Sissy Outing

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Sissy Outing

Tell a family member you are a sissy.




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Being a Girl for a Day with My Girlfriend

My name is Jerry and I’m 24 years old. Since I was a kid, I have been fascinated by feminine clothes. I used to admire my sister’s clothes and eventually got into crossdressing by wearing her outfits in secret. As time moved on, I tried resisting the urge to dress up as I didn’t have a lot of personal space inside my house.
And for a while, I stopped crossdressing. After few years, I got into a relationship with an amazing girl, Amanda. She was a beautiful & smart lady. We brought an apartment together and started living together. Things were really going great.
Amanda has a job at the pharmacy and I work as a freelancer. I spend a lot of time inside the apartment and there is a lot of Amanda’s clothes lying around. She has so many cute & hot outfits and I frequently wonder how those outfits would look on me.



One day, I woke up quite late because I was up all night working on a client’s project. I got into the shower and took a nice bath. When I came out of the shower, I noticed Amanda’s bra and panties lying in the hanger. Amanda had already left for work. The temptation was so strong and I couldn’t resist the urge to put on her bra and panties. My whole body shivered with excitement when I put them on.
It felt so wonderful to get in touch with my feminine side again. I walked around the apartment and spend almost 2 hours taking photos and looking at myself in the mirror. After that moment, I began to wear Amanda’s outfit more frequently but in total secret.
I would dive into her lingerie cabinet when she was at work and try on her latest lingerie. I would at most occasion get so indulged in dressing up that I forgot about time. I almost got caught two times and it was quite scary.
I thought about telling Amanda my crossdressing secret many times but I was really afraid she might break up with me after knowing. I decided not to tell her and see if my desire to crossdress fade out.
My interest in women’s lingerie grew bigger instead. I loved the feeling of wearing my girlfriend’s undies & her cute dresses, walking around the apartment and taking tons of photos & videos of myself.



One day, Amanda was away at work and I felt like checking her wardrobe to find something nice to wear. I picked a black mini dress and one of her sheer pantyhose. As I was pulling the pantyhose up through my legs, it suddenly ripped from the left side. My heart began to race and I got very nervous thinking Amanda would find out.
I undressed quickly and put the stuffs back in her closet. A few days passed and she didn’t mention anything about that, so I thought she must have missed it.
After few weeks, I decided to try on some of Amanda’s lingerie again. I picked out a red one from her closet and put them on. I walked around the room and couldn’t stop admiring myself in the mirror. As I was fantasizing about what to do next, I suddenly heard the front door open.
I froze with horror and couldn’t think about of what I should do next. It was Amanda, she was home early. She called out my name a few times but I was just too numb to respond. I decided to rush to the toilet and hide there. Amanda walked up into the bed room and called me again.



“Jerry, come out. We need to talk! I know you have been wearing my clothes.” Amanda said out loud.
My heart was pounding. How did she know about it, I wondered. I was really busted this time. I came out the toilet and Amanda had bit of a shock seeing me in her lingerie. I felt so embarrassed that I couldn’t even look at Amanda and explain.
“I knew something was up. After I started to notice my outfits & closet feeling a little strange, I decided to install a hidden cam to inspect. I thought you were bringing a girl in the apartment and cheating on me. But I have to tell you, I was quite surprised by what I found out instead and I think you know all about it.” She spoke glancing at me.
” I am so sorry Amanda, I wanted to tell you about this before but I never got the courage.” I replied, feeling quite guilty.
“Let me show you something. I am sure this will be very interesting for you.” She said while taking out her mobile.
Then she played a video. I was stunned, it was a video of me going through her stuffs and trying on her outfits & stuffs.



” I have a lot of videos like this that the camera managed to record. You have been really naughty, going through my stuffs without my permission. I am pretty mad but I was quite surprised that you like wearing my clothes.” Amanda said.
” I won’t do it again. Please forgive me for not telling you. I am really sorry Amanda. I hope you will give me second chance.” I pleaded.
” Yes, I will give you a second chance. I have made a perfect plan.” She said looking quite serious.
” I will do anything, just forgive me.” I replied.
” Fine, tomorrow you will spend a whole day as a girl with me. You will do everything that I tell you to do. You will be my girlfriend for a day. We will even go out shopping. Do you understand? .” Amanda said.<
I knew there was no chance of convincing her now so I nodded. Lot of emotion going through my head.
Next day, we woke up and Amanda gave me a full makeover after breakfast. First, she made me wear her padded bra and lace panty. Then, she took out a white top, black mini skirt and black sheer pantyhose. I put them on, feeling quite awkward in-front of Amanda. She was smiling the whole time.
After I got dressed, she combed my hair, then added some hair extensions and tied it back. Then she applied makeup on my face and painted my nails too. I felt quite nervous but equally excited.
Amanda, brought out some of her heels and told me to put them on. After trying out a few pairs, a black pair of heels really matched my size. She then told me to walk around in those heels. She probably wanted to check if I could walk in heels properly or not.



