Holly by Cathykay
I had known Holly for years - since I was 12 or 13, and we were at school together.
She had always been very sexy even then, when most boys of my age were a bit uncertain about girls and in my case especially.
I dreamt about her, but not like most of my contemporaries. I dreamt about being her.
She was the perfect girl, tall, slim, blonde, sexy, dirty evenShe boasted of course that she was not a virgin, and I loved o believe her, I loved to imagine what it had been like for her to feel a hard cock inside her, stretching and hurting her, hurting me, deep inside me, filling me with the hot white spunk I had already seen and tasted of my own.
As we became friends I would stay over at her house a lot - she lived in a large house, and had lots of sisters.
Like most families they kept a wash basket in the bathroom, and whenever I visited I would investigate it, and get the most of the piles of damp musty beautiful underwear I found there, occasionally, in fact always helping myself to something. As I got older I progressed to larger silkier sexier items, and there was nothing that I loved more than waving goodbye, to get on the bus, to catch the train, wearing a teddy or bra or tights underneath, knowing it was my secret, hoping to get caught, perhaps by accident, perhaps not. I remember once in a train station, on the way back from her birthday, boldly unzipping my trousers at the urinals, and praying that the man there would see my stiff dripping cock poking out of soft silk pink knickers, and as I nudged by trousers down further, to the tops of my stockings, I felt an incredible power as he whispered something to me
I missed my train, and tasted hot piss as he fucked my mouth while out of the window the everyday continued.
Holly continued to delight me as a role model - if only she knew I would wish, and as a source of surprises. In my later teens I slept in her bedroom, and she slept in the next room with her latest thug of a boyfriend. As I heard them begin to fuck - Holly fucked rather than made love, I let myself investigate her draws and cupboards. The tight black corset top, the soft silky G-String and Suspenders were exciting enough, but I also found something else she had boasted of, not knowing exactly how she teased me - her vibrator.
Before I had had to improvise, too embarrassed to buy one for myself, but the opportunity was too much to consider being caught now, so I lay back, took a deep breath, and plunged it rather clumsily in my ass. The pain was terrific, as it was much larger than the fingers and thumbs, and tampons, and pens and candles and other little experiments I had been used to, but I came almost at once, really soaking my belly with cum that stung as it left me, and after this shock I took the time to begin to actually fuck myself, rather than just tease my little puckered ass.
As next door I heard a rhythm of Holly getting a huge cock right where I wanted it, I kept up pace with her, and ended up falling asleep, drained and hurt and sore, with her dildo still buzzing away inside me.
When I woke in the morning I felt at first confused, and then of course frantic. I stripped, gently pulled the monster from my still sore little hole, wiped it clean, and tried to put everything back.
Holly never said anything, but she must have wondered why the batteries were flat in her little toyA few months after that I went off to university, as did Holly, and we lost touch.
Maybe 5 years later I was clubbing, or rather Cathy was clubbing. I had my favourite little black dress on, rubber knickers, bustier and stockings, and by midnight I was falling down drunk, offering to suck any cock that was put in front of my face.
I was bursting for the ladies room, so my belly sloshing with cum, and the acrid taste of it filling my mouth and nostrils I lurched into the ladies, and promptly locked myself in the cubicle, to undo all my bits and let my cock, as stiff as polished wood, spring out.
I was going to have to have a little wank, just to keep my self sane, so I spat onto the palm of my hand a mixture of saliva and ten men's spunk, and began to work it onto the length of my shaft, just teasing the head of my cock with my finger nails.
As I was beginning to cum I heard two people come in, a conversation, and then the frantic unbuckling and unzipping that always means quick frenetic sex. I tried to peek out of the door, and although I could not see much, it was clear that some huge guy was having a girl perched up on the basins, so I quietly undid the door, and with my cock still ready to explode in my other hand tried to see more.
The rink, the excitement, the nerves and perhaps the hot cum by now in my bloodstream, all made me dizzier than I expected and I crashed out of the cubicle in a most unladylike way, interrupting the events.
Of course, it was Holly.
She recognised me, but did not know what to say.
'Er. Hello' I croaked.
