This, like other stories, is fictional but based on real experiences of mine. It is written in the third person, which I find sexier than first person.
He had been out walking, really enjoying the vacation at the beach with his aunt and cousins. It seemed like two weeks was going by so fast! This was the highlight of the summer for him, surely.
He got back to the cottage, and there was no sound, no one was home. He spotted a note on the kitchen table:
We've all gone down to the water. Won't you come swimming with us? There are extra swim suits in the dresser in my bedroom, why don't you try some on and see if you can find one that fits . . . And the note was signed, Sally.
He had not been swimming, was too modest to appear on the beach clad only in his speedo trunks which revealed too much of himself as he experienced the beginnings of manhood and the uncontrollable erections which sometimes went along with it. How nice of her to figure that out and tell him in a note, so as not to embarrass him!
He entered her room and opened the dresser drawer. On one side, there were a couple of pairs of bathing trunks, well worn, but large and much less revealing than his speedos. He took out a red pair and laid it on the bed, and stepped out of his jeans and pulled off his tee shirt. Glancing back at the drawer, he took out a ladies swim suit, a pretty white one with a lingerie-style design: a short flippy skirt covering the white panty beneath it. He held it up against his already swelling penis and rubbed the silky smooth fabric across himself, feeling tremendous pleasure and excitement
Trembling slightly, he stepped into the panty of the suit and pulled it up around himself, putting the straps up and over his shoulders, and straightening the bottom and the skirt out with his hands. Mmmm this felt so delicious! He walked over to a full length mirror and looked at himself, felt a growing excitement, and was thrilled at the image of himself he saw reflected back.
Suddenly the screen door opened and his Aunt Sally walked in the room! He jumped with fright, and just as she saw him standing there in her pretty white swimsuit, he picked up the pair of red trunks and lamely said Oh hi I was just trying on bathing suits like you said to in the note ... His voice trailed off weakly.
Sally looked at him questioningly, her gaze slid down toward his middle where the bulge of his hard penis showed, even though the little skirt, then she looked back up at him and a sweet smile slowly spread across her face.
Oh, ok Billy, that's fine. I just came back to get my suntan lotion. I'm going back to the beach, please come join us. I suggest that the red trunks might be more appropriate for the beach, but I will say that you look VERY nice in that swim suit of mine, and you're welcome to try on the other one that's in the drawer. For that matter, please feel welcome to try on anything else you see in the dresser too!
And with that she walked out of the room, and into the kitchen to get her lotion. She was well aware what was going on with Billy, she'd raised two sons and seen them undergo the early teen years of desperate horniness, sometimes looking at Playboy images of scantily clad beauties, and yes, sometimes trying on her feminine clothing without being aware that she knew exactly what was happening. She was thinking, he's not really my nephew, he's more like some distant second cousin, what if I were to help him out of his misery a little bit, and relieve the bulging hard-on for him at least for a little while so he won't be so embarrassed to go to the beach?
Billy, she called out from the kitchen. Did you try on the two piece suit? she asked, giggling in a friendly way.
No, he said, as he pulled on the red trunks. Thanks anyway, he said a bit gruffly, still embarrassed.
She walked back in the room. I'm sorry if I startled you, she said. I do know what you are going through nowadays, and if you weren't too shy, maybe I could help you out a little bit?
What do you mean? he asked.
Well, I know that boys, well, really, young men like yourself, have urges and often need to seek ways to relieve those urges, if you get my meaning. It is not at all out of the ordinary for a young man to enjoy the excitement of trying on feminine clothing, which social taboos require him to do in secret. Maybe I could help by allowing you to try on some of my clothes, if I promise never to tell a single soul! And maybe we could even let you feel very good for a little while, and it could be a special secret between us, and you could grow safely into a man with some understanding of what it means to have and acknowledge the powerful feelings you were just getting when you had on that white swim suit.
Oh Aunt Sally, he said. You're so nice, and so understanding. But I am confused, I don't know what to do, what you want me to do.
She smiled. Oh, I'll show you and help you, Billy.
