


Busted and Hoodwinked

by walterio



Category: Transsexuals & Crossdressers
Published: 2009-07-12
Updated: 2009-07-12
Packaged: 2017-05-01 02:49:12
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/busted-and-hoodwinked
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: Two robbers are caught in the act by an Asian ladyboy.
Erotica Tags: Anal Sex, Cum Swallowing, Dildo Usage, Foursomes, Gay Sex, Group
Sex, Large Cock, Massive Cum Shots, Oral Sex, Threesomes
Average Rating: 4.36






        Busted and Hoodwinked


INTRODUCTION  
  
Mack and Barry were cell mates in prison which is where they first met. They
had both been convicted of burglary and breaking and entering. The befriended
each other while in prison and became lovers. Barry was gay and Mack became a
bisexual during their time in the same cell. Mack actually liked fucking Barry
and having Barry suck his cock. Mack had gotten comfortable jerking Barry off
but that was as far as he went. Mack liked it when he and Barry lay on their
sides fucking and Mack would give Barry a reach around and jerk him off.  
  
Barry was a handsome almost pretty blonde 25 year old. He was 5'8" tall and
weighed about 160 pounds. Barry had a very effeminate figure with smooth
flawless skin and a very curvy ass. Mack loved fucking Barry's ass. Barry had
an average size cock at about 6" and a little over 4" around. Mack on the
other hand was more macho. At 6'2" and 185 pounds he looked like an athlete.
Mack had brown hair and he was well endowed. His cock was just shy of 8" long
and just over 5" around. Mack liked his cock as it was above average but not
too big. Barry loved Mack's cock and he loved having it stuffed in his ass.  
  
The two of them made a pact to get together when they were released from jail.
Mack got out about 30 days before Barry and when Barry was released he looked
Mack up. The two of them shared the same parole officer and they decided to
share the same apartment. It wasn't long before Mack and Barry were planning
more heists. They were both skilled thieves and Barry could pick any lock he
ever came across. Barry got a job as a hairdresser and Mack worked as a
masseuse in the same salon. The two of them served the female clientele and it
didn't take much to get the women talking. Barry and Mack always learned the
social and travel plans of their customers, which made them easy pickings.  
  
Barry and Mack would hit the homes of their clients when they were out for an
evening or away on a trip. Barry and Mack would steal small valuable items
that could easily be misplaced or lost. They never hit the client's home big
so as not to draw suspicion to them and they always stole items that were
easily fenced. It didn't take long for them to run out of victims at the salon
so they decided to venture out into suburban neighborhoods. It was at one of
those homes that they had a memorable encounter.  
  
BUSTED AND HOODWINKED  
  
Barry and Mack were convinced that no one was at home when they broke into a
cute Cape Cod home. They were dressed in all black as always and they wore
black ski masks to conceal their faces. They moved stealthily along the pout
side of the home to the back porch where Barry easily pocked the lock. They
were inside within seconds and moved quietly through the house. They used
penlight flashlights to search for valuables in the home. Mack had made his
way into one of the bedrooms and was going through the closet and dresser when
he saw the living room lights come on and then he heard a voice other than
Barry's.  
  
"Alright, hold it right there and put your hands up," a female sounding voice
called out.  
  
Mack eased his way out of the bedroom trying to remain concealed as he checked
out the living room. He saw that the homeowner had her back to him. She was a
petite shapely Asian girl with long black hair over her shoulders. She was
wearing a negligee and panties and Mack could not help checking her out. She
had nice legs and a cute curvy ass and she was pointing a gun at his partner.  
  
"Take that mask off," the girl ordered.  
  
Barry peeled off his mask and Mack noticed that he was scared. It was the
first time Barry had been held at gun point and this was by a woman which
really made him nervous. Mack was waiting for an opportunity to take the woman
from behind and disarm her but he knew he had to be careful.  
  
"So you like to break into homes and steal people's treasures do you? Well I
have a treasure for you right here," the girl said waving the gun at Barry.
"You are kind of cute and you have a nice mouth. Bring that mouth over here
and sample my treasure. See how swollen my clit is. It is ready to be sucked."  
  
