Confessions of a Fuckboy: Jessica 1

The year was 1998. While this wasn't my first time as an unknowing participant of being 'the other man', it was the first one that actually I realized that I was the other man before it was revealed to me.

You see, for some reason, I was always considered the safe guy. I had the sort of personality that said 'Hey, I'm here to joke around and kid and be chill.' I never pressured women to have sex, nor did I directly go for it. However, it's always seemed to happen since well before puberty.

Part of it was because women talked to me. I'm sort of easy to talk to. I have this thing where I can keep my standards (hopefully), and not judge people for theirs. It may come from the fact that while alot of my family members are in law enforcement and the military, there's an even greater number that were -- at one -- less savory. Think dope boys and sugar babies, or even whores.

I'm fairly smart, and reasonably perceptive to some extent. I know when to call a spade a spade. I know when the jig is up. But, for some reason, I have always come across women that are better at obfuscating things, than I am at detecting them.

Anyway, Jessica 1 (as I call her now because I forgot her last name it was so long ago), was one of the first women that I fell prey to as a legal adult. There had been several before her, but they were in my pre-legal teens, so, I don't want to write about those.

See. Standards.

Anyway, I was working as a bagboy of all things at at a grocery store in the Midwest US. This store was one of several that shared the same name -- it rhymed with hire -- and I was just doing my thing while I worked my way through getting the certifications I needed in order to seem legitimate. The chosen field was web development, and I was going to the local community college to get this done.

Anyway, at that point, I was 6'4" and 220 pounds. While I wasn't ripped? I was solid. I carried my weight well. I was a 6 most days and was described as 'cute'. Auburn hair and hazel eyes with a sense of humor and ease about me that just gets people ready to talk. I also smiled alot naturally. Still do.

Anyway, Jessica was a steady customer. She'd always come in on the same day at the same time and always come to my line. Now, I'm going to say this -- and many will ask 'why?' -- but I was the best damned bagger in the company. Literally. I had won several 'bagging contests' at store openings.

Anyway, our store offered a policy that if the 'guest' requested help, the bagboy would have to do so. I didn't mind. I'm used to doing physical labor, and it got me off the line.

Now, Jessica. She was blonde (ugh), average height, and average build. She wasn['t a great prize in the grand scheme of things. She was plain jane for the most part. What she did have was a bad ass car. A Monte Carlo SS. I enjoyed looking at it. It was tricked out.

Anyway, she requested I escort her to load her bags, as usual, and I happily accepted. So, we're walking across the parking lot, and she looks over at me. "You are such a nice guy to do this for me." Now, I'm the sort that has boundaries, so I just say, "Thanks." You know. They know its your job, you know its your job. Why mention it and spoil the mood.

So, I'm there loading groceries into her trunk, when she reaches into her purse, and pulls out some folded up bills. Now, we aren't supposed to take tips, but if they don't tell, I won't. She passes me 10 bucks -- this is the first time -- and says. "I have to show my gratitude for you always being willing to help."

Well, its my job. But, who am I to argue. However, it seems like she can read my mind.

"I know it's your job, but you don't get all bent out of shape doing it. I appreciate that."

"Not a problem. It's nice to help someone I get along with. Gets me off the line. Besides, lets me spend more time talking to a beautiful woman."

Now, here's the thing. That was the first time I had said that to any customer. But, I was sort of feeling myself at that moment. I had just gotten laid the night before by a pretty hot chick, and well, I knew she was looking at the front of my khaki shorts. They were the sort of shorts that emphasized what I had without making me look like I wanted to emphasize it.

I mean, it might be my job, but I was testing the waters. What's going to happen? They fire me if she makes a complaint. Anyway, she blushed at the comment, and was a bit wordless. I tucked the 10 into my pocket, and told her "I'll see you next time." Headed back in.

Now, here's where it starts. One of the other girls I worked with, she generally ran and got everyone who wanted to put money in their lunch. That day, I ordered a Whopper Combo because burger was the place of choice, and I was hungry. Anyway, I went and passed her the 10, and when she unfolded it, she was like "Huh? There's a phone number and the name 'Jessica'."

