My Girlfriend's Sissy Friend With Benefits
Chapter 2

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,

Desc: Erotica Sex Story: Chapter 2 - 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.

“So, buddy, what gives? Or should I say, girlfriend, because, let’s face it, we’ve always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you’ve been more like a female friend or a gay male one or something like that. Anyway, let’s talk, openly now, about what Rain wants out of this relationship. I want honesty here. I want brutal candor, and yes, you can still wear that outfit. I’m actually giving that one to you, as your starter costume. It’s very cute on you. So, come on, tell the truth and shame the devil, mate,” Larissa urged her roommate, while pouring herself some more wine now that we were home.

“Larissa ... I’m in love with you. I know that you don’t love me back, though, which can be rough, but I’ve taken what I could get. It’s not perfect. It’s not ideal. I doubt that I will ever escape the friend zone to be your lover, especially now that you know what a sissy I am, but it’s more than most guys in my position get. That’s what I keep telling myself. As for others, well, the idea of Stan fucking me regularly would take some of the sting out of not going all the way. I would get laid, even if not in the way that most men do. I’m bisexual myself, so it makes sense on some level. Yes, I’m still a virgin, too. In all ways except getting to eat you out. I wouldn’t mind some limited improvements in my situation, though, since you asked so nicely,” Rain answered, blushing more than a little now, “Thanks for the outfit, anyway.”

“So, improvements ... yeah, I think that I’ve put you through enough tests. Our friendship hasn’t been very fair to you. We’ve been friends with benefits, but the benefits have all been so damn one-sided. Even though you enjoy them, quite a bit in fact, you haven’t gotten any action but what your tongue and your left hand give you. I haven’t had to make any sacrifices for us, and yes, there is an ‘us, ‘ much as I’ve pretended otherwise. I like you, even though I don’t love you. I think that you’re very sweet, very pretty, that’s a more fitting word than handsome in your particular case, but, anyway, you’re an Adonis. You’re a very attractive guy, just not in a rugged or manly way.

“I think that I have been so focused on finding Mr. Right that I’ve had tunnel vision to all else. Well, guess what, I’ve found Mr. Right, I think, and he’s a married, if separated guy who happens to be bisexual. And, you know what, that’s perfectly okay with me. But I have been blind and selfish and cruel. Not intending to be. Just how things are. I honestly thought that you would get bored with this at first and move on, like any other man would. Instead, you’ve stuck around and this relationship is so unprecedented for me that I didn’t recognize the warning signs that I had taken you for granted as a friend ... and, yes, as a lover.

“Someday, honey, someone’s going to snatch you away. Someone who treats you as you deserve and is willing to give you what you want and need in a relationship. Not now, perhaps, but someday. And that idea scares the living hell out of me, love, because I have realized that I want you here, ten, twenty, or even thirty years down the road. I still want you in my life. I’m afraid that our friendship will never be the same, either way, so better this way ... moving out of this friendship with benefits to something more than that. So, perhaps, if Stan is okay with this ... he is an arbitrator, right? He can help mediate this agreement. It’s in his best interests to do so, anyway, since he would benefit from the ground rules being clearly set between us ... all three of us. And he’s free to stipulate what he wants, too,” Larissa proposed.

“Okay, then, this is a bit unorthodox, but we can mostly operate from the essential formula of standard arbitration. How about this? Rain makes a proposal. Larissa, if she doesn’t quite want to go there, makes a counter-proposal, and we work our way toward middle ground on each issue. Sound fair?” I stipulated, somewhat amused by my new role, but willing to help my new girlfriend and her roommate out with this, especially since it was clear that she wasn’t out to impose monogamy or a double standard on me.

“Very well. I want some kind of return of handjob when I am in the mood for that. Is a handjob really too much to ask for here?” Rain came out with his first suggestion.

“Done. That’s no problem at all, sweetie. I will gladly help you choke the chicken. Is that all, or don’t you want a bit more than that? How about something more challenging?” Larissa agreed with a very sweet smile, but also a wink.

“Prostate massage, then. Can you bring yourself to also use your fingers and get me off that way sometimes? I know that’s a bit nastier, but it’s also quite intimate, and, well, a bit on the sensual side. It’s a very loving thing from my perspective,” Rain dared to ask for something a bit more intensive and Larissa broke out into a grin.

“Honey, with an arse like yours, I have no problem touching it that way, provided that it’s kept clean. Regular enemas and all that, which I was going to recommend, anyway, given that you’re likely to take Stan’s prick up your bum pretty soon, right, mate?” Larissa assured him, so far not put off by his initial requests.

“Agreed. I’ll gladly do that,” Rain answered without hesitation.