Mack watched in disbelief as the girl pulled her panties down past her pubes
and beckoned Barry to come and eat her pussy. Mack looked at her cute ass
again and decided that if he was able to subdue her that he would stick his
cock in her tight little ass. Mack watched as Barry moved over to the girl and
then dropped to his knees. Mack knew that Barry had never been with a woman
and he wondered if Barry would actually be able to eat her pussy. Mack stared
as Barry moved his face close to the woman and it seemed that he began eating
her. Mack's view was blocked by the girl's legs but he saw Barry's head moving
and he heard the girl groan.  
  
"That's it you have it. Suck my clit. Oh you are so good, keep sucking me
until I cum," the girl said excitedly.  
  
The girl was clearly distracted now and it seemed as if she would cum at any
second. Mack saw his opportunity and snuck up behind the petite Asian. As he
got closer he saw Barry's head bobbing as if he was sucking a cock rather than
eating a pussy. Mack then noticed that the Asian girl was really getting
excited as she closed her eyes and relaxed her guard.  
  
"Oh my, I'm cumming, hold me, hold me tight," she screamed as her body
trembled and she orgasmed.  
  
Barry reached up and grabbed the petite Asian by her shapely cute ass and
squeezed her buttocks as she bucked her hips in his face. It was the
opportunity that Mack had been waiting for and he moved quickly. He wrapped
one arm around her tiny waist and he grabbed the gun out of her other hand.
The gun came out of the girl's hand easily and as he held onto her he moved
his hand up to her tiny firm tits and squeezed them. Then looking over the
girl's shoulder he saw that his partner had not been eating pussy but sucking
on a small dick. Mack guessed that even hard the dick wasn't any bigger than 3
or 4 inches. No wonder Barry seemed unconcerned about eating pussy.  
  
"Well what have we here?" Mack said loudly as he fondled the Asian's tits and
rock hard nipples.  
  
Barry stood up and smiled as he studied the pretty Asian transsexual. "Mack
this is a real life transsexual. The kind that I see on the porn site listing
for Asian Ladyboys," Barry stated.  
  
"I think that our friend here owes you a blow job and I think that I'll fuck
that cute little hot ass," Mack said.  
  
Mack pulled the negligee off of the ladyboy and then pulled down the panties
and removed them. "What's your name darling?" Mack asked sarcastically.  
  
"Bo, my name is Bo," the Asian replied shyly.  
  
Barry and Mack dropped their pants and underwear and they were both sporting
stiff cocks ready for action. Bo looked at the two cocks and asked if Barry
could fuck him first since Mack had a bigger cock. Bo got down on all fours
and asked Mack to get the lube from the bathroom. Mack found the bathroom and
returned quickly with the lube handing it to Barry who promptly began to
grease up Bo's asshole. Bo groaned as Barry worked one then two fingers into
the cute shapely ass. Mack took up a position in front of Bo and moved his
cock toward the ladyboy's face. Barry greased up his cock and then eased it
into Bo's ass. At the same time Bo engulfed Mack's cock and began to suck on
it.  
  
Both Mack and Barry were turned on by the whole scene and it wouldn't be long
before they were shooting their loads in Bo's mouth and ass. Bo proved to be
an excellent cock sucker and was able to take most of Mack's cock in his
mouth. Bo also was very experienced in anal sex and he was able to use his
talented anal muscles to drive Barry crazy. Mack was the first to cum and he
flooded Bo's mouth shooting six streams of cum into it. Bo handled the barrage
easily and swallowed every drop of Mack's seed. Barry stiffened behind Bo and
drove his cock deep into Bo's asshole as he unleashed his load in Bo's rectum.
Bo massaged the stiff cock with his anal muscles and drained Barry's cock dry.  
  
