Jessica, My Very First Really Bad Date

Jessica: My Very first really bad Date #1

I have dodged a lot of bullets in my life. But, never have I been had I been in a relationship as complicated as the one that I had with my first girlfriend Jessica. Our entire relationship was based on dodging bullets.

        Jessica and I met at a mutual friend's birthday party in the fall of 1997. It was a fresh start for me, with new friends that I had acquired during the summer of my sophomore to junior year. I was still a Virgin and despite my valiant efforts to rid myself of this debacle, I was having very little luck with girls my own age. I was kind of a psuedo-wigger-jock/ budding video game nerd that had little to no tact in the dating world.

        I had joined the wrestling team just as the school year started and I was getting ripped quickly. I was in the best shape of my life, and liked to show off my body and my wrestling moves when given the opportunity. 

        The ratio of the birthday party was good, it was almost 2 girls for every boy (like that old Beach Boys song). The party consisted of about 8 freshman girls, 2 guys my age, 2 freshman boys and myself. My sex appeal may have doubled or tripled due to the fact that I had a car....and I was the only boy at the party who had a car.

        Only one of the girls was a walrus, and only two of the others were what I would have rendered Vaginaless Manatees....or if you wanna get all P.C. About it; I considered them "un-fuckable" at the time. That left me with 5 options and I knew exactly which one I wanted the most. It was Jessica.

        Jessica was the cutest girl I have ever seen in my life....to this day. I was instantly drawn to her every move and word. We were all watching some t.v. in the downstairs “kids room” which was collectively the size of my mom's entire house. However when Jessica got up to go to the bathroom I jacked her seat...which was the only open chair left in the room. As she had been in the bathroom our friend Michelle "the birthday girl" told me that Jessica liked me...so I knew I was already in. When she got back from the restroom, she smiled as she coyly whined about the fact that I had taken her seat. She was soooooo cute. She had gigantic brown eyes that seemed to make my heart skip a beat every time I looked at them. She had the face of an angel....well a short jewish angel anyways. She had a great big smile and thick perky lips. Her cheeks seemed to stay rosy all the time as if she had just gotten done taking a jog in the cold winter air. I informed her that I had saved her a seat, and she asked in a very sweet innocent voice; “oh, where is it?” I looked her right in her big brown eyes and said “Hold on, let me dust it off for you”. I then made the motion as if I was dusting off my lap. Everyone in the room saw and heard the conversation and the room exploded with laughter. I thought this would have scared her off but she jumped right on my lap like I was santa claus and proceeded to wrap her arms around me. 

        She couldn't have weighed more than 90 lbs but, she was surprisingly curvy for her age. I was 4 years older than her, which was the high school equivalent of being Hugh Hefner with one of the Olsen twins on his lap. This wide of an age gap was looked down on tremendously at the time. If I did anything with this girl beyond a hand shake or a hug, my tiny and incredibly unforgiving Bainbridge Island high school would know about it the next day and I would be labeled a cradle robber or a pedophile immediaely. This is a label that can stick with you throughout the rest of your high school career and render you un-datable to girls your own age until you graduate and move away. So, that being said, I pursued her with the notion that I would have to keep it a secret from everyone....which is good and bad. 

Bad; because a girl this cute should be shown off to the world. She was arm candy for sure.

Good; Because, I knew that anything I did with her, I was doing for myself because I actually liked her and I was attracted to her. She wasn't just a girl I was pursuing to show off to my friends.

        Michelle had a hot tub sitting right out the back door of the “kid's room”. I suggested that we all go for a dip. Michelle naturally had enough bathing suits to go around to all of the girls....Well except for the biggun “Britt” who unfortunately resembled a hairless bear.

        Secretly my suggestion to take a dip in the hot tub was not only to "douchingly" show off my own body, but I was also dying to see what kind of curves this adorable little tart was hiding under her sweatshirt and jeans. When she came outside with us, she kind of covered herself up with her arms over the bikini that she had picked out. When she got in the tub, she had no choice but to unleash the perfectly shaped mammaries that she had been holding so tightly with her arms. I couldn't take my eyes off of her. She was beautiful. She had the body of a fully developed 21 year old but she was just entering high school. I doubt she really knew what she had going for her, judging by the way she was trying to cover herself up. You could almost feel the jealousy beaming out of the eyes of the other girls who were definitely lacking one way or the other. She was without a doubt the best looking girl there and to top it off, she had the best body out of all of them. 5 of the girls just left their clothes on and opted out of the hot tub idea all together.

