Jim is happily married to Pamela. But he hides a little secret: he's always been attracted to transsexuals with large penises. Jim has always managed to keep these fantasies separate from his reality. That is, until a new colleague came to work at his company: Kate. Word spreads among his colleagues that Kate is transgender. This intrigues Jim, who has never met one personally.

Chapter 11: The crossdressing

Once I get home, I put on some comfortable clothes. I put on a pair of very tight leggings and a t-shirt. Then, my usual apron, and I start preparing dinner for my women.

Lucy, my little princess, is already tucked into her bed, her favorite stuffed bunny clutched tightly in her arms. She's been chattering about her new friend Kate all day, and it warms my heart to see her so happy.

I hear the front door open, and soon the sweet smell of perfume fills the air as Pamela and Kate enter the house. They're laughing about something, their heads close together in a private joke that only they understand. It's moments like these that make me fall in love with them all over again.

Seeing Pamela and Kate together, their laughter and banter so natural and easy, reminds me why I chose to embrace this unconventional life. I slip into the kitchen, the sound of their voices guiding me.

"You two are insufferable," I say, a playful grin on my face as I enter the kitchen. Pamela and Kate both turn to look at me, their faces flushed with laughter.

"Jim! You're home early," Pamela says, her eyes shining with happiness. She walks over to me, wrapping her arms around my waist and pulling me into a hug.

"I'm glad you're here," she murmurs into my chest.

I hug her back, breathing in her familiar scent, a mix of her signature perfume and the faint aroma of the coffee shop where she works. "Me too, Pam. Me too."

Kate approaches us, a warm smile on her face. "Welcome home, Jim. How was your day?"

I pull back from Pamela's embrace and turn to face Kate, taking her hand in mine. "It was good. Exhausting, but good. How about you two? What have you been up to?"

Pamela grins mischievously.

"We've been plotting world domination, of course. What else could two gorgeous women be up to?" she teases, playfully batting her eyelashes at Kate.

Kate rolls her eyes dramatically. "Oh, please. You know we've just been working on the business plan for the bookstore. That's all."

I chuckle, shaking my head. "Sounds like some serious 'plotting' to me. I'm excited to see what you two come up with. The bookstore is going to be amazing."

Pamela beams at me, her eyes shining with pride. "We have big plans.

It's going to be the best bookstore this town has ever seen," Pamela says, her voice filled with determination. She turns to Kate, her eyes sparkling with excitement. "And we're going to make sure it's the most inclusive and welcoming space possible. A place where everyone feels seen and heard."

Kate nods in agreement, her eyes shining with the same passion. "That's right. We're going to have a section dedicated to LGBTQ+ authors and books. A safe space for everyone to explore and discover new stories."

I can't help but feel a swell of pride and love for these two women.

Then Pamela notices my outfit and how the leggings accentuate the femininity of my legs and the firmness of my butt. “Is Lucy sleeping, Jim?” Pamela asks, her eyes taking in my apron and leggings, a small smile playing at the corners of her mouth.

“Yes, she is,” I reply, noticing the direction of her gaze. “Why, do you like what you see?” I tease, a playful smirk on my face.

Pamela’s smile grows, and she reaches out to stroke my cheek. “Always, Jim. I love you no matter what you’re wearing, but I must admit, I have a special fondness for your leggings. They show off your assets nicely,” she says, her voice low and sultry.

“I’ve always loved seeing you in them.”

“Well, I aim to please,” I say with a wink, giving her a quick peck on the lips.

Kate chuckles, looking back and forth between us. “You two are something else, you know that? Always flirting and playing around, even after all this time.”

“What can I say?” I grin. “I’m just a sucker for these two beautiful women.”

Anyway, I have enough holes for both of us.

It’s time to get down to business, Jim," Pamela said, eagerly rubbing her hands together as she sat down at the table.

Jim's eyes lingered on Pamela's hands for a moment before he turned to Kate, who was still standing by the counter, a playful smile on her face.

Then Pamela hands me a bag containing some women's underwear. "A gift for you." There's also a dress and a pair of red shoes. I look at her questioningly, but my heart starts beating faster and faster.

"Pam, what... what's this for?" I ask, trying to sound casual, but my voice betrays my excitement.

Pamela's smile widens, and she pats the chair next to her. "Come on, sit down. Kate and I have a little surprise for you."

Kate grins and walks over to the fridge, pulling out a bottle of wine. "I think it's time we celebrated our new business venture," she says, pouring three glasses.

