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Roll With It Again

Category: Group Sex
02.11.2024
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It wasn’t in the plan.

Donna and I had never actually thought about a real-life threesome using our strap-on. We talked about it lots, especially when we were in the middle of a fuck. It turned us both on. Our dirty talk focused on Donna’s friend Heather, who was safely a continent away and whose previous play with us hadn’t involved the strap-on.

That came later, after Donna told me she wanted to fuck ME with one of HER dildos.

The strap-on had become a regular (although not constant) part of our sex lives. I was turned on by sucking it, turned on by the aggressivity it brought out in Donna. She seemed to swagger a bit when she wore it, the dildo waggling back and forth as she walked around our bedroom or our living room.

Sometimes she’d keep a dildo in a pocket of her slacks. We’d be out for dinner, sitting close, and she’d take my hand. Guiding it up her leg to where the lump sat. I’d touch it, then her pussy. Meanwhile, she’d be walking her fingers up my leg to my cock and balls.

But just as everything changed the day Donna told me “I’d like to put this in you”, there was a sea change in our relationship the night we invited Emily to dinner.

Emily was a friend of a friend. She had moved to our city from the Midwest and our friends there had suggested we get in touch. We met for brunch — the ultimate safe first- meeting — and found out that a friend of our friends was likely to be someone we’d like too.

So we kept getting together.

Although we’d never been involved sexually with Tom and Jen, we knew they were more open to swinging than we were. They had gone a few times to Hedonism in the Caribbean, and they went to a club where they lived fairly often. And there were times, after a dinner or a concert, that we’d talk in bed about whether they had been with Emily.

She certainly was attractive. Blond, curly hair. Blue-green eyes. Fit, with what I suppose you’d call a dancer’s body — small breasts, small hips. A fondness for tanktops and a seeming dislike for bras; with her tits she didn’t need ’em anyway.

Let me tell you, we also talked about whether WE would be with Emily. That spiced things up in the bedroom. But it was a fantasy. One we shared. Sometimes we felt a little guilty about thinking of her that way. She’d talk about dating or something a little naughty, and Donna and I would make eye contact and I could tell she was thinking about how she had been saying to me last night how Emily’s ass would like in the air as she fucked her doggie style, and how turned on I’d be to be stroking Emily’s ass and sucking her nipples.

But then things changed.

It was over dinner. I’d made a pizza and some salad, and the three of us had had a bottle of nice wine … or two. We were sprawled out on our couches letting our full bellies subside and talking about anything and everything, and Tom and Jen came up in the conversation.

“They just got back from Hedo again,” Emily said. “Those guys…”

“Yeah, they’re wild and crazy,” Donna said. “It’s good to have someone like that around to remind you that you’re not totally whitebread.”

Emily looked at us. “Have you guys been to Hedo with them?” She seemed a bit flustered. “I mean, I’m just asking because they asked me and I said no.”

“No, we’re not that sexually adventurous,” I said. “I’m a little prudish about public sex, and from what I’ve read about Hedo, I think Donna and I like a little more control over who, where and when we, um…”

“Get laid, Steve. Spit it out,” Donna said. We all laughed.

“I guess I wasn’t sure if I’d be comfortable as a single there,” Emily said. “And if I didn’t find anyone I’d feel kinda stuck with Tom and Jen. And even though I love them, I’m not sure they’re my type.”

More eye contact between Donna and I. Hm.

“Em, I’m just gonna come out and ask this,” said Donna. “Are you bi?”

She blushed a little. Or maybe it was the Chianti. “Well, yeah. I’ve been with girls. Not a lot, but from time to time.’

I shifted my position. Somehow I was getting uncomfortable. Emily looked at me.

“Are you cool talking about this, Steve?”

“Are you kidding? My wife and our friend talking about their bisexuality? I may need another drink.”

We all laughed again.

Donna was leaned back against me on our couch. God bless her, she always was the brash one.

“Em, are we more your type than Tom and Jen?”

They both blushed. Me too.

“Are you asking just to know? Or are you… asking?”

This time both Donna and I spoke simultaneously. “A little column A, a little column B.” Sometimes being married was a good thing for shared thoughts.

