First off, I’m sorry for not updating you all on these events sooner.  Things have been really crazy over the past few months. But here is an an update on what has transpired between Illana, Mike, and me.  Since I already went over all the details in the last installment, I’ll just jump right in.

A couple of weeks had gone by since that night I secretly sucked off Mike. Illana, however, never brought it up. That left me confused and a little nervous. Had Mike told her? Was she just giving me an opportunity to confess? Or was Mike keeping our little secret? Part of me wished it was the latter, because if we really were going to try out this “throuple” idea, it would be nice to have a little secret with Mike, an intimacy only we shared.

When I thought like that, though, I got so flustered. I could not believe I was even contemplating a relationship of any type with a man. Just a few months ago, I was perfectly straight. But somehow Illana had transformed me into something different. I was now basically in a chastity cage for the majority of the time (and she had gradually reduced the size so at this point I was in a "micro flat" cage with basically no cock at all). At home, I was her “lesbian lover"—always dressed like the little innocent girl she wanted me to be. And now I had to come to grips with wherever this relationship was going.

So, in the end, I decided not to say anything, which became a huge source of anxiety over the next few weeks. I was constantly wondering if he had told her and they had gotten into a fight over me or something.

But then one night, as Illana and I were eating dinner together and finishing off a bottle of wine, she brought him up.

“So, about Mike,” she said.

Then she let silence hang in the air. My heart rate must have tripled as I waited for her to continue. She made sure we were looking each other straight in the eye before she went on.

“I don’t want you to think I’ve forgot about this throupling idea. I’m assuming you two must have had some connection, because he’s texted me asking about it a bunch since that night you picked him up.”

Illana was searching my eyes for clues. I sat as still as I could, breathing deeply and trying to calm my heart rate.

“Oh, yeah? I mean, he was pretty cool and all, but I’m not sure about this whole thing. I mean, I’ve never done anything with a guy before, and now you’re suggesting I date one.”

“We,” she interrupted, “I’m suggesting we date one.”

“Right,” I said, “we.”

There was a bit of tension in the air, but then Illana smiled and gave me her most sultry and seductive eyes.

“I think you could end up really enjoying it. Being a girl is so much fun. Getting all dolled up for a guy, the anticipation of how he’ll look at you, having him dote on you, telling you you’re beautiful, taking charge in every situation. It’s all so wonderful. Doesn’t that sound fun?”

I think I must have smiled while she was talking, because before I could say anything she continued.

“Yeah, I can tell you’re not that opposed to it. So why don’t we do this. Why don’t I setup a date for the three of us this Saturday?”

“Okay, I guess if it’s just going to be a trial thing, to see how things go,” I said.

“Of course!” Illana exclaimed, excitedly grabbing her phone and texting Mike.

***

Before I knew it, Saturday had come. Illana had gone shopping earlier in the day for our outfits, and she was so excited to start the process of getting us primped, plucked, and primed for our date. She had gotten herself a little black dress. It clung to all her curves and was short enough that when she bent over you could see a little peak of the red satin panties she was wearing. It had a plunging neckline that really accentuated her voluptuous cleavage. I got excited and felt the usual discomfort of my chastity cage when I saw how gorgeous she looked.

For me, fitting for her idea of me as an innocent girl, she got me a long-sleeve white top.

“To keep you modest,” she said.

But since it was a kind of first date, she had me put on a tight, faux-leather skirt over fishnets with a pink pumps, because she said that on a first date you have to give the guy at least a little glimpse of your body.

"So much for modesty," I said looking at myself in the mirror.

"Compared to me, babe, it is," she laughed.

Underneath my outfit, Illana had me wearing my sexiest matching pair of lacy, black bra and panties.

“Wearing sexy lingerie under a more modest outfit can really keep you feeling sexy on a date,” she told me.

Illana did her hair and makeup before turning to mine. She curled her long, auburn hair into sensual waves that fell around her shoulders. She offset her porcelain skin with dark, smoky eyes and dark red lips. Within the hour, everything about her was screaming sex and desire.

