Turnabout is Fair Play (closed)

I kept up my ministrations throughout the course of the third act. My fingers were soon slick with her juices, which oozed forth from her as if I'd turned a spigot. I was sorely tempted to take my hand away so I could lick my fingers clean.

I kept to my own set of rules. I stayed clear of direct contact with her clit; teasing that sensitive button seemed too easy. I also didn't slip more than a fingertip inside her. Best to give her a fighting chance.

While a few moans escaped her attempts to muffle them, Holly otherwise endured almost silently. Still, I could see the struggle not to cum was no easy one. Her nostrils flared with each inrush of breath and her impressive chest rose and fell quite noticeably. Even in the darkness, I could spot the hardness of her nipples.

Still, when the lights came up and I was compelled to retract my hand before anyone noticed it under her dress, Holly had yet to cum. Impressive.

As the audience began to depart, I took the opportunity to whisper an additional set of instructions to her. "Meet at the top of the parking garage in ten minutes." I turned away lest anyone notice the exchange.

The parking garage in question was just around the corner. The bank that owned offered discounted parking for theatergoers, so everybody parked there. However, the first four floors easily accommodated the audience's cars, so the remaining floors would be deserted at this hour - particularly the roof.
 
As he left, I began to doubt my own ability to stand. It had been so tough to sit through the play and not make a sound but now it seemed like I might get a reward for my struggle. Jacob's cock was still a fresh memory and one I wanted to relive soon.

To my amazement, I managed to stand and retrieve my wrap, slipping through the rush of patrons trying to get taxis at the theatre entrance and heading towards the parking garage, praying to find the elevator working. My luck was in and I rode to the top level, only needing to climb the stairs past here to the roof. It was deserted but open, the light wind made me shiver, or perhaps it was excitement. I glanced at my slim gold watch, it had been 8 minutes. Jacob didn't seem to be here yet so I waited, feeling the slickness of anticipation growing between my legs.
 
I spent some time schmoozing with various acquaintances on my way out the theater. It took me several minutes just cross the lobby. Consequently, when I finally made it to the roof of the parking garage, Holly was already there.

The pale bluish hue of the fluorescent lights wasn't the most flattering to her, but I thought she looked beautiful all the same. The autumn air was already tinged with winter's chill, so she rubbed her arms for warmth. I suspected the temperature wasn't entirely to blame for her rock hard nipples, though.

I offered no preliminaries. I strode directly to her and immediately put my hand beneath her dress. Her pussy remained as hot and damp as I'd left it in the theater.

I grinned at her. "Still want to cum?" I inquired. Her moan as my fingers caressed her tender folds was all the answer I needed.

"This way," I directed. Keeping one hand on her sex and the other on her upper arm, I walked her over to the concrete wall that bounded the edge of the roof. I faced her towards it and directed her to the street below. We faced the side nearest the theater, so the sidewalk was full of departing patrons.

Holly froze slightly, a not unnatural instinct when gazing at a multi-story drop to concrete pavement. While she was so distracted, I used my free hand to grasp her dress and haul it above the waist. In moments, Holly was standing at the wall, fully exposed.

"Time for the next performance,"I whispered in her ear as I began intensifying my fingers efforts on her pussy. "Let's hear you cum, Holly."

This time I didn't tease her clit, but ground my palm against it till she squealed. We were far too high up to be heard over the wind and noise of the street, but all a passerby would need do is look up to see a half-naked Holly with a man's hand buried in her crotch. I rubbed my hardening cock into her ass and pressed my hand more firmly against her pussy. "Cum for me!"
 
I gasped as his fingers brushed my skin, cupping my pussy and feeling it's wetness. A moan escaped from me, all my previous arousal jumping back to the surface. Jacob led me towards the edge of the roof, I seemed to move hips first, keeping the contact with his hand.

A fear of heights stilled me as I became a little dizzy but Jacob soon distracted me. My moans were growing louder and higher with desperation. I could feel the approach of the orgasm I'd fought in the theatre as his fingers thrust into me and his palm ground into my clitoris. I felt so exposed and it turned me on more than I expected. I pushed my ass back against Jacob's cock as I started to cum loudly and exquisitely.

"Oh god, yes! Oh! Yes, yes!" I screamed, not caring who could hear me, my legs starting to buckle. I reached behind me for Jacob as support.
 
Holly climaxed loud and hard. All that tension she'd built up holding off her orgasm hit her like a truck. She jerked so hard against me I nearly lost my grip.

Afterwards, she collapsed against me as if she'd lost all strength. I helped guide her down to the cement floor where she could lean back against the retaining wall for support. She leaned back, gasping for breath for several minutes.

I glanced over the edge. As expected, we were too high up for the folks on the sidewalk to hear - even Holly's full volume squeals. Still, I was pretty sure the prospect of being seen had enhanced her climax.

When Holly had recovered sufficiently, I helped her to her feet. Her dress was definitely in need of cleaning after sitting on dirty concrete, but the damp spots commemorating the explosiveness of her orgasm made that a given.

"I like listening to you cum," I growled, planting a kiss on her supple neck. "But listening to you has certain consequences...." I pointed to the unmistakable bulge in my pants. "Before we call it a night, I'm going to need you to take care of that."
 
I was breathless and dirty, half collapsed on the concrete with my chest heaving. Jacob pulled me to my feet and showed no signs of ending the night yet. Instead, he seemed to be offering a chance for me to exercise my improved skills.

My hands fell to his crotch, stroking his enormous bulge through his pants and making sure he was getting to full hardness, releasing him from his pants before the strain was too much. I stroked his full length with a hungry look in my eyes.

I wanted to show him that I could fit him into my mouth, knowing he was disappointed from the first time I'd tried. I fell to my knees and stretched my mouth open wide to take the tip into my warm lips.
 
