Memories - Work Prom

Emily and I dated secretly for almost a year before we were publicly out as a couple at work. I don't know why; it wasn't prohibited. I mean, I know why. She was younger than me by eleven years and wanted to make her way in the professional world without the stigma of dating someone more established.

So we hid things.

It wasn't like we avoided each other and I spent enough time around her that people must have know I like her (did I 'like like' her? of course). But they didn't know we were dating. Hence people trying to set her up. Hence guys at the office occasionally flirting with her or asking her out.

Well our office had a "work prom" event that Emily, as one of the new hires, as one of the pretty ones, as a friendly face, was asked to help plan and organize the event.

I went with her to pick a dress. It was a weird experience, an awkward dynamic. "You know we cant go together," she said.

"I know," I said.

"We can't even sit together," she said.

"Why not?" I asked.

"It would be awkward," she said, "you'd be sitting there staring at me like you're staring at me now."

Staring I was, staring at her as she posed in a scarlet red mini dress with a square neckline that emphasized her breasts, her waist, and her hips, black nylons, and ankle strap heels.

"I won't stare at you, Emily," I said.

"You'll stare at me," she said. "People will see you staring at me."

"Fine," I said.

**********

The week before our work prom, Emily took a box from her closet and brought it to me. 

"What's this?" I asked.

"Open it," she said.

Inside the box was an elaborate set of lingerie. A pinkish bra and panty set, a matching garter belt, a matching camisole and tap panty set, nylon stockings. "For prom," she said.

I looked at her, misunderstood. "For after?"

"After, sure," she said, "but to wear to prom."

"Your dress is too tight for all of this," I said.

"Of course," she said.

I looked at her, confused for a moment, the realization slowly dawning on me. "Emily, I...I can't," I said. I wore panties to work, sometime a bra, sometimes hosier, but never all this, never this much. Never layers and layers of lace and fabric.

"Of course you can," she said, "of course you will."

"Emily, people will...someone will..."

"If you can't be my date, sweetie, you can certainly be my pretty girl."

"Someone will see," I said.

"No one will see," she said. "I'm planning it, remember? The lights will be dimmed, you'll have a suit and tie on, at most someone would see a flash of nylon at your ankle, but they'll just assume it's dress socks."

"I have to wear socks," I said.

She shook her head, smiling at me. "No boy stuff," she said. "No boy underwear, no boy socks, just a suit, shirt, and tie, the rest is feminine."

"Emily..."

"No one will see," she said, "I promise. 

Because we couldn't go together, we didn't get ready together. I didn't see her that day until that night when I got to the venue, alone as I had the last several years.

I didn't see her at first, I got a drink, saw a couple of people I knew, watched their eyes, watched to see where they looked, what they knew, but it was nothing. I found a guy Mark I knew, one of the guys who had been flirting with Emily. He was sipping a whiskey to my white wine.

"Holy shit," he said.

"What?" I asked, confused, followed his gaze, saw Emily across the room smiling at us.

"She is fucking gorgeous," he said. 

"She's pretty," I said.

"She is fucking gorgeous," he said. "Fucking bend her over the edge of a table and fuck her gorgeous."

"Mark," I said.

"What?" he said. "Don't be a white knight, you know it's true."

"I...I don't think we should talk about a...a coworker like that," I said.

"Fair," he said, "she's out of your league, anyway."

"What's that supposed to mean?" I asked.

He looked at me, glanced at Emily. "No offense, bud, but if a guy like you caught a girl like that, you'd be the dog who catches the car."

"A guy like me?" I said.

He looked at me. We weren't friends, but it wasn't like he never talked to me.

"Dude, no offense, but you're kind of...soft. A girl like Emily goes for the masculine type, not the neat, carefully put-together type who seems soft underneath."

"Soft?" I asked, wincing at the thought of what I was wearing underneath my suit.

He shrugged, took another sip of whiskey.

"Yeah. Soft. The secretaries had a whole theory about you for a while. Figured you were gay. I'm not saying you are, just that there was talk. The way you dress, the way you talk, the whole careful thing. They were pretty convinced."

"That's...I' not," I said.

"Don't look so shocked. Half the floor thought it. Emily probably did too at some point. You're just not the type who sets off the usual alarms, you know? More the quiet, put-together type. Soft under the surface." He glanced past me toward Emily, then back.

