Sissy Mission 3 Rummage Sale Sissy
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The Rummage Sale free porn video
The Rummage Sale
By Margaret Jeanette
Margaret Strom was very happy. She had just sold an antique
dining room table with six chairs for over a thousand dollars. She
had gotten it at a rummage sale two towns over for a pittance and
now had realized a handsome profit on it. The sale assured that her
antique shop would be in the black for some time.
She was on her way home when she saw a rummage sale sign. She
parked across the street and surveyed the merchandise set out in
the driveway. She saw an end table that might be worthwhile
checking, then headed home to pick up her husband Jerry.
They went back to the rummage sale and she was amazed that they
were only asking five dollars for the table. She knew she could
sell it for much more than that. As she was looking Jerry was
checking out the other merchandise. He motioned her over and showed
her a pair of red flats. He thought she could wear something
besides the black shoes she always wore. To please him she tried
them on. They were too big.
He said, "That style shoe was what the girls all wore when I was
in high school. I always thought the red ones were sexy looking."
Margaret said, "You think they are sexy. You try them on."
He protested saying, "Those are women's shoes. I am not going to
try them on."
Margaret said in an icy voice, "I said try them on. Now, try them
on!"
He resignedly slipped his shoes off and tried them on. He said
they were a slight bit tight. Margaret took them and went and
bought the shoes and the table. Jerry helped her put the table in
her small pick-up truck.
They took the table to the store and when they got home Margaret
told him to put the red shoes on. He protested but after five
minutes found himself putting them on. He said they were too tight
and Margaret came back with a pair of nylon knee-highs and told him
to change socks and try them again. They fit much better. He was
surprised at how light they felt on his feet compared to his other
shoes.
He wore them for the whole evening not even thinking that he had
women's shoes on. At bedtime when he took them off Margaret told
him to put the nylons in the toes so he would have them when he
next wore the shoes. He took them off and put them in his closet
not intending on wearing them again.
The next day he was working on his newspaper column when he
decided to take a break. He went and poured a glass of his favorite
cran-grape drink and settled in the recliner. He was going to turn
the TV on but found himself thinking about the red shoes. He
wondered why his wife bought them and had him wear them. It was no
big deal but it made him think how he gave in to her. Then he
thought it made her happy so no big deal. Finally he went and
finished his column and E-mailed it to his distributor.
As usual when Margaret got home he had supper started and when
they wee eating Margaret said, "I'm surprised you aren't wearing
your sexy shoes. I thought you would be wearing them and all horny
when I got home."
Jerry responded, "Those shoes don't make me horny. Do your shoes
make you horny?'
Margaret told him, "No, but last night I got a little horny
seeing you in those red shoes. If you want any loving you may have
to wear them to excite me."
She thought to herself that this was a lie but she giggled to
herself that he would wear them to get a little loving. She
wondered how far she could take it. It made a wonderful game.
That night in bed they snuggled but when he wanted to make love
she told him she probably would when he wore his red shoes.
The next morning he thought about putting the red shoes on until
she left for the store but decided not to. During the day he
wondered about what she had said. Before he started supper he went
and put the nylons and red shoes on. When Margaret got home she
smiled when she saw him wearing the shoes. She made sure to give
him a passionate kiss.
That night in bed they made exquisite love. The next morning
Jerry told her that was the best sex they had ever had. Margaret
wondered how she could take it a little further. When she suggested
he wear the shoes all day he complied.
That day she studied the paper for rummage sales. She saw two
that she thought she would check out. The first one she checked on
the way back to the store from lunch. There wasn't anything that
interested her. After she closed the store she checked out the
other one. She didn't see anything for the store but saw a pair of
red shorts that she was sure would fit Jerry. They were only a
quarter so she bought them.
When she got home she kissed him hello and told him she had a
present for him. She said she would give it to him after supper.
After supper she showed him the shorts. She said they matched the
shoes perfectly and he should go and put them on so she could see
how he looked. She was so excited about hem he agreed to put them
on.
He went to the bedroom and removed his slacks and when he put
them on he was shocked that hey were trimmed with lace around the
leg openings and on the edge of the pockets. He was going to take
them off but decided to show her how silly he looked in them. They
were very tight on him.
