Sure Loser
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Just Another Pathetic Humiliated Loser free porn video
JUST ANOTHER PATHETIC HUMILIATED LOSER
By Sissy Gaye
Nancy knew about my submissive desires and my cross dressing and we had
experimented with her humiliating me in various ways, but it was always
private. Then one night when we were at a pool hall shooting a game, she
began to subtly humiliate me. We were playing straight pool--first one to
sink fifty balls was the winner.
There were three high-school-age girls playing at the table next to us. As
we played, Nancy began teasing me about how she was going to beat me in the
pool game. She started saying things that indicated we had made a bet over
the game, but we hadn't. She would laugh and say how she couldn't wait to
punish me for being a loser.
I'm not a great pool player but I'm okay. Nancy wasn't usually as good as
me, but this night she was really on top of her game. And I was not on top
of mine. In fact, the more she pulled ahead, the worse I got. Her teasing
had me really hard. So did her outfit. She was wearing a frilly
cream-colored blouse with billowy sleeves and a tight brown suede miniskirt
and boots. She knew how much I liked her blouse and as she would pass by me,
she'd rub it against me.
Eventually, the girls at the next table picked up on the stuff she was
saying and started to watch us play out of the corners of their eyes.
Then she sank a really tough shot and laughed out loud and said, loud enough
for them to hear, that she couldn't wait to see how silly and humiliated
I was going to look when I had to comply with her wishes as winner. One of
the girls said, "Excuse me, but I couldn't help overhearing. What are you
going to do to him if he loses?"
Nancy looked at me with an evil grin and told the girl, "I'm going to dress
him up in my mother's clothes every day for a week and make him walk my dog
around the block twice a day."
The girls all started cracking up. "What if you lose?" the first girl said.
"Well, I won't," said Nancy, "but if I did, I'd have to give him a blowjob
in the ticket booth at the movie
theater where we both work, while he sold tickets to customers." Well, the
girls were really interested now. They stopped playing their game and took
seats on a raised bench that looked over our table. They'd cheer when Nancy
made a shot or when I missed one.
It was Nancy 49 to me 38, when Nancy walked around in front of me to line up
what might be her winning shot. I was sort of in the way, but I thought I
was standing back far enough to not interfere and, trying to be cool and
restore some small shred of my dignity in front of these girls, I didn't
want to move. She looked back at where I was and lined up her shot.
I did not realize what shot she was lining up, though. Suddenly, she pulled
the stick back fast and hard
and the end smashed into my balls. I made a noise and doubled over. All I
could hear was the sound of
the girls laughing their asses off and congratulating Nancy on the best shot
of the night.
Nancy said, "If you don't move out of my way, I'll give you another."
Totally embarrassed and in considerable pain, I meekly moved aside and Nancy
sank her last shot.
The girls all cheered and chanted "Loser, loser, loser!".
Nancy walked over to me and laughed in my face. She slapped me across the
face. "Looks like you're
going to be prancing around the block twice a day in my mother's lingerie,"
she said. She started to turn
back to the girls then spun back towards me and brought the cue stick up
between my legs again,
hitting me right in the balls even harder than the first time. I crumpled
with a high-pitched cry and sat
on the bench, doubled over. The girls couldn't believe I just took it like
that. They started saying what a
wimp I was. Then they started teasing me about how stupid I was going to
look in Nancy's mother's
clothes.
"Get me a Coke, slaveboy," she ordered and I kind of crab-walked over to the
machines, trying to
relive the ache in my balls, and bought her a Coke. When I returned, Nancy
was sitting on the bench,
telling the girls about the various humiliating outfits she was going to
make me wear the following week
for dog walking duty.
"...then I'll make him do it in just a slip and stockings and high heels and
his hair tied up in a scarf..."
The girls were laughing and teasing me as I was made to gather up the pool
balls and cues and return
them. They asked if they could come watch me walk the dog in drag, but Nancy
told them that she didn't want people set up to see me. It had to be
spontaneous, so that I would have the hope that I could get through it
undetected and if I was seen, it was just my bad luck. They were
disappointed until she asked one of them for her address and promised to
mail her a picture of me performing my dog walking duties in drag. This was
fine with them and she got all three addresses. They each told me how much
they were looking forward to seeing my pictures and they hoped I'd be seen
by lots of people.
