Playtime with Isabelle Part I

It's hard to describe the work I'm in without being too specific and undermining the anonymity of some of the people involved. It's an outside job that involves a variety of, mostly, young people. Because it's also physically demanding, most of us are also pretty fit. We also travel a lot and being away from home that much does create a situation where romances often occur. 

As the years have gone by the group has become more professional and, even though romances still happen, it isn't the free for all it used to be.

In comes Isabelle. She was a waitress in a bar we would often frequent and a lot of us became friends with her. She was curious of what we were doing and wanted to join us. Because I was also a teacher I was asked to work with her. She was a very nice girl and I was looking forward to our co-operation.

Isabelle was a cute little girl, she seemed to be perpetually happy and her permanent smile made her very pleasant to be around with. Her good looks made her very popular with the guys and she loved the attention. When it was sunny outside she was not shy with flaunting her figure either.

The days were long and after a while we ran out of chit- chat. "What shall we talk about today?", she asked enthusiastically. "I don't know, ask me anything you like." 

"How often do you jerk off?"

She asked this without any hesitation, without any shame, without skipping a heartbeat. She didn't even look at me to see my reaction, she just kept on with her work like nothing happened. Trying to match her forthrightness I calmly answered: "It depends, on days where I'm occupied I jerk off once a day, as part of my morning routine, but on slow days usually 3 or 4 times."

This line of questioning went on for the rest of the time we were working together. I enjoy talking about masturbating and she was eager to learn everything. Needless to say, our chats made the time pass in a much nicer way. 

But after a while I had to ask: "Why are you asking all these questions? You have had boyfriends did they never share this with you?"

"No, I always thought it was kind of private." 

"You should try it, it's fun sharing this intimacy with someone you care about, and it's a great way of finding out what your partner likes."

"Maybe some day..."

The next morning, in my hotel room, I woke up because of a notification on my phone, it was a text message from Isabelle. 

"Good morning! Ready to get back to work?"

"Always! It's 6.30, what are you doing up so early?"

"The sun is shining and I'm just looking forward to getting back to work! What are you doing up? I hope I'm not interrupting anything? ;-)"

After the talk from the day before I felt I had nothing to hide: "You get no points for guessing what I'm doing now :-o "

"Omg! Seriously? Are you jerking off now?"

Nothing turns me on more than when a woman is so candid about masturbation. 

"Once a day keeps the prostate cancer away!"

This text conversation and the memory of the talks we had the day before got me worked up again and I was slowly stroking myself, waiting for her to reply, hoping I didn't scare her off with my straightforwardness. 

After a minute or so there was a soft knock on the door. I wrapped a blanket around myself and opened the door. Isabelle rushed in and closed the door behind herself, cautiously so no one saw her come in. "What are you doing here?"

"I was bored and thought I'd come to bother you", she answered. She sat on the edge of my bed, "just pretend I'm not here." I went back in bed, making sure I was covering myself and attempted some idle chit-chat. She interrupted me with a wicked smile; "Don't mind me, just continue with what you were doing." Accepting her dare I slid my hand under the cover and grabbed my erection, moving my fist slowly up and down, making sure my cover would also move in a way she could see. At the same time I was just looking at her, talking about work, acting like there was nothing going on. Isabelle didn't look at me, she was focussed on the movement of the blanket.

 "Are you really hard now, or are you just joking around?" Humming some stripper music I slowly uncovered myself. As soon as my cock became visible I quickly covered myself again.

"Stop it!", she demanded, a little irritated, and pulled my cover off, exposing me completely. Her eyes widened as she was now staring at my cock firm in my fist. I was caught as a deer in headlights. "You weren't joking! So, show me how you do it, tell me how you jerk off..."

"Euh...there isn't much to explain, is there? This is my foreskin, and I slide it back and forth over my cockhead and that feels like I'm fucking someone, I guess?"

"You have a big cockhead", she said quietly, as if just to herself.

"Yeah, I know, but my skin can stretch over it." I showed her by slowly pulling back the skin, exposing my shiny head, glistening from precum.

"It's so stretchy!" she said giddily. "Yeah, I used to put my finger in, it felt nice."

"How do you mean?"

I pulled my skin back, put my finger in my mouth to wetten it a little, then placed my finger on my cockhead, resting it on the cumslit. Then I slowly pulled the skin back up, covering the head and my fingertip. "See, this feels nice, and now I can move it around a little" and I traced my finger around the head. "Ha! I've never seen that before! Can I try?"

"I guess so."

I pulled back my skin and pointed my cock towards her. She moistened her finger and rested it on my purple head. I pulled up my skin and her finger was inside. "It's so warm!" And she slowly wiggled it around.

"So now what do you do?"

"Well...you just keep going untill you finish, I guess."

Isabelle made herself comfortable next to me and intently watched me stroke me cock. "Does the speed of you jacking it make a difference?" "Euh...it depends on how it feels and how close you are", I stuttered back.

"What do you do when you are close to cumming?"

"Well, I need to start deciding what to do with my cum."

"What do you mean? It just comes out, right?"

"Well, yeah...but where to put it, I mean."

"I don't get it, what are your options?"

In the meantime I'm loving her curiosity, and her eyes glued to my cock while I'm stroking it.

"I can get up and cum in the bathroom sink, or toilet, I can use a sock or boxershorts or I can go "au naturel" and cum over myself." Isabelle looked under the bed and reached out to find a pair of boxers tucked away under it.

"Ha! What do we have here? So, whatcha going to do this morning?", and she handed me my boxers.

"Dealers choice, you are my guest after all." 

"Go au naturel! I want to see it go!"

I kept jerking my cock for a minute in silence. Her eyes followed my hand as it went up and down, exposing my shining purple cockhead. "Are you ready?", I stumbled.

"Yes! Go for it!"

She watched intently as I grunted and shot my first stream of semen on my chest, followed by two more covering my stomach.

I let out a sigh of relief. "Holy shit! You do this every day?" I had to readjust myself because my cum was running down my chest and on to my sheets. "Yeah, that's why I usually cum in the sink; less cleaning up. Hand me my boxers will you?"

"Nope, leave it on...I think it suits you! Thanks for explaining everything to me."

She jumped up and left the room, leaving me covered in my own sticky mess.

I went down to the lobby for breakfast and she was there with some colleagues getting ready for work. I joined them and it was like nothing happened. During the day Isabelle was constantly joking about how my shirt was sticking to my chest and asking where the stains came from. 

I guess it satisfied her curiosity, she did text in the mornings to ask how I was doing, but she never came to have another look.

Time went by and after we were done working we all went home. 

But that was not the only tale of Isabelle...