Jug Loving Jerry
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Unsuspecting Jerry free porn video
UNSUSPECTING JERRY, PT. 1.
A little intro here, this is my second story and hopefully it will be
better than my first. I took more time with this one so maybe you will
see an improvement. Roughly ? of this is autobiographical with incidents
I have personally experienced spread out through the story. This time I
have added some photos that hopefully will help the story.
Jerry was small of frame, 5' 7" about 120 lbs. With a boyish looking
face, little body hair. He had been an outcast from his family ever since
shortly after college, so he only had himself to depend upon. His father
or mother would be of no help at any level.
One fine day Jerry found himself out of work, and couldn't find work in
his field. His funds run dangerously low so he decided to hop in his car
and head for another town and try his luck there. About 75 miles outside
town his car breaks down at a rest stop on the highway. Sitting on a
bench with not enough money to get the car fixed he looked pathetic and
was feeling quite hopeless. Then two very attractive women, Alexandria
and Sandra who are very athletic looking, are intrigued with his boyish
good looks and inquire as to why he is so downcast. Once they learn of
Jerry's situation they invite me to their home in the country. They offer
to let him stay at their house if he does chores around the house, to
which Jerry readily agrees.
Jerry's motto is any port in a storm at this point. One of the ladies
gets a friend to go and tow his car to her house but once they arrive
there his car is stolen along with everything in it. Going home, to their
house, all Jerry has are the clothes on his back. Nighttime comes and
Jerry is given a nightee to sleep in. It's all they have, so they say.
Next day, Alexandria gives Jerry a dress to wear while washing his
clothes. Jerry's clothes were really a mess as he had messed them up
desperately trying to get his car running by crawling under the car
reaching across the dirty grimy engine. So really it was either put all
those greasy grimy clothes back on after that wonderful bath the night
before or swallow his pride and don the dress, which he did.
Alexandria- "Here Jerry, you can wear this old dress of mine while you
wash the clothes, sorry about your misfortune in loosing all your clothes
in your stolen car but we can get you some more clothes later on."
Jerry- "Well I have to wear something and a dress is ok for a desperate
situation like this but you gotta promise me not to laugh."
Alexandra- "Sure Jerry, both Sandra and I have to leave right away so no
one will see you in it anyway, bye bye have fun in your new job today, we
have always wanted a maid and you are going to make us so happy so you
are helping us as much as we are helping you. No need to curtsy dear we
aren't that formal."
Before Jerry could respond about the comment of his being a maid and the
curtsy thing, Alexandra practically flew out the door leaving Jerry
holding his new dress and looking rather confused.
Jerry speaking to no one? "She probably was just making a funny about
that maid curtsy thing. Ha, guess it is kinda funny me a man curtsying
and being a maid. Ha ha."
While the clothes are washing Jerry goes about cleaning the house, when
he returns to the washer, he discovers that the grease stains simply will
not come out. And not only that but the grease smell is still there.
Being somewhat finicky about things like that he decides to chuck um into
the garbage, No sense worrying about it Alexandra will bring him some
pants when she comes home that evening.
Alexandra's house was quite disorderly due to the fact that she and her
room mate Sandra both worked and worked sometimes long hours. So Jerry
had plenty to do that first day sorting through this and that.
Jerry continued cleaning all day till they came home. Around 6:30 pm both
ladies arrive home and are amused to observe Jerry in Alexandra's dress.
Sandra- "Isn't that your dress our new maid has on Lexie?"
Alexandra- "Why Jerry I never imagined you would wear that dress all day,
but if you like it please feel free to continue wearing it. You look
stunning in that dress dear."
Jerry- "Ok see my clothes were ruined and I couldn't wash the grease out
of them so I had to wear your dress Alexandra."
Sandra- "yea sure you did Jerry. I think Jerry is a natural for wearing
dresses don't you Lexie?"
Alexandra- "It sure seems that way to me Sandy."
With that last comment both girls laugh and head for the living room and
plop down on the couch and go through the days mail leaving Jerry feeling
quite humiliated and stunned at the door.
Jerry- "Uh Alexandra didn't you say you would get me some clothes today
in town?"
Alexandra- "Oh I'm sorry Jerry I was so terribly busy today I completely
forgot but not to worry dear there's no big rush is there? I mean we are
secluded enough here that you can get along just fine in your new outfit
without any problems. Sandra and I am not the least bit concerned about
it. Do be a dear hon and bring us some tea. We both like to relax with a
cup at the end of the day. I'll have green tea and Sandy likes chai tea.
