1/6 Submissive Sissy Stories – BRING YOUR SISSY TO WORK DAY.

*Note: This is a continuation of the characters from my previous stories, Daddy Party and Play Date. I think it works as a stand alone story but if you like it be sure to check those out too.*

Amy and I stood obediently in the foyer of the Cooper’s well appointed brownstone. An hour earlier she and I had been sleeping soundly in her bed, cuddled together in our sheer baby doll nighties when Mrs Cooper had come in and told us it was time to get up. The previous evening had been my first sleep over at Amy’s house and Mr and Mrs Cooper (or Daddy and Mommy as they preferred to be called) had made me feel so very welcome in their home.

“It’s time to get up, gurls.” She sang as she bustled around Amy’s bedroom. She moved from the closet to the dresser, selecting clothes and laying out the day’s outfits. “It’s a beautiful day out today, ” she said as she opened the pink curtains, filling the room with bright morning light. “And today’s an important day… It’s Bring Your Sissy to Work Day!”

We slipped out from under the covers and sat on the edge of the bed as Mommy gestured to the two neatly laid piles of clothes she’d placed on the dresser. “Here are your outfits, now I need you both done up and ready to go by nine. Ok?”

“Yes Mommy.” we giggled in unison, rubbing the sleep from our eyes. Amy and I made our way to the bathroom and helped each other with our makeup and touched up our nail polish before selecting our wigs. I picked a short blond bob and Amy picked out a long auburn one, putting it up in a high ponytail.

Now we stood by the front door, examining ourselves in the large mirror. We were both wearing black glossy Mary janes, black knee high tights, grey pleated skirts with matching grey cardigan sweaters over white button up blouses.

We looked so cute! Like two private school girls as we touched up our lip gloss and smoothed our skirts over our exposed thighs. I picked out a white headband too, I liked that it matched my white lacy bra and tiny white g-string panties.

Daddy made his way downstairs first, smiling and holding a black coffee mug. He was dressed smartly in a dark suit and tie, ready for his day at the office.

“Good morning, gurls. You both look lovely today.”

“Thank you Daddy.” We both chimed as he kissed us each on the forehead. He slipped on his leather dress shoes and grabbed his keys from the small table.

“Amy, you’ll be coming into the office with me today and Jenny will be accompanying Mrs Cooper, sound good?”

“Yes Daddy.” We said again, giggling as we beamed up at him. He opened the door and gestured to Amy.

“We don’t want to be late. Have a good day, Jenny!” He said as he took Amy’s hand and led her outside, closing the door behind them.

A few moments later Mrs Cooper descended the stairs from the second floor. She was wearing a dark pantsuit with a powder blue top underneath, her signature cat’s eye glasses, black two inch heels and nails painted a deep maroon to match her short hair.

“Oh sweetie, you look wonderful.” She said to me as she brushed my bangs aside and planted a soft kiss on my glossy pink lips. “All set?”

I nodded and we headed out into the crisp morning air.

I sat in the passenger seat of her Mercedes sedan as we sped down the highway into the city. I wondered where we were going and what the day had in store for me.

I knew not to ask and to trust that Mommy would take good care of me but I could feel the nervous anticipation in my stomach and my shaved cock began to swell in my tight panties. It was exciting to be dressed in my sexy girly clothes out in public like this and I hoped I’d make Mrs Cooper proud, wherever we were headed.

She deftly weaved the car through the busy downtown, finally pulling into the lower parking garage of one of the city’s luxury hotels. She parked, grabbed her black leather briefcase and we got out.

Mrs Cooper took me by the hand and led me to the elevator, my heart was racing as I felt the gentle breeze blow under my short skirt as the elevator doors opened. We stepped inside and she pushed the button for the top floor.

“Now…” She said, “We’re going to meet up with some of Mommy’s work clients. Well, potential clients. I need to talk with them about some business things and then, if you’re a good gurl, Mommy will take you shopping after. How does that sound?”

“That sounds great!” I said, before I paused and added, “But what do you need me to do?”

She smiled and squeezed my hand in hers as she looked up at me. “You’ll know what to do, just follow your best judgement. You just be a good gurl.” She leaned in and kissed me again, deeper this time, pressing her body against mine, her hand resting on the bulge under my skirt. “And my sweet Jenny is always such a good gurl…”

I could feel myself blushing as she knocked on the door to the suite. “Relax,” Mrs Cooper said, “It’s just a business meeting, you don’t have to do anything you don’t feel comfortable with.”

