First Time

I was talking to my old friend Julie one night. A long time ago we’d been an item, but afterwards had stayed friends, retaining that intimacy that you have with someone you’ve once bedded. I wasn’t her first, but among her first few.  She’d been married for years now; I had been but am not at the moment, but knew better than to suggest a quick reminder.  We were talking about the modern style of courtship from our perspective as 40 year olds, the scary world of porn-informed extreme stuff that faced the new generation.

“I worry about my daughter Jane,” she said, “she’s never really had much to say about boys but she’s 18 and will be dealing with all this soon. I’d hate for her to have a bad first experience.  I know she’ll need a gentle introduction, but I can’t trust whichever boy she chooses to provide it for her.  They’ll be far too focused on their own satisfaction.”

I’d last seen Jane a year ago; even then she was recognisably similar to her mother when I had dated her, with sultry dark eyes, small high breasts, a slim waist, broad hips and a thigh gap waiting to be filled.  She must be really something by now, I thought.

“I was wondering,” Julie said, “whether you might do me a favour.”

“Of course,” I said, “whatever you want”.

“If she was willing, do you think you could do it? Show her what sex can be like?”

“I’d be happy to.”

I heard nothing from Julie for a few days, and I concluded that the awkward conversation with Jane had not reached a positive conclusion. In the meantime I found myself obsessing over the thought.  In the end Julie texted “Yes she’s up for it – she’ll come over on Friday night.”  I cleaned the flat, trying to tidy away the signifiers of old age. This should be a night she’ll always remember.

She arrived on time and we hugged. I followed her back into the flat, admiring her clothes – a pale satin blouse (no bra underneath), a short skirt tight to her ass, smooth bare legs and thin ankle socks.  We sat in the living room drinking soda  - I didn’t want her to be affected by drink.

She giggled. “Well this is awkward, isn’t it?”

“Your mum suggested it – she said you liked the idea.”

“I do,” she said.  She looked me up and down. I held my stomach in and tried to look my best.  She nodded and smiled, then came and sat right next to me, our thighs touching.  She rested her head on my shoulder, and spoke quietly.

“You will be gentle, won’t you? I’ve heard boys can be rough.”

“I’ll try,” I said, putting my arm around her shoulder, squeezing it slightly.  She turned to me and kissed my cheek; our lips met. I reached for her breasts, and I was surprised to find the nipple already hard. I felt her breath on my neck, and dropped my hand to her thighs, sliding under the skirt to her crotch, my palm covering her lightly-covered mound, my fingers curling between her buttocks, rubbing her perineum and asshole through the cloth. She pushed herself down against me and I could feel a surge of heat and moisture. 

“Come on,” she whispered, “let’s do this.”

I sat back and she stood up, giving her hips a wiggle, and walked over to the bed. She looked over her shoulder to me. “Stay there a moment,” she said.

She turned around and looked down to unbutton the blouse, letting is hang loose before shrugging it off her shoulders.  The breasts were now exposed in their perfect glory.  She pressed them, stroked the nipples, and sighed.  Then she reached down to the skirt, unzipped it, to leave just the panties, slightest of bush hairs visible above the waistband and on the inner thighs. She looked across at me, unapologetic, unashamed. I suppressed a groan of desire and stood up.  She jumped onto the bed, lay back, and slipped the panties off. 

Meanwhile I tried to keep looking at her while undressing myself.  My boxers were straining to contain my excitement; a drop of precum was already visible.  She looked across as I dropped them and stood before her. Her eyes widened.

“It’s so big,” she said in a worried voice, “are you sure it will fit?”

I shrugged. “This isn’t that big,” I said, “but if we’re careful you’ll make room anyway.”

She nodded and watched as I manoeuvred the condom on. I climbed onto the bed alongside her, revisited her breasts, and fingered her cunt. It felt hot and wet.  I moved my head downwards but she stopped me.

“Never mind that,” she said, “I want you inside me.”

I nudged her thighs fully apart and lay on top, supporting my weight on my hands. I felt my prick nudging at her groin. She moved herself gently until I was at the opening, and I pushed in a finger’s width. She gasped and I felt her push herself down, swallowing an inch of my shaft.  So tight, and so wet! I pushed a little further, expecting some resistance, but no, it slid in neatly.

“Yes,” she said, “oh yes”.

I pulled back until I was almost out and slid in again, making her yelp.  Her fingernails dug into my buttocks as she pulled me in tight, my shaft completely absorbed, my balls rubbing against her taint. Still inside her I raised my body and her hips lifted from the bed. I felt her muscles clench around the head.  She screamed as her back flexed and she came.  As her convulsions receded, I felt myself come too. She felt it too – she smiled and nodded.

We lay back, exhausted. 

She looked down at the drooping condom.

“No blood,” she said, “oh well.”

I took it off and tied it up.

“I’m not too surprised, though,” she continued, “it’s a bit late for that. I lost my virginity months ago.”

I paused.

“So what was this all about?” I asked.

“I wanted Mum to stay out of my business, and this seemed the quickest way to make the point.”

She patted my shoulder.

“You did well, though, it would have been a nice first time.”

“Thank you, I tried.”

She reached down to pick up her panties and started to dress.

“Was I better than her?” she asked mischievously.

“Much,” I said hoarsely.

She nodded.

“Right answer. Maybe we’ll do this again some time.   There’s so many firsts to cover.”