tagAnalA Boss, A Mentor, A Lover Ch. 05

A Boss, A Mentor, A Lover Ch. 05

byjohnwhoknew©

Carrie lay on the bed staring up at me seductively. She propped herself up on her elbows, and opened her legs widely, revealing her gorgeous sex to me. She was naked except for her silky black stockings and garter belt, and I could see glistening wetness shining between her legs. It was time for me to pleasure her, to pay her the same level of devotion she'd just shown me.

I unfastened the top button of my shirt. It was all I still had on; I'd removed my pants long ago when Carrie had sucked my cock so gloriously. "Do it, slowly," she prodded, "make it exquisite." It was the same demand I'd made of her earlier, and she was trying to get a rise out of me. I gave her no such pleasure.

"Only the master can make demands of the slave," I retorted, though I curled the corners of my lips up in a devious smile. "Now tell me you're sorry, and rub your clit in penance." The same wicked grin crossed her lips when I said this, but she didn't resist me.

"I'm sorry, master," she said submissively. As she said it she raised her right hand to her lips and licked three of her fingers, getting them dripping wet with her spit. She then lowered her hand between her legs and began rubbing the top of her pussy in a circular motion. Her breathing sped up slightly as she did so, but she kept her eyes fixed on mine.

I unfastened each button on my shirt slowly watching her. I could feel my cock twitch as it hardened watching Carrie masturbate. She noticed as well as her gaze dropped from my eyes to my crotch. Once completely unbuttoned, I threw my shirt on the floor then stripped my undershirt off quickly and tossed it aside. I stood naked before her, my cock hard and throbbing. Carrie squeezed her clit between her index and middle fingers as she made long sweeping strokes up and down her cunt, her eyes once again staring into mine.

I knelt down beside the bed. "You are so fucking sexy," I said in a deep and throaty voice, desperate with desire. "Get over here." As I said this I grabbed her behind her knees and pulled her toward the edge of the bed. She moaned at my aggression and fixed her gaze deep into my eyes as I gently rested her thighs on each of my shoulders and lowered my face agonizingly slowly into her sex. I maintained eye contact with her as I kissed her pussy lips softly, and pressed my tongue between them. Her stare was intense, as though she were urging me to eat her with her eyes. When my tongue grazed over her swollen clit she finally broke eye contact, dropping her head onto the mattress and arching her back to meet my soft, slow licks.

"Time to cum for me, slave," I whispered hungrily between laps of my tongue.

"Anything you say, master," she whispered back. As soon as she said this, I sucked down hard on her clit, engulfing it within my lips and mouth. I sucked it greedily and made soft, flicking licks over it repeatedly, maximizing the sensations for her. Carrie arched her back further, and reached her hand down onto the back of my head, grabbing a handful of my hair and pulling my face deeper into her. I put my hand just under my chin and pushed two fingers into her pussy. Her lips gripped my fingers tightly, and I hooked both fingers upward inside her searching for her G-Spot. When I found the tiny, soft, granulated area on the roof of her vagina, she bucked her hips in reaction and grunted.

I knew she was entering the throes of ecstasy now. I began a steady, unrelenting pace of long, hard licks from the entrance to her vagina up over her clit. As I licked, I massaged her G-Spot with soft, swirling strokes, working my fingers slowly into and out of her. Her clit was engorged and swollen, almost pulsating as I licked and sucked it fiercely. Carrie was moaning my name and swearing in a steady string of sexy profanity. "Oh Jim, oh fuck, Jim, fuck... me..."

I kept my pace steady and rhythmic, coaxing her toward her peak. As she neared climax, she bucked her hips into my face repeatedly, keeping her hand behind my head to hold my mouth firmly down on her sex. Her juices became thicker, and my mouth began to fill with her heavy fluid. Her breathing became frantic and quick; I knew she was about to cum in my mouth. But just as the moment seemed ready to engulf her, she put both hands on my cheeks and pushed my mouth off of her, sliding her hips back away from me suddenly, my fingers slipping out of her cunt.

"No!" she gasped breathlessly. "No, Jim, make me beg for it. Make your slave earn her orgasm." She lay on the bed panting, gazing up at me with pleading eyes. I knew how badly she wanted to cum, but still she was gearing this encounter for my pleasure.

"Ok, slave, come here and kiss me then," I told her, knowing full well that her pussy juice was heavy and thick on my face. She scooched herself forward on the bed and did as I asked, leaning forward and kissing me passionately, her tongue lapping her nectar off my lips and chin. After a minute of long, wet kisses, I affirmed my authority once again. "Now... beg me to eat your sweet pussy until you cum."