Now, I'm thinking "No Fucking Way." So, I grab it back, and jot down the number and note.

"Jessica. 513-Insert Number Here. Call after 6 pm." I then gave it back to the co-worker, because food. Anyway, It was 8 pm. I'd be there until midnight. I figured I'd wait until my day off the next day to call. So, I ate, and finished my shift. Went home, went to bed.

Next day I slept in (It was a day off), and then went to the mall because it was Saturday. Me and the bros always mall ratted on Saturday. Anyway, I had stuck her number into my wallet, and each time I bought something at the mall, I was reminded to call her. Smart me.

So, by the time 6 PM rolled around, I was ready to call. However, I didn't want to seem too anxious, so I waited until 7. Thank you Zack Morris for the advice (yes, I watched saved by the bell).

Anyway, it was a pager service. Luckily, I was using the phone of one of the restaurants that a friend worked at, so I hung up. I then got the number, and called it back, so that I could put the number of the phone that I was calling from in. Less than 5 minutes later, she called back.

"Hello?"

"Yeah, Jessica. It's me. Sean."

It may have taken her a moment to put name and voice together, because there was a few seconds then. "Oh. Yes. How are you?"

"Doing good. How about you?"

"Fine. How's your day been?"

"It's been ok. Been Mall Ratting a bit. Getting kind of bored and figured I'd call the number. I almost gave it away last night without realizing you'd given it to me."

I heard her giggle before she said. "Glad you saw it. So, is that all you're doing today?"

"Yeah. Between school and work, I don't have alot of free time, so I decided to come to the mall and waste time for once."

My co-worker was getting antsy, and my friends were staring at me, waiting for me to seal the deal as it were. Peer Pressure. Can't bitch out.

"Well, that's good. I've been bored after I got done cleaning up the house. The kids are over at their friends' house, and I'm here all alone." It was the sort of play that a chick gives to get you to invite her out. So, I did.

"How about you come out to the mall with me. We won't have much time, but we can go grab something to eat once the mall closes, if you want to."

"I'll be there in 15 minutes. Where you at?"

"I'm at cinnabon. Meet me there."

The next thing I know, the line is dead. My friends are all passing money around and slapping each other high 5's. Now, the reason for the money is bets. Normally, I don't go out of my way to get women. I just luck into them. My game at this point is a bit above rudimentary at best. The reason they were passing around high 5s, is because I literally had macked on this chick seamlessly, and they enjoyed watching the experience.

Now, here's the thing. Most of my friends have a chick that is mutually attracted, or actually have girlfriends. Me? I'm the only free agent in our group. At this point the girls walked up, and are wondering why the boys are going crazy. The guys tell the girls, and there's a bit of awkwardness, with names like 'player' being called toward me, but I give no fucks.

So, we sit down and eat the freely given cinnabons that my friend gave us, and eventually Jessica shows up. There's an unattached salty girl or two, but they are kept occupied by their friends. Mutual friend groups. Gotta love them.

Anyway, here's the thing about Jessica. At this point, I think she is 25. She doesn't wear alot of make up. She's fit. She looks like a cheerleader. She's wearing a crop top that shows her flat stomach while emphasizing her breasts, and a pair of shorts that accentuates her camel toe. She walks in, plops down in my lap, and lays a scorcher of a kiss on me. Like, tongue and all. Then, she rearranges herself so that she is straddling me.

Now, we are the only couple that are doing this, and I have one arm around her waist, holding her to me while she nuzzles against my shoulder and sucks on my neck. The other one is occupied with my Cinnabon. I'm still talking to my friends. I wind up sharing my cinnabon with her, and we go back out to ratting for the next couple of hours.

Anyway, mall closes. We all head to the parking lot. We're luckily all parked in the same general area, as there are 3 cars between all of us. Jessica pulls me toward the car she's driving. I'm thinking it's going to be the SS. Nah. This chick is driving a Porsche. Shit you not.

"So, are you coming with me Sean?" She asked this while dangling the keys in front of me. So, I'm like. "Yeah." and take the keys. Then, I pass my keys over to my dude -- the one who I was teaching to drive -- and tell him to follow us.

