Mary's 20 Labors Pt. 05

I had a wonderful dinner with 2 beautiful women. We came back to the hotel. We had a few more drinks while I got to look at 2 beautiful women in damn near sheer negligee. I also got to watch these beautiful women have lesbian sex with each other, also each others firsts. Now I am waking up naked with one on each side of me in bed naked.

Mary suggested a break and it turned into a nap. I am now awake and I am horny. When I realize for all the excitement there has been tonight I have only been involved in fucking Jen. I gently reach out each hand to start rubbing a nipple on each woman. In their sleep their bodies start to respond. Mary's nipple starts poking out stiff and hard. A little thicker and bigger than a pencil eraser. Jen's on the other hand kind of pokes out but it's more of a swollen areola with a stubby nipple on top of it.

It doesn't take long before they are both stirring and all three of us are smiling. I ask, "Anyone need a potty break or want to go wash up before round 2?"

Jen looks at me, "Round 2?? She made me cum in the restaurant. You made me cum after I ate out Mary. I came so hard when Jen went down on me I screamed. Then you damn near killed me with that toy. That's not Round 2."

I answer, "Sorry but the only fun I have participated in was cumming inside of you for Mary to lick out of you. I want a Round 2, and Mary is the star of the Round. I promised her a good fucking and I plan to deliver."

"Well when you put it like that you are right. Mary looks like you are up, but yes potty break first."

They both roll off the bed and head into the bathroom. Why do women always go in pairs to the bathroom? They seem to be taking a bit so I walk to the bathroom. The door isn't even closed and there they are leaning on each other almost in a hug with a washcloth in their hands wiping the other one's pussy, and they are just softly moaning.

"Alright, break it up you two."

They jump in surprise, but smile.

"Get on the bed on all fours side by side at the foot of the bed. If I see someone touching someone else when I come out there will be 10 spankings for the toucher & 5 for the touchee" I smack the closest ass, (Jen's) and tell them, "Out you go."

It takes me a minute to actually pee. I grab a cloth and give myself a quick wipe and head out. Neither of them where brave enough, and maybe stupid enough to be touching each other when I came out. Well except for touching side to side, hip to hip. I grab my phone and click, two asses and pussys on display. As I walk past them to get the butt plugs and lube I drag my hand across one ass to the other. As I pick up the plugs and lube I hear Mary groan a little and then Jen soothes her, "I will be right here holding your hand. If it gets too hard for you he will stop." and Jen just gives me a look.

"Maybe." and I smile with an evil grin.

I drizzle some lube on Mary's ass and I have a great idea. "Jen you have small fingers. Work the tip of your finger in her ass. Lube her up and stretch her open a bit."

Jen whispers something to Mary and stands up with me behind Mary. She catches some lube that has dribbled and takes the bottle from me. She lubes her finger, squirts a dollop on Mary's ass and rubs little by little. Rubbing in circles, applying pressure, backing off and rubbing more and circling more. On the third try Jen pops her finger in Mary's ass. She lets out a little oh but takes the finger. Jen holds it just in her ass for a minute and then pushes in a bit.

As she slides her finger in and out a bit she is soothing Mary, "It's ok...you have this...just a little at a time."

"Ok now the first plug." I say out loud. I grab Jen by the wrist and pull her finger out, and then nudge the plug against Mary's ass. I apply steady pressure and Mary swallows the plug with little more than a grunt. I walk over and sit on the bed in front of Mary and lay back. Blow me while you get used to the small plug.

Mary leans over and starts sucking me into her mouth. Bobbing up and down probably trying to make me cum fast. What they don't realize is I took Viagra when we got back to the room. I am not going soft for a while.

Jen is kneeling beside Mary, rubbing her back and trying to figure out what is going on. Mary isn't too keen on the butt plug, but I am forcing the issue. Why am I all of a sudden being an ass? I can see this all going through Jen's head.

It's been just about 5 minutes with the small plug. I look at Jen, "Get the medium plug lubed. Pull out the small and put the medium one in."

Jen looks at me like I am talking in a different language, "What?"

"You heard me. Put the medium one in."

"She needs more time to stretch to get ready for you."

"Five minutes with each and then I am fucking her ass."

Mary looks over her shoulder, "It's ok I told him I would, and I will. I can take it. Put it in."

