This happened a couple years ago, when I could still travel for work. This experienced roped in some of my favorite things- tension, past lovers, someone watching and enjoying herself, filming…. wonder if you’ve had something similar happen?
I dated Kate when we both lived on the west coast. Dating might be a strong word- we met for drinks for a few months went back to my place, watched movies, had lots of sex. No feelings really developed, but we had fun with each other and sometimes, that’s what counts. Of course, we communicated these things as well, and were always on the same page.
After a bit, she told me she was moving back to NYC. I thought this might happen and I think she started distancing herself to prep for the move which is totally fair. We only had one or two more hangouts after that and I was sad to see her go but happy for her in making a change that seemed right.
I travel to NYC a lot for work and despite this, over the years we managed to fall out of touch. Until last year. I can’t remember who reached out to who and on what social media but we ended up messaging and planning for “the next time I was in town.” I didn’t think that much of it, really. I’m all for a friendly drink and maybe there might be some mild flirting or suggestiveness from our former days, 5 years before.
Next work trip finally arrived and I booked my AirBnb and let her know which neighborhood I was staying in. I was a just a short cab ride away from where she lived and we made tentative plans- the type where “if we had time, we’d grab a drink”, etc. I think this was to maintain any sense of casualness, not overstate anything, etc.
A few weeks later and I was in Brooklyn again, going to meetings, working, grabbing drinks with friends. It was the second to last night that we had tentatively picked for getting together. We texted a few times making sure we were still on and then met up at a bar she suggested.
I walked in and she was already there- looking similar but different. It had been 5 years or so since I’d seen her in person, but saw some of her social media. Short black hair gone, now shorter blonde hair. Dressed in her usual short black skirt, boots, tights (are they thigh highs?) and something like three stringy tops all layered on each other.
We hugged and I grabbed a beer and joined her. Conversation was awkward at first but after a drink we fell into a more casual fun tone catching up, talking about work, our cities, etc. A friend of hers, Sarah walked past and said hi to both of us during our second drink. Sarah was a knock out- dressed in a similar way, longer hair, shorter skirt, a little more “elegant”. They chatted briefly, gave eachother a quick kiss goodbye on the lips and then Sarah took a seat at the bar. Kate and I went back to chatting.
We talked dating for a bit and somehow the topic of sextapes came up. “You don’t have one of us, do you?” she said. I hesitated- “Yeah… I filmed you one night you were at my place… but I’ll totally delete it right away if you want me to!!” She started laughing and said, “oh right, I remember!” Whew. At the time, we both agreed it was ok/ sexy to do, but the last thing I wanted was for her to feel uncomfortable about me still having it. I take that kind of thing seriously.
“So… do you watch it very often?” she smirked as she sipped her drink? “Honestly- not that often. The lighting is terrible- earlier phone and all.” It’s true. The video that I have on my computer (not on phone) was shot on an older iPhone and my room was very dimly lit at the time. You can hear me moaning a little as she sucked my cock and can make out her face a little. I remember turning it off when I realized you couldn’t see much. But she thought it was funny that I couldn’t see her face while she was sucking at the time and you can hear her gently laughing while my cock was in her mouth. It was kind of cute and I always kept it. The fact that I HAD it and it reminded me of her was sexier than just the would be more carnal shots of the video.
“So you never really watch it?” she replied, fake pouting. I laughed and said I still valued it, but it wasn’t the most graphic. “Well shit, “ she said, looking around. “If you’re going to have a fuck tape of me, it should be a good one, right?”
I nervously laughed, not totally sure what she was implying. I was a little wary since I didn’t want to assume anything and say the wrong thing/ get in trouble. I knew her to not take any shit from men, and I wasn’t about to say something sleazy to give her a reason.
“What do you mean…?” She had gotten up and walked up to the bar where her friend Sarah was sitting. They started talking and laughing a little. Then, both returned to the table, 3 shots in hand, one for each of us. “Let’s take these and then you call us a cab so you can show us your Airbnb.”
Oh! Ok. I guess that early drink, mild flirtation kinda panned out. Knowing that she was game, gave me a lot more confidence in the situation. “Perfect” was all I said and took down the shot immediately. While they drained theirs, I reached for my phone and dialed up a Lyft. We gathered our jackets and waited outside.
We piled in the Lyft with Kate sitting in the middle. I had my hands on her thigh immediately and I could tell Sarah was doing the same thing. I loooooove car play, but knew we didn’t have much time, so I decided to enjoy the tension for a bit and before I knew it, we were pulling up at the apartment building I was staying in.
Inside, I took both their coats and gave them (the very quick) tour. I poured them wine, leaving the bottle on the table, also brought out a bottle of whiskey i had, in case anyone wanted something stronger.
“So, let’s see it”, she said. We all circled around my laptop. I wouldn’t show the screen until I had her video up, though I did show her how I had it password protected. “Are those folders other girls you have?!” in mock surprise. “Yes- but they are all locked and no you can’t see them. Well, there are like three in here who have given that consent, but no others!” “Me me me!” she yelled so as her and Sarah were giggling, I pulled up the video I took of her sucking my cock five years earlier.
