Mary's 20 Labors Pt. 02

I should have put this at the beginning of Part 1, but this is my first attempt at this for publishing. Please forgive any grammatical or English Comp errors. School was 35 years ago. I will try to get better. A special thanks to astuffedshirt_perv for the creative criticism. She pointed out a missing piece of the puzzle if you will. I reworked Part 2 that I thought was ready to submit to correct that omission. Thank you astuffedshirt_perv.

*****

Monday 8AM

Mary is sitting outside my office and I have already told my assistant what I found Friday, and that Joe would be terminated. Mary's long tenure and excellent record has gotten her one last chance. I want to hear no rumors, but I want her to sit in on the meeting as a witness.

I call Mary in and ask her to close the door. I already have a letter written up. Basically saying she will report for a minimum of 20 therapy sessions to talk through her new drug issue. If she can get the therapist to say she is "good" this record will be sealed and never see the light of day again. All three of us sign it, and I ask my assistant to step out while I discuss some of the fine details with Mary.

I look at Mary and realize she is the perfect unassuming Mom. Not a MILF, but someones Mom. Nothing a teenager or young man would call a MILF, but there is certainly nothing wrong with her that a middle aged man would reject. Her boobs, C Cups sag a bit, her belly is fleshy and yes her hips and ass have flared out a bit with age. She has shoulder length brown hair that is a bit full and wavy, not flat, and brown eyes. When you look at her you notice her boobs stand out from her midriff just enough to be noticeable. There is nothing wrong with this mature sexy middle aged woman.

While we have both been with the company and are aware of one another. We have never worked together. She has always been on the floor on the production end. While I was in the mailroom, payroll & HR over the years. I know just about everyone, and they know me from coming to me over the years for payroll or HR issues. I have always been the friendly guy. You need help? I am happy to help. Mary has never seen this commanding side of me, and to be honest I am not 100% sure where it came from. Everything just started popping into my head Friday, but I will admit I enjoyed it. Ultimately Mary did too, but I need her to keep playing her part. While I may have recorded the encounter for my enjoyment. I could never send it out to the world with her name on it. I am just not that guy, and I hope she doesn't fully realize it. At least not anytime soon.

I ask Mary, "Do you understand the therapy sessions will cover your 20 Labors?"

I get a yes nod.

"Say it aloud Mary."

"Yes I understand." she replies.

"What do you understand?"

"The therapy sessions are a cover for my 20 Labors, of doing whatever you tell me to do." she answers.

I praise her, "Good girl. A friend of mine is an addiction therapist and one of her labors will be a nice thank you for him, since he will be emailing me "appointment confirmation" emails."

"Of course." she says rather flatly.

"Did your son go to his Dad's this past weekend or next weekend?"

She looks at me a bit strangely and then answers, "Next weekend."

"Good, I will pick you up Saturday afternoon and you will be going away overnight with me."

She just stares blankly not sure what to say.

I tell Mary, "I will let you know the specifics later, but I am thinking Thursday I am going to make an appointment for you to get a full body massage, and a Brazillian."

Yup that did it. She goes a tad pale.

I tell her, "Go clock in."

She sits for just a moment and gets up and walks out. Man this is going to be fun.

Later that day after making the appointment I go and hand Mary an envelope.

I say, "Here is the paperwork you requested earlier." and i just keep going since there are other people around. What's really inside it is the name address and time for her massage, and the cash to pay for it.

Thursday night I text Mary from a cheap burner smartphone so there are no records on my personal or business cell of all the calls and texts to come. She doesn't answer after a bit so I simply text. "Hercules, answer my text." That gets me a reply within 2 mins. I tell her to text me after her son is asleep and she is in bed.

About 10:30p I get a text, "I am in bed."

"Strip naked. Lay on top of your covers, and answer the Facetime I send you in a few minutes."

She answers Facetime and I can see bare shoulders and her face.

I tell her, "Hold the camera out and let me see if you are naked."

The angle changes and yes she is naked. Propped up in bed her darker areolas standing out against her paler skin with her nipples just showing a little pop.

"Spread your legs and let me see the results."

Things shift again and I can see she is a bit red, but baby smooth. She pans the camera back up to her face and I ask, "Did you get the massage first or the wax?"

Mary says, "The girl suggested the wax first, so when I left I would be leaving with the good feeling of the massage."

"When you left did she make sure you were feeling good? Your pussy looks a lot shinier than the rest of you."

"Wait did you know she would do that?"

I ask, "Do what? What did she do?"

Mary turns red enough for me to see on the phone and says, "The masseuse said at the end she had a nice oil to apply to lessen the sting."

"Are you upset because she wanted to rub some oil in and lessen the sting?"

"No."

I ask, "Was it exciting to have a woman rub oil into your pussy? Did it feel good when she rubbed your clit and fingered you?" I get no reply.

