Three times caught dressed fem. Twice while getting the mail, the mail box is across the road. First time I was wearing a tight t-shirt with big boobs and jeans. I dont have a wig and dont use makeup so a guy wearing womens clothing. Waited until no traffic was coming and went to the box. As I was turning to go back, there was my neighbor(male) standing at his box about 30 feet away...staring at me. I waved and crossed my arms over my boobs best I could and hurried back. Second time I was wearing pink t-shirt with big boobs and light gray Capri leggings. Got to the mail box with no cars in sight but as I turned I saw a car pulling up to the intersection about 75 yards away and turning in my direction. I ran best I could back to the house. Third time I was dressed in tight black pleather leggings and red t-shirt with big boobs. Stopped at the gas station to get gas. Went all the way to the end pump far from any other cars. Just as I started filling a delivery truck pulled up near by. The driver must have spotted me as he pulled in behind my car and waited. There were at least 5 other pumps he could have used. I could see him staring and laughing, looked like he was talking to someone on his phone. Since I was caught I made sure he got a good look. There was a time I got caught naked with a dildo up my ass by my sister in law. She came I to the house and I never heard her. When she came around the corner she gasped. There was no where to hide...she saw it all. I just froze. She stuttered a few times then said, "I'll come back later" turned and left. I could hear her giggling as she left. As far as I know, she has never said anything and she has never spoken of it to me.

Was out in the forest on a logging road with several water filled low spots between me and civilization so i thought i was pretty safe,water up to the doors on 4x4 truck. I had just set up my camcorder on tripod and stripped down and was just ready to use my dildo on my butt hole when i heard a cough ! grabbed my pants and hid behind truck when a guy came walking out of bush onto the road ! Berry picker ! Not sure how much he saw or how long he was there !

When I lived at home with my parents & sister, I would wait for them to go to bed then I would go down to our basement where I had a stash of clothes, makeup, heels, everything I needed to dress as a girl. I secretly have been taking things from my mother & sister for years, I would get dressed up as a girl then sneak out the back door & walk around the town. I loved being seen as the girl I so wanted to be. One night a car pulled up alongside of me & asked me if I needed a ride, I told the guy I could use a ride if he didn't mind that I was not really a girl but a boy dressed up like a girl, he said he didn't care so I got into his car.
He said his name was Mike, I told him my name was Joanne, he asked me why I was dressed as a girl, I told him it was because I wanted to be a girl. He then asked me if I had ever been with a man before, I told him I had not but I wanted to try it, he asked me if I wanted to try being with a man with him, I looked at him & smiled then said yes. He asked me if I minded if he drove us to the lake, he said he knew of a place where we could be alone, I told him I would like to go there then I slid over closer to him in the seat. He put his arm around me & I leaned into his arm & took his hand in mine.
We pulled into the lake & parked, as soon as Mike shut the car off, he leaned into me & started kissing me. I kissed him back & then felt his tongue trying to get into my mouth, I took his tongue into my mouth & sucked on it, we were in the car making out for a good 15 minutes before Mike said we should go. We got out & walked over to this broken up old gazebo, we went inside of it & there was a nice clear area. We sat on the broken wall & started kissing each other again, Mike started kissing my neck & worked his way up to my ear, when I felt him put his tongue into my ear I went nuts, I loved the way it felt & it made me feel like a real girl, I put my hand on his crotch & started rubbing his cock thru his pants.
It didn't take Mike long before he pulled out his semi erect cock & told me to get on my knees. I got on my knees & took his cock in my hand & began kissing it up & down the shaft, when I made my way back up his cock for the third time, I licked all around the head of his cock before I took it into my mouth. I liked having his cock in my mouth right from the start & I learned how to suck cock rather quickly. It didn't take me long before I had his entire length in my mouth & part way in my throat. When I tasted his pre cum, I knew I had to have more so I really started sucking on his dick. Mike put his hands on my head & started violently pumping in & out of my mouth causing me to choke & gag but I kept sucking.
Mike began to cum, I felt his load hit the back of my throat & I instinctively swallowed it but more & more cum kept filling my mouth faster then I could swallow, some of his cum was leaking out of the corners of my mouth & getting on my blouse & skirt, Mike finally slowed down & that gave me the time to swallow a lot of his cum. Mike took his cock from my mouth & I looked up at him & opened my mouth to show him all of his cum I had before I swallowed it, then I took his dick back into my mouth & cleaned off all of the cum. We got up to leave when 4 other guys walked into where we were, they all asked if I would suck them off as good as I sucked off the guy I was with. They said they watched me suck his dick from start to finish, I asked the men if they would mind if some of them fucked my ass while I sucked on the cocks of the other two men, they all agreed. By the time we were done, I was drenched in cum, my ass hurt really bad & my throat was really sore but I would do it again in a minute.

That story gave me such a boner. Joanne.

That story gave me such a boner. Joanne.

Years ago my ex caught me wearing her wedding dress a couple of years after we were married. I was wearing her nylon stockings, garter belt, wedding shoes, which fit me because I have slender feet. Anyway I was so aroused I had lifted the dress and was standing in front of a long mirror, masturbating furiously when she walked in the bedroom.

She was terribly upset and it changed things between us for the worst. But what I find funny now is that she was even more upset that her dress and undergarments fit me but not her.

H there, you answer your question, I've been caught several times, I've been dressing since i was a 12 years old sissy panty boy. So anyways i usually dress and play with myself at a few local cruising spots, but this day was a little different,.. I was wearing a French maid bustier with garters straps and thigh high fishnets,and my feet i had on a sexy pair of black patented leather 6" platform heels size 12 heels. I loved theses heels. Well anyways, the spot was empty, i didn't see one car coming down the road for about 20 minutes. So i got really horny. I had my cock hanging out the right side of my panties, it was nice and hard. I stepped out of my vehicle and I posed for a few pics with my hard cock throbbing, my door blew shut from the breeze and i keep stroking myself and tugging on my balls, posing and taking more pics,my cock was so hard when suddenly i heard a truck start up and he pulled out from behind some brush and was driving my way, i knew right away im busted. I can't get to my vehicle fast enough.I'm dressed like a little sissy cock sucker, how will i make it to my vehicle without being seen, Especially in 6" heels. Oh my i was so humiliated as i walked to my vehicle with my hard cock that wouldn't go down. I'm in lingerie and high heels. I covered my face in shame as he slowly drove past me. I was embarrassed yet i was aroused, i hopped in my vehicle and kept thinking if he recorded me, or if he watched me for a while, or what? I did notice he was a silver daddy, older probably in his 60s or 70s, which is just my type. But i always wondered if there's a video tape of me out there, or if came good while he watched me.. I drove up to where he was parked and i verified that he saw everything.. And i eventually came all over myself shortly afterwards, i was very turned on by then.. But i always drive all the way down first and then drive back to make sure nobody's there before i get to carried away..

It was a Friday and I was getting ready to go see someone so I had my sexy thong on and my belt didn't really fit so he seen my lines first time the second time by my sister