Stepmother Ch. 01

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A stepmother begins training an errant stepson.
1.5k words
4.24
218.5k
43

Part 1 of the 2 part series

Updated 11/01/2022
Created 01/08/2006
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THEN: The soft Side.

My stepmother and I had maintained a peculiar relationship, ever since she had had caught me trying to sneak one of my fathers girlie magazines back into his bedside cabinet; one that I had torn out a few pages from. At the time I was 18 and had just come home from boarding school for the summer holidays.

I have to admit I had always had fantasies of being dominated by a woman, not a cruel woman mind, but rather one who would enjoy playing a fantasy role as dominatrix while I indulged my pleasure in being dominated. In my stepmother I had found such a person.

She had covered for me with my dad, by disposing of the magazine in question and saying that she had found a particularly tasteless article that had offended her so much she had consigned the magazine to the garbage bin. Luckily dad did not question her further about it. I had never felt such humiliation in my life as I had upon her catching me, in her and my dad's bedroom, going through his bedside table with a girlie magazine in hand!

She had been really nice about it, after her initial disgust at the intrusion to their privacy, understanding that I had had little in the way of mature sex education, nor had I experienced my sexuality being confined to an all boys Catholic boarding school.

Anyway the upshot was that she would not show the magazine to my dad or tell him about my episode, but I would have to allow her to train me and bring out the repressed sexuality that was obviously longing for release. Though embarrassed beyond words, I agreed. So many feelings hit me at once that day, self loathing, fear, excitement (for my stepmother is a great looking lady and only 20 years my senior). She had done little that day really, just a beginning, a taste of what was to follow...she had asked me to strip in front of her, as she sat on the double bed, her tight jean clad long legs crossed and as calm as you imagine.

Looking back, I guess this was the moment when our new relationship was cemented. Had I refused where would we be now? But I didn't, I couldn't. So red faced and sweating mightily I had slowly and awkwardly removed my clothing down to my underpants. I looked at her, and she just smiled and repeated that I should strip for her.

The confusion I felt was overwhelming. A part of me was furious with her, furious with myself, wanting only to collect my clothes and rush off to my bedroom. I'm unsure why I stayed. Her calm demeanor I thought later had steadied me. She didn't laugh at me, though a small smile stayed upon her face as I fought my inner turmoil. Finally I did remove my underwear, and stood before her naked and somewhat frightened, unsure of myself.

She bid me come closer. I was as red as a beet now, as I was suddenly aware of her as a very sexy woman. As I stepped closer to her, my feelings of anger were subsiding and being replaced with wonder at what she might be about to do next. I stopped a meter from her and she bid me come closer still. Finally I stopped scant inches from her. Her knee was very close to my genitals. My penis was beginning to engorge. Slowly she stood up off the bed, her thigh touching my penis as she moved to her closet. I didn't see what she removed until she again stood in front of me.

It was a black silk scarf. Leaning into me she had wrapped it softly around my head, blindfolding me, while telling me to be still.

The scarf had been a revelation. It had removed me from the embarrassment, in some way isolated me from the situation and allowed me to enter a place where there was only wonder and feeling and total focus on the little touches of my stepmothers body as it touched mine. A brush of thigh against my penis, the touch of breast against an arm. So new was all this to me I was spellbound. I didn't want to move, less I awaken and find it was only a dream.

She had asked that I place my hands on my head and not move them, but to say if it got uncomfortable. She asked me to move my legs well apart. I found I was holding my breath for long periods. The next thing I felt was her hand, almost flutter up my inner right thigh and stop millimeters from my scrotum. Only to flutter like a breeze back down my left. This went on for several minutes, I could only dream in wanton agony of her touching my now swollen tumescent penis. I moaned her name in desire.

I felt her hand stop and sensed her move behind me, heard a drawer being opened and wondered what next. I wasn't scared however; she had asked me to let her know if I was in discomfort so I knew whatever she was up to would no doubt cause me more delicious gentle torment. But it wasn't really torment, it was wonder, at what power a women had, and how responsive I was to her.