Oh and there's a silver serving tray that you can bring it to us on. It's
right next to the breadbox. Hurry now dear."
Jerry- "But.......but....oooooh Ok"
Jerry then goes to the kitchen and prepares tea as directed and returns
with tea for both girls.
As he places the serving tray with tea and condiments on the coffee
table, Sandra speaks.
Sandra- "Thank you Jerry you're such a doll. Do be a good maid and
massage my back for me will you? I've had such a tense and hectic day, I
just need to totally unwind."
Jerry ? "But I'm not a maid. I'm just doing household chores and stuff
that doesn't make me a maid."
Alexandra- "Don't get all in a huff Jerry. It's just us and you are doing
maid work. What should she call you? Do be a good lawyer and get us a
drink? Do be a good mechanic and get us our supper? No the only thing
that works is maid so don't make a big deal about Look we both like you
and we know you've been stressed out this past year or so looking for
work so why not just enjoy your new job here. I mean all you have to do
is keep house and do a few things for us. Just enjoy this relaxing
carefree time. Humor us, we like having a maid. It isn't going to hurt
you is it? No it isn't."
Jerry- "Uhhh, well......"
Sandra- "We only want to help you Jerry, on the way home from work Lexie
and I both decided we could afford to pay you two hundred dollars a month
plus room and board. I know it's not much but you could relax and have a
stress free time while accumulating a small stake to get started again,
plus we aren't far from town and you could look for work there in the
future as well. We will keep the money for you till you decide to leave
and then in say 10 months you will have 2000 dollars, that's certainly
enough to get started again isn't it?"
Jerry- "Yea uh ok sounds good to me. Thanks girls I can't believe my good
fortune to stumble into you two in this desperate circumstance I have
found myself in."
Lexie and Sandra in unison- "You're welcome Jerry."
Jerry couldn't find any way around their logic and was led willingly into
10 months of servitude as a maid, unbeknownst to him.
Jerry- "Oh your massage Sandra."
Sandra- "Yes Jerry pay particularly close attention to the upper part of
my back that seems to be where the most tension is.
AHHHHHHHHHHHhhhhhhhhhhhh, yes that feels so good keep at it girl. Oh I'm
sorry Jerry the dress fooled me, I mean ?good boy, keep at it."
Lexie snickers slightly while opening her next envelope. Not knowing
quite what to think Jerry continues massaging Sandra's back and offers no
objection, as he is somewhat unsure of himself owing to how deftly
Alexandra so easily persuaded him to be a maid for 10 months.
Alexandria- "Jerry there is a cook book in the kitchen with all our
favorite meals in it called Cooking with herbs In it you will find all
the meals we like highlighted in yellow. I have here a menu here that I
prepared at work that contains what I want you to cook for us for the
rest of this week and all of next week. Please do follow the directions
exactly in the cookbook. We both like lots of herbs in our foods."
Jerry ? "Ok sure Alexandra."
Sandra- "Why don't you stop massaging me and go study that book some
Jerry. There are some wonderful herbs we use in cooking that are very
beneficial to your health. You will be surprised how wonderful herbs such
as fenugreek, saw palmetto, black kohosh, red clover, black nettle and
many others will make you feel. Also we are big on tofu and soy products,
and not much into meats except fish and chicken. We need these herbs
because they contain phytoestrogens, which are beneficial to our hormonal
balance. But don't worry they have little to no effect on men. I mean
lots of oriental men eat tofu and soy so don't worry your pretty little
head one bit dear."
Jerry- "Ok uh I'll go read some of the books now girls."
Alexandra- Aren't your legs just a little bit cold Jerry? It's getting a
little cooler now and wouldn't you like something on your legs to keep
them warm?"
Jerry- "Well yes, I only have this dress on not even any underwear and it
is a bit drafty, Do you have like some slacks I could wear?"
Alexandra- "No underwear, oh my we must fix that problem right away
dear."
Alexandra goes into her bedroom and returns with panties and pantyhose
and some Mary Jane shoes.
Jerry- "I can't wear those. Don't you have some long socks or something?
I can do without panties too."
Sandra- "Now don't be silly Jerry you have to have something to hold your
male member in. It bulges out slightly against the dress, you need
something on underneath to hold it in for modesty sake."