I sit down next to Pamela, my heart pounding with anticipation. "What are you two planning?" I ask, taking the glass of wine from Kate.

Pamela reaches into the bag and pulls out the red dress. It's a beautiful, form-fitting number that hugs the curves in all the right places. My eyes widen as she holds it up, and I can't help but feel a thrill of excitement. "What's this for?" I ask again, my voice barely above a whisper.

Kate smiles, handing me the underwear and the shoes. "Well, Jim, we've been thinking. We want to take this bookstore venture to the next level, and we thought, what better way to promote it than with a little...

exhibition?" Kate finishes, her eyes sparkling with a mix of mischief and excitement.

I swallow hard, my heart racing in my chest. "Exhibition? You mean... like, a public display?" I ask, my voice barely above a whisper.

Pamela nods, her eyes gleaming with anticipation. We want to make a splash with our grand opening, and we think this will certainly grab some attention."

I look at the dress in Pamela's hand, my mind racing with possibilities and fears. "But... I don't know if I can do that. What if someone recognizes me?

What if people judge me? What if they think I'm some kind of... freak?" I stammer, my voice barely above a whisper. I look up at Pamela and Kate, my eyes wide with fear and uncertainty.

Pamela takes my hand, her eyes soft and understanding. "Jim, we won't force you to do anything you're not comfortable with. But we think this could be a powerful way to celebrate who you are, to embrace your true self, and to show the world that there's nothing to be ashamed of.

"Let me see how I look. But if I look like a freak of nature, I'm out of the question." I go over there, put on silk stockings and lingerie over my laser-depilated body. Then I put on my dress. With my long hair, which I've had for a while, the Pilates exercises I do daily, and a light makeup, I look really good. I go back to the salon, after putting on my red high heels.

I have to admit, I look good. The dress hugs my curves in all the right places, making me feel confident and sexy. I take a deep breath, steeling myself for what's to come.

I step out of the bedroom, and Kate and Pamela both turn to look at me. Their jaws drop, and their eyes widen with surprise and appreciation.

"Wow," Kate breathes, his voice filled with awe. "You look... breathtaking, Kate."

Pamela nods in agreement, her eyes shining with unshed tears. "You're beautiful, Jim . Truly stunning," she whispers, her voice filled with emotion.

I take a deep breath, trying to calm the butterflies in my stomach. "So, what's the plan? How do you want me to...perform?"

Kate grins, her eyes sparkling with excitement. "Well, we thought it would be perfect if you could read a passage from one of our featured LGBTQ+ books. Something that really speaks to you, something that shows the world who you are and what this bookstore stands for."

I nod, my mind racing with the possibilities.

I've always loved reading, and the idea of sharing a passage that means something to me is both thrilling and terrifying.

"Which book did you have in mind?" I ask, trying to keep my voice steady.

Pamela smiles at me, her eyes shining with pride. "We thought you might like 'Fun Home' by Alison Bechdel. Her honest and raw portrayal of her own journey and the struggles she faced in coming to terms with her sexuality... it's powerful. And we think it would resonate with you, Jim."

I take a deep breath, the words already dancing on the tip of my tongue.

But before I can begin, Pamela reaches out and places a hand on my thigh, slowly sliding it up until her fingers brush against the lace of my underwear. I gasp, my body tensing at her touch, and Kate's eyes flash with desire.

"Fuck, you're gorgeous," Kate says, her voice like velvet. "You have no idea how hot it is to see you like this, to know that you're ours. That you're doing this for us, for our dream."

Pamela's fingers delve beneath the lace, stroking the dampening fabric of my panties.

"Fuck, you're gorgeous," Kate repeats, her voice thick with desire.

“My pregnant wife wants to fuck me with her big strap on?” Jim chuckles, her eyes gleaming with mischief. “Well, someone needs to fill your man pussy, and since you’re the one who got me all wet, I figure it’s only fair. Besides, I’ve been dreaming about fucking you for years, Jim., to fuck you dressed like a woman. It’s time to make that dream a reality.”

Pamela had already put on her strap-on and was watching Jim like a large carnivore studies the gazelle that had approached the waterhole to drink.

But she didn't want her husband to undress. God! How perfect he looked in that outfit that accentuated her ass and slim waist. She wanted to take him in his clothes. Like you take a woman during a quickie when you don't have the time or the means to undress. In that moment, she realised that, despite being a woman, she was a sexual predator towards Jim.

