Flirty banter with a friend led to mutual masturbation [MF]

This happened over a decade ago, when I was 23, still in a long-distance relationship after college, but one that was growing increasingly distant as she and I formed lives in separate cities, and it was starting to feel like a breakup was inevitable, although neither of us was quite ready to yet. We hadn't seen each other in a few months, and as a chronically horny twentysomething, the lack of sex was getting pretty rough. As we had started to become more distant, phone sex and sexting had also started to become more and more infrequent, and my horny thoughts were definitely increasingly turning to other women and men around me.

Around this time, a woman entered my friend group who was a coworker of a close friend. She was a free spirit - very flirty, confident, and openly sexual, going through a time of unattached sexual adventures, and talking about those adventures with an openness that allowed us to all live vicariously through her - and also made all the guys in our friend group seriously want her.

She was insanely hot - a brunette with a beautiful body, fit and muscular from the gym but with curves in all the right places, beautiful big tits, tattoos all over, and long wavy hair. And she had charisma - she was an extremely magnetic person, and between that, her openness about her sexuality, and her casually flirtatious nature, we were all crushing on her hard. Increasingly she was the one who I was thinking about whenever I jerked off, and I was barely thinking about my girlfriend when I jerked off at all. I had a feeling that she was particularly attracted to me along my friend group, since she seemed even a little bit more flirty with me than with the others, but I also thought that might have been wishful thinking. I also didn't give it too much serious thought, since I was in a relationship after all, and I was not looking to break up, nor was I looking to cheat.

But then one night that summer, during a week when my girlfriend and I were not talking after an argument, she threw a house party for our whole group of friends. A bunch of alcohol was consumed, a bunch of weed was smoked, and some strip card games were played, which saw her at one point get completely naked, and saw me get down to my underwear, trying hard to not get a boner in front of everyone looking at her. It turns out her nipples were pierced, and she shaved her pussy, and had even more tattoos than we knew...

Nothing sexual happened during the party after the strip games though, and clothes went back on, and the rest of the party went as expected. As the night wound down, I wound up being the last person there, having offered to stay and clean up since I lived just a bit over a mile away. Once everything was passably cleaned up, she and I wound up sitting in her living room sharing one last joint.

Then she said to me, with a more flirtatious voice than I'd been hearing the rest of the night, "so we've never wound up hanging out alone before... Tell me, what's your arrangement with your girlfriend? Are you allowed to play?"

She was looking me right in the face as she said it, hunger in her eyes. I felt blood rushing to my dick right away. It was a serious "devil on one shoulder, angel on the other" moment - I could have sex with this woman, who I had spent the whole summer jerking off thinking about, right now, and my girlfriend would never have to know, if I didn't feel guilty and tell her. But I knew I would feel guilty. Cheating was not in my nature, and I knew I could not do it.

"Sorry, no, we're exclusive." I told her instead.

"Damn, when you stayed to help clean up I was really hoping we could fuck" she said.

I was throbbing hard, looking at how hot she was, thinking about how good she looked naked earlier. My head swimming with booze and weed. "Well for what it's worth, telling you no just then was one of the hardest things I've ever done. I want to so bad. You are so fucking hot, I wish I could play with you."

"Oh yeah?" She said coyly.

"Yeah... I am absolutely going to jerk off thinking about you as soon as I get home, I promise you that."

"Well that's no fair!" She said, jokey flirtation in her voice, "for you to cum thinking about me and I don't get anything! I didn't even get to see your dick before, when we played the game you only got down to your boxers."

"Sorry!" I told her.

She bit her lower lip, looked at me deviously, and sprung her proposition: "I have a better idea - if you're going to jerk off thinking about me tonight, do it right here so I can watch. You'll stay in your chair, I'll stay in mine, I won't come over there and slide my pussy around you, as much as I want to, so you won't be cheating on your girlfriend. And I'll give you some motivation. Deal?"

I knew it was wrong - I knew that at bare minimum, that was being extremely generous with the line of what is cheating and what isn't. But I was absolutely blasted on beer and weed, and my boner was begging to be let out and indulged, so I accepted her questionable logic. "Deal."

"Take it out." She told me.

I unbuttoned and unzipped my pants, and pulled my hard cock out, and started slowly rubbing it.

"Oh fuck, that thing is nice - I love that head!" She told me.

"I'm glad you like it!" I said

"You're sure you don't want me on my knees in front of you sucking it?" she said

"Oh I absolutely want that, that's exactly what I'm imagining right now," I told her as I slowly stroked, "but I can't..."

"You just keep imagining it then," she said. "Oh and just so you know, I can deepthroat." Fuck, that drove me wild.

As I kept jerking off, she slowly unbuttoned her shirt, and took it off, followed by her bra, letting her beautiful pierced tits bounce free. "What are you thinking about right now?" She said. "I'm thinking about how much I wish I was fucking your pierced tits right now." "You could be..." She teased.

Her eyes were glued to my hand slowly rubbing up and down my cock. Then her hand slid into her shorts, and she started rubbing herself. "Ohhhh fuck..." I said. "See, isn't this better than both of us rubbing one out alone after you go home?" She said.

We sat like that for a while, in opposite chairs around the coffee table, her rubbing her clit inside her shorts, me stroking my cock openly in her living room. Then she said, "I'll be right back."

She got up and left the room, and came back a couple minutes later with a realistic-cock-shaped dildo and a bullet vibrator. She unbuttoned and unzipped her shorts and let them fall to the floor, and then she sat back in the chair, putting her feet up on the coffee table with her legs spread, revealing her glistening wet pussy. "You're sure you don't want to fuck me instead of this dildo? I won't tell anyone if you won't..." "I'm sure." I told her. "Imagine that it's you then... I definitely will be."

She parted her lips with the head of the dildo, and slid it into her with a moan. That she took the vibe and started massaging her clit with it. I was feeling ridiculously good, watching it all and continuing to jerk off. I was glad that I was so high - it was giving me some serious extra longevity.

Still, soon I got to the point where I was edging while watching her... I told her as much. "Good... I want to watch you shoot it everywhere for me," she said. I looked around, and thought it was good that she didn't have carpet.

"If we were fucking right now, where would you want me to cum?" I asked her.

"Where would you want to?" She responded.

"My girlfriend never lets me give her creampies... I would want to cum inside you!"

She gave me the naughtiest smirk. "Buy me the morning after pill tomorrow, and I'd let you breed me tonight." Oh fuuuuuck...

"I'm so close now too" she told me. "I could cum anytime." "You ready?" I said to her.

"Imagine filling me up" was all she said.

I did, and I started to cum, shooting ropes of semen all over her glass top coffee table and hardwood floors. "Oh fuck!" She gasped started to cum too.

When both of our orgasms were done, we just looked at each other for a moment, with naughty smiles. Then she looked at her glass top coffee table, then back up at me, and with a smile she leaned forward, and licked a rope of cum off the glass.

"Well that was a fun end to the night," she said. And then added, "even if we could have had a little more fun - we still could sometime you know." "If circumstances were different..." I told her.

My relationship did end up ending shortly thereafter, although my girlfriend never knew about that mutual masturbation session. As for me and that friend - we had fun a few more times.