An Office for Growth (SweetAnnie40 + sissykaitlin)

sissykaitlin

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Kelley sighed. It was a late night at the office, again. Standing and stretching he took the plans that he had been examining off of the drafting board and folded them up to put them in his cubby, for tomorrow. It had been a long day and he was ready to go home. But, tonight, he had some plans with friends to visit the local pub. Kelley was slim with medium length curly hair and wore a pair of skinny jeans that hugged his figure. At 29 he was used to working long hours and still having to find time to be social. But tonight was different, his boss was still in the office--he could see her light shining above the space that he occupied.

Walking up the stairs to her office he knocked and poked his head in. "I'm going to head out, Boss. I hope you have a good evening!"

Kelley smiled and waved before heading back down the stairs and slipping into his coat. Kelley had always been shy and reserved and it had remained true in the professional realm where he kept to himself and did the best work that he could. Kelley like it this way--he was able to keep his private life private while still being able to be as friendly as he wanted in the office and with his friends.

Kelley stopped in the restroom just before leaving and walked up to the urinal where he unzipped his fly and reached down slipping the black thong that he wore to the side so that he could pee. Kelley had been dressing privately for years but had never shared it with anyone. Rezipping his fly he flushed the toilet and threw his bag over his shoulder before heading to the pub that was about a half mile walk from the office.
 
Kelley was actually early to meet his friends so he grabbed a drink and a table. He was surprised to see his boss come into the pub not long after him. She caught his eye, gave him a smile warmer than she'd ever done at the office, and brought a glass of wine over for herself.

"May I join you for a minute?"

Kelley nodded. His boss, Angelique, was a statuesque woman much taller than him in her 4" high heels. She always dressed impeccably, suitable for business but definitely feminine, preferring skirts and dresses, satins and silks. Her raven hair was straight and long enough to tease her shoulder blades on her back.

She sat closer to him than she needed to and he smelled her intoxicating perfume over the general odor uproar of the pub.

"I was hoping we could chat for a few minutes. There's been something that I wanted to discuss with you but the office isn't the right place for it."

She took a drink of her wine, gathering her thoughts.

"You know women can tell you're wearing panties in the tight pants you wear, right?"
 
Kelley looked up from his drink and nodded. "Of course you can join me, Ms. Angelique." Kelley stood up quickly and ran around the table to pull out the chair for her. Blushing Kelley returned to his seat and took a sip of his beer before nearly choking on it. To prevent from spitting it everywhere he had a strong bout of coughing.

"What do you mean, Angelique?" Catching his breath Kelley's hand grabbed the table in front of him. "How could anyone tell anything that I'm wearing??" Shifting in his seat uncomfortably Kelley crossed his legs and make certain to pull down the back of his shirt. He had never been caught before, not even by his roommates and had gotten so used to dressing discreetly that he had assumed that he was being safe.

Kelley watched as she took a sip of her wine and wondered if he should just stand up and give an excuse for why he had to leave. Yet, he found himself stuck in plan unable to or unwilling to completely give himself up. Kelley's eyes scanned the pub as he watched for his friends to arrive but knowing them he entirely expected everyone to be late. Lifting his glass off the table, again, Kelley took another sip before waving the waitress down to bring him another. His eyes raised from the table and he made eye contact with Angelique--he could smell her perfume and was almost overwhelmed by how it clung to the air that surrounded her. It seemed, to him at least, to fit her presence in that it was strong and certainly confident.
 
"Oh men don't get it but we women see it pretty easily. Pantylines mostly but sometimes your shirt gets untucked in back and we can see your pink lace panty waistband or even more if you're digging around in the office supplies room."

She put her hand on his, feeling how he was trembling.

"But don't be afraid, honey. I won't tell anyone. It'll be a secret between us girls. But I'd love to know more..."
 
Kelley blushed at how forward she was being and how naive he had been to think that he was doing a good job of concealing his secret. "I...." Kelley took a sip of the drink in front of him. "I didn't know that anyone had caught me. I'm a little embarrassed, now!"

Kelley nearly jumped when she put her hand on top of his but looked up nervously and smiled.

