Undercover Girl - Chapter 4

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Undercover Girl-Chapter Four

By Katherine Day

(Copyright 2019)
(Marcus discovers his femininity, becoming one of the girls in an all-woman group of child welfare workers, while mystery lurks)

Chapter Four – A Night to Remember

It was a warm night and Amy and Marcus spent several hours on her balcony, sitting together in a two-seated swing chair.  They sipped the red wine that Marcus had brought and were well into a second bottle that Amy produced when she said, “Want to stay the night?” 
 
He was shocked.  Stay the night?  That would mean likely sleeping with her, maybe even making love.  No, he couldn’t do that.  It was wrong to sleep with his boss, wasn’t it?  But, what was he to do?  He’d never been in bed with a woman in his life, except with his mother and that ended when he turned twelve.  He wasn’t sure he was capable of making love to a woman, though he knew what had to be done.  Marcus wasn’t sure he could complete the act.  
 
“I couldn’t,” he said. 
 
“Why not?  You have a jealous girlfriend, do you?” 
 
He blushed.  A girlfriend?  Hardly. 
 
“You’ve had a lot of wine, Marcus.” 
 
Marcus didn’t answer; he realized he was getting a bit foggy-minded. 
 
“It’s getting chilly now, Marcus,” Amy said after several minutes of silence passed between the two.  “We’d better move inside.” 
 
Soon Marcus found himself sitting next to Amy on the sofa; the woman had turned on her large-screen television to a movie channel that was showing “Sleepless in Seattle” for the umpteenth time.  The sound was low and barely audible, but Marcus had seen the chick flick perhaps a dozen times and knew much of the dialogue anyway. 
 
Amy cuddled up against him and Marcus was surprised as she put her arm around his shoulders and began caressing his slender upper arm.   He stiffened slightly as he knew Amy would be feeling his soft, unmanly body, shaming his manhood.  But her touches were tender, and soon became comforting.  He succumbed into her arm and their faces grew close.  He nestled more tightly into her, smothering his head onto her breasts, the scent of her subtle perfume intermingling with musty smell of her growing perspiration. His penis was growing hard. 
 
“This is so nice, Marcus,” she said, looking into his eyes. 
 
“Yes, Amy,” he said, wanting to say something more romantic, but still worried about whether the woman would be offended.  He was ashamed at his own ineptitude with woman. 
 
“You’re uncomfortable, my dear?” Amy asked, apparently sensing his hesitancy. 
 
He wasn’t certain how to respond.  What was a man to do in this situation, he wondered?  Wasn’t the man to be the initiator, the one who made the advances? 
 
“You’ve never had a girlfriend, have you, darling?” she asked. 
 
“Not anything serious,” he said, realizing it was not the total truth.  The truth was too painful to admit to.  He was twenty-three years old and he’d never been on a date in his life, nor had he ever had a “girlfriend” in any sense of the word, unless he counted his mother. 
 
“Would you like to kiss me, darling?” she asked. 
 
Marcus never had a chance to answer; Amy’s lips were upon his, soft and gently at first and then with more passion.  He tasted the garlic-and-wine of her mouth, the intimacy of her exciting him and he returned the kiss with his own firmness and the two were locked in a sweet embrace.  He felt his lips being pushed apart and her tongue thrusting into his mouth, shocking him at first; it was stimulating and he could feel his penis growing harder and becoming painful.  He was afraid he would burst into a violent ejaculation, filling his panties (yes, he had taken to wearing panties daily under his male clothes).  
 
Suddenly Amy broke their embrace and move away from him.  She was panting heavily and Marcus was confused.  Her quick separation caused a softening of his penis. 
 
“You’re so passionate, Marcus,” she said. 
 
“Am I? Is that OK?” 
 
She laughed.  “Oh, my yes.  I loved your passion, and I’ll bet you’re a virgin, right?” 
 
He reddened, still ashamed to confess his lack of experience.  He didn’t answer, but it was obvious that Amy knew the answer. 
 
“There’s nothing wrong with that,” she said.  “You have lots of love in you my darling.” 
 
“You think so?”  
 
She smiled and nodded her head. 
 
“I better get going,” Marcus announced.   
 
“You’re not going anywhere,” she said.  “It’s after midnight and the buses will be few and far between.  You’ll stay here.” 
 
