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This work is copyrighted to the author © 2010.  Please
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Dolly The Chickenhawk
by Nesfdancer (nefstoryr@yahoo.ca)

***

This is the story of Dolly, who procures boys as shemale 
prostitutes. (Mm, Fm, ped, nc, rp, oral, anal, prost)

***

Dolly was a retired Madame and pimp. Her nickname was 
Dolly because she looked like Dolly Parton, big hair, 
big boobs, and a southern accent. In her heyday, she 
worked on the East coast, procuring and running young 
runaway boys for her high end escort service. That was 
years ago now, back in the good old days, before her 
drug trafficking arrest that put her out of business, 
before AIDS, before the "war on drugs", before a lot of 
things. 

Now she lived in a rundown RV motor home on the wrong 
side of the tracks, eking out a living on small time 
hustles, fencing, and scrounging. She was 59 years old 
now, still attractive, but heavier set. She was tanned, 
blue eyed, had nice long legs, platinum blonde hair and 
her bust size was a double-d. She no longer was on 
parole, not for 5 years now, and she stayed away from 
the heavy action.

Dolly was sick of the safe life. She was unable to make 
much from her meager earnings, and she longed for the 
days when she had money to spend. One afternoon, she was 
shopping in the mall, when she spotted a boy of no more 
than 11, cute, long brown hair, wandering alone. She 
realised he looked like Evan, a boy whom she pimped out 
almost 15 years earlier. She was sure he was dead by 
now, poor Evan, he always indulged in the shit too much. 

She remembered him sitting at the corner store as she 
drove past in her Lincoln that night, his long brown 
locks hiding his face, his long legs in cut-offs, his 
knee high socks and blue runners, and his pathetic 
squirms as she stuck him in the arm with that first hit 
of heroin, that was all the thing for a pimp in those 
days to use. The dress-up sessions, his first customer, 
a European banker woman with a fetish for pre teen boys, 
yes those were good days. 

She found herself following the boy in the mall, not too 
obviously, and watched him walk  past the hosiery 
section of the store, looking side glancing at all the 
racks of pantyhose. She figured he probably liked them, 
but was shy. She remembered a time when they would cry 
and fight her, as she told them what pretty things they 
were going to wear. She found herself fidgeting with her 
purse, but then realising that her syringe wasn't there, 
had not been in a long time. She left the store with a 
new plan, and thoughts of past glory.

Dolly acquired some items over the next few days, some 
morphine, some syringes, a bottle of ether, a decent 
switchblade, more decent vodka, and some hemp rope. She 
also fastened some gags from cloth strips. She then 
shopped the thrift stores and bought some girls clothes, 
summer dresses, tops, blouses, belts, ballet flats, 
white cable knee high socks, girls runners. She then 
stopped by a few other stores and bought girls sized 
tights, dance pink, black, and skaters flesh toned, and 
pantyhose, expensive black and cheap looking tan and 
some makeup.

Dolly parked her RV near a popular late night donut shop 
in a poor neighborhood, and staked it out over several 
nights, making sure she was legally parked. There was a 
bus stop near the shop, and seemed like a popular spot. 
On the second night after midnight she watched a dark 
haired boy of maybe 12?, dressed in jeans, grey top and 
white sneakers, walk past her RV and go to the donut 
shop. Dolly looked back and surmised he had come down 
the street probably a block or so. 

He was out very late, and she surmised he was probably 
with a single parent, if he had parents at all. She 
moved the RV down a block, parked and turned the lights 
out. She was dressed in a red dress, glossy white 
pantyhose, and high heels. She put a lot of makeup on, 
and had a black purse. She watched as the boy walked 
towards the RV. She got out, and walked towards him, 
looking as sexy as she could, click clacking along the 
pavement, timing it so they would meet behind the RV, to 
give her some cover.

The boy didn't seem concerned to see her, and she 
expertly dropped her purse on cue, dropping a few bills 
and some change. "Oh my, could you help me with that?" 
she asked demurely. The boy said "oh, ughh, sure", he 
had a sweet voice, and noticed he had long locks of 
black hair, pale blue eyes and a pretty face. Dolly 
hated boys with short hair, and much proffered a more 
moppish, feminine look. She stuck him in the ass with 
her syringe and pulled it out as she pretended to 
fumble. 

