Me, Myself and Janine

This story is about my relationship with Janine. We are still friends, though both happily married to other people. This all happened a long, long time ago. A time where meeting someone from the internet was relatively new and exciting. 

I noticed Janine's profile on msn (to give you an idea how long ago this was). The picture on her profile wasn't remarkable, but I was sending the same copy/pasted opening lines to tons of women, desperate for some attention, bored as I was. Janine was the only girl who replied.

We had a nice little chat and eventually I convinced her to turn on her cam. 

Her profile picture did NOT do her justice! I was struck by her beauty. Unfortunately I had to run for work. We would chat later that evening. That evening we chatted 'till dawn, it was amazing. "We should meet some day, what are you doing in the weekend?" she asked.

"The weekend? What are you doing tomorrow?" And that was how I first met Janine.

We met at her house and we had a great afternoon, just talking and getting to know each other. After I got home we chatted some more and she asked what I thought about our meeting. I admitted that I was, kind of, expecting a sexual encounter, but this was actually much better. She admitted the same. We decided to keep our relationship platonic to avoid complications. Janine was a woman who was used to getting what she wanted because of her beauty, and I was up for the challenge. 

Our friendship grew and it wasn't long before I start spending the night, helping her any way I could so she could focus on graduating. I would cook, walk her dog and, because she adored being pampered, pamper her. 

This is where we entered a grey area in our friendship. 

My pampering involved massages, nothing out of the ordinary, you might think, but also naked massages. Again, in some settings this is something good friends might do. Seeing my erection was nothing to be embarrassed about; we're all adults! I would pluck the hairs on her legs, and eventually also trim her pubic hair for a nice bikiniline. Obviously handeling her most intimate part was crossing some friendship line. But we acted like it was the most normal thing in the world. She would lay on the bed naked with her legs open. She would, very casually, fold open her lips and show me how she would like me to handle her pussy and what line I should follow to have her landing strip just the way she wanted it (she was very precise). The trick to plucking out hairs is to keep the skin stretched, so I would constantly have to cup her pussy do not to hurt her. Hair by hair I would work on her little blond bush. The hairs I plucked out I would carefully blow away, creating a warm breeze over her little button. It was obvious I was being tested, I would not let her win so easily and prove that "all men are just after one thing". Of course I couldn't control my body that much, I had a constant raging hard-on that was impossible to hide. After I was done, she inspected my work, and if she approved we would brush the hairs off her bed. There was a big wet stain where I was laying between her legs. "Where did this come from?" she asked like she didn't know already.

I just pointed at my cock that had a long clear drop of precum hanging off it. "Yeah...that might have been me," I admitted. "Would you like it if I worked on your pubes too?"

"No,thanks," I laughed, "if you touch my cock now we will have bigger stains to worry about!" She smiled and continued cleaning up and getting ready for bed.

That night we were getting ready to sleep as I spooned her. She snuggled in to get comfortable and her ass was rubbing against my cock. We were at a point where I didn't have to apologize for having my cock hard (we had gotten used to it from me handeling her pussy all the time). But after a while her "adjusting" seemed to get more deliberate. She was rubbing her pussy over my cock. "What are you doing?", I asked.

"I'm sorry, I just always get so hot from rubbing my pussy against a hard cock."

"Well, you shouldn't be doing it then, should you?", I said, reminding her of our platonic relationship.

"I'm just really curious how it would feel, how your cock would fit in my pussy. It's not real sex, it would be like trying on a pair of shoes."

Well, it's hard to fight that kind of logic. While we were still spooning, I reached over to part her lips and slid my cock in her. I pulled out and penetrated her once more as deep as I could. "So now you know, let's go to sleep, you need to get to work tomorrow." I pulled out and rolled over.

It was quiet for a minute, then I heard some rustling. "What are you doing?"

"Sorry, I need to fix this real quick."

"Fix what? What are you doing?, I asked faking innocence.

"I need to do something dirty", she answered. I wanted her to say it.

"How are you going to fix it?"

"I need to play with my pussy before I go to sleep, I've gotten so wet from rubbing my pussy against your cock."

"Go ahead...can I join you?"

She was silent for a second, "yeah..sure."

I was a warm evening, do we kicked the blankets off and looked at each other in the twilight. Her fingers were dancing over the pussy I had gotten to know so well. My cock felt warm and damp, still covered in the wetness that came from inside her. We lay silently next to each other sharing our most private moments. I watched as her fingers explored the folds of her pussy, dipping her fingers inside. As I looked in her eyes I saw her looking down at my cock, firmly in my fist, stroking in the same rythm as her fingers went over her pussy. As she looked I slowed down, letting her explore what I was doing to myself. I slowly pulled down my foreskin over my swollen cockhead that greeted her hungry eyes with a glimmer of wetness. I saw her smile as she arched her back, diving in her pussy with her fingers as she came. As she lay back down she turned her head to the side and stared at my cock. She put her hand om my stomach, "Would you like a tissue?"

"Do you want me to cum for you?" I answered.

"Let me see you cum for me." 

This was the first time she saw me cum, and I was glad I didn't disappoint. My head shot back as two, three bursts of hot cum shot over my stomach and chest. She smiled as she handed me some tissues to clean myself off with. 

Still, it seemed like nothing strange happened. We were just two good friends who needed to relieve ourselves. Nothing out of the ordinary. We went back to spooning each other, giggling a bit of how award it felt feeling my sticky cum between us.

The line between friends and lovers had shifted, but it was still there. We both fell asleep wondering where this path would lead us...