Then she turned to me. By now, my hair had grown passed my shoulders. Nonetheless, Illana weaved in some sandy-blonde extensions. She made sure my cheeks were pink with blush, my lips a lighter shade of red than hers. She plucked my brows into feminine arches. She spritzed her best perfume on my wrists and behind my ears.

“Just in case,” she said, implying that there was a chance Mike and I might kiss on this date, I supposed.

“One thing girls like to do before a date is send a cutesy picture to their man. Let's take a couple,” she said.

She stood in front of the mirror with her chest popped out and slightly bending down, really exposing her cleavage. She stuck her tongue out ever so slightly, giving off a real bad-girl vibe. She had me stand and turn around to "show off my best asset."

"Stick that ass out for Mike, baby," she giggled as she snapped the pic.

I did as she wanted, daydreaming about how Mike would react when he saw it. When I saw these pictures back to back, and I looked at the two of us in the mirror, I understood her intentions. Clearly, the image she wanted Mike to have of us was that she was the naughty one, and I was the nice "girl." I know from experience that men like both for different reasons, and she obviously knew that too. It was obvious that her intention in this throuple arrangement was for her and I to occupy different roles.

A few seconds after she sent the pictures, her phone buzzed and she let out a little seductive laugh.

“Mike said you look really hot!”

I couldn’t help myself, and I started blushing as my lips instinctively formed into a shy, school-girl smile.

“You’re too good at this,” I admitted.

“Before long, you’ll realize I’ve always known what’s best for us,” she replied.

***

Before long, Mike arrived and rang the doorbell. Illana put on her black, patent leather stilettos to complete her sultry vixen look. I reached for the doorknob, but Illana grabbed my hand, pulling my body close to ours until our chests were touching. She reached around and put her hand on my ass, giving it a hard squeeze as she pressed her lips onto mine. Her tongue pushed passed my lips and danced on my tongue. Then she broke off and whispered in my ear.

“Remember, babe, we’re in this together,” she said.

Illana opened the door. Mike was standing there with a giant, bad-boy grin on his face, looking us both up and down.

“My ladies are looking extra hot this evening!” he exclaimed.

“This is going to be a fun night. Are you girls ready?”

My face flushed. I couldn’t believe how much I enjoyed Mike referring to me as “lady” and “girl.” Illana had really done a number on my psyche since she first proposed, I started dressing more feminine all those months ago.

“Aw, thanks, babe. You don’t look so bad yourself,” Illana replied, taking the lead as always.

She went right up to him and kissed him in the same passionate, seductive way she had just done with me. When she broke the embrace, she looked back at me and winked.

“C’mon, darling. Our man has a great evening planned for us.”

Mike drove. Illana was in the passenger seat. I was in the back seat, my head swimming with an inundation of first-time feelings. I was nervous to be going out in public. I was nervous to be on my first “date” with a guy. And I was fighting slight feelings of jealousy as Mike’s hand gripped Illana’s exposed thigh as he drove. But I had to try my best on this date, so every time Mike made eye contact with me through the rearview mirror, I gave him little flirty smiles back.

We arrived at a trendy cocktail bar downtown. Mike led us to a secluded semi-circle booth in the corner. Illana got in the booth first, then Mike followed, and then me. Now Mike was sandwiched between his two dates, and he seemed to be enjoying every minute of it. Before long, the cocktails were flowing, and we all couldn’t help but get flirty.

Of course, Illana started it. By the time the second cosmopolitan was in her system, she had her leg slung over Mike’s lap and was whispering sweet nothings in his ear. I sat and watched closer than I ever had before how my girlfriend felt so free seducing another guy (as much as I could use the word “another” at this point).

Mike was enjoying himself too. His hands were all over Illana’s soft, smooth thighs. If the waiter hadn’t come over when he did, I imagined they would have started making out right there. But somehow modesty got the best of her and she slinked off Mike when he approached.

“Another round?” the waiter asked.

“Another cosmo for her,” Mike pointed at Illana, “and another prosecco for her,” he pointed at me, “and I’ll have another old fashioned.”

I had to admit that I loved the way Mike ordered for me. I also had to admit that I was getting a little jealous, but it was a confusing kind of jealousy, because I couldn’t tell if I was jealous that Illana was paying so much attention to Mike or if I was jealous that Mike wasn't paying attention to me. She must have sensed it, like she always does.

