Allegra
- 3 years ago
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It All Started With A Question! 2 free porn video
It was about three weeks after I had first met Jennifer, and I was back
having breakfast at that same little diner. Once again like before I
needed to go to that hardware store down the road. I had just arrived
and was sitting at the far end of the counter, getting ready to order my
breakfast, when out of nowhere I heard Jennifer's voice. She was walking
behind me, as I heard her say, "Hey - Hi-there Jack!"
I turned to see her heading for the same booth she was in a couple of
weeks ago.
So, I said, "Oh! Hi Jennifer!"
She looked back at me saying, "Want to join me over here?"
I said, "Sure I would love too. Let me let the waitress know I'm
moving."
Just then I heard the waitress say, "Don't worry I'll bring your coffee
over there."
The waitress had heard what I had said and followed me over to the booth
with mine and Jennifer's coffee. I said, "Thanks," and sat down in
Jennifer's booth. I took a quick look around as I sat down with
Jennifer, and realized once again, we seemed to be the only people over
on this side of the diner, just like the last time. This was great with
me, because it made it easier to talk with out others over hearing us.
Once I was seated in the booth, the waitress, put the two cups of coffee
down, and then took Jennifer's and my order. Jennifer and I made small
talk, which was mostly about what she had been doing over the last couple
of weeks.
I filled her in on what I had been up too, and that I had even gone to
one of my support group meetings the night before.
Our meals arrived just as Jennifer started to ask me how last night's
meeting went, and if I felt better about myself after the meeting. She
actually asked me whether I felt good about the meeting, or did I still
feel like something wasn't right?
"Wow." That was an odd question. How did she know I didn't feel right
after the meeting? I was wondering how she knew I felt kind of alone.
Heck I was even asking myself, why I had even gone to the meeting. I
remember that it seemed like all night long most of the other Gals / Guys
at the meeting didn't even talk to me.
That's when I heard Jennifer say something a little strange. She looked
me in the eyes as she said, "You know Jack after the last time we talked
I had time to think over all of what you had told me." She went on to
say she had something to ask me. She explained that she was about to
suggest something, but it was going to be completely up to me if I liked
what I heard.
I was little confused when she said that? I mean what kind of idea could
she have?
What she said next took me by complete by surprise and I was a little
shocked.
Jennifer told me that she really liked me, and that she would like to try
her hand at role-playing with me. She said she would like to role-play
as my Auntie. She thought that maybe she would even have a nanny help
take care of me if I wanted. She looked me right in the eye saying,
"It's all up to you, if you would like to try role-playing with me as
your auntie?" She gave a big smile as she said that she would love to try
being my auntie for maybe a full week?
This caught me completely off guard. I looked at her saying, "Let me get
this straight? You want to pretend to be my auntie and let me play at
being a little girl for a full week. Are you sure you're okay with this
idea? I mean you realize that you would be playing an Aunt to a guy
dressed as a little girl? The idea doesn't bother you, and you don't
think it's silly of me to want to dress up as a little girl?"
That's when to my surprise I heard her say, "Yes, I can't wait to try
this role play thing with you." She went on to say, "Actually, I'm
thrilled with the whole idea of playing your auntie, but I'm not sure how
I want to go about it just yet.
"You see Jack there's somethings you don't know about me. The one big
thing is, I'm a very rich lady, and when I say rich, I mean rich, rich,
like over $900 billion dollars rich. My husband died about three years
ago, leaving me his whole fortune. I own six factories, in six different
states, I have a mansion in each of those states. Plus, I own a yacht, a
private plane, and I even have a small villa in St Thomas over looking
Megan's Bay.
"As a matter of fact, one of the mansions, which is the smallest, is
where I stay a lot. It's just over in the next town. I'm really just a
normal gal Jack, who happens to have tons of money. Heck I was raised
here in this town and grow up around here. I wasn't from a rich family
and because of that I like helping others. I volunteer and give money to
a youth center in town and help out there twice a week.
