After the Gala

Story Info
She lets him take her home, she gives him a surprise.
2.6k words
4.37
48.3k
13
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
bobstales
bobstales
16 Followers

Climbing into Jack's car, I shook my head in disbelief, was I really going to join him for more drinks? We had just met that evening at the Board of Trustee's year end gala. I knew he had been involved with the administration for some time, I was a lowly secretary for the grounds crew supervisor; but we had hit it off at dinner, one of the dean's crazy ideas of mixing all staff up to encourage administration cooperation! After a nice dinner and a few drinks later, the dance and conversation fizzled out, and the married staff had left the party; the few remaining singles began to sneak from the function, most to their preferred clubs or bars.

Jack took my arm as our table excused itself and asked "Would you like to continue our conversation at a bottle club I belong to?"

He looked so handsome in his tweed blazer and khaki pants, I only hesitated for a moment before agreeing. I was new on the job and in the city, and having taken a taxi to the party, I felt safe enough with this gray haired gentleman. I self consciously pulled on my rather short, orange dress, the low seats in his car forced more of my legs to show than I was comfortable with at first; I even felt his eyes on them from time to time! We chatted about nothing in particular as he drove down the dark streets.

"Oh no," he groaned suddenly as he pulled up in front of a rather dark building, "apparently they have closed for the evening."

"Its fine, you can just take me home," I proffered, but his hand on my thigh interrupted me.

"You know, I have a brand new bottle of Jefferson's Straight Rye at home, perhaps we could break into that for a nightcap!" Jack suggested, obviously remembering our earlier discussion of the finer rye whiskeys currently on the market. He had seemed so surprised a young woman like me would appreciate a segmentation of liquors beyond Jagermeister and Jack Daniels! His hand was warm and strong on my thigh, waiting for my decision. I could only nod as the thrill of his touch burned through my body; my nipples hardening as a blush crossed my face as I was certain they pointed through the simple cloth of my dress!

"Certainly, that sounds delightful!" I finally managed to say as he pulled from the parking lot and before long we were on a two lane road, the housing more and more upscale until we pulled up the driveway of a pleasant looking house, not nearly as ostentatious as most of the others, but certainly well cared for and lived in.

I only had a moment or two to take in a view of the neighborhood before Jack opened the front door, and soon the door clicked shut behind me. He only turned on a single hall light to guide us to his kitchen, then another turn to comfortable den, complete with French doors overlooking a secluded patio. He offered me a seat as he opened a cabinet, pulling out an unopened bottle of Jefferson's and two rocks glasses. I primly sat on one of the stools against the bar he had set up there and watched as he grabbed ice for each glass and after a satisfying pop, he poured two fingers of the tasty rye into each glass. Offering a toast, he said "To another successful fall semester, nutty deans and their mixer ideas, and new friends!"

"To new friends!" I agreed sipping the hard liquor, feeling the gentle burn as it seeped down my throat, though the aromas of the excellent whiskey complimented it unusually well. "And to fine American rye." I said before a second taste, watching Jack turn and slide a CD into his stereo system, his eyes on my face as I recognized the soft bluesy sound of John Coltrane. Again this man surprised me with his seemingly eidetic memory; I smiled, wondering what he didn't know about his latest visitor.

A comfortable silence ensued as we enjoyed the music and rye, though I eventually got up and looked at the art and décor of the den, Jack offering up tidbits of information on each as I approached. Occasionally we would catch the other staring; again I felt that stirring below that made me wonder if tonite was going to end as well as it was currently going! I had finally wandered back to the bar, my glass empty, his was as well. Without a word, he poured us both another glass, adding more ice to mine as I giggled.

"I better find the ladies room." I finally admitted, grabbing my purse as he led me around a corner, the hallway narrow enough our bodies brushed together as I went left and he went right. Stopping for a moment, our eyes locking just long enough for us both to realize there was a connection, though him being a gentleman, he just smiled and opened the door for me. Safe inside, I took care of my bladder's suddenly dire needs before checking my makeup and hair in the mirror! Peering into my purse to ensure I had some protection, I clicked it shut, comfortable in knowing I had what I needed to make for an interesting night. Again I gazed into the mirror, adding a spritz of perfume on my cleavage, squeezing my breasts together, and following up with the requisite peering of my bum; I decide I am worthy of such a handsome man's attention and exit the bathroom. I step into the den, catching Jack humming along to the soulful tracks; I notice he has lost his jacket and tie, revealing a fit torso, no flab to be seen beneath his tight button down.