“Babe, why don’t you scooch a little closer to Mike? I don’t want to hog him,” she said while winking at me.

Mike took the hint. As I slid a little closer to him, he put his left arm around my shoulders. I felt butterflies in my stomach as I melted into his embrace. Mike spent the next twenty minutes fully fixated on me, seemingly ignoring Illana. He asked me all about myself, my likes and dislikes, my favorite music and movies. I gushed it all to him.

At one point, I noticed Illana lean in on his other ear and whisper something. I couldn’t quite make it out, but then all of a sudden, Mike leaned in and started kissing me. My knees got weak, and my hands were shaky. I felt so vulnerable, once again, with Mike’s strong, masculine body pressing on my feminized frame. Illana’s tongue had danced on mine just a few hours earlier, but now Mike’s was aggressively exploring my mouth. For anyone who’s been kissed by both women and men, you know the difference. It’s unmistakable. To top it all off, this man was kissing me in public.

Mike's hand found its way to my leg, slowly stroking up from my knee to my thigh. Without thinking, almost animalistically and instinctively, my legs parted. Right when they did, I couldn’t believe it. I had just opened my legs for a guy. What was happening to me?!

Mike took the unintended cue, and he let his hand follow my thigh up my skirt. I felt his fingers press against the flat disc of my chastity cage. I let out a moan. I felt my cage tighten, and then the blood redirected in ways I never thought possible. I felt warm in my belly and my hips. I felt tingling in places I never had before. It was almost like my body was instinctively preparing for something.

“Slow down, you two. We have a long night yet to go,” Illana giggled.

Mike pulled away, and I instantly felt lonely. I wanted him back. When my eyes refocused, I made eye contact with Illana, who had the biggest smile I’d ever seen her have on her face.

“Let’s go to the little girls’ room,” she said to me as she stood up.

She took me by the elbow and led the way.

“Oh my god, babe, I can’t believe you two kissed!” she exclaimed once we got inside the single-stall.

“I know. I can’t believe what’s happening out there,” I stammered.

“What do you mean, of course you can. You’re a hot girl on a date with a hot girl and a hot guy, of course, things are going to get a little steamy! I have to say, watching you two kiss got me so yet. Feel.”

She grabbed my hand and pulled it under her dress. I could feel the warm slickness of her fully aroused folds. I instinctively started to rub and her eyes rolled back a little.

“Okay, that’s enough,” she laughed as she pulled my hand away.

"Like I said, we have a long night.”

We fixed our makeup and then went back out to meet our man.

***

When we got back to the table, Mike had paid the tab and was standing to greet us.

"Well, ladies, now that we are sufficiently lubricated, why don't we find some place to dance?" he said more as an instruction than a question.

We followed Mike back out to the car. This time, he led, and Illana and I held hands as we walked behind him. I could tell people were looking at us, but I couldn't tell if it was because they were clocking me or whether it was just the typical stares a lesbian couple might get. Either way, the alcohol in my blood was making me care less and less.

When we arrived at the club, Mike got us yet another round of drinks. Illana was clearly feeling it. She always gets extremely horny and very flirty when she's been drinking, and this was no exception. She was all over Mike, sitting on his lap, grinding her hips to the beat of the booming bass filling the club. I got up from my seat and stood next to them. Mike's hand immediately grabbed hold my butt. He squeezed it hard, and then left it there, as if to claim it for himself.

While I was dizzy with my growing inebriation and lust, Illana reached over and grabbed my head, pulling it towards her and Mike's locked lips until the three of us embraced in a three-way kiss, each of our tongues dancing on the others'. I felt Illana's soft lips and Mike's beard scruff at the same time. The passion that was rising between the three of us was indescribable.

Mike broke the embrace, grabbed each of us by the ass, and started pushing us toward the dance floor. Illana and I surrounded him, each of us moving our hips on him. Mike grabbed me and spun me around so that my ass was moving back and forth on his crotch. Suddenly, I felt his bulge press on me. That only made me press back harder.