"Anyway, I'm not trying to start shit. Just saying a girl like her isn't looking for that. She's looking for someone who'll actually...you know..."

She was walking over towards us when Mark swore. "Fuck, Henderson," he said, nodding over at a couple who just walked in. Henderson was his department head. "Gotta go kiss the ring. Tell her I'll be back in a minute."

He downed his drink and walked over towards Henderson as Emily walked across the room. She approached me, gave me the hug two work friends give one another, and as she did, I felt her hand on my back, touching, checking, confirming. 

"I wore it," I said, Mark's words echoing in my head.

"Of course you did," she said. "What were you two talking about?"

"You," I said.

"Me?"

"You," I said, "like how badly he wants to..." The words caught in my mouth.

"Fuck me?" she laughed.

"Pretty much," I said.

"He's got a reputation," she said.

"What reputation?" I asked.

"With the secretaries."

"What kind of reputation?" I asked.

"They call him jelly."

"Jelly?"

She smiled. "The kind of guy that makes your legs go all jelly like when he fucks you."

"God, Emily," I said.

"It's amusing," she said, "seeing the two of you looking at me."

"Amusing, is it?" I said.

She looked around, made sure no one was in earshot. "One, the man, thinking only about fucking me and the other, the pretty little boy, thinking only about his soft, little penis, tucked safely away in his panties."

"You're enjoying this, aren't you?"

"Immensely," she said.

"He...he said you're out of my league," I said, my voice shaking slightly.

"I am," she smiled.

"He...he said a woman like you goes for the masculine type," I said.

She sipped her wine. "He's not wrong," she said.

"Emily..."

"Emily…" She tilted her head, still smiling, the red dress catching the low light just enough to make the square neckline look even more deliberate. 

"You're pouting," she said softly. "It's cute." 

"I'm not pouting." 

"You are. Soft little pout. My pretty little jealous that a man's looking at me. Her eyes flicked down my suit for half a second, like she could see straight through the jacket to the lace. 

"Emily, can...can you see," I asked, suddenly nervous.

She smiled. "No, it's our little secret that under that suit is the most feminine boy I know."

I blushed. "Emily..."

"Mark's not wrong about the masculine type. I do like a man who takes what he wants. Who doesn't need permission." 

I swallowed. "He was talking about… how he wants to fuck you. Explicitly. Like bending you over a table and..." 

She smiled wider, almost pleased. "I know." 

"You know?" 

"Of course I know," she said.

"But..."

"I put together the seating chart," she said, voice low and conversational, like she was discussing the weather. "Mark's sitting next to me at dinner. Right beside me. Close enough to get a good look every time I lean forward." 

I stared at her. "Why would you do that?" She took another slow sip of wine, watching me over the rim. 

"Maybe you shouldn't have picked out such a low-cut dress," she said lightly. "It does tend to give people ideas." 

"I didn't pick it so Mark could...could stare at you," I said.

"You picked it because I looked good in it," she said, still smiling. "And I do. You stared so hard in the store I thought you were going to forget we weren't supposed to be together. Now everyone else gets to stare a little too. Including Mark." 

I felt heat crawl up my neck. "You're enjoying this." 

"Immensely," she said, looking around casually like we were just colleagues talking about the weather. "And so are you. My pretty little secret, standing here in all that soft lace no one can see, getting jealous because the man who wants to bend me over a table is going to be sitting six inches from me at dinner." 

She stepped half a pace closer, close enough that I caught the faint scent of her perfume. "Don't worry. I'll make sure he behaves. Mostly. And if he doesn't…" Her voice dropped even lower. 

"If he doesn't?"

"You'll still be the only one who knows what's under your suit when I drag you somewhere private later." She let the words hang, eyes bright with that familiar mix of affection and mischief. "Now finish your wine like a good boy. Dinner seating starts in ten minutes. Try not to look too soft when you walk past his table."

I sat three tables away, close enough to see everything and far enough that no one would notice me watching. 

