by Jane Futa
“No, not at all-“
“Save it. You looked at my tally the other night and decided you’d just hone in on that.”
I had no more defenses. I decided to let her ridicule me.
“I earned that. I put up with so much as a woman.”
“I know-“ I said with honest sympathy. I remembered what Jeff had me do in the interview.
“If you think I’m just going to let you come in and take tips from me without some kind of punishment, you are in for a rude awakening.”
“Punishment?” I swallowed hard.
Suddenly, Cindy grabbed my jaw and turned it toward her. “Yes. You want to dress like a woman? You want to get tipped like a woman? Well you’re going to have to get punished like one, too.”
“What do you-“ Before I could finish, she had her lips pressing into me, her tongue sliding against mine. I wasn’t sure what Cindy’s objective was, but I had no problem with making out with her.
She hiked her skirt up her thighs and then placed one leg on either side of me. She straddled me and felt my hard cock against her pelvis.
“You’re already hard?” she asked with a laugh. She reached down and felt my shaft through the fabric. “And you’re so small!” She laughed again and I blushed. Despite being humiliated, my cock stiffened more.
“Wait here,” she said. She disappeared toward the right down a dark hallway. She flipped a light on in a bedroom and I heard a dresser door slide open. She returned quickly with a huge, purple dildo in her hand.
“What the-“
“You should be used to this,” she said, straddling me again. “Don’t tell me Jeff didn’t make you suck him off…”
I looked deep into her eyes. I didn’t deny or confirm it, but she could see in my expression that I did. “So if you like being a woman so much. If you like sucking cock so much then I want to watch you suck this.”
Cindy’s wilder than I ever imagined. I knew there was no escaping the situation, and I partly didn’t want to escape.
I parted my lips similarly to when I was preparing to take Jeff’s cock in my mouth. I watched Cindy raise the dildo above my head and dangle it teasingly. Then she pressed a thumb to my chin and tugged downward, opening my mouth more.
She rested the head of the purple cock on my lower lip. I stuck out my tongue to lick the underside of the tip. She laughed devilishly and then dipped the head in. I wrapped my lips around it and she smiled playfully.
“Good girl,” she said.
Good girl, I thought. I was beginning to fall in love with that expression. I just wanted to be Cindy’s good little girl for the night.
Cindy pushed the dildo further into my mouth until it was hitting the back of my throat. She held it in place and then grabbed one my hands. She moved my hand to her right breast and I squeezed it gently.
She leaned her head back and moaned. She rocked her hips over my hard cock and started sliding the dildo in and out of my mouth. She was getting off to punishing me. This idea only made my cock harden more.
Fuck she’s hot, I thought as she fucked my face with a dildo. I was suddenly excited for what the rest of the night had in store. She rocked her hips faster, fucked my face harder, and moaned louder. I reached for the strap of her dress and slid it down her shoulder. Then I pulled the fabric down below her tits and gawked at her bare breasts.
They were the most perfect set of tits I’d ever seen. Her nipples were hardened into small nubs with areolas the size of quarters. They were perfectly pink and I brushed my thumb across them, sending a wild energy through Cindy’s body.
“Ohh!” she cried as I fondled her breasts. She slid the cock in and out of my mouth and my head started to spin. I felt like both a man and a woman simultaneously. My senses were in overdrive.
She slid the cock out of my mouth and kissed me hard. I rolled her nipples in my fingers as she rocked against my hips.
She dropped the dildo to the side and lifted my dress up higher. Then she pulled my cock out through the side of my panties. She pushed her panties to the side and slid the tip of my cock into her wet pussy.
Fuck, this is strangely hot. I was fucking her with both of us wearing panties. It was so foreign and yet somehow familiar. She rode my tiny cock as we kissed, her tongue swirling around mine and my hands still on her breasts.
Moments later she was screaming and throwing her head back as she came on my small cock. Cindy was obviously a girl that new what she wanted. She required hardly any work from me.
When she finished cumming she climbed off of me and said, “Now it’s your turn.”