As we left, she said to me, "You know how hot it made me to humiliate you
like that?"
"I'm very glad you enjoyed yourself." I said truthfully. "I really liked it
too."
"Not as much as you're going to," she teased. "After all, I can't disappoint
those girls, now, can I? So
starting this weekend, you're going to walk my dog in my mother's clothes
and I'm going to take lots of
pictures to send to them. I can't wait to tell my Mother, she's going to get
a kick out of this."
I'd only gone out in drag a few times, mostly on Halloween, and my
experiences had not always been good. Since Nancy wanted to use her
Mother's clothes instead of my own pitifully small wardrobe to complete the
punishment, she decided that one day was enough punishment, but that her Mom
would have to be in on it.
Nancy's Mom Gloria was a sweet lady but she was the opposite of Nancy, who
was fun-loving but serious about her future and not a big party animal. By
contrast, Gloria was a recent divorcee who was making up for lost time like
crazy. She spent her days with her divorcee friends in a mad whirl of
shopping, drinking, country clubbing and chasing men. One night about two
weeks after the pool hall incident, I was having dinner with Nancy and
Gloria when Nancy brought up the subject of my losing the bet. She said
that as loser I had to be her slave for the day and do whatever she wanted
and I couldn't complain or refuse anything no matter how humiliating it was.
This seemed a few steps up from what we'd discussed, but Nancy just gave
me a smile and I fell right in line. Then she told her Mom about me
dressing in drag for the day.
Well, Gloria howled. Immediately after dinner, she went through her
basement closets, looking for "old" clothes I could wear for my punishment.
Whenever she stopped pulling things out, saying that should be enough, Nancy
would encourage her to find more. She told Gloria about the photos she
wanted to send to the girls from the pool hall and she said, "The more
outfits we have to choose from, the better. Besides he has to spend the
whole day in dresses, so I think he should give us a fashion show of lots of
different looks."
"Are you really going to make him walk the dog in a dress?" asked Gloria.
"Absolutely," said Nancy. "You think he's have let me off the hook if I'd
lost the bet?"
"What were you supposed to do if you lost?" Gloria wanted to know.
"He expected me to get down on my knees in the ticket booth at work and give
him a blowjob while he was selling tickets."
"My God, Nancy, what were you doing agreeing to a bet like that?" Gloria
wanted to know. The look she gave me showed that I was on her shit list for
thinking I could degrade her daughter that way. I was helpless to argue,
but the truth was that Nancy had thought that part of the bet up too, to
answer one of the girls in the pool hall. Not that I would have said no to
such an experience.
"Simple, Mom, I knew there was no way I was going to lose. He's a lousy
pool player. The first time we played, I had a terrible time letting him
win so he wouldn't feel all humiliated losing to a girl."
"So, you set him up for this?"
"Just like a pool hustler."
They both had a good laugh as I stood there filled with shame, my arms full
of the clothes I was going to wear.
It was decided that the following day, a Saturday, would be my day of
punishment. And to prepare me, Nancy spent the evening plucking my
eyebrows, shaving my legs, my chest and my back, and washing and curling my
hair. She had me dress in a pair of her Mom's panties and one of her bras,
then she had me put on pantyhose and a slip. Next, she did a dry run of my
makeup and got me into a pair of Gloria's old sandals that had only two-inch
heels and were just a little too small. These were all the kinds of things
we'd done before but always in private. This time Gloria stuck around to
watch the whole thing. She made comments continually, teasing me and
belittling me. And Nancy egged her on, knowing it was driving me wild. She
made me walk around to practice in the heels and they thought of a lot of
little errands to send me on around the house.
Finally, they put me into red satin blouse and a tight black knee-length
skirt and Nancy tied a silk scarf over the curlers in my hair.
"What's that for?" I asked.
"To cover your curlers while you're out," she said. "I've decided I want you
to walk the dog tonight as a warm-up."
I opened my mouth to protest, but she slapped my face. Just then, Gloria
came back from making tea.
