I had been enjoying regular meetings with my friend's father, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and always stockings or tights. I noticed how hard his erection would become at the sight of my pert bottom above sheer stocking tops and I made a point of allowing my skirt to ride up so he would catch a glimpse of my creamy white skin above my nylons as we drove along.

A few months into our relationship he broached the subject of his friends and asked if I would consider meeting up in a group setting. It turned out that Mr Webster was one of a number of local men who met up regularly, this being back in the 80s before the internet really existed. The gutter press today would probably refer to it as a "sex ring". I was initially reluctant but he reassured me that their meetings were exceedingly discreet and he also implied some financial reward for my participation. He was sure that I would be the centre of attention, which rather appealed to me so I agreed to go along.

A date was set for the following Friday evening since Mrs Webster was taking my schoolfriend to his university halls of residence and wouldn't be at home. I had a week to anticipate what awaited me and to decide what to wear for the occasion. Mr Webster asked me to go for something a little tarty, which seemed appropriate, so I decided on a little black lace mini dress which only came half way down my thighs. Under this I was going to wear a black basque, matching see through panties and sheer black 10 denier stockings. Black patent stiletto heels would complete the outfit.

Friday night came around and I knocked at Mr Webster's door. It was already dark but he ushered me in quickly. There were no houses opposite but there were neighbours either side of his large terraced house. I had plenty of time to get ready and took my time slipping into my lingerie and heels, making sure my garter straps were perfectly straight and neatly attached to the welts of my nylons. I slipped my black sheer panties over my suspender straps, sure that they wouldn't be staying on for long. They hugged my bottom beautifully.

I applied my makeup with equal care, getting my eyeliner just perfect with the green sparkle eyeshadow I'd bought specially. Heavy mascara accentuated my long eyelashes and blusher defined my cheekbones. I added my favourite scarlet lipstick and plenty of gloss to plump up my lips. Hair would be a short red bobbed look which I love to this day. Slipping on my 5 inch spike heels I took a step back to admire the girl looking back at me from Mrs Webster's full length mirror. Pretty slutty I thought but certainly the right look for the occasion.

"Well that's suitably tarty looking, Ginger," said Mr Webster as he walked in to check my progress, "The men are really going to enjoy their evening!"

I gave him a flirty twirl and he handed me a tall glass of vodka. Thoughtfully he'd popped a straw in it, with the twin purpose of not spoiling my lipstick and avoiding incriminating red marks on a glass...clever. After a couple of these my nerves were a little better and I was taken to his car which was parked in a covered bay at the back of the house. I tiptoed to avoid the distinctive sound of stiletto heels and got low in the passenger seat until we were clear of his street.

Minutes later we arrived at a local public house in the town centre which was shut for the evening. There was a small car park at the back and I was led in the back door of the lounge bar. The place was dimly lit but typical of those kinds of establishments, a small bar area, pool table and a little dance floor. The one unusual thing was what appeared to be a school gymnasium vaulting horse placed in the middle of the floor. It had been modified with the addition of four padded boards bolted to the sides, two at the front and two slightly lower ones at the back. The purpose of this was immediately obvious to me. As my eyes adjusted to the dim lighting I counted eight men in the room, sitting around drinking and in various states of undress. They eyed me up and down lasciviously.

I recognised one of them as the owner of the place, a heavily built man over six feet, the rest I didn't know.

"You've outdone yourself, Webster," he said, "She looks like a right little tramp, send her over here so I can get my money's worth."

I went over and he instructed me to take a cushion and get on my knees in front of him. My eyes widened as he undid his trousers, in awe of the cock that sprang out, eight solid inches even at half lob, the knob glistening with precum. Licking my lips, I tickled his pee slit with my tongue before taking his glans into my mouth. I then proceeded to bob my head up and down as best I could before resorting to masturbating his ever growing penis into my mouth since he was so enormously hung. He had one of the biggest, hardest dicks I have ever seen, all veiny and leaking clear liquid into my mouth as I struggled to stretch my lips around its girth. After a few minutes he withdrew...

