“He felt her red-tipped finger draw across his lips and his body seemed to shiver to her touch. He hardly took note as she lay him back on the silken sheets, running one hand thru his hair and the other down and under his frilly babydoll. His senses were overloaded; the touch of the silky nightgown on his body, the fragrance of the room, the sight of Carolyn bending as she ministered to him. Finally, as she caressed his lips with her own and he tasted the creamy red gloss that covered them, his whole body shuddered in spasm. His boyish juice exploded into the silken handkerchief.
Carolyn smiled down at their guest and gently cleaned him. He had never in his life felt so wondrous. Lifting his back from the cool sheets, she removed his robe, and now, dressed only in his babydoll with their matching panties, she pulled the coverlet over him. Kissing him on the forehead, she whispered, “Good-night, Chrissy; sleep tight.” She turned off the light and closed the door behind her, leaving the boy asleep and dreaming.
The boy’s sleep was filled with dreams that would have disturbed him had they remained in his memory more than a fleeting moment. In his dream, Christopher had found himself back at St. Mark’s Academy for Boys in the room he shared with two other students. What surprised him, however, was that while the other two wore their pajamas as they climbed into bed, Christopher found himself dressed in a blue satin gown. The dream was hardly surprising for that night, visiting the home of Mary, a local woman who had befriended him, he had, indeed, gone to bed dressed in a frilly nightie borrowed from her daughter’s wardrobe.
He awoke from his slumber suddenly, light streaming into the girlishly decorated bedroom as Carolyn, the beautiful housekeeper, flung the curtains wide.
“Wake up, sleepyhead,” whispered the maid in his ear. “Breakfast will be ready in just a few minutes.”
As the cobwebs cleared from his brain, the activities of the previous evening flooded back into his consciousness. As if somehow disbelieving, he quickly peeked beneath the satin sheet, blushing as his feminine attire was confirmed.
“Come on, sweetheart – we’ll have to hurry,” Carolyn said as she threw back the covers.
The teenage boy, startled, tried to cover himself, but the maid just grinned and, taking his hand, pulled him from the bed.
“Here, hon, slip on your robe and let’s wash your face,” she said, holding the diaphanous, lace-trimmed bed jacket. As the boy slipped his arms through the flowing sleeves, she smoothed it over his shoulders, letting it settle lightly over the much shorter pink babydoll.
Leading the youngster into the bathroom, she draped a fluffy towel around his shoulders and then, lathering a soft facecloth with fragrant soap, began to wash the sleep from his eyes. After rinsing the lather from his smooth skin, Carolyn gently patted his face dry with a soft absorbent towel. Just as the night before, Christopher stood passively, unsure of his feelings but somehow almost under a spell as everything was being done for him. Unused to such pampering, he found it quite pleasurable. Taking a toothbrush and even squeezing the paste on it for him, she said, “You finish brushing now, Chrissy; I’ll find your slippers.”
Newly refreshed, he sheepishly returned to the bedroom where Carolyn motioned him to the small seat facing the mirrored vanity. Seated before the mirror, his eyes were drawn to the lace trimmed bodice of his dressing gown. As the maid stood at his back, slowly brushing his longish blonde hair with an ornate silver brush, his mind reeled. “This is crazy,” he thought, “she’s treating me just like a little girl or something.” Despite his embarrassment, however, the more overpowering emotion was guilt, guilt that, beneath the blush, he actually delighted in her ministrations. He felt he should put a stop to all this, but the gentle stroking of the brush and the silky touch of his gown and panties on his skin seemed excuse enough to postpone any rebellion. His mind was brought back from his reverie as Carolyn knelt and slipped a pair of pink satin slippers over his feet.
The image of a princess being attended by her ladies-in-waiting rushed through Chris’ brain as the maid took his hand and brought him to his feet.
“Oh dear, we’ll have to hurry; we can’t leave Mistress waiting.”