Chapter 34 – Regrets

I couldn’t help asking her.

“Not even one?”

She smiled sadly.

“Yes… Not even one.”

I felt stupid for asking something that made her feel bad.

“Sorry…”

“Don’t worry about it, darling. It’s not anyone’s fault. You’re such a good child.”

She resumed caressing my hair. I vowed to make her feel as good as possible in exchange for her kindness. Since sucking on her chest was doing it for her, I did exactly that. As for my hands, they headed downwards, searching for any other spots she would like to get stimulated. My right hand massaged her inner thighs while the left one was already exploring the surroundings of her vagina.

Just like she stated previously, she wasn’t wet, even with the help of the baby role-play-like boob suckling. This didn’t deter me, though. I resolved to go for a long fight, increasing the stimulations until I got her in the right state. Because my head was locked in position, I had to use my hands for everything else. I carefully caressed and massaged the places I knew women were sensitive to, waiting until her body gave me the signs I hoped to see.

I worked on her tirelessly. After about ten minutes, what we both wanted finally happened. She started to moan lightly under my intense care and my fingers sensed some wetness appearing on the level of her crotch.

“You’re doing well, my gentle child. I’ll be ready for you if you work on my clitoris a little bit with your fingers.”

Happy that my hard work was paying off, I sent my right hand’s thumb to lightly knead her clitoris. She shivered a little at the initial contact but stayed impassive otherwise. Still, it worked well, After flickering her bean for about a minute, the flow of her fluids increased enough to move on to the next step. She stopped caressing my hair and took a step back.

“Lie down on the futon, darling.”

I obeyed her soft instruction and found myself on my back, my tool towering over my groin. She kneeled in between my legs and her head closed on my shaft. After taking it in hand, she kissed it a few times before putting it in her mouth. Just like most women did before, she smeared it with her saliva for a short while only to release it afterward.

Right after, she stood over my dick, her waist slowly dropping on it. I was looking forward to this a lot. Not only was the buildup to this point quite long but I also didn’t have much experience with the cowgirl position.

Lilah opened her pussy lips with two fingers when my tip was next to her cunt and continued her descent. I felt myself entering her wet vagina, her soft folds stimulating me on the way. She impaled herself until the end, my glans striking her cervix lightly deep inside her. She let out a moan of pleasure at the feeling.

“Mhmm! You’re very big, darling. It feels great. It’s been a while since I had sex too.”

“Really? Don’t you come here quite often?”

“I do but it’s not always possible to have a chance at sex and impregnation. I was lucky that I saw you coming in today.”

“I see.”

“I think my last sex was around two months ago. A young man got horny in front of me on the streets and we had sex on the fly.”

“I-I see.”

I hadn’t asked about her previous experience but the story was interesting, nonetheless. This was similar to what I witnessed on my way here too. This seemed to be one of the main ways for women to get sex but it was very reliant on luck.

She moved her hips up and down, stimulating both of us nicely, and I returned my attention to the act. She wasn’t very tight but her pussy was coiling around me, caressing my cock like she had caressed my head. It seemed like her twat was as gentle as she was because the feeling was very good. She continued to move up and down on me but slowed down after a few minutes.

“I’m sorry, darling. I don’t have as much stamina as back in the day. Can you move from below?”

“Oh, yes, of course. I shouldn’t have let you do all the work. My bad.”

“No, I told you to let me lead. I overestimated myself a bit. Don’t worry about anything. I’m well aroused and wet so you can fuck-bang me as hard as you want. You need to come quickly, right?”

I suddenly remembered the reason I was here in the first place.

Right! This is a test! I forgot about it because I was so into the sex!

I looked at the doctor who was watching everything from his desk. He saw my gaze and spoke.

“Don’t worry, I only started to count after the penetration. It’s only been a little more than four minutes so far.”

I sighed in relief. It would have been sad to fail for such a ridiculous reason. My future easy life was at stake here! I placed my hands on Lilah’s waist and announced.

“I’ll take on your offer, then. Please tell me if I go too hard.”

“Go ahead, darling.”

Without wasting any more time, I strongly raised my hips and sent a violent stroke of my dick into her older pussy. The sound of the sudden penetration resonated in the room, together with Lilah's shout of pleasure.

“Ooohhh! Amazing power, darling! It’s great! Go on like that!”

I thought I was the one who was supposed to get pleasured but of course, she was feeling it a lot too. I retracted my waist and sent a flurry of dicking into her soft cunt. The smell of our sex quickly spread around, arousing us even further. With my hands forcing her to stay in place, I was able to blast her twat from below at full strength, my tip poking her womb entrance many times over.