My bosses administrative assistant

Gareman

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Jun 2, 2000
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OOC: I'm looking for a female writer to play the role of my bosses administrative assistant (Carol Baker). I am new to the sales team at A & K Software, fresh out of college. Carol is a married woman in her mid to late forties who has taken me under her wing and given me many good pointers. She has a deep understanding of what Mr. Larkins wants from me and has helped me score points in the two months I have been with the company.

Carol is a conservative woman who has never cheated on her husband (Joe) of 28 years. She has 2 sons (Joe Jr, and Mark) who are both on their own now.

Our relationship is that of friends, but I suspect that will change very soon....

My character is Jason Chambers, 23 years old... 6'0" 180 lbs... blonde hair, blue eyes...

Any willing females ??????

IC: I hadn't expected anyone to be at the office this morning. Needing to finish up several important tasks, I thought I'd stop in today (Saturday) and get caught up...

Opening the door, I immediately smelled coffee brewing and noticed the lights on. I walked to my office, placed my briefcase on the desk and removed my coat. This winter had lasted way too long and I was really getting tired of having to bundle up every morning before leaving the house. Walking down the corridor to the kitchen area, I saw Carol pouring herself a cup of fresh-brewed coffee...

"Hey Carol, what brings you in on such a nasty day ?"
 
OOC: Gareman, this might be a bit of a stretch for me (married with grown kids), but I'd like to try, if you don't mind? Could be kind of fun!

Character Desicription: Carol Baker, 42, works out regularly, so the ravages of time are not as apparent. In fact, she has been told she still looks like a woman in her 30s. She's got dark auburn hair, green eyes, and is a little bit of a flirt. Loves her husband, but things have become a bit routine between them, though she would never think of doing anything to ruin or harm her marriage.

IC:
Waking up that morning, I kept thinking of that report that was due on Mr. Frank's desk first thing Tuesday morning. Mondays were always busy, and I wasn't sure if I would finish it in time so I figured I'd go into the office on Saturday and get some work done.

Slipping into a pair of snugly fitting jeans and a sweater that even I had to admit showed off my breasts to perfection, I bundled up and headed for the office. My husband would be busy in the basement all day with one or another of his projects anyway, so I might as well be productive.

When I arrive at the office, no one is there. That always gives me a creepy feeling, but then I should be able to complete that report rather quickly and get out of there. I step into the breakroom to make coffee to allow the caffein to wake up my brain. As I pour a cup of coffee, I suddenly hear a voice and jump, nearly spilling the entire cup.

"Oh, my god! Jason! You scared me half to death!" I smile at him as I catch my breath.

Starting to wipe up the spilled coffee, I see him begin to laugh, and I have to join in - it must have been a comical scene at that.

"I need to get that report finished for Mr. Frank today....you know how he can be about deadlines, remember? Thought I could get a lot done this morning. And what brings you in today? Shouldn't you be home nursing a hangover from last night, or recovering from going out with some nice girl?"

Jason was a cutie, I had to admit. I also had to keep telling myself that he was young enough to be my son - in fact, I believe one of my sons was probably around his age. Still, I never could keep myself from flirting with him...just a little. After all, no harm in that, is there? I mean, what would a good-looking young man see in a woman almost twice his age?
 
OOC: I'm sure you'll do a wonderful job SexyChele !!


IC: I wasn't used to seeing Carol dressed so casually. She usually wore very professional business clothing. I had to admit that she looked very good for a woman her age. The tight jeans and provocative sweater gave me a new appreciation for the nicely maintained body that was usually hidden from sight.

I fought unsuccessfully to keep my eyes from lingering on her round breasts. Ever since my early teen years, I have had a thing for older women. While my contemporaries lusted after classmates, I had always secretly fantasized about teachers and adminstrators.

Carol had somehow escaped my attention, flying below my radar and projecting a friendly, motherly image. Oh, there were the flirtatious comments that she threw at me, but I dismissed them as her way of breaking the ice and making me feel welcome in my new job. Now that my radar had zoomed in on her, I definitely hoped they were more than that.

Smiling back at her, I decided to flirt a little myself.

"I've got a little work to do on Mr. Frank's presentation," I replied.

"And what makes you think I'm looking for a 'Nice' girl ?" I said smiling a devilish grin. "I think I'd prefer one that is a little 'naughty'. Do you know anyone ?"

