Ch. 02: How to Ruin Good Sex

The following is from a series of true events I've experienced which I've decided to tell sequentially. I recommend reading them that way also. Part 3 was originally going to be Part 4 until I realized that I had forgotten a few details which actually changed the chronological order of events. Hope you enjoy.

I eventually ended my little arrangement from the previous story. It was wonderful and I still remember it fondly, but it was becoming risky. Not least because she admitted to sharing some of the details with a friend. So I had to seek something to replace it. That's when I found myself searching for someone online. I had a few ongoing conversations with a number of women including one that wanted me to fuck her and urinate on/in her. I seriously considered it but she wanted her boyfriend present and I didn't feel comfortable meeting both of them at the same time being they wanted to go straight to the deed with no getting to know each other. It seemed it could be a little unsafe especially because they wanted a hotel room. I also had some very steamy conversations with some others and exchanged both vanilla and erotic pictures. Eventually I connected with a woman we'll call Laura for privacy.

She was 23 years my senior at 55 and very attractive. She was also very open minded and said that she had an occasional male companion but was officially unattached. She said she was in "the lifestyle" and I could see she was very in touch with her sexual side despite being a grandmother.

We arranged to have lunch (pre-arranged that nothing further would happen) and met at a tavern where we talked about normal stuff; who we were, what we liked; then got onto how we ended up seeking sex online and what we liked in bed. We got along really well and had a great meal in the quiet tavern with no one but the staff around. The waitress definitely knew what was up, but who the fuck cared? Nevertheless, I was a bit overwhelmed by the whole experience, meeting someone online for the first time and someone so much more experienced than I was. We ended up leaving and continuing to talk but it didn't feel right at the moment despite the desire I had to plunge myself into her. I'd end up connecting with Laura down the line but this story is about someone else.

After Laura I took a break. It was a bit much. I returned probably a year later to the online scene and connected quickly with another woman. We can call her Nicole. She was in her mid 40's, married with kids and seeking some male companionship and attention. She was a short chunky blonde and unlike most men, when I say chunky, it's not a bad thing. I like curves and if a woman's body has a nice shape, the size isn't a factor for me. She also had extremely toned calves accentuated by the heels she wore in the pictures she sent me.

We exchanged a lot of erotic messages and pictures and described what we wanted to do to each other. She looked great in the form fitting dresses and heels she wore to work. We'd often exchange some really hot messages, photos and videos, sometimes taken while she was at work and I was instantly hooked when she told me she wanted to suck my "luscious cock." There was something incredibly hot about her using the word luscious. The chats were close to daily and sometimes lasted hours. She wanted to be my submissive secretary and serve me dutifully in my office. She also wanted to be handcuffed to the bed and taken. Of course I was eager to put her right to work.

Once she worked up the nerve, we agreed to meet at a hotel. I arrived and paid for the room, heading up alone. I sent her the room number and waited. Nicole arrived about a half hour later and knocked on the door. I opened it to see her in person for the first time. She was wearing a black dress that clung to each curve and ended above her knees. She also wore leopard print heels. I was very, very pleased.

We sat on the couch and talked a bit to get comfortable. I mentioned I'd brought handcuffs and she said she wasn't quite ready to try that our first time.

Understandable, so I was ok with that. The only odd thing was, she kept checking her phone as we talked... I mean a lot.

But we continued chatting and eventually got to undressing. I laid her back still in her panties and bra. Then I slid Nicole's panties off and explored her body with my hands and lips. We kissed. Tongues entwined, my hands worked from her cheek, over her shoulder, around one of her enormous breasts, down her side, over her belly, down her pelvis, and along her inner thigh; all while we kissed like high schoolers on a couch with their first love. I placed my palm over her warm cunt and began messaging. She moaned. After about five minutes of this the tension in her muscles began relaxing away and my middle finger over her slit began to attract some moister. I slipped it in slowly, up to the second knuckle. I worked it back and forth, in and out a few times, then full way in. I rose up on my knees and up toward her head for leverage as I began to hook the finger a little upward when I'd sensed she was warming up and getting into a good rhythm; to put pressure on her g spot as I made small, rapid shaking motions of my arm to tease her.

She engulfed my cock between her lips and sucked. We could only take so much of this and I eventually maneuvered over her to sink myself into her now soaking twat. I began to fuck her as I pulled down her bra straps and then the cups to reveal her beautiful full breasts.

We continued about 10 minutes when her head rolled sideways and she let out a wail. She orgasmed around my flesh as I pounded. I pushed on and I could feel her contract wildly around my pulsing member. She grunted and groaned like an animal, deep and husky.

When her orgasm subsided, I told Nicole I wanted her doggy. She rolled over to her hands and knees but something odd happened. Again, she checked her phone. I entered her anyway and as I grabbed her hips the phone went right back to the nightstand. I pounded and pounded, grabbing her shoulders and pulling back on her until I had nothing left. My knees were shot from giving her all I had and I loved it, so I told her to ride me. She tried to ride me reverse cowgirl but I told her I wanted to see her face and tits. She spun around and I cupped her breast as she bounced on my pole. I stared into her eyes. She was really a pretty woman. Genuinely the kind of lady who was a hidden beauty. A diamond in the rough so to speak. Her husband was a fool.

I looked her in the eyes and took in her breasts as they bounced over me, her long, straight, dirt blonde hair flowing down over her face. I felt myself about to cum and asked her. "Where should I cum," She replied with a question of her own, "are you ok with cumming inside me." With that I spontaneously exploded. My cock bobbed within her and sent streams of my seed into her womb. I pulsed, pulsed again, pulsed more, quivered in her and shuddered more of my seed into Nicole.

When I came down off the mountain, I rolled her back and fingered her to another more gentle orgasm, my cum coating her pussy and my fingers.

I laid next to her and tried to wrap my arm around her to lay together but she went for her phone. It was so weird. Then she said she'd better get going. I asked if she wanted to grab a shower and she declined. I left assuming she wasn't that into it/me. Interestingly, she messaged me again asking to meet up. I liked her, was attracted and enjoyed the sex but the weird vibe left me feeling uncomfortable. I explained how I felt and wished her the best but I never saw Nicole again.