"Oww!" he yelled.

"Oh, I'm sorry I caught you with the clip on my purse 
handle," she said. She had lost none of her touch, and 
the morphine was shot into the little twinks behind. 
Dolly opened the door of the RV, and gambled her mark 
was well mannered. He was and was waiting to give her 
the change he had scooped up, "thanks," she said. Then 
she pushed him from behind and half way into the RV. 

He panicked and tried to run but she smacked him with a 
sock full of wet sand, and he was momentarily stunned. 
He sank to his knees with a groan and was quickly hauled 
into the RV, his arms and legs limp and feeble. Dolly 
dragged him back to her bedroom, and threw him face down 
on the bed. She quickly tied him up with the hemp rope, 
not bothering to take his runners off yet. 

She quickly doused some ether on to a rag and made him 
breath it in until she knew he was properly stupefied. 
He moaned and thrashed as she knelt on his back and 
stuffed the doused rag on his nose and mouth, as he 
drifted off.

Within minutes she was driving to the far side of the 
city, and parked under an overpass, where a lot of 
drunks and drug addicts slept, it was perfect. The boy 
was feeling the morphine by now she was sure, and she 
untied him and rolled him over cradling him in her arms. 
His eyes opened slowly, "I, umm," was all he said. 

"You're a pretty thing aren't you," Dolly said to him, 
caressing his cheeks. She felt down between his legs to 
feel his crotch and squeezed his balls and penis, 
smiling at him. "I'm going to have to get you some new 
friends," she said to him. "I had a bigger place back in 
the day, but we will make do" she chuckled, and made him 
swallow several laxative tablets with some water. After 
a few hours she took him to the bathroom and let him 
evacuate his bowels, then she cleaned him up and brought 
him to bed to sleep.

Later that night she stripped off his clothes until he 
was naked, and let him lay on his back while she 
prepared a fresh shot of morphine. She raised his 
slender right arm up to her lap and slid the syringe 
into him. He moaned just slightly, but otherwise was 
fine. "Mmm, ya, take that, you will be craving my 
dreamer in no time." Dolly said to him. She fondled his 
limp penis, stroking him gently between her expert 
fingers until he nodded off. She left him in the RV and 
took his clothes over to a trash bin fire, and threw 
them in. 

She returned to the RV, and while he regained some 
consciousness, produced a pair of thick pink ballet 
tights for him, and pulled them on, then cut a small 
hole in the gusset. She then began his first lesson in 
sex. She took out a 6 inch cucumber, expertly peeled it 
to her liking by the sink and then approached, holding 
the phallus in her hand with a container of Crisco 
vegetable grease. 

He was made to spread his shapely legs over Dolly's 
shoulders, then she unceremoniously slid it into the 
boys rear end. The innocent boy felt the pressure, as 
his pink anus was probed by the invaders tip, and then 
with a push, his deflowering was at hand and he let out 
a moan of shock, discomfort and confusion. He was 
screwed by the greased up vegetable. 

"Oh no don't do that, please," he whimpered. 

Dolly smacked him with her open hand. "Shut your mouth 
and do as our told bitch," she said to him. The boy 
started to cry. Dolly fucked him with her "dink" to his 
squirms, weak kicks and moans. 

"Oh yes, take that you silly girl," she cooed to him, 
pistoning it into him repeatedly while his shapely 
calves were kicking over Dolly's shoulders. It made a 
sucking, squelching sound as it slid past his sphincter. 

She finally pulled it out bloody and wet, after his ass 
had been thoroughly ploughed. She held it up for him, 
and he could see it had gone deep into his bum. She 
wasn't done though with her lessons, and propped him up 
at the edge of the bed and slapped his butt with a wide 
leather strap until he could cry no more the strap his 
rear end until it was tender, a small run in his hosiery 
from the abuse. The boy was exhausted, drugged, raped, 
and slapped silly! 

