Sissy Wears Boyshorts

Nineteen year old Charlie lay pinned on his back by the impassioned brunette. Colleen had easily seduced the prissy boy and was now joyfully fucking him on her canopy bed.

Earlier in the day Charlie had delivered a roasted chicken sandwich that Colleen ordered from Panera. She spotted his girlish mannerisms, which intrigued her, and asked him inside.

"I'm all alone and I'd love to have someone to talk with" said Colleen as she batted her long lashes and smiled sweetly.

Colleen and the nervous boy sat together on her sofa and introduced themselves. She asked him to call her 'Miss Colleen'. Wasting no further time, the sensuous lady began teasing him.

"Do you know what boyshorts are?" she asked coyly.

Charlie understood that males were not supposed to know the styles of ladies underwear.

"No, Miss Colleen" he lied awkwardly "what are they?"

"Well let me show you dear. I just happen to be wearing a pair." Colleen smiled and daintily lifted the hem of her velvet circle skirt up to her chin.

Charlie gawked at the delightful panties adorning Colleen flat tummy and her ample hips. The shiny nylon material was baby blue with a spray of small white dots. Lace embellished the leg openings and a precious little ribbon bow sat at the middle of the narrow elastic waistband. The sissy had dreamed about having undies like these in his secret stash.

He continued staring until Colleen put a manicured index finger under his chin and lifted his gaze from her panties to her eyes. With her softest motherly voice she said "These are called boyshorts, Charlie. So, boys can wear them, too. They'd look really cute on you and I think you should try a pair. Come upstairs with me, dear."

Colleen led Charlie to her bedroom suite on the second floor and opened a dresser drawer of wonderfully pretty lingerie. Charlie stood enchanted by the lacy bras, fancy knickers, pettipants, camisoles and slips. They were much silkier and more feminine than his mother's collection. He wanted to wear all of them.

Colleen chose a pair of boyshorts trimmed in lace like hers but with lovely pink rose buds on an ivory tummy panel and she offered them to Charlie.

The shy boy would not take them from her though. So, she placed them back in the drawer.

"I'm not sure I should do this" he explained feebly "Maybe I should go home. Mother might be needing me."

"Am I going too fast for you dear?" Colleen asked "Maybe you'd like a little tour of my boudoir."

She showed Charlie her lighted makeup table which was full of Covergirl and Revlon beauty products along with hair curlers, fragrances and even a pair of silicone bra inserts. Charlie longed to sit at the table and make himself pretty.

Colleen read his thoughts and offered him a chair. After putting his hair in volumizing curlers, she painted his lips coral, gave him cat eyes and spritzed him with a lovely floral scent. Finally, she replaced his stud earrings with large gold hoops. Charley thought he had never looked so good.

"Thank you, Miss Colleen" he simpered "I feel so feminine!"

Then they explored Colleen's huge walk-in closet. There were dozens of pretty frocks of all types from chic cocktail dresses to floor-length ball gowns and even a vintage bridal gown with oodles of lace. Colleen and Charlie were about the same height and weight, so he guessed that they both wore the same dress size.

Colleen's closet also held racks of gorgeous high heel stilettos, strappy sandals and platform shoes in every color. Charlie could have happily spent all day in there.

Finally, they went to the in-suite bathroom where Colleen showed Charlie her favorite body washes and shampoos. Before leaving the bath she also showed the sissy where she kept her tampons and sanitary pads.

"I'll bet that a boy like you keeps a supply at home" said Colleen half in jest. When Charlie began to tremble she added in a reassuring voice "Don't worry, Charlie, I won't tell anyone."

"Now. Let's get those boyshorts for you."

They walked to the bureau and Colleen picked up the panties she had already selected.

"I have a lovely soft cup bra that will look pretty on you, too" she added.

This time Charlie accepted the feminine underthings. Colleen led him to her bed, pulled back the floral duvet and settled him on the satin sheets. Then she undressed the languid youth, gently pulled the dainty nylon boyshorts up his silky smooth legs and clasped the pretty Felina bra behind his back.

Charlie sensed that Colleen was going to fuck him but his nervousness had made him impotent. So, he began to get up off the bed intending to flee. Colleen expected this because nancy boys had run away from her before. She was not about to let this one get away. Colleen wrestled Charlie onto his back and lay on top of him.

"We're just going to get to know each other a little better honey" she cooed.

She kissed Charlie on his neck and nibbled his ear lobes. When he began to relax she moved her lips to his mouth and french kissed him.

Then in a moment of candor she asked "Do you think I'm pretty, Charlie?"

Colleen was very attractive and sexy, too. Her lustrous raven hair was shoulder length and wavy. Her Cupid's bow lips were painted the same bright red as her long manicured nails. Her succulent titties stuck straight out in their bullet bra as if begging to be fondled.

"Yes, Miss Colleen" he replied "You're the most beautiful woman I have ever seen!"

Colleen was touched by Charlie's admiration and she pressed on.

"Do you think you might fall in love with me, Charlie?"

"I think I'm already falling in love, Miss Colleen."

Colleen's pussy juices moistened the cotton crotch of her boyshorts when she heard the L-word. She removed her wet panties and pulled down Charlie's boyshorts, too. Then she spread her wet cootchie over Charlie's still flaccid dick.

She sensed his embarrassment at being too soft for screwing.

"Don't worry, Charlie. You won't disappoint me" she said "I am craving sex though. So I'm going to put a vibrator on your little dickie bird. You won't mind, will you?"

Without waiting for an answer Colleen slipped the elastic band of a small pulsing toy around the tip of Charlie's soft rod. Then she tucked the vibrating device and his shrunken weiner between her dewy thighs.

Colleen was a pro at masturbating with limp dicks and vibrators. She deftly moved Charlie's warm flesh and the sex toy around her pussy lips and clitty until she found the spot that gave her maximum pleasure. Then she held it in place for two wonderful orgasms.

Charlie was so excited by Colleen's arousal that he became semi-erect. Colleen noticed this.

"I'm going to stuff you inside me, Charlie" she said.

She removed the vibrator, forced his half-erect penis inside her cock-starved pussy and humped him until she climaxed two more times.

Charlie wasn't able to cum but he felt wonderful about penetrating the most intimate recess of Colleen's amazing body. She shared this feeling and kept Charlie's member tucked securely inside her.

Then the emotional, love-struck boy blurted out "Miss Colleen, I want to be your sissy maid. May I? Please!"

Colleen's heart leapt with joy when she heard Charlie's offer. She had always wanted a little minion and this sweet little pansy was applying for the position.

"Yes, my dear!" she exclaimed "I'll even buy you a black satin uniform with a frilly white apron."

"Can I have petticoats, too, Miss Colleen?" he pleaded.

"Yes, Charlie, and a corset with garters for your nylons and femboy shoes with bows on the toes!"

The two excited lovers beamed smiles to one another, hugged and kissed.

Hornier than ever, Colleen pushed the sissy's penis deeper inside her and fucked him with the full force of her ravenous cunt. Charlie was overwhelmed by Colleen's powerful lust and happily surrendered himself to her. As girlish feelings swept over the helpless sissy his dick stiffened.

With Colleen pounding him from above the euphoric ninny unleashed a gigantic load of spunk into her eager snatch. The lady was so stunned by Charlie's explosive ejaculation that she nearly fainted. After exchanging tender words the two exhausted lovers fell asleep in each other arms.

Our story has an almost perfect ending. There was one tiny hitch though -- almost too small to mention. Charlie had completely filled Colleen's pussy with his gooey cum. So, the dripping lady had to wear period panties for the remainder of the week.