This is a story of an introduction to crossdressing. Unlike most stories in this vein, it does not involve a guy, at least in the first person.
This is a story about a girl who begins her own personal journey into the world of cross dressing. Our hero is named Amy. She’s 19 years old, and attends the local University. Amy is there on an athletic scholarship. She’s a freestyle swimming star, with Olympic gold medal hopes and dreams. Amy stands about 5 ft 4 in and weighs in at 115 pounds.
Her firm, muscular body yields not one ounce of fat. With her short haircut, she could even be mistaken for a boy. And that fact is what now brings her great delight and fun.
It all started during her freshman year. The swim team was in the championship meet at Edison University. As Amy’s team, the Scepter State University Sharks, was the visiting team, they had the distinction of having to use the men’s locker room as their changing room. The other girls all laughed and joked about having to use the men’s locker room to change in before the meet. One of the girls joked about the possibility that they might surprise a naked hunk of a guy in the showers while they were changing. Some of the guys had left clothes in the lockers prompting Rachel Smith, yell out a loud “Oh Ick!” upon the discovery of a pair of balled up socks.
The enthusiasm of the big swim meet had the girls laughing and joking while they got dressed. Amy was psyched and ready to swim. And swim she did! She took first place in her three events. The girls went on to win to the championship. Amy tossed her swimsuit into the locker and quickly showered for the bus ride home. After she showered she pickup all the stuff on the floor of the locker and just stuffed them into her bag. She didn’t want to miss the ceremony back at school where they would award the medals and trophies. Little did she realize the prize she pickup up when she tossed her wet suit and towels into her duffel bag. Once home, Amy tossed her cold clammy clothes into the washing machine. After her clothes were laundered, she tossed the whole load into the dryer. She was so tired that she didn’t even bother to sort them out. She just hoisted the whole load into the dryer and hit the start button. As the dryer hummed, Amy curled up on her bed. Her mind was filled with the excitment of the win at the swim meet.
“Yes!” she exclaimed. “The championship! Next Olympic gold.” The excitement wasn’t enough to stop the sandman and soon she drifted off to sleep. Just then the buzzer went off on the dryer transporting Amy back from the arms of Morpheus to her apartment. She picked up her laundry basket and went over to the dryer. Amy opened the door and pulled out her laundry one piece at a time. Towels, panties, swimsuit, jockstrap…. jockstrap? …. jockstrap! “What the hell am I doing with a jockstrap?” Amy said out loud. Amy had never really seen a jockstrap up close, so she examined this strange garment with much interest. Sitting on a stool, she fiddled with the jock’s straps, stretching them.
“How does this work?”, she wondered. She held the jockstrap in front of her mid section, and smiled a mischievous grin. Amy’s curiosity was getting the best of her. “I wonder what it’s like to wear one of these things?” she thought. In one movement, she stripped out of her terry cloth robe, and was standing naked holding just the jockstrap. She slipped one leg in it, then the other, and then she pulled the jock up to her crotch.
Amy adjusted the pouch on her pussy, and then pulled the straps down over her rear, so she was wearing it like a guy would. It fit perfectly. Amy stood there, with her hands on her hips looking at herself in the mirror. This was neat, she thought. Crossing her arms over small breasts, hiding them, she thought she could pass for a guy. She sat on the chair with her legs apart, imagining her self as a guy. The thoughts in her head made her quite horny.
Amy got up from the chair and swaggered across the room and laid down her bed. Soon she was rubbing herself through the stiff fabric of the jockstrap’s pouch. Her clit was growing hard and erect, hard than it had ever been before. Her legs bucked and she climaxed in strong waves of erotic sensation. Amy lay there quietly, quite turned by what had just happened. She drifted off to a peaceful sleep.
When Amy woke up, she scratched her head. “What a crazy dream.” she thought, “me wearing a jockstrap.” She chuckled. As she stretched and yawned she felt something sticky and wet on her belly. Amy pulled the covers down a bit, and put her fingers in the liquid substance on her tummy.
Puzzled she sniffed at it. What the heck is this? Nah, it couldn’t be. She took a small taste. Salty. No way! Cum? Whose?
Totally bewildered, Amy pulled back the covers the whole way. She blinked in surprise to find that she was wearing the jock strap she had dreamed about. Then she got the shock of her life. There was some thing in it. Her eyes got as big as saucers. Amy pulled the wide waistband of the Bike jock down to find a penis and testicles. Her penis and her testicles. Amy shook her head in disbelief. She had a penis. She touched it and then jerked her hand back quickly as if she had received an electric shock. Her penis was stirring into life, and she getting an erection. Amy looked at the oddity of it all, from her small breasts down to the head her penis now peaking out of the waistband of the jock. It was getting harder, straining against the pouch of her Bike jock strap, and it was feeling really good.
Amy stuck her hand into the pouch of her jock. Feeling around she cupped her balls in her hand and felt the wrinkled skin of her new scrotum tighten. She freed her cock from its fabric prison allowing it to stand proudly erect. As if it had a voice of its own, she imagined she heard it calling out for a hand job. Amy began stroking her cock, up and down, up and down. She had never felt anything like this before. Sparks of sexual energy filled her body as she built to climax. Her back arched and she cried out as her testicles dispensed their warm wet load of semen. It was all stars and moons and planets! “What an orgasm!” she thought. Totally spent, Amy drifted off to sleep.
Soon she heard the buzzer on dryer going off alerting her to attend to her dry laundry. `Geez louise! What a weird dream,’ she said. Still a bit unsure, she slowly pulled back the covers, pausing only long enough to think, what if. Breathing a sigh, Amy found no jockstrap, and no penis, just her panties and their normal contents. She picked up her laundry basket and went over to the dryer. Amy opened the door and pulled out her laundry one piece at a time. Towels, panties, swimsuit, jockstrap….jockstrap?….jockstrap! Amy smiled…she knew just what to do next.