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Office Sissy

"A new office sissy meets a mistress."

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Author's Notes

"This is the second of a series (jennypout stories)."

Now that I was l spending time with Chris, (sissy) and Rachel, (in charge), I was feeling girly as I never had before. It affected the way I looked. I was keeping myself shaved smooth, all over.

I polished my nails (toes and fingers). I was wearing tighter pants and shirts. I usually wore sandals, without socks, my polished toes peeking out. One day I was sitting in my office and an officemate, Sheila, appeared at the door. When I looked up and said hi, she came in and shut the door behind her.

"You look very different these days," she said, smiling.

I hadn't officially come out as yet but it excited me that my new femininity was noticed.

"Yes," I said, deliberately putting a little lisp in my voice, and speaking a little softer. I had always loved Sheila's looks - and her manner. She was always very straightforward and assertive. She was attractive but not at all thin. She was tall, with nice legs, and a big bust. When I had my 'mommy' yearnings, which was often, she was always high up in my thoughts. Now here she was in my office, the door closed, and there I was, in my relatively girly look. 

"So you're gay?" she said.

I nodded, eager to confess, especially to a 'mommy'.

"Are you in a relationship now?" she asked.

I nodded again.

"With a guy?"

Another nod.

"So, tell me all about it," she said, sitting down across from me, settling in.

"What do you want to know?" I asked.

"Well, do you live together?"

"Yes," I said.

"So who's the woman in the relationship?"

"We're both pretty femme," I said, "but I guess of the two of us, it's me," I said.

"So what do the two of you do?" she asked. Then she smiled at me. "The sex, I mean."

I felt a thrill go through me. She was sitting close to me. Her legs were crossed and I could see her bare thighs. I loved this scene, having fantasized about it often enough, having to confess to a woman my submissive sissy desires and actions.

"He fucks me," I said, "whenever he wants. I'm very submissive. I like to do whatever I'm told, whatever he wants."

She sat back a bit and her skirt rode up so I could see more of her.

"What about women?" she said. "Do you like them too? Does he?"

"We both do," I said. "You'd call us 'bi' I guess. But what I like most is if a woman makes me do things."

She smiled again, this time sitting back and uncrossing her legs. Her hand was lazily playing at the top button of her blouse.

"Like what?" she said. "Makes you do what?"

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"Well, I'm really into women's feet," I said. "Whenever I see a woman's bare feet I get very excited. I wish I was kissing her feet, licking and sucking her toes, just being on the ground beneath her, like a pet or a slave."

"Wow," she said, "that's pretty hot." She slipped off her black leather short heeled shoes. "You like this?" she said.

"Yes," I said, in a soft voice.

"Show me," she said.

I sat on the floor in front of her and bent over to kiss the top of her foot, one then the other.

"Stand up," she said.

I did, standing quiet and still in front of her. She reached out and undid my pants, then dropped them and to my feet and I stepped out of them. I was wearing pink panties, my hardening cock evident through the thin silky material.

"Very nice," she said, her hand touching me, one finger tracing the length of my shaft.

I gasped with pleasure. 

"Sit," she said, and I did, at her feet again.

She touched my groin with her toes. I moaned and pressed against her. While one foot was at my groin, she lifted the other to my face, pressing her toes against my lips. This was heaven for me. I pressed and rocked against her with pleasure but I didn't come. Then she stood up. She undid her skirt and took it off. Then she slipped off her panties.

Putting her panties on the chair, she sat back down on them and spread her legs. She motioned me closer. I crawled between her legs. She moved to the edge of the chair and pulled me closer so that my face was at her pussy.

"Lick me," she said.

I began moving, my tongue up and down on her slit, against her clit at the top. Meanwhile, her feet were at my groin and I teased my cock on them.

I could feel her wetness on my tongue and lips. She was moving a little now, and she put her hand behind my head to press me harder into her. Suddenly she held me tight and still there, and I could feel her begin to come. It lasted long enough, with me pressed tight, for me to feel breathless.

I was filled with the smell of her, the taste of her juices, her pussy. When she finished she closed her eyes for a minute, then opened them and looked at me. I was still hard in my panties, not having come.

"What about you?" she said.

She put her foot there again and touched me until I came, in my panties. I was so wet, I wondered if I could wear my pants without the wet spot showing. I dressed anyway. She patted me on the cheek before she left.

"I'll visit you again," she said.

Published 
Written by jennypout
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