Her Futa Boss in Bed: A Shemale on Female Story Read online

  © 2017, Melody Harris

  Her Futa Boss in Bed

  A Shemale on Female Story

  Take a peek at what awaits you!

  Cassie sensed the moment of no return; they were going up to the bedroom to finish what they'd begun. She followed without hesitation, following her blond boss up the stairs. She watched the shapely curve of her ass in front of, waving in a cat-like motion as she made her way up the carpeted steps. They turned the corner as they came to the top of the steps and Sandra leaned back against the wall. Cassie kissed her again, pressing their breasts together and their tongues tied around each other outside their lips. She ran one hand down her curvy body, lower… and lower… until it came to a rest on that same rock-hard shaft. Her hesitation was much shorter this time. She slowly descended, taking her time as she dragged her tongue along her boss's skin until she was on her knees in front of her. She let her hands wander up her boss's smooth legs, feeling every inch of her thighs as she slowly lifted the front of her dress.

  Cassie tapped her foot nervously as the elevator stopped once again, well below where she needed to go. At this rate she could have taken the stairs. This must have been the third time she was late this week. The first time she got lucky, but this morning… this morning her boss spotted her. She was just going sitting in the chair when Ms. Wainwright walked out of her office and looked down her glasses at her. Now here she was, pacing back and forth in the elevator on her way back from lunch. Maybe if she worked in a smaller building? Too late now, of course. Cassie glanced down at her phone nervously, bringing the screen to life with a click of the button on the side.

  1:04. She was late, and she ran through the door to her office space. She slowed down, not wanting to draw attention, and walked through the cubicle farm, checking over her shoulder to see if anyone noticed her entrance. There were a couple coworkers absorbed in their own projects, far too busy to notice her walking between the desk. Her butt hit the seat and she rolled her legs under the desk, suddenly relieved to have gotten away with it.That was until she heard the familiar “tsk tsk” of a woman’s voice standing behind her.

  She turned her chair slowly to the side, completely unsurprised to see Ms. Sandra Wainwright standing there, leaning against the wall behind another cubicle wall. Was she hiding there just to catch her out? The thought terrified her, and Cassie found herself wondering what other jobs she might be qualified for. "I think we have a problem, Cassie," she said disapprovingly. Cassie just sort of hung her head in shame. This had been a hell of a week. She was fresh off a nasty, bitter divorce, and her return to the workplace had been anything but stellar. Whether it was dumb luck or her own distraction, she knew she was falling behind in the workplace. Now, the chickens had come home to roost. Her time was up.

  “I know,” she answered. Ms. Wainwright flashed her trademark glare at her. Something about this woman was always so… different. She was older than Cassie, somewhere in her late thirties compared to Cassie’s twenty-five. The way she carried herself, though, was like a school principal. She marched the hallways of the Chicago newspaper like a queen, managing her royal subjects through a combination of fear and intimidation. She was a harsh mistress, but there was no denying her success. Cassie heard the paper was failing miserably until Ms. Wainwright came on board, turning everything around with her harsh and unforgiving management style.

  Now, Cassie was eye to eye her. Sitting behind her desk, she felt completely vulnerable to the domineering woman. “See me before you leave today,” the unblinking blond woman told her. Cassie nodded her head and returned her attention to her desk. Well, she thought, if Ms. Wainwright was going to fire her she might have done it on the spot. Maybe she lucked out and got a second chance. Cassie returned to the stacks of paperwork on her desk and pulled one in front of her, but she knew that concentrating on her work was going to be impossible.

  It was her pet peeve, really. It’s the same feeling she got as a child, knowing that she was in trouble and waiting to her from her parents, the teacher, or the principal. As she sunk down into her chair, she felt like this was the equivalent of the principal promising to call her parents. She took a deep breath, exhaled, and did her best to concentrate.

