Of all the stories I’ve posted to GW Stories, this is the one I’m least proud of. Not because Lauren, my friend’s super sexy 23 year old brunette babysitter, isn’t a tremendous hookup, but because my buddy and his wife walked in on us and now are thinking of firing Lauren because of what they saw…
About three months ago, I was picking up my buddy Bobby for a basketball run we usually have on Saturday mornings. His wife was out of town for the weekend and he was watching the two kids on his own. That meant he was running very late so he had me come in to wait. While I was waiting in his kitchen he was getting his kids situated upstairs. The doorbell rang and he told me to get it, it was their babysitter for the day. This was the first time I saw Lauren and we both seemed a little taken aback when I opened the door. I was taken aback by how hot this woman was. She was dressed down in yoga pants and a long sleeve workout shirt, but she had incredible curves for such a short girl (5’3”). Her hair was pulled back in a pony tail and I remember she had the greatest smile, with big pearly whites and almost all of her teeth showing (think Margot Robbie-like smile, with Rachel Bilson features/curves).
I think she was taken aback expecting to see Bobby, but also I think she felt the same mutual attraction I did (she later confirmed). “You’re not Bobby?” She smirked and laughed as I let her in. I introduced myself and flirted with her for a quick ten seconds about how she’s here to save the day and she went upstairs to help with the kids. As she went up the stairs she gave me a sexy look back as she walked upstairs, probably because she saw me checking out her ass. Bobby came down shortly there after and we went off to our game, but on the way there I had to tease him how I couldn’t believe his wife let him hire a babysitter who was so hot. He laughed, but then seriously said, “she’s great. I’m serious, don’t try to fuck her.” Bobby knows my reputation.
I didn’t give it much of a thought the rest of the day, but when I got out of the shower getting ready to head out that night I opened insta to see that I had a new follow request from Lauren. I gave it 5 seconds of thought about what Bobby said, and then I accepted and friend requested her back. Her profile was filled of pictures of her out with friends or with some of the kids she babysat for (including Bobby’s kids) and she was as sexy as I imagined. I went to like a few of her photos that she looked best in but then realized Bobby and his wife were also insta friends with her. I worried they would see my likes on her private account, so I unliked them. Following her was one thing, but liking photos of her in a bikini and out in a little black dress was another.
She must have gotten a notification of my likes, because she liked a couple of my older photos and then DM’ed me “change your mind? lol.” That’s where we started chatting more frequently, just through DMs and this went on for a few weeks. I really made an effort not to force this because I know Bobby would be pissed, but she was fun to talk to and (have I mentioned) very attractive. She had a bubbly and infectious personality and you could tell why she would be good with kids. I was still wavering about how far to escalate our chats when she flat out just asked, “When are you going to ask me out?”
I told her about Bobby’s reservations, our decade age gap, and the fact that she worked for my close friend as all reasons it wasn’t a great idea even though I really wanted her. She brushed those all aside and I didn’t put up much a fight but I think we both got off a little bit on the fact that she was the one pursuing me and that we were doing something that came with some risk. We went out to dinner later that week, made out in a cocktail bar, and then I went back to her place and fucked for the first time.
The sex was really great and I loved how tight she felt, but I’m going to fast forward to a few months later when our hookups were finally discovered. Lauren and I had been hooking up for a few months and had been careful not to tell anyone. I was pretty upfront that this was all about fun and with our age difference, and her job, this likely wasn’t a long term relationship. She laughed in my face assuming she wanted anything more than that with me. She confidently said, “I’m the one who decides how far this goes hahaha.” But this night she was working and I was going to a mutual friends birthday party that Bobby and his wife would also be at. I had no intention of going over to see Lauren at their place but as I was talking to Bobby and his wife they made note about how they were considering getting a hotel for the night if Lauren could watch the kids for the night. They texted her and she said no problem and then I got a text from her that she wouldn’t be able to come by after they get home because she was staying there for the night.
