My Sexy AF Gay Supervisor Samantha

"Jake!" my boss Samantha called me from upstairs.

Unbelievable. Samantha had the worst timing.

"What do you want?!" I yelled from the kitchen downstairs. I probably shouldn't have sounded so crabby but I had finally got time to sit down and take a break. Working on a Saturday was bad enough and just she and I were there at the Hollywood mega-mansion staging it for an upcoming "Mega-open house" advertised by the realtor. Sam and I worked for a company called "Staging Los Angeles" and though Samantha had given me the dreary task of sorting books and putting items on shelves, her task involved creating a "sex cave" in one of the many mansion bedrooms. Welcome to Hollywood.

"Get up here!" Samantha yelled back at me. "Now!"

"Can't it wait?!" I asked with a hopeful tone. A few seconds passed and I thought I was in the clear.

"I said, NOW Jake!"

I let out a sigh and proceeded to rise. There was no use trying to salvage this situation. Samantha's annoying tone meant she was unhappy with something. Her hot temper could go from zero to 100 in seconds.

I jogged up the stairs to find Samantha leaning against the door to the first bedroom. We both had arrived at 7:30 a.m. and now it was a little past 10:30 a.m. I'd barely noticed her before because I was working downstairs, but I could see she had on a pair of jeans and an old tee-shirt without a bra.

Samantha Rodriguez could pull off a sexy Latina look if she really wanted to. She had a nice figure and gorgeous black hair but she was one of those people who only see imperfections in themselves. And yes, there were a few. Her face, for example, sported a few blemishes and she could probably stand to lose a few pounds but other than that she looked hot. She was one of those girls who could turn from an ugly duckling to a swan by just wearing makeup, high heels and a little black dress.

As usual, Samantha had tied her long black hair up in a messy bun. I could tell she had just finished looking for something because it appeared as though she'd been working out. Sweat glistened off her olive skin and she breathed a little heavy. It may seem a little weird to say, but my 32 year old supervisor actually has quite a nice body under all her unhappy attitude. Samantha's perky nipples strained the fabric of her t-shirt revealing a taut, tight stomach but her sexiest feature, however, is her ass. It's perfectly proportioned and looks great no matter what she's wearing. Even now I could see it pressed firmly against the frame of her door. I knew I shouldn't be thinking about these things, but I couldn't help it.

"What took you so long Jakey?" she asked, like I was her servant or something.

""This place is over 20,000 sq. ft," I complained, "That's almost half an acre."

"You're such a fucking baby," she said with a certain lack of concern in her voice, "Well I just wanted to let you know that Michelle will be here any minute now to help us out."

"Great," I groaned. "Hopefully she wasn't out drinking like last week."

Michelle was Samantha's girlfriend. That's right, my super-sexy supervisor Samantha was gay and proud of it which meant no matter how much I lusted after her, I'd never have a chance.

"Just let her in, okay?" she pleaded, grabbing my shoulder. "Okay?"

"Why can't you?" I asked.

"Look, just do me a favor and tell her to come upstairs, por fa?"

"Por fa" is short for "Por favor" which means "please" in Spanish and though I loathed the idea of having to greet Michelle, I could never say no to Samantha.

"Por supuesto," I answered which means "of course".

I don't know what it is, maybe it's Samantha's almond brown eyes and long black lashes. Or maybe it's because she's five years older than me. Or maybe it's because I too am Hispanic, tall and she often calls me "guapo" (handsome) or "flaco" (skinny) but I am completely whipped when it comes to her.

"Alright," I said, "I'll come get you when she's here-"

"No!" Samantha suddenly demanded. "Have her come directly upstairs without you. Okay? And remember to start staging the far living room."

*The FAR living room?*

She IS acting a little weird, I decided, because the far living room was on the other side of the massive two-story house. I nodded my head and rushed back downstairs to finish taking more books out of boxes. This was taking forever and the whole time, the thought of Samantha stripping naked slipped in and out of my mind. It was weird, I know, but I couldn't help it. Lesbian or not, Samantha ranked up there as one of the hottest girls I knew.

I barely got started again when I heard the doorbell ring. Michelle, I thought, it's got to be her. Nobody else rings this doorbell five times but this white girl. I reached the front door, swung it open and there stood Michelle. Short and heavyset, she had on jeans with a sleeveless t-shirt and with her colorful full arm-sleeve tattoo and blonde hair cut in a buzz: she looked totally masculine. "Is Sam here? She said she wanted to give me something?"

