“Put these on first,” Patricia said and held out a pair of red panties from the pile of clothes on the bed. They were tiny and girly, and I didn’t see how they would ever fit a guy like me, but Patricia wasn’t letting me get out of this. If I wanted to fuck her, I had to play by her rules.
“But… they—”
“Are you arguing with me?” Patricia asked and pulled the tresses of the whip through her fingers. “I don’t like boys who argue.”
“No, I’m not!”
I snatched the red thong from Patricia’s hand. My dick had gone soft by that point, most likely out of fear, so it only made a little bulge in the panties once I got them up my legs. I couldn’t believe that I was wearing women’s underwear! Had I lost my mind?
“Damn, Marvin. You look so sexy in those,” Patricia said as she took a step toward me. She placed a finger on my chest and ran it all the way down until it was at the waistline of the thong. She pulled on the fabric and made a whimpering sound as she took a look at my dick.
I jumped when she let the fabric snap back into place. She turned away from me and walked back over to the bed. She picked up a skirt and passed it to me.
The skirt was white with red stripes and went about halfway down my thighs. I told myself to stop, but then I took a look at Patricia, remembering why I was doing all this in the first place. Her lips felt so good around my dick, and truthfully, putting on panties and a skirt and whatever else was a small price to pay to feel those soft lips again.
“Twist your hips! Make the skirt dance!”
I looked down at my body awkwardly before putting my hands on my hips and moving like I didn’t have an ounce of rhythm. Patricia covered her mouth as she tried not to laugh, which she was failing miserably.
“Hey! Don’t laugh at me!”
“I’m not! I promise,” Patricia said as she did her best to stop laughing, which was a futile effort at best. She stifled a few more laughs as she took my right arm and lifted it above my head, twirling me in a circle.
I felt like a girl from a movie, and my heart exploded with desire. What did it matter that I was wearing a skirt? If I ignored all the stupid voices in my head, I actually felt fantastic. My cock was supported, and my legs could breathe. Wearing a skirt and panties was much more comfortable than I’d ever expected.
“You’re just missing a bra and your blouse.”
“A bra?” I asked in a weak voice.
“Yes! Did you think you could get all dressed up without one?”
“Women don’t always wear bras.”
“True, but you’re going to wear one if you want me to finish that blowjob that I started.”
I groaned and took the bra from Patricia’s hand. I was a lot less excited than I’d been a few moments ago when I was twirling around in a circle, feeling like a starlet in a movie.
“That’s my boy.”
“How do I even put this thing on?” I asked in a frustrated voice.
“It’s not hard! I promise!”
I made more disapproving sounds as Patricia helped me put on the bra, pulling it up my arms and fastening it into place. It was red like the panties and felt tight on my chest, but I didn’t hate it when I got a glance of my reflection in the bathroom mirror.
“You like it, don’t you?”
“No,” I said quickly.
Patricia chuckled and shook her head, and then she reached to grab a handful of tissue paper. She balled it up and stuffed it into my bra, doing the same thing with the other side. I covered my mouth in disbelief when I saw my reflection in the mirror.
“You’re looking pretty girly, aren’t you?”
“Yeah, but why are you doing this?”
“I like my guys on the girly side.”
“Really?” I asked, not quite believing Patricia. “You aren’t pranking me, are you?”
“Does this seem like a prank to you?”
“No, but—”
“Why are you doubting me, Marvin? I’m only trying to get my money’s worth. I did spend a lot to take you out to dinner, or did you forget?”
“No, I haven’t.”
“Good,” Patricia said and pushed me toward the door. We stepped out of her bathroom, and Patricia led me back to her vanity. She gave me a white blouse to put on. I was starting to get turned on by my reflection the more girly it became.
“Do you do this to a lot of guys?”
“Most guys run the second I pull out a razor. Guess you’re different from the rest,” Patricia said with a devilish grin.
I realized then that I could have fled. I could have left the second Patricia made her plans clear, but I didn’t. Patricia arranged a bunch of makeup on her vanity while I was lost in thought, wondering what it meant about me that I hadn’t left. Did I want to be feminized? Did I want to wear a skirt and panties and this makeup Patricia was about to apply?
“What if I told you to stop?”
“Then I would ask you to leave. Would you like to go?” Patricia asked and held the foundation she had in her hands close to her chest. “You’re free to leave. I’d be sad to see you go when you’re this close to becoming a sexy girl, but I would understand if you left.”
