Secret Cupids Ch. 03

This is a follow-up to Secret Cupid 1 and Secret Cupid 2; but while I definitely think you should go back and read those, this story actually works just as well without them.

I'd been looking forward to dinner at Madison's apartment -- and our after-dinner activities. Lately things had gone rather, well, stale, but last night we'd gone out to dinner and when we got back to my place, the sex had been great. Better than it had in weeks. Madison had seemed inspired, almost ripping off my clothes and hers and initiating a frantic 69 session. (and she swallowed every drop). Then she sucked me hard again and by the time I came in her pussy, we were both sweaty and exhausted.

Of course, last night was Valentine's Day. Could we hit those heights on February 15, an ordinary night?

Well... I guess not, I thought, when she opened the door to let me in: sitting on the couch was another woman. She looked to be in her early 20s, a few years younger than us. Not a romantic dinner for two, then.

I took off my coat. It was a raw February night and I have to admit, I might not have come to dinner if I'd known it would just be... dinner.

"Howard, this is Lin, a friend from work. And this is Howard, I've told you about him."

"Don't believe a word of it," I said with a grin.

"Oh?" Lin said to Madison with a totally straight face, "Then everything you said about his sexual prowess isn't true?" Then she cracked up, and so did Madison. I had to laugh too.

I'm used to me being the smartass in the room.

Well, I guess if I had to drive across town for just a small dinner party, at least it was fun: I'd met some other of Madison's co-workers and they were nice enough, but total nerds. Lin seemed to even loosen up Madison.

And of course at the end of the night, Lin would be leaving and I'd be spending the night, so there was that.

The three of us were having a good enough time that I was almost disappointed when it hit 11 and Lin said it was time to get home. She pulled out her phone, hit a few buttons, and said "Hmm..."

"Hmm?" Madison asked.

"Trying to get an Uber..." She hit a few more buttons. "Well, shit. Remember that storm they said might hit us last night? Seems it started a couple of hours ago. The roads are completely fucked. Mads, I can't get home. Nothing's running." Since her apartment is on the first floor, Madison had blackout curtains. They could have set off an atomic bomb, and we wouldn't have seen it.

"Okay, we can handle that. The couch folds out. No problem at all."

Well, a bit of a problem, because Madison's living room doubled as her bedroom. I'd have been fine with Lin hanging out a while longer, but I did have some hopes for the night.

Oh well...

So we had another drink or two, and Lin told us a college story that almost made me choke on mine.

Finally, Madison said "Okay, I've been thinking about the logistics." Of course she was: logistics is what Madison and Lin and their bunch were all about. "Howard, you use the bathroom first, wash up and everything, but don't come out until I tell you."

I went inside and brushed my teeth; then made sure my bladder was as empty as possible because I was pretty sure I'd be slipping off my pants under the blanket and sleeping in my boxers, and I didn't want to be wandering to the bathroom in the middle of the night.

Madison knocked on the door. "All clear."

I came out and saw both girls were wearing nightgowns. I was kind of surprised, I figured Lin would be doing the same as me, slipping off her pants under the blanket and sleeping in her panties, but I guess it made more sense for her to wear something of Madison's.

The nightgowns weren't see-through by any means, but I could tell that they were both wearing panties underneath and nothing else.

They'd already pulled open the couch.

"I'll be quick," Madison said, ducking into the bathroom.

"Oh, you can stop pretending not to stare," Lin said to me after a minute or two. "I know these are kind of thin." She wasn't doing anything to cover up, though. "You know," she said with a grin, "we had an argument over who would sleep where."

"Really now?"

"Really. And you and Mads have the bed."

"And does that mean you won the argument or lost the argument?"

"I'll never tell."

Madison came out of the bathroom, bedding in hand, and told Lin she'd left an unopened toothbrush next to the sink. She began pulling the bedding onto the couch.

As soon as Lin was gone, I came up behind her, reached under her short nightgown and grabbed her ass. "No time for a quickie?" I asked, jokingly.

