A one-night stand with my ex-wife’s best friend [FM]

After some encouragement in PMs coming out of an [AMA](https://www.reddit.com/r/NSFWIAMA/comments/pq2x91/i_m37_am_recently_divorced_but_have_managed_to/) I did in the the original throwaway account I had (u/fuckadaythrow2021, before I logged out and realized I had lost the passwords for both it and the email associated), I thought I would post a more detailed story here, and given the theme for the month, thought I would start with one of my more interesting one night stands over the last year. The backstory and set up is a little long, but there’s some action throughout.

I did an AMA last week that has more detail, but for some additional background, I’m a 37-year-old, recently divorced guy. That divorce was finalized last June, as in June of 2020, which was just a few months after our separation due to COVID that quickly made us both realize that we didn’t miss one another the way we should when living apart. After the divorce, I poured myself into working out, and my work, which was fortuitous, as our group ended up being acquired, resulting in a large pay day towards the end of the year. A non-compete, consulting fees, and some added flexibility to my schedule made me realize that I could greatly reduce my work schedule, have more time for myself and pursue some other endeavors, so I basically reduced my working hours to enough to make sure I had health insurance, and to cover the spousal and child support payments with a little left over for my own recurring expenses. Don’t get my wrong, I was still making more than enough for most, but due to some advantageous investments I had made, the lion’s share of my income was not coming from going to work. Thus, when late in the year, I decided to get back into the dating pool, I didn’t have the obstacle of trying to balance a full day of work, part time parenting, and meeting women, in my way.

Some other recently divorced, as well as perpetually single, friends convinced me to go all in on apps, and so I joined a few of them, from traditional dating apps, to the hookup apps, and even put a profile in on Seeking. Plunging in with both feet, I found myself finding a good amount of potential romantic relationships in no time, and now just had to figure out how to turn some swipes and matches into dates. Once I overcame that hurdle, I decided that my best approach was volume, and tried to arrange as many dates as I could, and within a couple days, I had meetups arranged at lunch and dinner for a solid week. Things were looking up on the dating front. It was my third dinner date of the week that really broke the ice for me, and after what was a pretty good casual dinner with wine on the patio of a restaurant near my house, an early closing time due to covid gave me an assist. When the waitress said they need to close up for the night, she looked at our half drank bottle and said she’d be happy to cork it to go for us. Just the opening I needed, and I offered an outdoor fireplace at the house I was renting, just a couple minute drive away. She took me up on the offer, and after finishing that bottle, and opening another that we drank half of, laughter turned to kissing, kissing to making out, and making out led to her taking my hand and leading me inside.

My lack of post-divorce hookups left me deficient in one key area, however, the procurement of protection. The 42-year-old mother of three in my bedroom was similarly ill equipped, as this was the first date she had gone on since her husband cheated on her, causing a split back in September. Because of the circumstances of her split, she had done a full STD panel, but unfortunately, was no longer on any birth control. Not a problem here, as I too was clean, and was 5 years post-vasectomy. And so, after a quick, but thorough, round of mutual oral foreplay, I found myself on my bed, with a 6-year-older milf straddling me cowgirl and trying to work my rock hard cock into her deliciously wet pussy. Now I don’t know who in my family I have to thank for some of the gifts I have been granted, but while I don’t have a great deal of length on my side, my girth has been both a blessing and a curse. And this night, for the first few minutes, I was cursing it. No matter how much she tried, it was not going in. But then, it was as if the gates of heaven, and well, the gates of her heavenly pussy, opened up, and she made her way down my shaft. The guttural sound she made as she did so echoed across my sparsely decorated bachelor pad bedroom. It took everything in my power not to release too early though, as I had ignored one of my good friend’s advice to rub one out before a date. I mean, this was my fifth date of the week, and thus far, nothing had happened. Unfortunately, that also meant it had been over a couple weeks since I had cum. Suffice to say, I was on a hair trigger. Luckily, my paramour was similarly quick to let go, and between a back and forth grinding of her clit on my pubic bone, and as she told me later, the slight upward curve of the head of my cock against her g-spot, she came quick and loud. Her orgasm was accompanied by a tightening that I couldn’t resist any further, and I found myself unloading all two weeks’ worth into her. It was a quick romp, but a satisfying one. After she climbed off of me, she looked down at her phone and after a quick curse word, told me that she had overrun her babysitter by 45 minutes and needed to run.