  **********

  The sun hung low on the horizon in the windows behind her. Cassie glanced up at the clock from her desk… it was almost time. Everyone worked on the same clock so no one had an excuse to stay too long or leave too early. If the working conditions weren't otherwise so , this level of micromanagement might have driven everyone crazy. It was hard to complain, though. Timeliness was just one of Ms. Wainwright's main concerns. She didn't want productivity lost to skipping out early – she said it would nickel and dime the company to death. Since things were going well, she might have been right.

  Cassie organized her desk and stacked the paperwork for the next day, though she wondered if that was a necessary step. For all she knew, she wouldn’t be coming back tomorrow at all. She pushed back her chair and stood up right as the clock struck five and took a few cautious steps to the boss’s door. With a deep breath, she hit the wooden door with her knuckles. Almost immediately, Ms. Wainwright’s voice called for her to come into the office.

  “You, um...” she stammered as she opened the door, “wanted to see me?”

  "Of course I wanted to see you, why else would I have called you in? Try to keep up," she said coolly. This wasn't off to a great start. "Take a seat," the older woman said, motioning to the chair in front of her desk. Cassie stepped forward into the dimly lit office, completely quiet except for the sound of Ms. Wainwright turning another page as she finished her own work. Cassie slipped into the seat, carefully crossing her legs and waiting patiently. The seconds ticked away as Sandra Wainwright examined the papers on her desk with the same look she gave the employees. Cassie watched nervously as she put the papers down and slipped her glasses off her face.

  She looked like an entirely different person without them. A little younger… more human. She was an attractive woman, too. Fair skinned, with long blond hair, and a curvy body that would get anyone's attention in the club. She flashed Cassie a half-smile. "So," she started, "we're having some trouble with timeliness?"

  "Um.. goose bumps's a new problem. I've just had a rough week," Cassie tried to explain. "Just… don’t fire me,” she pleaded. Ms. Wainwright took a good, stern look at her.

  “I should,” she said with a straight face. Cassie took a long moment looking into her stone-cold expression.

  “I know,” she answered. “I promise this isn’t what my work is normally like. Like I said, it’s a rough week.”

  “And I’m supposed to take it easy on everyone that walks through claiming they had a rough week. Jillian just had a baby a couple months ago. She started back at the paper last week and you don’t see her being late, do you?”

  “No," Cassie said again. She could feel her desperation mounting, what could she possibly say to end this fucking torture? "Please," she again asked, "I'll do anything."

  “Anything?" Ms. Wainwright seemed to latch onto the word like it held some special significant. "I've heard that before. Are you sure you actually mean it?"

  “Yes, positive. Really, I swear I would do anything to show you that I’m serious about this job.”

  Ms. Wainwright leaned back in her chair, putting her feet up on her desk as she folded her fingers across her stomach, locking them together as she continued to examine Cassie. Her blonde hair was backlit by the setting sun bursting through the windows behind her, painting the room in a sort of orange glow that shined off the sheer material of her dark stockings. She had these long
legs that seemed to starts at her heels and head to the ceiling. Her skirt looked just an inch too short under the circumstances.

  Cassie instantly noticed how strange this behavior was from her. "Anything?" Ms. Wainwright again asked.

  “Anything.”

  “Go on a date with me.”

  If Cassie had been taking a drink she would have sprayed it across the room. She blinked in confusion, looking around the room as if for the hidden camera she could find. “You said anything,” Ms. Wainwright reminded her.

  “Yes. I mean no, I mean… yes. Yes, I will. Even that! I just… I just didn’t know you… uh...” Cassie continued to stammer.

  “There's a lot you don't know about me, Cassie." She reached for the cup of coffee on her desk. "How about tonight then? Say around nine o'clock?" Cassie felt absolutely railroaded by the question. She said anything, didn't she? What the hell was she going to do now, turn around and walk out the door? Of course, that was an option… but she needed the money. Besides, it's just a date. What harm could come of it?

  “Nine o’clock,” she agreed in a shaking voice.

  “I have your address, I’ll see you tonight. And uh… wear something sexy.” Cassie nodded obediently and left the room, understanding that she was dismissed. She closed the door to her boss’s office and stared at the now-empty room of desk and cubicles. She leaned back against the door and looked up at the fluorescent ceiling lights. What the hell had she done?

