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College Head Interviews Blonde Transsexual Assistant

A college head hires his eager blonde transsexual assistant after a very thorough office fuck.

13 min read November 12, 2026New

The late afternoon light cut through the blinds of Barrett’s campus office and laid thin gold bars across the polished desk. At forty-five, the college head still carried the shoulders of a man who had rowed in his younger years, and the charcoal suit he wore for interviews fit him like a decision already made. The assistant position had sat open for three weeks. Résumés stacked beside his elbow, each one competent and forgettable, until the door opened and Joanna walked in.

She was twenty-two, and she moved like she knew exactly what that looked like on her. Blonde hair fell in a sleek sheet past her shoulders. The tiny black skirt barely covered the tops of her thighs. Sheer black stockings caught the light along her long legs, and the sky-high heels clicked once on the hardwood before she crossed the rug and stopped in front of his desk. Her white blouse was open at the throat just enough to show the hollow there. She smiled, warm and deliberate and entirely adult.

“Joanna,” she said, offering her hand. “I’m here for the assistant interview.”

Barrett stood. Her fingers were cool and sure in his. He felt the heat of her palm a second later and sat again a little slower than he meant to. “Please. Sit.”

She did, crossing one stockinged leg over the other so the skirt rode higher. The sheer nylon whispered. He kept his eyes on her face for as long as he could manage.

They went through the formal questions. Hours she could work. Software she knew. How she handled a crowded calendar and a difficult faculty meeting. Joanna answered in a low, clear voice, and every time she shifted, the skirt climbed another fraction. She uncrossed her legs, recrossed them the other way, and let one heel dangle from her toes before sliding it back on. The black stocking seam ran straight up the back of her calf. Barrett’s pen stopped moving.

“I want this job,” she said, meeting his eyes without blinking. “I read the posting twice. I know what an assistant to the college head actually does, and I know I’m good at it. I’m also not going to pretend I don’t notice the way you’re looking at me.”

The air in the office thickened. Barrett set the pen down. His pulse had moved into his throat. “And how am I looking at you?”

“Like a man who wants to see what happens if I uncross my legs and leave them that way.” She did it. The skirt barely held. Sheer black nylon, the pale skin above the stocking tops, the promise of more. “I’m twenty-two. You’re the head of this college. This is a professional interview. And I am still going to tell you that I will do whatever it takes to secure the position. Including things that aren’t on the job description. If you want that. If you want me.”

Barrett’s hands flattened on the desk. The attraction was immediate and mutual and no longer hiding behind the interview script. “That’s a dangerous thing to say in this office.”

“Only if you don’t want to hear it.” Her heel tapped once against the chair leg. A slow, teasing drag of nylon against nylon followed as she shifted again, letting him watch the muscle in her thigh. “Do you?”

He held her gaze. The formal interview was still technically happening. Both of them knew it had already become something else. Heat sat low in his gut, unmistakable, and the way her mouth curved said she felt the same pull and had no interest in pretending otherwise. “Keep talking,” he said. “I’m listening.”

Joanna stood. The movement was unhurried, a slow unfurling of those long legs in the sky-high heels. She turned, presenting her back, and the tiny skirt stretched across the curve of her ass. She looked over her shoulder, blonde hair sliding, and let him look for a long moment. The stockings ended high. The heels made her calves taut and elegant. She smoothed the skirt with both hands, not to cover herself but to show him the shape underneath, palms lingering, then turned again and came around the desk with that same deliberate click of heels.

She dropped to her knees on the rug between his chair and the drawers. The heels tucked neatly under her. From this close he could smell her perfume, something clean and warm, and see the faint sheen of the stockings where they caught the light along her thighs.

“I desire the position,” she said, voice steady and clear. “And I desire your cock. Both. I’m not confused about either one. I’m not offering this because I have to. I’m offering it because I want you, and I want the job, and I want you to know exactly what you’re getting if you hire me. If you want me to stop, say so now. If you want me to keep going, tell me.”

Barrett’s erection was already obvious against his suit pants, a thick ridge he no longer bothered to hide. He looked at her kneeling there, beautiful and certain, twenty-two and radiant in that tiny skirt and those sheer black stockings, and felt the last of his professional reserve give way. “I want you to keep going. I consent. Eagerly. God, Joanna. Yes.”

Her hands found him through the fabric. She stroked the length of him with a slow, measuring palm, feeling how hard he already was, tracing him from base to tip until his breath caught. A small satisfied sound left her throat. “There you are. I knew you’d be thick.”

He reached for her. She rose into the kiss without leaving her knees entirely, then stood into his arms as he pulled her up. Their mouths met hard. Her lipstick tasted faintly sweet. His hands slid down her back and cupped her ass through the thin skirt, squeezing, and she pressed into him, grinding once so he felt the unmistakable heat and hardness of her own cock against his thigh.

