During her senior year at West Dover High, Kerri Roberts skipped her ceramics final to sleep in, costing her the class valedictorian distinction bestowed upon her by her classmates. Her thighs ached from pushing herself passed her physical limits, but the main issue was the throbbing within her cranium. The night before she had done as many tequila shots as the rest of the girls track team after they won the state finals championship and twenty years later, Dr. Kerri Roberts didn’t regret it. As runner-up in the senior class vote, I was given the honor.

“To be honest, I had crippling anxiety back then and the last thing I wanted to do was talk to everyone at graduation. I was so relieved when they gave it to you. You gave a fantastic speech,” Kerri said, looking me in the eye and causing the same internal stimulation she did back in high school. Her extraordinary abilities at pretty much everything turned her natural humility into a fuel that intensified the fire of her charm. By age 38 Kerri had become a successful psychiatrist after leaving her family behind on the East Coast to carve out her own life in San Francisco, California. I took a job with a start-up after school which took off and now pays an enormous salary. I’ve remained single and as age forty is quickly approaching I’d like to settle down, but not quite yet. My lifestyle is not an easy one to give up.

“I’m glad I could help you out,” I said. “I thought a speech about second place was the way to go for our class. You were the only overachiever if I remember correctly.” 

“Overachiever?!” Kerri exclaimed. 

“Don’t deny it,” Her husband said, a little irritated. I wondered if it was perhaps the shitty cards in his hand, or if there was something negative going on between him and Kerri. ...Or if he sensed I was getting an erection thinking about the old days. Our West Dover graduating class was quite small so everyone was close with each other, but Kerri never hung out at the usual parties. She seemed to uniquely have a sincere amount of fun while competing on the soccer or track field, debating her teachers in class; even group study sessions seemed alive when Kerri was in them. She liked everyday fun and didn’t do drugs or get drunk with everybody else, which is what made the tequila story so scandalous.  

“I still can’t drink tequila,” Kerri said, ignoring her husband’s comment. 

“You’re very competitive,” her husband asserted more strongly, now looking for a response from his wife. 

“No I’m not,” Kerri said, her soft white cheeks blushing the color of pink roses. 

“You had to keep up with everybody else doing shots,” I said, providing evidence toward her husband’s accusation. “If you hadn’t been so competitive you wouldn’t have gotten so sick and missed the ceramics final.”

“How’d you know it was my ceramics class?”

The answer was that I had sought out gossip about Kerri since the day we met. She had completely hooked me at first sight. Whatever time of day she arrived in my vicinity the world suddenly became radiant. Everything about her was perfect; her face, her skin, her eyes, her smile, her voice, her posture, the way she smelled; like breezy hair product and grape lip gloss. The first time I did cocaine, about twenty years ago, just after I moved to the city and was invited to a party at the Top of the Mark, the euphoria immediately brought Kerri to mind. In high school, every moment we worked together on our World History project I was distracted by a desire to know what she tasted like. 

Her boyfriend back then was some asshole named Ryan, whom I didn’t think was an asshole until he started dating Kerri. The day I heard that they had sex while her parents were in Italy I became very jealous and legitimately depressed for a week. Later, after they broke up, Ryan confessed in the most sincerely tragic way possible that “her pussy was magic,” blaming the area between Kerri’s legs for the loss of his mind. After stealing money from his father to buy her jewelry, resulting in Kerri breaking up with him and apologizing personally to his parents, insisting she never asked for the necklaces and rings and earrings, Ryan became obsessed with trying to get her back and dropped out of school. Today he lives with his parents and manages a mattress store in Boston. 

“I know all sorts of random shit about you,” I said, deciding in that moment to push the social boundaries along with the stakes at the table. 

I host a monthly poker group at my house and told the group we needed some fresh blood, and two of the friends-of-friends-of-friends ended up being Kerri and her husband. Everyone had left about an hour ago, leaving just the three of us at the table. The fact of the matter was Kerri’s husband had no business wagering real money on cards, but I was enjoying reconnecting with Kerri so I kept him in the game. He was already down about nine thousand dollars with less than half of that remaining on the table. The pot of the current hand would knock him out of the game, and we both knew he didn't have the cards. My plan was to let him sweat while I reconnected with his wife for as long as I could get away with it.

