Friends with Benefits Leads to More

"You know I'm getting close, right?" I leaned over and whispered into her ear.

"MmmHmm." She replied.

I felt my balls riding up and clenched my ass in preparation for my first volley.

"Yessss." Sid said, as she quickly leaned down and engulfed the head of my cock in her mouth creating that familiar vacuum seal and sped up the pace of her hand.

I groaned as quietly as possible as my first rope of cum hit the back of Sid's throat and she swallowed. Then again, and again, and again. She swallowed each time, keeping up with my spasms as I shot each load into her mouth.

As Sid sucked the last dribble of cum from me, I opened my eyes and noticed our waitress was standing to my left, with her back to us, appearing to be casually standing and watching the DJ, while effectively blocking anyone's view of Sid sucking my cock from the tables off to our left.

I gently patted Sid on the back of her head and she looked up, smiling and licking her lips, then noticed the waitress who looked at Sid, then reached down and used her finger to wipe some cum off of Sid's chin, then slid her finger into her mouth as we both watched her enjoy her small sample of my cum. "MMMmmmmm."

Sid put my cock away and zipped me up. I had stopped finger fucking her as my own orgasm distracted me and Sid reached down, gently pulling my hand from between her legs and lifting it to her mouth so she could suck her own pussy juice from them.

"Have you ever tasted yourself on a man's cock?" I asked.

"Yes, but never after he's cum in me."

"I'll have to see what I can do about that."

"Definitely."

"Dance?" I asked.

"No. I think I'm ready to go." Sid replied, then leaned in and whispered, "I need to cum."

I signaled our waitress for the check and she came over shortly, "Leaving so soon?" She asked, clearly disappointed.

"Yes. We're danced out." As I handed her my credit card.

"Ok, well, the manager may be sending some of us home early cause of the light crowd tonight, so... um, take your time..."

I nodded towards Sid, "I think the engine is pretty well warmed up, so, not sure it'll take long. And my engine's definitely in neutral for a while."

"Well, maybe it'll work out, but if not, I'm sure I'll see you guys again soon, right?"

"No doubt." I replied.

In short order, we were headed out the door, once again, arm-in-arm, and once again, in the back seat of my car.

"I really can afford a nice hotel room, ya know."

"I'm sure you can, and will, but for now, I think the back seat is kinda cute." And with that, Sid slipped her shoes off, spun around in the seat and leaned back into me in the same position as last week.

I rested my hand only momentarily on her hip before sliding it down past the hem of her dress, then back up between her legs until I pressed up against her pussy and felt the same wetness and intense heat as I had last week, minus the panties.

My fingers slid into her pussy with ease and soon found her g-spot as my thumb again started to massage her clit.

"Wait." She said and lifted her hips enough gather her dress in a bunch above her hips, then leaned forward and pulled it over her head.

This was the first time I'd seen Sid completely naked. I imagined her tits were nice, but "nice" is a gross understatement - They were perfect! A little bigger than my fist - I would find out later, a nice, firm C cup, sitting up on her chest with nipples hard and erect slightly smaller than a pencil eraser.

"Wow! Absolutely beautiful!"

"You can tell me how beautiful my tits are later, right now I want you to suck on my nipples while you finger me."

I immediately pushed my fingers back into her and leaned down and covered the closest nipple with my lips.

She rolled her head back and closed her eyes, "oh my god that feels so fucking good. I love having my nipples sucked and nibbled."

Not missing her use of "nibbled," I placed my teeth around her nipple and began gently biting down, measuring her response.

A groan came from deep within her. Then, "Harder. Harder."

It briefly occurred to me that I wasn't sure if she meant I should bite down harder or finger-fuck her harder, so I went with the safe choice and did both, slamming my fingers into her g-spot, rubbing her clit on each inward push of my hand and increasing the pressure of my teeth on her nipple.

"OHHHHHHHH! FUCK! FUCK! FUCK! YESSSSSS!" She screamed loud enough that I worried that she might be heard by anyone near the car.

Her hips were thrusting up to meet my hand on each stroke. Her hand was on the back of my head holding me in place on her tit.

"Fuck me. Fuck me. FUCK ME! Oh my fucking god yessssss! Make me cum baby!"

She threw her head back again and her mouth opened as if to scream, but no sound came out. She arched her back and thrust her hips up, pinching her other nipple between her fingers so hard it was turning purple.