“I want to fuck you,” she said against his mouth, breathless and honest. “And I want you to fuck me. Right here. On this desk. In this office. Say you want it too.”

“I want it,” Barrett said. His voice had gone rough. He kissed her again, deeper, one hand in her blonde hair. “I want to fuck you. I want your mouth. I want your ass. I want you inside me. All of it. Take the clothes off. I need to see you.”

They undressed each other between kisses that kept breaking into words. His jacket hit the chair. Her blouse opened button by button under his fingers, revealing a black bra and the smooth warm skin of her stomach, which he kissed as he went. She worked his belt loose, then his zipper, and pushed his pants and boxers down together. His cock sprang free, thick and flushed, and she wrapped her hand around it with a pleased little sigh, stroking him slow while she looked up into his face.

“You’re gorgeous,” she murmured. “I want this in my mouth. I want it in my ass. I want to watch your face when I take you.”

He shoved the tiny skirt up rather than off at first, greedy for the sight of the stockings and the thin black garter straps and the panties stretched over the clear shape of her cock. Then the panties came down her long legs. She stepped out of them and left the heels and the stockings on, because he asked her to with his eyes and then with his mouth against her throat. Her cock was beautiful, smooth and already hard, and when he wrapped his hand around it she moaned into his shoulder and rocked into his fist.

“Look at you,” he said, stroking her while she stroked him, both of them shaking a little with how badly they wanted this. “Twenty-two and walking into my office dressed like that, teasing me through a whole interview. I’m forty-five and I’m harder than I’ve been in years. I want to fuck you until you can’t sit still in that chair.”

“Good,” Joanna said, kissing him again, open and hungry, her tongue sliding against his. “Then fuck me like you mean to hire me. And let me fuck you like I mean to stay. I want every inch of you, Barrett. Right now.”

She sank back to her knees without being asked, the sky-high heels braced on the rug, and took him into her mouth with a slow, worshipful slide. Barrett’s hand found the edge of the desk. Her lips were soft and hot, her tongue flattening under the head before she sank deeper, taking him until her nose brushed the trimmed hair at his base. She held there, throat working, eyes lifted to his, and the sight of that beautiful blonde face so eager around his cock made his knees threaten to buckle.

“Fuck,” he breathed. “Just like that. Don’t rush it. Let me feel your mouth.”

Joanna hummed and obeyed, pulling back only to lick him from root to tip, teasing the slit with the point of her tongue, then swallowing him again in a long, wet glide. Spit shone on her lips. She stroked what she couldn’t hold and sucked what she could, cheeks hollowing, one hand cupping his balls and rolling them gently while the other braced on his thigh. Every time he groaned she did it again, slower, deeper, as if the sound itself was something she wanted to taste. She pulled off just long enough to speak, voice husky.

“You taste so good. I could stay on my knees for you all afternoon. But I want more than your cock in my throat. I want you to bend me over this desk and fuck my ass. I’ve been thinking about it since I walked in. Tell me you want that.”

“I want that,” Barrett said, already reaching for her. “Stand up. Bend over. Keep the heels and the stockings on. I want to see them while I’m inside you.”

She rose, turned, and folded herself over the polished wood, cheek against a folder, tiny skirt bunched at her waist. The sheer black stockings framed the pale curves of her ass. Barrett opened the bottom drawer where he kept a small bottle of lubricant he had never expected to use in an interview, slicked his fingers, and pressed one carefully against her tight hole. She pushed back onto it with a needy sound.

“Yes. More. I’m ready for you. I want it. Please fuck me.”

He worked a second finger in, then a third, stretching her open while she moaned and rocked, her own cock hanging hard between her thighs, dripping onto the rug. When she was slick and open and begging in a broken voice, he lined himself up and pushed the head of his cock into her ass. The heat of her clenched around him. He went slow, inch by inch, one hand on her hip and the other spread between her shoulder blades, until he was buried to the hilt and both of them were shaking.

“God, you’re tight,” he growled. “So tight around me. You feel incredible.”

“Move,” Joanna gasped. “Fuck me. Don’t be gentle now. I can take it. I want to feel you tomorrow when I sit at that desk outside your door.”

He drew back and thrust in again, harder, the slap of his hips against her ass filling the quiet office. Doggy style over the desk, her heels planted, her blonde hair spilling across the wood, she took every stroke and asked for more. He reached under her and stroked her cock in time with his thrusts, and she cried out, pushing back to meet him, filthy and eager.

“Harder. Right there. Fill my ass. I want the whole college to wonder why their new assistant can’t walk straight, and I want you to be the only one who knows.”

“You want this job that badly?” he said, fucking her deeper, the desk creaking under them.

“I want the job and I want your cock,” she moaned. “Both. Don’t stop. Don’t you dare stop.”

He pounded her until his control frayed, then pulled out with a ragged breath, cock gleaming. “Your turn. I want you inside me. I want to know what that feels like with you.”

