Penetration

“Let's start in missionary position, Tess. If you want to take a break or stop anytime, it's okay. I won't rush you. We have all night.”

“Okay,” I said nervously. “Have you been with a vir... Nevermind.” It was a stupid question.

“Yes, you'll be fine.”

“I believe you.” I leaned back on his bed, propped up by a large pillow and the padded headboard. I spread my legs and put my feet on the bed with bent knees, which angled my pussy up slightly for him. “Will this work? I want to watch it go in.” Plus it would help keep some of his large weight off me in the beginning.

He nodded and complimented my body again and knelt between my legs. He kissed me again for a minute, letting me get used to some of his weight on me with that cock poking at my inner thigh. When he knelt upright, I reached out and clasped his cock. Good lord. “That thing is huge.”

I hadn't noticed the bottle of lube until he took it from the bedside table. “Watch out,” he said, and pumped a lot of it onto his erection and spread the gel around the entire length. I loved that he was prepared. He put on a condom without me asking and had lube ready. Unlike at the Crossfit Games, this time I was prepared. But I didn't have to get my own condom from my purse and demand he use protection. “Guide me in, Tess,” he commanded.

He was so masculine and confident. I obeyed immediately. I gave him a nervous grin and used two fingers to tease apart the large lips of my bare pussy. I gripped behind the slippery head with my other hand and brought the tip to my lips. I sobered up fast when that enormous dick pressed against my lady parts. I guided him down my slit, the large head covering the wide span of my splayed flaps until it reached my waiting hole. He applied just a tiny bit of pressure to indent my flesh around the hole and seat it at my entrance so it wouldn't slide off target. That was enough to make me gasp. This is really going to hurt. Let's do this. "Push,” I said.

I felt the forward pressure, but I waited and waited and nothing happened. He was a gentleman and didn't try to cram it up in there too hard. I felt him rock back and forth a few times to test me. “A little harder now,” he said softly. It started to hurt as the blunt head tried to squeeze in. I looked down, and the ridge of his head wasn't even inside! He tried a few more times, but with normal pressure, it just wouldn't go in. I might have just been too nervous. I don't think my hymen was even relevant yet. It seemed like the labia and flesh around the entrance wouldn't stretch enough. I was wincing, and he noticed and pulled back slightly.

“Sorry,” I said.

“No problem,” he said.

Pressure again. I put my hand down to signal a stop. It burned. “It won't go in,” I complained. But really, I knew it would. He just had to push harder and hurt me more.

Dr. White was being very patient. “No rush, we can take our time getting it in.” He got the lube out again, but this time put the gel on his fingers. “I'm going to dilate you more digitally to prepare you for intercourse,” he said.

“God it's sexy when you talk like that, doctor,” I said. I was kind of serious.

He chuckled. “Really?” he asked with a grin.

I nodded. Lubricant applied, he slid a slick finger into my pussy while kneeling between my legs. It went in no problem, and he really took his time working it in and out. My eyes alternated from his face back to his cock, which remained hard, pointed down and too massive to allow a high erection angle. He applied more lube and met my eyes.

Whoah. Sudden fullness. Stretching me, but good. I think. Pain, but just a little. “What...” I started.

“That's two fingers in your pussy. You're doing great. Are you okay?”

“Yeah, It hurts, but not bad.” I'd taken two of my own, but his were much larger. This felt more stretchy than when I used the dilator even. He was looking into my eyes intensely, gauging my reaction to the new sensations.

He left them in me, still, for a few seconds. Then: “Okay?” The digits were moving again.

“Uhhh,” I moaned. I felt the fingers slowly slide in and out a few times before answering. "Uncomfortable,” I replied. “Getting better.” I looked down and lifted my head and was able to see the two digits buried in my pussy. I relaxed my head and tried to also relax down there, and the pain went away quickly. The fingering was a good idea.

He pulled his fingers out and held them up for me. He wiped a finger on my knee, and I could see the red tint better on my light skin. “Progress,” he said.

I nodded. I naively thought he'd popped my cherry and it would all be smooth sailing after this. “Maybe you should put a towel down,” I suggested. He had white sheets.

“It's okay, don't worry.” Dr. White fingered me for a few minutes, adding more lube twice. His objective wasn't to make me come again. His fingers were there only to prepare me for cock. The in and out motion changed to a twisting motion, and I felt pressure on the sides of my vagina at different angles as he worked me. Then he curled them up and started tugging that that area just inside my pussy on the roof of my canal while his thumb hit my clit. Fucking awesome that was. Now it felt fantastic. It took me a minute to sort out what was happening. I knew about squirting and the potential this had. The sensations were fabulous, even as he got more aggressive pressing up against the roof of my vagina. The squishy sounds were quite entertaining as he rapidly pulled his fingers back and forth just a half inch or so. It sounded violent, but he wasn't hurting me at all or stretching me more. But the short, rapid movements were rocking my G-spot.