"OOOOHHHHHHH!" She wailed as her body tensed and then I felt it. All at once. Her pussy clinched around my fingers with a death grip that stopped all movement. She released her nipple and grabbed my hair, pulling me hard against her tit, and then her pussy unloaded a torrential flood onto my hand and arm.

"FUUUUUUUCK!" She screamed as the most intense orgasm I've ever seen a woman have crashed down on her, causing her body to tremble and quiver, her tits rising and falling as she gasped for air.

I held on as well as I could, limited by the fact that my right hand was held in place by the vise-like grip of her pussy.

"Fuck yes! Cum for me you slut!"

I caught movement out of the corner of my eye out the window and looked up to see our waitress with her arm angled down, clearly she was fingering herself - and her head back and mouth open as her own orgasm rattled through her body.

I looked back down at Sid and leaned in and kissed her. When I looked back up, our waitress was gone.

I was glad to feel Sid's pussy relaxing its grip on my fingers and gently eased them out of her.

She whimpered in disappointment as she felt my fingers slide out of her, opening her eyes slightly and watching as I brought my hand up to my mouth and tasted her sweet nectar.

"Oh. My. God. What did you do to me? I've never cum like that - ever."

"I guess my secrets' out. I have a red cape and an "S" on my chest."

"Smart ass."

"That was without a doubt the sexiest thing I've ever seen."

"You shoulda been on my side of it. Holy shit that was intense. I'm glad I finished you off in the club cause there's no way I'd be able to do anything after that."

Sid shivered slightly, "I think I'm cold, but I'm not sure I can feel my body yet."

I started sliding my hand between her legs, "Here, I think I can warm you up if you'd like."

"Oh fuck no! Keep those fingers to yourself mister. I'm so sensitive right now I'd probably explode if you touched me."

"Pussy." I goaded her.

"Prick." She jabbed back. "Speaking of which, is that what's poking me in the back?" She asked as she reached behind her and squeezed my rock-hard cock.

"Oh fuck. You're definitely gonna have to take a raincheck tonight baby, but I promise I'll make it up to you soon. Ok?"

"I'll hold you to that promise, but, yes, ok."

"Help me put my dress back on. My arms feel like they weigh a hundred pounds. God, I hope nobody saw me in the car like this."

"Well, we did have a little bit of an audience."

"No Way! I hope they don't know who we are."

"I'm pretty sure she knows who we are."

"Wait - the waitress?!"

"Yep."

"That little slut."

"How long did she watch?"

"Not sure, but based on her reaction, I think you both came at the same time."

"No way!"

"Yes way, and then when I looked back up, she was gone, but I think if I'd have looked up in time to wave her in, she would've jumped at the chance - I'm just not sure if she woulda devoured you or me."

"Mighta been fun either way." Then, turning to look at me, "So which would you have preferred, her sucking your cock or watching her lick my pussy?"

"Do I have to choose?"

"Pervert."

"Slut."

"Your slut sweetheart. Your slut."

"God, I wonder if I can sneak into the locker room and shower before I go home. One whiff of me and Mac's gonna know..."

"I'm pretty sure you'd set off the alarm if you tried to get into the building now, and, besides, do you really think he'll be surprised?"

"No, actually, I don't. Fuck it. What time is it?"

"A little past 1."

"Oh, fuck. Walk me to my car. I don't want him out looking for me or calling the cops,"

We straightened ourselves out as much as we could, and I walked Sid to her car. We kissed goodnight, then once she was in, I leaned into the car and kissed her again and slid my hand between her legs, almost reaching her pussy before she clamped her legs shut.

"Oh my god, you're an animal. Momma's pussy needs some rest baby."

"Oh sure. It's all about you isn't it."

"Fuck you."

"Is that a promise?"

"Definitely."

"Night Sid."

"Night sweetheart."

And so we moved easily into a regular pattern of spending time together - not every Friday, but usually every other week and sometimes back-to-back.

Most nights we were at the club - same table, same waitress if she was working - and she mostly was.

We never spoke with her about that night, but there were plenty of double-entendres and innuendos.

Sid had also developed a little code with the waitress, who's name was Hope, and if Sid said she'd be needing something to nibble on that night, we knew we could count on Hope arranging for the lights to be dimmed just a little darker and standing just to the left of our booth, blocking anyone from seeing Sid as she sucked my cock.

And about once a month, I would look up and see Hope watching us through the window, as she rubbed herself to her own orgasm.

