"Right here, Joe!"

I've been walking around this plaza surrounded by sidewalk cafes for more than five minutes, looking for Matt, whom I'm supposed to meet for dinner. That voice calling my name sure sounds like him, but I still don't see him.

Then I see a feminine figure waving from a table, smiling exuberantly.

"You finally found me! Mattie!" This person, who seems to have a higher version of what is otherwise Matt's voice, impishly says, "I thought I'd wait for a while and see if you could spot me on your own." I find myself drawn in an embrace, a kiss planted on my cheek, and a whisper in my ear. "You must have looked right at me ten times, baby."

Mattie, huh? I can roll with that, knowing that underneath the feminine veneer, it's Matt, all right. In drag.

Maybe "drag" is too coarse a word for how Mattie looks, which is nothing short of fetching. His short brown hair has been styled into a tousled pixie cut. And the makeup is subtle, with just a faint blush, modest mascara and eyeliner, and a splash of red lipstick. I've never thought about it, but his natural facial features aren't particularly masculine, so the overall effect really is that of a regular woman. His print dress, while not tight or revealing, is still sexy in a casual but sophisticated way, revealing some of his shoulders and back but not his too-muscular "cleavage." He's avoided going over the top with this look, and is quite passable. Nine out of ten people here wouldn't give his feminine appearance a second thought.

I'm sure giving it a second thought, and a third. Mattie looks fucking hot. I'd bang her. Er, him, I guess. I presume "Mattie" is just cross-dressing and not going full trans, so I keep using he/him in my mind.

"Nice to see you like this, Mattie," I reply after a beat, quickly realigning my perspective. I don't exactly know what is planned tonight, but I'm up for whatever adventure it is. "You look lovely tonight."

"Thank you, Joe," Mattie says, briefly placing a hand on top of mine after we sit. "I have some things to talk to you about tonight."

"I'm all ears," I say.

"Oh, you are a lot more body parts than that," Mattie flirts. Is that where this is going? Matt(ie) wants to dress up like a woman and see what it feels like to seduce me? Fine by me. We have been blowjob-trading buddies for nearly four years, but we have never progressed beyond that. No kissing, no cuddling, no butt stuff of any kind. He's all manly bluster and standoffishness when it comes to anything that might seem remotely ... intimate. We just suck each other off and resume watching the game, drinking our beers or whatever else we were doing.

That is, until last week at the county fair, when we hooked up with Brenda and Kaitlyn, wily women who conspired to get us to kiss each other. And despite his initial reluctance, Matt seemed to enjoy it as much as I did. I've been hoping the experience somehow cracked the door open a bit to the hidden room of his Bisexuality that I'm sure exists. Maybe Mattie can help pry it further open.

We start with some small talk, during which Mattie's demeanor is considerably different than that of ... well, Matt. He's more inquisitive of what's going on with me, bringing up aspects of my life that we've never discussed much before. Other than general awareness of my Bisexuality, he's never had much knowledge of my encounters with other men or of my relationships with women. Now he's finding out, even asking me questions like "And how did that make you feel?" as we go. When I share that my girlfriend from last Fall dumped me for being Bisexual, he places his hand on mine and empathetically declares, "That must have felt awful!" Except that I know it's Matt in there, it feels like I am speaking with a conventional cis woman, and not Matt. I haven't known Mattie before, but I like her. I mean, him.

The sommelier comes by to ask for our wine selections. I order a Barolo.

"And for the lady?"

"I don't know. Joey, what do you think I should have?" Mattie has a pleading expression on his face. And a leg now rubbing against mine, under the table.

"I think a Chianti."

"Nice choice, Joey," Mattie practically purrs.

I change the subject to his love life.

"Do you know why Matt and Sarah broke up after Graduation?" Interesting. Mattie is referring to Matt third-person. Anyway, he and Sarah dated for most of our Senior year, a beautiful and popular couple. Everyone thought they'd end up married.

"I figured because she was moving away for college."

"She would have gone to community college right here ... if she thought she and Matt had a future." This is something he's never shared.

"I had no idea. I'm really sorry."

"I think she had a hard time with Matt's attitude. You know, all the bravado, always being superficial and making everything into a joke." Okay, yes, that was Matt to a tee. Still is, mostly. "Basically being kind of juvenile."

"We were all juveniles."

"Yes, but now, turning twenty-two, it's time to grow up, get serious and smooth out the rough edges."

Uh-oh. "Serious?" Is Matt(ie) trying to initiate a relationship with me? After my failed romantic relationships with women, as well as plenty of physical relationships with men, I have started to toy with the idea of a more romantic-type relationship with a man, though more as a fallback option than what I really want. But with Matt? I'm not sure I could handle that, if for no other reason than the one Sarah left him over. He has never seemed like someone I could be emotionally intimate with. Well, until tonight. As Mattie.

