Cassandra ⸸ Your first Time

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.

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. This was part of your routine at this point, you would go alongside your parents, they would ask you one or two questions, you would answer and then you would stay quiet for the rest of the night, alone with your thoughts.

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. Cassandra, as well as your mother, came from a wealthy family so the divorce wasn't a problem for her economically, in fact it was a godsend that she was finally free again to do as she pleased.

When the day arrived and you and your mother went to her mansion, you couldn't help but feel your heart skip a beat at the sight of Cassandra. You didn't know what it was at the moment but the 39 year old woman was clearly having an effect on you. The way she talked, the sound of her voice, the shine in her eyes... It made you feel different and it made you want to get closer to her.

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 so you simply added a comment from time to time or giggled at a joke one of the two made. You were an introvert after all and it was the best you could do.

Cassandra, seeing how you were trying to be part of the conversation, decided to ask you about your personal life, about your friends and goals. It was a strange feeling, usually people would ask you small, unimportant questions before bringing their attention back to your mother but Cassandra was different, it felt as if she really cared about you... It made you feel seen, loved and the effect Cassandra was having on you didn't go unnoticed by her.

After the party ended and before you and your mother left her place, Cassandra approached you and gave you her number, hoping to talk to you again soon.

To your surprise and delight, you and Cassandra quickly became friends and talked almost daily on the phone, as the days passed, you became closer and closer to her and the feelings you had for the older woman became clearer. You realized that you weren't only a lesbian but also fell deeply in love with her, something that made your mind race, not knowing that Cassandra picked up on that the first night she ever saw you.

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, it was a hard thing to process but before you even knew it, her lips were interwined with yours. Your first kiss, the kiss that would change your relationship with Cassandra forever.

---

It has been three weeks now and Cassandra invited you to her mansion once more, saying that she had a surprise for you and it was obvious what she had planned for you... Sex, that word sent shivers dont your spine and it made your heart race. You knew it would have to happen eventually and that it was a normal part of relationships but you couldn't help but feel nervous and anxious.

You kept telling yourself that it would feel great, that there was nothing to be scared of but you couldn't help it, it was an unexplored territory and you didn't want to disappoint Cassandra, so you kept moving, getting closer and closer to her mansion.

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 "Don't worry, my love, I won't force you to do something you dont feel ready for yet..." She whispered softly, her tone of voice and hot breath against your skin sending jolts of pleasure through your body, making your nipples stiffen, something that Cassandra quickly noticed.

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 for your consent. "Do you want this, my dear?..."