering was called “taking somebody’s temperature”. So she told me it was my turn to take her temperature.

There she was face down and there was that bare ass again but I decided this was way past the point of her jumping up and acting like she couldn’t believe I had the nerve to do…whatever. So I spread her cheeks for a second, then wet my finger in my mouth and put it all the way in her ass. She didn’t flinch but she said “You’re supposed to ask if it hurts” so I said “Well, does it?” and she said “No”. Which confused me as to what her point was to having said anything in the first place then.

So I fingered her ass for a while and even at one point asked her if it was her turn again. She said no, it was still my turn, keep going. So I did. I was thinking to myself that this was freaking unbelievable. It was awesome and for all this all I did was take a finger in the ass? Incredible.

She eventually told me that was enough but she had more stuff to do next time if I wanted to play again. I didn’t want to appear too eager (being the cool guy I was and all) so I just said “Ok” like it was just another day. (In fact, it was quite a bit more.)

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:
1 Star2 Stars3 Stars4 Stars5 Stars
(average: 4.52 out of 50 votes)

By # # #


  • Reply Boob ID:1eebryqv12dw

    Will there be part 2????

  • Reply fan of richard ID:2ql4smrm4

    damn i need the second part man. even if you are not posting it i will give you my contact details so mail me over.

  • Reply [email protected] ID:yg1h5i68

    Good start. Part 2 please!

    • Richard ID:5sowhxud3

      I’ve been trying to start it but I’m realizing (the more I think about it) how unbelievable it appears in print lol I’ve had somewhat of an unusual life and narrating some of the things I’ve experienced makes it appear to some people that I’m just making up bullshit stories. The stories I like to read are the ones that seem real and believable but I know that my own are not like that, even though I’m just telling exactly what really, actually happened. 100% in real life happened. If that doesn’t make sense, here are two examples: One thing that I’d like to tell about sooner or later is about a girlfriend of mine cuckolding me in a very unusual way, and another time about me cuckolding this guy without knowing at the time that’s what I was doing. Even though the stories seem like complete bullshit, I was there and it happened lol Point is, I’m trying to tell the rest of this story about my babysitter, with all the details, but word it in such a way so that it isn’t instantly dismissed as bullshit. And that’s not proving to be easy lol