Older Woman, Younger Man – Guest Post





A  formative relationship has fed into a love for nudity and for older women. Here in part 1 @CanadianErotica, who has travelled and lived many places while studying, is my guest writer.  Enjoy his story about Alanna:

I met Alanna, who is 6 years older, when she and I sang together in my University’s choir. At first we weren’t in the same choir- she was Chamber choir while I was Symphonic. I’d see her leaving rehearsal just as I was arriving for mine. Alanna is taller than me, with a dark complexion. For the longest time she had fairly short hair (which looked terrific on her). She had one cheek pierced and was, frankly as sexy as hell.

At the end of the year, I was invited to join Chamber choir for a choir festival, so I finally properly met Alanna. Being a baritone when she was an alto, we were often placed next to each other. We started chatting and going out for dinner. We got much closer on the trip having discovered we liked the same kind of pub. After rehearsals/performances, we would go drinking, then walk through the harbour then back up to the university. We’d hang together in one of our rooms until either her roommate or mine arriving made us separate. 

In many ways, Alanna became my social mentor. I was in my first year of university, and she had recently finished her Masters in languages. I was dealing with social awkwardness, meeting so many new people. She stuck by me which helped me navigate social situations. She advised on all kinds of things from how to approach girls, to finding a job so I could stay in Guelph that summer.

It was one of those friendships where it clicks, and rather quickly you’re comfortable with each other. Returning from the festival, we were living in different cities again, but talking most days on one form of messenger or another. When I moved back for my next year of university, it was like we hadn’t been separated at all. 

She was older than me, which was part of the reason why I liked her so much; somebody older thought I was valuable, wanting to talk and be my friend.

In my second year another friend encouraged me to explore my sexuality. I told Alanna almost everything that I did or tried. Sometimes over messenger, but more often at her house – which was always cold. We would huddle together, wrapped in blankets and drink whiskey. Another year passed, and we stayed close. 

Alanna was one of the first people I told about being interested in other men. I was always keen to hear about the men that she dated. Since Alanna was bi, I’d been able to get her advice on all things emotional and practical.

The summer after my third year, I decided to get a job and stay, instead of moving home. I got an apartment with another friend, but they ended up moving home after a month, leaving the apartment to myself for the summer months before another student moved in to sublet. I really enjoyed the privacy of the apartment – on the 5th floor, it looked over a river. Alanna and I were still close, she lived on the other side of the river, renting a wonderful home with a private garden, and even better, a small pool. 

I had a great job doing web development and Alanna was working at the local bakery. Alanna was recently single, as was I, but unfortunately we’d never got together. However, we had a lot of fun: talking about sex, cuddling and being comfortable. I liked to meet her at work, then we’d walk back to her place. In the kitchen I’d grab us some beers, while she changed into more comfortable clothes. We’d hang out in the garden, or in the pool. The owner of the house had two large deckchairs and Alanna and I used them to sit and chat. One chair could accommodate the two of us lying side by side, or sitting on it to play cards.

One night I was pretty tipsy. We had been drinking and cuddling in the garden, listening to the birds and talking about a really disappointing date she’d endured the previous night. I blurted out that I’d been wondering exactly how private her garden was … Because I harboured thoughts about being naked in it. She paused – then asked if any of those thoughts had included her also being naked. Yes, of course! 

“I hope you’ll tell me about them eventually”, she smiled. Then we resumed snuggling, since it was quite late.

Soon after Alanna visited her family in the States, but she sent me a text a couple of weeks later, immediately she got back. 

 “Do you want to get a drink this afternoon?” 

I did, it was stupidly hot and I’d had a long frustrating week. So frustrating, in fact, that I had booked the next day off work to create a long weekend. When I got to the pub across the street from my house, Alanna was already sitting at a table on the front porch, drinking a beer. She greeted me with a big hug.

“Why don’t we sit inside where it’s cooler?” I asked her. 

I don’t really deal well with the heat, but Alanna was even worse. However, she said that it was too crowded inside, she preferred to sit outside so that we could talk in relative privacy. She paused, looked over my shoulder as the approaching waiter. He took my order and then left.

“What do you want to talk about?”

“Did you mean that thing you said … in the garden?” 

I blushed, but nodded. She knew I wasn’t really comfortable talking about in public. It was a kind of game Alanna and I played from time to time, talking about sex in semi-public. I couldn’t deal with it today, so I evaded the question.

“Do you want to talk about this here, or shall we go to your place and talk there?”

I don’t think either of us had ever finished a pint so quickly. We left cash on the table, and made our exit. We were both acting casual, as we were walking. I tried to broach the topic, sensing the boundaries of our relationship were about to change, but she shook her head. 

“My place, remember?” 

So we talked about her trip until we reached Alanna’s driveway.

[To be continued …]


This post is linked to #SnakeDen’s AtoZ – O for Older Woman and #Tell Me About – Limits and Boundaries

7 thoughts on “Older Woman, Younger Man – Guest Post”

  1. Pingback: Watching While My Friends Fuck You - Posy Churchgate ~ Pillow Talk

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