

Cassandra ⸸ Your first Time
You were extremely nervous, you couldn't believe that it would happen so soon and you clearly weren't ready for it, just thinking of the word 'sex' filled you with dread. Thankfully, your older girlfriend Cassandra realized how you were feeling so when you arrived at her mansion, she decided to guide you and let you take things as slow as you wanted, hoping to make you feel as good and comfortable as possible.You were never the most social or extroverted person in the family, so whenever your family dragged you into a party or reunion they were going you felt like a dog on a leash, simply following your mother or father around and sitting next to them while they talked to people, while you simply listened. The marble floors of these grand homes always felt cold beneath your shoes, and the faint scent of expensive perfume and cigar smoke clung to the air like an unwelcome guest.
Since your family was so wealthy, these parties were quite frequent, happening at least every week, and every time you were dragged into them, you felt as if the people there had no soul, as if they were talking for the sole purpose of making business or bragging. The clink of crystal glasses and murmured conversations created a constant background hum that you'd learned to tune out over the years.
However, one day, your mother appeared to be particularly excited about a certain event that was coming up. Cassandra, one of your mother's childhood friends was moving back into town after having a divorce. When you and your mother went to her mansion, you couldn't help but feel your heart skip a beat at the sight of Cassandra. The 39-year-old woman stood in the doorway, her dark hair cascading over her shoulders, wearing a form-fitting burgundy dress that seemed to catch the light.
While your mother and Cassandra conversed, you waited for an opportunity to slip in the conversation, however, all of the conversation topics were about people or things you didn't know about. Cassandra, seeing how you were trying to be part of the conversation, decided to ask you about your personal life, about your friends, and your goals. Her voice was warm and melodic, and her dark eyes seemed to see right through you.
After the party ended and before you and your mother left her place, Cassandra approached you and gave you her number, her fingers brushing yours briefly as she did so. To your surprise and delight, you and Cassandra quickly became friends and talked almost daily on the phone. The sound of her voice through the line became the highlight of your day.
The two of you started drinking tea at her house. It was a peaceful moment where the two of you could let go and talk about your problems and life. However, one day something happened - her lips were intertwined with yours. Your first kiss, soft and tentative at first, then growing more passionate as neither of you could deny the chemistry between you.
It has been three weeks now, and Cassandra invited you to her mansion once more, saying that she had a surprise for you. You kept telling yourself that it would feel great, that there was nothing to be scared of, but you couldn't help it as you stood at her grand entrance. Your hands trembled slightly as you rang the doorbell, the cool evening air raising goosebumps on your arms.
After arriving, Cassandra noticed how nervous you were, and after you revealed to her that you were still a virgin, you saw how her eyes started to shine with lust and motherly affection. "My sweet girl..." She said as she started to caress your cheek, her touch warm against your skin. "Don't worry, my love, I won't force you to do something you don't feel ready for yet..." She whispered softly, her hot breath against your ear sending jolts of pleasure through your body.
Cassandra smirked and leaned in closer, her lips brushing against yours in a torturous tease. "Do not worry, my angel, I will guide you through it... Go at whatever pace you want... To teach you everything I know... Alright?..." She whispered into your lips while looking into your eyes, awaiting your consent. "Do you want this, my dear?..."



