Any Given Fantasy Ch. 03

AUTHOR'S NOTE: The idea for these stories were inspired by "The Jerk-Off Sessions", written by the author Hearsz, who has given his permission to allow me to use a similar format.

*

My session with Ms. Grammer seemed to pass by faster than it usually did, with me mostly giving one worded answers as my mind why these blackouts were happening. My mind was completely exhausted from what had transpired over the hour with my fantasy/blackout of Alison Brie. So as our session was wrapping up I knew that another potential blackout was unlikely to happen as Ms. Grammer was wrapping things up.

To be honest I was still worried because Ms. Grammer wasn't no ugly duckling, she was a hot MILF. So it worked in my favor that our session was wrapping up.

"You're making progress Jake, that's good," Ms. Grammer said as I stood up from my seat.

If she only knew the things involving the blackouts that happened this morning a d afternoon. We shook hands and I quickly made my way out of her office. I closed the door behind me and hurried down the hallway wanting nothing more than to just get home.

****

Monday evening...

On my way home it went without a problem, but as I walked through the front door, it did play on my mind how I was going to get through the rest of the day, without letting my sexual urges take over sending me into another blackout. Especially since I'd basically be home by myself for the rest of the day, my dad on a business trip, my step mom staying at work late for after hours and my little sister was on some school camping field trip.

I treated myself to pizza for dinner and was planning on diving into some graduation project that wasn't due in a couple of weeks and then just go to bed early. I figured working on some boring project for most of the night would knock me the heck out, thus stopping any chance of a repeat of either of this morning and afternoon events.

I cleaned up after dinner and prepared my clothes for tomorrow, taking out some swimming trunks as well, as I hoped to hit the beach first thing in the morning as my class had a field trip and I decided against going, besides going to the beach was something that I usually did as the beach helped clear my head. Jumping on the couch, I decided to watch some TV while drinking a coke and working on my graduation project. I made sure to avoid channels and shows that could potentially trigger a blackout and lead me to the point of no return. I really couldn't afford to let this problem of mine keep affecting my life.

I wasn't much of a sports guy, but I figured watching sports would be the best way to go since it was the safest option. More specifically, some chess competition.

"There's no way I'll be seeing any cheerleaders in chess," I said out loud to myself.

After finishing my pizza and coke and with with chess competition coming to an end, I reached for the TV remote, looking to turn the volume down so I can finally put my full focus on my project, but to my dismay I accidentally turned the channel instead of turning down the TV.

It was now after midnight and I began to yawn as I got tired as I looked up at the TV, the mini guide popping up on the screen to tell me what channel I had turned to and it was a repeat of the show called "The Client List". When that show was on I heard about what it was about, but I never gotten a chance to watch it. There was a guy lying down on a table, with only a towel covering his private parts, talking to a woman who wasn't on screen at the time...

And then just like that I was gone. I blacked out and suddenly my eyes opened, but I was no longer in the living room. I looked around the room confused with surroundings.

"Sorry for the delay, I'll be out in just a second," a women said, not to far away, but still out of eyesight. As I laid there on what appeared to be a massage table, with just a towel covering me from my waist down to my feet. I was naked underneath, but the room was warm by the temperature turned up in the room and that's not evening including the excessive amount of scented candles.

The room looked oddly familiar, like I'd seen it before, but when the women from behind the screen walked out to greet me, it was someone I'd been familiar with since my early teens.

"Are we all nice and comfortable?" Jennifer Love Hewitt asked looking so damn sexy in a black see-through negligee, with red roses designs all over it.

The outfit hugged her exquisite figure tightly, showing off her long well toned legs down to her beige colored sandals. Her twin assets for which she was always well renowned for, were on show to my more than appreciative eyes and pleasure. Her outfit allowed me to hungrily eye her ample chest, with only the bottom half of Jen's 36C sized mammaries covered by the lacy material.

"I bet you've been looking forward to this all day huh? Waiting all day long, couldn't get your mind off of it, I bet," Jen asked seductively, running her pointer finger from the top of my chest, then her entire palm caressed my quivering stomach.

I couldn't even answer her as I was mesmerized by that delicious hanging rack. Jen let out a sexy little laugh as she dipped her fingers in a bowl of massage oil. She rubbed her hands together and gave me a quick smile, pressing her hands against my chest. She lathered my chest and stomach up with her oily fingers as I lie there admiring her skillful handy work.

