Me & Brittany had been going out for a while. We were both virgins, but had fooled around a bit. We were just waiting for the right moment. Well, one night at her house, we were both in the kitchen, where she was making a sundae.

I was wearing nothing special, just a white t-shirt and jeans with a cheap pair of black flip flops. She was looking good however, in a white tank top with no bra, a pair of jeans that didn't leave much to the imagination, and her brand new pair of blue and yellow Nike running shoes. She knew I had a thing for her running shoes, so she wore them quite a bit to tease me. She was going on filling the bowl with her condiments, when all of a sudden the bottle slipped from her hands and fell to the kitchen floor below. When the bottle hit the ground, a drop of chocolate shot out the end, narrowly missing her mint condition shoes. "Man, that was close. That almost got onto my shoes" she said, and I laughed weakly, secretly wishing the chocolate had gone 2 inches to the left, onto the laces of those sweet shoes. She asked me if I could pick it up for her, so I bent down and picked it up. Then, I got an idea. Without giving myself time to think about it, I gave the bottle a big squeeze, shooting a thick stream of chocolate all over her Nikes, covering the bright yellow laces and running down the sides in streams of brown. She shrieked a little bit, and looked down to see what I had done.

"WHY did you do that? Now these are ruined."
"I don't know."
"Well, I'm not happy. These were expensive!"

I got an idea.

"Can I lick them off for you?"
"...what?"
"I want to lick them off. Please?"

After thinking about it, she sighed, and grabbed a chair. I took my position on all fours in the floor. She grabbed the back of my shirt and yelled "You BETTER get them clean" as she shoved my face into the tops of her shoes. I felt the chocolate cover my face, but I didn't care. I ran my tongue up and down the laces of her right shoe, looking up every once in a while to see a look of pleasure on her face. I finished cleaning the one shoe, and moved on to the other. Afterwards, she exclaimed "NOW the chocolate got into the mesh. Are you happy now? I have to throw these out" as she took them off, revealing her beautiful feet and red-painted toes, and walked over towards the garbage. She stopped to look at me for a moment, and noticed the massive bulge in my pants.

"Wait...did that turn you on THAT much?
I nodded shamefully.
"Hmm. Interesting. Let's go up to my room."

She grabbed my hand and pulled in the direction of the stairs, putting the shoes back on first. Confused, I followed her. She instructed me to grab the can of whipped cream and bottle of chocolate on the way past, which I did. Once in her room, she pulled out a plastic garbage bag and spread it over her bed. She took the bottle of chocolate, looked at it a moment, and squirted it all over the front of my white t-shirt. "Hehe. Now we're even." she squealed. "Oh no, I don't want it to get on your jeans" she said, and she reached over towards them. However, instead of pulling them down or away, she pulled the waistband back and emptied what was left of the chocolate inside my boxers. Laughing, she said "I want it to get in your jeans!" as she watched the look on my face as the chocolate coated everything inside my underwear and began running down my legs. I could tell she had planned this before. She put down the empty bottle, and unzipped my jeans. Pulling them down, she awed at how stained my boxers had become with what seemed like only a small amount of chocolate. She then sat me down on the bed, and began licking slowly up my legs, ensuring she got every drop of chocolate on the way up. She then grabbed the can of whipped cream and sprayed it all over my rock hard penis. Giggling, she managed to fit the entire thing-whipped cream and all-inside her mouth, and she began to go to work. I started moaning with pleasure. Suddenly she stopped.

"I want sex."
"What?"
"Since these shoes are ruined anyway, I want them to be memorable to me. I want us to have sex, and I want the blood to drip onto them so I can always remember it. I'll take one, and you can have the other. It'll be something that we can always look at to remind us of this night"
"WHAT?????"
"Come on. Please? I let you ruin them to begin with."

With a mixture of excitement and confusion, I finished undressing. She took off what was left of her clothes, and got onto the bed, positioning one of the shoes under her pussy. After making sure this was really what she wanted to do, I put on the condom, and got into position.

"Ready?"
"Yes"

I began to enter her slippery and warm slit, slowly. She started to moan a bit. I met some resistance, and knew what it was. "I'm sorry" I yelled as I thrust forward with a huge amount of power, breaking through her hymen, and causing her to scream in a mixture of pleasure and pain. Blood began pouring out of her, which then dripped onto the shoe below. "Switch them!" she managed to get out, and I pulled away the blood-soaked shoe and put the other in it's place, which quickly became blood soaked itself. I re-entered her, and continued on with the process. After we were finished, the shoes had dried for the most part. She took one, and hid it in the back of her closet. I took mine, and wondered where in the world I could hide it. But it didn't matter. I had just lost my virginity, and combined it with one of my top fetishes. I didn't care what I had to do afterward to hide it.