The speed with which the date progressed from my outdoor fireplace, to making out, to sex, to her running out the door shocked me. But I guess that’s my new normal now. Interestingly, that was the only one of those dates that progressed so quickly. I had some great dates, got a lot of numbers, and made a couple other upgrades in my life. Due to a fortuitous investment with a friend, earlier in the fall I got a distribution check that dwarfed my salary, not only for the past year, but frankly, for the past several combined. I decided to use a chunk of it, sold my half of our his-and-hers Range Rovers, and bought myself a G550, as well as an Italian super car that is simultaneously completely impractical and absolutely worth it. The first holiday divorced was incredibly difficult, but I tried to make it worth it for our kids, even if it was splitting time. Other than that, I was entering 2021 on a high note, with a new lease on life. I made a New Year’s Resolution to take the social experiment from before the holidays and make it part of my routine, to try to regain a healthy and active sex life.

And so it began for me when I went to a small NYE party at the home of some friends. That night, I met Jessica, a 30 year old dental assistant. We drank too much champagne, made out at midnight, and after finding out that we lived a couple miles from one another, I suggested we split an Uber home. Once we were in the car, she read my mind, “my place or yours?” Hers was already the first stop in the app, so we ended the ride there. I had grown somewhat smarter in the preceding couple weeks, and brought protection with me this time. Jessica’s sparkly cocktail dress hit the floor as soon as the door was closed, and her braless augmented D cup breasts looked pretty fantastic as she pushed me down back on her couch. We made out, me still in a sport coat, shirt, jeans, and shoes, her in a black g-string and barefoot. I flipped her over and removed the g-string leading to my first encounter with a lasered pussy. So completely smooth, with no sign of stubble, it emphasized the longer, butterfly style labia that were already wet with arousal. I licked her to a quiet orgasm before she grabbed my shirt and pulled me up to standing in front of her. Unzipping my jeans, she pulled them and the boxer briefs down, pulling my semi out and sliding it into her mouth. I assume she thought that it was just going to get a touch longer and then firmer, as she seemed surprised when upon getting fully hard, it grew considerably bigger around, But undaunted, she spun around on the couch and brought her ass up into position in front of me. Putting on a condom, I pushed into her, getting an ‘oh shit, go slow.’ Jessica’s olive complexion looked great in the dim light, and the curves of her Italian hips and ass were bringing me to the edge. Not to mention, those butterfly labia were gripping me tightly. Jessica had been talking throughout, but again got quiet and started breathing heavy. Right after, she said to me, ‘are you close, I can’t usually take much more after cumming, especially not tonight.’ I told her I was holding back, hoping to make her cum, and she said she definitely did and then dirty talked a bit about it, which pushed me over the edge. I went to the bathroom to clean up and dispose of the condom and while in there, her two roommates came home. I came back out and we made small talk for a few minutes, but it was getting late, so I grabbed and uber and headed home.