“What do you mean?”
“Strip. Then get on your hands and knees.” She pointed to the floor and my eyes widened. I was in no position to deny her, though. I was still hopeful she would keep my secret safe.
I started to lift my dress up over my head. I was only in my bra and panties now and her eyes scanned my body with that hungry look in her eyes. “Leave those on. Hands and knees,” she repeated.
I stood from the couch and then dropped to my knees on the carpet. Then I leaned forward on my hands and waited for Cindy’s next move.
She lowered to her knees behind me and then pulled my panties down to my knees. She spanked my ass and a warm chill spread through me. Fuck this is crazy. But I’m so turned on right now.
Cindy brought a wet finger to my ass and wiggled it inside. “Fuck!” I cried as she brushed past my prostate. I’d never had anything fuck my ass before and I had no idea it would feel so good. Now it was all starting to come together. She was going to fuck me with the dildo.
It’s so huge! I thought. I was a little worried it would hurt more than feel good, but Cindy did say it would be punishment. I closed my eyes and prepared for the worst.
Cindy removed her finger and then spanked me again. That familiar warm chill crept along my spine. Then I felt a saliva covered cock head rest against my little asshole.
I bit my lower lip as I prepared. She pushed it in slowly at first. I felt my asshole stretch as wide as it could to accommodate the large, purple member.
“Fuck!” I cried out as it stretched me.
“Maybe you’ll think twice before stealing other people’s tips,” she said. “Let me hear you apologize.”
“I’m sorry. I’m really sorry,” I said with a strained voice as she pushed the dildo in further.
“Tell me you deserve to get fucked.”
“I deserve to get fucked.”
“Tell me how badly you want it.”
“Please give it to me!” I begged through the pain. Eventually, the dildo passed a threshold and started to feel pleasurable. I moaned at this and then Cindy giggled.
“You like getting your asshole fucked?”
“Mmhmm,” I said, feeling my cock stiffen more and more.
“That’s a good girl,” she said, nearly sending me over the edge. She pushed the cock all the way in and then pulled it out slowly.
“Fuck!” I cried out. She started pumping the cock in and out of my little asshole. Soon I felt my dickhead explode, sending warm cum all over Cindy’s carpet.
“Such a naughty girl,” she said, spanking me again. She laughed when she saw me cum. “You really do like this cock in your ass.”
I nodded, hanging my head in shame.
She pulled the dildo from my ass and pulled my panties up. I got up off my hands and leaned back on my feet. I spun around to face her to see her wiping the dildo with a wet towel.
“You’re not going to tell anyone, are you?” I asked.
“Hmmm,” she said.
“Please, please don’t!”
“I’ll make you a deal.”
“Anything.”
“We do this every Friday night and I won’t tell a soul. I’ll even let you keep making tips at the restaurant.”
“Really?” I asked, pleased by her request. After all, I did enjoy her fucking me.
“Really.”
I wrapped my arms around her and t
hanked her. She stroked my hair with her hand and kissed my forehead. “But if you miss one night. I’m outing you to everyone.”
“I won’t miss. I promise,” I told her.
“Good girl,” she said. I couldn’t help but smile when she said that.
Yes, I thought. I’m a good girl. And I couldn’t wait to prove how good of a girl I could be for Cindy.
Dressed Undercover
Chapter 1
I was the thinnest cop in the precinct. Nobody thought I’d make it through the physical training, but I’ve always been stronger than I looked. The other guys frequently teased me for my small size and often made jokes about my gender.
So it was no surprise when they decided I’d be perfect for the next undercover mission. They needed a woman but we only had one on the force who was mostly used to writing traffic tickets. It was a small town with a small precinct, and I was fairly new so the team knew I’d be able to fool our guy easily.
I wasn’t so sure about it myself. “Do I really have to dress up as a woman?” I asked the chief officer.
“It’s the only way, Rick. This guy doesn’t hire many men and we need you to have a job at his joint so you can see the inner workings. I know he’s laundering money through his strip club, I just need the proof.”