I smiled at her. I didn’t feel uncomfortable, I felt sexy in my cute outfit and I wanted to make her proud. I’d only known her for about a week but she’d been so integral to helping me embrace my sissy side and I didn’t want to let her down.

The door opened and a tall man in dress slacks, a white dress shirt and tie greeted us, smiling as he showed us inside. He was probably in his late forties, clean shaven with dark hair graying at his temples. “Michelle! So good to see you again, hope you found the place ok, ha ha ha.” The man kissed Mommy on the cheek and turned to me. “And who is this?”

“This is Jenny, she’s my assistant for the day. Say hello to Michael, Jenny.”

“Hi.” I demurred politely as he took my hand and kissed it. I giggled and curtsied slightly as the door closed behind us.

“Well hello Ms Jenny.” Michael said, holding my gaze as he smiled warmly. “Come on in, have a seat. Brian? We have guests!”

We made our way into the small living room area of the massive suite where I sat beside Mommy on the large plush sofa.

Brian, a younger man with dark skin and a shaved head who also wore a white shirt and tie sat at the desk typing on his laptop. He looked up and smiled.

“Hello. Hi Michelle… thanks for coming by.”

Mrs Cooper opened her briefcase and removed a stack of papers. She set about organizing them on the coffee table as Michael sat in the armchair across from us.

“Now I take it you had a chance to look over the contracts…” Mommy said and Michael nodded.

“Yes and everything looks good. I ran it by everyone in New York and they feel good about it.”

“Great! That’s good to hear. So I guess all we have left is to get these signed and we’ll be out of your hair.” Mommy removed a fountain pen from her blazer pocket and uncapped it, setting it down on the stack of papers.

“Yes…” Michael said, “Although there were a few concerns…”

Mommy stared at him, “You mean regarding the contract terms?”

“No…” Michael laughed, sitting back in the chair, “Nothing like that. The contracts look great. It was more of a concern regarding your company’s commitments to… client satisfaction.”

Mommy smiled slyly and placed her hand on my knee. “Oh…? And what are your concerns?”

Now Michael laughed. “Ha ha ha, it’s just that… we’re a small outfit and if we get into bed with you, metaphorically, we need to be assured that we’re getting the best client relationship we can. Y’know?”

Mommy laughed and squeezed my knee. “I think I know what you mean. And I want to assure you that our client’s overall happiness is priority number one for everyone in my firm. Jenny? Why don’t you go sit on Michael’s lap.”

I felt my cheeks flush bright pink and my stomach fluttered. I looked into her eyes and she nodded. “Go on.”

I stood and walked over to Michael as he spread his legs and patted his thigh. I smiled at him and sat down, smoothing my skirt as he placed his hand on my lower back.

Mommy continued, “As you can see on the attached packet, we have countless testimonials from our other clients and you’re more than welcome to follow up with any of them, I’m confident they’ll all sing our praises.”

Michael was staring up at me as I sat up straight with my hands resting on my knees. His one hand caressing my back while his other rested on my exposed thigh just below the hem of my short skirt.

“Oh I don’t doubt that.” He said to Mommy, his hand massaging my smooth thigh, “It’s just that we have several offers and I just want to make sure we’re signing with a company that’s prepared to do everything that we need. Is that you and your team?”

“I think you’ll find that is is,” Mommy said as she adjusted her glasses. “Jenny? Why don’t you show Michael just how committed we are to his overall satisfaction.”

“Yes Mommy.” I said. My heart was pounding as I turned to him. I could feel my cock straining against my tight panties. All of a sudden I understood why she’d brought me along today and I knew exactly how I could make her proud.

Michael placed his index finger against my soft glossy lips and I kissed it gently. Then gave it a little lick. He smiled and I began to suck it softly between my lips.

The three of us sat silently as he gently pushed two fingers into my mouth. I held his gaze and began to suck, swirling my tongue over his fingertips as Mommy looked on.

Brian looked up from his computer to watch and I was suddenly aware of Michael’s thick cock hardening in his pants under my leg. I sucked obediently on his digits as he fingered my wet mouth.

I was so turned on, I loved feeling their eyes on me like this as I gazed adoringly at Michael and he fed me his fingers. I felt so sexy in my girly uniform and I could tell by the look in his eyes that he liked it too.

