*** This is a story of fiction and is written with descriptions of explicit sexual acts between consenting individuals. None of it happened. If you are offended by this sort of thing or under the age of 18 then don't read it. *** Please consider a donation to Nifty.org.
MY SISSY ASSISTANT
A lot of businesses still refer to the employees that do mainly administrative and office work as a secretary but I made sure the job description said the position I posted would offer more than that. I really like them to know they'll be an equal partner and I'll consider their ideas and we'll assist each other. I'd gone through a few and I had an opening again. The work is fulfilling but it is not particularly difficult. You just need to pay attention to all the details. I am the only other employee in the office of my private consulting firm. It is just me and my assistant so we must be able to work closely and get along. I'd interviewed 3 applicants already when the buzzer rang for the next one. I am not sure what I was feeling when Emily breezed through the door. She just seemed very confident and I liked being near her immediately. She had blonde shoulder length hair, gorgeous red lips and wore a lovely dress and I couldn't stop staring at her hosed-covered legs. She wore high heels and her perfume was intoxicating. Her face was so innocent looking. She was very sexy. I invited her to take a seat across from me. We conversed for a while. She was very inexperienced professionally but it was only because she was so young. I had a feeling about her and she came across as the smartest person I'd ever interviewed. She was a natural. She had the cutest accent and my dick hardened and I wasn't sure why. At one point she hesitated and then continued to tell me that she had been born a boy. I was sitting across from a gorgeous confident femboy and I had no choice at this point but to hire her. She was so excited and reached across with her delicate hand and I grasped it. I couldn't stand up as she left or my erection would have been exposed. I told myself that I'd have to control that if I worked with her every day.
The following Monday she came in as I'd given her the entrance code. She was dressed very professionally and smelled glorious again. I spent most of the day orientating her with our processes and showing her where everything was. She picked up things very quickly and she loved laughing and I really enjoyed her easy presence. She and I occasionally touched lightly as people in close quarters do but it was never awkward. We had a natural chemistry and I knew I'd made the right hire. At the end of the day I brought her in and asked her to tell me more about her life. She kicked off her heels and tucked her gorgeous legs underneath her supple bottom on my office couch. I moved to a chair beside her. She already felt comfortable around me, I could tell. She said she'd always thought she was a boy and then recently she felt that she needed to display her femininity to the world. She said it was very organic and now all her thoughts were girly thoughts and she liked pleasing men. I was a little shocked by her openness but I let her continue. She still had her peepee and sometimes caged it up. She was very open with me and I actually loved it. I wanted no secrets. I'd divorced 5 years ago and I'd dated around but it never felt right. Something had been missing. We had such a lovely natural talk that I looked up and evening had fallen. She extended her legs and feet out in a stretch and her foot grazed my leg and I felt suddenly a little flushed. I told her to go on home and I'd see her bright and early at 7:30. After she left I could still feel her presence and I took out my dick and pounded it with her gorgeous face in my mind. It was intense as I orgasmed and softly called out her name. Emily!!!
When I arrived in the office the following morning I was greeted by a gorgeously smiling femboy with a cup of hot steaming coffee and sweet smile. She had taken notice of how I liked it and prepared it perfectly. She was blowing my mind and I would find it hard to concentrate when she was out at her desk and I was in my office. I made up silly things for us to meet about just so I didn't go too long without being near her. I'd go out and do something menial often just so I could see her. She was always diligently on-task and was great at the work. If she wasn't doing our work I found her studying for a test. She was studying business at a local college online. When we talked closely she often brushed my arm with a delicate touch. This tension went on for weeks. One Friday afternoon she came into the office unannounced and ask me to come sit by her on the couch. I was surprised but I never said no to this gorgeous sissy. I sat down next to her. She stood up and surprised me by sitting in my lap. She kicked off her heels and she said, "Daddy we need to get this out of the way so we can keep working together. We obviously have sexual chemistry." Then she kissed me with the most erotic kiss I'd ever shared with anyone. I was in shock but I went with it. Our tongues were intertwined. I leaned into her and our hands started exploring all over each other. I reached down and grazed my fingers up her hosed thigh and found her hardened boi clit. I rubbed it and she moaned in my ear with her hot breath and exploded in her hose. She reached in and scooped some onto her finger and sucked it into her mouth. We had a delicious cummy kiss and then she stood up and unzipped her dress and let it puddle on the floor. I was mesmerized by her smooth girly chest and soft skin. I was under her spell and she plopped down on her knees and asked, "Do you want me daddy?" I begged, "Yes baby. Please!! You are my adorable little sissy slut!" She freed my cock from my pants and gave it sweet little kisses. My dick was engorged and she slid her red hot lips over the head and started working my sensitive areas with her tongue and lips. She was very talented. She definitely knew all my spots! She took it deeper and gagged a little but kept working. She begged, "Give it to me daddy! Please!" I complied and eventually shot a huge load to the back of her throat. She opened mouth it to show me and said, "My cum and your cum in my mouth on the same day is just what I wanted daddy!" I was smitten. I think I knew what had been missing in my dating life. I needed a sissy!
She was an amazing assistant and we kept getting more projects for our firm. She was an even better lover but she wanted me to take her someday soon and make her all mine. I thought we could kill 2 birds and I invited her for a working weekend at my beach house. We flew in a private jet to the coast. The blowjob she gave me on the plane was one her best yet. We arrived and immediately got into our swimsuits. It was a private beach so I told her she could go naked if she wanted. The tiny suit she wore covered almost nothing anyway and came off quickly. We ran up and down and had a wonderful time in the surf. We returned home and she showered and I had lobster catered in for a small feast. She arrived to dinner and my jaw dropped. My gorgeous sissy was wearing a hugging little black dress with nude hose and some Fuck Me pumps! I was hard as we devoured our food while staring into her eyes. I just wanted to devour this delicious femboy! We settled in for a long make out session in the living area and then she stood up dropped her dress and beckoned me to the bedroom. I entered as she splayed out on the bed in only her pantyhose with no panties. Her legs were spread and she called me over with her finger. I got on top of her and started kissing her lips and neck. Our cocks rubbed together in sheer ecstasy. My mouth made its way across her sissy chest and ended up on her gorgeous toes. She looked up and said, "Daddy is this how you imagined me the first minute we met?" I quickly nodded and said, "Yes sweet girl." I jumped back on her. I breathed in her femininity and ripped a hole in her hose. I was naked immediately, I laid her legs on my shoulders and I pushed my cock toward its rightful home. I worked it in after we applied some lube and it quickly allowed entrance. It was very accepting of its new master and I pumped it in her more. She moaned, "Yes daddy! Take me! I'm your little sissy whore!" I drove my cock home and pounded that sweet tight sissy pussy. I was careful but still aggressive. Eventually my cock had had enough and our bodies convulsed together as I released a huge load into her gorgeous sissy pussy! She moaned and we stayed locked in our embrace whispering nasty sweet nothings to each other for hours. We got very little work done that weekend but we found each other.
Emily is the sweetest sissy assistant a man could ever hope to have. She is so smart and makes few mistakes. She is beautiful inside and out. I make love to her every day. Sometimes at the office bent over my desk and sometimes at the home we now share. I love to watch her get ready every morning as she sweetly applies her perfume or pulls pantyhose sensuously up her gorgeous legs. We love to shower together where I soap up her sweet little honey hole. Some days we never even get out of bed. I reach down into her pantyhose and make her moan as I kiss her wet femmy red lips! I work from home and she works my cock!! She really pays attention to the details! Sissy assistants are the best!!
Big thanks to my muse and motivation to write this story Emily!