One day when I was still at School (6th form), my Mum and Dad said they
we're going to my aunties for a long Weekend. Leaving on Thursday and
returning Sunday and I would be left at home.
Suddenly in a moment of brilliance an idea flashed through my head I
could spend the whole weekend Dressed (I had been cross-dressing as long
as I could remember)
Thursday couldn't come fast enough, I raced home from School in
anticipation. After having Dinner My parents asked if I was sure I would
be ok, I said yeah no problem as I have lots of home work.
After about 10 mins off they went, and I raced to the bathroom. I ran
myself a lovely hot bath with loads of Bubbles I even poured a small
amount of Perfume into the bath for good measure.
I had a long hot soak and then shaved all the hair off my body (I was
never that hairy) except for a little "landing strip" above my thingy. I
covered my body with Perfumed moisturiser and then applied some false
After they had dried I painted both my fingernails and toe nails with the
'Sluttiest' red I could find, put on a pair of red lace panties, and one
of my mum's silk nighties and curled up on the sofa with a cuppa and loads
of Woman's Own magazines. Eventually I fell asl**p, on waking I thought, I
should go to up bed as I still had school tomorrow, and I hadn't taken the
false nails off. I decided to leave the nails on, but go in the spare room
double bed as it was quite a feminine styled room. I fell asl**p in a
Silk nigthtie and matching panties, in a big pink double bed listening to
Celine Dion. On waking I could remember my dream, in it I was Police
Woman, when suddenly I had a terrible thought - I had left my alarm clock
in my room. I raced to my room to check the time and it was 8 o'clock, I
was late. All of a sudden I realised I had woke up without a hard on
(Something that had happened every day since I could remember). As I lay
on the bed thinking about that, I decided to Skive off school and spend
the day as a girl. I then had another brilliant idea why don't I dress up
as a girl from School.
Another hot perfumed bath, and shaving again (even though there was still
no hair) and into my Favourite Panties. A lovely red lace Tanga pair,
when I was trying decide what to do with thingy, my little hairless sack
started to shrink and my little balls gathered back up into my stomach, I
placed a hair band around my thingy and the loose sack and pulled my
thing between my legs - Job done. Since I first masturbated I have
explored my anus with a finger or two (Or three ;)) but I never felt I
was clean enough. Into the Kitchen cupboards I went, and found an old
turkey baster - Perfect, I few washes with soapy water and I was clean
inside as well as out. I decided to lube myself up, as I thought it would
make me feel more feminine, so lots of petroleum Jelly later and I was
set. Whilst I was lubing myself I accidently let out a bit of pee, but it
gave me a damp feeling between my legs. which I liked, so I decided not
to change my panties. I found out some surgical tape and wrapped in
around my body gathering a much flesh as I could to give me a small
amount of breast size (I learnt from Forum magazine). I went into my
parents room and found out a pair of Black Ribbed Tights (Pantyhose), as
I was pulling them on I noticed the time. It was only 8:15 I had misread
the time - Oh well I thought I might as well enjoy myself.
Pulling on Ribbed tights for the first time was one of the most memorable
moments of my life, it just felt so right.
I found a White non-lace bra and pulled it on and clipped it, I felt like
a million dollars. An elasticated skirt Black Skirt came next, it was
little bit long, but a few folds over the top, and it was about the same
size as the girls from School. I pulled on a clean white school shirt,
and I loved the way you could see the outline of the Bra underneath, next
came my school tie, and I was nearly dressed (For What?)
As I was rummaging in my mum's closet, I saw a pair of shoes I had never
seen her wear. Flat Black Soft leather loafers, they were one size
smaller than my own feet but I managed to squeeze into them.
I was about to put on my School Blazer, but when I looked in the mirror I
saw a very effeminate boy (Wearing a girls School uniform) looking back
at me. I suddenly wished I was a real girl, and started to feel a bit
emotional. I decided to go the whole way, I found a small pair of Silver
stud earrings (I hate gold and still do to this day),
When I was younger I had had my left ear pierced so that went in easily
enough, a bit of ice and pop, I had studs in both Ears. I was going to do
my Hair, when I thought - the girls at school wear a little bit of make-
up, into my Mums make-up case I went.
