Had some requests for the follow-up story with Kristin. You can read part 1 with Kristin here: https://www.reddit.com/r/gonewildstories/s/4PUKgpBwkS

One of the things I learned very early on about dealing with older women was that most had discovered the ability to just let things be or to let one moment be it. This seemed especially true when being the younger boy toy that was probably just fulfilling some sort of fantasy.

Ater the fantastic blowjob that day, Kristin and I never really fully spoke about it. I would see her at work when our schedules would align and it was our typical flirty back and forth. But, never any direct discussion about the fact that her mouth had devoured my cock or that I had sucked on her saggy mom tits or that my fingers had explored her asshole.

I would occasionally test a boundary or two and she did the same at times, but our relationship at that point was one where that kind of flirting was the norm, even prior to our hookup. It never really led to anything other than flirting. So, after a couple of months of no action between us, I had sorta chalked it up to one really fun memory and stopped thinking about what I’d do to her in the work bathroom or in my truck if given the chance.

That was until one night when we were both closing. It was late in the afternoon and I was called up to the service desk to pickup a return. When I got there, Kristin was there and she had her trademarked devilish grin on her face as I approached. I smiled and shook my head as I said, “what’s up, trouble?”. She replied, “I’ll give you some trouble, alright.” And I quickly snapped back, “yea yea yea, I’ve been waiting on that and I don’t think it’s ever happening.”

Now, it’s important to note that this kind of back and forth was normal for us and I wasn’t necessarily angling for anything in the moment. But, apparently it was the right moment or maybe this time I struck a nerve because Kristin just looked at me for a second. It was as if she was trying to formulate her words carefully. After a small inhale, she finally responded, “you know, I want to let you fuck my brains out, right? Like, you know that I want that really badly, right?” While our relationship to this point had been very playful and even raunchy in passing, it had never been anything remotely this direct. I looked back at her trying to analyze her in that moment and I simply said, “if you say so…” Her demeanor changed a bit and I could sense a bit of frustration from her as she moved closer to me. She looked to see if we were completely alone in that moment and leaned in. “Chris, I’m married. My husband is an asshole and he barely fucks me anymore, but I love him. Sucking your dick the other day made me feel alive again sexually. I want so badly for your big dick to be inside of me, but I also know that it’s wrong.” There was real vulnerability in that moment and even I felt a bit bad for any role that I had played in the relationship up to that moment. I was at a loss for words a bit and I just backed away and looked at her. Finally, I mustered my response, “Look, Kristin. The last thing I want to do is to make life difficult for you. You’re an awesome chick and we had a great moment in your car that one time. If that’s it. That’s it. If you want something more, you know where to find me. Either way, our secrets are safe with me.”

The response wasn’t a highly calculated or thought out one, but it was real and how I felt in the moment. I had no clue how she really wanted me to respond. I was a 21yr old dude looking to get his dick wet, nothing more really. She looked up at me at this point and said, “god, you’re hot. Why do you have to be so hot?”. I laughed, smiled and said, “I’ll see you later. I’ve gotta get back to my department. I meant what I said. No pressure here.”

Later that evening as things were winding down and the store was closing, I went up to the service desk to get my cart of returns. Kristin saw me approaching and motioned for me to come her way. I walked up and said, “what’s up?”. She moved closer and said, “fuck it.” I looked at her and said, “huh?”. She looked me in my eyes and said, “I want you to fuck me after work.”

I’ve gotta say, this caught me off guard. The previous conversation had me feeling like anything more was probably a long shot. And like 4hrs later here she is telling me she wanted it THAT NIGHT.

After reading her body language for a second I could tell she was serious and very nervous. I said, “sounds like you’ve thought this through and you have a plan. Tell me when and where and I’ll promise to make it worth it.”

“I’ve got the minivan today. You can fuck me in the back of that after work.” My dick started to grow in my pants immediately. She was direct and serious. This was really going to happen. This slutty milf with a magic mouth was going to let me fuck her in the back of her minivan.

The next hour felt like it took 4 days to go by. We were two of the last four to leave the store. We walked to our vehicles at the back of the parking lot and I noticed that Kristin had parked all the way in the back by the trees. Our coworkers got in their vehicles. We got in our separate vehicles and I started up my truck as if I was preparing to head out. I drove away towards the exit, but instead parked in the lot right next to ours. By the time I put the truck in park our coworkers were gone. I got out of my truck and walked towards Kristin’s minivan. As I approached I could tell the engine was on, but the headlights were off. There was no one in the drivers seat. I walked to the passenger door and opened it. I was greeted with, “wrong door, silly.” and I turned to the back seat to see Kristin butt naked.