"Please eat my sweet pussy until I cum, master," she implored. I pushed her shoulders gently back down onto the bed, and stood above her.

"First... turn over, slave," I commanded. Her eyes widened for a split second, but she obeyed instantly. She flipped over onto her stomach and raised her hips up off the bed ever so slightly. I hooked my fingers into the straps connecting her garter belt to her stockings and pulled gently upward. Carrie got the hint and pushed her ass up toward me. I knelt behind her and squeezed her ass cheeks, kneading my fingers into the soft flesh. Then I lowered my head slowly and ran a long, wet lick up the length of her ass crack.

"Oh... my... god," Carrie cooed in disbelief as I ran my tongue over her, putting heavy emphasis on the last word. It was the same utterance of disbelief she'd made the first time we fucked and I turned my attention to her ass. I guessed she wasn't used to being pleasured in such a way. I squeezed her ass with both hands again, this time spreading her cheeks gently apart. The taut, dark brown, little rosebud of her asshole puckered suddenly when my warm breath hit it. I flicked it lightly with the tip of my tongue several times, drawing little squeaks of pleasure from Carrie with each flick. Then I descended on it hungrily, lapping at it with hard, long strokes, getting it soaking wet and soft. She buried her face into a pillow to stifle her loud and guttural groans as I placed my palms flat on both of her cheeks and spread her as wide as I could, giving my tongue unhindered access to her tight hole.

She reached her hand up under herself and began to stroke her clit furiously. I hardened my tongue and pushed it as far as I could into her asshole, tongue-fucking her as deeply as I could go. Her groans began to border on screams as her fingers increased their intensity on her clit and I pushed my tongue furiously into her ass.

After several minutes, I finally pulled my tongue out of her ass and flipped myself over underneath her so I could lick her clit again. Carrie pushed herself up slightly so that she was sitting on my face. I pushed her hand out of the way and sucked hard on her engorged nub. She pulled her face out of the pillow and groaned as I licked her clit. "Oh fuck, I am so close, Jim," she cried. Hearing her say this I knew it was time to give her the pleasure she'd delayed so long. I reached my hand up and pushed my middle finger into her pussy and rested my index finger at the entrance to her asshole. I swirled my index finger around her hole several times, pushing very gently against the tight muscle holding it shut.

"Do it," she whimpered, letting me know she was ready to be entered. I pushed my finger in just past the muscular resistance, and left it inside her only as deep as the first knuckle. I swirled it gently around inside her ass as I stroked deeper into her cunt with my middle finger. I didn't want to hurt her by going too deeply too quickly. She, however, wanted no such courtesy. "Fucking do it," she demanded imploringly. At her request I pushed my index finger deeper into her asshole, all the way to the second knuckle. She groaned approvingly.

I then began stroking both fingers into and out of her, my middle finger in her cunt and my index finger in her ass. My fingers were separated by just a thin sliver of flesh, but it amazed me the difference in feel. Her pussy was tight and soft, but the velvety flesh yielded welcomingly and opened to my touch. Her asshole on the other hand was tight and muscular, and it gripped my finger firmly, almost resisting my entry. I could only imagine how heavenly it would feel to have her little hole wrapped around my shaft, to feel the strong ring of muscle squeezing my cock, while her soft, silken interior enveloped it with a warm, smooth sheath.

I continued to suck savagely on her clit as I sank my fingers even deeper into her. Soon both fingers were buried to the hilt and I was swirling them inside her to raise the intensity of her sensations. She bucked her hips wildly and moaned incoherently; I could tell her climax was nearly imminent. Just when I thought she couldn't possibly stand any more, she suddenly reached both of her hands down under my head and pressed her pelvis into my face so hard she cut off my breathing. Her orgasm washed over her like a wave and she punctuated it with a long, loud, "Ohhhhhhhhhhhh!" until even that was cut off by her pulsations and became just several rhythmic huffs of air involuntarily escaping her lungs. My fingers were buried as deeply into her as they could go, as the spasms of her climax caused the muscles of both her vagina and her asshole to pulsate rhythmically, squeezing hard on my fingers. It was as though her entire sex now had a pulse, and each beat sent wracking waves throughout her body.

I gradually slowed the intensity of my licks on her clit, and the swirling of my fingers inside her, as her orgasm began to subside. She released her grip on my head and freed my airway to breathe normally again. After several moments I slipped my fingers slowly out of her, and slid out from underneath her. I again stood by the side of the bed and looked down at her. She was on her hands and knees and looked back at me seductively.