I gauged her reaction, hoping I hadn't gone too far. I felt a flutter of excitement begin to shoot through my body. There was definitely something mischievious in those green eyes. I waited eagerly as she opened her mouth to speak...
 
I peered over my coffee mug at him, then gave him a small smile.

"What? You still not looking to settle down, yet? Still interested in sowing those wild oats, huh? And do you have many 'naughty' girls to keep you busy, Jason? It seems a good-looking young man such as you would have girls chasing after him all the time, I'll bet."

As I noticed his eyes drift over my body, I felt myself flush slightly. Turning, I start to busy myself with wiping down an already clean counter-top, hoping he won't see the slight pink that colors my cheeks.
 
I noticed a slightly embarrassed look cross her face, as I continued to eye her mature body. I liked the feeling of control it gave me to push her to her limits.

"Well Carol," I replied, "I wouldn't say they are beating a path to my door."

I smiled as I walked over, standing next to her to pour myself a cup of coffee. I intentionally stood closer than I needed to, invading her personal space...

"Since I moved here, two months ago, I've been so busy I haven't really had a chance to go out."

I finished pouring my coffee and continued standing close, turning to face her. There was a moment of slience, as we both took a breath, surveying our "conversational footing" and trying not to say anything too foolish.

"But thanks for the compliment... I mean... it means a lot to me."

Our eyes met again, and again mine strayed... studying her face...her neck...her breasts...

I waited for a response, wondering if she would move away to regain the necessary amout of personal space to feel comfortable.

I took a sip of coffee, my gaze returning to her mysterious eyes...
 
I barely caught what he said as Jason moved close to me to pour his coffee. The coffee maker was close to the wall, and I found myself with the wall behind me and Jason standing very close to me. I feel a bit uncomfortable, and start to feel flustered as I try to figure out exactly why.

As our eyes meet, I find myself breathing just a little faster than normal, especially as I notice his eyes drift downwards before coming back up to meet mine.

No, this can't be! I'm being ridiculous....he's just getting a cup of coffee, that's all. And, no, Carol, he is not checking you out. God, what am I thinking??

Still, I know that the pink in my cheeks is beginning to darken slightly.....and he's not moving even though he's poured his coffee.

"Well, um, Jason, the girls in this town certainly don't realize what they are missing then. I, for one, feel sorry for them. Ah, maybe you should try making more time to have a little fun, huh? It must be very lonely for you, and a girlfriend could really be a comfort to you."

God, what am I babbling on about? And why do I suddenly feel so uncomfortable being near to him? Involuntarily I find myself glancing over the length of his body and then realize what I've just done. Looking in his eyes once more, I can almost believe that he can read my mind.

"Well, I guess we should get to work, otherwise we could be standing here drinking one cup of coffee after another, exploring your love life!"

Cringing inwardly at my words, I pick up my cup and try to move past him.........
 
I smile inwardly, noticing her eyes scanning my body. I step back, giving her barely enough room to leave the coffee area.

"You're probably right," I answered, "we should get to work. But you've got to promise me that when we are finished, you'll give me some tips on where to find "naughty" women, in this town."

I take a sip of coffee, blatantly staring at her full breasts. I feel my cock begin to harden, imagining my hands squeezing those nice tits. Thinking about her, peeling off her sweater and bra and letting me enjoy her naked mounds is extremely exciting. I wonder what it would be like to have an older woman...

"By the way Carol," I ask boldly, "have you ever been "naughty" ?"
 
I try to slip past Jason, but there is only enough room if I brush slightly against him. I could almost swear he is standing there hoping for that to happen.

At his question about finding "naughty" girls, I hesitate...

"Well, Jason, I'm sure I wouldn't know. After all, I've been married to Joe for 25 years. Trust me, old married ladies don't know where to find the naughty girls."

I try to smile and play it off as simple flirting, but I can't mistake the look he is giving my breasts. As I look at his handsome face, I start to imagine what it would feel like to have his face buried between my breasts.

Almost as if he is ready my mind, he asks if I've ever been naughty. I blush bright red...

"Jason! I, uh, well, I suppose there were some times when I was younger that I did some, well, you know, things. Besides, it would all depend on what you mean by naughty, wouldn't it?"