By the end of the evening, both of us drunk, we had caught up with each other, and Holly was particularly pleased I thought, that I wanted to be a girl like her. She suggested that I come home with her that night, but I could not, and I do not think her boyfriend was especially impressed, so we swapped numbers, and agreed to meet up to go shopping. I returned to the dance floor, and ended up waking up with a squaddie, who never knew any better.
I rung her the following week, and was invited to her old house for the weekend, as her parents were away.
'Wear something sexy for me' she said
I will bring all my favourite things'
'No, wear something - I want to see Cathy walking through my door'
I did not know quite what to do - in a darkened club, in a taxi, or stealing away in the small hours I was passable, but early on a Friday evening, through Kings Cross Station? I could perhaps change on the train, but that might attract even more attention if it was busy. I went through every outfit, every dress, skirt, top I had, but they were all intended to catch the eye. I would receive a lot of attention, and did not really want it.
In the end, I decided that I could not possibly walk out of my house in broad daylight as Cathy. It was exciting when I thought about it, and loved the idea of being caught by the right person, but Mrs Yates downstairs would have a heart attack - she though that I was such a nice young man!
I went to Kings Cross, took a ticket for the latest train I could, First Class, and took my gamble - I slipped into the Gents to change. In the space provided it was not easy, but I had had my underwear on all day, so all it needed was a nice tight bra to draw just enough of my little tits together, a sweater and tight jeans. It was a bit of a cheat, but with enough make up, which I could touch up and tart up later, I would look fairly unremarkable - I hoped.
The only danger was in leaving the loos, but it was quiet, I dashed out, up the stairs and onto the concourse, I thought unnoticed.
I took my seat on the train, and stared out of the window, wondering what the weekend would be like. I knew that I was going to tell Holly everything about me, about how I used to wear her clothes, about how the dirty filthy tart in me was determined to be like her.
Half in a dream I did not really notice when the Gent opposite me whispered something.
'Sorry?' I had not heard him'
I said that you are a very sexy looking woman, and I would love to suck your cock'
'Pardon'
'Don't deny it please - I can see your cock, through your trousers, and I would love to suck you off'
We had 30 minutes to go, so I followed him into the toilets on the train, and despite the rattling train, I stood up while he eagerly unzipped me, and started to sniff at my red silky knickers. Already there was a dark stain spreading across them, and I could soon feel him nibble away at the top of my lace-covered cock. Before long I was beginning to pump cum into my knickers, and could feel it soak and spread and leak out, down the inside of my thighs - he eagerly moved his attention there, and I felt his tongue approach my groin, slurping and sucking all the way - his hands reached for my cock, and just as I watched it slide into his mouth I saw again my cum shoot out, and dribble down his face.
He carried on for so long that I nearly missed my stop and I certainly had no time to clean up, so I was felling very very sticky and dirty when I got out at the station.
It was dark by now, and my fear of being embarrassed was replaced by a fear of getting lost or even attacked.
I had not been for a long time, and even though I knew how to get to the house, in the dark, after such a long time, feeling so exposed, the walk seemed to last forever, and I stopped many times, thinking I could hear a voice, or footsteps, that would be followed by quicker steps, running, perhaps a knife, and I had images of being dragged off, perhaps bundled into a car, attacked, discovered, and then who knows what. I have had rape fantasies for as long as I can remember, but it was too frightening here - too out of my control, too real.
When Holly answered the door, I realised how much I wanted to make love with her. She was half dressed, all alone in that big house, purring like a kitten, and I wanted to touch her and taste her, and watch her face as she came, and be her little slutty lover.
She seemed to approve of the way I was dressed, and there was no awkwardness at all. She had thousands of questions, and seemed fascinated with me as I was now.
'Are you gay?'
'No - it's more complicated than that - I do not want to be a gay man, or .. Well, I want to be a gorgeous pouting sexy little girl, like you were, like you still are, and I want men and women to love me - men have to really want me as a dirty little girl - they have to be a bit rough with me.'
I told her later about the mixture of fear and excitement I had felt on the way from the station, and I told her about the man on the train, and she just wanted to hear more. I was sure she was getting turned on, and I tried to think of a way I could tell her that I wanted her, but I could not get the words out.
