Ruben Ch. 03

Monday and Tuesday I went to school as usual. I saw Ruben shortly during one of the breaks. We smiled at each other, but didn't speak. Later I texted him that we'll meet at the hotel the next day at 5 pm.

On Wednesday I arrived somewhat earlier. Ruben was already there. He chuckled and said that he arrived at 4 pm and tried to advance in geometry by himself, but his attempt was unsuccessful.

"Let's try together. I am confident that pretty soon you'll comprehend everything in the next chapter." I was very patient with Ruben. He was no genius, but no dummy either. Fifteen minutes later, his biggest hurdle in that part was now clear and we progressed faster.

At 7 pm he got mentally tired and declared that he was going to take a quick shower. Just like before, he came out naked, while drying himself with a towel. He said, "I promised a couple of friends to watch with them the basketball game. It starts at 8, so I'll leave now and see you again on Saturday. Is 10 am OK?"

"It's perfect."

And then he left.

...

That night I had a dream about us. Ruben and I were walking among many other people to a concert. Toward the stage the crowd was packed tightly together. We were fortunate to be in an area that had reasonable visibility. Ruben placed me in front of himself to see the show better. As the lights dimmed and the band began playing, the crowd started dancing and moving back and forth. Ruben was pushed against me. I leaned my body on his. Within short time I felt his pecker harden, pushing against my ass crack. I moved my hand backward and caressed his erect tool. He whispered, "Open my zipper." I looked around. It was dark and everybody was focusing on the stage. I unzipped his pants. He had no underwear and his prick jolted out of it's cage. He bent again, "Now lower your pants!" For some reason it didn't sound like an unusual request and I lowered my pants to my knees. I did not have my briefs on either. "Good boy. Now spread your legs slightly and I'll pop your cherry!" I wasn't sure that it was a good idea, "Ruben, there are too many people here. We won't have enough room..." He was adamant, "That's OK. You'll see." Then he stuck one finger through my sphincter. It didn't hurt at all. Subsequently he put inside me a second finger and it was OK, but tighter. "Nathan, relax now. My cock is next. His big hard organ slowly penetrated my hole. I expected it to hurt like hell, but it didn't! My puckered hole expanded easily and accommodated his massive organ without difficulty. Ruben began back and forth movements and I had a very pleasant internal massage. In fact my own penis started engorging, achieving maximum erection once Ruben reached his top speed ramming into me. We both came at the same time. My legs were wobbly and if it were not for Ruben's strong hands holding me and his huge cock impaling my bottom, I'd fall down during my earth shattering climax. After cumming, my dick shriveled, but Ruben's stayed hard and he kept it inside my ass throughout the concert...

I woke up by an outside noise and realized that I ejaculated during my dream and stained my briefs... I stayed in bed for few moments thinking, 'Am I afraid of our next step, or want it?... In retrospect, it was probably both.

...

Saturday morning we met in our room. Ruben smiled and declared, "Nathan, math first for at least 2 hours. Afterwards, whatever you want." We continued with algebra, but the progress was slower than what I wanted it to be. Neither one of us could concentrate on math. I wasn't sure about Ruben's reason, but mine was purely sexual! After my sex-in-public dream, I was emotionally ready to be invaded by my boyfriend and everything else was pushed aside...

At 12:15 Ruben stood up, "I think this is enough for this morning. My head is too full with mathematical formulas. Time to eat lunch and rest. We ate at the nearest Taco Bell and returned to our room.

He smirked, "So what would you like to do now?"

"Ruben, I am ready to do whatever YOU want..."

"Are you just saying it, or mean it?"

I looked him in the eye and whispered, "Please, make me yours, but be gentle."

He came toward me, slowly lifted my chin and kissed me tenderly on my lips. Then he blurted, "Nathan, let's undress and go to bed." As I was removing my clothes, I noticed him arranging something on the nearby dresser.

To say that I was scared sh.. was an underestimation, but down deep I knew that if I wanted to be with Ruben, I'd have to do it eventually. And I actually wished to to it. But having such a massive cock trying to penetrate my small anus... Even if he was extremely cautious, the size difference could tear my sphincter, causing irreparable damage... Trusting Ruben was the most important consideration. Hopefully, if he saw that his prick could not cross the barrier, he'd stop. I was concerned by the initial pain, but irreversible injury was by far the key issue!

I lied down with my face up. Ruben knelt in front of my face, signaling for me to suck him. It was comforting for 2 reasons - I liked having his pacifier in my mouth and... his cock was far away from the main target for now!...

I took him in my mouth and began slow, constant licking and sucking the way he liked it. His tool started it's ascent and expansion. It was a great feeling!

Meanwhile Ruben's hand trailed to my tummy and then caressed my small dick. It responded by jolting and rapid rise. Seconds later his fingers moved down, spreading my thighs apart. They wandered toward my perineum, smearing cool liquid around my puckered hole. Likely KY Jelly. My sphincter instinctively shut off. The fingers massaged the area in a slow circular way, relaxing the muscle. Then his forefinger poked my anus lightly and retreated. it did it several times before becoming more insistent and eventually invading the entrance. It didn't hurt at all, but it was a weird feeling... Ruben's finger moved gingerly in and out as well as around and around, enlarging the opening. Once the anus got used to his manipulation, a second finger followed. Although now there was a feeling of fullness, I did not suffer a bit. It was actually pleasurable... If I knew that only these 2 fingers would be my invaders, I'd be extremely happy! Ruben's fingers entered deeper, rubbing my prostate. I liked it. A lot... My penis started to harden again as my horniness increased. I sucked him harder now, hearing myself occasionally moaning.

