(Anonymous #1)


This happened when I was just about to turn eighteen and graduating.  My mother's girlfriend, Karen, gave birth to a beautiful baby about a year before.  A baby girl - her name is Christine.  Karen and my mother get along like soul mates, so they say. They do just about everything together. I'd swear at times they're inseparable.


Well, Karen got this job offer and was to start in two weeks. The job that was being offered to her at the time was running the bar and restaurant at the Hilton Hotel.  To her surprise she needed a baby setter. I remember her trying to find some one, but just couldn't find some one she could trust.  So, she and my mother were talking in the kitchen. I was in my bedroom trying to take a nap and heard Karen asking my mother if it would be possible if I could baby set Christine.  I thought for sure my mother was going to say 'Are you crazy?'.  But, to

my shocking ears, I heard her say, "That's a great idea."
I must remind you. I was sort of in my first full year of cross dressing.  I was looking forward to that whole summer of becoming feminine.  I remember getting rushes just thinking of playing in my mother's clothes every chance I got all summer long.  I also must tell you that I was not into any kind of sporting event of any kind.  My interest for that summer was becoming a young girl at every chance I got.

My mother, on the other hand, loved the fact that I wasn't into sports, that I always wanted to stay home.  She loved it so much that my chores was to do all the housework.  She taught me everything I know as of today.  I can cook, bake, do laundry, iron, fold. She even taught me how to sew - for my thirteen birthday she bought me this beautiful singer sewing machine. I loved

You must be wondering where my father was.  Well, he took off with this other woman when I was eight.  I remember that breaking my mother's heart.  All I wanted to do was to help her through that very painful time. I have to admit, my mother and I became very close. 

Well,  that following evening during supper, my mother brought it up to me, about babysetting all week, every week during the day, all summer long.  My heart dropped to my feet. I could feel my feminine side melt within.  I couldn't imagine not having the young girl come out for that whole summer.  I was shocked.  I didn't know what to say.
 Well, that following Monday morning my mother took me over to Karen's and dropped me off. As I watched her drive away, I felt so empty - lost is a better word.  Then suddenly I heard Karen asking me to come - in and she'd show me everything I need to know.  I must tell you, I've been over Karen's house many a times, visiting her with my mother a few times and there was a few times that I babysat for her so my mother and she could go out and party and be with adults.  I remember them saying that every time they went out. So, I must tell you that this wasn't my first time with Christine.  Matter of fact, she really liked me and I have to admit, I got very close to her.
As I entered the house, I was shocked.  There were dirty dishes every where, the Sunday paper was scattered from the kitchen to the dining room into the living room.  Baby formula was on the counter, kitchen table and the kitchen sink.  Now Karen walks me to the bathroom to show me where all the dippers are and, to my surprise, that, too, is a complete mess, with all her make-up scattered on the counter-top. Then I noticed something that gave me hope, to make me think that this isn't a bad idea after all.  I noticed two pair of her panties laying on the floor next to the tub, plus a pair of her panty hose that she took off, apparently because of a run. Then she took me directly to Christine's room, and I noticed her fast asleep, and that this was the most neat room in the house. Than it hit me.  I see that Karen was in one of her full slips.  She walks me to her bedroom and continues to get dressed.

As I watch her finally working her pair of pantyhose on and noticed her dropping her slip, she tells me the house is mind all mind do what I wish. Now she ask me to help her with her heels. As she sets on the edge of her bed, I slip them on. Than she ask for me to get her satin blue dress out of the closet.  As I'm helping her in this beautiful dress, I just about fainted. Now to my surprise, she wants me to help her with her curlers, so I did.  Then I brush her hair till she loved what she saw.  I was totally shell shocked - I thought I died and went to heaven.


 Well, as Karen was heading for the door, she stopped and turned. I could see the excitement in her eyes. Having a chance to prove herself at this job. A job she always wanted, It's what she studied for through out  college. Than she gives me a little peck on the cheek. Telling me thanks and that she loves me like her own  child.  Just as she was about to go outside. She stops again, as she turns, she ask. If you don't mind touching and going through my undergarments I would really appreciate you doing my laundry and maybe some house
work. At that moment, I know I died and went to heaven.  It seems like I couldn't say yes fast  enough.

 As I watched her back out of the drive, I could feel my feminine side working her way out. I could feel my emotions changing, from my voice, to my walk it was beautiful.  It was a month away from my Eighteenth birthday and summer is on it's way out and fall is stepping in.

Across the street there's this park. Where all summer long the boys and girls would play all their games. Now, I see the boys getting ready for football. At times as I feed Christine, I gaze out the kitchen window watching these young men preparing for football. I caught my self many a times watching this one good looking  Spanish guy. He would always come onto the field with just his tank-top and these very and I mean very tight  shorts. He was very dark, with long hair and very muscular. I couldn't keep my eyes off him.

