Cindy's Foreskin Obsession

"Oh my god, your cock is sooo cute! It's like a little elephant trunk,"

My heart raced the moment I heard that, I've always had a bit of anxiety around my cock, but the way Cindy said that wasn't teasing or bullying. I could see it in her eyes, she had this huge smile, and her hands were in this awkward position. She wanted to move her hands towards me but wanted to respect me.

"It's alright, you can touch it! Just be gentle please..."

With no hesitation, she gently pinched my flaccid cock's overhang, slowly rolling it between her thumb and index finger. Her soft touch was great, I saw my foreskin get softly and painlessly twisted. Her nails were short and very rounded off, painted bright green, I could feel the pads of her fingers and sometimes the hardness of her nails.

"I don't think any of my boyfriends ever had this, I want a closer look!"

She got on her stomach and her other hand started to pinch my foreskin. She started pulling my foreskin open without pulling it back with a gentle tension. She giggled a bit, happy that I was starting to get hard from her playing with my foreskin like that.

"So what is this? The cocks I've seen don't have this adorable hoodie! You clearly have a cockhead but it's hiding in all this skin!"

By the time she had finished saying that, I was fully erect, still fully covered by my long foreskin. I felt a soft kiss on the underside of my cock. I quietly gasped.

"It's my foreskin, it's meant to protect my cockhead and it also helps with sex by gliding back and forth. It's just that- ouch!!!"

"Oh my god, sorry, you said it could go back and forth, did I hurt you?"

"It hurt a little, my foreskin is a little long and tight is all. I'm gonna be okay, just don't pull it back all the way."

"How does this feel? Looks like you get wet like I do,"

And with that, I felt a finger slip into my foreskin. The underside of my cockhead was being touched and stroked helped by the precum making it pleasant rather than painful.

"Cindy, that feels so good!"

"I've fingered a lot of guys in their asses, but their cocks? This is new and really sexy!! You are super wet inside your hoodie!"

Now I was panting a little, my foreskin making her fingertip disappear and reappear with each push and pull of her finger. Cindy's smile was bigger than ever, she completely removed her finger out of my foreskin.

"You whimper so much, is your dick that sensitive? It's sweet, but why am I now seeing a foreskin? Playing with your cock makes so much more sense, it's more clit like and I can finger fuck the foreskin! What happened to all those other cocks?"

"Oh, well, chances are... those guys lost their foreskins from circumcision, a surgery. Likely when they were babies-"

I had stopped when I saw mix of anger, sadness, and confusion. She looked over my cock pulling at the skin from my cockhead to the shaft. Her face quickly went pale as she realized how painful circumcision would be and how much would be lost. She wasn't mad at me, it was an anger from events before we met.

"That's why they had those scars! That's why sometimes jacking them off was so weird and alien sometimes! They were great guys, but they were robbed! I feel sad for them..."

I went in to comfort her and pat her on the head, but she jumped up onto her knees and got behind me. Now sitting behind me, she tightly grabbed my cock. Her left arm held me tightly against her.

"I love jacking cocks off, I'm going to slowly jack you off. Tell me where I can safely pull your adorable hoodie down."

She started to pull my foreskin down the shaft, getting about halfway to the head. My words struggled to get out my mouth as I felt my ear being nibbled a bit, so I gently tapped her leg. Stopping her at the right moment.

And slowly jack me off she did. She would give me a few strokes, then let go to tease my foreskin, only to give me a few more strokes. I was whimpering even more after a few rounds of this.

"Cindy... fuck..."

"Hehehe, I love how much of a noisy guy you are. Your hoodie gives me another spot to tease and keep you hard without making you cum too fast."

I felt my foreskin rolling up and down rapidly. My cockhead was so slick with juices, my foreskin quickly covering my purple head and being partly retracted. I got so close to the edge, but Cindy stopped.

"I can't believe how easy it is to jack you off, Mark!! It's like your adorable hoodie does most of the work. I think I've teased you enough! Cum for me..."

Cindy's arm continued this time extra slow. She giggled into my ears.

"I noticed how much more you squirm and moan when I go gentle and slow. So I'll give you what you need, just cum for me..."

"Ooooh, shit!"

I shuddered from that command, but I wasn't quite there to cumming. So she strokes me a little deeper, giving my foreskin a slight stretch with each downstroke.

"Oh, that was so cute! You must like being commanded while your cock is in someone else's hand. Don't worry, I won't stop until you cum for me..."

I almost cry out loud, I saw my cockhead had turned in a super deep purple now. I could feel my face getting warm, my voice is almost high pitched as my body gets closer.

"Don't fight it, Mark. I know this must feel good for you, so please, cum for me!!"

I couldn't hold back anymore. I really made a loud moan from that command.

"Yes, Mistress- Auuugh!!"

I shot my cum extremely hard on my chest. I was shaking so much from that orgasm. Cindy was praising me and my foreskin but I was in another world so I didn't hear everything she said.

Cindy smiled at me as I recovered.

"Hehe, Mistress? You're surprisingly kinky, Mark! And you say that in the sweetest way too! I want to learn everything about foreskin!"

"Oh sure, that sounds like fun!"

And that was the start of a lot of foreskin kink adventures.