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You and the girls continue that game, and even Claire begins to loosen up, mainly due to the vodka. You end up completely naked, your cock only hidden by a sock (but kept erect by a shoelace tied around the base), as per Robin's dare. Robin however, was not so lucky, and is covering her most treasured bits with nothing but her hands, which occasionally slip and allow you to glance at her perky breasts. Lydia is tied to a chair, gagged with her panties, and covered with lipstick markings from Robin's plush lips, as per your own dare. Claire is now sleeping in her bed, having had way too much to drink, and you eye her beautiful ass poking out from her covers, marked with words like CUMSLUT and ANAL ONLY, the former having been written by you on her left asscheek.

You all begin to lose track of time and are only pulled back into reality by an unexpected knock on the door. "It's Mrs. Juniper, could you open the door so that I may speak with Alex?"

You all look back at eachother, and Robin quietly says, "Oh fuck! I'll clean up the table; Alex, untie Lyd!". You hurry round to the back of Lydia's chair and begin tearing at the restraints. Robin composes herself after putting away the vodka, "Just two minutes Mrs. Juniper, Alex is in the bathroom." she hurries to dress herself, and you simultaneously decide to give up on Lydia, so you pick her up and she squeals. You put her in the bathroom and she growls at you angrily through the gag, a little bit of drool dripping from her chin. "Sorry" you mouth to her, but close the door on her anyways.

You run to your clothes and hurry to put it on, skipping the underwear and just kicking them under your bed. You run to the door and turn around to see if the room looks presentable. Robin is dressed and gives you a thumbs up, but you point at Claire's lewd display and Robin runs over and pulls the sheets down. You feel your cock throbbing on the inside of your jeans, the shoelace still keeping all of the blood in it. Despite this, you open the door, and smile at Mrs. Juniper. She is immediately suspicious, "Where are Lydia and Claire?" she furrows her brow.

Robin gestures towards Claire's sleeping body, "She was really tired, so she decided to sleep a little earlier" she smiles. It seems to satisfy Mrs. Juniper, "and Lydia is taking a pi-" she stops her drunk self, "is in the bathroom."

She accepts it, but is still clearly aware that something is going on. "Okay, well Alex. Come with me, please."

Uh oh.

You come into her office, and you expect her to sit down, but instead she gestures for you to sit, so you do, and she opens the laptop in front of you, you see that it is open on pornhub, and you look up at her questioningly. "Well, you know what to do", she looks away and waves her arm nervously. She gestures towards the lubricant on the table, "go ahead, I need to... pump..."

She moves around to the other side of the desk, removing her blazer as she walks, and you see two massive wet spots where her nipples are. She sits on the desk facing away from you, unbuttoning her shirt. She looks over her shoulder, and says, "Well? Start masturbating". She flicks the machine on and it starts humming, quite loudly. You unbutton your pants and slip your extremely hard cock out. As you reach for the lubricant, she looks over her shoulder again, "Are you doing- OH!" she turns back around. "I'm sorry, Alex".

She grabs the cup and slips it onto her nipple, and she can't help but stifle a moan, the machine begins making tender suction sounds, and Mrs. Juniper occasionally gasps or moans. You apply generous lube onto your cock and begin to stroke yourself to the sight of Mrs. Juniper, softly mewing right in front of you. The two of you sit in her office, the silence only ever interrupted by the squelching of your hand stroking your cock, the milking machine pumping Mrs. Juniper's breast and her occasional moans and gasps. Eventually you reach the edge, and you hurry to look for something to catch your cum, remembering her warning about making a mess, but it's too late, and you shoot your load onto her desk, luckily missing any papers and the laptop.

"Uhm, Mrs. Juniper, I'm sorry." you say, embarrassed. She turns around but locks eyes with your cock for a moment and snaps around again, "Cover your penis, Alex!". You apologise again and stuff your wet semi into your pants. She takes the milking cup off of her tit, and puts it back into her bra, switching to cup to the other breast. She turns her head, "Well, at least you didn't hit anything important." she says, "Clean it up, Alex."

You throw the tissues into the bin under her desk and let her know it's clean. She turns off the machine and slips the milker off again, putting her now thoroughly milked breast into her shirt. She looks at the laptop and notices it's still on the front page. "Alex, you didn't use the laptop, do you not regularly watch porn?" she asks.

"I do, I just didn't feel like it today." you smile. She looks confused for a second, but slowly she begins to blush, and she turns away, fanning her face with her hands. "You may go. Remember, no funny business with the girls, especially not Lydia."