She gave me a few lessons about how to present myself as a girl. After some moments of practicing, she told me that we were going to the mall and do some shopping.
I hesitated but she wasn’t talking no for an answer. She persuaded me to get into the car and go to the mall. My heart was racing the whole time and I felt shy & nervous about my new appearance.
Luckily, when we reached the mall, it seemed less crowded. But I was really too scared to step outside. Finally, after quite a discussion, Amanda convinced me to step out of the car.
Then we went inside the mall, my heart racing faster with every step I took. It felt like everyone was just staring at me. I could feel butterflies in my stomach. I held Amanda close to me the whole time and she seemed to enjoy seeing me like that.
I didn’t speak the whole time while shopping, fearing people might point out that I wasn’t a girl actually. I just followed Amanda around like a needy child. After visiting a few shops, I begged to go back.
She finally agreed and we drove back home. When we reached the apartment, I was so relieved. My feet were killing me after wearing heels for a whole afternoon. It was a crazy experience that I couldn’t believe happened with me.
Amanda accepted my crossdressing later and now lets me crossdress inside the apartment. Sometimes, we go out with me dressed as her girlfriend and its always so exciting when that happens.
I would love someone to feminize me and take me out shopping I love wearing ladies clothing at home in Mansfield Nottinghamshire England
I would love to have a girlfriend like Amanda. I don’t think I could pass being a woman.
‘I love wearing a dress around the house only I AM 70 But look younger I am thin built with thin arms and legs NOT VERY STRONG So I AM SURE THERE IS LOTS OF WOMEN STRONGER THEN ME. I HAVE ALWAYS BEEN THIN But average height I DID GO TO A PHOTO STUDIO A FEW TIMES IN PRETTY DRESSES AND HAD THE MAKE UP GIRLS DO ME UP WHICH THEY ENJOYED I WEAR A SIZE 12
they told me I can pass as a average size girl with the right make up wigs because of my smaller size. and told me there is nothing wrong with wearing women clothes around the house if skirts or dresses ever get on the market for men I will be one of the first to wear them . its not right only women get to wear them especially because there is so many strong girls out there stronger then men ..
I wish you live next to me. Are with me
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A story
of Petticoat Love by Missy Sissy Bottoms!
I have been
a devotee of "lacy things" (petticoats & rumba
panties) for so many wonderful years. All and any feminine
clothing that is especially frilly, fluffy, and lacy and
feminine-flashy have been the best things in the world. From the
clothes of the fifties when girls wore petticoats as a matter of
fashion to ballerinas with their fantastic tutus -- they just
blew my mind! However, once I saw my first French maid I knew
that I was hooked. I soon owned several very sissified French
maid outfits. I discussed my penchant with my wife, but she
wasn't particularly interested in participating; however, she
understood my feelings and, in essence, told me to "have
fun".
My wife
never questioned my secret closet that was soon filled with sissy
clothes. It was just something that she preferred not to discuss,
although she never questioned either my manhood or my secret life
style.
Every
chance I got from then on, especially when she is out shopping,
working late, taking a business trip or just visiting, I become
"Missy". She knows that I do and simply lets me do my
thing. We never talk about it, as it is just a given. Thus my
wife enjoys herself even more because while she's out of the
house I do all of the cleaning , and, when she comes home, it's
to a
sparkling clean and organized house. She knows that I do wear
women's clothing when I clean the house, but she had no idea as
to the extent of my wardrobe and the extent of my commitment.
That commitment is simple: I go the whole nine yards when I'm the
maid, as my uniforms are extremely sissy, short, frilly, fluffy,
lacy and oh! so sexy, and are a combination SISSY- FEMININE-
GIRL- PET-PANSY.
Furthermore,
I assume the personality, persona and presentation equal to my
outfit. I am quite feminine, very sissified and extremely happy.
I believe that I am actually pretty and, because I am not a large
male, and I have acquired the mannerisms, movements and
expressions of a young girl, I am quite believable as a female.
Normally I wear either a tight, nearly transparent blouse, or a
clingy dress that emphasizes and shows off my breasts (silicone,
of course, but enough to
make me cry for happy). I wear lace wrist and ankle cuffs, the
very short skirts are designed to show off the abundance of silk
lacy petticoats. Neither my petticoats (always worn very short),
nor my dress, effectively hide my ruffled panties. My long,
slender legs (I keep them shaved) are well-shaped and quite
attractive, especially when I'm wearing black silk stockings. So
with a frothy, but little lacy maid's apron and pert, little lacy
maid's cap, I am quite the young lady who has been "collared
and cuffed" into domestic servitude.
I even make
up my face fully (which I am rather good at) and, with high heels
clicking, hips rolling, short, mincing steps and my pink feather
duster dusting, I am quite a lovely sissy-boy-girl. I sing and
skip around as I clean, blowing kisses, blushing, giggling in my
own fantasy world. I am an excellent housekeeper, and rarely is
my wife not satisfied with my performance.
Normally I
have time to change before my wife comes home. I will watch the
time carefully, so I won't be caught with my pants down and off
and replaced with girlie panties. Most of the time, she will call
before she comes home to ask me (1) if I'm having a good time,
(2) if all of my little household duties are done and (3) to tell
me that she was on her way home and when she would get there.
This gives me a chance to change, although I delay changing until
the last minute.
One
Saturday this past summer, I was so engrossed on being Missy I
forgot the time, and she had forgotten to call when I heard the
front door open and women's voices drifting back to the kitchen
where I was finishing tidying up. I realized immediately that she
was home and not alone. It turned out that her sister and one of
her girl friends had decided to come back to the house with her
for a cup of coffee. I was in the kitchen with no escape route. I
barely had time to hide in the small pantry nook which is in a
little out-of-the-way alcove off the kitchen. It has only one
entrance and is quite open, but can't be seen unless one walks to
the end of the kitchen and looked around the corner. It was a
dead end though. I couldn't hide. I couldn't change. I couldn't
escape. I couldn't move. My face was fully made-up and my outfit
so "oh-la-la." I did the only thing I could do: I
started to cry.
I was
shaking like a leaf, firmly believing that I would be exposed and
humiliated and embarrassed beyond belief. I had the good sense to
walk quietly on my two-inch heels and to contain my sissy sobs so
that they were more than muffled. My breathing was hard, but I
quickly gained control of myself and waited.
Without
thinking, my wife brought them directly into the kitchen. I froze
near panic as I heard them in the kitchen only within feet of my
position. Thankfully, the women immediately sat down at the
kitchen table which couldn't be seen (and vice versa) from the
pantry while my wife made coffee. As the coffee was stored in the
pantry, she had to go there. "Voila!" Who was standing
there, nearly in tears, shaking like a leaf and on the verge of
panic! It was I, and it must have made a shocking discovery. The
look of shock on her face at my presence and at my outfit quickly
turned to amusement as she realized that she hadn't called. She
smiled a really wicked smile and left me standing there like a
frightened pansy during a windstorm. I had to choke back tears,
afraid that I would burst out. I felt so soft and weak all over,
except for one significant part of me. The women had several cups
of coffee and discussed quite a few intimate thoughts and several
items of a purely feminine nature. I could hear everything, and I
would have been shocked and embarrassed, but I was too nervous. I
simply had to stand there, completely vulnerable and "little