Why were my breasts tingling as they were? And why was my heart racing as it was? No, I would just walk out of here, go to my desk, and start on that report.

I tried to flash Jason a smile as I slipped around him, when suddenly I felt his hand on my arm....
 
I can't explain what I was thinking... Maybe that was the problem, I wasn't thinking.

As Carol squeezed past me, I reached out and grasped her arm. Turning her to face me, I looked into her eyes...

"Do you really want to go to your desk and finish that report ?" I asked.

Her hand was trembling, as I took her cup of coffee and placed it onto the counter. My other hand remained on her arm.

Turning back to face her, I stared deeply into her eyes.

"You know Carol," I said, almost in a whisper. "I don't think I'm the only one here who could use a little fun."

My mind raced... I was extremely excited, but also a bit fearful. If she decided to file sexual harrassment charges, my job would be shit... I looked for a sign...anything, that would reassure me that I hadn't made a BIG mistake.

I waited for a response, prodding a little...

"Am I right ?"
 
His hand on me suddenly felt like fire burning through my skin. His eyes boring into mine, almost as if to my brain.

What was the question he asked me? Fun.....wanting to know if I could use a little fun....yes, that was it. When was the last time I had thought of having fun? The type Jason was referring to, or any other? Responsibility...that's what I had become well aquainted with over the years. And somehow fun had been edged out of the competition.

I look into Jason's eyes, and it is as if I can't pull them away. His meaning is unmistakable....or is it? Is he only trying to find out if I consider him to be an attractive man to feed his ego as he goes about his business?

I try to think back to the last time I had known a man who didn't have beer belly. A man who took his time to make himself attractive to women. Suddenly, I begin to imagine what Jason would look like without clothes - strong shoulders, flat belly, firm ass.

CAROL! My god, what are you thinking? Joe....think of Joe - a better husband a woman couldn't have. Considerate, good provider, generous. And yet......

I know my emotions must be playing across my face, and as I look at Jason I see him smile at me. Yes, he is aware of my struggle....somehow he is aware, though I've not uttered a word.

Looking Jason in the eye, trying to ignore the warmth of his hand on me, I speak to him almost breathlessly...

"Yes, Jason, all of us could use a little fun now and then. Some more than others, at times."

I feel his hand tighten slightly...
 
Carol's face said it all. I smiled as she acknowledged the need for "fun", but still sensed a reluctance, borne of 20 plus years of marriage and commitment to family...

"I understand your dilemma," I said in a quiet voice...almost a whisper.

Stepping forward, I place my left index finger gently on her upper lip and slowly begin tracing her mouth.

"The loving wife and mother, in you, enjoys the comfortable life it has taken all of these years to build... I'm sure you love your husband and don't want to do anything that may hurt him or jeopardize your relationship..."

As I spoke, I moved my finger along the upper edge of her lip, barely touching her skin...


"But..."

I moved my finger to the lower edger of her lip and began slowly tracing it...

"There is the other side...The adventurous part...that needs more. "

Stepping even closer, I took her hand and moved it down to the bulge in my pants.

"You've denied this part of you for so long... and now it's screaming for your attention. Remembering the passion of youth, it longs to go back... to forget all the obligations and responsibilty...to be free again. "

I hold her hand against my hardness, moving it along the length of my thick penis.

"How much longer can you deny this side ?"

As I ask the question, I place my finger between her lips, parting them slightly...

Lowering my head and placing my mouth to her ear, I offer these words, whispered...barely audible... "I'll make this easy for you...If you decide to continue living the life you've known, I will never make this offer again...But, if you decide to take the plunge...you are in it for the long haul...and the sky's the limit."
 
As Jason's finger lightly traces the outline of my lips, I begin to tremble. Have I ever experienced a man's hand so light on any part of my body before? No, I don't believe so. And though my mind was fighting, I found myself concentrating on his finger and discovered a strong urge to feel more than just his finger on my lips.

Then, suddenly, he takes my hand and places it on the bulge in his pants. My mind whirls at the thought that my hand is rubbing the hardness of another man besides Joe, the only man I'd ever known. The fact that the cock I was rubbing was that of a young man excited me even further. I feel his hand press my hand harder onto him, but he really doesn't have to do that. My hand is rubbing him of my own accord.

