Sissy Summer

When I was eighteen, and I was spending the summer hanging around town doing nothing and basically waiting for college to start so I could leave, my girlfriend was called Emily. I'd known her for a couple of years and we finally started going out just as school finished. She was a little short, blonde, very cute and, well, she liked us to match.

Match, you ask? Whatever do you mean?

Well. Quite often, when she bought new clothes, she'd buy something twice. One for her. One for me. What started as an innocent sex game the day her parents left for their summer cruise, involving me wearing a pair of her panties on a dare, ended up with me spending many a day lounging around her house in a dress.

Emily liked cute, girly clothes. Pleated miniskirts, colourful tights, long socks, tiny cardigans. Big bangles and headbands. Skinny jeans and denim shorts. Bright high heels and plain ballet flats. And dresses. Lots and lots of dresses. The first time we matched, it was because she'd lost too much weight to fit in her favourite dress anymore, so she bought a new one in a size down, and let me keep the original. It was strapless, with a pattern of red flowers, tight at the waist and with a big, puffy skirt held out by loads of netting. She had left me at home in front of the TV wearing some of her other clothes -- a purple miniskirt, black tights and white vest top -- and caught me completely by surprise when she crept through the door and bent over to whisper in my ear:

'Hiya sweetie! Come and see what I've got!'

I followed her up to her room and watched her strip off, pull the dress out of the bag and slip it over her head.

'Nice. But don't you already have one?' I asked as she twirled around to show it off.

'Yep. But, well, the old one didn't fit anymore. I guess it'd fit you though...' she winked.

I smiled. I had long admired that dress. I immediately stripped and dived for the closet, pulling it off its hanger and putting it on. Emily grinned.

'Cute!' she said as she dragged me to the mirror. 'Just look at us!'

I picked her up and pushed her against the wall as her hand reached under the skirts of my dress and our tights rubbed together in little 'swish' sounds.

Emily would allow me no shame and no embarrassment: the first time I ventured outside her house whilst matching her, we were both dressed in overly-tiny denim shorts over black tights, cute black ballet flats and tight black tshirts. 'C'mon, we need milk,' she said, grabbing me by the hand and pulling me off the couch. We were out the door and half way down the road to the store before I knew what was going on. With my hair grown out a little, my bra pushing out my shirt just enough and lipstick and mascara on my face, we earned only curious and longing stares instead of any disgust from men in the street as we pranced down the road. Another night, she dragged me out on the town in matching green dresses and heels. I was scared as we walked down the street holding hands and earning honks from passing drivers, but fortunately she allowed me the comfort of a only-slightly-creepy fetish club where I was free of being judged. As we danced and she entertained herself by trying to hook me up with guys, I felt like the belle of the ball.

Most days, though, we would just curl up in whatever we chose and watch TV or something before she dragged me to the bedroom. One of the best days of our summer relationship was the day after she found two identical wedding dresses in a thrift store. Call it weird if you like, but sitting with the massive skirts puffed out around us and our legs tangled up in white stockings and the fingers of our white lace-gloved hands intertwined was absolutely heavenly.

Emily had a rather dominant side that would come out every now and then. I arrived at her house one day and she answered the door in a short and very light, floaty pink summer dress. She also wore white lacy socks with ruffles around the ankles, and shiny black mary jane shoes. She looked so cute and I knew I would too as she grabbed me and pulled me through the door.

In her room, she lay on her bed and clicked her fingers, pointing to the floor -- the universal sign for me to get my ugly clothes off straight away. I pulled off my jeans and shirt and stood waiting excitedly for her to bring out my copy of her adorable outfit.

First, she threw me a white bra and panty set. They were shiny and satiny, and I eagerly pulled them on. She stood up to pull the dress over my head and zip it up, kissing me as I appeared from its pink folds. I then pulled on the socks and carefully arranged the ruffles, then she bent to buckle my shoes. We stood to admire how cute we looked in the mirror, and I was so overcome that I didn't notice her grab my hands and pull them behind my back.

Click!

She snapped my hands in to handcuffs and, giggling, pushed me back on to the bed. I lay helplessly on my side as she pulled a riding crop from a drawer.

'God, sweetie, why do you let me do these things to you? No other man would let me dress him up in the exact same clothes I wear every day!'

She used the riding crop to lift the front of my dress. 'See, you get off on it too!' she said, noticing my cock straining against my panties. 'I wouldn't even wear half of this stuff myself if it wasn't to humiliate you!'

She stroked my cock with the riding crop and I moaned.

'Quiet, precious, good girls don't make nasty noises.' She pulled open the drawer again and took out a baby's dummy. My eyes went wide as she stuffed it in my mouth. Ultimate humiliation. She kept stroking me with that riding crop and it was making me wild.

'Now, is my baby gonna be good?' she asked. I nodded, but secretly had a plan of my own. As much as she loved to be dominating, to push me around and dress me up in all sorts of girly outfits, I also knew she liked it a little bit rough.

'Good,' she said, and undid my handcuffs. I let her stroke my cock with her riding crop a few more times before I grabbed for it and pulled it out of her hands.

'Hey!' she said, in mock outrage. I stood up and faced her, using the crop to stroke and lightly whack her pussy. It was her turn to moan and I took advantage of her distracted state to push her down to her knees.

Emily looked up at me as I lifted my dress to place the skirts over her head. Pulling my cock out of my panties, used it to slap her face before I forced it in to her mouth, the dummy still in mine. She sucked hungrily and greedily, and I found it hard to stay standing, but eventually I pulled out of her mouth, lifted my dress out of the way and came all over her face. She smiled and licked at the drops closest to her mouth, but some escaped and dripped down to her breasts.

'You gonna clear that up, baby?' she asked.

'Of course!', and I knelt to lick her breasts clean. We both laughed and lay down on her bed to cuddle in our dresses.

It was one of the best summers of my life -- I've never felt more comfortable than when I was dressed in miniskirts and dresses that matched those a beautiful girl was wearing too. I would have stayed with her through college but, well, one day I caught her cheating on me with a girl who had a similar dress style to her. I guess I should have seen it coming.