It was early Wednesday evening, shortly before I was supposed to show up for my babysitting job at the Henderson’s, and I was getting a little nervous about what I had agreed to last week.
Steve was going to game night, and would be bringing Mike back with him for a little after-hours fun for the three of us. I wanted to make sure I was ready to enjoy everything they had planned for me.
I lay back on my bed, imagining them both embracing my body, hands stroking me everywhere, and then them sliding into me at the same time. I already had my largest butt plug in place, anticipating Mike’s impressive girth and enthusiasm for my ass.
I pushed my fingers deep inside me, wishing I had something a little bigger, while trying to imagine what it feels like having both holes filled at the same time.
I figured I’d find out soon enough, so I left the butt plug in as I got dressed in my favorite little plaid skirt and white tank top. I tried to calm my nerves while driving to the Henderson’s, but every movement reminded me of the plug and what the men would be doing to me later.
The Arrival
I must’ve still looked a little nervous when I got there, because when Steve opened the door, he had a concerned look on his face.
He pulled me in for a hug and kissed the top of my head. “Why do you look so worried?” he asked. “If you’re not ready for what we have planned this evening. Just let me know. I don’t ever want to push you too much.”
“I’m nervous, but also excited,” I admitted. “I’m sure you guys will both take good care of me.”
“Oh, we certainly plan to do that,” Steve said with a little laugh as he dipped down to give me a long, slow, proper kiss. My belly filled with butterflies when he brushed one hand over my hard nipple while kissing me.
“You make me want to skip game night and get straight to the after-party fun,” he murmured into my ear.
“I hope you’re not gone too long,” I said. “I’ll be watching the clock the whole time. Tell Mike I’m excited to see him too.”
Steve reluctantly broke away and left for his game night, and I went about my usual babysitting business.
Steve hadn’t mentioned it this time, but I know he usually likes me to pick out a sexy movie from his special stash. My last movie choice was the one that got me into this situation, so I figured I should be more careful this time.
I saw Steve had a new movie this time, Night Trips, about a woman having very sexy dreams, so that one seemed like a safe choice.
I slipped the movie into the VCR and got comfortable on the couch. It wasn’t long before I got really turned on by the movie, and figured I might as well pleasure myself until they got back.
I had my top pulled up and was pinching a nipple while my hand worked under my skirt, when I heard the jingle of keys in the door.
The Surprise Guest
I quickly pulled down my shirt and sat up, looking over the back of the couch. I was surprised to see three men walking in the door.
Before I could ask, Steve volunteered, “I know you said Mike was OK, but when Brian heard what we were doing, he wouldn’t let us leave without him!”
Brian looked a bit sheepish and quickly added, “I can just watch if you want. I had such a great time last week. I didn’t want to be left out. I hope it’s OK.”
“OK,” I said, thinking it over a bit. “Let’s just take this real slow and see where it goes.”
The men all looked at me with big smiles on their faces. Steve walked over and wrapped his arms around me, kissing my neck slowly, while the other men hung back nervously in the background.
Steve’s hand slid up my leg and pushed my panties aside, working his fingers into me.
“So nice and wet already,” he whispered into my ear. I could see the other men behind him moving closer.
Steve glanced at the screen behind me. “Night Trips? Nice choice, Raven,” he said. “I can’t wait to make all your dirty little dreams come true.”
I looked at the screen to see that things had evolved into an all-out gangbang. There were at least five men working their way around a beautiful woman with long dark hair.
I took a cue from the scene and knelt down in front of Steve. Then I brazenly reached out and pulled his zipper down, watching his big cock pop out, hard and ready for me.
As I took him into my mouth, I heard the sounds of the other men loosening their pants, and could see them moving in even closer.
“Why don’t you give the other boys some attention, too?” Steve asked after a few moments.
I turned my head to see two hard cocks pointing at me, so I took one in my hand and one in my mouth.
I heard both men groan with pleasure, and felt Steve’s hand on the back of my head, encouraging me to take Brian’s cock even further down my throat.
I worked them all one by one as they stood around me with their pants at their ankles.
“You’re doing so well, baby,” Steve said with encouragement. “Why don’t you show us your favorite little present? Or is it the big present this time? Haha,” he laughed.
The Pleasure Buffet
The men all moved to sit on the couch, all three dicks pointing straight in the air. It was quite a sight.
I pulled my tank top up and let my full DDs bounce out of it before taking it off. As the men watched, I ran my hands over my breasts, taking time to tug at each nipple. I was turning myself on as much as I was turning them on.
