As a only child I was not like some of the lucky girls on here who were able to gain access to sisters wardrobes. If I was lucky I was able to gain access to my mother’s clothes on rare occasions. My earliest memory of dressing was when I was about 7 or 8. I remember playing in the room I shared with my mother in my granddads house. The washing basket was kept in there. I remember one day spending what seemed like hours playing dress up with the dirty washing. In hindsight I was probably 10 minutes, but it seemed like an age. I remember putting my mum’s panties and skirt on over my clothes, and trying different combinations.
Now I have to admit that I don’t remember dressing again after that for quite some time. Calling it dressing is really giving it a label that is not needed, I was just a child messing about with innocence of sexually and what conforms to the normal. Around this time my granddad had been very ill and he had to sell his house to pay for the home that he needed to be in after his surgery, and where he would spend the next 9 years of his life before he passed away.
The next part of my life was spent away from where I had lived before. I met my father for the first time, and meet other children from different cultures and generally had a different lifestyle. I went from being the butcher’s grandson in the small town I lived in, to one of the kids that lives in the top block of council houses. I lived with my mother in various different areas of a town until we got a proper house, not a flat or maisonette. I made friends with most of the kids on the road and my mum made friends with quite a few of the single mums on the road. It got to the point where we would stay at one parents’ house on a Friday or Saturday night with a babysitter while our parents went out mainly looking to get laid, although we didn’t know that at the time. By all accounts sometimes they would get lucky, sometimes they wouldn’t.
I remember for some reason me and a couple of my friends were messing about in my mum’s bedroom one day, when one of the other boys found a stash of condoms. We all took one to see what they were like and returned the others. We counted them about a week later after one of the mums’ nights out and there was 2 missing. We were about 13 at the time, so we knew enough to know that my mum had been having sex, but she didn’t have a boyfriend and I never met anyone she had met.
One of the mum’s brothers had separated from his girlfriend who he lived with and needed a place to stay. The sister suggested that he move into the spare room in my mum’s house. He was in his mid 20’s and saw himself as a bit of a ladies’ man.
On one of the night of one of the mums’ nights out the babysitter called to say that she wasn’t well and wouldn’t be able to work. There was a change of plans and all the kids (7 of us in total) were to stay at my house and my mum volunteered to stay home and look after us. As you can imagine 7 kids into 1 bedroom doesn’t go. Four of the boys slept in my room, the 2 girls in the living room and I slept in my mums’ double bed. I remember going to be and thinking it was weird to have so much room and that was about it. I however woke up about 3 in the morning. I could hear whispers, it was John the lodger and my mum. I could tell that John was kissing my mum and that my mum was whispering not to do anything in front of me. John however had other ideas and seemed to carry on. After not to long I could tell that there was some movement and some panting noises. The movement and noises stopped and John went back to his room.
I then went back to sleep.
A few weeks later and the mums’ were going out again, everyone was staying at my house again and we had the babysitter. I can remember my mum asking me if she looked nice before she went out. She was wearing black shoes with a small heel, black tights (they could have been stockings) and a knee length black dress with long sleeves and a black silky ribbon at the back. She did look really nice. As usual the mums’ went out and we all went to bed. We had the same sleeping arrangements as last time everyone stayed at my house.
About 4.30 I remember looking at the clock as I heard noises coming up the stairs. I guessed it was just my mum getting in. However she had company. Again I could hear mum and John whispering I could hear them kissing as well. They came into my mums’ room and John asked my mum what I was doing there. She said about the sleeping arrangements. I remember my mum saying that I was a deep sleeper and I could sleep through anything. Again they were on the bed, I could hear them kissing and making other noises I could feel my mums’ leg against my back. I knew that she must have been on her back with her legs open. Again I just laid there however this time my cock was as hard as iron. I remember the two of them carrying on for a while and John left my mums’ room around half 5. The next morning I woke up before my mum and she was asleep on the bed still in her dress. Looking back now I know what they had been getting up to with me just inches away.
A few weeks later John had a new girlfriend and moved out. My mum then met a man at work and we moved into his house about a month after I first met him. This wasn’t long before my 14th birthday.
Once we moved in with my mum’s new bloke life changed again. I moved school and the level of work expected was higher so I had to study more and harder to catch up. The school I had been at previously had been a failing ones in the city. The area that I now lived in was better than the council estate that I had become used to over the last few years, but it was also the red light area of the city.
One Sunday afternoon I was asked if I wanted to go to the pub up the road with my mum and her bloke. I jumped at the chance as I hadn’t been in a pub before. My mum and her bloke used to go up there most Sunday afternoons and sometimes on a Saturday night. I was 14 so I was able to be left, plus the buy across the corridor in the flats used to keep an eye on me. He was an interesting character, who was very clever but also used to go on 2 week cider benders with his friends. They were all harmless and we would sometime play cricket in the car park. He also used to help me with my homework which was a bonus.
Anyway back to the Sunday afternoon in the pub, at first I found it strange being in there. Then I got introduced to some of my mum’s bloke’s friends. They were a lesbian couple who seemed quite friendly, however one of them had more of a man’s voice than I would have expected from a woman. I chose to ignore it and not embarrass myself and them by asking about it. I did however ask once we got home. I knew that a bit about transvestites from when we first moved into the council maisonette and we had a man who lived next to us, but he used to go out dressed as a tarty woman most nights. I had it explained to me that Di used to be a man, but had had operations to make him into a woman. They said that they had expected me to pick up on this and that if I wanted to chat about it Di was quite happy to talk about it to me. At first I didn’t like to ask, but once I got to know Di and her partner more I felt more at ease to ask questions.
