Ashley's Tail - Cover

Ashley's Tail

Copyright© 2017 by Mark Gander

Chapter 1

Erotica Sex Story: Chapter 1 - A Halloween fling with a hostess dressed as a she-devil leads to even more pleasures for an unhappily married businessman. Surprises might yet await them all.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Ma/Ma   Mult   Consensual   Drunk/Drugged   BiSexual   Heterosexual   Workplace   Paranormal   Magic   Sharing   Slut Wife   Incest   Brother   Sister   Father   Daughter   Rough   Gang Bang   Group Sex   Harem   Orgy   Polygamy/Polyamory   Swinging   Interracial   Black Male   White Male   White Female   Oriental Female   Hispanic Female   Anal Sex   Analingus   First   Oral Sex   Pegging   Petting   Pregnancy   Squirting   Big Breasts   Public Sex   Halloween  

I was thankfully in a very relaxed mood that Halloween, probably due to not having to deal with trick or treaters this time around. My twins were spending Halloween with their mother. Although I missed them and enjoyed their company, I wanted to kick back and have some beer, not spend the evening answering doors when I was alone. I much preferred to do something more adult with my time. I opted to walk to the nearest tavern, not a mile from my house (I kept it because Tracy, my estranged wife, opted to move in with her boyfriend). With any luck, I might find a girl or two and take them back home for some booty.

When I arrived at the bar and grill, I was greeted by a tall, lively blonde with red horns and an equally red tail, protruding from beneath her black miniskirt, that she playfully wagged whenever she felt like it. She had blue-grey eyes and her golden hair was long and wavy, too. I had to admit that just being around her was infectious, putting me in a much better mood overall. She also had legs and an ass to die for, at the risk of sounding too ghoulish (well, it was Halloween, after all).

“Hey, I’m Ashley. Let me show you your table,” the hostess winked at me as she guided me to my booth.

“Thank you, Ashley, and nice to meet you. I love the outfit, by the way,” I grinned at her and she smiled back.

“Yeah, I’m a bit of a she-devil at times, so it fits. Karen will wait on you, by the way. I hope that you like gingers, too,” Ashley winked again, as a saucy redhead came up to me with some ice water and leaned over just enough to show me her cleavage from her Black Widow outfit.

“Karen here. Any thoughts on your drinks or are you ready to order right now?” the crimson cougar inquired.

“Jack and Coke for starters. So, that’s two staffers at this place ... new management?” I probed, just being curious.

“Jack and Coke it is. And not exactly. Two of our regulars quit for the most obvious reason: they married each other and moved out of state. Who’d have thought it? Then again, who could tell? They just never told a soul that they loved each other that much, Kristy and Trish, that is. Nobody had a clue that they were a couple in the first place, or that they were lesbians, for that matter. They were very quiet about it until their last day, when they both came out and announced their engagement, or so I’ve been told by Brian. Trish was a bit tomboyish, from what I heard, but now she’s gone all-out butch, or so Brian informs me,” Karen intimated with a hearty laugh.

Karen took her time walking away, thus letting me get a very nice and enjoyable view of her booty through her black leather pants, which wasn’t bad at all for what I had to guess was a woman in her late thirties or early forties. There wasn’t much, if any, sag to her ass, certainly less than what understandable sag there was to her impressive bust. Between Ashley and her, my blood temperature was more than a little on the rise. Karen kept herself together pretty damn well and I loved her freckles, even if they weren’t what one expected from Natasha Romanoff.

“So, you like Karen, then?” Ashley broke into my thoughts, much to my surprise since she was the hostess.

“She’s very ... likeable, I must say. As are you, of course,” I smiled at Ashley, enjoying the view of her.

“So I see,” Ashley looked down at my bulge as it grew in front of her, “someone wants dessert, doesn’t he?”

“That obvious and thirsty, am I?” I chuckled a bit, perhaps a little flustered.

“Honey, you don’t have to explain or blush or anything. Certainly don’t apologize. It’s very flattering, both to me and to her, I think. What if I told you that she’s my roommate as well as my colleague?” Ashley asked me, distracting me from my surprise at how she chose to spend her break.

“I would be lying if I claimed that some ... very pornographic ... fantasies didn’t come immediately to mind,” I confessed, getting a wink from Ashley, just as she walked away, her tail swishing again with delight.

Karen returned right then with my highball, and at that point, she asked me, “So, have you decided what you want, other than Ashley’s ass, that is?”

“And other than yours?” I teased her back, making her blush to my shock.

“Yes, other than that,” Karen clearly enjoyed the flirtation.

“I’ll have the surf and turf, in fact. Baked potato, plenty of butter, cheese, sour cream, and chives, plus asparagus, of course. Tomato basil soup for the appetizer, by the way,” I grinned, even as Karen leaned over again to show me more of her freckled cleavage.

“I love your taste in cuisine. Tell me, how is it that you’re dining alone, anyway?” Karen inquired, perhaps for herself, perhaps for Ashley, or perhaps for both.