"Don't make me come yet honey, I'm going to fuck you in the ass with this later..." His tone was threatening, but I felt a knot of excitement in the pit of my stomach at the prospect.

By this time a couple of the men had completely undressed and led me by the arms to the vaulting apparatus. I was ordered to get onto it and assume a position on all fours with my knees and elbows on the pads at the sides. My panties were quickly removed and I was acutely aware that my rear opening was at just the right height and angle for a man standing behind to penetrate me. The two men secured my waist, wrists and ankles with buckled leather straps, immobilising me completely. Seconds later I felt my anus being moistened then some kind of syringe was inserted into me, followed immediately by a large quantity of lubricant injected deep inside my rectum. Mr Webster came over, poured an entire bottle of poppers into a polythene bag and held it tightly over my mouth and nose. I had no choice but to inhale the fumes. This was a routine he often used on me just before penetration.

Within seconds my head was spinning and I could hear my pulse pounding in my temples. As my skin flushed with heat from the effects of the amyl, one of the men suddenly pulled my head back, shoved his erection down my throat and proceeded to fuck my mouth. I started to choke but managed to suppress my gag reflex as he used my open mouth the same way he presumably used his wife's cunt. The other man got behind me. Stuffing his hands down my stocking tops, he pushed his erect penis into my helpless bottom. I tried to squeal but the cock filling my throat prevented anything more than a muffled groan. I could see camera flashes going off as the two men began to spitroast me, sodomising my mouth and ass with no mercy whatsoever. This continued for several minutes until the man behind me gave a final thrust and, gripping my hips, shot his entire load deep inside me. This triggered the guy in my mouth who ejaculated a series of thick creamy spurts straight into my stomach before withdrawing. His semen dribbled obscenely from my ravaged lips and pooled on the floor beneath.

The savage fucking I had just endured must have aroused the other men and they proceeded to take turns screwing my mouth and ass bareback. On more than one occasion a cock was pulled out of my rectum and, still dripping with lube, stuffed straight into my mouth. Mr Webster was clearly in charge of pain relief and he used a plastic kitchen funnel and tubing to pour neat vodka straight into my mouth, making sure I swallowed before administering more poppers to keep me submissive and loosened up. After nearly an hour of brutal fucking, every man in the room had emptied his balls either up my ass or down my throat, all except the bar owner who had been watching the entire proceedings and masturbating his fat swollen cock.

When his turn came he stood behind my exposed buttocks, pulled back his foreskin, and pressed his enormous mushroom head against my well used hole. Fully erect his penis had to be at least nine inches long and thick as a cucumber. With a powerful thrust he was inside me, knob to balls in one vicious movement. I cried out in pain but my protests were soon stifled by a red ballgag, which was quickly inserted in my mouth to shut me up, and buckled at the back of my head. I bucked involuntarily against the bench's restraining straps but there was to be no escape from this girl's ordeal.

Someone put the bag of poppers over my head and, ignoring my attempts at struggling, secured it with a ligature around my neck. My head was swimming within seconds of breathing in the amyl nitrite fumes, as my body fought helplessly against the relentless penetration from behind. I could feel the bar owner's heavy balls slapping against me every time his cock bottomed out. My guts felt like they were going to burst as he impaled me repeatedly, though mercifully he didn't last too long. I was on the verge of passing out from lack of air and inhaling so much amyl when the tempo of his thrusts suddenly quickened.

"I'm shooting a fucking baby into you, you dirty little bitch," he taunted, as his hot cum filled my ruined ass whilst the others observed. His thick veiny meat twitched and pulsed inside me as he gushed rope after rope of scalding cum deep inside my boy cunt. Satisfied, he withdrew his penis from my gaping hole, and as he removed the ballgag and released my restraints I could feel his sperm trickle from my bottom.

Following the evening's festivities I was driven home, my hole thoroughly stretched and with semen oozing into my sheer panties. This was to be the start of a new phase in my transition from boy to sissy. I now had access to all the cock a girl could ever want, but my next adventure is a story for another time...