So, my life just completely changed last week, and I’m still trying to process the feelings and hoping writing this all out will help. But before I get to what happened, I should give a little background.

I’ve been dating Illana for about a year now. I met her while bowling with friends one night. She had a big, bold personality that really struck me (not to mention her big and bold curves). Being a very submissive guy, I’ve always been attracted to the more dominant women in my life, and Illana was no exception. Thankfully, I’ve been burned enough in the past that I’m just up front about it now. I told Illana on our first date that I prefer to be more submissive in relationships and to let the girl take charge of things. Illana was very keen on being the dominant one in the relationship, and we’ve been together ever since.

Right from the get-go, she took charge of our sex life. Even though she’s the one getting fucked, I always feel like the bottom. When she gets horny, she usually just pushes me on the bed and rides me like her life depends on it. She never (I mean never) gives me head, which sometimes bums me out, but it’s not my place to ask for that kind of thing in our relationship. I, however, go down on her nearly every day.

Her control of our relationship doesn’t just take place in the bedroom, even when we’re out in public, it’s clear to everyone that she’s the one in charge. She even orders my food for me when we’re out in public sometimes.

About six months into our relationship, after she had finished riding me into oblivion one night, we were lying in bed doing our typical pillow talk, and she brought up the idea of dressing me more feminine when we were going to be intimate. I was hesitant at first, but she explained that she’s always had a bit of a lesbian fetish and that since I was basically the girl in the relationship, it just made sense to live out that fantasy with me. At first, I was a little shocked and resisted the idea. But I’m not one to resist much, and after she brought it up a few more times, I agreed to try it.

Illana, in true Illana fashion, has gone full steam ahead. She bought me a handful of outfits, mostly skirts and slinky tops, some leggings, pantyhose, and, of course, an assortment of bras and panties and wigs. The first time I dressed for her, she made me shave my body hair first. She said that she really wanted a lesbian experience, and so I had to be as girly as possible. Once I was smooth all over, which I must admit was a truly exhilarating experience, she sat me down and put my makeup on.

Now here’s something I didn’t expect: I really loved it! I loved the way it felt to get all dolled up and pampered by her. I loved the way the clothes felt on me. And I especially loved the way our smooth skin felt when it touched each other. Needless to say, for the last six months, our sexual encounters have been of the “lesbian” variety: me dressed like a college girl and her an authoritative older woman making me please her in any way she wants—at least that’s the fantasy she likes the most.

Ilana even introduced chastity into our relationship. Since I was her little lesbian lover now, she said, I didn’t need to use “my clit” anymore. I don’t know why, but I guess it’s my submissive nature and how much I was falling in love with her and our “lesbian” affair, but I agreed. For the last six months, I’ve been in chastity basically every day, feminized by Illana at least two-three times a week, and the only part of me that has been close to her pussy since then is my mouth. And, for some reason, I’ve never been happier.

But then Illana sprung another twist on our relationship. About three months ago, she shocked me again. One night after I had finished going down on her, her pussy covered in the red lipstick I was wearing, she told me that she had been getting cravings to get fucked by a really dominant guy, to have the tables turned so she could be the submissive one for once. I was really blown away. I didn’t know what to say but, as usual, Illana knew just what to say to convince me this was okay. Within the week, she had created a Tinder profile and, of course, was flooded with interested guys looking to hook up.

She made sure to include me in picking out how the guy she would hook up with. In my life growing up as a man, I never thought that one day I’d be sitting around in a plaid skirt, sheer stockings, wearing a lacey bra and panty set, my dick that hadn’t seen a vagina in three months locked in chastity, and helping my girlfriend pick out another guy to fuck her. But there I was.

She really seemed to be focusing on bad boy types—lots of tattoos, muscular, a little dangerous-looking. But thankfully, I was able to steer her towards someone that looked a little safer to me, and he was more handsome too. His name was Mike. He was older than both of us (we’re in our late twenties, and he is in his late 30s). He was clean cut and had an athletic build. I couldn’t believe when I was watching them chat back and forth at how horny I was getting. I don’t know if it was the chastity, the feminization, or what, but I was actually getting hot thinking about Mike fucking Illana good and hard, making her his bitch. Maybe it had to do with how dominate she was to me and the thrill of the role reversal. I really didn’t know.