He pulled his hand back and tilted his head up towards me as I leaned in and kissed him on the lips. Softly at first but then deeper, our tongues sliding together as I shifted my hips, pressing my smooth ass against his bulge. His hand returned to my thigh and slowly slid up under my skirt. I whimpered softly as his fingers began to trace my thick panty bulge.

Brian stood up and made his way over to us. I felt his hand on the back of my head as Michael and I made out. I turned to look up at him and he leaned down, kissing me as Michael’s hand massaged me under my skirt. Brian held my chin in his hand and smiled down at me.

I could tell the men liked me and my heart pounded as I watched him unbuckle his belt and unfasten his trousers. With one swift movement he slipped his thick black cock out over his boxer briefs, letting it hang fully erect just inches from my face. I nearly gasped at the size of it! Easily the biggest I’d see since my short time as “Jenny”, at least nine inches and so smooth and thick.

He caressed the back of my neck and nodded as I leaned in, instinctively closing my pink lips around his thick pronounced head. His cock easily filled my entire mouth and I whimpered softly as he moaned. I started massaging the underside with my tongue as I gently pumped my lips up and down his thick shaft.

“Mmmm, you were hungry weren’t you, sweetie?” Michael asked as he flipped my skirt up, exposing my smooth thighs and the bulge in my tight little panties as his hand stroked my cock through my white g-string.

“Mmmm hmmmm….” I said, rocking my hips back and forth over his heavy erection as Brian fed me his beautiful hard dick.

Mommy sat back and twisted the top off of one of the bottles of water on the table. She took a long sip as she watched me and I knew I was going to make her so proud today.

“Oh yessss…” Brian hissed, “Good gurl…”

“Look how hard she is!” Michael exclaimed as he pulled my panties aside and began stroking my hard hairless cock.

Brian pumped his hips gently, driving his big dick deep into my mouth. He was so big and I wasn’t sure I’d be able to take the whole thing but I knew I’d do my best. He moaned again as I caressed his heavy balls and pushed his cock deeper into my throat.

Michael slipped out from under me and guided me to kneel on the chair with my elbows resting on the back. As Brian fed me, Michael stood and slipped out of his pants and shirt, revealing his toned muscular body. He slid down his blue bikini briefs and began stroking his thick cock. He was so big too! Not as big as Brian but still…

He stood beside Brian and presented his massive erection to me. I took Brian in my hand and stroked him as I sunk my lips over Michael’s big dick. It felt so good as it slid between my lips. I began swapping my wet hungry mouth back and forth between them, taking one cock all the way down, then the other, slurping and sucking, coating their juicy erections with my saliva as Brian removed his shirt and tie.

I felt so lucky, so spoiled to have these two giant dicks to suck, pumping my wet mouth and tongue over both of them like a greedy slut.

They were both so fit and muscular, their wonderful cocks filling my mouth and causing me to whimper. Brian was shaved smooth all over while Michael had very light body hair, his pubes trimmed very neat and short where they tickled my nose when I took him all the way to the base.

They held my head in place and I gasped as they both stuffed their cocks into my mouth at the same time. My lips stretched to accommodate them, drooling down my chin as their hard slippery cocks slid together and pumped in and out of my lips.

I felt so good, so slutty taking the two of them like this. Holding each of them in my hands and sliding their wet thick heads together, dragging my tongue along the length of their cocks, whimpering like a good gurl as the men fucked my mouth like a tight pussy.

It occurred to me that I hadn’t spoken to my girlfriend in a few days. I’d been so lost in the experience of my sissification that I’d forgotten to call her all week.

I wondered what she was up to at that moment, as I, her loyal boyfriend was dressed as a gurl and servicing the two biggest cocks I’d ever seen. I wondered what she’d think.

Michael reached down and flipped my skirt up over my ass. HIs fingers traced the back strap of my g-string down between my smooth cheeks and resumed massaging my panty bulge as it hung heavy between my thighs.

He tugged at my sweater and I unbuttoned it, pulling my sweater and blouse off over my head as Brian unfastened my mini skirt. The men pulled me to my feet, sandwiching me between their firm bodies, their hands caressing me all over as I moaned and they kissed my face and neck.

I was so exposed, wearing only my little bra, panties, thigh highs and shiny shoes as the men fondled me, pressing their hard thick cocks against my smooth body.

“Mmmm, such a sexy gurl…” Brian whispered in my ear as he squeezed my hard nipples and ground his cock against my ass. Michael kissed my neck as he stroked his massive cock against my panty bulge. I looked over to see Mommy sitting back on the couch.