Barry and Mack remained hard and they started to change positions when Bo
asked them to take off all their clothes. Barry and Mack quickly and with
seconds they were as naked as Bo. Mack moved behind Bo and caressed Bo's
lovely buttocks as he stroked his own cock. Barry had already fed his cock to
Bo's mouth and Bo reached between Barry's legs to finger Barry's asshole. Mack
then eased his cock slowly into Bo's ass savoring every moment of the slow
patient anal penetration. Mack really liked Bo's sweet curvy ass and he was
glad that he had already cum once so that it would be a while before he would
cum in Bo's ass.  
  
This wasn't the first time that Barry and Mack had double teamed another guy
but it was Mack's first transsexual or ladyboy as Barry called him. Mack
studied Bo's features as he fucked him and it was like he was fucking a girl
in the ass. Bo looked so much like a girl that it was actually a little
intimidating. Mack caressed Bo's shapely ass as he drilled it with his
impressive cock and Bo groaned every time that Mack went a little deeper. Bo
excellent cock sucking skills made Barry cum quicker than he expected. Mack
watched as his partner stiffened and shot his load into Bo's mouth. Mack
wasn't even close to cumming again and he was in no rush as he loved fucking
Bo's hot ass.  
  
Barry fell back on the floor and watched as Mack reamed Bo's asshole. Bo
grunted and groaned as Mack pounded his ass and drove his cock in deep. The
sound of their skin slapping together filled the room as Mack's thighs smacked
against Bo's ass. Mack loved watching the cute ass cheeks jiggle each time he
drove his cock home. Bo pleaded with Mack to fuck him faster and to give him
his cum. Mack picked up the pace and drilled Bo's ass until his body finally
stiffened and he shot a huge load into Bo's ass. Mack stayed pressed against
the pretty Asian ladyboy and allowed his cock to be milked by Bo's talented
anal muscles. Unable to stand the tingling sensations any longer, Mack pulled
out of Bo's ass. Mack watched as his load oozed out of Bo's asshole and
trickled down over Bo's ball sac. It was an unbelievable sight and one that
Mack relished.  
  
Bo was hard again and this time he wanted to fuck. Barry cooperated by getting
on all fours and Bo greased up Barry's asshole. Bo pushed his little dick into
Barry's ass and Barry, being used to Mack's big cock, almost giggled as the
tiny stiff pecker entered him. Barry felt it was like one of Mack's fingers in
his ass. Bo was pressing against Barry's buttocks so that he could keep his
cock in Barry's ass. He only moved it in and out about an inch so that it
wouldn't slip out. Mack stroked his own cock as he watched the two of them
fuck. He decided that he would like to fuck Bo's hot little Asian ass again.
Just then the front door opened and everyone turned towards it.  
  
"Holy shit it's Nicky," gasped Bo.  
  
"What the hell is going on here? You little slut, I'm only gone for a few
hours and your fucking two strangers," Nicky screamed.  
  
Mack assumed that Nicky and Bo were lovers but Nicky was even prettier than
Bo. Mack wondered if Nicky was also a ladyboy. Nicky stormed over to Bo as if
to strike at him. But Mack intervened and grabbed a hold of Nicky who
struggled in his grasp.  
  
"Let go of me you bastard, you cocksucker," Nicky yelled.  
  
That comment pissed Mack off so he wrestled Nicky down to the floor. "We'll
see who the cocksucker is," Mack threatened.  
  
"Fuck him, fuck Nicky," Bo called out.  
  
Mack realized that his cock was hardening again and he decided to find out
about Nicky. He heard Bo say him loud and clear so he was sure that Nicky was
another ladyboy. Mack pinned Nicky's arms behind his back and he pulled
Nicky's skirt up baring his pantyhose covered ass. Nicky's ass was even
rounder and curvier than Bo's ass. Mack felt his cock stiffen and he was fully
erect. He tried to keep Nicky's arms pinned and pull down the pantyhose at the
same time. Mack had trouble with the struggling Nicky and then Bo came to his
aid.  
  
Bo took a hold of the back of the pantyhose and ripped them apart. Both of
Nicky's ass cheeks were now naked as they poked through the hose. Bo then took
the lube and greased Nicky's asshole and then applied more lube to Mack's
cock. Nicky was still pinned to the floor with Mack holding his arms. The
pantyhose were torn open enough for Mack to get at Nicky's ass even though it
was still intact around his waist. Bo guided Mack's cock toward Nicky's ass
and Nicky grunted and feebly protested when Mack's cock slid in slowly.  
  
