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Jojo3000

TS 49
Washington US
Joined August 2008
May 5

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All about Jojo3000

I have been dressing since I was about 14.

I played dares with a friend of mine which often included us wanking. One time he dared me to walk around the house wearing his mother's black lacy knickers, the forfeit if I did not was that he would tell everyone at school I wanked off in front of him. Even though I felt totally humiliated wearing knickers standing in front of him, the feel of them on my cock was such a turn on. When I went home I kept thinking about that feeling and went into my mother's underwear draw. I found a pair of her tights and wanked while wearing them. I got such a kick out of it but the tights were covered in cum and had to hide them in my room, they were the first of many fem things I would have to hide because I shot my load while wearing them!<

My friend did not mention the incident for a couple of weeks, we continued playing dares which usually ended in us wanking, then he asked me again to wear his mother's knickers and stockings. I was so turned on my little prick went hard instantly. We both went into her room and rummaged through her underwear draw and found satin black knickers, suspender belt and black stockings. I put them on loving every bit of the sensual soft feel of them. When I turned round my friend was lying on the bed, he had stripped off and was wearing his mother's slip with his huge cock erect, stroking it through the silky material. He admitted to me then he had been having regular wanking sessions in his mother's and sister's underwear. The wanking session we had that day was fantastic.
This became a regular thing every Thursday, his parents would be out shopping and we would go into his mum's bedroom and dress up in her underwear. We started playing dares again while we were dressed. We used to write the dares on pieces of paper and we had to do what ever was written on the piece we selected from the pile. One day while we were both wearing his mum's tights I picked a dare from the pile and it simply said "Wank me off". Innocently I had not expected things to go in this direction but looking back now it was obvious things would end up like this.
So I started rubbing his penis through the nylon of his mum's tights until he came. We were both a bit ashamed and he told me to go. I went home wearing the tights under my clothes and I quickly jerked off when I got home.
We were now starting to collect worn underwear from aunts, other friends mothers etc. and had a huge collection and we started playing another game. We had a large collection of pictures of page three girls and we would pick one at random and dress as close as possible like the girl in the picture. I picked out, once, a beautiful brunette who was completely naked except for a pair of high heels. My heart started racing at the thought of wearing them. This time we were at my house so I looked through my mum's shoes and found a pair of court shoes size six. I squeezed my feet into them and I swear I almost came just putting them on. My friend John was wanking himself furiously looking at me. "Put some stockings on as well and wank me off" he said. I did as he had asked and when I made him come he watched while I splashed my spunk over the stockings and heels.
I was playing the "girl" role more often than John when we met up. Sometimes John would just bring some teddy or camisole or basque he had taken and I would dress up and play with his penis until he came. Also I had started wearing lipstick and sometimes I rubbed it on my cock end.
One day I decided to go the whole way and dress up fully. It was a Saturday and my parents said they were going out for the night and I thought about dressing up all day, my heart pounding and my penis erect. I waited about twenty minutes after they had gone out to make sure I would not get caught. Then I went into my mum's room. I opened up her underwear draw and pulled out a suspender belt, black stockings and satin black knickers. Out from her cupboard I picked a black dress and some sexy high heels that had a bow on. I lay them out on the bed and stripped off. First I put on the suspender belt and rolled those lovely stockings up my legs, next the knickers and dress. I slipped on the heels and wobbled till I was in front of the mirror. It wasn't a good look! But I did not care my cock was so hard I thought I would come without touching it. I went to the bathroom to put on some lipstick and tied my long hair back and tottered back in front of the mirror and started wanking. Then I heard someone in the house, I was terrified and ran into my own room and climbed into bed hoping whoever it was would not come into my room. I lay there not daring to move and I could hear the person coming upstairs and going into my parents bedroom and thought one of them had come back and they had caught me dressed. Then there was a knock on the door and a voice said "Jo are you in?" It was my friend John and the relief came over me in a waves "Yes" I replied my voice shaky and he opened the door. "What yer doing?" he asked "Er nothing" I replied pulling the duvet over me. "You wearing lipstick?!" he laughed and I blushed. John pulled the duvet off the bed revealing my full feminised body, he let out a gasp "You dirty bastard!" he exclaimed.