"So tonight is about exploring your feminine side, Mattie?"

"You could say that, Joey. What do you think so far?" he asks coyly.

"I think it's very becoming, actually." I've never been drawn to cross-dressing porn, but seeing and conversing with Mattie like this is turning me on immensely. Not only do I feel like I'm talking to a genuinely feminine version of Matt here, but the idea of a lovely lady like this packing a rod has my own fully hardened.

"I just found out that Sarah is finishing her degree early," Mattie shares. "And thinking of moving back." Now there's a bigger bombshell than Matt in drag. Maybe tonight's "feminine-side" exploration is about him dialing back the masculinity to better appeal to her?

"And how do you feel about seeing her again?"

"Matt still loves her. And wants her back." Bingo.

"And you think toning down the hard-guy image will help." I lower my voice and lean forward, looking directly in Mattie's eyes. "If I'm honest, I'm finding what you are doing here very, very attractive. Mattie. But I think it might be further than Sarah would need you to go." It might well scare her off if he shows up for her as Mattie, I'm thinking.

"You don't know that since she was with Matt, Sarah's mostly dated women. So exploring the feminine facet might be more appealing to her than you realize. I'm trying it on in full tonight, to get a feel for it. Don't worry, Matt won't completely turn into Mattie. But he is learning a thing or two."

"I didn't even know about this feminine side until tonight, Mattie."

"Oh, Mattie's always been in here," he says, putting his hand on his heart. "But Matt's always kept her locked in the basement."

Or closet, I briefly think. No, that isn't right. Matt's not closeted, and not gay, even if one minute ago I thought he might be about to come Out as well as declare his love for me. Whew! That bullet dodged, it's clear this is all to appeal to a woman. His beloved Sarah, no less.

Shyly, he says, "You must know that Matt is making himself very vulnerable to reveal Mattie to you in this way."

"I understand that, Mattie," I empathize, taking his hand. "I will not violate your trust, or use any of this against Matt. What happens between Mattie and me stays with Mattie and me."

"Thank you. So ... you remember last weekend?" Mattie asks plaintively. "When Matt kissed his first man?"

"Yes. How did he feel about that?"

"He liked it more than he expected. Different from kissing a girl, maybe even in a good way. But I - Mattie - have wondered for a long time what that would be like, and I loved it."

"I liked kissing Matt too, and I think I might enjoy kissing Mattie even more." So Matt(ie) has been suppressing the urge to kiss me for a long time? What else is locked in that closet ... er, basement?

Just then, the waiter comes by to take our orders. And the same thing happens as with the wine. I'm forced to order for Mattie again, and he practically beams at me when I step up and do so.

"You see, Joe, Matt hates being told what to do, and had a hard time when Sarah tried to. But sometimes Mattie likes it." Leaning in, he murmurs, "Last weekend, when you and Matt sucked each other in front of Kaitlyn and Brenda? And you smacked his cheek with your throbbing cock and commanded Matt to, in your exact words, 'Suck it!'"

"Yes, I did that."

"Matt was fine with it, having already decided to suck you anyway. But Mattie? Mattie leaked about an ounce of precum when you did that."

Okay, now I get it. To Mattie, being feminine also means being submissive. That's been true of exactly zero women I've ever been with, but I can roll with this.

"Well, then you listen to me, Mattie," I say authoritatively. "When we are done with this meal, we are going to go back to your place, and you are going to suck me off." His eyes widen and brighten. "You are going to suck me like a woman does, not like a man. And you are going to take my cum in your mouth before you get any pleasure for yourself." His face brightens. I find this almost disturbingly empowering, but I take care to thread the needle here. "Only after you have made me cum and shown me you deserve it, will I touch you down there. But I will be gentle and will not abuse you. I will give you your release too. Once you have begged for it. What do you think of that plan?"

"I just leaked again, Joe," Mattie confesses, resting his elbow on the table and his chin on his hand, blinking his slightly-thicker-than-normal eyelashes coquettishly. "I do hope you will pay for the dinner."

"Of course."

"Do you know why?" I shrug. "Because, Joe", he says slowly and deliberately, "it is only after I have received some kind of payment that I can truly be ... your whore."

I almost choke on my food.

"And I hope there will be more than just cocksucking on the menu. You've done that with Matt a hundred times. But Mattie might be ready to go ..." After a pause, he lowers his voice and breathily, dramatically concludes, "... all the way."

I almost choke on my food again.

After I compose myself, pay for dinner and lead Mattie out of the restaurant by the hand, we round a corner and I pull him into an embrace, and a kiss. He waits for my tongue to enter his mouth, but then returns my lingual thrusts enthusiastically, rubbing his hands on my butt cheeks. We make out for a lot longer than we did last week for Brenda's and Kaitlyn's benefit.