"Don't you dare fuck me you bastard," Nicky screamed.  
  
But Bo just as vocal called out, "Yeah fuck him, fuck his ass."  
  
Mack started moving his cock in and out of Nicky's ass and it was obvious that
his wasn't the first cock in there. Nicky loosened up quickly and soon Mack
was gliding in and out of the pretty Asian's ass. Barry now had moved closer
to watch his partner fuck Bo's lover. Barry noticed that Nicky's cock was
erect and it strained against the pantyhose as if seeking to be let free.
Barry reached over and rubbed his hand up and down Nicky's enclosed shaft as
Mack continued his anal assault.  
  
Mack noticed that Nicky had given up the struggle so he released Nicky's arms.
Nicky placed his arms on the floor and arched his back accentuating his
shapely ass. Barry continued to stroke the stiff 4 inch pecker in the
pantyhose as Mack pushed the back of Nicky's sweater up baring his back. Mack
then unclasped the bra and let Nicky's tits spill into his hands. Mack
massaged the firm globes as he continued to ream Nicky's ass. Then Nicky
screamed again.  
  
"Oh God, I'm cumming," Nicky called out.  
  
Mack felt Nicky's body tense up as Nicky shot his load into his pantyhose.
Mack felt Nicky's anal muscles tighten around his cock each time Nicky's cock
pulsed and spewed. Nicky's pantyhose were drenched as he had really shot a
huge wad. Nicky was just beginning to relax when he felt Mack's cum shoot into
his ass. Nicky felt the thick cock pulsate as it filled Nicky's ass with
semen. Mack was absolutely drained at this point and he just collapsed on top
of Nicky's body. Then Nicky fell forward onto the floor with Mack on top of
him. The two of them remained motionless for several minutes until Nicky
begged Mack to move off of him. Mack rolled to his side and over on his back.  
  
"Gotcha Mack!" Barry said with a hearty laugh.  
  
"What do you mean gotcha?" Mack asked in surprise.  
  
"The three of us set this up. You've been hoodwinked pal," Barry replied.  
  
"You mean that you know these two," Mack said in shock.  
  
"I sure do. I do Bo and Nicky's hair and when their hair is drying we have
some fun in the salon. Just like you do with those frustrated housewives who
come in for a massage," Barry added.  
  
Barry was right; Mack often fucked some of the housewives during their
massage. Now Mack knew that Barry was getting his share of action at the salon
too. Mack looked at Barry, then at Bo and Nicky and then he laughed loudly.
They had certainly pulled one over on him.  
  
"God look at my pantyhose it's ruined," Nicky said and they all laughed.  
  
Nicky then added, "That is the first time I ever came in my hose. It was a
very erotic feeling."  
  
Nicky took off the pantyhose and the rest of his clothes so that he was as
naked as the others. The four of them sat around drinking and telling stories
until it was time to retire. Mack and Barry were invited to spend the night
and they graciously accepted. Mack and Barry were shown to the guest room and
then Bo and Nicky retired to their own bedroom. Mack and Barry were tired and
sated so they went right off to sleep as soon as they were in bed.  
  
SUNDAY MORNING  
  
Mack woke up before Barry and he was grateful it was Sunday and they didn't
have to go to work. Mack went to the bathroom and freshened up after relieving
himself. He returned to the guest bedroom with every intention of fucking
Barry that morning but when he returned Barry was gone. Mack looked for Barry
checking the living room and kitchen. Mack smiled when he saw all the clothes
scattered around the living room and he had a quick flashback to the night
before. Mack then decided to check the master bedroom and sure enough Barry
was with Bo and Nicky. Bo and Nicky were on their sides in a 69 position and
Barry was behind Bo fucking him in the ass. Barry smiled at Mack when he
spotted him in the doorway.  
  