When she saw him she told him they made her hot. She told him to
keep them on. He was mortified that she acted that way but did as
she said. That night they made passionate love. She told him over
and over how sexy he looked in red. He just enjoyed the attention.
The next day as he was working on his column he thought about the
wonderful lovemaking the night before. He worried about where this
was leading but decided it wasn't so bad wearing the shoes and
shorts. He didn't want anyone else to see him but Margaret was all
right to see him as it made her hotter than hot.
That night she told him she sold the end table for one hundred
ten dollars. She said that was over a hundred-dollar profit on it.
She was so happy that her happiness overflowed into him. After
supper they sat and watched TV for a while then went to bed.
Jerry started kissing her but she was distant. Finally she said
she didn't feel like doing anything and turned over with her back
to him. He knew it was senseless to continue trying to make love to
her. The next morning he got up and when the two of them were
getting dressed he decided to wear the shoes and shorts. He told
her he was afraid the shorts would burst if he bent over. She said
she could help.
She handed him a pair of nylon panties. It was a plain white pair
and she told him to put them on. He complied and noticed the shorts
slid over the panties easier than over his cotton under shorts.
They ate breakfast together and after she left he went to work on
his column. It was hard to concentrate as he was horny but enjoying
the feeling of the panties against his manhood.
That night when Margaret came home she was carrying a bag from a
department store. She laid what looked to him like a dozen pair of
red panties out on the counter. She told him he should have his own
panties and not have to borrow hers.
Jerry asked, "Do they all have to be so feminine with all that
lace and ruffles? Couldn't you find some plain ones?"
Margaret told him, "No, all the red ones were like this. Besides
the sexier the panties the sexier you will feel. Now, go put them
in your underwear drawer."
He took them and when he tried to put them in the drawer there
wasn't room for them. Margaret solved the problem by removing all
of his old under shorts. He wondered what she was going to do with
them but didn't ask.
That night they made love that included what was the hardest he
had ever cum. When they were done he was pleasantly spent. He laid
there and enjoyed the afterglow. The next morning when they were
getting dressed he asked where his other under shorts had gone.
Margaret told him they were in the bag for the thrift store. She
said she was going to drop it off on the way to work. This
disturbed him a little bit but he didn't think it was worth it to
argue with her about it.
That night when Margaret got home she was all over him. They were
close to making love before supper. Jerry enjoyed every minute of
it. Shortly after supper they started some passionate kissing. Soon
they were making love in the living room.
As they made love Margaret said, "You need more red clothes.
Should I pick some more up for you to wear while these are in the
wash? What do you think?"
He replied, "Yes, I guess so. That makes sense." He was on the
edge of cumming.
She asked, "Will you wear whatever I pick up as long as it is
red?"
He was starting to cum. He gasped, "Yes, oh ye-e-e-e-e-s!"
He came in a torrent. This was the best he had ever felt. There
was nothing in the world like this feeling. After they finished he
was going to the bathroom when he thought about what he had agreed
to. He thought she would maybe pick up a red shirt and red slacks
for him to wear.
When it was time to go to bed they kissed and hugged and fell
asleep in each other's embrace. The next morning they had one of
the most enjoyable breakfasts they had ever had. Margaret was
laughing and joking like she never had before. Jerry loved this new
Margaret.
Jerry felt so good he finished two columns that day. For supper
he made his almost famous bar-b-qued chicken. Margaret was so gushy
that they almost skipped supper. After supper she took him into the
bedroom.
She had him strip to his panties, and then she attached a pair of
breast forms to his chest. Then she pulled out a red long-line bra.
He protested but she asked him if the sex wasn't great lately. He
told her it was. She convinced him to go along with her. When she
pulled a red garter belt and red stockings out he thought about
ending it right there but allowed her to slip the stockings up his
legs and attach them to the garter belt.
When she slipped the red silk slip over his head he wanted to
scream for her to stop but nothing came out of his mouth. She had
him step into a red knit dress that seemed tight on him. He didn't
notice the tightness at first being in shock. When she slipped a
pair of red heels on his feet he was finally getting things back in
place.
Jerry protested, "Isn't this going a little too far? You can't
expect me to wear a dress do you?"
Margaret said, "You agreed to wear whatever I got you in red,
didn't you?"
He responded, "You couldn't find a red shirt and slacks?"