I’ll never forget that first night she went out with Mike. I sat in our apartment, my mind and heart racing with all kinds of emotions. I was horny, jealous, scared, and every other type of emotion I knew existed and some I didn’t. The plan was for them first to go out to dinner, and then, if she liked him, to get a hotel room near the restaurant. I remember sitting in our apartment, my tiny cock straining in its chastity cage, as I watched her location on my phone go from the restaurant to the hotel room—so I knew without a doubt that the love of my life, Illana, was getting fucked by this complete stranger who I had never met. I wanted nothing more than to jerk off to relieve the emotions, but I was still locked in chastity and Illana had the key. I even tried grabbing one of her vibrators and vibrating my cage, but I just couldn’t find relief.

When Illana came home, she had this blissful sort of satisfaction on her face that I have to admit she had never had when we had been together. She seemed feminine and free, but once she saw me dressed up when she got home, a switch flipped. She became the dominant Illana I had known. She walked right up to me and started kissing me hard and heavy. She tasted different, and I just had to assume that I was tasting some aftertaste of whatever she had done with Mike—I just tried not to imagine what in that moment. She grabbed my painted fingers and pulled them to her still-wet pussy and asked me if I could feel how swollen she was. I could feel that it was true, and that she had some sticky residue left in her panties.

She told me Mike was easily three times bigger than me, the biggest she had had, and that he had fucked her exactly how had she had been needing. Then she grabbed my caged cock and laughed and went to bed.

Illana and Mike have been seeing each other about once a week since then. She tells me that she’s never been happier because she gets to have the best of all her fantasies—she gets to get railed by a dominant, masculine man and then have a lesbian lover back at home. And I have to admit, I’ve never been happier either, even despite the cage bringing me to a near-constant level of horniness lately. Although this hasn’t been a lifelong fantasy, I’ve come to fully embrace being Ilana’s little femine tart that she keeps at home; there’s just something so satisfying about giving her what she wants.

And that brings us to what transpired last week.

Illana told me that she wanted to bring Mike back to our place. Mike has known about me for a while now and, for obvious reasons, isn’t particularly threatened by Illana’s boy/girlfriend. Illana said that since she and Mike had been a thing for a while now, that maybe we should start experimenting with throupling. She told me that Mike seemed interested in the idea. And, once again, I had to admit to her that the idea didn’t seem that crazy. She told me that, obviously, it would be more like her dating the both of us, and that she didn’t expect anything from me towards him—which made the whole thing sound better—because I’d never been attracted to guys. I even told her that one night when she asked if I’d ever want to be treated like a girl by a guy instead of her.

So last Friday was the day we were all supposed to meet to see how it felt all being together. Mike was out at a bar with his friends, and Illana was supposed to pick him up and bring him over. But I guess she had a few too many glasses of wine (probably to calm her nerves) and so she asked me to go pick him up.

Earlier that night, Illana had really gone all out in dolling me up for the evening. She did my nails and toes, really spent a long time getting my makeup just right—my smokey eye, blush cheeks, and red glossy lips were all immaculate. She had styled my wig with long, loose waves. I was wearing her favorite floral gypsy halter top, along with a plaid mini skirt and polka dot stockings. Underneath it all, I was wearing a pair of pink, polka dot silk panties and a push-up bra. Despite looking really hot (in my humble opinion), I was nervous to go out in public. I had never been dressed in public before. But Illana gave me Mike’s number and said I could just text him when I got to the bar and I wouldn’t have to go in.

My heart pounded as I drove the twenty minutes to the bar where Mike was. I had strange mix of anxiety from being dressed as a girl outside our apartment for the first time, and also from being about to meet the guy that was regularly fucking my girlfriend. But, thankfully, I got to the bar safely. I texted the number she gave me and told Mike I was outside.

I watched him and a couple of his friends come out of the bar, and he made eye contact with me through the windshield. He smiled at me, then seemed to say goodbye to his friends and started walking toward the car. My hands and knees were shaking, and my stomach was filled with butterflies.

Mike got in the passenger seat of the car and said “Thanks” for picking him up. He stared me in the eyes at first and then let his gaze wander down from my eyes to my torso, hips, and then down to my legs. I’d never had a man look at me like that before. But, then again, I’d never been dressed like a girl in heat in front of one before.

“I have to say,” Mike said laughingly, “when Illana told me about you, I never expected you to look like this.”

I laughed nervously and said, “Like what, exactly?”

