Part 1
I sat outside the coffee shop in the warm breeze, slowly spinning the paper cup in front of me. I chuckled at myself for still feeling butterflies... I'd met many women to role-play fantasies with this way, but still. You just never know who's really going to show up.
"Are you Eric?"
I practically jumped out of my seat as I heard her voice behind me, but I slowly turned and could hardly believe my eyes. This girl was very young... barely college age, and stunning. She was very petite, a little over 5 feet tall, thin and slender with perky breasts that I could barely keep my eyes away from. Her legs were nearly bare as just a short jean skirt covered her bottom half, with a tight tank top that barely revealed a flat, toned stomach. "Ashley." I smile. "Have a seat."
She smiled and seemed to sigh in relief. I wondered to myself how many times she had tried to meet men this way and ended up not getting what she bargained for. She sat at the table and started gently stroking her hair, and gorgeous green eyes making fleeting contact with mine. "Sorry, I'm just a little nervous."
"No problem." I gazed deeply into her. "So tell me what's on your mind."
She pushed her hair behind her ear, took a deep breath, and sighed slowly. Her eyes met mine and held them. She began trembling visibly, her petite hands shaking and gripping each other to try to mask it. I leaned forward and took both of her small hands in one of mine and squeezed them softly. "It's okay. You don't have to be scared."
"I'm still a virgin", she blurted out suddenly. I did my best to mask any surprise, and remained silent. A sexy girl like this? A virgin? You've got to be kidding me.
"I mean, I don't want to be. I'm nineteen! And I've had boyfriends. Lots... of boyfriends. And I WANT... to... you know. And I've tried to, a bunch of times." I watched her carefully and let her continue. "But... every time, right when we get to the point when... you know... well, I get really..." Her voice barely cracked and her lip quivered almost imperceptibly, "scared. And I start to, maybe, freak out a little bit. Every guy that I've been with, when we get to that point, and I start... you know, freaking out, he gets scared of pushing further and stops. My last boyfriend...." Her voice trailed off and a tear formed at one eye, but she quickly swept it away. "He tried really hard, and I really wanted him to do it. I begged him to just do it, no matter what I said, I begged him to not stop and just... take it from me. And he said he would, but, when he was about to do it, I really freaked out. I think I might have hit him or... scratched him maybe. He got up and left. He... he broke up with me the next day... with a... text..." Her voice trailed off and her lip quivered, her eyes welling up. She wiped the tears away angrily and shook her head. "Sorry."
"It's okay, you don't have to say sorry." I studied her for a moment. "So, if I'm understanding you correctly, you'd like my help getting past this."
"Yes, exactly. I need a strong, confident guy... like you... to just... you know." She sighed, and her eyes flashed with anger... maybe even hatred. Hatred at the weak men who had dated her, who didn't have it in them to give her what she needed. Her eyes bored into mine, "Just take me. Take me and, no matter what I say or do, don't stop. Just... take it from me. I want to put this behind me. I want to... be able to have a normal relationship with a guy."
I nodded slowly as I carefully studied her. I almost sounded too good to be true, but I could tell she was sincere. Her eyes practically begged me. "When would you like to do this?"
She stroked her hair again and breathed deeply, visibly calmer now. "Are you doing anything right now?"
Part 2
The drive to my house was made mostly in silence, other than a little small talk. She was surprisingly calm... hopeful, even. From time to time I would turn my head and gaze at her body, letting my eyes wander down her soft, delicate neck, undressing her with my eyes, my cock bulging in anticipation as my glance fell to her slender legs, that short skirt that barely covered her tight virgin pussy. I took a deep breath, taking in her soft scent, as I pulled into my driveway.