Finding Jenny

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.