"No need for you to be nervous or anything. Feel free to touch me wherever and whenever you like, I'm all yours for the night," Jen said as she started to oil up each of my arms.

As she leaned over me to massage my right arm, my decision was made up for me, as she bent that plump ass of hers out for my amusement. While she continued to massage my chest, I reached out to run a hand up her firm soft thighs, squeezing them lightly with my fingertips. As I ran my fingers upon her hot pussy, all I could think about was how I'd love to fuck her good.

It seemed as if Jennifer loved that I was giving her equal attention. She enjoyed it even more as my hand sneaked around to the back of her legs, teasingly snaking up them and then under her short, short negligee, and upon her tasty looking rump. She squealed in delight as I pinched and fondled her ass, running my fingers in between her enticing ass crack. I gave her ass I good slap that made her wiggle her ass for me as she gave me a seductive smirk.

The actress starlet now seemed like the one being given the special treatment, as she started to push her backside against my invading hand. Leaning back up, she took a hold of the bowl of massage oil, held it against her chest and poured it all over her amazing grand cleavage.

The oil completely soaked the front of her sexy negligee, my cock now starting to twitch as her hard nipples became visible through the thin material. Jennifer took my hand from her thigh and placed it upon her oily breast, motioning me to fondle her large tit. Her breast was as full, soft and warm as I'd imagined since I first discovered her.

My cock started to elongate and thicken as I felt up each of her juicy oil covered tits, the towel covering it beginning to make a tent. As I played with Jennifer Love Hewitt's fantastic orbs, she resumed oiling me up around me stomach. I could see she only had eyes for one thing, as she slid my towel down and onto the ground.

"Oh damn," she exclaimed, in shock at how hard she had made me. I have to say I was somewhat surprised too, as I was so horny that I felt hot. The look of lust that crossed Jen's face as she gazed at my hard cock, was making me more horny than ever.

Dipping her fingers in oil again, I groaned as her soft hand closed around my hard throbbing cock, the puddle of oil that initially sat in the palm of her hand now ran down my cock and over my balls. Jennifer started stroking up and down the length of my cock, my grip tightening upon her breasts as she did this. My oiled up cock made it easy for her to slide her delicate fingers up and down my large cock.

With a flick of her free hand, Jen slipped both of the straps off each of her shoulders, allowing her succulent tits to hang free only inches from my face. Her areola was a darker shade of brown to the hard pointy nipple, which sat so perfectly in the center of each of Jen's magnificent breasts. Like a child desperate for candy, I wasted no time in grabbing those big tits forcefully in each hand, mashing them together which caused Jennifer to grip and stroke my cock with equal intensity.

As I pinched and tweaked those pointy nipples, Jen had started to caress the head of my cock with each tip of her thumb and fingers, rubbing the head of my cock. Her silky fingers felt so good on the tip of my cock, and when she rubbed her spare hand over my balls. it felt like I could be about to experience the eruption of a lifetime.

Jen's delectable fingers caressed each of my balls and hard cock so effortlessly, as it soon became a game of who could get the other off first. Keeping one hand on her chest, I slipped a hand underneath the front of her short negligee, and in between her legs. To my delight she wasn't wearing any panties, which allowed me to run my fingers across her juicy pussy lips, already wet from my breast play.

As Jennifer ran her fingers through my pubic hair, I used my pointer finger and thumb to part her fleshy pussy entrance, and slide one of my pointer finger up inside her warm wet opening. The heavy chested brunette's eyes closed in lust as she accepted my invading finger, her body wriggling to help me slide a second finger inside of her. As her stroking of my cock became more slick, my fingers jabbed upward inside her just as quickly. Jen looked so sexy as she moaned and bit her bottom lip, and it was at that time I could feel her warm juices start to gloss my entire working hand.

As I continued to finger fuck the busty celebrity, Jennifer released my cock. Then with a single look, a reach behind to her back, the faint sound of a zipper moving down, and her negligee dropping to the floor, leaving her completely nude in front of me. My cock bobbed freely against my stomach at the sight of Jennifer Love Hewitt's naked body, with two of my fingers still inside her warm entrance.