“What if he actually makes me strip?” I asked.
“You’re a cop. He can’t make you do anything.”
That didn’t make me feel any better. Our guy’s name was Lyle and he was loosely connected to a large drug operation that filtered into our small town. He seemed to think it’d go unnoticed, but he was wrong. It was my job to get in there and catch some sort of proof, but my hands were shaking just thinking about it.
Lyle was possibly dangerous and that only because the guys above him were even more dangerous. If I got caught crossdressing and being a cop, I don’t know what he’d do to me, and I didn’t want to think about it.
“Pick a name for yourself and take these with you,” said the chief, handing me a duffle bag across his desk. I unzipped it to find a pile of women’s clothing tossed inside. I gulped as I reached in to feel the fabric. It was soft enough, but too delicate for a man. I wondered if it would be easy to see my cock through the thin, dainty fabric.
I guess this is the one time it’s good to be small, I thought. Usually I was embarrassed by my tiny cock, but it might just be the thing that saves me from being caught.
I exhaled and left the office, sliding the duffle bag under my desk.
“Heeey Rick,” said Sam, the sleaziest cop in the precinct. “You gonna dress real purty for Lyle?”
“Shut up,” I responded weakly, feeling my cheeks flush. A few of the guys around us laughed, and I could feel their eyes on me, picturing me dressed as a woman.
Suddenly Katherine, our only female cop, came over. “I’m so sorry I couldn’t do it,” she said with a sympathetic look. “I don’t know the first thing about going undercover.”
“It’s okay,” I said. “I wouldn’t want to put you in that kind of danger.”
“You’re fine with it?”
“As fine as I was in Chicago.”
“Why did you move down here, anyway?”
“I thought I was getting away from the big crime when I left a big city. Figures I’d be tasked with the most dangerous gig here,” I said.
She flashed me a look of pity before heading back to her desk. The other guys finally stopped watching me and teasing me, and I felt more alone than ever. I’d gone undercover before, but never dressed as a woman. I started to feel terrified that I wouldn’t be able to pull it off.
I finished up the rest of my paperwork and then headed home. Once in my apartment, I threw the duffle bag on the bed and returned to the kitchen for a beer. I popped the top and looked down the hallway at the bedroom. I had no intentions of trying on the clothes before it was time to fool Lyle, but something about that bright green duffle bag was calling toward me.
I ignored it and sat on the couch. I turned on the television hoping to distract myself. It worked for a few minutes, but I started to become restless. I laid my hands in my lap and jerked me knees up and down. I felt like I had just finished several espressos rather than a beer.
I got up and paced the floor, rubbing my neck nervously. My mind kept thinking about the duffle bag. Maybe it’d be good to make sure everything fits, I thought.
No. No. It’s just queer to go try it on for no real reason.
But who would know? It’s only you in this lonely apartment.
My mind fought with itself back and forth. I wasn’t sure why I was worried about trying on some clothes or why I almost wanted to.
It’s just innocent curiosity, I told myself.
I returned to the sofa, trying to relax one more time. My body only became tenser and my mind became more curious. Fuck it, I thought. I stood up from the sofa and tore my shirt off. Then I went into the bedroom, closed the blinds and locked the door.
Then I stood at the end of the bed, staring at the duffle bag.
Chapter 2
It felt like I was staring at it for hours rather than minutes. I reached out with shaky hands and slowly unzipped it. I slid the top flap to the back and gazed upon the varying textures and fabrics. I wasn’t even sure which items were in there for me yet.
I reached my hands in and bunched the fabric in my fingers. Then I turned the bag upside down and emptied it of its taboo contents. I watched the lace and silk and soft cotton fall elegantly on the bed. Then I tossed the duffle bag to the side.
I let out a long exhale and spread out the pieces. There were two dresses, one in purple and one in black. I held the purple up to my body and noticed the skirt flared out. Next, I held up the black one and saw that the skirt was more fitted.