"Stop it. It you were that quick, I'd have dumped you by now."

"Maybe you could..."

"Well, I could suck you, but she'd probably come out when I was halfway through, and that would make it a very unpleasant night for you. But you do need to strip down to your boxers and get under the blanket before she's done." I did, and she joined me.

Other than the first time we'd slept together, when she pulled her panties back on after the sex, this was the first time we'd been in bed together and not naked.

Lin came out, switched off the lights, and said "shit!" as she walked into an end table before finding her way to the couch.

We said our goodnights, and settled in. Madison and I soon found herself in a spooning position, with my dick press up against her panties.

Not too frustrating.

The thought of a stealth fuck did cross my mind -- obviously -- but Madison is loud. Which is normally a good thing, a really hot thing, but not tonight.

I was almost asleep (surprisingly) when I felt Madison stirring. She sat up and pulled the nightgown over her head. "Lin's right there," I whispered-- not that I wasn't fine with her taking it off.

"It's dark," she whispered back. "Besides, you've both seen me naked before." That startled me for a moment, then I realized she meant Lin had seen her topless when they changed earlier.

We settled back in, my arms wrapped around her ribcage. I'd have preferred my hand on one of her breasts, but since we couldn't fuck, that wouldn't have done either of us any favors.

Eventually, we both fell asleep.

I woke up about an hour later to Madison lightly kissing my back. I thought that was odd -- a few years go I had a girlfriend who did that when she wanted me to wake up for sex, but Madison never did -- but I liked it.

But wait, I still had my arms around her.

I let go of Madison and turned around, even though I knew I wouldn't be able to see anything. It was probably also pointless for me to reach out a hand, but I did anyway and closed it on a naked breast. "Lin, what are you doing?"

"I got lonely," she whispered back. Even in the dark, I could "see" her grin.

"You should really go back to the couch."

"And you should really take your hand off my boob, yet here we are."

She was right: I did still have my hand there. It felt nice.

As long as my hand was there, and she was okay with it, I began stroking her breast. Her nipple was already rock-hard, and I wondered whether she'd been playing with herself before she came over to the bed. That might explain things.

She reached down and grabbed my hard dick through my boxers.

This was crazy: Madison and I had never cheated on each other, even when things were rocky, but that's exactly what I was about to do. With her friend. With Madison right there in the bed?? No, I wasn't that crazy. "Let's go to the couch," I whispered.

"And leave me all alone?" Madison asked in a normal voice.

I'm sure I would have lost my erection if Lin hadn't reached inside my boxers and wrapped her hand around it.

Madison put her hand on my belly, very close to Lin's hand. My eyes were just becoming adjusted enough to the dark that I could vaguely see her. "Don't worry," she told me, "we had a deal."

Madison turned on the nighttable lamp, to the lowest setting: just enough light so we could see one another.

"A what?" I asked, as she removed her hand from me and pulled her panties down, leaving her naked. She spread her legs and Lin let go of my dick and crawled over to her. I noticed for the first time that she was completely naked too.

"Madison," I said, "you're, I mean..."

"No," she told me. "But we were talking the other night, and we decided this was something we wanted to try."

"You're welcome not to join us," Lin added, and again I could "hear" the mischievous grin.

"Oh fuck!" Madison suddenly said loudly, and I knew Lin's tongue had just made contact with her clit. And then "Lin would probably be doing this even better if she had a dick in her."

Well, who was I to stand in the way to Lin doing a better job of eating my girlfriend's pussy?

I got behind Lin, and slid my dick into her wet pussy. I swear, it felt as if it were sucking my dick in. She did seem to be going at Madison's pussy with increased fervor, and Madison's thrashing about increased.

"Is Lin's pussy wet for you?" Madison gasped between loud groans. "Isn't it hot, so wet, so sweet, oh my fucking god yes!"

Lin was groaning into Madison's pussy as Madison came, and I continued to I fuck her hard.,

I was suddenly struck by the possibility that I was still asleep and was dreaming all this -- which really seemed the more likely prospect -- but if I was, please God don't let me wake up any time soon!