The next morning, I shook off a light hangover, and went for my morning run. It was pretty brisk, but it felt good, even on only five hours sleep. After a shower, I decided to go grab coffee at a coffee shop. Given the social distancing restrictions, the line extended out the door. The girl behind me in line was a cute, tall (probably 5’9” is my guess) black girl. She was wearing a black dress. I assumed this was a walk of shame for her, but didn’t want to ask that specifically, so instead asked her if she had a fun New Year’s Eve. Turns out, it was a work uniform, and she had just gotten off the graveyard shift, and was grabbing coffee before catching the bus home. My bad, As we stood there, waiting for the line to move through, I kept up the conversation, and when we got to the front of it, I placed my order and then said, ‘and I’ll pay for whatever she is having as well.’ We made a little more small talk as we waited, and then when the drinks were ready, asked if she wanted to hang out while we drank them. She said sure, but was worried about missing her bus. I told her that if she missed it, I’d be happy to drive her wherever she needs to go. And so 30 minutes later, Kiara, the 20 year old waitress, found herself riding across town in an Italian sports car. There was some light flirtation over coffee, but once she was in the car, the prey became the predator and her hand found its way over the center console and onto my leg. When we pulled into a only slightly sketchy apartment complex, I tried to put the thought out of my head that my little experiment into regaining my confidence could cost me my car, if not my life. I helped Kiara out of the car, and she said, ‘I would have thanked you in the car, but its sort of tiny. Do you want to come upstairs?’ I decided to roll the dice and take her up on it. When we got into her apartment, she told me her sister, with whom she lives, was at work, so we wouldn’t be disturbed. She quickly turned and kissed me, before pulling back and saying, ‘this dress smells like work, don’t you think’ pulling it over her head. Her bra and underwear were mismatched, which didn’t really matter as they were both discarded immediately after the dress came off. I only got a brief look at her trimmed pussy as she squatted down in front of me and pulled down the joggers I was wearing. Without saying another word, she went to work, sucking on my cock with one hand around the base, and the other rubbing her clit. By this point, I was only six hours removed from Jessica, but even still, Kiara’s technique and suction was incredible, and I found myself nearing the point of no return. I said to her, ‘You’re gonna make me cum”, and she moved to go even faster. Within a minute, I was cumming in her mouth. She swallowed it all and then stood up and said to me, ‘take me to dinner next time and we can do more.’ We exchanged numbers and I left as she went to take a shower.

It was two days later when I had the realization Hannah, the just turned 18 waitress I met before New Year’s and grabbed lunch with on the 2nd, and Kimberly, the 37-year-old preschool teacher I had seen at the gym before Christmas, and saw again and went out with on the 3rd, had meant I had a streak going of every day of 2021 thus far, I had had some form of hookup. Now, 3 days in a row is barely a streak. But, it was proof that the resolution I had made was working, and now I was committed to it. So thus I set off on a concerted effort to make as many connections as I could, and see where this thing would go. One thing I did do differently after Kimberly was to set up a spreadsheet to track who I had met, where I met, them, etc. I had always been a science geek growing up, and I figured there could be some interesting trends in the data. So every night, or every next morning, depending, I took down as much information as I could gather about the women with whom I was hooking up.

Which then leads to the hookup that I even started this entire post. This one, I think is one of two most unusual one night stands of 2021 to date. At the time, I was just entering what has now become an actual consistent relationship, but we had not yet figured out what that meant or otherwise put any parameters on it. It was the end of June, and the day before, I had texted McKenna, the girl I had been sort of seeing off and on for about a month. We hadn’t really talked for about a week, after a little bit of a fight we had had. The fight itself was sort of odd, and came out of what had been some pretty hot sex. She had come over in the afternoon, and after some great foreplay, we were going at it from behind, and when it came time to cum, I pulled out and came on her back. About a half hour later, we started fucking again, this time missionary, and after she came, I pulled out and came on her cute B-cup chest. We then went out to get something to eat. After dinner, we watched a little Netflix, but quickly ended up having sex again, this time with her on the bed and me standing at the foot of it. Again, she came, and after a few more minutes, when I was ready, I pulled out came on her face (not a surprise facial, we discussed). Then, before falling asleep, we went one more time, with her riding me, she told me she wanted me to cum in her, I told her I love it when she sucks my cock straight from her pussy and I cum in her mouth. We switched positions and when I was close, I pulled out and brought my cock up to her mouth. She opened her mouth, and eagerly (or so I thought), sucked me off to completion and swallowed. After that, we fell asleep.

