Chapter 3

I surprised myself by not hesitating for an instant. I hadn’t really thought about this scenario specifically, but I guess subconsciously I had been almost hoping for this to happen ever since lunch.

“Yes Jill, I would like that very much”, I responded quietly. I picked up her hand and raised it to my lips to kiss it. She squeezed the hand gently in return.

“Are you sure?”, she asked again. “I mean, Amanda and all that...”

“Jill, if there is one thing this fucking pandemic has taught me, it is that you have to live for the present. I’m not going to spend the next twenty years wondering ‘what if’ like I did the last twenty.”

She squeezed my hand again wordlessly, this time a little firmer. Her face showed all the emotion though, a mix of regret for the past, excitement for the present and a twinkle of horniness for the immediate future.

“Well, we’re wasting our time here then if that’s decided”, she said with a bit of a giggle. She waved to the waitress signalling for the check that quickly arrived. She signed the charges to her room and I added a $20 bill for a tip as we headed to the elevators.

As we waited for the elevator, ‘Micky’ and ‘Trey’ walked up and stood beside us. They looked much worse for wear than we did. Trey’s face had a small lipstick smudge on his upper lip, evidence no doubt of a recent make-out session that he had failed to properly conceal. He nodded wordlessly at us as they waited in silence.

The elevator finally arrived and we all entered, joined by another two guys who seemed to be work colleagues. One of them took the orders for the floor numbers and pressed the relevant buttons. The guys were on floors 5 and 6 respectively, Trey was on 15, and Jillian’s room was on 23.

As the elevator doors closed, I spotted something out of the corner of my eye. The couple were standing in the opposite corner of the elevator car with Trey leaning against the back wall and Micky standing in front of him. As the elevator rose to its first stop, his hands slowly lifted the back of her dress and began playing with her ass. She in turn reached her hands back and was stroking his penis through his trousers. I nudged Jillian and wordlessly signalled to her with my eyes to have a look. She glanced that way and stifled a giggle.

“Looks like she isn’t wearing panties”, she whispered at me out of the corner of her mouth.

The elevator stopped on the fifth floor and the door opened. One of the guys stepped out, mumbling “good night” under his breath. The door closed again for the short journey to the sixth floor but Trey stayed frozen in position for the few seconds that this took. The second guy also exited the elevator, leaving just the four of us for the remainder of the journey.

As the doors closed, Trey started moving his hands again to knead Micky’s butt cheeks. Despite their attempts to be inconspicuous, it was obvious that her dress was hiked up a lot higher than it would normally be. For her part, Micky had her eyes closed and was drawing deep breaths as her hands groped her partner’s groin. I looked at Jillian and she rolled her eyes with a smile as we both pretended to look away. The elevator slowed down on the fifteenth floor and Micky quickly broke away, smoothing down her dress as she tried to avoid eye contact. Trey shuffled behind sporting a conspicuous bulge in the crotch of his khakis.

As they walked out of the elevator, Jillian called after them.

“You guys make sure you have fun tonight!”

Micky turned around in a mix of shock and embarassment, her face blushing red and her jaw dropping open in surprise. Jill just grinned as the doors silently closed between them and the elevator began to move up again.

“Oh lord, you didn’t just do that?”, I asked as I tried to control my giggles.

“Well, why should she get to have all the fun!”

“I think HE had a pretty fun filled elevator ride too judging by the uh, evidence”

“Haha yeah. Almost made me wish that I had worn a dress like that today!”

I chuckled.

“If I had known you wanted someone to feel up your ass, I could have stuck my hand down the back of your jeans!”

Jillian giggled.

“I may take you up on that in a few minutes...”

The elevator reached its final stop and we exited. Jillian held my hand in hers as we walked down the corridor to her room, letting go only to fish her key card out of her pocket and open the door. She stepped in first and I followed, the door closing behind me with a quiet click.

The curtains on the far side were open, bathing the entire room in moonlight streaming in from the large floor to ceiling windows. I walked over and took in the sight of the town spread out below - we had a wonderful view from way up on the 23rd floor. Meanwhile, Jillian sat on the arm of the love seat next to me and I rested my arm on her shoulder.

“So”, she finally said after a long silence. “Now what? Its been so long since I actually had to seduce somebody”.

I moved to the love seat and sat down, patting the seat next to me for her to follow. She sat down next to me and snuggled up into the crook of my arm. It somehow felt both comfortable and awkward at the same time. I stroked her arm in the quiet of the room, our breathing the only sound audible over the dull background hum of the airconditioning. She let out a sigh and I kissed the top of her head gently.

“Jillian, are you having doubts about this?”, I asked gently. “We don’t need to do anything if it makes you uncomfortable.”

She twisted around to look at me, the moonlight falling across the locks of hair on her forehead.

“No, its the exact opposite. I’m scared of doing the wrong thing and fucking it up again somehow”.

I leaned in and kissed her gently on the lips. She sighed again, this time more out of relief than apprehension.

