It was the first Sunday of September, 1973, and Jackie had the blues. It was the summer before his first year at the U, and it had been uneventful, particularly in the romance department. He was attractive enough, slim and sandy-haired with striking blue eyes, but shy; even as a lifeguard, he didn't attract much attention from the girls on the beach, and he never knew how to initiate things with them. So, he'd started the summer alone, and was ending it that way.
He finished his last shift on the beach stand and packed away all the gear for the winter. When he was done, he walked back to the small boarding house beyond the dunes, to shower and finish packing for his trip up to college the next day.
Heading around back to the outside shower, he passed the innkeeper's daughter, Lulumae, who was on the patio, putting away beach chairs for the season. She was a strawberry blonde about a year younger than him. She was an active and athletic girl, but also cute, part Southern belle and part freckled tomboy. She was always running to the beach and into the water and back, so she wore her hair short in an easy-maintenance style. She always wore loose-fitting sundresses, as she did today, that left her physical features a matter of speculation. Jackie regarded her from time to time, but she was always busy, and he was always tongue-tied. Another missed opportunity, he thought to himself, glumly.
As he entered the outside shower, he heard thunder in the distance, and as he stepped out of his trunks it began to rain. Naked, he turned on the shower and sat on a little redwood bench while it warmed up.
Jackie always found it a little sexy to be naked in the outdoors, and frequently it gave him an erection. This time was no different. He toyed idly with his cock and ran a hand over his nipples, and was suddenly overwhelmed by the urge to jerk off. Checking the door, he felt the latch was closed, if a little loose. No worries, he thought; it was really starting to rain out there, and nobody would want the shower. He leaned back on the wooden bench and extended his legs under the warm running water, and began to stroke himself.
As he surrendered to the delicious sensation of masturbating out of doors, he noticed a woman's one-piece swimsuit hanging on a nail on the back of the door. Jackie was always a little bit fond of women's clothes, particularly stretchy things like his sister's swimsuits and mom's panty girdle. When he was lonely, he would from time to time put on something from their dressers or the laundry. He would imagine himself as a girl while he got himself off. He was not a crossdresser in the sense that he wanted to dress all the way up and go out as a girl; he just liked the tightness of spandex around his chest and his ass. He recalled that now, as he regarded the swimsuit on the door.
I shouldn't do this, he thought to himself. I don't know who's suit that is, and they would surely object. However, his growing desire and his tightening penis were urging him on, and it was almost involuntary. He reached up for the swimsuit. It had a pretty floral pattern, with shoulder straps and stiff bra cups. The bottom was like a bikini, covered by a little skirt with the same flowers on it. Jackie decided. He slipped his feet into the swimsuit and pulled it slowly up, over his hips. His erection disappeared into the tight panty and the little skirt brushed his cock. He pulled the top over his two arms, and the bra cups cradled his natural chest flesh, and caressed his nipples.
Hoo, boy, Jackie thought, I better not come all over this suit. He pulled the crotch of the bikini panty aside, and pulled his erection and his testicles through it, so they were outside the suit. This way, his orgasm would not end up all over the swimsuit.
Standing, he leaned back against the shower wall opposite the door, and began to jerk it in earnest. A cracked mirror hung from the door where the swimsuit had hung, and in the dim light he looked like a pretty, athletic girl in her bathing suit. His pulse began to race, and the threw his head back in ecstasy.
"Holy fuckin' shit," a girl's voice said suddenly. Lulumae stood in the open doorway.
Jackie was paralyzed, with fear and embarrassment, and also incredible arousal. He could not speak. The rain poured down behind her in the doorway, which Lulumae left ajar. A smile began to spread over her face. "Boy, is that my fuckin' bathing suit?"
Jackie was further stunned by the realization, that yes, it was her bathing suit, and he was wearing it and holding his engorged dick in his hand, and he was more or less helpless. He still couldn't speak.
"This latch don't work too good," Lulumae said, wryly. "You queer?" She asked him.
"No," Jackie whispered.
"You like boys?"
"No!" he replied, emphatically.
"So you like girls . . . but you also like girl's clothes."
"Yes."
She paused and regarded him. "You like me?" She asked.
"Oh, yeah!" Jackie managed to say.
"Well, all right darling. Now we understand each other. I came in to get out of the rain, but I could use a shower too. You keep that on if you want," she offered, referring to the swimsuit.
Jackie watched, thunderstruck, as Lulumae pulled the sundress over her head and stepped out of her panties. He had never been so sexually aroused in his entire life. She was a little shorter than he, but only a little, with smallish breasts that were obviously still developing, and pointedly erect nipples. She was slim but muscular, with a perfect ass and a thin furze of red hair over her pussy.
She faced Jackie and showed herself to him, completely nude.
"This good for you, Princess?" Gesturing to the hook on the back of the door where her clothes were hung, she said, "Maybe you want to wear my dress and panties too?"
Jackie lost it. He instantly climaxed with those words. He hadn't even touched himself, he just came. His cock spasmed uncontrollably, firing semen in all directions, on the swimsuit, on his legs, on Lulumae's tits and belly. He sort of passed out from the release, and lay back on the bench, blissed out.
Lulumae rinsed herself off, then turned the shower on Jackie, who was revived by the feeling of warm water washing over him.
She laughed. "Shit, darlin', that was fast. I was hoping to have a little fun with you. Better slip out of that suit so I can wring it out." She slipped the straps off his shoulders and pulled the suit down and off his legs. His cock was still erect.
Crouched naked between his legs, with the warm water running over them, Lulumae said, "Well, hell, sweet-ass, you gonna be ready to go again soon after all!"
Jackie was rising to the occasion, but was full of conflicted emotions. "Nobody's ever seen me wear clothes like that before. Nobody knows."
"Except me?" she asked, with a mischievous twinkle.
"Yes! And I don't understand. You're a girl but you don't mind? You don't think it's ..."
"Oh, fuck no, Jackie. I'm what you call a free spirit. I blow with the wind, and take pleasure wherever I find it. I like sex a lot, and I like it all different ways. Boys, girls, indoors, outdoors, I will have sex fuckin' anywhere, with anybody. And I wear whatever kind of fuckin' clothes I want, and wear 'em anywhere I want, but boys can't. Never fuckin' understood that."
