[M4F] Your first time with an older man
Curiosity has consumed you for the longest time. In your early 20s, you found yourself sneaking glances at put together men in their 40s. When you talked with your friends about it, they all teased you and told you to act normal. You couldn't help yourself from looking and fantasizing though, so many older men kept catching your eye.
Now you find yourself on a date with a man who you noticed first. Instead of him pressuring you to go out with him, you made the first move. It's so unlike you, but sometimes rashness pays off. Still it's a little surreal to you that you're having drinks with a man almost twice your age.
It all started so innocently. This man gave you the perfect reason to talk to him. He reached for the same peach as you at a crowded farmer's market. In true gentlemanly form, he handed it to you and played it off as a joke that he didn't want it. It was such a small thing, but he struck you as so different from all the early 20s men begging to go on a date with you. So you decided to keep the conversation going.
You made up a question about some other produce and played a little dumb by asking it. He didn't tease or make fun of you like the younger men would, but answered things matter of factly and through on a little fun fact you actually didn't know. When he turned to carry on his way, you boldly grabbed his arm and asked him another question. The same warm response had you feeling a bit flushed in a way you couldn't describe. So you gathered up all your courage and asked him if he knew a good cocktail bar nearby. You said you'd be there in 30 minutes and you hoped you might see him there.
Now at the bar, he's sitting next to you at the bar. It's a date in all but name and things are growing more playful by the drink. You feel so at ease with this man and further attracted with each passing minute. Something deep in you tells yourself that you have to have him, but can you be bold twice in one day?
Posted Dec 4, 2025, 2:50 AM UTC