PG 13 last part #23 now added hope you enjoy
A guy having breakfast at a small diner, meets a lady, and then unexpected things start to happen.
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Part 1
The Next Part

this will start off with a PG13 but later may have some R rating

hope you enjoy



Part #1

,

It all started on a nice, cool, Saturday morning, in late October. The year 1971, and I’m sitting alone at the far end of a counter, in an old style diner. The diner is not my normal breakfast hang out.  I was mainly here, because one of the best and largest hardware stores in the area was right near by, and that’s where I was headed next. 

 

After I finished my breakfast, I paid the waitress, and left a nice tip. The waitress left to ring up my payment as I stood up to leave. I was turning to head out the door, when I heard a really nice sounding female voice from behind me. However, what she said shocked me, and had me in a slight panic, as I heard the lady say.

 

 I really like those lavender panties you’re wearing.

 

Tell me are they the real lacey kind?”

 

I quickly turned around, and at the same time put my hand behind me, checking to see if my panties were actually showing. Sure enough my tee shirt had ridden up, and my jeans were hanging down a little, so that my lavender panties were showing way above my belt line. I started to fix and adjust my shirt and pants, making sure the panties weren’t showing anymore. At the same time I looked over to where I heard that soft, sultry voice. My eyes came to rest on a very pretty lady, who looked to be in her late 20’s, or early 30’s. She was seated almost right behind me in the last booth, and as our eyes met she gave me this really nice warm inviting smile and then winked at me.

 

I finished fixing myself up, and readjusting everything, but still in a slight panic. Still in a panic I turned my attention to who was nearby. I looked down to the other end of the counter to see if anyone else was close enough to see or hear what she had said. I was hoping no one was near enough to have overheard her remarks about the panties!  I was also embarrassed to think that everyone may have seen me adjusting my clothes. Luckily for me, everyone else in the diner was at the far other end of the restaurant, including the waitress. They were all busy talking about something or other.

 

 That’s when I heard the same woman ask me another question. So I turned my attention back to her as she asked.

 

 Do you wear panties all the time?

 

“If so what’s your favorite color, and what style to you like the best”?

 

“Maybe you like the full brief”?  No!

 

I think you’re more of a high cut pantie style person right?

 

Not wanting anyone else to hear what she was saying, I walked closer to where she was seated. Figuring my secret was already out, I told her “Yes” I do wear them all the time”.

 

I’m not sure why I kept talking, but I went on to explain that I’ve been wearing panties on and off since back when I was about seven-years-old. As for my favorite color what else I said, of cause I liked pink or lavender the best, and my favorite style is the high cut nylon spandex that is trimmed with nice lace accents. I figured this would throw her off balance and stop her from asking any more embarrassing questions. Boy was I wrong about that!

 

She looked at me with a surprised look saying “wow”! I like a guy who is honest, especially someone who would admit that he likes wearing lacey panties all the time. Then she gave me another big smile saying, I never met a guy that I knew for sure wore panties, but I guess most guys who do, would try to keep that a big secret right?

 

I was a little taken back by her statement! I mean a lady who is okay with a guy wearing panties? Really!

 

She then asked me if I was going any place important, or did I have time to sit down and talk a while.

 

I was now a little curious about this lady. So I told her that I wasn’t in any big rush, and that I could hang around a while to talk. I sat down across from her in the booth, as she called the waitress over, and ordered me another cup of coffee, telling her to put it on her tab. We made small talk for a while, sipping on the coffees.

 

I then said you know we have been talking for almost ten minutes now, and I still don’t know your name?

 

She replied “Oh”! My name is Jennifer, “what’s yours”? So I told her that my name was Jack. 

 

Jennifer said, “Glad to meet you Jack”, and I answered “same here Jennifer”.

 

We did some more small talk, with questions, like my age, if I had a job and what type of work did I do?

 

I told her I worked at a nursing home as the head of maintenance, and that I was 26 years old. The Next thing I hear her say is, “No Way”!

