My First Time with Anni

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A young woman's first time with a waitress.
2.6k words
4.47
58.7k
43

Part 1 of the 2 part series

Updated 10/16/2022
Created 07/13/2014
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"Oh no, don't tell that story!"

Freddy winked and smiled at me from across the table. "Well now you know I have to." He looked at the other two people and began without pause, "We went to pick up some of Cass's crap from Jeremy's place." Everyone, including myself, made a face at the sound of my ex-boyfriend's name. "Yeah, I know. Of course he was sitting in front of his computer, hand down his pants and screaming racial slurs at the poor people on the other end of his headset when we walked in. He hadn't even gotten up to let us in. Told us is was open. So, we walked into the bedroom and started grabbing everything of Cass's. I looked at the nightstand and saw this thing sitting there and asked her what it was. She looked up and, without missing a beat, informed me that it was the penis cozy she'd knit him." By this point in the retelling, Freddy was almost doubled over laughing and clutching his stomach. Across from me, Tammy was wiping tears from her eyes and shaking her head.

"Oh God, Cass," Andrew said to me. "Why?"

I shrugged and sipped my margarita before saying, "It was all I could make. It started as a potholder and..." It hit me: the absurdity of it, penis cozy and all, and I began laughing hysterically. My one and only knitting project had been a cozy for my ex-boyfriend's penis.

"Do you guys still need a minute?" our waitress asked, looking at us suspiciously. We must have appeared crazy, the four of us mid-hysterics, if you did not know the cozy story. She looked to be in her mid-twenties, had long blonde hair and the greenest eyes I'd ever seen. They have to be contacts, I thought.

"No," Andrew said. "We're ready."

We gave our orders and she took the menus. When she grabbed mine, our fingertips touched and a shiver ran up my spine. Stupid, I thought, but when I glanced up, she was staring at me. I'd never been with a woman, even in college, but there was something there.

A second after she left, Freddy whistled. "Girl."


"What?" Andrew asked. Tammy smiled and kissed him on the cheek.

"It's always the straight mend who have the worst gaydar," Freddy said.

I hit him. "No, it wasn't anything like that." But my protest sounded weak, even to me.

Tammy shook her head. "I don't know, Cass. She's cute."

Freddy nodded. "Go for it. You deserve a little fun after all the crap you dealt with with Jeremy." Easy for you to say, I thought. You've been out since you were fifteen. I'd always found some girls attractive, but I'd never thought of myself as a lesbian.

When the check came, Anni had written, "Thank you!" with her phone number underneath. Freddy shoved it in my purse.

We parted with Andrew and Tammy in front of the restaurant and walked to Freddy's car. He and I had been roommates for two years and it was great. We were both neat freaks with a touch of OCD, never fought over the same guy and loved eating Ben and Jerry's Phish Food while watching Disney movies on Netflix.

"You'll thank me later," he said without preamble when we got in the car.

"What?"

"Anni's number." He turned to face me. "Call her. She was into you. I know these things. And you do deserve it."

I nodded. He was right. Freddy often was. I'd been with Jeremy for eight months before things went south. Then, I'd stayed with him for another miserable three before finally calling it quits. Honestly, he was so addicted to video games that I don't know if he registered my absence. Well, probably only when he got hungry and had to leave the virtual world to fix himself a sandwich.

When we got home, we said goodnight and went to our rooms. I washed my face and changed into sweats and a tank top. Sitting on my bed, I held my phone in one hand and the receipt in the other. I debated with myself for ten minutes before I dialed.

She picked up on the third ring. "Hello?"

"Hi, it's Cassie, from tonight."

"Table seven, pasta primavera." She laughed, a deep, smokey and seductive sound. "How are you?"

"I'm good, thanks. Is this an okay time for you?"

"Yeah, I just got home."


"How are you?" I settled back against my pillows and stretched my legs out.

"Better now that you called."

I smiled and felt a pull low in my stomach. We stayed up past midnight taking and made plans to get coffee the next morning.

I couldn't find anything to wear. I had half of the contents of my closet on my bed and the other half scattered across my floor when Freddy knocked at nine. "What happened?"

"I'm having coffee with Anni in thirty minutes and I don't know what to wear. Guys don't care as long as they can see a little boob," I whined.

Freddy walked over and took my by the shoulders. "You're over-thinking again. Wear what you feel comfortable in. It's just coffee." He smiled. "Lesbian coffee, yes, but coffee nevertheless."

