CHAPTER 1: CAUGHT IN THE ACT I was driving across town, the sun dipping low in the sky, casting a golden hue over everything. My hands gripped the steering wheel just a little too tightly, my thoughts already racing ahead of me. Billie Joe and Becca were out of town, and I had been volunteered to take care of their cats. I didn’t really want to be left with this task but no one else was available so I reluctantly agreed.I don’t know Billie Joe or Becca that well but Billie Joe had been on my mind often and I caught myself checking her Instagram on a regular basis. Her fiery red hair, her curves that seemed to defy gravity, her large breasts, and those nipple piercings—oh, the piercings. I’d only seen a glimpse of the outline of them once in person, when she’d worn a tank top that left little to the imagination. Her Instagram was a minefield of temptation, filled with photos that made my pulse quicken and my imagination run wild. I couldn’t help it. She was intoxicating.I pulled up to their small house, which they were renting while they were attending Idaho State University. I parked on the street and walked up to their door, reached for the key under the front mat and let myself in. The cats greeted me as I stepped inside, their soft meows filling the quiet space. The scent of floral perfume lingered in the air, sweet and inviting, and I couldn’t help but associate it with her. I made my way to the kitchen, filling the cats’ bowls and water dish.I said on the couch in the living room to give the cats some attention before I left. But as I sat there, my eyes wandered, looking around at their belongings. Don’t do it, I told myself. You’re here for the cats, not to snoop. But her bedroom door, across from the living room, was slightly ajar, and the temptation was too much.I stood up, my heart pounding as I approached her room. My hand trembled as I pushed the door open, the hinges creaking softly. Her room is just how I imagined—messy in a way that felt intentional, like she’d thrown clothes around in a hurry. Her perfume lingered in the air, a mix of something floral and something muskier. My eyes landed on the dresser, where a small pile of lingerie sat, as if waiting for me.I stepped closer, my breath hitching as I picked up the strapless, black lace bra. It was soft to the touch, delicate yet daring. Beneath it was a matching pair of small panties. My stomach twisted with guilt, but the curiosity was overpowering. I raised the panties to my nose, inhaling deeply. Her scent was intoxicating—sweet, musky, and undeniably her. I couldn’t help myself and slowly licked the inside of her panties, where her pussy and butthole would rest. I let out an unintentional, soft moan as I did this.I glanced over to her closet, spotting a stunning pair of white high heels. I’d seen her wear them in one of her Instagram posts, and the memory alone was enough to send a shiver down my spine. I stepped over to her closet and picked up one of the shoes. No way, I told myself. This is too far. But as I held the shoes in my hands, imagining the straps wrapped around my ankles, I felt a rush of excitement that I couldn’t ignore.Just really quick, I thought. I’ll just try on her lingerie, this pair of high heels, and one outfit, then get dressed and leave. No harm done.I frantically stripped off my clothes, letting them fall to the floor in a careless heap. My Adderall had kicked in earlier, leaving my penis shrunken and soft—barely half an inch long, curling in on itself. It looked more like a small clit than anything else, and that only added to the thrill.I step into and pull on the panties, the lace soft against my skin. They fit snugly, covering my tiny clit and tight boy pussy. The feeling of the panties slipping between my cheeks sends a rush of excitement through my body. I reach back and spread my cheeks to allow the fabric to rest directly on my hole. Next came the bra, the cups too large for my chest. I tighten it all the way, helping it fit snug against my body, feeling a strange sense of empowerment as I looked in the floor length mirror on the other side of her room. I glance through her closet and find a short, strapless, pink dress. She wore this same dress in the Instagram post where she was wearing the white high heeled shoes. I slip the dress on quickly and slide the zipper