Chapter 108: Chapter 107

“O-okay. You can lie down then.” Anna declared.

I raised an eyebrow, but I didn’t hesitate to lie down into the position she asked. I was a bit surprised that Anna wanted to take charge, but every girl had her fantasy about how their first time was going to be, and it looked like she wanted to be in charge. Thankfully, with the sight of her naked body in the moonlit night, along with the memory of her seeping pussy on my lips, I was able to remain fully erect. I unzipped my pants and then allowed my cock to pop out into the night air.

Anna’s eyes seemed to jump to my cock immediately. Whether she was just admiring it or felt a bit intimidated, I couldn’t say.  She did gulp and lick her lips before finally lifting her leg and throwing it over, straddling me. I was surprised to see that she didn’t choose to face me, but was instead facing away. She didn’t immediately mount my dick but instead straddled my abdomen. All I could see was her bareback and her butt. Her butt was neither a nice bubble but, nor something flat. Anna had always been cute but wasn’t particularly remarkable in looks, which was probably why she had no experience.

In my world, she would have been bugged by hundreds of guys desperate to bang her, even with normal looks. Yet, in this world, she was a geeky virgin whose first time she was eagerly going to hand to me.

“I think your penis is hot,” she said, her hand coming out and stroking it.

Although I couldn’t see her, I could feel the palm of her hand rub up and down it. She reached down and squeezed my balls. It was almost like she was touching them just for the gratification of feeling a cock in her hand. Her fingers wrapped around and squeezed it. It was like she was building herself up for the next moment. That moment came as she scooted forward, her wet pussy leaving a trail along my shirt that she seemed oblivious of.

She pushed her cunt up against the top of my cock. I could feel the wet heat of her slit and the tangled hair of her bush. She rocked her hips, not sticking my cock in, but allowing her slit to rub up and down my cock, making it wet with her juices. Whether she was just playing with it for fun, or this was part of some video she had watched, who knew. If I asked, such a question would surely embarrass her, so I kept my mouth shut.

Her hips seemed to move faster and faster, her body humping against the side of my cock. The feeling was great, and so was the view. Her butt shifting back and forth was mesmerizing, and so I reached out and squeezed it. She let out a moan, and while I could probably cum like this, I wanted to stick in inside her.

“I want to fuck your pussy.” I said.

“You want that pussy?” She asked her voice slightly higher pitch than usual.

“Yes.”

“Tell me you want that pussy.” She moaned.

“I want your pussy.”

“Tell me you want that tight pussy.”

I didn’t take Anna for such a dirty talker, but I guess it was the good girls who were secretly the baddest. I grinned slightly to myself.

“I want your tight pussy.”

“Yeah… fuck… yeah… your hungry little cock wants to invade my tight little pussy. Do you want to fuck my cunt? You want your big dick in my cunt?”

“Fuck, I want it so bad!” I decided to play along.

“Hah…Hah… y-yeah… ahhhhn…” She started panting and moaning, and I felt the lips wrapped around the top of my cock twitch suddenly.

Her movements slowed, and her body shook. I couldn’t help but let out a noise of surprise.

“Did you just cum?”

“… no.”

“Seriously… did you orgasm?”

“I-I didn’t.” she declared, even as I felt wet juices leaking all over my dick.

“It’s okay if it happens…”

“I didn’t cum yet! Th-that’s just… a precum!”

“It happens to lots of girls…” I was deliberately teasing her now.

“My pussy can take your cock! I’m not some one time and done!” She sounded slightly angry, slightly desperate.

She lifted her butt, and then reached down and spread her labia with one hand. The other grabbed my dick and lined it up.

“Anna…”

“See? Now fuck my pussy!” She lowered herself down.

Her slit was wet and slippery against my erection, and rather than popping in, it popped out the front, causing my dick to once again slide up her slit. I was very good and made sure not to laugh at all. Anna was trying hard, and if I destroyed all of her self-esteem, then what kind of boyfriend would I be? I reached out and grabbed her butt, helping her bring it back up as she made a second try. This time, she grabbed the root of my cock with her hands and then planted the head of my cock between her lips.  

She started wiggling her butt, moving side to side to make sure that my cock was going in the right hole and didn’t miss again. Her legs started to bend as my cock slowly began to push into her. Her body quivered slightly as my head popped into her hole. She stopped at that point to get a breath. Her tight pussy was pressing down on my cock. Perhaps, she had come to see just how big it was and what she must accommodate.

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She wiggled her hips some more, change the angle several times. After each adjustment, she let her knees fall slightly, pushing my cock into her vagina a little bit at a time. The lack of speaking showed how much concentration she had as she tried to take my cock. I had read online that taking it all at once on their first go was a sense of pride for women. Anna had already failed at that, but as long as she could take it all, she was determined. I could see a droplet of blood run down my dick just under her ass, but she persisted in lowering it even more.

