(I have several older posts if you’d like a more thorough backstory on everything, but to sum it up: I had a many-years long sexual relationship with my friend’s mom that started over a decade ago and has sporadically continued until fairly recently, including a couple of meetups with my now wife and Mia (the friend’s mom, and how I’ll refer to her from now on). We haven’t seen each other in a while now, but chat once in a while and usually end up reminiscing a bit about past encounters we’ve shared, which inspired this post!)
In my early college days, even though I moved a couple hours away, Mia and I stayed in touch pretty consistently, texting a lot and usually sharing dirty pictures and messages at some point each week. I would always make it a point to go see her when I’d be in town visiting from school, with my two lengthiest visits of the year often coming around Thanksgiving and Christmas, when I’d stay for a few days straight (or more when it was winter break). This gave us plenty of time to get together, usually later in the evening, and helped create some of our favorite memories together. Unlike in the earlier years when her kids still lived at home and them and all of their friends were in and out of the house constantly, she finally had an empty nest. Along with an empty house to ourselves, we’d also been sharing more and more of our kinkier sides with each other via the many texts and calls while I was away at school. This resulted in her buying a few sex toys to keep around the house, including a couple of different sized and shaped vibrating dildos. This was my first visit after she’d gotten herself a big, thick purple dildo (8-10 inches, probably?) with a slight upward curve in the shaft and vibration settings galore. After weeks of talking about it and her sending pics playing with it, we were both ready to really explore our options in person. This is how it went (as best I can remember it):
It was well after dark and Mia (probably early 40s, I was about 20) had finally gotten off the phone with her sister to let me know it was okay to come over. I knew it was supposed to happen that night at some point, so was ready and waiting for her text. She had already “done her routine”, I remember her saying, which had me hard as a rock with anticipation as I drove over. She liked knowing I would come in hard, I think, and I certainly liked knowing she’d be waiting for me as wet as possible.
She let me in through the side door wearing sweat pants and a t-shirt, which disappointed me at first, and asked me to get her a glass of water while she continued on to the living room. She’d expressed an interest in being more dominant in some ways, while still being dominated in other ways, so I was prepared for some of that. But I wasn’t prepared for her confidence that night.
I walked into the living room and the TV was off, with the room being lit by Christmas lights and those little battery powered candles on shelves on end tables around the room. Mia was sitting in the middle of her big sectional couch and was no longer wearing the sweat pants and t-shirt she was when she’d welcomed me inside. Now she was in a sexy red lingerie piece that she’d been teasing me with pictures of, leaned back with her legs spread and heels on the edge of the couch, showing off the split in the crotch of her get-up, her hairless pussy lips glistening and almost blossoming out from the frilly fabric. She was running her finger up and down her slit, dipping it into her clearly wet hole, and back up to circle her clit. She was looking me in the eyes, but I just stared at her pussy while she played with it. I’m sure I stood there watching for a beat too long, but I couldn’t look away or move for fear she’d stop. Instead, she helped break the trance by telling me to undress and “come suck momma’s clit”, all of which about made me explode right then and there.
I could hear the vibrating sound before I even had my pants off. I looked back from where I was laying my clothes and she had the purple dildo in her hand, running the head of it between her lips while she messed with the vibrate setting. By the time I was naked and getting on my knees between her legs, she had the first few inches inside of her and was spinning it around but not going any deeper. I went ahead and did what I knew she wanted me to, which was spin it inside her like she was doing while I sucked her clit. It took a little time to clumsily find my rhythm, but did all of the tricks she had taught me over the years. Slow long licks and quick flicks from side to side, tongue swirls and taking it between my lips and sucking while I licked the tip from inside my mouth. The whole time I worked the vibrator in circles, starting to push it deeper as she got more animated, pushing her hips open further and beginning to hump my face as best she could. Before long it was in her to the hilt and I was licking her clit as best I could while she bucked her hips with her first orgasm. She let me know as she started to cum, telling me to suck her clit hard (“suck it harder for me baby”) and to fuck her deeper. I let her ride it out for a bit, pushing the dildo down so the curved head pushed up against her pussy walls as I started to pulled it out, but she clamped her legs down and trapped the dildo inside of her. I was also stuck between her legs as she reached down and took hold of the dildo, loosening her leg grip a bit and telling me, “I want you both in there at the same time.”