  **********

  Cassie leaned into the mirror and checked her makeup one last time. Her boss would be here any minute now, and she sure as hell wasn't going to let anything go wrong. She tried to assure herself that this didn't make her a lesbian, but after her divorce, it probably couldn't hurt to try anyway, could it? She shook the thought away, trying not to get caught up in labels. It was just a date anyway, who said that anything was going to… happen?

  She took a step back from the mirror and checked herself out. She wore a slinky black dress that accentuated her curves, and her long, reddish brown hair flowed freely down her back in loose curls. She even put on some fishnets stockings, putting the outfit completely over the top. With the finishing touches of deep red lipstick, she looked ready to hit the club, or maybe even the streets. It might have been a little over the top, but she was sexy and comfortable, so the outfit was a winner. Cassie was just about to tweak her makeup when she heard the sound of her doorbell ring through the house. There was her date.

  The word date made her skin tingle with a combination of excitement and dread. First time for everything, she though. Cassie grabbed her shoes and walked quickly down the stairs of her small, quiet home outside the city. She opened the door to see her boss. "Wow," she said breathlessly. Ms. Wainwright knew how to dress up. She had on a bright red dress, with cleavage piled high, showing the full length of her gorgeous, bare legs. She looked ready for the stripper pole, and suddenly Cassie didn't feel quite so much like she was pushing the envelope with her outfit.

  “I’m glad you approve,” her boss said.

  “Let me get my coat,” Cassie said, but her boss took a step inside. She pulled a bottle of wine out from behind her back.

  “I think we’ll be staying in. I brought the wine,” she said coolly.

  “Oh, our outfits seem like a bit of waste,” Cassie said with a sheepish grin.

  “Not to me,” her voice said in a suddenly deeper, more seductive voice. She watched Ms. Wainwright’s eyes wander up and down her body, covering her every curve. “Have I ever told you how much I like fishnets?” she asked, biting her lips. Cassie felt self-conscious, tucking a loose strand of hair behind her ear.

  “No, I don’t think you have. Well, let me take that bottle, Ms. Wa..”

  “Sandra,” her boss interrupted.

  “Sandra. I'll go open this bottle. Make yourself comfortable," she gestured to the couch and took the bottle back to the kitchen. Cassie placed the bottle on a counter and reached for the corkscrew. She noticed her hand shaking violently. The nerves were getting to her, maybe the wine would be a good idea, anyway. Cassie barely managed to carry the two glasses with her nervous hands, walking slowly as she came out from the kitchen, afraid she'd embarrass herself with a spill. "So… Sandra… how'd your day go?" she asked, taking a sip almost immediately. Somehow, calling her by her first name was stranger than being on a date with her. She swallowed hard and reached the bottle to top off her glass. She was going to need this.

  “Not bad, I’d say. I had this employee that was late again… third time this week, but she doesn’t know that I saw all three.” Cassie blushed and looked down at the ground. “I decided to give her another chance though. She’s just too sexy to not have around.” This time she nearly choked on her wine. Sandra shot her a sly grin, clearly taking pleasure in making her uncomfortable. “Problem?”

  “No!” Cassie blurted out. “Nope… just uh… listening.” She took another swig of wine as they sat in silence for another couple moments. It was strong stuff, a few sips in and she could already feel a warm fuzziness settling into her thoughts. Her racing heart started to slow a little, calmed by the universal, social lubricant that is alcohol. Sandra shifted over on the couch a little more, bringing her body closer to Cassie’s, canceling the moment’s rest her heart had managed.

  She lowered a hand onto Cassie’s leg. Apparently, the moment had arrived. Something would happen tonight. Cassie had to wonder if doing this with her boss would help her keep her job, and what that said about either of them. It was too obvious, too insulting, a question to ask, though; she would have to keep that thought to herself. She looked down at the older woman’s hand slowly running up and down her thigh, feeling her creamy skin through the spaces in the fishnet stockings.

