Road Trip

Another workday traveling. Another boring anonymous hotel... though this one is a small improvement from the usual dumps where my company books me. It even has a bar! I figure I've earned a glass of wine and I head on down. I'm still wearing my work clothes - a blue dress, sensible heels, stockings. I sit down near the end of the bar, and there you are.

You are decent looking in an early-40s, anonymous hotel sort of way. Clearly you're every bit as tired of business travel as I am. And unlike the younger guys in the place, at least you are having a proper man's drink - I can smell the bourbon in the glass.

We chat. People always figure out I am transgender after a couple minutes. I'm sure you know, and that's fine. What matters now is a banal conversation about the usual stuff with a human being who doesn't care about my gender. They're just similarly sick of speakerphones, conference rooms and getting the goddamn middle seat on Delta.

I'm almost done with my drink, and I should be thinking about dinner. It's not going to be with you, and you and I both immediately sense that. Just a pleasant half-hour oasis before a solitary dinner, review of some work files and an early bedtime.

You drop your phone, and swear mildly as you stretch down from the barstool to retrieve it. My head is drawn to the movement, and in that one glance I cannot believe my luck! Your shirt lifted up just a little in the back as you reached, and I saw it. The tag attached to the panties that I now know you are wearing under those gray trousers...

I need to make a decision, and fast. You've just finished your drink. I can see the ring on your left hand. I can also tell that you're not the type to cheat - or at least, not often. Neither am I. But even as the sensible part of me asks "what the fuck are you doing?!?!", I know exactly what the fuck I am doing!

I've leaned in close to your ear before you notice and whisper "I love your taste in pretty panties!" You turn bright red faster than I ever imagined possible... And then the stammering begins "well I you see it's uh and oh wait". I put my right finger to your lips to shush you, and my left hand lightly touches your right thigh.

You look forward at the bar with a look between angry, ashamed, and (yes) aroused. It's quite a performance! I lean in again, my lips almost touching your ear. "I absolutely love it when guys wear panties. It's incredibly sexy. I'll bet your cock and ass look absolutely luscious." I lick your ear - just a tiny bit, playfully. I pull my head back a bit as you turn to me. My left hand feels the fabric on your slacks tug a bit...

In a normal voice I ask if perhaps we should have another drink. You motion the bartender over; he gives you a knowing smile. He may not know why or how, but he has seen this sort of thing play out over and over. I rest my left hand a little more fully on your thigh; with my right I lightly caress your face and point it to the mirror over the bar so I can whisper in your ear again.

My head is a little further back. I can smell your cologne and feel the scratchiness of your neck against my cheek. "I saw the Victoria's Secret tag, but didn't actually see the panties. Are they satin? silk? lace? How are they cut?" You turn your head a little toward me, but I can hear your whisper fine in the quiet bar and nobody else is nearby. "Th- they're satin and lace... not new. Green. Not a thong but not granny style." I giggle a little and whisper "you have a hard time saying panties, don't you?" You nod.

Nobody pays us the slightest attention. I lick your ear again, and nibble the lobe. "I can say it for you, all you want. Green satin and lace panties from Victoria's Secret? Probably bikini panties - or maybe hipsters." I feel the fabric in your slacks twitch again. Now my hand is fully resting on your thigh. I kiss you on the neck and move my hand up and in... and now I feel exactly what I thought I might find. You start a bit as my hand feels the lacy elastic of your thigh-high stockings through your slacks!

I giggle again and give your thigh a playful squeeze. Then I feel YOUR hand cupping the top of my ass, at least so far as the barstool will let you. I lift my hand from your thigh and yours goes right to the available spot on my own thigh. The dress is a wrap and my stocking-clad leg is right there for the taking. As you explore a bit, I ask you to tell me about it.

