Man to Woman

by Jane Futa

  She didn’t need to command me. I couldn’t contain my cries. “Fuck, fuck!”

  She pushed it in harder and faster, and my body shook against the chair. My cock swayed in the cold air and I could feel the head swelling. I was going to explode.

  “I’m going to come!” I cried with my eyes shut tight.

  “Yes, come for me,” said Carol, petting my head again.

  My cock shot white ropes across the fabric of her expensive executive chairs. She kept petting me while she fucked my ass. When my body stopped quivering she removed the dildo from my ass with a chuckle.

  “So you won’t tell anyone about this?” I asked. I turned around after collecting my clothes and started to get dressed. She moved back to her desk and wrapped the cock up in a towel she kept in her desk.

  “A deal is a deal,” she said. “I haven’t ruled you out for the job, by the way. I just need to see you interact with my son first. Maybe we’ll have more days like today as well?” She raised an eyebrow curiously.

  I looked at her in shock. She still wanted me for the job? Or maybe she just wanted me around as her little toy…

  Either way, I was interested in both. “Sure,” I said.

  She smiled. “Good girl,” she said.

  My Boss’s Daughter

  Chapter 1

  The first time I met Scarlet was at a company picnic. Most of the employees brought their families. There was a barbecue, games, and a conservative atmosphere. Well…conservative other than Scarlet.

  She was the boss’s daughter and she had just turned 18. Despite her young age, she had a daredevil attitude and way with commanding people. She took after her father in that way. She was beautiful from head to toe. Long, wavy blonde hair and long legs to match. The day of the picnic she wore a red halter top dress with white flowers all over it. She also wore matching red lipstick. It was hard to keep my eyes off her, but I knew I’d have to if I wanted to keep my job.

  She’d always been a trouble maker, but the day she turned 18 she set her sights on humiliating her dad’s employees. One guy got fired because Matt, our boss, caught him fucking her in the company bathroom. There were rumors speculating what position they were in when they were caught, but I couldn’t let my mind go there, or I knew I’d be next.

  There was no such thing as self-control around her. It was best to just avoid her altogether until she eventually set her sights on you. Then it would take a miracle to keep her away. Unfortunately for me, I was her new target on the day of the company picnic.

  I had just finished eating and decided to take a leak. The park that held the picnic had nice restrooms in their own building. I crossed the long field to get to them, and in doing so, I must’ve singled myself out too much. Scarlet saw me and followed soon after. I had no idea until I was in the bathroom that she had walked behind me the whole way.

  I closed the bathroom door behind me and pulled my cock out of my pants to piss. I surveyed it, frowning slightly at its small size. I knew I could never please a sexy woman like Scarlet with a penis like this. Maybe if the rest of my body was more masculine, it would make up for it. Unfortunately, I was small all over. Even my limbs were delicate and womanly.

  When I finished pissing, cock still in hand, the door swung open. I didn’t look up at first, because I assumed it was another guy coming in to use the bathroom. Then I heard her voice.

  “Oh my god! It’s so small!” said Scarlet, to my horror. I looked up quickly and saw her standing in the doorway with her hands pressed against the frame. Her eyes were wide and she started laughing. I quickly shoved my tiny cock back in my pants and hung my head.

  “This is the guy’s restroom,” I told her in a weak voice. Who cares if she thinks I’m small? Fucking her would only get me fired anyway. Still the insult stung a little bit, and I didn’t have much self-confidence to begin with.

  “Are you sure?” she asked. “I could’ve sworn it was the women’s, and you certainly couldn’t be a man with a cock like that.”

  “Read the sign,” I shot back, still too weak to be intimidating.

  “You know, you kind of look like a girl too,” she added.

  I shoved my hands into my pants pockets as I looked at the floor. I shifted my foot across the cement, pushing dirt around with the toe of my shoe.

  “I bet you’re even wearing women’s panties,” she said.

  I looked up at her. “No. What makes you think that?”

  “Well if you aren’t, you should be.”

