I slept with my ex-wife’s best friend’s daughter [MF]

This is a long build up.. I think it helps knowing all of the backstory here.

When I married my ex-wife almost 20 years ago, her maid of honor was her best friend Alyssa. Alyssa was 20 years old, and had a baby (Madison) when she was younger. Alyssa was a single mother, who desperately tried to find a man, any man, to stick around and help raise her kid. (mostly a money problem)

For the next few years, we did as much as we could to help out. We weren’t making much money ourselves, so we babysat while she was out fucking random guys.. or I’d pay an overdue electric bill she left open on the table for us to see.

Alyssa eventually got a guy to stick around, and moved a few hours away. We barely saw her and Madison for the next 17 years. The new guy seemed decent enough, and Madison grew up to have a somewhat normal life.

Fast forward to the year 2020. Alyssa and Madison needed to move back to town because Madison’s step-dad died of cancer, and Alyssa was out of a job due to the covid shut-down. My divorce was finalized in 2013 but I still managed to kept mostly in touch via social media with Alyssa. Out of the blue, I get a call from Alyssa to help her and Madison move back home (I have a large truck that I stupidly put all over social media so everyone knows). I agree to help, and set off one weekend summer day with my truck and trailer to help.

I spend the next few months helping Alyssa and Madison when I can. I’m not handy by any means, but I do my best to play the part when they need something done in their new apartment. Madison has grown up to be a very good looking young woman. She’s nerdy in a great way, blond, and very tiny. She’s about 5’1” and probably can’t weigh more than 100 lbs. She is always wearing a hoodie, even in the summer. Even with the baggy clothes, I can tell she’s no more than an A cup. She reminds me of a tad less attractive version of Anna Kendrick.

Alyssa gets some bullshit job, and is gone most days from mid-afternoon to right before midnight. I’m in and out of their apartment doing various things/errands for them a few times a week. Mostly picking up pandemic groceries (they only have 1 car). I do my best over the summer and into winter to not fit into a husband role or even a father-figure role to these women. Madison is in her 2nd year of college, and is doing all her work from home in the fall. We chat on and off when I’m there about who the fuck knows what… I’m usually there for all of 10 mins before I split.

Towards winter of 2020 I start noticing Madison wearing less and less clothes when I’m around. I’ve never seen this girl without a hoodie and baggy pants on. When I’m over, even with Alyssa around, she starts wearing shirts with no bra, and yoga pants. I don’t think too much of this (meaning her doing this for my benefit), but do jerk off a few times to thoughts of her little 20 year old body. In the weeks to follow, I start showing up with any excuse I can make, just to get a look at and talk with Madison. We both play a lot of video games and eventually find out that we both play call of duty on xbox live. I take a chance and get her gamer tag and invite her to play one night.

It turns out, Madison comes out of her shy shell when she’s playing video games. We end up playing for a few months almost every night together. She’s a lot of fun, and we talk about pretty intimate things. During this time, I am worried that she’s making me out to be a father figure she’s missing. I have zero desire to fill that role for anyone, and decide I should probably cut back a bit on the gaming with her. I also stupidly hoped I could fuck her one day.. a pipe dream.. and our conversations were not heading in that direction at all… and I was too much of a scared pussy to take them in that direction. I was 38 years old spending most of my time with a 20 year old. I didn’t feel like I was doing anything wrong, but something just didn’t feel right about it… probably because I wanted to fuck her.

I start spending less and less time online gaming, and less time going to their house to deliver groceries. Unless I’m specifically asked to help, I barely do anything anymore. Months go by and I’ve pretty much stopped playing video games.. Alyssa has also been moved to an earlier shift. and it’s easier for her to shop and be home earlier.

One day in mid 2021 I got a text from Madison to call her, she needed to ask me something. I call, and she goes on about wanting to rent a hotel room for her friend’s 21st birthday at a casino. She asks if I can help them get the room.. I of course agree, and we came up with a simple plan for me to check into a room, hand the keys over and jet out of there.

The day comes and I pick up Madison and head to the hotel.
“You don’t look dressed for a party,” I say.
“I’m gonna use the gym at the hotel before my friends arrive,”” she responded.

Madison is dressed in tight yoga pants and a hoodie. A few minutes into the car ride, she unbuckles her seat belt and takes off her hoodie.
I’m floored by how great her tiny body looks. She has a tight yoga top on, and for a second I take my eyes off the road and get a glimpse of her tight stomach.
I don’t say anything. My heart starts to race a bit and my mind wonders. Is she into me? Do I try something with her? I’m way too nervous.