And you do. The embarrassment even when you were a k**, the fear, the wife who would never understand. The panties and stockings are hers, you can't buy your own stuff - would never be able to shop in person and can't risk a delivery to the house. It's a super turn-on and always has been. Does that make you gay? A crossdresser? A sissy? Your hand leaves my thigh and you turn back to the bar, as though you cannot believe what you just confessed to a total stranger.

I lean back in, for a third time. This time my hand is on your upper thigh.. I turn my wrist and the back of my hand grazes your cock. "Don't worry about names or labels. For now all that matters is that I want to please you. I don't want your name or your phone number. No strings. I just want this moment. But if I don't get to see you out of those clothes and in your sexy panties I'm just gonna burst!" I kiss you on the lips as you reach for your wallet to settle the bill.

Before we know it we are in my hotel room, kissing furiously as I stroke you through your slacks. I guide you to the bed and sit you down, as I start unbuttoning your shirt. You let me undo your belt, and then unbutton and unzip those gray slacks.

Yes, the panties are green and lacy... with an impressive bulge that hints at an enjoyable time to follow! I start to gently rub your manhood and you groan a bit, as you lie back on the bed. I tease you for a minute or two, first with my hand and then with my tongue tracing light lines through the panties. The tracing turns into kissing, and then I take you into my mouth with the panties still between us. One of the few advantages of being transgender is familiarity with this particular equipment... and I am determined to give you the very best!

After a little bit of this oral foreplay I lift my head and ask "Do you prefer me in my bra and panties, or would you rather see me in some lingerie?" You don't immediately answer. I stand up in front of you, untie the wrap on my dress, open it. You probably recognize the matched Wacoal set in deep purple, though the lacy thigh-highs are a UK brand that you don't usually see here. "Get undressed and I will be right back!" I say. I grab something from my suitcase and slip into the bathroom to let you shuck off your clothes.

A few minutes later, I emerge wearing a red Flora Nikrooz babydoll with a sheer body and the matching skimpy bikini panties. My black stockings are still on - as are your cream colored ones, along with that gorgeous cock still straining until that skimpy fabric. You're comfortably laid out on the bed, and so it's quite reasonable for you to ask why when I tell you to stand up. But you do it, even without expecting an answer.... though I do have my reasons.

I turn you to the bed where I sit down on the edge. I'm eye level with your chest, as my hand goes between your legs. Gently stroking, pausing now and then to feel your muscular thighs under the stockings. With my other hand I gently tease one nipple as I let my tongue work the other one. You groan again, this time louder. I feel your luscious cock spring to full strength and shift to the side as it pushes the front of your panties to the limit. After a minute of working your nipples, I stand to kiss you some more. As my tongue and yours collide, I let your cock over the waistband of those confining panties. It is every bit as gorgeous as I hoped. I stroke it for a minute and a bead of moisture immediately forms at the tip. My finger deftly probes and brings it up; as my head pulls back from our kiss I enjoy my first taste of your love.

I'm not interested in waiting and neither are you. I kneel in front of you. My hands glide up and down over the panties still covering the bottom of your cock, every now and then gently tracing and squeezing your swollen balls. And I take you into my mouth. You gasp, and I do as well. It has been...what...ages? since I last did this? Probably in college. But it's so right and so perfect and now I just want to make you explode in passion!!!!

But not right away. I start stroking you slowly as my tongue works gently on your head. My other hand slides behind to fondle your ass through the back of those increasingly strained panties. As I do my work you open your legs a bit - just as your lovely shaft obligingly gives up a couple more precious drops. I lick my middle finger, run it through your wetness, and slide it between your legs, through the lacy leg opening, and up to your hot ass... just probing and slightly pushing in. You push your pelvis into my face a bit more - your bush tickles my nose and chin - but you clearly don't want me to stop. I take you all the way back into my mouth again, so that both my hands can concentrate on exploring your fine ass over and under the panties. To my surprise, deep-throating you comes as naturally as anything. You put your hands on the sides of my head and I can sense you are getting close...

