I was having lunch with Fiona in the library cafeteria one day when Ben joined us. He was looking very smug and mischievous, and he handed me a present wrapped in silver paper. "Go on," he said. "Open it."
I unwrapped it carefully, and laughed. Fiona grabbed it from me for a closer look. "What is it?" she asked.
"It's a butt plug," I explained. Medium-sized, and worryingly large for all that. This was the Monday before that Saturday at his parents' place. I was still an anal virgin, although I had been enjoying Ben's finger in my ass recently while his tongue was busy elsewhere.
Fiona, in contrast, had no interest in anything anal. She handed the butt plug back quickly. "That goes in your..." She trailed off, unwilling even to say it.
"My ass. Yes." I turned to Ben. "Now?"
"No time like the present," he said, grinning.
I took my present, and the tube of lube he handed to me, into the toilets. In the privacy of a cubicle, I slicked the plug with lube, and spent a minute fingering my ass, readying it. I placed the plug on the seat and slowly lowered myself onto it. The pointed end slipped easily into my tight ring, but I soon felt resistance as the plug widened, stretching me deliciously. For a moment I feared it wouldn't go in, that it was simply too big for me. The feeling of being stretched so wide was exquisite, intoxicating. And then suddenly it pushed through, slotting into place.
For a minute I just sat there, loving the strange feeling of my ass being full, then stood, adjusted my skirt, and left the cubicle. I looked at myself in the mirror. Smartly dressed, nothing to suggest a woman with a butt plug and no knickers, except my face looked a little flushed, and the points of my nipples pushed visibly against the fabric of my shirt.
I rejoined the others, conscious with every step of that unfamiliar pressure. I felt another pressure also, a very familiar wetness. But I pretended innocence, as if nothing special had happened, and munched away at my sandwich while Ben and Fiona studied me.
"Did you do it?" Fiona whispered, blushing.
"Would you like one?" I replied.
"No!" she hissed.
Ben chuckled to himself, saying nothing, but I enjoyed the fresh hunger in his eyes as he watched me. After lunch he followed me through the library to an aisle in a quiet corner (education in schools, I think). He pushed me back against the books and kissed me while his fingers bunched my skirt up and searched underneath, finding the hard base of the plug.
The bulge in his pants pressed hard against my crotch. "I'm sorry, Sir," I said cruelly, "but you'll just have to wait till tonight." I fixed my skirt and walked off, waving goodbye.
I quickly grew accustomed to the plug. More than anything, the knowledge that only Ben and Fiona knew I wore it, that everyone else was oblivious, was what excited me the most. Going knickerless was a delicious tease, but the plug was a dirty secret. I imagined being hit by a car, and doctors discovering first my lack of underwear - shock! - and then the butt plug - horror!
Getting home that night, Ben was waiting, prepared. He didn't let me undress at all, just dragged me to the bed, lifted my skirt and pushed into me. I loved his urgent hunger, his need for me. I loved the feel of his thick cock filling me while the plug was buried in my ass. My orgasm, when I came, felt twice as intense as usual, and seemed to last twice as long, as my ass clenched about that intruder.
I wore that plug every day that week, finding it easier each time I pressed it into place, and so I wasn't wholly unprepared when Mr Appreciative's slender length went where no man had gone before. To be honest, though, I was a little overwhelmed by everything that was going on at the time and can't say I enjoyed my first anal experience beyond the knowledge that it was happening; at least it wasn't painful.