The Thing About Libby

When did I first meet Libby? It must have been when I first went down to the town, when I was 20, and going out with Sandra, my first girlfriend. Sandra wasn't a very satisfactory girlfriend but she was my first, so I was eternally grateful to her. She was sassy and sexy and, in spite of that, rather prudish, at least with me, and refused to take all of her clothes off for the entire time we were going out with each other. It didn't stop us from having sex, but it did stop us from having a totally brilliant time with each other.

Yes, that was when I met Libby, who was a teenager then, 14 or something, rather pompous and with rather a lot of puppy fat. She was bespectacled and bookish and her parents were hippies and she only hung out with us hard-drinking twentynothings long enough to register silent disapproval of us, before going off to dig the garden or make rice or do one of the other hippy teenage things she used to do. She was a pain in the ass.

Then Sandra and I broke up and she moved back to the town, where she'd grown up, whereas I stayed in the city, where I belonged. Six years passed. I had other girlfriends and I didn't think of Sandra much, and I had a lot of fun, and I became more exploratory, and I got a good job and I enjoyed myself.

And then, that New Year's, I was single, and Sandra, out of the pity of her heart or her sense of mischief, invited me down to the town to spend New Year's with her and her friends. For some reason, that year, it was the best offer I had, so I took it.

I wasn't long in Sandra's house, reacquainting myself with her and her friends, before I came to think that I'd made a big mistake. What I had once taken in Sandra to be coolness now seemed like dullness. Her friends were all obsessed with goings-on in the town and they seemed to be stuck where they had been six years earlier. I sat there and made polite and drank beer in the pub but really, all I wanted to do was go back to the city.

But then I spotted a girl on the edge of things, joking with Sandra and her friends, engaging in intense conversation with various people. She was tall for a girl, with glasses, dark-coloured, with narrow eyes and a broad, ironic mouth, and what looked like a good body; her t-shirt and jeans outlined her very nicely and suggested a certain robust, country-bred frame, the kind of girl who did a lot of cycling and climbing but who also liked a square meal, even if it was mostly composed of lentils.

It took me a few minutes to realise that this was Libby.

Of course, I thought. It was six years on; I was 26, she must be 20. Libby was college-aged, by this point. A few discreet enquiries revealed that she was in college, working towards a BA in Womens' Studies.

Well, that in itself was interesting, if not entirely unpredictable, I thought. It made perfect sense that Libby would have become a 20-year-old feminist. But then, I noticed a curious effect of my asking about her; people would answer my queries, but also glance at Libby with something like trepidation. There seemed to be a slightly warning look in their eyes, as if they advised me to keep away from her.

It crystallised when I was talking to someone about her and Sandra herself came over, her face cheerfully flushed with wine, and said "Who are you talking about?"

"Alex was just asking about Libby," said Cathy, the friend I'd been chatting to. Sandra's eyes widened and she stared at me.

"Oh my god, Alex," she said fervently, laying a protective hand on my arm. "I'm serious. I love Libby, but, don't go near her. She'll eat you alive."

"Why?" I said. "What does she do?"

Sandra's face twisted thoughtfully.

"She's ... imbibed a lot of notions up in college," she said. "I dunno. I think. So I've heard, from anyone who's been with her. She's a bit difficult."

"I like a challenge," I said, smiling. Sandra looked at me pityingly.

"God help you, Alex," she said, "you've always been a strange boy."

And she moved off.

I spent the next half-hour or so quietly manoeuvring myself into a position where I could talk to Libby. She was buried deep in conversation with a girl I knew, Lorraine, a very sweet if not exactly intellectual type whose relationship with her boyfriend Carl was the stuff of legend in this town; they'd been together forever, it was understood that one day they'd get married, but in the meantime they were content to carry on as though they were still dating. I could see that Lorraine was trying to keep up with Libby, but that the entire time she had one arm resting on Carl's leg and was increasingly stroking her boyfriend as if to signal her own faithfulness to Libby. Finally, Libby laughed at something Lorraine said and got off the arm of the sofa where she'd been perched for an hour and headed to the kitchen.

I went after her and found her looking in the fridge. She pulled out a beer, straightened up and glanced at me, then looked again and smiled briefly.

"Hello," she said.

"Hi," I said.

"Alex, right?"

"Yes."

"I remember you."

"I remember you, too," I said, smiling. Libby eased open her beer and had a sip, looking at me appraisingly, then moved aside to let me into the fridge. I got a beer as well, and leaned against the kitchen counter, opening it.

