Reposting because I did the tag wrong the first time.
I’ve written about some related adventures in other subreddits if you’re curious, but I’ll give a quick recap here.
Maggie was a woman I dated for a few years at the beginning of my career as a writer. A redhead, short and curvy, leaning toward the chubby side of that range in all fairness. She was blessed with the biggest breasts I’ve ever had the opportunity to play with. I was on a book tour when events transpired to open up our relationship. It was me sharing her with other men at first, and that remained mostly the case. There were certainly women in the mix as well, but adding guys was far more common.
So threesomes were nothing new to us at the time where this story starts. We had, in fact, been placing ads online looking for new guys to play with her. We’d usually give it some blunt, smutty title bragging about her large breasts, but make it clear we were looking for decently cool guys, not just any random cock. At this point, we’d had luck with a couple of guys with this method, including one that remains a good friend of both of us to this day.
We’d always meet the guys at a neutral location, usually the coffee shop near our apartment. A couple of the baristas had absolutely figured out what was going on, which is a story for another time. This day, we were waiting for “Bobby” to show up. He had the perfect personality when we talked to him over email and text, and he hadn’t rushed in with a dick pic. In fact, he had agreed to meet up with us after sending us a neck-down photo, and with only a description of Maggie, similar to the one I gave above. So there we were at the coffee shop, with Maggie in a wrap dress that was almost more like a robe in how it fastened together with a belt.
A few minutes before “Bobby” was due to arrive, I see Maggie looking shocked. A whispered question to her explained why.
“This guy Dan that I work with just walked in,” she said softly. “Gonna be awkward as hell if he sees us meeting and leaving with some random guy.”
She and Dan exchanged a little wave but didn’t speak to each other. He, in fact, went and sat on the complete opposite side of the coffee shop, which was a relief…at first.
Time passed, and our date didn’t seem to have shown up. It was about five minutes after he was supposed to be there that Maggie and I figured out what by now is probably obvious to the reader.
I left it up to her. If she wanted to slip out and not say anything, I’d be fine with that. “No, I have to know,” was her reply.
I pulled out my phone, send “Bobby” a text, and waited. A moment later, Dan looked up, over in our direction, and stared for a long moment.
To his credit, he didn’t freak out. He took a deep breath, collected himself, and walked over.
“I guess you’re Bobby now,” Maggie joked awkwardly as Dan approached. We had given him my (super common) first name, but not hers, so he was equally blindsided by the new revelation.
The two of them had a brief, nervous conversation about work before falling silent. It fell to me to either nudge the situation to either a conclusion or to the next chapter.
“So, does this…change anything about the interest level here?” I said, less confident than I wanted it to sound.
Dan cleared his throat and spoke first. “I…no. I mean, not for me. But if it would be too weird, we can…”
“No, I’m good,” Maggie interrupted. “We can head home now in fact, if you’d like.”
Both of them were blushing profusely at this point, and my heart was pounding in its own right. This certainly added a new spin to things, one that could go either way.
It was a short walk back to our apartment, and I watched the dynamic between the two of them. Dan was checking Maggie out with the look of someone who had thought about it before but never expected anything to come of it. Maggie seemed to be almost ignoring him, but in a way that wasn’t hostile or avoidant. If I was reading it right, she was letting him have his looks without amping anything up…almost as if she was waiting for him to change his mind.
We made it back to the apartment, and after the obligatory “nice place” from Dan, he finally put some clearer words to his thoughts. “Not going to lie, I never would have thought you were into something like this, Maggie. I mean, even with the accurate description you gave, it never crossed my mind until I saw you guys sitting at the shop.”
Maggie relaxed into it a bit, even as Dan babbled a bit. “Have you ever thought about me like that before?”
It took Dan a bit to formulate a response. “I…ah…I mean, yeah. Yeah, absolutely. A lot of the guys at work talk about your tits when you’re not around.” He saw the error of that statement the moment he said it, the realization hitting twice as hard when he saw Maggie wince.
“Are you going to tell all of those guys about this later, then?”
“No, no, no…of course not! I…I’d just as soon they not know that I answered an ad about…that. You know what I mean?”
Maggie laughed, and some of the tension left the room. “At least some of the IT department would be jealous if they knew you’d even made it this far.”
“Ha, totally,” Dan admitted. “Especially Nick. He…” Dan paused as if he was worried that he’d already said too much, but was already past the point of turning back. “Nick is really fucking into you.”
Maggie nodded confidently, her usual ease in situations like this returning. “Don’t worry, I’ve seen him staring at my chest before,” she said, laughing a bit under her words. “Bet he’d love to change places with you right now, huh?”
