Older Women Pt. 01: Alanna

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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 topkapı escort 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.

“Ok. Let’s talk about this.” She pulled away, but grabbed my hand and pulled me after her.

I expected we would sit in the living room, or the garden, but she kept on going, down steps to the lower end of the house, where the kitchen and her bedroom was, I’d never been inside before.

She led me in, pulling me over to her bed. It was large, a king size, with a rough-hewn piece of wood as the headboard, and a large blanket on the diagonal over her duvet. She kicked off her shoes, and then crawled on top, where she lay on her side, looking at me. She patted the adjacent space on the bed.

“Come talk to me.”

I joined her, also lying on my side, about a foot from her. We lightly touched fingers and played with each other’s hand.

“Yes, I meant it.” I smiled, and tried not to blush (although of course I did).

Alanna took charge, as she often did. And, frankly, I didn’t want to push things, so was quite happy for her to decide what to do next. She told me to grab some beers from the kitchen, and some towels from the linen closet, then take off everything except my boxers. I was to set everything up outside, and she’d join me.

I over-eagerly bounded from the bed (as she told me later), gathering everything as instructed. I had been dressed in shorts and a t-shirt, boxers and birkenstocks, so it didn’t take me very long to get naked. It was still very hot when I got outside into the garden, so I selected the side where we’d be mostly in the shade, with good views of the river. I placed the deck chairs next to each other. The garden had a section of bushes creating a kind of barrier between Alanna’s bedroom and where I put the chairs.

I lay down on the towel, crossed my arms behind my head, closing my eyes to bask in the sun. It was only a few moments until Alanna came out to join me, I had been straining to hear her footsteps in the grass.

“Don’t open your eyes, not yet.” I heard her drag her chair so it was actually touching mine — I had laid them about two feet apart. “If we’re going to do this, we need to be close enough to touch. I’m surprised you brought both over.”

I rolled towards her voice, my eyes still shut. I knew she wasn’t lying on her chair, she must be standing next to it.

“Okay. Are you sure you want to do this?”

“Yeah.” My pulse drummed in my ears. “I’ve been thinking about it … well for a while.”

“Okay. Then you can open your eyes”

I was still wearing my boxers as she’d asked, but Alanna had changed completely. She was wearing a long, very sheer silk robe, tied loosely at the waist, and a pair of tall espadrille wedges, d’orsay, black with an ankle strap. I knew she had bought them a couple of weeks before, we had gone shopping to buy things for her trip. I had fantasized about them on a number of occasions, including the day before. She had told me about the robe, she often told me about exes who had bought her lingerie and various gifts, which she still had.

“I thought we’d start like this. Partially because of the tease… ümraniye escort and partly because it might be fun for us to take off the last things together.”

Alanna lay down on her deckchair, the robe draping, and took her beer from me. Looking pointedly at the distance between us, she crooked her finger. “If you want, you can come closer.”

Underneath the robe, she was totally naked and it was everything that I had dreamed about and nothing like, at the same time. I had definitely had started to identify a certain aesthetic that for me was the ideal older woman, but to be honest I didn’t realize until writing this now how much Alanna influenced that development. She was taller than me, just, although I loved it when she wore heels (which she rarely did). Curvy. I’ve always appreciated more buxom women.

Alanna’s breasts were perfect. Large, round, and rather lower set on her chest than one might have expected from what she usually wore (she had excellent and gorgeous bras). Oval areolas, taller than they were wide, and both slightly at an angle. Her body was right and perfect, and gorgeous. I loved the way that her breasts hung while she lay on her side, looking at me. I was transfixed.

She chuckled and I blushed. We opened our beers, and we talked for a while about her trip. She asked about a date that I had gone on. I always appreciated her asking lots of questions about dates, because I felt intensely curious about her dates and her sex life. When our beers were drunk the conversation sort of ground to a halt. She asked another question, and I answered it, then our eyes met. Her gaze was level.

I honestly couldn’t say how long she’d been watching me, because I hadn’t been looking at her face. I was admiring her body, every inch and angle that I could without moving so much that she’d notice. Of course she did notice. Not just my gaze, but my hardening cock, and the dark spot slowly growing on my boxers from my precum.

“Is this what you had in mind, when you thought about us being naked together in my back garden?”

I just nodded. She gently used a finger to cause a ripple in the hem of her gown. “Really, this was it? Things didn’t go any further?”

I looked up at her, finally meeting her eyes. She wasn’t teasing me, she was earnestly curious and a bit quizzical. “No, I thought about other things too.”

“Just now, or before as well?”

“Definitely before. Since Choir tour.”

“Have you thought about us in the garden naked, or just fantasized about me?”

“Fantasizing… thinking about us together in the garden ever since I moved into my apartment” I flapped my hand, vaguely in the direction of my building.

“I guessed you might have. Would you be comfortable if we took this to the next step?”

“What is the next step?”

“I’ll take off my robe, and you can take off your boxers.”

“Okay. I’d like that.”

“Do you want me to keep my shoes on? I thought you might like them”

I nodded. Alanna reached over, and gently lifted my chin so that I was looking at her.

“Are you sure you’re comfortable doing this? I don’t want to mess anything up. I’m not going to leave the choir, I’m not giving things up.” She was firm, determined.

“Yes, I do.”

She stood up, undid her robe and set it on the end of her lounger. I was, much less dignified, I simply rolled onto my back, pushed my boxers down with both hands, and left them on the chair by my feet. Alanna lay back down, slightly further away than she was before. She looked at me, smiling slightly. I was grinning like somebody whose dream had come true.

“What comes next?” I asked.

“Well, I’m not sure. You know I don’t plan my fantasies out as detailed as you.” She reached to tap me on the nose. “But, we don’t have to rush. Let’s get comfortable with this first.” she moved back on her lounger. “Come join me, please? We can talk, if we want, or just relax.”

So I did, and we spent the first while facing each other, my upper hand on her hip, and her upper hand on my leg. At first we didn’t talk about sex, but we did later. Alanna enjoyed watching my cock get harder (she teased me gently when it got softer again.. though never for very long).

I loved watching her nipples get harder, and the way she squirmed slightly, and got wet as we talked about the various fantasies I’d had. (Not all of yenibosna escort them, but a few.)

We got hungry, made dinner, and then afterwards she put back on her robe back on, and offered me a lightweight one. The night ended with us cuddling and watching a movie together, then I got dressed and returned to my apartment.

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.

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