Margaret told him, "You look so good in red and with the red
panties and all I thought these clothes were more fitting for you.
Now come and let me put some lipstick on you."
She led him to her vanity and picked the reddest lipstick she
could find. She noticed as she applied it his shoulders sagged a
bit. She giggled to herself inwardly.
She planted a big kiss on his cheek telling him she didn't want
to ruin his lipstick. She told him to walk around to get used to
the heels. As he was walking she showed him three other dresses she
had picked up for him to wear and two other slips. When she showed
him three other red bras she told him to find which style he wanted
and she would get him more.
He was flabbergasted at all of this news. He never thought she
would be coming with dresses for him. He couldn't believe how happy
and buoyant she seemed.
She came by him and handed him a red purse and told him his
wallet and some other necessities were in it. She told him to come
along as the stores wee open over an hour yet. She pulled him out
he door and opened the passenger side door for him. He sat down in
a daze.
She got in and started to drive. As she was driving she said,
"When you get in the car sit down on the seat then keep your knees
together and swing your legs in. It will preserve your modesty."
She parked in front of a store and when she led him in he saw it
was a Wig Fashion Boutique store. They looked at wigs until a
saleslady came by them. Margaret told the lady they wee looking for
a medium length wig probably in black. The saleslady showed them
five different medium length wigs. Margaret selected one and had
the lady put it on his head. She loved the way it looked with the
bangs covering his forehead and the curls on the side and in back.
They bought it and a wig cap.
He wore it out of the store. She drove for about three blocks
then stopped at a store where she had his ears pierced in two
places on each ear. She selected a gold stud for one hole and a red
stone stud for the lower. She also picked out three pairs of dangly
earrings that were each red with different styles of dangles.
He couldn't believe this was happening to him. He couldn't
believe she was actually doing this to him. He wondered what she
was thinking, dressing him in a dress. He just could not think of
a way to tell her that he didn't want to wear a dress.
As they were heading home Margaret said to him, "I know you would
rather wear a shirt and jeans but you look so cute in that dress.
I really appreciate you doing this for me. It makes me feel very
warm just knowing you are wearing those clothes and when I see you
in them it causes little explosions with my feelings. I know you
are too good to me but I love it. Tomorrow why don't you wear that
red one with the white lace trim? I think that will look great on
you. Oh, here's where we can get you some cosmetics."
She pulled in and parked in front of an all night drug store.
Inside she talked to the cosmetic saleslady. The saleslady said she
was done in ten minutes but would help them pick out the right
shades that would match her complexion. Margaret told the lady it
was for him and the cosmetic lady said no problem. The lady started
to pick colors for eye shadow, lipstick, foundation and blush. When
the lady suggested some perfume, Margaret agreed. The lady was
working over but didn't mind as she was earning a good commission
on the sales. They finally settled on White Lilac perfume.
By the time they were done he had over eighty dollars worth of
cosmetics, perfume and make-up remover. Margaret told him to pay
for it and when he opened his purse a tampon fell out. He blushed
when he saw what it was and the saleslady told him not to be
embarrassed about a tampon falling out of a purse.
When they got into the car he said, "Let's go home. I've had
enough shopping. This is embarrassing shopping for all of these
things."
Margaret said, "Did any of the salespeople embarrass you? No, I
didn't see any do anything to embarrass you. Maybe tomorrow you
should go shopping and get some more outfits. What do you think?"
He said he didn't think he could do that. When they got home and
got everything put away they enjoyed a hot chocolate before going
to bed. After he was undressed Margaret reached into the last bag
on the bed and pulled out a red nightgown and a red baby doll
pajama outfit. She told him to choose which one he wanted to wear.
When he had the baby doll outfit on he looked at all the lace and
little bows on the top. He thought this wasn't right. Margaret told
him to go into the bathroom am spray some White Lilac perfume on
himself. He did as she requested and returned to the bedroom.
She went wild grabbing him and kissing him on the lips hard. Then
she forced her tongue into his mouth. She pushed him down on the
bed on his back and pulled the panties down around his knees. He
was very hard and she mounted him. They came at almost the exact
same second very hard. They were both spent.