So, it was me, Jessica, Michelle and Kylie. Kylie was kind of chubby but not hard to look at. She had a cute face, but “Anthony” (one of the guys I came with) kind of had dibs on her (not that I was interested, but dibs are dibs man)  Michelle, who I had known for a while, surprised me a bit. She had a skinny frame but, she was an early developer too. She still hadn't developed hips like Jessica but her top half was looking very grown up.(She had big boobies)

I caught Jessica looking at my body and I moved over to her. I grabbed onto her in a hugging motion with my hands to her side so she could rest her hands on my shoulders as I whispered in her ear. “You have an amazing body”. She started to back up (blushing a little bit) and ran her hand down my chest and said out loud: “I was going to say the same thing to you”.

        It was on!!!! We started making out hard! I knew she was inexperienced because she was kissing me as if she was a starving Wolverine and I was the fresh carcass of a fat bunny rabbit.

        We were in our own little world long enough to scare off whoever had been surrounding or sharing the hot tub with us. Our disgusting display of instant animal attraction had probably gotten to the point where everyone who had seen our interaction was probably convinced that we were going to just start making babies right there in front of god and everyone.

        I asked her if she wanted to get dressed and wrestle in the bed room, and despite how cheesy that sounds, she actually agreed. We grabbed our towels and headed back inside. We sort of dodged everyone inside and ducked over to the one open bed room to start our wrestling match.

        Honestly for the first couple of minutes I really did just show her wrestling moves, but the whole time I would just pin her so I could kiss her again. She was seriously the cutest girl I had ever seen and I couldn't help myself.

        We tired ourselves out from wrestling and just sat on the bed and talked. I rarely ask, but I asked her full name. She said Jessica Tolliver.....”get the fuck out” I exclaimed. “You aren't related to Erika Tolliver are you”? She looked at me whimsically and said “Ya, that's my sister”. “Oh, fuck” “we probably shouldn't be talking”. As I stood up and started getting my stuff together in order to go. “Your sister hates my guts”. I said, as I was zipping up my jeans. “Why would she hate you”, Jessica asked. “Well, your sister had a pretty bad entrance into our school and I may or may not have started a rumor or two about her”...”She may or may not want to exact some revenge”. “Oh, really? What kind of rumor?” Jessica shot back.

        Ok, fine...to be fair, when you live in a small town or worse yet; an island. People get excited about new people very easily. This cute new girl showed up with blueish green hair "Erika", and “Christian” (one of my friends) had sex with her within a week of her appearance. Christian never elaborated on whether or not if was good or fun or whatever, but I made up the stories for him...because I was a liar and a douchebag....and frankly a little bit jealous. We had a small, tight knit set of friends that were incredibly unsuccessful with girls and my friend “Christian” seemed to just have the best luck out of all of us. I guess I just lived vicariously through him and decided to make his story more interesting. After watching a bunch of 1980's VHS porn that clearly stated that pubic hair was not only ok, but standard. I started a rumor that Erika Tolliver's “Carpet” matched her “Drapes”. I never meant to have her reputation so battered and destroyed but by the next day she went from a girl named “Erika Tolliver” to a girl named “2000 flushes”. Which actually became a best seller on my drink recipe list this year....

        I left the party with my buddies without even exchanging numbers with Jessica. It was supposed to be a one night stand. I told my guy friends the story and left out the details of actually fooling around with her. Even though I trusted them, it would have only been a matter of days before one of them cracked and I would end up getting a black eye from 2000 flushes.

        Jessica remained on my mind for weeks. I don’t know what possessed me to do it, but I looked up Toliver in the phone book, and since there was only one listing, I called the number and pretended to be one of Jessica’s guy friends. I had a full blown conversation with Jessica’s dad as someone else before he finally passed the phone to Jessica.

Jessica: Hello?

Hef: Hi

Jessica: who is this?

Hef: It’s Hef

Jessica: who?

Hef: Hef, the guy who wrestled you after hot tubbing a few weeks ago.

Jessica: Oh my god! How did you get my number?

Hef: It was in the phone book.

Jessica: Oh…duh. So, whats up?

Hef: I want to see you again.

There was a pause in both of our conversation as we both knew how difficult that would actually be.

Jessica: well, how are we going to do that?

Hef: Can you go to the football game on Friday?

Jessica: Ya, I was already planning on going.

Hef: can you disappear for an hour or so to hang out with me?

