Older Woman, Younger Man (3) – Defining Moment

The slow burn of flirtation & teasing between good friends reaches a defining moment in this third segment.   [3 minute read]

Image by Victoria Borodinova on Pixabay


This Guest Post is part of a reminiscence written by Canadian Erotica – who makes no secret of his fascination for older women.


We didn’t see each other the rest of the weekend, as Alanna went to the local music festival. But our intimacy had settled into a nice routine. We hung out two or three times a week, usually ending up in her backyard at the end of the night, especially if the weather was good. We weren’t always nude, but at most times we were only partially dressed. I finished work before her, so sometimes we’d make plans to meet up right after. She showed me how to get in without the key, so I could go over after work, and relax in the garden, or work on my laptop until she got home. 

We developed a code. If she was in the mood for us to go nude together, she would text me when to come over, adding “Don’t bother to bring your swimsuit”. If she texted me early in the work day, those messages made it difficult to concentrate, but it was worth my while.

We frequently discussed my fantasies and each of our turn-ons. In a few short weeks things moved forward, sexually. We progressed from cuddling and the rare grazing touch, to each of us masturbating then texting each other about it afterwards.

I think that ‘bemused’ was the best word to describe Alanna’s initial reaction when I told her a prime reason I enjoyed fantasizing about her was that she was an older woman. 

“Six years! Just!” was her reaction, and she lightly flicked my chest. We faced each other on one of the deckchairs, in the middle of the garden, a few weeks later. She tapped her finger on her pursed lips, thinking. “So what is it about me as an older lady that turns you on? Just that you can have me?”

“Can I?”

“Maybe, but you didn’t answer the question.”

So I explained that I was attracted to her, despite being younger. She did her quirky smirk thing, and ran her fingers down my chest, over my boxers, and for the first time slipped her hand through the opening to fully wrap her fingers around my cock. She leaned forward and whispered in my ear.

 “I bought something special for you today… I think you might enjoy it. Stay here. Don’t touch your cock. When I text, come into the bedroom through the garden door.” She squeezed again, grabbed my boxers to pull them off of me, and walked back into the house.

I did as instructed. I lay back, arms behind my head, careful not to touch my cock. After a short time, my phone buzzed.

[come in, loverboy]

The door to her bedroom was left open. “Just close the screen door”. She was in her walk-in closet. “Don’t come and look. Sit on the chair, and close your eyes.”

I heard a rustle, and a click of heels. What felt like her (gloved) hand trailed gently over my chest and thighs before settling on my cock and squeezing it. “Now, you may look”.

Alanna was standing in front of me, hips canted to the right. She had on a pair of shoes I hadn’t seen before – Slingbacks with  a long pointy toe, and a sexy stacked heel. She’d teamed these with patterned tights, an amazing pencil skirt and jacket, worn with a bra underneath. She had applied classic red lipstick and wore a hat, with a veil, the kind you see in a 40s noir film.

“What do you think?”

“I think I want to lift up your skirt and fuck you”

“In a rush are we?” But she came over, hiked up her skirt and straddled me. 

Her heels dug into the backs of my legs, and I could tell she wasn’t wearing any panties. She shifted so that she could move back and forth along my shaft. She was already quite wet. I always liked to see how wet I could get her when we talked about sex.

“This will just get in the way really”, she discarded her jacket onto the bed, next to us. 

I pulled her in close to me, revelling in kissing her, and feeling her breasts in the satin bra pressed against my chest, as she ground on my cock.

~ ~ ~ ~

That was not our only time together, but was the beginning of a fun few weeks before school started again. That fall we both started dating others, then later we grew apart a bit when I moved to do my MA. It wasn’t until I was in the UK doing my PhD that we grew close again. In some ways, it was just like before, talking about dates and sex and similar kinds of intimacies. But we were both older, so the older woman/younger man aspects of my previous fantasies had been replaced by other things that we shared. 

That summer with Alanna was pivotal, being the first time I acted directly on my fantasies about an older woman.

I’ve linked to Kilted Wookie’s #PenisProject and #4Thoughts and Fiction : Defining Moment Follow these links for other great content


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