Cassie Loves Alphas

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(Girlfriend sharing story, haters beware! In the Loving Wives category since Literotica will put it there regardless of what I label it}

Part One- The Boss

I stared in the mirror as I applied my lipstick. It was a, "classy whore," look, which I suppose was what I was actually going for and not the "total whore," thing. To be technically correct, I believe I'm more of a slut than an actual whore. I mean, I'm not getting paid for it, other than a nice fancy dinner or something.

I wasn't the only one looking at my reflection. Paul, who I'll describe for now as my boyfriend or significant other, was staring intently at me. Bless his heart, I don't understand him, why he enjoys the things he does but I'm not arguing. The things I enjoy often match up with what he enjoys and if sometimes other people get pleased as a consequence, good for everyone. You see, I wasn't putting the lipstick on for Paul, or wearing the tight, form fitting skirt that went well above the knee or the top which allowed quite a bit of cleavage to show. I'm pretty blessed up there, to be honest. I'm curvy, as the fat girls like to say, but I'm not actually fat. I have nice hips, a big, tight ass, and tits probably too big for my frame. I stand a little over five feet and my tits are a "B" cup if I want them to spill out, or a "C" cup if I need them held in.

Why am I putting on lipstick and wearing a dress where every curve of me is on display if it's not for Paul? Because I have a date, with his boss, actually. Frank is one of those driven business types. He's much older, he's probably in his early 50's while Paul is 43 and I just turned 35. It was Paul's idea, of course.

Paul's mind is...kinky, to put it bluntly. He has all sorts of ideas on relationships that include swinging, or as the kids like to say now, shades of "polyamory." His ex-wife had quite a few experiences with other men while they were married, only a few of which Paul agreed to. He said he secretly actually enjoyed it as long as he was aware of what was going on, not so much, of course, when she "strayed" without telling him. She wasn't the information sharing type, though. Too bad for her, I bet she'd have been allowed to do a lot more if she'd only confided in him. In the end, though, she left him for someone she'd hooked up with through the internet. I think that's what she was after the whole time.

But here he was eyeing me while I lewdly smacked my lips so that he'd fully understand what it would sound like wrapped around another guy's cock. I asked myself, "what's the big deal, it's not like I haven't sucked cocks before for him, well, for both of us, of course."

I guess I should back up a little. I'd never been in this type of relationship. In fact, most of my relationships were plainly abusive. Most of them were liars and cheats. I always thought all men thought this way, that they were somehow "entitled" to cheat, while women had to toe the line in the relationship or else they were the worst kind of skanks or sluts. I found out this wasn't the case with Paul. I've been slutty before, in truth, but only when I was unattached or only for my significant other when I was. I'd not cheated, nor lied about my behavior, which I cannot say is true about the men I've been with. Currently, leading up to meeting Paul, I had a few friends who turned into friends with benefits, and several....okay, quite a few guys who were "on the list" as potentials, based on their attraction to me. I was actually looking forward to checking that list off.

In no way was I looking to get into another committed, monogamous relationship. I missed my sexually free days, especially coming out of three relationships back to back to back, including my former marriage. I had no intention of falling right back into another one. I didn't want another man who controlled me either with jealousy or emotional manipulation. My ex-husband was the master of that, he cheated freely and openly yet was nearly violently jealous of any attention I got, even if it was a look from a stranger, which I had no control over. When I'd catch him cheating, he'd lie to my face, even, like one time, when he had the woman's pussy juice slathered all over his face. It took therapy and a lot of support to get out of his clutches and thankfully I did. I was looking forward to letting my inner slut out.

Then, I ran into Paul. He's smart, funny, hot "AF" as the kids say (kids say a lot, apparently). I didn't plan it. We got introduced by "friends of friends." We had an instant chemical attraction, the sex was fantastic. I harbored my old fears, however. One morning, after a night of outrageously good sex, Paul caught me crying, still in bed, sore but fulfilled. He looked heartbroken when I told him that I was having second thoughts about becoming more "attached" than we were. I told him what I feared. I didn't want to hurt him if I didn't want to be just "his." For so long I'd longed to be the one with the control, the one to just use someone for physical pleasure. I wanted to be the one who would enjoy, deny, tease at my leisure. My fear was I was falling into another trap with Paul and that I'd again have to stifle my freedoms.

