My Hermaphrodite Boss Pt. 02

Chapter 3

"Hmmm, I can stay like this for hours just looking at you. I think I'm in love." Jasmine held me in her arms as we both laid naked in her king size bed. She had satin blue sheets and dim blue light, mirrors on the ceiling and on the walls. They reflected our images. A chain of two naked bodies stretching away to infinity, mine lithe and brownish, hers white and curvy. I would have enjoyed the situation if I didn't feel so angry with my own helplessness.

"You're cute even when you're moody." She caressed my cheek slowly and then gave me a light kiss on the lips. Another kiss followed then another. She pinched my nipple and took a mock bite out at it.

"Ouch."

"You're tender, I like that. I love to play rough sometimes."

"I don't."

"You'll learn." She gave me another tender kiss and then attacked with a lustful French-kiss, lingering for a few seconds, leaving me out of breath. She hugged me close, crushing me against her marvellous bosom. I felt her rigid rod between my legs, bobbing up and down, patting my ass cheeks.

"My bottom needs some licking." She turned around on her stomach. Her ass was pear shaped and very feminine. I kissed it and licked both mounds. Like velvet. She moaned and grabbed her ass cheeks. She spread them, displaying the pink ring. A closed gate to her hermaphrodite bowels. "Now insert your tongue, you know where."

I sniffed, luckily from her position she couldn't see the face I made. "That's disgusting."

"Oh, Ian, what am I gonna do with you?"

"Give me a raise and say you're sorry."

"I like my ass licked and you're gonna ream it, through and through. That's part of the whole package."

"Sorry, you'll have to do without boot licking, sorry, butt licking."

She flipped on her back. "I know it's gonna be fun training you. You're such a nerd. Too bad it'll have to wait. I'm going to Italy tomorrow. I should just pack you in one of the suitcases."

"I don't want to come."

She grabbed my cock. "Sure?"

"Positive."

She twisted my cock till it hurt. "You can't anyway, but I'll expect you to come along on my next trip. Do you play bondage games with Sue?"

"Huh? We were just in Italy."

"And now we're in SM, try to keep up. Well, do you?"

"You seem to know everything about me. Do you really need an answer? Ouch." I cried as my cock was twisted again. "We tried role playing once, but I couldn't resist laughing when Sue said she had me in her power. That sort of ruined it."

"Cute. There's a set of handcuffs in the upper drawer, the one beside you."

"Want me to tie you up?"

She slapped my bottom. "Giddy up."

I opened the closet to a world of bizarre toys. "You have a subscription to your local sex shop? I mean, you could start renting equipment." I counted at least six dildos, as well as love eggs, numerous videos, leather and tons of stuff for which I had no idea of their purpose. "What type of handcuffs do you like? You have a leather set and several with fur? Why do you need so many? You do orgies in here?"

"Just bring two sets you like."

"I don't even like the idea of tying you up."

"Have no fear then, I don't intend to be for a moment."

"Oh", I said. "How about normal sex? Don't you like the normal stuff?"

"I love anal." She smiled. "Do you and Sue...? "

"S... sometimes." I lied. Sue never let me even touch the place where the sun don't shine.

"You mean never. I see it got your attention, though." She winked at my dick that was rising up to the sound of the magical words 'Anal Sex'.

I blushed. "Well you caught me. It's a fantasy of sorts."

"Be a good boy and we'll sort out your fantasy right now."

I forced a grin from ear to ear to show that I'm the best kid ever.

"Just put the handcuffs on both wrists. Oh, and that stupid grin is a complete turn off."

I hesitated for a second but the thought of sinking my dick inside that marvellous pear-shaped ass won me over. I put the two handcuffs on. "Hope you've got keys for those."

"You know where to start looking for them, in case they're misplaced." Jasmine grabbed the right hand handcuff an attached it to the left bedpost, forcing me to lie on my left side.

"That's hardly convenient, I mean if you like spooning, you should tie my hand further to the right."

"In a second, dear." She grabbed the second handcuff and pulled my left arm from under me, flipping me onto my stomach.

"Hey." I tried to pull but she quickly attached the handcuff to the left bedpost. I blinked stupidly. My arms were stretched and my face mashed against her blue sheets. "Why you did that for? You're not gonna whip me or anything cause that's fucking...Awwww" I cried as she slapped my ass.

"No, I'm not into that stuff. Though now that you mention it." She slapped me real hard on my bottom again.

"Auwww." I howled in fright and pain.

"That's for calling me demented, bitch."

