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The Initiation

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My story begins in a small southern Ontario town, during a hot muggy summer. I was seventeen years old, and full of raging hormones. My neighbor, Mrs. Sarah MacClaren, was every teen males fantasy. Long thick cascading blonde hair that flowed down over her shoulders, a golden brown tan, hypnotic blue eyes, pouty lips and those breasts, wow, large and firm (36DD) and nipples that could poke your eyes out. Her legs where wonderful.

I lusted after this lady for the last two years and thought that here goes another summer of masturbating and fucking bimbos.

This was to change today, unbeknownst to me. The day started out with my mother asking me to go over to Mrs.MacClaren’s place, and help her move some furniture as her husband and son where away as usual playing golf.

I knocked on the door. Mrs. MacClaren answered wearing a short mini skirt, high heels and a blouse that showed the ampleness of her breasts. She said, “Come in Max, how are you?” “Ok I guess.” “Listen Max,” she said, “could you help me move the furniture in the bedroom, as I’m going to paint today; this is the last room in the house that needs doing.” I asked her if she was painting the closet, and if she was that we should cover the clothes or remove them to another room. She said move them to the next room. I nearly fell over, when I opened the door to her closet. Lingerie the likes I have only seen in a Victoria Secrets’ catalog. Touching these items makes me feel hot and flushed, caused my heart to beat so fast that I’m sure that she could hear it in the next room. I finished the task and was about to leave when Mrs.MacClaren said, “Max thanks for the help. I was wondering if you would come by tonight and join me for supper. I hate eating alone,” she said, “and call me Sarah, Mrs. MacClaren makes me feel old, okay?”

I go home, but my hard on is so stiff it aches. I begin to fantasize about Sarah naked and offering her mouth to me to fuck, which only makes me harder. I begin to stroke my thick meaty cock and it was not long before I spewed loads of cum all over myself. Now I needed to rest and fell into a deep sleep. Some time later, I hear my mother yell down to me that Mrs.MacClaren is on the phone. “Hello, Max are you coming over for supper?”

“What time is it?” I said. “Five thirty,”she replied. “Oh! I’m so sorry, yes but I’ll be a little later as I need to shower and shave.”

She said bring what you need and do it over here or we will end up eating a dry supper.

I quickly grab my dress pants, clean socks and underwear, a golf shirt and dress shoes along with my razor and cologne and head over to her place.

I knocked at Sarah’s’ door and she said come in. It’s me Sarah, Max. Washroom is on your left, hurry up.

I go in, get undressed and placed my dirty clothes into her hamper. I hopped into the shower and began washing myself. The water was warm, relaxing and so invigorating that I took an hour in the shower. I stepped out of the shower to find my clothes where gone…all of them.

I grabbed the robe on the back of the door, put it on and went out to look for Sarah. There she was in the living room wearing black stiletto heels, black seamed silk stockings, black lace panties and corset with elbow length black lace gloves carrying what appeared to be a collar and riding crop. She said come here Max, now! I swallowed and complied. Sarah where are my clothes? she replied right here, handing me several gift-wrapped boxes.

“I have a surprise for you,” she said,”but first things first.” She reached next to her and picked up a beautiful long silk scarf; then she placed it over my eyes securing it behind my head. I felt vulnerable, unsure, insecure which is what she wanted I am sure.

Then I felt her place her hands on my shoulders and trace a path down to my nipples, she squeezed them between her fingers making me wince. Oh what a feeling. Her hands moved back towards my shoulders this time pushing the robe off of them.

I stood naked in her living room, blindfolded and at her mercy. She said, “From henceforth I will be known only to you as Mistress Sarah. You however will have to earn your name, slave.”

She then secured my wrist behind my back with another scarf. I started to get frightened. She took something silky feeling and started caressing my nipples with it. My nipples jumped to attention as my Mistress stroked them. She proceeded to lead me into another room.

