My Girlfriend's Sissy Friend With Benefits
Chapter 1

Copyright© 2016 by Mark Gander

Erotica Sex Story: Chapter 1 - Stan has just gotten closer to sexy waitress Larissa when he learns her secret: a best friend with benefits who likes to eat her pussy after sex, but doesn't get to fuck her. That's only the tip of the iceberg on the fun and games that ensues when he agrees to move in and fuck them both.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Mult   Consensual   Romantic   Gay   BiSexual   Heterosexual   CrossDressing   Slut Wife   Wife Watching   Incest   Brother   Sister   BDSM   DomSub   MaleDom   FemaleDom   Spanking   Rough   Light Bond   Swinging   Gang Bang   Group Sex   Orgy   Harem   Polygamy/Polyamory   Interracial   White Couple   White Male   White Female   Oriental Male   Oriental Female   Hispanic Female   First   Oral Sex   Anal Sex   Masturbation   Petting   Fisting   Sex Toys   Squirting   Lactation   Pregnancy   Cream Pie   Exhibitionism   Voyeurism   Double Penetration   Tit-Fucking   Analingus   Small Breasts   Big Breasts   Menstrual Play   Public Sex   Nudism  

“Look, Stan, there’s ... there’s something that I have to tell you and explain. It’s not easy. In fact, it’s very fucking weird, even to me, even while I’ve been letting it happen. I have to level with you, because, well, you and I have been flirting for a good while now and I’m smart enough to realize that you want me. Hell, I want you, too. This is very ... very bizarre. Please don’t judge me just yet. Hopefully, we can work out a deal of some kind that lets us date or whatever,” Larissa shocked me with her sudden confession.

“Hey, I’m bisexual. I get strange, okay. If you’re going to come out and tell me that you’re bisexual, too, then, well, that’s something that I can handle as well. There, I’ve come out to you. I don’t think that you’re going to get much stranger than that, are you?” I admitted to my long-time crush, at least in part to make it easier for her to open up and be vulnerable with me.

“Okay, you’re bi. Well, perhaps we can work something out for that, too. Perhaps not. Can we table that for a moment, though? That’s not nearly as bizarre as my secret. You know my best friend Rain, right? Short guy, kind of petite? Slim fellow. Slender, even. Okay, here it goes. He’s something of a friend with benefits. Just not the benefits that you might think. He eats me out, before dates ... and after them. It’s gotten to where I’m a total slut on dates, at least partly for his benefit. He really likes the creampies.

“At first ... at first, I think that it was honestly an attempt to escape the so-called ‘friend zone.’ Some of it was an honest desire to help. Some of it, though, was his actual kink and his submissive nature. I don’t fuck him and he knows that I never will. I just don’t want him that way. At first, I felt bad about it, especially since he doesn’t seem to date or fuck or anything like that. Near as I can tell, he’s still a virgin. Even so, he likes it ... and I like it. What he and I have ... it just plain works. I know, I know. Probable buzzkill. You’ll think that I’m a man-hating, feminazi bitch who emasculates men for fun.

“It’s not that way, though. If you want to break it off, though, I really understand. You would hardly be the first. I have to tell a guy before I get too serious, because I don’t want them thinking of me as a cheater. I don’t cheat. I just have this arrangement with Rain where he licks me clean after sex. It’s at the point that we’re roommates now, just so he can eat me out afterward. On the plus side, if you agree to this, you won’t be under any pressure to lick me down there. Rain can do all that for you. The foreplay and such. You reap the rewards, plain and simple. We discovered, quite by accident, that he likes it enough to focus so much on it, perhaps to the detriment of his own social or sex life.

“You might go so far as to say that eating me out IS his sex life ... and his social life. We even have dates of sort after the dates at times ... or between dates. It’s not that romantic, at least as much as you would think. He brings me flowers ... and we kiss, but we never have sex. We shower together and shop together, but I never call him my boyfriend or anything like that. We’re not a couple. He snuggles me now and then, but he doesn’t spend the night in my bed. He has his own. He’s basically at my beck and call, and no, I’m not at his. I don’t go down on him. It’s a completely unfair, lopsided relationship, except that he enjoys it and so do I.

“Penny for your thoughts, Stan? Now you know why I was slow to make a move on you. It’s tough to admit all this, to bare my soul and admit to a rather strange relationship that society would treat harshly and condemn with harsh terms. They’d call him a cuckold or whatever. It’s not really like that. If he wanted to fuck a girl or guy at some point, I wouldn’t object. I would probably resent it if he got so serious about one that he stopped doing what he does for me, though. He’s not my lover. He is my friend ... with benefits. Oral benefits, that is,” Larissa might have blushed if her olive skin allowed it, but being Greek, she didn’t.