I hit him on the arm and smiled. "Not helping, Fred."

He fished out a pair of dark skinny jeans and a green sweater. "Wear your black sandals and curl your hair a bit." He kissed my cheek. "Have fun. Tell me everything later."

At nine-twenty, I walked into the coffee shop a block away from Anni's restaurant and saw her sitting at a table by the window. She smiled and stood as I approached.

"What do you want?"

"Oh, um, I can get it."

She shook her head. "No, I asked you out. So tell me what you want or I'll get you the craziest drink on the menu."

I laughed. "Okay, grande vanilla latte."

She nodded. "Be right back."

Over two rounds of coffee and a split blueberry scone, we talked about everything. I learned that she was an only child; I have an older sister. She was raised on the East coast but had moved to the West when her parents divorced ten years ago to live with her mom and swore she was never living through another East coast winter. I was born and raised in the Bay Area but loved to travel. She'd dated boys in high school and came out during her freshman year at a public university an hour south of here. I'd had three serious boyfriends but didn't think I'd ever get married.

We went to a bistro down the street and had lunch. The more we talked, the more I feel for her. Everything from the way she moved her fingers while she talked to the impressions she did of people as she spoke of them pulled me in. She was light, funny and beautiful. I found out her eyes were natural, not contacts though she did dye the ends of her hair. I had forgotten what it felt like to go out with someone and talk for hours. There were no lulls, no pauses or silences during the four hours we spent together that day.

Her shift started at three. I couldn't believe my disappointment as she walked me to my car.

"When are you free next?" she asked. "Maybe we could get dinner and a drink?"

"Yeah, that sounds great. How does Monday work for you?"

"Perfect," she smiled. "We'll go to that new steak place downtown." Before I knew what she was doing, she leaned over and kissed my cheek. "Say seven?"

I nodded. "Yep. See you then."

Monday was only day after that, but time stretched out into what felt like months. I could barely concentrate on simple tasks. I almost broke two glasses washing the dishes and stained a load of whites an okay shade of pink. Freddy looked at me with pity as I walked by with my laundry basket.

Finally, Monday night arrived.

She picked me up at seven on the dot and looked amazing in a deep purple top that brought out her green eyes, black pants and a gray leather jacket. I was glad I'd dressed up a bit in dark wash skinny jeans, a floaty blouse and heeled boots. She shamelessly looked me up and down. I blushed when she said, "Damn but do you look good."

The steakhouse was new and owned by the same couple who owned the restaurant Anni worked at. We got the best table in the house, a complimentary bottle of Chianti and more than a few glances from other diners. I kept fidgeting with my napkin. It was weird, being out with a woman. I felt like people couldn't tell if we were friends or more, but they were going to stare until they figured it out.

"Relax, Cassie," Anni said after our salads were served. "You look like you're breaking the law instead of having dinner."

I felt horrible, not because she'd said it harshly, but because she was right. "I'm sorry. This is lovely. I'm just not used to..."

"Being stared at? Because I'd think you would be by now."

"Why?"

She laughed. "You're stunning." I snorted but her face remained serious. "You think I'm joking? Cass, you're beautiful. I'm sure people stare all the time."

"Um, thank you."

She smiled. "Just relax."

I nodded. "I'm not used to being out on a date."

"You think this is a date?" My stomach dropped until she winked. "Gotcha. Why aren't you used to dating? Haven't done it in a while?"

"Yeah, partly. I mean, I've been on a few blind dates since I broke up with Jeremy, but something was missing. That spark, you know?"

She looked at me and said, "Oh I know." She sipped her wine. Every time her lips, stained by her lipstick and the wine, wrapped around the rim of her wineglass, I got a little wet.

We finished dinner and she asked as she paid the check, "Would you like to come back to my place for that drink? I'm just a few blocks away in the square." I nodded. I couldn't imagine what we would do once we got to her apartment but I couldn't wait to find out.

"Wow, this place is amazing," I said as she took my jacket. Her apartment had twelve foot ceilings large windows that looked onto the town square below, exposed beams and a fireplace.

"Thanks. It works for now," she said. She walked around the counter, opened the fridge, pulled a bottle out and asked, "Chardonnay okay?"

I nodded and she took two glasses out of the cabinet. She poured without spilling a drop and handed me one. I sipped and was surprised at its smooth, crisp taste. "Wow, this is really good."