"What else would you like to know, Ms? I've... I've always dressed, I guess. I had thought that I was being discreet but maybe I wasn't doing so well." Kelley took another pull of his drink and looked up making eyes Angelique. "Do you know when the others were supposed to be joining us?"
 
"I was thinking you might want to give your friends a rain check and we can go somewhere quiet to talk. i have so many questions..."
 
Kelley nodded. "Sure, Ms." Pulling his phone out Kelley quickly texted his friends letting him know that he was having to back out on their plans. "Where would you like to go?"

Kelley took another swig of his drink and placed back on the table, empty. Feeling a little emboldened by the alcohol Kelley stood up and walked behind Angelique's chair--pulling it out so that she could stand. "I'll follow you, Angelique."
 
She smiles and leads Kelley out of the restaurant. Walking behind her resonated strongly with Kelley... a dominant woman in charge... leading him...

They end up at a smoky little bar where she orders a couple drinks.

"So, honey, tell me about your first time..."
 
Kelley blushed and sat across from Angelique. Taking a sip from the drink that she ordered--feeling slightly more emboldened with some liquid courage. "Well..." Kelley blushed. "It all really began when I started finding panties lying around the house... I mean, not to be weird, but I just always thought they were so sexy! And then once I moved out one of my old roommates would leave her panties lying around. I think she knew about my fascination and she just got more and more bold..."

Kelley drifted off thinking about finding the dirty panties lying around his old apartment. Kelley took another sip of his drink and looked up at Angelique. "You probably think I'm just some perv... I'm sorry that you caught me--I thought I was being more subtle than I was."

Kelley crossed his legs and met Angelique's eye.
 
"Not at all, at least, you're the kind of perv I find particularly... interesting," I comment, sipping my wine. "Now, what did you do with those.. dirty... panties? Don't leave out any details!"
 
Kelley blushed a deep crimson and took a long sip of his beer. "This is so embarrassing, Angelique!" Kelley shifted in his seat and recrossed his legs before taking another long drink. But Angelique remained where she sat and did not move her eyes not leaving his.

"Well..." Kelley gulped and took another swig of his drink. "I first sniffed them, Ms." Kelley blushed an even deeper shade of red. "Then I tried them on..." Kelley trailed off and bit his lower lip--hoping he did not have to go any further.
 
"And how did putting on girl's panties make you feel? Did it excite you and make your little cock all hard?" Her eyes flashed with intensity and possibly even arousal! "Did it make you want to be a girl, a slutty girl?"
 
Kelley blushed at how forward Angelique was being. He had never ever admitted his fetish nor his desires to anyone and here she was commanding him to tell her. Kelley uncrossed and recrossed his legs, again. "Well, yes, Ms. It made me excited." Kelley though back on his first time wearing panties. "I felt... naughty, Ms. and i knew that I wanted to try it again."
 
Kelley tries to recross his legs yet again but she puts a hand on his knee.

"Does crossing your legs make the panties feel good?"

She takes another drink. "I've known a couple boys who really wanted to dress like girls. It has frankly fascinated me. It is so interesting how the littlest things get them so aroused and eager to please. Are you eager to please?"
 
Kelley blushed. "No, Ms. Angelique. It reminds me that I have panties on under my jeans. And helps to remember to not get too excited."

Kelley took another deep pull on his drink and tried to convince himself to relax. "I am very eager to please, Angelique. I do my very best to fulfill and perform my duties every day."
 
"I wonder if you would perform well with other duties, duties outside the office, at my home. I'm rather a strict taskmaster but I can reward girls like you in very special ways. How do you think that sounds?"
 
"That sounds fun, Angelique! Would I still be working in the office...?" Kelley sat back not quite believing what he was hearing, coming from his boss of all people. Kelley wondered if Angelique still wanted him to come to work in the office or what exactly she had in mind for him.
 
"This wouldn't affect your work at the office... at least initially," teases Angelique. "It would be for weekends or evenings at my home. If you are interested in knowing more, we could visit my home tonight and I can show you some things..."
 