“I suppose that your traditional family doesn’t get why you don’t date or marry him, either,” I observed astutely, making her laugh.

“Yeah, pretty much. They’re always asking about him as if he’s my soulmate or whatever. ‘That Rain, what a weird name, but he is such a nice boy.’ That sort of thing. How in the world do I explain this to them? It’s probably not going to end, either, Stan. I don’t see an end in sight. They’d love you, but they’d still wonder what was wrong with me that I can’t marry Rain. You on the other hand ... how hard did I have to work to convince you to go on a date with me? I know that you’re married, too. I’m not stupid. Separated, but still married. Not sure what that’s about, but I don’t judge. Is that because you’re bi?” Larissa asked me and I nodded.

“Yes, it is. Look, Larissa. When Jessica and I first got together, we were convinced that we had sown all of our wild oats, gotten all of our kinky fun behind us, and that was that. I wasn’t truly monogamous, never have been, but I dealt with it. I sacrificed. That is until a drunken party where ... let’s just say that one thing led to another, and before I knew it, I was in bed with both Jessica and her brother, Tim. We never got together again, especially since it was awkward as hell, but after that, the genie was out of the bottle and I admitted that I was bisexual to her.

“That’s when she locked me out of the house, quite illegally, I might add, and took her brother as her lover. I’m not joking about that, either. They’re lovers, even now. I’m out of the picture. She was so mad that I proved to be bi that she dumped me for her own brother. Weird? You don’t know the half of weird, Larissa,” I chuckled as my new date reacted in shock.

“I call bullshit on that one, honey. She didn’t dump you for being bi. She dumped you because she wanted her own brother. After all, didn’t this incident prove that he was bi, too?” Larissa stunned me by her ability to shred Jessica’s warped logic, “Trust me when I tell you this, babe ... she will want you back in her bed so fast your head will spin once she realizes what a great thing she gave up in you. I don’t know you too well, but I know you well enough.”

“Well, that would explain why she didn’t file for divorce yet,” I remarked ruefully.

“Exactly, babe. Okay, remember when I said that we could work something out and you said something similar. Perhaps we can ... you know, work something out for the three of us ... five if you count your wife and her brother. She doesn’t want rid of you permanently. She wants to sample her brother in a way that lets her experience him alone and compare him to you. She’ll find, I think, that he’s more fun when you’re included. Mark my words. I have a feel for this kind of thing. The kinky and the oddball, freaky stuff, that is. My parents have no fucking idea how vanilla I’m not. I was, but not since Rain and I got started down this path. I don’t think that she has given thought to the consequences of her actions, but perhaps she needs them shoved into her face.

“So, here’s one idea. I need a boyfriend. Not a husband so much as a boyfriend. A regular partner, partly to keep my folks off my back. I’m thinking that I ... I keep Rain as a friend with benefits, while I let you fuck me. As my boyfriend. Here’s the really funny part ... I’ve discovered that Rain likes to wear my panties and such. How he got into that, I have no idea.

“But, anyway, it’s not fair to Rain that he doesn’t get any other companionship. Not fair to you, either. You’re bi. Could you possibly fuck him as well as me? I might even get into the mood to let him fuck me then. I’m not sure. The thing is that he and I have discussed the possibility of him with another man, and he’s always talking about ... wearing my panties and pretending to be me. I think that he gets off on the idea of being in my position, since he can’t be in the other man’s. He’d get more out of it this way than he already does. What do you think, Stan?” Larissa swallowed hard on her wine as she asked me this.

“Okay, so let me get this straight here. You’re proposing that, while waiting for my wife and her brother to come to their senses about me, I take you regularly to bed ... and your male friend as well. The same friend who likes to eat you out after sex and wear your panties. The same friend who gets off on fantasizing about being you. Well, do you want me to move in or just visit?” I asked her bluntly.

“Crash indefinitely. I know that your wife will take you back or rather ask you to take her back ... and that her brother will be part of the deal. That’s fine with me. You’d just visit me a lot after that. I wouldn’t want you to drop me ... or Rain. That’s kind of the thing. I know that I made it sound perhaps temporary, but it’s not really. Stay with me as long as it takes, fuck me and Rain each, and wait her out. She’ll cave. Just please don’t drop me, or Rain, afterward. I really do like you that way. Have ever since the day that we met, in fact. I think that I actually fell in love with you at first sight. Yeah, corny, stupid even, but there it is. Coup de foudre. The thunderclap,” Larissa admitted to me at last, while touching my hand.