“Scott… Why did you stop playing call of duty with me?” Asked Madison.
“Oh… I.. uh.. Have just been busy with work,” I responded.
“I miss playing. I don’t have many friends that play video games,” said Madison.
Madison puts her hand on my leg and rubs it. My heart starts to race so hard, i’m afraid my apple watch warning is going to go off.
“I want you to come up to the hotel room with me,” she said.
I’m shocked, and can feel the blood rushing into my cock.
“Really, for what?” I asked.. Still in disbelief.
Madison moves her hand and starts rubbing my hard cock.
“you know what for, she says”

I spend the next 5 mins of the drive in disbelief, but also giving her the opportunity to back out. I explain our age difference and how it’s not a great idea to be fucking around with someone so much older. She tells me to check her into the hotel, and we’ll see what happens.

We arrive at the hotel and valet my truck. I tuck my cock into my waistband and luckily i’m wearing a sport coat and untucked shirt to hide it. I check-into the hotel and meet Madison in the lobby to hand her the keys. I reach out to give her the set, still giving her time to rethink this whole thing. Instead of taking the keys, she grabs my free hand and leads me to the elevators.

We say nothing this whole time. Still holding hands in the lobby waiting for the elevators.
On the elevator holding hands.. complete silence.
In the hallway walking to the room. complete silence, hand in my sweaty, nervous hand.

I wave the key over the magnetic door lock, and swing the door open. Madison follows, throws her bag on the ground and pushes me up against the wall before the door even has time to shut. She grabs my head down to her height and kisses me like i’ve never been kissed before. I’m instantly rock hard again, her tight yoga fit body pressed up against my cock. She obviously notices, and moves her right hand down and rubs my cock through my jeans.

I pick her up easily and carry her to the bed where I throw her down. We still haven’t spoken a word since the car ride. I don’t even bother taking off her shoes. I start kissing her neck, her tits over her top, and down to her stomach. I take her yoga pants down just past her ass, push her legs up against her chest, and begin eating her pussy like i’ve never eaten pussy before. She’s surprisingly wet. The wettest I’ve ever felt a woman. I’m turned on by how clean shaven her pussy is, and how good she smells. I softly, yet vigorously, make out with her pussy like it’s the last pussy I’ll ever get to eat. The first words spoken come fast and come often now.. “Oh Scott.. Oh fuck.. Fuck yes..” All thoughts of me being scared she might be a virgin are out the window.. I stick one finger in her pussy and begin making the “come here” motion while softly sucking and licking her clit. I’m enjoying making her squirm, and eventually she comes hard and fast. Grabbing the back of my head while her whole body shakes. Her half clothed legs with her shoes still on up in the air. She lets out a big exhale and I pull her down off the bed and force her onto her knees. She immediately knows why and her hands frantically search for my button and zipper. My pants barely get down past my ass before my cock is in her mouth. She wastes no time sucking hard and fast.. no teasing, no taking her time. She fondles my balls and sucks my cock so good I’m ready to come in what seems to be less than a min.. I tell her I’m coming and release a week’s worth of backed up come into her mouth. Madison drops back against the bed and exhales all while my come is dripping out of her mouth onto her sports tank top.

“That was intense,” I say.
“That was fucking hot,” she responds.

I ask Madison to join me in the shower to get cleaned up.. I of course had more plans for her. I turn on the shower and come back to the room. We kick off our shoes and pants. I step towards her and press my somewhat flaccid cock onto her stomach. I take her top off to reveal the perkiest tits i’ve ever had the pleasure of seeing in person.
This is close to what they look like: https://external-preview.redd.it/1a9RypTqu4wY5A9iGi5LTp45xFcxexmY-OLENjPXAhw.jpg?auto=webp&s=d429cd50534a584babdb154096eb8d68825193c6

I fondle her tits for a few seconds before leading her to the bathroom. I fully undress and we enter the shower. All plans on maybe washing each other go out the door as soon as we enter the shower.. We stand under the water making out… my hand finds its way back to her still dripping wet pussy. She moans again, and her wetness combined with obvious pleasure are enough to get me hard again. I spin her around, bend my knees to come down to her level, and enter her from behind. https://cdn.sex.com/images/pinporn/2020/07/24/23362250.gif?width=620

I once again feel like i’m going to come instantly.. I pull out and drop to my knees and start eating her pussy again. https://cdn.sex.com/images/pinporn/2018/12/10/20334909.gif?width=620
After a few minutes Madison is coming again. She’s not holding back. “FUCK YES… FUCK YES” she screams over and over again. I flip onto my ass and pull her down to sit on my cock. I ask her if she’s on the pill and she says yes.. I know i’m not going to last long, but I hold out for a few minutes while she rides me and I worship her tiny body.
https://cdn.sex.com/images/pinporn/2016/11/13/16895572.gif?width=620

I tell her i’m about to come and she grinds harder until I unload again, this time deep inside her little pussy. She drops down and lays on me.. we spend the next 10 mins or so catching our breath.

Source: reddit.com/r/gonewildstories/comments/svtm6w/i_slept_with_my_exwifes_best_friends_daughter_mf