She smiled. "Thanks, I got it from the restaurant. Want to sit on the couch?"

We sat and talked for a bit. I felt the wine going to my head. It was that buzz you get while the alcohol takes the edge off yet you're still in control. I could smell her perfume. it was musky, heady and more intoxicating than the wine. At one point, she leaned over to put her glass on the coffee table and her hair fell off her shoulder, exposing her white neck. My pussy clenched imagining licking the tender spot where her neck met her shoulder.

She sat back, propped her head on her hand and looked at me. "I want to kiss you so much right now," she said. There was no push behind her words, no force, just desire and fact.

I set my glass next to hers and said, "Okay."

She leaned close so that our noses almost touched, held my head between her hands and pressed her lips against mine. They were the softest lips I have ever been kissed by and tasted of the Chardonnay. I reached up and pulled her closer. She responded by nipping my bottom lip. I opened my mouth and allowed her tongue to invade. I shifted so that I was straddling her without breaking contact. My hips rocked back and forth. The friction between our pants and her finger pinching a nipple made my pussy wet.

"You want it?" she asked.

I moaned, "Yes."

She laughed softly, leaned down and sucked my nipple through my shirt. Her eyes were open and locked onto mine. It was the most erotic thing and I bit my lip as she sucked harder. It pulled from my tit to my pussy and I rocked harder on top of her. The pain was exquisite. Her cool fingers lifted the hem of my shirt and lazily made their way up to my bra. I pulled my shirt off, not caring that anyone below in the square would see everything. Let them watch, I thought recklessly as she sucked my other nipple through my bra while kneading my other tit wet from her saliva. When I almost couldn't stand it anymore, she unhooked my bra and I finally felt her hot mouth take my nipple in. She pulled, sucked, nipped and flicked my nipple with her tongue. When she used just the tip, I exploded, soaking my panties.

After a few seconds, she began clawing at my pants and I tugged her shirt off. Soon we were both just wearing our underwear.

She slid out from under me and said, "Lie back." She knelt on the rug and spread my knees. There was a wet spot on my panties that she kissed before pulling my clit into her mouth. I arched my back and clawed at the couch. Every time she tugged, my climax built inside me. I propped my feet on the coffee table to let her eat my entire pussy.

"You're so wet," she whispered against my pussy lips as she pulled my underwear off. Her tongue licked the length of my slit. I moaned and closed my eyes. I felt her stick a finger inside me while her mouth worked my clit in circles. My orgasm rolled through my entire body and I saw stars.

It took a minute for my body to stop shuddering. I leaned down and kissed her, tasting myself on her lips.

"Now you," I said. She nodded and sat on the couch. I leaned down and sucked the hard bud of her nipple. Her breasts were full, bigger than my C cups, and I loved the feel as I held them in my hands. I lowered my hand to her underwear, easily found her swollen clit and flicked it.

"God," she moaned. "Yes Cass, more."

I flicked her nipple with my tongue and rubbed her clit faster. I could tell she was getting closer, I so said, "I want to taste you."

She smiled. "I've wanted you to say that since I met you."

I kissed her breasts, her chest and stomach and the top of her underwear, loving as how I got lower, her breathing intensified. With one tug, I had her underwear in my hands.

"Smell them," she said. I looked her in the eyes, brought the thong to my nose and inhaled her musty pussy scent. She moaned. Her pussy was shaved and I could see the lips shining. I wrapped my mouth around her clit, sucked the nub into my mouth as I reached up and played with her nipples. She pushed her pussy into my face and I stuck a finger into her hole. I pulled, sucked and fucked her until I felt her pussy walls contract around my finger as juices leaked out.

She pulled me into her lap and kissed me. "God, that was amazing. You eat pussy like a natural. I can only imagine what you'll do with a strap on."

My stomach clenched. The night was only beginning.

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4 Comments
fishingrod48fishingrod48almost 5 years ago
Well Written

I hope you plan to continue this because it's brilliant

plumberdonplumberdonover 9 years ago
Beautiful

Loved it. Nice job of building up the feelings. Do write more on Annie. Thanks

visioneervisioneerover 9 years ago

Well-written and very erotic. Beautiful build up to the sex. Nice work.

AnonymousAnonymousalmost 10 years ago
Can't wait for part 2!

Love the sexy buildup & delivery here. I hope you'll continue this story! I can't wait to read more.

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