You are currently reading from the Top 5 Series.
The summer I left before college, I fell in love with a man named Jesse whom I had met in front of a Best Buy on a trip to Montauk one night. Now, the reason I say man is because he was six years older than me. Looking back, I can see why my mother was wary of him – but, as many of you know, I’m not one for usually caring what my mother thinks.
I wouldn’t go so far as to say that I was attracted to Jesse because he was older – but there was definitely something about being with someone who already knew who they were and what the world could be about. I was, in many ways, a child.
Jesse was the first man who taught me about what it meant for a girl to be sexy – I began to walk differently, talk differently…dressed differently. Suddenly I wasn’t rolling out of bed in day worn jeans and t-shirts – I was putting outfits together and, well, accessorizing. But I found that it wasn’t enough – I didn’t want to just look older, I wanted to be older. And I thought I knew just the way how…
“You want to go where?” Sam laughed.
“Victoria’s Secret.” I said, “I want to get something really nice for tonight.”
“Ooooh,” Sam laughed, “I see. I guess we could go check it out.”
You see, my mother thought I was staying over Sam’s house – I was really going to sleep over at Jesse’s place. He had been asking me to spend the night and I couldn’t bring myself to tell him that I needed to ask my mother first.
Now, before we go any further, I want to make a few things clear: 1) Jesse and I were both aware of each other’s age, 2) Jesse and I had had sex prior to the night of the sleepover and 3) Jesse was always respectful of my limits.
As I just mentioned, Jesse and I had been intimate before this night but I felt like this was my grand entrance into adult life and I wanted to look the part. I was spending the night in the house of a man I cared for very deeply – I was going to make love to him and I wanted to assert myself as a woman.
I spent $274 on black thigh high stockings, a garter belt, a black and red lace corset complete with a very uncomfortable matching thong. Suffice to say, I meant business.
Sam was kind enough to lace me up and put me together once we got home. Jesse arrived to pick me up from her house just as I managed to find my way through my favorite t shirt.
“You look nice.” he said.
“Oh yeah? You don’t look so bad yourself.”
Jesse and I had just gotten in from having one of the best Italian dinners of my young life. He threw his keys on the marble island in his kitchen and asked if I wanted a glass of wine.
“Sure.” I said, “I’m just going to go upstairs and freshen up.”
I tore off my t shirt as I made my way down the hallway to his room and began to carefully take off my jeans. I searched through my bag for the black and red lace heels I had purchased from Charlotte Rousse and donned one of Jesse’s white, man-tailored, button down work shirts…and left it unbuttoned, obviously.
I tousled my hair just like the girls did in the movies and looked in the mirror one last time before I walked out to make my move. And damn it, I looked fucking good.
I felt like such a bad ass walking down the hall way to the stairs – the button down shirt showed just enough and the heels matched the corset perfectly. The garters held up the garters divinely and I was so excited to show Jesse just how sexy I could be.
I descended down the stairs and sauntered into the kitchen whipping my hair from side to side and said, “Well, are you coming to take care of business or what?”
“Holy fucking shit…” I heard a man that wasn’t Jesse laugh.
I looked up to see five men I didn’t know standing in Jesse’s kitchen and screamed as I struggled to cover myself. “Who the fuck are you?”
“Lauren?!?!” Jesse screamed, “I thought you were waiting for me upstairs?”
“Oh my God.” I screamed, running for the stairs.
As I attempted to get up the stairs without tripping, I heard one of Jesse’s friends ask, “Damn Jesse…how fucking old is that girl? I didn’t know you could get hoo…”
“I’m not a fucking HOOKER!” I screamed, still ascending.
I threw myself onto the bed and began to cry. Jesse arrived five minutes later, “Lauren,” he half-sighed, half-laughed, “Are you okay?”
“I’m an idiot!” I sobbed.
“Come on,” he smiled, taking me in his arms, “You’re not an idiot. I just wish you had told me you were…well…”
“Dressed like a hooker?” I laughed.
“Yeah,” he said. “No worries though. I like it – it’s mighty sexy. So sexy, in fact, that I almost don’t blame them for asking!”
“Well, if I am then you’ve run up quite a tab.”
Jesse and I had amazing sex that night, and we went to dinner with his friends the next week and assured that I was not a hooker but that I was a mail order bride. It took them a minute to get that we were kidding 🙂