Whatever resistance he thought of had since left, and he 
lay back and nodded off, as the drug he was given began 
to make him dopy and unfocused. The rapist Madame then 
wiped him clean with a towel and let him lay down and 
sulk for awhile, and from his first anal experience. 

"Get used to that, and get used to the girls clothes 
darling, you're going to be wearing them a lot," Dolly 
said to him as he drifted off.

After an hour the transformation to a girl proper began. 
First thing was the expensive glossy black tights, that 
she pulled on to him while he dozed. Then the blue 
Japanese sailors top, like they wore as a school 
uniform. He looked very nice. She combed out his hair 
and but in a pink barrette to keep it to one side, and 
then applied some lipstick and some blue eye shadow and 
dark eye liner. Last she slipped on the blue skirt that 
matched his top, and some black velvet flats that seemed 
to fit. 

She lay him supine and had gave him some hair spray to 
keep it all just so. He looked like a little 12 year old 
girl all ready for private school. He moaned and turned 
on his side. He was high, and only semi-conscious, 
riding the high of the painkiller injections, now at 
full force in his bloodstream. Dolly as feeling the rush 
of power, she loved the feeling of controlling tender 
boy flesh to her purposes. Why had she ever stopped? she 
didn't know.

The boy regained some consciousness, and found himself 
in the lap of the pimp, his vision blurry "Shh, don't 
fret little girl" she said to him, and held up a small 
mirror, she made him look at himself. She stroked his 
glossy legs and under his skirt, and he became aware of 
his new wardrobe and look. "I'm calling you Susan," the 
lady said to him. "Don't worry, it's all fine." And she 
massaged his private mound again under his skirt.

"Oohhh, no," he moaned in a quiet voice. 

Her new boy was left to doze on the bed while Dolly 
drove to the transvestite hooker part of town. She made 
some inquiries as to where to set up shop and parked 
near a rundown area. She checked on Susan, who was 
sleeping restlessly, and got out to spread the word that 
she had a fresh rear end for sale. 

"It's 10 bills," Dolly said to Susan's first customer, a 
horny Mexican pill junky. "He's a novice so I'll give 
you a discount for breaking his ass in properly" she 
said, and let him in. "You have a half hour," and Dolly 
waited in the cab of the RV.

The man went into the RV and drew back the cheap bead 
curtains to see the boy laying down on the double bed, 
and he approached the drugged twink. Soon they were 
kissing deeply, he had his arms around his prize, and 
was tasting the expensive lipstick with his tongue and 
smelling the boys feminine perfumes wafting in the air. 

The junkie's jeans could scarcely cover his manhood, 
engorged, and he tugged away at his shorts to expose 
himself. He moved the boys head to his cock as he 
straddled him, and the boy did as he was bidden, 
covering his cockhead with his red lips, smacking and 
sucking, amateurish yes, but effective enough for the 
purpose, and the boy could see the man's dink clearly, 
erect, his ball-sack large and the long tool tasting odd 
in his small mouth, he had to open very wide to get his 
lips around it. 

He was too stoned to resist, and was lost in a dizzy 
haze of drugged cocksucking. The "john" pulled his cock 
out of "Susan's" mouth and turned the petite boy-girl 
over on the bed and before he knew it was attempting 
entry into his rear end, his lust red hot for the young 
behind. He grabbed a pillow and made the under aged 
victim lay down over it, getting his ass elevated for 
the big moment. He massaged the boys ass through his 
tights, and then them down and off, leaving his smooth 
buttocks exposed.

"Please, don't, don't hurt my bum, it's still sore," 
Susan managed to sputter as the rapist speared for the 
third time into the boys hole, his stiff tool amply 
greased up with the sex lube. He felt his tip finally 
slide into the target of his lust, the small anal 
passage, and it was glorious. "Ughhhmm!" he moaned, the 
boys legs apart. There was a wet, piston like as the 
man's tool slid into the warm, tight hole "Ohhh! Holy 
shit..." Susan cried out breathlessly. Was it worth the 
money, the man thought? Hell yes.