"Am I everything you dreamed I would be?" she asked so sultry.

"Oh hell yes Jennifer. More than I had ever imagined," I replied.

Jennifer's voluptous figure, large tits and gorgeous face were mine to savor, but things were only just starting to heat up. Taking a firm hold of my cock again, Jen leant forward which allowed my fingers to delve inside her to the first knuckle, causing a slight moan from the actress.

She moved her chest toward my groin area, holding my dick about halfway up and pointing the head toward her areola and hard nipple. Jennifer rubbed the crown around her nipple and rubbed it in circles, then doing the same with the other. She smacked my cock against her fleshy orb, her twins giggling as she did this. I fingered her more frantically now, and it was that point she wanted to continue the massage in a different direction.

As we released our hands from each other, Jennifer coated her hands with some more oil and teased me some more by pouring it over her huge breasts. I watched as it dripped down her taut stomach and in between her thighs and down her shapely legs. I wanked my cock as I watched her feel up her big tits, my eyes widening as her oiled up titflesh seemed to expand in her hands as she greased them up. She lathered every inch of her womanly body up, and without a word, hopped up onto the table, and sat her glorious shaven haven over my surprised face.

So there I was, lying naked on a massage table with Jennifer Love Hewitt's oil drenched body on top of mine, her hand stroking my dick, and her full round ass and shaved pussy just centimeters from my face. I prodded and probed at her fleshy goodness, running my fingers along her juicy slit. I parted her aroused pussy lips, gazing at her offering, and without anymore hesitation, dove my face in with intent, attacking her dripping hole with my tongue.

"Ugh, oh fuck yes!" Jennifer exclaimed, the sudden action taking her by surprise. Her stroking of my cock had slowed a little bit, as she took time to relish my tongue and mouth lapping at her tasty pussy. I stroked my tongue back and forth across her tasty slit, her warm honey pot getting more delicious with each drip of juice that leaked out of her.

Jennifer squeezed my cock each time my tongue flicked over her clit, her doing this was letting me know that I was hitting the right spot. She reached back with her oily fingers to grab one of her plump butt cheeks, pulling it to one side in order for me to get my tongue inside her deeper.

I could feel Jennifer's moaning breath upon the tip of my cock, and knew those sweet soft lips were ever so close to the head of my cock. I desperately wanted her to open up her pretty mouth and wrapped those exquisite lips all the way down my cock, but the more I ate out her peachy tasting cunt, the more she seemed to await the next move with my tongue, rather than attend to my throbbing cock. Her husky sounding grunts spurred me on further.

Jennifer slid her slippery body back and forth across mine as I continued my oral assault on her pussy. Her large mammaries were pressed against my stomach, and I could feel her eraser like nipples digging into me. Her tits had felt great in my hands, but even better now that they were essentially massaging the front part of my body.

As I rested my hands on the back of each of her sweaty thighs, Jennifer resumed her elegant stroking of my dick, using both of her hands now. Her body raised slightly off of mine, allowing me to look in between our heaving frames, and get a good view of what she was doing in between my legs. It was as though she was willing to do anything to make me cum and then the dirty talk started.

"Mmm, your cock looks so yummy baby. I've massaged plenty of men, but your cock is impressive, ugh!," She moaned.

My cock was throbbing like crazy now, every word Jen uttered seemed to cause more than a few tingles in my balls as I now fingered her dripping cunt with harder strokes, while watching her attend to my more than ready to burst cock. Our multiple pleasuring seemed to be in sync now. As my tongue licked up her moist slit, her hands slid up and down my oily cock within the same time.

"I wanna give you a treat baby, just for you. A titty fuck," Jennifer said seductively. My eyes lit up at the thought of getting to fuck Jennifer Love Hewitt's big tits.

She gets down on her and drops forward between my knees, her gargantuan cleavage wrapped around my crotch and her hands on my knees. She has a sexy smirk on her face.

"Do you want my big soft oiled titties?" She teases, her cleavage still jiggling uncontrollably near my rapidly hardening cock.

"Oh you know I want your tits you hot slut", I interjected, as I mash those massive c cups together and give them a good squeeze. "My cock is gonna ride right between those awesome titties of yours!"