He laid awake for quite a while thinking about how he was wearing
dresses and worried that he should feel more determined to get out
of them. He thought about how nice it felt wearing them and that he
wasn't hurting anyone wearing a dress but it just wasn't right. He
thought about some of the things Margaret and he had done in the
past and finally thought about how it could be worse.
When he fell asleep he dreamt about going somewhere wearing a
dress. It was some sort of store and he was trying a formal on. He
was giggling and carrying on something fierce. It was so real that
he woke up and it took a while before he realized it was only a
dream.
He woke up again quite early for him, but felt refreshed and
ready to go. He got up and decided he was going to wear a shirt and
slacks. But he couldn't button the shirt over the breast forms, so
he decided to put on a dress. He selected one that had a scalloped
edge at the hem and had bell sleeves decorated with small red bows.
He had breakfast ready by the time Margaret got up. She was
eating her toasted English muffin and drinking her orange juice as
she watched him refill his coffee cup and come to sit down.
Margaret said, "You are getting very good at walking in the
heels. It excites me to see your rear sway so much. You are making
me so very happy. When we bought those shoes I never thought it
would go this far but I am happy it has. You have been so
understanding through all of this"
Jerry said, "In a way I like the feel of the dresses but it
doesn't seem right, me as a man wearing a dress. I like the way you
respond when I am in a dress but wish sometimes I could wear a
shirt and slacks. This morning I wanted to put a shirt and slacks
on but I couldn't button the shirt over these breast forms."
Margaret said, "You look so much better in that dress than in
your dull shirt and slacks. You give me a feeling that I am married
to someone exciting who isn't afraid to try something different
just for me."
Jerry laughed and said, "It's different all right. Now, why don't
you try something different for me? Today you are wearing a black
pants suit, why don't you wear something more feminine. You have me
wearing extremely feminine clothes, why don't you try to wear more
feminine clothes?"
Margaret said, "These clothes go with owning the store. They
project an image to the customer. They tell the customer I am all
business. If I wear a frilly dress then the customer thinks they
are dealing with a dumb woman and I can't have that."
Jerry said, "So when you are home you are still a business woman
first and a woman second. Is that what you are telling me?"
Margaret said, "No, not at all. At home I am your wife and
lover."
Jerry responded, "Then why don't you change into something more
sexy and feminine when you get home?"
Margaret replied, "I really never thought about it. For all that
you have done for me I owe you to try to look sexy for you. You
pick out a dress or any outfit for me to wear and tonight when I
get home I'll change into it. How does that sound?"
He told her that sounded good and they finished breakfast and she
left for work. He went to work on his column and when going to get
a can of pop noticed the delightful feel of the skirt swirling
around his legs. He didn't know why but he felt pretty. He went
into the bedroom and looked at himself in the full-length mirror.
What he saw was a good-looking woman, not a beauty pageant winner
but a good-looking woman nonetheless. He giggled to himself when he
twirled around watching the skirt billow out. Then he got the
feeling again that it wasn't right to feel this way. Finally he
went to finish his column.
The column was finished and he read his E-mails. One from his
distributor praised his last few columns and told him that they had
received many positive responses. He was extremely happy as he
signed off and went to get some lunch.
After lunch he decided to find a sexy outfit for Margaret to wear
that night. When he looked in her closet he was amazed that he
couldn't find a single item of clothing that could be considered
sexy. He noticed she didn't have a single pair of high heel shoes.
He had never noticed before that she always wore pants suits and
never skirts and blouses. He thought to himself, when it comes to
clothes she is in a rut.
He didn't put out any clothes for her to wear. When she got home
she kissed him and told him how lovely he looked. She looked in the
bedroom and when she didn't see anything on the bed to change into
she assumed he had forgotten. She was glad because she didn't feel
like changing anyhow.
At supper Jerry said, "I looked in your closet today but I
couldn't find one single item I would say is sexy. I was totally
surprised not to find any dresses or even skirts in your closet.
You are thirty-three years old and all I found is gramma clothes.
Also, I didn't find a single pair of heels. Are you really that old
that you never wear any clothes with color in them? I am wondering
if you have me in these dresses because you are afraid to wear
something like them yourself. Is that what is happening?"