"Come and join us Mack. Nicky has been waiting for you to fuck him again,"
Barry stated.  
  
Mack's cock was hard by the time he got in bed and behind Nicky. Barry reached
over and handed Mack a tube of lube so that he could crease Nicky's asshole.
Mack applied the lube liberally to Nicky's ass and his own cock before sliding
his cock back in Nicky's ass. Nicky placed her hand on Mack's thigh as to
guide the penetration assuring that he didn't go too deep at first. Once Nicky
loosened up he removed his hand from Mack's thigh and Mack pushed his cock in
all the way emitting a gasp from Nicky. Mack watched the scene before him as
he fucked Nicky in the ass. He could see Nicky sucking on Bo's tiny dick and
he watched as Barry slammed his cock into Bo's ass.  
  
The two Asians came first that morning but Barry and Mack were close behind
them. Mack saw Bo's body tighten and he assumed that Bo ejaculated into
Nicky's mouth. Then Mack felt Nicky's anal muscles tighten around his cock and
he was sure that Nicky had cum in Bo's mouth. Mack then came in Nicky's ass
and once again flooded it with a massive load. The four of them remained in
the same position until all cocks were milled or sucked dry and then they
separated. Mack and Barry were very capable of cumming three sometimes four
times a day and they were already for a second round.  
  
Barry and Mack had Bo and Nicky get on all fours next to each other and this
time Barry fucked Nicky and Mack fucked Bo. Mack was as turned on as ever as
he fucked the cute Asian ladyboy. Mack had never seen anything like them and
he was very drawn to their petite femininity. He loved their cute tits and
hard nipples. He loved their petite frames and jet black hair but most of all
he loved their round perfect asses. As Mack fucked Bo again he caressed Bo's
curvy buttocks as he watched his cock slide in and out of Bo' bubble butt.
Mack at times looked over at the other couple next to him and watched Barry's
cock slide in and out of Nicky's perfect ass.  
  
Even though Mack had already cum once that morning the eroticism of the moment
got to him. He felt that familiar tingling in his scrotum and then the surge
of semen as it flowed through his cock. He drove his cock deep into Bo's
asshole and held it there as he fired a barrage of cum into the petite tight
ass. Bo once again used his anal muscles to squeeze Mack's cock and drain it
of his semen. Mack was in no hurry to pull out of Bo' ass and he left his cock
buried to hilt in Bo's ass. Mack caressed Bo's curvy buttocks as he once again
marveled at the smooth and flawless skin. Mack looked back over at his partner
and watched Barry fuck Nicky until Barry ejaculated in Nicky's ass.  
  
The four of them decided to take a shower and although it was very crowded
with four people it was fun. They soaped and washed each other's bodies and
Mack loved running his hands over the soapy slick bodies of Bo and Nicky. The
four of them got turned on again and headed back to bed. This time Bo sucked
on Mack's cock while Barry and Nicky moved into a 69 position and sucked each
other's cock. Bo swung his body around so that Mack could play with his small
stiff cock. Bo pushed his hips close to Mack's face in an effort to get Mack
to take the little pecker in his mouth. Mack had never sucked a cock in his
life but as he looked at the cute erect cock in front of him, he was tempted.  
  
"Go ahead Mack suck my clit. Eat my boy pussy," Bo whispered.  
  
Mack looked long at the little hard dick and then convinced himself it
wouldn't be so bad. He thought that it couldn't be that different than sucking
an oversized clit and he had done that plenty of times. Mack took the small
stiff cock into his mouth and began to suck on it. Bo gasped and cooed when
the warm mouth surrounded his cock. Mack was surprised how easy it was to suck
Bo's cock and when Bo came in Mack's mouth, Mack did not spit the cock out.
Mack drank down the oriental nectar that spewed into his mouth much like he
would swallow a woman's love juice. Mack was surprised how sweet and salty
Bo's cum tasted and he was not at all repulsed by the act.  