I thought back to what it had felt like to have his throbbing member between my lips and my mouth watered. Mike's hands were suddenly all over me, caressing me up and down, rubbing my thighs, my hips, my stomach. My chastity cage was holding on for dear life, and I could once again feel the pressure building inside me.

Suddenly, Illana cut between us. She faced Mike head-on. She wrapped her leg around his and started grinding her panty-covered pussy lips on his thigh. They started making out, and she bit his lip. We continued dancing like that for a few more songs, and then Mike led us off the dance floor.

"Ladies, you two are so fucking hot out there. You're driving me crazy. How about we head back to your place?"

And so we went.

***

Mike was all over us as we stumbled through our apartment door. Illana wasted absolutely no time taking Mike's shirt off, exposing his hairy chest and physique. I somehow thought about my own body in comparison. I don't think I ever exuded that kind of manliness, and especially not knowing that my manhood was locked flat in a cage and my chest was covered with a lacy bra.

Mike returned the favor and put his hands under Illana's hemline, pulling it upward until she was standing in her bra and panties before him. I stood by and watched Mike start to kiss her neck (which I know gets her going like nothing else). She put her leg up over him, and I watched Mike's fingers find their way under her panties and start to penetrate her sopping-wet folds.

I had never actually seen Illana with 'another guy' before. I had heard stories, seen pictures, and heard her moans through the wall, but I had never seen it up close like this before. I actually started to feel jealous. I think it was that jealousy that led me to walk up to the two of them and interject.

I got in between them and started kissing my girlfriend as hard and as passionately as I could. I moved Mike's manly fingers out of her and replaced them with my own soft, moisturized, painted fingers, plunging them into Illana's now-swelling lips. She moaned with a pleasure that was just for me. I knew her body so well.

I was so focused on pleasuring Illana that I didn't even realize she was pleasuring Mike; that is, until he came up beside me and pressed his hard cock into my side. Illana's hand was on it, and she was stroking him. She broke off our kiss and looked me in the eye.

"Baby, I want you to help me suck Mike's cock right now, would that be okay with you?" she asked.

Speechless, I nodded my head in agreement. Illana grabbed my hand, never breaking eye contact, pulling us to our knees. She was still stroking Mike's cock with her right hand when she raised her left hand under my chin, pulling me into her for a passionate kiss. When our lips parted, she moved towards Mike's pulsing, veiny member. I could see that our kissing had really turned him on, because precum was already leaking from his tip.

That's what Illana went for first. She dragged her tongue from underneath his head to the top of his helmet, pickup up every drop of precum along the way and swallowing it. She opened her lips and let Mike penetrate her mouth with his cock. She bobbed her head back and forth, lubricating him with her saliva. The slurping and sucking sounds filled the air.

"Fuck yeah, suck that cock, baby," Mike moaned while looking me at me, giving me a coy wink.

Illana pulled off his cock and leaned toward me. She pressed the precum that had collected on her tongue onto mine. I could taste the familiar taste of Mike's cock all over her.

"Doesn't his cock taste good?" she whispered in my ear.

"Mmm. It does," I answered.

"Then suck it for me baby. Show Mike what good girlfriends we can be."

Hearing this, Mike turned his hips toward me, his wobbling cock now standing stiff before me.

I opened my mouth, and Mike thrust his hips. His cock was now inside my mouth and I instinctively started sucking, just as I had done a few weeks prior.

"Oh my god, baby, you're doing it!" Illana giggled.

Little did she know this wasn't the first time Mike had used my mouth for his pleasure.

Illana leaned back against the counter and started fingering herself as she watched her boyfriend-turned-girlfriend suck her new boyfriend's hard cock in front of her. I moved my hands to Mike's hairy thighs, feeling their masculinity, thinking about how I would never be like that again. Somehow, I was getting more pleasure from pleasing a man with my mouth than I had ever gotten from any other sexual experience. There was no turning back now.

Illana shifted forward and crawled back to Mike's cock, hungry for more. We started sucking him together, taking turns moving our tongues over his rock-hard shaft. She moved under and sucked his balls while I sucked the tip of his head, then we switched.

