Gambling Was to Blame
Copyright© 2026 by Guisamo
Chapter 3: The New Calculation
True Story Sex Story: Chapter 3: The New Calculation - Hi, I have to tell you a secret, gambling has me hooked. I've gone bankrupt a couple of times in my life, but we got out of the hole by taking out loans at a bank where the manager is a friend from school. I promised my wife I wouldn't gamble again, but I ran into another friend from school I hadn't seen in ages. He's a Black guy we used to call "Pigeon," not because he was a little bird, but because of the size of his penis.
Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa Gay BiSexual Cheating Cuckold Slut Wife Wimp Husband Group Sex Orgy Interracial Black Male White Male White Female Anal Sex Double Penetration Masturbation Oral Sex Safe Sex Big Breasts
Pichón greeted us in the same place, but this time there was a table covered with papers. Selena was dressed as he had demanded: a short black skirt, no panties, and a see-through blouse with no bra. I was wearing only sweatpants with no underwear, as he had ordered.
“Ten thousand,” Pichón said, snapping his fingers. “Plus late fees: fifteen thousand. At this rate, you’ll never get out.”
Selena bit her lip. I felt the familiar knot of anxiety in my stomach, mixed with something darker.
“New plan,” Pichón continued, approaching Selena and lifting her skirt to reveal her shaved pubic hair to the three men waiting in the shadows. “Selena works weekends. You, hubby, Wednesdays and Fridays. And together, special services that pay triple.”
Premium Service: The Submissive Couple
The first night of “working together” they took us to a four-star hotel. A client: a German executive who paid two thousand euros to “experience authentic marital submission.”
We were ordered to undress in front of him. The German, tall, blond, with metal-framed glasses, sat in a leather armchair without taking off his suit.
“Fuck her,” he ordered in English with a heavy accent, pointing at Selena. “Do it in front of me. I want to see your faces while you penetrate her.”
I obeyed. Selena leaned over the coffee table, resting her hands on the cold glass. Her reflection was multiplied in the mirror on the ceiling. I positioned myself behind her, noticing how wet she already was, always ready, always prepared to be used.
When I entered her, the German approached. He watched us fuck for five minutes, his hand in the crotch of his pants. Then he spoke:
“Now you,” he pointed at me. “On your knees. Clean her up.”
I withdrew from Selena, seeing my own erection glistening with her juices. I fell to my knees. The German man took Selena by the shoulders, sat her on the edge of the table, and spread her legs in front of my face.
“Tongue in. Deep. I want to hear her moan.”
I savored our mixture, the salty, metallic taste of our combined arousal. Selena grabbed my hair, guiding my head, rubbing herself against my mouth while the German man pinched her nipples until they were red and hard.
“Good,” the German man said. “Now for the next step.”
He pulled a leather harness with a thick, eight-centimeter black dildo from his briefcase.
“Put it on,” he ordered. “And fuck her while I fuck you.”
Pichón, who was watching from the corner, nodded. It was part of the service. The “sandwich” paid triple.
They put the harness on me. Selena got on all fours on the bed. I positioned myself behind her, inserting the dildo into her already open vagina. The German finally undressed, revealing a thick, upward-curving erection, its head glistening with precum.
“Don’t move,” he ordered, positioning himself behind me.
I felt his hands part my buttocks. The cold of the lubricant. And then the pressure. Different from Pichón’s fist, but just as invasive. The German entered my anus with a sharp thrust, making me gasp, pushing me forward, which in turn made the dildo penetrate Selena deeper.
That’s how we moved. A human chain of pleasure and humiliation. Each thrust from the German made me penetrate Selena. She moaned, I moaned, the German breathed heavily behind me.
“Good pair,” the German growled, speeding up. “Very good. I’m going to come inside you, husband. And you’ll come inside your wife. At the same time. That’s an order.”
And so it was. When I felt the German’s liquid heat engulfing me, my own orgasm exploded, pulsing in the void as the dildo remained buried inside Selena. She reached her own climax three seconds later, contracting around the black rubber, spurting onto the hotel’s silk sheets.
Two thousand euros. Paid in one hour.
Standard Service: Husband Wednesdays
Wednesdays were for me alone. Pichón discovered a market for “humiliated married men,” and he exploited that niche.
The first session: a group of four construction workers Pichón knew. Big men, with calloused hands, used to physical labor. They paid five hundred euros each to “use a white husband’s mouth.”
They made me kneel on a construction container, on an old mattress. One after another, they pulled down their work pants, revealing workers’ cocks: thick, veiny, smelling of a day’s work sweat, unwashed, with unkempt pubic hair.
“Open up,” each one ordered.
And I obeyed. One after the other, I took them in my mouth, learning to relax my jaw, to breathe through my nose, to use my tongue at the base while the head hit my throat. The first one came quickly, surprised by my forced enthusiasm. The second took longer, gripping my head with both hands, using my mouth like a masturbator, without restraint. The third wanted me to lick his balls first, at length, while he masturbated, before inserting his swollen glans between my lips.
The fourth one was the hardest. He didn’t come in my mouth. I wanted more.
“Pichón said he could fuck you,” he said, looking toward where Pichón was smoking by the door.
Pichón nodded.
They laid me on my back on the mattress, lifted my legs, one of them held my ankles while the construction worker, still wearing his hard hat, applied more lubricant to his cock and my already used anus.
“Squeeze,” he ordered. “I want to feel you resisting.”
