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My Girlfriend’s Sissy Roommate Ch. 04

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“So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it’s between you and Rain, and I think that it’s rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn’t go so far as to call him a cuckold in the typical sense, as you’re offering him more than many cuckolds get, but he’s a wittol, I suppose, in addition to being a sissy sub,” I asked Larissa as we felt each other up in the shower once we were both clean.

“Yeah, I suppose that his positive and grateful attitude helped. Then again, that attitude wasn’t surprising from a man who has basically escaped the friend zone entirely, and mostly through my good graces, not any action of his own. A lot of it, though, is the sheer beauty of what we have and the feeling that I took his love for granted. I also wanted to impress you, I think, and the more loving I am to both of you, the more impressed that you seem to be. Not that you seemed to judge me, but the more generous I was to Rain, the more you seemed to take pride in me.

“Also, hey, there is a certain sensuality to a full menage a trois, isn’t there, where three people all make love to each other and bond completely? Nothing against a V, of course, which was partially what I intended at first, but this just seems more … seamless, more satisfying to everyone, at least to me. Still, I do want you along for the honeymoon, the bachelor party, and all that jazz. I want to make love to both of my guys, have them enjoy each other as well, and wake up the day after my wedding to the glorious feeling of completion for all of us, no feelings of alienation, loss, jealousy, etc. No one feeling lonely or shut out.

“I would like for Rain to wear lingerie under his tuxedo at the wedding if possible, and then women’s clothing as much as possible during the honeymoon, playing the party fully. I also wonder if perhaps we can arrange it for my hen party to happen on a different day than the bachelor party, and for both Rain and you to show up and get reverse gang-banged by any ladies interested in that. Could you strip for us, you and Rain, and maybe even fuck him in front of us? Then maybe both of you could get busy with the ladies, as I indicated, including me, of course.

“Maybe if you wore masks, they wouldn’t realize who it was, and that would add to the fun. I love the idea of Rain and you both getting some strange at last, though I’d want him to eat me out … and maybe eat them out afterward, too. The whole concept is too … stimulating to forget!” Larissa asked me excitedly.

“So … Rain and I, at your bachelorette party, in lieu of the usual strippers, being essentially used as fuckmeat for the whole time, entertaining you both, and then Rain cleaning up both his mess and mine … you do realize that these ladies will think that we’re actual strippers and want to slip money in our underpants, right? Sounds fine and fun with me, although I wonder what the married women and their husbands will do if some of them cheat.

“Oh, well, they’re grown-ups. If they want to stray, they’re going to stray, and that would be just as true with professional strippers as with amateurs. I don’t have great dance moves, but I get the feeling that this won’t be an artistic performance, anyway. It would be almost entertaining to see some of these women in a conference room for divorce arbitration, taking money from them and their husbands after they are divorced for fucking none other than Rain and me,” I chuckled, admitting to myself that at what Larissa called “hen” parties (apparently, that was an Anglophile term for bachelorette parties), ironically because of a marriage, women would risk their own marriages by fucking other men.

“Well, don’t worry, I’ll find a way to make it up to the husbands if that happens, with your permission,” Larissa teased me as we dried off, but I think that she was in earnest and I liked the way that she thought.

“Or we can work together on that, and then I would use my arbitration skills, lock them in rooms together, and wear them down,” I chuckled at that, “I would even do that pro bono.”

“I bet that you would, especially if it turned into an orgy,” Larissa licked her lips, even as we walked and Rain stood naked and ready for a shower of his own.

“Guilty as charged. Alright, lover boy, time for your shower,” I teased Rain as he rushed to the bathroom to wash up.

Once he was out of earshot, I then asked Larissa, “And then there’s his bachelor party to consider.”