Jessica: I can try

            I met up with Jessica at the game that Friday night and Bogarted her from her friends. We found a safe place a few miles down the street to make out at. It was down a long dirt road that forks off into an abandoned logging road. It was as safe a place as any.

This went on for weeks, every time there was a home game, we would make plans to meet up at the game and drive off to our little make out spot in the woods. It was awesome…well until football season ended and we had to get a little bit more creative.

For Christmas I bought Jessica a fire escape ladder for her bedroom.(Even though she was a practicing Jew)

I did the whole "romantic pebble throwing at the window at midnight thing". She would climb down her fire escape ladder and we would go to our little make out spot or just sneak into the woods behind her house. We started getting to the point where we were feeling each other up and getting a little freakier, but still didn’t remove any clothing. Not that we weren’t interested but we were both not quite ready for that next step. I was still in Catholic confirmation and my Grandmother, (along with one of my Aunts) grilled me about pre-marital sex and I promised them that I would remain abstinent until I was married.

I actually stayed true to that for well over a year with Jessica. Even though we were extremely sexually attracted to each other, we kept the pants on, until one day……

We agreed to stay home “Sick” on the same day, so we would have the whole day together. We had gotten past all of the heavy petting and although I had no issues with going down on her, she still had trouble getting past the heavy petting and moving to oral. To Jessica: The idea of having my penis in her mouth had the same sexual appeal as driving a freight train covered in tabasco sauce right into her asshole.

        She remained “hands only” for the better part of a year…which I was fine with until we became sexually active and started running out of ideas for lubrication. It wouldn’t have been such a bad thing if the relationship wasn’t a secret, and the few chances we actually got to get intimate were only for a small period of time.

        It was mid April and he weaher was warming up, Jessica and I went to different schools, but her school was on the way to my house so made plans to pick her up during our lunch break and try to pull off a quickie in time to get her back to school on time.

        I raced to her school where she was waiting patiently for me out front, alone. She hopped in my maroon 1982 Ford Crown Victoria (old cop car). We sped all the way to my mom’s house and started undressing eachother the second we got through the door. I didn’t even have my pants or shirt off before she was layed out on my bed and I was on top of her. 

        My mom and sister had just adopted a wayward kitty and it had some bowel control problems. The whole house smelled like shit....human shit, but I had warned Jessica in advance to plug her nose until we get into my room. I kept my door shut most of the time to avoid the stench of liquid kitty stool, which unfortunately traps all of the hot air from the sun into my room like a greenhouse.

        We were both short of breath as I kicked my bedroom door open with Jessica wrapped around my torso like a friggin spider monkey. she ripped off her pants but left her shirt on, as I finished dropping my pants to the ground. I looked at the clock. It was 11:46am, in order to get her back to school in time we, had exactly 4 minutes to get this done. My mouth was too dry to service her orally and even if Jessica had the ambition to blow me for a bit, she couldn’t produce enough saliva to do any good. I looked around my room with my pants around my ankles, desperate for anything that could pass for lube.

        I would have sold my soul for a tube of neosporin or a tub of moisturizing lotion...hell I would have been fine with a stick of butter. Our hands and mouths were all over each other. We were busier than a Hornets nest on meth, but we were dehydrated and lacking the necessary fluids for our sexual rendezvous. I had to think fast or this wasn't going to happen, and if it didn't happen, it would surely fuck up my Chi for the rest of the week. Not to mention the blue balls that would be agitating me for rest of the day.

        I adjusted my eyes into every nook and cranny of my little bedroom, as I was laying on top of her. It was dark, yet hot. The only thing that even resembled liquid within reaching distance was a squeeze bottle of Hershey’s chocolate syrup that I had jacked from the kitchen a few nights prior; to make chocolate milk. I didn’t even ask Jessica if she thought it would work. I just squeezed a big handful of the chocolate syrup right onto her belly and hand forced it down to her girly parts as I removed her underwear. She seemed to like it, even though she didn't actually see what it was. I suppose I could have just given her a heads up, but I wasn't about to ruin the passion for a second to inform her what exactly I was putting into her vahoo. I sadly didn’t give a whole lot of thought into foreplay and just forced myself into her after I felt as though the chocolate sauce had gotten her sufficiently lubricated. She didn't seem to mind....in fact, by the time I had gotten my swollen member all the way in, she was incredibly moist. She seemed totally into it for the short time we were allotted and despite our time crunch, it felt amazing.

