Penetration

I obeyed warily. I felt so now, my pink parts shaved and exposed for her pleasure. After all the men, including John, I'd rejected for sex, now I was going to lose it like this.

“Have you used a dildo before? Because if your jay is already broken in, I might as well go ahead and take you with no mercy like the slut you are. Otherwise I'll go easy on you at first.”

I'd already answered this question before the match. “No,” I said, thinking I'd never heard my pussy referred to as a “jay” before. Maybe a play on the second syllable of “vagina?” I was less than four years older than Tess, but it felt like more. Yet she was one of the cool kids growing up, and that showed; she was way more alpha.

“Really? As slutty as you act?”

“Just a finger, I swear,” I said, weirdly feeling like I had to prove my innocence before she stripped it away from me.

“Get lower. Face in the mat, girl. There you go. Reach back and spread your cheeks. Let's see if you were being honest. Keep spreading. I want to examine your genitals.”

And here comes the virginity check. I had to turn my face to the side, and already my cheeks were more apart, my pussy more exposed. I reached back, as ordered, and pulled them apart more. I felt her grip on my butt cheeks also, and she had a perfect view of my most intimate parts. I gripped the flesh by my lips and pulled towards my anus and out, in a practiced movement to expose my opening. I knew it was what she wanted to see.

”I'm impressed. You really haven't popped your cherry yet.”

“Whatever,” I said. Tess ignored the offense and spit loudly, spraying my butthole in a demeaning move, treating me like a porn star. Then she stood, hovering over me, her legs spread around my body. She reached down and lifted my breasts off the mat and cupped them. I felt the textured bottom of the dildo as it aligned with the small of my back. I was nervous, and I lifted my torso up and went back on my hands.

“These tits are ridiculous. They hang so far,” she said, mocking my sagging tissue. Then she painfully squeezed both nipples. Both my nipples hung far enough to brush the mat even in this position.

“Ow!” I whined. I liked to have my nipples pinched lightly, but I had to be closer to orgasm. Now, it just hurt. Then she jiggled both breasts before slapping the right one hard. “Arggh!” I groaned.

"Ramya,” she said softly, leaving a long pause before continuing. “I'm going to destroy you. Do you need a safe word or something?”

“Would it matter? Do what makes you happy,” was my response.

“Good answer. I was going to do that anyway.” Tess was pushing my upper back down. I went to my elbows and arched my back, figuring I might as well do my part.

I sensed the large tip to the intimidating phallus slide down my butt crack and stop on my anus. She gave it a gentle push, but no way was it going in my backdoor without lube.

“Want me to fuck you in the ass instead?” she asked.

“Yes, please,” I begged. This would save my virginity. Was she serious? I knew deep down I craved it in my pussy, I just didn't want to admit it. I was getting turned on as a submissive. The dildo slid down a little more, and Tess gave it a jiggle and seated the head perfectly the entrance to my virgin pussy.

“You wish,” she said. “Let's test the waters a bit,” she said as she began to ease the shaft forward.

My opening dilated readily, allowing the head, half-shrouded in fake foreskin, to slide inside. The first raised dimple at the tip of the shaft and the ribbed underneath rubbed the skin at my introitus, and my muscles widened to allow the head to pass into me and press against my hymen. It felt absolutely fucking huge. There was just no way this was going to fit. “Ooof, ow,” I began to whine. “Tess, go slow.” She paused for me, but did not withdraw. “It hurts a lot already,” I said, regaining my composure. I put a little more arch in my back, ready to accept my fate. She noticed my acquiescence.

That's when Tess pulled the dildo out of me with a loud slurp. She had penetrated almost as far as Jamal, and that had been a while ago. This dildo was almost as wide.

“I'm going to lube you up first. I was just testing you. I respect you, Ramya. You could have walked away on your word. I will still take what's mine, but my hope is that you will enjoy this.”

“I'll try,” I said with a nervous chuckle.

Then I heard the unmistakable sound of the flip top of the lube bottle. A finger slid into my pussy first, snug, tight, but no problem. Tess was generous with the slippery gel, and she reapplied once and fingered me for a minute. I released my cheeks and used my elbows to support me in doggie, and Tess didn't object.

I knew what was coming next, so I wasn't surprised when I felt more pressure, more girth, resistance. I yielded surprisingly readily, and two slender, slick fingers passed into me for the first time! “Uhh!” I groaned in surprise. My pussy stretched more than it ever had. I felt it give, a little, opening for her, but it didn't really hurt. The dildo was definitely bigger, but it had not penetrated this far, through my opening and the protective maidenhead serving as the gateway to womanhood.

I realized I was holding tension in my kegel muscles in a failed effort at protecting my opening from damage, adding to the tightness. I relaxed as best as I could, and I heard a slight hiss of escaping air. Tess began to slowly push her fingers in and out with accompanying squishy sounds. With the extra width of two versus one finger and the air gaps, two fingers in my pussy were noisier than one.