Joanna’s eyes went dark with pleasure. She straightened, still in the heels and the ruined skirt and the black stockings, and kissed him hard while she slicked her own cock with the same lubricant. Barrett bent over the desk in her place, pants around his ankles, heart hammering. She pressed against him, the head of her cock nudging his hole, and waited.

“Tell me,” she said. “I need to hear you want it.”

“I want it. Fuck my ass. Fuck me hard. I consent. I need you in me.”

She pushed in slowly at first, letting him adjust, one hand stroking his back, murmuring praise. When he groaned and pushed back, she sank the rest of the way and held still, buried deep, both of them panting. Then she began to move. Long strokes at first, then harder, her hips snapping, the heels giving her leverage as she fucked him over his own desk. Barrett stroked himself in a tight fist, the dual sensation overwhelming, her cock hitting him just right while his own throbbed in his hand.

“Look at you,” she teased, voice warm and filthy. “College head bent over his desk, taking my cock like you were made for it. You feel so good around me. So hot. I’m going to fuck you until you beg, and then you’re going to put me on my back and finish in my ass. Deal?”

“Deal,” he managed, stroking faster. “God, Joanna. You’re perfect. Don’t stop. Fuck me. Just like that.”

She did, relentless and careful at once, one hand wrapped around his hip, the other sliding up to grip his shoulder. The office filled with the sound of skin and breath and the low, desperate things they said to each other. When Barrett’s thighs started to shake she eased out, turned him, and let him take her again.

He lifted her onto the desk, swept a stack of résumés aside, and laid her back among the scattered papers. Missionary, her long legs in the sheer black stockings hooked over his arms, the sky-high heels framing his ribs. He pushed back into her ass in one smooth thrust and she arched, mouth open, blonde hair fanned across the wood.

“Yes. Yes. Fuck me. Fill me up. I want to feel you come inside me.”

“Not until you do,” he said, and wrapped his hand around her cock again, stroking her in rhythm with every deep thrust. “I want to watch you. I want to see that beautiful face when you lose it. Come for me, Joanna. Come while I’m fucking your tight ass.”

She met his eyes, teasing even now, biting her lip, rolling her hips to take him deeper. “You first. No. Together. I want us together. Harder. Talk to me. Tell me I’m hired. Tell me you’re going to keep fucking me in this office until I know every inch of this desk.”

“You’re hired if you want it,” he groaned, pounding into her, the desk thumping the wall. “You’re mine in this office. My assistant. My gorgeous girl. Take it. Take my cock. I’m close. I’m so close.”

“Me too. Don’t stop. Don’t stop. Barrett—”

Her cock pulsed in his fist and she came with a sharp, helpless cry, thick streaks painting her stomach and his wrist, her ass clenching around him in rhythmic waves. The tightness dragged him over the edge. He drove in deep and came hard, spilling inside her, hips jerking, a rough sound torn out of his chest as he emptied himself. They stayed locked together through the aftershocks, gasping, her heels still hooked behind him, his forehead dropped to her shoulder, both of them shaking and grinning like people who had just gotten exactly what they wanted.

When he could move again he eased out of her, careful, and she sat up on the edge of the desk, flushed and radiant, cum shining on her skin. She reached for him with a satisfied smile, slid off the desk onto those sky-high heels, and sank gracefully to her knees one more time. Her mouth closed around his softening cock, warm and gentle, cleaning him with slow, thorough licks, tasting both of them, humming softly until he was clean and shivering. She kissed the tip, then rose.

Joanna found her panties, stepped into them, and smoothed the tiny black skirt back down over the sheer stockings. She checked the seams, adjusted a garter strap, buttoned her blouse, and ran her fingers through her blonde hair until she looked almost as composed as she had walking in, only brighter, a little wrecked around the mouth. Then she sat back down in the chair across from him, crossed her legs, and waited.

Barrett dressed with less grace, tucking himself away, straightening his tie with hands that still trembled. He looked at her across the desk, at the woman who had teased him through an interview and then fucked him until he forgot the questions, and felt the decision settle cleanly.

“The position is yours,” he said. “Assistant to the college head. Starting Monday. If you still want it.”

Joanna’s smile was slow and satisfied. “I want it. I accept.”

“And this,” he added, glancing at the desk, at the rug, at the heels still crossed at her ankle. “We continue this. Regularly. Here. When the door is locked and the work is done. Or before. Whenever we both want it.”

“Agreed,” she said. She uncrossed her legs, let him see the stockings one more time, and recrossed them with deliberate care. Already she was scheming the next time, turning over the calendar in her head, the late afternoons when his schedule went quiet and she could lock the outer door, kick those heels off or keep them on, bend him over the desk again or ride him in his chair until the blinds rattled. Monday, she thought, smiling at him across the scattered résumés. Monday she would wear the same skirt, the same sheer black stockings, and she would make sure he remembered exactly why he had hired her.

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