Alexandra- "Yes dear and pantyhose are so warm and comfy, you will find
doing house work in pantyhose all day will feel like a massage for your
legs. Now don't be silly, I picked out some panties that are a perfect
match for your new dress and these pantyhose will look much nicer on you
than long socks. Long socks tend to droop down and it is such a hassle to
keep pulling them up during the day, so let's not hear another word about
it and you go in your bedroom right this instant and put these on. I
won't hear another word about it."
With that she presses the garments in his hands and gently shoves Jerry
on his back towards the bedroom door. It all seemed just so logical Jerry
couldn't find any reason to protest. But then Jerry wasn't the brightest
kid on the block. Taking the clothes and moving towards his bedroom Jerry
responded, "Ok I guess so."
Sandra- "I'm sure the shoes will fit you're feel look the same size as
mine Jerry."
Alexandra- "Do hurry Jerry, you need to serve our supper. We are both
hungry and want to eat now."
Jerry- "Ok , I'll be out in a jiff."
Jerry went into his room and hurriedly put the hose and panties and shoes
on. Returning to the living room both girls noticed how nice his legs
looked in pantyhose.
Sandra- "Jerry I swear you have prettier legs than I do. All that little
light colored peach fuss hair on your legs isn't even noticeable when
they are all hosed up. Great legs girl."
Alexandra- "I'll second that Sandra, fabulous legs Jerry. You should be
very proud of them. I bet you've gotten lots of comments about those legs
haven't you Jerry?'"
Jerry- "IIIIIIIIIIIi sorta have been a little ashamed of them actually.
My cousin told me I have fat legs like a girl and my girlfriend told me
that she wished she had my legs, and guys say stuff like 'where's the
hair.' So I have kinda hid them from public view because of those
comments in the past."
Alexandra- "Here Jerry is a sweater with pink and white horizontal
stripes. It's getting a bit cool now that the sun is setting."
?
Sandra- "You shouldn't be so self conscious Jerry, If I had legs like
that I'd show them off. You need to as well. Hike your skirt up a little
dear and do a little spin for us. Let us see those thighs. Come on now
don't be shy."
Jerry slowly hikes his skirt up half way up his thighs and slowly turns
to the almost ogling stare of both girls.
Alexandra- "Fantastic thighs Jerry great legs girl you gotta show those
legs off they are a real asset."
Jerry- "I'm not a girl."
Alexandra- "I know, I know, I know dear, just got a little carried away
there, but you do have such great legs. It'll be fun to see them around
the house while you are our maid. They are quite decorative and give an
air of elegance to our house just like a piece of fine furniture. Now
move those gorgeous gams and put out our dinner on the table hon."
Confused once again Jerry walks to the kitchen in his Mary Janes and
prepares the dinning room table for the evening meal. It wasn't much just
some chicken and dumplings but the girls thought it tasted great.
Alexandra- "great cook Jerry, can't wait till you fix our normal fare
tomorrow. Don't forget lots of herbs dear."
Jerry- "Yea ok Alexandra."
Sandra- "Jerry Lexie and I have been thinking, since you've agreed to be
our maid for 10 months would you mind to much saying yes ma'am and 'no
ma'am' from now on? It would really help with this maid fantasy we have.
Most people never have maids and this may be the only time in our lives
we have one so would you mind too much? It's not really too much to ask
is it?"
Jerry thinks about this briefly and as usual is convinced by the
persuasiveness of Sandra's words.
Jerry ? "Yes ma'am I'll be glad to. And no ma'am it's not to much
trouble."
Alexandra- "Good Girl."
Jerry- "But I don't know about this good girl stuff ma'am. Couldn't we do
without that please."
Alexandra- "Oh come now Jerry you're in a dress with hose and Mary
Jane's, you've got to expect us to slip once in a while. When anyone sees
someone in a dress that looks like a girl as you do now, that person
can't be blamed for occasionally slipping and referring to you as a girl
now can he or she? Come on it's no big deal. You're wearing a dress and
you look fairly convincing as a girl what do you expect?"
Jerry once again is twisted around their fingers. He just can't seem to
out wit them. They just make too much sense.
Sandra comes over to Jerry and lightly fluffs out his hair, which covers
his ears.
Sandra- "There with a little work on your hair no one would be the wiser.
