"It's never your dream job. As soon as you get it, you start dreaming bigger."
"Honestly," said Longboard, "That's been my career."
"Your career ain't over yet."
"True," said Longboard, "But I might be interesting in making some changes."
"What changes?"
"We'll see," said Longboard, "I've got several things on my mind."
"You're the head of a company that did $303 million turnover last year. You've always got several things on your mind."
"That is true," said Longboard.
"So what's on your mind?"
"A million things," said Longboard, "And nothing."
"How's that possible?"
"I went from a high school dropout to sitting atop a diversified insurance conglomerate, what does that tell you?" said Longboard.
"Anything's possible."
"Anything is," said Longboard. He got quiet for a while. His body language was still more vulnerable than he ever displayed in the office. I leaned over on my side. I was still in my black T-shirt dress, no cleavage but arms showing. I was trying to listen and look good while doing it. Longboard went on. He opened up. I don't know why but he just started telling me things about himself that I never knew. There was always the power balance of information in relationships. With employees, the boss always knew more about the employee. For starters, he knew my salary. I didn't know his exactly. When profits were up, I'm sure he took home more. But I didn't know what he was taking home. He drove an Alfa 8C. But maybe it was leased. A lot of dudes on the Island drove light pickup trucks, even if they had money. Pick-ups were great because they compensated any outdoor sport, especially water sports. Driving a supercar almost said I'm a prick. You couldn't tote a surfboard with a supercar. You couldn't carry waterskies, tow a jet ski or a boat. There was no hitch on a supercar. There was something above the line about driving one in O'ahu. Guys who lived like that usually spent big always, because they had to set themselves apart. Longboard could have been living on credit to maintain appearances. A lot of guys who were supposed to be big on the Island were that way. Maybe they had some money but they lived outside the range they could afford. That was common in Hawaii. Between the refined beach bods and the premium property prices, there was a lot to spend money on. Longboard had seen my resume. I had seen his news article. Even though he was a high-profile figure, I felt like he knew more about me than I did about him. But every word that came out of his mouth tipped the balance. I started to learn more and more about him.
He was actually avoiding me because he was wondering how I felt about him or more accurately how I felt him. He was worried that he might have been too big for me. Apparently he had seen that happen before. He had some awkward encounters. It was Denise, his first long-term girlfriend that let him know it was his size. The first time they had sex her labia swelled up. He had to dial a non-emergency medical line. She had to sit in a bathtub of warm water to get the swelling down. But Denise stayed, partially out of naïveté. She was a virgin before Longboard. She didn't know anything else about sex. She thought the pain was part and parcel of the act. She resigned herself to woman-up and take it. Besides, Longboard wasn't a boy. He was a man. But he didn't let his male-character prevent him from being a nice guy. And Denise discovered another thing about being with a well-hung Alpha-male, bragging rights. Her girlfriends didn't even know their vag could swell up like Denise described. It was intriguing. The rest of Denise's cat-pack wondered if they could handle it, like Denise did. They began to complain where they hadn't complained before. They stayed away from athletes because of the co-ed counselling. The freshmen girls had been treated to an orientation lecture that told them the average campus rapist was typically of a more athletic build. So most of Denise's girls dated the T-shirt-wearing gamer guys. Because of Denise, they began to see it as a raw deal. They sat around at LAN parties bored out of their skull, watching their boyfriends play Halo. When they tried to be a 'good girlfriend' and take a turn at the controller. They got a litany of commands in their ear and before they realized the difference between the X and Y buttons, the screen went red and they were told their turn was up. They returned to their boyfriend's dorm to try and feel what they could feel. They realized they were focusing during sex. They realized they were with the wrong guy. Guys who lived their lives in a virtual world, virtually did things in the real world. Denise asked them if the gamer guys shot pixels, instead of sperm. They probably did was the consensus. Denise told Longboard that she and her girlfriends had coined the phrase Don't Get Focused, Get Fucked.