Emily made a noncomittal sound. The room got realllly quiet. Eye contact was being made in various pairings around the room.

Suddenly Emily stood up. Shit, I thought. She’s offended and she’s leaving. Then her hands went to her blouse. She opened a button. Then another. And another. As she got to her fifth button, she looked at us. “Am I the only one who’s going to get naked here?”

Donna stood up and walked over to her. Pushed Em’s hands away. Unbuttoned her last buttons, then pushed her blouse off her shoulders. Her nipples were coral pink, and erect. I watched my wife kiss her — our — friend on the lips, softly at first, then harder. Tongues came out.

That discomfort I felt earlier was becoming steadily worse.

I walked up behind Donna and reached between her and Emily to cup her breasts in the scoop-neck t-shirt she had on. Emily pushed her breasts against the backs of my hands. Donna pushed her ass against my crotch, and my cock throbbed.

The girls broke their kiss, and Emily reached past Donna with her hand to touch my cheek. She and I kissed over Donna’s shoulder. I was tingling.

As our kiss ended, I felt I had to say something. I swallowed.

“Okay. Ground rules. Donna and I are very open. We also don’t want you to feel weird. We want you to feel good about this. And we don’t want to ruin our friendship. If it isn’t amazing, no problem. And if we’re uncomfortable afterward, we should talk about it rather than let it grow. Deal?”

“Deal.”

The girls turned to me. “Off with your shirts!” cried Emily.

________

Five minutes later, we were in our bedroom, with some music on in the background and some candles lit on the dressers. Naked. Clothes lay on the floor in three untidy piles.

Donna pushed Emily down on the bed. I was torn between wanting to watch and wanting to play. Play won.

As I walked to the bed, Donna looked over. “Get the pink one, Steve?”

That was her favorite vibrator.

I got it. I watched as she lay down on her side next to Emily. I got on the other side, and we both grasped the vibrator and stroked it along her pussy lips. Emily gasped, reached down to my cock and stroked it, looking at me, then at Donna for tacit approval. Donna reached over Emily and put her hand over Em’s as she jacked me off slowly.

“He likes it wet,” she said, and brought Emily’s hand to her mouth, licking the fingers and moistening them for lubrication. Meanwhile, I was touching Emily’s clit with my thumb. Her pussy was starting to glisten, and it looked delicious.

We spent some time just playing with each other, and then I moved to Emily’s pussy. She gasped again as my mouth covered her lips and my tongue moved inside her. Saltysweetness on my tongue as I breathed through my nose and got busy. As I looked up, Donna was kissing Emily on the mouth, the cheek, the neck, licking her ear. The vibrator was on the bed now. Flesh on flesh was what we wanted. I could feel cold wetness as I lay on my stomach and my cock drooled precum onto the sheets.

Emily was making sounds of approval as Donna played with her nipples. Emily’s hands were clutching the bedsheets.

I got up, reached for the night stand. We had some condoms in there for use with the strap-on when we both wanted to play with the dildo. Thank God.

As I rolled on the condom, I said “Donna, can I fuck our guest first? I want to be a good host.”

Donna smiled. “Only if I get to help put that cock in her pussy.” She grasped my penis and I moved into position. Her hand put Emily and I together, and Emily gasped a third time. My cockhead was just inside her, and the warm enfolding wetness was exquisite. Donna’s fingers tickled my balls, moved to my ass. I felt a finger delicately prod at my anus. I slid forward and moved down to kiss Emily, maximizing our body contact.

“Steve,” Emily said. “Your cock is so hard. Oh fuck, it’s hard.”

“No wonder… Look who it’s fucking.”

Donna had a finger in my ass and I moved my legs outside Emily’s to make it easier for her to finger-fuck me.

“Steve likes his ass played with,” said Donna. “Can you tell?”

“Oh yeah.” Em and I were panting together.

“You know what has made us think for a long time? Me fucking him with a strapon while he fucks someone else.”

I stopped thrusting, and my dick twitched in Emily’s pussy. I felt her muscles contract around me, almost encouraging me to start pushing again. She took a breath.

“Missionary or doggie?” Lights started flashing in my head. This was going to happen.