Dan started to state his agreement but froze momentarily when he realized that Maggie was pulling open the front of her dress to reveal the bright purple bra she has on underneath it. Lacy, but not see-through, the plunge in the front revealed more of Maggie’s tits than he’d likely ever seen before.
“I…yeah. Holy fuck. Yeah, Nick would…lose his mind, yeah.”
Maggie kept working the dress open, until the matching panties were revealed below the bra, along with everything else between. “Bet he’d love a picture of this,” she said. Dan thankfully saw the comment for the playful tease it was and didn’t reach for his phone. He simply nodded and looked her up and down as her dress fell to her feet.
I moved into position for a better view as Maggie approached Dan, wearing nothing but the purple lingerie and her kitten-heel boots. I felt lucky that things were still happening despite the coincidence of our choice of partner.
“And you promise you aren’t going tell Nick about this?” Maggie asked, her chest no more than a few inches away from him.
Dan swallowed hard. “Promise,” he said at just above a whisper.
“Good.” With that, she gently pushed him back onto the nearby couch. She was straddling him by the time they landed and grinding against him a moment after that.
I settled into a nearby chair as they started to kiss. This was…well, I won’t say old-hat exactly, but something I knew how to handle. By the time Dan was cupping Maggie’s huge tits and burying his face between them, I was already rock hard and stroking through my pants.
Dan got Maggie’s bra off a short time after that, the words “holy fuck” coming out in a near-growl as he saw her tits bare for the first time. I chuckled from my nearby vantage; I still thought that sometimes when she undressed, so I could hardly blame him for his response.
All the grinding had them both moaning after a while, and Maggie slid off of Dan’s lap and to her knees in front of him. He stared down at her in awe as she urgently worked on his belt, button, and zipper to get into his pants. She had his thick cock out in no time, and her lips around it fast enough that Dan and I both gasped.
For the first time since we’d arrived at the house, Dan looked over at me. I think he was trying to assess if I was cool with everything, but the sight of me now working my own pants open eased his concern. He gave a strained laugh, looking down at Maggie’s head bouncing up and down on his cock, then back at me.
“God, she is fucking GOOD at this,” he said, moaning lightly.
“Practice,” I responded immediately, my own cock now sliding into my hand. “Lots of practice.”
Maggie let out a chuckling moan around Dan’s shaft, never breaking her rhythm.
I waited a couple of minutes before I allowed myself to slide off of the chair I was in and make my way over to their scene. While stroking myself, I moved alongside Maggie, pulling the panties down from over her rather thick ass.
Maggie sighed appreciatively as I ran my hands over her full backside, while Dan was looking down across her body with great interest. When I gave Maggie’s ass a playful slap, Dan grinned deliriously.
“You like it?” I asked, grabbing Maggie’s ass firmly with both hands and jiggling it.
“Love it,” Dan answered, his voice shaking in a way that alerted me to the fact that Maggie’s blowjob was putting him at risk of this being a rather quick session. I gave Maggie a firm nudge, enough that her mouth popped off of Dan’s cock as she looked up.
She took the hint without any explanation and rotated her body to face me instead. Within a minute or so I was lying on my back on the floor with Maggie’s lips wrapped around me, as Dan started playing with Maggie’s ass-cheeks.
Maggie’s expression, and pace at sucking me, made it abundantly clear when Dan started to finger her. It was even clearer when he had squirmed around in the limited space enough to start licking her pussy from behind.
It didn’t take long after that for her face to rise up from my lap. After staring at me for a moment with wild eyes and a low moan, she turned her head in Dan’s direction. “I…need you…to fuck me. There….mmm…should be condoms in that….drawer there.”
Dan was more than ready to change it up, and was fumbling in the drawer almost instantly. It took a couple of minutes, but soon Dan was wrapped up and thrusting deep into Maggie.
Now, I mentioned this wasn’t our first time, but this was beyond any doubt the LOUDEST it had ever gotten that quickly. Dan himself was a grunter and a dirty talker once he got going, and clearly his simple “mmm, yeah, take that cock, fucking take it” hit a nerve for her. She later told me that it, combined with the mild taboo of it being a coworker, started to get her off way quicker than expected.
I’d also love to tell you that we rotated through nine more positions that night, that it lasted for hours…but no. For whatever perfect reason, our enthusiasm just built off of one another. We by no means came at the same time with porn star perfection, but everyone DID get off to the point of needing a break, all just from the classic spitroast position. And there is almost no possible way our neighbors didn’t overhear.
We did hook up with Dan several more times after that, though. To the best of my knowledge, he didn’t tell the rest of the IT team, either. :D
Source: reddit.com/r/gonewildstories/comments/q7cnzc/online_hookup_ad_goeswrongthen_right_long_mfm