After hours of drinking wine, and talking, and watching her beautiful face drop every time I told her another story that told her about another part of me, we went to bed, I with my make up still on, a little frustrated, but happy at least to have told her everything. She had not reacted at all when I had told her about all of the clothes of hers or her sisters, or even her mom, that I had worn, and a few that I had 'borrowed'. In fact she loved the story about a particular pair of white fluted knickers that I ended up having to wear for a week in Spain, three days in France, and by the time I lost them in Dover were Black. Maybe because I was drunk, or maybe because it was about time, I told her about the night I spent in the room next to her and her boyfriend, exactly what I did, and at her insistence what it was like. I was sure that she was getting very turned on by it all, but never dared to ask her.
Saturday morning came, we woke late, and I came to breakfast in a tee shirt and shorts, only to be told that I should really be Cathy all weekend, so I changed into a light silky dressing gown Holly lent me. It was a little difficult to keep myself covered up - I did not make the best choice of knickers, but I changed again before we went out, and kept myself firmly undercover in a miniskirt that showed just the tops of my stockings, and a very tight top over my most padded bra.
We went into the local town, and bolder and braver than the night before I let Holly take me around the shops, being girly and giggling and trying on make up, and even flirting a little.
We went home in the late afternoon, Holly driving her open toped car, and both of us enjoying some very meaningful looks from the tanned men around us.
We had a light dinner, and went into the garden, to chat and drink. I kissed her, and hoped that she would understand.
Holly started to tell me about her university years, and talked of boyfriends, and of a couple of girlfriends too - she could see that I was getting excited, and went into more detail than girls might usually share. She told me about sitting in front of the fire, with her friend, and having an irresistible urge for a wank. Holly actually used that word - she always had talked dirty and it was one of the things I loved about her. She told me how she loved to play with herself, to watch her finger slide down to her clit, to watch her thumb slip in and out of her pussy, and feel the glow and buck of orgasm as it came.
As she excused herself, her friend had said 'Do it here - I know where you are going, I know what you are doing - I want to watch.'
As Holly told me this, she began to lift her own long skirt, and rub her legs together, and her hand started to climb to her crotch.
I did not move - I listened as she told me the story, and watched in the half darkness as she pleasured herself through her thick silky knickers, and felt as if it were me, my sex that was being treated to this mixture of delicacy and abuse.
After she came, her story ended, and she slid off her chair, stood up, and walked into the house. I followed into the living room, where she lay on the settee.
I closed in on her, and moved my face towards her now exposed crotch. It smelt strongly of sex, her sex a smell I remembered from years before, and I could not resist the chance now to taste it.
With nothing in my mind apart from the sight sound and smell of her at last I approached, quickly moving from the tops of her thighs to the perfect pink opening which she offered to me. I caught her flowing juices eagerly, and lapped them up.
"Fuck me little girl" she whispered - with no more mention of my dress, I lifted up my own skirt and let my cock which was itself already hard glistening and an angry red colour spring from the confines where it had been caught between the gusset of my knickers and my suspender belt - I scrabbled at my panties and let them rest at my ankles as I mounted her and slipped in my girlcock as I though of it - as I pushed effortlessly into her, seemingly forever I closed my eyes and imagined how we would look to the world - two young girls grinding our pussies together as if we were stuck with glue - I desperately wanted to watch this and be watched as we fucked hard like two filthy little tarts. No matter what my experiences with men, and god knows how much I loved cock, there was nothing as feminine as sex like this.
We made love very very slowly, as I tried my best to keep in control, making slow movements as our juices mingled inside her only to pour out every time I withdrew my cock so I could see the tip at her pussy lips and dribble past her and my thighs, sticking to me and staining the tops of my stockings with our dark musky mixed sex.
As I started to lose control, and feel myself coming Holly started to wrap her legs behind me, holding me still deep inside her, a little longer each stroke as if to control me - then as I thought we would stay trapped in this still brink never quite touching ecstasy that we could both see and taste in our dry mouths, I felt hands pushing down on my back.
I tried to turn, and caught a glimpse of a dark balaclava and a mans torso, his trousers half undone, and a cock as big as my arm descending upon us both. Without a word I felt this monster of hot iron like flesh pushing at my arsehole, and quickly gouging into me, feeling as though it would turn me inside out.