Emily leaned in whenever Mark spoke, the square neckline of her red dress dipping just enough to make the movement deliberate. His eyes dropped every time, quick, greedy glances that lingered on the soft swell of her breasts before climbing back to her face with a grin. She didn't pull away. She didn't adjust the fabric. She simply stayed there, smiling, letting him look. She knew she was teasing him but her occasional glances at me let me know she was teasing me too. That's what made it so hard to watch: she was teasing me without letting him know what was going on.

The jealousy hit first, sharp and immediate, a tight band around my ribs exactly where the band of my bra pressed against my skin. But it didn't stay pure. It twisted almost at once into something hotter, heavier, that sank low in my stomach and pressed against the nylon of the panties I was wearing. Every time his gaze slid downward I felt the garter straps tugging gently at my stocking tops, the soft weight of the camisole under my shirt, the way the panties held me. Soft and tucked. Carefully put-together. Exactly what he had called me earlier. 

Their sexual tension reached me like heat from an open flame. I could almost feel the low current running between them, the way her laughter stayed a fraction too long, the way his shoulders angled toward her, the quiet certainty that if the room emptied he would have her bent over the nearest table without hesitation. Watching it made my pulse quicken. It was erotic in a way that shamed me: seeing the woman I loved flirt so openly with another man, offering him the view I was only allowed in secret, made my mouth go dry and my skin feel too tight under my suit. 

That same sight reinforced every quiet doubt I carried. I was the one in soft, pretty lingerie, in stockings, the one who had been called soft, the one who sat neatly in his chair while a masculine man claimed Emily's attention. The inadequacy should have hurt. Instead it fed the excitement, turning the jealousy into a low, constant ache that was almost pleasurable. The more openly he looked, the more deliberately she leaned, the more I felt the contrast between us...and the more that contrast aroused me. He was a man, the type of man that got women like Emily. The type of man who fucked women like Emily.

I wasn't. Not with any woman, not with Emily. I knew this...I was soft, feminine, quick. I was never the type who possessed a woman, never the type a woman craved. I was the type that felt shame when he entered a woman, was afraid how quickly it would be over, who knew he could never be enough to satisfy a woman like a man does.

And then the deeper current rose. 

Watching her flirt so effortlessly with a real man while I sat three tables away, secretly feminized under my suit, dragged every old feeling of inadequacy to the surface at once. Years of quiet comparisons, of sensing I was never quite enough, of knowing I moved through the world more carefully, more softly than the men around me. Everything I had spent a lifetime trying to keep buried came rushing up in a single, breathless wave. Mark laughed at something she said and leaned closer; she didn't retreat. She offered him the easy, unguarded attention I only received behind closed doors. 

I wondered, not for the first time, why she had picked me. 

Why choose the man who wore layers of lace and stockings beneath his clothes, the one the secretaries had once assumed was gay, the one who sat here soft and carefully composed, when she could so clearly command the interest of someone like Mark--someone who looked at her with open hunger and no hesitation? The question sat heavy in my chest, mixing with the heat of the lingerie against my skin and the sharp, shameful thrill of watching her. It didn't make me want to leave. It made me want to stay exactly where I was, feeling every inch of the gap between us, while she smiled at another man and I remained her pretty, hidden secret three tables away.

Watching him, I wondered yet again, why me?

After dinner, at an appropriate time, Emily came up to me, took my hand and squeezed it. "Let's get out of here," she said.

I looked around. Several tables away sat Mark. Two tables from him sat two women in Emily's age cohort. All three watched us, watched Emily take my hand, watched her smile, watched her walk out with me. I guessed it was public knowledge now, and I wondered what Mark thought seeing her walk out with me.

Outside the venue the night air was cool against my face. Emily didn't let go of my hand. She just kept walking, heels clicking on the pavement, red dress swaying, until we reached her car. She drove. I sat in the passenger seat feeling every layer of lace and nylon under my suit, the garter straps shifting whenever I moved, the soft weight of the camisole against my chest. Neither of us spoke much on the ride. The silence wasn't empty; it was charged with everything that had happened at the table three seats away from me.

Her apartment was quiet when we stepped inside. She locked the door, kicked off her heels, and turned to face me in the soft light of the living room.

"Suit off," she said simply.