“...Remember the Junior Class trip to Philly?” I asked Kerri, knowing just how seriously I was escalating things just by bringing it up. 

“We should go,” Kerri told her husband. “It’s late.”

“I’ll raise you a thousand,” Kerri’s husband said, throwing eight red poker chips at the pot in the middle while his mind raced through paranoid possibilities of what might have happened on the Junior Class trip to Philly. 

The truth was that nothing happened in Philly, except our travel group got very stoned and I didn’t realize Kerri was still with us on the bus, or how loudly I was speaking, when I revealed to Marlow just how much I wanted to fuck Kerri, and all the ways I wanted to do it. I had been considering the topic for a few years and delivered a very long and detailed description, unaware that Kerri was listening to every word.

“Yeah okay,” I said, tossing a handful of red chips from my rather large pile. “Is that eight?” I said, playfully squinting at the pile. “Shit, it’s ten. I guess I raise.”

I was thinking the evening was about to end, but Kerri’s husband glared at me for a few seconds too long, during which time I both became irritated by the challenge, and developed an impulse to satisfy an itch. 

“Actually,” I said after counting the remainder of his money and raising him twice as much. “I need a new watch and like the look of yours. You have good taste,” I said, looking at Kerri. “If you feel strong about your hand, toss that watch in the middle and let’s see what you’ve got.”

Kerri’s husband softened his glare while he considered the challenge. He wanted to fight, but was nervous. I could tell he needed some coaxing. 

“C’mon, I just threw a ton of money in there and we’re talking about a retro Casio for fuck sake.” I thought maybe insulting him would do the trick and it did. Within an hour I had him signing IOU’s just for the fun of it. 

“I want to go home,” Kerri said. 

“So go!” her husband snapped, finishing the last of the whiskey in his glass, angry about the mounting debt he owed me.

“We came together.”

“Uber,” he said. 

“We should all call it a night,” I said, sensing how angry Kerri had become with her husband's behavior. “I’m just fucking around with these anyway,” I laughed, referencing the IOU’s. Somehow, this infuriated Kerri’s husband. 

“I don’t need your fucking pity,” he said. “You’ll get your money.”

“I’m not taking your kid's college fund,” I joked. “Just take away from this evening that you are completely shitty at cards, and I’ll be happy. That will be my act of service for the month.”

“Fuck you!” he shouted. 

“Relax, man,” I said. “I don’t need your money. You made a mistake, maybe you have a bit of a gambling problem, I don’t know. But you’re lucky because I’m cool. Typically Tiny enforces the game around here, but this stays between us, okay? I don’t want you to worry.” I tore up the IOUs and stuffed them in his empty glass. 

“You arrogant little prick,” he said. 

“Dude, go home,” I said. “You’re drunk. And you have nothing I want.” I looked at Kerri. “Except for her.” 

“What?” Kerri said. 

“Sorry, I know you’re not really his. I just mean that you both are married, and I’d like to fuck you.” I looked at Kerri’s husband. “ Is she worth…” For dramatic effect I dumped the shredded IOU on the table. “Ten grand? Roughly?” 

Both Kerri and her husband remained silent, stunned by my suggestion. 

“You saw Tiny earlier, standing by the door. Big fucking guy with the scar on his face. The guy who gave him the scar isn’t around anymore. Tiny doesn’t collect at a convenient time. He’ll come to your work. Before lunch. Pick you up by your ankles and tip you upside down and shake the ten grand out of you.” I said, glaring into Kerri’s husband’s eyes. 

“C’mon,” I smiled. “You don’t fuck her anymore, anyway. Not because you don’t want to, but she’s not into it anymore. It’s obvious.”

“What are you suggesting?” her husband asked. 

“Wait a minute,” Kerri said. “I’m not some object, like your fucking watch. I’m not your property and you can’t gamble with me.”

“Well, we’re not gambling with you,” I clarified. “The gambling is over, we’re discussing using you to settle the debt from your husband’s bad gamble.”

“Same difference,” Kerri said. “The answer is no.”

“Fair enough,” I said. 

Kerri’s husband wobbled a bit from the booze as he stood from the chair, and both turned for the door. 

