Naughty Secret Affair

Your roleplay starts with you and Jenna setting up separate dates at a decadent bar downtown Vancouver. You arrive separately; you're a complete stranger to her, someone who has caught her eye in the crowded room. Jenna, in her modest yet tantalizing dressing style, captivates your attention. Her teasing demeanor draws you in, and you find yourself unable to resist her allure. The thrill of forbidden excitement that accompanies the risk of being caught adds to the spicy undertones of this game.
After drink or two, you notice her handsome date for the evening; a friend of yours in on the role-play scenario, arriving to whisk her away. Unable to hold back your jealousy, you make an excuse to follow them out unnoticed, tracing them to the intimate back booth of the bar. Jenna's playful glances and the mild flirtation towards her date arouse feelings of voyeuristic pleasure and jealousy in you.
The roleplay ends with you turning the tables - Jenna's date insists he had to leave and you, seeing the opportunity, seduce her. This secret affair culminates in the confines of your shared home, where hidden passions seep into reality, oblivious to the world outside.

You'll need to brief your friend about the role he'll be playing in this scenario. Setting up a safe word or gesture with Jenna is crucial in order to maintain comfort and consent throughout the roleplay. The beauty of indulging in fantasy is in its controlled environment, so remember to keep it light and fun.
Plan the setting, ambiance, and location beforehand. Pick a downtown bar that suits your budget and offers intimate spots. Dressing according to the theme will be very important; Jenna should dress modestly yet enticingly, matching the overall teasing nature of the scenario. You, to fit as her potential affair, should dress in a way that accentuates your most charming features.
Finally, you'll need to prepare at home, turning your bedroom into a lair of secretive lust. Candlelight, soft music, plush bedding, all contribute to the mood of the evening.

The key to this role-play is maintaining the aura of secrecy and teasing - ensure that Jenna achieves this with her dressing and behavior. You should embody the character of a smitten stranger, allowing the scenario to awaken the thrill of forbidden fruit.
Remember, roleplay is all about comfort and fun, establish boundaries, use safe words, and respect each other's comfort levels. Nothing is sexier than consent.
At home, let the ambiance do half the work for you. Make the environment sensual and inviting, use scent, sound, and touch to your advantage. And most importantly, enjoy the game! This role-play is not only about exploring taboo subjects but also about deepening the bond between you and Jenna.