Secret Cupids

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Double Penetration

Please note that this story is not loaded with wild and graphic sex. If that’s what you’re looking for, and I don’t blame you if you are, Literotica has tens of thousands of stories that will better fit your needs.

***

“Just remember, nerds,” Ally told us, “we’ve got our party tomorrow. So no working 14 hours, okay?”

Okay, first of all we weren’t nerds: we were geeks. And as for 14-hour work days… yeah, okay, that was normal for us. Tech start-ups don’t succeed on their own, you know (and we were doing quite well indeed). But that’s why Ally insists we all go out to dinner together or something once a week, so we don’t burn out.

She’s the boss. She insists we’re all equal partners here, but every group needs somebody in charge: otherwise there’s be nobody to make us take the occasional evening off.

“Yes, boss,” I told her.

“Not the boss,” she said for the millionth time.

Back in December she organized a holiday party with Secret Santas. I drew her name, so I bought her a coffee mug inscribed with NOT THE BOSS.

With two of us 3000 miles away in New Jersey pitching our product to a software company, and Lana in Arizona with her sick mother – Ally had to order her to go, threatening to cancel her access codes if she didn’t – we were down to eight of us for the party (the party was just for us geeks, so Madison’s boyfriend wouldn’t be coming, and neither would my wife – which, the way things have been going at home, was probably for the best).

“And remember,” Ally added. “Red.”

Ally could be kind of bossy, for a non-boss, but she did come up with off-beat ideas. Having ten of us form an Iron Man team last year (that’s a swimming/running/biking competition) wasn’t her best one, but it was memorable. Highly embarrassing, but memorable.

So the next day, we were all sent home at 3, and met up in a suite in the Washington Hotel at 7. It was decorated entirely in red (just as we’d been ordered to wear nothing but red, even down to our underwear). The guys all wore red sneakers, since you can’t really find red men’s shoes. Red wine was served, and there was plenty of Red Bull in the fridge (which had been wrapped in red crepe). The hors d’oeuvres were red, we were going to have pasta with red clam sauce for dinner… you get the idea: red.

It was a Day Before Valentine’s Day party, and I thought we were lucky Ally didn’t make us wear nothing but cherub wings (though I’d gotten a look at some of the women’s figures during the Iron Man fiasco, so I wouldn’t have minded that at all).

Tonight, though Jamie was wearing a dress (which, I couldn’t help noticing, complimented her slim figure), everybody else was dressed pretty much how we dressed for work. Except, you know, in red.

Ally had packed her iPhone with music and since there were four guys and four women, she insisted we partner up randomly for each dance. I’m pretty sure the last time I’d danced was at my wedding, but I ended up with Lin, a whiz-kid programmer a few years younger than the rest of us, barely out of college. She and I did a respectable job dancing to Little Red Corvette – compared to everybody else, anyway. But 99 Red Balloons didn’t go well for anybody and when Snoopy and the Red Baron came on, Madison and Alex threw red m&m’s at Ally.

A slow version of Red Red Wine gave us our first slow dance and – fortified by the actual red wine – Madison and I just swayed with the music as we held one another. I really enjoyed it, probably more than my wife and her boyfriend would have appreciated.

“That wasn’t half bad,” Ally said. “Any objections to changing partners and playing that one again?”

Nobody did, and this time I ended up with Ally.

I was surprised both by how soft she felt as she pressed into me, and the fact that I couldn’t feel any bra strap on her back.

A waitress came in (not dressed in red, horrors!), set up a table, and served dinner. Ally held four envelopes fanned out in her hand, and each of the women took one before seating herself.

Dinner conversation was a bit loud, probably loosened by the wine. None of us at the company were really social animals, but we were all very comfortable around one another. Fellow geeks, you know.

At the end of the meal, the girls all opened their envelopes and looked at the cards inside.

Then Ally turned the music back on. Only slow numbers now. I recognized “Lady in Red” and the oldie “Roses Are Red,” but other than that who knows?

Ally kicked off her shoes, and pulled me to my feet to dance some more. I didn’t object. I knew it was probably inappropriate, but I let my hand run down her back, and kind of liked the fact that she wasn’t wearing a bra. She didn’t seem to mind my hand at all.

The other girls kicked off their shoes as well, and each grabbed a guy.

