First Time Panty Boy With the Babysitter

I know this sounds like a young boys dream but i can assure its true. When I was 10 and my babysitter was 16 she would pick me up and drive me to her house until my parents got out of work. My babysitters parents were both also at work. She was a cheerleader and practice was her class of the day so would drive home in the outfit and change right when we got there.

It took me awhile but i found out if I quietly went on the kitchen porch i could see into her bedroom window. Due to the layout of the house when I saw her leave her bedroom I could get back into the kichen  undetected. So I got used to seeing her silky bikini panties everyday. I would get disappointed when she would wear thongs as I am more attracted to full back panties.

One day I don't know why I said it but I blurted out, "I like the ones from yesterday better"

she said, "What ones?", I responded by stammering out, "your underwear."

With her response I obviously knew she had been teasing me on purpose by leaving the blinds open. She took me to her room handed me her silky bikini panties and said, "You mean these" I took them home and wore them to school the next day. And when I got to her house, I once again don't know what came over me, but I just ripped my pants down to show her I was wearing her panties. She led me to her room with a smile on her face, once there she removed her skirt and I was living my fantasy. She then put the skirt on me, and layed me down on her bed. She stradled me wearing her panties which was the single greatest moment in my life until she reached up my skirt. Her soft touch through my silky panties was overwhelming, it didnt' take long for me to finish.

The next day my parents picked me up from school claiming Laura was sick, same thing the next two days. Eventually she "moved away" I never saw her again but always have the memories.

l49331 l49331
18-21, M
36 Responses May 15, 2008

I wore panties the first time when i was 14. I wet myself while at my cousin's for the weekend. Her mother made me take off my clothes and told me to put on my pajamas. Before I did however she left the room and came back with a pair of my cousin's panties for me to wear. I put them on and then put my pajamas on. I was so turned on that I asked my cousin if I could wear her panties whenever I was over there. She thought it was cool so she encouraged it. I started borrowing my step sister's panties at home. Pretty soon she caught me but told me she already knew since my cousin had told her. I remember she said to me "I always thought you were too pretty to be a boy." Anyway, several months later I got in trouble at school. The headmistress called my stepmother and when I got home I was met by her and told to immediately go to her bedroom. I knew what that meant. She went over to the front hall closet and took out the brown leather strap she used for spanking my sisters and I. She had me walk up the stairs ahead of her and marched me into her large bedroom suite. She then called in my sisters which was the way she did it. They had to watch. I was told to take my jeans off. I hesitated and then she got very firm. "Take them off now or you'll get more of the strap than you bargained for. Then get over to the chair and bend over." I turned around and faced the chair she used when we were strapped. I slowly undid my jeans and let them slide off. "What's this?" "Wearing panties? Whose are they?" I told her they were my sister's. "Fine. We'll discuss this later now bend over and pull your panties down." She then waited a minute and started the beating. She gave me 20 hard lashes with the belt. Then she told me to get dressed. That evening at dinner she brought up the panties and asked me how long I had been wearing them. I knew I had to tell the truth because she would call my aunt and verify everything I said and if I lied I would end up with another strapping. When I told her everything she only said, "well, I suppose you could do worse things." I considered that permission. In my third year of high school I decided to start wearing makeup. I'd put it on as soon as I got home from school. I always wore panties of some sort and started in pantyhose as well during my junior year. This was the beginning. After living as a girl in my head I finally had the courage to tell my mother than I wanted to consider changing gender. She and my sisters were totally supportive. I'm at the beginning of the process now. I can't wait for my breasts to develop to the point where I need a bra>

I'm sad that you never saw her again. But great memory, and great story!<br />
Thank you! :)

What a great story. Just adore wearing panties and lingerie that women have me wear. Had an experience when I was younger also and have been wearing panties ever since.

great story nread.sound fun

I love wearing panties too

I wear pantie when I can so exciting I get mine from people's houses I work in always used I wash them eventually when then scent as gone

omg i wish that happened to me

i am 13 and wear my sister (14) clothes all the time! i have been caught once and she now lets me wear whatever i want, whenever i want!

I was 9 when my babysitter asked if I would like to wear her panties and I said yes. they were yellow nylon full cuts with transparent front. I loved them and immediately got hard. I came downstairs and opened my pants to show her. From them on I would wear moms panties to jack off. I am 68 and am wearing 2 pair of nylon panties as I write this.

Panties are addictive as I never get tired of the feeling.

Cetainly is a dream I have relished over the years. Still wear my wifes every day, all soft silky bikini cut ones!

Fantastic story. I am still wearing thirty years after my first experience of being caught in panties

man LOVE the story. reminds me of similar experiences. LUCKY you

Wow that is just so hot<br />
<br />
I so want to have an experince like that.<br />
And me a cross-dressing straight boy

wow amazing

wow amazing

wish that happend to me

wish that happend to me

What a wonderful experience. <br />
Boys with pannies.

AMazing story, I have some panties you might be interested in just message me!!!

Nice story!

nice..lucky guy.

nice..lucky guy.

u should have boned what the hell were u thinking!!

good story i also wore girls underwear with my babysitter but i wore her thongs and tights

wished it happened to me

I wish I could have been that lucky when I was his age.

That story is every panty-wearing boys ' dream!

awsome story!! I first wore panties when I was 10 yo..I wore my cousina panties,,she was 12 yo..she loved to see me in her panties!!!

I am dumb struck on this story. You are 10 yrs old, she is sexteen. I thought the male hormones didn't kick in to 13rs or older. I can't picture you being able to make a rise statment at 10 yrs old. sorry can't believe it

what are you talking about i was mastubating to ****** at six and my briefs were a major part of my turn on

I hope she does an enjoying every moment *smile*

Girl on Girl is always fun. The feeling of satin against satin is electric. Great Babysitter Story.

Man I wish I was so lucky

Wonderful memory to cherish.

Damn, your hopes & dreams of more dashed! A scenario many of us would like to live over again & again, if were that Lucky!

My guess was she didn't want that to happen again, but I dont know for sure