"L-Let me go, t-this is too embarrassing." Anna pleaded as she tried to close her leg, only to have Kate holding firm.

"I''m doing this for your good. You don''t want to have an extremely painful first time, do you?"

Despite Anna not saying anything, her inaction tells Kate everything she needs as she moves her hands up.

"What are you waiting for?"

Xiaoyun finally took action as he forcefully ripped the silk covering Anna''s crotch, revealing her labia to a man for the first time.

Unlike Kate, Anna''s opening looked extremely pink, almost as if she had put makeup on it.

With a clear liquid around the entrance, it was clear her body was already turned on.

Still, there was nowhere near enough for Xiaoyun to enter inside without causing Anna too much pain.

"Don''t move, okay? Xiaoyun and I are going to try to make it as gentle as possible."

Anna nodded again as she watched Xiaoyun''s cock gently brushing over her labia with his finger resuming playing with her clitoris.

"Hm!"

Seeing a tear falling from Anna''s eyes made Xiaoyun immediately stop, only allowing the tip of his cock to enter inside.

"You okay?" Xiaoyun softly asked as he caressed her face gently.

Anna tried to nod, but she had to bite her lips to hide the urge to scream out in pain.

Even though her inside was already soaking wet, Xiaoyun''s size was simply too much for her first time.

"If you want, I can make it smaller——"

"N-No, it''s fine. I-I can handle it."

Despite Anna''s stubbornness in wanting to take on Xiaoyun as it is, he secretly shifted his body to be a little smaller.

Just enough that Anna''s frowning finally disappeared, as she thought her body was starting to get used to it.

"I''m going to start moving in, okay?"

As Xiaoyun gently moved his hip forward, he could feel the pushback his cock faced.

Soon, a few drops of blood began to leak out, indicating her first time was now finally gone.

"Congrats, you did it," Kate whispered as her hands still firmly held onto her lower knees.

Anna looked a little relieved as if her virginity had been a burden rather than something she wanted to keep.

"T-Thank you——Hm!"

"I should be the one saying thank you... You saved your body this long just for me."

As Xiaoyun finished speaking, he could finally begin to move much more freely inside Anna''s vagina.

He could feel the pain on her face was starting to subdue. Her body was starting to feel pleasure instead.

With more and more exploration inside her vagina, Xiaoyun soon found her weak spots.

"Anna, you don''t have to hold in your moan. Just let it all out."

Kate''s suggestion was completely ignored as Anna refused to open her mouth to moan out loud.

Meanwhile, Xiaoyun didn''t bother at all, as he was too focused on making her feel good first.

"Hm!——This is what sex feels like——Hm!——I-It feel so much better than I imagined it to be——Hm!"

The two finally understood what Xiaoyun meant by it as he moved his finger to spread her labia apart slowly.

"This is what Kate''s hymen looked like in the past... It looks beautiful, doesn''t it?"

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Kate''s face blushed redder than ever as she still couldn''t believe what Xiaoyun had done to her body.

At the same time, deep inside her heart, she was extremely grateful for him fulfilling her wish.

"I never knew it looked like that..."

Just as Anna was about to reach her hands forward, Kate quickly pushed it to the side.

"S-Stop it. I''m not just some sex ed toy." Kate argued as she tried to cover herself, only to have her hands pushed away again.

"Anna, can you help me?"

Within seconds, Anna immediately understood what Xiaoyun meant by it as she moved behind Kate before grabbing onto her thighs.

Legs apart, with another woman behind her, Kate was back in the position Anna had been acting in just a few minutes earlier.

"Would our dear husband take his wife''s virginity?" Anna whispered as she held on firmly.

Not wasting any time, Xiaoyun moved forward before pressing his body directly onto Kate.

"Ah!——T-This is too big——Hm!——I-It hurts!"

Kate groaned in pain as Xiaoyun shoved his cock halfway in rather than just letting the tip in.

"You''re so much tighter than before..." Xiaoyun murmured as he slowly pulled back to the tip.

"You idiot. What do you think you had just done to me?"

Kate held in her tears as she had now experienced losing her hymen for the second time in her life.

With drops of blood landing onto the bedsheet, the two had officially lost their ''virginity'' on the same day.

"Sorry... I thought I had just healed the layer. I must have accidentally overdid it."

Despite Xiaoyun''s apology, his hip hasn''t slow down at all as he began pushing in again.

Soon, the pain slowly disappeared, and Kate started to moan in pleasure again as Xiaoyun quickly reached her sweet spot.

"Ah!——Y-You can go harder——Hm!——I miss this feeling so much!——Ah!

Hm!——I love your giant cock!——Fuck me harder please——Hm!"

As Kate began to move her hips along with Xiaoyun, Anna was a little shocked by how lewd her best friend looked.

It was almost a completely different person, with her lewd, moaning sound echoing the room.

"Kate, do you want me to cum inside?" Xiaoyun asked as he was starting to feel his limit.

"Just cum inside me!——Hm!——I don''t care anymore!"

Kate''s answer shocked Anna a little as she let go of her thighs, allowing her to wrap around his hip fully.

"Cumming!"

As Xiaoyun let out his first load of the night, Kate finally couldn''t hold it any longer as they both climaxed at the same time.

With Kate''s womb filling up more and more, she couldn''t hold back and climax again and again.

After what felt like forever to Kate, Xiaoyun finally pulled out of her body before gently putting her next to Anna.