"Fuck, oh fuck," he moaned.

This went on for about ten minutes. Then Illana got up.

"I can't take it anymore. I need you to fuck me!" she said, almost gutturally, to Mike.

Without hesitation, Mike picked her up by the hips and set her ass on the kitchen counter. He took off her panties and then took a few steps toward me, putting Illana's panties under my nose.

"This is what a real man does to a woman," he said.

I could smell Illana's sex all over them. I knew he was right. There was something different about that smell that I had never been able to coerce.

"Take it easy, baby," Illana interjected, "that's because she's not a man. She's a woman... or, at least, she will be soon. Now come over and shove that cock in me."

Mike turned around, spread Illana's legs, and plunged his cock into her.

"Oh fuck, that cock feels good!" she gasped.

My cage ached. My legs were shaking. My head was spinning. I watched as Mike thrusted himself into my girlfriend over and over and over again. Her juices were dripping down onto the surface of our kitchen counter, pooling and glistening. She was looking directly into his eyes with a feminine lust I had never seen. Mike was doing something to her I never could: fucking his masculinity into her willing cunt.

I watched as her toes curled and she orgasmed from being fucked, another thing I had never been able to do for her. In that moment, I thought I fully understood why she craved Mike's masculinity. But I didn't. Not yet.

After Illana went limp following her orgasmic thrall, Mike pulled his glistening cock out of her. He hadn't cum yet. I got back down on my knees in front of him and started sucking Illana's juices off of him. He let me for a few moments. But he had other ideas.

He picked me up by my chin until I was standing before him. He gave me a deep, passionate kiss, squeezing my ass cheeks so hard it almost hurt. My knees went weak. Then he turned me around. I felt him stick his cock between my thighs, moving it back and forth slowly. He leaned into my ear, pressing his dominance onto me.

"I want to fuck this ass tonight," he breathed into me.

I was temporarily frozen with the thought. Illana got up and walked in front me, once again giving me that comforting, persuasive stare. She put her hands on my cheeks.

"You've come so far, baby," she said.

"You're not a boy anymore. You're my sexy girlfriend. But you need to be made a woman tonight. We need to show Mike you're ready to be his girlfriend too. Are you ready for that?"

"Anything for you," I replied.

Illana beamed.

"Mike, let's make this special for her. Let's head to the bedroom," she said.

Illana grabbed my hand and led me to our shared bedroom, where I would soon have my feminine-virginity taken before her eyes. Both her and Mike surrounded me, kissing me, feeling every inch of me with their hands. I was dizzy with lust and feminine energy. I had never felt so desired, so beautiful, so sexy. I couldn't tell whose hands were whose, whose lips were whose, who was taking one piece of my clothing off at a time. But, before I knew it, I was naked. All three of us were. The only difference was that I still had one thing on--the chastity cage that ensured any bit of masculinity I had left was out of sight.

Mike leaned in and put his manly arms around me. He leaned in and parted my lips with his tongue. He pushed his fingers hard onto my flat cage, moving it slowly in circles as if it were a clit. No matter the biology, somehow it felt the same in this moment. Mike's fingers were warming me up somehow. I felt my hips opening, my ass relaxing, priming itself for what it knew was coming.

Illana came near and turned me around, pulling me onto all fours on our shared bed. I heard a 'click' and then watched as she poured lube over her fingers. Then she was out of view, behind me. I could hear her rubbing the slick liquid over Mike's cock, which was going to be fucking me soon. I knew it. I was ready.

Suddenly, Illana's fingers were inside me. Being penetrated was a completely new feeling. I felt full. I felt stimulated in a way I never had before. She leaned in and kissed me while she did it. She was warming me up for what she had been planning for weeks, for months, now.

"Are you ready?" she asked me one more time.

"Mmhmm," is all I could manage to moan.

I felt her fingers pull out, and then I felt the tip of Mike's hard cock press against my wet hole.

"Go slowly," Illana whispered to him.

He did. He pushed forward slowly, but confidently. I gasped as my body tightened, feeling something it never had before.

"Relax, baby. You're so fucking hot right now. Let Mike make a woman out of you," Illana whispered lustfully into my ear.

