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How it all started

 
 

By *owie144 OP   TV/TS
over a year ago

halesowen

think I was about 8 or 9; I lived with my family at Chaddersley

Road Kings Norton Birmingham. My mother had just given

birth to my younger brother, on Sundays to help get me out

of the flat and from under my mothers feet I was packed off

to the local Sunday school. This was just down the road from

us at the local church hall. I did not mind going there, as

there was this very pretty girl called Emma (she was 10 years

old) I was infatuated with her. One Sunday I was playing

with Emma when she said, “ I am going to the toilet” as usual

I followed her like a little lap dog. I was waiting outside

the toilet when one of the teachers Mr Cant passed by he asked,

“what are you doing outside the girls toilet.” “ I am waiting

for my friend Emma” I replied. “ This is not the first time

I have seen you waiting here! Is it?” Not thinking I said

“so what”. “I will show you so what, if you like waiting here

I will make you use these toilets all the time with the girl’s.”

Emma came out and we went off playing.

The next Sunday I went to the school as normal, Emma was not

there (it transpired that she had to go to a family birthday

party). Mr Cant came down the hall, he told me to follow him

I followed. He took me to a side room and produced a ribbon

from his pocket, “I will teach you to loiter around girl’s

toilets” he said tying the ribbon into my hair. “ Now go outside

and play with the girl’s and if you want the toilet you must

use the girl’s.” I has horrified, this man made me follow

him to the hall and took great pleasure in my humiliation.

I was made to sit down, all the boys made fun of me I cried!

At the end of the school he said if I told my parents he would

tell them I was naughty and deserved it. I was to frightened

and upset to tell anyone!

To upset and frightened I never went to the school the next

2 weeks. The next Sunday the door of the flat was knocked,

Emma’s mother was there, and my mother asked her in. She

explained who she was and asked my mother if I could go to

her house to play with Emma (as she was feeling unwell).

My mother agreed, “off you go and be good” “ yes I will mother”

I replied. Emma’s mother took me to her house, Emma was waiting

for me, and she was wearing the prettiest dress “made out

of satin and lace that I had ever seen.) She told me that her

mother had found out what the teacher had done to me and was

not pleased. She said “mother has said that you can come

here every Sunday so we can play” I was very happy, this made

sure that I would not have to see that Mr Cant again.

Over the next few months Emma and I had great times, we played

indoors and out, she always dressed in the finest clothes,

sometimes she would let me try on some of the things. Emma’s

mother June invited me to go to a party with them. I was happy

I had never been to a proper party before. June took me home

and asked my mother if I could go with them. “Yes of course

he can go, ” she said to June, she replied “as the party is

on a Saturday night will it be alright if Dennis stays the

weekend with us and I will collect him on Friday and return

with him on Sunday evening” “Of course it will be OK!” I could

not wait for the next weekend to arrive. On Friday night

Emma arrived with June to collect me, “all set to go” June

asked “yes” I replied, rushing out of the door. My mother

had put all of my clothes in a bag for me to take with me, but

in my haste to rushing about I forgot to pick it up. On arriving

at Emma’s house I said to June “I have forgot my bag with all

of my clothes in” “do not worry Dennis I will collect it later.”

She forgot. “Dennis I have forgot to collect your bag” June

said. “Never mind you can put on some of Emma’s pyjamas, ”

she produced 2 pairs one for Emma and one for me they were

plain floral ones with a touch of lace around the arms and

legs, we put them on and went off to bed.

The next day June put out some of Emma’s things for me to put

on till she went for my clothes, not thinking or saying anything,

I dressed and went out to play with Emma in the garden, June

watched as we played, Emma and I came inside and went of to

her room to play we had a good time with her dolls and things,

that I never give a thought that I was wearing her clothes.