on the side of the dress closed. My breath coming in short, uneven gasps.Then, my favorite thing, the shoes. I have always enjoyed wearing high heeled shoes and don’t know why. I sat down on her bed, feeling the cold sheets against my cheeks. I slid the heels onto my bare feet, wrapping the straps around my ankles and fastening them. I knew that I wouldn’t be able to get them off quickly if I strapped them all the way, but I didn’t care. The sense of being trapped by the shoes only brought even more of a thrill. The six-inch heels make me feel taller, more confident, and undeniably slutty.I stood up, wobbling slightly at first, but quickly finding my balance. The floor length mirror caught my eye again, and I couldn’t help but stare at myself. Oh my, I thought. I look… sexy. What a little sissy slut you are. The short dress left the bottom of my cheeks exposed, it hugged my stomach tightly, and wrapped around the bra perfectly. The heels elongated my legs, rounding my glutes, making me feel sexy, desirable—.And then I saw it.A metallic butt plug, resting on her bedside table, gleaming in the sunlight streaming through the window. My breath hitched as I slowly stepped towards it. I picked it up, turning it over in my hands. It was cool, heavy, and had a pink gem on the end—intimidating, yet exciting. My imagination ran wild, imagining Billie Joe putting it inside herself, imagining what it would feel like inside me, how it would look.“Umm, what the hell are you doing?”The sound of her voice made my heart leap out of my chest and I froze. The butt plug slipped from my fingers, clattering to the floor. I instinctively whipped my head around towards the sound of the voice. Billie Joe stood in the doorway, her arms crossed over her chest, her expression unreadable.“I—uh—” I stammered, my face burning with embarrassment. “I was just… checking on the cats and the house.”Her eyebrows shot up. “In my bedroom?”I swallowed hard, my heart pounding in my chest. “I—I didn’t mean to—”“You’re wearing my clothes,” she interrupted, her voice low, almost—dangerous.I glanced down at myself, the reality of the situation hitting me like a ton of bricks. “I… I can explain.”She stepped closer, her eyes roaming over me, taking in every detail. The way my legs looked in her heels, the way her dress hugged my body. Her lips curved into a small smile.“Do you like wearing my clothes, Aaron?” she asked, her voice dripping with something I couldn’t quite place.When she said my name out loud, my heart skipped a beat. I opened my mouth to respond, but no words came out. My heart was racing, my mind a whirlwind of thoughts and emotions. I have done some cross dressing in the past but no one knows about it. She took another step closer, she reached out and gently touched my arm.“Answer me,” she said, her voice soft, yet commanding.I swallowed hard, my throat dry. “I… I’m so sorry.”She tilted her head, her expression seemed to be one of curiosity.Her hand gently touched my side, her long manicured fingernails tracing down the dress towards my hip. I could feel the heat of her touch through the fabric, and it sent a shiver down my spine.“Huh,” she muttered. I expected her to start berating me or judging me for wanting to wear women’s clothes. After what felt like an eternity, she finally broke the silence, “You actually look pretty cute, honey,” her voice sweet, soft, and curious. She sat down on the bed and said, “Come here. Stand here so I can get a good look at you, sweetie.”My heart dropped in my chest and I froze, unable to move my legs. “Come on, don’t be shy honey,” she said. I can’t believe this is happening…But what am I supposed to do, she caught me wearing her clothes. I have to do anything she says otherwise she might tell someone. I reluctantly obeyed, taking a few steps before turning to face her. I couldn’t believe this was happening.“Good girl,” she muttered. “Now, give me a little twirl.”I felt my face turn bright red when she called me a good girl, and I sheepishly looked down at the floor, avoiding eye contact. But again, I obeyed and gave her a slow twirl. I have never felt this exposed before.“Wow…that outfit really does suit you, honey. But, I think it’s missing something…” she said in a soft, sweet tone, before slowly reaching down and picking up the butt plug off of the floor.