I left the party a little while later and was texting Lauren on my ride home. I told her how I missed her and she then she sent me a sexy selfie or her in her bra and panties on Bobby’s couch and told me to come over… we had the place to ourselves and the kids were fast asleep. I knew it was wrong, but I liked that, so I sent her a sexy selfie of me (she loves those) and I went over to Bobby’s place. She left the door unlocked and told me to come in…
I walked to the living room and she was under a blanket watching some movie nearly asleep but she perked up when I came in. She rose up off the couch and the blanket dropped in she was only in her purple bra and thong. I bit my lip looking down at her sexy body as she asked me if I had fun tonight, “mhmm” basically ignoring her questions as my hands explored her perfect skin. We kissed briefly as her hands went around my shoulders taking off my jacket and then around my waist as she dropped to her knees. Her pretty eyes looked up at me as she undid my belt and took out my hard cock with her tiny hands and engulfed it with her lips. After a few sucks, she pulled away to unhook her bra revealing her perky tits and giggled sexily before she started working my cock again. One of her hands cupped my balls as the other hang onto my jeans that we still wrapped around my knee caps. Her ponytail bobbed as those lips contributed to a slurping sound from her saliva layering my shaft.
After I was fully hard I pulled out of her pretty mouth and laid her back onto my friend’s nice sofa. She was smart enough to put a blanket underneath her before laying down. I was on my knees looking down on her and I took one of her legs and put it up against my shoulder as I lined up my big hard cock with her tight pussy. She moaned through her closed lips and her eyes closed in ecstasy as I started entering her pussy. “That’s good right there… that’s so good right there” she told me as I started picking up the pace. One of her tits bounced in her hand beneath here from each of my thrusts while the other tit bounced more wildly without her other hand there for support. That other hand was rubbing her pussy as I started rolling my hips into her even faster than before. Before long she was begging me to get deeper and “fuck me from behind.”
She quickly got on all fours on the couch and I got off my knees to stand behind her. I gripped her ass with my hands for a moment before bitting one ass cheek. Then I moved my hands to her waist and started going back inside her from behind. She moaned into a pillow at first thrust before getting more used to the sensation. “ooo, ooo, yeah, oo, yeah just like that, oh it feels so good Brian…” The smacking of my body on her ass not quiet anymore as she tried to quietly moan, “You feel so deep, that’s so good… (she wasn’t quiet).” I reached my hand around so she could suck my finger to be quiet but she almost immediately spit it out to tell me “I’m going to cum.” Before she could finish the sentence her tight pussy got even tighter as it clenched around my cock.
I pulled out of her soaked pussy and she had me sit on the couch. She faced away from me and lowered herself on to my cock. She used my cock like a pogo stick as she began bouncing on it looking back at me as my cock disappeared inside her with each bounce. Once I had regained some stamina I started thrusting back up into her, which really drove her wild and I had completely forgotten about us trying to remain somewhat quiet for the sleeping kids upstairs. That pounding came to an abrupt stop when we heard, “what the fuck!” from Bobby’s wife who could see Lauren bouncing head from across the room.
She hopped of my cock and used the blanket to cover nude body and I reached to the floor to find my jeans. The shock on their faces when they not only saw their cute babysitter getting fucked only got worse when they saw it was me doing it. Bobby went from slightly entertained to pissed when he saw it was me, “what the fuck man!” as I stood next to his couch buttoning up my jeans.
We both apologized, Lauren profusely, but I realized it was better just to get out now and worry about the apologies later. This was the heat of the moment, and frankly I was still hard adding to the awkwardness. I told Bobby that I was sorry and I would call him tomorrow and it was my fault. Lauren started to tear up a bit and that softened Bobby’s wife a bit so that she wasn’t screaming anymore.
Lauren stayed at my place that night and we didn’t fuck again that night even though I wanted too. We went back over to Bobby’s the next day to explain that we had been together for a few months and we didn’t want this to get in the way of Lauren’s job. We realized doing this while she was babysitting was wrong but we had a noise monitor that would have alerted us if either of their 5 or 7 year old kids had an emergency. They were not happy but I felt we did what we could and I tried to take the blame for it all, which Lauren fought back against.
She’s still worried about losing her relationship with this family, but we’re still hooking up so I think she has her priorities. Sometimes I worry my priorities are out of whack…
Source: reddit.com/r/gonewildstories/comments/12bs2es/i_fucked_my_good_friends_babysitter_f23_in_his
Tbh, if you both are single I would high five you as a friend and tell you to get the fuck out of my house haha.