I hesitated only a second. Then I shrugged out of the jacket, loosened the tie, unbuttoned the shirt. Each piece of "boy" clothing that came off made the rest of me feel more exposed. The camisole came into view first, the pinkish lace any nylon over the matching bra, soft fabric clinging to my chest. Emily watched without speaking, eyes bright. I unbuckled the belt, pushed the trousers down, and stepped out of them. The garter belt, the stockings, the tap panties, everything she had chosen for me, was fully visible now.

She walked a slow circle around me, one finger trailing lightly along the edge of a garter strap, then over the soft swell of the camisole.

"Still perfect," she murmured. "No one saw a thing. Just like I promised."

I stood there in the lingerie, suit discarded on the floor, feeling the familiar mixture of shame and heat. "Emily…" 

She stepped in front of me, close enough that I could smell her perfume again, the same scent that had drifted across the table while Mark stared at her neckline.

"You want to know why I picked you," she said. It wasn't a question.

I nodded. My voice came out quieter than I expected. "Yes. After tonight…after watching him look at you like that…I keep wondering. Why me? Why this?"

She reached up and adjusted one of the bra straps on my shoulder, gentle, almost tender. "Mark is exactly what he looks like. Loud. Hungry. The kind of man who would bend a woman over a table and not think twice about it. Half the secretaries already know what that's like. He would fuck me hard and leave me satisfied in the way those kinds of men do."

I swallowed. The image flashed through my mind again, her leaning forward, him watching, and the panties tightened slightly around me.

"But I don't want that as the whole story," she continued. "I watched you for months before we ever spoke properly. The careful way you dress. The way you listen more than you talk. The soft edges everyone else mistook for something else. The secretaries thought you were gay. I thought you were gay. Mark thinks you're soft. They're both half right and completely wrong."

Her hand drifted down, fingertips brushing the lace of the camisole, then lower, resting lightly over the front of the panties where I was tucked and soft.

"I saw someone who gets hard from the contrast. Who feels the gap and doesn't run from it. Who can sit three tables away in stockings and a garter belt while another man undresses me with his eyes, and instead of leaving or starting a fight, he stays. He feels every strap. He feels how small he is." Her hand was gently touching my soft, tucked penis. "He knows this wasn't made for a woman, that even though he likes to do it, he knows it doesn't belong inside a woman."

"Emily," I mumbled, my legs buckling.

"He knows whatever he was born, he isn't a man and will never be a man and that's why he gets so excited seeing his lover flirt with a man.

I exhaled shakily. "That's…that's what I felt. Watching you. The jealousy. The heat. The way it made me feel even softer."

"I know," she said. "That's why I sat him next to me. That's why I leaned in. That's why I let him look. I wanted you to feel it. All of it. The inadequacy. The shame. The way it turns into something else when you know you're still the one I'm taking home."

She guided me toward the bedroom, still in the full set of lingerie, still soft and carefully composed under her hands. Once we were inside she sat on the edge of the bed and pulled me to stand between her knees.

"You asked what I saw in you," she said, looking up. "I saw the boy who would wear this for me. Who would let me dress him up and send him into a room full of people who have no idea. Who would watch me flirt with a real man and still come home soft and tucked and aching. Wishing he could be inside me but knowing that's not his place. Mark can want me. He can stare. He can imagine bending me over whatever surface he likes. But you're the one in the lace. You're the one who knows exactly how soft he is. And you're the one I chose."

Her fingers hooked into the waistband of the panties, tugging them down just enough to free me.

"Now tell me," she said, voice low and warm, "what it felt like. Every time he looked at my tits. Every time I smiled at him. Tell me how soft it made you feel."

I did. Standing there in the rest of the lingerie, stockings still clipped to the garter belt, I told her everything, the tight band of jealousy around my ribs, the way it sank lower and pressed against the nylon, the shame of knowing I could never take her the way he would, the strange, burning pleasure of remaining her pretty little secret while the rest of the room watched her walk out with me.

She listened, smiling that same small, knowing smile, and when I finished she pulled me down onto the bed with her."Good boy," she whispered against my mouth. 

"That's exactly why I picked you," she said.

"Emily..." I was out of the panties, exposed, swollen. "Can I...can we..."

"Does it belong inside a woman?" She asked.

"N...no," I said.

She climbed on top of me, trapped me against her body, against her wet pussy. "Then you have your answer," she said.

"But I...we...you let me...sometimes," I said.

"Who belongs inside a woman?" she asked.