  The idea of wearing women’s panties sounded utterly ridiculous. I started to think she was crazier than she looked. I watched Scarlet shut the door and lock it behind her. Fuck, I thought. What is she doing?

  She walked toward me, her hips swaying deliciously as she approached. She crept closer and closer until her young, curvy body was inches away from mine. I felt my cock harden a little but knew it was too small for her to see through my pants. Her round blue eyes looked up at me sweetly and she bit her bottom lip.

  Then I saw her reach for the hem of her dress and slowly lift it up her legs, until she revealed a silk pink thong.

  “What-what are you doing?” I asked, awkwardly stuttering over my words.

  “I’m giving you what you want.”

  Oh no, oh no. We’re going to fuck and I’m going to get fired. She reached for the waist of her thong and pulled it down over her hips. She slid it slowly down her thighs, her face nearing my crotch as she bent over to remove them.

  I watched her slowly step out of them, and noticed she was wearing white ballet flats. Then she stood back up, holding her panties in front of my face.

  “Here you go,” she said.

  “What am I supposed to do with those?”

  She laughed. “Wear them, of course.”

  “Ha ha,” I said, rolling my eyes at her suggestion. Suddenly her face became very serious. Her eyebrows furrowed and her eyes narrowed. She formed a small pout with her ruby red lips and I became genuinely afraid.

  “If you don’t, I’ll just tell Daddy that you tried to fuck me in here.”

  “How do I know you won’t tell him either way?” I challenged.

  “Hmmm. I guess you don’t. But this way you at least have a chance…”

  She smiled a devilish smile and dangled the panties in front of me, teasingly. I snatched them quickly from her hand and she started laughing.

  “Well?” I asked, looking toward the door to suggest she leave.

  “Oh no. I have to see you put them on. You know, to make sure you’re actually wearing them.”

  I sighed heavily. Then, in front of my boss’s daughter, I unfastened my pants and slid them to the floor. I removed my shoes and kicked off the rest of the bunched fabric that lay at my ankles.

  Next, I removed my white briefs. “What am I supposed to do with these then?” I asked her. She grabbed them from my hand and stuffed them into her little white purse.

  “There,” she said.

  “What if your dad finds them?”

  “He won’t. He doesn’t dare go through my purse after the last time.”

  I wasn’t sure I even wanted to know. This girl had some serious balls to control Matt like that. Matt was as stern of a boss as they come, and I just couldn’t imagine him being pushed around by an 18 year old.

  I swallowed hard as I looked at the pink panties I held in my hand. I looked up at Scarlet for a moment, with a pleading expression. Please don’t make me do this, I thought. But she only raised her eyebrow and folded her arms across her chest. I exhaled and bent over to step into them.

  I heard her giggling as I slid them up my legs and I couldn’t be sure if she was laughing at my small penis or the fact that I was actually going through with her demand. I felt utterly humiliated as I secured the waistband around my hips.

  However, as soon as the soft, cool silk snugly wrapped around my small cock, I couldn’t help but sigh with pleasure. It was the most amazing thing I’d ever felt and it didn’t even matter
that this girl was laughing at me.

  “Oh my god!” she cried. “You actually like it?”

  How is she so good at reading me? I wondered. I couldn’t believe my expression had changed enough to let her in on my new secret pleasure.

  “Oh ho ho! This is classic!” she cried out as she laughed.

  I reached down and slid my pants back up, fastening the buckle at my waist. My pants felt new against the silk thong. I started to wonder how it would feel to walk around wearing this thong. I wondered if anyone would be able to tell that something was different, or if I’d have my own little secret. Well, a secret that I shared with the mischievous Scarlet.

  “What are you going to do?” I asked her in regards to being completely bare underneath her dress.

  “Oh I go commando all the time,” she said. The image of her pussy being so exposed at a company picnic got my cock hard. I felt it push stubbornly against the tight thong. Feeling it rub against the silk felt so exotic. It was going to be hard to go out to the picnic without jacking off first.