“That feels really good actually,” I said. “A little weird. I might pee on your bed.”

“Then it's working. We can keep going. I'll make you come like crazy. Or...” His voice trailed off as he glanced at his cock.

“Sex. I want to try again,” I answered. I grinned and arched my eyebrows.

“I was hoping you'd say that,” he said. He was already kneeling between my legs, so he quickly added more lube to his cock. His eyes met mine again when I felt the blunt tip against my lips. I nodded. “With respects, I can't wait to fuck you,” he said. I grinned big. I was determined and ready this time.

He was already pushing in, and of course it hurt. But it hurt different this time. He was definitely squeezing in, and the pain was targeted against the tightness and tissues inside me that specifically blocked his entrance. He was about to pop my cherry. I leaned up, and I saw the ridge of his enormous cockhead still outside the hole, but barely visible outside my labia. And then I shuddered in surprise as it passed into me. I was opening to him, and my pussy burned like a mother fucker as the head disappeared into the hot hole of my pussy. “Arggh! Ow. Fuck.” I reflexively put my hand on his hip to slow his entry. I might have asked him to stop; I don't recall. He respected me instantly, slowly easing himself back out with a plop.

He was smiling down at me. I grinned back. I was ready for this. “Sorry. I got this.”

“You're doing great. You were almost there. I promise it will get better after we finish working it in.”

There was a pause as I gathered my courage, the dull ache in my pussy reminding me of the task at hand. “Okay. I'm ready.”

“Do you want to be on top, Tess? At least until we get started.”

“Sure,” I replied. I wanted him to take charge, and that meant typically he'd be on top controlling pace. But I knew with this man, he was always in control. He would be my guide; my tutor. He would get me through this even if I lowered myself on his cock.

I eagerly straddled Dr. White, fitting on top of his body nicely. It was awkward for a few seconds as I tried to lift up enough to fit his penis at my entrance. He chuckled, knowing his length was a challenge when pointed straight up. “Come forward,” he said.

“Take you at an angle,” I agreed. I reached between my legs and once again fitted him at my entrance, starting with a motion to more push back to take him versus squatting down. I spent a few minutes just experimenting with the tip as it barely pushed in, changing the angle of my body and trying to get a sense of my muscles in the front of my pussy, which weren't quite engaged yet. I kissed him a lot, and he was so patient. Gradually his hips started moving though, making slight nudges upward, seeking entrance. I chuckled. On the cusp of victory, I sensed the right thing to do was to drag it out and tease him. I felt the rush of first time excitement, and I delayed now as much for my pleasure and anticipation. “Patience, Doctor. I promise you'll get to fuck me soon,” I teased.

“John,” he replied.

I pushed back more, and I felt the head fully enter me again. It hurt and stretched my tiny opening, but I embraced it. I lifted off and made more descents to that point, really pushing on the third to feel it burn more, and I could sense my tightness resisting further advance. “Uhh!” I moaned. Part of his shaft was in me now, and my tissues that blocked him were stretched and ached to pop to relieve the pressure.

Dr. White's eyes closed for a second as he enjoyed the sensations. I was stimulating the head of his cock now with my inexperienced pussy muscles, trying to grip him, with promise of more. He opened his eyes, and I grinned. I knew I had him now. I leaned down to share one more kiss before the big event. “This is it,” I whispered.

“Side down my cock, baby,” he coaxed. "Come on, Tess, get there."

I'd already noticed he seemed to penetrate easier when I was more upright. I leaned back carefully, feeling the pressure inside against my tightness increase until I was sitting tall over him. I grabbed his hands and put them on my hips and grinned. I relaxed my leg muscles and let my hips slowly come down, and as I did so, that thick cock tore me open as it began to slide deeper inside. The good doctor had prepared me well, and my body would not deny him again.

I squinched my face in pain as my body yielded to accept this massive cock “Oww. Argg!” It hurt like a mother-fucker. He in me now; a part of me, at least halfway. "It's stretching me so much, John, Oh my God, I don't know... I definitely felt it pop.”

Already he was sinking into me further. I was still letting my weight fall, and he was pulling my hips, guiding more of himself into me. My pussy spread open around this gigantic member as a few more inches slid inside me. I grimaced, the muscles in my stomach and legs completely tense as I was impaled. “There you go. It's in you now. You're doing great,” he said.