“Damn, girl. You are tighter than me. Don't worry, I will stretch you out.”

“Thanks,” I laughed. “You don't have to if you don't want to.”

“Oh I want, and I'm gonna.”

In and out, slowly picking up pace, Tess finger-fucked me, and I opened up and got used to it. She added lube, then she started widening my hole, pressing slowly against the bottom of my pussy first, slowly stretching the opening towards my anus. I gasped. It hurt, but not bad. She worked her way around the perimeter, stretching and loosening. When she curled her fingers towards my G-spot, it felt amazing. I hadn't really explored this with my single-finger self-love before.

“Yeah, you like that, don't you?” Tess teased. “Your pussy hole is getting bigger finally.” To my groan in response, she added, “You know this can only help you with what's next.”

Tess worked me more, now in a twisting motion with her fingers, in an out. With her fingers slightly bent, I felt the knuckles more, giving her a wider profile to dilate my hole even more. When she finally pulled out, I thought I might actually have a chance at taking this monster cock.

Tess was pulling my cheeks, tugging at my labia to look. “You still need to pop. I made the opening bigger, but your hymen is intact.”

“Then it's not too late. You don't have to do this, Tess.”

“Doing it,” she replied.

“It should be my future husband's job to do this, not yours.”

Tess slapped my ass hard enough to jostle my tits. I groaned in surprise. “You made the bet. Your virginity is mine, Ramya. Roll over. I want to see the look on your face when I take it.”

“Okay...” I muttered weakly as I rolled to my back.

“Spread you legs really wide for me. Bend your knees and hold your thighs for me like a slut, yeah like that. Hold yourself open and give me room to work.”

I did as ordered and watched Tess' athletic figure move between my legs, kneeling, preparing to insert the dildo. She paused long enough to add generous amounts of lube to the dildo, then pushed the tip perfectly at my entrance, parting the lips. “Oh God,” I whispered. I looked her in the eyes, memorizing her face. Her body was amazing, her face gorgeous. She was powerful and confident, and she desired me more than anyone at that moment. In a strange way, she was more worthy of this task as any of the numerous men that had asked to fuck me.

Tess grinned, looking up to meet my eyes as she pushed, a gentle nudge to let me know the end was near. She paused with the head seated at my entrance, the tip already in the hole, the wide ridge of the fat head sitting just outside, waiting impatiently to slide inside. “I know everything about you, Ramya. You drove away the only man you ever loved, and he told me everything.” I shook my head no, but I couldn't deny it. “And I read up on your culture, what you gave him up for. It will all be for nothing when I take your virginity. This is a really big cock between my legs; way bigger than any Indian man that would propose. Your pussy will be loose, and you won't bleed on your wedding night. Your husband will know you are whore. You will be worth nothing to men in your culture when you leave tonight.” I shook my head no. “But I know you want it. Beg for it, Ramya. Beg me to fuck you.”

She didn't wait for an answer. “Uhh!” I gasped as Tess pushed, the large head disappearing inside my virgin pussy. It burned as the stretch began, and I knew I was about to pop. This was a familiar feeling thanks to Jamal. This was my limit; I had never been penetrated deeper than this with something this thick. “Tess! Please, it's not too late. You don't have to do this.” It was barely a whisper; a pathetic beg that just emboldened my conqueror more. But deep down, I wanted it anyway. Put it in. Fuck me, Tess, please...

Tess looked at my pussy with a grin, pulling the dildo out and sliding the head back in a few times. Then the next push was harder, and that fat head entered my canal again. “Ramya, my dear. Don't worry. I am setting you free,” she said as she delivered the fateful stroke. The wide shaft behind the head began to slide inside. I felt one of the raised nubs on the shaft and every contour of that head with the fake foreskin as the blunt rod slid inside. Then a second nub, and it really started to hurt. Tess paused, leaned down, and she kissed me on the lips. Then she stayed low, her breath hot on my face, her eyes boring into mine as she pushed. “You're mine...”

I felt another nub on the top of the cock as more length slid inside... and with it now a very distinct popping sensation. “Aieeee!” I cried as my hymen tore and a fiery pain explosion rippled through me. Holy fucking hell it hurts! Tess' grin turned into a glorious smile. She pecked my lips as I stared through her in shock, then to the side to avoid her stare. This wasn't normal. I knew already this wasn't a quick snip and immediate recovery, with the dainty virgin loving sex on the second thrust. I felt flesh ripping and tearing, and I already felt overly stuffed and full, like I had to tear beyond just the hymen. “Too fucking big, damn it!” I swore. Two more inches of the dildo its way into my throbbing, hungry pussy, ushering in more pain, shame, and remorse. I was now penetrated deeper than I had ever been, and now with devastating thickness. My pussy had yielded its intact hymen, the guardian and proof of my virtue, and my vagina itself was stretching, adapting, remolding itself around the thick dong, never to return to its pristine, marriage-ready state.