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I Became the Matchmaker Between My Father and Wife - Chapter 299 

The father had always had a special fondness for Xiaoying's anus. Firstly, when he gave Xiaoying oral sex, he loved to lick and tease her anus, perhaps because it could bring her to orgasm, or perhaps because he liked the smell of Xiaoying's anus.
Secondly, her father had repeatedly inserted his fingers into Xiaoying's anus, performing finger rape on her, and Xiaoying never objected much, perhaps leaving some room for the attack on her anus.
Xiaoying gently swayed her hips back and forth, and her father could tell from the contractions of her anus the frequency of her physical pleasure.
"Mmm...ah..."
Just as Xiaoying was swaying her body and moaning softly, she suddenly let out a scream that was completely out of place. It was a scream, and the cause of this scream was her father.
It turned out that after watching Xiaoying's contracting anus for a while, a sly smile appeared on his satisfied face. He then extended his index finger and gently placed it between his crotch and Xiaoying's buttocks. Xiaoying then slowly moved her finger forward towards her anus. Unaware of this, Xiaoying swayed her body, and as she leaned her buttocks towards her father's crotch, her anus bumped right into his finger. Her father's finger remained motionless, and Xiaoying's anus offered itself up to him.
Xiaoying, who was focused on enjoying the pleasure brought by her father's penis, was suddenly stimulated in the anus without any warning. Although her father only inserted his fingertip into her anus a little bit, the stimulation and surprise it brought to Xiaoying was unparalleled.
Xiaoying's swaying body had to stop temporarily. The feeling was clear but abrupt. Xiaoying seemed to want to verify it, and her hips slowly leaned back tentatively again, but at this moment her father withdrew his fingers.
When Xiaoying's buttocks rested against her father's crotch, she didn't notice his fingers. A hint of doubt appeared on her face. Had she just been mistaken? Xiaoying tried again, slowly swaying a few times, but found nothing unusual. She then resumed swaying at a faster pace. At this moment, her father mischievously extended his fingers again.
"Mmm... Ah..."
Xiaoying's anus suddenly collided with her father's fingers again. This time, her father used a little force to slowly extend his fingers forward, resulting in his hand penetrating Xiaoying's anus more deeply than before, inserting a full halfway. This time, Xiaoying seemed to have learned her lesson. Just as her father was about to withdraw his fingers, Xiaoying reached behind her and accurately grabbed her father's hand. Her father was stunned; he hadn't expected Xiaoying to react so quickly. When Xiaoying grabbed her father's hand, she turned to look behind her. This was the first time their eyes had met since they started doggy style. Xiaoying revealed a "It really was you" expression, her face showing a hint of anger and scorn. Her father just grinned, because he could tell that Xiaoying didn't seem truly angry.
The scene was rather bizarre. Xiaoying was in a doggy-style position, and she turned her head to look at her father reproachfully. Her hand was still holding her father's hand, and half of the fingers of her father's hand that was being held out were still inserted into Xiaoying's anus.
The scene fell silent, and as I watched Xiaoying and her father's hands clasped together, I fell into deep thought. Was Xiaoying suddenly grabbing her father's hand to "catch him in the act" or to prevent her father's fingers from being pulled out of her anus?
Could it be that Xiaoying actually enjoys her father's fingering of her anus? After about half a minute, Xiaoying turned her head back, but her hand did not let go of her father's hand. After pausing for a while, she gently swayed her body again, and her father's penis moved in and out of Xiaoying's vagina again. Originally, the connection between the two bodies was only one point, that is, the penis and the vagina, but now there was another point, the father's finger and Xiaoying's anus. At this moment, the two connection points maintained the same speed and direction of friction and insertion.
After Xiaoying grabbed the hand that her father was using to insert into her anus, Xiaoying is now essentially allowing her father's fingers to be inserted into her anus.
"Ahhhhhh..."
Xiaoying's originally weak moans suddenly grew louder, and the reason for the increased volume was that Xiaoying's body was being stimulated in one more place...her anus.
Slowly, Xiaoying let go of her father's hand, and her father realized Xiaoying's intention. He kept his hand in that position, letting Xiaoying swallow his penis and fingers into her body through her vagina and anus.
Looking at this scene, my body was numb. Xiaoying had already willingly accepted fingering, so how far away was anal sex? I had already mustered up a lot of courage to watch this, but now I really wanted to back down. My hand was tightly gripping the mouse, and the cursor was on the close button for the monitoring screen, but I hesitated to click it. I didn't know if there would be footage of Xiaoying and her father having anal sex next.
Xiaoying and I had never engaged in anal sex before, and I had never even considered it. Perhaps it's related to personal preferences. I always felt that the anus is a human excretory organ, and using it for sexual intercourse would violate normal physiological laws and be considered a rather perverted behavior. So I never had that thought, and Xiaoying never mentioned it either. In the past, I thought that Xiaoying and I had similar personalities and interests, and that she shared the same views as me.
Previously, when I saw my father fingering Xiaoying's anus, I thought it was because Xiaoying was briefly lost in the throes of orgasm and didn't care about such things. But now, seeing Xiaoying actively letting her father's fingers penetrate her anus, and her expression so comfortable, and her moans clearly changed, proves that she enjoys and accepts this alternative method. Perhaps she had thought about it before but never brought it up with me, after all, she is always so virtuous and reserved in front of me. Now I realize that there are many unknown sides to Xiaoying.
I used to be able to control Xiaoying and my father's sex life, or at least predict the scene and manner of their encounters. But now I'm truly afraid. This time, it was also my father and Xiaoying's sex, even though they'd had sex countless times before. But this time was different. The stimulation it gave me was even stronger than their first time, because Xiaoying on screen seemed so unfamiliar. Tonight's initiative, her voice, her moans, her expressions, her mannerisms… I felt like she wasn't my beloved wife.
"ah……"
As Xiaoying let out a soft yet incredibly seductive moan through my headphones, my thoughts were pulled back to reality. I saw Xiaoying's buttocks pressed tightly against my father's hips, while his fingers and penis were deeply inserted into her anus and vagina. Xiaoying's head was tilted back, her face contorted in struggle, and her snow-white body trembled slightly. Her fingers, gripping the windowsill, were taut and white, showing the force she was exerting. Her buttocks were also trembling slightly, and soon, thick fluid began to drip from the gap between their intertwined genitals.
At first, there were only a few drops of liquid, but it gradually increased. After a while, the liquid became just a few drops again, and finally, no more liquid dripped between Xiaoying's buttocks and her father's crotch.
Seeing Xiaoying like this, I knew she had climaxed. Although her moans weren't loud, her body's reaction was intense. Most importantly, this was Xiaoying's first orgasm during gentle intercourse. Her previous orgasms were always from rapid, vigorous thrusting. But this time, Xiaoying was in control, gently swaying her body, actively allowing her father's penis to slowly and gently enter her body again and again. Yet, Xiaoying still climaxed. It seemed that this gentle, proactive approach had brought her orgasm even faster than the vigorous thrusts her father had just unleashed. What could be the reason for this? I couldn't help but ponder this question…

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