Patricia didn’t move as she waited for me to decide. I glanced over my shoulder at her bedroom door several times, but I couldn’t stop imagining how sad I would be on the drive home. Sad that I hadn’t gotten my dick sucked and sad that I wouldn’t have seen my completed look.
“You promise not to tell anyone about tonight?”
“Who would I tell?” Patricia asked with a laugh.
“I don’t know. My boss?”
“You’re worried about nothing, Marvin. Tonight is about you and me and nothing else. Plus, I wasn’t supposed to bring you home after dinner. That wasn’t part of the rules.”
I stared into Patricia’s blue eyes, trying to decide if I could trust her. On the one hand, I wanted nothing more than to continue down the road I was on, but then again, there was the chance that she could tell everyone at my office that she’d dressed me up as a girl before we had sex.
“Don’t be so nervous, Marvin.”
Patricia placed her hand on my thigh. It made me feel a touch calmer, but I was still terrified and paranoid that Patricia had a hidden camera or something in her room. I looked around again, not noticing anything suspicious, and then I shrugged.
“So, are you staying?”
“Yeah, I guess.”
“You’ll look so cute with a bit of makeup!”
I groaned as Patricia picked up the foundation that she’d been holding a minute ago and prepared it for my face. She explained what she was doing as she dusted and painted my face, using a bunch of different objects. I couldn’t keep up with or understand half of what she was saying, but I looked pretty fucking sexy when she stopped and told me that I was ready.
“What do you think?” she asked after I’d stared at myself for a few seconds.
“I look incredible,” I said. “I don’t even look like the same person. How did you do this?”
“I’ll teach you one day if you’d like.”
“Is that you asking for a second date?”
“Maybe,” she said with a wicked grin. “You’re so cute and girly, even without a wig.”
“Should we take a picture?”
“I thought you were worried about everyone finding out,” Patricia said and crossed her arms over her chest.
“I am, but I look so good!”
Patricia smiled and picked up my phone from the vanity, passing it to me, daring me to take a picture. She might have thought I was bluffing, but I wasn’t. I opened the camera and placed my arm over Patricia’s shoulder as we both smiled broadly. I took several pictures, more mesmerized by my own face than I’d ever been.
“It’s amazing, isn’t it?”
“I can’t believe you made me look like this,” I said as I stared at the photo of us on my screen. We looked like two girls who were ready to go out for the night. “You really find me more attractive like this?”
Patricia shrugged. “It might be weird, but yeah, I do. I’ve always liked guys who were in touch with their feminine sides, so when I paid for dinner with you, I was hoping I could convince you to get dressed up like a girl.”
“So, what happens now?”
Patricia grinned and turned toward me, reaching out to wrap her hand around the back of my neck. She pulled me close to her, and I moaned when our painted lips touched. She moaned too, sliding her tongue into my mouth.
I wondered if Patricia was getting as wet as I was hard while we kissed. I’d never been with a woman who was so direct, so confident, and I wanted her to take charge. I wanted her to tell me exactly what she wanted me to do, and to my surprise and delight, she did exactly that.
“You have some things to do before I suck your dick.”
“What?” I asked in a breath.
“Eat my pussy.”
“Sure!”
My dick throbbed at Patricia’s request. She stood and grabbed my wrist, leading me to the center of her bedroom. She lifted her dress and revealed her thong, which was wet to the touch. Patricia moaned loudly as I pressed my fingers more firmly against her pantie-clad pussy.
“Pull them off!”
“Whatever you wish,” I said. I didn’t want to upset Patricia, or she would pull out the whip, and I had a feeling that she wouldn’t be shy about using it.
I got Patricia’s panties down to her ankles and stared up into her beautiful blue eyes as I moved my face closer to her womanhood. I loved the smell of arousal on her pussy as my face got close, and I loved her taste even more. I smashed my flattened tongue against Patricia’s pussy, soaking up as much of her girly nectar as I could.
Patricia’s legs shook as I held the back of her thighs and continued licking her womanhood. She pushed on the back of my head as she let out a loud scream, which only encouraged me. I lost all sense of myself as I licked her pussy, making up for the two years that I hadn’t had any.
“Fuck! Fuck, Marvin!”
I ignored Patricia’s screams and pleas for me to stop, too lost in the moment. I wanted to feel her hot pussy cumming all over my mouth, so I kept licking until Patricia was hollering and holding my face against her womanhood.
She came all over me.
It felt like heaven.
Patricia collapsed into my arms. My mouth was all wet and messy, but I didn’t care, and she didn’t stop me when I bent down to kiss her, even though my lips were covered in her juices. We made out like we were lovers on the run, and we were only getting started.