My fingertips brush his wrist as I take the offered glass, licking my lips just before I take another sip, Jack's eyes clearly sliding down my face and over my breasts. Realizing he is just too much of a gentleman, I set my glass down on the bar and wrap my arms around his neck, closing the distance quickly I press my lips to his. The kiss lasted for a much longer time than I would have expected, opening my eyes, I find Jack peering back at me, his hands warm and reassuring on my sides! He pulls me closer, his firm chest so strong against my breasts, as my hips close against his; I feel the bulge reflecting his arousal for me against my pelvis.

"Oh my god!" I croon against his mouth, tasting more than the rye. I recognize the scent of his manliness and lust as our hands explore each other's arms, backs and sides. Again we kiss, a bit more urgency reflected as his tongue pushes past mine, his hands clutching my bum tightly and my nipples respond, so hard and tight against his chest. I smile against his mouth as I feel his fingers slowly pull my short dress up, stopping for a second as he finds my nearly nude butt, only the thin strip of my panties running down my crack keeping me decent, a definite requirement with my tight dress. My hands, meanwhile have explored his strong back and shoulders, they begin to shake with a thrill as I slowly unfasten his belt and his khakis. Leaving his lips after one last hot, wet kiss, I drop to my knees and pull his zipper down.

Peering up into Jack's eyes, my hand pushes into his boxers, a whimsical moan escapes my mouth as I find his shaft, so hot and throbbing to my cool fingers. Deftly I pull his rod out into the cool air of the room; the only sound is his gasp as I bring his fat tip to my mouth, kissing away the drop of precum that had already oozed out for me. Slurping it up without a blush, I begin to stroke his veined length just below my lips, though I stop to tease him occasionally, delighted that I find him harder as I kiss down the side of his rigid member. I keep my small hand around his manhood as I lick each of his heavy balls, so full of his seed, just waiting for me to coax it out of him! My cool hand replaces my tongue on his sack, feeling them warm and erotic as I again push my lips down his shaft. Over and over again, up and down my mouth and fingers make love to Jack's lovely manhood, he leans back against the bar, smiling down at me, his new blonde lover. His growls of pleasure match my efforts, soon his hands rest gently on my head, guiding me at his pace, my mouth the instrument driving his pleasure! My fingers caress and explore his heavy ball sack; I can feel his body pulse as my fingertips stray behind them, his legs spreading automatically. My hand twists around his throbbing shaft as it goes up and down, I love having a man at the mercy of my mouth and hands! Faster and faster I slobber down his cock, my fingers wet now, I can feel his body tensing in a most familiar way.

He suddenly pulls me to my feet by my armpits, his cock wetly slapping against my stomach as his mouth ferociously attacks mine, his tongue and lips milking my mouth of our taste, I melt into him in response. His hands push the straps of my dress off both shoulders as our mouths crush together; my hands not idle, as I unbutton his shirt, his chest warm, the light fuzz of hair welcome to my touch. I almost laugh out loud as his hands so gleefully go to my modest breasts, stroking and caressing me, only stopping as I push his shirt down his arms. Soon we again are embraced, my breasts pushing into his chest, his thick cock prodding into my pelvis, eager to find a purchase in my body! I push my body against Jack, wanting him to know I want him as well.

Our kisses slow, and now nude, Jack takes my hand and leads me into the adjoining bedroom. I slowly pull my dress down my body, finally standing in just my heels and pink panties, "God I want this man" I think to myself, watching him as he settles down onto the bed. Turning my back to him, I ease my pink panties down my legs, leaving my bare bum and back open to his view. Reaching down, I push at my clit, aroused at the intimacy before hiding it between my legs as I turn back around to face the handsome man there. I slide onto the bed, brushing my pelvis against the luxurious comforter, resting alongside Jack, my hand rubbing his chest and abs and thigh, tickling my fingers along his cock, stroking his now steel-hard member. Not passive, he rolls me onto my back so that I am beneath him, his cock grinding against my thigh. Before I can stop him, his hand goes between my legs, a look of confusion crosses behind his eyes as he finds the base of my clit, his fingers taking only a moment to measure me to my tip, his touch causes me to get hard, soon my hard 5 inches are encased in his grip as my clit frees itself from the prison of my thighs where I try to hide it from the world.