Jen pats Mary's ass and pulls out the small one with a pop. Then lines up the medium and starts sliding in and hits some resistance for the last ⅓. I suggest just pushing it in, but instead Jen backs it off and pushes in. Backs off and pushes in, each in stroke pushing a little more in. Then on the third or forth push Mary grunts louder and takes it all, and buries her face in the bedsheets beside me. Jen crawls up to her. I can hear them talking but can't make out the whispers.

Then Jen turns to me, "Enough is enough. Mary can't take it. I am pulling it out."

"No don't" Mary screams.

"But honey it's hurting you."

"I can't say no to him."

"Yes you can." Jen looks at me and says, "No! See you can."

"No I can't. I made a promise I can not break."

"What are you talking about. You can promise to try anal. You tried. It hurts, end of story."

I chime in and say "...end of story. What a curious thing to say. Have you ever heard the story of Hercules 12 Labors Jen?"

Jen stares at me for a minute, "Yes. What does Hercules have to do with Mary getting her ass fucked when it's plain to me she doesn't want to?"

"Mary & I made an agreement to avoid her losing her job, retirement, & pension for being caught doing drugs at work."

Jen looks at Mary, "What did you do?"

Mary starts crying, "I can't talk about it." and looks at me.

"She is bound by the agreement not to talk to anyone about it or to risk the video of our first fuck to seal the deal if you will getting posted everywhere with her name tagged on it. She agreed to 1 Labor for each year with the company to save her job. To do as I say when I say. No saying no, ever."

Jen is looking at me in disbelief, "What kind of asshole are you?"

"I am the asshole that talked you, with Mary's help, into joining us tonight. I am the asshole you begged to have fuck you earlier. And now I am the asshole that is going to fuck Mary in the ass."

I reach for the plug to pull it out, but Jen's hand is faster. She puts her hand over the plug, looks at me and says, "No, fuck my ass instead. Fuck it as hard as you want but leave her ass alone."

Mary wails, "No. I have to do this."

I start thinking, "Well you aren't saying no Mary. Jen is offering herself as an ass slut to take your place for all anal sex."

"No, she isn't. Do it fuck my ass."

Jen looks at me, "Don't move." and pulls her hand away. She crawls up to cradle Mary's head in her lap. "It's ok honey I can do this. It is obviously too painful for you. I can't watch him tear you in two. I have had rough anal before, I can take it."

Mary just sobs in her lap. "No no no"

"Well wait a minute who says I am agreeing to this? I have a nice tight ass right in front of me why shouldn't I fuck it?

With venom in her voice Jen says, "You are an asshole."

"OK Mary's ass it is and I reach for the plug."

"No wait. I am sorry. I will take it. Fuck my ass."

"Well that's fine for tonight, but what about in the future when I feel the need for anal. Mary will have to take it then. Why put it off? Rip the bandaid now if you will."

"You promise to leave her ass alone period and you can rip into me all night. Fuck my ass all night, but you promise to leave her ass alone."

"Wait, give up a third of my fucking options period for 1 night? Not enough. If you want me to give up a third you have to give a third."

Mary was still crying, "No I can't let her. I can do it."

Jen strokes her hair soothing her, "Looks at me and says and what do you mean I have to give a third?"

"After tonight Mary would have had 15 of 20 labors left. If I count it off and am being generous, 1) the night she agreed to the labors and we fucked, 2) Naked on her couch fingering herself so I could walk in and fuck her, 3) letting the salewoman at the toy store kneel in front of her, remove her shorts and watch Mary from 12 inches away insert her new toy, 4) the threesome tonight with you, and finally 5) the fucking you will both get in the AM. You promise to join her for 5. Tonight, tomorrow and 4 more and to be clear. You can Never Say NO! I will allow Mary a pass on anal, but only Mary. Your ass is fair game Anytime I Want. You promise to stay until we check out in the AM. From this moment going forward no saying no. I tell you to do something, you do it, period."

Again Mary sobs, "No Jen please I can't let you."

"You aren't letting me. I am doing it" She grabs to lube from me and flops on her back.

She squirts some lube on her hand, picks up her legs and starts lubing her ass. "It's been a while but I like it on my back. Take the plug out of Mary. Stick your dick in my ass and I will consider this agreement a done deal."

"Sorry dear you don't dictate the terms. For now the plug stays in Mary as I fuck her pussy with her on her back. You will get on all fours above her and when I feel the need I will pull out of her pussy and fuck your ass. You can console each other as I DP Mary and ass fuck you."

"Fine you win."

