Test his oral skills and save my virginity

Good call. This guy? He was fun, but I could think of so many reasons it would be a horrible idea to have sex with him, and even trying to take just the head of his massive cock was a huge risk. But I wasn't going to let the guy go home without getting me off! If I gave him a blowjob now, which I admit I would love, I had a feeling he'd be going home without making me come. I wanted him to earn his first.

If you'd told me now that in half an hour Jamal's cock would be buried completely inside my body, I'd never have believed it...

"Make me come, Jamal. You owe me one. Is that by chance in your skill set?"

"Hell yeah, girl. Give me a taste."

"Good for you. Anyway I'm much more likely to make bad decisions after some great oral sex."

Shit, Becky, why did you say that?

I'm sure I've said this before throughout my story, but after a few close calls early in my dating life after losing the weight, I only let John go down on me, because I trusted him with boundaries. Guys always got pushy for sex after getting me off, and inevitably they'd try to finger me, which risked my hymen. Then I'd feel guilty as a modern women for valuing the physical evidence of my virginity, so it was best to just avoid the situation. Plus John gave superior head, making everyone else a letdown.

Jamal was no exception. I knew I could come simply because I was so horny, but he had no clue. Points for enthusiasm, though!

I spread my legs wide, confident in my own bedroom even with the bright lights. He went straight for the pink parts, which was okay since I was fully primed. He licked everywhere, and I mean everywhere. Even my butthole got a good cleansing! My clit was firing on all cylinders, but it was only accessed sporadically with no intention since he was all over the place, licking my labia and lower. His bad head turned into a good tease, as I was arching my back, pressing my butt into the mattress to try to bring my clit lower to help him find it. My crack wasn't tall, so there wasn't much real estate to work with as it is.

A few minutes went by, then Jamal was lifting my legs to get better access. I went with it, bending my legs back at the knees and holding them in the air, figuring I had nothing to lose. This time the tip of his tongue was parting my lips, followed by him easily pushing into my slick hole. The soft, pliable contours of his tongue didn't challenge my virginity, although I felt tight around it, so I allowed it.

He then stayed on the hole, focusing on tonguing me while I gripped the back of my thighs to hold my legs up and apart. It was different, but the sensations were great. When he finally pulled out his tongue and went up to the clit, I gasped in surprise and suddenly was very close to an orgasm. That's when Jamal snuck in a finger, sliding easily into my heated, wet channel. "Jamal..." I started to object, but just like when he stuck a finger up me in my truck, I let him get away with it. It felt damn good.

"Yeah, baby? Does that feel good?"

Instead of complaining like I should have, I just said, "Yeah, I guess. I'm close."

But I had made him talk, and once I did that, his mouth didn't find my clit right away. Instead, he worked the finger in and out, his thumb finding my clit occasionally to keep me on the edge. It occurred to me maybe he had more skills than I gave him credit for. He'd get me off for sure eventually, but his real objective was to talk me into sex. That finger inside me, stimulating my core, was the correct path. When he asked if I had any lube, I reached into my nightstand without even thinking. I kept it there in case I ever tried intercourse after the failed attempt with John, and I liked lube when using a vibrator externally against my genitals. "Just one, though."

But I'm not sure he heard that part, and I chose to ignore it when he lubed up two fingers in full view. Hot breath on my clit made that a distant memory. Then one finger was in, and I noticed the help of the lube even though I was at peak arousal. I splayed my legs wide and bent my knees again. When he eased a second pudgy finger into my virgin pussy, I felt the sudden increase in girth and a mild stretch, but no pain or resistance. "Uhh! Easy," I moaned. He had enough sense to go slow, and the fingers immediately began to flow in and out. I heard squishy sounds and a hiss of escaping air. It felt so damn good, and I was so oddly proud to have gained new ground, I didn't object. Instead, after a few more seconds, I said, "Jamal, you're being a bad boy. I said one finger."

"You got this, girl. Feels good, right?"