"How, what, is this?" he stumbles through the not uncommon questions.

"Sorry, so sorry." I mumble, trying to free myself from beneath his body, from out of his grasp. I find myself conflicted, the urge to flee offset by the grip Jack keeps on the obvious male part on my otherwise feminine body.

"Shush." He says, recognizing my fears, "You are safe with me." comforting me, beginning to stroke my arousal faster and faster; I can feel his manhood surge back to life against my thigh, his moment of doubt passing by quickly. "I would have never." He starts to say before I press my fingers to his mouth.

"It's because I don't share myself with just anyone." I say quietly, hips moving in time to his stroking, his acceptance a huge turn on. It seems only a moment later I cry out, spurting my liquid across his hand, onto my stomach. I clutch at his shoulder and the bed as I shudder through the orgasm; it had been so long since another person had granted me such a pleasure as this. Jack continued to stroke me until my erection faded, his fingers having to be satisfied with smearing my mess over my shaft and balls. My fingers were no longer lazy; I began stroking up and down Jack's body, over his chest and bum, down around his drooling cock and heavy ball sack. My fingernails tracing around his firm body, desire still raging through my body and his; Jack rolls on top of me, grinding his cock into my pelvis, alongside my soft cock. I respond, rubbing back up against him, my cum smearing between us, his hands on my head, holding my face to his as he kisses me, my legs instinctively wrapping around his bum, trapping him against me! The heat of our bodies and my white fluids making for a sticky but pleasurable grinding of our pelvises, my hands clutching Jack's ass as his desire builds.

"Want me?" I ask, kissing him, his only reply a groan. I roll him onto his back and grabbing a heavily lubed condom from my purse, I slide it onto his rigid cock, down, inch by inch, the cool and hot of the moment making us focus only on his 7 inches of hardness. I wank Jack for a couple of moments before straddling him, and then, holding his cock upright I ease myself down on him, our eyes locked as his fat tip pushes into me, slowly I push down until Jack fills my ass so completely.

"Unnhh," I groan, slowly riding him, as I stroke my clit, so pleased I had hid my secret from him so long. Jack's manhood filling me so well with each thrust, it rubbing my prostate over and over as he holds my bum, though I control the speed and depth at which he enters me. My clit swells again as we make sweet love, throbbing in my hand as my ass pinches so tightly around Jack's thick meat. My hands rest on his chest, toying with his nipples as I force myself down his veined length again and again!

"Come for me baby!" I beg, finally reaching a hand behind, fingernails lightly scratching at his tight balls, encouraging him to release his hot, thick cum into my hot hole, almost demanding it as I bounce so hard, my clit slapping my stomach and then his as we rut.

Jack's hands aren't idle, exploring my breasts, my clit, and my ass, helping to slam me down, his breathing more and more ragged until "Fuck Yes" he hollers, arching his back as his hands force me down onto his lap, I feel him explode, coating my inner tract with his white-hot cum! I continue to slide myself up and down his shaft, milking every bit of his hot juice from his balls, Jack caressing my sides as his orgasm rolls over him. I involuntarily squeeze him, trapping him in my bum, he responds by clutching me to him, kissing me hard.

bobstales
bobstales
16 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
tobytimtobytimalmost 5 years ago

Good, liked. it, would do the same,. Ch 2 needed

AnonymousAnonymousover 7 years ago
Found it

Yes, I really wish I was jack in this story

AnonymousAnonymousabout 12 years ago

Awesome!!

james_38671james_38671about 12 years ago
yes

VERY HOT MADE ME WANT TO BE THERE FOR SURE , YUMME

Share this Story

Similar Stories

His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
She Has a What?! Teaching his roommate how to use her assets.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
The Girl Next Door Ch. 01 The new girl.in Transgender & Crossdressers
A Surprising Landlady A new tenant gets an unexpected but welcome surprise.in Transgender & Crossdressers
More Stories