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Stunning Transsexual Boss's First Time Threesome

Boss's first threesome with her eager male intern and her hung best friend.

9 min read November 13, 2026New

Reid had asked first, and Joanna had made him say it where she could hear every word.

She was thirty-four, a stunning executive who had wanted for years to fuck and be fucked in the same night, with a man and with a woman. Reid was twenty-two, an intern whose reviews belonged to the program director and not to her. Weeks of office banter had been mutual, his jokes as bold as hers once the floor emptied. In the garage she had drawn the line in plain speech: if he wanted her home, he had to ask; if he never asked, his file would not move; if he came and changed his mind, he could leave and the internship would stay exactly what it was.

He asked that night. The text still glowed on her phone. I want your place. I want to fuck you and I want you to fuck me. If Petra is willing, I want her too. I'll wear sweats I can lose fast because I want them off. Only if you want me there.

Petra, twenty-eight, Joanna's gorgeous best friend and as much a woman as Joanna was, had read it over her shoulder and said yes out loud. They wrote back together. Come if you mean it. Petra is in. This is not work. Turn the car around and tomorrow at the office will not feel it. We stop the second anyone says stop.

His answer was one word. Coming.

Petra waited in the bedroom in sheer black lingerie, the fabric cupping the heavy line of her cock, listening for the door. Every yes had already been spoken in the thread: lingerie, oral, anal, a first threesome, no surprises, no orders. Her skin prickled with the simple fact of being wanted.

The bell rang. Joanna opened the door in a smoke-colored robe, legs bare. Reid stood flushed in gray sweats and a thin shirt, already hard enough to tent the cotton. He looked at her eyes before her body.

"Still your choice," she said.

"Still mine," he said. "I drove here for your cock and for mine in you. Petra too, if she still wants me. Nothing about the internship got me in this elevator."

"I still want you," Petra called, not yet in the room. "I'll wait until you say my name."

"I want you in it," Reid said.

Joanna kissed him, and he kissed her back like the answer had been living in his mouth all week.

She walked him to the wide couch and sat, robe falling open around the thick, flushed length of her cock. Reid dropped to his knees because he wanted to, sweats shoved to his thighs, his own cock bobbing free, wet at the tip.

"Tell me," she said.

"I want your cock in my mouth," he said. "Slow. I want you to talk while I do it. I want Petra to walk in and see me like this."

"Then take it."

He wrapped his lips around her and sank down, tongue pressed flat, tasting salt and skin. Joanna's head tipped back. She fed him inch by inch, one hand in his hair, never pushing past what he took. He moaned around her and reached between his own legs, stroking himself while he worshipped her.

"Petra's going to come in wearing the same sheer set I have under this robe," Joanna said, voice rough. "Matching lingerie. She's going to put that pretty cock against your mouth and then we're going to open you up. You still want your ass fucked tonight?"

He pulled off, spit shining on his chin. "Yes. I want you in my ass. I want her mouth on me while you do it. Don't stop talking."

She turned him and bent him over the couch arm, still in the sweatpants tangled at his ankles, and slicked two fingers with lube from the side table. "Color if you need out. Green if you want more."

"Green," he said, and pushed back onto her fingers.

She worked him open with slow, filthy patience, crooking until his thighs shook, then replaced her fingers with her tongue, licking the rim while her free hand stroked his cock. He cursed, rocking, dripping onto the upholstery. She slid a finger back in beside her tongue and he sobbed a yes.

"Petra," Joanna called, mouth wet against him. "He said your name. Come in if you still want this."

Heels clicked. Petra stepped into the light in exquisite black lingerie that matched the set Joanna shrugged out of the robe to reveal: sheer bra, tiny panties strained over a hard cock, garter straps framing long thighs. She was stunning, lipstick dark, eyes hungry.

"Jesus," Reid breathed. "You're both—yes. I want both of you. Come here."

"Say it again," Petra said, smiling, already close enough that he could smell her perfume.

"I want the three of us. First time. I want your mouths, your cocks, your asses. I want to be fucked and I want to fuck. Green."

"Green," Joanna said.

"Green," Petra said.

They stripped him the rest of the way and let him peel their panties aside rather than off, cocks springing free against matching sheer. Hands and mouths found skin at once. Petra kissed him deep while Joanna sucked the head of his cock, then they traded, Petra swallowing him while Joanna offered her own cock to his mouth again. He licked Petra's balls while she stroked Joanna, and Joanna bent to mouth Petra's shaft until all three of them were panting, lingerie crooked, consent spoken between every new touch.

"Couch," Joanna said. "Doggy. I fuck him. Petra, his cock, if he wants your mouth."

"I want her mouth," Reid said, already climbing up, ass presented, hole shining. "Fuck me. Don't be gentle unless I ask."

Joanna lined up and pushed in, slow through the first thick inch, then deeper when he groaned and shoved back. She seated herself to the base and held, feeling him flutter and grip. Petra knelt in front of him, lingerie straps biting her hips, and took his cock into her throat as Joanna started to thrust.

The rhythm locked. Joanna's hips slapped his ass, her cock dragging over the spot that made him shake, while Petra sucked him wet and loud, hand twisting at the base, eyes up to watch his face come apart. Reid's voice broke into filth.

"Harder. Fuck my ass. Petra, don't you dare stop. I can feel both of you. God, her cock is so deep."

"Take it," Joanna snarled, gripping his hips, pounding now, balls swinging against him. "Pretty intern hole, squeezing me like you were built for it. You asked for this cock. Milk it."