Mary rolls over on her back, and I grab her thighs and pull her right to the edge of the bed. I watch as Jen crawls over her. I pull her back a tad and push her ass down. I leave them so they are stomach to stomach with Jen just a tad forward. Now I can pull out of one and shift up or down a little and into the other.

I reach out and grab the plug by it's base and wiggle a bit. Mary is whimpering. She has a tight grip on it. I reach down, line myself up and try to slide into Mary's pussy, but she is a bit dry. I grab the lube squirt some on her lips and some on my dick and then slide right in.

Mary cries out a bit, "It's so tight."

Jen is trying to sooth her, "Focus on me. Open your eyes, and look at me. I am here. I will protect you and she leans down to kiss Mary."

I have never felt something like this before. Its hard but the soft feeling of her flesh in her pussy rubbing against me as I fuck in and out of Mary. I pull out of Mary and line up with Jen's ass and push myself in. I can feel her body stiffens and she lets out a real groan and seems to be grunting on every stroke.

Now it's Mary's turn, She has her arms draped around Jen's neck. Holding Jen tight. "It's ok honey. I am right here. I am so sorry you have to do this for me. I pull out and start to line up to fuck Mary again when I notice Jen's ass starts to close.

"No, no we can't have that." I say and I grab the final large plug and shove it in Jen's ass.

She lets out a small scream and then groans, "Jesus that's big. So big. Oh god."

"I will be nice too. Since Jen now has a plug I will take Mary's out."

I pull it out, and Mary lets out a small yelp. I drop it and slide my dick in her pussy and start stroking in and out, and all I get is a moan. For all the hype about DP, not feeling that hard soft feeling of the plug in her ass is better. She has a nice tight pussy. It doesn't take much and Mary's moans are turning to pleasure again.

I pull out of Mary. I pull the plug out of Jen and she gasps. Before she can finish the gasp I am fucking her and the gasp turns to a grunt. She has her face buried in Mary's neck again grunting with every stroke.

"Is this what you wanted Jen? Is this the hard ass fucking you wanted? I ask.

She doesn't lift her head from Mary's hug but I hear her say, "You call this hard."

This one is going to take a little breaking I see. I grab her hips and start giving it everything I have. Now she is screaming, but won't cry uncle.

Mary begs, "Please stop. You are hurting her."

I stop buried into Jen's ass all the way. "I will stop the real hard fucking if you make me a promise."

"Anything. You are hurting her."

"One of Jen's labors will include getting DP'd by me and you with a strap on. You will have to fuck her pussy and ass hard. Don't fuck her hard she will get punished not you."

Mary looks at Jen and Jen just nods yes.

"OK." Mary says.

I pull out of Jen, shove the large plug back in and line up to start fucking Mary. I am sliding in and out of Mary and decide it's time to teach Jen who's boss. I reach up and start pulling on the plug. A little bit more pressure and her ass stretches and it pops out, and Jen grunts loudly. I don't even pull it out all the way and I am pushing it back in. Hard steady pressure and she stretches back open and swallows it. She yelps and again I am pulling it out. In and out, in and out I go.

About 5 or 6 times when she finally cries uncle. "Please leave it in or out. That wide base going in and out feels like I am giving birth."

"So you want to mouth off and say how tough you are." and I shove it in. "you call that hard" and I pull it out. "Fuck me hard" and I shove it in.

Now I have broken her. She is sniffling and crying

Mary changes tactics, she looks at me from under Jen, "Please I agreed to you deal. Please stop causing her pain. We will do as you ask."

"See Jen that wasn't hard. I am not a monster. Mary asked nicely and I will comply." I say.

Will one quick pull the large plug is out with a small scream. That turns into a bigger scream when her gaping ass doesn't have time to close and I am back to fucking her ass. I am not fucking her as hard as I was, but I am not being gentle.

I am hearing Mary try to sooth her. Jen gasping, sniffling and crying. She hasn't mouthed off so maybe she is starting to learn.

I decide I want a picture of them like this and pull out of Jen, and tell them not to move. I grab my phone and as I am framing the shot. I get an odd ring. I click accept and this is odd. When am I looking at the face of the waitress from earlier, Lisa? Oh shit it's Facetime...

That's when I hear a shocked giggle, "Well I guess you guys are still up. I almost didn't call. My coworker Irene talked me into it but I insisted she come with me."

It takes a second to register that they are looking at Mary's well used and lubed pussy, and Jen's still gaping ass. I hit the little circle button so they see me.