"You did know?"

I laughed, "Of course I knew. I sent you there because it's known to give happy endings with a nice tip. I also stopped there about 2hrs before your appointment and told the girl I would tip her another $100 if she would place the 2 GoPro cameras in a good spot so I could get a good view of the action."

She goes pale again.

"I figured if I was paying I should get some enjoyment too. I was outside waiting for you to leave. After you left I went in and picked up the cameras. I just finished watching it. Man did you cum hard. I have to say it seems like she has talented hands. Rubbing your clit with one and sliding 2 fingers in and out, now that's talent. Put the camera back on your pussy. Slide a finger in there and spread those lips. I am betting you are still wet." I tell her.

All I hear is a sigh and some shuffling and her glistening pussy is back in view. I then see her hand come down, rubbing and spreading her lips. Sure enough she is wet and she slides 2 fingers right in.

"Don't stop but put the camera back on your face." She comes into view and I tell her, "Be honest. Did you orgasm from the happy ending because it felt good or because it was a woman?"

"Both."

"Would you want to try having sex with a woman?"

"I think so." she answers.

I ask, "Would you want to try fingering and licking another woman's pussy, and make her wet like you are now?"

"I think so."

"Are you thinking about the woman that fingered you earlier."

"Yes." she says quietly.

"Well then I promise you one of your labors will be with a woman. Hopefully I can arrange a threesome with a woman for you. For now I want to watch your face as you cum. I want you to stop talking. Think about whatever you like and make yourself cum so I can watch your face as you do." I tell her.

A few minutes later she did just that. Her face got a little scrunched up like she was concentrating and then the aaahhhh look and a gasp/moan.

A minute or so later she looked sheepishly at the phone and says, "Did you like that?"

"Yes I did."

She asks, "Can I watch you cum? I have never seen a man cum."

"You mean you have never actually seen a man's sperm shoot out of him?"

"No, I have always been curious. It's always been in me or in a condom."

I instruct her, "Saturday at 11:45AM you will have your luggage ready to go and be dressed. Then at noontime you will strip naked leaving all your clothes on the floor, and lean back on the couch and finger yourself with your front door unlocked. I will walk in, and fuck you before we leave. I will pull out and cum on your boobs so you can watch a man shoot his cum for the first time."

She smiles a bit and says, "Ok."

I think her inner freak is starting to find its way to the surface.

Saturday 12:01p I turn the knob to her front door and it opens. I hear a nervous voice, "Hello?". I don't answer and a little higher pitch, "Hello?" I slowly walk towards the voice and she is half sitting up pulling a blanket to her.

"Don't you dare." I say firmly.

She drops the blanket and lays back.

"I am sorry I was nervous it wasn't you."

"I didn't tell you to stop. Keep fingering yourself." I tell her.

As I am taking off my clothes I ask, "Who else would just walk into your house?"

"My son, ex and sometimes my sister."

"It would be a tad funny if you got caught fingering yourself by your son. Probably an image he would never get out of his head. The others, well you are an adult and can do what you want. What would your sister do if she walked in say 5 minutes from now and saw me fucking you, your pussy making sloppy wet sounds, your tits bouncing and you moaning?" I ask.

"She would probably scream and leave. Knowing her she would want me to tell her I am ok first."

I am now naked and I grab her by the hand and pull her up to a standing position. Grab her by the hips and turn her around 180, and push her onto the couch in the doggie position. I step towards her and rub my dick between her wet lips and feel her opening line up, and I slide right in. One smooth easy stroke that makes her gasp. Grabbing her hips stroke by stroke I increase the tempo. It doesn't take long for the wet slurping, skin on skin slapping and some moaning and groaning from both of us to be the only sounds in the room. Before I know it I have to pull out if I am going to honor my promise.

All I get to say is, "OK"

She is spinning around kneeling in front of me. She bobs her head on me once or twice and then just strokes me. I can tell by how she is holding me I wont be cumming on her boobs, but probably chin and neck. Sure enough I pop. The first spurt hitting her chin. She opens her mouth in shock and gets the second on her tongue and lips. She then gets smart and points me down. The final spurt and dribbles landing on her chest. She has a look of amusement and wonder on her face as I put my hand on the back of her head. As I pull her forward she opens her mouth and sucks me in. Her tongue running around the head of my dick licking me clean. She then starts sucking as she pulls off me with a slurp and pop.

I sit on the couch and she sits next to me alternating between rubbing my cum into her skin and licking the larger globs off her fingers as she scoops it up.

"Did you like that?" I ask.

She shyly grins and answers, "Yes I had never seen it shoot out before."

"Well I may not have the volume of a younger man but I vow this weekend no cum will go inside of you. Only on you so you can watch it come out."

She starts to stand up, and I smack her on the ass. "Now get dressed we have some shopping to do."