"I asked," he gasped. "I want it. Petra, your mouth—I'm close—"

"Not yet," Petra said, pulling off with a filthy slurp, stroking him just shy of the edge. "Switch. I want to watch him fuck you."

They moved without losing the heat. Joanna lay back on the wide couch, lingerie bra still on, legs spread, hole already slick from the plug she had worn while she waited and then worked out with two fingers while Reid watched and nodded. "In me," she said. "Missionary. I want to feel you come close and not yet. Petra, my mouth. Sit if you want it."

"I want your tongue," Petra said, and straddled Joanna's face, sheer panties yanked aside, cock heavy against Joanna's lips.

Reid pushed into Joanna's tight hole and swore. She was hot and clutching, and she moaned around Petra's cock as he bottomed out. He fucked her in long strokes, watching Petra rock on Joanna's mouth, Joanna's throat working, mascara perfect, hands gripping Petra's thighs in welcome. Petra reached down and stroked Joanna's spit-wet cock in time with Reid's thrusts.

"Look at you," Petra panted. "Getting fucked while you suck me. Our first time and you're already greedy."

Joanna pulled off just long enough to say, "Deeper, Reid. I want it. Petra, feed me. Green, both of you."

"Green," Reid said, and drove in harder, the wet sound obscene.

"Green," Petra said, and slid back onto Joanna's tongue, then into her mouth, fucking her face in shallow, careful thrusts Joanna met with hungry pulls.

They rotated again when Joanna tapped Petra's thigh, a signal they had agreed on: pause, speak, move. Petra swung off. Reid pulled out shining. Joanna stood, cock dripping, and bent Petra over the couch arm, lingerie garters framing the ass she wanted.

"My turn to fuck you," Joanna said. "Reid, her mouth, if she wants your cock back."

"I want it," Petra said, cheek against the cushion, looking back. "Fuck my ass, Joanna. Reid, get in my throat. I want to be used by both of you. I asked for this."

Joanna slicked her cock and pressed in. Petra opened around her with a broken, delighted sound, pushing back until Joanna was buried. Reid stepped in front and Petra swallowed him to the root, gagging softly and staying there because she chose to, eyes watering, hand signaling a thumbs-up they had set as yes. Joanna fucked her in deep, grinding strokes, one hand on Petra's hip, the other reaching under to stroke Petra's cock where it swung and leaked.

"Spit-roast her," Reid groaned. "God, Petra, your mouth. Joanna, I can see your cock moving in her."

"Then look," Joanna said. "She's taking me so well. Our first threesome and she's already dripping on the floor."

They switched until the room blurred with sweat. Reid on his back, both women in crooked lingerie kneeling over him, double oral on Joanna while he sucked Petra, then the reverse, his mouth stretched around Joanna's cock while Petra and Joanna kissed and stroked him together. Joanna bent him over again and fucked his ass while Petra licked his cock from below, their mouths meeting around him when Joanna leaned down. Petra took Reid's cock in her ass, slow and vocal, yes and harder and don't stop, while Joanna stood beside them and fed her cock into Petra's mouth, then into Reid's, trading holes and lips until spit shone on all three chins.

"Both of you on me," Joanna ordered, and they obeyed because they wanted to, dropping to their knees in ruined sheer sets to suck her together, tongues sliding along her shaft, kissing each other around the head, Reid's fingers in her ass while Petra stroked her balls. Joanna's thighs trembled.

"I'm going to come," she warned. "Where?"

"On our faces," Petra said.

"On our tongues," Reid said. "Then I want to come in Petra while you watch, and I want you to make her come on me. All of it. We said yes."

Joanna stroked herself between their open mouths and came in thick pulses, striping Reid's lips and Petra's cheek, the rest caught on their tongues as they lapped her clean and kissed the mess between them. She was still twitching when she pushed Petra onto her back, lingerie askew, and guided Reid into Petra's hole.

"Fuck her," Joanna said, breathless. "I'll take her cock in my mouth. Come when she does if you can."

Reid drove into Petra and Joanna swallowed Petra's cock, sucking hard, hand working what her mouth could not hold. Petra came first, crying out, spilling down Joanna's throat in hot jolts, ass clenching around Reid until he lost it and flooded her, hips jerking, groan ripped out of him. Joanna pulled off, face a wreck of lipstick and cum, and stroked herself back to a second, sharper orgasm across Petra's stomach and Reid's softening cock, marking both of them while they shook through the aftershocks.

They collapsed in a tangle on the couch, lingerie twisted, straps snapped, skin slick with sweat and streaked with cum. Lazy kisses passed the taste around. Joanna laughed, filthy and satisfied, one hand still wrapped around Reid's spent cock, the other cupping Petra's sticky shaft.

"First threesome," she said. "I fucked his ass and he fucked mine. I took Petra and she took both of us. Exactly the night I wanted, top and bottom, and you two begged for every inch."

Reid licked a stripe of her cum off Petra's collarbone and grinned. "Worth the drive. I'd get on my knees in this wrecked lingerie again before the sweat even dries."

Petra dragged Joanna's fingers through the mess on her stomach and pushed them into Reid's mouth, then her own, sharing it. "Good. Because I'm not done being full of him, and I want your cock back in my ass while he watches and gets hard again."

Joanna spread Petra's thighs, pressed the head of her still-slick cock to that used, dripping hole, and sank back in to the base while Reid stroked himself awake beside them.

"Open up and take it," Joanna growled. "Both of you are going to stay sloppy, stuffed, and dripping with my cum until none of you can walk."

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