Helen & Even: the Beginning

It was my first year after graduating from college and I was working in an office and not having much fun. The best part of the job was a small group of co-workers who would go out after work and party the night away. There were five of us. We all were in different sections of the company but met up one night at an office party. We left the office party and went to a bar, getting as drunk as possible. It was a bonding experience and we began hanging out every week.

The funniest person in the group by far was Helen. She had a sharp tongue and knew how to use it. She also had no trouble talking about her love life after a few drinks. We all heard about her long-time love from Paris and their on again-off again romance. In time we also knew about their sex life. They would spend weeks apart, and then meet up only to have rabbit sex for hours on end. In time, we even knew how thick Josan’s cock was and that is was uncircumcised. This was the type of woman Helen was.

As the months passed, we all knew about each other’s sex lives but knew the most about Helen’s because she was so willing to tell story after story about her sexual experiences. Helen eventually left Josan and I left my girlfriend, and we were talking with each other near the end of a long night of barhopping.

Helen was like me, we were serial monogamists. We just didn’t feel comfortable cheating on our partners or sharing them. Helen told me that she was almost 30 and frustrated because she promised herself that she would try all these different sexual experiences before she was 30 and wasn’t close to completing the list yet. I listened to her and expressed similar frustrations because I didn’t think that I would ever try some of the unusual sexual things that I was excited to try.

After another round of drinks, we started to share our lists. They were very similar. Our faces lit up every time we had an item in common. We both agreed that it would be so difficult to try those things while in committed relationships, bitched a bit more, and then the evening ended.

A week later, we found ourselves at the same bar. Helen rushed up to me and told me that we needed to talk. She had an idea. She asked how I felt about her. I told her how much I liked hanging out with her and that she was the funniest person I knew. She asked if I thought she was pretty. Helen was 29 and about 5’5” with long dark red hair. She wore slightly heavy eyeliner to accentuate her green eyes and had light skin and a devilish smile. I couldn’t tell exactly what her body looked like because she always wore fabric-friendly blouses or sweaters and knee-length skirts, but she had beautiful legs and a tight stomach with a gold belly ring. I told her the truth – she was hot. She lastly asked me if I was attracted to her and wanted to date her. I told her that she was very attractive, but didn’t really consider her a possible girlfriend up to that point. She smiled and basically told me that she thought the same things about me. So why was that making her so happy?

Helen revealed that she was thinking about our previous conversation and wanted to do something about it. She wanted us to act or pose like a couple and have sex with other couples so that we could live out a few of our fantasies. By that point, I was smiling from ear to ear. During that long conversation, we worked out some of the details and ground rules of our enterprise. One rule was that we would never have sex together without another couple joining us. That would keep us from ever falling for each other. We were friends, that’s all. It’s just that not all friends have group sex with other couples.

We met later that weekend at Helen’s house. We went online and chose two online dating/swinging sites that we both liked. After a very fun conversation, we composed our ads. The last thing to do was the photos. She had a digital camera, so we took one shot together with her on my lap smiling at the camera. We then decided to take one nude picture each. We flipped a coin, and I undressed first. Helen sat there at the computer watching me undress and loved every difficult moment. I couldn’t look her in the eye without laughing, so I looked at the wall behind her and stripped. She seemed to like my chest when I took off my shirt. Her smile got wider. I lost my shoes, sock and pants, and then turned away from her. I could feel her staring at my ass.

Slowly I pulled down my boxers, and I heard Helen laughing and saying, “mmm…” I couldn’t take the discomfort any longer, so I turned around quickly. She looked at my face, then slowly gazed down my torso, until I saw her eyeing my flaccid cock. She became quiet. My cock is not enormous but is bigger and wider than most. She began acting self-conscious and making small talk but kept staring at my cock. I asked her if she liked what se saw. She replied that she was quite excited to have me as a partner.

She brought the camera to her face, and then pulled it down. “I think you have to be er…erect for the photo,” she said. I asked what I should do. There was a long pause. Helen suggested that she strip. “It might help.”

I sat at her seat, and she stood up. She stood facing away and took off her shirt. I saw quite a few little freckles on her shoulders with her black bra straps crossing her back.

Helen kicked off her shoes and pulled down her jeans. Again I saw the cutest little freckles all over her perfectly round ass. She was wearing a black thong. I could barely wait for more.

She decided to ease down her thong next. She took her time, and I enjoyed the view. Her hands then went behind her back to her bra strap. She unhooked it, pulled it over her shoulders, one at a time, and let it drop to the floor. I caught a brief glance at the side of her left breast and was surprised. It couldn’t be.

Helen turned around, and it was true. She was top-heavy. Much more than I ever guessed. She must have worked so hard to cover her breasts up and draw attention away from them. She did a great job, because she had to have at least c-cups. Her lovely breasts resembled large teardrops and were so natural. They actually hung. Their weight was pulling them down her torso. They were full, elegantly rounded in light skin and the occasional freckle until you reached her nipples. They were pinkish red and wide, about the size of a half-dollar. They just sat there, relaxed, and I first thought that I had to see them erect.

I realized that I was staring and looked up to her face. Her eyes rolled away as if she was embarrassed by her breasts. My eyes ran back to her breasts and then inched down her stomach. She had a neatly trimmed mound of auburn fur that led you to her vagina. Her legs were mostly together but I caught a glimpse of her red labia and very tip of her clit. She had to have a pretty large clit for me to see the tip of it.

She asked me what I thought. I told her that I had never seen a more beautiful woman. She smiled and almost teared up, composed herself, and asked me to grab the camera. She posed with her hands on her hips and a wide smile on her face. The picture was perfect.

She looked at my cock and saw that it was growing. She told me to touch it and pump it while she posed for me. She leaned forward to accentuate her breasts and then turned away opening her legs a bit and sticking her ass out. I was hard.

She took the camera from me and told me to stretch out my legs, rest my head on my hand, and give that “fuck me” look. I did as I was told and she snapped away. The pictures were ready for posting.

I asked if she was as frustrated as I was that we had all those ground rules. She was. Helen then said that we had no rules about having sex with ourselves just rules about sex with each other if no other couple was there. We finished off our computer work, and she led me to her bedroom.

Helen lay on her bed and told me to sit on the chair across from her bed. We sat across from each other as naked as can be. She then ordered me to “jack off!” She said that she would do the same. I grabbed my cock with my right hand and began pumping away, making sure that she had a nice view and that I could stare at her. She parted her legs, so that I could see her face framed between her knees. She then used her left hand to rub her vagina and clit while she flicked her nipple with the other hand.

Wow, her child is going to be very happy with her tits. Her large areola had eraser-head nipples sprouting from them. Her middle finger also loved her clit. She really was jacking off like I was. Who would come first?

Helen asked me to walk over to her and stand next to the bed, and then ordered me to continue pumping my cock. She saw that my cockhead was becoming engorged. She then inched closer to me and told me to cum on her tits. When someone like Helen is naked next to you, masturbating, and ordering you to cum on her amazing tits, let’s just say that you do it and it takes no effort whatsoever. She could make a million dollars a year working at a sperm bank and convincing men to cum on command.

I felt my cock get really warm in my fist and saw the head blow up like a balloon. Soon I was shooting my cum all over her breasts and moaning uncontrollably. Helen kept repeating “fuck yeah,” rubbed my cum into her breasts, and feverishly rubbed her clit until she came with a loud “ahhhh!” She took her wet fingers from her snatch and brought one up to my mouth. I stared at her and sucked it. Her eyes closed and body relaxed.

When were we going to find the right couple to start our exploration?