Her suit pants were unfastened and her right hand was inside her panties as she stared into my eyes, nodding her approval. Michael noticed her too.

“Wanna join us?” He asked her and she laughed.

“Oh, let’s try to keep our relationship professional, Michael. Besides, I’m a married woman. But Jenny is more than capable of giving you whatever you need. You boys have fun.”

“Suit yourself…” Michael said as his attention returned to me and he led me over to the king sized bed. Brian followed and guided me to sit on the edge of the mattress, parting my thighs and dropping down to his knees. He started kissing my smooth thighs, higher and higher until I felt his lips on the hard bulge in my panties.

I opened my lips to gasp but Michael slipped his cock into my mouth and I moaned as I started sucking his thick smooth cock. Brian pulled my panties aside and took me in his mouth, sucking softly, savoring my hard hairless panty cock. It felt incredible.

I felt so comfortable as “Jenny” now that I’d had so much practice and was finally able to let go and embrace my sissy desires. Sucking Michael as Brian expertly massaged my big gurl dick with his soft lips and tongue, I was whimpering and looking up at Michael, finally feeling not like I was dressed AS Jenny, but that I WAS Jenny. Jenny the femboy. Jenny the sissy. Jenny the cock slut.

Across the room I could see Mommy rubbing herself and breathing heavily as she watched the two men have their way with me. Brian pulled me up onto the bed and positioned me on all fours as Michael stood, feeding me his cock. I arched my back as I felt Brian get behind me, planting soft kisses on my ass. He slid the back strap of my little g-string to the side and I shuddered as he dragged his hot wet tongue over my tight boipussy.

His hand cupped my smooth throbbing cock, stroking me as he ate me out. Waves of pleasure rushed through me as I pressed back into his face and took Michael deep into my throat. I gagged slightly as he held my head in place. “That’s it… good gurl… suck that big cock…”

he moaned as tears ran down my cheeks. It felt so good! I relaxed my jaw and slid my tongue out as he gently pushed deeper, all the way to the base. He pulled out slightly then slid back in, slowly fucking my hungry mouth as Brian’s hypnotic licking caused my eyes to roll back in my head.

Brian got to his knees and positioned himself behind me, dragging his thick erection between my cheeks, my boipussy slick with his saliva.

“I wanna feel how tight your sweet pussy is on my big cock…” He said as he pressed his thick head into me. I tried to yelp but my voice was muffled by Michael’s dick. All that escaped my mouth was a gurgled moan as his giant cock slipped inside of me causing my whole body to tremble with pleasure. It was so big!

It felt amazing, hitting all the right spots as he gently sawed in and out. I was completely at their mercy, kneeling as the two men fucked me from both ends.

Brian gripped my smooth skinny hips as he built to a hot rhythm, fucking me steadily, pumping me full of his beautiful black cock. Micheal’s thick fleshy erection muffled my moans of joy as I drooled down my chin, both men fucking to the same rhythm, reducing me to their personal sissy fuck doll.

They continued like this for a while, thrusting, grunting and moaning as I took every last inch of their big cocks. I loved the sensation of total submission, servicing both of them with my tight slender body, my hard panty cock bouncing with each thrust and dripping precum all over the comforter.

Michael pulled back and I felt Brian slow down. Something exchanged between them and they moved to swap places, Michael’s cock slid effortlessly into my eager boipussy as Brian caressed my cheek and offered me his glistening dick. I took him in my mouth without hesitation, my eyes watering as his long hard cock pressed against the back of my throat.

They resumed fucking me and I was overjoyed. I couldn’t see Mommy anymore but I hoped I was putting on a good show for her, I hoped I was doing a good job and impressing her business clients but judging but their moans I was sure I was doing a more than adequate job. They flipped me over onto my back and I held my knees to my chest as they continued pumping me full of their big cocks.

The feeling was indescribable, submitting like this, allowing myself to be used my the fit hung men it was incredible. This angle felt amazing, Michael’s dick was sliding deeper than before and I could feel myself shaking involuntarily. I knew I was about to cum but I didn’t want to stop, it all felt too good.

Brian squeezed my hard nipples through my thin white bra and my thighs started to tremble as my heavy smooth balls tightened and my cock began to pulse. Brian pulled out of my mouth and erupted all over my face, his thick hot cum coating my lips and cheeks as he shot rope after rope of white salty cum all over my pretty face.