It was Denise that helped Longboard really understand women. After their first time, Longboard decided he would take it easy. Denise didn't want it that way. She wanted to get her money's worth. If her boyfriend had a big dick, Denise wanted him to go big. She didn't just want dick. He had to relearn how to be in bed. He wasn't timid but he wasn't Alpha. He just didn't want to dial for medical help again. He had to relearn how to play rough with girls. Denise taught him it was ok to be passionate. I could hear in his voice there was a part of him that would always be loyal to her. She taught him the world was ok with him in it. It seems his dad didn't always make sure that point was clear. That was powerful.
After graduation, Longboard broke up with Denise because it was the thing to do. She was joining the Peace Corps and he moved to Ohio to work for Proctor & Gamble in their employee benefits section. That's how he developed an interest in insurance. He wasn't there at P&G long. He went to work for one of their benefits providers. And learned the mechanism of the insurance business and paid close attention to how to manage the incoming cash flow. But Longboard stayed in touch with Denise. In touch was tough. It wasn't closer. It wasn't closeness. But it was cliché--the normal questions and the normal updates. Longboard got tired of the charade. But it made no sense to bring up nonsense. They weren't getting back together. Distance was defiant. It gave Longboard a subtle sense of longing or frustration. He didn't know which. So Longboard worked at the insurance company and went to school for his MBA. Like high school, he didn't finish. Because he started college late, he didn't feel so interested in his master's. He thinks it was because he was three years older than the average student because of working for his dad and the time it took him to get his GED. Then he stopped talking. He looked at me.
Longboard grabbed as much of my boob as he could. Foreplay. I deserved it for listening. He knew it. I knew the game was on. I tagged him. He tagged back. I was it. Longboard clapped his hands and let the dark room swallow us. Longboard moved in behind me--I not knowing where the light switch was. At first it was a game of tag but it became hide-n-go-seek. I thought he would pause long enough to turn the lights back on. The lights didn't come on. And suddenly I couldn't clap my hands together. He held them. Longboard found himself pushed. It wasn't hard but it was hard enough to force him to the middle of the bed. With the space between, I stood up off the bed. The lack of light took away the thing that got him instant respect, his size. No one could see him in the dark and he couldn't see himself. But being big made him easy to find. I grabbed his leg to be sure where he was. I jumped back on the bed next to him. Longboard felt a hard slap to the low meat of his left buttock. The slap was slightly off target. It was pretty accurate given the dark. But I couldn't find exactly the spot I wanted in the dark.
"You know the thing about being named Dawn?"
"What's that?" said Longboard.
"I like to do it in the dark."
"Really?" asked Longboard.
"No, but you can't blame a girl for being clever."
"No you can't," said Longboard. I clapped my hands. The world changed. Longboard had his eyelids extended trying to see what he could in the dark room. Clapping my hands caused subtle pink lights to fire on. It wasn't the overhead lights. It wasn't so easy as clapping the lights on and off. There was a program. The pink lights were tethered to the ceiling like the ceiling had been lassoed.
"Pink Pepper," said Longboard.
"And what's that?"
"This is called the Pink Pepper Suite," said Longboard.
"I didn't know. But then I didn't ask."
"They try to keep it modern," said Longboard
"That explains the bathroom."
"I saw you on stage," said Longboard, "How come you didn't show me moves like that earlier in the week?"
"That's on stage." I stretched my head down to my feet while bouncing my shoulders. The move took only two seconds. But it was professional. It gave Longboard a few pricks to his balls. It was the kind of attraction of a woman to a guitar player. It wasn't the semi-sexual gestures he made with his hands. It was the work behind the gestures. To finger a guitar like a rock star and make it sound intelligent took work. To bust out a twerk with instant rhythm, while laying on a bed took practice as well. It was something most men didn't realized about a woman, because men never mentioned it when they were together. They admitted to liking big tits or a nice ass. Hard work was almost never mentioned even though it was true for all men. They like a hard worker.