"Baby, you came so hard," I said, almost in disbelief. It was true. Carrie's orgasms were very intense. Perhaps more than any other woman I'd brought to climax, Carrie's orgasms seemed to grip her entire body, as though she had pent-up energy, aggression and desire stored inside and they all came erupting out of her simultaneously.

"I know, baby," she replied, "you drive me so fucking crazy it just makes me explode."

"I love the way you explode," I told her, then I reached my right hand down and began stroking my cock. It was rock hard by this point and I was dying to put it inside her, to feel her warm, moist softness. She watched me stroke myself with wide eyes for several moments, her jaw hanging agape.

Finally she said, "If you don't fuck me now, I'm going to go absolutely insane." I wanted to dive right into her immediately, but I couldn't resist continuing our little game.

"How many fucking times do I have to tell you to ask me nicely when you want things, slave?" I asked tauntingly. Her eyes flared momentarily, her brows furrowing impudently. But again she relented and appeased me.

"Please fuck me, master. You made me cum so hard, I just want to please you now." Upon saying this she reached both hands underneath herself and ran her fingers along either side of her pussy. She used her index fingers to spread her petals apart and open her cunt widely. It was such an incredibly beautiful sight; the entrance to her vagina was dark pink, almost red, engorged as it was from her orgasm. Her lips were puffy and swollen, and her wetness glistened invitingly.

After drinking in this beautiful sight for a moment, I kneeled on the bed behind her and positioned myself just above her. I pressed the head of my cock against the entrance to her vagina, and teased her once again. "Beg for it, slave."

"Please fuck me, master," she cooed.

"I'm not convinced you really want it. Convince me."

"Please fuck my pussy, master, I want it so bad."

"I'm almost fucking convinced, baby; tell me your pussy is wet for me."

"My pussy is soaking wet for you, master."

"Now tell me you've wanted this all day."

"I've wanted this all day every day for a year."

"Oh god baby, me too. Now tell me you wore that suit to make me want to fuck you."

"No," she replied matter-of-factly and turned back to look me in the eyes. "I wore the suit because ever since that day you told me how sexy I look in it, every second I'm wearing it around you I get soaking wet between my legs." She jutted her lower jaw out and flared her nostrils in defiance when she said this, expecting me to hold it against her, to force punishment upon my slave for not doing as I asked. But the realization that came with hearing her say it, to now know that she desired me as badly as I did her, made a wave of affection wash over me. I forgot our game and instead reached my left hand out to grip her hip and pull her gently into me. With my right hand I guided my cock past the tight resistance at her entrance, and sank it deep into her cunt, gently and smoothly.

Carrie gasped for a moment when my cock pushed into her, popping past her threshold and spreading her open. Her eyes rolled up for an instant as I entered her, but then she looked deep into my eyes again, urging me to take her completely. As I sank deeper we both moaned contentedly, our bodies reunited at last. I thrust as deeply into her as I could, then held my cock still inside her. I wrapped my arms around underneath her, and pulled her body into mine. I buried my face into her neck and whispered in her ear. "God, I've dreamed about this moment."

"Oh, Jim," she moaned. I ran kisses along her earlobe and down the nape of her neck, flicking my tongue in her sensitive areas to turn her on. I backed my cock out slowly, all the way to the tip, then sunk it in again just as slowly. After I'd repeated this slow, smooth thrusting several times, I began to quicken the pace. I leaned back behind her and grabbed her hips with both hands, guiding her motions as I began thrusting in and out of her quicker and quicker. Carrie swirled her hips in a circular motion with my thrusts, meeting my rhythm stroke for stroke. The sensation felt amazing, our bodies in sync and working perfectly together. I pulled her close to me and ground my hips against her thighs, her ass pressing into me.

"Fuck, Carrie, you feel so fucking good," I moaned.

"Mmmm, do you like the way I feel inside?"

I buried my cock to the hilt and pulled back on her hips, pinning her ass to me with my cock plunged deep into her pussy. "God yes," I said, "you're so warm and tight." I began swirling my hips and Carrie followed suit. She twisted around and put her hand on the back of my neck, pulling me down to kiss her. She pushed her tongue into my mouth and swirled it around, mimicking the motion of our sex. I sucked her tongue and massaged it with my own, never breaking rhythm with my thrusts. After kissing passionately and aggressively for several moments, Carrie finally broke the kiss.

"You like me nice and warm and tight?" she asked breathily.

I kissed her again several times. Between kisses I said, "God... yes... I just wonder..."

Carrie broke off our kiss again. "Wonder what?"