I stood up while she held the dildo inside of her, my cock was hard as a rock from all of the excitement and probably already dripping pre-cum. She couldn’t help herself and told me, “Come here. Straddle me.” I still wasn’t used to hearing her be so forward and confident, but it was making her hotter than ever to me and I was happy to oblige anything she asked of me. I ended up fucking her face on the couch, straddling her while she sat there and played with her pussy. I could hear the wetness and vibrating coming from below me, and could see the purple shaft sinking into her, glowing in the soft white Christmas lights as her head bounced on my cock while I held it between my hands. It had gotten to the point where I was sinking my cock down her throat to the hilt with every thrust and it was getting difficult to hold back. I told her just before I started cumming that I was about to unload, so she wasn’t too caught off guard but still a little surprised. She LOVES having a load shot deep inside her pussy and gets a little disappointed anytime one doesn’t go there (she said she just loves the way it feels as it fills her up), but she was still happy enough to swallow my load in the moment, fortunately.
She needed a drink of the water after all of that and we took a little breather, making our way back to the bedroom to attempt what we’d talked so much about in those late night sexts: double stuffing her pussy with two cocks, mine and the dildo. We both enjoyed stretching her pussy out from time to time, and I had been dabbling with fisting her for years after some early kinky conversations we’d had, opening the door for this moment.
After all of the dildo fucking she’d already received that night her pussy was wet and somewhat agape. I easily slid two fingers inside, then another, and slowly another. Eventually I had my fist inside of her and began wiggling me fingers inside of her, rubbing around on her pussy walls everywhere I could touch. Eventually she demanded that I fuck her. I pulled my hand out and grabbed the dildo, putting it on the setting she liked (with a little bit of help from her). I slid it inside of her first, positioning myself between her legs while she laid on her back with her legs spread feet up. I struggled a bit to make that work so she turned over on all fours and opened her hips for me. I put the dildo in and worked it in to the hilt, then pushed down on it to make room for my cock inside her opening. It was really tight at first, but I was able get my head in and slowly started sliding in from there. As soon as the head of my cock popped into her stretched hole she gasped a little and tensed, then relaxed and started to move her hips back, pushing my cock deeper inside of her. I could feel the dildo vibrating the very tip of my cock all the way to my balls and it got more and more intense the deeper inside of her I went. Finally both me and the dildo were inside Mia to the hilt. I just held where I was at that point because the vibration was so intense I was almost frozen. She had reached back between her legs to hold the dildo and had started moving it in circles inside of her, making it rub my cock in different places in the process.
I don’t know who started humping the other first, but eventually we both kind of loosened up and started really figuring out what was possible and what wasn’t with the dildo and my cock inside of her pussy as the same time. I would thrust and fuck while she held the dildo still, then vice versa. Then we would alternate thrusts, my cock then the dildo alternating as rhythmically as we could inside of her pussy. She was cumming with varying intensity throughout it all, but really started to shake and buck with the alternating thing (at least when it worked, that one was tricky to time out). She would eventually squirt all over the dildo and my cock, which I noticed as she flooded my balls with warmth as she moaned and bucked her hips. It was rare up to that point for her to squirt, so that really kicked all factors up to 11 for a bit. I fucked her harder and harder and told her I wanted to cum on her tits (it was my thing), but she pulled the dildo out and pushed back onto my cock and just said, “In my pussy baby, in my pussy” (it was her thing). At that point I was well past the point of no return and let loose, shooting ropes of cum into her while I held her hips against mine, both of us pushing into the other so we’d go just a little bit deeper with every spasm of my cock inside of her.
At this point she was pretty spent for a while, collapsing to the bed and panting heavily while curling up under the covers. I got a towel so we could clean ourselves up a bit and wipe up my cum that had dripped out of her as she recovered and then crawled across the sheets. We both laid around in a bit of post coital bliss for a while, then she got up to make a drink and I went to get my clothes and get dressed. We chatted in the kitchen for a bit and just kind of caught up for a while, then hugged good and tight and I left. We actually kissed on the lips before I left that night, which we hadn’t done a lot up to that point (only once or twice in the heat of the moment).
We played around with double penetration and double stuffing as much as we could after that, but only another time or two could come close to, or surpass, that first night together with an empty house and plenty of time on our hands. Those were always the best times together, hopefully with more to come as we all get older. Maybe the holidays will afford us some rare opportunity this year!
Source: reddit.com/r/gonewildstories/comments/z0oi6t/reminiscing_about_holiday_visits_with_my_friends