Hooking up with the guy I used to babysit [FM]

Not often I experience being the older woman, but I did this week.

I’ve been browsing Tinder a lot lately. I do it for conversation as much as anything else these days, and tend to have it set to only show women, since I find they seem to be more willing to have a chat without necessarily wanting to escalate things. Every so often, for reasons I don’t get, profiles outside my search filter show up (usually super likes, I think). So I’m sitting at home on the sofa idly swiping left and right when I notice a boy who’s super liked me. I like him back, because he’s cute and it’s only polite when someone does that, then go back to talking to a vegan girl who is trying, and failing, to put me off meat.

I get a message from the super like guy saying long time no see and referring to me by my full name. I go by ‘Jay’, and you wouldn’t really guess my full name from that, so the only people who know it tend to be those I’ve known since I was a kid. I go back to his profile with a mild sense of alarm, because my bio is a fairly abrupt request to stop inviting me to threesomes and a joke about anal- not family friend-friendly. Anyway, the guy- Tom- is an 18 year-old redhead. A full 7 years younger than me. He looks familiar, and it’s only after looking at a couple of his photos that I realise I used to babysit him when I was at school.

I say hi back and we catch up on the last few years, but he keeps steering the conversation towards sex. First just asking if I’ve had a threesome before (I’ve had more than one- hence why I’m sick of them), then going back to other things, like the time he saw me naked in the changing room when I took him and his sister to the swimming baths, or when I had to tell him off once for grabbing my boobs like a little sex pest. Needless to say, these aren’t sexy memories for me, but he’s clearly after something now, and it plants the seed in my brain.

It turns out he works on the street I live on, so we make plans for what I insist will be a platonic lunch… until he shows up. He’s very tall, and clearly takes care of himself. His forearms make me squirmy and he has an amazing sleeve tattoo. The kid I babysat actually has a tattoo!

We get talking, and he can tell I’m flustered, because he quickly moves to sit beside rather than opposite me. As conversation moves on, he puts his hand on my knee, and slowly starts running his fingers up and down my inner leg. I’m wearing a short dress because the weather’s nice, so the feeling of his hand on my bare skin has me getting progressively wetter. Eventually he asks to see my flat, and I can’t say yes fast enough.

It’s only a short walk back, but there’s a knot of familiar tension in my belly the whole way, particularly when he opens a door for me and ushers me through with a hand on the small of my back. We say hi to the concierge, who clearly knows I’m about to get fucked, and that only makes it worse. We get to the lift, and once the doors close behind us Tom is on me. This kid I used to babysit pins me to the wall and kisses me roughly, with one of his hands gently on my throat. I open my mouth to his tongue and let him in, feeling all kinds of messed up for doing so.

The lift gets us to my floor too soon, and we make the short walk to my door with his hand under my dress fondling my arse. I fumble with the keys, and when I drop them he just stays still, forcing to drop my head to right beside his crotch as I pick them up. When I do get the door open, he pushes me inside, slams it closed and has me up against the wall again. He has a fistful of my hair in one hand, and with the other he reaches under my dress, pulls my soaked thong to the side and strokes my clit with his knuckles for just a second before sliding first one, then a second finger fully inside me.

I’m still gasping from the sudden fullness when he starts pumping his fingers in and out. He goes back to kissing me, but the whole thing is so intense that I’m moaning too much to kiss back. Instead, he yanks my head to the side and starts licking and sucking on my neck. Then, as if only just remembering the exist, he pulls back and looks at my boobs. Even if I hadn’t already told him I wasn’t wearing a bra, he’d know now because my nipples are hard and showing. He slips his fingers out of my pussy and, ignoring the look I was giving him hoping he’d make me suck them, licks them for himself. He yanks my dress down to free my boobs and immediately takes one in his mouth. He tells me that he likes that I now have a nipple ring, which just reminds me of the whole babysitter-babysittee dynamic and the whole boob munching aspect gets a little freudian for me, so I push him away and slide my back down the wall to bring my head level with his crotch again.

He goes to open his suit pants, and the snap of his belt as he unfastens it gets me right back in the mood. I take over and yank his pants and boxers down in one go to release his dick. Contrary to popular opinion, some dicks are attractive in their own right, and this guy had a nice dick, with perfectly groomed pubic hair. I had to have it.

I took him in my mouth, slowly at first, paying the head its due respect. Then I remembered he was 18, and probably hadn’t shagged a girl who knew what she was doing yet, so I took in more, and more until his entire cock was filling my mouth and throat. I looked up at him with my most innocent expression, and saw the face of a boy who was about to nut straight into my oesophagus if I didn’t release him soon.

I pulled out without so much as gagging and he just said ‘fuck’ and ejaculated all over my face. Bless him, it wasn’t intentional, but it pissed me off no end at the time. Partly because I had my makeup done all nice, and partly because I’d wanted to feel him fill up my pussy with that cum. Still, even as I chastised him for lacking control, I fed myself his cum and cleaned off his cock with my mouth. Then I pointed out that he’d taken a 1 hour 20 minute lunch break and was probably fired by this point. He hurried out the door with his shirt untucked and me still sat on the floor half-naked.

That afternoon, I fucked myself senseless with a dildo and he got a bollocking for being late. I’m back in work now, so we’ve not had the chance to meet up again yet. Plus, I’m going to make him sweat on whether or not he gets to fuck me. I’m sadistic like that. Oh well, onwards and upwards. Have a great week, everyone!

Source: reddit.com/r/gonewildstories/comments/cyjxd0/hooking_up_with_the_guy_i_used_to_babysit_fm