A little bit of Foundation, Mascara and Coloured lip-gloss and I was a
Lots of Hairspray, Backcombing and the hairdryer and I looked just like a
girl from school. I decided to make myself a cuppa, as I went into the
kitchen, I put on my Old school blazer, which was a little smaller, and
sprayed myself with some of my mum's perfume.
As I was making myself a cuppa, I was oblivious to the world around me
(Which was to be my undoing - But more of that later)
Kelli (Was my favourite girls name at school) then had another one of her
bright ideas, she wanted to explore the outside world. I grabbed one of
my mum's hand bags which looked like a little rucksack, and into placed, a
small old purse, a few tampons, a small bottle of perfume, some pens and
pencils and a blank school workbook. I was ready.
As I stood at the backdoor I was shaking with trepidation and excitement,
I unlocked the door and placed a spare key under the mat, and Kelli
stepped out into the big wide world.
I had all intentions of working around the block then going home, when I
realised I was at the bustop, and one of my Mums friends 'Mrs Jones' was
"Hello deary not at school?" She asked, she hadn't realised who I was but
I had to think fast. I pointed to my face and made a slight grunting
noise. "Oh going to the dentist, you poor dear. You need the number
twelve bus here it comes"
I was kind of stuck if I ran off it would have looked very odd, so I tried
to play it cool.
As we boarded the bus Mrs Jones said "Two to the town centre, have you
got the right change dear?"
As I was going into the purse I stared to shake and next thing a tampon
fell onto the floor! "Don't worry honey it has happened to us all, as she
sat down I suddenly and for no reason sat down next to her! I crossed my
legs as girly as I could and stared out the window.
"You look really familiar honey, do I know you parents?" She asked.
I sorta half squeaked half grunt I don't think so.
As I stared out the window, I thought to myself 'You and your bright
ideas' The rest of journey was uneventful and within half an hour, we got
off the Bus at the town centre.
"Hope everything goes ok at the Dentist honey" and Mrs Jones went on her
My initial thoughts were to get straight back on the bus, but it was the
same bus with the same driver - I wanted to feel like a girl so off into
the town centre I went. As I was walking past the shops (Its a Mall) I
noticed my reflection - It was of a Girly School Girl - I felt divine.
I went in all the Ladies clothes shops, if anyone asked me I just pointed
to my face and nobody batted an eyelid. I even went into the Ladies
toilets not a second glance.
I stared to get brave, I had my lunch in McDonalds, went in WH Smith and
bought a Girls magazine, walked around for a bit more and then saw the
time - It was nearly Two The Schools come out at Three, so I would only
just get home before them.
A very uneventful journey home, and then that was when things went wrong.
As I placed my key in the door it wouldn't turn.
Suddenly the door opened and there was Terry (name changed) my parents
"Hello Princess, you had better come in before someone see's you!"
I was shaking as I stepped through the door.
"Your parents asked me to check on you, and I noticed this morning the
Curtains still drawn, so I came to see if you were ok, but saw you
through the Kitchen window.
Shit I had been seen when I making a cuppa.
"Don't worry, I won't tell now what do I call you"
"Kelli" I murmured,
Now I think we should have a cuppa
My hands were shaking as I made us both a Coffee.
I said that I was going to get changed, and he said stay like that I
think you look so natural, and I have always had a soft spot for you.
He brushed his hand across my Neck, which sent tingles down my spine, I
was putty in his hands.
I watched as he lit a cigarette and realised that this 40 year old man
was very attractive, he was suntanned and like to Keep fit.
Shall we go into the Lounge Hun, he said with a glint in his eye.
I walked in front of him and his hand brushed my bottom, it felt sooo
We chatted for about an hour, and he had the ability to make me feel
comfortable, and special.
He asked me about the Petroleum Jelly he had seen lying on the dresser,
and asked me if I was Gay. I started to Cry and he rushed over to hug me.
Here I was dressed as School Girl, Crying in the arms of an older man.
He lightly kissed the side of my face, and I turned and kissed him fully
on the lips. It was one of the most passionate kisses ever.
He asked me if this was what I truly wanted, and something came over me,
I Kissed him again, but this time with tongues and slid a hand down to
Crotch and he had a massive hard on.
