Chapter 2: Annie
Chapter one told you about the circumstances that led to my first affair. After I slept with my husband's friend Bob, our sex life began to change more rapidly. Tom had already had his second little fling. I was now 24, married for 5 years with three kids. I still had my cheerleader figure, 5-8, 135, 36d-27-37, long legs, brown hair and green eyes. I knew by this time that I was very attractive to men and that I was considered very pretty as well. Earlier I had lacked confidence in myself. Tom kept encouraging me to sleep with other men. I hadn't done it again, but we fantasized about it all the time. He asked me what I thought of various guys and then had me pretend I was fucking them as we made love. It got him incredibly turned on!
It was during this time between my first and second affair that we introduced sex toys into our marriage. Tom wanted to watch me fuck somebody, but I was not at all interested in doing that. He would have me masturbate and watch me, having me tell him a fantasy about another guy fucking me (usually a named friend of ours) as I masturbated myself with my fingers. One night he suggested that I use something to put in me as a substitute for a cock. He suggested a banana, but we didn't have any. We did have some cucumbers!
Tom told me to wait while he washed one and then he returned to the bedroom. As I fantasized out loud about having another guy, he began to play with my cunt, rubbing the cucumber around the opening and against my thighs. I was actually beginning to want it in me! I was pretending it was our neighbor. He was a nice guy whose wife had left him with two kids. My hips were pumping slowly as I lay on my back. Tom was rubbing my tits and my cunt. Slowly he pushed the cucumber in as I talked about Herb, the neighbor. It was like I could see and feel his cock going into me! It really felt great!
As I rubbed my clit, Tom slid the cucumber in and out of me. He was jacking off with his other hand while I described Herb fucking me. Tom came quickly, but I needed more. He continued to pump it in and out. Then he pulled it all the way out. I opened my eyes and said, "What are you doing? I'm almost there!"
I had barely spoken when I felt it going back in. Tom had another cucumber, this one much bigger! It was so big, that I couldn't take it at first. I told him no, just use the first one. But he slowly pushed it in and out, giving me more and more each time. I didn't like what was happening, but I wanted to cum, so I let him continue. This one was as big around as a beer can, and well over a foot long. My hips continued to pump automatically. After just a few minutes I was taking it all in except a few inches that Tom held onto. I really let go and started calling Herb's name begging for his cock! Tom got hard again and put his cock in my mouth, I sucked him and fucked that big cucumber until we both came!
Tom told me that he wanted me to do that with him and another guy for real. I told him no way, fantasy would have to be enough. We repeated that sexual fantasy many times, with many objects. Once we used a large ring bologna. It was much better as it flexed like a real cock. It was big and thick and I could have as much length as I wanted. Also it was curved, like Bob, the only guy I had fucked besides Tom. I would kneel on all fours and Tom would ram it in and out while I sucked his cock. It drove him wild to think of me having another guy in me from behind as I sucked him. This kind of fantasy play made our sex life together better than ever before. Tom went wild over my stories and I enjoyed thinking about other guys. Eventually a rubber cock shaped dildo replaced the vegetables and bologna.