Here pucker up for me dear let's see what a little lipstick will do for
you."
Jerry spiraling down hill fast checkmated at every turn is quickly
discovering he is no match for these girls.
Jerry- "But I don't need lipstick come on. There's no reason for it."
Alexandra- "Jerry you agreed to be our maid, you know it's our fantasy.
No one will see you, Humor us, you've got a deal of a lifetime here. WE
just want some maid service for a while. And you are becoming such an
ornament to our home with every turn we're making here. First you're
svelte, teen like slender body looks so adorable in that dress then your
gorgeous legs. Your fluffed out hair looking so elegantly fashionably
female. So put the lipstick on dear you are gorgeous we want our maid to
be pleasing to the eye as well as pleasing in her chores."
Jerry- "but I don't know something seems wrong about this."
Sandra- "Trust me on this one Jerry. Don't spoil it for us. I don't want
to be mean but you have no place to go and no money so humor us. I mean
what's it going to hurt you really to put a little lipstick on ? What's
the big deal anyway. You're in a dress, pantyhose , Mary Janes girly hair
do, now really what's the big deal about a little lipstick dear?"
Before Jerry could respond Sandra firmly grasped Jerry's cheeks puckering
them up and before you could say boo was applying red lipstick on Jerry's
lips."
Alexandra- "Stunning you look absolutely stunning Jerry, try raising your
voice just a little for effect. And no one will ever think you're a guy.
Try it."
Jerry tired of resisting and always loosing gives in this time without a
struggle. And slightly modifies his voice to a slightly higher range.
Jerry ? "Yes ma'am."
Sandra- "I can't believe it he sounds just like a girl."
Jerry blushing and wanting to hide bows his head and smiles slightly.
Alexandra rises from the couch and pulls some eye shadow out of her purse
and holds Jerry's face similarly as did Sandra.
Alexandra- "Hold still Jerry don't move."
With that Lexie applies light blue eye shadow and rouge to Jerry's cheeks
and mascara as well.
Alexandra- "My my my Jerry you are quite a knock out of a girl."
Jerry feeling totally without any will power anymore and so humiliated
and controlled can only offers a weak, "But I, uh I mean".
Alexandra- "Get the digital cam Sandra, this is too good to miss. Photo
shoot time Jerry. Let's see you walk around the room here, Sandra get
lots of photos. Come on Jerry don't be bashful."
Jerry walks around the room like a guy but that's no good for Sandra.
Sandra- "No, no , no Jerry put one foot directly in front of the other
and sway those hips a little, not too much though. Come on girl strut
your stuff. Pucker those lips. That's it you go girl go."
"CLICK, CLICK , CLICK, CLICK" as she snaps photo after photo of Jerry in
fashion mode.
Next day Jerry awakes to find a new dress on his bed laid there for him
during the night by someone. Jerry puts it on along with the hose and
panties and shoes and goes out to prepare breakfast. Both girls hurriedly
dress come down from upstairs and gulp down their food and coffee and
dart out the door. As Sandra is leaving she tells Jerry to be absolutely
sure that he puts his make up on before they return home in the evening.
Giving Jerry a stern warning Sandra says, "Remember hon, if you upset us
there is no reason we can't show you the door right this instant."
With that comment, as if for emphasis, she somewhat roughly grabs my face
and lightly shakes it to show she means business.
Jerry is stunned once again and fear floods back in again at the prospect
of being homeless and penniless. As he watches them both drive away Jerry
realizes it is decision time. He could pull his old greasy clothes out of
the garbage and hike into town and make his way to the local homeless
shelter, or bite the bullet and play girl for a while. Neither choice is
very appealing to Jerry but the fear of being around so many big and mean
and rough characters as frequent the missions and homeless shelters. Fear
because of Jerry's slight build convinces him to stick it out as a girl
but just for a while. Returning to his room he sees a make up kit laid
out for him. Staring at it for a long while he finally reaches for the
lipstick and looks in the mirror. He applies the lipstick then the rouge
then all of it. On the bed, which he didn't, notice upon coming in is a
padded bra with a note from Sandra.
"Jerrie:
Please put this bra on to fill out your dress better..
Love,
Sandra."
Shaking, Jerry drops the note. Looks at the bra, and forces himself to
remove his dress and put the bra on, telling himself, "It's only for a
little while."
To be continued.
Tamera
- 05.12.2020
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