The next morning, I got up to make us both breakfast and coffee. When I brought it to her, she said I was being weird, and wouldn’t cum inside her. She said it was sketch, and if a girl says cum in me, you should do it. ‘It’s not like I’m trying to get pregnant.’ I said she was crazy, which is quite possibly the worst thing I could have said in the moment. So we argued a bit, and she got dressed and left. So then fast forward a few days. I text McKenna to see if she has plans for the 4th of July. We got to texting more, she told me she was sorry, said she missed me, and then sent me some nudes. We made plans for dinner and it was a date. I picked her up, and she looked fantastic. She also clearly had plans as in addition to her purse, she had a small overnight bag. Always a good sign. Dinner was great, and on the drive home, she showed me just how good her Brazilian waxer had done for her the day before. When we got to my place, there was no pretense, and we immediately headed for the bedroom. I spent a considerable amount of time going down on her, and brought McKenna to two orgasms before she got into doggystyle on the edge of my bed. I was still fully clothed, and quickly got out of that condition before pushing into her. I absolutely love that initial penetration, especially when I either haven’t been with someone before, or when I haven’t been with them in a while. With McKenna, even four days felt like a while. Being inside of her felt incredible and she was doing everything in her power to get me to cum, quickly. When I was close, I had planned to just cum inside her, but she surprised me by pulling off and taking me into her mouth, looking up at me with her gorgeous eyes, while my cock unloaded into her mouth. We laid down and watched HBO for a while she played with her phone, sending snaps to some friends, and played with my cock. About an hour later, her naked body next to me, and my cock in her hands had me back to full mast, and I asked if she wanted to go for a second round. She finished up a message to her bestie, and climbed on to ride me cowgirl. This wasn’t a slow sensual cowgirl, this was a fast, almost twerking, and both she and I got close to climax quickly. She came first, and immediately after, hopped off and plunged me cock as far as she could take it into her mouth, pumping me with a couple fingers and thumb as she worked the head and upper shaft with her lips. It was less than a minute before I came again into her mouth.

The next morning, McKenna woke me up with a blowjob. I’m not sure how soon before I woke up she had started, but by the time I was fully awake, I was not only totally hard, I was fairly close to cumming. It didn’t take too much longer before I unloaded in her mouth. I actually had to go into work that morning, but told her she could stay, swim, lounge around, whatever she wanted to do. I came back mid afternoon to find her sunning herself by my pool, wearing a pair of thong underwear. Her chest looked gorgeous, tanned and slick with sweat and Sun Bum. I stripped off what I was wearing, and walked out to the deck. ‘You’re a little overdressed for skinny dipping, aren’t you?’ She giggled at me and said, ‘welcome back!’ before taking off the thong. She had the lightest tan lines from the thong or whatever swim suits she wore recently, as clearly, there was some bottomless tanning going on as well given the color. I had full intentions of actually jumping in the water, but seeing her oiled up body naked by the side of the pool, I instead moved right up to her, threw her legs over the arms of the Adirondack chair she was sitting in, and went down on her freshly waxed pussy. McKenna was biting her hand, trying to hold back the moans, since we were outside in a not quite urban, not quite suburban backyard. After about eight or ten minutes, she came hard, barely able to stifle the moans. I was hard at that point, and decided I couldn’t pass up how sexy she looked in that position (legs up and over the armrests), and pushed forward into her. I pumped myself into her, and even though we had had two rounds the night before, was turned on enough that my climax came surprisingly fast. Her slick tan chest was so enticing that when it was time to cum, I pulled out and came directly onto her breasts. Apparently, that was a poor choice on my part. I could tell something was off, and after taking a shower to rinse off, she got dressed and we went to get something to eat. She was quiet, and sort of pouting throughout dinner. After I grabbed the check and we went to the car, she asked if I could take her home.

Which now, actually leads to the one night stand I wanted to share in this post. When I got back home, I saw I had a text from Jodi. Jodi is one of my ex-wife’s best friends, and was one-half of one of our couple friends before they got divorced a couple years ago. It had been a while since Jodi and I had talked, so her text sort of came out of the blue to me. She originally texted since it was the anniversary of the divorce, and she wanted to see how I was doing. We exchanged some back and forth on that, when she texted, ‘it had been so long since I had seen you, I didn’t get a chance to talk to you at the party, you look great.’ (Our twins birthday had been a couple weeks prior, and while there were lots of mutual friends there, I tried as much as possible to stick to the dads I knew from their school and a couple others). We caught up a little more, and I thought that was that. Then she sent a ‘so what are you up 2?’ If I’m not mistaken, I thought, Jodi is maybe flirting with me. How bizarre. I mean, she’s always been a little flirtations. You know the type, the kind that even when married and talking to other married guys, fawns over the littlest things, and generally loves to have every guy wrapped around their finger. So, I felt like sure, she’s flirting, but it’s just Jodi. So, I flirted back, because, why not. It was now 11pm, and we had been chatting back and forth intermittently for about 90 minutes. We got on the topic of post divorce love lives and how dating was going. We both had been dating (well, obviously for me given the preceding paragraphs), but nothing too serious. She then typed ‘brb, getting another bottle of wine’. So clearly, Jodi was already a bottle in and slightly lubricated for this text conversation. The discussion got more and more risqué, with more stories about dating, apps, her getting hit on, dating older men with ED, all sorts of things.

