Bare-Faced Cheek

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.

The following week - on Wednesday, I think - Ben cornered me in medieval folklore just before lunch. We kissed hello, and I pressed my hand against his crotch, feeling the hard urgency contained within his jeans. "Later," I laughed, and bent down to replace my books on the bottom shelf - well aware that my own bottom shelf was thus presented teasingly to Ben. I hoped he would take advantage and slip his hand beneath my skirt, knew that his fingers would touch the plug and move between my thighs to discover how wet I was becoming.

But it wasn't his fingers that pressed between my thighs. His hand on my back forced me to stay bent over, and his stiff cock, wrapped in protective latex, nudged at my entrance, pushed between my lips, thrust impatiently into my pussy, stretching me deliciously, a little painfully. He fucked me slowly at first, but quickly built up speed, until the unmistakeable sound of cock pounding pussy would have made any nearby librarians rush to shush us. ("Excuse me, sir, but would you mind fucking her a little more gently? People are trying to study.")

No librarians interrupted us. Two student girls passed the aisle at one point, stopped in amazement and watched us for a few seconds before wandering off in a gale of laughter. I was too close to my climax at the time to care, and it seemed the sight of the girls watching us was enough to trigger Ben's climax. We came together, Ben's cock pulsing while I tightened about him.

Possibly the funniest thing we did was on the plane over to Paris. Fiona, Ben and I decided to have a nice romantic weekend in the city of love, and while queuing at security we were joking about joining the mile high club, but it's not really possible on a short flight in a tiny jet.

The flight itself was just over an hour, which is just enough time for the flight crew to serve drinks and biscuits before the final descent starts. There were two seats either side of the central aisle, and we had booked three of the four seats in the last row, on the off chance we could sneak into the toilet for a quickie. We didn't do that, but the plane wasn't full and we had the back row to ourselves.

Ben took the window seat and I sat next to him. During take off I gained access to his cockpit and with my hand on the stick I helped him to gain altitude. A little later we had a ten minute window of opportunity, while the flight attendants worked slowly towards the tail with the trolley. I leaned over and worked him with my mouth, using long deep strokes (as well as I could in that awkward position), determined to make him come.

And I did, and the trolley was still three rows away. I sat back, grinning happily while Ben tidied himself away. I was still smiling when the flight attendant asked me, "Would you like something else to drink?" The shocked expression on my face had Fiona giggling for hours. (It became a long-running private joke between us to use that exact question whenever Ben or Fiona were offering to get me a drink.)

Our hotel room was a family room with a large double bed and also a single bed, though of course we never used the single. It was on the third floor, and the large window looked out at another much larger hotel. Anyone there looking out of their windows could easily see into our room, and we chose not to draw the curtains.

We got back to the room late on the Friday after an excellent meal and a little too much wine. Even Fiona was relaxed enough for us to show her off to the world. We switched the main light off but left the reading lights on, enough to both reveal us and silhouette us to any curious watchers.

We stood in front of the window, stripping slowly, then Fiona knelt to take Ben's rising cock in her mouth. I love doing this, but I'd had my turn that day. Fiona took her time, making love to it with her lips and tongue. I sat on the bed watching this beautiful scene for a while, then lay on the floor behind her and worked my head between her thighs until her pussy was poised above my thirsty mouth.

The position was awkward, but I was able to attend to her pleasure, licking her wet lips, caressing her clit, kissing it, sucking it. Her hips thrust against my head in a gentle rhythm as her own head bobbed up and down Ben's hungry shaft.

As Ben started to get close, he withdrew and asked us to sixty-nine. We shifted position, me still on the floor but Fiona now facing the other way. Although officially we were girlfriends, we didn't have sex with each other very often, so going down on me was a relatively new experience for Fiona. Ben sat on the bed watching as we devoured each other's tender flesh.

A movement caught my eye. A silhouette in one of the windows that looked out at us. I was sure it was a woman, standing naked with legs slightly apart. I lost sight of her as Ben knelt above my head and pushed his beautiful cock deep into the pussy I was tonguing. I licked along his length as he thrust in and out of her, wishing he didn't need to wear a condom - I don't like the flavour. (We always insisted on condoms for vaginal penetration.)

After a while he asked to swap, and Fiona rolled over onto her back. I knelt up and looked over at the figure watching us. It was definitely a woman, definitely watching us. I moved into position and bent to resume my attack on Fiona's gorgeous pussy. I loved that we were being watched. I hoped the woman was fingering herself to a lovely orgasm as she watched us. I wondered whether we could invite her over.

Ben knelt behind me and pressed the head of his cock against the tight ring of my ass. He had removed his condom and was slick with cool lube. We'd done anal a few times by that point, and I was still wearing the plug regularly, but Ben's cock is thick. He had to really force it against my ass to open me. The combination of Fiona's tongue on my clit and the head of Ben's cock pushing into my ass triggered a powerful orgasm. I cried out as my tight muscles clenched around the intruder, and I felt Fiona drinking the sudden rush of my juices.

I lay there on top of Fiona for a minute, unable to think, my entire awareness being that cock stretching my ass. And then he started to move and the pain-pleasure of his cock sliding into me triggered another mini-orgasm. He built up a rhythm, and I recovered enough to pay attention again to Fiona, licking her clit in time with the cock fucking my ass.

I was in heaven. Ass-fucking clit-licking heaven. I wanted it to last forever, but Ben's panting grew heavier, and heavier, until he cried out, his cock thrust hard and deep into my ass, and the glorious sensation of his cum filling me triggered another amazing orgasm, and I lost all control as I convulsed helplessly about his pulsing member.

Ben pulled out of me slowly, and I crawled off Fiona. I lay on my back, my ass towards the window, showing the woman (and anyone else who watched) exactly what Ben had done to me, though it was probably too dark for them to see anything. Ben and Fiona climbed onto the bed to play more, but I was happy to lie there by the window while my cum-filled ass slowly recovered.