"Yes. Be careful. This is my first time with two fingers, and I can't let you pop my cherry."

"Okay, baby."

Of course he'd possibly already popped my cherry, and my reminder of being a virgin was just making him more determined. Strange that I didn't mind!

"Slow," I repeated. I got the phone and made sure it was recording, then held it up to record the fingers in my hole to tease John with later. Jamal laughed and kept it up. I was actually getting his face in the video now for sure, but he didn't seem to care, and I felt he owed me since he wasn't respecting boundaries anyway.

After a minute, Jamal paused to add more lube to his fingers, and I definitely noticed the ease of their passage. I felt looser already. I knew now for sure he was preparing me for intercourse with his enormous member, and it was up to me to enjoy the ride as long as I wanted while setting the limits. "Don't you dare put in three fingers," I accosted him playfully. "I've never been fucked, and three of those is like a normal cock. And make me come already!"

Jamal chuckled. "Okay, girl."

In and out flowed the fingers. He was kneeling now, giving up all pretense of cunnilingus. I started moaning, because I just couldn't help myself. His monster cock, fully hard, was now in view, waiting to pounce.

That feeling of pressure and tension, like I was about to tear, eased as I got used to my widest insertion. He sensed it and pushed his fingers in and out faster, my moans and the squishy sounds escalating with the pace. Two fingers were a lot noisier than one!

Jamal slowed the fucking motion and changed to a twisting motion with his fingers inside me, opening, stretching me out. Slowly, gaining a little space at a time. It didn't hurt, but I knew I was opening more, and I was so annoyed that I loved it and couldn't just tell him to stop. “Whoah, easy there,” I said. "I can feel my pussy stretching." I put my hand on his, but it was more a symbolic gesture. I did nothing to stop the fingering.

His answer was to find my clit with his thumb, giving me my first direct stimulation at just the right time to defeat my resolve. Clumsy, but effective. The fingers flowed in and out easier now as I built up to a well-deserved climax. Jamal took the opportunity to add firm pressure with his fingers toward the bottom of my hole, deliberately dilating the opening. My pussy burned a little for the first time as it yielded to his .

"Uggg..." I moaned. "Whew. Wai... Ow, shit, that hurts, Jamal, no more," I said, putting a hand down to signal him.

"Not yet, girl," he said. Instead of pulling the fingers out, he released the pressure but left the fingers in, and immediately the discomfort went away. Then the digits curled up, pressing firmly into the G-spot area, instantly filling my head with joyous pleasure. This was amazing! He worked them in and out slowly, and I let him continue. He was no longer stretching my pussy beyond what it was used to, and the G-spot sensations were unfamiliar to me and most welcomed!

"Come for me now, Becky," he said.

"Finally, geez," I joked. He was laying between my legs now, his tongue coming back into play against my clit. I think this was the first time he called me by my name and not "Baby", which might have helped. He didn't have to wait long. The orgasm came quickly, and I even almost had to call some of it back. I wanted to push with the tremors, but I felt so open down there, and combined with the two fingers pressing up in me hard, I had the weird sensation of holding back pee. This would have been my intro class to squirting had I let go enough. It didn't matter that I held back, because as it was, the orgasm was epic.

I was giggling with all offenses forgiven when Jamal came on top of me for the kiss, my legs weak and limp on the mattress. He tasted like lube and my own secretions, and I had to give him credit. "I'm going to be annoyed if you popped my cherry,” I said, but there was no conviction behind my words, and he knew it.

"It's got to come off some time, girl," he said, so damn cocky and sure of himself.

"Get off," I said. He actually looked dejected. "Just for a second, I want to check. Don't judge."

Because I was half-Indian, that meant my culture was obsessed with virginity, or at least I built it up that way in my head.. That meant I was obsessed with virginity. When I leaned over to get the hand mirror from my bedside table, a noisy, wet queef escaped my lubed, stretched hole. I was horrified a second before realizing what it was. I think this was my first one, or at least my first one that loud! Jamal just laughed it off. "Your fault," I said. "I can't believe I let you use two fingers. I never let anyone use two. Hold this for me, I want to check my virginity."