She approached him like a cat that had spotted its prey. Pamela's eyes were fixed on Jim's neck, where the shirt was slightly open and it was possible to see the Adam's apple moving up and down with his breath. She licked her lips, anticipating the taste of his skin.

Pamela leaned in, her breath hot on Jim's neck. She could feel his heart racing, his pulse pounding against her lips. She savored the moment, the scent of his cologne and the warmth of his skin filling her senses. Then, with a slow, deliberate motion, she ran her tongue along the length of his neck, tasting the salt of his sweat and the faint musk of his body.

Jim trembled under her touch, his breath hitching in his chest.

Pamela's hands roamed over his back, her fingers tracing the curve of his spine before moving to the zipper of his dress. She fumbled with the fastening, her fingers clumsy with anticipation, and finally, with a swift tug, she pulled it down, leaving Jim's body exposed.

Jim gasped as the cool air hit his bare skin, his nipples hardening into tight buds. He felt vulnerable, yet powerful, like a goddess on display. Pamela's eyes roamed over him, taking in every curve and line, her gaze lingering on the neatly trimmed hair on his chest and the firm muscles of his stomach.

"You're perfect," she murmured, her voice thick with desire.

Jim, swaying his hips mischievously, turns to his wife, biting his lower lip: “You say that because you love me, but look at me: I’m a mess with this ruined hairdo and the color of my nail polish that doesn’t match the color of my lingerie!” he laughs nervously.

Pamela, now completely aroused by her husband’s transformed appearance, steps closer, her breath hot on Jim’s cheek. “Don’t you dare say that,” she growls softly, her tongue darting out to flick at Jim’s earlobe. “You look hot as fuck, Jim. You look gorgeous, and I want to taste every inch of you.” She leans in, her mouth capturing Jim’s in a searing kiss, her tongue exploring the depths of his mouth.

Pamela trails kisses down Jim’s neck, her fingers tangling in his hair, and pausing at the base of his throat, she whispers, “You’re mine, Jim.

“You’re ours, Jim. Or rather, you two are mine, to be more precise.” Kate intervened, placing a hand on Pamela’s belly, even though the signs of pregnancy were far from visible.

“I impregnated your wife, and if nature allowed it, I would impregnate you too, and, dressed like that, you look quite the sweetheart. But I understand that Pamela has realized she shares my predilection for men who feel like women, and it's only right that she exercises her sacrosanct right to take what's hers. I only hope she'll share some of this bounty.” Kate continued.

"You belong to us, Jim. And we're going to enjoy every fucking inch of you tonight."

Jim shuddered with anticipation and desire, his body responding to their words and touches. He felt a wetness between his thighs, his panties already soaked through. He looked into Pamela's eyes, seeing the same hunger and lust reflected back at him.

"Yes," he whispered, his voice barely above a moan. "I'm yours. Take me, both of you."

Pamela grasped the strap-on, the base of it already well inserted into Pamela’s pussy. Her hand grabbing the girth of it aiming to his asshole. "This will be good, Jim," Pamela said, her voice husky and thick with desire. "Or, rather, do you prefer that I call you Samantha? We're going to make you feel so good."

"I can't wait," Jim said, his voice barely a whisper as his anticipation grew.

Pamela ran her fingers over the head of the strap-on, spreading some of the lube she had applied earlier. She then pressed the tip against Jim's asshole, and slowly, she began to push inside.

Jim gasped, his body tensing as he felt himself being filled. "Fuck, that's big," he said, his voice strained with the effort.

He tried to relax, knowing that resistance would only make it worse. He felt like he was being split in two, the pressure intense and overwhelming.

Pamela watched Jim's face, her own lips parted in a silent moan. "Shh, baby," she whispered, running her free hand through his hair. "You can take it. You're doing so good."

Kate, who had been watching from the side, stepped closer, her eyes hungry. "Let me help," she said, her voice low and husky. She reached out, her hand cupping Jim's balls through his panties, making him moan. "You feel so fucking good, Jim.

So tight and hot," Pamela groaned, her eyes locked on Jim's face as she slowly pushed the rest of the strap-on inside him. "I've dreamt of this moment for so long."

Jim panted, his body adjusting to the intrusion, the pain slowly subsiding into a strange mix of pleasure and discomfort. He looked up at Pamela, his eyes filled with tears and gratitude. "You feel so fucking big, Pam. Like you're filling me up completely."