I squeezed. In vain. He entered with a hoarse groan, filling me, stretching me, claiming my body as conquered territory. He lasted twenty minutes, varying the rhythm, watching my face as he penetrated me, enjoying my humiliation. When he finally came, he did it deep, withdrawing only so that the last spurt fell onto my stomach, marking me with his semen.
Two thousand euros. Four men. My throat irritated, my anus sore, my dignity in ruins.
Selena’s Service: Weekends
Selena had more clients. More demand. Her female body was a magnet for depravity.
The following Saturday, Pichón took her to a bachelor party. Twelve men. Three thousand euros for “full group service.”
She told me the details that night, while I treated her with creams, kissing her bruises. She was sitting in the bathtub, the warm water enveloping her swollen sex.
“They made me kneel in the middle,” she said, her voice distant. “One after the other. Some only wanted my mouth. Others, my vagina. Three ... three wanted my ass.”
She touched herself absentmindedly as she spoke, her fingers finding her clitoris underwater.
“The groom ... the groom was the last. He wanted to ‘try it before getting married.’ He fucked me for half an hour, looking me in the eyes, asking if my husband knew I was being used like this. I told him yes. That you knew everything.” That excited you.
She came in the bathtub, remembering, as I held her, my own erection pressing against her back.
The Monthly Balance
At the end of the month:
Selena: eight weekends, four bachelorette parties, two “couple services” = twelve thousand euros.
Husband: four Wednesdays, two group Fridays, three couple services = six thousand euros.
Total paid: eighteen thousand.
But the interest had grown. The original debt, with late fees and Pichón’s “management fees,” was now twenty-two thousand euros.
“You’re still in the red,” Pichón said, showing us the paper. “But you’re on the right track.”
He looked at us, assessing us. Selena with her new sex worker body: more confident, more open, more desirable. Me with my new submissiveness: more docile, more trained, more useful.
“I have a proposal,” Pichón said. “A special client.” Pay ten thousand in one go. But it requires ... total commitment. Both of us. For a full week. At his villa. No limits. A temporary slavery contract.
Selena and I looked at each other. In her eyes, I saw the same calculation I was making. One week. Ten thousand. Almost half the debt.
“We accept,” we said in unison.
Pichón smiled, showing his gold teeth.
“I knew you would. Get ready. The client arrives on Friday. And he has ... very specific tastes.”
He put the paper in his briefcase. The debt kept growing. But now we were more than just debtors. We were his star attraction. His perfect match.
And for the first time, I didn’t know if I ever wanted the debt to end.
The Special Client’s Week
On Friday morning, Pichón picked us up in a black Mercedes with tinted windows. He didn’t tell us the client’s name. He just handed us an envelope with the rules.
“Read, sign, obey. One week. Ten thousand euros. Debt paid in full.”
The envelope contained photos of a modern, secluded villa on the coast with high walls. And a list:
Rules for the week:
Permanent nudity on the property
24-hour sexual availability
No limits on practices
Use of both spouses by the client and their guests
Visual documentation permitted
Temporary body marking permitted
Selena and I exchanged glances. We signed.
Day 1: The Introduction
They dropped us off at the villa’s entrance at sunset. The client was waiting for us in the garden: a sixty-year-old man, gray-haired, with the body of someone who had taken care of his health his whole life, but with eyes that revealed decades of refined perversions. His name was Viktor, and he spoke with a Russian accent softened by years in Western Europe.
“Pichón told me about you,” he said, circling Selena, inspecting her like someone examining a horse. “The wife used by dozens. The husband, newly initiated. Perfect.”
He ordered us to undress right there in the marble garden. The sea breeze made our skin prickle. Viktor walked around us, fully dressed in his white linen suit, occasionally touching us: Selena’s nipple, my flaccid penis, the curve of his hip, the mark I still had on my ass from last Wednesday.
“Come in,” he said finally. “The week begins.”
The villa was a labyrinth of dark luxuries. Rooms with mirrored ceilings, furniture designed for sex, a playroom that would put any Berlin BDSM club to shame.
Viktor led us to the main room. Three other men were waiting: two his age, one younger, thirty, athletic, with the look of someone who enjoys inflicting pain.
“My partners,” Viktor introduced. “For this week, you belong to them too. But first, the welcoming ceremony.”
They positioned us facing each other, kneeling, naked. Selena and I, face to face, inches apart. I could smell her perfume, feel her breath.
“Fuck her,” Viktor ordered. “Now. I want to see how you move inside your wife while my friends watch.”
I entered Selena right there, on the Persian rug in the living room, while four men sat in leather armchairs with glasses of whiskey. I penetrated her slowly, aware of every glance, every judgment. Selena moaned, not just from pleasure, but from the performance. We knew we were on display.
“Enough,” Viktor said after five minutes. “Now for the next step. Separate them.”
They separated us. They took me to one side of the room, Selena to the other. The athletic young man, whom Viktor called Dmitri, approached me with a black box.
“Your wife will be used by us,” Viktor said, as two of his friends approached Selena, beginning to touch her. “And you ... you will be trained.”
Dmitri opened the box. Anal plugs of different sizes, all larger than anything I had ever felt before. They turned me on my side, lubricated me with something cold that numbed me slightly, and began the training.
The first one went in easily, a black cone that filled me but didn’t stretch me too much. The second one hurt, a thick cylinder that Dmitri inserted with circular motions, twisting it inside me, opening me up. The third was torture: a kind of oval, enormous egg that Dmitri pushed in insistently while I moaned, clutching the rug, feeling my body give way, my anus dilate to accept the invasion.
“Good,” Viktor said, watching. “You can receive me tomorrow. And my friends.”