I had tears in my eyes. "How should I call you then, mistress?"

"Awwww." I howled as she hit me on the other cheek.

"That's for being smart. And 'Jasmine' will do. By the way, that's hardly the behaviour of a good boy. I'm inclined just to forget about the anal sex."

"In that position I doubt that you would be even able to crawl under me."

"Funny." She said. I heard her walk to the closet. Next I heard a click as she put a handcuff on one leg then on the other. She then attached them to the bed's other end. I was spread-eagled on my stomach. Naked. It reminded me of a virgin tied to an alter in a B-movie, about to be sacrificed. It made me feel silly. "Woof." I exhaled as Jasmine jumped on my back. I saw her in the mirror holding a small tube and like lightning it hit me.

"No fucking way, Jasmine."

"You think?"

"No! Hell no! Untie me up this instant. The deal is off!"

She pressed the tube and a bluish gel came forth. "You said anal was a fantasy of sorts."

"You know exactly what I meant."

She laughed and started rubbing the gel on her erect monster. She took her time, slowly massaging the monster head. She squeezed her hand around it, making wet sounds.

"You can't! I won't!" I started wiggling like a maniac trying to get her off me.

She slid backward and pressed her rod between my already spread ass cheeks. The gel was cool against my crack.

"Jasmine, don't. I can't do this, I've never done it. You'll kill me."

She moved forward and backward. In the mirror her eyes were closed and she was moaning. Her penis on my spread cheeks looked like a oversized sausage in a bun. "Your ass is dreamy. Wiggle some more for me."

I did in hope of making her finish, sparing me the unthinkable.

She responded enthusiastically, pressing hard against my butt.

Using the limited movement I was given I tried attuning to her rhythm, pressing against her shoving prick. We danced that dance for ten minutes, full of soft moaning by her and silent prayer by me that she wouldn't go forth with her plan. Anal sex never looked so frightening.

"Oh, you're just soooo damn good. Clench those butt cheeks." I did and she moaned and kissed the back of my neck. She then lay down on top of me, her huge breasts enveloping my head. Rubbing herself like a dog on a bitch in heat. "Ohhh, sweet baby, I'm gonna come. Ohhhhh. She sunk her teeth into my shoulder. I want to come inside you, babe."

I clenched my ass in fear.

"Oh, shit, babe I'm coming." She rose and spread my ass cheeks. The mushroom head bumped against my virgin opening but then she started coming. I saw her in the mirror spurting huge jets of white goo onto my ass and back. I've never seen anything like it. The volume of her jism was appalling. No wonder I couldn't keep it in my mouth. She kept it going for three more spurts then she wiped the rest on my ass and rose.

"Babe, you're just too damn sexy. I've never came so fast before, twice. Thrice, if you count the vaginal paradise you gave me. You're amazing."

"Thanks, I think. Can you untie me now? I think I had enough humiliation for one night."

"Ok, but first clean me."

"I'll need my hands, do you have wet baby towels or something."

She jumped from the bed and placed her now quickly dwindling cock at my mouth.

"Oh, fuck that."

"I thought we were past the 'I don't suck cock' stage?" She pressed the mushroom head to my lips.

I rolled my eyes and opened wide.

"Mind the teeth." She slapped me lightly on the cheek. "It's time you learnt."

It was soft now in my mouth and against my tongue. A different feeling. The gel didn't have as bad taste a taste as I feared. I rubbed my tongue against the corona and spat out the dick head and the cum.

"Don't spit, swallow."

"Hell if I will."

"Ian. Ian." She nodded her head. "For now just suck it like a lollipop."

"It's clean."

"Only when I say it is." She pressed the head again against my lips.

With little choice I started sucking the huge mushroom head. My neck was starting to ache from the position and I hoped she would decide my torment might end soon.

My mobile sang My Little China Girl.

"Sue is actually Korean." My boss grabbed my pants. She found my mobile in the left pocket. "Hello, Sue. This is Jasmine Richardson. Yep, Ian's boss." She put her hand over the mouthpiece. "Who the hell told you to stop?" She said to me. I started sucking again. "So you're the girlfriend I'm depriving of Ian's presence. I'm terribly sorry for the inconvenience. "

"He's really preoccupied with what we're doing right now. He can't talk."

"I know it's late, but we have some tasks that need accomplishing. You know what, Sue? Just choose any restaurant you want and I'll let you and your boyfriend have a free dinner. At the company expense, just to say how appreciative I am at Ian taking his work so seriously."

"Super. Feel free."

"A couple of hours."