He unzipped his jeans, and lowered his Boxers and Jeans to the floor. I
knew what to do next. I dropped to my knees and started to kiss his
Massive Penis. "Put your lips round it Kelli" I dutifully obliged and
began to suck him long and hard. I used one hand to massage his massive
Balls and with the other started to Wank him.
Quicker and Quicker I went until my jaw started to Ache. "I am about to
come" I was going to pull away but a gentle hand on the back of my head
held me in place.
His Penis stared to throb and pulsate on my Tongue, then a Torrent of cum
Sprayed into my mouth, I kept my lips as tightly shut as I could so as
not to make a mess. I started to gag, So Terry went to pull away but I
grabbed him and started to swallow. As the Creamy mixture slid down my
throat it felt so natural, that I started to feel a Wetness In my Panties
I had cum without having a hard-on.
I let his now shrinking Penis slip from my mouth, and curled up on the
settee, with my head in his lap, with Terry stroking my Neck.
I awoke some time later, with the flash of a Camera. I started to Panic
but Terry told me not to worry as the Pictures of his young girlfriend
were for me.
I have a present for you he said and gave me a carrier bag (How romantic)
Inside was a Basque, Matching thong, Stockings and a pair of high heels.
"There my wife's but its not like she wears them, why don't you put them
on?" I said ok and went to go up stairs and he followed me, I was going
to shut the spare room door, but Terry said after what we did earlier it
shouldn't really matter, so stripped down and put on the sexy underwear
for him. "Shall we have a bit of fun, Kelli?"
He threw me onto the bed and jumped on top of me, pinning me down and
gave me a very wet passionate kiss. " I could fall in love with you
sweetheart" he said. I was melting.
He tied my hands behind my back with the Ribbed tights I had worn
earlier, and rolled me onto my back. "Don't worry I won't hurt you!"
Next he stuffed the Red lace panties into my mouth, I could taste
something musty, and could have spat them out had I really wanted. He
pulled the Basque down and started to tweak my nipple, making me squirm
with ecstasy. What came next was a total shock, he grabbed a Coat hanger,
the type for trousers that kinda clamps and clamped it onto my nipples. I
moaned and came right there and then. He pulled down my thong and Scooped
up the cum with the red panties, and got me to lick it off and then
replaced the panties in my mouth. He asked if I wanted to lose my
virginity, to which I just nodded, I was so overcome with the whole
situation. I was rolled on my back and told to spread my legs, then bend
them and grab the high heels.
I felt his fingers at my love hole as he lubed me up good and proper,
first one rough finger, then two, then three I thought I would be ripped
apart, but he was quite gentle allowing me to get accustomed to the
"Are you sure you want this?" he said as he placed his massive dick to my
hole. I couldn't reply because of the gag, so I pushed back slightly. I
thought I would be torn in two as he entered me, and then he stopped.
He stayed as he was until I had got used to the size, then started to
slowly Slide in and out. It was the most amazing feeling ever, I gripped
tighter onto the heels as Terry asked me if I was ready. Ready for what I
thought and he suddenly pushed himself fully into me, he had only been
half the way in. My thing was pulsing into the thong as I was being
fucked by this man, this lovely man had taken my virginity, and was
screwing me hard and deep. I had one of those moments where everything
felt so right, when he lay down on top of me, forcing all the weight onto
my clamped nipples, it was intense, he gripped me around my waist and he
speeded up, and started to fuck me for all he was worth, I was wailing
like the slut I felt like, he let out a loud groan as I felt his seed
spew inside me, as it sprayed inside me, I started to cum, again without
having a hard-on. All too soon it was over, I lay there shuddering wide
open as Terry took a few pictures of his well Fucked girl. He untied the
tights from around my hands and rolled me over. I let out a gasp as he
removed the panties from my mouth. "Sweet Kelli, I love you" he said as
he removed the coat hanger from my nipples, I screamed as the bl**d rushed
back to my nipples. "Aah poor baby" he said as he lightly kissed my
nipples. He scooped the cum from the thong and got me to lick it off,
inserted a tampon into me and I fell asl**p in his arms with the taste of
cum on my tongue and a tampon inside my well fucked hole.
I awoke about 6 O'clock Saturday morning on my own feeling very sore 'Down
there'. As I got up I saw a little love note saying 'Kelli, My Love see
ya soon, signed T'