Jodi then told me a story that my ex-wife, Vanessa, had shown a group of her friends some pics of my dick, along with some light sexy times (fooling around, oral, etc, no hardcore stuff though). One pic was right after a Halloween party, where I had dressed as Thor, and she had gone as Black Widow. As a result, the girls on had nicknamed my dick “Thor’s Hammer.” Apparently, when Vanessa and I had broken up, a text message chain went around about Thor’s Hammer going to waste, and someone said ‘I volunteer to see if I’m worthy’ before three others called dibs as well. I assured her that none of Vanessa’s friends had tried to prove their worth, but she’d have to tell me some time which four said they wanted to. She was pretty quick to reply that she was the first one to express interest, with a tongue out emoji. That was followed up with ‘I think I’m drunk… I shouldn’t have told you that story.’ I replied that I figured, but I would still hold it against her next time I saw her. She replied, ‘I’m not sure holding it against me will satisfy me.’ Oh wow, she went there. She then said, ‘Can I see it?’

Me: ‘What do you mean, like now?’

Jodi: ‘Yeah send me a pic?’

Me: ‘What do I get in return?’

Jodi: ‘What do you want?’ ‘

Me: Send me a pic first’

Jodi: ‘A pic of what?’

Me: ‘What you’re wearing right now’

Jodi: ‘OK, just a sec’

‘Shit, I just spilled wine all over myself’

‘That didn’t go as planned’

And then a pic came through of Jodi in a white tanktop, splatted in quite a few places with red wine, including right above her left breast, causing the fabric to show through to her nipple, not that the fabric on the right breast was doing much to obscure that nipple. Jodi had gotten a fantastic augmentation done a few years ago, before the divorce, which her ex-husband had bragged out repeatedly. It did appear that they were worth the money, and the D-cups were still high and tight, without looking so firm to be reminiscent of bolted on breasts. Below the tank top was a tiny black mesh thong, and given she was sitting with her knees up, taking a pic into a mirror, the mesh showed that she didn’t have a hair on her pussy, and had a nicely shaped cleft and hood.

Me: ‘Sorry about your shirt, but hot pic’

Jodi: ‘So where’s mine?’

I had on a pair of grey boxer briefs with a pouch, that look exaggerated even when flaccid. But the text discussion, and the pic of Jodi, had gotten me hard. I snapped the pic and shot it over to her.

Jodi: ‘Was hoping for one without the clothes’

Me: ‘That’s an in person exclusive’

Jodi: ‘Is that an invitation?’

Me: ‘For you, always!’

‘But seriously, it’s late and you’ve had a lot of wine. Was fun chatting, we should do this again’

Jodi: ‘Boo. I guess good night then’

Then next morning, I got up early and did my run around sunrise. Around 7am, I got a text from Jodi…

‘I had wicked dreams last night and when I woke up went back through our convo’

‘Sorry if I came across as too drunk. I was tipsy, but not drunk’

‘Eric has the girls this week, and I’m going to cancel my Zoom meetings for the day.’

Pic comes through of Jodi, in front of the same mirror, same position, no tank top, no mesh thong.

‘Is this enough of an invitation?’

Me: ‘I can be there in 10 minutes’

Jodi: ‘I’ll open the garage, the last thing I need is the neighbors seeing that ridiculous car’