Her fingers shimmied up and down my back, from shoulder blades to buttocks, up and down my sides so it almost tickled, from nipples to pubic hair, then back to shoulders. Down to buttocks, a finger gently probing, back to shoulders, back to buttocks, probing deeper. Suddenly her reassuring words to relax, just relax and allow it to happen. Trusting her more now I tried and suddenly the feel of cold and slippery right at the entrance to my anus. I gasped out loud, and suddenly felt a slim pressure pushing against my sphincter.

I tensed momentarily but quickly relaxed involuntarily as I felt her hand creep between my legs to lightly grasp my testicles, and squeeze gently. As I relaxed, I felt my anus penetrated by whatever it was she held. I felt it sliding deeper and deeper until I shuddered as it hit what I now know to be my prostate. Suddenly there was a humming vibration, shocking in its intensity but wondrous in the pleasure it bestowed.

In a few moments I felt my penis surge and jerk as she squeezed some cold gel onto it. Then her hands were ever so gently wrapped around my now pulsating member and she slowly began to stroke me. So slowly, but I knew I'd come in a few seconds. She stopped and began tugging my balls down with her slippery hand, releasing them when they were stretched and starting again, as if milking a cow single handedly. Then back to my penis, even more gently. Her other hand working the thing in my arse in and out.

"Please Marilyn", I cried. "Shhh", was all she replied.

I couldn't believe my desperation, I had to come, I just needed to rub a little harder than she was giving me. I tried jerking my hips into her hand to gain more friction but all that did was make her slow down even more.

It wasn't long before my young body could take no more. I needed to come now! I didn't care how, I just had to come. I dropped my hands to grasp my cock and suddenly the vibrator was off and out of my arse, and the blindfold pulled off. And suddenly here I was back in the present.

"Hold on for just a sec Mike", She said, " I'll just get a tissue to wipe your cock for you."

Somehow I stopped myself from jerking off all over the floor. Thinking that once she had the tissue she would finish me off.

A few seconds later there she was dabbing at my sensitive cock with a paper tissue.

"But I haven't come yet?" I demanded somewhat angrily.

With a smile she looked up at me and said, "Who is training who here?" "Now", She said, "I want you to have a shower right now, and I do not want you to come until I give you permission. I know it'll be difficult but trust me. I'll never take you beyond your limits."

Well that was the beginning of our new relationship. That night as I tossed and turned, unable to sleep due to sexual frustration, I wondered at what I had gotten myself in for and was beginning to touch myself, when my bedroom door opened.

"Hmm," Smiled my stepmother, " I said I wouldn't take you beyond your limits, didn't I?"

"Yes." I grumbled. Embarrassed at being caught in the act.

"Lay back and let me finish our first lesson." She said.

I did, then suddenly the same scarf fluttered over my face, blindfolding me again.

The next hour was a study in frustration, gasping, heaving sweating ecstatic release that will stay with me forever.

End Of Part One. Part 2 to follow in a couple of days..a lot more heavy. If you enjoyed this I'd really appreciate a vote and any feedback you care to give. Thanks.

Next comes

NOW: The Hard Side.

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  • COMMENTS
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10 Comments
AnonymousAnonymousover 2 years ago

This is truly realistic. It invokes surrender in me as a reader to what comes. You see, many a time I feel thrown into some form of judgement or resistance reading stories on this site. Not in this one! Thank you for writing!

Jan, the Netherlands

oliver57oliver57almost 4 years ago
Excellent

You perfectly portray life I wanted at 18!

AnonymousAnonymousabout 9 years ago
Absolutely Awesome

Part one was a great story, I can't wait for the rest! Keep it coming.

AnonymousAnonymousover 13 years ago
DAmn !!

I hope to hell you finish this story !!!!

AnonymousAnonymousover 15 years ago
Waiting.... And You Don't Want to Keep Me Waiting!

Dear SpeedoLight,

I've just read your Stepmother story, chapter 1. In it you promised to write more. Steve, Mike, David, whatever your name is young man, you must write the next chapter as promised. You may not touch your cock or orgasm until the next section is complete, is that clear? I'll be waiting for your response, first as an apology comment here in this space, and second as the submission of your story.

Governess

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