At the end of the number, Lin left the group for a moment, pulled off her sweatshirt, and tossed it onto a chair. Of course everybody applauded and wolf-whistled, bostancı escort bayan even though she was wearing a red tank-top underneath. Probably because we’d had some wine so we were acting even less mature that usual.

But really, the sweatshirt must have been really warm for dancing.

She chose me for the next dance and yeah, I did place my hand on her back in a way that I could feel whether she was wearing a bra – though I’m not sure she could have been wearing one under that top without it showing.

I wondered whether, if her breasts weren’t pressed against my chest, I would have seen her nipples poking through in front.

I had a feeling Lin could tell I was thinking impure thoughts.

When the song ended, we switched partners again. I got Madison. Before I wrapped my arm around her, I realized she was wearing a bra because she’d unbuttoned enough buttons on her shirt to let the very top of a red bra (of course) peek out. And since she’s pretty short, and I’m kind of tall, I had a really nice view.

As before, I was really enjoying the feel of her body pressed against mine. As before, we swayed rather than actually danced.

I looked around and saw Jorge pretty openly caressing Lin’s back through her tank top as they danced.

I had a feeling when I got home I’d be fucking the hell out of my wife for the first time in weeks.

Right now, though, I’d have given anything to unbutton Madison’s blouse a bit more.

When the song ended, and the next one didn’t immediately begin, Ally said “Bob, Jorge, Tom, Alex, since everybody seemed to enjoy Secret Santa, we girls decided to do a Secret Cupid for Valentine’s Day.”

“Secret Cupid?” Tom asked.

Lin waved her card. “It means I’m your date for the rest of the party.”

“You’re all okay with that?” I asked, looking at Madison. Okay, looking down Madison’s blouse. If there were going to be any reservations, they’d likely to have come from her or me, since we both had significant others.

She smiled and nodded.

“Okay,” Ally said, “let’s get the music started, and let’s find our partners.”

Jamie moved over to me and smiled, and I put my arm around her back. She reached back and pushed it down, until it was resting on her ass. Through her dress, but then the dress wasn’t terribly long.

I noticed that Lin, before dancing with Tom, had untucked the bottom of her tank top from the waist of her jeans, so as she danced enough of her midriff came exposed to show her belly button ring.

I think Madison undid one more button before dancing with Jorge, but I couldn’t be sure.

Ally and Alex were back at the table, wine glasses in hand.

The music picked up tempo. We were dancing to something I later learned was called something like “Red, Hot Jazz.” I missed not being able to hold Jamie, but I was getting occasional peeks of her red panties.

“I’m definitely getting my exercise for the day,” Madison said. “Or the week.”

“I think Ally’s trying to dance us to death,” Jamie said.

“Like The Red Shoes,” Lin said, “How appropriate.” None of us got it.

She rolled up the bottom of her tank top to just below her breasts, to cool down a bit.

The song ended and Madison said “Potty break. Don’t go anywhere, Jorge.”

“I wouldn’t think of it,” he said.

She looked around, momentarily befuddled by all the doors leading out the room. “Bathroom’s there,” Ally pointed.

Jamie’s dress had a zipper in front from the neckline to about the ribcage. She gestured at it, and said in a teasing voice “Would you pull that down for me just a bit, Bob?”

“Um… how far?” I asked.

“A bit,” she said.

Well, that was dangerously non-specific.

I grabbed the zipper and pulled it down, very tentatively, until just the very top of her very light red bra was showing, the same as Madison. Since Jamie was so slim, I realized, her bra was there for decorum’s sake rather than because she needed support, so it was thin enough to be see-through.

I could see the sweat beaded up on the swells of her small breasts.

“Thanks,” she told me, “that’s a lot more comfortable.”

“My pleasure,” I said. “Any time.”

A few minutes later, when Madison came out of the bathroom, it was evident that she’d left her bra behind: instead of the top of her bra showing, the top couple of inches of her breasts were. Jorge didn’t seem to mind at all.

“Hey, Bob,” Lin called over.

“Yeah?”

“Big favor to ask.”

“Hm?”

“Can I borrow your shirt?”

“Say what now?”

“Swear to God, I’m dying in these jeans. You’re tall enough that your shirt would fit me like a dress. A short dress, but it beats dancing in my panties.”

“Nobody would mind,” Tom said.

She gave him her middle finger.

“Sure, I guess,” I said. I’d prefer she were half naked than me, but there was logic to her suggestion. I unbuttoned my shirt. Good thing I’m in reasonably good shape for a ümraniye escort geek. Way too thin, but it could be worse.

