Lipstick Lesbian Tales #1: My First Time (Sample)

A few years ago, Claire and I worked as fashion models for a department store catalog. Tedium in the workplace made us hope to hit the big time someday and head to New York to strut the runway. But alas, our dreams remained dreams, and the forty-plus work week weighed on us. Most of the time we spent in the makeup chair waiting for the set call. With a lot of time to kill, we grew rather close talking about sex, men, and fashion. 

I had a crush on Claire since the day I met her, but I never revealed my feelings. I’m straight, but it wasn’t the first time I gushed over a woman. A girl at college and a waitress at my last job both tempted me. I never crossed the line because I thought, “What would people think?” Images of my mother or my current boyfriend scolding me entered my mind to quiet those forbidden desires. Nevertheless, they remained. And over time, they grew into a sexual longing difficult to suppress.

The day started like any other. We arrived early, hit the makeup chair, got done up, and then waited for our call. Waiting could stretch into hours while they perfected the lighting and set. As usual, we finished getting made up, chatted about the news, and killed time.

After a few minutes, Claire rose and said, “Do I look okay?” 

She stood tall and stunning. Her long, dark brown hair flowed silky and straight. Her feline features conveyed mischievousness. Her beautiful lips, painted with heartbreaker-pink lip gloss, framed a slacked mouth more open than closed like Bardot. This accessible quality carried sensuality. Pearly white teeth stressed the lower part of her features. Her eyebrows, plucked to perfection, hinted at refined living. A cerulean blue dress seemed painted on her taut body.

Of course, I said, “You look great!”

She laughed and said, “So do you, honey.”

I lived pretty that day and most others. Nobody ever called me ugly. In those days, I tried to be modest, but I was a model for Christ’s sake. I didn’t like to compare, but Claire and I preferred different styles. I wore my hair in a lighter brown that flowed in luscious spheroidal waves. My skin glowed a brighter white than Claire’s darkly tanned body. I wore my lipstick carmine red like my dress. I looked at my ample bust and then to Claire’s smaller breasts. It was nice to have something on her.

Claire’s voice pulled me out of my musing. “Hey, did you see that new model across the hall?”

“No, I haven’t. What’s her story?” I replied.

Claire turned to the mirror, fidgeted with a hair lock, and said, “Well, I know little about her. I feel silly saying this, but she’s boiling hot. Makes me feel a little lacking.”

I murmured, “Oh, that’s silly. You’re beautiful. Jesus.” I raised my voice a little and added, “I can’t believe you. You’re so gorgeous.”

“No, I’m not. I’m barely thirty and my tits are sagging. My skin isn’t any better.”

“Well, that’s ridiculous. I think you’re beautiful.” I turned and made eye contact with her in the mirror.

“Stop,” she said.

“I’m not joking. If I had a penis, I’d date you. You’re a model for God’s sake, and a pretty one too.” I averted her eyes as I held the chair’s back.

“What if you had a penis? Would you date me?” she said as I felt her eyes on me.

I looked back at her in confusion. 

She moved a little closer, and I realized she had crept nearer inch by inch this whole time. I didn’t know what to say. Was she coming on to me?

“Ha-ha. Just messing with you,” she giggled.

I laughed in relief, but another emotion overcame me. Disappointment, with all its regret, gripped me as I realized I truly wanted her. I needed her comment about having a penis to be serious. An emotional clash raged within until I relented in exasperation. Am I a lesbian? Is it possible?

She noticed I became lost in thought, so she tapped me on the shoulder. I looked her in the eyes. I searched her face for another signal. None came. I turned away.

She said, “Hey, what’s wrong? Your mood changed. Did I say something wicked?”

“No, it’s just that—”

“What?” she interrupted.

Her body moved a little closer. Desire flickered through my loins. Did I want her? Banishing the thoughts again, I said, “I’m not sure…” I hesitated. Why don’t you tell her?

Reading my body language, Claire put her hand on my shoulder to reassure me. Then, she said, “I know what’s going on.”

I asked sheepishly, “You do?”

She nodded, placed her pinky fingernail into her mouth, appeared lost in thought for a moment, and then said, “Can I tell you a story?”

“Sure.”

“Years ago, I was on a shoot. Back when I lived in Chicago. Do you remember me talking about that job? Honestly, it was terrible—just the worst. Long hours. Longer than ours. So much set-up.”

I nodded.

She continued, “Well, I worked many late nights with this wonderful woman. We became the go-to models, so we worked fourteen hours a day. One evening turned out to be especially hard, so by the night’s end we were dead tired.

I studied her face. Her modesty earlier was unfounded. Her beauty scintillated. I noticed this as I studied her long hair styled in 70s retro for the shoot. It swayed silky-smooth and smelled wonderful. I wanted to bury my nose into it, but I restrained myself.

Her voice broke me out of another daydream.

“After work, we headed to a local bar and downed a few drinks, talked shit about the photographer and his leering eyes, and ventured into a deeper conversation. At about midnight, she asked me if I wanted to have a drink at her tenement. I agreed, so we headed over in a taxi. During the ride, she sent vibes that confused me. I thought she was hitting on me.”

My eyes widened and fear overcame me. Did she know I wanted her?

She pretended not to notice my expression and added, “Well, it turns out she was coming on, alright. When we got to her apartment, she put on some dreamy music, poured us more drinks, and then we talked on the couch for about an hour. We chatted about men at work: what we loved about them, what we hated, and if they were hung like a horse.”

She paused for a moment to take a drink of water and then continued, “After about an hour, she leaned over and placed her hand on my knee…”

To Be Continued…

If you want to read the bundled lesbian collection, please check out Lipstick Lesbian Tales: The Bundle or for a print collection see Lipstick Lesbian Tales: The Collection.

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