Fridays at the Guardian Angel

All characters are the age of 18 or older.

*****

"Three kings" announced Jackie, flipping her cards, "What crap hand do you got so I can take your money?" Smoke bellowed out her nose like a dragon, floating to the face of the blonde on her lap forcing a cough from the captive princess.

"Full house" Said a calm Mari, nose in her wine glass. "Maybe if you weren't such a cocky bitch you might actually win one of these nights."

"I'm going to crack through that cold shell of yours one of these days, ice queen. And besides if I'm not having fun then what's the point in playing?" Jackie turned her attention to me, "OK miss detective, I can tell we blew your fucking mind with that fairy tale of Kris popping off inside her high school sweetheart-"

"Fuck you" grunted Kris, not looking up from the deck she shuffled.

"I know we're sometimes a bit of a mystery to you normals, so please, ask away." Jackie continued, ignoring Kris' comment.

"Normals?"

Kris tossed cards around the table, two landing in front of Mari. "Slang for females, meaning non-futanari" Explained the dark haired beauty as she took a sip from her glass of red wine.

I rubbed my temples. "I'm still stuck on a few things from Kris' story." Kris looked up at me, meeting my eyes for the first time of the night.

"You think I'm lying?"

"No no!" I stammered, holding my hands up in a sign of peace. "I just don't get it. Like, in TV shows and celebrities, futanari just seem so interesting. I just don't get why..." I trailed off.

"Why we would hide it?" Cass finished my sentence for me. I answered her with a nod. "Not everyone wants that kind of attention and not everyone wants to be different from everyone else. At a young age like that it's scary to know that you're completely different from everyone you know. Those of us that reveal our gender in high school do often gain popularity, but suddenly your life is under a microscope. It becomes a hassle, especially because high schoolers can be so damn mean."

My memory drifted back to my high school days, I knew my fair share of bullies who searched for anything out of place on their peers to pick at. It made sense to me.

"Parents also often encourage their kids to hide their gender during high school as well. Bear in mind we may live different lives than you normals, but we're still human." Cass continued, "We're still as hot blooded and stupid as every other girl as a teenager. When a young futanari embraces her newfound sexuality without maturing you get disasters like our heroine over here." Cass nodded towards Jackie who was trying to hold back laughter and failing.

"I made it a personal goal of mine to get as many of my school's administration knocked up before I graduated." Jackie choked between laughs, "My principal's water broke during graduation. Good times..." She sighed lost in memories.

"The fact there may be a little version of you running around somewhere terrifies me." Cass muttered in disbelief. Jackie continued to laugh.

"Ok, I get that bit now. But Kris, you said you only knew Sam about a week before she demanded you to have sex. I know she was young and impulsive, but that just seems a little crazy." My eyebrows raised as I asked.

"Sam was pretty handsy, she would hug me all the time so it was probably confusing for her." Kris softly replied, hiding behind her bangs.

I maintained a confused stare.

"What Kris is trying to say..." Started Mari, "is that she probably got some of her oils on Sam throughout the week, likely confusing the teenager." My blank stare continued, this time directed at Mari. She rolled her eyes and went on. "When we Futanari are aroused, the oils on our skin act as aphrodisiacs when they come into contact with a female. You probably felt a jolt when you shook Jackie's hand earlier." Mari sighed. "Because she's always aroused."

"Hell yeah!" confirmed Jackie.

I remembered the warm tingles I felt when I shook hands with Jackie, suddenly realizing it was feelings of lust, I turned bright red. I hid my eyes from Jackie's side of the table and began to babble, "I mean, I just don't think, I mean-"

"Don't worry little fish, I may act like a bitch but I'm not a psychopath. Besides, I've already got my catch of the day." Jackie squeezed the inner thigh of her beautiful captive who winced. "Ok, maybe I am a bit of a psycho!" Jackie gave out a hearty laugh.

Giving a sigh of relief, I turned my attention back to the other members of the table just in time to see Kris break eye contact with me. Her cheeks were bright red as she stared into her glass. I sudeenly remembered the sensation when I shook Kris' hand. "Kris..." I started.

Kris closed her eyes and blurted out, "I've got a thing for redheads! I'm sorry!" Her face disappeared into her hands. "Is that your natural color?" she asked, voice muffled by her hands.

"Uh, yeah." I blushed.

"Wow...it's beautiful." whispered Kris, who emerged from her fingers to look up at me with a blush. A silence fell over the table.

I flushed a bright red. I found myself thinking about my future and how Tess and I had talked about having kids one day. Looking at Kris I imagined a girl with her short curly bob and my flaming-red hair. The idea didn't sound so bad to me actually. I gave a soft smile, "Thank you."

"What the fuck!" yelled Jackie shattering the moment. "She's your type?!" Jerking a finger at Kris, demanding an answer.

The table shook with laughter while Kris and I attempted to turn invisible; even the beautiful angry mute on Jackie's lap gave a chuckle.

"You could learn a thing or two." Said a smiling Mari, nodding towards Jackie.

"Fuck that, I've gotten by just fine without that cute puppy love shit." Grunted Jackie.

"From a young age too apparently." I was desperately trying to change the subject, "Your principal, really?"

"Now that's a goddamn story" Jackie roared, suddenly in a much better mood. "Listen close miss detective."

*****

Emily Westgate leaned back in her leather office chair resting her hands behind the tight black bun of her hair. She took in the sight of her office, awards and certificates lined the walls, photographs of her with important women lined her desk, and old books from ages passed filled her shelves. It was the perfect environment for a woman of her stature, so fitting for the principal of United Academy.

Things had been looking up for Emily. In the span of ten backbreaking years she had turned the academy from an average high school that produced average students to highest rated school in the city. Unity's sports teams brought home regional and state titles, and the school's test scores were the best in its 50 year history.

Emily's sights however were set far higher, her current goal set on a now open seat for the district's board of directors. Winning the seat would be a launch pad for public office, and with her amazing accomplishments at Unity, the seat was all but secure. She had opponents, but her successes and experience outshined anything her competitors had to offer.

A buzz echoed from the phone on her desk and a metallic voice echoed out the speaker. "Mrs. Westgate, Jaqueline is here for you."

Despite Emily's achievements, she still had a few headaches to deal with. Jaqueline was one of those headaches. Emily sat up, adjusting her dark suit jacket and sharp black skirt. She was the symbol of authority, a professional woman who solved problems with an iron fist. "Send her in" she ordered.

Her office door jerked open revealing the major thorn in her side. "Welcome Miss Jaqueline. Please, have a seat" she calmly said, gesturing to exquisite the leather loveseat in across from her desk.

The student let her heavy windowless office door slam shut behind her as she strode in. Emily grew instantly annoyed at the sight of her, as per usual her uniform was a mess. Her white button down shirt fell loose, untucked from her black school skirt, which was rolled up well above the knee. She was missing her leather dress shoes instead opting for a pair of bright red sneakers to go with her white knee socks. Her dark ponytail bobbed as the student confidently strode over and plopped down on the seat, leaning back and spreading her legs in a confident demeanor.

Emily did her best to maintain a polite smile. "How can I help you today?"

Jackie leaned forward and gave a big smile, showing off sharp white teeth. "You can help me by reversing that expulsion you gave Yvette."

This was not a surprise to Emily. Jaqueline and Yvette were partners in crime, raising hell all over the school and being general problem children. It was their senior year and Emily couldn't wait for them to finally leave. Emily was convinced Jackie ran so wild due to her status as a Futanari, making her somewhat untouchable. In Yvette's case however, she was removed before graduation; a packet of marijuana found in her locker solved that headache. Emily maintained her polite expression, "You know our policy here Jaqueline, and we do not tolerate illegal drugs on school grounds."

Jackie's smile hadn't left her face, a discomfort for Emily. "Now you and I both know you set her up, those drugs were planted." Jackie was practically chewing on the words through her smile.

A cord rang in the back of Emily's mind, but she didn't show it. The allegation was true, Emily had planted the drugs in the locker. Aside from being a pain in the ass, Yvette had a strange pleasure in failing state exams. She seemed to get sick pleasure from knowing she was dragging the average of the school down with her. Emily solved the problem like she solved most problems, she got rid of them.

"Now Jaqueline," Emily began "I know you're upset about your friend but that's no reason to go around with these absurd allegations."

Jackie's smile was still going strong. Emily's stomach began to twist with an uneasy feeling. "I figured you might say something dumb like that. Have a watch teach." Jackie slid her phone across the desk, coming to a skidding stop in front of Emily as a video sprang to life on the screen.

The image revealed an office with walls covered by certificates, awards, and photographs of important looking women. A leather loveseat much like the one Jackie was sitting on rested across from a large office chair not unlike the one Emily was currently sitting in. The large oak desk in the middle of the frame was identical to the one the phone was currently resting on, except this desk had the school nurse sitting atop it. Her legs were spread and head arched back in a soundless scream, body convulsing and both hands grasping the dark hair of a head buried between her thighs. Emily's stomach dropped as the nurse's body steadied and a face similar to her own emerged from between shaking legs.

Panic overtook her. Frantically she fumbled with the phone, deleting the video. "Where did you get this!?" she hissed at the smiling viper across from her.

"I wonder what your wife would think, home taking care of your children while you're playing doctor with the nurse."

"Don't fuck with me." Emily had broken character. "You will tell me where you got this or so help me god."

"Or what?" Jackie asked. She was relaxed, laying back with arms behind her head like she didn't have a care in the world. "You're asking the wrong question here teach. You're should be asking if that was the only copy of your little home video."

Emily's eyes danced around the room, lost in panic. Her focus on work had not been kind to her marriage. Her relationship with her wife was warm but the sexual flame had flickered out between them years ago. The new nurse for this school year had that spark she missed, and Emily had reached out and taken it. She cursed herself for being so sloppy. Their rendezvous had been going on for a couple months in her office, a space she thought safe with its thick soundproof walls and locked door.

She met the little viper's eyes, a fear growing in her chest. "What do you want?"

Jackie belted out a laugh, "Alright! Now we're talking!" Her smile vanished and she narrowed her gaze, taking on a suddenly serious tone. "It's a simple deal really. You do as I ask, and your little secret lives and dies on the various places I have it stashed. Refuse, and it may or may not end up online and e-mailed to every student in school. "

Hate was not a strong enough word for how Emily felt about the little demon across from her, but she was stuck. Thoughts raced through her mind. She was sure there had to be a way out of this, there was no way this brat had trapped her. If this video got out she would never be able to show her face in the world of politics, possibly have to resign, and her marriage? The kids? It was over. Emily composed herself back into a professional persona.

"Very well Jacqueline, your friend Yvette was it? This little misunderstanding can be cleared up with little issue." Emily yielded.

"Very good." Jackie nodded.

"Indeed. Now if you excuse me I have much to do, and I would appreciate if you kept this conversation between- Miss Jacqueline?"

Jackie had stood up mid-sentence and unfastened her skirt which dropped to the floor. Jackie rested a hand on the bulge of her white cotton panties. Emily jumped to her feet, horrified. "What the hell are you doing?!" she demanded.

"Well I was so impressed by those oral skills of yours from the mix-tape that I thought I might try them for myself. So if you would be so kind." Jackie's erect cock bounced as it broke free from their cotton prison.

Emily recoiled in horror, speechless she struggled to find words for how disgusted she felt.

"No?" Jackie asked as she stroked her erect length. "Ok then." She reached down and grabbed her phone, still on Emily's desk.

"What are you doing?" Emily demanded, avoiding the sight of Jackie's hairless cock.

"Calling a friend, they owe me a favor." Jackie responded in a casual tone.

"Wait, wait, stop, please!" Begged Emily. Jackie froze phone to her ear, eyes locked on Emily with a raised eyebrow. Emily's mind was close to bursting, was there really no way out of this?

There wasn't.

Emily inhaled deeply. "Fine."

"Glad to hear it!" Jackie tossed the phone back to the desk, returning to focus on stroking her stiff shaft. "Now let's see what you got."

Emily slowly shuffled around her desk and stopped in front of Jackie. Nearly half a head taller, Emily locked eyes with the student, a facial expression of hate plastered on her face. She felt a hand rest on her shoulder with a soft push downward. Emily sunk to her knees her teeth locked in a grimace.

"Oh and don't get any funny ideas. If anything happened to me, that doesn't mean your secret's safe. So that means watch those teeth you slut."

Emily felt the force of her words. The little shit had thought of everything, she was at her mercy and there was nothing she could do about it. From her position on the floor Jackie's erect rod bobbed inches from Emily's face. Bracing herself she wrapped her fingers around the base of the smoothe shaft and after a moment of hesitation, leaned forward taking the head in her lips.

"Atta girl." Sighed Jackie, placing her hand on the bun of Emily's hair and gave a slight push towards her crotch. Emily slid further along the girl-cock, lips flowing over the head onto the shaft. She closed her eyes in a wince, she never had anything this large inside her before and the cock tasted salty like body sweat. The hand holding her bun jerked her head back, mouth slipping off the cock with a 'pop'.

Jackie jerked her bun down, forcing her face to look up at her. Jackie bent over, her face close to Emily's, "I don't think you're taking this as seriously as you should be. You have five minutes to make me cum or I make you famous."

"You wouldn't dare." Emily whispered

"I have my principal on her knees sucking me off. Fucking try me." Jackie's expression made Emily's heart sink, mind breaking into a panic. Grasping the girl-cock she took Jackie's length in her mouth as deep as she could. She bobbed up and down with loud slurps, hand pumping at the base of the shaft. Jackie rubbed the top of her principal's head sighing soft moans with each slurp.

"Ah yeah, that's good you slut." Jackie breathed, eyes closed. Emily mentally winced at her words, but continued her work slurping down her student's shaft. Her tongue desperately massaged at the head of the cock in her throat as she pistoned along the member. Saliva dripped down the sides of her mouth, flowing down her chin. Streaks of red lipstick streaked along Jackie's shaft, stroked clean from Emily's lips. Emily sucked with as much pressure as she could muster in a desperate attempt for cum to burst from the cock in her mouth as fast as possible.

"Allow me." Jackie said, hands taking a firm grip of the bun of Emily's hair. Jackie jerked her hips forward, shoving her cock to the base down the throat of her principal. Emily gagged, her throat unable to handle the massive girth now inside her. Maintaining the firm grip of Emily's head Jackie rocked her hips, forcing her entire length in and out the wet lips. With each thrust Emily gagged and her face pressed against the Jackie's crotch. Sweat covered Emily's face from the abuse, tears poured down her face leaving black trails of ruined mascara. Moans, slurping, choking, and gagging echoed off the walls as the face-fucking continued.

Jackie's pace quickened as she slammed Emily's face on her cock. "Yeah, this is what you deserve you slut, you fucking bitch. This is your goddamn place." Jackie moaned. Emily's vison grew blurry from the abuse and lack of oxygen. "This-is-your-goddamn-place" Jackie grunted in time with each forceful thrust, slamming Emily's face into her crotch.

The hand holding Emily's bun jerked back, ripping her off Jackie's cock and held her dizzy head up. Trails of saliva trailed from the shaft to her lips. Jackie's legs shook as a stream of cum struck Emily on the forehead, a trail flowing down over her eye. Jackie grunted and shook, each time tremor releasing another stream of sticky cum onto Emily's shivering face. Emily winced with each strike, giving a quiet whine as her face was covered with the sticky mess. Jackie stroked her cock, and with a final grunt shot one final splurt of cum on Emily's eyebrow, which dripped down across her eye.

On her knees, Emily turned and spat out the mixture of saliva and cum that had pooled on her mouth. Cock still in hand, Jackie fell back on the couch with a plop and sighed. "Just what I needed, Teach."

A heap on the floor, Emily choked and panted in a desperate effort to fill empty lungs. Her jaw ached from being forced open, and her throat was sore from having a cock shoved down it. The rope of semen hanging from her eyebrow swung into her eye. Attempts to wipe the white goo from her eye socket only made it burn worse.

Emily slowly regained her breath, her panting turning to sobs of humiliation.

"Perfect!" Jackie shouted as she jumped up from the loveseat, still stroking her shaft. She swiped her phone off the desk and grabbed Emily's chin, jerking her face to look up. "Smile" mocked Jackie, snapping a picture of Emily's cum-covered face. "What do you think Mrs. movie star?" Jackie asked showing the image to the sobbing Emily.

She didn't recognize the person in the photograph. What was once a clean professional face, sharp make up and proper hair in a tight bun was gone. Instead she saw a face covered in black flowing tears of mascara, smears of saliva and lipstick ran in trails down the sides of lips. The tight black bun was replaced by messy frazzled hair, wet with sweat and cum. The woman in the photo had a miserable expression, made worse by ropes of cum splattered across every surface of her face. "I give it 8 out of 10." Mocked Jackie, sitting back down on the couch.