The last vestages of resistance are breaking down within me, with the closeness of Jason and the bulge of his hardening cock under my hand. My responsibilities were rapidly fading, and I was even able to push Joe out of my mind.

Once again, I could imagine what it would be like to be young and desirable, to have the attention of a man - young, strong, virile.

As Jason leans close to me to whisper in my ear, I find myself holding my breath. As he begins to back away from me, I place my hand on his cheek and draw him to me, my lips searching for his......
 
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I lowered my mouth to hers, the softness of her lips touching mine felt great. Her hand continued stroking my penis through my pants... Moving my right hand from her arm, down to her waist, I found the bottom of her sweater and began sliding it up underneath the soft material...

My other hand unhooked the button on my jeans and unzipped the fly, allowing Carol easier access to my long, thick cock... Now the only thing separating her from my manhood was my bikini underwear...

Opening my mouth slightly, I allowed my tongue to move forward, pressing against her closed lips, trying to pry them apart...


God this was wonderful... A true fantasy of mine... having an older woman... willing and ready to be with me.... And something told me that Carol would be special...
 
As Jason's lips touch mine, I feel the desire that once burned in my veins once more come alive. As his hand slid up under my sweater, I shuddered with delight as he touched the skin just below my breast. Afraid of feeling that, yet wanting him to continue, I pressed towards his hand, moaning softly under his lips.

My hands discovered his jeans were open, and running my hands inside, I feel his cock - long, hard, read. Running my hands lightly along the material separating me from feeling him, I feel his body tighten slightly. Running my along the top of his underwear, tickling his belly, I slowly push my hand lower, lower, under the material until I can claim the prize I want. My fingers brushing lightly against his cock, teasing him, testing the length of him.

As his tongue presses towards my lips, I part them and allow him entry. As his tongue probs the inner warm of my mouth, I feel his hand softly squeezing my breast, finding the nipple pressing against the lace of the bra that I'm wearing. I push myself harder into his hand, wanting to feel skin on skin, his fingers toying and playing with the nipple, pulling it, and rolling it between his fingers.

Slowly, I start to slide his jeans and underwear over his hips, freeing his erection from the confines of the denim in which it was encased. As I do, I feel him start to lift my sweater over my body....revealing my lace covered breasts to him....
 
Carol opens her mouth, allowing my tongue to dart in. My right hand fondles one of her full breasts, pinching her thick nipple through the fabric of her bra. The seemingly reserved older woman is giving herself willingly.

I peel off her sweater, allowing me easy access to her large round mounds. Reaching behind her to release the clasp...both hands now slide under her lace bra and begin kneading her fleshy tits.

Our mouths are locked together, tongues meeting...jousting playfully...

I feel her lower my jeans and briefs, my thick cock springing upward... ready for action..

My fingers begin pinching and twisting her hard thick nipples... she moans slightly, encouraging me to continue... God I want this woman... more than I have ever wanted any other....
 
I feel Jason's tongue darting into my mouth, as his hand reaches under my sweater and takes hold of my breast. I lean into him, wanting to feel more and am rewarded when his fingers find my engorged nipple.

As he pulls my sweater over my head, I suddenly feel a little vulnerable and very naughty which fires my passion even more. As I feel my bra leave my body, my breasts free, I feel Jason kneading and squeezing my breasts with a certain urgency.

As I lower his clothing to past his hips, I notice his cock spring forth.....thick, hard, demanding attention. At the same time, Jason is pinching and twisting my nipples hard, and causing me to moan under his lips.

I take hold of his cock in my hands, and run my fingers lightly over it almost memorizing it by touch. I trace over the head, and around the ridge, finding the sensitive spot on the underside that causes is cock to twitch and bob. My fingers make their way down his thick shaft, tracing the veins until they reach the pubic bone. With my right hand, I begin to lightly stroke Jason, while my other hand reaches down and grabs his balls, lighty kneading and massaging his sac.

I feel Jason begin to move his hips slightly towards me, and I break our kiss long enough to whisper ...

"Jason, I want to feel this thick cock in my mouth. I would love to kneel down right here and suck on your cock right now."

I feel his hands tighten on my breasts, as his mouth resumes it search of mine, and I wonder if he has heard....
 
I kiss Carol deeply, digging my fingers into the flesh of her large breasts...

Slowly, I move my mouth from hers...placing it to her ear.