Illana's reassurance worked. I relaxed. I felt Mike's girth start to spread me open. It felt like a paint can was being shoved inside me, but I did my best to stay calm and let it happen.

"Oh fuck, oh fuck," I started to pant as now it felt like Mike was hitting something that couldn't be passed through.

I couldn't tell whether he was all the way inside of me or not. It felt like he had hit a wall and there was no further he could go. But then it happened. He hit something just right, and my body opened up for him. I felt his cock rush into me. I felt hairy, manly thighs press into my shaved, feminine, soft backside. My whole body started to shake.

"That's it," Illana gasped, leaning into kiss me.

"Now you're going to feel how good it is to be fucked."

Illana started making out with me as Mike started thrusting. He was slow and steady at first, but started picking up power and pace as he went. New sensations flooded my body. Ripples of electricity, starting from the point of my penetration, pulsed through my body. Slowly but steadily, every bit of pain and discomfort I had initially felt transformed into sheer feminine pleasure.

Before long, Mike wasn't the only one working. I felt my body start to rock back into him. He was fucking me and I was loving it.

"You love this, baby, I can tell. You love getting fucked by Mike's hard cock don't you?"

I moaned unintelligibly.

"Tell me you love getting fucked," Illana said.

I couldn't lie. I was loving it. I was loving being submissive, spread open, letting Mike fuck me into ecstasy. I loved the way Mike's hands gripped my hips and pulled me back so his cock could go deeper and deeper inside me. I loved every new sensation I was feeling.

"I love getting fucked," I moaned.

"How does she feel?" Illana asked Mike.

"Fuck, her ass feels amazing! I could fuck her all night."

He pulled out, and I instantly felt empty. The second Mike's cock was out of me, I wanted it back in. Thankfully, it was just a brief pause to change positions. Mike grabbed my hips and twisted me over so that I was on my back. He grabbed the insides of my knees and rolled me backward. I had never felt so out of control, so completely dominated by anyone. Here I was, my cock locked in a cage with my gaping ass being tilted back by this superior man.

Mike shoved his cock back inside me, and I felt whole again. He leaned in and started kissing me deeply as his cock explored every inch of my insides. Illana must have been ready for this, because she got on top and set her still-wet pussy on my face. I started licking her while Mike was fucking me. They started kissing over me, the three of us giving each other immense pleasure.

Before long, I could feel Mike's pace quickening. I knew he was getting to the point of no return. And in that moment I wanted nothing more than for him to fill him with his hot, sticky cum. I wanted to be bred. I wanted him to shoot his seed as deep inside me as it could go. I suddenly had visions of being impregnated by Mike, of carrying Mike's baby inside me. Then I felt my whole body shake with pleasure as cum leaked from my soft clit out of my cage.

"Oh fuck," Mike grunted.

Mike's thighs were slapping against my ass harder and harder as stars filled my eyes and I went to a mental space I had never felt before. And then he exploded, shooting his seed as deep inside me as his cock could thrust. He held his cock in me until it got soft. I was satisfied in that moment, but I knew I would want to get fucked again before long. It was too good. It was the best pleasure I had ever felt. It made me feel so whole, so perfectly submissive.

"Mike just came in you, baby. You're a real woman now," Illana said while stroking my ass.

After a little clean up, the three of us fell asleep in the same bed. Mike in the middle, his girls on either side.

***

EPILOGUE:

Mike, Illana, and I decided to give throupling a shot. We "dated" each other for a few more weeks, which was filled with more sex than I'd ever had in my life. Sex for me now was getting fucked, and I loved every minute of it. Unfortunately, we found out that Mike was cheating on us. Men! So frustrating! We were sucking and fucking him at least 3 times a week, but for some reason he decided to still stick it in some bartender one night. Illana caught him by sneaking a peak at his phone. Illana has a zero-tolerance policy on cheaters, and so we broke it off with him. Illana and I are still together, but we haven't found the right guy to bring into our relationship. She still sees the occasional guy on her own, but hasn't found the right one to introduce to me yet. But I can't wait for the day that she finds a suitable guy so that I can be a man's girlfriend once again.