He then pulled down his trousers and said "Suck me off bitch" laughing. I got down on all fours and started licking the end of his huge dick. He pulled my head forward and forced me to take the full length of it and I gagged a little but kept sucking. It did not take long before he came in my mouth. He left quickly, I felt so ashamed and used.
He started coming to my house more often hoping my parents would be out and when they were I would dress up for him. He would lie on the bed while I gave him oral pleasure.
Not long after this his mother found his collection of underwear and porn and he had to throw it all out. I have never discovered the conversation he had with her after she found her things in his bedroom, covered in his and my come stains. A couple of weeks later my mum found her tights and high heels in my cupboard while she was cleaning. I had worn them the previous night and forgot to put them back. She asked me about them and I made up some stupid story about a fancy dress I was going to, I don't think she believed me. So we stopped dressing up and having our sucking and wanking sessions. Once however, much later I caught him in the shower wearing a pair of his sister Gillian's knickers, I joined him in the shower and we sucked each other off and that was the last time I had his cock in my mouth. I see John occasionally and wonder if he still likes the odd pull in his wifes panties and the things we did never ever get mentioned.
I stopped dressing completely for about four years. I was about twenty when I started again. One night when I was drunk after going to see some strippers at a local bar, I came home horny as hell. For some reason I went through my mother's knicker draw and found some fishnet stockings and a white suspender belt and a black knickers. I wore them all night in bed wanking. After all that time not dressing I had forgotten abou the feel of those soft feminine things on my skin and how much of a turn on it was wearing someone elses things.
The following week I came home from work and wore some stockings and suspenders under my clothes and went out to buy porn from a local newsagent. The thrill of it drove me insane and I walked around the streets looking for somewhere to relive my erect cock unfortunately there was nowhere so I went home. I started doing this two or three times a week. Also at this time I found out what I was - Transvestite - the word was written in the phone number section of the dirty magazines I had bought and of course I would dress up , phone the numbers to hear some sexy woman ordering me about and telling me what a dirty slut I was.
Once when I went out late at night I was almost caught by my neighbours daughter. I had on a pair of tights under a long trench coat and I passed her in the street, the wind blew up my coat but luckily she did not turn to see me.
Not long after this my mum and dad split up and I left work. My mother moved away so I was denied the use of her things but I did manage to take some underwear and a dress before she left. Boredom set in as I was at home most of the day as a result my crossdressing increased and the games I played became more and more odd. I found out that while dressed I would like things inserted up my arse - carrots, joysticks, chocolate bars and candlesicks. Being bound up was also another thing I liked and used ties and a dog chain to tie myself to the bed.
My imagination went wild but I was held back by the lack of clothes. I started buying stockings from a shop near me and used to get odd looks from the female owner. The schoolgirl look was easiest to achieve using some of my old uniform and I would lean over a chair while dressed and spanking my arse.
My dad had been on holiday and met a girl called Jackie and every few weeks she would come up to our house to stay. We did not get on and was pleased when she went home. However she had left some of her clothes in our spare room including a pair of M and S black knickers and a black teddy. To say I was thrilled was an understatement. I put on the black teddy and chained my self to the radiator, teasing myself while smelling the crotch of her panties.
Jackie came to our house on a regular basis and on a regular basis she would leave items of clothing. She wore some sexy things too. One night while they were out I went through her case and found a pair of black stockings purple suspender belt and a matching pair of knickers and of course wanked myself silly wearing them in front of the full length mirror. Her daughter used to stop with us too and I wore her tights a couple of times. I was never sure if they knew what I was doing but bizarrely I found a pair of said daughter's tights in one of my coat pockets.