I even waived her in once to see what she'd do and her eyes got big, but she quickly shook her head no and we both watched as she came on her own fingers and then sucked them clean, blew us a kiss and skipped off.

On more than one occasion, I offered to get Sid and I a room at the Marriott next door, or have her follow me to my place, but she was afraid that she'd fall asleep after we fucked and not wake up until morning; so, it was finger-fucking, pussy licking, titty nibbling and blowjobs in the back seat.

It was one of our Friday-night-at-the-club nights when I couldn't quite put my finger on it, but something about the night felt different.

Sid seemed playful as ever, but slightly distracted.

We danced, drank, laughed, touched and I fingered her pussy, but she only occasionally squeezed my cock - never taking it out to jerk off or suck.

The night, as always, was still sexually charged, I just had a sense that something was different.

I asked her if she was ok and she assured me that she was more than ok, so I dropped it and decided to just enjoy the evening as usual.

Then, around 9:30, Sid leaned over and whispered, "Walk me to my car."

She looked at the puzzled expression on my face and said, "I'm taking you home for a nightcap."

I was about to ask one of the million questions that immediately popped into my head, when she reached up and put her finger to my lips in a shushing motion, "Don't talk. Just walk me to my car and follow me home."

I started to motion Hope for our check, "I already took care of it. Let's go." And she leaned over and passionately kissed me.

We started the journey to her house with a million questions running through my mind. Fortunately, it was a fairly quick trip and in short order I was walking up to the front door, where Sid was waiting for me.

She smiled as I approached, then leaned in and kissed me on the lips, "I don't really know where this is going, but..." She didn't get to finish her thought because we both turned towards the front door as it opened and Mac was standing there with a drink in each hand.

"I called him and told him I was bringing you home for a nightcap."

"Bourbon neat for you," Mac said as he handed me a drink, "and rocks for you." He said to Sid.

"Thanks Mac, that's a helluva greeting!" I said with a smile and extended my hand.

"My pleasure. You would be Nick?" And we shook hands. "That I would."

"Thank you sweetheart." Sid said to Mac, taking her drink and leaning in to kiss him on the cheek as we both walked in.

"Very nice!" I said, looking around at what I could see of the house.

"Mac will give you the grand tour while I run upstairs and change real quick - make sure you two knock before you come into the bedroom!" And Mac & I both watched as she walked upstairs.

"Drink ok?"

"Perfect. Blanton's?"

"You do know your Bourbons, Nick - yep. Come on in. This is my study."

It was the quintessential study - dark wood desk and built-ins. "I can do most of my work from here so I only go into the office about once a week."

"Nice commute."

Mac laughed, "Yeah, and I can zoom into meetings wearing a shirt and tie and no pants."

"I hear ya. Someone should do a survey to find out what percentage of people join a virtual meeting only dressed from the waist up."

"For sure. Numbers' gotta be high." We both laughed.

We proceeded through the remainder of the first floor, then Mac looked at his watch, "I think we've given her enough time to change." And we started up the stairs.

Mac showed me through the various rooms of the upper level before arriving at a closed set of double doors.

"Knock, knock! Are you decent?"

"I'm always decent and I'm also dressed! Come in."

Sid was barefoot and had changed into a pair of ass-hugging skinny jeans and a cute little white cotton blouse that left no doubt that she wasn't wearing a bra.

The Master Suite was impressive, as you would expect of a luxury home. A king-sized bed centered on one wall, a separate sitting area, two huge walk-in closets and a en suite fit for a king - and queen.

"Nicely done. So, this is where the magic happens."

"Well, it's where the magic used to happen." Came Mac's reply.

"Sorry," I replied, "didn't mean to touch on a sore subject."

"It's cool," Mac replied, "I'm 11 years older than Sid and, well, we're just in different places when it comes to that..."

I was feeling a bit awkward thinking about what Sid and I had been doing with each other, when my thoughts were interrupted by Sid, "Which is why I'm glad I met you!" She said, walking up and kissing me on the lips right in front of Mac, then turning to Mac, "Right honey?" Kissing him on the cheek, then walking towards the doors.

Mac looked at me with raised eyebrows and an expression that said he'd resigned himself to the fact that Sid was going to get what she wants, so no sense in arguing about it.

Sid led the way out of the bedroom, "Let's go downstairs, I need a fresh drink."