"Yep," I answered, "She told me to tell you she's upstairs. Just knock. First door on your right."

"Cool, cool beans" she said, Michelle gave me a thumbs up, stumbled and fell down. I rushed over to help her to her feet and as I did, I realized with her pale face, she looked like shit. She smelled like a brewery too.

"Uh, hey. I gotta puke. Is there a bathroom around here?" Michelle grabbed hold of her stomach, "I think I'm coming down with something."

"Yeah, there's at least five bathrooms. Try the door just down the hall to your left," I advised, trying to sound helpful. "There's a bed in that adjoining bedroom too, if you need to rest."

"Thanks" she said. She pulled at my arm and looked up at me. "Hey, Can you tell Samantha I'm not feeling well? I drank rum like a fucking sailor last night."

"Yeah. No problemo."

*Leave me to work while two lesbians get to play,* was all I was thinking.

I jogged up the stairs but before I got halfway up, I could hear the unmistakable sound of barfing coming from the bathroom downstairs.

Disgusting, I thought. I just cleaned that frickin' bathroom. I reached Samantha's door and lightly knocked. "Come in!" her voice called from the other side of the door. I opened it and walked in to find Samantha nude and wearing a blindfold sprawled out on the bed the movers had brought the day before.

Remember, this was supposed to be staged as a "Sex Cave" so the room was semi-dark lit up with red lights. Soft music played. We had staged it yesterday by setting out some whips and leather boots. Plus a huge canopy bed in the room was a mirror hanging high above the bed. We had also attached velvet ropes with handcuffs for both feet and hands, and there were mirrors everywhere.

I stood there stunned, completely paralyzed by fear because I wasn't sure if my sexy Latina supervisor, buck naked, could see me. Yes, she was wearing a blindfold but she had propped up her head with a pillow with another pillow under the small of her back. Yes, she lie there spread full-eagle but what if she could see me?

From my view I could see she had let her long black hair down and had on red lipstick. I sort of wanted to apologize and run out of the room, but I also wanted to take a picture with my cell phone and share it on Insty: then I noticed something. Sam's one hand was still untied. This meant she could easily remove her blindfold and bust me. Knowing her, I'd be in deep shit.

"Michelle?" Samantha called out to the room. "Hurry, close the door. I need you to handcuff me, I can't do it by myself."

Oh shit! What should I do? Samantha was trying to surprise Michelle with an incredibly sexy display. And yes she looked incredibly sexy.

I had been silent for a while now.

Without me barely touching it, the door closed softly behind me.

"What do you think?" my supervisor cooed. Her lovely brown skin glistened and I could see everything from her perky brown nipples to her completely shaven pussy. "You likey?"

Hell yes! I wanted to say. My heart thumped loudly in my chest as I licked my lips. *Get out now!* my brain screamed. But my knees quivered and wouldn't obey.

"Come on, handcuff me, NOW," Samantha demanded, waving the free handcuff with her one hand. My brain was mush, but my legs moved on their own. I was now inches away from my supervisor's exposed body. Samantha wiggled her bottom half a little, she must have been very excited for this. I could see the snail trail she'd left on the sheet. My supervisor's pussy was wet!

"Get undressed! What are you waiting for? I told you we'd have the whole place to ourselves!"

This is so wrong, I thought. She's my fucking supervisor, my fucking gay boss! She'll know it's me. I should just walk out of the room, head back downstairs and go back to the kitchen. What if Michelle comes up here? But as I clamped shut the handcuff onto Samantha's wrist, my cock had already made up its mind.

I started by taking off my shoes and socks. Then I removed my shirt, pants and undies; and my hard dick sprang out as I moved from the foot of the bed and crawled on hands and knees to my supervisor's pussy. I took a deep breath and very gently stuck out my tongue. *Do it like a chick would do it* I thought to myself.

"Oh shit!" Samantha squeaked. "Your nose is fucking cold."

Starting at the base, I gently licked the left bottom of one fold. I lapped her pussy like I would a peach. But inside I was freaking out. I'm actually eating my supervisor's pussy right now. I had imagined her body naked before but never dreamed I'd have a chance to touch her like this.

"Mmmm," Samantha moaned as I lapped her softly. She couldn't touch my head so I took my time. Eventually, she breathed deeper and deeper so I decided to stick a finger into her crotch, then two, and I moved my fingers slowly, and gently in a "come here" motion while at the same time, I spread my tongue flat. She could only feel the bottom of my tongue. I did it as softly as a chick might and I paused. I stopped to look up. I could see her nipples were erect. That was a good sign.

