He was remembering how nice it was to play a game of dress-up with his cousin when she was about 12 and he was about 9 or so - they'd meet up in their grandma's attic when no one else was home, and try on some of the clothes in the old trunks up there.
Now he was 15 and she was about 17 - and they were enjoying getting to know each other again, it had been a while since they'd been together. The rest of the family went out for a day of shopping, and they were left alone after breakfast.
While she was still in her room dressing, he wandered up into the attic and began looking through some old suitcases and trunks. In one, he found a collection of women's and girls summer clothing. Searching through,he found a lovely black bathing suit and pulled it out. It consisted of a pair of black 'bottoms', or panties, full cut and shiny, and a top which was like a short bra-dress, with a flippy skirt, of the same material as the panties.
He listened at the stairs to make sure she wasn't nearby, then he removed his clothes and pulled on the panties. As he did so he began to get an erection, which felt really good to him inside the panties. Next he slid the dress part of the bathing suit on over his head and shoulders, and smoothed the skirt down over his belly. Looking in the full length mirror, he saw that the skirt didn't quite cover the panties, so they peeked out around his butt.
He thought he heard her moving around so he quickly took off the swimsuit and put his clothes back on. As soon as he had, she climbed up the stairs to the attic and saw him looking innocently through the trunk of clothing.
'Hi,' she said. 'Whatcha doing?'
'Oh, just looking through these old clothes - '
She smiled. 'I remember when we were kids we used to try things on - remember that?'
She came over and looked over his shoulder, then reached on and pulled out the same black swimsuit he had just been wearing! 'Hmmm - I seem to remember we both tried this on didn't we!' And she laughed. 'I bet it would fit me better now than it did back in those days.'
She took the swimsuit behind a screen that stood on the corner and emerged a few moments later wearing it. He thought she looked great, and his hard cock throbbed in his jeans. She came over and looked in the trunk at some other things, then pulled out a pretty white chiffon dress and some underthings, and went back behind the screen and changed into them.
When she came out he was really getting horny and wanted to try on some girls' things in the worst way. It was almost as if she read his mind: 'So - do you like this dress? Isn't it pretty? I remember how much you liked pretty things when you were a little boy - now somehow I have the idea you would like to put on that bathing suit I was just wearing!'
He stammered 'How did you guess that?'
She said, 'Oh, it wasn't really just a guess - I peeked up here a few minutes ago and saw you with it on! And if you'll put it on again, I'd love to see you in it!'
Shyly, he picked up the suit and went behind the screen. His dick was still hard as he pulled up the panties and then slipped on the dress part of the suit. As he emerged from behind the curtain, she was sitting on the floor in her pretty dress, knees up. He could see her silky white panties under the filmy dress and he got even more turned on.
'You look so sweet in that bathing suit,' she said. 'Turn around.'
He did so and she whistled softly. 'Mmmm you are VERY pretty, my sweet cousin. I think we ought to see if there is a dress in here for you to try on too!'
She went over to the turnks and began searching through them, while he squirmed a little to try to ease the tension in his hard penis. After a couple of minutes, she turned to him and held out an armful of clothing. 'OK sweetie - now you go behind the screen and put on EVERYTHING here, ok? And then we'll see if we can be nice to one another in our pretty dresses, ok?'
She looked so beautiful to him the way she was dressed - her dress was so white and silky, and smooth, and swirly, and the outline of her body in panties and a bra - he wanted very much to share that feeling with her.
So her went behind the screen and placed the clothing on the bed that was back there. After he took off the bathing suit he stroked his hard penis for a minute, which felt SO good - but he realized he'd better stop that right now and get dressed in the clothes she had picked out for him.
He looked through the bundle of clothing. There was a pair of full cut brief panties, white silk with small ruffles at the back and sides. He smiled at them, remembered looking at them when he was a boy. Now he was thrilled to be holding them. He removed the bathing suit, and pulled the new panties slowly up his legs as warm thrills ran up and down his legs. Then he took the lacy padded bra and slipped it over his shoulders and fastened it in the back.
Next he slid into the creamy white slip and adjusted its straps on his shoulders.
The fluffy white party dress was next. As he buttoned it up the front, he was amazed at how well it fit him. This was fun!
'Hey - what are you doing back there anyhow? Aren't you dressed yet?' she called from out in the room.
He walked out from behind the screen and she gasped ast the sight of him. 'Oh my! You look dreamy!' she cried. 'Who ever thought you'd look so sexy and so pretty at the same time. You darling boy - come over here please!'
As he approached her she held out her arms and they hugged, and he could see them as a couple in the mirror by the wall. The sight and feel of all that silky white material on both of them had given him the hardest imaginable erection, as he felt himself pressing up against her.