June collected my bag and later that evening we went off

to the party, Emma was wearing her best dress she looked

good, we had a good time there, music, dancing and plenty

of pop and food, being a normal boy I’m afraid I overdone

it slightly and felt quite sick! I told June that I felt unwell;

she said that we would be leaving soon. Back at Emma’s house

it was time for bed, we went upstairs undressed and got ready

for bed. I do not know if it was fate but instead of putting

on my pyjamas I dressed in the ones I had on the night before.

June came up and tucked us in she said, “Dennis you have put

on Emma’s pyjamas? Never mind you like those don’t you”

“yes” I replied.

The next morning being Sunday, June explained that they

were off to church, did I want to go with them, “yes please.”

June took Emma off to get dressed, she had on her best dress

I looked at it with envy, Emma noticed I was staring “Dennis

mother said if you like, when we get back you can try on my

dress.” Not thinking I said, “I would love to try it on.”

June came down the stairs and asked Emma “did you ask Dennis”

“yes mother he would like to” “O you sweet thing Dennis,

I am sure you will look very nice, Emma has told me that you

like wearing her clothes. ” I was in a daze all through church

I could not stop thinking about putting on the dress, it

was ages before the church had finished, and we went back

to Emma’s house, on arrival I rushed out of the car to the

door. “You cannot wait to get inside can you Dennis” June

said, “Do not be inpatient we have all the afternoon before

you have to go home” inside Emma went off to her room June

and I followed, June had laid out some of Emma’s underwear

a plain white vest with frills around the arms, white cotton

knickers with a little pink bow in the middle (I had seen

Emma wearing these before) and white tights. Emma took

off her dress and laid it down besides the underwear. “Dennis

we will go out of the room now so you can get dressed, I have

put on all the things you will need to wear, do put them all

on no one will see you but us, ” with this they both left the

room. I undressed and started to put on the clothes, first

the knickers then the vest and socks finally the dress,

I looked in the mirror I was very happy. I went down the stairs

to be greeted by Emma and June “Dennis you do look nice in

my dress, mother you were right, he looks right as a girl

it does suit him.” June came over and produced a brush and

brushed my hair into a different style, “ he looks even better

now” she replied. Emma and I continued playing for the rest

of the afternoon, with me dressed in her clothes. Over the

next 3 years we dressed and played all the time with the clothes

getting older and sexier. Our cotton knickers were replaced

with nylon ones and a bra was introduced as Emma’s breasts

had begun to form. June took pleasure in buying nice underwear

for both Emma and myself; I think it was these garments,

which changed our situation. One day while out shopping

for things she had brought the most gorgeous pair of yellow

nylon French knickers and matching bra for her, I looked

on in astonishment at these, they were beautiful, June

had seen the look on my face! Back at their house I could not

look as she opened the bag and took out her new underwear,

June sent Emma out for some milk from the shop 10 minutes

down the road, I stopped in, she then went off to her room

to try them on, I was alone in the house with June (not for

the first time) I went up stairs to go to the bathroom, as

I passed her bedroom the door was open wide I could not stop

myself looking in. June had her back to me and was looking

at herself in the full-length mirror of here wardrobe,

she was stunning in the yellow bra and French knickers,

“don’t stand there looking at me Dennis, ” she said “come

in come in quickly and close the door” I did not think that

she could see me, but she could through the mirror. I entered

her room, she turned around facing me, I could not take my

eyes from her body, I stared at her breasts and at her knickers,

she walked over to me, took my hand and put it on her breasts,

they felt hard to touch, (her nipples were erect as I now

know, ) She put her hand on the front of my trousers and to

my astonishment my cock went hard, (this wilily was only

to wee out off I thought) she took of my trousers and put my

hand on the front of her knickers pushing my fingers around

her fanny, she put a pair of knickers on me and rubbed her

hand over them, still working my fingers around her with

her other hand, I came inside the knickers (My first orgasm)

she finished herself off. After this things were never

the same I did not want to play with Emma, but wanted to play

with her mother June, we had some good times, June taught

me how to make love and to please her, but she would always

let me wear the knickers that she had worn for sex.

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