Late one night I'm going over to hang out at the apartment of a girl I'm seeing; let's call her Amy. Amy and I have known each other for a while, and we mess around on occasion. It's nothing real serious, but we are far more than just friends with benefits. We honestly care for each other, but we realize that our personalities are not really compatible enough for us to truly work out as a real couple. But we're always there for each other and want nothing more than for the other to be happy.
I find a parking spot around 6:30 and head over to her apartment. I'm expecting a normal night with Amy. We'll watch a movie or some TV for a while, talk for a while and get something to eat, then mess around a bit and cuddle. I'll probably sleep over like I always do.
I arrive at her apartment and ring her doorbell. She comes downstairs to let me in and everything seems normal. We go upstairs together; and to my surprise there is someone else in the apartment with her already. A very cute girl who looks a couple years younger than Amy. She has long hair, glasses, freckles, and sort of a shy demeanor. Amy quickly introduces her friend.
"This is Jen."
She shyly looks me in the eyes and sticks out her hand. Having no clue exactly what's going on, I shake her hand and introduce myself. We all talk for a few minutes until Amy finally clues me in on what she had planned.
"You're probably wondering why my friend Jen is here."
I nod.
"This will probably seem weird but; Jen is a lesbian. She's never been with a guy before; but she's curious. I told her I knew a really sweet guy she could be comfortable with if she really wanted to experiment"
My face immediately goes red. I look over at Jen and notice that she's blushing too. But then she looks into my eyes and smiles shyly.
"Maybe you two should sit a little closer" Amy laughs.
So I move over onto the couch right next to Jen. We stare into each others eyes for what seems like forever. I finally work up the nerve to start leaning forward, and almost instinctively she does the same. Our lips meet, just a peck at first, but before long I'm sliding my tongue into her mouth. She's such a great kisser; we kiss for almost five minutes. I hear Amy opening the door to her bedroom in the background
"Maybe you guys would be more comfortable in here."