TL;DR Girlfriend and I watched stimulating content on Tivo, talked about it a lot, joined an “adult” dating site, and ended up having a full swap with our friends.
Anna (not her real name) and I met when we were both dating other people. I always liked her, and about a year after my own breakup, I happened to bump into her, randomly, in Boston. We ended up going for dinner and drinks, and I spent the first weekend at her condo. We ended up getting a new place and started living together about 6 months after that.
Anna was just insanely great, and I knew that I got super lucky here (I’m far from a troll, but dang did I “date up” here). Highly intelligent, quirky sense of humor, affectionate, charming beyond belief, highly sexual, and she was also a total smoke show, a tall brunette with a fabulous body. She loved wearing dresses and heels (my favorite!), and also had this exhibitionist streak. Any time we’d go some place warm for vacation, she’d wear these smaller-than-normal bikinis. Men would flock to her, and I was more than fine with that; you see, I felt that Anna, like me, might be interested in — let’s call them “extracurriculars”. Any time that a guy or two would hit on her / flirt with her, she’d practically drag me back to the room and ride me with reckless abandon.
Still, Anna and I never discussed extracurriculars, or at least we hadn’t yet. It was just too early for me to talk about how I dated a married woman, how an ex and I used to swap, or my experiences with other men. Besides, Anna was great in every way. But then it happened… as it always does.
Anna and I just got a Tivo. It was very early in its production, and while it was cool and useful, it would totally botch auto recordings — that were supposed to match our viewing preferences. Let’s say that we’d watch a lot of sports; well, Tivo would frequently auto record from “Animal Planet”. Why? No idea. It was super weird and annoying. So, this one Friday night, we were both exhausted from hard weeks at work, and we just sat in front of the TV like zombies, sipping on some wine. Anna thumbed through the menu on Tivo, and found this movie called “Excitement Island” (I forget the exact name at this point). She was like, “WTF this is? Oh, that kinda real porn.” Then she shrugged and asked if I wanted to watch.
We’d watched porn together before, so I said why not. This movie was about a couple who were seduced into swapping with another couple. While the sex scenes were simulated, I admit that the movie was somewhat well done, and that it definitely created a stirring in my sweatpants. I could hear Anna’s labored breathing as she sat next to me, catching the heaving of her chest through my peripheral vision. She reached out and grabbed my hand, shoving it down the front of her thong. For what seemed like an hour I edged her, making slow circles with my middle finger around her clit, periodically snaking my middle finger into her soaking wet pussy. Anna narrated about how much this movie excited her amongst the various other items of dirty talk as I continued edging her.
She came with a fury towards the end of the scene where the swap was coming to an end. She threw my hand off her crotch, jumping off the couch, and stripped naked in front of me. She pulled me off the couch, and practically ripped the sweatsuit off my body — before shoving me back down and climbing on top of me, wasting no time before shoving me inside of her. I was all revved up, grabbing each of her butt cheeks in my hands, slamming her pelvis into mine, but she told me to slow down, and let her set the pace.
Instead she took deliberately slow strokes before plopping down on me — while maintaining intense eye contact. Anna always did this when she wanted to discuss something during sex, and I was always willing to be a captive audience. “That movie was just so thrilling…” *plop* “So hot…” *plop* “I always wondered what it would be like to experience something like that…” *plop* My eyes grew wide. “I mean, have you ever…”
“Tried it?” I interrupted her.
“Yeah,” she responded.
“Yes.”
“Oh my god! I knew that you were a sex fiend!” *plop* “Tell me all about it.” *plop* “Did you love it?!”
“Yes, it was very exciting, and while it happened out of the blue with some friends of ours, we’d already discussed it to death beforehand, so it turned out to be a pretty cool night. Very enlightening.” *plop*
Anna practically screamed as she came, her cunt aggressively squeezing my cock. But she kept going. I think that if I wasn’t being so cautious in the way that I worded things, I would’ve nutted already. In terms of hotness and how my girlfriend just told me that she was into extracurriculars like this — was absolutely one of the hottest things that I had ever heard.
After she came down from her orgasm, still slowly fucking me, she started in again. “Wow, I mean, were you jealous?” she asked. *plop*
“Yes, but, it comes down to good jealous versus bad jealous.”