Suddenly both his fingers pulled out of my ass and I felt uncomfortable emptiness. I wanted my hole filled again, but I could not express myself with my mouth full of his huge cock. Seconds later a cool slippery object probed the partially open anus and entered easily in. It was somewhat larger than the 2 fingers and rounder. As it progressed further inside, the diameter grew, gradually stretching my sphincter more and more. In the beginning I liked the new 'thing' filling me again, but later it started aching. Ruben did not advance further, letting my ass adjust to the new invader, making only minor movements. Within less than a minute I felt better and began pushing the device deeper into my butt.

Without advance warning, I heard a buzzing sound and it started vibrating. I was not ready for the vibrator and initially my whole body quivered, but I got used to it and started loving the feeling. Slowly the object was pushed deeper, until it reached the sensitive area behind my prostate. My body jolted up once and an immediate sense of arousal with needing to pee enveloped me. I groaned loudly.

Ruben looked at me with a comforting smile and whispered, "It's OK Nathan, take it easy. I won't hurt you..." His reassuring voice calmed me down. My arousal took over. My ass began again to counter the vibrator's in-and-out movements.

Then he removed his rock hard cock from my mouth and smeared it with jelly. He moved between my legs and lift them over his large shoulders. Then Ruben pulled out the vibrator and put it aside.

His warm member touched my anus and gently pushed it forward. It was larger than the vibrator and I felt my sphincter struggling to accommodate the bigger size invader. Ruben was very careful to push mildly and retreat and then do it again. The force he applied has increased only slightly every time he was poking the hole.

After a minute the head was in. It hurt somewhat, but Ruben knew when to stop and wait for the pain to subside. A moment later he added more KY jelly and began pushing it in again. Actually, once the head was in, the smooth veiny shaft entered more easily! Slowly but surely he was advancing forward. I was still having some pain, but it was tolerable. The pain was minor and the cock did not rip my ass...

Ruben started cautious back and forth pounding of my ass hole. The giant cock was massaging my prostate and the constant slippery friction on my anal membrane was very enjoyable. My prick, that got deflated when the pain started, became hard again.

I gazed at Ruben and whispered, "I love your patience. I have no more pain. And your big cock dancing inside me makes me horny as hell. I am going to cum soon..."

Ruben face lighted and the shoving in and out became more intense.

About a minute later I felt both his breathing and heart rate rising. My orgasm started seconds later. It was amazing! It was so different than the orgasm I experienced while masturbating. It was deeper, longer and MUCH more powerful... As my body was beginning to relax again, Ruben groaned like a wounded animal and his cock was pounding me fast and strong like a jackhammer. It wasn't painful. In fact it was very pleasurable! His massive tool jerked and ejaculated several times in my bowels, filling me with large amount of spunk.

When he was done, he rolled over on his back and tried to catch his breath. I turned on my tummy, not wanting the seed to get on the sheets. We both rested like that for a couple of minutes and then I constricted my ass the best I could and rushed to the bathroom. I started the shower to mask the noises and sat on the toilet. Everything leaked without too much noise. Then I went to the tub and stayed under the pouring hot water for several minutes, thinking about the new experience.

My ass was no longer virgin! Considering that it was my first time, the pain was very tolerable, mainly because of Ruben's extra preparation and patience. I was very grateful to him, especially taking into account that we had to deal with significant mismatch in sizes between his humongous cock and my tiny anus. And after the successful benign penetration, I reached the best climax of my life!!!

I was very happy after our intercourse. The near future with Ruben looked very promising.

I came out of the bathroom naked and clean. Ruben was asleep. I lied by him and short time later I was in la la land too.

...

I woke up with Ruben's big palm caressing my back lightly. It was 5 pm. He smiled, "Nathan, I had a very pleasant experience before falling asleep. But please, before talking about it and the implications, let's spend 2 more hours on the damn math, otherwise I'll feel guilty..."

I grinned, "OK big guy."

We continued with geometry, moving to theorems, parallelograms and trigonometry. Neither one of us was able to concentrate too much and the progress was slow. What I thought would take us 2 hours, we finished in 3. At the end Ruben seemed completely out of it and we had to stop.

He Chuckled, "Thank you for being patient, trying hard to insert so much knowledge into my straw-filled head."

I smirked, "Ruben, it's your reward for being patient with me. After all, you inserted something hard into MY body..."

His throaty laugh broke the ice, "Naughty boy! I like you. I admit that it wasn't easy for me to be so slow before taking your cherry, but it was worth it. Now we know that it's doable and your ass had enlarged some already. Next times it should be much easier and we both can enjoy more."

I looked him in the eye, "Ruben, you were perfect. When you were inside me, I didn't suffer and in fact had the best orgasm of my life."

"Nathan, you know what it means - Now you belong to me..."

I chortled, "Yes daddy..."

he laughed, "Who's your daddy? Oh, it's me now..."

We ate dinner at an Italian restaurant. We celebrated my first time with a glass of white wine. As we were munching on our food, I peeked at Ruben, thinking to myself that I was very happy with him. I was his math tutor and he was my protector, lover and... new daddy.