Kate, who had been patiently waiting, stepped forward and kissed Jim deeply, her hand still cupping his balls. "You're so brave, Jim.

Taking it so well," Kate murmured, her lips brushing against Jim's as she broke the kiss. She looked into his eyes, seeing the mixture of pain and pleasure reflected back at her. "Let's make this even better for you, hmm?"

Pamela completely loses control seeing her husband dressed as a woman storm under her. "Move, shake that little ass for me! Take it all in my latex dick. How I would like to have a real one, just like Kat's. Do you know that, Jim? I've always wanted to have such a big dick! Since we started dating I've always liked your feminine way of treating me. But I never imagined you were such a whore!”

Pamela praises, her hand now freely exploring Jim’s body, squeezing and caressing his ass, his hips, his thighs. The sight of Jim’s helpless, vulnerable body makes her ache with desire and hunger.

Pamela moves closer, her latex-clad penis thrusting inside him.

“I’m fucking you, Jim,” Pamela growls, her voice thick with lust. “I’m fucking you hard and deep and you’re going to take every fucking inch of my cock.

You’re mine, Jim, all mine, and you’re going to feel me deep inside you, do you understand?” Pamela hissed, her eyes blazing with lust and desire.

Jim nodded, his eyes watering with tears of pain and pleasure. He clenched his teeth and whimpered as Pamela thrust her hips forward, filling him completely. He could feel every thick, veined inch of her strap-on cock, the latex stretching him wide and filling him completely.

“Good boy,” Pamela purred, her voice thick with desire. “You look so fucking hot like this, Jim. A real fucking slut for me and Kate.

And you're going to take it like a good little whore, aren't you, Jim?"

Jim whimpered, his body shuddering with each thrust. The pain was intense, but it was mixed with a pleasure so raw and primal that he couldn't get enough. He looked up at Pamela, his eyes filled with tears, and nodded.

"Yes, Pam. I'm yours. I'll take it all. Just... just fuck me, please," he begged, his voice hoarse with desire and pain.

Pamela grinned, her eyes gleaming with triumph. "That's what I wanted to hear, you little slut.

Now, let's see you move that ass like the whore you are," Pamela growls, gripping Jim's hips tighter as she begins to fuck him harder, her latex-clad cock slamming into him with a wet, smacking sound.

Jim grunts with each thrust, his body trembling with the effort of taking Pamela's massive cock. He grips the sheets beneath him, his knuckles turning white as he tries to brace himself against the onslaught. But Pamela is relentless, her hips moving like a piston as she pounds into him, claiming him as her own.

"You like that, don't you, slut? You like feeling my big cock fill you up, don't you?" she taunts, her voice harsh and raw.

Jim can only moan in response, his body on fire with a mix of pain and pleasure. His ass burns with every thrust, but he can feel his own cock, trapped in his panties, growing harder and leaking precum. He spreads his legs wider, trying to take more of Pamela's cock, desperate to feel every inch of her.

Kate, watching from the side, is turned on beyond belief.

She can't believe how hot Jim looks dressed like this, how eager he is to please, how much he's taking. She knows she has to join in, has to feel a part of this. She walks over to where Pamela is fucking Jim and presses her body against his back. "I want in on this too," she growls in his ear.

Jim turns his head to look at Kate, his eyes filled with desire and need. "Please, Kate," he begs. "Please help me take this. I need you both."

Kate smiles, her hand cupping Jim's ass cheek roughly.

Kate grabs a lock of hair behind the back of Jim's neck and forces him towards her cock. The move is sudden and instinctively Jim makes a gesture to move aff. But Kate keeps him in position by tightening her grip on his hair even more: "Where do you think you're going, slut? This is your place. Suck it! Use that mouth for what you do best!”

Kate snaps, her voice commanding as she guides Jim's head towards her crotch. Jim whimpers, but doesn't resist, his lips parting as they brush against the head of Kate's hard cock. He can taste the pre-cum leaking from the tip, and he eagerly licks it off, moaning at the salty taste.

Kate groans, her hips thrusting forward as Jim takes more of her cock into his mouth. "Fuck, you're good at this," she breathes, her voice thick with lust. Jim looks up at her, his eyes watering as he tries to take more of her length.

Kate pushes forward, and Jim's nose presses against the curly hair at the base of her cock. He gags, and Kate pulls back, letting him catch his breath.