The tone of Amy’s voice was firm and determined; Marcus would stay with her that night.  After all it was now Saturday morning and Marcus had a whole weekend free, with nothing much to do but his laundry and perhaps take in a movie by himself.  His time off was lonely; he missed weekends at home with his mother. 
 
“I have a big queen-sized bed and there’ll plenty of room for both of us,” she said. 
 
“I can sleep on the sofa,” he said.  “You don’t have to share your bed.” 
 
“I don’t snore, Marcus,” she laughed. 
 
“You know we shouldn’t sleep together . . . ah . . . er . . . unless  . . . ah . . .” 
 
“Unless we’re going to make love,” she completed the sentence for him. 
 
“Yes,” he agreed. 
 
“Marcus, we won’t be making love, as you call it, for two reasons, darling.  First of all, we’re co-workers and we should not get too involved with each other so quickly and, secondly, you’re a virgin and I want your first experience to be with someone you really care for.  OK?” 
 
“I care for you, Amy,” he blurted out. 
 
The woman shook her head negatively.  “Not in that way, darling.  Maybe sometime in the future.  Right now, we’re just friends, OK?” 
 
Marcus felt a bit embarrassed by his sudden outburst that he “cared” for Amy; he truly did, an affection that had grown from his first day on the job.  After all, the age difference wasn’t too great, just seven years, he had periodically reasoned.  The fact that they were co-workers and she was his immediate superior troubled him; such workplace romances rarely seemed to work out. 
 
“Marcus, I really like you, I truly, really do, but we must cool off.  I was wrong in encouraging this,” Amy said. 
 
“No, you weren’t,” he argued. 
 
Amy didn’t answer. 
 
***** 
“Here, you may wear this to sleep in,” Amy said.  The two had finished cleaning up the kitchen and they had retired to Amy’s bedroom.  The two had giggled often as they washed the dirty plates from dinner and cleaned the wineglasses.  The buzz that Marcus had felt from the wine had tapered off and he was feeling more clear-headed.  He was beginning to question why he was staying the night, but Amy had been insistent and he had no reasonable excuse to refuse the offer, outside of his own shyness and wariness over what was appearing more and more to be a romantic encounter.   
 
“That’s one of your nightgowns, isn’t it?” he asked. 
 
“Yes, put it on.  It’s something to sleep in,” she said. 
 
“But?” 
 
“It’s clean if that’s what you’re asking.” 
 
“No, but it’s a woman’s gown.” 
 
“So?” 
 
“OK,” Marcus said, a bit embarrassed at being asked to wear a woman’s gown. 
 
“You’ll look darling in it,” she teased.  “You can change in the bathroom, and you may want to keep your briefs on.” 
 
Marcus smiled, realizing he was already wearing women’s panties.  Maybe the gown was just made for him. 
 
A few minutes later, he emerged from the bathroom, wearing the pink baby doll style nightgown.  It was a little loose on him, since Amy had a huskier body. 
 
“My, you are the picture of loveliness,” Amy said.  She was wearing a similar style gown, but of peach color. 
 
“You are too, Amy,” he said. 
 
“Gimme a hug,” Amy said reaching out to Marcus.  The two hugged for a long time and Marcus looked over her shoulder to the full-length mirror. 
 
“We look like sisters,” he said, breaking the embrace and turning her toward the mirror. 
 
“Yeah, we do.  The short, fat one and the pretty one,” she said, beginning to laugh. 
 
“Well, maybe two pretty sisters, one a little shorter than the other,” he corrected. 
 
They tumbled into bed together, quickly separating under the covers, Marcus to the left side of the bed and Amy to the right.  The width of the bed was enough to keep them apart for the night.  He fell asleep almost immediately, perhaps due to the amount of wine he drank and perhaps also due to the contentment he felt with Amy.   
 
***** 
Marcus awoke to the scents of toast and brewed coffee; for a moment, he imagined he was back home in Wisconsin, his mother preparing a full breakfast for him.  It had become a regular Saturday morning ritual between mother and son, the one day they were usually at home, unburdened with the need to arise for work or school schedules. 
 
From the smells of the room, however, the sweet feminine aromas of cosmetics, potpourri and perfumes, he realized he was not back in his old childhood bedroom.  His head ached, and he remembered all the wine he had the previous night.  He smiled to himself; he was in Amy’s bed wearing her nightgown; he briefly thought how Amy had treated him as her girlfriend. 
 