I drove my SUV over instead, but still parked it in her garage, just to be safe. She met me at the door from the garage to the house, still totally naked. Her 38-year-old body was in great shape. 5’6”, probably 130 pounds, clearly the time she spent with her trainer was paying off. Even though it was before 8 in the morning, her blonde hair was styled, and she had some light makeup on, maybe a little more than light on her eyes. The effect was altogether hot. She grabbed my hand and said, ‘follow me’. As she walked in front of me, I took in the rest of her naked body. I had always had a thing for her ass, although according to Vanessa, it was one of the things Jodi was not a huge fan of herself, always thinking it was a little too big for her body. To the point that when we had pool parties or took a group trip to the beach, Jodi was uniformly always wearing a cover up over her hips. Now seeing it in all its splendor, sure it was slightly disproportionate to her torso, but in a sexy way. It didn’t hurt that I always also thought of her ass in a sexual way, since her ex-husband, Eric, would routinely find ways of bringing up anal sex, dropping it into jokes, make remarks about how well he was doing at work and that he was going to go home and fuck Jodi in the ass to celebrate. In any event, here I was, in her house, her without a stitch on, leading me to her bedroom. When we got there, she immediately started undressing me. I hadn’t really dressed up for the occasion, and just had on a t-shirt, workout shorts, socks and running shoes, but the shoes were left at the door, so it was quick work to have me naked as well, and her hand immediately grabbed my dick.

‘Fuck that is a great dick. I honestly don’t know how Vanessa could give this up. I don’t know how Gary even competes’ (Gary is Vanessa’s new boyfriend). As she was saying that, she was dropping to her knees in front of me, and started kissing the head of my cock, before sliding her tongue down, around, and then back up the other side of my cock. She then attempted to put her mouth around it, which was a bit of a feat for her. She pulled off and said, ‘I’ve never been with a guy that I couldn’t really fit their cock in my mouth, this is unreal’ She went back to it and struggled to give a halfway decent blowjob for a few more minutes, before I pulled her up and said, ‘let me return the favor, lie down.’ She replied, ‘I can cum a lot easier if I’m on top, why don’t you lie down.’ So I did, and she came up and straddled my face. Jodi’s pussy had really puffy outer labia, with great inner lips, and a comparatively large clit. As I had seen in the photos she sent, the cameltoe/cleft formed by her labia and the larger clit hood was absolutely picturesque. As she lowered herself onto me, the position made her lips open up a little more, and there was a little gape too as she came down. Her pussy was delicious, and perhaps the arousal of the situation, the morning, the head she gave, all contributed to it being extraordinarily wet. As I licked her pussy, she rocked herself back and forth. She was also reaching back and stroking my dick while she did. She then paused for a second, and slightly shifted, bring a leg up and over before spinning and repositioning, now facing down towards my feet. ‘I hope you don’t mind, it’s easier for me to stroke you, and I just want to watch your cock while you do this’. I of course didn’t mind at all, and was now afforded the opportunity to see the asshole between those two glorious ass cheeks that were resting right above my face. I continued licking, she continued rocking and within a few more minutes I could see her pussy and ass contracting repeatedly while she moaned.

Her pussy was soaked now, between her own wetness and my saliva. She had been stroking me the entire time, lubricating her hand with her own saliva, and it was a wet mess as well. She moved her way down my body, and without hesitation, positioned the thick head of my cock against her now open, wet labia. She pushed her body down, and while there was some resistance, once the head had entered her, she slid down with a moan. Jodi then proceeded to ride me reverse cowgirl for probably 10 minutes. She had one hand holding on to my balls, and ever time she felt them tighten, she would slow her motion, and pull them away from me. Holy hell she was edging me inside of her and it was magnificent. I meanwhile, had both hands on that glorious ass, and was slowly making my way inward, until I had a thumb resting against her asshole. When I pushed a little, it elicited another moan. I brought my thumb back up to my mouth, coated it in saliva, and returned it, pushing further in this time. ‘oh fuck, have you ever heard you have big hands? Your thumb feels as big as Eric’s dick back there.’ I stayed silent but kept up the ass play, while she continued to milk my bare cock with her pussy. Even as good as she was with edging, eventually I hit my limit and say, ‘oh fuck, I’m going to cum’. I thought for sure she would pull off, but she ground her body down even more, and held my balls as I came, deep inside her. After my orgasm subsided, she laid back against my chest, my cock still inside her as it slowly deflated. She turned her head and kissed me, which I realized was the first kiss we had shared since I arrived. The kiss got deeper, and I swear, I felt some life return to my dick. But then she popped up, and her movement pushed me out of her. She looked down at my cock, and then bent down and took it into her mouth. ‘Well now I can actually fit it in my mouth, and I have to say, you taste good. We taste good together.’

