Danielle likes to play dress up whenever we get together, but she never gets dolled up herself it’s always me she dresses. I’ve been cross dressing since college, but none of my girlfriends have ever been as accepting of my hobby as Danielle. While some of them let me dress up around them, no one has ever taken as much pleasure in my cross dressing as my current girlfriend.
When she was over last week, she decided that we should switch roles. She was going to make me up like a woman, and she was going to dress like a man. “Someone has to wear the pants in this relationship,” she insisted with a laugh. It wasn’t going to be a traditional date by any means, but it sounded like something we could both enjoy, and I was intrigued by the idea of dressing my very feminine girlfriend in a suit and tie.
Danielle had come prepared for the game with a suitcase full of clothing and accessories. She’d found a men’s suit that was small enough to fit her without giving up its masculine shape, and she’d even bought boxers and an undershirt to complete the look. She’d also found an outfit for me. She’d picked out a kimono wrap dress that would give the illusion that I had curves underneath, and a pair of suede, open toed heels plus some new lingerie. I couldn’t wait to put it all on!
Before we could start dressing, Danielle insisted on a shower. I’d already shaved and exfoliated that morning, knowing she was coming over, so I had a feeling she wasn’t worried about prepping me for my dress. When she stripped me down and pulled me into the shower, my suspicions were confirmed. She lathered a washcloth with soap and started to caress me with it, but I could tell she wasn’t as interested in getting me clean as she was in getting down and dirty. She started stroking my cock with the sudsy cloth, and it didn’t take long for her to get me hard. Eventually I took the washcloth from her and started rubbing it down her back and over her breasts, trying to get her as aroused as I was.
Within five minutes I was fucking her against the tiled wall, holding her right leg up while I thrust into her. Our bodies slid against each other, and I loved the feel of her soft, soapy tits gliding over my chest. It was one of the hottest sensations I’d ever experienced, and I pushed her more firmly against the wall so I could really pump into her. I was so turned on that it didn’t take much more effort before I shot off inside her.
Danielle didn’t come with me, but she didn’t seem to mind. She let me finish up and then pushed me away so we could finish our shower.
After we finished washing up and had dried off, Danielle set to work on getting me ready for the second half of our date. She didn’t let me do anything to help all I could do was sit back and let her pamper me. She slathered me with lotion, rubbing it in until it was completely absorbed. She did the same with moisturizer on my face, and special cream for my eyes. Then it was time for the makeup, my favorite part.
As much as I love dressing up, I love the makeup even more. A good dress and a pair of heels can do wonders for my figure, but I think that “putting on my face” is what really transforms me. Danielle is even better at putting on makeup than I am for obvious reasons and I was excited to have her make me over. I closed my eyes and let her work. She was quick and careful, and I felt her fingers apply the foundation before I felt all kinds of brushes caress my face as she put on my eye shadow and rouge. I had no way of knowing what I’d look like when she was done with me, but I knew I didn’t have to worry with Danielle in charge.
She was finished sooner than I would’ve been, and the last thing I felt before she let me look in the mirror was her pulling one of my wigs into place. When I opened my eyes to take in the finished look, I was blown away with what Danielle had done in such a short time. My skin looked like porcelain, and though I could tell I was wearing makeup, I didn’t look over the top like a drag queen or anything. And my hair! There was really nothing spectacular about it, to be honest, but it was gorgeous in its simplicity, and it was much more elegant than my usual bed head look.
Danielle didn’t stop there. She led me back into the bedroom and helped me step into my panties, pulling them up my legs and trailing her soft fingers along my skin as she did so. I felt my dick getting hard again, and I wondered if she’d bought me a spare pair of undies in case I ruined the first pair. I didn’t know if I could handle all the attention she was giving me without shooting off again.
Before I could think too much about my panty situation, Danielle wrapped her fist tightly around the base of my cock, effectively putting an end to my worries. She looked up into my eyes and smirked as she pulled the underwear the rest of the way up, my cock now covered by the thin material. “There will be time for that later,” she assured me, patting my dick. Then she simply grabbed my bra from the bed and continued to dress me.
She slid the bra straps up my arms and hooked it in place behind my back before picking up the dress and helping me slide my arms into the wide sleeves. She wrapped the front panels around my waist and tied it shut before cinching it with a wide leather belt.
Danielle was naked the entire time she dressed me, but I was so focused on my own wardrobe that I barely noticed hers. It wasn’t until she helped me slip my feet into my new heels that I remembered she was going to dress up, too. She directed me to sit in my reading chair in the corner of my bedroom and then started to do the sexiest reverse striptease I’d ever witnessed.
She stepped into her boxers, wiggling her hips as she pulled them up, and then she pulled the fitted undershirt over her A cup breasts, flattening them the slightest bit. I’d never really watched Danielle get dressed, and seeing her putting on her boxers and suit was much more arousing than I’d anticipated. As she pulled her crisp black slacks up her legs, I felt my cock getting hard, and as she tucked in her white button down shirt I knew I’d have to fuck her one more time before we left on our date.
Somehow Danielle managed to get her jacket, tie and loafers on before I finally pushed myself out of my chair and grabbed her. I pulled her close and kissed her hard, smearing my lipstick. I thought she’d be mad that I was messing up our outfits and my makeup with my sudden display of passion, but she only pulled me closer and worked her hands under my dress to pull down my panties. Meanwhile, I worked her shirt out of her waistband and unzipped her fly, thankful she’d bought men’s boxers so I didn’t have to try to get her pants all the way off. I tugged her pants down enough to bare her boxers and pushed my hand through the opening at the front.
I pushed a finger into her through the fly in her shorts and felt her dripping wet pussy envelop my digit. I stroked her pussy a few times before she pulled away from me and lay back on the bed, beckoning me to follow her. I quickly climbed onto the bed and lay above her, pushing my dress out of the way and easing my cock into her cunt through the fly of her shorts. There was still a lot of clothing to get in the way of wandering hands and mouths, but it didn’t interfere with the fucking, and I pumped into her quickly, forgetting about being a woman for a few minutes.
We were both so hot that it didn’t take more than a couple minutes to get us both off, and we came within seconds of each other. Afterward, Danielle helped me straighten my hair and makeup and put my dress back in place, and I helped her glue on a fake mustache and sideburns. We’d planned to go out to dinner, but we were afraid another urge to fuck would hit, so we ordered in instead. Good thing, too, because halfway through the meal Danielle crawled under the table to suck my cock.
Now that we’ve figured out which of us wears the pants, we’re going to try to actually leave the house next time we swap roles. Even if we don’t, though, I’ll be satisfied. As long as I get to strut my stuff for my girlfriend or should I say boyfriend I’m happy.
Mr. Craig W., San Diego, California