“I’m going through a divorce, it seems. Rough business. She left me for another man and moved in with him. Hence the cheater’s mark where my wedding band used to be,” I explained, showing the lack of a ring.

“Yeah, I’m divorced myself. I know the feeling. Guess we have something in common. He left me for another man, too,” Karen laughed in a bittersweet way that showed some pain, but also acceptance.

“Gay? I guess that you can’t do much about that, can ya? Can’t grow a dick any more than I can turn black for Tracy. She’s a Queen of Spades now. Only likes the dark meat. Even wears the anklet and tattoo. You can’t blame them for what they like, but it still hurts like a kick to the balls. How’s this for irony? She was the one who wanted marriage, when I was younger, wanted to wait until marriage for sex, too. We got married young, before I knew what I really wanted, or she did, for that matter. Religious parents in her case. I wonder what they think of her shacking up with another man now.

“Me? I was just a good Jewish boy who didn’t know any better back then. Saul Weintraub, by the way. Parents thought that I goofed up by wedding a goy, but they gave their blessing, figuring that if I changed my mind, I could always divorce her. That’s the upside of not growing up Christian, I guess. A bit more pragmatic take on marriage and family. Christians can often be a bit foolish about these things. Mind you, I’m Reform, not Orthodox, certainly not kosher,” I chuckled a bit more, as Karen gave me a very sympathetic laugh.

“Yeah, aren’t we a pair? Hey, I’ve gotta place your order, but I must admit that I look forward to coming back to your table, hon,” Karen assured me, lightly caressing my shoulder as she left.

“So, quite the treat, isn’t she?” I heard Ashley speak to me again, making me turn my head to face her.

“That she is, as are you. That’s the trouble with me. Despite years of marriage, I’ve never quite lost the wandering eye. I’ve never been happy with that aspect of marriage, though I miss many others. I guess that it’s a blessing in disguise now. I’m free to be what I really am, a very much polyamorous fellow. No more monogamy for me. I won’t lie. I still love her and I’m still hurt by her leaving me, but it’s for the best. She and I have little in common, if anything, anymore,” I shrugged, to which Ashley reacted by stroking my cheek.

“Yeah, my ex-boyfriend was a piece of shit and I’m glad to be rid of him. The only good that he ever did me was ridding me of that damn virginity bullshit. People speak of losing it like that’s a bad thing, but I don’t miss my cherry at all. He left me, too, believe it or not, but I probably would have left him if he hadn’t, eventually. I don’t have any virgin holes left, but that’s a good thing, if you ask me. I know what I like and why I like it.

“I like being fucked hard. I like older men. I have no time or patience for overgrown boys or boyish men or whatever. I like my men to be in control, but still let me be girly ... you know, girlish at times. Playful, mischievous. I like to be the junior partner, the sex toy, the private plaything of my lovers. Fuckmeat. I am that. I’m fuckmeat for a guy like that ... a guy like you, in fact. My ambition is to basically find myself older, preferably married guys and be their personal cum slut for the rest of my days,” Ashley presented herself rather candidly, with unmistakable sensuality.

“Why preferably married, I’m just curious?” I probed, just as Karen returned with my soup.

“Because Ashley likes to free a man from his marriage vows, as a man should be freed, while still knowing that he stays married so that he’ll never try to marry her himself. The last thing that she wants to is walk down the aisle, am I right? At least not with a normal, typical hubby, who might get jealous, that is, I know that much,” Karen explained as she set my soup down and I began eating it with the complimentary bread.

“Yeah, marriage would be tough to do, because I intend to be fuckmeat for my married boyfriend or boyfriends first. That might still leave some for a hubby or whatever, and I wouldn’t mind him having fuckmeat of his own, but he’d never be my priority. That would be the sticking point, assuming that he was even willing to share. No, marriage seems a bit difficult and awkward for me,” Ashley gave her parting shot as she returned to her hostess duties, “by the way, I suck and fuck Brian, my very married boss, and I don’t intend to stop.”

“Damn, makes me almost wish that I was still actively married, but to a different sort of woman than Tracy, of course,” I commented to Karen, who snickered.

“How about me? You could marry me, move in with us or have us move in with you, and then you’d have the perfect wife-and-mistress or wife-and-cumslut package already preset for you. I wouldn’t mind in the least if you took Ashley as a lover. Hell, I’d be very eager to try to seduce her myself. I hoped that she wouldn’t mind that. What do you say, honey? A ginger cougar slut to wife and a blonde cumslut girlfriend on the side. I can’t promise to be faithful in any sense, as I get it on with Brian now and then myself, but I doubt that you’d mind, would you?” Karen proposed marriage rather brazenly.

“Well, then, I think that we might well have a deal, ma’am,” I laughed, but the tone of my voice made it plain that I was in earnest, as did my facial expressions.

“I hoped as much. It’s rare to find a like-minded guy. What do you do for a living, by the way?” Karen asked me before returning to her duties.