His memories were foggy; he remembered much of what had happened, his sharing of the bed with the solid firm body of Amy Dacosta, his falling asleep almost immediately but then waking to Amy’s hugs and kisses, his own excitement and erections, his declarations of affection for the older woman.  What else did he do during the night, he wondered?  Certainly, he did not end his virginity, he knew, but what else did he do? 
 
Just then the door opened and Amy stood there momentarily, smiling.  “Good, you’re awake, sleeping beauty.” 
 
“Hi, guess I better be up, eh?” 
 
“Yep, coffee and a nice breakfast awaits, dear Miranda,” she said using the female name she and his co-workers had tagged him with. 
 
“Oh?  You didn’t have to do that.  Just gimme my clothes and I’ll be on my way,” he said. 
 
“No way, cutie, you’re having breakfast and then we’ll see what we’d like to do,” she announced.  “You don’t have any plans for the day, do you?” 
 
“No, nothing but some studying for my class, but I guess that can wait.” 

“What class is that, darling?”

“I decided I should start on my masters and am taking a class at the ‘U’,” he said, referring to the local branch of the state university.

“Good, girl,” she said, handing him a pink robe and a pair of fluffy slippers.  “Go brush your teeth, freshen up and come one down for breakfast.  You can shower later.  There’s a new toothbrush in the bathroom you can use.” 
 
“Oh?” 
 
“Yes, I keep it for occasions like this,” Amy said, giving him a wink. 
 
“You must do this often,” Marcus said in a teasing tone. 
 
“Hardly,” she laughed.  “You’re the first.” 
 
“I’m honored,” he said. 
 
“You’re special, but don’t let that go to your pretty little head.  Now, get going, I’ll be starting on the quiche soon.”  She turned and left the room. 
 
***** 
Amy set up their breakfast on the same small table upon which they had their supper the previous night.  The tiny Pullman kitchen opened onto a small dining area.  Again, she had placed a white table covering with cloth napkins neatly arranged with sparkling silverware.  Goblets of water with ice stood before each place setting; the partially burned candles stood in their silver holders as they had last night.  They were unlit. 
 
Marcus was stunned by the loveliness of the table setting.  “All this for me?” 
 
“Yes, dear Miranda.  It’s great to have someone to cook for,” Amy said emerging from the kitchen with an orange juice container in her hand.  He was curiously pleased that Amy kept using his female name. 
 
She prepared a spinach quiche for them, coupled with toast and jam; the quiche was magnificent, light and fluffy and yet tasty.  It was obvious, Amy had used spices to great advantage in the quiche. 
 
“It was delicious.  Where did you get that skill, Amy?” he asked. 
 
“I’m from a typical Italian family and as the only girl mom insisted I learn to cook.  A way to winning a man’s heart, she used to say, is through his tummy.  Only it hasn’t worked very well for me, as you can see.  It’s just kept me fat.” 
 
“I’m certain it’ll work sometime soon for you,” Marcus said.  “Any man would be lucky to have you.” 
 
“I guess it worked with you, Marcus,” she said, reverting to his male name. 
 
“I guess, only I’m hardly the ‘hunk’ of a guy you deserve,” he said. 
 
Amy merely smiled at Marcus.  He wasn’t sure how to take her silence; did she agree with his self-assessed observation?  Or, maybe she found him appealing for some reason that he could fathom?   
 
“Let me help you clean up here, Amy,” he volunteered when they had finished eating. 
 
“Nonsense,” she retorted.  “I can clean up here in a jiffy.  You just go and get your shower and pretty yourself up, Miranda.” 
 
“You’re calling me Miranda now?” he said, framing it as a question. 
 
“Of course, darling.  You’re too lovely to be called something like Marcus.” 
 
He blushed, not certain how to respond.  Him, a girl named Miranda?  It was a lovely name, he thought. 
 
“You’re so cute when you blush, or did I already tell you that?” she asked, adding a little giggle. 
 
As if on cue, Marcus responded, placing his hand in a girlish manner to his face, shyly looking to one side.  Sitting there in the nightgown and pink robe, his long hair straggly from his night in bed, he felt truly feminine.  In truth, however, he wasn’t a girl, so how could he be sure how a girl would feel? 
 