“You’re right, I can barely see myself!” We watched it through a couple times, commenting on it, etc. I would sneak looks at both of them as we clicked play a second and third time, my cock stiffening in my jeans. Sarah said, “i know you can do better than that…”. Kate looked at me- “can Sarah film me sucking your cock on your newer phone now?”
“Yes, a thousand times yes”, I replied and handed my phone to Sarah. Kate somehow removed all three of her tops at once and got down in between my legs. Sarah giggled and positioned herself. Kate then yelled, “WAIT! Make sure that lighting is good.” We all three laughed and Sarah adjusted the lighting- dark, but still able to see us, thanks to this newer model phone.
Kate took me all the way down her throat practically right away- I think to show she meant business. She then backed off a little bit, teasing the tip of my cock while Sarah hovered around getting the best shots. As Kate’s head bobbed up and down, Sarah sat next to me on the couch. I put my hand on her thigh, tracing her stockings and going a little up her skirt. “No sir, mister- that’s as far as you go.” she said as she kept filming. “Loud and clear”, I moaned, though another kink of mine is having an audience, so I was perfectly happy for her to just watch. Expressing boundaries is important, after all.
Sarah did follow suit and took off her top and hiked her skirt up, all while keeping a steady hand, camera pointed at Kate doing her best work. She stopped and looked at her friend, wiping her mouth, “How’s it looking? Better?” “Oh god, yeah” Sarah replied.
With that affirmation, Kate went back to slowly running her tongue up and down the length of my dick, occasionally looking up and smiling at me. I’d smile back, really loving the playfulness of it all. As she moved faster and faster and I let out more moans, I let slip, “wait.. i don’t want to come just yet…” She slowed to a stop and said, “good- my turn.” She helped me up, switching spots with me, my dick aching for release.
She flopped back onto the couch, pulled off her skirt, but left her thigh highs. “You remembered”, I smiled as I opened her legs. She grinned as we both recalled I liked certain types of dress up like this. She put her hand in my hair as I leaned in closer to her nearly shaved pussy. She was already wet, so i teased around her lips, gradually getting my fingers involved. I looked up once, but feeling camera shy, went right back to business. I’m glad I looked though- by that time, Sarah had her own skirt off, just watching but filming with only one hand as he other hand was buried in her panties. I caught the two women grinning at each other right as I got back to work.
I continued, getting Kate closer and closer to coming. I didn’t want her to have that yet, so it was my turn to pull her up and re-position her. I laid her flat on her back, opening her legs again as I hovered over her. I started teasing her clit with just the tip of my cock. For a moment, I forgot about Sarah who had to reposition. She got her camera right in close on my dick as I pushed it gently into Kate’s pussy as we both gasped. Five years later and she still felt amazing. I started slow, feeling her hips rise up and meet me, until we started moving in unison. Sarah had slumped low in a chair, her legs fully open and dripping as she played with her naked pussy. “Hold.. that camera…. straight…” Kate managed to gasp as I thrust in and out and all three of us laughed together. I placed Kate’s ankles onto my shoulders and repositioned a little bit, aiming more down inside of her… deeper.
I kept watching Sarah play with her pussy off to the side. Of course, I wanted her to join. I wanted to watch Kate touch her and wondered if they had ever played. For now, I didn’t want to be greedy of course since I so loved watching a woman masturbate and love even more if she’s turned on by watching me.
I looked down at Kate again, as she smiled up at me. I’d slowed a little, momentarily distracted. Needed to change it up, so I pulled Kate up again, turned her around and bent her over the couch, pushing into her from behind. Sarah moved again, getting the best shot as Kate started to get even more vocal. I always knew she liked it like this, and I remembered just how to hit that right spot over and over. I reached around, certain to use my fingers on her clit and sure enough after about a minute of this, Kate let out the sweetest moan that turned into a short scream. Sarah had thrown one leg up over the couch, rubbing herself faster and faster. Later, I’d see this is where it got pretty shakey for a bit, but I didn’t mind one bit.
“I’m gonna come soon.. “ I heaved out and Kate pulled me out of her. She quickly got in front of me and as we were both panting, she said, “and now for the big finish” as she knelt down. I started laughing a little as I came all over her tits and chin. Sarah had just started to come as well and tried to get the come shot in frame like a good videographer.
All three of us fell onto the couch, sweating, covered in come, awkwardly laughing. “We remembered all each other’s spots!” explained Kate, which I found pretty adorable. As we were catching our breath, of course I asked if they’d done this before. Sarah replied, “we’ve fooled around a few times together for fun, but never filming like this. I loved it!”.
After a little clean up we poured some more drinks while I offloaded the footage. I never keep incriminating stuff on my phone for long. We settled in and cuddled up together to watch the show.
“Yep- way better than the last one”, Kate said.
Source: reddit.com/r/gonewildstories/comments/kn9ud9/mff_an_old_flame_and_making_a_better_sex_tape_in
Damn!! Amazing.