Madison was really into this, for somebody who'd never been with a woman before.

But more importantly, Lin couldn't seem to get enough of Madison's pussy or my dick.

And Madison had her hands on the back of Lin's, forcing Lin to suck on her harder -- something she hates when I do it to her.

None of this mattered to me, though, as long as I was fucking Lin: the best Day After Valentine's Day present ever!

But there was no way I was going to last as long as I wanted to. "Can I...?" I gasped.

"Cum in her," Madison shouted. "Fill her pussy with your cum, and I'll suck it all out of her."

"Oh!" Lin said excitedly, as she thrust herself even harder against my dick.

That was all I could take, and I started to cum like crazy. I usually try to last as long as possible but come on, I was proud to have held out as long as I had.

"His cum is mine," Madison said, and the next thing I knew I was lying on my back, trying to catch my breath, and the girls were in a 69 position. Madison was eagerly licking my cum out of her friend's pussy.

Really, a few days ago I thought she'd given up on sex completely, and now she seemed insatiable.

After making Lin cum loudly, Madison "came up for air" long enough to look over at me. Until she did, I really hadn't realized my dick was rock hard again. "Go into the bathroom and get the Vaseline," she told me.

Could she mean...?

When I got back, they were still going at one another's pussies, but they were on their sides now. "Do it," Madison said. "I want you to do it."

Well, I guess if she was ever going to agree to anal sex, this would be the night.

I think I put so much Vaseline on my dick, there was more Vaseline than dick. I slid into her ass very slowly; but I think whatever apprehension she had was drowned out by Lin eating out her pussy.

And then I started to actually fuck her, and it's as if a switch had been flipped. With a dick in her ass and a tongue in her pussy, she began twitching like a live wire. A loudly-groaning live wire.

I'd never had anal sex before, and I'm pretty sure Madison hadn't either.

Lin began eating her more aggressively. I also sped up what I was doing, still careful not to hurt her.

She was lost in the sensations, and of course her mouth was still on Lin's pussy, licking her almost manically, so she was getting the benefit as well. And then...

Madison came. I can't say for certain it was the hardest I'd ever seen her cum. It was certainly the loudest, and I wouldn't be surprise if it woke some of our neighbors.

(Fortunately they'd probably heard her cumming loudly in the past, and wouldn't call the police)

Lin took her mouth from her pussy. I could see her face coated with Madison's juices (and, I suppose, my cum). I very carefully eased my dick, still rock-hard, from Madison's ass.

"I think we broke her," Lin said with a smile.

She was right: Madison was basically a rag doll, without the strength to move. Almost unconscious, and happily so.

Lin looked at my dick. "Oh, and that can't be comfortable."

"Not even a little," I agreed. "but totally worth it."

"Well, I'd love to help you out; but honestly, there isn't anyplace I'm willing to take that thing fresh from Madison's ass."

"I understand--"

"Except."

"Except?"

"Take it to the shower."

She didn't have to ask me twice. I got into the shower with her (and we both needed it anyway), and I washed my dick.

And then she washed my dick.

And then she crouched down and took my dick into her mouth.

And when the blow job was done, when she'd sucked me dry, I felt as limp as my dick. We stumbled back into the bedroom, barely drying ourselves, and dropped into bed on either side of Madison.

#

I woke up to Madison, as naked as I was, gently stroking my disk.

I looked past her and confirmed that Lin joining us hadn't been a dream.

There was no way Madison was going to get me hard at that point -- it had only been a few hours since she and Lin had worn me out -- but it was a nice way to wake up.

Madison retreated into the bathroom to take a shower. I began getting dressed, all the while watching Lin's naked body sprawled out on the bed. Thinking about how suddenly, and unexpectedly, a disappointing night had turned into one I could only have fantasized about.

I was about to pay the price; but however long it was going to take me to shovel out my car after last night's blizzard, it would have been well worth it.

I drew back the curtains. The street, the sidewalks... totally clear. Not a single snowflake had fallen.