A Night of Cheating

Author's note: This story is fiction. It may be the first in a series, depending on response. As a first time author on this site, I welcome constructive criticism. Enjoy!

I was anxiously awaiting her arrival, a little nervous. I had never cheated on my wife before, and I had never been with another woman. The next twenty-four hours promised pleasures the likes of which I had never felt before. Of course, all I could think of was my wife.

Her name is Lisa. She is beautiful, kind, loving, and not at all interested in sex. Our marriage would be blissfully happy (at least for me) if it weren't so sexually frustrating. So, with my wife out of town, I had turned to Craigslist personal ads to try to find a partner in adultery. It turns out that is a tedious task, with all the spam, but that is where I discovered Jenny.

Jenny is older than me, in her early forties compared to my late twenties. She did not seem to be stunningly beautiful, but she still looked good in her pictures. More importantly, from our chats I could tell she was wild. She was willing to do almost anything that can be done between a man and a woman. She claimed to love giving head. She expressed a willingness to try whatever I wanted to try. She understood my position as a happily married man, and she was willing to help me out with my problem. I knew tonight would be a night to remember. It was already 5:00; she would be here any minute.

And yet, I was still daydreaming about my wife, wishing it had not come to this, wishing that she had been more willing to at least try to satisfy me. In five years of marriage, we had yet to venture beyond the missionary position. She never gave me oral sex, or allowed me to give it to her. Forget about any kind of sexual variety; she expected me to be happy with plain sex every few weeks, and could not understand why I was upset about it.

A knock at the door woke me from my reverie. I was trembling a bit when I stepped to the door and opened it.

There she was, Jenny, with shining blond hair, deep green eyes, and a hesitant smile. "I thought you would chicken out on me," she said.

"No, I need this. More than you know."

She stepped into the apartment and I shut the door behind her. "Nice place," she said, seemingly expecting some kind of brilliant, witty response. "Yes, it is," was all I could muster.

She turned and looked sharply into my eyes. "You are still thinking about backing out, aren't you?"

I could not lie to her. So instead, I blurted out: "I can't stop thinking about Anne. I don't know why. I want this, I really do, but she is in my head and I can't push her out."

"Let me try," she said, and she planted her lips on mine and forced her tongue into my mouth. I reciprocated, timidly at first, then succumbing to the passion of the kiss. I felt a stirring in my pants, and I knew that I was doing something I needed to do. But I still thought of Anne.

"You said you have never fucked anyone but your wife, right?" said Jenny as she walked over to the living room couch. I shook my head. She beckoned me over, and I sat down.

"Then we had better start quickly, and get you to shoot your first load of the night. It is going to be quick, powerful, and messy. Lay down." She got up as I obliged, stretching out on the couch. She slowly removed her T-shirt, revealing large breasts held in by a black lace bra. I watched, speechless, as she stripped before me; I felt my crotch getting warmer and my pants seemed to be getting smaller. Her shoes came off, then her pants, revelaing panties to match the bra. Without saying a word, she reached down to unbuckle and remove my belt, unbuttoned and unzipped my pants, and removed them, revealing my white boxers. My erection was clearly visible, nearly bursting out of my boxers by now. "Let's release him, okay?" Jenny purred sweetly. I could only nod, dumbfounded by what was happening.

She began to gently stroke my cock, now standing at attention. She smiled, but said nothing. Slowly she lowered her face to my crotch, and gently ran her tongue up the underside of my shaft. I could not believe the sensation; I felt like I might blow my load right there. Then she gave my a wicked grin, and I watched as the head of my cock disappeared between her lips.

The sensation was indescribable. I had never felt anything like it. Her warm, wet mouth felt more like a pussy than I expected, but her lips and tongue were actively massaging my cock in a way that no cunt ever could. At first, she just took the head into her mouth, then another inch. Before I knew it she was sucking on about three inches of it, with her hand still stroking the rest. I moaned in pleasure, thinking again that I might blow my load, but somehow I still held off. "I bet you aren't thinking about your wife now," she said mischeviously, taking her mouth off of me and giving me another wicked grin.

"No," I muttered under my breath, shaking my head.

She stroked my cock with her hand, three times, slowly, then in one smooth motion she took the entire thing in her mouth. I could feel the head hitting the back of her throat, and I nearly fainted from the sheer pleasure. I moaned loudly, my whole body trembling, as she began to fuck me with her face.

I felt the cum welling up inside, and I knew I wouldn't last much longer. I felt it rise up and prepare to shoot down Jenny's throat. "I'm cumming," I shouted, immediately thinking what a lame thing it was to say.

Jenny pulled my cock most of the way out of her mouth, holding the head and about an inch of the shaft in. I felt the semen begin to shoot out, undoubtedly coating the back of Jenny's mouth, as she moaned some encouragement for me. Her moan only drove me further over the edge, as I shot spurt after spurt into her willing mouth. She did not lose a drop.

When I was finished, she let me cock leave her mouth with a small "pop." She looked right into my eyes, a mouth still full of cum, and said "Mmm..." before she swallowed. I could scarcely believe that any of it had happened, but I did not feel even the slightest pang of guilt or regret.

"So, are you still thinking about your wife?" she asked. I could honestly say no. This was going to be a fun night...