As summer past by and I got to know most of Karen's clothes. I was being very confident in dressing up.   I must say I felt a little uncomfortable when Christine was up so lots of times I was in one of Karen's many  spring jackets. I got to know more of her clothing than my mother's. I knew of every colored panty she owns. Her bras, there were some that pinch me, than there was some that fit so right, I'd swear I wasn't in a bra.  Karen's wardrobe was much more feminine than my mother's. Karen loves dresses more than my mother.

So with that said, there was many more half and full slips.  Plus she loved her garter-belts,  along with her sheer stockings. I don't think I have to tell you, but I loved babysetting for Karen.
I noticed that I couldn't turn off my feminine feelings as quickly as I used to. It seemed my feminine side wanted to stay out and enjoy the life she was being offered and I'm wondering if Karen or my mother ever noticed. Down deep I don't think so. But, it was getting to the point where I even didn't notice.

 Well, it was a very busy weekend night, Friday to be exact. My mother and Karen were asked out by  two very young men, Karen claims they were just a few years older than me. But, old enough to party. They met them across the street, where they were playing some touch football the weekend before. And it so happens that my mother and Karen were jogging by and that's where they met. Before you know it, they had a date. I got to admit, my mother and Karen back then were some pretty woman. To be asked out by these two young men was no surprise to me.

At this club where my mother and Karen frequent a lot, that weekend was one of those very sexy nights. Where all the woman would dress up in very sexy clothing. I remember Karen and Mother going shopping for there clothes. Well, it was going to be one of my very feminine nights for me, Especially babysetting for Karen. I found her beautiful wedding dress in the back of her closet. It was in a large box, but it wasn't vacuumed. The day I found that dress I started looking for her under garments and found each item. Knowing where each Item was and that I was going to be a bride for the first time in my life, that night could not come quick enough.

After finishing my chores at home and my mother was ready to go. We were finally on our way to my  wedding day. As my mother and I entered Karen's house, like always she wasn't ready. All we could see was Karen running around in her bra, garter-belt, stockings and heels. Than she yells at me to help her with her hair, than finally with her dress.  Finally, off they went.  It was something like nine o'clock p.m. I had Christine fed, washed and dressed for bed. 

Now it was my time. Feeling my excitement within, I could feel my feminine side wanting desperately to step out. As time passed by, it was around ten-thirty. I looked in Karen's full length mirror she had in her bedroom next to her bed. All I could see was a woman that is always wanting to come out and feel life. I felt so different, I felt like I always should . I could feel the softness of every square inch of Karen's undergarments.  My hair was perfect, my make-up, I finally got my eye shadow  just right, my lip stick, it followed my lips perfectly.

 Suddenly, I could hear keys at the front door. My heart starts to pump, I started to feel light headed. Looking at her clock on her dresser, I could see it was only eleven-fifteen. Karen and my mother were not to be home till two or three in the morning. Now I could hear the front door opening and Karen talking to someone.  Now I was desperately trying to think of where to hide, but then I was hoping that maybe she was not going to come in her bedroom. So I tip-toed to her bedroom door (feeling her undergarments rubbing up against my sheer stockings), I heard her say something again. But this time it wasn't my mother, it was her date. Now as I'm up against her door I could hear her say to him that she's got to change in something more comfortable. With my heart racing, my eyes were starting to tear, so as Karen opens the bedroom door I jump under her covers. Feeling the wedding dress all around me, I try to flatten it out so that it doesn't puff up the sheets so much. Suddenly I think of my make-up and the lights go on.


Well, with not a very surprised look, Karen turns to her date and says that she'll be out in bit. Than she shuts the door slowly. As she turns towards me she has this very  promising smile. Karen sees me crying like a baby and comes and sits on the side of her bed, to comfort me.  I never felt so embarrassed  in my entire life, I told her.  I told her I don't know what over came me and I'm asking her not to tell my mother.  With that promising smile, she leans in towards me and gives me a kiss on my cheek.  As she stands up she says.  Honey, your mother and I knew about  your dressing in our clothes. There's nothing wrong with it.  You are who you are.

Than she asked me to get out of bed so she can see who I really I'm. Than ask me to stop crying, so that I don't ruin my mascara.  That's when she told me, with a very surprised look, that I'm very pretty and that I'm very good with make-up. So as I calmed down, she ask me to help her with her dress, that she had to change it along with her undergarments. I asked why - she wouldn't tell me.  After she was cleaned up and changed. She turns from the door and says. Don't ever be ashamed of yourself, you are who you are and you're very pretty at that!

Return to "Embarrassing Moments" Main page

Return to Homepage