"Sorry about that. Can I see Irene?" The next thing I know another cute young lady is on the screen. I can tell they are in a car together. "You are both more than welcome to join us, but we have a strict dress code. Everyone must be naked. When you knock at the door Mary and Jen will greet you at the door naked and help you take off your clothes."

Irene's face is a bit blank, and just gets out, "What?"

Lisa looks at her and says, "You told me to call them. To take a chance. No backing down now. We are leaving the parking lot and we will see you in 15-20 minutes."

The women haven't moved so I take the picture I wanted. I look at them and say, "You have 15 minutes to clean up and get ready for our guests."

Jen speaks up, "Guests? What? Those 2 young girls. You want us to greet them naked and take off their clothes."

"To start with yes. Jen, you just agreed to help Mary with her labors. Remember the part, Never say no, EVER? Are you saying no? Should I just ask you to leave, and after you are gone fuck Mary's ass?"

She sighs, "No." and looks at Mary and the two just hug.

"Unless you want to be opening the door with lots of lube on your ass & pussy I would go get cleaned up for our guests."

They glare a tad but walk into the bathroom together this time closing the door. It takes them a few minutes but they come out. Sit on the couch together naked and snuggle into each other. I get up and go to the bathroom. Wipe myself clean of lube, and head out of the bathroom. I sit across from the ladies and look at my phone. It's just a few minutes later and there is a light knock.

"No covering up ladies. Open the door, let them in and help them strip. Once they are naked each of you take one by the hand and lead them to the bed."

I look and see the 2 young women walk in. I can hear the introductions, and then I hear an, "I can get that." "Oh here let me help." "I can take those off, oh" Before I know it from around the corner comes walking Mary with Lisa's hand in hers, and Jen with Irene's in hers. They are heading for the bed when I suggest, "Why don't you all get comfortable and we can play 20 questions to get acquainted."

I turn the chair so I am facing the bed and stretch out my legs letting my hard on just stick up. I catch Irene looking at it. "Does it look ok to you Irene? Do you think you want to eventually take a ride on it?"

She smirks, "Maybe"

"Ok fair enough. So 20 Questions, and I am first. Before today has anyone actually had sex, or gone down on another woman?"

No one raises their hand and Lisa just looks at Mary & Jen, "Really?"

Mary looks down a bit, "Jen had just met us at a clothing store earlier today. We asked her to join us for dinner & dessert and she said yes."

Lisa with a shocked look on her face, "Wow I figured with what was going on in the booth you guys had umm, done this before."

"OK Lisa that's your question." I say

"Really?"

"Yup see just like that you said Really as a question. Guests first so Irene it's your turn."

Irene is a solid girl. Very top heavy, an easy D that sag under their own weight, she isn't fat but just thick and there. She is a strong girl.

Irene looks nervous like she can't decide to ask what's on her mind. Finally a quiet question, "Can I kiss you?"

"Who are you talking to, Irene? I can't tell since you are looking at your feet." I ask.

She looks up and points at Mary.

"I think that's a great idea. Irene you kiss Mary, and Jen & Lisa can kiss. Give each other a nice 30 second passionate hello kiss, then Mary & Jen will swap for another nice kiss hello, and then Jen you will kiss Mary & Irene you can kiss Lisa. That way we can be sure everyone has kissed everyone hello. Well at least for you ladies."

Mary moves over and holds Irene's face and leans in and kisses her. Lisa is watching this and looks at Jen and smiles but moves over towards her. They meet in the middle if you will and start kissing. I have to say it's a heady thing watching this.

"Time." I call out. The ladies break their kisses and Irene and Lisa swap places, and it starts again.

Again, "Time.' I call out and Jen moves towards Mary and they are being a little more passionate with each other. Lisa and Irene shuffle places and see this and watch for a minute.

Irene looks at Lisa, "Are we really doing this?"

All I here from Lisa is, "Uh huh"

Irene asks, "What happens in the hotel stays in the hotel?"

Lisa smiles, "Oh yes." and leans into Irene and they kiss

I say nothing this time and I let them continue kissing. At one point Lisa looks at Mary & Jen still kissing and watches them for a moment before turning her attention back to Irene, but never breaking the kiss. There is nothing but soft sighs and kissing sounds for probably 1-2 minutes.

I clear my throat and the 2 pairs break. " I would normally say ladies first but I am looking at 4 beautiful ladies right now. So I will say guests first. Irene and Lisa would you like to give or receive first?"