Punished for my Crime.
It's no wonder I grew up weird. A set of older triplet sisters, a pilot father who was away more often
than he was home and a mother who seemed to resent most males. My earliest memories are of my sisters
dressing me as if I was one of their dolls. By the time I was 16 my sisters had moved out to attend
college, my father was home even less as he was piloting international flights to pay for three
daughters at college and it was just Mom and I. She mostly left me alone but when she said jump I
waited for the order to come down, she was not a woman to cross.
I have pretty fair complexion and I have to say it but my face does have a girly look. My arms are thin
and my fingers long and slim. I play some tennis and golf so I'm not bulked up with muscle. I hadn't
even shaved yet as I had very little body hair and what I did have is very pale to match my blond hair.
I know from my days of being made over by my sisters that it did not take much work make up wise to
transform me into a passable girl and I even remember them taking me out once dressed up as their
Like most young guys discovering sex I started with cheap porn mags with pictures of cheap women then
moved on to better books with better pictures of better looking women. Being left at home alone gave me
the chance to move up to videos and I spent many an afternoon jerking off to my favourite vid sex. I
don't know how you acquire a fetish but I found my jerking off sessions were more intense if I had some
of my sisters underwear with me at the time. Eventually I was wearing their panties when I masturbated
or sleeping while wearing a pair of pantyhose. I didn't actually think of them when I was doing it but
they had so many different styles and materials and the feel of the fabrics on my cock was so much
different to my basic cotton underpants it just seemed to add to my enjoyment of jerkin' off.
My sisters had not taken even half their clothes when they moved out using the house as a free storage
locker. This was fine by me as I had access to all of their stuff and I was careful to wash anything
that got stained and ironed and put back. Then came that day. I had got a new vid and was anxious to
check it out. The girl on the cover was wearing a skirt and blouse combo that were a close match to
some clothes of my sisters so I was going to dress up in the same outfit while I watched it. Mom yelled
at me that she was going out and would be back later so as soon as the car left the drive I was in my
sisters room getting my outfit together.
I put on a crisp white blouse and a short red and black checked, pleat skirt. I could see some of her
red panties in the cover pics so I found a pair that looked the same and I then added some thigh high
stockings but as I'm not that tall I pulled them nearly all the way to the top of my legs. I went to
the TV and popped in the vid and sat back to enjoy the afternoon. Wow, it was amazing how close I had
got the outfit. One thing I never was into was bra's so while the woman in the vid had tits busting
from a bright red bra that stretched the fabric of her blouse I stayed flat.
I was so into watching this woman do a slow strip pole dance that I didn't hear my Mom come back in. I
don't how long she watched me watching the vid but suddenly she was between me and the television and
she looked set to explode. She called me everything from sicko, to pervert, to creep and I dashed out
of her way as she made a grab at me and headed for my room. I slammed the door closed and sat on the
floor with my back against it to stop her pushing in.
Mom was rather subdued when she talked to me through the door explaining that she just wanted a quiet
chat about sex and that maybe we should have had that talk earlier. It fooled me because I expected her
to rant and rave all afternoon and try to kick the door in. I cautiously opened the door and Mom pushed
her way in glaring at me with a look to kill. Her breating was deep and loud as she tried to hold her
feelings in check. Amazingly we did talk in a mostly civilised way for about ten minutes until she
asked about why I felt the need to dress like one of my sisters. I was mumbling some answer when
suddenly Mom grabbed my arm and dragged me into her room and sat me down at her make up table.
Next thing is I'm in the middle of a whirlwind of activity as my Mom applies makeup to me and works at
my hair. Then she rushed from the room and was back seconds later with a small lacy bra that had the
cups filled with padding and told me to put it on then she was gone again and I could hear her in the
girls room rummaging in the wardrobe. I put on the bra and replaced the blouse as Mom came back with an
assortment of shoes and boots for me to try on. I tried walking in several pairs until Mom settled on a
pair of white boots that came to just under my knee. They also had a chuncky cube heel that made it
easier to walk. Finally she gave me a small purse to sling from my shoulder to complete the outfit. As
I turned to face her the repeated flash from her camera nearly blinded me. I felt calm and relaxed as
Mom gave me the once over and a slight nod.
She took one more thing from my sisters room and then took me out to the car. I got in while trying to
see if any neighbours were looking but it was all clear. As we drove Mom told me that I was to do
whatever I was told to do when we got to our destination and not to let on that I was a guy as it might
not be exactly safe. My calm face was now a worried one and as we pulled into the carpark of a bar I
was scared. Mom handed me a pair of glasses to put on. They had belonged to one of my sisters who had
wanted to look smart so wore them even though they were not perscription.