“Indeed. Please get him laid as well as yourself. I mean it. I don’t care if you have to slip him some money or pay the stripper extra yourself, but do it. It’s casino oyna high time that Rain got some action, and you for that matter, since you probably haven’t had much yet since Jessica and Tim evicted you from your own home. You know, that really stinks, by the way. Perhaps you need to take legal action and force things to a conclusion … you know, file for separation. I mean, I know that it just happened, but the sooner that you act, the sooner that she feels a swift kick in the ass to change her fucking mind!” Larissa spoke up, even as she and I made out furiously.

“Yeah, I don’t want her beating me to the punch. I cleaned out my share of the account, of course, and I wouldn’t be surprised if she contacted me to complain about that. I have to also prepare for the possibility that she’s in love with Tim and is done with me. I know what you said, but that’s still a very real risk. I’m just on the verge of cancelling her credit cards as well, but we’ll see.

“As an arbitrator, I know all the tricks, because people gripe at me about what their spouses do all the time. In fact, most recently, one man bitched at me because his estranged husband, yes, they were a gay couple, had shut off his electricity to avoid paying the bill. Now, that was pretty low, and I had to read the offending party the Riot Act, even though the victim had been cheating on him with his ex,” I laughed in spite of myself.

“I can only imagine,” Larissa snickered at hearing about that case, “He must have been extremely steamed at his husband to do that to him!”

“Trust me, though, straight and lesbian couples do stuff that is about equally as mean and vicious. One man was so angry about his wife’s adultery that he sent her pet Chihuahua to the pound and had to agree to pay the fees to get him returned to her custody. One wife was so furious at what her husband did with her sister that she set fire to his car and I had to get the cost of the vehicle deducted from her alimony, which caused her to get angry all over again over not getting as much as she hoped for that time.

“I had to remind her that she could have been prosecuted for arson and possibly insurance fraud if the investigators, adjusters, and police had gotten involved. She still wasn’t happy, but she settled down a bit after that and agreed to the generally quite sensible deal that I laid out for them. After all, she still got alimony for years of putting him through medical school. Anyway, yeah, people do some horrible things to each other during a divorce, trust me,” I coughed as I fought back a bit of a smirk.

“You mean like kicking their husbands out of their own homes?” Larissa needled me a bit, even as she began caressing my buns and I started fondling her ass.

“Yeah, exactly like that, illegally to boot,” I grimaced at that reminder, but Larissa made it up to me by practically raping my mouth with her tongue.

“Anyway, back to Rain … I care about him a lot, even if I’m also in love with you. I think … I think that my feelings for him are growing and I hope that you don’t get jealous over that,” Larissa changed the subject and I nodded.

“I figured that was only a matter of time. The guy has been patient. He has been very loving and selfless, even, and it wouldn’t be too shocking, given your level of intimacy, for him to wear you down, though plenty of times that never happens at all. I know enough about you, though, to understand that it would be quite likely in your case. You don’t have an ungrateful bone in your body, do you?” I told my new girlfriend, even as we made out all over again, just as Rain finished his shower and walked back toward us.

“Late night snack time?” Rain asked us, clearly famished.

“Oh, God, yes! How about something very unhealthy, such as kettle corn? We can watch a film, eat the kettle corn and some soda, and then … then the three of us can fuck like bunnies once more. Like that plan? It’s up to Master, of course. He’s the boss now,” Larissa proposed, evidently in the mood to “Netflix and chill” in more ways than one.

“I’m game. How about we find out what movies are playing on the streaming stick here?” I grinned as Rain started up the kettle corn, a nice, big, fattening bag of it for the three of us on our three-way date.

“So, after the movie, should Rain and I … you know, go ahead and ‘terminate’ his virginity at last? Make sweet love to each other?” Larissa asked aloud, laughing as I selected Terminator as the movie of choice.

“Yes, I think that would very much be in order, babe. I wouldn’t mind Rain’s sloppy seconds at all, especially since he would be cleaning up, anyway. He should wait until we’re both done fucking you, though, so that he could have a larger creampie to eat,” I winked at both of canlı casino them, making Rain blush and Larissa show her lovely dimples.

“Well, sweetie, looks like your virgin days are over!” Larissa told Rain in front of me, between taking bites of the kernels and making out with both of us.

