Mary's Unexpected Escapade Ch. 09

This is Chapter 9 of Mary's Unexpected Escapade.

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I woke up again. Finally Friday! David has something planned for me today, and I wonder what it is.

I grabbed my clean dildo and strap and put them in my bag. Maybe he'll want me to use it.

At school, I greet Charlotte and tell her something might happen at the back today and give her a wink. She smiles back and keeps walking down the hallway in the opposite direction.

Fast forward, and it's soon lunchtime. I've been excited all day, wondering what David will get me.

Ah, he did mention anal sex. Maybe it's that?

The bell rings, and I go out back and get to David's car. I look behind me, and Charlotte has followed me as well. I wave her to me, and I get inside.

I kiss David, and shortly after, the rear doors open up, and Charlotte sits inside with us. They greet each other before David hands me a bag. It's heavy!

I take the first thing out. It's four packs of black panties with some frills!

I went through more, and it's a package of different-sized dildos. It starts from very small to more normal-sized ones.

I find a weird balloon thing and ask him what it is.

"It's an anal douche. It's to ensure there's no mess when someone is in your rear.

I start blushing. I look at Charlotte, and she's very interested in what I'm pulling out of the bag.

I take out more and find a rope and pink hand-cuffs. He wants to bind me down in the future, I guess!

I grab more stuff and find a butt-plug. I know what this is for!

I take more out and find some oil-based lube. "Don't use an oil-based lube with condoms." David tells me. Ok, I'll remember that.

I pick up the last thing and find a strap with a ball on it. Oh, it's for the mouth? A gag-ball was it called? This is almost too much! I start imagining myself using all these. I'm tied up with a butt plug inside me, using the gag-ball while tied up to the rope.

I look at Charlotte, and she asks to take a look at it, and I give her the bag.

"You can change into your new panties now."

I do and give him my old and put on the new. These feel off somehow.

David leaves the door and opens mine. He pulls my legs out and gets between my legs.

"He's not gonna take off my underpants before licking?" I think.

But then, he licks my pussy! How?

I let out a moan and looked down. The panties can be split open to give access. So it can look like an ordinary panty, but you can open it up to provide access to... Men or their parts.

Charlotte watches David eating me out. I signal Charlotte that I wish to kiss her, and she obeys.

Kissing my teacher while my boyfriend is eating me out is so hot I feel my juices flow out into his mouth. And after some time, David pulls down his pants and asks me to give him my ass.

I tell him to wait as I climb into the backseat and start undressing Charlotte.

I whisper into her ears, asking if she wants my boyfriend's cock. She thinks for a bit before nodding. I continue undressing her and grab her breasts and start licking and sucking. David opens the door so that he can take a closer look. I focus on her torso while David focuses on her pussy, and she enters a world of ecstasy. David gets on top of her while I make space so he can put his cock inside her. David grabs his cock and glides it up and down her slit before pushing inside her.

She starts moaning as his cock slowly enters her almost unused pussy.

I try my best with the bit of space we have to align my cunt to Charlotte's mouth.

After a while of fucking, licking, and moaning, I see David struggling. He's close.

I get off her, lean down to Charlotte, and whisper into her ear if she wants his cum, and she looks back with needy eyes. "Then I'll make him cum inside you. Would you like that?" I whispered into her ears so David doesn't hear anything. She looked deep into my eyes before whispering, "I'm not on the pill." I smile and turn back to David and whisper:

"Pretend to be cumming inside her, but pull out and fill my mouth," I whispered to him.

David smiles, and I get on top of Charlotte in a 69 position to more easily capture his cum.

"Oh Charlotte, I'm gonna cum inside you now."

"Oh god!" She cried out.

"Get ready, here it comes!" David replied.

This gets me so hot and bothered! I wished he was fucking me instead!

As his breathing gets needy and he closes in on his orgasm, Charlotte wraps her legs around him, preventing him from pulling out.

Oh no.

"Aaah, oh god, wait!" he says as he tries to pull out, but it is to no avail. She keeps her legs too tightly wrapped around his butt. He tried his best to keep himself from blowing, but he was too close. His cock pulsed and delivered one shot of cum inside her, he couldn't hold back anymore and pushed as deep as he could to deliver the rest.

I can see his cock violently throb inside my teacher. He could make her pregnant!

