I have a best friend named Lilly. We've known each other for about 14 years now. We met in senior year of high school. We are now 30 years old. She was always the more outgoing one. Me? Not so much. I go out once in a while. I'm an attractive woman. I have very big natural breasts. Long black hair. And green eyes. I'm just very inexperienced. I am quite shy. But I was ready to let my hair down and have some fun. So when Halloween came around I was pretty much willing to do anything. She asked if I would like to attend a halloween party with her. Lilly said she had the costumes already. That made me a little worried. She liked to dress quite obscene. I remember the one time we went to a rock concert. She dressed in a sexy black studded bustier. With tight leather mini shorts. And patent leather boots that came up to her knees. Not to mention the red and black fishnets. She did catch the eye of the guitarist. After the show he asked her backstage. But that's another story. I do wish I was that outgoing, and brave.
She called and said she'd be here in about an hour. As I opened the door stood this statuesque 5'9" goddess. She had the prettiest long golden hair. Crystal blue eyes. And enormous tits. Plus, she had the sexiest tattoo of a cobra wrapped around her upper thigh. I've never felt sexually attracted to her. That is not until now. She was wearing a long black leather jacket. It's what was underneath that made me shudder. Lilly was wearing a prisoner outfit. The top was a black and white striped corset. Pulled tight in the back with a leather strap. Her nipples were sticking out for all to see. The bottom was a little pleated skirt. If you can call it that. When she bent over I could see her every inch of her ass. Even though she did have a piece of sting for underwear on. Plus she had the most luscious pair of sheer black lace thigh highs I think I've ever seen. She pulls out of the bag pretty much the same outfit for me. Except I was the prison guard. We decided to into the bedroom to get dressed. I have a queen size victorian canopy bed. I also have this beautiful ottoman so I can get onto the bed with ease. I sat down and started to put my stockings on. I don't think I have ever worn thigh highs before.
Lilly decided I might need a little help. She approached me and told me to extend my leg. So I did. I felt so torn. I could feel myself getting hot. She is my best friend. And a girl. I thought. Which needless to say, I have never been with a woman. This is the first time she's touched my legs in such a tender way. She began to roll it up my leg. When she had arrived at my thigh, I felt a tingle shoot through my body. I know she knew because she had this little smirk on her face. Then it was my other legs turn. This time when she reached my thigh I let out a little moan. She definitely heard that. Lilly asked me if she was turning me on. I replied with a smile.