Doin’ the Boss Ch. 09

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May 16, 2023 // By:analsex // No Comment

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American Dad

Just when my life got a little normal, it twisted pretzel-like into thirty three and a third percent more difficult.

And it’s all because of Stephanie Crawford.

It has been a while since I’ve written for Literotica, but quite frankly there wasn’t much I thought readers would want to look over. I was still living with my boyfriend, still cavorting with my former boss, the still married but endlessly horny K. Linford Little (see “Doin’ the Boss” series in Mature section), still working as a senior administrative assistant and still taking some part-time college classes.

If anything, things had gotten tamer than in some of my recent stories because Mr. Little’s job had taken him to the road a lot more, so we weren’t doing naughty things as much. Not that we stopped seeing each other, as Mr. Little had an addiction or oral sex that the best 12-step program in the land couldn’t stop.

But things were, uh, a little bit more mundane. Or as my mom used to say, there was nothing to write home about. Not that I would write anything home to her about my relationship with Mr. Little…she’d keel over and die.

The man had this thing for blow jobs, not that most guys don’t. But he was, well, insatiable. I swear, I could suck him off one minute and he’d be up and hard rubbing cock all over my face the next. Not that he could get off twice in succession, at least hardly ever, but he’d still love for me to suck on his cock for as long as my mouth would let me, savoring every slippery slide up and down his manhood.

The fact that he was 180 degrees from my current boyfriend Roger was likely a plus. Roger was a two-or-three screw a week guy, and oral sex was just a prelude to fucking. That was something we’d do every Saturday night, maybe Sunday morning too, and sometimes do during the week.

He claimed sex drained him, and he had a hard time staying sharp at work if we screwed during the week. Still he was a great lover, he bought me all kinds of nice gifts, and in nearly every regard was a keeper. But the little bit he didn’t give me — the living on the edge, knock your socks off, curl your toes up stuff — was something I realized I hated to give up.

Hence, my re-hooking up a couple years ago with Mr. Little. The now 50-plus guy caught my fancy when I worked for him, and we hooked up first after work then during work for quick, naughty sex. He made promises, I believed him, but when I realized he wasn’t going to leave his wife Mary I left him in the dust. Or so I thought.

Despite other relationships, something was missing, and I realized it was Mr. Little. We got back together with a different goal…we knew we’d never hook up full time, just get together for all the things missing at home, both of our homes.

It has been a whirlwind, pleasing relationship. We get together for sensual fun often, several times a week if possible. Always with a look over our shoulder, always making sure his wife didn’t have an inkling of his extracurricular activities. Mr. Little liked to push the envelope, for while we stopped fooling around in his office we did manage to find places where a little seclusion went a long way.

Parking garages, both stand alone and at full malls, as well as local parks, train station parking lots, bike trails and of course the good old automobile worked well for what we had in mind. The danger of semi-public cavorting merely added to the excitement.

Somehow that all brought to mind Stephanie Crawford, a girl who attended home room with me in high school and a close friend throughout those formative years. We spent many pajama parties together, where the usual topics of conversation was shopping and boys.

We of course were in love with several movie stars and musicians, but those fantasies were supplemented with a heavy dating schedule. Stephanie lost her virginity to Ryan Thatcher in the back seat of his dad’s SUV parked by a local lake on the outskirts of Cherry Hill, New Jersey. I still had my maidenhood, but wasn’t a prude by any means. I learned early on how to satisfy a date with my hand, and later my mouth.

“I don’t know how you can do that, it’s disgusting,” remarked Stephanie one Saturday night at a sleepover at her house after a movie, dinner and make out session with our boyfriends. On those occasions, neither of the boys went home with blue balls.

“I think Erik was a little miffed we didn’t do “it” in the car the other night,” said Stephanie with a laugh about her current boyfriend. “Erik is used to getting some each week and last week he didn’t. I think he’d have done me in front of an audience if I let him.”

“Hey, the guys went home happy,” I replied, mentioning our hands had a long evening pulling their dicks off to a hearty explosion. “What did he expect, you to spread those pretty legs of you right in front of us.”

Stephanie shook her head. “Pulleeze,” said my friend. “I think he thought you two might go for a walk or something.”

We laughed at how guys viewed nocturnal activities in different ways. My date, Glenn, was euphoric over having Karaköy escort bayan me toss off his cock, while Erik, who was used to practicing pushups on Stephanie, was a little put off having to act like they’d never done “it” and settle for a hand job.