 

For some reason she had a hard time believing I was that old. With a smile on her face she said I figured you for sixteen to maybe eighteen at the most. Jennifer then asked me if I ever dressed up completely or did I just like wearing undies and lingerie? She also wanted to know if I was married and if so, what my wife thought about my dressing,

 

Wow this gal is right up front with her questions!

 

So I told her that I wasn’t married, and that currently I didn’t even have a girlfriend. I went on to explain that yes I do dress up completely about twice a month. I also mentioned that I belonged to a cross-dresser’s support group, and that once a month we have meetings. I informed her that I would go to the meetings and change there, because we had a room to change in for the guys who could not come dressed. I went on to tell her how sometimes I would get dressed at home to go to the meeting, but that it all depended on how dark it was outside, and if anyone was home next door. I explained how I have some very young kids living on both sides of me, and I wouldn’t want them or their parents to see me dressed as a lady. I felt the kids were way too young to understand.

 

Jennifer replied that it was a good point and she could understand how I felt. We talked some more, and she was very interested in my cross-dressing, as she asked more & more question. Like do I have a feminine name? To which I said yes, when dressed I use the name Jillian, or Jill. While answering some other questions she had, I tried explaining how being a crossdressers feels, and how long I have been hiding my dressing from others. I even explained why it felt so good. I figured if she is that interested in cross-dressing; why not try explaining as much as I could to her. The more people know and understand us, the better it is for all of us cross-dressers.

 

Next she wanted to know if I had any pictures of myself dressed, because she was curious about how I might look all done up. I reached for my wallet and took out my ID card for the support group and another picture I carry with me. I mentioned that when driving dressed, if I should get pulled over, I would hand this ID card over with my license. I told her that the card had a picture of me dressed from the chest up, but most important was on the back of the card it explained that I was a cross-dresser, and dressing for my own pleasure. This way the cop wouldn’t think I was trying to hide my identity.

 

She took the card and the other picture giving them the once over, while also checking me out. After about two minutes of checking the card, the picture, and me. She said I like what I see. You look really cute in that photo and you almost pass. The Only problem I see is you look more like a young girl, maybe ten or twelve-years-old, rather than an adult in these pictures.

 

I said “thanks” but you’re right! I know I don’t pass that well as a woman. To start with I’m way too short, as I’m only 4ft- 7-inches tall. Plus besides being small, I have slim shoulders and arms, and a very young and feminine looking face. Like you said when I’m dressed up I look more like a young girl trying to play dress up, in her mother’s clothes, rather than an adult woman.

 

I explained that because of my size I have such a big problem finding things to wear, as the clothes in the ladies department kind of hang on me. Then if & when I do buy an outfit; most times I need to get it tailored to fit, which makes the cost almost double the price of the outfit. That’s one of the reasons I will end up buying my clothes from the Junior Miss department, or even the Kids department.  The problem there is the Junior Miss and kids departments really don’t have anything that looks grown up, which is another big problem for me.  It’s also one of the reason I don’t go out in public that much.  Of cause that in a way leads to another problem.

 

Jennifer asked.  “Oh and what kind of problem would that be”?

 

I said the problem of staying home while all dressed up.

 

She looked at me with this questioning look as I started to explain.

 

Think of it like this, just like any lady, when you’re all dressed-up; you want to show off how great you believe you look. It’s like any girl or lady would feel. Here you are all dressed up pretty and feeling great inside ready to go out and show off how great you look, but you can’t”.

 

I call it the “Pretty Girl in the Cage Syndrome”.  You are dressed to the nines, feeling oh so pretty and happy about how you look, and wanting to show off to the world.  Only there’s no place to go that you could pass, and even worse you could end up being made as a guy who’s dressed as a girl.  Okay let’s face it a guy walking around in a junior miss outfit can cause some stares and create serious problems if you don’t look just right.  So to be safe you end up just hanging around your house, or apartment, wishing you could really pass.

 

Imagine how it feels being stuck in a room at home, feeling like you are in a cage. You start feeling really down about yourself, and hating that God made you this way.  Next thing you know you start hating how you look, even though you just spent an hour or more, with your make-up and wig getting yourself all dolled up.  That’s when the Jealousy kicks in, and you start wishing you could be like some of the other Gals / Guys, who look so great, with more shapely bodies and faces that can pass with ease.  Those gals get to go out dress in great looking outfits, in public anytime they want. That’s when you really start getting mad at yourself for thinking you could pass like they do, and you start taking everything off, feeling really depressed, guilty, and thinking just how unfair the world can be.