"Yes, I'm afraid so. I'll tell him. Bye, Bye. It's been a real pleasure."

Jasmine hung up. "A real pleasure." She said. "Your girlfriend said you should work hard."

I felt her cock go rigid in my mouth again and spat it out.

"She sounds nice, your girlfriend. I envy her." She patted my cheek and looked down with mock surprise at her erect member. "You've done it again, in record time. Naughty boy." She went back to the closet and pulled out a small canister. I heard a hiss and saw her spraying something on her dick.

"What the hell are you doing now, Jasmine?"

"It's called Stud Spray."

"What's it for?"

"It nulls the feeling on the penis, extends ejaculation. Ten seconds with you and I'm shooting like there's no tomorrow. I can't help that you're just so damn hot. Just looking at your naked butt makes me wanna shoot."

"You said you'll release me."

"I lied. I want you impaled on my dick like nothing I ever wanted before."

"I don't want to. That's rape."

"That's heaven on earth, baby." She started rubbing the gel again.

"Jasmine, please no."

She jumped on the bed between my spread legs. I saw her in the mirror pouring gel on my open crack. The gel felt cold against my skin but not too much to be unpleasant.

"Relax honey." She said "I've never done it with a virgin before, but I do know that unless you'll relax, it's gonna hurt like hell."

"Easy for you to say. Jasmine, please, I'll do what you want, just don't do this."

"That's exactly what I want. I've been aching to put my sausage in your hot bun from the moment I saw you." She spread my ass cheeks and I felt her stretching my shit ring.

"Aowwwwwww." I yowled as I felt her finger enter me.

"Shhhhhhhh. Relax" She waited for a few seconds with her finger inside my virgin butt. "Don't clench."

My anus rebelled against the foreign flesh inside it and I pushed tying to expel her. When that didn't work I pushed my pelvis deeper into the bed. Jasmine responded by sticking her finger deeper into me. I froze in panic.

She started wiggling her finger inside my anus. I felt the cool gel inside my butt.

"Ready for a second?"

"Second what? Auwwww" I shouted when I felt a second finger enter me. Like she did with the first, she waited a few seconds with he fingers inside. "Just concentrate on breathing deep," she said, and kissed me gently on my back.

"Jasmine?" I tried my most reasonable voice.

"What, sweetie?" She started buggering me with her fingers. My butt clenched and unclenched around them.

"That hurts."

"You'll get used to it." She inserted a third finger and I clenched in pain.

"Take it out, please, that's really uncomfortable." I breathed in and out forcefully.

"You have such a tight bum hole. Remember, the pain is only in your head."

"No, it's in my ass. Auwwwwwwww" I shouted when she started moving three fingers inside me.

"Don't be such a baby."

"Why are you doing this?"

"What?" She pulled her fingers out and I exhaled in relief. "I could have jumped you and broken you in a single thrust. Instead I take the time lubricating you, massaging your anus and readying it to accommodate my penis. It takes a whole lot of will-power, and all you do is complain. I guess there is no pleasing some people." She wiped her fingers on my ass.

I felt her touch my crack again, this time it wasn't her finger. She didn't go for rubbing against me this time. I closed my eyes and inhaled deeply.

"Don't! Just breathe normally and try to relax."

I whimpered in response.

She stretched my ass with both hands. I felt my hole open and exposed. She rubbed the head against my pink clenched anal ring. "Just breathe." She pushed a little. I tried to wiggle myself free.

"Auwwwwwwww." I cried as she smacked my buttock. I looked in the mirror, it was quite red.

"Stop that." She leaned forward, adding more pressure with her huge head on my poor anal ring.

Nothing happened. She was just too big. She pushed with more force.

"Ouwwwwwwwwwwwwwwwww." I yowled as I felt my sphincter stretch beyond possibility.

She moved back.

I started breathing again.

I saw her reach for the gel tube. She connected the head with my ass ring and squeezed, flooding my anus with the cold gel. "Open wide and bite on this." She placed her pillow in my mouth.

My body was pouring sweat from glands I didn't know I had.

Jasmine placed her huge head at my opening again. She used the fingers of one hand to stretch my anal ring and with the other she pushed the bulbous head. The ring slowly gave-in and more of her head pushed forward.

I howled into the pillow. I felt my anal muscles stretching to the point of being ripped. Millimetre by agonizing millimetre. Like a white-hot rod was inserted into my anus. Beyond the pain I heard her moaning from far away. The mushroom head slowly made its way. Thank god for the gel or I would have fainted.