"We're going to head home and get ready for Rocky."

Now, you might be asking what Rocky is. It's the Rocky Horror Picture Show. Every Saturday Night at midnight, the local art theater played it on the big screen. It was a Big Fucking Deal for our group. So, we all race home, with me and Jessica beating everyone by like, 10 minutes, and get ready for RHPS.

The thing about our showing is that there is a small troupe of people that live act the scenes going on in the movie as it plays on the big screen. You might be wondering why I'm mentioning this. I play the live action part of Eddie. Portrayed by Meatloaf. The old rock guy.

So, anyway, all the girls are rushing around trying to put together their Big Tittied Goth Girl outfits with a bit of unique flair (for this week), and the guys are taking turns scrubbing their balls and pits before refreshing their deodorant. Me? I'm busy getting my dick sucked by Jessica.

When we entered the apartment, she literally pinned me to the wall, dropped to her knees, and fished my cock out. Then deep throated me. This was after she had been piecing me up on the ride home. So, there she is going to town, while everyone else is getting ready. In front of everyone. I don't complain at all when she shoves her face against my stomach when I tell her I'm about to cum. She swallows it all down.

I am the last of the guys to get his bird bath and freshen up, and we are back on the road.

I will say that my group is a sliver of the people that show up for RHPS. There are 250 seats in the theatre, and it is always full. We are a dozen people. So, I pull in in the Porsche, revving the engine as I do. It's the back parking lot. People who are gathered scatter to make way. I help Jess out. Yes, she is already Jess. I introduce her. We hang out for an hour, then the show show starts.

I switch over to my Eddie outfit, and sit in the back with Jess. She has her shorts off as soon as the lights go down, and I am fingerbanging her in between call backs, while she is alternating between giving me a hand job, and sucking me off. By the time its my turn to enter the live show? I've cum twice, and am sort of exhausted. Regardless, I give the same stellar performance, running around and singing.

Now, I'm an introvert by nature, but I really love doing this shit. I caught the acting bug when I was in High School Drama club, and this scratches that itch. Needless to say, i give my performance, dying exceptionally well at the end, and then make my way off stage. Me and Jess sit through the rest of the show, with me fingerbanging her to multiple orgasms. Then, we all make our way to Denny's.

Now, the whole group fills up the Denny's at 2 am. Some of us have snuck in booze or have drank. Me? Nah. I'm driving. Jess? Liquored up from one of the girls in our group passing her a vodka water bottle in between orgasms. She's one of the unattached girls, who is Bi. So there's plenty of spit swapping while this is all going down between me and each of the girls.

Anyway, I order for me and Jess, and Jess reaches into her little clutch purse, and hands me a 50 dollar bill so that I can maintain my position as The Man and pay, even though it is her money. Jess then proceeds most of my fries. Like wtf dude?

Anyway, we stay at Denny's until 4, and then we all head home for the after party.

Now, here's the thing. Our apartment is actually an over under duplex with a shared entry. We keep the doors open on the weekend. We provide substantial amounts of bud and liquor. Nakedness generally happens to some degree or another. These after parties keep going generally well into Sunday,

Me and Jess? We catch a buzz, and then I fold her like an origami paper. Poundtown for several hours, condom free. Our bi friend? Joined us at some point and took her measure of cock while having her face buried in Jess' snatch, and vice versa for the girls. Anyway, 2 pm Sunday, jess has to suddenly book out, and we part ways.

The next time she comes into the store, she requests me to help her with her groceries. This time is different, because I pound her out in the back of her before going back into the store.

This pattern repeats itself for a couple of months, until suddenly, she stops showing up. However, in that time, I learned quite a bit. She was 35, and had 2 kids, close to my age. She worked a day care that she owned. The children belonged to corporate execs and the like.

Anyway, she stopped showing up for a couple of months, then suddenly she was there. She had a pregnant belly. However, she told me we had to stop as her husband was getting suspicious. She thanked me, and we only talked in passing after that.

I dunno if the kid was mine or her husband's. However, she eventually stopped showing up at the store.