Jennifer licks her lips seductively, as she reaches down and slowly starts jerking me off again, allowing her mega-mams to drop freely. I grab the towel over me and toss it on the floor releasing my hard cock and prepare to lay it right between her milky-white bosom.

Her sexy brown eyes widen in anticipation as I grasp my cock and point it directly towards her chest...

"Fuck... Hot damn!" I mutter under strained breath as I ease my thick, hard rod between Jennifer's massive mammaries... "They feel so damn soft!" I groan in ecstasy.

Jennifer has a slutty, smile on face as her hands are now gripping her tits tightly around my cock and pumping up and down in a nice tight vice. I'm in awe at how soft and warm her breast are, her tits are so soft and supple.

"Oh yeah slut!" I spit out at her, placing my hands over her own as we both grip and slide her ample bosom tightly around my cock.

"Damn your tits are so fucking soft! So fucking big! I always jerked off thinking a out this, but now it's happening. Feels so good!" I manage to say through grunts, thrusting and undulating my hips up and down to the sawing motions my cock is now experiencing within the confines of her billowy chest.

"Oh yeah you naughty boy," Jennifer retorts, beads of sweat forming on her forehead and between her cleavage from the steamy hot tit fuck that's taking place.

"Oh, baby you're my special client. You cock feels so good between my breast... You like fucking my titties don't you baby? You like the way my big boobs bounce and jiggle all over your cock, huh? Do it baby, do it! Fuck my tits! Fuck'em harder!" she challenges, her breath coming in short, breathless gasps as I continue to pummel her famous hooters, my hips going up and down at hyper speed.

"Oh fuck! Oh fuck!," I scream, reveling in the sublime pleasures of her fleshy melons imprisoning my seething cock as it continues to plow forward and back between the MILF's milk jugs.

"Oh damn, I love fuckin' your tits you sexy bitch! All those times I jerked off to you, watching you tease me with those massive melons - now I'm finally fucking them! Feels so fuckin' good!"

I was surprised with what I was saying, but it was true and I couldn't help it.

"That's it, baby," Jennifer groans, continuing to pump my cock with her titty-trap, "keep pumpin that cock between my tits! Your fucking the tits that a lot of men want to fuck so do it baby! Fuck'em hard! Fuck'em long! Fuck'em deep! I wanna feel your cum all over my titties! Grease'em up with your cum!"

With the sensation of fucking Jennifer Love Hewitt's oiled big tits and the way she's dirty talking, I wasn't sure if I could hold out from cumming much longer, but I knew if I also wanted to fuck her, I better try harder to hold out.

"Arrrgh!" I groan, her dirty talk getting me so charged up, "Spit on your tits, baby! Spit on my cock, get it nice and lubed up!" I firmly tell her.

"Whatever the client wants," Jennifer said with a slutty smirk.

Smiling, Jennifer tilts her chin down and lets loose a long dribble of her saliva all over her cleavage and the head of my cock, as it continues to poke up through her mountainous cans. She even teases the tip of my cock by licking the top of the head, causing my eyes to roll into the back of my head from the extreme pleasure. Soon her tits and cock are all greasy, covered in oil and spit. I still continue to hammer her chest in a non-stop crescendo of melon-balling lust filled frenzy.

I can feel my cock beginning to throb and know that it won't be much longer...

"Come on, shoot that delicious cum all over my big titties," Jennifer begged, as she slickly jerked my cock, trying to force it.

"Or maybe you want to paint my face with that tasty cum. Go on, do it! Cum on my pretty face and big tits, I want it bad!" She said through moans and grunts.

I dropped my head back and closed my eyes, feeling my cock about to burst. I raised my hips as she stroked me, her spare hand now squeezing and fondling my balls. That did it..

"Mmmph f... fuck! Oh fuck! Here it comes!" I yelled, the hot sperm in my balls rocketed up the long length of my cock and spewed firstly into Jen's agape mouth, the next upon her rosy cheek, upon her pretty lips, and finally all over her big tits.

Jennifer Love Hewitt kept milking my cock, the remaining cum bubbling out of the tip and rolling down my shaft and upon her oily stroking hand. As the last of my cum exited my cock, and Jen had pulled on it for the final time, my eyes closed shut...

TO BE CONTINUED