"Mmmm," Samantha repeated, "ooh, ooh, ooh." I returned to her pussy and ran my tongue from just above where my fingers had entered her vagina, up over her clitoris, then held my tongue still. She began to push against my tongue, back and forth, back and forth. Then I stopped.

I looked up and saw her erect nipples so I gently spider-touched her breasts, gently making circles around her nipples with my fingers.

Then I returned to her pussy and mimicked what my fingers had done to her vagina but this time with my tongue. I poked it in and out a few times as far as I could. Finally, I returned to her clitoris and just sucked on her whole clitoral region. Then I stopped.

I looked up. God, what great tits! I touched her right nipple and pinched it -- but not too hard.

Pre-cum was dripping from my cock, so I added the drops to my tongue.

Using this precum as a lube, I returned to lick the upper left quadrant of her clitoris. Nothing fancy. I just used the tip of my tongue with the lube on the upper left quadrant of her clit, keeping a steady rhythm. Unexpectedly, she squirted. I could actually feel a spray of watery fluid. It felt scalding hot as she orgasmed.

I waited, and then I gently soaked my tongue's taste buds in her pussy. The sensation felt incredible, so I started doing figure 8's on her clit, up and down and around and around in a steady movement until she spoke.

"Jake," Samantha moaned, "Please, stop it, dude, it's too sensitive." When she said my name, I froze.

"What, you didn't think I could tell it was you with that fucking sandpaper chin-stubble?" she complained. "What the hell happened to Michelle?"

"She fell down and went to the bathroom, started puking. Said she drank too much last night. I knocked and came to tell you but..."

"Oh shut up and just fuck me."

"You really want me to fuck you?" I said in disbelief.

"Well, first I want you to lick my asshole," she demanded.

"Um, okay."

She wriggled her bottom so I spread her cheeks apart to reveal her asshole and I began to lick her ass deeply. I couldn't believe my own supervisor would be into something this kinky. I wondered if this was something she and Michelle normally did... or if I might be getting this experience because she still considered me to be inferior. Like I was beneath her. Either way, I didn't care.

As I licked her butthole, she started making noises that sounded like moaning and laughing at the same time.

"What the fuck are you doing, dude, digging a hole to China?" she joked.

I swirled my tongue around her hole, trying to push it in a little deeper.

"Okay stop. Just stop it, will you?" Samantha told me, "it kinda hurts." I gave her ass a small smack in response.

"And please take off this fucking blindfold too," she ordered. I did as she commanded. Her pretty brown eyes looked up at me. Her long eyelashes had mascara and her makeup highlighted her face to full effect. She looked quite pretty.

"You do want to fuck me, don't you?" she said it more like a statement than a question. She waited. "I mean, you already ate my pussy and my asshole, so just say it. I want to fuck you, Samantha."

"Okay, I want to fuck you, Samantha."

"Well, sorry, but you can't. Ha ha."

My heart sank. God. What a bitch. I stood up. It's okay. I'm not going to do anything against her will. For the first time in my life, I think she really saw how her words affected me because my semi-erect penis began to go limp.

"Wait, I was just kidding," she told me. "Jake, I'm kidding. I want you to fuck me. For reals. I haven't had a dick in me in a long time. So if you wanna do me, do me."

"You're serious," I responded. I turned and she grinned as she looked up at me.

"Dame su camote."

I stopped and looked at her for guidance. *Camote* in Spanish means "sweet potato" so she had said, "Give me your sweet potato."

"Yo quiero su pinoche bonita," (I want your pretty crotch) I said.

"Well, you can fuck me in my pussy," she yelled. "But not in my ass."

I leaped back onto the bed and on both knees, faced her. Because her hands were restrained and she couldn't resist me, I took the chance to take her face in my two hands and kiss her luscious red lips. As our tongues danced together, I could feel her hairless pussy rubbing against my hard belly.

My dick got hard just thinking about her hairless cunt so I spit a bit of saliva, rubbed it on my dick and stuck it into Samantha's wet entrance, slowly. My fat penis stretches out to a good eight inches when fully erect but despite what many people think, not every woman finds a big tool enjoyable. For this reason I moved slowly allowing Samantha's hot folds to slowly engulf my throbbing member. She couldn't move her hands so I lifted her ass up to position her better. My cock strained against her tightness and sunk even deeper. God her pussy felt hot. "Mmmff" She moaned. What the hell am I doing, I thought. Am I really going to fuck my boss?

Yes I was.

I pushed forward even further, practically splitting Samantha's hot wet pussy apart.

"God, your cock! It's big." Samantha whispered. Her eyes looked up and turned a darker shade of brown as I pushed in and out deeper and deeper inside her. I kissed her again, just a brief one.

I wanted to savor the moment, looking into her large eyes but she had shut them. It was like she was looking down. I couldn't hold back for long so I began pumping a little faster. I was trying to act cool but truthfully I felt like I would lose control at any second. Samantha's hot little pussy gripped me tight and squeezed my shaft like a tight fist and then as I held still, she fucked me faster and faster. I could feel her cunt muscles clamping down and releasing... I didn't think I could last one second more.

"Oh god, oh god, oh god, oh god, uh!" Samantha yelped with each pull. Her eyes opened wide so I thrust in even deeper and kissed her lips.

I'm fucking my supervisor, my SUPERVISOR, who has never had a real dick inside her! My gay AF supervisor feels my dick! I couldn't it take much more. Samantha started violently bucking against me so I grabbed hold of her ass cheeks and my dick reached even deeper inside.

"Oh my god!," Samantha bucked against me hard, "Fuck me, Jack!"

*Jack?* I thought, a little confused. My name is Jake* but who the hell cared?!

I pushed one last time and ejaculated. Cum spurt out my cock like a bullet as I shot my load deep inside her tight pussy. My brown ass squeezed tight and relaxed as I released squirt after squirt - a gusher that lasted over a minute. Samantha orgasmed with me too and soon we both shook and spasmed involuntarily. My mouth went dry and I pushed my lips against Samantha's red lips and we french kissed. Her hot-body and erect nipples pressed against my chest until I finally felt my dick go limp, and I moved off her. I could see our combined juices leak down from the crack of her pussy onto the sheets.

"Oh shit, that was a good one," Samantha breathed. "Now get me out of these fucking handcuffs before someone walks in and sees us."

"You mean like Michelle?" I asked. "Would she be pissed if she saw you?"

"I don't know. She didn't come home last night so to be honest, I think she's seeing someone else," she told me. "I texted her seven or eight times and she didn't answer me. It's her loss."

"Can I ask you a question? Was that your first time with a dude?" I wanted to know.

"No," she looked up with a smile. "Honey, I've had lots of boyfriends. The last one cheated on me. But you know what? Something good is going to come from this. I mean, now I remember why I like guys and I realize it's not just guys who cheat."

That made sense. She was bisexual.

I rose from the poster bed and removed the handcuffs from Samantha's hands. Once free, she looked up at me admiring my hard body. Then she reached over and playfully pinched my cock. Semen apparently still dangled there because I could see the dew on one of her fingers. She licked it and looked sexy as hell

"One thing: you didn't use protection, honey."

My heart sunk deep in my chest as I shook my head. "Yeah, I'm sorry. I'm clean. No diseases."

"Well, if you want to do this with me again, we're gonna have to buy you some protection okay?"

I nodded in agreement and realized she had said "we". Awesome.

Samantha tugged at her t-shirt to put it back on. "Come on, let's get the fuck out of here."

I dressed quickly and I had just made it out the door, shutting it behind me, when I saw Michelle. She was slowly chugging her way up the stairs so I stopped.

"How are you feeling?" I asked.

"Better," she answered. "Thanks for asking."

"Yeah. No problem."

I passed her as I started back down the stairs and paused at the sound of Samantha opening the door. I looked back and at first I thought she looked at me in horror, but then composed herself.

"So, I hear you weren't feeling well," Samantha said with a doubtful tone in her voice.

"Well, I'm feeling much better now," Michelle said. "Much better."

"Really? That's good, I'm glad to hear that. How was Cynthia's party?"

"Good. You said you had something for me here? Or was that just a sick joke?"

"A sick joke? Michelle, I am wondering where we're going with our relationship."

"Yeah, well. Do we really have to do this? Here? With him listening in?" Michelle indicated me.

Samantha eyed me. "Why? What does he have to do with anything?"

"You must be joking. I could hear the two of you fucking. The whole town could hear you. So to answer your question, Samantha, this relationship is going nowhere. Absolutely nowhere."

"Great, then that makes two of us, because I know all about you and Cynthia."

Michelle turned and started down the stairs but stopped. She turned and looked up at Samantha paused for one last jab: "Yeah? Well, just so you know, Cynthia eats my pussy better. And she doesn't snore like you."