I tossed it over to her. “Whew,” she said. “Sweaty!”

“Hey, you’re welcome,” I shouted back. “Feel free not to wear it.”

We were both just kidding around, of course.

She ducked into the bathroom and came back a minute later holding both her tank top and her jeans, which she put down on a chair.

She’d misjudged: my shirt didn’t come down quite as far on her as she’d thought, and we could all confirm she was wearing red panties as instructed. She saw that we saw, and shrugged – nothing to be done about it now – and went back to dancing.

Tom placed his hand on Lin’s ass as they went back to dancing – or more accurately, right on the back of her panties. I’m sure she must have told him to, because Tom’s probably the shyest of all us guys.

“You can do the same thing,” Jamie said softly.

“Are you sure?” I asked her. Because she didn’t sound sure. I had the feeling this was all going further – or at least faster – than she’d expected it to, but she didn’t want to be the one to put the brakes on for everybody.

“When I bought these panties for tonight, I figured somebody would be seeing them.”

Which wasn’t exactly the answer to the question asked, but I cupped her left ass cheek through her silky red panties. It had been long time since I’d cupped any woman’s ass cheek other than my wife’s.

God knows how long it had been since I’d cupped my wife’s. I don’t know whether she even owns a pair of silky red panties at this point.

Jamie sighed softly, then buried her head in my (sparse) chest hair as we danced.

Then the music stopped. Ally’s phone was still on the table, but she and Alex were gone. “Um, her play list must have ended,” he said, burying the lede: that Ally and Alex had slipped off to one of the side rooms.

He went to the table, pressed a few buttons on her phone, and the music started up again with Little Red Corvette. When Jorge got back to Madison, she said “welcome back,” and kissed him on the lips.

As soon as Jamie noticed, she kissed me, and then Tom kissed Lin.

And soon there was a lot more kissing than dancing, which none of us minded at all.

I had both hands on Jamie’s ass now, pulling her tightly against my body. I’m pretty sure her panties were completely exposed by now, but nobody would have noticed.

I hoped this wasn’t going to create awkwardness in the workplace tomorrow.

“Oh,” I head Lin say, and I glanced over to see that not only were her panties completely exposed, but my shirt (which she was wearing) was half unbuttoned and she and Tom were groping one another. I couldn’t see her breasts, but Tom probably could.

“Eyes over here Bob,” Jamie said when she saw I was glancing over at Lin. Jamie yanked the zipper on the front of her dress down as far as it went, to just above her navel, exposing the left cup of her bra. Which was sheer enough to give me a nice view of her nipple and areola.

Okay, she had my complete attention now. She pressed her body against mine as we danced very closely, and I’m sure I could feel the warmth of her breasts against my chest. I could see Lin pulling Tom’s t-shirt over his had and throwing it into a corner of the room. At least I wasn’t the only bare-chested guy anymore.

The song ended and Jamie shouted “Fuck!” as she stepped away from me. It took me a moment to realize what had happened: with her dress unzipped so far down, once we separated it just slipped off her shoulders and fell to her waist. I pretended not to stare, then she just let it fall to the ground and stepped out of it. “Screw it,” she said. “Everybody could already see my bra and panties, so what difference does it make?”

Well, it did, but it was fine with me.

On the room, I noticed Madison and Jorge slipping into one of the bedrooms. I could only see Madison from the back, and just for a moment, but I’m pretty sure she was carrying her shirt in her hand.

“Screw it,” Lin said, “everybody can already see my tits, so what difference does it make?” We couldn’t, but nobody was going to contradict her.

She unbuttoned the final two buttons of her shirt – my shirt, technically – and tossed it onto the floor next to Tom’s. I actually saw her breasts for only a moment, because Tom pulled her up against his own body and slid a hand down the back of her panties as they danced.

I reached behind Jamie and unclasped her bra, gambling that she wouldn’t mind at this point.

She didn’t and she stepped back as her bra fell away, exposing her small, perfect breasts. Even though we’d been platonic friends since college, I’d be lying if I said I hadn’t wondered about them.

What I really wanted to do was take her hard, erect nipples in my mouth, but that might have been too much, so I kissed her instead, with both of my hands on the back of her panties (same as her bra, her panties escort kartal were thin enough to be almost see-through).