Charlotte cries out in orgasm, and I know what she's going through! It feels so good to have his cum shooting hard inside you, doesn't it? I watch them both enjoying their orgasm, and David smiles at me throughout everything. Despite the risk of knocking up two girls, he's in his little dreamland now as Charlotte is going through the end of her orgasm. David pulls out, and I look into her pussy. Nothing. No cum leaking out. I wanted to taste it, but her body kept it to herself.

I instruct her to switch places with me, so she's on top. David and I spread her pussy and see a large load of cum resting inside her. David wastes no time and takes a picture before filming. We watch his cum, slowly move out, and I catch it with my mouth as I start eating out her pussy.

Charlotte moans as I stick my tongue inside her to eat her creampied pussy, and she returns the favor by eating me out. David films two girls eating each other out before we both have our climaxes.

I looked inside her pussy, and I had drained the cum inside her.

If he knocks her up, and she keeps it, will he keep both of us? His own little harem.

We rest a bit before noticing lunch is almost over, so we pack our stuff and get ready. I kept my new panties on for the day, though. I think I'll need more to keep using them every day.

While returning, I asked Charlotte if she was safe, and she nodded.

"My period starts in 4 days, so I should be safe."

"That method isn't entirely certain, you know? When I fuck other people, I make sure they wear a condom. What if my ovulation is later or earlier than the calendar?"

"It'll be fine."

"Ok. Did it feel good?"

"Yes! You didn't joke when you said you felt it shoot inside me. Oh wow."

"Remember, he's my boyfriend. You may borrow him only sometimes."

She smiled and accepted.

"As a matter of fact, if you want more fun, how about we meet up again on Sunday? We are going to have an orgy."

Her eyes and mouth open wide.

"Yes. Me, David, then another student here and a friend, then another friend. I thought I'd fuck both David and the other guy, but maybe you should have him?"

She says nothing, still imagining the prospect of so many people fucking.

"Let's exchange numbers, I'll contact you, and we'll pick you up if you're up for it."

We exchange and go back to class.

Wait. Would Sally like this many people? She was cautious when it was just me. And she's still a virgin and very shy. I should ask her first.

Some hours later, school is over.

I see Sal' on her way out, and I stop her.

"So. Sal'. You know about this Sunday, right?"

"Yes." She said and started to blush.

"Well, would you be comfortable having many people there?"

"How many?"

"Six. Me, you, my boyfriend, your partner, your partner's friend, and another girl-friend of mine. If you are not comfortable, I'll just make it so it's only us three or you two.."

She seems to be thinking a lot.

"Is it normal to be that many?"

"Not normally. It's just two people, right? Like me and my boyfriend, me and you two days ago. And the original plan was me, you, my boyfriend and your partner, but your partner's friend will be very lonely if he's left out, so I wanted him too, then we got my other girl-friend to join so he doesn't need to be lonely."

"I understand. I don't want to be a bother. They can come."

"You sure? We will all be naked."

"It's ok. Besides, then I can see the different shapes of penises, right?"

I giggle, "Sure you can! You can even taste them if you want!"

Sally slaps my shoulder and calls me a baddy.

We say our goodbyes, and I head home.

I pick up one change of clothes and head out, wishing my Mom and Dad a good weekend, as I'll stay at my boyfriend's place this weekend too.

David picks me up, and we head home to his place.

Once we enter, I take off all my clothes and hang them at the entrance, and he starts making some preparations around his house.

Walking around naked in the house feels good!

I grab my phone. I could message Jeremy, but how about I just do a video call?

I call him, and my video turns on with my breasts in full view.

He answers and starts laughing.

"Oh wow, hello there!"

"Are you with Oscar?"

"Yeah, he's here."

Oscar appears on the screen.

He starts smiling as he sees my naked breasts. It feels good to have people looking at me!

"So Oscar missed me?"

He starts smiling.

"Do you want to have sex again?"

"Sure!" He replied.

"Then can you both come to meet us on Sunday?"

"Yeah sure!" They both say excitedly.

"Oscar, you will have an important mission this time. You will give a virgin her first time. So be very gentle with her, ok? As gentle as you were with me."

He gets very excited and nods.

"And Jeremy, I got a horny friend for you to fuck. She's a little bit older than Oscar's partner."

"... ok!" He laughs.

"Mary, come!" It's David.

"Ok, guys, I'll figure out where we'll do it and call you guys later, ok?"