So I pull back, and my hands are now on your thighs again. I push on them to turn you around, me now kneeling behind you. With one hand I reach between your legs and continue slowly working your rock-hard shaft - pausing occasionally to gently trace the head with my long fingers. The other hand slides your panties down just below your throbbing balls, and then moves to your ass. I open you up, just enough to get my tongue on your tight rosette. As I begin gently massaging your back door, you move your hands to open yourself further. My finger and my tongue continue their work as I thoroughly enjoy my sexy submission to your ass.

I could probably lick your ass all night, but I'm neglecting the other bits! I draw my head back a bit and you, unprompted, turn around. This time your cock is immediately in my mouth, and again I can kiss your bush on every stroke. You and I are moving in passionate unison, your breath getting raspier. I feel everything tense up, and ...

Wow.

As the first taste of your astringent, salty lust hits, it is like time stops. I realize that I've never actually had a man come in my mouth before! And then the waves are everywhere: my throat, my cheeks, my tongue. My entire mouth is awash from your bitter, bleachy load. Before I can swallow, a little escapes my mouth and drops to your panties. The rest I happily drink down. Nobody in their right mind could say they like the taste, but at that moment if you could have come ten more times in as many minutes I would have lustily taken every drop!

I remain kneeling in front of you for a minute, licking your cock and balls - waiting for that last little bit of come to emerge. After it does and I take it onto my tongue, you shudder a bit, pull back and flop your back onto the waiting bed. I climb next to you, my stockinged leg lightly d****d over yours, gently feeling down your chest. As I glide your panties back up into place (and you stiffen a bit! amazing.) my fingers detect the little wet spot where my eager lips failed me. "Sorry about that." Fortunately, you seem to be the forgiving type. I get up, walk over to my suitcase, and take out a fresh Natori thong. "Let's get you into some clean panties." You stand up, and I kneel again before you. I gently ease down the lacy green Victoria's Secret panties that started off this crazy hour, and help you into the red thong. When I see your sexy/tasty ass beautifully surround the tiny panties, I'm ready to go at it again.

Instead, I suggest that you grab your clothes, go into the bathroom and dress. I can see a flicker of disappointment in your eyes. "Please don't worry," I reassure you. "I'm not done with you yet. I just had an idea..." And so off you go to clean up. I quickly throw off the babydoll and stockings, slip into a beige Chantelle bra and matching hipster, a short casual skirt and a cream colored top. I'm just getting my shoes on as you come out. I'm quickly getting addicted to that face and definitely that body. I kiss you, and you open the door for us to leave. I suggest that I drive, since I know where we are going. "Dinner?" you say. "Yes, but we have an errand to run on the way."

The shopping mall is as boring and anonymous as the hotel, but it does have a decent Macy's inside. We're holding hands. At this hour there aren't many customers, as I lead you toward the lingerie section. For a moment you tense up - perhaps you think I am here to embarrass you? Far from it. "It seems silly for you not to have a chance to do some shopping," I say. Once you realize that you can shop for yourself with me as cover, you smile and kiss me right there in the middle of the department. We spend an enjoyable 20 minutes or so, me picking up and examining the various panties and other intimates - showing them to you for approval. At one moment I accidentally back into you; you are hard as a rock! As we wander around, we trade the occasional grab and pinch. I shop for lingerie all the time but I realize what an opportunity this is for you. So do you, apparently! By the time we get to the register, I'm holding a half dozen panties of different styles and colors, a softcup bra, a chemise, a half slip and three pairs of thigh-high stockings. The bored sales associate rings us up. As you put down your credit card, I thank you for "all my gifts" and give you a big kiss.

We walk out of the store and I hand you your bag of treasures. You turn me toward you and lean in. I'm not usually one for public displays of affection... But in this anonymous town in the middle of nowhere, I figure an exception is in order.

Eventually our lips and tongues part, and we continue to the car. We're off to a mediocre meal, livened up by plenty of sexy talk about your new collection. And then we return to my room...

But that's another story.

Tracypanties, Spring 2018