        We didn’t do anything interesting or unusual during our quickie. We had a mission, and that was to get off in less than four minutes. It was a very passionate quickie but we didn't have time to really enjoy it, so I thrust hard into her and without holding back any force: “Here comes the cookies!” I pulled out and shot a solid 10 round report all over the tight knit black t-shirt that covered her chest and belly. I was worked up like a Tiger in a cage being prodded by a dozen noisy Asian school children. I roared in immense pleasure as the multiple blasts of liquid sea monkeys splattered her sweaty yet fully clothed, perfect upper body. A couple of the shots cleared her entire body and hit the bedframe behind her head, but the majority actually landed right on her face and to make matters worse...mostly in her eyes.

        I was shaking in pure delight as I looked at the clock, it was 11:52. I looked at Jessica who was blindly trying to put her underwear back on while I still had myself mounted on top of her. “Ooopsie”, I spouted like a Mousekateer accidentally missing a song que on the Disney channel. I had sweat dripping from my nose and eyebrows onto her shirt. I got off of her slowly and wiped the sweat from my nose and brow with my forearm and suddenly noticed something remarkable:

Wow! I had unconsciously created a diagram of the entire solar system with my sweat and duck butter.....and Jessica's face was the sun. Rad!

    We did it with our shirts on in late spring. It was hotter than Hell's kitchen in that house and we were right in the oven. I got off of Jessica and quickly got my pants back on. I started walking down the dark hallway towards the front door as I was fitting my belt back into my belt buckle. I needed to get some fresh air immediately, and water...lots of water. I got to the front door right as I finished maneuvering my belt back on, when I noticed my grandmothers car in the driveway. “What the fuck?” I said out loud. What? Jessica's voice pouted shyly behind me.

There was no one in the car, what is going on? I thought i was being "punked" waaaay before "punked" existed as I  panicking in my own psychological conundrum.

        Then the door handle turned quickly to expose the bright spring light, as well as my Grandmother and my mom. (As if I wasn't already sweating hard enough) I had no excuse for being at the house during lunch time. Mom made me a sack lunch that day, and saw to it that I didn't leave home without it. I was in shock, which was mild to the horror that must have been going through Jessica's mind. She was blinded by semen. She looked like she had been crying, and she had the entire solar system sprayed all over her in the form of body fluid. The whole house smelled like shit and I had brown stuff all over my hand.

My grandmother was the first to enter the house. She looked at both of us in silence as she grabbed a couple of the grocery bags from the front porch and quickly glided past us to the kitchen. My mom followed right behind her, she looked at both of us as we were squinting at the light. What are you doing here? Mom asked.

I cleverly hid my chocolate sauce hand behind my back to dispose of the evidence.

H: Oh, uhhh.. I just wanted to show off our new kitty.

Mom: You know that grandma and I took her to the vet this morning right?

I did know, but I thought it would be an all day event...seeing as how the Veterinary clinic was almost an hour away.

H: Oh, really? Bummer...i was so excited to see our little baby. Well, we better get going. Gotta get back to school on time.

Mom: (now looking at Jessica....actually, more like looking through Jessica) Who is your friend?

H: Oh this is my friend Jennifer, I have to get her back to class.

Mom: Okaaaay, Nice to meet you Jennifer. (with a subtle hint of disappointment in her voice)

        I got Jessica back to school on time and got myself back on time as well. Whew! That was a close one I thought. I don't even think mom and grandma suspected anything, I was off the hook....or so I thought.

        When I got home after school, grandma's car was still in the driveway. I was half way expecting to hear a lecture from my mom and possibly my grandma about leaving the school for lunch when I have a perfectly good sack lunch that mom made for me. Instead, mom pulled me aside into the living room very nonchalantly so I was out of grandma's view.

Mom:“I just wanted to ask you a quick question”.

H: Yes, mom I did eat the sack lunch you made me...and thank you, it was delicious.

Mom: No, its about your friend Jennifer.

H: oh, yeah...we just met and she said she liked kittens so I invited her to come over and see our new little kitty.

Mom, turned around and finished what she was organizing in the fridge for a few seconds and came back to me, as I was lazily leaning against the kitchen table waiting for her to get to the point so I could call Jessica and let her know we were off the hook....instead....Mom dropped the bomb.

Mom: Is Jennifer on her period?

H: What?

Mom: Look at your shirt, (pause). Oh, and I think it's about time you start washing your own sheets, blankets and pillow cases. 