Both Stephanie and I were thought to be “good girls” by our parents, who would likely have a heart attack if they knew of our night time activities. They made sure they were around when guys were visiting, so we took playtime to the road when the desire hit. “You know, Stephie, it’s a little embarrassing messing around in the same car, but it’s also sort of exciting, The sounds, hearing the rustle of clothes, the heavy breathing, it gets me hot listening. And then when I have a dick in my hand while listening, it’s, well, hotter.”

Stephanie laughed. “Imagine if we were actually doing it in the car, bet that would really get you hot,” said my friend.

“Yea, maybe we’d take pictures!” I replied, ducking as Stephanie swung her pillow at me.

Stephanie and I would continue our banter well into the wee hours, trading stories, talking about boyfriends, nerds and bitches we came in contact with.

A week after our sleepover we double dated once more, heading to our favorite make out spot near the lake. We loved it there, so secluded, water rippling nearby, and of most importance, never patrolled by the local constable until very late in the evening.

It was Glenn’s turn to drive, and he had his dad’s SUV. As soon as we left the movie I scooted over to be next to Glenn, my head on his shoulder, while Erik and Stephanie immediately began making out. I heard rustling from behind, and imagined Erik’s hands slipping under Stephanie’s blouse or maybe sliding up her thighs.

The twosome in the back made out for the 20 minute ride, making me a bit jealous that they were getting such a head start. But since we switched seats weekly, nobody had an advantage of more room to spread out…so to speak.

When we got to the lake Stephanie and Erik were making out hot and heavy. Taking matters into my hands, I unzipped Glenn’s pants and reached into his boxers for my favorite pole…the hard pillar poking out the unleashed fabric. “Oh, Robyn, that feels so good,” whispered my boyfriend as I slowly stroked his manhood. “You have such nice hands,” I heard him coo.

I slowly traded spit with Glenn as I played with his hardening cock. He unbuttoned a couple of my blouse buttons and snaked his hand inside, plopping a breast out of my cotton bra. He rubbed my nipple as I tantalizingly ran my fingers up and down his manhood. We were lost in our lovemaking when we heard a gasp from the rear seat.

Glenn whispered in my ear, “they’re fucking, Robyn, they’re fucking.”

That brought a gasp from me, as I couldn’t believe my tramp friend was actually having sex while Glenn and I were in the front seat. Still, I really wasn’t surprised, because I had a feeling on one of these dates Stephanie would spread her pretty thighs for her never say die, horny boyfriend.

Glenn, of course, was impressed with the tangled twosome in the back seat. “Come on, Robyn, let’s do it. I want your pussy,” he groaned as I pushed his hand away from my virginal slit. “NO!” was my reply.

I had seen several of my friends get knocked up, ending dreams of college and in many cases a wonderful wedding. I wasn’t a prude, I loved experimenting with sex, but I just didn’t want to chance things. Still, it was so erotic peering over the headrest and seeing Erik pumping between Stephanie’s spread legs. Erik’s ass glimmered in the moonlight, and while I couldn’t actually see his cock or her pussy I surely heard and smelled the sounds of sex.

Looking at Glenn, I knew even one of my A-1 hand jobs would not satisfy his manly urges this night, and besides, I was feeling very frisky. So as he tried to feel me up I decided to take things a step further. Uh huh, young Glenn was going to get a blow job.

It was not the first one I had given, as two guys — Kevin and Scott — had their cocks cleaned by my lips. At first I was a novice, but with a little practice I was able to get into the swing of giving a very good blow job. A bonafide, card-carrying if there was such a thing, fellatrix.

Those days my blow jobs weren’t as practiced as today. Today Mr. Little said my mouth took his breath away. Back then I mostly jerked their cocks with my hand and sucked hard and fast on the tip…guys loved it.

That night I pushed Glenn back in the driver’s seat, knelt on the passenger side, and played with his bulging dick while Stephanie was groaning, moaning and getting laid in the back seat. That action spurred me on, and I looked at Glenn’s dick like it was a bowl of chocolate ice cream.

It looked tasty, and I bent my head toward it to check it out. First I licked the sides of the throbbing cock and then stroked it from the base while slurping the tip. The cock pulsated as I maneuvered my mouth around it. Glenn moaned as I worked the dick, and I think he forgot Escort Kayaşehir all about Stephanie spreading her legs several feet away.