“I’d get your payment in order as soon as possible. You don’t want Tiny waiting around your office tomorrow. He has a very short attention span and becomes chatty.” 

They both stopped.

“...I thought,” Kerri started to say.

“He told me to fuck off, and that he didn’t need my pity, and that I’ll get my money. That’s what he said, so…”

“But I was…” Kerri’s husband started to say.

“Well, whatever you were, that’s what you said. So either you win it all back tonight, or prepare your co-workers for an uncomfortable visit tomorrow from a debt collector. ...That would be Tiny, in case you’re bad with riddles.”

“What do you mean, win it all back?” Kerri asked.

“I like your idea about gambling with you,” I told Kerri. “Frankly, it makes my dick hard. And now I want to find out if my fantasies about you match up with the real thing,” I said. “I want you to suck my dick until I cum in your mouth.”

“No,” Kerri said. “Not happening.” 

“It might not! That’s the gamble. Not if your husband wins. One game of blackjack. He wins, I forgive the debt. All ten grand. I win, you suck my dick and swallow.”

They both remained quiet, which I took as a sign of victory. 

“I mean my God, it’s just a blow job,” I laughed. 

Kerri and her husband exchanged a look, and within the look they agreed to go for it. I told Kerri to stand in a neutral area, equally between her husband and I, which she did as if following some sort of rule. The truth was I found treating her like a commodity incredibly erotic. 

“The thing is,” I said, starting my trash talk early because I knew it’d be a short game and I was eager to have Kerri’s lips around my cock. “Kerri might not want to fuck me. Maybe I’m not her type. Maybe she doesn’t think of me that way. I can accept that. But, I certainly want to fuck her. It’s personal. For me it’s very personal. I love everything about her. And I’ve thought about fucking her a million times in a million different ways. So… I hope I win,” I smiled. “I think she’s the most beautiful thing I’ve ever seen in my life. And I’m very rich and have seen some Ahhh-mazing shit.”

Kerri’s husband didn’t say anything, and after a long pause indicated that he would like another card. 

“But….” I continued. “Kerri does want to fuck somebody. I mean, not me, but I get the feeling she wants someone to fuck her. Somebody to fuck her. Some body. And while on the one hand I’m me, on the other hand, I’m also a body. So the math works. You know how I know that? That Kerri needs to get fucked? Because I agree that she doesn’t want to fuck me, yet she is still here. Waiting, right there-” I pointed to Kerri, standing uncomfortably by the couch in the living room. “Her family is loaded. They have tons of money. They could cover ten grand. So… why did she agree to it? Maybe it’s to get back at you,” I paused, looking directly at Kerri’s husband, “But I don’t think those feelings are there for you. She’s not flirting with me to get back at you or to make you jealous or something. This isn’t about you. It’s about her.” 

I stopped. From the look on Kerri’s husband’s face, the card he asked for busted his hand. He had lost but couldn’t admit it yet. Then I looked at Kerri, her face tilted down toward the floor, appearing ashamed. 

“Look at her,” I told her husband, and he did. “She looks fucking guilty,” I laughed. “Guilty of needing some new dick. Well, I have great news,” I paused, causing Kerri to look to me. “I have an amazing dick. You’re going to love sucking it.”

“Do you want to suck my dick?” I asked. 

“Yes,” Kerri quietly admitted after a long pause. 

“I know you do,” I said, then looked to her husband. “Are you going to flip those cards over and we’ll make it official?” I asked her husband. Nine of Clubs, Three of Hearts, King of Spades. 

“You’re welcome to watch,” I told her husband as I quickly stood up and pulled my pants down past my thighs; my erect cock in a nearly comic fashion springing into view.  I had been hard thinking about Kerri all night and saw no point in waiting around. “I’m probably going to cum in five seconds,” I muttered to myself. 

“Hey Kerri, grab a pillow from the couch for your knees and get over here,” I told her. I nearly came just by seeing her comply with my instructions. 

As Kerri dropped the pillow and knelt in front of my rigid dick, I noticed her husband fondling himself. 

“Hey, I have an idea,” I said, looking down at Kerri, enjoying the way she was looking at my cock; eyes wide, her chest heaving. She licked her lips and I decided to push the boundary.