"M...men," I managed to say.

"Men like Mark?" she asked. "Someone who turn women into jelly?"

"Yes," I moaned softly as I felt her wet pussy against me. 

"Someone a woman can actually feel inside her?"

"Emily..."

"Someone who doesn't squirt just being around a woman?"

Her word sounded cruel and maybe they were but they were words I needed to hear, words the hurt but words that reinforced the truth of what I am.

"He's never looked at me like that before," she said. "I mean he's looked, but never like that, never with such hungry, I want to fuck you eyes."

"I...I saw him," I said.

"I know," she said, "and you were such a good boy. Sitting quietly across the room, letting me have my space, letting me flirt with him, knowing your place."

"I...I felt so...so emasculated," I said.

"Of course you did, which was the whole point.

"I just felt like...like I wasn't supposed to...like my place was to..."

"Watch," she finished for me, voice soft but certain. She rocked her hips once, slow, letting the wet heat of her drag along the length of me without letting me inside. "To sit there in your pretty things and watch a real man want me. To feel every inch of how soft you are while he looked at me like that.

"I nodded, throat tight. "Yes. I kept thinking…he could take you. Right there if he wanted. And I couldn't stop him. I wouldn't even try. I'd just…stay soft and tucked and let it happen."

Emily's smile turned warmer, almost proud. "That's exactly what I felt from across the room. Every time I leaned forward and let him look, I could feel you watching. Feel how small it made you. How hard it made you in your pretty lingerie." Her fingers traced the edge of a stocking top, then drifted higher to rest over my heart. "I liked it. I liked knowing the only one in that room who actually gets to touch me is the one who knows he doesn't belong inside me."

I swallowed. The words hurt the way they always did. They were sharp and precise, but still they made me pulse against her. "It felt like…like I was less. Like the secretaries were right. Soft. Not really a man at all. And watching him stare at your breasts, hearing him talk about bending you over a table…it just confirmed it. I wanted to be angry. I wanted to be jealous the normal way. But all I could feel was how perfect the lingerie felt and how right it was that I was the one sitting three tables away in panties."

She leaned down and kissed the corner of my mouth, gentle. "Good. That's what I wanted you to feel. Because I felt powerful. Desired. Wanted by someone who would actually fuck me the way a woman like me is supposed to be fucked. And at the same time I felt…chosen. By you. The boy who would wear everything I picked out and still come home with me. Who would let me put Mark next to me just so I could watch the jealousy turn you softer, make you feel more vulnerable, more feminine, mine."

Her hips moved again, a slow, teasing slide. "I kept glancing at you on purpose. Every time his eyes dropped I looked for yours. I wanted to see the shame on your face. The way you swallowed. The way you sat so carefully so no one would notice the outline of the garter belt. It made me wetter than anything he said."

I exhaled shakily. "I was so excited it hurt. And so soft at the same time. Like my body knew it wasn't allowed to be anything else. Like the only thing that made sense was staying tucked and pretty while you let him want you."

Emily's voice dropped lower, intimate. "That's why I chose you. Not in spite of the softness because of it. I've no doubt Mark could make my legs turn jelly, other men like him obviously have. He can take what he wants and leave a woman aching in the good way. But he can't give me this." She pressed down just enough that the head of me kissed her entrance without entering. "This quiet, perfect little girl pretending to be a boy, who knows exactly what he is and still gets so excited from watching me be wanted by someone else. Who will look me in the eye and admit his place is not inside me."

I trembled under her. "I…I still want it. Even knowing. I still want to be inside you sometimes."

"I know you do," she murmured, almost tender. "And sometimes I let you. Because it's sweet. Because it makes you feel even smaller afterward. But not tonight." She lifted slightly, denying even that brief contact. "Tonight you stay outside where you belong. You tell me how it felt every time he looked. You thank me for letting him sit so close. And then you stay right here, pretty and and aching, while I decide whether you get to squirt or not."

I nodded, eyes stinging a little, small penis held uselessly against her thigh. "Thank you. For letting him sit next to you. For leaning in. For making me watch. It…it made me feel exactly what I am."

She smiled, kissed me properly this time, slow and claiming. "My pretty little secret. My soft boy in lace. That's why I picked you. And that's why you're the only one I brought home."