It sent me over the edge and wailed loudly as I came hard, my smooth hard cock throbbing as I shot my sweet gurl cum all over my stomach and chest. My head was spinning, dizzy from the incredibly strong orgasm as Brian leaned down, kissing me as he licked his cum from my lips.

Michael increased his tempo, holding my ankles as he jackhammered away on me, his big dick pumping in and out. He pulled out suddenly and came, his hot cum splattering all over my hard throbbing cock as I whimpered, gasping for air and looked up at the two men gratefully, obediently, like a good, well fucked gurl.

The men laughed and shared a satisfied look between themselves before complimenting me on a job well done.

“That was wonderful, baby…” Brian said as he kissed my cum soaked lips.

“What a good gurl… thank you sweetie…” Michael said as he kissed me, savoring the taste of Brian’s sweet cum.

Across the room I heard Mommy let out a whimper and sigh loudly. I knew what that meant, my performance had been to her liking and she’d cum while watching me. I stood and sauntered over to the couch where I kneeled on the couch cushion beside her.

I gazed into her eyes as she offered me her glistening fingers and I proceeded to take them in my mouth, licking and sucking her sweet pussy juice from her manicured fingers.

“Was that good, Mommy?” I asked hopefully and she flashed me a warm, loving smile.

“Yes, baby… you did so good…” She said as she patted my cheek and kissed me softly. “Now why don’t you go clean yourself up and get dressed, we have some paper work to finish up here.”

I hopped up and gathered my clothes before making my way to the bathroom. I used a towel to wipe up all the cum from my body and face before touching up my make up and slipping back into my clothes.

Exiting the bathroom I watched as Mommy stood and placed the signed contract into her briefcase before shaking hands with the two sweaty, naked men.

“Looks like we’re all set Michael. I want to thank you for your trust and look forward to working with your company.”

Michael laughed, “Ha ha, oh the pleasure was all ours. Thanks for including that signing bonus… She’s wonderful.”

I stood beside Mommy and she led me to the door.

“It was so nice to meet you Jenny!” Brian said and I giggled, curtsying again and smiling at the two men before Mommy and I headed out into the hallway to wait for the elevator.

We rode down to the parking garage in silence, Mommy gripping my soft hand in hers. We got to the car and she opened the back door and turned to me, pulling me to her body and kissing me hard.

“You did so good today, sweetie. You made Mommy so proud.” I beamed at her, smiling and feeling so good that I’d helped her with her business deal.

“Thank you Mommy.”

“Mmmm, now Mommy need one more thing from you, ok?”

“Yes Mommy. Anything.”

She climbed into the backseat, wriggling out of her dress pants and spreading her legs wide before motioning for me to come to her.

I crawled in and she gripped my hair, pulling my face down between her legs. I pressed my lips against her lacy black panties and started kissing her, dragging my tongue along her panty wrapped slit. She pulled that to the side and I closed my lips over her juicy bald pussy, my mouth immediately filled with the taste of her sweet juice as I tongued her slit.

She moaned pulling me closer and thrusting against my face. My lips found her stiff little clit and I sucked down, swirling my tongue as she held my head.

“Yessss…. Mommy’s sweet little sissy gurl…” She moaned, “You made me soo wet taking those big cocks… such a good gurl…. Now eat Mommy’s pretty pussy…”

Pride swelled through me as I ate her, I was so happy that she was pleased with me, so glad to know I’d turned her on. I sucked and licked her until her thighs began shaking and she let out a high pitched moan, shuddering as her body shook and she came hard against my face.

I carefully licked up her juice from her soft fleshy lips as she caught her breath. She pulled me up to face her and she kissed me again, softly, sharing the taste of her sweet little pussy.

“You did so well today. I couldn’t have closed this deal with out you.”

“Of course, Mommy… I’d do anything for you.”

She smiled and slid her pants back on. “Now what do you say we go get lunch?”

We hopped in the front seat and pulled out of the garage. We spent the rest of the day together. After lunch at a fancy cafe, she took me to Victoria’s Secret and bought me some sexy new things to wear and then to the adult toy store where she bought me a few things she said we’d try out later.

As we drove back to her house I thought about Amy and wondered if she had as good a day as I did. I couldn’t wait to tell her all about the fun I’d had.

“I assume you’ll be sleeping over again tonight?” She asked and I nodded. “Good. I’m sure Daddy and Amy will want to hear all about your big day.”

My heart raced as I pictured it. As Mommy drove she kept her hand on my smooth thigh and it made me feel so safe and content, like a good gurl.

THE END.