"Are you down for new year," she said.

"I am."

"Good," she said. "Sandra's very hospitable."

"You're in college now," I said.

"I am," she said.

"How's it going?"

"Really good," she said, nodding. "I like it very much. I think I'm going to do a Masters."

"Good for you," I said. "You should."

"Thanks," she said. "Did you do one? I can't remember."

"No," I said, smiling. "I went straight into the business."

"But you're doing pretty well," she said. I was amused at how little of a sense of humour Libby still had. At this point in a conversation, most people liked to make the odd nervous, self-deprecating joke, to signal to the other person their own normality and approachability. Libby wasn't interested in that. She had still not acquired any social skills worth mentioning.

"I think so, yes," she said.

"You look great," I said. She smiled, making eye contact with me for the first time.

"Thanks," she said. "So do you."

"Thank you," I said, inclining my head politely.

"I haven't seen you in what, five years," she said. "I was a lot chubbier when I was younger."

"I'm surprised you remember me," I said. "We barely spoke."

"Oh, I remember you," she said. "I mean, I remember everyone. But I also remember you."

"It's always nice to hear that," I said, grinning. Libby seemed to see the humour in this and her wide mouth split into a brief grin. Then she knotted her brows together once more.

"It's very weird, seeing all Sandra's friends come back here," she said. "It feels like I've grown up and you've all stayed the same."

"It is a bit like that," I said. "I mean, I hope we've all matured slightly. In a non-boring kind of way. But you've definitely grown up."

"Oh, I have," Libby said. "I've learned a lot."

"What kind of thing?"

"Mostly about what goes on between men and women," said Libby. "I was so naïve. I think I was a bit grossed out by it all when I was younger. Now I'm much more accepting of difference."

"What do you mean by 'difference'?" I said.

"Just, the different ways in which men and women can relate to each other," she said. "I'm very interested in the ways in which they can connect."

"So am I," I said.

"Yes," she said, smiling at me. "Like, you're flirting with me, now, for example."

I was taken aback, and it took me a moment to recover myself.

"Yes," I admitted. "I am."

"Why are you doing that?" she said. "Do you just do that with all women, or do you find me attractive?"

"I do it because I find you attractive," I said.

"Okay," she said, nodding. "That's good, because I find you attractive."

"That's ... great, from my perspective," I said, and we both laughed.

"But I do have to warn you," she said, "that I don't really believe in the traditional male and female roles in sex. I'm not interested in perpetuating that."

"You're not interested in sex?" I said.

"No," Libby said, "I am interested in it. I mean, I like sex. Just not the usual, boring, vanilla sex that most men and women have."

"Ah," I said, somewhat mystified, but interested. "I see. I think."

"So," Libby said, and here, at last, she actually caught herself, blushed slightly and laughed, "if you were at all ... um ... interested, in ..."

"In flirting with you?"

"Yes," she said, "in flirting with me, then if you're only after boring vanilla sex, I'm afraid you're going to be disappointed."

"I'm not especially interested in boring sex, no," I said. "I don't think most people are."

"You know what I mean, though," she said.

"I'm not sure that I do," I said, truthfully.

We were silent for a moment. Libby stared at the floor thoughtfully, then looked at me, eyeing me, then pushed her glasses back up her nose.

"Perhaps kissing me would be something you could do, now," she said.

"That I can do," I said, and I moved over to her and she lifted her face - she was slightly shorter than me - and looked up at me, her eyes shining, her lips parted.

I put my hands on her bejeaned hips and felt her freeze, ever so slightly, then I kissed her, and she kissed me back. She leaned into me and I felt the warmth and fullness of her breasts on my chest. She was a good kisser.

We kissed for what must have been a few minutes before she withdrew and looked at me, a little shyly.

"We could continue this in my room," she breathed, and I nodded. She took my hand and led me out of the kitchen, down a corridor, up the stairs, across the landing and into a bedroom.

Ten minutes later we were lying fully clothed on her bed and my hand was inside her shirt and we were kissing, our bodies entwined. I was silently congratulating myself on having successfully scored with this smart, interesting, voluptuous girl. Her body was straining against mine and I knew it couldn't be long before we were getting a lot more intimate.

Then Libby drew away from my face and looked at me seriously.

"Alex," she said, "I want to have sex with you."

"Good," I said, smiling. "I want to have sex with you."

"But we have to do it on my terms," she said.

I paused for a moment.

I'm not some jock who just thinks that girls are for conquering. I was brought up to believe in feminism, and I think that when a woman tells you that she wants something that's within your power to give, you should give it to her. I wasn't sure what Libby meant by her 'terms' but I guessed that somewhere along the line she'd been fucked over by some asshole and that she had difficulty with intimacy. That was okay; I had difficulty with intimacy myself. I didn't see why I shouldn't go along with whatever she wanted.

"Okay," I said. "You let me know what you want to do, and let's do it."

She smiled.

"You mean it?" she said.

"Of course," I said. "I don't want you to do anything you're not comfortable with."

"You're sweet," she said, and kissed me. Then she got off the bed and stood on the carpet.

"Take off everything except your pants," she said. I smiled at her and sat up, pulling my shirt and t-shirt off, then I pulled off my socks and unbuttoned my jeans and rolled them off.

In just my boxer shorts, I sat on the bed, feeling exposed as Libby stood before me, fully clothed and calm and in charge.

"Now," she said, "get on all fours. Facing the headboard."

I did as she asked, and felt her eyes on me the whole time, feeling intrigued and excited and increasingly vulnerable, which was a turn-on. My erection was poking at the front of my shorts.

"You see," Libby said in a professorial voice, as if she were in a tutorial room, "the female body is usually the recipient of the male gaze, and is usually the territory that the male body occupies. I'm not happy with that and I want to do things differently."

"Okay," I said.

"I bet you've looked at a lot of porn in your life," she said.

I sensed that it would be unwise to be completely honest in my answer.

"Not that much," I said.

"But you've seen a lot of naked women. In pictures."

"I've seen some in real life, too."

"While you yourself have remained at a privileged distance."

"Not all the time," I said.

"But come on, Alex," she said, and there was a faint undertone of urgency in her voice. I sensed that she wanted me to cooperate with her. "Generally."

"Generally, yes," I said.

"And now you have a clothed woman looking at you," she said.

"I'm not naked, though," I said, looking her in the eye.

"Not yet," she said, returning my gaze boldly. "How does it make you feel?"

"Vulnerable," I said, truthfully. "I feel like you could do anything you wanted to me."

"Could I?" she said innocently.

"It looks like it," I said, feeling her gaze on my bare back and shoulders and flank, seeing her glance at my dark blue boxers.

"Say it," she said softly, walking over to her bedside table and staring down at me.

"You can do anything you want to me," I said quietly, looking up at her.

"You know it's not going the other way," she murmured. "You can't do anything you want to me."

"I don't care," I breathed. "I want you to do what you want to me."

"Anything?"

"I mean," I said, "I assume you're not going to do anything ... juvenile or dangerous."

"Oh no," Libby whispered, "I'm very grown-up," and she pulled open her bedside table drawer and extracted a dark blue sleep mask of the kind they used on aeroplanes.

I looked at it and blinked, as I realised what she was going to do with it.

Sure enough, she reached down and put it on me, covering my eyes. I gasped. Then I felt her hands on my bare shoulders, caressing me, and she stroked all the way down my bare torso and flanks until she reached my boxers.

She slowly, very slowly, began to drag them down over my hips, first of all uncovering the top of my bum, and as I gasped again with arousal she slowly uncovered the whole of my bare bottom, leaving the front still covering my genitals.

"You don't often get the woman stripping the man naked," she murmured. "I think it's quite interesting. How do you feel now?"

"Very exposed," I breathed. "I'm almost naked."

"You didn't think it would be like this, did you?" she said.

"No," I admitted.

"You didn't think it would be me with all the power, and you with none, did you?"

"No," I gasped as she pulled the boxers down over the tops of my thighs, and the front part slowly uncovered my stiff cock, which sprang free. As soon as my genitals were uncovered she quickly pulled the boxers down to my knees, over them and off my ankles.

I was on all fours, naked and blindfold on the bed, passive and receptive, her willing victim.

"Now you're totally naked, Alex," Libby said. "And you still haven't seen me naked. Do you feel humiliated?"

"A little bit," I admitted, but I was also aroused. Libby ran her hands over my naked body, deliberately pushing her fingers into my every last nook and cranny, feeling me, showing me that there was nowhere she wouldn't and couldn't touch me. I remained on all fours, moaning softly with humiliation and desire. She grasped my cock and pulled on it experimentally a couple of times and that made me whimper.

"Alex," she said softly, "do you know what I'm going to do?"

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"No," I breathed.

"I know you want to have sex with me," she said, "but what I'm going to do is, I'm going to fuck you, and I'm not going to ask for your consent. Now, obviously, if you don't want that to happen you're free to get off the bed and get dressed and leave. I couldn't stop you. But otherwise you're going to find out what it's like for someone to just take you whether you asked for it or not."

I felt her fingers on her left hand, smearing copious amounts of some cool gel between my naked buttocks.

"Oh god," I moaned.

"Yes," Libby murmured. "That's how I'm going to do it. Have you ever had anyone in there?"

"No," I gasped, as she pushed her finger against the tight bud of my anal muscle and massaged it.

"Well," she said firmly, "you're going to now."

"Oh, please ..." I moaned.

"Come on," she said sharply. "You wanted to have sex with me, and you're going to have sex with me. Just not the way you planned it."

"O-okay," I gasped, feeling Libby push me further and further, making me submit, making me understand that she was in charge, and that what I wanted meant nothing, and that that was what she was in this for.

Her steady pushing at my anus with her finger was making me loose, and I was breathing regularly, making myself relax, forcing myself to see the mental image of the naked young man on a bed, on all fours, blindfolded, submitting to a naked girl who was preparing him for one of the ultimate humiliations. It was me. I had walked into this, I had wanted Libby, and she had made it crystal clear how she wanted me. I had nobody to blame but myself.

And, to tell the truth, I was incredibly aroused by being forced to be so passive, so submissive; Libby was strong and dominant and she wanted a sissy boy, and I was willing to be that. I had never known I had it in me to be such a femme boy, yet here I was, moaning as a girl I hardly knew stripped me naked and prepared me for ...

Then she got off the bed, and there was a pause during which I heard a drawer being opened and various items of clothing moving around, and then the bed shifted and I felt her bare legs against mine.

Was she naked? No. She leaned over and I felt her bra-covered boobs, heavy on my back, and then I opened my mouth in shock as I felt the head of the strap-on dildo pressing slowly and inexorably between my naked buttocks. I reached behind me blindly and felt her panty-covered hips, and the webbing of the strap-on. There was no way that Libby was going to get naked for my benefit. Not if she didn't have to

"Oh yes," Libby groaned. "Oh fuck, that's hot, Alex. Yes. Do you know what I'm going to do to you now?"

"Yes," I whimpered.

"There's nothing I love more," she purred, "than the sight of a beautiful naked man getting arse-fucked by a girl."

"Ohhhh!" I gasped as I felt her leaning in, putting pressure on my anus, and I shuddered, and she stroked me like I was a champion racehorse, and patted my bare arse, and stroked my cock, and I heaved a deep breath, and she leaned in again, and I went "OoooaaaAAAUUNNNHHHHH!" as Libby, gasping, slowly forced her dildo into my anus, and penetrated me.

"Uuunhhh!" I whimpered, almost sobbing, as Libby dominated me. This girl I'd known as a chubby, over-serious teenager was now a poised, confident 20-year-old, and she was breaking my dignity into a million pieces and turning me into her whimpering sissy boi in the process. I felt Libby thrust her strong country girl's hips forward and her dildo slid deep into my rectum, occupying me, impaling me on her.

"Do you like that, Alex?" she gasped as she pulled the dildo half-out of me and pushed it in again.

"Yes," I moaned. "Ohhh ... god."

"Ohh, that feels so fucking good," she gasped, and she pulled half-out of me and pushed in again. The plastic rod was filling my ass and my mouth was hanging open and I was clawing the air helplessly as Libby fucked me.

"Wow," Libby chuckled, "you're really into this, aren't you? Some guys only put up with it but not you."

"Yes," I whimpered.

"You like it, Alex?" she gasped. "You like the feeling of being arse-fucked?"

"Yes."

"Have you ever had it from a guy?"

"No."

"I wonder if you'd like it. I think you would. Mmm ... that's something I'd love to see. You being mounted by a guy." Libby sounded delighted. I couldn't help myself, my cock was as stiff as a rod and my body was shaking as she fucked me and I was desperate to cum. I reached forward and grabbed the bedspread in my hands and clutched it for dear life. Being sodomised by Libby was the most overwhelming sex I'd ever had and it was fucking with me on every level - physically, intellectually, emotionally, I was being turned inside out by a girl with a strap-on.