The thought of how much work I was willing to do gave Longboard 70% of the erection he wanted to have. He started to unzip his pants even before he took off his shirt. I saw him taking apart his belt and knew something from experience. The guys who were shy about their size never unzipped early. The guys who were eager to impress had their stack ready to show. Denise had a hand in it. The speed at which Longboard pulled out his dick undermined just how big it was. The first thing I noticed was that he was shaved. I liked it. But I didn't remember him being shaved before. It made a man seem clean, made me feel thought of. I guess he was trying to make it more pleasant for me than on his desktop. Maybe it was an apology of sorts. I knew Longboard was big but not big enough to make me say damn without opening my mouth. I let it out through my nostrils. In the pink light, it almost looked like produce, a long zucchini or cucumber. It was so wide it looked foreign, like from someplace where I had never encountered the locals. I thought of somewhere in Africa. The word Congo came to mind. It looked like something wild, uncivilized. And it was pointing directly at me. I felt my heart skip a beat. It felt like I was being held underwater for a second too long. I inhaled realizing I was depriving myself of air.
I never really saw his dick before. I just got it. But it wasn't really on display because he just took me, no foreplay--no talk. I had seen a lot of dick, some bigger than others. But this time I was at a loss for words. I thought of a joke. That's why they call us Whoa-man! It was something to lighten the mood without killing it. But I was never corny. But Longboard's penis looked like it belonged on something besides a man. Even the low pink light wasn't enough to cover up the angry vein on top of his dick that had been suddenly woken up. The vein bulged in the middle, forming what looked like a knot on top of his dong. It looked nautical, like a submarine. Just the size and shape made it look designed for deep sea diving. I regained my composure. Longboard reached in his pocket for something. I could hear the subtle manipulation of a wrapper. He pulled out a Trojan Magnum condom. I had never actually used a Magnum before. Something about the word Magnum made me realize I was in a different zone. I reminded myself I had taken it before. The average woman was only stocked for average-sized dicks. I tried to play down my anxiety. I know it sounds weird that it bothered me. But the first time I think I was running on adrenaline. But I played it like a big girl.
I grabbed the condom packet from his hand. I held out the condom.
"Magnum."
"I've never broken one so if it isn't broke..." said Longboard.
"Even if it breaks, keep going until Dawn comes."
"Until Dawn comes?" said Longboard.
"It's democratic, you can interpret that any way you want."
"I'm good with interpretation," said Longboard.
"In either case I'll be alright."
"OK," said Longboard. I tore open the package and lifted Longboard's hard inches. He was so long, his penis didn't really stand. I could feel he was hard. But his dick leaned down. I had seen so many erections but I hadn't seen it all. Longboard's cock was so big it brought in the laws of physics. His erection had too far to go to angle upward. He was just too big for the laws at play. There wasn't enough pressure to push him up. Nature was brilliant. If his dick stood at full attention, I might've almost been afraid of it. It was the first time I got full view of it. The first time he just took me in the office and there was so much passion behind it that I started to secrete and he just came right in. I didn't notice anything about how he was hung.
But I realized it couldn't go high. As I held it, I noticed that my fingers didn't contact. There was space between my index finger and thumb. I held him tight but his dick took up too much space for me to close my fingers together. I slipped the latex layer over his heated cock, realizing how much I had to pull for the condom to extend over the surface. He pulled his briefs down and crawled through his pants. He pushed my dress up and pulled my pants down to my heels. I guess I was tense or some string of stress from the week was still in me because I strained with his size. He was strong, that I didn't mind. But I still hadn't gotten wet enough to fully conform all the way around his huge cock. I felt brittle. It wasn't that I was dry. It was that the condom mostly was. It gave me the feeling of opening wide for the dentist with dry salt lips. That was essentially what was happening. I could feel my juices leaving when Longboard pulled back. He pulled my T-shirt dress up over my face so I couldn't see. The pink light could penetrate the loops of thread, so that I could see Longboard's shadow moving over me as he thrusted. His thrusts were extended. He had a long swing. He pulled back for time, then jammed forward and held his penis deep inside me. He didn't move it. He just held it there. It didn't feel sexual. It just felt like being penetrated. There was having a dick inside and then there was being penetrated. Longboard was so long, so wide and so hard that he was way back where others couldn't go. He was pressed against the back wall, driving his hard rod against the last layer of me. It felt like that part was asleep and had been woken up. In the back of my mind, I could hear my pussy's voice saying, What are you doing back here? Then Longboard left, pulling his broad bone back. As he slid out, I could feel the confusion of my vagina wall. And hear its voice in my mind. What the fuck was that? It was as if my vag forgot all about Tuesday. It was the same man, same manhood. But both me and my veejayjay were more tense than Tuesday. I was a little too in my head for my own good. For some reason, the spur of the moment was a blessing for desk surfing on Longboard's mahogany workspace. But I was overloaded by the feeling of his chunky cock busting my baby-making chops and the hard palpitations of my heart.
