Halloween Won

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Status: In Progress  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

When people divorce, there are so many issues. When an order of separation is given, our freedom is not what we planned.

Thirteen years ago I had Halloween Party One. Thirteen years ago I was in the midst of my divorce and I was legally separated for three months. Three months of the straight and narrow path. Working, volunteering, kick boxing, and selling the last home that we had while we were married.

In the summer and early fall the only good time I gave myself was buggy boarding at the beach and going to movies alone.

The papers signed by both parties claimed an independence from each other while we fought like pit bulls to divide up the money. Nothing new about this game.

By early October with the ocean cooling off, I needed another outlet. Joining up on a dating site was a move that I was willing to try for a limited time.

I put myself on the net with an alias, but also with a true description of who I was and what I was going through at the time.

Separated man desires to meet single, divorced, or separated woman. You must be over forty, have no children hanging around and depending on you. I will promise to be a gentleman when you want me to be a gentleman. I will cuddle you if you need cuddling, and I will be discreet. No actively married women PLEASE.”

I put it out there on the network. No picture, no telephone number, no address.

The responses began coming back within minutes. There were women that responded with their pictures, more discrete women that asked me for more information. I sifted through the responses of those women with eloquent thought out replies, and began to write about myself to them.

I am above average in height, I have a full head of hair, I am height weight proportionate. I do not smoke, drink some wine. I do like to be honest and I would like a woman that will be intimate only if she is willing, because I am.”

Those that I wrote back to often had some interesting questions for me to answer.

What would you do to me that would make me want to moan with pleasure?”

I thought about that question for several minutes. I didn’t want to be seen on a date. If I was seen around town with any woman it would make me look worse in a judges eyes to be with someone else. It might be construed as a planned marriage departure and cost me more. So I wrote:

I will meet you at a lavish room and slowly undress you, pick you up and carry you to bed, nude. I will have baby oil that I will apply to your back, massaging out all the knots and tired muscles, trying to get you as loose as possible. I will massage your legs, your feet, your calves, your arms, you hands. The last portion of your back that I will work on is you ass. Here I will find the sacral joint and then work down to your coccyx and the G spot. These areas are very often tired and sore from sitting. I will rub your gluttonous muscles until they are rosy red. Then and only then will I softly roll you over. Before working on your front I will strip so the you will see my erect cock with lubing ejaculate dripping because I am so excited to be with you. Your upper body gets nicer treatment. I massage you breasts and slowly work them out to your nipples until they are hard. I will rub down to your abdomen muscles and massage them. People forget these muscles! Finally I am close to the Victoria V where your pubis, vagina and clitoris are waiting. I will look in your eyes questioning if I should continue? You smile and languidly nod your head. I have a surprise for you with my oil. It is a vibrating dildo that I oil up and turn on. I insert it in your vagina while spreading your labia lips with my fingers. I move this device in, out, around and around. I am reading your body and when I know that you are ready, I move the dildo to your clitoris and tease around until your body is moving to it with a will of it’s own. Then I begin the grand finale of working that clit enough that you shudder, spasm, and moan mewing shit, shit, shit.

I laughed to myself when I got a reply from this woman that she had fingered herself off while reading my reply. She went to my whittled down list that I had narrowed down to a few. It was charming and happiness when those that responded and did not want to go onward wished me luck. Xoxo, interested what happens next, keep up with your great responses!

I finally narrowed my search down to two, like the “American Bachelor”. They had sent me provocative pictures without their faces being completely visible. I made my decision based on a bare glimpse of one provocative picture and a note saying that we were only a one night stand. Name the date!

I didn’t want my picture on the internet for public perusal. I know that she felt the same way after more written notes. It came to me in a flash of erotic imagination.

We could meet at any place of your choice on Halloween. We both must have our face made up to disguise our faces. Everything else is up to you and me. You may give your friends a heads up, carry mace, an air horn, or be yourself. I promise you that I am safe. I will meet you where you desire and we’ll make it a wonderful twelve hours.”

She quickly replied: “Get a corner room at the street level at the Ramada on Ocean Boulevard. Have keys available at 4PM. I won’t pick up my keys, so don’t bother snooping. We will meet at 8:30PM Halloween outside the room.”