"Ohhh, mmmm..." Susan whimpered in pain and disbelief, 
biting his lower lip. "I'm going to fuck with a real 
cock, boy. Now lay still and spread your thighs while I 
bugger you," the older man spat, not to be trifled with.

"Susan" felt the fleshy staff sink into him, filling his 
bowels with a wet pressure, he could feel the junkies 
unwashed 8 inch prick slide deeper and deeper into his 
rear end, searing a painful path. He was being fucked up 
the ass!" and the pain was unbearable, and he cried out 
in shrill squeaks.

His "lover" held his waist firm, ignoring the childish, 
silly pleas, and Susan was pinned on his stomach as he 
was turned into a woman. It did hurt so! and Susan 
whimpered as his prized innocence was traded for one 
hundred dollars, the white sheets stained with his red 
lipstick as he thrashed around feebly, trying to 
dislodge the invader.

The mating was filled with moans and cries, the man 
fucked the cross dressed boy hooker in a frenzy, 
remembering a young boy of similar age who had come to 
his condo door one Halloween a few years past, before 
his problems with drugs, dressed as a music video 
dancer, complete with fishnets and a lycra skirt. His 
memory coming back to how he secretly wanted him, to 
show him what dressing like a tart could cost him, 
wondering what it would be like to ambush the naive boy 
in the bushes, yes, it was a dark fantasy he kept to 
himself. 

Long minutes past, the squeak of the bed, Susan's 
whimpers, the wet, slapping sound as the prick drove 
deep and thighs smacked together, each thrust loosening 
the boys tight sphincter muscles and rendering any 
resistance quite futile.

After several minutes the junkie paused, and pulled out, 
"hold still" he said. Susan felt the huge dink slip out 
with a wet , and felt incredible relief, but the 
assailant quickly squirted more lube into him directly 
from the bottle, and it felt cool in his bottom, and 
also stung. A subconscious part of Susan wanted to be 
filled again, but he feared the man's cock. He felt the 
dink slide into him once more, quite easily this time, 
filling him quite completely, and the rhythm renewed. 
Soon after an eruption of come flooded Susan's anal 
passage.

"Ohh, oh my god, take that you cock tease bitch!" the 
man said, as he thrust his final victorious spasms of 
conquest. He let his snake spurt warm juice into the 
boys tender insides, his chute with his warm, frothy 
potency. The man pulled his tool out for the last time, 
stained with blood, come, and lube, it was an 
impressive, thickly veined staff of rape. 

"Don't fret princess, it's all over," he said in a 
hoarse voice. He wiped his prick on the boy's discarded 
tights and then he stumbled off the bed, to collect his 
own clothes.

Susan was left face down on the bed, and he lay for 
quite some time, curled up, holding his knees and oozing 
fresh come from his red, wet, tender hole. He knew that 
he had been forever changed by the drilling he received 
from his first real man, his first lover, and that he 
would be a girl at heart from now on. Susan felt his 
rear end get a damp wipe from his mistress, to clean him 
up.

Dolly pulled the stunned and raped boy to her and went 
down on him, sucking his tender prick with her expert 
mouth, she managed to get him hard for awhile, and she 
wanted to ensure Susan knew all the things his tender 
body could provide. She then brought back her bottle of 
morphine to the edge of the bed, and prepared another 
needle. 

The boy was rolled over on his smooth naked ass and he 
felt the sting of the syringe, "all better now hmmm, no 
need to worry when Dolly looks after you", she said, 
then the familiar tug on his legs as he was dressed in a 
pair of glossy white nylons, and left on the bed to 
sleep it off, freshly drugged.

Dolly was back in business.

A month later Susan was working outside the RV, dressed 
in short red wig, silver lipstick, a long sleeved pink 
spandex dress, glossy pink tights and knee high black 
pigskin boots. She was a shemale cocksucker in every 
respect, her memories of boyhood forgotten to the street 
life. She smiled as the cars went by, and was watched 
closely by Dolly, who was keeping her candy from her 
until she turned a trick. Susan craved the relief the 
injections brought, and knew only Dolly could make her 
feel better. "You better get that thumb out when cars 
pass or you will get a spanking!" she reminded her from 
the RV window. 

