Annabelle

Annabelle made a career built by being the boss. And bossy. I never noticed the woman in her; she was my boss, and that's it. You did as you were told, reaching your sales targets. I did have a good relationship with her because I was always in the top three of best-selling sales managers. Every single year. But I kept to myself, getting my sales numbers in a steady, continuous flow. She worked remotely, and we saw her maybe once a month, if at all, which was fine by me.

As far as I could remember, she was 34 years old, perhaps 5.6 ft. (1.7 m), had brown hair and brown eyes, and had a good, hourglass figure. I did notice some time ago that her breasts were larger than her butt, but she always wore business suits, so it was hard to say. I guessed a 70F (32DD) could be possible, but like I said, I wasn't sure. We didn't even know if she was straight or lesbian; she could have been both. Some of the guys thought she was a lez, but I always said to them that tough women can be just as straight. We all concluded that her career was the most important thing for her, so she was not a real gossip topic. We focused on the new 20-something female trainees and if we had a chance with them.

We didn't go to any sales exhibitions during the Corona time, but Corona was behind us, and she asked us in our weekly meetings who would like to go. I didn't say anything, not wanting to. Some said yes, and then, once all were quiet, Annabelle said to me in our video conference that I was coming too. I smiled, because I had been dodging fairs for years, knowing that one day I had to go again. The good thing was that whenever Annabelle was joining us at a fair, we would have a five-star hotel, instead of a four-star hotel, and the restaurants where we would have our dinners were normally much better than usual. Work hard, play hard, I guess.

We all went by train, and God forbid, she sat next to me. At first, we had our laptops open, but the internet was terrible, and we could not work. So, after futilely trying, we both sighed at the same time and closed the laptops. We laughed at our synced frustration, and we started chatting about all kinds of things, but work.

The conversation flowed easier than I expected. We moved from industry gossip to travel stories, then to the kind of personal territory that usually stays off-limits between management and staff. Annabelle was very different when she wasn't in boss mode—witty, surprisingly self-deprecating, with a laugh that came from deep in her chest. She shifted in her seat, turning her body toward me, and her knee brushed against mine. Neither of us pulled away.

"You know," she said, her voice dropping to a conspiratorial murmur, "I've always appreciated how you handle yourself. Steady. Reliable. You don't make a fuss, but you always deliver."

"Thank you," I said, feeling the heat of her attention. "I learned from the best."

“I like men who can deliver.” She whispered as she looked me straight in the eyes. “Deliver more than once.”

Her hand found my thigh. It started as a casual pat—good job, well done—but her palm stayed there, heavy and warm through the thin fabric of my trousers. My breath caught as her fingers began to move, tracing small circles that moved higher with each caress. The fabric did nothing to dampen the sensation of her nails grazing a trail on my skin.

"Annabelle—" I started, but she cut me off with a look, her brown eyes dark and knowing.

"Shh," she whispered. "No one can see. The seats are too high."

Her hand travelled upward, finding my growing cock straining against my zipper. She traced the outline of my cock with one manicured nail, her touch deliberate and teasing me through the material. I was already half-hard from proximity alone, but her attention made me swell rapidly, the outline becoming unmistakable.

"Well," she purred, her fingers curling around my shaft through the fabric, measuring my length. "Someone's happy to see me after all."

I groaned softly, my hips bucking involuntarily into her grip. "Fuck, Annabelle..."

"Language," she chided, but her smile was wicked. She squeezed gently, her thumb pressing against the sensitive ridge beneath the head. "But yes. I think we need to have a quick meeting. A very private one."

Her hand slid down to cup my balls, then back up to trace the full length of my erection. My cock throbbed against her palm, desperate for more direct contact.

"Toilet," she breathed, her lips nearly touching my ear. Her hot breath made me shiver. "Five minutes. Give me a head start. And she squeezed once more, her nails digging in just enough to make me gasp, "Make sure you're ready for me."

She withdrew her hand with agonizing slowness, her fingertips dragging across my trapped erection one more time. Then she stood up, smoothing her skirt with businesslike efficiency, and walked toward the end of the carriage without looking back.

The five minutes were pure torture for me. I sat there with a raging hard-on, trying to look casual while my heart hammered against my ribs. When I finally rose and made my way to the toilet, my cock was still thick and fully erect against my stomach, impossible to hide.

