My Girlfriend's Sissy Roommate Ch. 02

"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?"

"Yes ... okay, here it goes. I want Rain to marry me. There, I think that he is due this honour at last. It's only right. Stan would still be my boyfriend, but Rain would be my sissy hubby. Don't worry, love. No extreme cucky stuff. No chastity or orgasm denial. As if I could ever try to prevent Rain from having pleasure. He deserves more pleasure, not less. And, in the interests of properly consummating our union, he should get to fuck me after all. At least the one time, maybe more during the honeymoon. It's only right. You can't get married and not get to fuck your bride.

"But, and this is key, no sex of that type until the wedding night. I want, for the sake of a little play with this whole thing, to make Rain wait until we get married to do that. After that, he gets to fuck my quim as much as he likes, on the condition that you're fucking his arse or mine while he does. You must be included in the honeymoon, the wedding night, and all such fun. After that, he can fuck my arse, too, but not until then. Both holes open up to him only after the wedding, and only with the clear stipulation that you're included in the festivities.

"You're also to be his best man and get him some action of some kind during his bachelor party. Sound fair? I'm marrying him because he deserves some recognition and love and such. I love him, but I'm not in love with him. Still, he's going to be my husband and I don't feel right denying him my body once that takes place. Before then, sure, because he's my friend and roommate, but not once we take vows. This also gets me a more secure place in the country and makes my parents a bit happier. What they don't know won't hurt them.

"Just don't think that this is going to change our dynamic too much, Rain. I still want you to lick me down there after Stan has fucked me. I still want to know that you're my sissy, even more so now that you will be tempted to act all jealous like many husbands do. You won't get like that, will you? You'll know your place, my sweet subby, sissy boi?" Larissa flirted very brazenly while stroking his dick and mine.

"Of course ... I love what we do. In fact, I kind of want to try earning my red wings," Rain shocked us all.

"You want to go down on me when I'm rare and bloody? Have at it, mate. Bon appetit! I shall enjoy that for sure. I also want to rim Rain a bit from time to time. I think that he would be quite yummy back there, as long as he's clean," Larissa offered, turning all three of us on, "I wouldn't mind licking you, too, as long as you're rather clean as well."

"And what about his whole sissy routine? How far do we wish to take this?" I interjected, trying to steer the relationship toward more completion ... Rain would clearly never be that happy until or unless he got to fully explore sissy slutdom.

"Well, at work and stuff like that, on social occasions, I'd be more conservative, I think. In private, though ... well, I kinda want to take it much further. Sorry, but I just do. I want to shop for girly clothes, wear them at home, any place where I have privacy or where people understand and accept what a sissy I am. I'd like to be your sissy slut. Her husband and roommate and friend with benefits, yes, her boi, if you will. But your sissy slut, sir. The idea is a real turn-on, wearing frilly things, maybe even exploring cosplay a bit more, and generally being the sissy boi that I was born to be," Rain asserted, not shocking either of us, except by his sudden candor.

"A sissy needs to be smooth, dear. Can you handle losing all of your body hair? Staying clean-shaven? Maybe keeping your hair nice and long, perhaps in a ponytail most of the time, so that while a superficial glance won't reveal what a pansy you are, at home, you can literally let your hair down. I think that this would be great. It would let you be yourself in the right environments, where no one would judge you. Also, we badly need to shop for lady clothes for you, and maybe reduce your male wardrobe by at least half. You'll be spending a lot more time looking girly, so might as well get busy with it.

"I'm going to love turning you into a lady whenever I get the chance. Makeovers, manicures, pedicures, etc. The works. Find the right panties for you, the right eyeliner, mascara, lipstick, and blush. The right lingerie, though this was a start for sure. I love the idea of you turning men's heads as a girl, when deep inside your panties, you have a sweet little prick tucked away. You have a very girlish figure, anyway, so that helps. See, I knew that we were girlfriends at heart, even if you're in love with me," Larissa continued playing with Rain's dick and mine, the wine starting to hit her hard.

"Well, I think that we have a pact of sorts. A covenant or understanding between us. Is there anything else?" I asked them both.

"Just that, whenever Jessica and Tim come to their senses, I will be happy for you, but I really meant what I said about wanting to continue as your girlfriend. I don't care who else you fuck, okay, I do, but only in a supportive way ... I just want to remain lovers. You, me, and Rain. I would never ask you to be faithful to us. As for whether we're faithful to you, maybe we should play that one by ear ... Master.

"Yes, I want to submit to you a bit, possibly even get a collar someday, and I hope that Rain comes to feel the same way, either about me or about you. Either way, it will benefit you, either directly or indirectly, especially since you get to fuck us both," Larissa licked her lips at the idea of our new arrangement, while still toying with both cocks.

"What about breeding?" Rain asked.

"Whatever happens, happens, babe. I don't mind the idea of both of you getting a chance to knock me up. Either way, I'd be a happy and horny mother-to-be. Count on that. If there is some doubt, there's no reason for you to dispute paternity, right?" Larissa suggested.

"Excellent point, Mistress. I should not question that. Yes, I want to get collared by Larissa here, I have realized. Call her Mistress. Be her slave, but your sissy slut, if that makes sense. You would dominate me together, but in different ways. Parallel kinks and relationships, if you will. And I want our wedding vows to indicate that I am to love, honor, and obey her, not vice versa," Rain declared.

"Sweetheart, that is a splendid idea, but that does mean two weddings. My parents will insist upon a proper Greek Orthodox wedding mass. So, what I think that we should do is, after that, have a sort of separate wedding where we write our own vows. Only certain folks would attend that one, as opposed to the other, more public and churchy ordeal. Our vows would also leave out the 'forsaking all others, ' for obvious reasons. So, is everyone all in one accord? I don't know about you two, but I'm ready for what I've wanted ever since I first met Stan ... I want him to fuck me at last!" Larissa announced, pulling me and Rain both close to make out with each of us.

I couldn't have agreed more with that if I tried, especially when Larissa hiked up her dress and bent over, her panties down at her ankles as Rain began licking her ass. As I slid my cock into Larissa's warm, wet pussy, which soaked itself even more with every stroke of my dick and Rain's tongue, I could feel her body heat rise as her hips moved in rhythm following my own. I was bareback with another woman for the first time since Jessica kicked me out of my own damn house, and God, it felt glorious! When I started pulling Larissa's lovely, curly hair, I discovered just how much she had craved me ... every bit as much as I had hungered for her.

There was no jealous wife and there were no pesky wedding vows to stop me now. That sexy Greek goddess was mine at last, and I was going to own her, for the rest of my life! As much as I wanted Jessica and Tim back in my arms, I was going to be happy whatever they did. Three or five, I had come home to what worked for me. I was free to be poly for a change, at last, and I wasn't going to return to monogamy at any price!