After I spilled it all to him he left the room to make coffee and process what I'd said. He returned quite a bit later after thinking about things.

He said, "you want your freedom to be who you want to be, and who you are, which is pretty fantastic, by the way. I want to be with you, but I don't want to smother you. I've had my relationships, too. I'm not looking to tie you down....though I know you like that sort of thing," he joked.

"I really like you....in fact....I'm afraid I....love you," I sniffed. "But, I really don't want to be anyone's fiancé....or wife right now. I'm just afraid that's where this is headed."

"Because things have gone so well?" he kidded.

"Right, actually. It's usually AFTER the commitment that all hell breaks loose and things fall apart."

"Anything is possible," he admitted. "I just really enjoy you, and not just your amazing body and your skills....oh my god, your skills," he beamed. "It's also talking to you, laughing, enjoying our conversations. I love you too, if that means anything."

"So what should we do?" I asked.

"Why don't you be who you want to be, do what you want, but still hang out with me....or even more, if that suits you. We should at least try it before blowing the whole thing up."

"You wouldn't mind me....sowing my oats?" I grinned bashfully. "I mean I know you've had experience with cheating before but I don't want to cheat. I want to be able to....and then tell it all to you. In fact, our working together, sharing, discussing then having the "after" together would be the best. Could you....do that, accept me back, after fully know what I'd just done?"

"I'm thinking I might....actually enjoy it," he admitted. "To have a wonderful woman, free to do as she chooses, yet still wants to share everything with me? That's kind of my dream scenario, actually. I never understood the whole cuckold thing, where the guy is clueless that his wife or girlfriend is banging everyone behind his back. I totally hate hate hate the sissy, small dick, cock cage, bull humiliating things with a passion. But, sharing in it, being a part of it, maybe even helping suggest things or, on occasion, direct things? That might be something I've thought about before," he admitted with a shy grin.

"I...uh....have more than a couple one night stands in mind. It's been years of built up frustration. I have kind of a "fantasy list," I said, red faced.

"Wow, that's awesome. Truthfully, how many guys?"

"What? How many are on the list? I don't know, really. It's not a written down list," I laughed. "But....let's see...." I was doing the math in my head. "Probably a dozen or so that I know would be into it. I'm NOT saying I'd have sex with all of them, just that all of them are possibilities."

He nodded. "But you'd tell me about it, beforehand? I mean, when you can, but after as well?"

I had never thought about that possibility, I had considered it an all or nothing, a deal breaker. Here was a man who I was totally infatuated with, willing to be my partner, even in this. "I....think I'd really like that," I smiled.

"Still, it might be a lot," I said with some shame, knowing my desires. "I mean you could handle some guy, say, getting my mouth before we, say get together and have a nice dinner?"

"You don't believe me when I say I'd like it?" he wondered.

"It's asking a lot," I said, shrugging.

His face got serious, focused. "How determined are YOU?" he fired back. "You have a dozen guys on your list? Prove it. Pick one, I don't care who, and I don't care how you do it, but have his cum in your stomach when we meet up for dinner at, say, 7 at O'Reilly's."

That's how it began. Embarrassingly, I called up one of my ex fwb's and basically told him I missed his dick in my mouth, so that I could meet Paul on time. It almost felt like I had to beg him to "let" me suck him, which added to its shameful nature. True to his word Paul kept nothing but a smile his face the whole time, including when he pounded my pussy really good at the end of the night.

Since then I've had a few more episodes with Jerry, including allowing him to fuck me. It allowed Paul to tick off another item off his sexual bucket list, the "sloppy seconds" thing He insists he wants more of that, he went on and on about how good my pussy felt "after."

Our sexual "to do" list is quite similar. He also is very turned on by the "stranger" thing, which excites me as well, but which we just haven't tried yet. He really opened up about the cuckold, er, stag thing as well. Turns out he liked a hell of a lot of the ideas, other than the ones above that he ruled out completely. We both agreed that each time, the before and after sex would be some of the most amazing sex we've ever had (which was proven the times I had been with Jerry).