I knocked softly. The door cracked open, her hand snaked out to pull me inside, and then she was on me.

Annabelle had transformed. Her jacket was gone, her blouse unbuttoned to reveal a lace bra struggling to contain her heavy breasts—definitely big tits, I realized, as they pressed against my chest. She pushed me against the locked door and dropped to her knees with practiced efficiency.

"Let's see what we're working with," she muttered, her fingers flying to my belt.

She freed my cock with a hungry sound. It sprang out, thick and veined, the head already slick with pre-cum. Annabelle did not hesitate. She wrapped one hand around the base and took me into her mouth in one smooth motion, her lips stretching around my girth.

"Jesus," I hissed, my head falling back against the toilet door.

She was skilled—too experienced for this to be her first time in a train toilet. Her tongue swirled around the sensitive underside of my cockhead while her hand worked my shaft in tight, twisting strokes. She took me deeper, relaxing her throat until her nose pressed against my pubic bone, her eyes watering but never breaking contact with mine. The obscene wet sounds of her sucking filled the small space.

Her free hand cupped my balls, rolling them gently, then travelled back to press against my very sensitive perineum. I groaned, my hips involuntarily jerking forward, and she took it, letting me fuck her mouth in shallow thrusts. She pulled back with a gasp, saliva stringing from her lips to my cock, then dove back down, sucking hard on me, hollowing her cheeks, which made my knees weak.

She worked me for what felt like hours but was probably only minutes, varying her rhythm—fast and shallow, then slow and deep, her tongue fluttering against my frenulum. I was close, my balls tightening, when she suddenly pulled off me with a wet slushy pop.

"You're ready for me," she declared, standing up. Her lips were swollen and red, her eyes glazed with lust. "Sit down."

The toilet seat was down, clean enough for this. I sat, my cock standing straight up, glistening with her spit. Annabelle hiked her skirt around her waist—no panties, just garter straps and stockings framing her shaved pussy, already glistening with arousal.

She straddled me, her hands on my shoulders for balance, and positioned herself above my throbbing shaft. The head of my cock touched her wet folds, and we both moaned at the contact.

"Bare," she whispered. "I want to feel your meat. All of you."

Then she impaled herself.

"Fuck!" we cried out in unison.

She was tight—her tunnel heat gripping me like a fist as she sank down, inch by inch. Her eyes rolled back, her mouth opening in a silent cry as she took my full length, her ass finally settling against my thighs. We stayed like that for a moment, joined completely, feeling each other's heartbeat through the flesh, which connected us together.

Then she began to ride.

Annabelle set a brutal pace from the start. She lifted herself until just the tip remained inside, then slammed back down, the sound of flesh meeting flesh echoing off the metal walls. But then she shifted, arching backward in abandon, her head thrown back so her curly brown hair stayed behind her shoulders, her mouth open uttering soft moans. Her heavy F-cup breasts swayed with each downward impalement, her nipples hard and jutting out from the pink globes as she bounced on my cock.

My hands grabbed her waist, fingers pulling her down harder onto my throbbing cock each time she lifted up. The position gave me a perfect view of where we joined—her shaved pussy stretched tight around my thick shaft, her labia sucking down on me, creating a vacuum, gripping me like a wet vise as she sank down to the root.

"Look at me," she panted, her voice ragged. "Watch me fuck you."

She rolled her hips in circles, grinding her clit against my pelvic bone, her inner walls cramping down around my cock. The movement made her breasts bounce obscenely, the flesh rippling with each impact. Her stomach muscles tensed and released as she controlled the rhythm—slow, teasing rises where her pussy lips dragged along my shaft, clinging to every vein, then sudden, brutal drops that made us both groan as I bottomed out inside her.

The train's motion added to ours, rocking her forward so her nipples brushed against my face. I caught one in my mouth, sucking hard, and she cried out, her pussy clamping down on me. Her hands came up to grip the handrail above her for leverage, giving her the angle to piston up and down faster, her ass slapping against my thighs with wet, rhythmic slaps.

"So deep," she whimpered, her eyes rolling back. "You're so fucking deep inside me."

I could feel every ridge of her tight channel, the way she squeezed me on the upstroke, trying to keep me inside, then released just enough to let me slam back up into her cervix. She was soaked, her juices coating my balls, making the seat beneath us slick. Her clit was swollen and visible, peeking out from its hood, grinding against me with each rotation of her hips.