Holly reached for my crotch and felt the swell of my cock through the fine wool of my pants. I gave her the nod to proceed and she began fishing my thick shaft through my fly. Once it dangled before her, she began stroking it till the stiffened pole was nearly parallel to the ground.

I was about to suggest a position, but Holly took my throbbing member in both hands and brought it to her lips. I lowered my eyebrows. "Are you sure you want to do that? It seemed a bit too much for you last time," I cautioned.

Holly nodded emphatically, so I shrugged. "Okay. Just be careful."

Holly spread her lips wide and fed my cock inside. Even with her jaws spread, her teeth lightly brushed the outer rim of the crown, but soon she had the full head ensconced. But whereas she could barely handle that this time, she continued to take me further inside. I braced myself for the possibility of her gagging, but moments later I felt my cock brush up against the entrance to her throat; Holly didn't even flinch.

"Quite the improvement," I praised. "I think someone has been practicing." Holly's mouthful precluded most facial expressions, but I think the look in her eye suggested pride and satisfaction with her performance.

Still, when she began attempting to shove me deeper, I intervened. "Easy. Baby steps. Deep throating something this thick) isn't easy. Don't push yourself farther than you're ready for. How about you get me nice and wet and then I'll pound that lovely pussy of yours?"
 
It was possibly the strangest and most degrading thing I had ever been proud of and yet here I was. Jacob's cock was a challenge but I had risen to it well. He stopped me from pushing further, clearly eager to fuck me in a more traditional way and that wasn't something I was about to pass up.

Just to show him that I know my own limits, I pushed a little further anyway. My eyes watered but I didn't gag just yet. Satisfied, I began sucking the part of him I could reach, wetting him thoroughly in preparation for my pussy. Already I could feel the ache of longing deep in my belly.
 
Holly actually seemed game to try more, but after all this foreplay, my balls were aching for release. I guided Holly off my cock and then helped her to her feet. I then walked her back over to the wall and had her bend forward with her hands atop concrete.

I pulled her dress up above her waist, exposing her naked lower body. Bent over as she was, her pussy lips poked through her thighs. I traced over the tender, glistening flesh, eliciting a soft gasp from Holly. Using my index and middle fingers, I splayed her lips wide with on hand as I guided my cockhead towards her pussy with the other.

"God, you're tight," I grunted as I slid the first few inches in. Even having fucked her before, I was still mildly surprised at how snugly sh gripped my member. I kept slowly plowing forward, my girth plunging deeper and deeper into her warm center.

I glanced over her shoulder. The foot traffic below had started to thin out, but a few theater-goers still filed past. "Just think what those folks would see if they looked up," I chuckled. "Your little pussy getting split open right above them. Such a naughty girl - fucking in public!"
 
I gasped as Jacob eased the first few inches of his monster cock into my wet, waiting pussy. My memories of the last time had already been tempered and I was reminded anew of just how well he filled me.

My eyeline was filled with the street below us as he thrust deeper and deeper into me.

"Oh yes, so naughty!" I panted, half crazed with desire. The possibility of being caught was something that had never excited me so much, no matter how slim the chance. I could see people which meant they would be able to see me if they just looked. My arousal reached new heights as Jacob gripped my hips and drove powerfully into my pussy.
 
Even wet as she was, it took some effort to bury myself inside her. Her tight pussy clung to me like a second skin

Holly arched her back against me. One hand rubbed across her abdomen, tracing the thick shaft she was impaled on through the fabric of her dress. I gave her a few moments to adjust to my size before I began thrusting.

Holly provided delightful vocal accompaniment to my efforts. Her moans were interspersed with gasping confessions about how much she loved my huge cock. Even with the street noise and wind, I half expected someone on the sidewalk to suddenly take note of the commotion above.

But when I felt my cock swell in advance of my own explosion and added my own orgasmic grunts to the mix, the passers-by continued on unaware. I fountained my seed deep within Holly and no one on the street below had a clue.
 
The exposed and public element of this illicit rendezvous excited me to heights I had never experienced before. The moans and lewd words that spewed from my mouth seemed almost designed to draw attention to us but as enticing as the risk was, Jacob's cock was still my main focus as he thrust again and again into my throbbing pussy. He had me crying out for more as he filled me.

Jacob had me on my third orgasm before his own arrived, adding a depth to my own pleasure with his groans and grunts and the twitches of his spasming cock.

I laid my head on my arms, resting against the cool concrete and panting heavily.

"Wow." The word was just a whisper.
 
Holly collapsed onto her arms, leaning heavily on the concrete wall. I couldn't fault her for being a tad worn out. After such a long foreplay session in the theater, she'd slammed through multiple orgasms in relatively quick succession.

I still had life in me yet, but it was chilly on that rooftop. As much as I might like to spread eagle Holly on the hood of a parked car, I think I'd prefer doing it when it was warmer.

I pulled out of Holly. As usual, a small gush of our commingled fluids followed soon after. I gathered up the ends of her dress and wiped off my softening cock; given the liberal spotting of her own juices on the fabric, one more stain would scarcely make a difference.

"Not bad, Holly," I commented. "I wasn't sure you could control yourself as well as you did in the theater. We'll have to do that again sometime."

I finished tucking myself back in my pants and straightened my tie. "I won't need you again till the new moon. I've got something special in mind. You'll need a black evening dress and lingerie to match. I'm sure someone like you has quite the variety in her closet, but I thought I'd give you advance notice in case you wanted an excuse to go shopping." I grinned; imagining Holly trying on outfits had a certain salacious quality.

"I'll provide more details as the date grows closer. Till then." I gave Holly a nod and strode off in the direction of my car.
 
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