Jamal was cool with whatever I wanted to do, even while promoting his own agenda. Thus he didn't act like it was weird at all to hold a mirror for me as I spread my legs, then my lips with my fingers, to examine my vaginal opening. I felt the laxity in my introitus and knew his digits had stretched me.

Jamal's fingering was a deliberate, intentional threat to my virginity:

"You can also stretch your hymen yourself through a relatively simple procedure. Place a finger into your vagina (you can slick it up first with lube) and apply pressure on the vaginal entrance by pressing downward toward the anus. Keep the pressure on for a few minutes, and then release it. Repeat this procedure several times, each time with a little more pressure. Then insert two fingers and apply pressure to the sides of the vaginal entrance, in addition to the downward stretching. You can repeat this process... in order to help reduce any discomfort during your first vaginal intercourse."

It looked almost exactly the same. The intact hymen there, around the perimeter, just like before. Puzzled, I retracted my lips more, pulling flesh taut to ensure the opening was revealed to its fullest extent. Here, my trained eye noticed subtle differences. The opening was perhaps a bit larger, with the flesh creased back, but no tears. I saw no signs of trauma or bleeding. I felt like such a slut. Yet I would still present as a virgin on my wedding night. Yay, silly me.

Jamal was shaking his head, playfully mocking me. "You good, girl?"

"Yeah. No thanks to you."

"You loved it, come on, girl. You came hard."

Jamal eased himself back on me, between my legs. "It was a good one, I'll give you that," I said with a grin as we kissed.

He already had to lean forward to kiss me since I was taller, and that inevitably brought his cock to my crotch. His lips curled to a grin as we kissed and the wide head pressed against my lips again. I shook my head. "Don't even think about it." Even as I rejected him, my body language was screaming for him to fuck me. If I was serious about not having sex, I'd already have been sucking his cock instead of letting him lay on top of me with his cock at my door.

Jamal kissed me some more, than lifted his torso off me and got the phone I'd set aside. He handed it to me to unlock with a grin, which I did, then started the video. "Recording," I said. Jamal pointed it down at me, and I smiled up like a fool, loving the attention and the great tease I'd give John later.

"Damn, you're sexy, girl. You got an amazing body. Grab my cock and rub it in your pussy a little for the shot."

"I don't know, Jamal, I shouldn't. I've already done way more than I should." But I knew it wouldn't stop there.

He's going to try to insert the head of his penis again. And where the head goes, the rest follows.

By now I knew I was highly likely to let Jamal fuck me. He wasn't John, the man I loved, nor was he an Indian man that would be my future husband. Dr. John White was the logical choice for taking my virginity, yet I hadn't done it. I was ready to admit I loved him. But I knew if I fucked him I would lose that sexual tension that had been building side by side with our love, so instead I was about to gift my V-card to the man I cared the least for, but was still worthy. Interestingly, I knew fucking Jamal might actually increase the sexual tension and chemistry with John. Why wait when I wanted to get laid so bad. Here was Jamal, a man with a worthy cock to do the duties. He was legendary, and my pussy deserved that.

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Author's note:

I have an observation I'd like to share before Jamal fucks me in either of the next chapters. I often see a myth that is spread throughout society, completely false, only to have that corrected with an equally false over-reaction.

Myth: losing your virginity always will hurt.

Counter-argument, equally wrong and damaging: Sex should never hurt the first time if you are prepared correctly and fully relaxed and turned on.

The truth: Foreplay and arousal helps a lot. It will take away pain, but it might not take away enough to make your first time painless, and that's okay.

Coming up is the pain-free version of my deflowering with a very large penis. I believe it is possible, although unlikely. Enjoy, and let me know what you think.

I present several versions depending on your favorite position for the epic moment.