I drove to Billie Joe and Becca's house to take care of their cats while they were out of town. I couldn't resist the temptation to snoop in Billie Joe's room, and I ended up trying on her clothes and shoes. Billie Joe returned home and caught me in her room, wearing her lingerie and heels, and she was curious about it.

CHAPTER 1: CAUGHT IN THE ACT

I was driving across town, the sun dipping low in the sky, casting a golden hue over everything. My hands gripped the steering wheel just a little too tightly, my thoughts already racing ahead of me. Billie Joe and Becca were out of town, and I had been volunteered to take care of their cats. I didn’t really want to be left with this task but no one else was available so I reluctantly agreed.

I don’t know Billie Joe or Becca that well but Billie Joe had been on my mind often and I caught myself checking her Instagram on a regular basis. Her fiery red hair, her curves that seemed to defy gravity, her large breasts, and those nipple piercings—oh, the piercings. I’d only seen a glimpse of the outline of them once in person, when she’d worn a tank top that left little to the imagination. Her Instagram was a minefield of temptation, filled with photos that made my pulse quicken and my imagination run wild. I couldn’t help it. She was intoxicating.

I pulled up to their small house, which they were renting while they were attending Idaho State University. I parked on the street and walked up to their door, reached for the key under the front mat and let myself in. The cats greeted me as I stepped inside, their soft meows filling the quiet space. The scent of floral perfume lingered in the air, sweet and inviting, and I couldn’t help but associate it with her. I made my way to the kitchen, filling the cats’ bowls and water dish.

I said on the couch in the living room to give the cats some attention before I left. But as I sat there, my eyes wandered, looking around at their belongings. Don’t do it, I told myself. You’re here for the cats, not to snoop. But her bedroom door, across from the living room, was slightly ajar, and the temptation was too much.

I stood up, my heart pounding as I approached her room. My hand trembled as I pushed the door open, the hinges creaking softly. Her room is just how I imagined—messy in a way that felt intentional, like she’d thrown clothes around in a hurry. Her perfume lingered in the air, a mix of something floral and something muskier. My eyes landed on the dresser, where a small pile of lingerie sat, as if waiting for me.

I stepped closer, my breath hitching as I picked up the strapless, black lace bra. It was soft to the touch, delicate yet daring. Beneath it was a matching pair of small panties. My stomach twisted with guilt, but the curiosity was overpowering. I raised the panties to my nose, inhaling deeply. Her scent was intoxicating—sweet, musky, and undeniably her. I couldn’t help myself and slowly licked the inside of her panties, where her pussy and butthole would rest. I let out an unintentional, soft moan as I did this.

I glanced over to her closet, spotting a stunning pair of white high heels. I’d seen her wear them in one of her Instagram posts, and the memory alone was enough to send a shiver down my spine. I stepped over to her closet and picked up one of the shoes. No way, I told myself. This is too far. But as I held the shoes in my hands, imagining the straps wrapped around my ankles, I felt a rush of excitement that I couldn’t ignore.

Just really quick, I thought. I’ll just try on her lingerie, this pair of high heels, and one outfit, then get dressed and leave. No harm done.

I frantically stripped off my clothes, letting them fall to the floor in a careless heap. My Adderall had kicked in earlier, leaving my penis shrunken and soft—barely half an inch long, curling in on itself. It looked more like a small clit than anything else, and that only added to the thrill.

I step into and pull on the panties, the lace soft against my skin. They fit snugly, covering my tiny clit and tight boy pussy. The feeling of the panties slipping between my cheeks sends a rush of excitement through my body. I reach back and spread my cheeks to allow the fabric to rest directly on my hole. Next came the bra, the cups too large for my chest. I tighten it all the way, helping it fit snug against my body, feeling a strange sense of empowerment as I looked in the floor length mirror on the other side of her room. 

I glance through her closet and find a short, strapless, pink dress. She wore this same dress in the Instagram post where she was wearing the white high heeled shoes. I slip the dress on quickly and slide the zipper on the side of the dress closed. My breath coming in short, uneven gasps.