Tom and Lin were showing no such constraints: They were all over one another, and Lin was pulling Tom’s pants down past his knees.

Almost naked, they made their way over to the couch. Tom laid Lin down, knelt at her side, and starting sucking on her nipples, then began working his way down to her panties.

I know I should have looked away, but I’d never seen anybody else having sex before. I’m pretty sure Jamie hadn’t wither.

When Tom began pulling Lin’s panties down, Jamie took my hand and led me to one of the bedrooms and pushed the door closed behind us.

“Bob,” Jamie said, “what happens at the Secret Cupid Party stays in the Secret Cupid Party, right? Because I don’t think either of us can stop now.”

“No, I definitely don’t want to stop,” I said, and without hesitation Jamie loosened my belt, pulled down my pants and briefs together, and when my hard dick sprung free, she took it in her mouth. “Jamie?”

She opened her mouth and released my dick for a moment. “Bob, I expect a good fuck out of you, maybe two, and I don’t think you’re going to last very long the first time.”

I couldn’t argue with that, and she went back to sucking me. Maybe it was the excitement of doing this with somebody other than my wife for the first ever, but this was definitely the best blow job of my life.

And, unfortunately, the quickest: as she’d predicted, I didn’t last two minutes before erupting in her mouth. She tried swallowing it all, but a lot of my cum dribbled down her chin and onto her naked chest.

I took a mental photo of her cum-covered breasts.

“You’d better have it in you to get it up again, Bob, or I’m going to have to kill- oh, never mind, you’re almost hard again. Not bad.”

“I think you can take a lot of credit for that,” I said. “I know what will get me ready even faster.” I pushed her down onto the bed, and pulled off what there was of her panties. “Besides, fair is fair.”

I moved my face to her crotch – she didn’t trim her bush, but her hair was fine and sparse – and lightly licked her clit. “Bob, what are- nobody’s ever- oh…”

I stopped what I was doing. “Is this okay?”

“Yes. Yes, it’s just… nobody’s ever gone down on me before. But yeah, very okay.”

As life-long geek, I wasn’t accustomed to being more sexually experienced than anybody in any aspect, and somehow this alone brought my dick to full attention.

I was dying to sink it into Jamie’s wet pussy, but for now I was entirely focused on licking and sucking her, and feeling her writhe under me, and groan loudly. It was so hot, knowing that nobody had ever done this to her before.

“Ohhh… fuck…,” she said in a guttural voice and her body stiffened, then relaxed. “I can’t believe nobody’s ever done that to me before. Okay, now lie down on your back, because I really need that hard cock in me, right now.”

I did as she said, and she crawled on top of me and lowered her body onto my hard cock. She was so wet that I was balls-deep in her in a second.

It wasn’t until hours later that my brain even processed the fact that I was cheating on my wife.

She bounced up and down on me… well, “wantonly” was the first word that came to mind. She was still hot as hell after having me go down on her, and I had all the stamina she could ask for since she’d already made me cum once.

I played with her small, sexy breasts to the extend that I could keep my hands on them as she bounced around.

After about five minutes I told her to get on her knees, and I began fucking her from behind.

(We were loud. Really loud. I thought at the time we might have been, but the next day Ally told me she and Alex got so turned on listening to us, they ended up going another round. I was a mixture of proud and embarrassed)

Finally Jamie got on her back and spread her legs wide, and we finished up in the missionary position. And when I say “finished up,” I mean we were at it for a while.

She was cumming like crazy and I swear, every time I saw her shudder, my cock got harder.

But finally I knew we were near the end. “Can I cum inside you?” I asked.

“You fucking better,” she said, and I came so long and hard, I almost passed out.

I’m actually not kidding about that: I rolled off of her and I think within a minute we were both asleep.

I woke up – as disoriented as you’d expect – a few minutes before midnight, spooning Jamie. She must have woken up around the same time, and began slowly grinding her ass against my cock. It began waking up as well, and eventually I slid it back into her pussy and we fucked slowly and lazily until my body surrendered the last drops of cum it possibly could have produced tonight.

Then we kissed deeply and I said, in a low voice, “I have to go.”

“I know.”

“Sorry.”

“It’s okay,” she said, “I understand.”

Everybody else could spend the night, but I was married so I had to go home. But first I went out to the main room to gather Jamie’s clothing because I didn’t think that, in the light of day, she’d feel comfortable walking out there in nothing more than her tiny panties.

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