Swallowing excitedly, Ryan held Jessica’s beautiful legs with both hands. His thick, hard and hot cock hung under his crotch, as mighty as a spear. He slowly advanced forward and reached the entrance of her virgin hole.
However, because Jessica white pussy was too tight and her labia were tightly closed together without any gap, Ryan tried for a long time but failed to insert it. As a last resort, he used both hands to separate the two plump and tender pink labia, revealing a needle-sized flesh hole, and then he stuffed a small part of the glans into it.
"No, don’t...Ryan...it hurts, I’m not ready yet...really...please...can you please take it out..." Jessica’s expression became anxious, her eyes filled with pain and pleading.
Ryan turned a deaf ear to all of this. The pleasure coming from his lower body made him feel very comfortable. Before the formal insertion, just by pushing open the labia and inserting it into the hole, he could feel the strong squeeze. The two labia bit the glans tightly, and the feeling it brought was indescribable.
Holding her slender waist, Ryan pushed forward with force, and the huge glans forced open the tight virgin hole and went straight in.
"Ahhhhhhh..." The pain of her vagina being stretched open made Jessica scream. Ryan clenched his teeth, not daring to stop at all. He thrust his waist hard with all his strength, driving the glans inside.
After squeezing open a layer of thin membrane that had almost no blocking effect, the penis went straight into the deep of the vagina.
Ryan naturally knew that it was the hymen of Jessica. With the insertion of his penis, another virgin was also taken into his pocket. However, Ryan now had no time to sigh. The layers of flesh that kept squeezing in from all directions almost crushed his penis.
Even though he thought his penis was as hard as iron, he felt that it was about to be cut off by Jessica’s virgin hole.
When he was breaking the virginity of the other two women, Mia’s vagina was the tightest. It was very difficult for him to even move when he was breaking her virginity.
However, compared with Jessica’s vagina, it was still a bit weaker. Ryan just inserted his penis into the vagina, and before he could move it, he felt like ejaculating because of the squeezing inside the vagina. The feeling was even getting stronger and stronger.
He gritted his teeth, ignoring the crazy screams and cries of Jessica under his crotch, and thrust his waist hard. Because Jessica’s pussy was too tight, every thrust consumed a lot of his strength. The cock almost rubbed against her tight and tender pussy and moved forward. The pink labia soon turned red from the friction.
Seeing the miserable scene of the little Lolita losing her virginity, Mia couldn’t help but feel very pitiful, so she took the initiative to support her tired body, slowly walked behind the table and supported her body, "Don’t be afraid, relax, it will be over soon..." She kept comforting the poor little girl.
Mia took the initiative to support Jessica, which saved Ryan a lot of energy. For him, the pleasure of fucking a virgin’s pussy was naturally incomparable, but for Jessica, a virgin, this was undoubtedly the most horrible punishment in the world.
"Ah… It hurts… I can’t take it anymore… My lower body is going to break… It hurts so much… Aaaaaa…"
Jessica face was pale, her beautiful eyes rolling upwards, her fingers clenching so hard that her knuckles turned white. If it weren’t for Mia and Ryan supporting her, she would have collapsed to the ground or slumped onto the table in agony.
"It feels so good...hiss...you’re so tight down there...it feels amazing..."
Ryan groaned in ecstasy. The intense pleasure was driving him wild. He thrust his hips hard, pounding into the tender, delicate hole of Jessica again and again. Her once-perfect white pussy was now a ruined mess.
The pain in her lower body was so overwhelming that Jessica instinctively clamped her legs together, squeezing Ryan’s waist, which only made her vagina even tighter.
Ryan had to force her legs apart again, spreading them wide to almost 180 degrees, while Mia held her body from behind to give him better access.
The pain of having her legs forcibly spread apart left Jessica looking utterly devastated. Before she could protest, another brutal thrust from Ryan nearly knocked her unconscious: "Ahhhhh... don’t be so rough... I’m going to die... go slower... my lower body is breaking ahhhhhh..."
With her legs spread so wide, her vagina finally became easier to penetrate. Gradually, Ryan realized there was still a small part of his penis that hadn’t been fully inserted, his glans already pressing against her cervix.
Seeking even greater pleasure, Ryan signaled Mia to hold her steady against the table. Then, gathering his strength, he thrust forward with even more ferocity.
"Ahhhhhhhhhh…I can’t take it anymore…It hurts so much…I’m going crazy…Ahhhhhhh…Ouch~"
The moment her cervix was hit, she completely lost control. She couldn’t hold onto Ryan’s shoulders anymore, her body twisting wildly as she tried to escape the unbearable pain.
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If Mia hadn’t been holding her from behind, she would have collapsed. Even so, Mia, leaning against the table, struggled to keep her steady. Her own body, still weak from her recent orgasm, could barely stand. Ryan, however, only fucked her harder, slamming into Jessica’s cervix repeatedly, determined to break through her uterus.
The poor girl screamed in agony, her pretty face contorted in pain, tears and saliva streaming down her cheeks. Her petite body spasmed uncontrollably, as if she couldn’t endure any more.
"Ah... so good... hiss..." With one final, brutal thrust, Ryan’s glans pushed past the narrow cervix and plunged deep into Jessica’s uterus.
Jessica’s eyes rolled back, and she nearly fainted from the overwhelming sensation. But for Ryan, the pleasure was indescribable. Her pussy was impossibly tight, and because her vagina was so small and his cock so large, he could actually push his glans into her uterus.
This meant her cervix clamped down on his glans, allowing his cock to be ravaged and sucked by different parts of her body from front to back, amplifying the pleasure exponentially.