"Anyhow I think you have a very interesting story, and I would love to
see you all dolled up in a cute frilly little girl's outfit. I think you
would look adorable all dolled up.
"So, here's what I have in mind, but only if you would like to try
something like this. I can make arrangements for you to stay with me, as
my little niece for a week?
"My question to you is, would you consider staying with me as my niece
from let's say, this Friday night to maybe next Friday or even next
Saturday morning, or heck maybe even that whole weekend too. I mean it's
only if you really want to try this out? Plus, if you're not happy with
how things go. You can always leave any time you want too."
I sat there for a couple of minutes going over this whole idea in my mind
before I said, "Wow!" You mean I can spend over seven days or more with
you, dressed twenty-four hours a day, as a little girl. Gees, that
really sounds like it could be a lot of fun? Are you sure you want to do
this?"
Jennifer gave me this look, while saying, "Yes I'm sure, but you must
understand, if we do this I would have to be completely in charge, just
as if you were a little girl. That means what I say goes, including what
you wear, how you are treated. Plus, if I feel you need a spanking, you
will get it. I think you should really think about this before you say
yes, because if I want you dressed up in a really frilly outfit so I can
take you out to a fancy restaurant as my niece; Honey that's just what
will happen. I'm not saying I would do that; it's just a reference so
you understand. If you are okay with me being in charge of your life for
a full seven to ten days, then all you need to do is say yes?"
By this time my stomach was doing flip-flops, my heart was racing over
ninety miles an hour, and I felt dizzy. I was completely speechless,
because I was still trying to take in what was just said. All I could do
at the time was shake my head up & down yes.
Jennifer asked me if I was saying yes to her offer. She said if that was
a Yes, then she would expect me at her place this Friday at about 4:00
o'clock in the afternoon. She went on to say that I could bring a couple
of my own frilly outfits, and my dolly if I want. She then told me that
she will be supplying me with everything else I would need. When I say
everything, I mean everything right down to the panties you will be
wearing.
I just looked at her saying, "Okay, but before I really say Yes, I really
need to know why you are doing this. I mean you must have some kind of
reason behind this offer."
She went on to explain that she always wanted a little girl she could
spoil, by throwing big birthday parties for, or dressing her up in real
cute frilly outfits. Take her out to places like the park or even a
fancy restaurant, maybe even to a movie. But my husband died before we
had any children. This would be like having the daughter I always
wanted. Plus, I'm pretty sure it would also make all of your fantasies
come true.
I sat there thinking her idea over for a moment or two and then I said,
"Okay first off if I don't like how it's going, I can leave any time I
want right?"
She said, "Yes that's right, if you're not happy, then you can leave at
any time."
To which I said, "WOW!" I can't believe my ears. I guess I'm saying the
answer is a big "YES! I would love for us to try this. You can count on
me being there at 3:30 on Friday for sure."
Jennifer said, "That's great! Now there's one more thing I need you to
do. I need you to come with me right after we finish eating. I hope you
don't mind, but I kind of figured you would like this idea. So, I took
the liberty of making an appointment with my seamstress. This way she
can take some measurement for me, as I want to have a couple of real
pretty and frilly outfits made just for you."
I said, "Oh no Jennifer! You really don't need to do that, honest."
Jennifer said, "But I really want to, and I won't take no for an answer.
Plus, I have the money, so why not."
Once we finished our breakfast and an extra cup of coffee, we got up to
leave. Jennifer left a big tip and paid both of our bills. We then went
outside, got in her car, and headed on over to her seamstress.
Could this really be happening???
We arrived at the seamstress's house in no time at all. Once inside, I
was asked to strip down to my underwear. I look at Jennifer in a state
of shock saying, "I don't think I can do that, and you know why!"
Jennifer looked back with a little giggle saying, "Don't worry sweetie.
I have already told Mary all about what you wear for undies. Plus, silly
I want you to really think hard about this. If Mary is going to be
making you some cute frilly little girl dresses for you, don't you think
she may have figured out that you like girlie things?"