“What?” *plop*
“Bad jealous is when you don’t want something to happen, but it happens anyway, you have no control over it, and there is jealousy and resentment. Good jealous is when you are in a situation where you feel a little bit nervous and apprehensive, and yeah you’re *slightly* jealous that somebody else is fucking your girlfriend or whatever, but at the same time the fluttering of your heart and the weakness in your knees, along with the pleasure that you’re also receiving, all the while doing something that society says that you shouldn’t be doing, makes good jealous the jealous that you want to have. Do you know what I mean?”
“Ohhhh… good jealous sounds amazing. I would love to experience good jealous!” *plop*
“Mmm, so you really want me to share you with another man?”
Anna started telling me insanely detailed descriptions of her past sex life, as she picked up the pace. *plop plop plop plop plop* She grabbed, pinched, and held on to my nipples, pushing me over the edge. We slowed down the pace and kissed until I plopped out of her.
We showered together before falling asleep. Anna told me that it was going to be Naked Saturday before heading downstairs to make coffee. Naked Saturday involved us spending the entire day naked, and usually having a lot of sexy talk and sex. Suffice it to say that I really liked Naked Saturday. I came down naked, and Anna was mostly naked except for the sexy heels that she was wearing. Man, could that woman press my buttons! I came up behind her and kissed her neck, my semi hardness rubbing up and down her crack.
I grabbed a cup of coffee and sat down next to the island in the kitchen.
“So did you think about it more? I couldn’t stop thinking about it all last night, and I just can’t get it out of my mind.”
“So, you’re serious about it?” I replied. But we’d definitely have find a way to do this, because once a thought got into Anna’s head, it would never leave. Like, ever.
“Yup, but the problem is that I don’t know where to start.”
“The internet, most likely.”
We headed to our office room, and I sat in the chair in front of the computer. Anna said, “no fair, why do you get to drive?” I was about to get out of the chair, when Anna plopped down on my lap. I couldn’t really see what she was searching for from my vantage point, but as always, she narrated. “Oh, here’s one, it says that it’s free. Wait, no, it’s terrible.” At some point during her exploration I entered her, and I basically just sat there with my hard cock inside of her wetness, she periodically turning her head to kiss me, or rocking her hips for a couple of pumps with me inside of her.
Finally she found one, but we had to pay for it. It was like $50 for a few months, and she signed up for it. The site had a lot of profiles, a lot of pictures (for that time at least), and a lot of couples who appeared to be within a reasonable distance from us. We debated putting our pictures up there, but at the time it was a nuisance because you had to take the picture, download it from your camera, and put it up on the site; plus there was no way to have “private” pictures. We also used to walk to work, 3 miles each way. Those were harder times.
By that point I’d bent Anna over the desk, and was pounding her from behind, with my thumb in her asshole. It took her some time to complete our profile since she kept mistyping and having to hit the delete key to fix things. HAHA! Finally she finished it, and clicked the submit button, reading everything back to me. It sounded perfect, and I finished in her right after her last word, but little did we know…
The number of single guys reaching out to us (even though Anna was crystal clear that NO single guys were wanted) was out of control. We did reach out to a couple of couples, and couldn’t wait to hear back. Saturday was basically that: sex, check to see if we got new messages on this adult site, have a glass of wine, more sex, check the messages, repeat.
Anna and I used to double date with our friends Ben and Maggie (not their real names). Ben and Maggie had been married for about 5 years, and weren’t sure if they wanted to start a family. Anna knew Maggie from work, and Ben and I hit it off instantly as well. Ben was a large physical specimen like myself, save for his full head of hair, but Maggie was different than Anna in every way. While Anna was fit and tall and bold and a knockout, Maggie was a short, petite, shy redhead with pale skin who was extremely shy — until she had a few drinks, that is. Still, Maggie was a cutie. And I’m pretty sure that Anna crushed on Ben a bit, but I didn’t really bring it up — since there was no context… until now.
I left the house early on Sunday to meet up with Ben. He and I shared the hobby(ies) of fishing, drinking beer, and cigars. Both Anna and Maggie hated cigars (and fishing!), so we spent our fishing time away from the ladies, enjoying our pretty foul (yet enjoyable) habit(s).
Anna was going to meet up with Maggie later to do some shopping at the mall, maybe have a light meal and a few glasses of wine. As I drove to the boat launch, I wondered if Anna would tell Maggie about her swapping fantasy. I heard them talking before at our home, a few drinks in, and Anna and Maggie had these detailed and visceral conversations about Ben and I as lovers, and the kinds of things that they wanted and enjoyed. I never brought it up with Anna, because why would I have at that point? But I couldn’t wait to get to get home and see if Anna had anything to tell me. With history as my guide, she almost certainly would. I couldn’t wait.
