Caught With My Skirt Up!

I started wearing panties and bras when I was about 12.  I would do it when my parents were out and dress up.  I would put on my mom's bra and panties along with pantyhose.  When it got dark, I put on a t-shirt and shorts.  I would walk outside and go to a park about 2 blocks away.  There I would take off my t-shirt and walk around with my bra showing.  Sometimes there would be other people at the park but with it being dusk, they could not really tell that I was not a girl.  Later I would walk around in just my bra and panties.  It really turned me on.

SAs the years moved on, I continued to crossdress, to the point of putting on makeup and wigs.  I have acquired quite a wardrobe over the years.  I crossdress daily in sexy panties, matching push-up bras, and either hose or thigh high stockings.  I have many skirts and sexy blouses, many of them see-through.  This is where I got caught.

I was living in an apartment with a male roommate. I am 6'1" tall, 178 lbs, with blue eyes.  I was 25 and had a real good looking girlfriend named Susan.  My roomie was going out so I did my usual; go to my room and start making myself up.  I put on my makeup and medium brown, long haired wig.  Than I chose a black push up bra, 38B front closure that helped my breasts look larger.  I than selected black sheer pantyhose and rolled them up my legs.  A red and black lace pair of bikini panties finished off my lingerie.  Going to my closet, I picked a red sheer silky blouse with a black mini skirt.  Tucking in the blouse, I looked in the mirror and liked what I saw!

At this time, I thought I heard a door open but when I looked in my bedroom, I did not see anybody.  Going back to my mirror, I adjusted my mini skirt and re did my lipstick.  As I turned around, Susan was standing there looking at me!!!  Not knowing what to do, I just stood there blushing.  She spoke first.  "I thought that something was going on, and now I see!  Do you do this often?"  

Without thinking, I stammered "Yes, almost every day."  She seemed somewhat amused by my appearance and moved towards me.  "Does this make you feel sexy wearing womens clothes?"  

"Yes" I replied.  I could not look her in the eyes, I felt ashamed and yet excited at the same time!!  What would she do, what would her reaction be?  I did not have long to find out!

Susan came up to me and reached down under my skirt.  She grabbed my little **** which had gotten amazingly hard and said "Your little clitty seems to be quite excited by my catching you all dressed up!"  She rubbed my nipples thru my blouse and bra.  I was about to shoot in my panties!  She told me to stand there and not move.  Going over to my dresser, she started looking thru my drawers.  Finally she found the strap-on that I had hidden.  She said that if I were going to look like a girl, I should be screwed like a girl.  She told me to bend over with my hands on my bed.  Doing as I was told, she came behind me and pushed my skirt up and started playing with my clitty thru my panties and hose.  As she did this, I could not help but moan.  "Don't you dare moan in pleasure you ****"  she snapped.  "I will tell you when you can do anything!"  With that, she pulled down my panties and hosereveal my hole.  "Do not move" she ordered.  With this, she went into my bathroom and came back in a couple of minutes.  She had taken her shorts off and had put on the strap on!  I knew what she was about to do!

"I am going to teach you a lesson you ****!"  She moved behind me and rubbed the tip of the ***** by my hole.  "You are going to have to take this without any lubricant since you have been so bad, but that is probably how you like it anyway" she sneared.  With that she pushed the tip hard into my hole as I gasped with the force of the push.  She worked it in and out pushing harder each time.   I had never had it rammed in with so much force, but actually liked it.  She worked it until most of it was in and she started a rhythm as she pushed harder and harder.  I was gasping as she ****** me hard.  My clitty was about to explode as she pumped me in and out.  "You like this you little *****?  Do you go out all dressed up you ****?" she asked. 
"Answer me ****!" she demanded.

"Ohhh, yes it feels good" I moaned.  "I do go out all dressed up 2-3 times per week" I said between thrusts.  

"I'll bet you get ****** all the time" she said as she pushed it in all the way and than pulled all the way out.  As she jammed it all the way in, she said, "*** in your panties *****! I want to see you smear your *** all over them!"  I was already soooo close, it was not going to take long.  I began rubbing my clitty thru my panties and hose.  My clitty was leaking *** all over already and the feeling was sensational.  I could see Susan ******* me in my mirror.  Watching this, I started to moan.  "I'm getting ready to squirt all over" I said.  "*** in  your panties, I want to see it" Susan replied.  I moaned loudly as my first wad shot into my panties and soaked thru into my hose.  I moaned again as I could not control it.  *** shot out in spurts.  I kept pummping my clitty as I could not stop *******.  My panties were soaked as were my hose.  Finishing *******, Susan pulled out of me.  I slumped down on the bed.

"You shot more than you do when we have sex" Susan said.  "Maybe you need to dress up to get excited" she said.  I kind of like having my own sexy **** to do what I want with.  I think this will be fun!  "You will do things I want and I will not tell your roommate or anybody else your secret.  I will call you and tell you how to dress, and you will obey.  Do this, you will have fun and new experiences!  If you do not, you will be exposed to everybody" Susan told me. 

I agreed to Susan's conditions.  We had many sessions, sometimes alone, sometimes with girlfriends, sometimes with guys but they were all fun.  This went on for about 3 years until we split apart.  I now live by myself, am 36 and dress most of the time.  I am supposed to start a new job in a couple of weeks and I interviewed for it as a woman so I may be able to live like one!
chrisnolin chrisnolin
36-40, M
4 Responses Jul 26, 2010

You got me so excited !

It will be fantastice working as a Woman!! Hope you got the job!

Terrific story. Wish it were me.

Wow, that story made me so hottt!!! You are one lucky person to have had that happen.