I gathered her beautifully silky auburn colored hair in a fist and spanked my rock hard cock against her cheek repeatedly, landing each time with a heavy “thunk thunk thunk.” 

“Go ahead and pull your dick out. You have to keep stroking at whatever pace you like, but if you cum before me then you lose,” I said to her husband. “If you win, I’ll give you ten grand. How does that sound?”

Kerri’s husband was super eager to both watch his wife suck a stranger's dick, and to get ten grand, so he dropped his pants instantly, stroking at a very slow speed. I smiled, pleased that he didn’t think to ask what would happen if he lost. 

I couldn’t help myself and leaned down and kissed Kerri on the mouth. Long, firm and wet. 

“Alright Kerri baby, suck my dick,” I whispered in her ear, pushing her head down over my cock. I almost lost it and shot my load down her throat when I felt the warmth of her tongue and heard a cute grunt because I had taken her by surprise. I had masturbated for much of my life imagining this scenario and the reality was mind-blowing. 

I looked down, admiring her beauty, stroking her cheek with the back of my hand while she sucked me. 

“You’re an amazing cock sucker, Kerri,” I told her. “Fuck, I love your mouth.”

She pulled away and began licking my balls. 

“Ooohhhh fuck, that’s right, Kerri. Lick my balls baby,” I pressed her into my balls and lifted my leg, shoving her face into my taint. “Will you lick my asshole baby? Lick my asshole Kerri. Ohhhh fuck yes.”

After a few seconds, I pulled back and positioned Kerri again with her mouth around my dick, holding her hair into a ponytail while I put my hips into slowly face fucking her. I’ve done every drug I’ve encountered and I had never felt so euphoric in my life. I managed to open my eyes to peek at her husband, who was at this point furiously masturbating. I knew he wouldn’t last another few seconds and I began to laugh. 

“Nice!” I said, and pulled Kerri off of my dick, just in time for her to see her husband cum all over himself. I leaned down and took Kerri’s face in my hands. 

“I win! So I’m going to cum in your pussy,” I told her. Her breathing was fast and heavy while her eyes were directed at the floor. I lifted her head and looked into her eyes. “You liked sucking my dick, didn’t you?” I asked. She nodded her head. “Tell me.”

“Yes,” she said quietly. 

“So your husband can hear,” I said. “Tell him how much you liked sucking my dick.”

“I like sucking your dick,” Kerri said.

“How much?”

“A lot,” Kerri said. “I love having a cock in my mouth,” she said, before sucking my dick again without the help of my hands on her head.

“Ohhhh good girl, Kerri. Your mouth is lovely,” I commended her, petting her head while looking at her husband. He was still hard and stroking again. 

“You just sit right where you are,” I told her husband while I bent Kerri over the poker table and pulled her pants below her ass. “You want me to fuck you?” I asked her. “Do you want to feel a dick in your pussy? Do you need to be stretched out?”

“M hm,” she responded quietly in the affirmative, spreading her legs and wiggling her ass in anticipation. 

I spanked her very hard, causing her to scream. I rubbed my cock between her asscheeks. “Do you want me to fuck you?” I growled in her ear. “I can’t fucking hear you.”

“Yes!” she screamed, her eyes tearing up from the sting on her ass. 

“Say please fuck me,” I told her. ‘

“Please fuck me,” Kerri repeated. 

I shoved my thick cock into her dripping wet pussy as hard and as deeply as I could, causing her body to tense. She screamed again. I grabbed her hair and pulled her up to my face. 

“Does that feel good?”  

“YES…” she groaned. 

“Does it feel good to have a big cock inside of you?”

“Yes,” she groaned again. 

“Is my cock bigger than his?” I wondered. 

“Yes,” she said. 

“I see,” I pushed her back down on the table, spanked her again and began fucking her fast and hard. 

“Tell me how much you like it, Kerri. Tell me how much you like taking my cock.”’

“What?” she said. 

I reached my hand beneath her shirt and fondled her breast. Feeling it inside my hand, then pinching the nipple. 

“Do you want my cum in you?” 

“I do,” she said. 

“Tell me how much you like getting fucked. Tell me how much you want me to cum in you,” I said. 

