My [21m] mom’s friend [43f] let me suck on her tits and jerked me off while drunk after I brought up a dirty secret from her past

So wild title, but hear me out. This happened over the summer.

This may break some rules but I hope not, anyways, this bitch is a party animal, she’s married and in a very good and very bad at times relationship, she has 4 kids and has an absolute milf body. She’s been best friends with my mom for as long as I can remember really, let’s call her Sara.

Sara and her husband aren’t rich but they’re pretty well off, and so this year, she invited my single mother and I to vacation with her and her family to Miami Beach.

Now her oldest kid is only 17, so there’s a bit of an age difference and we don’t have a lot in common, but my mom and Sara are fun to be around especially when we all drink. My mom is super laid back with me and so us drinking together has been going on for a few years.

Sidetracked a bit, so anyways, this vacation was going to go great, until Sara’s husband got covid a few weeks before we were supposed to leave. He would have been fine to go but he ended up deciding to stay back, so eventually the day came, my mom and I and then Sara and her 4 kids all loaded up on the plane and flew down to Miami, it was going to be great.

So we planned on being there for about a week, but we only got two hotel rooms to save money. We were the adults so Sara, her husband, then my mom and I would share one room, then Sara’s 4 kids would share the other room nextdoor. Being an only child with a single mother, we were close enough to where we could sleep with each other and it not be weird, so it was whatever. But since Sara’s husband wasn’t there, it was just us 3 in the room instead.

Like I said, Sara is a party gal and she brings out the worst in my mom in that regard, the first thing we did when we got to Miami was hit the infamous Miami beaches, but we stopped at the liquor store first so Sara could pick up some handles. We got to the beach, sat in the sand, and soaked in the summer sun. This is how I spent the better part of that week there.

And I’m ngl, on like the third or fourth day of the trip, I started losing it a bit. Going that long without busting a nut was incredibly irregular for me due to the fact that I have such a high libido, so the reality of the situation started settling in a bit. Walking to the beach on the third day, having two sexy middle aged “single” women with me, it was getting me a bit.

When they laid out on the sand and tanned, it was hard not to stare at both, I even started peeking glances at my mom, I couldn’t help it, the two had similar bodies and since my mom had been single for so long, she knew how to be sexy.

Now at this point in the trip, Sara was finally getting the cracks to show in my mom, and the both started drinking pretty heavily on this day, I still stayed relatively sober, but the two had been drinking so much that it was time for another alcohol run. My mom said she wanted to go for a swim for a bit and asked if I would go with Sara to go get some more booze back at the hotel room, so I said sure while my mom would stay with Sara’s kids at the beach.

Sara and I begin walking up the beach and she’s not doing to well, she’s stumbling a bit and holding onto me and stuff, and I begin to think that this isn’t a good idea and that she might need to settle down for a bit.

But it was me who needed to settle down too. Just something about feeling her sun tan lotioned skin in my arms, her leaning against me, this alpha male instinct took over in me, and I started getting aroused, and as you probably know, it is impossible to hid even a slight chub in swim trunks, it was bulging too much.

We made it through the hotel lobby and into the elevator before it really started showing up, and the drunk bastard took notice of it too, and she goes “What’s this?” And laughs as she grabs me cock over my trunks and laughs as she holds it for a second. It completely caught me off guard and I tell her stop right away and she just laughs. I was at a loss for words, but the horniness in me loved it.

The elevator opens, we stumble to our room, her drunk, me horny, it was rough. I get her to our room and sit her on the bed before I sorta laugh off what just happened. That was when I decided to remind her of the time that she did something similar to me when I was “younger” to tease her and kinda poke fun at the situation.

(So I don’t get the post removed. In this instance, again, she was drunk but it didn’t hurt me or anything so I never held it against her or hated her for it. She flashed me in the back seat of a car and “made” me touch her breasts. It could be perceived as very wrong and I guess in a way it was, but I loved it, so I usually just made fun of her for it but she hated when I brought it up, especially in front of my mom despite my mom being ok with it now after I assured her numerous times I was ok)

As soon as I brought that up, she seemed to have gotten super serious and she, in her drunken state, got this pouty puppy face and said “Awww baby I’m so sorry about that” and she gets up and stumbles over to my mom and I’s bed. Now I was still horny at this point and I was losing my good decision making skills, and she sorta put her hand on my thigh for balance before sitting down next to me and she like hugged me and said “I’m so sorry is there anyway I can make it up to you?”