I quickly closed the passenger door, opened the slider and climbed in. As I did, I was greeted with Kristin opening her legs spread eagle. She held her legs back with her hands and said, “I don’t have much time.”.

I didn’t need much more of an invitation. I slid off my boots and then my pants. While I was maneuvering my way out of my clothes I couldn’t help but stare at her exposed holes and saggy tits. This was a body that had seen some miles and that turned me on.

My cock was already rock hard and I moved myself towards her. She rested on the back bench seat and I myself positioned on the floor between the 2 captains chairs. I lowered my mouth down towards her pussy. It looked like it had been beaten up pretty good over the years and to this day is probably the sloppiest looking cunt I’ve ever seen in person. I loved that though. I loved that this imperfect woman sat there in that moment and wanted me inside of her. I sloppily began eating her pussy. Working my way around her labia and her clit and pushing my tongue deep inside her hole at every chance. I wasn’t trying to make her cum. On the contrary, I was just trying to make her feel as dirty as possible. She squirmed in the seat and pulled her legs back further. I could tell she was loving every moment of it. I stared at her big pink asshole as it stared back. I instantly knew what I wanted. I began to flick my tongue across it then circling it repeatedly. I transitioned to licking up and down her crack from her pussy to her asshole. She loved it. Eventually I settled on the ass and began really applying pressure with my tongue as I simultaneously started rubbing her clit. Keeping up this tandem of movements I was able to stare a glimpse up at her as she was squeezing her sexy hanging titties. That’s when I started pushing my tongue in and out of her worn(yet sexy) asshole. I picked up the pace with my fingers on her clit and soon I could hear say, “oh god. Oh fuck. Oh shit.” I buried my tongue deep in her ass as I felt her legs start to shake. She let the orgasm grip ahold of her and began to writhe. I slid my tongue from her asshole and sat up to look at her. She was in a state of disbelief and commented, “are you sure you’re 21? I’ve never had anyone do that before.”

I smiled and pulled her in for a kiss. Now burying my tongue deep in her mouth giving her a taste of her ass that she neither requested nor denied.

After a moment, she pulled away and motioned for me to sit down. At which time I followed along. My cock was at full attention as she positioned herself on the floor in front of me. I knew she didn’t have much time and part of me wanted to go straight to fucking one of her holes, but I also wasn’t going to turn down some more of her expert cock sucking skills. And she did not disappoint. This time she had the advantage of leverage from her position compared to the last time and she made great use. Immediately my toes began to curl as she took all of me into her mouth repeatedly with ease. She was using twice as much spit as last time as well and soon the pool of her saliva that was aggregating around the base of my cock and her hands proved to be the best lube for her expert hands to massage my balls as she throated the shit out of my cock.

Now, I could have easily painted the back of her throat like last time, but I needed to fuck her. That was the stated purpose for why we were here. I grunted as she sucked on one of my balls so hard that it made me squirm. Immediately after I pushed her back and away. With watery eyes and a spit covered face she caught her breath and apologized for the rough treatment of my left testicle. I assured her it was fine, I just needed to be inside of her. “ I know you don’t have much time and I know you want this inside of you.” She stared back and me wiping saliva from her face and said, “yes, I do. But, you can only fuck my ass. I’ll feel better about being a terrible wife if you don’t fuck my pussy this time.”

This revelation and request sort of caught me off guard. I smiled and said, “are you sure?” To which she replied, “yes, I want you raw. I want to feel all of you and I’m not on birth control. Fuck my ass as hard as you want and you can cum in it.” The matter of factness with how she conveyed this command is still to this day one of the sexiest sluttiest things I’ve ever heard. Thinking back it doesn’t come as a great surprise as our flirting often got kinda raunchy. This was the type of encounter I sort of always fantasized we’d have.

I was no stranger to anal at this point in my life. Even though I was in my very early 20’s I had encountered several partners who wanted my larger than average cock in their asses. In hindsight, I think that Kristin was lucky that I had experience. Because rather than just shove my saliva soaked cock immediately into her worn looking asshole I eased myself in. Simultaneously moving her hand to her clit for her and inserting my thumb into her sloppy wet pussy. As she began to build a rhythm with her hand on her clit I could feel her asshole begin to relax. I coated the rest of my shaft with some more spit and slowly guided another inch or two into her as she began to push back on it. Soon I was fucking her with 3-4 inches of my cock and slow but steady strokes. Her breathing was starting to relax and she confidently said, “I’m ready for it all.”