"Almost in baby. This is sooooo good. You're so tight."

A final thrust and something gave in. I screamed once more as the mushroom head popped inside me and the sphincters closed behind it, enveloping her rod in a warm loving grasp.

"Shhhhhhhhhhhh.... Baby, it's just me. Shhhhhh. Mommy is here inside her little angel." She kissed me gently on the back of my neck, "Oh, your ass is a dream, baby. If you could only know what it feels like."

Like agony. I spat into the pillow. "I'm probably bleeding right now." My voice came out in short bursts. My ass sent me warm pulses of hot pain.

"Only a little."

"What?"

"Just kidding. The gel took care of that." She pressed forward. It was like an anaconda was slithering inside my anus, splitting me apart. I looked in the mirror. Her penis was buried in my ass. It would have made a sexy picture if I wasn't in such pain.

"Your cherry is officially popped, love."

"Great, I would like to say thanks to mom and dad and all the wonderful people, auwwwwww." I shouted as she pushed further.

"You're adorable."

"Please take it out, Jasmine. I'll do anything."

"Anything?"

"Anything, just take it out."

"Ok." To my amazement she pulled back. The huge rod popped out of my suffering rectum. The pressure was gone and I started breathing again. "Anything does include you begging so nicely while I bugger you."

"Oh, god, please not again."

"Yep, that's it. Now for my part." She pressed again.

"Auwwwwwwwwww." This time my scream without the pillow must have gone through the floor to the neighbours downstairs. I hoped some of them had consciences enough to check who was being tortured upstairs, or better still, call the police. There was that enormous pressure and the same horrible pain but this time it went in more smoothly. There was a pop and my anus again enveloped her monstrous penis head. I felt her corona scraping my inner walls.

She tried to put the pillow in my mouth. I refused to open it. She grabbed onto something, it was her pink panties. Jasmine pinched my nose and waited for me to inhale. Then she reconsidered and pushed herself viciously inside me. I howled in pain and she took the opportunity to stuff my mouth with the pink panties. She didn't push the garment all the way in before I succeeded clenching my jaws. She kept her fingers on my nose though. This time there was no air coming through my mouth. I had to open wide and she stuffed the panties entirely in. I tried pushing it out with my tongue, but she slapped me hard when she saw what I was trying to do. "I'll put a masking tape over your yapper if you try that." There was no anger in her voice. Looking at her in the mirror I saw her smiling that inferno smile of hers. I bet she was enjoying herself immensely, and not just from the penetration. I decided to stop struggling, thus leaving her devoid of one pleasure. A small victory.

"Bite down, lover boy. One. Two. Three. Here we go." She rotated her pelvis forward. Slowly, controlling the movement. I thought she would cleave me in two. Inch by agonizing inch.

"Squeeze that ass like you're trying to shit me out. You want me out, do you?"

More than anything in the world, right now. I squeezed and pushed, activating muscles in my butt I didn't know I had.

"Oh my god, that's so good, you're milking me."

In the mirror Jasmine was smiling in bliss. I didn't know that at the time but my but squeezing didn't do shit in expelling her out. It actually helped her get deeper, which was exactly what she intended.

"Squeeze, little bunny. Squeeze for mommy."

I pushed as hard as I could making her moan. My lubricated anus made wet squishy sounds around her pulsating member.

"Half way there." She said. "Your ass feels soooo good." She leaned forward and kissed my head. "I know it's painful right now, but it'll become easier once we do it more often. Just one more push, love." She pressed again. My scream was muffled this time. Jasmine licked salty tears from the corner of my eye. I felt her huge sack of balls touching my ass.

"Three quarters of the way in. I guess that's ok for first time. You can call me anything but inconsiderate. Ohhhhh, but that feels heavenly." She pulled back slowly until only her penis' head was buried inside my ass. Then she slowly pushed again. "Oh, Ian." She huffed and moaned. In the mirror I saw I wasn't the only one sweating. "I'll go slowly because it's the first time for you."

Jasmine started building up a rhythm. Forward and backward. The huge anaconda slithered and scraped the walls of my anus. I tried to relax, praying she would finish fast. I had trouble enough breathing. In my own small world of agony I could hear her moaning. She sent one arm beneath me and grabbed my cock. Amazingly, despite the pain it was erect. She didn't make a smart remark, instead she started jerking me off to the rhythm of her own thrusts.

It lasted forever. Agonizing slow thrust followed by a moment of short respite as she pulled. The stud spray must have done its part. It also nullified some of the pain in my ass to the point of being bearable.