I could see the pink light hitchhiking its way through my cotton T-shirt dress and it made me feel like I was seeing what his dick saw--some dark pink space. Between my accelerated heartbeat and his dick jabbing against the inside of me. I had a mild headache and my fight or flight response took off like it robbed a liquor store. I couldn't see much and I was pinned with my panties around my ankles and my dress over my eyes. He pulled my bra down and I could feel his dry tongue on my tits. He kind of motor-boated me with his tongue. My boobs were sizeable but they were fake. It actually made it easier to feel what was happening to them. I could feel Longboard's long thick fingers weighing on the skin, forcing it against compacted gel underneath. But my fight-or-flight instinct was still ringing the alarm. I knew Longboard was long-winded because he got me once in his office and once in the conference room. He was just getting started. But I couldn't handle much more. I was just off my game. I thought I was game-ready until tip off. Now I just had to get his tip out. And I could feel it all the way to where my space ended. It felt somewhat insensitive. It felt like the back of my vag was making a final stand. We got vital organs in here you know? But Longboard's bombardment kept coming. I could feel the walls of my vag bending, trying not to let him draw blood, but I was getting so dry. I could even feel some of my dry juice on the outside of my pussy lips, lef
t there by Longboard dragging that shit out. We need that lube you know? The fight-or-flight hit my brain and I developed a strategy. Fight. Lean in and grab his ass and work him like smashing. Flight. Tell him he was hurting me and offer to finish him with a blow job.
My hands were still pinned, so I wiggled my right wrist and tucked my thumb in. I was able to slide my hand out but it burned my skin pretty bad. His grip was that tight. I started to yell, not like he was hurting me but like I was enjoying it. Yes...Y-Y-Y-Yes...Hank...Hank...Hank. I should have been yelling: Stop. Stop. Stop. But for some reason I cared that he got his. I realized some dudes I fucked cuz they were hot. But thinking about it, I didn't care if their balls let loose or not. But Longboard was my boss and there was that promotion. And then I didn't want to penalize him. He felt something. That was clear by him opening up to me. And why should there be a penalty for having a big dick. He worked hard and built a big company. And I benefitted from that because it provided me with a neat little job. And I'm not gonna lose sight of all that because I couldn't handle his hog. That idea didn't seem right to me. And then there was the story about that Denise girl. If she could ride him all the way, then so could I. With my one free hand, I slid in on his dick. It hurt so much my already useless eyes rolled back in my head. But I kept screaming his name. I slid my right leg through my panties, heel and all. I slung that leg around his waist and grabbed his thigh with my hand. I dug my nails deep into his thigh to let him feel my tension. As he thrusted harder seeing he was having some effect, I screamed louder and louder and louder. I took my free right hand and started rubbing my boobs like I was out of my mind. For sure, he thought he was fucking my brains out. In reality, he was letting my blood out but I wasn't doing it all for nothing. His thrusts became faster and wilder, less exact. He went back to beast mode and just started fucking me like on the Discovery Channel. It was just that constant in and out rubbing his dick every which way. He was thrusting so much I could feel his dick coming at different angles. Fuck me. Fuck me, Hank. Fuck me with that big dick. I had used that line before. I had a boy who liked to hear me talk dirty during sex. It helped him keep his hard-on and it helped him finish. But this was the first time I actually felt honest about saying Fuck me with that big dick. That was exactly what was happening.
Longboard (Desk Surfing Series Book 1) Page 8