 

Jennifer looked at me saying, oh-my! That’s so sad!

 

So what you’re saying is, when your dressed you’re never really happy about how you look?

 

I said well not really, I think I’m like any other cross-dresser. I love getting all dolled up any chance I can. You could say that When dressed we try to really look as feminine as possible. No matter what shape or size our bodies are. Once we are dressed and look in the mirror, our minds will see ourselves as beautiful ladies. As for myself I kind have learned a few tricks and ways to feel much better about my small size and figure over the years. I think now it’s easier for me when I’m home alone and dressed, but it’s very complicated to explain to someone who is not a cross-dresser.

 

Jennifer said, Go ahead and explain, I would love to listen and understand. This is so very interesting to me and I have the time. So go head explain.

 

Part #2

 

I was a little shocked that Jennifer wanted to hear more.

 

I started off saying that I just hope you don’t think of me as being to strange, with what I’m about to tell you”?

 

I had the feeling that Jennifer seemed very interested in what I was about to tell her. So I went on to explain that when I’m dressed I feel like any lady that is dressed up nicely. I feel that I need to go out someplace, anyplace, maybe just for a drive, or walk, even if just to a drive-in-movie. Only in my mind I know I really can’t pass as a woman, because I look so young. Plus like I said before, there are other reasons I don’t leave my apartment dressed.  There are two really nice families, with kids, on each side of me.  How do you explain this to them?  Would there really understand why I am dressed like a female?

 

I knew deep down that I had to find a way to feel good about myself, while dressed at home. That’s when I remembered what it was like, when I was small and growing up. Back in the early fifties I had fun at home playing dress-up in one of my sister’s dresses.  There was no need for me to leave the house.  I was able to play with my sister’s dolls and things, while dressed in one of her frilly party dresses, with the crinoline, and the cute rumba panties. I knew no one was going to be home for a long while, so I had full run of the house pretending I was a little girl, playing with my sister’s stuff.

 

I was going to try to relive that time when I felt good. Seeing that I’m so short and small in size I decided to check into the size charts for little girls. I found out that I was actually pretty close to the same size as an eight-year-old girl.  Knowing this I started to go to some thrift shops, and Salvation Army stores to look for any cute little girl’s outfits in an eight-year-olds size.  To my shock I found a couple of real cute frilly little girl style dresses that would fit me.  Matter of fact in one store I found what I now call my dream dress.  It was a fancy little girl’s “Beauty Pageant Outfit”. You know the kind that a little girl would wear to compete in one of those, little miss beauty pageants. I found out that the outfit came complete with matching crinoline, rhumba panties, socks, and even a cute bonnet or hat all in a size that would fit me.

 

It was my lucky day, because it was near Halloween.  So I told the lady running the store that I was there to find a Halloween costume.  I led her to believe my girlfriend and I were going as Jack and Jill, but that I would be going as Jill, and my girlfriend as Jack.  Anyhow while the lady was helping me look for something I could wear; she found this pageant outfit.  I said wow do you think it would fit me?

 

She held it up against me saying it just might?  I was in heaven when the lady then said well there’s only one way to find out. That’s to go and try it on.  She led me over to a dressing room saying go ahead and try the dress and crinoline on.  About three minutes later I came out of the dressing room wearing the outfit.  She had me turn around so she could zip it up.  All I heard her say was wow it fits you prefect and looks great on you.  You almost look like a little girl, with your long hair in that outfit.  All you need to do is put your hair in pigtails and I bet you could pass as a little girl in that dress.

 

I thanked her and told her I would take the whole outfit right down to the frilly little girl’s bonnet or hat.  Once I paid for it, I thanked her for her help.  She then made me promise to take pictures and bring them in so she could see me all done up, which I must confess, I did take some pictures and showed them to her.