"Oh yeah! I guess you're right about that."
So, I stripped down to my lacey panties and tee shirt. After what seemed
like an hour Mary was done taking my measurements. Heck she even asked
me what size little girl shoes I took, and if I wore a bra and if so what
was my cup size. I answered a dozen more question for both ladies, while
I got dressed. Once dressed Jennifer & I both thanked her for her time,
as Jennifer told her she would be in touch with just what kind of outfits
she wanted. We both said bye and head back out to Jennifer's car so she
could take me back to my truck. We arrive back at the dinner and as I
said my good byes, she gave me a peck on the cheek, saying, "I expect to
see you around 4:00PM on Friday. Bye sweetie."
As I was getting out of her car she handed me a card with her address and
telephone number on it. She told me if there were any problems to please
call her at the number on the card. The last thing she said to me before
she drove off was, "Now I want you to have fun dreaming about what we
will be doing, and all the fun we will be having this weekend and all of
next week."
As far as I was concerned this was going to be the greatest weekend ever.
I was actually looking forward to being dressed as a little girl for the
weekend and all of next week. Seeing I had tons of vacation days, I went
into work the next day and made arrangements to take off for a week.
Plus, I also asked for that coming Friday as a vacation day. I figured I
could work Thursday and pack what I'm taking on Friday morning. All I
can say is the rest of the week passed slowly, as I couldn't wait for
Thursday afternoon.
Thursday was finally here and all day long I kept going over in my head
everything I wanted to bring with me. I was able to get off early, which
gave plenty of time to pack and get ready for the next day. Once I
arrive home I started going through my cutest outfits, getting them ready
to be packed. I went over each item making sure it was just what I
wanted to bring. I even packed the beauty pageant outfit, complete with
the crinoline, matching rumba panties, frilly socks, and frilly hat. I
checked to make sure I had a couple of pair of my really cute rumba
panties, hair ribbons and socks. Plus, my pink and black Mary Janes. I
then packed some guys clothes, even though I wasn't sure if I would need
them or not. I found Sarah Jane my doll, and packed her too, with all of
her matching outfits that she had. When I was done I had two very large
suitcases pack full of my little girl outfits.
I didn't sleep that good all night, as all I kept thinking about was
Friday afternoon. I was up early the next day, got dressed and went to
breakfast. I mentioned to my friends at the local coffee shop that I was
going away for about a week. I figured this way no one would be looking
for me to help them with some project till next Saturday. The day went
by so slowly, but finally it was 3-pm, my truck was packed, and I was on
my way to the address on the card.
It didn't take too long to get to Jennifer's house. I drove up to the
large gates in front of the address on the card and was amazed at how
large her place looked. The guard at the gate asked for my name, which I
gave him. He said, "Oh yes you are expected, go right on up to the front
entrance sir." He pressed a button and the large metal gates swung
opened. I slowly drove on up the long winding driveway and arrived at
the front of the mansion. I parked my truck off to the side of the
driveway, got out, and grabbing my two large suitcases. Then I turned
and headed up to ring the front door bell.
I felt a little nervous as I walked up to the front door of the mansion,
mainly because I was starting to get cold feet. I wasn't really sure if
I wanted to do this or not. It was starting to dawn on me that I was
going to have someone I only met a couple of times role-play as my aunt.
Plus, I was going to let her have complete control over me, just as if I
were a little five-year-old. I started thinking maybe this isn't such a
great idea, and I should turn around now and get the heck out of here. I
knew once I pushed that button on doorbell, there was no turning back.
Well I never had a chance to push the doorbell, because as I reached the
top step and was getting ready to turn and leave, the door opened.
Standing there was this very pretty young lady who looked to be in her
late twenties, dressed in a nice gray uniform, with a white apron.
She looked at me saying, "You must be Jack? Come on in, you are
expected.
"The man at the front gate called to say you were here. I was watching
for you to pull up, come in and make yourself comfortable."