I booked the room, picked up my credit card key and notified the desk manager that there would be another key pick up. I tipped her to be sure she understood.

At my temporary dwellings I waited until sundown and then made up my face like that rock star with the long tongue. I put on a long sleeved muscle shirt, skinny jeans and my Doc Martins. Looking at the stranger in the mirror I gave a shrug, walked out to my car and drove to the room.

At 8:25PM I walked toward the room and knocked. There was no answer. Then around the corner walks a woman with her face painted as Grizabella, the female cat from the Broadway show, “Cats”. She walked up and playfully purred.

I said, “Happy Halloween, I’m Michael.”

She smiled at me, and said, “Well then Michael, I’m Rachel.”

We looked each other up and down. Rachel was wearing a black tube knit dress with a tail sewn on her back side. I wasn’t sure what was underneath, but I liked what I was taking in with my eyes. Rachel was around five feet eight inches and was definitely height weight proportional. Her hair was the tawny color like a tabby cat.

I motioned to her to come closer to me and she sidled up moving like a cat might slink if it was a woman.

“Thank you for meeting me.” I said. “I hope that you may find me pleasing enough to continue moving forward. I like your face, your dress, your aura, and I love a purring…...”

She laughed and said, “Pussy!”

She made the first move outside the room and placed her hands on each of my shoulders, looking me in the eyes. “Rules I go by. I am not into anal anything. I will not be hit, yelled at, or forced into any situation I am uncomfortable with. I have means to make you stop. You might be missing a testicle or two if you go too far.”

She then came right against my body and tenderly kissed my lips.

“Do you have rules?” she asked.

“If I ask you to slow down so I don’t orgasm until I desire, would that bother you?”

She laughed and shook her long beautiful hair.

She said to me, “Insert your card and open, and then close the door.”

I did that and thankfully it turned green. I opened and closed the door.

She then got her computer card and it turned green. She opened the door and walked in, her ass swaying back and forth under the black tube dress. I followed her in as she put her pocket book on the dresser by the bed. She reached down and pulled back the bed spread and the sheets. She then turned around and ever so slowly pulled the black tube dress to the floor. She didn’t have anything on underneath but her beautiful freckled skin. I then noticed that her fingernails and toe nails were manicured and painted shiny black. The pubic hairs were very neatly trimmed back and left about one half of an inch long. Her breasts were the size of large lemons with that type of pointy end. Large aureoles and nipples about the size of her finger tips.

“Do you like what you see Michael?” she whispered.

I nodded my head as she walked to me and got the bottom of my muscle shirt and pulled it up and over my head, throwing it to a chair. She raked me on my chest softly with her nails and then reached around my shoulders to pull us groin to groin. We began to do that dirty dancing that wasn’t fair. My skinny jeans were still on and she was nude. She giggled, got my belt buckle unclasped and then unbuttoned and unzipped my fly. She reached to each side of my hips and wriggled my jeans down to my ankles. Her face passed my quivering cock and she gave it a quick kiss as she got to her knees, unlaced my Doc Martins and took them off one by one. Then she took my jeans all the way off, a leg at a time.

Rachel slowly stood up and had her hands on the side of my body all the way as she stood up.

“I know you didn’t bring that oil and that dildo,” she began, “But I have it right there in my pocketbook ready for you to put to full use.”

She took my hand and pulled me toward the bed, reached in her pocketbook and pulled out a small bottle of baby oil and a six inch pink dildo with the switch on the end. She also took out a small tube of hand sanitizing lotion and motioned toward my hands and sprayed it into my palms. As I lathered my hands she sprayed some onto her hands and then lathered my penis for about forever.

“We can’t be too clean, can we?” she asked.

I didn’t need to pick her up and place her on the bed. She jumped onto it face down and was tickled with herself, laughing as she got into her massage position.

“Michael, you are still an amateur at this internet dating. But I like you. You are so good at writing descriptions and about other topics that I selected you from my choice of a dozen men.” she said.

I was reeling from the idea that she was the woman that fingered herself to my writing and was now lying in bed naked, except for her painted face.

I got the baby oil and went to work, spending a good twenty minutes on her back, neck, legs, feet and arms. Then as written, I rubbed her ass and worked on the sacral area. Before making her ass rosy Rachel said, “Spank me Michael. Not too hard, but not too soft.”