"Fuck me, fuck me, fuck me," she shouted, losing all composure, her bossy attitude completely gone.

I thrust up to meet her downward strokes, our bodies colliding with enough force to shake the metal walls. Her breasts bounced violently now, the flesh rippling, nipples pointing toward the ceiling as she arched back further, offering herself completely. I stood up, lifting her with me, and quickly pulled out to turn her around and to bend her over the small sink. Her reflection in the mirror was obscene—mouth open, breasts swaying, her professional mask completely gone. I drove my rampant cock back into her from behind, gripping her waist with both hands, pounding her with deep, upward shoves that made her squeal.

"Right there, right there… OH!” she cried, pushing back against me.

Her second orgasm hit her harder than the first one. She bit her own arm to muffle her scream, her pussy convulsing so hard I had to fight to stay inside her. She was soaking now, her arousal running down her thighs, making every thrust slippery and loud.

I reached around to rub her clit in fast, small circles while I fucked her with short, brutal thrusts. Her third climax built slowly, her whole body trembling, her moans rising into cries of lust until she broke, shuddering uncontrollably around my cock, her knees buckling so I had to hold her up.

"Now," she gasped. "Come now. Give it to me."

I couldn't have stopped if I wanted to. I buried myself to the hilt, my hips jerking uncontrollably as my orgasm crashed through me.

As my cock swells and erupts inside her, Annabelle's cunt responds with a vengeance, her inner muscles clamping down in rhythmic, milking contractions that seem to have a mind of their own. Each pulse of my orgasm triggers a corresponding squeeze from her velvety walls, her pussy gripping my shaft like a fist determined to wring out every drop of my cum. The sensation is maddening—her wet heat undulates around me, the ridged texture of her G-spot dragging against my sensitive underside as she grinds down, her body instinctively knowing exactly how to extract my seed. She doesn't stop moving, rolling her hips in tight, desperate circles that make her swollen lips drag against my base, the suction audible and obscene as she refuses to let me soften, her cunt fluttering and spasming with aftershocks that force involuntary grunts from my throat.

I can feel her milking me dry, her pussy working my length in waves that travel from her entrance to her cervix, each contraction drawing my cum deeper while simultaneously pulling more from my balls. She leans forward, her heavy breasts pressing against my chest, her nipples hard points that scrape my skin as she whispers, "Give me everything," against my neck. Her internal muscles don't relent—they squeeze, release, then squeeze harder, the wet slap of our joined bodies replaced by the lewd sound of her stuffed pussy squelching around my spent cock. Even as I finish, she continues to ride me slowly, her cunt massaging my hypersensitive shaft, milking out the final drops until I'm trembling, overstimulated, and completely drained yet still trapped in her relentless, hungry grip.

I emptied myself completely, my vision going white at the edges, until I was spent and softening inside her. Never in my life has cumming hurt my balls so much.

"Well," Annabelle finally said, her voice hoarse but carrying that familiar authoritative edge. "I think this sales trip is going to be very productive."

She squeezed me internally one last time, making me gasp, before slowly disengaging. I watched, transfixed, as my cum began to leak from her swollen, well-used pussy, running down her inner thigh.

"Five minutes," she said, wiping herself clean with tissues and adjusting her skirt with practiced efficiency. "Then follow me back. And wipe that satisfied smirk off your face, Sales Manager. We have work to do."

She left first, looking as composed as ever—if one didn't notice the flush on her cheeks and the slight wobble in her step. I leaned against the sink, catching my breath, already wondering what the five-star hotel would bring.

The train rattled into the main train station of the city, and I smiled. This was going to be a very interesting exhibition week.

The moment we arrived at the hotel check-in, she, as usual, took over, changing my room reservation.

“We need two single rooms with connecting doors.” She said to the counter clerk.

The young girl reacted professionally and quickly gave us two new room numbers.

But she couldn’t help adding a little extra spice to the situation, telling Annabelle that the connecting doors can only be locked from her room and not from mine.

“Good to know.” Annabelle reacted, caressing my crotch in plain view and making my dormant cock twitch. “It will be unlocked day and night.”

The clerk smiled, loving the way Annabelle decided for me. Deciding what would be best for her cock.

To be continued.