The Bet

My name is Stefanos and I'm 23 years old. My best friend is Giorgos, and we have another friend, Dinos—all the same age. One night, the three of us went out, and after a few drinks we started talking about older women. Giorgos insisted that any woman over 45, if given the chance, would sleep with someone much younger—even if he were the same age as or even a friend of her son. I agreed that some might, but said most wouldn't actually go through with it because at that age they think more maturely and logically, and especially among the women we know, not a single one would do it.

Then Giorgos challenged me to a bet, saying he could even seduce my mother if given the chance. I took it as a joke, but he was serious—he said he'd go for it, and if he failed, he'd give me 300 euros; if he succeeded, I'd give him 100. Confident in my mother's integrity and tempted by the 300 euros, I agreed.

Before I continue, let me describe my mother's appearance. She's 48, with black shoulder-length hair, about 1.65 meters tall, no more than 65 kilos, and has a full, generous bust. Overall, despite her age, she remains a very attractive woman. A few days later, while my older brother was away on vacation, my father had to leave the village overnight for work. The perfect opportunity had arrived for me to win the bet.

That day finally came. Late in the afternoon, my friends arrived at my house. We locked ourselves in my room with loud music playing so no one could hear us, going over the final details of our plan. We got ready to leave, pretending we were going out for the night. I told my mother that Dinos and I were heading into town, while Giorgos was going to visit his girlfriend in the neighboring village. In reality, we went to the village café, after Giorgos had left his phone somewhere in the living room. About 20 minutes later, Giorgos took my phone and called his own (with caller ID blocked, of course). My mother answered, saying his phone was there, and Giorgos said he'd come by to pick it up.

The plan was now in its final stage, and I could already feel the 300 euros in my pocket. Giorgos and I left the café while Dinos stayed behind. We reached the house, and I quietly climbed through the window of my bedroom from the balcony—the window I'd left open earlier—while my mother opened the door to Giorgos, who was ringing the bell. I crept close to my bedroom door to clearly hear my friend's rejection by my mother. But Giorgos went straight for it. He admitted he'd deliberately left his phone behind and that he'd been waiting for a chance to be alone with her. My mother replied that aside from being married and never having cheated on my father, he was also best friends with her son—me. I remember her asking how it was possible for a nice young guy his age, who had a girlfriend his own age, to want a woman her age. Then Giorgos said he'd been in love with her and fascinated by her since he was a boy, that my mother had featured heavily in his sexual fantasies, and that she'd been the reason for many of his teenage masturbations. He went on to say that with my father and brother away and me not expected back for a long time, this might be his only chance to fulfill his dream. And while I was waiting to hear the sound of my mother slapping Giorgos across the face, absolute silence followed—and a few seconds later, I heard the door to my parents' bedroom close.

I stayed in my room for a moment, first thinking of leaving, but then decided I should see with my own eyes if anything was really happening. I walked quietly toward the bedroom and put my eye to the keyhole (the door was parallel to the bed, giving me a general view of the room).

The sight, of course, wasn't what I'd hoped for: my mother was on her knees, wearing only a black bra and black panties, giving Giorgos a blowjob. He was already completely naked, slowly pulling off her bra while playing with her nipples. After sucking him for a while, Giorgos lay down on the bed, and my mother, first removing her panties, climbed onto his cock and started riding him wildly. I didn't know whether to stay or leave—the initial shock had been replaced by sudden arousal.

Meanwhile, the couple changed positions. Now my mother was lying on her back with her legs in the air, and Giorgos was on top of her, fucking her furiously. Then he pulled out and slid his cock between her breasts. She used both hands to squeeze her tits around his shaft. It was only a matter of seconds before he came—exactly as I expected. He shot all over her face, covering it completely with cum, and she used her fingers to gather it from her cheeks and lips, putting it into her mouth. Finally, it was over, I thought to myself, and I returned to my room, waiting to hear them leave and go to the bathroom—but I heard no noise. Oh, we're probably in for a second round, I thought. And I was right.

Carefully, I went back to the keyhole. Giorgos was now lying on his back, and my mother, having wiped her face, was giving him another blowjob. This time, it was slower—she took his entire cock into her mouth and held it there for a long time, while he fingered her ass. As soon as his cock was hard again, she got up and sat on him once more, this time backwards (so that he was looking at her back). She moved up and down, rubbing her clit at the same time, until Giorgos suddenly flipped her onto all fours and thrust into her ass. My mother screamed, but told him to keep going, and he started fucking her ass hard, his hands gripping her waist.

I'm ashamed to admit it, but I was fully erect and had my hand on my cock.

How could I not get hard when, aside from seeing everything, I could also hear her moans and words—like "Rip me apart, baby," "Fuck me, you little slut," and "What a cock this woman has"—echoing through the house?

He pushed her face down into the bed and fucked her from above while she kept moaning, clutching the sheets from both pain and pleasure, until he came again, this time all over her back. Then he took her hand, smeared her back with his cum, and lay on top of her, kissing her on the cheek. I heard her say it had been amazing, but it couldn't happen again because she loved my father and didn't want to jeopardize my friendship with Giorgos. I, who had by then come in my pants, returned to my room while they went to the bathroom. When I heard the shower running, I changed my underwear and climbed back out the window, going a little further down to wait for Giorgos. A little later he came out too and asked me if I saw everything. Silent, I took out and gave him the 100 euros and we headed for the café. There, Dinos was waiting for us and asked what happened. Giorgos immediately answered that at the last minute we canceled the bet and he just went in and got his phone and that we had been sitting and talking, just the two of us, outside my house all that time.

I went back home, my mother was asleep while sleep wouldn't come to me. I was thinking about the events of the day, that I was the one responsible for cheating on my father, me and our stupid bet, but on the other hand I said that what she did was her own choice, she could have rejected him but she didn't, and in the end she enjoyed what she did and that maybe it was also a repressed desire of hers at some point to be with a younger man, after all, it would refresh her and strengthen her relationship with my father. That's why it was better she went with my friend rather than with someone else who would tell everyone and make us the talk of the village.

In the morning when I got up I saw my mother in quite a good mood, I went to Giorgos's house, thanked him for not telling Dinos and he promised me that he wouldn't tell anyone and that it would never happen again. On my way back home again, I was searching to find what was ultimately the worst part: the money I lost? That my mother cheated on my father? That she got fucked by my best friend, or maybe that I got hard and came watching my mother get fucked? The positive is that I learned that older women like younger men and I made sure to take advantage of that. Sorry if I bored you, but I believe it was worth the effort.