We hang up, and I follow David upstairs. He has my bag with all the toys and holds the anal douche and lube.

"First, you need to clean your rear."

I'll spare you the details, but he fills up the balloon with water, lubes it, and fills up my ass.

It felt perfect! I can just imagine how it will feel to have a cock shooting its cum inside me!

After repeating this a few times, we move on.

Now is the time to open up my butt. I get on all fours, and David starts with his little finger until I feel comfortable. Then he goes for the smallest dildo, and we work ourselves up in size.

My ass feels so good! I never knew anal would feel this good!

It's like a tiny pleasurable stinging feeling as my body is getting filled up with the dildo. David switches to a larger size as my ass adjusts to the dildo. Oh god, it feels so good! The larger, the better!

After almost half an hour of this, he goes for something larger. It's getting a bit tough now.

"You need to try to push it out as if you are doing a number 2."

I do as he says, and the dildo slides in easier. He takes it out and replaces it with the butt-plug. My butt feels so lubed up and full!

"Oh my god, this feels so good!"

"Good to hear! I think we should let you stay with this inside you so your butt can adjust." We rest for a while until David continues.

"How long has it been since you shaved?"

I look down. My pubes had started growing again.

"Shall we shave you?" I nod. Wanting my pussy to look more presentable.

He grabs his barber kit. It's not the woman's shaves that I use, but it got the job done. After a few minutes, my pussy is as bald as the day I was born!

"Ok, let's head into the shower!

Before heading into the shower, I turned around to look at my cute butt.

I spread my cheeks and saw the crystal holder of the butt-plug. My butt looks so cute now!

We just showered together. This time I sucked his cock, hoping he would be ready for another round, but it only got semi-hard. Guess he'll be ready tonight then, after dumping his load inside my teacher. Gosh, what if she actually gets pregnant? The chance is low, but seriously.

We finish our shower and head down. The butt plug feels so good as I'm walking around the house! I start looking outside the window while David is doing something else. I am wondering if people will spot me.

I keep looking, and everyone who passes by doesn't notice me at all. I grab a chair to be more comfortable. It seems like this will take some time.

And 30 minutes later, the same guy I sucked off last weekend appears! I stand up, wondering if he'll look this way again. He does!

I wave him to me again like last time, and he starts smiling, coming up our driveway.

I open the door, and he comes in like last time, knowing what will probably happen.

I get down on my knees and drag off his sweatpants. His cock smells lovely!

I put it in my mouth and start sucking; we say nothing to each other. The sound of sucking seems to have David interested, so I spot him peeking around the corner, making no sounds.

Aaah, his cock is very stiff, but I can't fuck him here unless David comes with condoms...

What if I try anal?

I stand up. "Want to fuck and cum inside me?"

He nods and grabs his cock, and starts grinding on my pussy.

"Not that hole," I say and smile. I squat down a bit and take out the butt plug, and some lube falls out.

I lay down on my back on the sofa, pulling my legs up. I'm facing David. He's watching intently.

The guy follows me and aims for my ass, but it penetrates my pussy.

He seemed to want to fuck and cum inside my pussy, so he went at it, thrusting into my pussy.

Aaah... It feels so good... But no, he can't have it.

I pull him out and aim for my butt, and he pushes in slowly.

The spit and my vaginal juices had buttered him up, but still, I was very tight.

I try doing as David requested last time and "push" out. And bam! He's inside!

"Oh my god! It feels so good!" I say as he enters. His cock is on the smaller size, which made all this possible.

He starts thrusting into my ass, and I fuck myself with a finger in my pussy while rubbing my clit.

"It's so tight!" he says.

"I know. Fuck my ass!"

The slippery lube, together with our fluids, feels so good! It stopped hurting and instead made me feel whole.

I see a desperate look on the young man as I grab his butt and beg him to cum inside me.

After a few thrusts, he cums deep inside my ass as he lets out a moan.

Like David, I can actually feel the cum shooting inside me. I think my ass is more sensitive than my pussy in this regard.

With every spurt of cum, I felt his warmth spread inside me.

After a while, he kisses me, and I kiss him back, just to make this less awkward for him.

"Do you want to go out on a date with me?"

I try my best to hold down a laugh.

"Sorry, but I'm taken," I point behind him. He turns and sees David smiling. "Feel free to come over every weekend if you want to cum inside my ass!"