“Oh, God, I’m so stiff just thinking of it, but can I wear lingerie while you fuck me, and can it be … missionary style? I want to look into your eyes the first time, Mistress!” Rain requested, to which both Larissa and I nodded after reading each other’s facial expressions.

“Oh, fuck, that would be so sexy, to deflower you while you’re in a frilly slip or lacy chemise! This time would just be one-on-one, I think. Not sure if I would hold you to the threesome rule with the all of the other encounters or not, but your first time is special. We want it to be intimate and personal, don’t we? Not that I would ask Stan to leave the room … you don’t mind him watching, I think, nor do I, but yeah, the first time for Rainwater Garner Willis, that’s a big deal, especially in your late 20s, no less!” Larissa remarked as we watched Arnold Schwarzenegger do his best at wreaking havoc on Los Angeles.

“Yeah, best if I stay in the room, to coach if nothing else. I can possibly give him and you both pointers on this sort of thing, just as you can guide him in how to pleasure a woman during the act. I would recommend one change, though. Cowgirl style allows eye contact as well and gives the woman the chance to control the pace, which with a virgin is a very good idea. I wish that my first sex with a woman had been cowgirl style, in fact. It would have made it easier to avoid cumming so fast and disappointing my first partner, as it happened,” I suggested, not mentioning that my first had been my cousin Svetlana, and it was more about consoling her after a break-up than anything else.

“That thought occurred to me, but I wasn’t sure if there was another reason that Rain wanted missionary style,” Larissa beamed while sandwiched between us and handling both of our dicks.

“No other reason. I just, I think, got hung up on the sentimentality of it being my first time, but Stan actually has a point. I know that I’ll make mistakes during my first penetration of a woman, but I would like for Larissa to enjoy it as much and as long as possible,” Rain blushed as he agreed with my suggestion, “It can still be romantic in the cowgirl position, I suppose.”

“Oh, absolutely, trust me. So, cowgirl it is, then, while wearing a sexy little number to be the sissy that he is the first time that he gets laid!” Larissa licked her lips at that idea, “I like that, because it means that I’ll be making love to the real Rain, the true dandy inside him, my best friend who really has such a feminine nature to him and always has. I’ve always loved how gentle and how effeminate he is, which I feel is his true persona, so … making love to that side of him will be much more intimate in my view.

“You’ve always been my very best friend, Rain, the one that I could love and trust that way for years. That’s who you are and I want to show my love for you tonight. Tonight, subbie though you are, let me serve you, mate. Let tonight be about what you need. You’ve always looked out for me. Now, it’s time to look out for you.”

“Pause the film. Let’s see this in action. You’re both so ready for this that I can’t even fathom how much you could be prepared. Doll him up and get him ready. This is gonna be pretty sweet to watch, very hot!” I smiled at both of them by this point, with the movie maybe a quarter along.

Sure enough, Larissa took Rain to the other room and got him very sissified, down to manicured and painted fingers to pedicured toes to sanded feet to a lacy negiglee and blue silk panties. After his wig, lipstick, rouge, and mascara were applied, Rain looked far more like a woman than I had ever seen a man be in person. His genitals, butt, and taint were properly hairless and smooth, and there was absolutely no doubt that he made a great sissy, especially with his physique. Not to be outdone, Larissa was dressed to the nines all over again, making me feel like a slouch for a bit, though no one really cared at this point.

I had to keep un-pausing, playing, rewinding, and pausing the Netflix while I waited for the girls, but when they appeared, it was more than worth the trouble. It honestly appeared to be a lesbian act for several minutes there, as Larissa and Rain kissed passionately and with tongue, sucking face with considerable enthusiasm. My cock was very stiff as I watched both of them descend to the couch to start making love to each other. They seemed a bit awkward at first, but both soon relaxed, and then their physical intimacy began in earnest.