She noticed it too. 'Oh sweetie - I can tell you are so hard. What's that like? I have always wondered what a boy's hard penis must be like.'
He didn't quite know what to say, he was feeling so excited. She rubbed his back and waist with her hands as she leaned back and looked at his eyes.
'Oh darling - may I touch you there a little bit?' Without waiting for a response, she slid her hand around the front of his dress and down across his hard member. As her hand brushed back and forth across the silky material he felt waves of excitement passing though him. Her hand closed across him and squeezed just a little bit.
'Sit back here on the couch my dear sweetboy,' she said. As he did so she knelt in front of him and lifted up the front of his creamy white dress, and placed both hands on the front of his panties. 'Let me touch you please, I am so very interested in that big hard cock you have!'
He leaned back against the cushion and breathed deeply as she slid her hand down inside the front of his panties and grasped the head of his cock in both hands. He looked at her in her own white party dress, and could see the outline of her breasts inside it.
'Will you open your dress up some so I can see you too?' he asked.
She stepped back smiling 'Of course darling.'
She began unbuttoning the front buttons on her dress, slowly. As they came undone, he saw first her lacy bra, then the top of her panties - they were full cut like his and very shiny and silky. Her belly was a lovely shape and as she continued to unbutton he could see the slight bulge of her pussy at the bottom of the panties.
He had pulled his dress back down over his knees while she was doing this, but continued lying back, and his dick was still as hard as ever, throbbing a little. He had trouble keeping his hands off himself, and finally as he watched her unbuttoning herself, his hand strayed back to the front of his own lovely white dress.
She noticed this and said 'Well - I can see you are enjoying this aren't you my pretty boy. Tell me: is this the first time you have dressed up like a girl?'
'No,' he admitted. 'I do like the way if feels - but with you it is so different - I love the way you look and the way you are so sexy. Your underwear is so pretty!'
She came over to him, her dress still on but unbuttoned all the way down now. She got on her knees on the couch, one on either side of his legs, and sat down with her panties touching his pretty dress. Then she slowly lifted up the front of his dress again and pressed her pussy against his hard cock, both of them still wearing pretty panties, and she rubbed back and forth a little bit.
'I can see you like this!' she said. She put her hands across his front, smoothing the silky material of the dress across the bra he was wearing. Then she began unbuttoning the front of his dress just like she had done her own a few minutes earlier. Exposing the lacy bra he had on, she slid a hand underneath it and massaged his nipple, sending thrills of desire through him - all the while she was rubbing her pussy against his still hard cock.
She leaned forward across him, took his face in both hands, and kissed him genltly on the lips, while slowly humping her hips up and down on top of him. She murmurred into his ear, 'I would love to make you feel just as good as you can dear sweetie - tell me what you want me to do!'
He said 'Would you undress me slowly? And touch me? Please?!'
She leaned back and lifted the front of his dress again. Then she said 'sit forward for a minute, Doll-baby.'
She kissed the front of his silky panties, then sliding a finger inside the waistband on either side, slowly pulled them down, exposing his big hard cock.
'Mmmmm that looks so nice!' she exclaimed. Pulling his silky, ruffled panties down and off of his legs, she leaned forward again, and, wrapping the panties around the shaft of his hard cock, she began to gently slide them up and down on him. He writhed in pleasure as her grip and tempo slowly increased.
'You like this don't you Baby-doll!' she said with a smile. 'I know you like this - I watched you do this to yourself one time when you didn't know I was looking!'
With that revelation, she began stroking more vigorously and he felt the beginning of the warm and intense feeling he loved so well when he played with panties by himself. But this was different - as he felt himself rising toward climax, she took the panties away, and, grasping the shaft of his cock firmly with both hands, she leaned over and began gently jacking him between her breasts. He was overwhelmed with sexual feeling and then began to come in long throbbing pulses. She kept her breasts together holding him as he came, until his throbbing subsided.
'There!' she said. 'Wasn't that nice, you pretty thing!' And she smiled a big sweet smile that made him feel so very good.
Later, after they had gone downstairs to have some lunch, she asked him 'Hey - you want to go upstairs and play some more?'
He smiled. 'Sure - I really enjoyed this morning and it might be fun to play dress-up some more.'
She smiled broadly. 'I know what you like now - and there were some other really pretty things up there we could both wear for each other - and see what happens!'
She took his hand and led him back up the attic stairs. Walking over to the closet, she opened it and began looking at things.
'Look at this!' she exclaimed. 'A beautiful wedding dress! And I bet it will fit you, darling.'