My friend's father, Mr Webster, had turned out to be anything but the pillar of the community he pretended to be. Despite his regular Sunday church attendance with Mrs Webster, it transpired he also enjoyed the company of other men. He was certainly enjoying me, and within a few weeks I had fallen into the role of his sissy girlfriend and was acting accordingly.

Discretion was obviously important to him so when I was visiting my school friend, Mr Webster would slip me a little note with a place and time to meet and I would confirm with a nod or a wink if it suited. Typically that would be a quiet corner of town and I would keep low in the passenger seat until he had driven well out of town, then he would find a lonely layby or forest carpark and I would change into one of his preferred outfits. His favourite was my schoolgirl outfit, black pleated skirt and white blouse, with the black stockings, suspenders and black Mary Jane heels he had bought for me. I had been experimenting with makeup too and, being a tad effeminate, was quite passable as a girl.

When I was dressed I always felt excited and couldn't wait to take my mature lover's large penis into my mouth. Mr Webster informed me that his wife performed oral sex on him but wouldn't allow him to ejaculate in her mouth. I was only too happy to perform that duty for him and enjoyed fellating him in the drivers seat until his semen filled my throat.

I was happy with this arrangement as it fulfilled my love of crossdressing and desire for cock but after a few meetings Mr Webster informed me that he wanted to try something else...

One evening he drove me to a forest far from town and parked a half mile or so up a secluded lane in the middle of a heavily wooded area. I was feeling deliciously feminine in my schoolgirl skirt and sheer stockings, this time with a pair of black stiletto pumps. He told me to get out of the car and led me by the arm into the trees. He was carrying a pillow and a little plastic box, the purpose of which escaped me. He stood with his back against a tree and put the pillow in front of him, pushing me down by the shoulders so I was forced to kneel. I obediently took his erection between my lips and proceeded to suck him off, bobbing my lips back and forth and performing the twisting action with my hand which Mrs Webster apparently used to bring him to a speedy climax.

After a few minutes of administering the best blowjob I could muster, I was told to stop. Unusual, I thought, but the reason was soon clear to me. Mr Webster found a grassy spot and put the pillow on the ground. I was then instructed to remove my panties and get on all fours with my knees apart on the pillow. My heart quickened and my mouth became dry with the growing realisation of what was about to happen. I looked around to see him get on his knees behind me, working his erect penis to its fully engorged eight inches. He was clearly aroused by the sight of my creamy white buttocks framed by black sheer stockings and suspender straps.

He took a bottle of lubricant from the box and applied a good amount to my exposed bottom and his penis. He then took a small brown glass bottle and put a tissue in a little polythene bag, pouring some of the liquid on the tissue. He told me the liquid was poppers and it would make it easier when he took my virginity.

I knelt submissively as he pressed the head of his cock against my rosebud. He then held the polythene bag over my mouth and nose and ordered me to inhale deeply. I complied and after a few deep breaths my face flushed with heat, my heart was pounding and a feeling of slutty dizziness overwhelmed me. Suddenly he grabbed me by the hips and pushed his massive swollen head into me. I cried out in pain but he told me to push down like I was trying to push him out. My anus immediately opened and his length slid into me in a single movement. I felt his balls slap against my ass and gasped in surprise. I knew now there was no escape for me.

Mr Webster began thrusting into me relentlessly. Each time I tried to move forward he gripped my buttocks and pulled me back, burying his immense erection as far inside me as he possibly could. My eyes were wide and I cried like a stuck pig as he showed his little virgin no mercy or consideration. I was simply a receptacle to be used. After ten minutes of brutal fucking I sensed him quicken and suddenly he groaned as I felt his scalding semen gush deep inside my rectum, at least six creamy spurts. Satisfied, he slowly withdrew and I felt his warm sperm trickle out and down the backs of my legs.

So that was the end of Ginger's virginity and the beginning of my anal adventures. Mr Webster enjoyed his young whore regularly and occasionally shared me with a friend, but that's a story for another time...