Shortly I discovered it was her bedroom as she sat me down on her bed. My Mistress ordered me to raise one leg. I felt a silk-like material rub against my leg and then the other. “Stand up slave,” she said and I followed instructions immediately. Well an hour goes by and my whole body is tingling with the sensation of soft sensual material that is arousing me like no other sensation I have felt before.

Then panic started setting in as I become aware of more than one person is in the room.

She took the blindfold off and sitting there are three other women dressed in some of the sexiest lingerie.To my horror, I catch a glimpse of myself in the mirror facing me.

Here I stand, dressed in pinks stockings and garter belt with matching panties, a pink babydoll trimmed in white lace in front of four women who I frequently fantasized about.

Mistress Sarah ordered me over to stand in front of Katrina, a women that could be compared to wine(gets better with age). “Kneel you little sissy,” she said. As I did Dom Katrina opened her legs and ordered me to lick her wet pussy. She spread her legs as my face buried itself between her clean shaved cunt. I began by sucking on the lips of her pussy alternating from one to another. Her breathing sped up with every stroke of my tongue and caress of my lips on her pussy. It was not long before she was climaxing feverishly. The others watched on and masturbated themselves causing a stirring in my own loins. Diana then spoke and suggested finishing the transformation. All agreed.

My hands were untied, and I was led into a powder room, sat down in front of a big mirror that had all kinds of makeup. They looked through several magazines pointing and whispering and finally agreeing on something. They looked at me and smiled.

The next hour was filled with my legs and chest being shaved, foundation being applied, eyebrows being shaped, and finally lipstick and eye shadow being applied. Then more whispering, another nod and a long dark wig were placed on my head. One of the other mistresses, Linda styled my new hair.

My physical transformation was complete, they seemed pleased with themselves.

Tying my hands behind my back, I was led back to the living room. They pulled out a video camera and started taping. Linda sat in the leather armchair and said, “Bitch get your ass over here.” I complied. Now she said, “Bend over my knee slave.” I did as told to. She pulled my panties down and began to spank my ass with the palm of her hand. I felt the sting of her hand on each cheek. The feeling went from one of pain to arousal. My cock started to throb and I knew she could feel it between her thighs. Mistress Linda ordered me up and Sarah walked over to me. All the other mistresses seemed to acknowledge her leadership. Sarah took my cock into her mouth and started sucking furiously. I could feel my cock slide in and out of her mouth, my cum starting to build up in depths of my loins. After about fifteen minutes of constant sucking, licking, squeezing, she pulled me out of her mouth and ordered me cum on her face. I came and came like never before.

My mistress then ordered me to make each woman cum by eating their wet juicy pussies. Each cunt was wetter than the last, leaving my face drenched in pussy juices.

My mistress stood me up and lead me over to the kitchen table where my wrist were unfastened . I was bent over the table and my wrist where attached to the legs on the opposite side of the table. When I was secured each of them applied ten hard whacks to my ass with a wooden spoon. I could feel my cheeks tingling, my cock stirring.

Sarah spoke, “Ladies our little virgin requires some special attention.” I heard sounds then quiet fell across the room. My ass suddenly felt a sudden pressure, and the feeling of something entering me was evident.

Mistress Sarah said we are going to fuck that pretty little ass of yours just like all those teen sluts you fucked. The huge strap-on slid in and out of me faster and faster, then deeper and deeper. Sarah then rammed that dick of hers slow and deep, cuming several times. Each mistress took their place behind me and reamed my ass until they came.

Finally I was untied and ordered to clean each cunt with my mouth. After completing my required duty they then handed me an envelope. I opened it and on a piece of paper was a name: Sheila. I read it. Mistress Sarah then said, “This is your new name, Sheila.”

Thus began a summer of discovery and initiations.

 – The End –

This entry was posted on Sunday, October 30th, 2011 at 1:34 pm and is filed under Anal, BDSM, Bondage, Domination, Sex Stories, Spanking, Submission. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.

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