“I mean,” he leaned in a little closer toward me, “you’re kind of hot, if you don’t mind me saying.”

I could feel my cheeks flush and the butterflies in my stomach were spinning a thousand miles a minute.

“Let’s get back to Illana, shall we?” is all I could mutter out.

I put the car in drive and took off toward Illana’s and my apartment. But about five minutes down the road, Mike put his hand on my thigh and started squeezing and rubbing it. I was frozen, trying to ignore it, but for some reason I didn’t think to move it away. Then he started speaking again.

“I can’t wait to fuck Illana later,” he said while using his other hand to grab his crotch, which I couldn’t help noticing out of the corner of my eye.

“She’s such a good lay. I mean, you know that, or at least you must have at some point, right?” He laughed. “The way her pussy just grabs onto my cock drives me wild!”

My cheeks flushed, and I could feel my locked cock, which hadn’t touched Illana’s pussy in months but could remember the feeling, squirming inside its cage.

“There’s just one problem,” he said. He let the silence hang in air. After a few seconds, the silence got to be too much.

“What problem?” I asked.

Mike smiled, tracing his finger up and down my stocking-clad thigh, sending electricity from his finger through my skin.

“Illana likes me to go for as long as I can. I mean, she really likes when I fuck her until she’s swollen, y’know? But I haven’t cum in over week, so I’m afraid I’m going to bust too quick for her. That’s a problem I’m sure you know well.”

His dig cut deep. She must have told him about how, back when I actually used my cock on her, I couldn’t last more than a few minutes. But I couldn’t quite understand what he was getting at.

“And?” I asked.

“Well, I was thinking that since we’re thinking about making this a three-way relationship, or whatever Illana was yammering on about last time I fucked her, that maybe you could help me out with that.”

Right as he said that last part, his hand went up my skirt and pressed on my cage, sending shockwaves through my body that I wasn’t expecting and nearly sending us off the road as my hands jerked the wheel of the car.

“Whoa, girl, ease up,” he said.

I don’t know why, but when he called me “girl,” my stomach starting turning from butterflies to a sort of warmth I’d never experienced before, like a sort of yearning.

“Why don’t we pull over here and discuss this,” Mike said pointing at a side road, “just pull off here and go up a ways so we don’t look suspicious from the main road.”

For reasons still unknown to me, I obeyed—like I always do. When I finally pulled over, I had to speak my mind.

“Listen, Mike, I don’t think you have the right idea here. This thing Illana wants us to do is for you and me to both date her. I’m not into guys.”

“How do you know?” he asked.

“What do you mean?” I asked back.

His hand found its way back to my cage, and he pushed on it with the perfect pressure and tilt, moving it up and down.

“Have you ever been with a guy?” he asked, another question for a question. I couldn’t answer because I couldn’t find the words. Mike’s hand was doing something to me that made it so I couldn’t explain.

“Why don’t we find out if you sure about that?” he said.

Mike then leaned in and kissed me. I resisted at first, but then, for some reason, I let him keep going. His lips just felt so good on mine. Illana was always forceful and dominant with me, but this felt like a whole other level. Somewhere deep in my mind, I guess, there’s was always been a safety with her, because biologically I was still stronger. That wasn’t the case with Mike. Mike was bigger and stronger with me, and that left me with a new kind of submissive vulnerability I hadn’t ever experienced.

I let Mike’s tongue enter my mouth and let his hands start moving all over my body. He squeezed my chest, then dragged his hand to my hip. He then reached his muscular arm fully around my hips and put his hand under my butt. He squeezed it hard, almost to the point that it hurt, but not quite. And then he somehow lifted me with that arm and pulled me over the center counsel onto his lap, facing him.

I naturally opened my legs so that I could straddle him in the passenger seat.

“Mmm, that's it, girl,” he moaned, further fueling whatever these new sensations in me were.

I started grinding my hips on him and I could feel his cock getting hard underneath me. And, not like I thought Illana would ever lie to me, but she was right about his size. It felt like a log underneath me growing harder by the second.

“Take it out,” he commanded before sinking his lips on my neck and kissing me hard.

Following his instruction, I reached down underneath me and unzipped his pants, reaching past the open fly of his boxer briefs to pull out his hard cock. It felt so unbelievably strange, not bad strange, but just a sensation I’d never thought I’d have, feeling a cock in my hand. It was hard and soft at the same time; it was warm and powerful. His cock put mine to shame—not that it mattered since mine was locked away.