kitten" frightened. My wife decided that she would have some
fun with me and scare me even more than I already was. She told
them how I did all of the cleaning, although she didn't mention
how I was dressed when I cleaned the house. Her sister raved that
a man, any man, would be so compliant and considerate. Her girl
friend laughed. My sister-in-law was shocked to hear that I did
all of the housecleaning as well as the laundry, ironing, etc.
Her girl friend called me "well-trained". My
sister-in-law was really interested to learn that my wife did
nothing domestic including taking care of her own wardrobe when
"I did such a wonderful job".
My wife
made several intimations that only I realized that she was trying
to embarrass me even more than I already was. She was actually
flirting with the truth, and I wouldn't have been surprised if
she had sent her sister into the pantry "to get
something." She told the women that I was an excellent
housekeeper, almost like a maid (and she did use that word). That
she only had to write down tasks for me to do, and I would
quickly obey (she emphasized the word). Her sister opined that
maybe I was a sissy at heart. "Who cares," said my
wife, "I love him and he's terrific."
My wife's
friend left, but my sister-in-law lingered for over an hour. I
had to stand there as quiet as a mouse, a little girl mouse at
that. After she left, my wife laughed and laughed and then
allowed me to go upstairs and change. She followed me up the
stairs and made comments about my ruffled derriere, the bounce of
my petticoats, the cute little walk I had and that she never
realized what a pretty husband she had. I loved it but was afraid
to tell her the feelings that swept over me.
My wife
still doesn't participate in my domestic life except to give me
orders. I WOULD LOVE TO TELL MY WIFE THAT I WANTED A REPEAT
PERFORMANCE. She must have assumed that I rather enjoyed myself.
She has made comments about how she "wouldn't" always
call before she came home and she "wouldn't" always be
alone and she "may" come in from either the front of
the house or the back. "Maybe," she has mentioned that
I would have to serve her and her sister on the front veranda As
for my sister-in-law, when I see her now she will ask if all of
my "little" household work is done. She will smile
(actually smirk) at me. I will catch her staring at me and I
realize what she must be thinking. I also get the feeling that
she quickly picks up on any (un) masculine activity, remark, etc.
that I make. She doesn't really suspect, but I think she's
awfully close to it. I have caught her looking at me in such a
way that I believe she is mentally undressing me. I fantasize
that she is trying to picture me in a French maid's uniform.
This is a
true experience but, "unfortunately" it hasn't been
repeated and I do want it to happen again, only I want my wife to
have her sister make the coffee. Missy Sissy Bottoms


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