The SUV smelled of sex as we worked in our own little world. I felt the vehicle rock, much of it propelled by the back seat action. I wanted to look at what was going on there, but, well, I was a little busy. Even if I wanted to I don’t think Glenn’s hand atop my head would have let me sneak a look at anything but his knob.

It was awkward in the front seat, and my free hand held onto the top of the driver’s seat to maintain my balance. I bobbed my head around the tip of his cocksickle, enjoying much of the six inch cock in my slimy mouth. A warm hand grasp mine other hand, and I assumed it was Glenn’s. Soon, though, I realized my mistake as I felt Glenn’s two hands caressing my tits.

I must have slowed as the thought was processed in my mind and Glenn pleaded with me to move a little faster. My hand was entwined, though, with Erik’s, a though which sent a ripple through my swollen pussy. When Glenn reached over and rubbed my warm crotch I immediately began to cum which in turn sent by boyfriend over the edge. His cock started throbbing then spurting so much cum I couldn’t contain it all in my mouth.

Those days I normally spit out the slimy seed, but this night was different. I swallowed. At least as much as I could, and it wasn’t all that bad…a little salty maybe, but tasty in its own way. Some got on my blouse, some on his seat, and I swallowed the rest.

The coupling couple in the back seat were also groaning what seemed like orgasms, at least Erik and I found out later Stephanie too. I glanced over the seat and caught a glimpse of Erik pulling away from his girlfriend. I’ll never forget the look of satisfaction on Steph’s face, but what struck me was how her legs were spread so wide. I couldn’t see her pussy in the darkness but I surely could smell the sex.

Why was I remembering nights like that one? Stephanie and I had countless nights out together, and hardly ever talked about Erik or Glenn for that matter. Both were from days gone by. Still, this was simple. I ran into Erik at Dunkin Donuts, and all of a sudden those days and nights came back to me as if they occurred yesterday.

At first I didn’t recognize him, but once I heard the voice say, “Hi Robyn!” I immediately knew who it was. We exchanged pleasantries, laughed over coffee and donuts, and traded stories about what we’d been doing. Erik was a soon to be married successful banker, heading for the Big Apple where he’d be commanding a six figure salary.

I made him promise to call me when he made his first multimillion dollar deal, and he smiled. “I’ve already done some of those, how about a $10-million deal?”

Laughing at myself, I said sure.

We stared at each other, not wanting to leave but knowing we should. I was supposed to meet Mr. Little after his golf game, and Erik needed to buy some gifts for his wedding party.

Still, we hustled up another coffee and continued our reminiscing. Somewhere along the way we reminisced about those nights wrestling in automobiles.

“You had a cute ass,” I joked. “And I think Stephanie loved your attention.”

“Glenn seemed to like your, uh, oral attention,” replied Erik. “But I never did get to see your bare behind, and that just wasn’t fair.”

We spoke about old times like they were yesterday. Of things we missed, of times we wished we had over again and other times we’re happy were gone. Then Erik stunned me.

“There were times when I pretended you were blowing me when I was screwing Stephanie,” said the guy. “I know it sounds crazy, but, well, Stephanie was a great lay and I loved it but she wasn’t into blow jobs. And there Glenn was getting them all the time.”

I laughed and told Erik how Glenn was always complaining about “only” getting a blow job when he was banging Stephanie. To each his own.

As the afternoon progressed we confessed this and that to each other. How Stephanie liked to have her ass fingered when he was pounding her, how Glenn loved to have his balls kissed while I’d jerk him off to completion. Ah, those were the days.

Erik reminded me of the time we held hands. That special time when he was banging Stephanie and I was blowing Glenn. “I saw your hand there and just thought it was so hot to be holding it while doing Stephanie. It was quite hot.”

“And to think I thought at first it was Glenn’s hand,” I replied. “I didn’t know it was you right away, and when I realized Glenn was enjoying himself too much for me to stop what I was doing.”

Erik looked at me and smiled. “That’s so sweet.”

Changing the subject, I asked about his upcoming nuptials, and joked that I needed to get them a present.

“No need, unless you want to give me one,” slyly said the guy.

“So what do you need?”

Erik looked deeply into my eyes, smiled, and mouthed, “Well, let’s see. Maybe a tire iron, or a tie, or a pair of cuff links. Aw, who am I kidding, I don’t need Küçükçekmece escort those things. I need, uh…”

“What?” I asked.

