Riding the Jessie Train

Everyone was pretty worn out by this point, but none more than Jessie. Cum leaked from Jessie's holes as first Andrew and then Ben withdrew from her and the mass of human flesh disassembled. As I backed away and started to pick up my clothes, that guilt plagued my mind that maybe we had gone too far, but I quickly suppressed it.

We guys got dressed and did a little cleaning and freshening up while Jessie had rolled over in the bed, breathing heavily as she appeared to doze off. Her hair was untidily spread over the pillow, her limbs weakly lying on the blankets. Her body gleamed in the dim light from being coated in sweat, both hers and ours. My heart went out to my friend. She looked incredibly sexy lying there in only her high heels, having probably bit off more than she could chew. It took three strong men, but this sex goddess may have met her match.

Ben and Andrew left once they were dressed. Andrew asked if I was going to stay with Jessie, which I affirmed. Those moments were pretty awkward, but I was able to be comfortable and reflect on what had just transpired once the other guys left. The temptation to take a picture of Jessie as she lay there soaked in sweat and half-conscious at best was excruciating, but I didn't want to violate her trust.

About 45 minutes after the other boys left, Jessie finally sat up. Upon seeing me, she smiled sweetly and asked if I had had fun. She didn't complain of any discomfort, but I could only imagine she felt wrecked, both physically and mentally. I let her shower and change into some shorts and a t-shirt, and then I showered as well before we decided to spend the evening together in that cheap room Jessie had rented for the night.

After the sun had gone down, things officially went too far. That night ended with that true culmination of 10 years of friendship and sexual frustration with Jessie as I finally had passionate, intimate sex with her. While we would end up coming clean with Jessie's husband, who surprisingly didn't completely lose his cool, I probably wouldn't be joining their marital activities for a long time, if ever again, which was a shame. But the temptation to fuck her that night was simply too strong. Once it got dark, Jessie decided to spend the night, not needing to explain to anyone where she was because she was a grown woman. Eventually, being bored and tired, not to mention the factor of all the sexual activity in which we'd been involved, it was inevitable that we got naked and made love.

It started with harmless hand stuff. Hand stuff became oral, and oral became Jessie on her back, under the covers, taking my cock over and over again in her pussy as I lay on top of her with her arms around me. We kissed and fucked intensely for at least 30 minutes, my cock raging despite being worked hard that day. When it was over, I was both as satisfied as I'd ever been and ridden with guilt because I'd fucked another man's wife without his consent, participation or even knowledge. However, while pressed against Jessie and stroking hard and fast into her twat with no one else's involvement for the first time, I'd be lying if I said it was anything short of a divine experience.

When we were finished, we both had orgasms. I pulled out just in time to cum on her face one more time while she continued to lie on her back and started to catch her breath. Relaxed and content, we fell peacefully asleep, even in that sketchy motel, but when we awoke, we knew we had done wrong. We weren't awkward with each other or anything, though. We agreed we had fun, both during the the gangbang and our intimate sex. We even didn't want to close the door on future threesomes with her husband, but with his trust violated and the lines blurred, we thought it better to just enjoy the memories, let things go back to normal and move on with our lives.

Since then, I've grown content with the thought that my sexual exploits with Jessie are likely in the past. They were wild, hot, dirty and fun, and I'd always have those memories. Now, though, I was free to move on, to open the door for experiences with girls who didn't live more than 500 miles away from me and who weren't married. I soon realized that double penetration was not only still a possibility, but something I could experiment more with as I pursued sexual encounters.

"Try Craigslist," Jessie suggested via text one day. "Let me know how it goes. I want to hear everything."