"Oh Joey, Mattie has wanted to do this with you for a long time," he gasps.

"Well, I must say, as much as I like Matt, I'm glad he's letting Mattie be in charge tonight."

"Oh, I'm not in charge, Joe," he says, nibbling on my ear. "I need you to be the one in charge tonight. Just so you know, Sarah likes to be in charge sometimes, and Matt would never let him. So I need you to show him - and me - how to surrender to someone else's direction."

Aha. the picture is ever more clear. Tonight's show of vulnerability is about exploring not just his feminine side, but his submissive side for Sarah. Which is not quite the same thing to me. But maybe, to Matt(ie), it is.

< = = = = = = = = >

We race to his house, and his bedroom, where we make out again and I start feeling him up. I squeeze the modest mounds under the dress, through the pads under his bra, to pinch his nipples.

"Ohhh, yes, Joe!"

I reach between his legs and find ... not much. He's been tucking. So I reach behind him to unzip the dress, watching the thin fabric flow across his shoulders and slip to the floor. Damn, in his black lace bra and panties, his affect is still feminine enough that I could still be with a small-breasted cis woman (with unshaved legs, anyway) and not a man.

That changes as I pull off the panties and release his straining cock. There's a mess of precum wetting the hairs on one thigh, validating his earlier leakage confession. Smirking, I say, "Mattie, I'm going to get you excited, and then I'm going to make you wait," as I kneel and lick the precum off his leg, and then the end of his penis. I give the tip quick flicks with my tongue, several seconds apart, to prolong things.

"Yesss," he hisses, seeming to approve of this approach. "Tease me, Joe!" I take just half the glans in my mouth and withdraw, drawing a moan. Then I slip my lips just over the coronal ridge and pull back again, flicking my tongue across his pisshole and releasing another moan from further within his depths. I give him a quick half-stroke with my hand, then stop. Another moan. Finally, I take half the length into my mouth and keep it there, working the underside with my tongue, and stroke the bottom part of his cock vigorously. All this for ten or fifteen seconds, until I can see his ecstasy building.

Then I stop it all, standing up. I undress myself and reveal my erection, gently but firmly placing my hand on his head and pushing downward. "It's time for you to suck me, Mattie. You are going to suck me well, and you are going to suck me ladylike, but you are going to suck me to orgasm as quickly as you possibly can. I am desperate to fill your dirty mouth with my cleansing jizz."

Mattie kneels and looks up teasingly. "Now, Master?"

"Yes, now!" I direct, grabbing it with my hand to smack his cheek with it, just like I did last week.

A taunting look still on his face, he tentatively sticks out his tongue he licks the tip halfheartedly. Oh, he's testing me.

"Suck my cock, whore!" I command, making sure it sounds insistent, not angry. "Suck it now!" I again dick-slap his cheek. I see a drop of precum ooze out of his cock and leave a damp little dot on the carpet.

Mattie now takes in my meat fully. Matt is already a pretty good cocksucker, and knows all the tricks to do with his tongue, with varying rhythms and with gently cupping my balls to make a man feel good. But while Matt might occasionally glance up at me while blowing me, Mattie locks a plaintive gaze up onto my eyes the whole time. I guess that's the "feminine" part of this blowjob.

"Is that good, Master?" Mattie pleads.

"Yes, very good work, whore." I'm already pretty worked up and will cum soon. "Now bring me home."

"Yes, Master." He continues his mouthwork but brings his hand into the action, stroking the lower part of the shaft enthusiastically and provoking a rapid, rip-roaring climax.

"Don't swallow," I gasp as I start squirting his mouth full of cum, reveling in the ecstasy of his firm, rouged lips. I produce so much that he'd have to start gulping to contain it all, so some leaks out and dribbles down his chin. "Now take off your slutty bra, drool out my cum, and rub it all over your tits."

This makes quite a slippery mess. I fling Mattie down onto the bed and climb on top, kissing her briefly but focusing mostly on slurping my semen off his mostly-smooth chest and his hairy nipples, something else Matt would never, ever let me do. I chew on his nipples, hard enough to make him squeal, while giving his cock just the occasional teasing stroke.

"Yes, Master! Harder!"

I move back up to kiss him, stroking him more determinedly while I place my slippery unit against his, making him moan continuously with pleasure. "Do you think Matt ever knew that having a guy stroke and frot and kiss you at the same time feels almost as good as having him suck you?"

"Mattie always suspected so," he pouts, "but Matt wouldn't let him." Triumphially he adds, "And Mattie was right."

"Good. Now you tell Matt that next time he's with me, we will not start with blowjobs. We're going to do this together, until we both spew all over each other's cocks."