  It was… exciting. There was something about the attention, something that flattered her whether or not she’d ever even thought about being with another woman. “I have something to tell you,” Sandra said, placing her glass on the coffee table.

  “That.. you’re a lesbian? Cause, I think I figured that out, Ms… I mean, Sandra.”

  “No. Well, yes, but not that.” Now it was Sandra’s turn to look nervous. Cassie was confused by the sudden shift in mood. Sandra reached for Cassie’s hand, folded neatly across her leg, and grabbed it. Her boss slowly pulled her hand over to her body… she was expecting her to place it on her leg, but then she kept lowering her hand slowly onto her…

  “Wait, what?" Cassie asked. Her eyes opened wide in a combination of shock and confusion. Her hand was resting on a solid, rock-hard bulge underneath her boss's dress. For a moment, she thought she saw a look of vulnerability in Sandra's normally steely eyes. She sat there, with her hand on this completely unexpected cock underneath her dress for what felt like a small eternity. Neither of them did or said anything as the seconds ticked away in silence.

  Cassie caved. It was already the strangest night of her life, why not just go all the way with it? She moved her hand back and forth, pressing her palm against her cock. It was large, firm, and not at all unpleasant, really. Well, at least with what she could tell through the many layers of the dress.

  Sandra reacted instantly. She leaned her body over and pressed her lips against Cassie’s. The younger woman was nearly frozen with nerves, but as she felt the warmth of her face against her lips, the smoothness of her lips; she slowly parted her lips and let Sandra’s tongue slip into her mouth. Her boss pressed her tongue deeply into her mouth, kissing her passionately and sloppily. She returned the favor, driving her tongue in circles around her boss’s. A million thoughts swirled through her head, ranging from confusion to fear, with more than a little arousal in the mix. Her lips were so soft… her body… her hand drifted off the firm cock and slowly ran up Sandra’s torso, cupping a large breast in her hand. She squeezed slightly, feeling the weight of it in her hand.

  Sandra returned the favor, sliding both hands up Cassie's body. She hooked the straps of her little black dress with her fingers and pulled
them to the side, dragging her bra straps along with them. Her mouth broke away from Cassie's and began the long journey from her lips to her shoulder; she dragged her tongue along the sensitive skin of her neck, with her hot breath sending goose bumps across the younger woman's body. Her hands continued to drift lower and lower on her body until the slid into the cups of her bra. Sandra tweaked Cassie's nipples between her fingertips. "Oh my God," Cassie whispered breathlessly.

  Her boss's fingers clasped onto her dress and pulled down, shoving the material down around her waist. She sat on the couch next to Sandra, her chest completely exposed. Her boss ran the back of her hand up and down her body, admiring it. "They're so pretty..." she said with a soft grin. Sandra bit her lip before she couldn't resist any longer, diving her lips straight towards one of Cassie's nipples, pointed in the cold air conditioning of her living room. Her warm mouth engulfed her sensitive nipples, making her gasp in delight. Sandra groaned in delight at the taste of her body, her hands feeling their way across her skin while her mouth took in her tits. Cassie ran a hand through her blond hair, feeling her way down to her back where she ran her fingers back and forth for a moment before grabbing onto the zipper of her dress and pulling it down. She was as the tight material of the dress peeled away from her back, exposing a purple bra strap behind her. With a practiced hand only a woman can have, she flicked it open.

  Sandra leaned back, letting her dress fall off her shoulders along with her bra, exposing her enormous tits. They were beautiful… large, with the just the right amount of firmness and silver-dollar nipples. Cassie caressed one in her hand as Sandra’s hand pulled her head forward. She still didn’t know how she felt about this whole thing, and now she was about to suck on these tits… but they were gorgeous. She gave in to her temptations and leaned forward, sucking forcefully on one nipple. Her mass of flesh pulled into her mouth, and she slid her tongue up and down wetly against it. Sandra’s body squirmed in response, and her breathing deepened. She wrapped her arms around Cassie’s head and pulled her against her chest, smashing her face deeply into her enormous tits.