“That first time when I showed up at your fine Australian-style restaurant, where you were the hostess, but you wore that tiny mini skirt that left precious little to the imagination? Yeah, I kind of figured that you were a wild child, at least somewhat. I just didn’t know if it was the kind of wild that I liked ... or that would like me back. Damn, those curls of yours, too. Nice dark brown with a tinge of coppery red. Yes, I do recall that quite well. Those long, swarthy legs of yours, smooth and slick as well. You’re from there, too, aren’t you? Greek ancestry, but Aussie attitude,” I commented as she winked at me.

“Yes, I suppose that my accent is a bizarre mix of Aussie and Greek. Hard for some people to place. I was born in Salonika, but grew up in Perth. You know, Western Australia and all that entails. I sometimes slip and use Aussie terms, too, like fanny and bum and arse and all that,” Larissa giggled, “So ... my curls? You liked them? Seriously?”

“Yes, I’ve got a thing for women with curly hair, I admit. Something about it. Not required, just look at Jessica and you can see that. Still, definite bonus. So, you’re in earnest about me keeping you on the side, are you? And your best buddy Rain as well. Are you sure that he’s not, you know, transgender?” I asked her more intimately.

“Not positive either way on that front, love, but I am about you sticking it in my holes and his. Where are you staying, by the way?” Larissa probed further.

“Motel down the street. I wouldn’t mind moving out of that. It costs me a bit to stay there, money that could go to better uses,” I shrugged.

“Well, there you go. Instead of paying rent on a room, you crash at my place and fuck both me and Rain, my lifelong best friend. He’s really been a friend that no girl ever could be. I owe him so much, but I’m in love with you, not him. I can’t choose that kind of thing and I suppose that’s what makes life so interesting, instead of easy and dull. This way, instead of boring monogamy, we have a neat little menage a trois, don’t we? He’s partially escaped the friend zone, not sure if he can do more than that, but he does like what we do, so what can I say? He wants more, but he thoroughly loves what he has with me. It’s hard to explain,” Larissa assured me with a deep soul kiss as she stunned me by paying the bill.

“I don’t know if you’re rich or poor, but this is my first real chance to prove how much I worship you. I really do, Stan. What’s that short for, by the way? Stanley?” she asked me with yet another kiss while I paid the tip, much to her amusement.

“Stanislav. Yes, I’m Slavic. Polish-Byelorussian to be precise. Family came from a town in what was once Poland, later was added to Belarus. So ... out of curiosity, Rain has the money in this quasi-romance of yours, doesn’t he?” I inquired, quite certain of that indeed.

“Yeah, he does. He’s a bit of a tech geek and really smart. Has invented some real gizmos and made money off them. It’s just that he worships me with the same ardor as I do with you. I can’t help it and neither can he. We don’t pick who we love and don’t love, after all. It’s a chain or cycle. You’re in love with Jessica. I’m love with you. He’s in love with me,” Larissa observed.

“Very true. And she’s in love with Tim,” I added, while helping my date to her car ... I was rusty with dating etiquette and found much of chivalry a bit hypocritical given the whole feminist push for “equality,” but I was also still affected by Old World attitudes at times.

“Jessica ... she was your date that first night, when you and I met, wasn’t she? The really cute Latina,” Larissa licked her lips as we got into her car, a Mercedes-Benz (did Rain pay for that, too).

“Yes, she was. But she’s half-Brazilian, half-Thai. True story. All woman, though. Tim, for his part, is her half-brother. Half-Thai, half-Irish. Yeah, long story on that. Part of me thinks that her Catholicism is part of why she won’t actually divorce me. Not sure about that, though. She’s an odd Catholic, but she is one,” I laughed at that while we headed to Larissa’s place. We had a lot to discover there, as we realized when we walked in on Rain ... half-naked in a negligee and crotchless panties, including lace and stockings ... and heels.

“Rainwater Garner Willis, what is the meaning of this?” Larissa called Rain by his full name ... did I mention what hippies his parents had been?

“Um ... well, I didn’t expect you back so soon. Sorry, I’ll put it back. Please forgive me!” Rain pleaded, kneeling before Larissa.

“Shhh ... don’t be silly. I’ve been very selfish in this whole relationship. Far too long. Sure, you enjoyed it, but mostly I used that as an excuse to get what I wanted from you. The least I could do is show more understanding of you. Besides, you’re a real beauty in that outfit. Don’t you agree, Stan? He’s quite the sissy ... prissy and pretty. It’s time that we talked, Rain. This talk is long overdue,” Larissa told him, putting her fingers to his lips, “Hope that you don’t mind Stan tagging along. He’s staying with us for a while, and after we’re done talking, I hope that you and I will get fucked nice and hard by him.”

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