The closest we'd come up to that point with a stranger is the "pizza dare" thing. We order a lot from Door Dash or Uber eats so it has been a progressing game of tease. We both agree that the whole scenario is so clichéd, like porn ruined the whole idea. Still, I've teased quite a few with lots of cleavage and occasionally panty shots. The trouble with reality is, the guys aren't usually "the type." I've had mostly pimply faced 18 year olds who'd probably cum from seeing my tits, or the mid thirties fat guys who still probably live in their mom's basement and play video games all day. Worse is the creepy vibe giving guys who might be serial killers in their spare time. We both agree that random guys knowing our address and our proclivities might not be the best idea. Still, we haven't totally ruled it out, if the situation fits.

Back to the "boss" night. I asked, "do you remember the first time I sucked off Jerry for you?"

He grinned with a blush. "Hell yeah, it was like breaking our virginity, our first experience together."

"Guys really like my mouth," I said, purposely putting the knife in. I enjoy sucking cock, I really do (I know, a woman actually LIKING it, gotta be fake, right?) Actually, I'm lying, I love it. It's one of my favorite things to do, so if I'm fake, so be it.

That was one of his kinks. He liked the poking, the teasing, the embarrassment, as long as he knew it was coming from a good place. He loved me tormenting him like that. He'd never stand for anyone else doing it, however, like one of my "lovers." If they tried that they get punched in the face, no doubt. Paul may be 40 something, but he's still built and ripped "for an old guy." He was and still is plenty athletic. This isn't about "my guy can beat up your guy," or anything, it's just pointing out he would take exception to anyone trying to make him out to be a "sissy" or anything. He is not a small dick, sissy cuckold type, he just likes his girl (me! yay!) to have fun and share it with him. He loves ME laying on the humiliation, though. I try to keep him on his toes.

This whole night was because of him, and that kink. This was HIS boss, after all. I was going to go out with his boss with the purpose of "at least" sucking his cock, all because it would embarrass Paul. It wasn't about Frank embarrassing him, it was about me doing it. We both would know that I did it, that I sucked off his boss. That was the embarrassment kink, always having to face his boss, knowing he got the best of his girlfriend. I didn't really care for Frank, he was a pig. He's a, "me too," chauvinist, arrogant fucker. Strangely, it was also something that gave me a little extra "something," knowing a guy like that was getting me.

"Can't believe you'll have to go in Monday and look at that guy's cocky face knowing he blew his nuts in your girlfriend's mouth!" (Again, he loves it). I could see him squirming at the thought.

"Yeah, that's going to be tough. But, you are ticking off some of MY fantasy list points with each thing. Sex with boss is definitely on there."

It's been refreshing and honestly life changing for me. I mean, here I was getting my lips ready to slather all over some other guy's cock and Paul was grinning like a fool. Frank was his boss, and kind of a jerk. He berated his employees, was crude around their wives and girlfriends and basically presented himself as proudly arrogant. Why would I have anything to do with a guy like that, especially after my prior experiences? Because it was what Paul wanted....ok, maybe I wanted it too, a little....

You see, I really get off on guys and their cockiness. It's just that, in my prior relationships, the guys could never turn it off. The very thing that attracted me to them sexually was also the thing they used to get themselves more "fluff" on the side. But in this case, I basically could have my cake and eat it, too.

Why Frank? It started at one of the company parties a couple weeks ago. Frank is one of those blessed guys that get better looking with age. His hair was half grey, the salt and pepper thing only making him look even more distinguished. To me he looked like he was straight out of a Godfather movie, I'm guessing he's Italian by his last name and looks (not trying to be racist, that's just what I picture in my head). He's handsome and he knows it. He was a bit drunk and was loudly proclaiming what an accomplished lover he was. The rest of us were nodding appropriately, after all, he was boss, while rolling our eyes. Still, the man knew what he wanted and his arrogance kind of....interested me. He asked me to dance and while leaning in to whisper things he'd like to do to me his hands wandered all over me. We were off in the corner, covered by just a bit of darkness, but still quite exposed. He didn't care, he pressed on by sliding his fingers under my dress, across my pubic mound, with a leer.

I excused myself and found Paul. He was smirking. "Having fun?" He'd obviously been watching.

"God, that man is such a pig," I groaned. "Did you see him pawing me like he owned me? Jeez, in front of you, and everyone."