I had not spanked women much. If anything, when I was single they were into bondage and make pretend wrestling, wanting to be pinned; literally.

So I started slapping her ass cheeks. She moved them around and they got red, then redder. Suddenly she shuddered and gasped.

“Well now, that’s number one, not like I’m keeping count!” she moaned.

I rolled her over and massaged her front down to her pussy. Her wonderful large nipples engorged and she opened her legs to a forty five degree angle with bent knees. I got her dildo and she smiled at me and said, “Pink for breast cancer month.”

This area I was much more accustomed to manipulating under my control. Prior to turning on the switch I used the dildo as a dildo and moved it in and out of her cervix. When her shoulders and arms started moving and she was adjusting her body I knew that she was ready for her crescendo. I turned on the vibrating pink pussy manipulator to her clitoris and kissed my way up to her mouth. We shared our tongues and our juices. I nuzzled her neck by her ear and playfully bit, but not enough to make a bruise.

Rachel came with a rush like she was sneezing out of her vagina. She sat upright and shook with the effort of her climax.

“Whoops, I did it again,” she said as she shivered. She leaned over and took my cock in her mouth and I swear she was humming the big show tune to “Cats.” Memories.

I didn’t last any more then three minutes before I ejaculated in her mouth. Rachel wasn’t the swallowing type, but she took a quarter of a cup in her mouth before she spit it into her hand.

“Yo doggie,” she said.

The remainder of the night was more of the same and even more then I expected. My face was made up like that rock star with the long tongue and she wanted me to eat her pussy. I thought about cats mating and I mounted Rachel while she lay flat on her stomach so I could enter her.

About four AM we were delirious with love making.

Rachel said, “Michael, you can fuck me in the ass if you’d like.”

I was shocked but pleasantly surprised. I had only done this to my wife without a condom and got a bad urinary tract infection. In my skinny jeans I had one rubber. Rachel mustered up one more erection and rolled my rubber on. She reached into her pocketbook and pulled out a small tube of KY jelly.

“Always prepared,” she noted.

I think that Rachel had done this before because she got a pillow under her cervix and gave me instructions as I entered this nebulous area.

The tightness, the mastery, the submissiveness of it all was almost more then I could comprehend. I came and came in that condom and slowly withdrew.

Rachel turned to me and kissed me.

“We had an adventure Michael, I will miss you for awhile.”

Rachel got out of bed and left before dawn. I shrugged and decided to do the same. We both left our computer door cards on the dresser with my five dollar tip.


It was three weeks later when I was in the Judges chamber with my lawyer, my soon to be divorced wife, the Judge, and a transcription writer. Everything was flowing well when into the room walked a woman with familiar hair, gait, and something else?

She handed my attorney some paper work and at the same time whispered, “Meow” in my ear. She also handed me a folded piece of paper and walked out.


The divorce was settled with equity and honest judgment. I walked out of the courthouse and got into my car. Only then did I unfold the note.


Michael, you should never leave your laptop unlocked where ever you go. I am the paralegal for your attorney that had more then an itch for you. When you took a break, I went into your computer, discovered where you were and what you were up to at that time. You are a fabulous amateur. I had a wonderful night and I hope that you did, R.”

Submitted: October 23, 2017

© Copyright 2021 Michael Arlis. All rights reserved.

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Add Your Comments:


Amy F. Turner

Mmm, mmm, mmm to the fab amateur! This was a hot piece of wonderful writing, MA! Whoo hoo! Now that he knows who she is will he try to contact her for something more than a one night stand?

Mon, October 23rd, 2017 2:28am


Will she let him?

Mon, October 23rd, 2017 7:17am

Amy F. Turner

Of course otherwise why reveal herself if not interested in more play now that he is free?

Mon, October 23rd, 2017 5:38pm


She exposes herself because that is her biggest turn on. When his idea of Halloween disguises is presented she is becomes totally hot and bothered. She also laid plenty of rules out that she took back one by one. Maybe they will meet again.....

Mon, October 23rd, 2017 10:47am


So much for all the rules, huh? A fantastic journey!

Thu, December 14th, 2017 11:57pm


Costumes make everything different. MA

Thu, December 14th, 2017 7:22pm

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