“So, let’s review here. So far, unqualified agreement about the handjobs. More qualified about the prostate massages, with a clear accord on the cleansing process. What next? Any other, further proposals?” I summarized and did my best to move things along to bolder, riskier ideas.

“Yes, okay, I guess that I can be more daring, then. I want some kind of penetrative sex. Someone penetrating something here. So far, it’s all soft, foreplay stuff, and that’s nice, but it doesn’t join us physically. It doesn’t provide the same intimacy as our bodies merging into one for even a short time. It doesn’t have us ... well, fucking, for lack of a better word. So, how about pegging? I know that’s not technically me fucking her, but it IS her fucking me, and that’s further along than we have been,” Rain dared to take things in a direction that I didn’t expect, still a bit hesitant to go for broke, but definitely making progress.

“Hmmm ... sure, I have entertained some thoughts of that. Rain really does have a nice bum. I have occasionally admired it and had impulses to do things to an arse that sweet. So, yes, I have researched pegging, just last night, in fact, with an eye toward possibly expanding the intimacy between Rain and me to include that. If you want pegging, I’m willing to give it a shot, at least. Mind if I make a proposal of my own, though? Is that too ... out of the box?” Larissa countered with her own idea.

“Well, it’s a trifle out of turn, I suppose, but not entirely. You are expected to make counter-offers, anyway, it just usually follows resistance to the initial proposal,” I noted with some mirth.

“Okay ... I like where this is going. His bum. What about my bum? How about it, Rain? Would you be open to licking and fingering it? Pleasuring it. I would love some more attention to it. Pretty please? You could even slip dildos in there. My arse is a nice one, right?” Larissa suggested.

“Oh, God, that was more than I dared to hope for ... you’ve never even suggested or hinted at ass play, and I feared to propose it, for fear that it was even more risque than anything to do with your pussy. Yes, I would love to lick, finger, and otherwise play with your booty, Larissa!” Rain answered with delight ... and a very stiff rod.

“So, lot’s of ass play. I wouldn’t mind some of that myself. Both your ass and Rain’s, I might add,” I laughed.

“Oh, love, you have no idea just how much you’re going to get use my arse! And Rain’s a given, I should imagine,” Larissa pointed out.

“Yes, we’ve strongly hinted around, but I wanted it clear that I would like to do more than just fuck it. I want to play with it, finger it, and such. And definitely with yours,” I smiled at them.

“Okay, then ... here’s the big one. Some head. Is it too much to ask for a blowjob now and then? You wouldn’t have to swallow. Suck it and spit it out, if you wish,” Rain asked, somewhat pained now.

“Well, this is why we have arbitration. Counter-proposal time. I don’t really want to go down on you. Sorry, but I don’t. Not yet, anyway. Please, don’t get hurt. It’s just that ... for me, kneeling to suck a cock, there’s something to it that I want to reserve for Stan, at least for now. It’s hard to describe, but perhaps it’s that it puts the man in a position where he is undeniably a man. At least in that position.

“So, instead of that, I propose to suck it during a sixty-nine. Every time ... and we snowball kiss each other. Each time. I taste Stan’s cum from my fanny and you taste your cum on my lips. Deal? That’s when we don’t do it as foreplay, of course. No snowball that time, but definitely kiss afterward. This ... would be you in an almost lesbian form of oral sex, where your sissiness could come out to play more. It’s softer, more sensual, not you fucking my face as if it’s a quim,” Larissa rebutted.

“So, what do you make of that, Rain?” I asked him to further things along.

“Yes, that’s acceptable. I could go for that,” he blushed now.

“Well, so far, you’ve given quite a bit of ground, even if you modified the terms, Larissa. Any proposals of your own, before hearing further from Rain here?” I asked my saucy new girlfriend, who had certainly shocked me with her openness to Rain’s desperate moves toward more intimacy than they had enjoyed before.

“Okay, I would like to propose, as suggested before, that Rain be completely a slut for you, Stan. I mean, you know, go all the way, bend over for you, suck your dick whenever you wish it, be available for your sexual needs, just as he has been, and hopefully still will be, for mine. We’ve been playing at this for a bit, but we both know that this menage a trois works best if it’s a more complete one, where Stan and Rain are able to bond ... physically.

“I think that we both know who is the Top and who the bottom in this particular arrangement, too. I like the idea of having this in common with Rain. Sharing a man, a stud, a lover. And, yes, I very much want to experience Stan up my arse, too. I’m Greek, after all. My people have winked at men with other men for millennia. Including wives who used to look the other way when buggery took place. Besides, Rain needs someone who can completely fuck him,” Larissa proposed what we all knew had been coming, anyway.

“Of course. Absolutely,” Rain was now stiff as could be, his cute little prick hard with excitement after all of this sex talk.

“Same here,” I grinned now, “Anything else, Larissa, or do we go back to what Rain wants?”

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