The bar was dark with small down lights in the ceiling providing illumination. The room had about fifty
people in it mostly guys, but some women, everyone looked like they were on a break from an office for
lunch. Music played in the background and a few people were dancing. Along one wall almost in complete
darkness were a row of booths. Mom ordered some drinks and found a table. She told me that if I wanted
to be like my sisters then this was the place to start. No sooner did she finish talking when I guy
came to our table and asked if anyone wanted to dance. Mom explained that we were here for some "lunch"
and we had to be back at the office in an hour so we could only do some "regular" dancing. The guy
nodded as if he understood and then reached for my arm. I looked at Mom but she just grinned as he led
He was a head taller than me and from his shirt it seems his name was Mike and he worked for a
construction company. We arrived on the dance floor as a slow number started and he held me in tight
and just swayed to the beat. One hand held me in the middle of the back while his other hand drifted
lower and slipped under my skirt grabbing a big handful of my arse. He moved his hand over the material
of my panties and ran a finger along my butt crack. I squirmed a bit which he took to mean I was
enjoying it. Now his other hand slid down to join the other and holding a butt cheek each he lifted me
level with his face and planted a sloppy kiss on me forcing his tongue in and swirling it around my
He put me back down and placed a hand on my "breast". He told me he preferred woman with bigger tits
but younger was still better. My arse and breast were getting a thorough mauling and by the time the
song finished I was not sure I could sit comfortably. He then led me to a booth along the darkend wall
and let me get in first and then he sat blocking any chance of escape. He pulled a curtain across the
end of the booth so that anyone could see our heads but nothing below table level.
While he began pawing and kissing me one of my hands brushed against his pants and felt his hardening
penis. He stopped for a moment and undid his belt and trousers finally freeing his semi hard erection
and placing my hand on it. I gripped it and felt it grow firmer. He leant back against the booth seat
and closed his eyes as I pumped his penis dreading what may come next. Out of the darkness a waitress
arrived and left a beer on the table. It didn't even schock her to see a guy getting jerked off in her
He looked at his watch and then started pushing me under the table telling me my lunch time was nearly
over. I was on my knees under the table facing his short, thick penis. I had watched enough vids to
know what to do but again I was grossed out. He told me to hurray up and his voice had that edge of
impatience. One last deep breath and I wrapped my lips around the head letting my tongue run over it as
I adapted to the size. I slid a few inches in and then pulled back. Then his hand was on the back of my
head pushing it in place as his hips came off the seat to fuck my face.
I bobbed my head as I jerked his penis making slurping sounds and running my tongue along the shaft all
in an effort to get him off as quickly as possible. At last I felt his body tense and the grip on my
head firmed as he shot his load down my throat. I coughed and spluttered as he emptied his balls into
my mouth but I didn't loose any. He let me up as he put his penis back in his pants. As I sat up Mom
was right there talking to Mike explaining that I was new to the office and not very "experienced" in
doing lunch so maybe next time she could be his lunch date. He seemed happy as he got out of his seat
and made his way to the door.
Mom sat down and finished the beer while I got my self back together. She offered my a mouthful and I
used the beer to wash away the last traces of cum from my mouth. We gave him enough time to leave and
then we headed out but if I thought my lesson was over I was sadly mistaken. We drove home and I headed
for my room to take off the outfit but Mom stopped me and explained that this is what happens when
you're a female. Now she told me to go and kneel on her bed and to not look around until I was told. I
could hear her undressing behind me and I was imaginging all sorts of things happening. My cock was
getting hard with anticipation.
Mom pushed me so I fell onto all four's then flipped the skirt up over my back. Next she pulled aside
the panties from my arse. Her hand snaked between my legs to my throbbing erection rubbing the length
before slipping to my balls to roll them and coat them with some type of cream. She applied more cream
to my arse smearing it over the cheeks and into the crack. This caressing of my private parts put me at
ease so I was not expecting to feel anything nudging my arse hole. Then Mom told me that if my crime
was dressing as a girl then I would receive the appropriate punishment. With that she pushed forward
and the strap on dildo she wore penatrated my virgin butt. I let out a cry of pain but she told me it
hurt more when a girl lost her virginity.
She held my hips as the dildo slid deeper into my arse. As if sensing that I was up to taking it Mom
increased her rhythm pounding my backside to release her own frustrations. She was savage with her
assult slapping her hand on my butt cheeks as she relentlessly drove the plastic phallus into me. My
arm and leg muscles quivered with the strain of supporting myself in this position as well as the
pressure from my mothers weight each time she lay across me.
I lost track of how long she fucked my arse as I was overcome with both the pain and pleasure of the
moment. Finally the dildo slid from my arse but my hole still felt like a ring of fire. I heard the
clips unsnap and them my naked mother fell on the bed next to me her hair slick with perspiration from
her exertions. I was still on all four's and dazed from treatment I had just received when my mother
said "Fuck her". I was slow to react so she grabbed my cock and jerked it towards her I turned to face
her and again she said to fuck her but in a more forceful tone.
I positioned myself between her legs and slid my cock forward until I felt the heat of her cunt. I was
nervous and it was a couple of jabs of my cock until I slid into her. I let the head enter and was
easing into her when she thrust her hips forward to meet me and as smooth as silk I slid into her my
full length. From then on she was wild as our bodies mashed against each other in a frantic dance of
lust. I tried to fuck her as hard as she had done me letting my hip bones clash with hers. I was
concentrating so deeply on the in and out motion of fucking that I never did anything to her tits or
even try to kiss her.
It was just pure animal lust until I could no longer hold back and I pushed her legs up and my cock
down to go as deep as I could into her cunt. As I dumped the load of cum from my balls back into the
womb I had sprung from I thought of swallowing the cum at lunch. All I could hear was both of us
grunting as my cock spasmed another shot into the dark. Finally I rolled over and Mom had drifted off
into a semi sleep state so I made my way to the shower to clean up.
While this was the first time Mom dressed me up it was not the last and over the next few years we went
out lots of times and had sex with a number of people, both men and women. I finally moved away, got
married and had a family but sometimes when I'm home alone I'll slip on a pair of my wife's panties and
jerk off as I watch a porno DVD.
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