Then, my favorite thing, the shoes. I have always enjoyed wearing high heeled shoes and don’t know why. I sat down on her bed, feeling the cold sheets against my cheeks. I slid the heels onto my bare feet, wrapping the straps around my ankles and fastening them. I knew that I wouldn’t be able to get them off quickly if I strapped them all the way, but I didn’t care. The sense of being trapped by the shoes only brought even more of a thrill. The six-inch heels make me feel taller, more confident, and undeniably slutty.

I stood up, wobbling slightly at first, but quickly finding my balance. The floor length mirror caught my eye again, and I couldn’t help but stare at myself. Oh my, I thought. I look… sexy. What a little sissy slut you are. The short dress left the bottom of my cheeks exposed, it hugged my stomach tightly, and wrapped around the bra perfectly. The heels elongated my legs, rounding my glutes, making me feel sexy, desirable—.

And then I saw it.

A metallic butt plug, resting on her bedside table, gleaming in the sunlight streaming through the window. My breath hitched as I slowly stepped towards it. I picked it up, turning it over in my hands. It was cool, heavy, and had a pink gem on the end—intimidating, yet exciting. My imagination ran wild, imagining Billie Joe putting it inside herself, imagining what it would feel like inside me, how it would look.

“Umm, what the hell are you doing?”

The sound of her voice made my heart leap out of my chest and I froze. The butt plug slipped from my fingers, clattering to the floor. I instinctively whipped my head around towards the sound of the voice. Billie Joe stood in the doorway, her arms crossed over her chest, her expression unreadable.

“I—uh—” I stammered, my face burning with embarrassment. “I was just… checking on the cats and the house.”

Her eyebrows shot up. “In my bedroom?”

I swallowed hard, my heart pounding in my chest. “I—I didn’t mean to—”

“You’re wearing my clothes,” she interrupted, her voice low, almost—dangerous.

I glanced down at myself, the reality of the situation hitting me like a ton of bricks. “I… I can explain.”

She stepped closer, her eyes roaming over me, taking in every detail. The way my legs looked in her heels, the way her dress hugged my body. Her lips curved into a small smile.

“Do you like wearing my clothes, Aaron?” she asked, her voice dripping with something I couldn’t quite place.

When she said my name out loud, my heart skipped a beat. I opened my mouth to respond, but no words came out. My heart was racing, my mind a whirlwind of thoughts and emotions. I have done some cross dressing in the past but no one knows about it.

She took another step closer, she reached out and gently touched my arm.

“Answer me,” she said, her voice soft, yet commanding.

I swallowed hard, my throat dry. “I… I’m so sorry.”

She tilted her head, her expression seemed to be one of curiosity.

Her hand gently touched my side, her long manicured fingernails tracing down the dress towards my hip. I could feel the heat of her touch through the fabric, and it sent a shiver down my spine.

“Huh,” she muttered. 

I expected her to start berating me or judging me for wanting to wear women’s clothes. 

After what felt like an eternity, she finally broke the silence, “You actually look pretty cute, honey,” her voice sweet, soft, and curious. 

She sat down on the bed and said, “Come here. Stand here so I can get a good look at you, sweetie.”

My heart dropped in my chest and I froze, unable to move my legs. “Come on, don’t be shy honey,” she said. 

I can’t believe this is happening…But what am I supposed to do, she caught me wearing her clothes. I have to do anything she says otherwise she might tell someone.

I reluctantly obeyed, taking a few steps before turning to face her. I couldn’t believe this was happening.

“Good girl,” she muttered. “Now, give me a little twirl.”

I felt my face turn bright red when she called me a good girl, and I sheepishly looked down at the floor, avoiding eye contact. But again, I obeyed and gave her a slow twirl. I have never felt this exposed before.

“Wow…that outfit really does suit you, honey. But, I think it’s missing something…” she said in a soft, sweet tone, before slowly reaching down and picking up the butt plug off of the floor.

A man named Aaron, driven by curiosity and a secret attraction, crosses a line when he decides to try on his friend's lingerie while taking care of her cats. He finds himself in a compromising position when she returns home unexpectedly, leading to a tense and revealing confrontation.

Bonding with Billie Joe

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