When Mack and Bo separated they saw that Nicky and Barry were still in a 69
position but that Barry was now on the bottom. Mack had not cum in Bo's mouth
and he was still hard so he took aim at Nicky's ass again. His cock slid in
easily as Nicky's ass had been stretched enough by Mack's cock from the
earlier fucking. Barry watched as his partner's cock slid into Nicky's ass
above him and he reached up and tickled Mack's taut ball sac. Bo went to the
dresser and retrieved a fake rubber cock. Mack watched as Bo greased up the
dildo that was about the same size as Mack's cock. Bo then moved down the bed
and pushed the dildo into Barry's ass. Barry grunted at the intrusion but
handled the fake cock easily.  
  
Bo fucked Barry with the dildo as Barry sucked on Nick's cock. Mack continued
to fuck Nicky's sweet ass as Nicky sucked Barry's cock. Then they all seemed
to cum in unison. Barry drank down Nicky's dick juice as Nicky's swallowed
Barry's load. Mack filled Nicky's ass yet again with a substantial load and
Nicky wondered how Mack could still cum so much. Mack eased his cock out of
Nicky's ass and as he did his cum oozed out and trickled down over Nicky's
balls onto Barry's face. Barry moved his mouth so that he could catch the
semen as it dribbled over Nicky's testicles.  
  
The four of them then collapsed on the bed together as they were totally
fucked out and the sex was done for that day. Minutes later they showered,
dressed and then decided to go out for brunch. They spent hours together at
the restaurant relaxing, drinking coffee and reading the Sunday paper. It was
almost 3:00 PM when Mack and Barry left for home. They thanked Bo and Nicky
for a wonderful weekend and Mack once again congratulated on pulling off his
seduction. Outside the restaurant Bo stepped up to Mack and kissed him and
then Nicky kissed him as well. They also both kissed Barry goodbye and said
they hoped to get together again soon. To the passersby, it looked like two
men kissing their Asian girlfriends goodbye.  
  
At home that evening Mack teased Barry about becoming a lady boy. "You would
be great as a girl," Mack started.  
  
"Forget it," Barry snapped and then laughed at the suggestion.  
  
"No really, you could let your blonde hair grow down to your shoulders. You
could start taking female hormones and we could get you some breast implants,"
Mack continued.  
  
"Yeah and then what happens the day you get tired of fucking me and move out.
What am I supposed to do then if I look like a girl?" Barry snapped again this
time appearing annoyed at the suggestion.  
  
"Well you would be a good looking ladyboy and you could find another guy,"
Mack replied and then laughed at the absurdity of his suggestion.  
  
"Yeah, well it's not going to happen. If you want to fuck ladyboys, Bo and
Nicky will be waiting for you," Barry said and then added, "I am quite content
sucking your cock and having you fuck me just the way I am."  
  
"I am too," Mack admitted.  
  
That night in bed they were both too worn out for any sex. Mack laid in bed
thinking about Bo and Nicky and he still had a difficult time believing that
he had sucked Bo's little cock and swallowed his cum. Mack wasn't sure if he
would ever suck another person's cock but at the same time he was sure he
would suck Bo's again in the right situation. Mack knew that Barry would be
thrilled if Mack ever agreed to suck him but that was not in the immediate
future. Mack fell asleep thinking about Bo and Nicky and had very pleasant
dreams about them. In fact the dreams were so pleasant that Mack woke up in
the middle of the night with a raging hard-on. He slipped out of bed to get
some lube and he greased up his cock thoroughly. Mack got back into bed and
snuggled up behind Barry.  
  
Barry was on his side and Mack moved in close and slipped his slick dick into
Barry's ass. Barry just moaned and didn't move as if he was still sleeping.
Mack fucked Barry slowly until he came in Barry's ass. The two of them stayed
in the spoon position and fell back asleep with Mack's cock still in Barry's
ass. Sometime during the night Mack's cock softened and slid out of its snug
sheath nestled between the two bodies. The two of them slept soundly through
the rest of the night. Tomorrow it would be back to work but Mack's life had
been changed forever. He would look forward to the days when Nicky and Bo came
to the salon to have their hair done by Barry and then get a massage from Mack
as they had promised.




End file.