 

Later that same day in another thrift shop I found three pair of Mary Jane’s in my size, which came in different colors. So I bought all three pair. The next day I went out and found myself this real pretty 18-inch doll, plus a dolls baby carriage, and to boot some clothes to dress the doll in.  I also picked up some other items I thought a little girl would play with, like a couple of coloring books, crayons, and even a tea party set.

 

I was hoping that now I would no long be bothered by wanting to go out while dressed, because dressed as a little girl I would feel good about staying home alone.  You know I was right as I started to feel much better, when I was dressed as a little girl.  Sometimes I would even watch a TV show like Sesame Street, while holding my doll, and sipping juice out of a Sippy-cup.

 

 Other times I would just sit and color in a princess coloring book, or play with my dolly, while drinking from the Sippy cup.  Now I no longer feel trapped in that cage like I felt, when dressing as a woman.  I can now dress as a little girl and play in my apartment, because there is no reason for a little girl to go out, as she has all she wants in the house.  There are some drawbacks like not interacting with others, but I do feel better

 

As I was explaining this to Jennifer, she was looking at me with this funny gaze.  Seeing the look on her face, I said, “okay I kind of told you that you might not understand, and think I’m a little strange”.

 

That’s when she said, “OH NO sweetie”!  I do understand where you are coming from, but wouldn’t you like to have a friend or someone else there too, perhaps another person as a playmate to play with?  How about someone who also likes to dress as a little girl, or maybe someone to role play as the person in charge, like a mommy figure or Nanny type person.  It’s got to be very lonely dressing and role-playing all by yourself?  I mean having someone else there to role-play, would that make it more real feeling, so you would feel like you are little girl?

 

I said sure that would be great, but most of the people I have met or know, who dress, don’t dress as little girls.  Plus let’s face it; it’s not easy finding a lady, who would want to role play as a Mommy or Nanny to some guy, who dresses as a little girl.

 

Jennifer said. “Well I guess you are right about that, but have you looked”?

 

She had a point, as I said not really, mainly because I have no idea how to look for someone like that. What would I do?  Place a personal ad in the paper?

 

YES! I can see it now!

 

Lady wanted to role-play as a Mommy or Nanny to adult male, who likes to dress and pretend to be a little girl”.

 

Yep that should go over really great in the want ads?

 

Jennifer gave a big giggle to that statement. After which she said, well I guess you’re right about that.

 

We talked some more and I could tell she was definitely interested in knowing more about me, and my cross-dressing.

 

 We talked some more when she looked at her watch saying; oh my Jack look at the time, I real have to go.  While getting ready to leave Jennifer mentioned that she comes to this little diner a lot, and hopefully she would see me again sometime.

 

I told her that I would look forward to the next time we should meet, and we both left.

 

As I drove to the hardware store I kept thinking about Jennifer, and that maybe I found a new friend. Hopefully we will meet and talk again. (That was going to happen a lot soon then I thought)

 

To be continued:

 

 

 

 

 

 

 

 

 

 

The Next Part
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shamrock
dear,,,, LIT JILLY,,,, I like your story,,,, and I hope you have Jennifer be the mommy or nanny for jack,,,, where Jennifer can say I can help you jack with your dresses as a little girl BUT with diapers too so you can feel like a little girl     
HI,,,, I am shamrock & I am a male ,,,,  I wear diapers and i love to be bandaged up by female nurses and diapered by them,,,,,,,,, THANK YOU ALL    
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Mellsissy
Don't ruin it by going straight to diapers.  Keep it going just like it is.  There is a lot of us sissies that don't wear diapers.
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sissybabydreams
wonderful first couple of parts, kept it going in the same fashion and I am quite sure that you will have a firm favourite on your hands.

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shamrock
dear,,,, LIT JILLY,,,, first of all,,,, I like your story,,,, and I see you take my idea ,,, it ok,,,, and I see jack want to be a toddler girl of 8 year old and my idea is maybe Jennifer can trick jack in wetting the bed for three night straight after the weekend and than put jack in diapers treat him as baby girl from now on ,,,, that my idea,,,, and Jennifer want him be 4 year old toddler  PS,,,, I help baby butch on his stories  
HI,,,, I am shamrock & I am a male ,,,,  I wear diapers and i love to be bandaged up by female nurses and diapered by them,,,,,,,,, THANK YOU ALL    
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LIT JILLY
I'm glad everyone is enjoying the story so far. There are a lot more surprises to come, and maybe way down the line in some parts there will be some baby time "I THINK  " grins we will have to just wait and see.