She was panting very hard, and her body glowed in the starlight with a sheen of sweat. Finally, her knees met the ground with only an inch of my shaft still outside of her pussy.

“It feels wonderful,” I assured her, not even having to lie.

Her pussy was tight and wet. I had no reason to complain. When I noticed her not responding, I reached out and grabbed her hips, and then forced the last inch down.

“Ahhhn…” She moaned, her body shaking.

“You okay?” I asked.

“Yes…” she said through clenched teeth. “I guess I’m not a virgin anymore.”

We remained like that for a few minutes as she recovered. When she finally could start moving again, she started to raise her butt up and down. She moved very slowly, and as a result, I was able to last. I had gotten pretty horny already, and I just wanted to grab her and hump her. However, with that, I’d be done in a few minutes. Like this, I could keep enjoying her pussy for the immediate future.

I decided to resist my primal urges and put my hands behind my head. I watched Anna’s naked body as she continued to bounce up and down on my cock. The longer she went, the more confidence she had, and the more aggressive she grew.

“You like that, baby?” She asked.

“Yeah, baby,” I responded, biting my lip.

“I’m riding your big cock. It’s filling my tight pussy up so much. I hope it’s tight enough for you. Yo-you can stick it in my butt if it’s not.” Her voice slipped as she said that.

“I want to cum in your pussy though.” I teased.

“Ahhh… c-cum.” She panted, her body still moving up and down even as we talked. “You can cum. I’m not on protection, but I’ll just take a morning-after pill.”

“Are you sure?” I asked.

“Y-yeah… I want Noah’s c-cum in me too.” She declared.

“Then… make me cum.” I teased.

Something about my words seemed to strike Anna, and she suddenly pulled up. My dick slid out of her pussy, flapping back against my stomach. My dick was covered in her lewd juices at this point, and the rich scent of her body filled our little hidden clearing. She spun around so she was facing me, and I could see her red, swollen pussy lips, and a hungry gaze in her eyes. She reached down and grabbed my cock again, jumping back on me and then sliding my cock back into her pussy. This time, she was able to get it all the way in with a single slide.

She grabbed my arms and then shoved them over my head, and she started to bounce up and down, using my hands as leverage. She was moving so much that her breasts bounced side to side a few inches above my face. I lifted my head and found my lips could just reach her nipples every time they swayed back and forth. I couldn’t help but latch on and suck them as her hips worked my cock aggressively.

“Ahhhn… oh… yes… Noah… fuck… I love your cock. I love it. Give me that cock. Give it!” she moaned.

I started thrusting up, each time our wet part slapped together it created a loud thwacking noise. We were in the middle of a public park, and we were no longer attempting to be quiet in the slightest. If anyone was even remotely near us, they’d be able to hear everything we were doing. Her hands abandoned my wrist and she grabbed my hair, her butt violently shaking as she tried to smother my cock with her pussy in every thrust.

My free hands reached down and grabbed her ass, gripping her cheeks tightly. I started thrusting up with rough, hard thrusts, and every time I went up, my hands pulled her ass toward me, slamming our bits together even more roughly.

“Cum! Cum in me! Cum in my pussy, Noah!” She growled forcefully, her eyes almost predatory.

Even if she hadn’t asked, I had reached my limit. She continued to pump her hips, fucking away as my cock started to unleash the contents of my balls deep inside her. I spurted load after load into her hot, wet pussy, but Anna didn’t stop riding me. She kept fucking my dick all through my orgasm as if she was afraid of missing a single drop of my cum.

I thought that my cumming would lead to her stopping, but rather than slow down, Anna started to speed up. Even as gobs of cum leaked out, she still bounced her ass up and down, slapping her pussy down onto my dick wetly.

“Ahhh! Ahhh! Ahhh!” She moaned, her hands pulling my hair as she bit my chin.

Her teeth let go as she let out another yell. “I’m gonna cum! Noah… I’m almost there!”

It was strange. In most of my encounters, we usually came at the same time, or even if I came, they would have already cum. It was true that Anna had already cum a few times tonight, but it appeared like that wasn’t enough for her. Even though I had finished, she wanted to have one last orgasm. Was this how a woman who had already cum felt as her man pounded away at her?

I didn’t know, but a part of myself I hadn’t felt in a long time, the part of myself that had pride as a man, realized I absolutely couldn’t lose wood until I made her cum. Even though I had already finished and was tired, I willed my cock to remain stiff. I reached out and grabbed her hips, and then started helping her, thrusting up deep into her soaking wet snatch.

“Yes! Yes! Yes! There! Yes!” She started shaking, her eyes rolling up in her head for a second as her body began to spasm.

I could feel my cock gripped so tightly I thought she might take it with her if she stood. Anna threw herself down on me, her mouth finding mine. She began to kiss and hump me aggressively, her body completely wild like an animal as her body flew into an orgasm on top of me.

I could only describe it all with one word, intense. The quiet and reserved Anna was probably the most dominant and wild of any girl I had been with. Who would have guessed?

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