I was 12 or 13when i noticed my moms clothing. I often wondered what it was like to dress as a woman so when my parents where out one night, i tryed my moms bra and panties on.
I put a pair of my dads winter socks in the bra to fill the bra out (my mom has large tits) I looked in the mirror and liked what i saw. I continued to dress up for along time, then i found my mothers dildos in the night stand, i would fantisize about what it would feel like to suck on a real cock while i sucked and licked the dildo.
When i was 14i thought i would be fun to fuck my ass with my moms dildo, I was dressed in my mothers clothing, bra, panties, garder belt with stokings and a nice blue dress that was slit up the side. I pretended i was sleeping and a burgler entered my home and found me dressed like this and wanted to fuck me.
I stood in front of the mirror and took my dress and panties off, all the while thinking the boy in the mirror was ordering my to so. I went to the bed and sat down, I then slowly lubed my ass with vaseline, inserting a finger then two in my ass. It felt tight and hot, at first it hurt alittle but as my ass loosened up it felt good, I sat up and put the dildo to my ass and pushed down slowly untill i felt the head of the dildo touch my ass, then i took a deep breath and sat down slowly, the dildo parted my ass and was inside me, it sent painfull shockes up my ass and i took it out quickly but the pain did not stop right away, a few seconds later i was ready to try again, This time the dildo entered much easyer, I sat there my leggs holding me in place and realized the dildo was only i my ass about 1 inch, I slowly pushed down untill i dident think any more would go in and then i pulled it almost out then i pushed down again.
I felt great and started to go faster and faster until a came without touching my self. I just kept bouncing up and down for what seamed like hours.
I came two times that night and thought this was the best feling of my life. I continued to dress up all through my teens and twentys untill i got marred in my mid twentys. I dident tell my wife what i liked by myself. But i was misurable. I devorsed and started to dress up again in my early thertys.
I started to go out dressed as a woman at night, walking in the park by the river when one night i was spotted by the police, I was horrafied and had nowere to hide. So i just kept walking until i was face to face with both of them.
Thay asked me what i was doing in the park at that time as they were shining a flash light on my? I said just out for a walk. the taller of the two said the park was closed and i should not be there. I just wanted to get out of there and said i was going to my car that was parked in the parking lot by the lake.
H e said ok and walked me to my car all the while my high heals where clicking on the sidewalk, The shorter officer said i should dress more conservitivly as i was wareing a short skirt and top that showed more skin then most would show, But i dident think i was going to be talking to two men let alone two police officers.
I got in the car and started it up and drove home watching as they stood there. I was so exited that when i got home i noticed i had come in my satin panties. I striped my top and skirt off and jerked off thinking of my incounter. A few months later, I found an adult movie and book store in th city i live in and told myself i should go there some time, So one night when i was dressed as a woman i went in and looked around.
I was scared shitless but walked around looking any way. The man at the counter kept looking at me as there was nobody els there.
I was trying to stay behind some shelves but they were only alittle higher then my belly.I thought to myself if he wanted to look, what could i do about it. I looked at everything thay had and decided to buy an 8inch cyberskin dildo and some lube. I walked up to the counter and boldly put my purchases in the counter, the man said is there anything else i can get you with a smerk on his face, i said what is in through the curtan at the back? He said the coin oporated peep shows, i thought ok i will watch a couple of showes and then buy my things and go but then 2 men walked in and i turnd red and thought what do they want.
The 2 men got some tokens and whent downstairs.
I asked the man behind the counter what was down there and he said more peep shows. i said ok and bought son tokens myself and went to the back of the store and whent in through the curtan. I saw about 15 cubicles inside and whent in one in the middle. there were holes on each side of the chair and a tv screan behind glass.
I put a token in the slot and a movie came up. It showed a redhead sucking this cock and i sat down to watch. a short time latter i discovered the cock was on a shemale, I was totaly blowen away. I did not think this was possable to have a cock and tits wow. I kept pumping tokens in to the slot and watched with all my atention and did not notice the cubicle next to me was now occupied, suddenly i herd a voice say suck me baby. I looked around and saw a cock sticking through the hole, i looked at in for a second and thought this was my chance to taste a real cock for the first time.
I was scared and said not with out a condom on, thinking he would leave but he pulled the cock back an a few seconds latter put it back through the hole again this time with a condom on, he said now suck bitch. I got on my knees and looked at it up close and like i was under some trance i opened my mouth and put the head of his cock in my mouth.
I was hard yet spongy at the same time. It was also hot not like my past experence with my moms dildo. I started to suck harder and deeper, then he pulled his cock back through the hole and i thought i hurt him but all he said was meat him in the end cubicle and left. i stayed there for another min or so then headed down to meet my new friend.
i opened the door and saw the man with the cock i had just been sucking siting there. I went in and sat down, (this cubicle had more room in it) i said hi, he said he had to stop me or i was going to make him cum. i just looked at him and he said i could continue now, i got between his legs and went at it again this time he put his hands in my head and pushed down and let me come up again then he would push down again.
I thought i was going to gag but i dident, after a few minites he took one hand and put it on my lower back by my ass, i shot up in a hury and he said it was ok.
I said i was not looking for any of that. He just smiled and said what did i want then, I told him i lost a bet with my husband and this is what i had to do to pay up. He said that was ok but becouse i sucked one mean cock he just wanted to know if i wanted to fuck.
I again said no and tryed to stand up but he put his hands on my shoulders and said ok can you finnish the blowgob. ok i said and went back to the cock, I started to lick from the bace of the shaft all the way to the tip then put his cock back in my mouth (all the while thinking this cock would feel good in my ass but was scared at the same time).
I sucked for a few min then his cock started to swell in my mouth and i thought this is it, suddenly he pulled his cock out of my mouth and riped the condom off and came all over my face, I tryed to get away but was too late.
His first shot landed on my lips and the second across my nose and eyes. I was suprised and just sat there as he stood up pulled his pants up and said thankx and left. I used some tishu to clean my face and went back to the front counter to make my purchase and left. When i got home i fucked my self with my new toy thinking of the man i just sucked.