When I was 19, I had a brief fling with an older woman. I won’t go into the age difference but suffice to say many would frown. While I can understand people’s fears or concerns, I look back at that relationship fondly. We were two people who knew what we wanted and found it with each other for a time.
For my part, I’d long lusted after older women. Even today, my fantasies often see me adopt the role of a young student being taken by a powerful, wilful teacher, or perhaps being the shy girl next door seduced by a domineering neighbour. Back then, I was still adjusting to my sexuality, breaking away from the bonds of almost two decades of conditioning that I should be straight. I wanted someone with experience, who could help me be who I truly was. She, along with several others during that time, took on that role. I’m forever grateful for it.
For her part, she worked a stressful job. She had neither the time nor inclination for committed relationships. She just wanted someone who would be ready to fuck when she needed to relax. Somebody who could be there when she wanted to vent. A girl who wasn’t going to ask more from her than she could give and instead be satisfied with what she could offer.
On one particular night, I had arrived at her house bringing with me some wine and a couple of packets of menthol cigarettes. She’d prepared a light meal for the two of us. Savage Garden played in the background as it so often did when we got together. I blushed as she complimented me—she was always forthcoming with compliments.
Any hang-ups I had about my body disappeared when I was with her. Those birthmarks I had grown to hate growing up had become a source of pride. My breasts, which sit between a B and a C-cup no longer felt quite so irritating. When I was with her, I felt like the most beautiful girl in the world. The way she’d stroke my cheek, whisper into my ear and plant gentle, lingering kisses on my lips always made me feel so desired.
Her hand down my top, my nipples between her fingers and her hot breath on my neck, she pushed me down on the couch, straddling over me but before she could go further, her phone rang. I tried to get her to ignore it but to no avail. A friend was calling, upset about something that had happened earlier that day.
She agreed to her friend coming over for a bit. The youthfully selfish side of me was slightly put out about this and I asked whether she wanted me to leave. She said no, and instead slipped twenty quid into my hand and asked me to pop to the off licence for more booze.
By the time I got back, her friend was already there. I had briefly met her before, but she didn’t recognise me. The two chatted, consoling each other over their various stresses while I sat quietly, sipping some Smirnoff Ice and smoking some cigarettes. I felt like a bit of a third wheel, in all honesty. Occasionally one of them would ask me something, and I’d try as best as I could to involve myself in the conversation but soon, they’d be skipping down memory lane again, reminiscing about times that I never knew.
By the time the clock hit 1am, a fair amount of alcohol had been consumed. Whatever had been bothering my date’s friend earlier seemed a distant memory. At that point, the conversation started to change.
My date asked me to come lay across her lap, drunkenly joking that I had been neglecting her. I did as she asked, and at first, she merely continued chatting with her friend while absent-mindedly caressing my body through my clothes. Before long, my date and her friend were discussing their respective love lifes, or lack thereof, and as they did so, the hands caressing my body began to find their way underneath my clothes. As though it were the most natural thing in the world to do in front of her friend, she unbuttoned my jeans and slid her hand down into my panties.
At that point I noticed her friend’s eyes on me. She looked me up and down, both confused and intrigued, as my date played with my cunt.
“Do you mind?” my date said, flicking her eyes towards her friend.
I shook my head.
Her friend shuffled a little closer, a nervous curiosity written on her face. My date gently slipped me out of her lap and onto the floor and removed my top.
“Is this OK?” her friend asked.
“You can say no,” my date added.
Instead, I nodded. The mix of curiosity and hunger in her friend’s face turned me on. As she reached out, I took her hand and placed it on my breast and leaned forward to kiss her. As she gave in to her own desires, our tongues finally met, swirling in each other’s mouth.
My date stood up and took a pack of cigarettes. “You two can use the spare room if you like, but I’d like Sara back at some point.”
And with that, she kissed me on the cheek and went upstairs.
Her friend and I continued to kiss. She seemed enthralled by my body, not wanting to take her hands off it. Eventually, she suggested we go to the spare room and I followed her. No sooner had the door closed, but her arms were around me. We kissed some more until she pulled back nervously, her prior confidence giving in to doubt. She told me she wasn’t sure what to do next.
I wasn’t used to being in control during encounters with other women, but I was pretty sure she’d never had any. Locking my fingers with hers, I led her to the bed, laying her down and slipped her clothes off. She asked whether I was sure, and I planted a kiss on her soft, nervous lips. Her body responded to my every touch. Each kiss met with a moan or gasp, every soft caress met with a hesitant writhing. I wanted her cautiousness to dissipate, and for her to let herself go.
In that moment, she was an angel with flowing auburn locks resting on perfectly formed breasts. I fondled every inch of her, teasing her with my fingers, and then my tongue, until the breathless cries of “please” and “don’t stop” trickled from her mouth. As she got closer, she finally truly lost herself. Her hands wrapped around the back of my head, forcing me into her wet slit that ground against my mouth until she came, legs quivering around me. To this day, the sight of a beautiful woman in a post-orgasmic haze is as satisfying to me as an orgasm of my own.
Once she had collected herself, she giggled for a while. We held each other and kissed some more until she told me I best run off to the other bedroom. I kissed her goodnight and joined my date, who simply thanked me and told me to lie back while she gave me a little reward.