"Yeah Carol," I respond. "I want you to suck my cock...."

My hands slide up to her shoulders... pressing down slightly... encouraging her to kneel...

I watch as she lowers herself down to the floor... Her sexy green eyes looking back up at me...

God she looks so beautiful. I think back to a woman I knew in highschool. Her name was Linda. She lived down the block a few houses and although she didn't have the looks of a beauty-queen, she had "something". She was a married woman with kids my age.

I delivered her paper ... and I remember one day I went over to collect... she was alone... we started to BS about nothing... I made a move on her... she swore me to secrecy... and gave me the best blow-job I've ever had...

Something told me that Carol would top that... Maybe it was the mischievous way she was looking at me as she lowered her mouth to my cock...
 
As I kneeled before Jason, I continued to look up at him. This was one skill that I knew I still possessed and was able to do well.

Leaning towards his impressive cock, I stopped just inches away and brought my hands up to cover it. With my fingers, I lightly stroked his cock following the contour and veins and sliding my fingers around the ridge. Running one finger nail lightly down the shaft, I didn't stop until I reached his balls and tickled the skin of his sac. I look up at Jason, and his face is a mask of lust and desire. I can tell he wants me to take his cock into my mouth, and yet, he also wants to see what I will do next.

Taking one hand I begin to lightly stroke the base of his cock, while the other hand playes with the tightness of the head. To my delight, it does not take long before a see the drop of precum begin to form at the tip. Leaning in the last few inches, my tongue circles the head lazily making its way up to the that delicious droplet. When my tongue finally gets a taste I moan at the taste of him, pressing my tongue firmly into the slit at the top wanting more. Drawing back, I allow my tongue to glide over the head and run along the ridge relishing the feel of him, the taste of him.

Slowly, while looking up at him, my lips close around the head and I begin to suck lightly. My hand starts to stroke with more fimness, as I move my other hand to his balls.....stroking, kneading, lightly squeezing.

As I continue to suck the head, I rub my breasts against his legs, my nipples yearning for friction and to be assaulted. I feel Jason place one hand on the back of my head and the other on my shoulder as he pushes me towards him, wanting me to take even more of his cock into my mouth....
 
Carol is a master with her mouth... Her patience and experience are an incredible combination. She teases my eager cock...stroking it with her fingers and lightly licking it... I could tell that this was not going to be an average blow-job...

Watching her work was such a turn-on... Her sweet motherly face, performing such a non-motherly act was driving me crazy, as was her incredible technique... Her deep green eyes, looking up at me... her sweet lips encircling my throbbing cock...

I reached down and applied pressure to the back of her head... forcing more of my needy penis into her mouth... she accepted it easily...allowing my cock to slide past her smooth tongue and begin it's journey into her throat...

I couldn't help thinking about her husband...what would his reaction be, if he knew his wife was in the office, sucking my cock...The thought was surprisingly exciting to me...the forbidden always seems so much more tittilating...

Taking a handful of her hair...I pushed my hips forward and slid more of my hard meat into her open mouth...God this was going to be a great day !!!
 
As I teased Jason's hardness with my lips, tongue, and fingers, I felt him suddenly grab my hair and push his hips towards my face. My scalp screamed as my hair was pulled, but I felt the sensation oddly erotic with raw sexuality.

As I felt Jason's erection enter my mouth fully, I sucked as hard as I could, and soon he was buried in my mouth, my nose up against his belly. My hand kept playing with the sac that contained his balls, as my other hand reached around and started to grab his firm ass, feeling the muscles tighten and ripple.

As Jason begins to move against my mouth, I suck the length of him, my tongue darting and flicking and still teasing him. My fingers find the crack of his ass, and I lightly rake my nails downward as I hear him gasp. Finding what I want, I linger at his sweet puckered hole, my nail gingerly playing with him as his hips move with ever increasing speed. Slowly, I insert my nail into his sensitive flesh and feel him tighten slightly. Pushing with increasing fervency, my finger slowly slides in past the ring of muscles until it finally has entered him. I begin to slide my finger into his ass as he moves against my mouth.

Grabbing my hair with both hands, he keeps my head still as he fucks my open mouth, my hands playing with his balls and with his ass.....my finger probing ever more deeply into him. I feel his cock begin to swell in my mouth and know that he must be close. In answer I suck as hard as I can, while I gently insert a second finger, stretching Jason slightly while pumping my fingers into his ass.