She got up and went to her kitchen to get a glass of water, and I followed right after. We stood together in her kitchen, which was effectively all glass panels, looking out onto a tightly manicured lawn and pool, both of us totally naked.

Jodi: ‘That was great, I’m glad I didn’t chicken out on sending you that text this morning.’

Me: ‘It was great, so thanks for the morning text. So what do you want to do now?’

Jodi: ‘I don’t know, what do you want to do?’

Me: ‘Do it again?’

Jodi: ‘I think that sounds like a good plan’

We went back to her bedroom, and made out some more, between exploring each others bodies. I told her I loved her ass. I then brought up the comment she made when my thumb was in her asshole. ‘So Eric wasn’t joking when he talked about fucking your ass, huh?’

Jodi: ‘He joked about that?’

Me: ‘Yeah, joked about it, talked about it, like all the time. I mean, I don’t blame him, with an ass like that, I would be wanting it all the time as well.’

Jodi: ‘It was like his thing. He loved anal. He was the first guy I ever did it with. Well, actually, the only guy I have ever done it with.’

Me: ‘No one since?’

Jodi: ‘Nope, just him. Went from like once a week to then never.’

Me: ‘Wow, once a week, good for you two!’

Jodi: ‘Ha, yeah, some good it did us.’

Me: ‘Yeah, I guess so. But hey, Vanessa and I did it once, and same result, so, you know.’

‘Ever use toys or anything’

Jodi: ‘In my ass, or at all? I mean, the answer is yes to both, so not sure the clarification mattered.’

Me: ‘Oh fun, can I see your toys? That could be fun.’

Jodi: ‘Sure, but no judgment, okay?’

She then took me into her closet where she had a fingerprint lockable safe, and inside, a fairly nice toy collection. A few butt plugs, a Hitachi, a couple clit vibes, and a few dildos of various sizes. ‘What’s the biggest thing you’ve had in your ass?’ She pointed to the large butt plug, still a respectable amount, but decently smaller than my cock in girth. ‘Never this one?’ pointing to the largest of her dildos.

Jodi: ‘No, never, the other one a few times, but never that one.’

Me: ‘Let’s try a couple of these out’, grabbing a few and a bottle of lube that was in the case.

I led her back to the bed, and told her to go face down with her hips slightly raised, and slid a pillow below her. I then started to eat her pussy from behind, before moving my tongue up to her ass. She moaned loudly, ‘oh that feels so good.’ I licked around her asshole, into the hole, and then back around while sliding my middle finger into her. She moaned as the ring tighted around my finger. I lubed it up again with some spit, and after a few minutes of sliding in and out, added a second finger. I then grabbed a medium sized plug and slid that into her. I then laid down and said, ‘why don’t you get back into your favorite position and I’ll make you cum again.’ When she did, I could taste the difference in her pussy, the wetness combined with my cum from our earlier fucking. Her lips and clit were engorged though, and I made quick work of another orgasm from her, the contractions pulsing the plug against my chin while she did . She got up, and said, ‘Seriously, I need to tell Vanessa thank you.’

Me: ‘yeah, let’s not go there.’ She got up towards her bathroom, and was starting to remove the plug, when I grabbed her hand and said, ‘come on back here, I’m not done with you.’ I brought her back to the bed, laid her back down over the pillow, and slowly worked that plug out of her. I then brought my mouth back down to her ass and lick a circle around her now slightly stretched asshole. I then returned to the small pile of toys, and grabbed the larger plug, applying more lube to it. As I pushed it in, slowly, she started to exhale and breath deeper. ‘oh fuck, it has been a while since I have had that in me.’ I worked it into her and then grabbed the clit suction vibe. She said, ‘That’s so good, but don’t let me cum, if I cum, I’m going to need that plug out of me.’ So I kept the vibe on her, but as she would get close, I’d pull it off, bringing her to the precipice, then back off, then back to the edge, then back off, repeatedly.

I could tell she was incredibly worked up, and said, ‘Jodi, I want to fuck you in the ass’

‘Oh fuck, yes, do it, fuck me’

‘Fuck you where?’