I dug through the fabric again and found a few sexy tops along with some very short shorts. I guess I needed skimpy clothes if I was going to be convincing as someone trying to land a gig at a strip joint.
I can’t believe I agreed to this, I thought. But I knew why I did. Nobody at the precinct took me seriously and there weren’t enough major crimes in town to prove my worth. Catching this guy Lyle could earn their respect.
Wouldn’t dressing as a woman to catch him though have the opposite effect I wanted? I tried not to think about that too much. After all, they wouldn’t see me as a woman.
Suddenly, something pink caught my eye. A small triangle of fabric peaked out from underneath a pair of shorts. I moved the shorts to the side and saw that it was a tiny lace thong. Panties too?
I wondered if the panties were a joke. Sam probably tossed these in here. I couldn’t think of why I would need women’s panties to convince Lyle. It’s not like I could strip for him, anyway. He’d certainly see my cock no matter how tiny it was. Then I’d be a dead man.
“Ha, ha, Sam,” I said aloud tossing the panties to the side. I thought about which outfit to try on first. “A dress ought to be easy enough.”
A strange sensation shot through me as I said the word “dress” aloud. Me, a man, in a dress… I exhaled again. I picked up the purple one that flared so as not to be too restricted just yet.
I slid it over my head, pushing my arms through the short sleeves. Then I secured it around my waist, watching it flare out over my pants. It hugged my chest perfectly and the narrow cut around my waist made me feel feminine.
Maybe this won’t be so hard, I thought. If the clothes could help me feel feminine, then I could act feminine too. I lifted the skirt up and unfastened my pants. Then I slid them down and kicked them to the side.
I stared down at my legs. They were hairy enough to need a shave, but the hair was light blonde and barely noticeable. I could almost imagine them as women’s legs. I tilted my hips from side to side, shifting my weight from one foot to the other. I was practicing my girly poses.
I was surprised at how comfortable I felt in the material. What are women always complaining about? This dress is kind of fun…and for a split
second I was mortified.
Am I really enjoying this? My heart pounded in my chest. I decided to run to the nearest mirror to convince myself that I couldn’t pull this off, that I didn’t really look and feel like a woman. But the mirror only made things worse.
I didn’t just look like a woman. I looked like the hottest woman I’d ever seen! Apart from the short hair, I was hardly distinguishable as a man. My jaw dropped due to horror and attraction at the same time, but the transformation was growing on me.
I brought my hands to my waist, feeling the fabric cinch in just above my hips. Then I moved my hands up to my chest, pretending I had small breasts that I was caressing. I gasped at the double identity I suddenly had. I was both an attractive woman, and a man groping an attractive woman. It was enough to make my head spin.
My eye landed on the pink fabric through the mirror’s reflection. I turned around and stared at it daringly. The panties were just a joke, I reminded myself, but I suddenly had an urge to try them on. No one will know.
I removed my boxers slowly. I moved toward the bed and picked up the small fabric. I slid my legs in through the holes and exhaled as the thin, lacy material glided up my legs. My eyelids closed. The hairs on the back of my neck stood on end. My cock stiffened.
When the fabric touched my cock and balls I felt a teasing warmth spread through my pelvis. I suddenly wanted to fuck something…no, be fucked by someone.
This is getting weird, I thought, concerned by the pleasure building through my body. I secured the thong on my waist and let the fabric cradle my small dick and balls. Then I dropped the dress down and walked back toward the mirror.
Each step felt new as the thong shifted along my ass. Fuck this is hot. My cock stiffened more, the head now pulsing with desire. When I reached the mirror, I pulled the dress skirt up just enough to see the panties. It looked and felt like being a real woman. I could hardly see my cock through the thin fabric.
I ran my hands up my thighs and over my new thong. I turned to look at my ass in the pink panties and was shocked to see that my ass looked even hotter. I bent over slowly, admiring the way the strap slid between my perfect, round ass cheeks. I’d never found myself so attractive before. Normally, I had low self-esteem.