“Doggie, I think,” said Donna. “Pull out, Steve. Let our guest get ready for me to fuck both of you.”

“Both of us?”

“One first-hand, one second-hand.”

I pulled out. My heart was hammering in my chest.

Donna grabbed the strapon and put it on, standing by the bed. Meanwhile, Emily rolled over and grabbed it, put it in her mouth, then stood up. I watched her kiss my wife while she caressed the dildo, then Donna’s tits, then the dildo again. My cock was jittering around on my stomach like spit on a frying pan.

“You are the two hottest people I’ve ever met,” said Emily.

“You’re raising our temperature,” I said, and stood behind Emily, putting my cock in the cleft between her butt cheeks. I was drooling precum into the condom like crazy as I felt her sweet ass against my shaft.

Donna reached for the lube in our night table, spread some on the dildo. My ass quivered inside. I broke off from humping Emily and grabbed a Liberator wedge. Grabbed Emily’s hand, said “Come here, baby. Time to make the chain.”

She lay down on the bed, face down, ass in the air on the wedge. Donna leaned to kiss her.

“I’m glad it’s you, Emily. This might not ever have happened,” she said.

“Thank you Donna.”

I was behind her then, cock pointing to two o’clock, or maybe one-thirty. Her ass had fine downy blond hairglints in the candlelight. I bent down, kissed her rosebud. Then moved to her pussy, tasted what was flowing there. I came back up to my knees, scooched closer, and … ahhh, my god.

She was like heated honey inside. I slid in in one stroke, not impeded by the curtains of flesh that parted for me.

Then I felt Donna put her cockhead at the gate of my ass. She leaned over, said “Ready?”

I tried to calm my leaping heart. “Y-yeah.”

She pushed into my ass, just an inch or two. I tensed.

“Okay, lover?”

“Soooo hot. Slow, k?”

“Oh yeah.”

Emily beneath us both, now slightly rotating her hips on my cock like a sensuous dancer.

And then it was inch by inch into my ass. Donna’s cock, which never wilted, was in me to the hilt, we three impaled on a stake of pleasure like three paid bills on a nail. We stilled for a moment, all three.

“Oh God, so full.” I could feel Donna’s dildo against my prostate, against even the root of my cock. “Oh god.” I started to thrust slightly, and Emily pushed into me with a throaty growl. Then I felt Donna find the rhythm, reinforcing my thrusts.

“I’m fucking you, Emily,” she said. “I’m fucking you with my cock and with Steve’s, do you feel it?” Emily’s breath was heavy. “You’re our little friend who wanted this and now you’re getting it, Steve’s big dick in you and my big dick in him and both of us fucking you and you’re getting so horny…”

Donna’s talent for dirty talk was unique. And uniquely suited to increasing our rhythm. Emily reached back to my hips with one hand, moaned and grabbed me. Donna reached under to tickle my balls.

We kept rolling downhill faster like a landslide, flesh and rubber mixed together in a blend we couldn’t distinguish between any more. And then Emily spasmed, her legs twitched together for a moment, her pussy grabbed my cock and I was gone. Donna pushed in all the way and held it. I think she could feel my cock’s spasms as I came inside Emily with what felt like a geyser of cum.

I shouted something. I’m not sure what. I reared back as the cum jetted out of me and into Emily, held back by the rubber. Donna grabbed my nipples, never able to leave well enough alone. Motes of light circled in my vision.

I heard Emily cry out and it was like she was a million miles away and in my head at the same time.

And then it subsided. I pulled out, bit by bit. And so did Donna. Emily sighed as my cockhead left her cunt and I moved back. She rolled over and up to a sitting position, grabbed Donna.

She devoured Donna’s mouth with hers. She was in no way spent. My cock kept twitching, as if it had something to say and wanted to get someone’s attention. But right now, it was all Donna and Emily.

She pushed Donna onto the bed and unbuckled the dildo, took it off. She attacked Donna’s pussy like a thirsty man at a spring. Donna’s nipples were hard, her breasts rising and falling.

I had taken the condom off by then nad tossed it at our wastebasket, missed. I knee walked up to Donna’s side, kissed her, touched her breasts.

“I love you, baby.”

She kissed me back hard.

Emily and I brought her home.

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