The guy looked at me and smiled. “Well, if you want to give me a present I would treasure forever, you could give me a blow job. That’s been a long desire of mine, to have you give me one.”

His request floored me. The guy hadn’t seen me in years, he was about to be married. And while I have been a little promiscuous I wasn’t a slut. Over the last seven years I had “been” with only three guys. While not chaste I wasn’t jumping in the sack every week with a different banana.

Was he kidding. Was this some kind of a joke I wondered?

So while I was surprised by his admission, I was even more surprised by my reply. Maybe it was because of Mr. Little’s recent admission that he’d fucked his wife before having me suck his pussy-tasting dick, but my answer was quick and to the point.

“I’d love to suck your dick, Erik, I’ve wanted that for a long, long time,” was the reply in my mind.

I stared at the guy before saying, “What about your fiancée? I think she might have a problem with that.”

“Well, I won’t tell her if you won’t tell her,” was Erik’s smiling response. “Come on, you know you’ve always wondered…”

My mind was jumbled.

“Now?” I asked.

“Uh huh.”

My oh my, I couldn’t believe it. We slipped out of Starbucks as if we were shoplifters evading the prying eyes of security guards.

“I’m parked on the on the way up to the top floor of the lot, let’s head there,” said the guy I hadn’t seen in years.

“Head is the operative term,” was my sly, smiling reply.

Erik laughed, “I love the way you think!”

We walked to the stairwell, not bothering to walk all the way down the bottom floor to the elevator. On the way upstairs he held my hand as if we’d been seeing each other forever. My mind was all jumbled as I really couldn’t believe where we were going or what we were going to do. On one hand it was so bad, on the other it was so erotic.

Sure enough, his car was parked well away from prying eyes. Looking around, I realized only if someone really wanted to park up here there was a good chance we’d be alone. He punched open the doors, looked around, and pulled me close. There, in the mall parking lot, I kissed a guy I hadn’t seen in years. It was toe-curling.

We slipped into the back seat and made out like horny teenagers, swapping spit and stroking each other’s bodies like long-lost lovers. I felt his cock tenting in his trousers and decided to unleash the monster from its unwanted confinement. “Umm, yes,” groaned the guy as I slowly unzipped his jeans.

Reaching inside his undies I felt for his cock, which wasn’t fully hard but getting there. It was sort of semi-hard, and I felt around it and his balls like I was exploring a new land. In a way, I guess I was. I continued to stroke his cock through his underwear while he moved closer and kissed me.

I glanced around, felt we were alone, and pulled out the hardening piece of man meat. Looking at the cock, I realized it was a lot like I had pictured. I guessed it was a bit longer than six inches, decent girth, and pleasantly pulsating. A nice cock. I thought to myself how wicked this way, blowing a guy who I barely knew.

I like looking at cocks, but I love sucking them, and I wasn’t about to wait and get spooked. I lowered my head and licked the tip then moved down to the base, alternating kisses and licks on the man meat. Erik groaned when I licked his balls and I knew he was loving what I was doing.

Reaching down I held the base of his cock between my fingers, jerking the dick to full hardness. I kissed the tip again, sort of savoring it in my mouth while jerking the base. His cock was velvet, and I liked the feeling of it pulsating in my mouth.

While sucking I decided to try something a little new, something I had read in Cosmo. I continued to jerk the base of the cock with one hand, but then circled the cock just below the mushroom head with my thump and index finger. That ring around the tip of the cock meant my mouth only licked and suck the top inch or so, and I made sure I gave that part of his dick all the love and attention it could possibly get.

Slobbering all over it, the moisture cascaded down the shaft and soon the dick was very wet to my touch.

“Oh my Robyn that’s so fucking good,” said the guy, his dick throbbing to my touches.

That spurred me on and I continued my sucking episode. I couldn’t help thinking of Stephanie and wondered what she’d say if she knew I was sucking her old boyfriend’s cock. I wondered whether I’d have the guts to tell her about this little rendezvous when she returned from her business trip to Tucson.

Erik was obviously loving my mouth attention and knew he wouldn’t hold out long. But the guy surprised me, pushing my head off his cock and asking me to scoot around a little so that he could feel my ass. At first I was put aback, because I knew he had been ready to cum, but then I was honored he wanted to last a little longer…you know, sort of sampling even more of my oral skills. He played with my ass for a while, gradually lifting my skirt and slithering his hand down my panties for a feel of flesh. Once that was accomplished he pulled my head back onto his cock and I restarted my cocksucking.

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