"Yes, Master. I'm pretty sure Matt wants that now,"

I sense that once again, Mattie is getting pretty excited. I stop jerking and accuse, "Are you getting ready to cum, Mattie?"

"Oh my God, yes, Joey! Please make me cum!"

"Not quite yet. There's one more thing you have to do to earn it."

He whimpers, almost reaching to touch himself, but I stop that with a sharp look and get myself on all fours. "Lick my ass, dirty Mattie, and then fuck me!"

Now, if kissing a man on the lips was new territory for Matt last week, kissing a guy on the asshole is a new continent. Nevertheless, he dives in and starts bathing my perineum and ass-crack with his tongue, eventually flicking it back and forth across my aperture. I moan in appreciation.

"Is that good, Master?"

"Very good. Now I want you to lube your finger and slide it in me." A manly finger deftly slips inside, exciting as many nerve endings just inside my rectum as there are on the tip of my penis. "Pull it back out and push it in again." I'm ecstatic with pleasure from this, even having just cum. "Keep doing that. Finger-fuck me, you dirty slut!"

Mattie does this, in and out, then starts to flex his finger inside me, at one point brushing my p-spot and causing me to leak semen. Notices this, he keeps rubbing his fingertip across the gland, causing me to moan loudly ... and make a bit of a mess on the bedspread. "Am I making you feel good, Joey baby?" Mattie asks affectionately, gently kissing my back.

I can only nod and gasp in reply, making a mental note to get finger-banged a lot more often. "And you've just earned the chance to cum, baby. Are you ready?"

"God, yesss." The finger withdraws and I feel Matt(ie)'s cock pressing up against me. I relax my butthole for him, having learned how over the past year, and he slides in. I swear, every goddamned time I do this, I realize I'd forgotten just how good it feels.

"Oh Joey, you're as warm and tight inside as a virgin cunt! I may not last long."

"Let yourself go, Mattie. Cum for me and me alone. Fill my tight ass!"

Sure enough, within seconds he is gasping with pleasure and whitewashing my colon with his glorious goo, making his cock and my asshole a slippery, sloppy mess. He collapses on me, kissing me tenderly on the back of my neck and declaring, "That was sooo good, Joey."

"Good, but you're not done, Mattie," I caution, feeling the sexual equivalent of red mist clouding my judgment. I roughly flip him on his back before he can enjoy any post-coital relaxation. I press my cock against his dry asshole, barely restraining myself enough. "You said you want to go 'all the way' tonight, baby?"

"Yes, Master. I did say that."

"Good. Because I'm going to fuck you like you've never been fucked before."

"That will almost assuredly be true," he giggles, still in his feminine voice as he spreads his legs, "because I have never been fucked before. Your cunt isn't really virginal, it just feels that way. But mine is. Do it, Joey." He beggingly implores, "Take me now, please?"

No words are spoken as I lube us up. His latest feminine supplication having calmed me, I apply gentle penile pressure against his opening. "Relax, baby, just let it open on its own," I say, stroking his cheek and giving him tender kisses. "We'll take our time, and it will let me in when it's ready." After a few seconds, we start making out again, and I sense a little dilation down there. I press in a fraction of an inch, then his hole clamps down. I squeeze his nipples and he starts to unclench again. Now I feel safe to apply more pressure, and I soon feel the rim of my cockhead passing beyond his constriction, into the warm void beyond. Having opened Mattie sufficiently, I shove in my remaining few inches, leading him to grunt primally.

"Fuuuck!" he exclaims in a lower voice than I'd expect from Mattie, as I notice his own cum starting to leak out of my ass and down my balls. Has he slipped out of character? Am I fucking Matt now? I don't care, I'm happy to fuck either or both, taking long strokes that leave the colon empty, and then drilling my way in again. Whoever I'm fucking wraps his arms tightly around my neck for the most passionate kiss we've had yet, and despite having already orgasmed, I soon find myself hurtling over the precipice again, filling Mattie's virgin canal with the manly syrup that it has lacked for too many years.

Still excited and in his lower voice, his cock oozing, Matt says, "Holy shit, I had no idea it would feel so good to have a hot cock inside me. I should have started doing this years ago."

< = = = = = = = = >

Chuckling sheepishly with the realization that he's broken character, Mattie returns to his higher voice. "I mean, Matt should have started doing that years ago," he giggles as he pulls me into a post-intercourse cuddle that I would normally do only with a woman (although a friend recently taught me is okay with a man too). "After this, he's going to want you to fuck him too."

"I look forward to that."

"Thank you for your openmindedness and discretion in indulging me tonight, Joe. I think you will see a more well-rounded Matt after this, and not just sexually. As will Sarah."

Although I don't know it yet, next week Sarah will let me know exactly what she thinks of the new Matt.