One weekend my mum and her partner were doing down south to do a booze cruise so I was to stay with Di and her partner. I had quite a good time, they were gone from the Thursday night through to the Sunday night. At this stage I was nearly 15 and was a lot more aware of things, I also had discovered the art of wanking and wet dreams. On the Saturday night we were watching a film, the postman always knocks twice. I remember seeing the scene where Jack Nicholson has sex with the woman across the kitchen table. That was going to be my going to sleep though. The next morning I woke up in a mess as I had had a wet dream. I was embarrassed by this however I stripped the bed and asked where the clean sheets were. Di told me and then came running after me, but it was too late I had found a foam dildo along with some other sex toys in the airing cupboard. Di was quite calm about it and explained that where she had the surgery to make her a woman that she need to put the foam dildo inside her every couple of days to make sure everything stayed as it should. I still to this day don’t know if that is true.
Skipping ahead to when I was nearly 16. I would like to say that I was like most 16 year old boys, however I wasn’t. I did like girls and I would ask them out in the hope that I might get to do things with them. However I mainly ended up being friends with the girls I fancied. The bulk of my friends were female. I suppose spending time with mainly girls I started to take more notice of what they wore and things that they liked. I really liked looking at girls when they were wearing tights, their legs just looked so good. It was also around this time that I started to babysit for the woman that lived in the flat above us. She had two kids, 1 boy and 1 girl. They were 8 and 6. They were quite easy to look after and they would be in bed for 8 or half past on a Saturday night. That left me with control of the telly and food in the fridge. One night I remember going to the toilet and the lid wasn’t properly on the washing basket. I could see a peach pastel colour pair of Helen’s panties (the woman I babaysat for). I decided to pick them up and sniff them, I bit perverted I know, but I was 16 at the time. I ended up spending extra time in the bathroom after that releasing my urge to wank. After I had cum I felt bad and made sure that I put everything back as it was.
The next week when I babysat once I was sure that the kids were settled I disappeared to the bathroom again to see what was in the washing basket this week. The basket was fuller than the previous week. At the top of the basket was a pair of white foral patterned panties. I began to sniff them as before. I then noticed a white bra with the same pattern on. I remember looking at the label and seeing the size was 34c, and the panties were size 12. There was also a pair of jeans that Helen always looked attractive in and a white top. For whatever reason I decieded that I would strip of and put Helens clothes on. I wanted to feel as sexy as she did while wearing the clothes. The clothes fitted quite well as I was a similar size chest and waist. Once they were on I admired myself in the mirror and pleasured myself to my reflection.
This pattern went on for weeks, I even go brave and would check out what clothes that Helen had in her drawer and wardrobe. If there was nothing suitable in the washing I would just put her clean clothes on.
One day I noticed that my mum had been sorting out her clothes. Once of my jobs was to put the rubbish out. As I was taking the rubbish out I caught one of the bags and it ripped. It was the one that had the clothes that my mum was getting rid of. I got a new bag and stuffed it all into it expect one item. It was the dress that she had been wearing on that night when she had sex with John. I decided that I would keep that and sneak it up to Helens next time I babysat. The next weekend seemed to take forever to come round . I made sure that I saved some homework so I could put the dress in my school bag and take it up to Helens. I knew that I could get to some of her sexy panties and stockings. That night I got myself dressed up and looked at myself in the mirror. Helen’s makeup bag was still in the bathroom so I decided to put some lipstick one. I felt very sexy, I then went on pleasure myself, and I came the most I ever had up to that time.
I knew that I like that feeling and I wanted to repeat it. I know that I wouldn’t be able to steal any of Helen’s clothes to go with the dress so I decided to try and get my own. At the time I got £5 pocket money per week. The flat that we lived in was above a shop and a couple of door away was a chemist. I sometimes used to go in there and pick stuff up for my mum or her bloke. However this time I decided that I would buy myself some tights. I would have stolen some from my mum, but she never seemed to wear them, plus she had put on a bit of weight. So I nervously went up to the counter with a pair of opaque tights and a can of lynx. That was my pocket money gone. I tucked the tights into my waistband and covered them with my t-shirt. I went straight to my room and hid them with the black dress. The next day my mum and her bloke were going to a boot fair so I knew I would have the place to myself. Once I had heard them go I went into their room and went into my mums underwear drawer. I pulled out a bra that was tucked away at the back and a pair of panties from the bottom of the pile. I was hoping that they wouldn’t be missed. While I was in there I also found a vibrator. I decided to take that with me. I went to the bathroom and stripped off out of my clothes. First I put the stolen panties on, then the bra, then the tights and finished off with the dress. I them used some socks from the washing basket to stuff the bra. I put on some of my mums lipstick and eye shadow as well. I stood there looking into the mirror, and I looked good, however my cock was normally really hard by now wasn’t. I decided to rub myself and think sexy thoughts. My mind wandered back to the night that John had fucked my mum while she wore this dress. My cock started to tingle. I got the vibrator and turned it on I ran it over my cock and balls. I liked the way it felt on the bit between my balls and my bum. I then decided that I wanted to know what it would have been like for my mum. I grabbed the baby oil that was in the bathroom cabinet and smeared some on my bum hole. I slowly worked one finger in, then two. I then tried to sit on the vibrator I was really painful and I slowly lowered myself onto it. However once it was it It was such an intense feeling. I then finished myself off. After I cleaned myself up and realised how confused I was. I liked girls, but I also liked being the girl.
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