“We’re not kids anymore Jill. We both know there is no ideal situation to hold out for. We can either seize the moment and do something about it, or let it go and look back at it later and ask ‘what if?’”

“Jesus Georgie, you are so fucking right”, she said as she swung her leg over my lap to straddle me. Her hands moved up to grab my face as she leaned in and kissed me with gusto. I felt her tongue pushing at my lips and I reciprocated. She tasted similar to what my brain recalled from all those years ago, with a faint tinge of the alcohol from earlier this evening. I moved my hands to the small of her back, reaching under the blouse so that they rested on bare skin. It felt smooth and cool. I stroked her gently as our kiss cooled from the initial frenzy into a more comfortable rhythm.

I felt her hands move to my front, trying to undo my shirt buttons but struggling to do so. She broke the kiss and pulled back slightly to allow herself a bit of space to get things done. Our eyes locked as she slowly unbuttoned the shirt all the way to the bottom, leaving just the tails tucked into my trousers.

“Up!”, she commanded and I raised my hips slightly, allowing her to pull them free. Her hands began to rub my bare chest as she moved back in to continue our interrupted kiss.

I ran my own hands up the back of her blouse, unclipping her bra for easier access. She leaned back for a second and pulled her blouse completely off over her head, the bra tangled up in the cloth. I leaned back momentarily to take in the view of her breasts. These were not the perky teenage breasts that I used to masturbate about all those years ago, but they had matured into something beautiful nonetheless. They sagged slightly, giving away the fact that she was nearly 40 now and had been through three pregnancies. Her nipples were amazing, huge dark circles that jumped out from the pale skin that they rested upon, the tips almost calling out to be sucked. She wasn’t chubby by any means, her top half had just the right amount of extra flesh, but not enough to hide the faint stretch marks on her belly.

I felt my cock hardening in my pants and I guess Jillian could sense that too. She knelt on the floor in front of me and began to kiss her way down my chest, pausing a second to give my belly button a quick lick. She reached my waist and began to undo my belt as I just sat back and watched. It took only a few seconds before she had the belt off and the trousers unzipped. I lifted my hips again and she pulled them off, leaving me in just my tented boxers. Her hand brushed gently over my erection through the cloth as she moved her face up to kiss me again.

“Oooh Georgie”, she whispered seductively at me, wiggling her tits so that her nipples teased against my chest. “Do you know how long I’ve wanted to play with your cock? Is he ready for me now?”

I nodded mutely. She put her fingers under my waist band and yanked the boxers down in one quick motion, leaving me exposed with my prick waving in the cool moonlight. She moved her head closer to it and slowly examined it from all angles. Her warm breath tickled slightly and it twitched as I became more aroused. A tiny drop of precum was visible on the head, so she stuck out the tip of her tongue and licked it up.

“Just sit back now and enjoy”, she said with a smile as she took my cock into her mouth. It felt a bit surreal to be honest, for so many years this had been one of my fantasies, but now I was actually watching Jillian suck me off.

For her part, Jillian seemed to be enjoying it too. She constantly varied her technique, sometimes taking me deep into her mouth, sometimes stroking my shaft as she kissed around the knob, sometimes licking me up and down. Every time I felt like I was coming close and tensed up slightly, she backed off, letting things calm down before resuming her ministrations. She kept this up for a while, not that I was complaining. Finally, she looked up at me with a grin.

“I can see you’re loving this Georgie, but its time I got a drink”, she joked. “You’re going to come in my mouth with everything you have, and I am going to swallow every single drop of it!”. Her lips closed around me once more, but this time much more purposefully. She increased the suction around my shaft as she built up a rhythm and I could feel myself reaching the point of no return.

“Oh God, I’m cumming Jill”, I gasped as I felt myself begin to erupt. She kept her lips locked tightly around me as I spurted again, filling her mouth with cum. I felt her swallow as my third spurt released, the intensity finally diminishing. She slowly eased her lips off my penis and swallowed again, opening her mouth to show me that every single drop had indeed been consumed.

I leaned back, completely spent, as she got up off her knees and straddled me again. I felt her jeans brushing against my thighs as she took my face in her hands and kissed me deeply. She tasted slightly salty, the remnants of my cum leaving an after taste, but I didn’t care as I kissed her back with a passion. After a minute or so we broke it off and she rested her face on my shoulder.

“You know Georgie, I wondered what you would taste like ever since that night after the party”, she confessed. “I really should have done this for you back then.”

I kissed her gently as my hands worked their way up to her bare breasts. I caressed them as she let out a soft moan. I trailed my lips down her neck with gentle kisses until I reached her nipples and kissed each of them in turn. My tongue traced gentle circles around them and I could see them hardening in the coolness of the room. I decided to go one step further and took an erect nipple into my mouth and sucked on it. Jillian let out a little squeak, but pushed my head down deeper into her cleavage. I alternated the sucking with short licks from my tongue and even the occasional gentle nibble. In the meanwhile, my hands had drifted down to her denim clad butt. I squeezed the cheeks gently and ran my hands over the sensual curves.