I gave in against my better judgment and entered the house, just as
Jennifer came out of the large living room. She was so happy to see me
saying. "There you are Jack. Where did you park your vehicle?
I told her that I left my truck right outside over to one side of the
driveway.
She said, "That's good spot, I'll have someone move it to the garage area
later. I was worried you would change your mind. I'm so glad you came.
I think this weekend and all of next week is going to be so much fun."
While answering her I realized I started to mumble my words, "Hum, a, ah,
yes I guess." I'm hoping it will be too! But in my head, I was still a
little worried, and wondering if now was the time I should turn and run?
About that time Jennifer said, "Let me introduce you to the staff that
will be here with us this weekend."
All of a sudden, I now had a new worry!
I'm thinking, "Staff? Wait! What Staff? As I mumbled out the words,
"Your staff is going to be here with us too?"
I'm thinking she never mentioned anything about staff being here?
So again, in a shocked voice I said, "Your staff?" Like, "Ah --- others
are going to be ---Ah here --- with us, ---- while I'm, you know
dressed?"
Jennifer's reply was, "Why of course, I can't watch over you every
minute, and I need some of my staff to run this place, but don't worry, I
only have my two best maids, my cook, and my chauffeur staying with us.
The chauffeur is here in case we need to go someplace. Plus, everyone
has promised to make your stay here as wonderful as can be.
"So, Jack, let me introduce you to the staff."
"This is, 'Kay,' whom you have already met, as she was the one who
answered the door.
"Next, we have 'Rose.' who is wearing the white uniform with the pinkish
apron. She will be your nanny, while you are here with us, and she will
be in charge of you when I'm not around.
"Lastly, we have my wonderful chef 'Molly,' who will be making all the
great meals we will be sharing.
"There is also my chauffeur, 'Thomas,' whom you will meet later."
While she was talking and introducing everyone, I was still stuck on the
words.
"She Will Be Your Nanny."
I'm thinking Nanny! Someone besides Jennifer is going to be looking
after me, while I'm pretending to be a little girl?
I'm now stress out, and not really sure about this idea anymore? Do I
really want this to happen, or should I just turn and run out the door as
fast as my feet will carry me?
That's when reality set in, as everything Jennifer was saying started to
sink in. Dang that means Jennifer had informed her staff of what we had
plan for this weekend! Plus, she said they promised her that they are
going to do whatever it takes to make my stay here as a little girl very
enjoyable?
At this point I was at a loss for words, scared to death, and in one big
panic. I just stood there sweating and trying to take everything in that
Jennifer had just told me. All I was thinking about right then was which
way was the front door, and how the heck can I get out of here? All I
wanted to do was to turn and run for the door, leave and forget the whole
deal.
Jennifer must have sensed something was wrong, as she looked right into
my eyes, while saying, "Come on Jack you need to relax. I can see it in
your eyes that you are a little upset and maybe a little worried but try
to relax and enjoy yourself. Honest sweetie it's not as bad as you may
think! I promise that you will love every minute of your stay here."
She then told Kay to take my bags up to my room.
The next thing I know my bags are on the way up the stairs, while I stood
frozen in place, still in a state of shock.
I'm thinking okay seeing the bags are headed upstairs already I'll stay
for a day or two. Heck she did say I could leave anytime I wanted to, so
let's see how everything goes.
That's when Jennifer hit me with something I didn't expected.
Dang, I was just starting to relax a little, when I heard Jennifer say
something about "RULES".
Now this new problem got me. I'm thinking, "WHAT RULES?"
Again, I started to panic. Heck we never talked about any kind of rules?
I heard her started to explain that there were a few rules that I had to
know about and need to follow, or I would be punished like any little
five or six-year-old.
Dang what is going on here? No one said anything about RULES!
I remember clearly that nothing was said about rules?
Wait a minute, what kind of rules could she have in mind anyhow?
Well I guess I was about to find out.
To be continued.
Jayla
- 26.01.2023
- 17
- 0