They started stroking themselves as I pushed my skirt and panties down and turned around. I gave them the little ass shake I knew they liked.
“Fuck that’s hot. She’s wearing the big one! I know she’s planning on letting me in the back door again,” Mike said from the couch. His voice was practically vibrating with excitement.
“We’ll get to that, but come over here and let us enjoy that body of yours a little first,” Steve said.
I wasn’t sure where I should go, and then Steve patted his legs and said, “Just lie across us and let us enjoy you like a delicious buffet.”
So, I stretched myself out, naked, across all three men’s laps.
My head was in Mike’s lap, my torso in Steve’s lap, and my legs were across Brian.
Mike wasted no time burying his face in my tits, giving each nipple a teasing lick and a rhythmic sucking.
I felt Steve’s hand rubbing my clit as Brian explored just how wet my pussy was. Once he felt how slick I’d become, he didn’t hesitate to put two, then three fingers into me.
Brian began to finger fuck me deep, while Steve worked my clit and Mike lavished attention on each nipple. He would suck one all the way into his mouth, stretching it out and letting it go with a loud pop.
“Why don’t you make use of your mouth while you’re right there?” he suggested, in between his mouthfuls of tit.
I turned my head to where his thick cock towered above me. I was face-to-face with his balls, so I opened my mouth, sucking them in gently.
“Oh yeah, I like that. Why don’t you go a little lower?” he said, as he grabbed his cock and scrotum, and tugged both up, exposing his taint underneath.
I put my tongue out and licked up and down as far as I could go.
Mike was moaning while pumping his body up and down against my tongue.
I was so busy pleasuring Mike that I almost forgot what the guys were doing to me down below, until Brian slipped a fourth finger in.
“Does this feel good, Raven? he asked tentatively, working his thumb into me as well.
“Yes, I think I can take it,” I said as Mike sat back down and guided his cock into my mouth.
I felt Brian working his hand into me, as I tried working more of Mike’s massive girth into my mouth.
I was so wet and worked up that Brian’s fist didn’t meet much resistance, and with a slow, steady pressure, I felt his whole hand slide inside.
My pussy closed around his wrist, and he rested his hand for a moment to let me get used to the feeling of being so full.
He started gently pumping in and out, and I looked down in amazement at the arm buried deep in my pussy.
“Keep going,” I said as I rocked my hips, fucking his fist harder and faster.
Steve’s slow circles on my clit sped up, and Mike’s mouth returned to my nipples.
I heard a strangled noise, something between a moan and a scream, and realized it was coming from me. As I was orgasming, each wave sent a gush of liquid out between my legs, covering Brian and Steve.
Brian slowly withdrew his fist as I lay there, limp after such an intense release.
“Wow! I didn’t know you were a squirter!” Mike said.
“Neither did I,” I said in shock. I wasn’t even sure what exactly had just happened. I just knew it felt amazing.
Getting Air Tight
“Now that we know you are good and warmed up, I think you should sit on my lap,” Steve said, making it obvious it was his erect cock he wanted me to sit on.
I straddled Steve, still sopping wet from my orgasm, and easily slid down his big shaft. Just as he started fucking me, Mike knelt down behind me.
“We can get this out of the way now,” he said as he pulled the plug out of my ass. “I’m so glad you invited us back. Just once wasn’t enough. I haven’t been able to stop thinking about fucking your ass again.”
Instead of getting right to it, he surprised me by plunging his tongue into my asshole, while Steve was fucking me slowly. Then Mike moved his tongue, lower and lower, until he was licking my pussy as I was being fucked.
That was something I hadn’t expected! It seems these men may be a little closer than I thought.
After Mike gave me a thorough licking, he stood up, and I realized what was about to finally happen. He must have seen me tense up for a moment, because next he said, “Relax, baby. We’re gonna make you feel good all over again.”
I could feel him pressing himself up against my asshole, still slick with his spit and lube from the plug.
Mike took his time, and I knew I needed to relax my body so I could enjoy it without it hurting. I felt the pressure start to intensify, and I wondered if he would be able to fit in at the same time Steve was in my pussy.
Steve withdrew all the way just as I felt the head of Mike’s cock push through my asshole. Every time Steve withdrew, Mike would push in a little more. Once he got himself all the way in, he and Steve worked at opposite tempos, one pushing in while the other pulled out.
They kept this up for a bit until I was ready for them to thrust at the same time, filling me as I’d never been filled before.