Big Hugs & Kisses to All
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Jessica Loordes
Love the story. Its so cute when the two talk and Jennifer is so easy to talk to and listen as she breaks down the Jack's barriers and brings him out slowly. I am sure she will have him trapped soon in a sweet and silky sissy trap. I cannot wait to see how this develops. Please hope to see this soon! Jessica
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LIT JILLY
parts may come a little slower as I did something to my right thumb and it hurts like hell. the doc has in a brace so it's slowing down my typing .

have ne fear we will get the story moving along somehow.
BIG HUGS & KISSSES
LIT JILLY
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shamrock
dear,,,, LIT JILLY,,,,, thank you from all of us and I hope your thumb get betting and we hope  jennifer surprises for jilly is real good one and YES I like your story  
HI,,,, I am shamrock & I am a male ,,,,  I wear diapers and i love to be bandaged up by female nurses and diapered by them,,,,,,,,, THANK YOU ALL    
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krystalasbaby
looks like jack getting more then he expected.  can not wait to hear the rules
krystala's sissy baby
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shamrock
dear LIT JILLY,,,,FIRST OF ALL I LIKE YOUR STORY and I can't wait to see what dress rose going to put on jilly and maybe after three day & night they can trick jilly in wet the bed so they can make him go from 4 year old to half year old little girl still wet the bed and I just saying and please don't get mad at me it only Idea,,,,,  
HI,,,, I am shamrock & I am a male ,,,,  I wear diapers and i love to be bandaged up by female nurses and diapered by them,,,,,,,,, THANK YOU ALL    
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shamrock
dear,,,, LIT JILLY,,,, WOW,,  it sound like the dress is real pretty to me and I hope Jennifer love the dress and all,,,, and I hope Jennifer keep jilly in the dress long after the lady friend leave and are you going to surprise us when Jennifer have jilly dresses as a 5 year old toddler girl we hope so,,,, PS i like your story 
HI,,,, I am shamrock & I am a male ,,,,  I wear diapers and i love to be bandaged up by female nurses and diapered by them,,,,,,,,, THANK YOU ALL    
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Mellsissy
Love the story so far. Keep it up. 
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krystalasbaby
i love the frillies what other surprises r coming
krystala's sissy baby
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krystalasbaby
krystala's sissy baby
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sissydina218
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LIT JILLY
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annabellacheff
lots of love
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krystalasbaby
krystala's sissy baby
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annabellacheff
awe that was a wonderful part. im just curious if jill will ask to stay with  jennifer forever and ever cant wait to see what happens next.
lots of love
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krystalasbaby
wow a real gurly bday party. remember mine as a boy not neaarly as fun as this sounded.
 
krystala's sissy baby
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sissydina218
absolutely love this story, love seeing jillian and her progression into being a little girl and how much she gets to enjoy it, especially loved the last part about the birthday all the little girls sounded like they had so much fun. can't wait to see how the rest of her birthday and the time after goes.
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annabellacheff
 wonderful part. cant wait to see whats next.
lots of love
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krystalasbaby
can not get last 2 chptrs to come up
krystala's sissy baby
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~*Christie Luv*~
@ Sissy Baby Tammy
  Hey hun! It's now fixed! =)
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LIT JILLY
what happen I can find my story in the story section  I can find it only under my activeties   I went to post another part only its not there ??????
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Baby Butch
@ LIT JILLY
 Hello Lit Jilly, I found this story under Forum/Stories. Today I was able to access page 12 which is part 17. If you are still having problems click on Contact at the bottom of the Menu to reach Christie our Webmissy.
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princesspullups
thank you miss Jennifer,this is a beautiful story - just what dreams are made of please keep it going. I envy miss jillian, wish I could meet a lady who would turn me into a little baby girl xx  
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