Kelley nodded not entirely certain what he was agreeing to but curious about what Angelique had in mind and confident that he could keep himself together enough to say no if he needed to. "Sure, Angelique, I'd love to see what you had in mind for me..." Kelley trailed off and took a sip of his drink.
 
They made quick arrangements with Angelique providing Kelley her address and instructions to arrive at 7pm.

"I also want you to wear your girliest stuff. I really want you to go all out. What you choose to wear when you walk to the front door of my house will tell me so much about you."

With that, she left him with a powerful kiss that left Kelley feeling weak and submissive. Maybe it was all the drinks he'd been sipping but his mind was spinning...


---

Angelique had made all the preparations and had showered again, careful to not get her long hair wet. Not enough time to dry it before her new sissy pet was going to arrive. She had all sorts of ideas as she wandered into her boudoir to browse through her extensive collection of elaborate lingerie and outfits. Her hands brushed across a dozen before stopping at a blood red satin corset with matching ruffled panties. With a grin, remembering when she bought the corset... from that red head in Pasadena... the one she'd made lick her privates after helping her put the corset on. Mmmm, she'd been a hell of a pussy licker and for a moment, Angelique wondered if she should have invited the girl back to her hotel for a wild night. Ah well, opportunity missed.

Once she had the corset cinched up tight around her body, she admired her hourglass shape in the mirror and how it really put her large breasts on display. The panties fit perfectly, hugging her full round ass. On top of it, she put on one of her special party dresses, black satin with a deep V neckline in front to reveal her cleavage. Black 5" stiletto heels and black thigh high stockings attached to garters from the corset completed the ensemble.

She glanced at what she'd laid out in the "special guest room" on the first floor and the "equipment" in the furnished basement. She'd only had time to have a quick drink of wine before the doorbell rang. Right on time. She opened it, anxious to see how much of a sissy and how daring Kelley... no Kelly was...
 
Kelley sat outside of Angelique's home and shifted around in his seat--looking about nervously. He had been instructed to come dressed in his girliest stuff and still couldn't believe that he was here doing this. For his boss nonetheless. Underneath his jeans and shirt he wore white lingerie with matching gloves pulled over his fingers. He knew it was sexy but hadn't wanted to give anything away to his roommates and had decided leaving the house dressed normally made sense. From his bag Kelley pulled a pink dress. Kelley laid his seat back and fixed up his dress so that he was wearing it. It was dark out and with the tinted windows Kelley knew that no one could see inside of the car. The final items Kelley pulled out of his bag was a short pink wig and a pair of low black heels.

Kelley rang the bell and looked back over his shoulder nervously. Not wanting to be spotted and not sure how passable he was. Kelley heard the door open and his mouth dropped open. "Oh..." Kelley was almost at a lost for words. "Hello Ms Angelique." His eyes swept over Angelique's figure. Noticing her perfect thighs and how her dress accentuated her breasts and hugged her hips. Kelley stood for a moment forgetting that he was standing outside for anyone walking by to see but not wanting to walk-in Angelique's home without being invited. "How are you, Ms?"
 
(Very hot images, thanks!

Are you interested in shifting to first person in our writing?)

"I'm fine, Kelly, just fine," I say with a smile, looking you up and down but not inviting you in just yet. "I must say I... am... impressed. You're really a total sissy, aren't you?"
 
I blush and meet your eyes. "I am well..." I look over my shoulder nervous to be caught by someone walking by. "Yes Miss Angelique, I am." I blush and raise my hand to my cheek knowing that I am going red. "How are you, Miss Angelique?"
 
I pull up the bottom of your dress to show off your panties and your rigid clit. I give it a caress as you hear the sounds of people nearing the corner. When they arrive you'll be totally exposed.

"Do you want to cum inside or would you rather I kept touching you until you get "wet" right here?"
 
My hands reach towards the dress that you have lifted and I start to tug at it hesitantly. Not wanting to get caught in such a public setting with my firm cock sticking out of the dress that I have slipped into. I look over my shoulder hearing the people getting closer and I turn to you my eyes pleading.

"Please bring me in, Ms. Angelique. I don't want to be embarrassed! Let alone arrested!" I tug sharply on the dress and I can hear it tearing but know that I am a little more covered up, at lest.
 
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