“H-hurry up, okay…?” Mary said, glancing back.

As her words met his ears, he nodded before gulping, finally pushing his large tip against her entrance.

Due to the combination of his sizely member and her tight, untrained hole, he had to slowly spread her entrance with his tip as he pushed in carefully.

“D-daiki, be gentle, please…” Mary asked through a quiet moan that escaped her lips, causing her to cover her mouth with her hand. 

He was more focused on actually letting his girthy member fit into her taut pussy, looking down as he watched it slide in as a snail’s pace. 

It was soaked, lathered in her own juices, yet even the abundant lubricant made it an arduous task. 

As he finally worked up the forwardness to take control and hold onto her hips, he pushed in most of his length with a nice thrust that planted his tip directly against her cervix, giving it a small kiss.

It was his first experience with the concept that might as well be mythical to a twenty-four-year-old virgin like himself: “the warmth of a vagina”--and it was even better than he had dreamed. He could feel her walls grip and squeeze his shift, tensing up around it with its soft, wet, and warm texture as if trying to milk him. 

This is what I’ve been missing–?! He thought. 

The moment the head of his cock met her cervix, a moan left her lips again, slipping through her fingers.

He hit the jackpot; though he was a virgin, at least before this very moment, he knew most girls didn’t exactly enjoy their cervix being met. 

However, as he tested the waters and pressed his cock down against her womb barrier, he felt her tight, warm walls clench around his length, squeezing it aa her legs quivered. 

Damn, she’s sensitive, isn’t she? He thought.

He had yet to begin thrusting yet it seemed length and girth alone, stretching her petite hole, was enough to make her quiver there, helpless as her juices spilled onto the ground. 

“Are you…a virgin?” He decided to ask.

“N-no…” Mary answered through muffled moans, “…maybe…”

He didn’t need her to admit it for him to know, going by the way she received it: Mary was gripping onto either side of the large crate she was bent over, keeping her mouth covered to hide her moans from those who passed by the dark alleyway. 

As he continued to slowly push in deeper, surprised at how her cave seemed to allow more of his length over time as she grew more into it, he finally fit himself balls deep inside. 

“Ngh…!” Mary’s muffled moan escaped. 

With his entire shaft embedded into her warm, tightening hole, his larger, heavier balls were pressed up against her small, but smooth pair. 

Tears finally escaped Mary’s amber eyes, trailing down her soft, pale cheeks as she kept her hand covering her mouth, with the other clenching onto the side of the crate. 

It’s big–too big! It hurts, but feels amazing…way more amazing than painful–! Mary thought. 

As she sat there, only able to stare at the shadow-cast brick wall while being thrust into, her hips were tightly held in his surprisingly strong hands, slightly lifting her feet from the ground that were already hardly there as she had to tiptoe due to her short stature. 

Lifted up slightly, Mary’s hole was beginning to experience a similar roughness than her throat did as he was overflowing with primal urges now, beginning to slide his length back and forth as her lips gripped around his shaft, trying to prevent him from pulling out, though he didn’t plan to. 

“D-daiki, slow down…!” Mary told him. 

The more he pumped into her, the easier it became to thrust as her pussy adjusted to his length and girth, shaping itself to his size and exuding juices that made the process come easier. 

Still, he hardly listened to her as he pressed against her, beginning to thrust rapidly as their balls slapped together with each movement, causing Mary to learn completely against the crate with a mixture of moans and pants leaving her soft, pink lips. 

“...D-don’t finish inside…!” Mary called out between pants. 

It was as she could feel his cock swelling up inside of her, throbbing and twitching vigorously within her as he seemed to hear at least those words from her. 

After a few more seconds of aggressive pumps into her, he pulled out against the will of her tight, gripping walls, sliding it out just in time to shoot out his hefty amount of semen directly against her pussy lips. 

“Nngh…” Mary moaned quietly, laying her upper-half against the crate as she came as well with her smooth, pale appendage releasing onto the ground below. 

In the aftermath of the deed while Mary laid there for a minute, still and panting, and he stood there with his cock finally going limp, the semen had painted her rear with slid down, soaking past her balls and enveloping her cock in his juices.