Mac and I followed and I thought I saw a slight stagger in Sid's stride. By my count, she'd had several strong drinks and very little, if anything to eat, so she had to be feeling the effects.

We entered the family room, "Top that off for ya?" Mac asked, reaching for my glass.

"Sure, thanks."

"Same thing for you honey - or are you switching to wine?"

"I'd better switch to wine, I think that bourbon is going straight to my head." She said, handing her empty glass to Mac and looking at me with a wink.

"Come." She said, licking her upper lip and dragging her palm across my cock as she walked over and took a seat in the center of the couch and patted the cushion next to her, "Sit next to me."

I sat next to her just as Mac returned with fresh drinks, "A little top-off on the Blanton's," he said, handing me my drink, "And your favorite Cab Sauv, cheers!" "Cheers!" Sid and I both said as we all clinked our glasses together in a group toast.

Mac started to walk over and sit on the other side of Sid, "Oh, honey, before you sit down, would you put on some music Nick and I can dance to?"

"Sure. I can do that from my phone." Mac replied, sitting down.

Within a few seconds, music began playing and filled the room. I couldn't see speakers anywhere. "Impressive."

"Thanks. Damn system cost me over 45 thousand. I just wanted a nice system and reached out to a buddy of mine who does this for a living and by the time he got done he handed me a bill for 45k - and told me he discounted it from the 65k it would normally cost if we weren't friends."

"Damn."

"Yeah. That's what I said too."

"I like it." Said Sid, setting her drink down and standing. "Let's dance."

I took her hand and looked at Mac with a shrug.

"I wouldn't argue with her if I was you - besides, I couldn't keep a beat if my life depended on it."

I joined Sid in the middle of the room where we embraced and danced to some soft jazz that begged to be heard in the dark, smoky environment of an exclusive speakeasy.

It was easy to close my eyes and forget that Mac was even in the same room with us. I turned us so that I could see Mac and our eyes met as he lifted his glass and nodded as if to say, "she's all yours buddy."

I winked back - not really sure what else to do and decided to stop thinking about it and just dance.

Sid felt good in my arms. Natural. Our bodies molded together and our steps in unison as if we'd been dancing together for years.

I felt her lift her head up from my chest and looked down to see her looking up at me. We kissed. Slowly. Sensually. My cock was already beginning to awaken from the closeness of our bodies. Now it was wide awake.

Sid's tongue pressed against my lips and into my mouth, where mine met hers - our tongues engaging in a dance of their own.

We'd been dancing through several songs and admittedly, the alcohol was emboldening me, so as my back was to Mac, I slid both of my hands down Sid's back and cupped her ass through her tight jeans.

I opened my eyes as I felt Sid gently break our kiss. She was looking up at me and her eyes were darting back and forth between me and Mac, over my shoulder. I smiled and we kept turning until Sid's back was to Mac, leaving no doubt that he could see that my hands were cupping and squeezing her ass. I looked at Mac and he was watching my hands, so I pulled them up a bit and then pushed them down into her back pockets and continued squeezing and pulling her even more tightly against my cock.

He took a sip of his drink as he reached down and adjusted his dick, never taking his eyes off of my hands.

I stopped turning us and we danced in place, gently rocking back and forth as I watched Mac watching my hands. He never looked up at me, but adjusted his dick a couple more times, giving it a squeeze each time.

I felt Sid look up at me again, "You do know my husband is sitting right over there, right?" She said softly. Her eyes were filled with lust.

"Uh huh." I replied, "and I think he's enjoying the show." And nodded toward Mac.

Sid turned her head as we both could see that Mac was very focused on my hands and her ass, as he squeezed and stroked his dick through his slacks.

"I think you're right." She said, as she snaked her hand between us and searched out my cock, giving it a squeeze as she closed her hand around the bulge in my slacks. "MMMmmmm." She moaned softly. "Seems like you're enjoying putting on the show too."

"Yes I am." I said, as I started slowly turning us again knowing that in a few moments, Mac would be able to tell that her arm was angled down between us.

As we began turning again, Mac looked up at me. I winked at him and he nodded quickly. I stopped turning us, pulled just slightly away from Sid, leaned down and whispered in her ear, "Take it out." Never breaking eye contact with Mac.

"Oh, yessss" she replied in a whimper, and brought her other hand between us. I heard and felt my zipper go down and felt her snake her hand into my boxer briefs and pull out my cock, pointing it straight up between us and stroking it.