Like I said, my judgment was fading, I “joked”, “Yeah, show me your boobs again” and without hesitation, this bitch goes “Well ok” and pulls her breasts out of her top and smiles. I’m blown away, and my cock instantly got harder than before. I’m staring in awe for a few seconds before she goes “Better?” And I in my trace go “Uhhh… yeah” and then she sits there for a second and then in her sadder voice, she goes, “Noooo that’s not good enough” and she stands up guys, gets in front of me, and she walks her breasts into my face and says “Here”

I kinda push away a bit before she says “noo please I want to apologize” and she cups her breats and points it right into my face, her nipples grazing my cheek and chin. Finally, I give in, the horniness got to me, and I start sucking on her, fuck it felt amazing. She walks into me and falls ontop of me basically crushing my cock with her right breast in my mouth. I let out an “ahhhh” and she says “What, what’s the matter?” As I rolled her off and said “You crushed my dick”

She goes “I’m sorry” and then she goes “here” and reaches down into my pants and starts jerking me off. She’s being kinda rough and she’s pulling at me by saying “come here, lay down” and since she had a firm grip, I followed. I laid down as she pulled my trunks down to my thighs and I laid down in the bed as she layed down next to me but basically on top of me as she jerked me off feeding me her nipples to suck on.

I was so horny, I lasted maybe 3 minutes before I exploded all over my chest, her hand, and the bed. One of my best nuts ever, it was amazing. Having her tits in my face as she jerked me off was legendary.

But as soon as it was done, we both snapped back to reality really quick, it sobered her because she said “oh my God, what have I done” and got up and ran as best she could to the bathroom and shut the door before she started crying. She kept yelling out “oh my God I’m so sorry” “please forgive me I’m so sorry” “what have I done” “your mom’s going to kill me”, things like that.

I kept trying to get her to calm down and tell her that it was OK and stuff, but she wouldn’t believe me. She just cried and cried in the bathroom. So, since my mom and I are close, I decided to call her.

She called me back as soon as she got back to her phone a few minutes later, and I explained the situation. I basically told her that it had been a long time since I had jerked off so I was super aroused and that I joked about “the incident” with Sara since she groped me in the elevator that she felt super guilty again and wanted to make it up to me before proceeding to show me her tits again. Then mom said “Is that all she did?” And I said “well no” and mom asked “what happened?” And I said “well… she told me I could suck on it, so i did” and I chuckled a bit and she goes “Oh my God” and started cracking up and then she said “well did you take care of yourself?” And then I said “she kinda helped with that a bit too” and my goes “Oh my God, Sara!!” Through her laughing, so mom wasn’t worried.

But then I said “but now Sara is super disappointed and she’s crying in the bathroom, can you come up and tell her it’s ok and everything again” and mom was laughing saying cheeky remarks like asking if the only reason I came on the trip was to hookup with Sara and stuff. Truth is, I felt pretty guilty too, but it was super sexy.

A few minutes later, mom got back from the beach and she made some cheeky remark saying something like “Why are you crying Sara? It sounded like you had fun” and that made Sara cry some more before my mom opened the door and went in and consoled her while I awkwardly laid in my bed.

She came out and walked over to me and then asked me if I was actually ok, like mom sobered up a bit now too. I reassured her I was and she hugged me and I said sorry again and she was like “It’s ok son, I get it, you’re young and haven’t gotten it out of your system in a while, being in that situation, I don’t blame you. As long as you’re ok”

A few minutes later Sara came out and still sniffling apologized to me again and I apologized too but then my mom was there kinda fueling the fire saying things like “Sara it’s ok he’s a young guy here with two milfs like us, you can’t blame him for wanting to get a little frisky” and then she was like “I’m sure he loved it, it’s ok” and I nodded in approval before Sara finally lightened up and walked over to me and asked if we could hug it out, and so I did, and we both apologized to each other before my mom added another smart ass remark saying something like “Do I need to leave the room for round two? Was that hug too much for you son?” Directed at me and Sara laughed finally and said “I need a nap”

The rest of the trip and the time since has been excellent. It was just a one time thing. It was super hot, but we’re close. We’re family friends, plus she’s married. But every so often, even a few days ago which reminded me to share this, mom likes to give us a hard time about it to Sara’s displeasure. Sara spilled her drink on her shirt and it was white and she didn’t have a bra on, so Sara goes “OMG sorry!!” to me tries to cover up quickly and then my mom goes “You let him suck on it remember, it’s ok if he sees it” and Sara shot mom a look. I chuckled before going to my room and blowing a load.

Thanks for reading, I hope you enjoyed as much as I enjoyed reminiscing.

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