  “Ready?” she said, still giggling slightly.

  “We can’t leave together,” I said.

  “I know, silly. You go first. I’ll wait until the coast is clear.”

  I nodded and then looked at her longingly. This girl could be the death of me, I thought. I put my shoes on and headed for the door. I breathed in deep and exhaled before unlocking it and stepping out into the harsh, exposing sunlight.

  Certainly everyone will know, I thought. Then I made my way across the field toward the happy, unsuspecting families.

  With each step I took, I felt the silk shift against my skin. It was the perfect fabric choice for such a warm day and I was starting to hate my plain cotton briefs. I could almost see myself wearing these more often. No one would have to know.

  The strap of the thong rode up my ass, between my cheeks. The front hugged my cock and balls tightly and I was stimulated with each new movement of my body. Something about wearing Scarlet’s thong made me want to sway my hips like she did. Despite my normal appearance on the outside, I suddenly wanted to be more feminine.

  What’s happening to me? I wondered as I approached the families. A group of kids ran by me quickly, startling me for a moment. You can do this, Steve, I told myself. Nobody knows what you’re hiding.

  Then I looked back toward the bathrooms. I saw Scarlet sneaking out of the men’s room quickly and rushing across the field. Nobody knows unless she tells them. Suddenly, my heart started to race at the idea of her completely humiliating me in front of everyone. But my racing heart was accompanied by a strange ecstasy rather than complete panic. Surprisingly, I enjoyed the thought.

  I knew, however, that the fantasy was more appealing than the reality. I knew if she blabbed, I’d never be able to face these people again and would likely lose my job. My heart beat faster and faster the closer she got. I felt like it would explode when she rushed immediately up to her father.

  I watched her stand on her toes to whisper something in his ear. Fuck, fuck, fuck! She’s telling him that I’m wearing her panties right now!

  I started to panic, but at the same time felt my dick grow harder. Thank goodness I’m small, I thought. Nothing would be more humiliating than getting a visible erection around everyone I work with.

  Matt turned his head to look at me. I tried to brush it off by giving him a smile, but then I saw him walk toward me. Shit, shit! He’s going to reprimand me and fire me.

  “Steve!” he cried as he closed the safe distance between us.

  “Hey boss,” I said nervously.

  “I just wanted to shake your hand, my boy,” he said, reaching his hand out for mine. With an utterly confused expression, I reciprocated the handshake. “My daughter just told me of the fantastic deed you did.”

  I looked at her as if I could figure out what she had said by surveying her body language. When I turned up with nothing, I looked back at Matt.

  “You know, with the cigarette?”

  “Right, right,” I said, shaking my head. What the hell is he talking about?

  “She told me about how she went to the bathrooms to smoke up but you convinced her not to. I’ve been trying to get her off smoking for years, but she never listens to me. You’re a good man, Steve.” He slapped my back confidently and smiled.

  “Of course,” I said. “No problem.”

  “We need more people like you in this company,” he said, leaning in close so that no one else could hear. “Keep an eye out for Scarlet, will you?”

  I swallowed hard as I thought about her naked pussy under her dress. “Absolutely, sir.”

  Chapter 2

  The next time I saw Scarlet was at take-your-daughter-to-work-day. Thankfully, I was single and without any kids to bring, but I knew that day that Scarlet would show up. I had barely slept a wink the night before, knowing that she might seek me out after the company picnic. I was still confused why she talked me up to Matt when she could’ve said nothing, but I was still grateful for it.

  Maybe she’s just building me up for when it’ll inevitably come crashing down, I thought.

  I tried to hide in my cubicle all day, but I would occasionally see her walk by. She’d sneakily glance at me, but quickly skip away before anyone else could notice. She wore tight jeans and a black, low cut tank top that hugged her breasts perfectly. I overheard my boss scolding her for her attire.

  “The point of this day is to inspire you to do something great with yourself. That outfit is hardly going to cut it in the workforce.”