"I'm doing it! they guys been bye three times, but he 
won't stop," Susan protested.

"Don't take a tone with me bitch, work it," Dolly 
reminded her, Susan wanted a cock to suck, she just 
wanted get inside and get her medicine, the boots hurt 
as a well, as they were new. "Don't get those tights 
dirty either, I only have the one pair to go with that 
dress," Dolly said. 

"All right, god!" Susan said exasperated, and adjusted 
them a bit, making sure the seams at the back were not 
twisted around, her water balloon filled bra was making 
her too hot too, but she didn't complain. 

A dark sedan pulled up and stopped with a white man of 
about 40 inside. "Get in baby" he said. Susan slid in 
the front seat, all smiles, and told him to park a block 
away. The man undid his pants and got the blowjob he was 
looking for, holding down Susan's bobbing head until she 
was done. The man thought of raping the young whore 
anally with no condom but thought better of it, he would 
come back another time, with a friend.

Afterwards, Susan got dropped off a block away from the 
RV. She threw aside the used, lipstick stained condom 
and walked past the rundown crack houses and other 
whores who worked the strip. Susan walked confidently in 
her boots, past the older whores, "March that white ass 
baby, or I'll work you some here," a black pimp said to 
him.

Susan ignored him. Felix was always on him about working 
his stall, but she knew Dolly had more street muscle and 
so she wasn't touched. Susan sauntered past, and flipped 
a finger at the black pimp with the big gold tooth and 
animal skin hat. 

"I'm spoken for," she said sarcastically, batting her 
thick eye lashes, to the hoots and calls of a few of the 
other trannies and regular prostitutes, and sashayed on 
past. Susan stopped to talk to "Funtasia" a new young 
tranny whore whom she knew from the corner, in Felix's 
employ, and bummed a new lipstick off her for a 
cigarette and a light. 

"Fuck, I need a hit, it's been slow today, fucking 
tourists," Funtasia said. "Double up your pantyhose too 
girl, you're going to freeze tonight in that thing," 
Susan offered in advice.

"Felix isn't wearing that mesh dress on his skinny white 
ass," she said with a smirk. 

"True enough girlfriend, just think if I didn't hook up 
with Felix at the bus stop I wouldn't be living this 
glamorous life," she said sarcastically with a laugh, 
and she held out her long, shapely, silky leg showed off 
her 4-inch black pumps, and with that, they parted 
company. A few minutes later Susan was home, re did her 
lipstick in the rear view mirror, and came inside to 
give Dolly her money. 

That's how it worked, she had no other thoughts than to 
please her corner-mother and be rewarded with the heroin 
she was now being given four times a day, to keep her 
hooked and dependant.

Dolly was satisfied with Susan's transformation from a 
boy to a cheap street walker. She did the four things 
required of a hooker in a pimps brood, she stood at the 
corner with her thumb out, she got into cars and sucked 
cock, and she returned with the money, and she took her 
fix. That's all that was required. 

Dolly liked to think of it in very basic terms. Her rape 
of the boy had broken his will, as she knew it would, 
and coupled with the forced addiction to drugs, he was 
now a shemale whore, and her property. Felix's girls 
watched her to ensure she never went too far, and she 
had a $500 finders tag on her ass, as a finder's fee to 
anybody that brought her back if she tried to stray, but 
those days had long since past. 

She also acquired female hormone shots for Susan, and 
soon she would sporting a nice set of genuine apple 
sized boobs, as well as delaying any male puberty 
development. Dolly arranged a trade with Felix for 
hormone shots for Funtasia, in exchange for decent, high 
grade smack, which Felix had a good tap on from an 
associate. Despite being a competitor, pimps watched out 
for each other's interests, if it was mutually 
beneficial.

Dolly thought of renting a crack house with a few more 
rooms, and expanding her operation, she was on the rise 
again, and would need fresh talent to maximise her 
profit, yes she thought, that was a wonderful idea.

THE END

*Feedback always welcome at Nefstoryr@yahoo.ca*

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

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