        Mom was calmer than a Grey Whale on Heroin. She turned around and faced her organizing project as I looked at my freshly cleaned white t-shirt. This was the white t-shirt that I had to convince/ beg my mom to buy me a few days prior, and even though the principle behind buying this shirt was to have it fit waaaay to big on me, she sent it through the wash so it would shrink enough to fit my 5'9” 139 lb frame and still be 2 sizes too big (since that was what wigger-jock-nerds wore) . I lifted up the bottom of my shirt which hung well over my waist line and out of my line of site. I suddenly turned white and started to sweat. I knew what she and grandma had seen...The brown, the red, the smell of shit all over the house. Jessica's eyes plastered shut with the same substance that had created a rather fashionable outer space diagram on her upper torso. It looked bad, i mean...it was bad, but it looked even worse. My sweet innocent Catholic grandmother must have thought I was some sort of deviant. She was probably expecting a sexually aroused donkey and a little midget man to follow us out of my bedroom while cracking a whip at us.

        It wasn't so much the sight of my shirt at that moment but, suddenly I could smell my shirt very clearly and i could now clarify why I had been craving Reese's peanut butter cups all day. I stood there like a deaf, mute, jackass staring at the kitchen table, I wondered how I hadn't noticed in the last 3 hours that I had a giant brown and red V at the base of my white shirt...right in my crotch. Her period blood was the same rusty smell as the peanut butter filling of Reese's peanut butter cups, and of course we had just used Hershey's chocolate syrup for lubrication which coated the coppery peanut butter smell with sweet cocoa. The faint smell of one of americas most delicious confections...emitting from my junk actually made me crave a Reese's Peanut butter cup. I was in shock. I wonder how many kids noticed the brown and red V, on my crotch as i was walking down the halls? (as if my wigger/ jock outfit wasn't  ridiculous looking enough before) Could they smell it too?

        I was horrified about the situation as it was, but the real horror didn't really hit Jessica and I until the next morning. 

    I Firmly believe that Hershey's Chocolate Syrup should come with a warning label: "Do not use for lubrication". When you think about chocolate syrup you tend to have an idea that it is a thick liquidy substance much like KY Jelly. What you may fail to realize is that Hershey's Chocolate syrup is almost purely made up of sugar. Sugar is abrasive, and when mixed with syrup...you have the equivalent of wet sticky sandpaper. The morning after our Hershey's experiment, I went to take a morning piss like I do every morning. Only this time, when I pulled out my one eyed monkey, it felt like i had just pulled it out of a sock full of sulfuric acid. My trouser snake, had the worst case of road rash I had ever seen. It looked like i had been fucking an economy sized pencil sharpener. I can't even imagine what Jessica was going through. 

    I had been dying to talk to her all day. I must have gone through a tube and a half of extra strength neosporin throughout the school day. I took so many bathroom breaks that my teachers and classmates must have thought I had a wicked case of the shits. I waited till 5 to call her, when i knew she would be home. I once again pretended to be her friend Brian for 5 minutes with her dad, and then I finally got on the phone with her. 

H: Hey Jessica, how are you?

J: I just got back from the doctor.....not good

H: I had a feeling, what did they tell you?

J: I have something called a yeast infection.

H: Ewwww, what is that?

J: You don't want to know. 

H: Is there anything i can do to make it better?

J: Ya, can you get me a glass of milk and a spoon?

    Just kidding, she didn't really say that. She did however have a yeast infection for a couple of weeks, the same road rash that I had experienced was apparently 10 fold for her. Her sweet little girl parts may never be the same again. I healed like a champ and was ready to get back in the batter's box (no pun intended). However, Jessica had a little bit of Sexual PTSD over the whole chocolate sauce fiasco, and our love life quickly died. Jessica missed a few days of school due to our chocolate sauce soir'e, and she was forced to tell her parents what actually happened. Naturally Jessica's older sister Erika (aka 2000 flushes) got wind of it and spread the word that I was a pedophile, since I had fornicated with her little sister. Well, much to my surprise; it didn't seem to have much of an affect on our tiny high school community. In fact, it may have actually attracted a few of the girls in the school that had a secret food fetish. Jessica on the other hand was nicknamed "Hershey squirt" for the remaining years of her highschool career. 

         Thats how I turned the Tolivers into "Hershey Squirt" and "2000 Flushes", and that was one really bad, really painful date.

        Sadly I threw the Reese's peanut butter cup shirt away, but I should have hung it up on my wall somewhere. That shirt would forever be the original relic of 101 really bad dates. A mascot of sorts.

"By the way: I sill love Reese's Peanut Butter Cups"

-D-Archangel