Margaret's jaw had dropped and finally after a long silence said,
"I never realized that I had gotten in such a rut. When I go
shopping I always buy black or dark colors. Now that you mention it
I haven't worn any bright colors since high school. In answer to
your question I do not want you in dresses because I am afraid to
wear them. I have never really given it a thought. Something has to
change and I know it has to be me. I am thin enough to find
something sexy for you, especially after all you have done for me."
That night Margaret totally surprised Jerry by taking the breast
forms off so he could wear his regular men's clothes the following
day. On his own he put the floor length nightgown on for bed. He
looked at her and saw she had a plain cotton nightgown on. He
mentioned it to her and she had to agree that she looked like a
gramma going to bed.
The next day he did his column and then mowed the lawn. When he
got in the house the answering machine was beeping. It was Margaret
telling him she needed a hand to get some things she had bought at
a rummage sale. He called her and agreed to meet her at the
rummage sale. She gave him the address and he left.
He arrived at the sale site before she did. When she arrived she
told him the dresser and tobacco stand were hers. He put the
tobacco stand in the back of her truck. Together they got the
dresser in the truck. He told her he would follow her back to the
store to get it unloaded.
When they had it unloaded and in the store she opened the top
drawer and took out two dresses. One was yellow with blue flowers
and was trimmed with lace. The other was white on top and had a
black skirt. It looked to him that it was a mini skirt. She told
him to take them home and hang them in her closet. She told him she
might be a little late for supper as she had some shopping to do
after she closed the store.
When she came in she was carrying a lot of bags and one fairly
good-sized box. She was laden down pretty good. He told her they
were having a casserole for supper and she told him she would be
back in fifteen minutes, twenty tops. He set the table and waited.
When she came out he was flabbergasted. She was wearing a lacy
cr?me colored top that left her midriff bare and a black mini skirt
with black mesh nylons and a pair of black heels. She was wearing
the reddest lipstick he had ever seen her wear. He fell in love all
over again with her.
Jerry said, "How could you hide that all these years. You look
like a dream. You are beautiful. I love you!"
They kissed and Margaret realized that she had been missing
something for a long time. They enjoyed supper with an animated
discussion. Jerry was on top of the world knowing that he had
gotten her to look at herself rather than at him for feminine
clothing.
It was short lived as she said; "Now all we need is for you to
get dressed all sexy. You turn me on in your red dresses. After
supper why don't you fix yourself up for me."
Very reluctantly he agreed and after supper he changed into the
red dress with white piping trim. The skirt was a straight one that
was tight on him but he wore it for her. When he came out Margaret
let out a whistle. He blushed and she said, "You look really,
really pretty when you blush like that."
He thought for a minute then decided to let the whole thing hit
the fan. He said, "We have to talk. I know you like to see me in a
dress. There are some things I like about wearing a dress but it is
not customary for a man to wear a dress. I put on a dress for you
only because I love you. I don't want to hurt your feelings but it
bothers me quite a bit when I am wearing a dress. You are the most
important thing in my life and I'll do whatever you want but I
would hope you would reconsider your requests for me to wear a
dress so often."
Margaret looked shocked at first, then she listened with full
attention. She answered him saying, "If you didn't look so sexy to
me in a dress I wouldn't ask you to wear one. You are asking me to
reconsider how often I ask you to wear a dress. How often is
reasonable?"
He told her maybe twice or three times a week is more than he
would care to but he would if that was what she wanted. She sat and
he could tell she was thinking very hard.
Finally she asked, "How about Tuesdays and Thursdays one week and
Monday, Wednesday and Friday the next week. That gives you one week
of twice and me a week of three times. It is Wednesday now. Could
you wear a dress for the rest of this week then start the Tuesday
and Thursday next week?"
He replied, "I think I can. Now can you promise me that you will
try to dress sexier at least on the days I will be wearing a
dress?"
Margaret said, "Dear, I'll try to dress sexier everyday just for
you. Besides when I looked at myself in the mirror tonight I felt
really good about how I looked. I felt sexy without thinking about
you in your dress. I never thought I could feel like a schoolgirl
again but you have awakened the schoolgirl in me. For that I thank
you."
Jerry said, "You'll always be my school girl sweetheart. That
will never change. Just so you know, I may wear a dress on some
days that aren't on the list. Those will be days that I want you to
know especially how much I love you!"
And once again they went to bed, both of them feeling passionate
and loving.
end
(c) 2004 by Margaret Jeanette
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