Claire and Her Boss

Claire started growing more comfortable as the minutes passed. She relaxed her grip on my legs and began opening her throat a little for my incursion. She kept eye contact whenever she wasn't suppressing a gag reflex. Her mouth felt wonderful, she knew when to apply suction and when to move her tongue for stimulation. After about five minutes I released my hold on her hair and reached down to unhook the strap of her dress. The top fell, exposing her magnificent breasts. She was probably a B-cup but on her small frame they looked disproportionately large. Given her age they were obviously pert and firm, with perfect nipples the size of a small coin. I leaned over as she continued laboring on my cock and fondled each of her breasts as if inspecting a prize. When I was done I reached lower to pull the material of her dress up, she let my dick come out of her mouth with a delightful pop sound and reached up to let me pull her dress off of her delicious, petite body.

She took advantage of the interruption to catch her breath and began working my cock with one small hand. Claire looked up at me obediently and I realized how large the head of my member was compared to her young face. Her hair was disheveled after my rough treatment and her mascara was just a bit displaced from gagging-related eye wetness.

"Is this what you wanted, sir?" she asked. I nodded politely, running my fingers through her hair again. I grabbed hold of her little head and pushed her down to my balls, which were growing more in need of release with every passing second. I forced her to tend to my hefty, hairy sack with her teen mouth and it was absolute bliss. I looked down, admiring the view, and was fixated on the length of her toned back ending in a small, teenaged butt. That butt, which would inevitably be mine, was resting on the heels of her white chucks... the only things I allowed her to keep wearing.

That sight drove me wild and a pulled her head back up and, without warning, re-entered her mouth with vigor and dominance. This time I put both hands on her head and took her young throat for my pleasure. She squirmed below me as I started fucking her tiny, hot mouth with my outrageously mismatched dick. Her hands went up to the front of my legs and attempted to press me back as she shifted on her knees and let out audible gags. She was not able to maintain eye contact but that didn't matter to me now. I swatted her hands away from my legs.

"Cross your wrists behind your back, Claire," I ordered, "You don't get to resist." She did as she was told but I noticed with some reluctance, it was probably a lot to take in... being facefucked by your boss without warning.

Once I decided the deepest she could take me still left two more inches of shaft I finally relented. She came up for air like she had been drowned, panting and breathless. I let go of her hair and picked her up from under her shoulders. I took a moment to admire the drool running down her chin to her chest and the now trails of mascara cascading down her face. She batted her eyes, her eyelashes had clumped together in places, and gave me a look of astonishment, fear, and anticipation all rolled into one. I spun her around by her shoulders and leaned back into the desk with her facing away from me. From there I pulled her slight little hips back until my dick was resting from her buttcrack to the middle of her back.

"You can say no," I said, "But you won't be working for me if you do."

"You won't fit!" she insisted, I could hear the tiniest, tiniest undertone of longing in her voice. Deep down she wanted it, even if she wasn't going to admit it. I reached my right hand around to smack her left buttcheek and hip then pulled her by the hair to lean back into me.

"It won't fit, sir," I corrected, "And I promise it will."

With that I pressed her forward slightly and began rubbing my tip against her pussy. She wasn't wrong to be concerned, even after coating myself with her juices I could just barely push the tip of my cock into her small, warm, and unbelievably tight fuckhole. I could see her grimace as the tip forced its way in after a minute or two of my efforts, forcing her vaginal walls to contract and make room for the invasion.

Once securely inside I grabbed onto her hips and pulled her back, demanding another inch or so of her cunt. She let out a gasp and rested her hands back onto my legs. I looked down and could just make out that her pussy lips had formed an air tight grip on my cock.

I let her adjust to my size and then began pulling on her hips, guiding her to bounce up and down on me. Slowly her teen pussy accepted about four inches of me but she was in noticeable distress. Her converse-clad feet squirmed, her calves clenched, and she was clearly trying to breathe through the experience, but she continued on... knowing the consequences.

"Mmmm fuck that old cock, Claire," I ordered.

"Yes, sir." she struggled to whisper. I leaned up and wrapped my hands around her to explore her young breasts and taut stomach before letting my right hand roam downward and rest on the front of her bald pussy. I began to work her inexperienced clit with expert skill and I noticed, as I did, she was able to get the fifth inch of my dick into her little box.

"Does that feel good, sweetie," I asked, "Do you like pleasing your boss's older cock with your tight little pussy?" She nodded slowly and, finally, let out a soft moan. I didn't give her a chance to soak it in, instead I stood up and pressed her whole body forward... forcing her to put her hands on the floor in a down-dog position. I grabbed her hips and pulled them upward, making Claire come to the balls of her feet to maintain her balance and then, as you probably suspect, I began ramming my cock into that gorgeous young girl.

Claire gasped, moaned, protested... everything. I smacked her little ass hard.

"Shut the fuck up," I ordered, "People are starting to come into the office." She bit her lips and endured. I didn't think she'd walk the same ever again. Luckily for her this whole experience and the weeks I went without orgasm had come to a quick resolution, I was ready to burst. After just a few minutes of having my way with her 18-year old body I let go of her hips, she dropped to the floor panting. I grabbed her by the hair and pulled her up to face me, sitting on her bottom and pressed against my arm chair. There was no escape for her.

I positioned my cock to her mouth and she, having lost all energy to resist, accepted my member into her submissive, elfin face. I made just a few deep pumps, feeling her throat one more time, then pulled out to where only the tip was contained in her soft little mouth. I let out a deep guttural moan as two month's worth of cum coursed through my balls and shaft and exploded into Claire's waiting, helpless tongue and throat. She closed her eyes and I felt a sigh of relief flood over her. One hand remained on her head, firmly, and the other had found its way down to her chin and throat and grasped onto them for extra control. I came for what felt like hours but it was definitely five or six large bursts. When I had finally been relieved of the last drop I pulled out of her mouth. Just a little bit of my cum escaped onto her lips but Claire, years beyond her experience, knew to show me the prize floating on her tongue. I had created an entire pool in her mouth and she looked up at me with the flare of a girl impressed with her reward before dutifully swallowing my load. She then opened her mouth again to show me it was gone.

"So," she started, "Do I get to keep my job, sir?" She raised her eyebrows, clearly flirting with me. I let a smile escape and rubbed her cheek, which still showed some redness from where I smacked it.

"Keep this up," I said, "And you'll get a raise."

"Oh," Claire answered, "I didn't think I had a choice." She then took to cleaning my shaft with her tongue. "Not that I want one, sir."

I smiled and watched this pretty young thing clean my dick with the mouth I had just wrecked. She then stood up, put her dress back on, zipped me up, and turned to walk out. She stopped at the door to give me a wink and then playfully lifted her dress to show me one more time the pantyless body underneath.

"Let me know if you need anything else, sir," she said as she closed the door. I knew this was just the start of a beautiful experience.