I needed no further invitation and started giving her my entire cock at this point. It was glorious. This slutty older coworker of mine was spread out in the back seat of her minivan taking all 8.5” of my cock in her married asshole. As she adjusted to my full girth she placed 2 fingers in her gloriously sloppy pussy and began to absolutely blast herself to the rhythm of the assfucking I was giving her. Maybe 2 minutes into this I could feel her asshole clench my cock tightly. She stopped blasting her pussy with her 4 fingers and slapped me on the chest and let out a shriek. After several convulsions her asshole spit my cock out and she looked up at me and breathlessly said, “holy fuck that was amazing.”

“I’ve got maybe 5 mins before I have to go. Can you cum in my ass in 5 mins? I want to go home with your cum in my asshole.”

I chuckled and moved her aside as I sat down on the soaking wet bench seat. I knew exactly what I wanted.

“Sit that little ass right on my cock.” I said as I positioned her how I wanted her. “If you’ve only got 5 minutes you better ride this cock well and fill up that asshole quick.”

Sensing quickly that I had turned the tables on her, Kristin turned to face the dashboard and lowered her ass onto my bulging cock in a crouching position. First crouching over it and pumping up and down whilst her feet were on the ground. Then with some help from me she brought her feet up on the bench seat and grabbed the backs of the captains chairs in front of us while leaning forward. I wish I could have seen what this looked like from the front as the site of this married milf body moving up and down on my big young white cock all while her big hangers flapped back and forth must have been an imperfect masterpiece. The idea of what it looked like from the front coupled with what it looked like and felt like from my vantage point brought me to the brink. I started mumbling “fuck yes. Just like that.” Sensing this Kristin picked up the pace thinking that she was about to drain my balls. But, I had a slightly different idea. I reached out and grabbed her hips. Whispering in her ear to hold onto that seat tight because l I was about to fuck her little asshole as hard as I could. “Do it.” She whispered back.

And do it I did. I gripped her hips and furiously fucked her asshole from below. It felt incredible. I could feel the tip of my cock reach an area that I wasn’t hitting before and the sensation of that drove me to an explosive orgasm. One where I grunted and pumped every drop of cum that I had in me into her hungry milf hole. I remember the orgasm so vividly because it was one where I literally shook afterwards. Grunting and still pumping as my legs shook.

Kristin climbed off of me spilling some of my seed into my lap and onto her bench seat. I was spent.

She knelt before me and licked the head of my spasming cock. I almost jumped out of the seat. She giggled and said, “you may have enjoyed that almost as much as I did. Good!”

I kissed her and told her that she felt amazing. To which she replied, “oh Chris, I think you know how sexy you are. I’m not sure why you wanted to do that with ME, but I’m glad you did.”

“Anytime.” I said.

We both got dressed and I got out of the van, looked around and walked back to my truck.

Kristin drove away. Grinning at me the whole way by.

Two days later I saw her at work. She seemed a bit off. She said that she thinks her husband knows that she did something the night of our rendezvous. I asked her how and if she was ok. She told me that it was the weirdest thing. That at first he was accusing her and he was angry. She said she denied anything of the sort and they went to bed angry. The next day he came to her and said he didn’t believe her. But, here’s where it got hella crazy… He said that he didn’t blame her if she did. He said that he knew he hadn’t given her much attention and that he never tried to fuck her anymore. She said that she didn’t know what to say so she just listened. He went on about how he was sorry and how she didn’t deserve that.

I sat there in a bit of disbelief as I didn’t see any of this coming. That’s when the story went way left. Kristin said that they had sex. And then they had sex again. She said they had sex 6 times in 2 days and that was more than they’d done it in over a year. She told me that it was a welcome development and that she wouldn’t be able to fuck me again. I shook my head and laughed. I told her that I was happy for her and that I really enjoyed our time together. Then we hugged it out at work and both went back to work.

Blasting this guy’s wife’s asshole in the back of their minivan really re-awakened their sex life and their marriage. Still one of the stranger developments I’ve ever experienced.

Kristin did pay it forward a bit though when she told several of our female coworkers that I had a big dick. Those stories for another time!