“I own a chain of liquor stores, ma’am. I expanded it from three to five shops. Before that, I was a uniformed police officer for about seven years. I quit the force when my uncle left me the business and I couldn’t let it fall into the wrong hands. Too many jobs and the family fortune at stake. I tend to cut discounts for cops, of course, especially my former colleagues from the Sheriff’s Department. Well, we can talk it over, you, Ashley, and me, and see what we work out together. I don’t know how long the divorce will take, though, just a word of warning, as the wife and I are haggling over the terms,” I told her as she headed back to work.

“Or maybe she’s having second thoughts,” another female voice spoke up, a very curvy, buxom brunette who could have men drooling in her own right, “Hi, I’m Michelle, Brian’s wife. Yes, I know what kind of husband I have. I knew it from day one. I don’t mind. It gives me time to fuck around, too, you know. Yes, he knows what a slut his wife is, too, and he doesn’t mind for the exact same reasons.”

“Well, I applaud his taste in women, threefold. You’re enough to draw attention by yourself, but adding the other two ... wow, how does he get anything done but sex?” I laughed, inviting Michelle to sit across from me.

“Don’t worry about them. Their jobs are safe, both through me and through him. Hell, I’ve been screwing Karen for a while now and everyone knows it. I brought her into the job, did she tell you that? I’m a horny slut for cock, sure, but I’m a big one for pussy, too, not to mention ass of both kinds, and Karen’s ass is a dessert all its own. More than worth licking,” Michelle laughed as Karen returned, this time with another Jack and Coke without me asking, “by the way, your money’s no good here. You’re my lover now ... and Karen’s ... and Ashley’s. You’re going to help Brian satisfy us, aren’t you?”

“So ... you weren’t too broken up over your ex leaving you, then, were you?” I asked Karen, who kissed me in front of Michelle, and then kissed her as well.

“Honey, I never claimed to be the world’s best wife. But, yes, I was hurt. I knew that he was fucking around, of course. I didn’t mind that. Why should I, when I was doing it, too? I even knew that he was doing it entirely with men, but I wasn’t going to judge that, either, as long as he fucked me, too. I looked the other way constantly, but he decided that I wasn’t good enough, because he wasn’t attracted to me at all anymore, if he ever was. I think that I was his beard. With a different sort of man, this could work, though. You’re more my type than Rich ever was, aren’t you?” Karen proposed, licking her lips as she left to check on the status of the meal.

“By the way, your food and service are now top priority. You get your drinks refilled, your supper plated, and everything, ASAP, no grief at all. Dessert and all that jazz,” Michelle informed me as she sat in her tavern wench costume.

“Yeah, he’s our favorite customer, ain’t he?” Ashley told me as she walked by us, flashing me just enough of her buns under her skirt to leave me a message.

“Very much so. By the way, you now have a date tonight. No more stag for you. You’re on a date with me and that means very special treatment indeed now. I’m co-owner of this here dining establishment and I contribute very much to its success, as Brian knows for sure. I think that I’ll have the salmon myself, with a seasoned rice pilaf, steamed broccoli, and a nice, hearty minestrone soup.

“Can you tell that I’m Italian? You can keep your highballs. I’m strictly a wine girl. A nice, good old-fashioned Riesling, don’t you agree? For dessert, some tiramisu ... delicious!” Brian’s missus all but took over my evening, but that was okay ... she was treating me as an honored guest, after all.

“Wow ... I definitely didn’t expect to have a date tonight, but a sexy, happily married woman whose husband owns the place with her and who gives the blessing for her to be one of my lovers ... wow! Not to mention that you’re such great company,” I reacted with amazement.

“Look at you, sweet talker! I see another reason to want you! Oh, and here comes Karen with your entree!” Michelle informed me, as Karen indeed brought my main course, leaning over yet again to give me a great view of her bosom as she did so.

“Is there a catch to this, other than having to keep myself in good enough shape to service three women?” I chuckled now, even as Ashley winked at me from her post while greeting new patrons.

“Sure, there is. There always is. Brian is ... well, sterile. We just recently found this out. Knowing that I’m not faithful, anyway, and having always looked the other way with me ... he gave me his blessing to have another man do the deed. It was the first time that either of us basically admitted what we already knew, that we both have lovers on the side. I’ve chosen you, so how about it? You’d have to breed all of his children, since I want them to have the same birth father, if that’s okay with you. I don’t have that many childbearing years left, though I’m a bit younger than Brian, of course, but each time, I want you to sire the brats on me,” Michelle licked her lips at the idea of me breeding her.

“Oh, damn ... so when are you going to be ... how do I put it, fertile?” I asked Michelle.

“Not tonight, though Ashley is. That’s why it’s her night with you, and she plans to snatch you away pretty soon for a bit to pump and dump, if you will. Trust me, we’ll set this up for you fairly soon ... for you to impregnate all of us. Karen, Ashley, and me. Any other questions, lover?” Michelle asked me as I dug into my steak and shrimp.

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