I leaned back and slid my hands from her hips onto her ass. I squeezed her ass cheeks in both hands and pushed them wide apart. Carrie's jaw swung open as I spread her, and she jutted her lower jaw out and fixed her gaze upon me as though she could read my thoughts. I ran my finger in a little circle around her asshole, pressing gently against her soft, sensitive flesh, still moist from my earlier ministrations. "I wonder... how warm and tight your little asshole must be," I said lustily, letting my finger slip slightly inside her, her muscle gripping it tightly. I slowed my thrusts into her pussy down to an excruciatingly slow and deliberate pace, teasing her. She continued to thrust her hips back and forth into me, sliding my cock in and out of her. All the while she maintained eye contact with me, willing me to fuck her harder.

Finally, after several moments, she said, "Then why don't you find out?" When she said this, I pushed my finger deeper into her ass, and leaned down and kissed her mouth again. This time I pushed my tongue into her mouth, and she massaged it with hers. I pulled back gently and my cock slipped slowly out of her pussy. I broke off our kiss then made a trail of kisses and licks down her back until I came to her ass crack. I pulled my finger out of her asshole and replaced it with my tongue, swirling it in circles and pushing it gently inside her. Carrie dropped her face onto the bed and groaned throatily. I ate her ass lustily for several minutes, moaning along with Carrie as I lapped at her hole.

Once I had her ass dripping wet again, I raised myself up behind her and pressed the tip of my cock into her crack. "You want me to find out how tight your little ass is?" I asked her.

"Oh god, yes, do it," she moaned.

"Do what? Tell me, slave."

"Fuck my ass and see how tight it is for you."

"It's for me?"

"Oh fuck yes, it's all yours." Hearing her tell me her asshole was all mine drove me over the edge. I spit onto my palm and rubbed my saliva over the tip of my cock, which was still wet from Carrie's pussy. Once I rubbed it with my spit it became slick and lubricated, ready to enter her. I then pressed my cock forward against her hole, guiding it with my thumb on the tip. She gasped as her hole opened and enveloped the tip of my cock. I paused before letting it sink any deeper, knowing she would need a moment to get used to its size. I kissed the back of her neck softly, reassuring her that I wouldn't move too aggressively and hurt her. She moaned in response to my kisses, then urged me to give her more. "Do it," she prodded, just as she had earlier.

I thrust my hips forward gently at her request and groaned as my cock sank slowly and deeply into her. Her sphincter muscle clenched tightly around my shaft, gripping it firmly. Once inside her, I let her ass cheeks go so that they would tighten around my cock and provide a cushion for my thrusting. I put my hands on her hips and pulled her back into me, providing leverage so that I could bury my cock into her ass as deeply as it could go.

"Mmmmff," Carrie spluttered as the girth of my cock sank deeper into her. Her breathing had become shallow and I knew she was adjusting to having something as big as my cock inside her. I willed myself to hold still so that I didn't hurt her; it wasn't easy with how warm and satiny her tight little asshole felt on my dick. After several moments her breathing steadied and she reached her hand back onto my hip, willing me to give her more. I relaxed at her urging and plunged my cock into her as deeply as it would go. This time she moaned contentedly as I filled her, adjusting completely to how stretched her hole was to accommodate me. She arched her back and growled into my ear, "Fuck me, master."

I grabbed a handful of her hair to keep her back arched, and slid my cock slowly out of her to the tip. Then I sank back into her, slowly but determinedly. She groaned with my thrusting but it wasn't from pain. She was adjusted to my size and I could tell it was starting to feel pleasurable for her. I slowly increased the rhythm and depth of each thrust until we were fucking loudly and aggressively. Carrie was grunting on every thrust into her, almost shouting with intensity. "Uh... uh... uh... fuck yes!" she yelled.

I, in turn, groaned into her ear on every thrust, a sound primal and animalistic from deep in my throat. It felt so unbelievably filthy and naughty to be fucking this woman in her ass. On one hand, Myers was right. She did come off like an ice queen at work. Based solely on how she acted in the office, one couldn't possibly imagine she would be willing to take it in the ass. She always had control at work; she always knew the answer to everything and she insisted on being one step ahead in every matter. She was calculating and exacting, not cold exactly, but she always wanted to be in control and she always commanded unequivocal respect. It was impossible to imagine, knowing her solely professionally, that she would sacrifice her control this much. That she would open her most secret place and share it willingly and lovingly. Yet here I was, balls-deep in her asshole, thrusting into her with wanton abandon.

Report Story

byjohnwhoknew© 12 comments/ 107085 views/ 22 favorites

Share the love

Report a Bug

Next
4 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel