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Finding Jenny

Category: Anal Sex
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Jenny was my best and oldest friend. And it was because of Jenny that Mark had left me.

Some of my other friends claimed not to see why Jenny and I were so close. We had known each other since our first day in college. I had been wandering around the room on Freshers’ Day, wondering which if any of the idiotic-looking societies I should be joining, when I had collided with some sort of small, soft object.

A lot of papers and folders spilled across the floor, and a loud London voice went “Oh for fuck’s fucking sake.” I mumbled an apology and stepped back. A small person with an improbable hat was looking up at me and grinning.

“It’s okay, it’s not your fault,” she said. “I’m just being a clumsy fuckwit as usual.” She knelt down and began to retrieve her papers. I knelt next to her.

“You’re new here too?” she said. I nodded. She leaned forward and whispered, “Doesn’t this look like a bunch of total tossers? Would you ever in your wildest dreams join one of these wanky societies?”

“No, not really,” I said, grinning. She stuffed the last of her papers into a bulging bag and leaned in closer with a wicked smile.

“You want to go and get rat-arsed instead?” she murmured. I said I thought that that was a great idea. She grabbed my arm and dragged me off to the student bar.

That was Jenny. She had Irish parents, but had grown up in Hackney. She was small, with large, dark brown eyes, a wide mouth, a mop of black hair that was usually scraped back into a ponytail, and a remarkably foul mouth. I liked her instantly. After the seventh vodka and tonic she tried drunkenly to snog me, but when I politely (if slightly slurringly) explained that I wasn’t interested in girls, she didn’t seem at all fazed and curled up on the bar seat with a fresh drink in her hand.

During that first year in college, I lost my virginity to a strapping American politics student called Brian who invited me for a squash game one evening, beat me soundly, and then came up behind me in the shower afterwards, grabbed my cock and started kissing the back of my neck. I had never gone any further than sucking off a couple of the older boys in my school, so this was a little unexpected, but very pleasant. “I’m not gay,” Brian whispered in my ear a little too earnestly, and I said breathlessly that I totally understood. He told me that I had an ass like a girl’s, and rubbed a bar of soap between my buttocks before pressing me against the wall and working his cock into me. I couldn’t believe the pain, at first – it felt like somebody was sticking a truncheon up my arse. I whimpered and had some hysterical thoughts about U.S. imperialism, but between Brian’s insistences that he wasn’t gay, and his steady hauling on my cock, and his tender urging of me to relax, I quickly learned to relax and take him inside me, and soon he was fucking me energetically against the tiled wall while I groaned with ecstasy. At least one student entered the shower area, saw us, let out a startled “Jasus!” and fled.

Brian left me lying face down on the tiled floor, the showers hissing water onto my naked body, my semen curling away from me in tiny white threads as the water flowed over me, my arse feeling like it was on fire. I got dressed and sought out Jenny, eager to tell her what had happened. We celebrated with whiskey in her flat. After that I acquired a certain notoriety as the guy who had been fucked in the showers; it meant that most of the rugger-buggers didn’t go near me for fear of contamination, except for the drunken one or two who turned up at my flat late at night for a bit of furtive and delicious buggery, while the predatory seniors sought me out for a bit of light relief. I didn’t mind; I liked it, and I kept Brian’s secret (for some reason none of this notoriety stuck to him). Maybe he really wasn’t gay after all, because three weeks later he was going out with Jenny, although he dumped her for being “too weird”. We both decided that he was a prick and a user, and that it was a lesson to us in the fickleness of men.

Over the next four years, hardly a day went past in which we didn’t see each other, and by the time we graduated we were best mates. We looked out for each other. At first I think it tickled Jenny to think that her best friend was a gay man, but later it became a positive asset. She went through a stage, shortly after leaving college, of being a chronic boyfriend-stealer, and lost many of her old friends in the process. Jenny’s relationships were like Tolkien’s dwarves; short, intense, ugly and bad-tempered. She knew that if she rang me up in tears at 1 a.m., I would bicycle over with a bottle of wine and a stupid video. In turn, I knew that if I was ever in a maudlin mood about how I would never find the right guy – which was often – that she would soon be round my flat wearing yet another of her ridiculous forms of headgear, to drag me out for a night on the piss.

Once – just once, when we were both particularly lonely, and spectacularly drunk – we had slept together. Well, at any rate, we had passed out in the same bed in our underwear, and at about five in the morning I had passed out of a restless sleep to find Jenny dozily fingering my cock. I was vaguely wondering what she was doing when I realized that I actually had an erection. Then I noticed that she was sitting up in bed and taking off her bra, then slipping out of her panties. Then she was sitting astride me, trying to get me inside her. In the chilly dawn light I saw that Jenny’s breasts were almost imperceptible; she had two shallow raised areas where other women had bosoms. She looked weirdly small and young. Her hair was hanging over her face. She was breathing hard, and trying to find the right position for my rapidly slackening penis to get into her.

“What are you doing?” I asked sleepily. She stopped, frozen, and then relaxed a little.

“Oh,” she mumbled, “I just thought, fuck it, you know…I, uh…”

“It’s okay,” I said, drifting off to sleep, “you can if you want to.”

But she didn’t. I felt her sitting astride me for a moment longer, then she got off and put her pants back on again. Then I was asleep. When I woke up the next day, she wasn’t there, but I found her sitting in the kitchen drinking coffee and holding her head. We never mentioned what had happened, and the next time I saw her she was the same as usual.

That was years ago. We went on. Jenny went to work as a child psychologist, which was, as I pointed out to her, the perfect career choice for somebody who was herself not all that far removed from childhood, and by the way it was not cool to try and hit your friends there, and did she mind, that was my bloody copy of Now she was using as a weapon. I became, to her lasting and enormous amusement, a civil servant in the Office of the Registrar for Civil Marriages. (“You! Marrying people! No wonder this country’s in such a fucking mess.”) We still saw each other as often as possible, and it was probably that, as much as anything else, that fucked up my relationship with Mark.

I had met Mark at, of all places, a wedding. He was a few years older than me, tall, funny, intelligent and well-educated. I took him back to my flat that night and we had a bottle of wine before he pulled me into the bedroom, stripped me of my clothes, flung me down on my back and fucked me better than anyone had ever fucked me before.

I couldn’t get enough of him. Mark was by far the most skilled lover I had ever had, not to mention the most entertaining companion. Apart, of course, from Jenny, who was my closest friend. There was only one thing about him that annoyed or perplexed me, which was that he always needed to be on top. There was never anything very mutual about our lovemaking; he fucked me, I sucked him off, but not the other way around. When he was inside me I almost always got so aroused that I came anyway, and even if I didn’t he would reach around me to finish me, but I had a vague regret that I never got to enter him.

It didn’t really matter. I admired Mark so much that I didn’t want it any other way. He loaned me books, we had long conversations about writers and movies we admired, we even went to the theatre, which up until then had been something you couldn’t pay me to do. I liked the new me that was emerging. I was thirty; it was time to get serious, to be grown up, cultured, erudite, all that stuff.

Need I point out that Jenny fucking hated Mark?

I invited her round for dinner with the two of us. I was eager to introduce my oldest friend to my newest lover. I made lasagna; I was in such a haze of happiness that I barely noticed the peculiarly frequent silences, the increasing fixity of Jenny’s smile, Mark’s desperate attempts at small talk. Later in bed, I said to Mark, “So what do you think?”

“She’s, um…not quite what I expected,” he said cheerfully.

“Why, what did you expect?”

“Oh, uh…somebody a little more…like you, probably.”

“What do you mean, like me?” I asked.

“Well, you know. Serious. Um, grounded.”

“You think I’m serious and grounded and she’s not?” I didn’t know whether to be affronted at the implied insult to Jenny, or flattered at the implied compliment to me.

“No no no,” said Mark. “I mean, she’s really nice and everything.”

Jenny was less diplomatic. “He seems really nice and everything,” she said to me over lunch in town, “but he’s a bit of a…git, isn’t he?”

“What you mean?”

“Well, sort of snobbish, and stuck-up, and pretentious. Going on about bloody ballet all night.”

“He likes ballet!”

“That’s no reason to go on about it.” Jenny swigged from her third glass of wine.

“There’s nothing wrong with ballet. You don’t know what you’re talking about, so just fuck off,” I said, plunged into a bad mood. “And by the way, you drink too much.”

“You fuck off,” she said, refilling my glass. I put my hand over it to stop her, and she poured Shiraz all over my hand. “Oh fuck,” she said, sounding not very contrite. “Sorry about that.”

So Jenny and I stopped seeing each other quite so much. I knew she was jealous because I was spending more time with Mark, but I didn’t give a shit. Mark was way more fun than her anyway, what with her endless men troubles and her clinginess and her general desire to want to spend most evenings round at my flat watching stupid movies and talking back to the screen. Looking at Jenny through Mark’s eyes, I could see just how shallow and silly she was. She was apparently content to spend her whole life going out with idiots for a couple of weeks at a time, just to get a quick shag, without ever wanting to sit down and really talk to someone. I couldn’t understand why we had spent so much time together. I had Mark; he cared for me. He took the initiative in bed and out of it. He was my lover, my mentor, my friend. I knew I had to break away from Jenny or I’d never become a real person.

Then one day, I had a conversation with Jenny that made me start thinking. She had dragged me out for coffee, and we were sitting in silence.

“You want to do anything this evening?” she said hopefully.

“Nah,” I said. “Kind of busy. We’re going out with some of Mark’s friends.”

“What about tomorrow?”

“Mark doesn’t like going out on Saturdays.”

“What about just you? Can’t you come on your own?”

“Mark doesn’t really like it.”

“Fucking Mark!” she exploded. “Mark Mark Mark! I’m sick of it, all you ever talk about is what he wants and what about me, don’t I want things too?” She grabbed her bag and stormed out of the café before I could stop her. I got the strangest impression she was actually about to burst into tears.

I finished my coffee and went out to get that night’s dinner, and as I was wandering around the supermarket I began to wonder if maybe Jenny wasn’t right. Perhaps I was relying on Mark to make up my mind for me about things. After all, I had tried to like ballet but deep down I knew that it was really just people jumping around in tight costumes; theatre had been more fun, but I didn’t want to sit through any more classical music concerts.

Plus, I thought as I stood in the queue for the checkout, what was I turning into? A bloody housewife. Here I was, doing the shopping, for the meal I knew Mark was expecting me to cook; later we would curl up in front of a highbrow video before Mark announced that it was time for bed, which meant him fucking me before dropping off to sleep – this was my new, adult life? Wasn’t it just a bit…heterosexual? I might as well have the operation and change my name to Petra.

I’m not going to go into the words that passed between me and Mark that night; I can look back on them now without regret, but it took a hell of a long time, even considering what happened afterwards; let’s just say that what started as a suggestion from me that maybe we were a bit unequal in terms of power in the relationship ended up in shouting, tears (from me), a saucepan thrown at the head (also from me), the accusation that I was a ignorant brat who didn’t know the meaning of gratitude and responsibility (from him); the accusation, from me obviously, that he was a crypto-straight control freak who didn’t know how to have fun unless it was in a foreign language.

You know that bit in Catch-22 when the hero is looking after a wounded airman who he thinks just has a leg wound, but then it turns out that the guy has had his guts blown out, because they suddenly spill all over the floor of the aeroplane? That’s what the fight was like. I thought we were fine, and that I had just had a couple of small problems. It turned out that we were not fine at all.

It may seem unlikely, but it didn’t end in one of us walking out of the flat. First Mark recovered his temper, then I stopped crying and yelling, and then he said in sober terms that it was clear that if neither of us were making the other happy then there was no point in continuing on together. I overheard myself agreeing that this was the case, and we hugged and shed a couple more tears, and then he packed some stuff and left.

I got shitfaced and went to bed for twenty-four hours. While I was asleep, Mark came and silently removed the few things he’d left in the flat, including the key, which he slid under the mat and which Jenny subsequently found a few hours later, which is why I woke up to find her kneeling on the bed looking worried and shaking me.

I wasn’t in any mood to see her or anyone else. I had managed to sleep through the worst of a hangover, and I was hungry. Jenny was all efficiency, turning on the oven, bringing out wine and Marks & Spencer ready meals. I showered and shaved, and grunted my way past her attempts at conversation. We ate, and then we retired to the sofa. Jenny curled up at the other end of it. She looked infuriatingly fresh and pretty, in a white cotton shirt and jeans. I felt like Swamp Thing; I was alone, I was old, I was single again and nobody would ever, ever love me.

Eventually I started to tell her what had happened. She listened seriously, making little clucking and sighing sounds of understanding and sympathy. As I got closer and closer to the part where Mark left, I started to lose my air of stoical composure and by the time I got to the end, I was crying again. Jenny stroked my arm sadly, then pulled herself down to my end of the sofa and gave me a hug.

“I miss him, Jenny,” I sobbed into her cotton shirt. “I fucked it up, I was too demanding and now he’s gone and I miss him.”

“You weren’t too demanding,” she murmured. “It’s not your fault.”

“It is my fault,” I wailed. “I wasn’t mature enough for him. He needs someone better than me.”

“That’s crap,” she said soothingly. “There’s nothing wrong with you. You’re perfect as you are.”

“If I’m perfect, why did he leave me?”

“Because he was…” she started, then collected herself. “Because…he wasn’t right for you.”

“There’s nobody right for me,” I muttered, wiping my nose.

“Don’t say that!” she urged me, clutching my arm. “There’s somebody right for everyone. I really believe that. There is somebody out there who is perfect for you and you’re perfect for them.”

“Oh Jenny,” I said, “that is such bollocks and you know it! Think of how many people die alone. Most people never meet their soulmate.”

“Some do,” she said, folding her legs under her and looking hurt.

“Yeah, well I’d like to meet them. You see, that’s the sort of crap you’re always coming out with. Mark was right about you, you have these ridiculous romantic ideals that nobody can ever live up to and that’s why every guy you go out with it’s just stupid sex and that’s it. Face it, Jenny, you and me are on the shelf. We might as well give up cause the older we get, the less likely it is that we’re ever gonna meet the right people.”

Jenny was staring at me, looking pale. Her black hair was touched with strands of grey at the temples, and her eyes had acquired fine laughter lines at the corner, but apart from that she hardly seemed older than when I first met her, and certainly no more mature.

“Maybe,” she said quietly, “we already know the right people.”

“Oh really?” I said. “Who? Tell me, cause I’d love to know!”

She was silent. Then she lit a cigarette (were her hands trembling?) Then she said, in an even smaller voice, “I really love you, Pete.”

“Yeah,” I grunted, turning my face to the TV. “You know, same here. But that’s not much good to me, is it? You being a girl, and everything.”

Jenny sat for a moment in silence. Then she drained her glass and left the room.

I watched TV and drank wine for a while. I was sorry for myself, and angry with Jenny for being coy and sentimental when I wanted her to be funny and contemptuous. Now I was going to have to calm her down and get her back into a good mood. I muttered a curse, then I got up and went into the kitchen, where I knew she would be sitting and smoking and waiting for me to apologise.

But she wasn’t in the kitchen. I checked the hall; she hadn’t snuck out of the flat, her hat and coat were still on the peg. I knocked on the bathroom door, which swung open into darkness; I turned on the light, but the room was empty. I was starting to get worried.

The only place left was my bedroom. The door was shut. I knocked on it; there was no reply.

“Jenny? You in there?”

There was nothing, then a muffled noise of assent.

“Look, I’m sorry, I was being mean. Come on. Come out and let’s get pissed.”

There was nothing. I pushed open the door and went in.

The main light was off; only the bedside light was on. Jenny was lying face down on my bed, her arms folded beneath her forehead, her face buried in the pillow. She was completely naked. Her clothes were scattered over the floor. I caught my breath; of all the things I had or hadn’t expected, this had never even entered my mind. Was she sick? Was she having a nap?

“Are you okay?” I asked. She nodded her head without looking up. I detected a slight shake in her shoulders.

It seemed totally wrong to be looking at my friend like this. It was sort of obscene; the smooth skin of her back sloping down to the base of her spine, then curving steeply up over the twin mounded hills of her buttocks, and sloping down her bare legs. This was for her lovers, not for me. I could see how smooth her skin was; she had a small mole over her right shoulder blade, and another on the left side of her ribcage. How many times had I lain on the bed like that, waiting for Mark to take me, or Greg or Aidan or Donal? What did Jenny think she was up to?

“What are you doing?” I asked. She turned her head slowly and looked at me; her face was red and blurry with tears.

“You never listen to me,” she sobbed. “I told you I love you and you don’t listen. I’ve always loved you but you’re such a fucking idiot you don’t notice. I want to be with you.”

She looked at me miserably through the film of tears, her pale, naked body shaking. I wanted her to cover up, this was all wrong, I shouldn’t be seeing this…

“Jenny,” I said, “I love you too but…we can’t, it’s no good, I mean…I wish, I really do, I wish we could make it work, but we just…we just can’t. I do love you, really, I do, but I can’t love you like…like that. I like boys.”

She looked at me steadily, and I felt a wave of love and pity for this young woman I thought I’d known so well. Then I hated myself for pitying her; then, and this hurt most of all, I hated her for inspiring my pity.

“You could make me your boy,” she said softly.

It took me a moment to work out what she meant. When I realized, I was horrified at the sacrifice Jenny was offering. I didn’t want her to do that. I didn’t even fancy her. Did I?

I looked again at her short, naked body, the swell of her hips, the slight curve of her breasts just visible underneath her, flattened against the dark purple bedspread. My anger was growing. All of a sudden I did want to do it. I wanted to take Jenny and show her just what she was suggesting, to make her feel the pain and indignity, to violate her, to end this one way or the other. I knew it would mean the end of our friendship. If that was how she wanted it, fine. I didn’t fucking care.

No, a voice said, don’t be so stupid. You don’t want to do that. You have to talk her out of it. You have to rescue this before it goes any further.

“You don’t want that,” I said.

Jenny closed her eyes for a moment, then opened them. “Pete,” she said, “you do like me a little bit?”

“Of course I do,” I said. And it was almost entirely true.

“Why do you think I can’t hang on to a guy for longer than three weeks?” she said, her lip trembling.

“Because you’re an emotional retard?” I forced a smile onto my face.

“Because most of them don’t like sleeping with boys,” she said tonelessly. “Now do you see why I’ve always loved you?”

I stood still for a moment, trying to work this out. When I finally understood, when the truth hit me, something squeezed tight in my chest and my throat started to ache and my eyes filled with tears. A stupid grin was spreading all over my face, and she was smiling at me, and we were both crying.

“Jenny,” I said sincerely, “you’re a fucking idiot.”

“So are you,” she sniffed.

“I know,” I nodded. We looked into each other’s eyes for a long, long moment.

Then I stood up, and I started to undress. I let my gaze take in Jenny’s body. She stretched her arms luxuriously over her head and gave a little sigh. I pulled my jeans down, and my shorts after them. Then I got onto the bed and sat astride my friend’s thighs.

“How many times have you done this?” I asked.

“I dunno,” she murmured. “A couple of dozen. Maybe more.” I had a brief mental image of dozens of nameless, faceless men mounting Jenny, dozens of pricks tunneling into her asshole; all of them merely preliminaries, dry runs, training, for the man she had been waiting for all these years. I took the KY from the bedside drawer and squeezed a generous gob onto my fingers, then I pressed it between her round, soft ass cheeks, softer than any man’s I’d ever known, and she breathed deeply. I put more on my cock, and then I lay full length on top of Jenny, kissing her face and feeling her tremble slightly beneath me.

“I love you, Jenny,” I whispered. “I love you, Pete,” she sighed, and opened her legs a little.

I guided a finger between Jenny’s buttocks and stroked her anus. She drew a sharp breath. I circled the tight little ring of muscle, and then pushed my fingertip into the bud, opening her up. She went “Oh!” and tensed up. I soothed her, stroking her back with my other hand, then I worked my finger further inside her. Jenny made a harsh, low noise in her throat as I pushed my finger up into her rectum, then I gently squeezed a second finger into her ass. She clutched the bedspread.

“Are you okay?” I whispered. She nodded, biting her lip. I moved my fingers around inside her ass a little, loosening her. She grimaced again and her breath hissed through clenched teeth, but she was beginning to open up.

“You ready?” I said.

“Say it,” she breathed.

“Say what?”

“Say what you’re going to do to me.”

“I’m gonna put my cock in your arse,” I said into the delicate folds of her ear, and she shut her eyes tight, squirming a little, and gasped. I pulled my fingers out of her, and guided my cock down between her buttocks. Jenny seemed to press herself into the bedspread, as if to try to get away from me. I eased the swollen tip of my cock up against her anus, and I raised myself over her a little.

“Oh Pete,” she sighed. “Do it.”

I let my weight force the tip of my cock down into Jenny’s arse. She shut her eyes tight and her face contorted, and as her breath came out she went “AANH!” loudly, arching her back. I slowly, but firmly, pushed deeper into her and she let out a guttural moan with each stroke, her fists twisting the bedspread, her face red and shining with sweat, her small body squirming beneath me. I was so aroused I had to force myself to keep from fucking her straight away; I wanted to guide her into it. By the time her anus was closed around the base of my cock, Jenny was panting for breath and weeping.

“Oh, please…” she whimpered.

“What?” I whispered to her.

“Fuck my arse, Pete,” she sobbed. “Please…”

I began to ease in and out of her arse with the longest, slowest strokes I could make. Each time I went in, Jenny relaxed, and her breath hissed out of her; each time I pulled out, she tensed, and moaned thickly. She was holding onto the bedspread tightly, her legs were moving like a swimmer’s. She pushed her hips back against me, forcing herself down on the impaling shaft of my cock and squirming as if she were being pulled in all directions. I speeded up a little, fucking her harder and less gently, and she bared her teeth, her eyes tightly shut, and gasped “Oh Jesus!”

With each stroke that I made, I felt like I was falling into Jenny; losing a part of myself that I no longer needed, finding myself more truly in this encounter with my friend, the woman who felt herself to be a boy, now giving herself up to me utterly and soaking up the pain and the pleasure of it, all the years we had wasted in not admitting to each other that it was each other that we wanted. And I felt that in her tears and her gasps and her moans, Jenny was burning away the part of herself that she had built up over the years to protect herself from the fear that I wouldn’t want her. I reached around Jenny’s waist – how many men had I done this for! – and began to stroke her, discovering the new and unfamiliar topography of her sex, and she let out a shuddering half-scream. I placed my other hand over her face, and she licked my palm deliriously as my fingers pressed into her closed eyes. I buried my face in the damp mop of her black hair and felt my orgasm building. Jenny sprawled beneath me, pushing her face into my hand, feeling my cock bulging into her ass, her naked body shining with sweat as I stretched my legs out over hers and forced myself into her, and I felt her tight little ass muscles milking my entire length as that delicious heat exploded through me and I felt the warm liquid filling her up and flowing around me as she screamed into my palm, shaking and collapsing into a small limp form beneath me.

I went limp too, and sagged down on top of her back, gasping for breath, dry-mouthed and aching. We lay there for a while, too spent to speak, too shocked to find any words, just feeling each other breathing. I could feel a small pulse inside Jenny’s arse, beating furiously. I giggled into the back of her neck and she made a small, muffled giggle in response.

Then I rolled gingerly off her, pulling my slick, softening cock out of her. There was a little blood. I had expected more.

“Are you okay?” I whispered. She lay still for a moment and then, without rolling onto her side, turned her head and smiled at me.

“I’m great,” she breathed. “Can we do it again?”

I rolled onto my back and laughed. Jenny let go of the bedspread, reached down for my hand and squeezed it. I squeezed back. A little while later we got up and had a bath together, talking to each other softly, mostly about things we had done together over the years. We drank some more wine in the bath, then I dried her off and made her bend over while I pushed a couple of blobs of Savlon into her pink, damp anus, smacking her while she giggled. Then we went back to bed.

As we lay in the darkness, our limbs twined together, I felt happy and contented.

That weekend, my mother opened her front door on Sunday evening to find me standing there, hand in hand with a diminutive figure in jeans, an old jacket that was quite a bit too big, and a strange peaked leather cap.

“Hi,” I said. “I think you know Jenny, don’t you, mum?”

“Hello, Mrs Mahon,” said Jenny, smiling and taking off her cap to reveal a short pageboy haircut.

“Hello, Jenny,” said mum, looking confused. “So – um, what should I call you?”

“Oh God,” said Jenny, glancing at me and tightening her grip on my hand. “I dunno. Let’s just say ‘friend’, shall we?”

We went in.

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