"Relax, Jim," Kate says, running a hand through his hair. "Take it slow. You can take it all if you just relax."

Jim nods, taking a deep breath through his nose. He looks up at Kate, his eyes filled with desire and submission, and opens his mouth wide. Kate guides her cock back to his lips, and this time, Jim takes it all in, his nose pressing against her pubic hair.

Kate groans, her hips bucking instinctively.

"Fuck, Jim, you're a natural at this. You're making me feel so fucking good." She grips his hair tighter, urging him to take more of her cock.

Jim eagerly obliges, taking her deep into his throat, the sensation of being filled at both ends sending shockwaves of pleasure through his body. He can taste the saltiness of her precum, mixed with the lube and the faint tang of latex from Pamela's strap-on. He moans around Kate's cock, the vibrations sending a shiver through her body.

Pamela watches the scene unfold, her own arousal growing with each thrust.

"You know Jim? I think you passed the exam! From now on I'll call you Rose. At least when you're dressed like this to take our dicks. Right, Kate?”

Pamela urged, her breath ragged as she drove her latex-clad cock into Jim, her hips moving in a primal rhythm that sent shivers down his spine.

Jim tried to respond, but Kate's cock was filling his mouth, preventing any coherent words from escaping. He could only moan in agreement, the vibrations of his voice sending shudders through Kate's body.

“Fuck, that's so hot,” Kate groaned, her grip on Jim's hair tightening as she began to thrust his head back and forth on her cock.

“You look so fucking perfect, Rose. A real little slut, aren't you?”

Jim whimpered around Kate's cock, his eyes tearing up as he took her deep into his throat. The feeling of being filled, both mouth and ass, was overwhelming, and he could feel his own cock throbbing in time with the rhythm set by Pamela and Kate.

Pamela, feeling the change in Jim's body language, looked down at him with a mixture of lust and wonder. “Look at you, Rose,” she panted, her hips moving faster, her latex cock pounding into Jim's ass.

“You're nothing but a slutty little fucktoy for me and Kate. You're not even human anymore, are you, Rose? You're just a hole for us to fill.”

Jim moaned, his mouth still full of Kate's cock, the vibrations sending waves of pleasure through her. He could feel every inch of Pamela's strap-on, the latex stretching his ass wide, the sensation of being filled and used like this driving him wild.

“That's right, Rose,” Kate agreed, her voice thick with lust. “You're ours now. Our little whore.

Our little secret. Our little slut." Pamela's grip on Jim's hips tightens as she sets a brutal pace, her thighs slapping against Jim's ass with each thrust. The sound of flesh against latex fills the room, a symphony of primal lust.

Jim is a mess of moans and whimpers, his body trembling with the force of Pamela's assault. His ass is on fire, the pain and pleasure melting together into an overwhelming sensation. He can feel every vein of Pamela's latex cock, every inch as it stretches him wide. He takes it, oh God, he takes it all.

His ass clenches around the latex cock, and his body shudders with each pump. Pamela is relentless, her hips a piston, her fingers bruising his flesh as she drives into him. He feels like he's going to split in two, but he wants more. He needs more.

He's not just a hole, not just a fucktoy. He's theirs, and he wants to be used, to be filled, to be claimed. He wants to beg for it, to scream for it, to be a good little slut for them.

Kate, watching them fuck, is so turned on she can't stand it.

The two women come simultaneously flooding Rose with sperm and vaginal fluids. The completely gramed face, the makeup smeared and the hair dishevelled. Yet such an erotic image of their sexual toy.

Rose, propped on all fours, gasping and moaning as they fucked her senseless. Pamela's face was slick with sweat, her body glistening as she pounded into Rose's ass, her powerful hips driving her latex cock deeper with every thrust. Kate's hands gripped Rose's hips, her fingers digging into the soft flesh as she watched Pamela fuck their shared slut.

"Fuck her harder, Pam," Kate urged, her voice hoarse with desire. "Make her feel every inch of your cock."

Pamela obliged, her hips slapping against Rose's ass with brutal force.

The sound of flesh against latex filled the room, a symphony of lust and primal desire. Rose moaned, her body shaking with each thrust, her ass clenching tightly around Pamela's cock.

"That's it, Rose. Take it like a good little whore," Pamela growled, her voice thick with lust. "Take my big cock, you fucking slut."

The two women continued to pound Jim/Rose relentlessly for quite a while longer. Until the three of them, exhausted, collapsed on the bed.