I was about twenty-two now and had started working again and had a girlfriend. I had only being going out with her for a couple of weeks when she found my girly things in a cupboard and I told her they were things left by Jackie but she did not seem convinced. I would wear gf's clothes over the next five years that I lived with her in our own home. She almost caught me several times. The first was when she went to her classes after work. I was dressed in her basque and black stockings and had started taking pictures of myself and had them laid out on the floor wanking furiously over them. Then I heard a knock at the door and I panicked and stripped off throwing everything underneath a TV stand in the spare room. The knocking at the door was getting loud and agitated, I quickly got dressed and ran downstairs. My gf had come back early due to a power cut. Luckily I had bolted the door and lied about listening to music with headphones on and that I could not hear her. She was not very happy and was from then on suspicious of anything and everyting I did. I removed the clothing and pictures later and hid everything in a gap in the wall of a cupboard. We never really had a good relationship and sex had become a chore. I started taking more and more risks and dressd in her things while she was in the house. Also I had started wearing her aunties clothes who lived just round the corner from us. After five years and taking so many risks it was only a matter of time before I got caught and it happened when I was at work and gf rang me and said we needed to talk when I got home.
When I got home she had found some things of hers I had been wearing including a white suspender belt that had come stains on it. We talked about my crossdressing there and then and it was a relief at last to tell her and she was ok with it...to start with. She even gave me some of her knickers to wear and I was so turned on. Over the next few weeks we had some of the best sex we'd had mainly because I was so horny because she knew about my dressing. But I wanted to take it further, I wanted to wear her underwear and fuck her. Again while she was out I put on her basque with a pair of her holdup stockings and she came home early, she was not impressed and did not talk to me for a week. The final straw came for her when she found a pair of stockings I had bought full of my spunk and we split up not long after.
Freedom then to do what I liked...
The first night after we split I bought a pair of white stockings, put on a pair of high heels and paraded around my house like a dirty slut. My gf had left some of her make up and I wore that too. The following weekend I went to town and bought a purple suspender belt with matching slip and knickers from a charity shop along with a pair of high heels. My trips to this shop were frequent and the same woman served me every time but she did not mind me even though it was obvious what I was doing. She was not bothered where or who the money came from. I also purchased a maid uniform from a novelty shop and stockings from a department store. During my holidays I would spend days dressed as a maid doing the chores in my house.
I had gone back to buying porn and was quite surprised and shocked at the quantity and perversion of some of the tranny mags. I found a telephone number for contacting cd's but nothing came of it at that time. But I did get myself off while dressed chatting to other trannies and cd's.
I could not afford to live in that big house on my own so I sold up and moved in with my friends daughter, Katie and what a great idea that turned out to be! She was 23 and very sexy. she dressed like a sexy sultry secretary for work. Of course while she was out I could not help myself trying on a few of her things! In her underwear draw I found lots of thongs some of which I took. She also owned one of the biggest dildos I have ever seen and on occasion i forced it up my tight hole and wanked dressed in front of the full length mirror. I wore her black basque with a pink trim and matching panties and luckily because she was a big girl I could get her shoes on no problem. I put on a pair of her thigh high boots over the top of her fishnet stockings.
We lived near a park and at night I would wear her frilly things under my male clothes and go to the park. I would strip off and put on a pair of heels and parade around like a slut wanking myself off. Looking back I got such a kick out of it and I think I wanted to get caught.
I rang the tranny phoneline and I wanked off with a guy called Colin and he told me all the filthy things he would do to me.
I started ringing the phoneline and leaving my number looking for a meet but nothing happened until a guy from newcastle sent me a text message asking if I was available to meet up. It took a couple of days until we were both free to meet. While we were texting he told me he had a tights fetish and loved to wear high heels. So one night duing the week I met him outside my local pub and he drove me back to Katie's and we went into her bedroom. I was already wearing a basque, stockings and knickers under my suit and I stripped off in front of him I was so hard dropping my pants to reveal my sexy lingerie. He had stripped too and was wearing 10 denier tights with his massive cock sticking out. I lay on the bed while he put his cock between my stocking clad thighs and wanked himself. Then we swapped places and i put my cock between his legs and licked the heels of his stilettoes. He came first all over my stockings then I shot my load over his thighs. We arranged to meet again but nothing ever came of it and I never saw him again. My biggest regret was that I did not suck him off.