“You’re a natural beauty,” Amy said, leaning in to kiss him lightly on the lips.  “Go, now, get your shower.  You’ll see some clothes on the bed that you can try on.  They should fit you, I think.” 
 
***** 
Marcus found scented soaps and lotions laid out in the bathroom; having little choice he used them and emerged, his body scented with a subtle sweet odor that emitted femininity.  He applied the lotion to his arms and back and legs, massaging his soft flesh.  As he used the dryer on his hair, he viewed himself in the mirror, admiring the lovely girlishness of his body, its pale, hairless skin, slender arms and narrow shoulders.  He smiled at the image. 
 
He left the bathroom, wondering what Amy had in store for him.  It was obvious that Amy Dacosta had taken charge of his life; she was in command and he welcomed it.  In the past, he had turned to his mother for direction; he would still be looking to her for advice, of course, but he wondered whether Amy would now also become his confidant.  Was she trying to change him from a pathetic young man into a beautiful young woman?  And did he want that? 
 
“I guess she wants me to be Miranda for the day,” he said aloud even though no one was there to hear him. 
 
He smiled at the prospect.  On the bed, he spied a blouse and shorts, obviously meant for a girl, as well as a beige panty with lace trim and a discreet ribbon on the top hem.  And, to his astonishment, a matching bra with breast forms.  A pair of light tan sandals sat next to the bed. 
 
“Are you done, Miranda?” he could hear Amy’s voice outside the bedroom door. 
 
“Yes, but I’m without clothes.” 
 
The door burst open and Amy entered.  Marcus tried to protest, but she continued in.  He started to cover his private parts with his hands. 
 
“No need to cover that,” she said.  “I’m not interested in that.” 
 
“But,” he protested.  He hated anyone to see his tiny piece of manhood, trying always to hide it in the showers at high school after gym classes.  How he hated those sessions! 
 
“Shut up and try these panties on. Leave the tags on in case I have to take them back,” she ordered. 
 
He noticed there were price tags on all the clothing and looked questioningly at Amy.  “You bought these for me?” 
 
“Yes, and I hope you like them,” she said. 
 
“But, I’m not sure I can pay you for them, Amy,” Marcus said. 
 
“You don’t have to.  I just want my girl to look pretty and to be happy in them.  Nothing’s too good for her.” 
 
“I’ll still pay you, but it’ll take a few weeks,” he said. 
 
“Nonsense.  Wear and enjoy, pretty one.” 
 
Marcus was excited to try them on and he was so grateful to Amy that he dropped the towel that covered part of his body and hugged Amy in the total nude.   She took him in her arms willingly and caressed his soft, smooth skin kissing him voraciously.  His penis grew hard as he pressed against her. 
 
“My darling Miranda,” Amy said breathlessly. 
 
Marcus’ breathing grew short as he felt Amy's fingers playing with the soft flesh of his man tits.  He felt his nipples grow hard and he began panting heavily.  He succumbed easily to the more aggressive actions of his new friend.  He felt the strength of her arms as she moved him easily to fit her growing emotions, Amy's own breath growing more heavily. 
 
“Oh Amy, you want me as your girlfriend, don’t you?  You never wanted me as a man.” 
 
“Yes, my darling, and you’re just about the loveliest girl a girl like me would want.” 
 
They held each other tightly for a long time, before Amy broke away.  “We better stop now, or you’ll need to shower again,” she said. 
 
***** 
She helped Marcus put on the panties and bra, with the breast forms to create budding breasts like you’d find on a thirteen-year-old girl; she led him into the bathroom, and ordered him to sit on a stool while she brushed his longish hair so that it hung straight with a slight bob, adding bangs across his forehead.  As she worked, Amy's hands caressed his smooth skin, seeming at times too linger at soft parts of his anatomy.  Finally, she finished brushing his hair, fixing it with a holding spray.  She had him turn in the chair to face her. 
 
"You have such lovely skin, Miranda, I don't think you need lots of makeup," Amy said.  "You could be such a natural girl, Miranda.  How I envy you!" 
 
She explained that she was applying light foundation, followed by a bit of coloring for his cheeks.  Marcus followed her instructions with interest, musing that if he was to be like most women he'd have to learn to apply his own makeup.  She applied a light eyeliner and trimmed his eyebrows slightly. 
 
