Jimmy could scarcely blink as he watched Jenny leave the room, padding into the hallway in her stocking feet. Involuntarily he stared at the baby doll as it draped lightly down her back, just enough to cover her panties–an outfit that had made him toss and turn so a mere 24 hours ago. Only now she had on tights, like the ones he admired on her legs so many times in the past. And even though her body was more modestly covered by this surprising addition, he found himself even more attracted to her.
He leaned the door closed and turned off the light, his revery both distracted and deepened by the sensation of his own tights stretched across his legs, pulling softly at his toes with every step. Trembling slightly, he walked over to the bed and turned on a little night light next to the nightstand, decorated with an angel motif. He simply had to look at what he was wearing for a moment before he went to bed.
The satin material of his pink sheath was warming up quickly, and as he sat on the bed and pressed his nylon-clad legs together he felt the warm insulation of the tights start to ease his chill. He couldn't believe that he was wearing Jenny's nightie again! The feeling was so intensely tingly he didn't even dare touch his own body or legs and make things worse. Or better. It still had a few wrinkles from when she wore it the night before. He smiled and felt his cheeks turn a gentle pink as he thought of Jenny's little kisses.
He heard Mrs. Dale approaching in the hall. Feeling suddenly embarassed, he tried to get into bed, but had to pull off some of the decorative pillows first. He felt her eyes on him as he piled them up on the floor. "I'm glad to see you're finally getting into bed, Jimmy–tomorrow's going to be a long day. And look how careful you are with these old pillows! I'm going to tell your mother what a nice houseguest you are."
He pulled back the covers and was about to jump in when he felt her hand on his arm, and then on his bottom as she repeated her inspection from the night before by lifting up the back of his nightie. Jimmy's face went red as a tomato as she paused, her voice soft and low as she made a questioning noise. She lifted the hem up higher, and then tugged at the waistband of the tights. "Whats this? I didn't notice you were wearing tights–maybe my eyes aren't used to the dark."
Although he had no reason to believe so, Jimmy got the sense that Mrs. Dale knew he was wearing tights as soon as she walked in the room. Maybe she wanted him to take them off? Maybe she had seen Jenny in hers, and was alarmed by the unusual intimacy of the two of them putting on such a garment together? Maybe this was all wrong? All these thoughts flew threw his head in the brief moment that she pulled back the tights just enough to confirm that he had on the lacy pink panties. He felt an unwanted surge in front, underneath these layers of nylon.
"Good, you've got your panties on." She let go of the waistband with a snap, and as his nightie floated down, she patted him twice on his rear to prompt him to climb into bed. Grateful to have the covers to hide under, Jimmy settled in as she kissed his cheek. "Did Jenny make you wear tights to bed? She gets a little enthusiastic sometimes–maybe more than she should. Are you comfortable with them on?"
"I'm okay, Mrs. Dale. Jenny was just worried that I'd be cold. She's just helping me out."
"Oh Jimmy, you are a real treasure–your mother is going to be very happy to hear how good you've been!" She kissed him one more time, said goodnight, and left. With a sigh of relief, Jimmy sank deeper into his pillow. He was too wiped out from all this excitement and embarassment that he couldn't be bothered to turn off the nightlight. He fell asleep surprisingly fast.
In the middle of the night, he woke abruptly. He had been dreaming about Jenny leading a pack of girls in chasing him through the school. They caught him repeatedly and took off parts of his clothes, finding girls underwear underneath.
His panties and tights could scarcely contain his erection. He kicked off some of the covers to cool down, hoping his excitement would subside enough so he could go to the bathroom. He was immediately flushed with tingles though, as he saw the lace trim of his nightie, and felt his nylon legs slide together. Frustrated, he pulled the covers back up.
The dream had been so vivid, his night had been so crazy. Almost against his will, he felt his hands slide over his chest and stomach. He tried to see if he could go back to sleep, but was kept in his fitful state by the visions of girls, all wearing dresses from that Sears catalog. And tights. As his hands wandered over his own tights, he imagined they were Jenny's hands uncovering the feminine garments under his school clothes. He tossed and turned hoping in vain to get back to sleep, but unable to keep still. When he decided he better get up, he opened his eyes and immediately saw the pink straps of his nightie and a small bit of lace trim peaking out from under the sheets.
It was all too much for him. The feeling of his clothes, the smell of Jenny's perfume, the crazy dream, and thoughts of Jenny's embrace–what finally did him in was his earnest attempt to get up. The feeling of the tights over his panties as he tried to rise overcame him and he collapsed back down shuddering in convulsions.