"What was that?" asked Gloria.
"I had to slap this little girly," said Nancy. "She's trying to get out of
her punishment."
"Oh dear," said Gloria. "That's very naughty. Perhaps she needs a
spanking. Should I get you a hairbrush or would you rather use one of the
ping-pong paddles?"
"Ping-pong paddle, I think," said Nancy, "unless you'd rather be a good
girl."
"Okay," I said. "I'll walk the dog."
"Oh, you're no fun. You could have let me spank you for a while first."
Turned out walking the dog was not that simple. First they had to take my
picture, then give me all sorts of instructions on whose house not to let
the dog pee in front of, and finally I was sent off with the dog and a
baggie in case the dog pooped.
The walk down her driveway was so thrilling. It was a cool night with a
mild breeze and the feeling of the slip rubbing against my thighs was making
me very horny. They had the driveway lights on and were watching me from the
front door. I'd been given quick instructions on how to walk in a ladylike
fashion, but it was hard when a 80 pound Irish Setter is pulling you along.
The walk around the block was pretty uneventful, except for the fear that
flooded through me every time a car went by. At the end of the opposite
side of her block, right after the dog took his dump and I was leaning over
to pick it up, Gloria's car suddenly glided up next to me and Nancy leaned
out with the camera. FLASH!! She took my picture as I straightened up with
the baggie full of dogshit in my hand. I was so humiliated. I just knew I
was going to look like a total asshole in that picture.
When I got back, Nancy decided that I should also take out the garbage in
drag, but before I went, she made me take off the blouse and skirt. Then
she photographed me in the driveway carrying the garbage can in just a slip
and a headscarf. A car went by as I was out at the curb and I was terrified
of who might be seeing me in this state, but whoever it was just kept
driving. When I got back to the house, Nancy had locked me out. I rang the
doorbell a few times, but when there was no answer, I sat down on a deck
chair to wait for her to take pity on me.
She left me outside for about 20 minutes, then she let me in. She had me
change into a negligee and peignoir set and we went through to have a last
cup of tea with Gloria before going to bed.
At that point, Nancy announced that the following day, I would be their
servant, doing housework and cooking so that she and her Mom could have a
well-deserved day off. Since I already did some cooking and lots of chores
around the house, this was no big deal to me, but the chance to do it while
dressed in drag was delicious.
Nancy decided that servants couldn't sleep with the mistress of the house,
so I was plunked down on an air mattress in the basement.
I was awoken the next morning when Nancy poured a pitcher of ice cold water
on me with Gloria watching and laughing. "Oh, Nancy," she said, "you're
going to drown the poor thing."
I was hustled upstairs to get my hair combed out and then fresh makeup was
applied. I remember the first outfit they put me in. It was a soft, pink,
crepe blouse with big ruffles at the cuffs and around the neck paired with a
silky gray floral skirt. Under it, I wore a pink bra and panty set and a
pink slip with a lot of lace trim. I've always had a slip fetish and,
knowing this, Nancy made me walk around in just the slip to start fixing the
breakfast, before they put me in the blouse and skirt for my first dog
walking expedition of the day.
Again, I was photographed several times with and without the dog and then I
was sent off to do my duty.
This was a much scarier walk as the sun was coming up and there were people
out and about, including a paperboy who kept circling me and two little
girls who wanted to pet the dog. I guess I looked okay, since they didn't
pay any attention to me, but I was shaking by the time I returned to Nancy's
house. She and Gloria were just getting out of the car so I knew they'd
been following me taking pictures.
"Aren't you just adorable in that outfit," said Gloria. "You know, I never
wear it anymore, so it's yours if you like. I insist."
One look at Nancy told me I'd better be gracious, so I curtsied and thanked
Gloria and assured her I would wear it often. This got them both howling
again. I was changed into an old housedress for serving breakfast, which I
was not allowed to eat. Then it was a skirt and sweater combination for
pictures in the backyard. I went through a half-dozen changes in outfit
before lunch, which I served on the deck in the closest thing they had to a
French maid outfit, a black slip, a ruffled white blouse, black stockings
and heels, and a large white lace handkerchief folded and pinned to my hair.