"I think you look best in outfits that are modest and not too showy, kind of like you're a sweet young girl from the country with simple and lovely styles," she said.  
 
He watched in the mirror as Amy did her work, marveling at how easily she had transformed him into a plain, but truly fetching young woman.  He hated to admit it to himself, but he felt the girl looking back at him could best be called "cute."  He offered a girlish flick of his hand into his hair that brought smiles to the two faces he saw in the mirror, those of Amy and Miranda.  
 
"Today, you're Miranda, my darling," Amy said.  "We're in for a perfectly magical day." 
 
"Magical?" He asked, wondering what Amy had in mind and worrying that he may be in for a bit more than he was ready for.  He realized she obviously wanted him to be her girlfriend for the day. 
 
"Just don't you worry, darling.  You're such a pretty little thing," Amy said, hugging him again.  It was as if Amy couldn't keep her hands off of him. 
 
She instructed Marcus to sit down on the vanity seat, while she sat down in front of him on the floor.  "Now gimme your right foot," she ordered. 
 
"What are you doing?" 
 
"You'll need your toes painted.  You're wearing open-toed sandals today," she announced. 
 
"But," he began to protest. 
 
"No 'buts' darling.  You need some color down there." 
     
He obediently did as he was told.  Amy took his foot, caressing it gently.  She looked up at him and smiled. 
 
"Such a lovely foot, and your skin is so soft and smooth.  Do you put lotion on them?" 
 
Marcus blushed.  "Every day I guess.  I don't like getting calluses." 
 
Amy leaned down and kissed the foot, even licking briefly around the big toe.  He watched carefully examine the nails. 
 
"You keep them trimmed, too, I see." 
 
Amy applied a natural color, with a hint of pink, to each nail, her strokes lovingly applied.  She blew on the toes to hurry the drying and then repeated the process on the left foot. 
 
Marcus found he enjoyed his friend's artistry; rarely had anyone paid much attention to him, except for his mother, of course.  He felt he had become the love object of Amy, a strange position since Amy was his boss and much older.  The love interest involved him as a female, as Miranda.  
 
"Now, here's what we'll put on for now," Amy said, reaching onto the bed for the orange-red shorts and teal-colored ruffled peasant-style blouse. 

He took shorts and noticed tags were still attached. “Did you buy these, too?”

“Yes,” she said. “I just thought these would be divine on you.”

Marcus smiled at the woman’s observation, eager to try them on. She took the shorts from him, found a scissors in the vanity and cut the tags and then did the same to the blouse.

“There, you can put these on now,” she said, handing them back to him.
 
"Aren't they too short?" He asked.  Marcus was worried that they might show part of his crotch and perhaps even his male part.   
 
"No, hon, that's what all girls with pretty legs wear," Amy said.  "I can't 'cause my legs are too fat, but your legs are absolutely gorgeous." 
 
He put on the clothes and then posed in front of a full-length mirror that Amy had on her closet door, trying all sorts of what he considered feminine gestures. 
 
"Such a cute ass, too," Amy said, gently patting his bottom, following the round curves with her fingers.   

(To be continued)
(Thanks to Eric for proof-reading and other editing help)

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Comments

I was very glad to see more of this story......

D. Eden's picture

It took me a few days to find the time to read it, but it was well worth it.

Amy obviously has plans for Miranda, and she is definitely the dominant in this relationship. I can’t help but wonder just where she plans to take this - how far she plans to push Marcus into being Miranda.

Marcus appears to be a natural submissive and is taking to this like a fish to water as well.

Looking forward to seeing more!

D. Eden

Dum Vivimus, Vivamus

Rock rolling down hill

Jamie Lee's picture

Oh yeah, Amy has it bad for Marcus/Marinda, even though she's his boss--which could become tricky.

It really sounds as though Marcus's mom never allowed him to spread his own wings and find himself. She treated him like a adult baby, someone who always needed care.

And now Amy has become his mom, girlfriend, taking care of him as his mom did. Except it's Miranda she's taking care of and wanting.

Marcus has wanted what Amy is doing to him a long time, but maybe things are moving too fast for him?

Others have feelings too.

Looking good gidl

Alice-s's picture

A bit of Rannas Doll in the plot.