Growing Pains & Pleasures

Chapter 4: Annie E.

It had taken twelve months to progress from a naïve young mother who had known no man except her husband, to a woman who realized she had the ability to direct her life on her own. Before, Tom was my only source of how the world really worked. Now it was clear that things could be quite different for me than anything I had ever imagined. Growing up, I always saw myself as the typical wife and mother, raising kids, supporting my husband in his career, joining the PTA and being a faithful typical wife. I never imagined being with other men or using my body to influence a man's behavior. My wardrobe was conservative and I hid my body with my clothing. I only owned one "sexy nightgown". It was just a semi-sheer black gown, nothing really sexy at all. The rest were flannel or heavy robes. That was the way life was before I slept with Bob and then Herb.

As I explained earlier, it started with my husband's fantasies about other men and me. After he had a brief affair, he encouraged me to experiment. After much fantasy role playing with him, I finally slept once with Bob, a friend of ours. I began to open up sexually after that, role playing with and for my husband's pleasure. We used a dildo, and I would pretend out loud, to be fucking guys we knew as we made love. Not quite a year after Bob, I slept with my neighbor Herb two times in just a week! We had already developed a strong non-sexual friendship and were soul mates. This let me see a side of myself I didn't know existed.

I could do anything I wanted and I could control what happened with me sexually. My husband knew about both of these men and encouraged me to continue. He got tremendous sexual gratification from my affairs. This became a source of great psychological pain for me. I wondered if he loved me, or would one day hate me for what I had done. How could he send a woman he loved to another man's bed? After I slept with Herb, Tom got kinkier in his requests for fantasies. He wanted to have a threesome with another man and me. He wanted fantasies about me with multiple partners! These things had never even entered my mind. I had a hard time making up fantasies about them because they were so different from what I had always thought about sexually.

Herb and I continued our friendship, but I didn't go to bed with him again right away. Tom gave me several opportunities over the summer, but I never felt quite right about it. The fantasies with Tom were giving me lots to think about, and after the second time with Herb (when we did everything possible), I just didn't think that I would do it again. Herb and I talked about sex and our fantasies too.

In the fall, Tom started teaching some adult classes and would be gone two or three evenings a week until 11 pm. On one of those nights, I had just taken a hot bath, after putting the kids to bed. I had lay in the tub and masturbated as I relaxed. When I thought about calling Herb, I felt guilt pains. "I shouldn't do this." I told myself. But the feelings were very strong. Tom called between classes to say he would be late as a couple of them were going to stop for a beer. I told Tom what I was feeling. He said, " Don't feel guilty! I want you to do it! Just tell me everything that happens and be ready for me when I get home!"

I decided to make one of Herb's fantasies come true. My hair was still wet, and I had a robe on. I grabbed my raincoat from the closet, dropped the robe, put on some high heels. Naked beneath my coat, I went next door and knocked. Herb came to the door, peeking out the window to see who was knocking this late. When he saw it was me, he opened the door a little and said, "Come in. I'm not dressed, let me run upstairs and put some pants on." Leaving the door open, he headed for the stairs. I came in, shutting the door behind me and said, " Can I watch?" as I followed him up the stairs. He had only his shorts on. When I went into his bedroom, he was grabbing his jeans from the chair. I walked to him and kissed him. He dropped the jeans, looked at me and pushed me back on the bed.

I'll never forget the look on his face when he started to open my raincoat and saw me totally naked underneath. I started to kick off my heels, but he said, "Leave them on!" As I pulled my arms out of my coat, he dropped his shorts to the floor. I pulled one leg up onto the bed, lying on my back on my raincoat, with my other leg still hanging over the bed. Herb came toward me. His cock touched my thigh as he started move into me, and he moaned, cumming all over me before he ever got in me!

He fell on top of me almost crying and apologizing for cumming so quick. I told him it was not a problem, as I knew how to take care of that! We kissed and touched. He licked and sucked my cunt and I sucked his soft cock until he got hard again. He laid me back on the bed and I raised legs high and pulled my knees back to my chest, still wearing my heels. As I spread myself as wide as I could, Herb lowered himself down and into my cunt. He slid in without any resistance. Slowly pumping in and out, he fucked me until I was moaning with pleasure! His hands slid up my thighs and grabbing my ankles beneath my heels, he raised my legs straight up and out. He really started pounding me now, I thought I should be splitting in half as I looked at my heels in his hands, spread as wide as his arms could reach! But it felt wonderful! Herb came again in a few minutes. Although I was highly aroused, I didn't cum. I felt very happy. We lay on the bed and laughed about how surprised he had been. He threatened to get even someday and I hoped he would!

As a final note to this chapter in my life, I must tell you what happened when Tom came home. After a few minutes of kissing and fondling, I put my coat back on and left Herb's house and went back home. It was just after 11pm and I had just gone into the bedroom and put on a shirt when Tom came in. I was surprised and said, " I thought you were going to be late?" He told me he couldn't wait! He tore my shirt off and began sucking and kissing my breasts. He put his fingers into my cunt and as he pushed them in, I felt Herb's cum release and start flowing out. The awareness that I was about to have a second cock in me in less than a half-hour suddenly hit me! I was so hot I wanted it NOW! I responded to Tom with more passion than ever before! He went wild, plunging his cock into me and telling how he could feel my cunt just squeezing and sucking him in! He was right! Tom had always told me that a woman got really loose after being fucked and that's why they called it "sloppy seconds". But they're wrong! It was slippery and wet, but I could feel the inside of my cunt tightly wrapped around Tom as he banged in and out. It was not sloppy or too big at all! Tom came pretty fast, but I was satisfied too!

Then Tom told me that he had left school as soon as he hung up. He came right home, parked in the next block and walked to the house. I was already gone when he got there. He said he looked in Herb's windows and didn't see us downstairs, so he climbed up on the garage roof and tried to see into the bedroom window. He told me that he could see Herb and I from time to time, but not clearly. He did see my legs in the air and Herb's back as he was pounding into me. Tom masturbated on the roof! He watched until I went home. Then he went back and brought the car home. I was angry and upset that he had watched! I refused to tell him what had happened, including the thing about the raincoat. In fact I now realize that the anger slowed my sexual development significantly. The way I felt about having two cocks in me in a matter of minutes had been tremendous! I loved the sense of power it had given me! But the resentment over being spied on pushed those feelings back for some time!