"I did," he smiled. "It looked like you were enjoying the attention."

"I most certainly did NOT!" I said reflexively.

"Look, you know I don't care," Paul said calmly. "It just looked like you were getting a little flushed there, and not just from dancing. Weren't you getting a little....wet?"

He caught me, I knew he could check if he wanted to. "I....guess, a little," I admitted sheepishly.

"I mean, isn't he the type of guy you always talk about when I'm getting you off? Don't you have a secret kink for that kind of handsy, pushy jerk?"

"You know I do," I admitted shamefully. "But, he's your BOSS! I cant, I mean, I shouldn't..... what are you saying....you want me to....do what?"

"I don't know, really. It IS a lot. Whatever gets you off. I'm into it, whatever makes you horny. Just watching you two like that has got me having to try and stifle my hard on. If you like him all over you, let it happen."

"What if he wants....you know, more?" I was waiting for the go ahead from him. I didn't want to guess wrong.

He sighed. "Do what you are comfortable with. If you want to do more, try to do it a little more privately," he joked.

"Well, I'm not giving it up for him, not now, not tonight."

I saw Paul's face form a slight disappointed pout before he caught himself.

"I said tonight. Doesn't rule out anything, he may....get his fingers wet just yet, though."

I saw Paul's face light up. Even though he'd constantly told me what he was into I still was finding hard to believe he'd like....THAT. I was finding out his commitment to it, though.

I went back to dance and let Frank's fingers wander a little more. He maneuvered me into a dark corner and had his fingers probing my wetness under my panties until he got a thick finger in me. I allowed it only for a few agonizing seconds before I pulled away with a grin to go back to Paul.

"Oh, so you are just a tease," he sniffed. "Look, I've got other things I'm working on," he grinned evilly, "but I like what you've got, all of it," he said crudely, while looking totally down my blouse, which I had purposely tried to show off with such a low top. He smirked with that arrogance I was used to. "You know where I work if you decide to stop fighting your very nature."

My knees felt like jelly walking back to Paul. Frank's commanding tone had gotten to me, hit me to my core. Out of the corner of my eye I saw one of Paul's coworkers. She gave me a disgusted look like, "I know what you must've been doing." I wondered if Paul cared about office innuendo, because things like this were bound to get around.

To his credit, he steadfastly stuck to his position. "Whatever gets us off is what's important, I'll deal with the rest, even if it is embarrassing." I still wasn't sure. But, the experiment was eventually going to happen.

Back to preparing for his boss. Paul was sitting eagerly on the edge of the bed. He was ogling my ass as I finished the lipstick and gave him an exaggerated sexy air smooch. He's all man, first of all. As he said, there's no sissy, cock cage, small dick fetish in him (all fine if you are into that, he and I just are not). I've never met a man so skilled with his tongue and fingers. Paul's cock is beautiful, not huge, but most definitely not small. He's not the biggest I've had, but any bigger than his tends to hurt, and not in a good way. We're a perfect match sexually. We'd been together 6 months and over that time had slowly opened the "stag/vixen/shared girlfriend" door with Jerry.

Honestly, he'd been pressing for this for most of that time, since that first "cheating" blowjob. I had still been stuck on disbelief, like, if I actually did anything, he'd totally freak out and I'd lose what we had. His constant assurance had swayed me, well that, and Frank's fabulous fingers. This was something else, though. It wasn't just that I was going to be "with" some guy, it was THIS guy, his boss. He'd have to live with pretty steep consequences.

"You know I'm just probably going to smudge these all over that guy's big dick," I grinned mischievously at his rapt look in the mirror.

"How do you know he's big? Usually braggarts are covering up for their lack of size."

"Um, he was grinding it against me on the dance floor, remember? You know that I'm not a size queen, but big is big, and if it tweaks you a little to know that he is, then, so be it," I smirked.

"Yeah, it kind of does," he admitted with shame.

"I guess we should talk about this, hon. I mean, I SAID I'd suck him off, but guys like this, they are relentless. You know he'll probably ask for more. Wait, he won't ask, he'll just take it."

"So what would you do if you were on a date, no boyfriend? He's the alpha type. Wouldn't you do what you needed to do to get off? Isn't that your biggest kink?"