  “But Daddy! I don’t need to work when you make us so much money,” she said with big doe eyes.

  “Yes I do make a lot of money,” he touted. “But you still need to learn some discipline and responsibility. I want you to stop getting into so much trouble, Sweetie.” Matt’s office was right behind my cubicle, so I could hear a great deal of what went on in there.

  I tried to avoid the bathroom as much as I could, but eventually I had to go. I looked around the office to make sure there was no sign of Scarlet and I scurried off.

  I had washed her delicate pink panties in case she wanted them back, but I couldn’t help wearing them just one more time. I decided it would be good to wear them on that day because if she asked for them, I’d have them on hand. And I figured I could go commando just this once at the office. Ultimately, though, I hoped she wouldn’t confront me at all. I wanted to keep the panties, but I also didn’t want to get fired for interacting with her in the wrong way.

  I walked into the bathroom and planted my feet firmly at a urinal. I pushed the silky fabric to the side so I could sneak my dick out through the zipper hole in my pants. I was careful so that if anyone came in, they wouldn’t see the panties. At the same time, feeling the fabric tighten and bunch on one side of my cock was stimulating. I was half tempted to go into a stall and jack off right there at work.

  Scarlet had impeccable timing. She came in again when my tiny cock was out. I shoved it back in quickly and she locked the door behind her again.

  She giggled as she approached me. “Do you have my panties?” she whispered in my ear. I looked down at her large breasts which were almost touching me. I wanted to reach out and grab them so badly, but I knew that was the wrong thing to do.

  “Yes, actually,” I told her as I pulled my pants down partly to show off the pink silk.

  “I should’ve guessed you’d be wearing them. You’re such a little sissy girl,” she teased while poking my chest.

  “Let me just get out of them and then you can have them back.”

  “Oh no, no,” she said. “I don’t want them back. In fact, I have something to add to them today.”

  “What do you mean?”

  She giggled and swung a larger, black purse around to the front of her. Then she pulled out a soft pink lace bra.

  “No, no,” I said. “I couldn’t possibly wear that. Everyone would see through my shirt.”

  “No they won’t. Don’t
you have a jacket or anything you could wear over it?”

  “Yes, but I’d have to walk all the way back to my desk without a jacket, and those padded cups would poke out through my shirt.”

  “Don’t be such a wuss. It’s either this or I tell Daddy that you tried to rape me.”

  I exhaled deeply. I wasn’t sure how much longer this kind of relationship could go on. While I loved the adventure, the stakes were pretty high. “Okay,” I said, hanging my head.

  “Good girl,” she said as she giggled. She handed the bra to me and then stepped back toward the wall, leaning against it while she watched. “Strip for me,” she said.

  “Everything?”

  “Of course, silly. I want to see how good the panties and bra look together on you.”

  “What if someone needs to use the bathroom?”

  “They can wait.”

  My heart raced. I knew at any moment someone could be knocking on the locked door of the bathroom trying to come in. And when they figured it was locked they might just go ask Matt to find someone to unlock it. It wouldn’t be long before they’d find out I was in there alone with Scarlet, wearing women’s lingerie.

  I eyed the door worriedly, but knew there was no escape. I lifted my hands to the top button of my shirt and slipped it out of the keyhole. I turned my attention to Scarlet and saw that she was biting her lip while giving me a daring glare. I couldn’t help but take one more look at her round breasts as they practically burst from her top.

  My dick hardened as I thought about her body. When my shirt was unbuttoned completely, I slipped it slowly down my arms and tossed it over the bathroom stall that was next to me.

  “You don’t look manly at all!” she teased when she saw my muscle-less chest. “You’re going to look so pretty in a bra.”

  I felt insulted at first, but hearing her call me pretty changed my attitude quickly. I looked over my shoulder at the mirror behind me. Could I really be pretty? Suddenly, I was eager to put on the bra that Scarlet had brought for me. I held it up to my face to inspect it. I’d never put on a bra before. It smelled like sweet flowers, probably from Scarlet’s perfume.