Brian sat on the couch beside us, jerking off while enjoying the show. Steve and Mike became lost in their own actions as they stuffed both holes simultaneously with intensity.
I wondered if they could feel each other through the thin membrane separating their dicks inside me.
I saw Brian had gotten up from the couch and walked behind it.
“There’s only one more thing that would make this perfect,” he said as he put his hand on the back of my head and started guiding it to his dick. “I think it’s time we made you air-tight.”
This wasn’t part of my original plans, but I didn’t resist. I was so caught up in the moment that having a dick fill every hole was the only thing I wanted.
We all became a blur of furious fucking, with all three dicks pumping into me as I bounced up and down on Steve’s lap.
The only pause in the action is when Mike would pull out, spread my ass, and give it a few more licks. I know he liked to see how much his fat dick stretched me each time.
Mike and Steve kept going until they came almost at the same time, and I never felt so much cum shooting into me at once. It felt like a hose had been unleashed.
“Oh, baby girl, that was so good,” Steve said, teasing my nipples while I still worked Brian in my mouth.
Steve worked his way lower and lower, and I knew he was going down to lick me clean. I loved that he did that.
Brian surprised me when he pulled out and told me to open my mouth. He tapped his dick a few times on my tongue before jerking off into my open mouth and on my face.
I swallowed and licked my lips before turning around to Steve. He licked the cum off my cheek before kissing me.
“Did you have fun?” he asked.
I saw Mike and Brian were already getting dressed, and I suddenly felt a little shy sitting there totally naked.
“Yes,” I said as I lay my head on Steve’s shoulder. “I did enjoy myself.”
“And we enjoyed you as well,” he said, putting his arm around me.
The Party Invite
While Steve cuddled me on the couch, I heard Mike shout from across the room, “Invite her to the party next week!”
“Party?” I asked.
“I think I mentioned the neighborhood parties to you? They can get a little…adventurous if you stay late.” Steve’s smile as he said this told me exactly what kind of adventures he was referring to.
Still, I asked, “How adventurous?”
“Well, you might end up with more than one partner, or more than one at a time, and it would be out in the open where everyone is watching. But I know you’re not a shy one once you get going,” he said with a wink.
I started blushing, thinking of how they must think of me, turning into their little willing slut in such a short span of time.
But I was having such a good time, and the thought of all those people watching was turning me on. The more I thought about it, the more excited I got.
“Would all of you be there?” I said, gesturing to the other guys.
“Yes,” said Steve. “Us and some of the guys from last week. Our wives, too.”
“Barbara will be there?” I said, perking up at her name. “Then yes, I would love to go.” I had been fantasizing a lot lately about exploring more things with her.
“You know, you’re going to be very popular,” Steve said, looking my bare body up and down, which reminded me how naked I was.
I grabbed my top and skirt off the floor, as Steve got up to get dressed.
“Can’t wait to see you next week!” Mike and Brian yelled as they walked out the door.
“That ass is gonna be mine again!” Mike added.
“Very, very popular,” Steve chuckled as he waved at his friends.
He turned a bit serious then and said, “There will be a lot of people there from the neighborhood, so I just want to make sure you know that. And it may shock you a bit, but we’ve seen your mom there a few times.”
“My mom?” I said, my eyes wide with shock as he’s suspected. I couldn’t imagine my mom going to one of these parties.
“Yes,” Steve said. “I didn’t want to take the chance of her showing up and surprising you. You might want to talk to her before next week. Find out if she’s going. I’ll understand if you need to back out.”
“OK,” I said cautiously. “I’ll bring it up and see what she says. I’m very curious now. I didn’t know she had a sexy side. Maybe that’s where I got it.” I smiled and gave Steve a teasing look.
“I’ve never seen your mom participate yet, but I know she likes to watch,” Steve said. Then added, “I wouldn’t mind getting a piece of that myself.”
My mouth fell open when he said that. But then, why wouldn’t he want to get with her? She looked like a slightly older version of me.
“The party will be Saturday night, at Mike’s house, starting at eight. Wear your usual outfit and the butt plug. I know everyone will like seeing that.”
“I’m looking forward to it,” I said and kissed him goodbye.
“So am I,” Steve said. “And the rest of the neighborhood, when they find out you’re going to be there.”
I could hear him still laughing as I walked to my car.
As I sat down in my car, I realized I was a little sore from the workout they had given me. I might need to go home and practice a little more to make sure I’m good and ready for this party.
As I drove away, I wondered, am I really ready to make all their naughtiest babysitter fantasies come true?