"Tight little bitch aren't you" who was he talking to? Me or Holly - what was going on - how had this happened - I was being
"Rape - its not rape little girls - this is fun - you would not dress like a slut if you weren't one - or are you just playing pretend? It's too late for that, but you need a little lube I guess - try this"
As I felt him pull the hot intruder from my burning sore torn arse he rubbed something cold onto me and into my hole - I smelt butter and recognised its feel as it melted into me and on me - then once again I felt him punch into my tight little arse with his enormous cock - going deeper now, right until I felt, after what seemed like a 100 mile journey of pain into my behind. His balls banging against my now wet greasy behind
"that's good blood and butter - makes it easier for me and for you - now lets see if you cant manage space for a little spunk too"
Unlike Holly and I this was fast rough sex, all the time Holly underneath me holding my cock inside her, watching the face behind my shoulders, smiling, occasionally closing her eyes as his cock thundered through me to her - she began to tighten further as he pounded faster and faster into my behind, my pain getting worse as her pleasure increased - as he raped me he made love to her, and she used me as a barrier, squeezing me tight while he loosened me from behind and abused and hurt my little ass more and more and more.
It seemed to go on forever, all the time Holly coming and letting out sighs then cries then screams - I tried to scream to, but with pain as I felt myself getting bruised and broken inside and out, feeling hot butter and blood and shit burst from me in fits and starts as his cock pounded me to jelly, but he quickly put a hand around my mouth, and putting more of his weight onto me to compensate effectively paralysed me as a huge tool to fuck Holly with.
Eventually he began to slow and go deeper into me, and I yielded, relaxing, ready to pass out just as he let out a roar, and almost launched me off the sofa with a thrust that felt as though he had climbed right inside me, and at once I felt gallons of his hot thick spunk at once fill me and begin to escape from me - I could feel every drop and drip as it worked a course past my asshole, down my bottom cheeks, over the tops of my thighs and being caught by my stockings.
My attacker lay still for sometime, until he leant pass me to kiss Holly deeply and I tried to struggle away - I was too weak though and he grabbed at my hair and stopped me with ease.
He pushed his knee into my back, and held me down, with my arms behind my back
"Such a pretty little girl, I don't think. Look at you, covered in spunk and blood and butter and dirt - if I could I would shit on you, you tart - playing with yourself, listening to us fucking, jacking off into Holly's panties - do you think we didn't know? We all knew what a freak you are - well this is what you want isn't it?"
Without warning he lifted me by the middle and I felt him shove something else in my sore but now wide open arse - I felt the hum as he turned it on, and shoved it to the hilt into me, my ring just beginning to close around it as it disappeared into me
"Bitch - well you are my fuck toy now - "
He dragged me, bent double through the French Windows, while holly watched - and threw me onto the lawn like a prize for her
"Do it" she squealed with delight
"Suck this slut" he offered his cock and even in the dark I could see it glisten with what I knew was my shit and blood, his spunk, and I could smell the rancid fatty butter that I could still feel churning inside my ass
With no choice I started to open my mouth, and fell backwards away as he thrust it at me.
"Take it all in and clean it nicely" he said leaning over me to give me no real choice in the matter.
After I had cleaned his cock, and then retched as he began to piss in my mouth, Holly cried "That's enough" and ran to my side.
He seethed as she took me off, and bathed me and explained that she was sorry, but he had been angry for all these years, and she had a kind of rape fantasy and well she was glad it had not got out of hand.
As I slept I had all sorts of ideas and images rushing through my mind - I realised how sexy the whole thing had been - raped and fucking and being hurt and being a tart and being a girl and I woke with a start - it was still dark, I was sore, and I had a little blood still to mop up - my ass was still sore but as I thought of what it had taken earlier I tingled and shivered - I washed myself, taking my time with my tender little ass, dressed in one of Holly's nighties - see through and ostrich feathers! And slipped into their room, into their bed without waking them. I Could hear him mumble as I took his big dick in my hands, and started to nibble Holly's Nipples..
Cathykay is a shameless tv hussy who likes to dress up as a schoolgirl and get gangbanged .... sigh, but most of the time I just read and write about it - tell me what you think at cathykay69@hotmail.com and write me, and tell me what you would do with a stretched sissy slut like me