Nancy decided that since there was a servant to handle the dog walking, old
Beau would be treated to three walks today. That allowed her to send me out
in the middle of the afternoon in a peasant blouse and a long floral skirt.
That was the worst part of the whole day as there were people everywhere and
I was sure they could all tell I was a guy in drag. But no one shouted or
pointed or chased me, so I guess I did okay.
The rest of the afternoon was spent shooting pictures of me in different
outfits walking the dog up and down the driveway. As dusk approached, the
wind picked up and dark clouds moved in. Before long, the rain started and
as we came through the garage to shoot what was supposed to be the last set
of dog walking pictures, the sky opened up and the deluge began. I was
wearing a creamy satin blouse with long puffy sleeves that ended in cuffs
with large black buttons and a pair of silky brown long culotte type things
that Nancy called palazzo pants. I stopped at the edge of the garage. But
Nancy insisted I go on. "Beau loves the rain and this will make it look
like the photos were taken on different days," she reasoned. "So you take
him down to the end of the driveway, wait about a minute to make sure you're
good and soaked, then come back and pose right there by the car."
I told her she was cruel and beautiful and, after giving her a long kiss, I
went out to be drenched for her amusement. By the time I got back, Gloria
was standing there too, laughing at my drowned rat appearance. Nancy
insisted I turn this way and that until she got the perfect pose. Gloria
remarked on how cruel she was being and then said, if it was up to her, I'd
suffer far greater humiliations for daring to think I could force Nancy to
blow me at work.
"Like what, Mom?" asked Nancy, fanning the flames with a wicked grin.
"Like that ping-pong paddle spanking for one thing."
"Okay." She turned to me and said, "Slave, I order you to submit to Mistress
Gloria for forty whacks on your ass with a ping-pong paddle. Now!" I
curtsied and came into the garage, dripping.
She pulled the blouse and pants off me and made me bend over a sofa in the
basement, soaking wet in just a bra and panties. When Gloria's first couple
of whacks seemed too timid, Nancy grabbed the paddle and gave her a ten
stroke demonstration, which was not deducted from the total. Gloria did
much better after that.
After my ass gleamed red, even through the yellow panties I was wearing,
Nancy asked her Mom what else she would recommend for my punishment. "Well,
he should give you a blowjob."
"Mom, I don't have a dick."
"No, but you have a dildo don't you?"
So, the next thing I knew, I was dressed in an old green chiffon cocktail
dress and was down on my knees in front of Nancy, sucking her dildo through
the fly of her jeans as Gloria watched and commented on my cock sucking
technique. When it came time for Nancy to "cum", Gloria took a jar of mayo
from the fridge and flung spoonfuls of it in my face to simulate the jism.
I sat there and let them laugh for a good long time. The humiliation was
absolutely incredible.
Finally, it was late enough for my final dog walk. Making good on the
promise she'd made to the girls, Nancy made me do the honors in a slip and a
headscarf. This time I was really terrified because I wasn't just in drag,
I was in lingerie, which wasn't only embarrassing, but might have been
illegal for all I knew.
Fortunately, although the rain had stopped, the late hour and weather kept
the streets pretty clear and the only really embarrassing moment was when
Nancy popped up out of a bush a couple of houses down from her own and took
my picture.
It was late, when we sat down in our negligees and peignoirs for late night
tea and Gloria congratulated me on being such a good sport. I told her
honestly that I had lost the bet, fair and square, and I loved Nancy, so I'd
had no choice but to sacrifice my dignity for their amusement. I told her
that I had deserved the ridicule that had been heaped upon me and I would
never again be foolish enough to make a bet against Nancy over a pool game.
It was only then that Gloria realized she could have made my day even more
humiliating by inviting over some of her girlfriends, in particular Margie,
a blonde bombshell with an incredibly abrasive personality who delighted in
emasculating any man in her path. I was glad I had escaped having her see
me the way I'd been tormented today.
"That's okay, Mom," said Nancy. "I'll get him to make another bet before
long and we'll have the whole gang over to watch the fun."
"Don't bet on it," I said, but I didn't really mean it.
THE END
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