I enjoyed her for as long as possible while she rambled about needing to be fucked; squeezing her breasts, playfully pinching her nipples, mixing in hard and soft spanks upon her ass, kissing her along her spine while fucking her from behind. Just before I pulled out to avoid cumming too soon, I felt her ass cheeks tighten around my cock, and her back arch a little higher. 

“Oh no!” she exclaimed. “Oh no!” she said again. “Oh no!” she repeated, and I laughed at her innocent sounding pre-orgasm mantra. “I’m going to…” 

“I know you are, Kerri. Cum for me slut,” I said, giving her a hard thwack upon her ass, pulling her hair and putting some extra hips into her. 

Once her body trembles and moaning had subsided, I removed my cock from her stretched cunt, slick with her cum, and positioned Kerri on her back. I wanted to look into her eyes as I claimed her.

She was tired; exhausted from being on the receiving end of my obsession with her. Again, I spanked her soaked pussy with my hard dick. “I’m not going to last long,” I admitted, causing her to laugh. I slowly pressed inside, hoping to enjoy every second before I shot my load. Her body was damp with sweat, her eyes sleepy, and the quiet moaning coming from her mouth as I fucked her was devastatingly erotic. 

“You know something Kerri? Your pussy is magic,” I said. She smiled and I fucked her harder, squeezing her thighs in my hands. “You’re so fucking wet,” I said, pulling my cock out to give myself a rest and tapping it on her stomach. “Look at all of that.”

“Say, I’m fucking wet from your big thick cock,” I told her. 

“I’m fucking soaking wet from your cock,” Kerri said. 

I pressed my cock inside of her again, enjoying seeing her head tilt back and eyes close from the sensation of me being inside of her again. 

“Does it hurt?” I asked.

“A little. But I like it,” she said. 

“Kerri,” I began fucking her harder, holding her above her waist, watching her tits bounce from my thrusts. “Kerri, Kerri, Kerri,” I said. 

“What what what?” She smiled as I fucked her harder, enjoying playing with her this way.

“Have you ever been fucked in the ass?”

“No,” she said.. 

“Do you want me to fuck you in the ass? Right now?” I asked.

“Yes,” she said, very quietly after a very long pause. 

I positioned her legs on my shoulders, lifting her ass above the table. I pressed the head of my hard cock against the tight bud of her asshole. 

As I slowly pushed the head of my cock inside, I put my hand firmly around her neck. 

“How do you like taking my cock in your ass?” 

“I like it,” she whispered. “Slowwww?” she begged as I pushed in just a bit more deeply. She gasped and I paused, waiting for her to adjust. 

She was very tight. I stretched her as slowly as possible, both for her benefit as well because I was afraid I’d cum at any second. Her begging for ‘slowww' made things even harder. Once she was able to take my thickness, when I was about half way in, I took another break and pulled out. 

“Bend over,” I said, and I was pleased at how easily Kerri obeyed my orders. She bent over the table and arched her back, giving her ass to me. I knelt behind her and tongued her asshole, licking and kissing her ass. I noted the freckles that I could not have imagined when I dared dream about assfucking her. I took a position standing behind her, and let her feel my length and girth between her cheeks. 

“Alright slut, I can’t take it anymore. You ready?” I asked. 

“Mmhm,” she said as if she knew what I had in mind. I put my right hand on her shoulder and pulled her hair with my left, and then fucked her asshole as hard and fast as I could. After about thirty seconds or so my cock began to ooze cum and then the biggest orgasm of my life took over. 

After ten to twenty hard thrusts that nearly broke the table I pulled out, and Kerri remained in position; legs spread apart standing on the floor, bent over, stomach on the table. 

“What are you doing?” she asked in a post-orgasm dream-like state, aware that something was taking place behind her.

“Souvenir,” I said, taking photos. “I’ll send you one. What’s your number” I asked. 

“Why? Do you own me now?” Kerri asked, only half-joking.

“Yes,” I said, not at all joking. “I do.”

Kerri began to stand up. 

“No, stay like that. I like you bent over with my cum running down your thigh,” I said. 

Kerri smiled, and resumed the position, “Okay,” she said.

“I’m so glad we reconnected.”