I moved out from katie's and lived back home for awhile and discovered lots of other cd's on a website and joined yahoo to chat to them. One guy who lived near me had a webcam and he would dress up on cam and wank off for me. So I went out and bought a cam so i could do the same for him. While we were chatting he mentioned a place where cd's met up and he had sucked a guy off there while wearing his wife's stockings and panties, the thought of this turned me on but when he asked to meet me there I bottled out.
Of course he was talking about dogging but I did not realise this until I googled the place name he had mentioned. It sounded very dangerous but exciting and I kept thinking about going there and it took me a long time before I had the courage to give it a go.
So I put on a white suspender belt a black thong and black stockings and put my clothes over the top of them. I took the bus to the place that was mentioned. When I got off the bus I started walking around looking to see if there was anyone around but there was nothing but hedges and I started to think I had made a mistake. However it was still a bit light and I had been told most of the action happened when it was dark so I stuck around for a bit. While waiting I noticed something in one of the hedgerows - a worn holdup stocking - it was covered in cum stains I was so excited now I almost popped!
I continued walking as it was getting daker a few cars turned up and nervously I kept eyeing the drivers. Then I noticed some of the cars a second time, they were driving round in circles checking the place out. By this time I had been there so long my cock was rock hard and I was so horny I thought bugger it and found a little corner of hedge that wasn't too exposed to the road and pulled down my jeans. A car came by and I lost my bottle again. I pulled up my trousers but too late the guy in the car looked at my stockings and knickers grinning. I felt fithy and sexy!
Another car had parked up opposite where I was and the driver got out and went behind a gap in the hedge. I followed him my heart pounding my dick ready to explode. When I got through the gap there was a forty-odd year old bald guy wanking his cock furiously. "Alright?"
he said. I gulped at the size of his penis it was fucking huge. "Hello" I said shyly, he was eyeing me up and down still masturbaing. I then pulled down my jeans to my ankles exposing my feminine under garments the man started wanking faster and said "Fucking hell I love it"
I got down on all fours and took the full length of that man's prick in my mouth. I must have been too eager as he told me to slow down and he was rough with me forcing his cock to back of my mouth touching my throat. A car passed by the otherside of the hedge and I pulled away from him but he said everything was ok. "I have been a naughty girl" i said to him and he gasped and spun me around so that my panty clad arse was near him and he administered a spanking slapping my bum harder and harder. He turned me round to face him again and he shoved his engorged penis into my waiting mouth. It wasn't long before I could feel his cock twitch and I waited for him to come in my mouth but he pulled it out and he jizzed all over my face. "That was fucking great" he said after emptying himself on my lips and he pulled up his trousers and disappeared through the hedge.
I was still on all fours in my stockings I felt exposed, humiliated like a dirty little slut - it was fantastic! I waited a bit to see if anyone else would be coming but nothing happened so I put my trousers back on went through the hedge back into the lane. When I got there there was a line of about four or five cars with their headlights on. I was so turned on I dropped my pants again and wanked off in front of the first car. The drivers all smiled or winked at me as I went by them.
#Transgender #Regular #Washington #UnitedStates #US

Gender

TS

Age

49

Last Comments

Avatar arlesson
arlesson
January 12th, 2015
why don'tyou start a blog JoJo ??? You have an interesting bio, girl...
Avatar Soph
Soph
July 9th, 2013
Stunning him ply stunning hugs soph
Avatar Soph
Soph
July 9th, 2013
Stunning hugs soph xx
Avatar chloe
chloe
December 2nd, 2012
great bio. xx
Avatar rihana
rihana
November 16th, 2012
Nice profile xx
Avatar SandraTV
SandraTV
February 10th, 2011
mmmmmmmmmm very sexy babe xxx
Avatar annatvuk
annatvuk
February 5th, 2011
mmm hiya x
Avatar Xxjohnross
Xxjohnross
August 17th, 2010
You sound very interesting
Avatar tvapril
tvapril
January 31st, 2010
Blowing you a kiss!
Avatar Rosecd69
Rosecd69
January 31st, 2010
Big Hug!