"Ok..." He seemed a bit disappointed. Guess he harbored feelings for me.

He pulls out, and I prepare for the cum to leak out, but nothing comes out.

He dressed himself and left the door.

David comes around the corner and takes a look at my ass.

"It's not coming out?" I ask him.

"You probably need to push it."

"If I don't push, will the cum stay inside me?"

"Yeah."

I get on my legs again and smile at David.

"Ok then! It'll just have to stay there!"

He laughed and got up as well.

I hug him. "Thank you for showing me this! It felt so wonderful. I don't need to ask people to pull out anymore!"

He laughed again. "You are welcome, my little vixen. You want some more fun?"

I smile up at him.

"Ok, then let's go upstairs again. We are going to increase the size a little bit more."

He grabs the butt-plug, and we go upstairs to his bathroom. He holds the dildo from last time and plays with my butt with it while I'm on all fours. This time it is much easier to get in.

"Is this ok? Not too big?"

"It's actually nice."

"Ok." He said as he grabbed the largest dildo of the bunch. It's almost as big as his cock. Will it fit?"

Boy, was this a fight!

For 5 minutes, we slowly pushed it in, reapplied lube, waited, applied lube, waited.

When he finally got it in, my butt felt like it was close to ripping, but it also felt so good!

"I think you are ready!"

He starts pleasuring me with the dildo for some time, and it stops feeling sore.

He pulls it out, and I can feel my butt gaping.

"Come!" And I followed him. He leaves the door, and I stop at the entrance. "Why are you standing there? Come!"

"But it's still daylight! It's not even evening yet!" I told David.

"Do as you are told, and I'll make you feel good." He answered.

Oh wow... Isn't this illegal? If we get caught, I'll be in big trouble.

"Can I wear something first?"

"No."

I take a deep breath and head outside. I feel myself covering my breasts and pussy for the first time in a long time now.

My heart rises, and I feel almost like fainting. I look around, and no one is walking outside, so I start to relax.

David keeps walking, and I follow him. I walk naked out of his driveway.

"Don't cover yourself. Let everyone watch."

I relax my arms and legs as well as I can.

He took me to his neighbor and handed me a condom.

"Just go in there."

I almost ran to their door to avoid being seen by others. I open the door; it's not locked? I head inside and close the door.

"Hello? Who is it?" I hear a man ask before I hear some steps.

"A horny woman who wants a good fuck!" My body was shaking! I touch my pussy, and it's soaking! The fear and excitement had distracted me from the mess I was making down there.

A man comes into view, and he sees a naked girl holding a condom.

"You again? Hey, Stanley! The woman is here."

The chubby friend comes after him.

"So, the girl wanted some more fun? How about we do it in the back?"

I follow them and enter back. They had a nice pool and a large table with a parasol and some garden chairs to rest on. The chubby guy pulls my arm and sits me down on one of the chairs.

"So. Two cocks and one condom. How do you suppose this will work out?"

I smile. "Which one wants to go bareback, and who wants to wear protection?" The chubby guy smiled, "I wanna go bareback."

"Ok!" I signal the other guy to lay down on the grass. The chair likely can't handle all of us. He does, and I apply the condom and ease myself on his cock. I look back at the chubby guy before spreading my ass. "Here you go!" The chubby guy might have felt cheated. He probably imagined fucking my raw pussy. Sorry! Another time!

"Wait, let me suck it first!"

He stands next to me as I start sucking his cock while I ride the cock, and making sure to spit a bit on it to lube it up.

"Now!" I demand of him.

Stanley gets behind me and pushes his cock into my ass. Oh god, it's larger than the young guy I fucked just earlier! Right now, I had two dicks inside! I've never felt this full before in my life!

They start thrusting into my ass and pussy. Oh my god, it feels so good!

When one pulls out, the other pushes in. My body gets completely overwhelmed by their cocks fucking me good.

"Oh fuck... Keep fucking me! This feels... Amazing!"

"She likes it!"

My pussy and ass were on fire now... If only David were here to see it.

They kept fucking me for a while until I heard Stanley say something. I couldn't quite tell what he was saying over my moans, but the other guy heard it.

They stop fucking, and Stanley held my arms together so I couldn't move.

They stop fucking and pull out of my ass and pussy.

"Why are you pulling out? Wanna switch?"

They say nothing until I feel Stanley push his raw cock into my pussy!