After a moment he was still, his heart beating furiously. Then he took stock of what happened. With dread, he sat up, pulled up the nightie in front, and looked to see what the nightlight would reveal. A small stain on the front of the tights, near the waistband, confirmed what he already knew. He pulled them down, and gained some small relief when he found that the little panties were pretty much dry–his tossing and turning had caused things to get rearranged abit down there.
Quietly, he stood up and peeked out the door to see if he could get to the bathroom unnoticed. The house was dark. He snuck out into the hall, and bumped into something on the floor before he made it to the bathroom. Once inside, he did his best to clean up his tights with tissue, the bathroom fan covering the noise he made. He then pulled down tights and panties together to sit on the toilet, thinking that if perhaps he had remembered to do this before going to bed, he might not have woken up in the middle of such dreams and been in the mess he was in now!
He thought about taking the tights off altogether, but was sure there'd be questions in the morning if he did. So he pulled everything snugly back up, washed his hands, and turned off the light to give himself a moment to get used to the dark. He opened the door to leave, only to bump into Jenny in the hall! He knew it was her both by her height and by the nylon-covered toes he stepped on.
"Are you okay, Jimmy?" she whispered. She reached for his shoulder, but first found his chest. As she moved her hand, he felt a strap slide off his shoulder. "I heard you get up, and I thought you might be feeling sick."
Jimmy took her hand as he shrugged his strap back up, and said "I'm fine, Jenny, I -uh, well, I just had to go to the bathroom." She reached around with her other hand to give him a quick hug.
"You were in there awhile, so I got worried. I'm glad you're okay. Is my nightie too cold? How do you like wearing my good tights?"
Jimmy was deeply grateful for the dark, but was feeling uncomfortable talking about this, after what he'd just experienced. "Well, um, they sure do keep my legs warm."
"I never even checked to see if they fit you. Do they fit? Are they too small? Where do they come up to?" Her hands found his waist and pressed around through his nightie to find the waistband. "They should stretch enough to fit you," she whispered as her fingers somehow wormed into the waistband and began pulling his tights higher up his waist. In the very dim light of the hallway his white thighs became uncovered and he felt more exposed than if he had been naked. He instinctively tried to pull back, but bumped into the doorframe.
"They fit perfectly, Jenny! They're like, well, um, well they fit better than anything I've ever worn. They're so snug and all..." Jimmy felt like an idiot talking about this, but was almost helpless to stop. Luckily, Jenny did.
"Okay, good. My turn for the bathroom. Good night Jenny Two!" She slid past him and closed the door.
"Good night, Jenny One" he said as he finally snuck back to his room, thanking his lucky stars that he hadn't taken the tights off. He sank into bed and fell asleep quickly and deeply. Tomorrow he'd figure out how to clean her tights and get through another day.
Comments
such a sissy...
Jimmy is such a sissy...! oh...!
I love this story.
Jenny is so open to him, touching him, kissing him,
because she knows nothing will happen!
He is not like the boys at school, always trying
something with her, he is simply a sissy,
and even though he loves the smell of Jenny's clothes
and finds girls pretty, he won't try anything
and will shy away from any "attacks" coming
from Jenny.
I can understand him, worn girls' clothes
were the most delicious things on Earth when I was
his age!
Thank you for this beautiful story...
Gaby.
Poor Jimmy! :)
He's still dealing with conflicted emotions, but (perhaps because he's so enamoured of Jenny) he doesn't try to cover up the fact he's enjoying wearing her clothes - even though he hasn't shown any crossdressing tendencies before. As for Jenny - I think she's also attracted to Jimmy - especially when Jimmy wears her clothes - and is keen to (gently!) get the attention of Jimmy's "flagpole"...
I like the way everything's done semi-innocently - although Jenny is thrilled to see Jimmy in her clothes, as far as we know there wasn't any pre-planning before he arrived - and if it wasn't for him fortuitously forgetting to pack his PJs (and perhaps fondling her undies upon arrival), he might not have had such an intimate appreciation of feminine nightwear...
It's all very gentle, likely to remain part time, and there's only a miniscule amount of coercion involved - so unlike Gaby, I'd be very hesitant to use the 'S' word, especially as it tends to be negative connotations, being frequently associated with stories in the forced fem / sexual slavery sub-genres.
There are 10 kinds of people in the world - those who understand binary and those who don't...
As the right side of the brain controls the left side of the body, then only left-handers are in their right mind!