As kaçak casino I watched, Larissa lay there with her thighs spread and Rain ate her out with relish. He licked her repeatedly to get here where she needed to be for the next act, of course. He sucked her clit more than once, too, making her shiver as they enjoyed each other’s bodies. Clearly, if nothing else, his position as her pussy-licker was perfectly safe. Few men could eat pussy that well and I was embarrassed at how much better a cunnilinguist Rain was than me. He might need pointers on penetration, but he could teach me a thing or two about eating a woman out to her satisfaction. Her hands held his head in place as if afraid he would suddenly stop and her moans and sighs of pleasure could be heard for miles away.

By the time that Larissa came down enough for Rain to stop, I almost felt like applauding, as it had been a virtuoso level of accomplishment at pleasuring my new girlfriend. Larissa looked down at him with incredible love and tenderness as she pulled him up to her face and tasted herself on his lips and tongue while making out with him. I had been too drunk to feel compersion with Jessica and Tim, plus their actions later had prevented anything but rage and heartache, but this time I actually experienced it, watching my girlfriend sample her own juices from her fiance’s mouth.

Now, of course, it was time for Larissa to prove her selfless intentions toward Rain, and that she did in spades. She slid their panties down, pushed him onto his back, and eased her sweet, very soaked pussy down onto his dick to begin riding it and take his virginity at last. Still wearing her own chemise, but baring her lovely ass to me, Larissa now lifted her slip above her head and showed off her wonderful breasts to her roommate as she rode him for the first time in his life. The fact that it was bareback made it so much more wonderful, especially as I had thoughts of Rain and I putting twins in her fertile womb from this night’s sexual liaisons. It certainly added to the intimacy of the moment and made it plain that Rain would indeed be cleaning up his mess as well as mine after we both came inside her.

I was as hard as steel, but I focused on letting my cock go limp for now, so as to keep it from cumming too soon inside Larissa once it was my turn from all of the excitement. I wanted to see this coupling as it happened without distractions as well, but it was very tough to prevent my dick from hardening as I saw Larissa kiss, caress, and ride Rain, who was very much in the moment with her. I knew that Rain would probably be excited as well as when it was my turn, but he at least would have just cum, so that would make it easier on him. I didn’t envy him, though. He would be the one on clean-up duty, after all, even if he obviously enjoyed that role.

For a virgin, Rain definitely lasted longer than expected, especially with the occasional tips that I gave Larissa and him, as well as her riding him rather than him mounting her. Even so, it was soon plain that he couldn’t hold out much longer than he had, and by now Larissa’s toes curled from the orgasm that took place from his attentions on her sensitive twat. When he touched her breasts during the act, and then her buttocks, she absolutely lost it. I watched her bare bottom move as she let out a scream of ecstasy before tightening and squeezing out every drop of his spunk from his balls. Larissa slumped on top of Rain and kissed him softly, more than once, whispering words of affection for him in his ears as he held her in his arms for some cuddling that I didn’t wish to disturb.

I turned the movie back and we all silently watched it together for a good while, giving everyone a chance to chill before any more hanky-panky. I wanted them to have a chance to bask in the aftermath of their first sexual congress together and they seemed to appreciate that fact. They needed their intimate moments, just as she and I would … and to be frank, most likely, he and I would in time as well. The movie reached its conclusion and the credits rolled, and they were still snuggled up together, Larissa softly crying as Rain stroked her hair and neither of them caring about their smeared makeup.

I dozed off for probably an hour or so before I felt two tongues and pairs of lips on my cock, which caused me to open my eyes and see Larissa and Rain teaming up to give me an incredibly sensual blowjob together. Both of them looked absolutely eager and pleased with themselves, and from the way that Larissa acted, I could tell that in my slumber, Rain had already cleaned her up quite well, thank you very much! There was no doubt anymore, as Larissa and Rain gave me serious head in unison … all three of us were completely involved with each other. We were intimate with each other in every sense of the word. We were complete. We were lovers. Whatever happened with Jessica and Tim, I was good. I was loved. I was no longer alone.

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