‘Fuck my ass’

I reached down and slowly worked the plug out of her before bringing her up to a doggystyle position. Her ass looked even better in that position than it had reverse cowgirl or laying down. I added more lube, and then put some on my cock, which was hard as a rock in anticipation. Her ass had been stretched by the two plugs at this point, but as I placed the head of my cock against it, there was still some good resistance, I pushed in and she moaned. It wasn’t long before I had worked half of the shaft into her ass, resting 30 seconds or so each inch along the way. Once she was comfortable, I handed her the clit vibe to use on herself. I started to pick up my pace a little. The thing about one night stands, is you always have to sort of make some educated guesses about how hard someone can go, especially if the one night stand involves anal. Even a girl who is willing to do anal in a one night stand may not be willing to get absolutely pounded. But as I picked up the pace, Jodi’s moans turned more into a moan and dirty talk, and there was no hesitation or request for relief. Within 10 minutes, I was now at a furious pace. It was like an otherworldly experience. Here was my ex-wife’s best friend, getting her ass absolutely destroyed by my cock. We had traveled as couples together, had known each other since she and Vanessas were in a mom’s club together. This gorgeous woman who was a banking executive by day, woke up this morning and sent a nude pic to her best friend’s ex-husband, hoping he would come over to fuck her, and now he is balls deep in her ass. All of those thoughts and feelings hit me, right as she started her orgasm. The vaginal and anal contractions that accompanied her other orgasms of the morning came through, and they clenched down on my cock, squeezing it as I continued my thrusts. The pulsing squeezes were too much for me, and my own climax started, this one perhaps even bigger than my first one earlier that morning. Once I was spent, I pulled out of her ass, a wet sucking sound accompanying the head of my cock pulling out of her ass. The cum in her ass started to leak, as her hole was gaping a touch still.

Jodi excused herself to the bathroom, while I stepped into her shower to clean off. I was still getting the temperate and shower height adjusted when Jodi opened the shower door and joined me. She turned me around and kissed me, deeply, grabbing my cock and stroking it. I had yet to wash off, so it was still coated in lube, cum, and her fluids. She stroked it a couple times, and I managed to get a little firmer, and she then dropped down to squat in the shower in front of me. I saw her looking at my cock, then up at me, and then back at my cock. She moved her head forward, placing my cock against her lips. While the shower was running, it was focused on my back, and there was little to no water washing down the front, so my cock was still comparatively fresh from the ass fucking we just shared.

Me: ‘Wow, you’re a dirtier girl than I thought you were.’

Jodi: ‘Eric always begged me to do this, never felt it in the moment’

I didn’t even get a chance to reply before she took my cock into her mouth. I watched her sucking the head, then licking the shaft, before she moved up, grabbed the body wash and started washing my body and cock. Taking me in her mouth like that was surely one of the hottest things I had ever seen a girl do, and my year so far had been full of hot women do hot things. She continued washing me off, moving behind me, and using the water from the shower to rinse her mouth and lips off. As she washed me, she started kissing on my body, moving back and forth down my back, around to my chest, and back to my now clean, and semi-stiff, cock. She moved below my cock and started licking and sucking on my ball sack, like my cock rested on her face. She then continued the licking and sucking while stroking me, my cock getting harder as she did. What she did next though completely took me by surprise, not because of the act, but because it was her. She moved her way behind me and still holding onto my cock, pushed her face up between the cheeks of my ass. She pulled back and told me to lean forward against the wall of the shower, and went back to it, this time, fully getting against my asshole, where I felt her tongue extend out. She proceeded to give me a wet and noisy rimjob, just absolutely slathering my asshole with her saliva while she stroked my cock. A few other women had given me rimjobs this year, but hers was amongst the best. I was basically fully hard at this point, when she got a phone notification from the bathroom counter. She pulled back and got up, leaning out the glass shower door. ‘Shit, I have a call in 30 minutes that my assistant wasn’t able to cancel. We’ll need to finish this later.’

Me: ‘Do you need me to get out of here?’

Jodi: ‘No, you can just hang out in the other room, it shouldn’t be more than an hour long call.’

******
Well, this got too long, so I’m going to split it into two different posts.

Source: reddit.com/r/gonewildstories/comments/ptgyy1/a_onenight_stand_with_my_exwifes_best_friend_fm