Ben and I hit the lake, and it was as if nothing changed. Ben and I were fundamentally different. One of us was conservative, and one of us was not. But our cores were identical, we were on the same page about how we interacted with our partners, and we both liked to rib each other, and to laugh. I’d only known him for a year at that point, but I really liked hanging out with him.
We were pretty much in the middle of the lake when he stopped engaging. He took a slug of his beer, and a draw from his cigar, and he stared into the distance. I hadn’t seen him like this before.
“Dude, what’s on your mind?” I asked. “You are just staring into space right now.”
“Well, uhh, I don’t know how to say this, and I know that you and I talk about Maggie and Anna here and there, but, there’s this thing.”
“This thing?”
“So, uhh, well, you know that we’re pretty conservative, right?”
“Yeah. I mean, you both complained about Al Gore for almost a year,” I joked.
“Yeah, but that isn’t it.”
“It’s not?”
“No, so, ahh, well… we both intend to stay married and all that, and I love her to death, as she does me, but…” He took a deep breath. “We both enjoy having sex with other people, like sometimes together, and other times… separately.”
I choked on the drag that I just took from the cigar. I thought that Ben was going to tell me about a cancer diagnosis or something. I coughed and coughed and coughed.
“Dude, knock it off,” he joked. “You’re going to scare the fish away.”
I laughed and coughed and laughed and coughed. Ben’s face got beet red.
“I’m sorry, Ben. I’m (coughing) sorry. For real. But there’s also this thing on our end.”
“What thing?”
I relayed the story about the Tivo and how it had weird ways of profiling our viewing habits, how Anna and I watched this bawdy soft core movie about couples’ swapping, and how she blew my mind when she said that she would be interested in it.”
“Wait, so you’re going to do it?” he asked.
“She was pretty insistent, even yesterday morning. I mean, I left before she woke up this morning, and if she was awake she probably would’ve brought it up again. As you know, Anna is like that…”
“Yeah, I know, brother. So what are you going to do?”
“Well, Ben. We joined this adult site, and it was pretty shitty out of the gate. So we’ll have to figure it out. I mean I have experience with this type of th-”
“Wait, you’ve done this before?”
“Well, you’ve often said that you think of liberals as self-righteous assholes who enjoy fucking around, and maybe there’s truth to that after all?”
Ben laughed. “But now I guess we’re self-righteous conservative assholes who also enjoy fucking around?”
We both laughed.
“Oh god, dude,” Ben continued. “What are the chances of… this kind of playing out like this?”
“Are you saying that you want to swap with us? I know that you have eyes for Anna and all… It’s fine. I don’t care, and I’m glad. Anna is pure sex, and is incredibly charismatic, and all of those things that we’ve talked about before.”
“She’s pure se-?”
“Oh, yes,” I interrupted. “It’s pretty fucking remarkable. I was, again, shocked that she even talked about swapping, like, at all. But, what about Maggie?”
“You have no idea, man. She gets a head of steam, then watch out. Plus she thinks that you’re super cute.”
Interesting… “Know what’s great, man?” I asked.
“No, I have no clue.”
“As you know, Maggie and Anna are hanging out today. And you know what Anna is going to do?”
Ben boggled for a moment or so. “Holy shit, she’s going to tell Maggie everything!”
“That is my thinking at the moment. I can’t wait to get home.”
“Neither can I!”
With that, Ben pulled up the anchor and we basically raced across the lake to the launch, and a few hours in, we’d caught *zero* fish. We got the boat on the trailer, then stood in the parking lot brushing our teeth, flossing, gargling Listerine, and so on. It takes a LOT to get cigar off the breath, and I think that we both had issues of connecting with and of passionately “reconnecting” with our partners. Then Ben and I drove home feverishly, but separately.
The water was running when I got home. I tossed my fishing clothing on the floor of the laundry room. Anna was in the shower upstairs, and I pulled back the curtain before joining her.
She was surprised to see me, she turned around, and we kissed.
“Hey, babe,” she squealed. “You’ll never believe what happened when I was hanging out with Maggie today!”
And that, my friends, is going to be discussed in Part II of this series.
Source: reddit.com/r/gonewildstories/comments/yy1fkt/mf_extracurriculars_part_i
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