Working Late with Maggie

Working Late with Maggie

Posted on November 14, 2015

Hello, I want to tell a story, about my first love with a shemale who just happened to be my boss. I worked at a bed, bath, and beyond store. I had worked there for about 1 year and a half, and my boss really liked me. I always went and picked up her lunch with mine, never messed up. Her name was Margaret, but I always called her Maggie.

In fact, I was the only worker that was allowed to call her that. I thought she was beautiful, she had slender legs. Her breasts and rear were curved perfectly. However, it wasn't just her body I loved. She had the face of an angel. She always had a bright smile, that was accompanied by her passionate blue eyes. She had short brown hair with blonde highlights. We would always talk about our favorite sit-coms and so forth. 

However on this night, she had wrote down for me to do the late shift. Which was strange, for she never asked me to do so. I had nothing to do, so I figured what the hell. When 2 am came, almost everyone was leaving. Everyone except myself and Maggie. Then she called me over to her office. I was a bit nervous, as people usually went to her office, when they were in trouble.

Upon entry, I saw she had a serious look on her face. She spoke to me softly, but stern. "Be a dear, and please lock that door." she said. That made me even more nervous. I did as she said, and she sat down, and crossed those beautiful bronze legs of hers. "You've been staring at me...and not in a professional manner." she said. I gasped and tried to shake my head. "Such a good worker, but you can't stare at me like that at work. It's not professional, and you know better than that." she said.

I put my head down in shame, for I knew she was right. I had to be a man and accept whatever punishment I would get. Which would probably be a loss in hours or something. But what she said next blew my mind. She stared back at me and smiled. "If you want some private time with me, my office is right here. But first, there is something you should know. I'm not exactly what you think I am." she added and stood. She then lifted her skirt a bit, and I saw her erection forming through her silk underwear.

Most guys would have left, maybe even quit. But seeing her hidden cock throb, and looking at her face which was turning red from the fact that I was looking at her in such a way, I found hot. 

She looked at me "Are you okay with me like this?" she asked. All I could do is nod. "Maggie, you will always be Maggie to me. No matter what's between your legs, you're the best boss I've ever had and I will always stare at you that way." I said with a smile.

She then grinned. "That's great, but talk is cheap. If I remember correctly, your resume said that you were open to new things, and were always willing to do any type of job. Well...suck me...give me a blowjob..." she said and grinned.

I couldn't believe it, my mind was going all over the place. How did it get to this. Staring at your boss, usually got you fired, or even a warning of sexual harassment. But Maggie was asking me to suck her off in work. Was this a trick? To see how far I was willing to go. But my lust for my boss was so high, I didn't even care anymore.

I slowly walked to her and took a deep breath. "Yes Maggie..." I said and dropped to my knees, I pulled down her underwear and felt her cock playfully smack me in the face. It was already dripping precum. I stroked it softly, and instantly heard Maggie let out a deep sigh. She seemed to be very sensitive. 

In my life I always went down on girls, in fact I had a reputation for it. But I had never sucked a cock before. I had to just go from what I remember girls did to me. I stroked it, and licked the tip of Maggie's cock. I heard her bite her bottom lip and mutter the words "Oh fuck...". The taste wasn't that bad, I actually liked it. But knowing the pleasure I was giving my boss, made me like it even more.

I began to bob my head back and forth, slurping it as I took it deeper. I then felt her hand caress my head, and felt her thrust in my mouth. My sucking sonds grew louder, and her thrusts were rougher almost primal. As I looked up at her innocently, she would moan and look down at me. " always were my favorite worker...suck it...suck me...mmmm such a good boy...oh I love your tongue...shit...I'll cum soon if you keep this up..." she moaned.

I was scared, but curious to what cum tasted like. So I began to bob my head faster, letting my tongue trace circles around the cock that was swimming in my mouth. I could taste the precum leaking more and more in my mouth. But her face told me all I needed to know. Then I saw her lean her head back and let out a high pitched moan. "There...I'm cumming...shit...your mouth is making me cum...ahhh...fuck..." she moaned, and the taste of her cock was over taken by these thick and hot strands of liquid that marked my tongue. I was expecting a nasty taste, but I could taste bits of strawberry. As I swallowed it felt like her cock was releasing hot spurts of strawberry yogurt. I swallowed it all, and even cleaned Maggie's cock for her.

I then stood and smiled, and laughed with her. She hugged me and wiped some remaining off the side of my lips. " looks like I gave you quite a mouthful...are you okay?" she said in a caring voice, as she laughed with me. 

"Yeah...I'm a big boy, I can handle it." I replied.

She then smiled "I've got an idea...we've come this far, no one is working but you and me. Let's go to the bed department downstairs. I want to make it up to you. Do you want to fuck me?" she said. 

All I could do was nod.

She grinned and took my hand. "That's the answer I was looking for." she added and led me to the bed department. Upon arrival, she rested on the bed, and spread her legs. I felt like I was dreaming. I actually was getting the chance to fuck my boss on the bed at work. My heart was racing.

" know how I don't like to be kept waiting..." she said and I nodded quickly removing my jeans and boxers. I then climbed on top of her and was under the covers. I rubbed my cock up against her tight hole and saw her whole body shiver in pleasure. Then my cock slipped inside of her. My eyes rolled to the back of my head as I felt nothing but her warmth and her rear clenching tightly on my cock. "Oh're so tight..." I moaned as I rocked my hips back and forth slowly. Feeling the pleasuring sensations of those hot, long, and wet strokes. 

"'re so big...right there..."she said looking up at me. I placed my hand on her cock. It was still wet from the blowjob I previously gave her. I stroked and thrust over and over. Until I felt her ass open up for me. Our skin began to clap loudly as I increased the pace. It was so warm being inside Maggie, that beads of sweat appeared on my forehead. She pulled me down and kissed me deeply. Her hands were cupping my cheeks, it was so romantic. I then would release the kiss and look down at her. She was panting heavily from my deep penetration. I leaned up, and let her legs, rest on my shoulder. I would then suck on her toes, as I would thrust harder and deeper than ever before. This sent Maggie over the edge.

"Jesus...oh fuck...faster...mmm...suck my you did my cock baby...use that tongue more." she moaned. I did as I was told and fell back on top of her. "OH Maggie...I'm gonna cum..." I declared and tried to pull out. But her legs moved from my shoulders to my waist. Wrapping around me tightly, so I couldn't escape. I released my seed deep in her. She screamed, and as I looked down I saw her own cock erupt like a volcano. It was as if my cum shot right through her rear and through her cock. I then licked her cum from her stomach and sucked her cock clean.

"Mmmm...that is so fucking sexy..." she said and we rested in the bed together. 

"Tomorrow, come to me at the same time if you're up for a new experience. Because I want a piece of my favorite employee's ass." she said with a grin.

I smiled. "Well, I'm always up for a new experience."

Story by: mightymax1234