I look up at his face and see a contortion of passion, lust, and release, as his seed begins to make its way upwards, towards my waiting mouth.
 
I wanted to hang on...to enjoy the tremendous pleasure Carol was providing...to soak up my surroundings....

But then she began inserting a finger into my anus...and oh man, did I lose control...

Gripping her hair with both hands, I begin fucking her mouth. My hard cock pumping past her soft lips and sliding against her tongue...Carol was phenomenal...never losing control... responding well to my sudden desire to slam my long prick down her open throat...

I studied her face...so beautiful...so wordly...so sexy...

And then it started...

The first wave struck suddenly, the thick jet of cum erupting from my cock and into her mouth...I had no time to warn her...No opportunity to let her bail out...my cum rocketed from my penis and began splashing against her tongue and down her throat...

"Oh Carol," I screamed as the pleasure overwhelmed me... "Oh yeah, suck my cock !!!"
 
His hands tangled in my hair, his cock pumping my waiting mouth, all was a sensual experience that caused me to suck his cock even harder. When I felt the first spurts of his white cream hit the back of my throat, I moaned deeply wanting more. I was not disappointed as Jason continued to spray my mouth and throat with his cum.

Swallowing hard to keep up, I closed my eyes to concentrate on the wonderful feeling of Jason's cock pumping his seed into my waiting and willing mouth.

As I feel him begin to stop, I take his cock from my mouth and continue stroking him, milking the last drop of cum from his body. Licking the last drop from him, I lightly lick his now semi-hard cock very gently as I look up at him.

My pussy is on fire, and I am so wet I feel that even my jeans must be soaked. God, it has been so long since any man has made me feel this sexy and desirable.

I'm taken from my reverie as I feel Jason pull me to my feet...
 
I pull Carol to her feet....bending down, I pick her up... slipping my right arm behind her knees and begin carrying her down the hall... She wraps her arms around my neck...

Purposefully I stride to my office, placing her down on my desk...

"Lie back Carol," I instruct. "Let's get these jeans off of you."

I unhook the button of her jeans and slide the zipper down...pulling the material down over her hips...

She lifts her butt, allowing me to continue down her legs...

Sliding her shoes and knee-highs off, I slip her jeans over her feet and off... her panties follow shortly...

"That's great," I whisper, kneeling at the end of the desk. Spreading her legs, I place them on my shoulders... And then... I slide my hands up her inner thighs and touch her... the moistness of her pussy excites me....
 
As Jason picked me up in his arms, I suddenly felt so sexy. The last time a man had carried me was when my husband had done so on our wedding day.

My husband once again briefly crossed my mind as we headed to Jason's office. Here I had a husband who had been faithful for over 20 years of marriage, and I'm on my knees in the break room at work sucking the cock of a man who could easily be my son! I start to feel a little uncomfortable, and then I hear Jason's words to lie back.

He speaks with such authority that I simply obey. I feel his hands undoing my jeans. I feel the jeans being pulled from my body, along with my shoes. When my panties are removed I realize just how open and vulnerable I am to this man. I resist the urge to try to cover myself.....and I fight to put my husband's shocked face from my mind.

Suddenly, my legs are over Jason's shoulders and his hands are on my inner thighs. I shudder from the delightful feeling, wondering what delights are in store. As Jason's fingers brush the soft moistness of my sex, all thoughts except what he was doing to me are wiped from my thoughts. His fingers run the length of my outer lips, glistening with the wetness of my pussy. I glance down at Jason, and see him grinning up at me. Oh yes, he knows how turned on I'm getting watching him and feeling him react to my body.

I jump as his fingers lightly trace the softer inner lips, stopping at the entrance to my sex. He moves his finger lightly in circles, just enough so I can hear the juices coming from my body. I begin to moan and move my hips towards Jason, wanting to feel filled. His fingers lightly move up to my clit, and he gives my little nub of pleasure a light rub, chuckling at the sudden gasp and shudder that I cannot help but produce.

As my breathing increases, my breasts heaving, I feel his finger enter my pussy and I cry out. At the same time I feel his breath, drawing ever closer to my sex. I find I am holding my breath.....I've never felt a man's tongue on my clit before, will this be the first time?
 
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