She closed the drawer the swim suits were in and opened the top dresser drawer. Searching around in it, she took out a pair of lacy white brief panties, and a lacy white bra that matched.
Here put these on, and the a dress over top of them. She got a pretty summer sun-dress out of the closet and hung it on the door. I'll be in the kitchen, let me know when you are dressed. She smiled brightly and walked out of the room.
His penis was hard and throbbing again, as he took off the red swim trunks and pulled on the panties. MMmmm they felt good against his manhood. He looked at the bra and was overwhelmed by the idea of it. But he took the dress off the hangar and slid it down over his shoulders it seemed to fit perfectly, and as he looked at himself in the mirror he thought he really did look a lot like a very pretty girl. In the mirror he noticed that she was standing in the door watching him, and he was now really excited and horny.
She came back into the room and said Ok Billy now just relax, and sit down on the bed, because I know your knees are feeling a bit weak aren't they?
He sat down and just nodded, to excited to speak. What was going to happen now?
She stood in front of the mirror, smoothed the sun dress she was wearing down over herself, and said, looking at him in the mirror, Isn't girls underwear special? Haven't you always wanted to get just a little bit better look at it than you have been able to? Well, wearing it yourself is a very good way to do that. And here's another good way
With that she reached behind her back, unzipped the dress she had on, slipped the straps off her shoulders, and let it fall to the floor. She stood before him wearing panties just like the ones he had on! and a bra, and nothing else. She turned slowly around in front of the mirror, swaying a little, making sure he got an eyeful of her slender but very curvy figure.
He writhed on the bed, feeling the smooth fabric of the dress all over himself, and the special feel of the silky panties underneath. This was so exciting but he couldn't think what to do next. He fought a tremendous urge to put his hand down on his penis, and as if she was reading his mind she said softly, Billy: It's ok to touch yourself when you're feeling like this, you know. Some men even find it especially exciting to do that when a woman is watching them!
Oh Aunt Sally! I'm too shy to do that in front of you!
She spoke very softly. Relax, Billy. Ok lean back against the pillow and close your eyes for a minute.
He leaned back and closed his eyes, and she stepped closer to him and began gently stroking his chest. He felt a thrill as she slid the fabric back and forth over his naked skin. Then she slid her hands down to his waist and then along his sides, over his hips. She could feel the panties beneath the dress.
Do you like wearing my panties? she asked softly. He nodded, still keeping his eyes closed.
You can open you eyes now, Billy.
He opened his eyes and she was standing in front of him touching him through the dress and the panties. She had removed her bra, and her beautiful breasts moved from side to side as she touched him. He stared at her belly and the panties she had on. She slid her hands up under the skirt of his dress, and slowly lifted it up and let it rest at his waist, and then touched him lightly on his rock-hard penis though the panties. She smiled at him and said, Relax some more Billy, let yourself enjoy this.
Then she put her hands under the waist band of the panties, and pulled them down and slid them off his legs and over his feet, dropping them lightly on the floor. Then she took his hard cock in both her hands and began stroking him gently, saying Oooohhh Billy, does this feel good? Do you like this? Don't answer, I know you do.
She stroked him steadily and gently, kept going, then gradually increased her hold and the tempo of the stroking, he was panting heavily now, she could feel him getting harder, she held him more tightly now, one hand around the shaft of his dick just below the head, and the other hand below alternately stroking his shaft and his balls. She was moaning softly. Then he started to come in gasping spurts, thrusting his hips up and down, feeling the tremendous ecstasy of his first assisted orgasm, and she moaned in pleasure at his excitement.
He finished coming, but she kept her hands firmly on him as the pleasure lingered and lasted long. Finally his cock began to subside, and she released him and leaned over and kissed him softly on the mouth.
Billy this will always be our little secret, and maybe some day we can do it again.
With that, she quickly put her bra back on, slipped into her dress, and left the room, saying, OK, young MAN as soon as you can, get your swim suit on and join us down on the beach! She peeked into the room as he was adjusting the swim trunks around his still slightly hard cock, smiled, and said Oh and you really DID look cute in my white swimsuit-maybe you'll try it on again for me some time! She grinned and left, the screen door slamming behind her.