“Mmmm, that’s it, stroke me,” Mike moaned.

I used my knees to lift myself up a bit and switched back to the driver seat. I then gripped Mike’s hard cock and started giving him the best hand job I could. After all, he needed to cum now so that he could last longer when he fucked my girlfriend later, right? I mixed up my strokes with a couple of gentle squeezes on his balls. I tried to remember what I had liked before Illana had made me her girlfriend and tried to replicate that for Mike’s pleasure.

Mike leaned in and kissed me again, this time with the passion and lust of a man who was in the throes of having his hard meat missile stroked by the pastel-painted fingernails of his feminine pleaser.

“Fuck that feels good,” he whispered in my ear. “So much for not liking guys,” he laughed.

He pulled away, and then I realized that his hand was behind my neck, and he was gently pulling me downward. As if on command, I let his hand guide my head down until my face was inches from his prolific manhood. A bit of panic set in. Was I really about to suck Mike’s cock—this guy I had really only met a few minutes ago. Was I really this slutty? But then I thought about how Illana had probably sucked him off dozens of times by now, and about how this cock had just last week been inside the love of my life and probably would be in less than an hour from now, so how bad could it be for me to do to him what Illana had done and would continue to do?

So, I opened my mouth and let Mike’s muscular arm push me down until his cock had fully parted my lips and was resting in between my cheeks on my tongue. I could taste his salty precum, and it made my mouth start to water. Mike had two hands on my head now, and he was gently moving my head up and down, sliding his hard cock into my now slick mouth. I curved my tongue to give him a moist tunnel to fuck and started sucking harder to give him suction.

“That’s so good. You suck a good dick,” Mike sighed out with pleasure.

His encouragement made me work his cock even harder. I was on a mission now. I wanted to give him the best blowjob he’d ever had, even better than from Illana. Before long, I was licking and gently sucking his balls, working my hand on his shaft as my tongue swirled around his head. This went on for what had to be ten minutes before I could feel his cock start to pulse on my tongue.

“Fuck, I’m going to cum,” he said.

I just kept going, knowing that within seconds, this man I had just met would be squirting baby batter into my throat. And then it exploded, shooting rope after rope on my tongue. I swallowed as fast as I could, but there was too much and some of it started leaking out onto my chin.

Mike put his finger under my chin and lifted my face up until I was at eye level with him.

“Missed some,” he said while he scooped up the cum from my chin and pushed it into my mouth.

Like a true slut, I sucked it off his finger and swallowed. Then it hit me. What had I just done? I was dressed as a sluttly girl, my cock (which hadn’t so much as been near a pussy in months) was aching in a chastity cage, and I could feel another guy’s cum sliding down my esophagus. But despite whatever negative feelings I was having, I also felt extremely satisfied knowing I had coaxed out this reward, that I had pleased Mike so well.

“I think I’m going to like this throuple thing,” Mike sighed.

“Yeah, I guess we have some things to figure out,” I said. “But let’s not tell Illana about this. At least not yet.”

Mike gave me a knowing smile and lovingly pinched my cheek.

“In due time,” he said.

I composed myself and drove us both back to our apartment. By the time we got there, Illana was three sheets to the wind drunk and basically jumped Mike’s bones when he walked through the door. He picked up her up and carried her to the bedroom without hesitation. And for the next hour, I heard Illana’s panting, drunken, lustful moans and screams of pleasure coming from our bedroom. I could hear the slap-slap of his thighs on hers, his balls on her ass. Having been inside her and having just become intimately equated with his cock, I could imagine exactly what was happening. After Mike finished, it got quiet, and I assumed they both fell asleep. I took off my skirt, top, and tights, and got into a little nighty that I like to sleep in and curled up on the couch.

I woke up in the morning to Mike leaving, giving Illana a deep, passionate kiss as he walked out the door. But just as he left, he gave me a little wink.

I haven’t yet told Illana that I sucked Mike’s cock. I’m not sure if he’s told her. If so, she hasn’t brought it up. And she hasn’t really brought up the “throuple” idea since that night either. But now that Mike unleashed a new feminine desire within me, I can’t stop thinking about what it might be like to Illana’s girlfriend and Mike’s girlfriend. I’m still trying to figure out exactly how to broach this with her.