I flew home for the weekend and the next week I was in a different city. Each day I woke up thinking about him and how it felt to cum with his huge cock inside me. On Monday I even went out to an adult bookstore and bought a huge dildo and I tried to replicate the orgasm. While I could get my cock to twitch and milk a little cum out, it was nothing like the orgasm I had with him. I was also checking my email often hoping to hear from him. Wednesday, I even set up the same chatroom hoping to see him, but all I got was random horny men who wanted me to send a picture.
It was the following weekend when I got the email I had been hoping for. It simply said, "would like to see you when you are back." The email was scary and arousing. I was not comfortable with being gay. In fact, I felt a lot of guilt by what I had done, but I was so turned on by the thought of being fucked by him again. It was literally all I fantasized about. Any time I thought about sex, I either relived it in my mind or made up some variation of it. I would get hard at my desk thinking about it and in the early morning before I was fully awake I would start thinking about it. This would lead me to masturbation in the shower reliving him fucking me, but after the orgasm, guilt would come and I angrily finish my shower, dress quickly and promise myself, I was done with it. A few hours later as my libido bounded back things were different.
I sent him an email and babbled via writing as I do. I wanted to know what to do to make him happy. It was very difficult to get much out of him via email. After a few days of trying, I invited him back to the chatroom the next evening to talk. It was typing chat and not video chat and I did most of the typing. It was more successful though. We ended up chatting and I was able to find out more about what he liked and disliked. Over the next three weeks we spent many evenings chatting. I was thoroughly enjoying it. I would order room service in my hotel and then take my clothes off and log in. I would masturbate for hours chatting with him. It was mostly me talking dirty to him and telling him all the ways I wanted to please him. He did let me know what he liked though. I gradually figured out that he liked women and men. Well, he just liked sex. He also had a fantasy of having sex with the typical white MILF soccer mom.
We chatted in the chat room each night for the next few weeks. I would create a private room and wait for him to come in. He did not know it, but I was bringing more female clothes and more toys with me each week. I would dress in a bra and panties each night as I got online to chat with him. I normally traveled without checked luggage and I did not want the Xray of my carry-on to have a dildo so I would improvise. I would take an ace wrap and wrap a shampoo bottle up, cover it with a condom and put it in my ass so I could enjoy a nice full feeling as I chatted. I would masturbate each night as I tried to find out what turned him on as the same time that I tried to make him cum every night. I was hoping that turning him on would make him want me more.
One night as we were chatting, he asked me how I had cum without anything touching my cock. While he was fucking me on the bed as I lay with my legs over his shoulders and he was standing at the foot of the bed, I had cum with only anal sex and nothing stimulating my cock. I had no idea how it had happened. He seemed intrigued about this and kept asking me questions. Since he was so interested in it, I tried to use to arouse him.
"I don't know, I have never cum like that before. Normally I have to masturbate for a long time before I can cum."
"We weren't fucking long at all. I fucked you on the floor for a few minutes and you came in less than 2 minutes when we got up on the bed."
"I know. I don't know why, but it was so wonderful. I am so sorry I came so quickly, but your cock felt so good. Every time you pushed into me, I got closer and the way you slowly pulled out felt so good."
Sitting in the hotel room, I was rock hard and ready to cum. I was playing with my cock as it leaked precum. I got up and got a condom from my toiletries to keep the precum from getting everywhere.
I hoped he was not too disappointed that I came so quickly so I said, "I hope you are not disappointed that you turned me on so much that I came so quickly. I promise next time I will really try to not cum before you. I really only want to please you. I don't need an orgasm as long as I please you." I did not really mean this. It was a fantasy of mine, but I really love cumming.
His reply came a few moments later. "It was good you kept going. Most guys quit after they cum."
I am not most guys, and I will not be a guy next time. I will be your sexy soccer mom and I will keep going as long as you will. I want to fulfill all of your needs and fantasies."
"Let's see how sexy a soccer mom you can be."
The week I was to work in his town, I changed my flight and arrived late Sunday night so I could prepare and be ready for him Monday night for Monday night football. He had told me that he liked to go watch it with his friends, but I convinced him to come to the Residence Inn to watch it with me. I would make him dinner, snacks, bring him beers and make him happy. On Monday morning when I was normally flying to my workplace, I was grocery shopping instead. I bought dinner for a meal, snacks to feed him, and beer. I wanted to have everything to make him happy. As I shopped, I imagined that I was already dressed and was shopping for him as the soccer mom getting ready for her next date with her lover. I was probably mincing down the aisles and I was acting effeminate as I bent over and picked up my groceries. By the end I was turned with my little fantasy and ready to see him. I had to keep myself from masturbating as I returned to the hotel and put the groceries away.
I left work early enough and got to the hotel to get ready. I had laid out my clothes and prepped as much as possible. I did my makeup and put on fake nails that were 1 inch past the tips of my fingers that were painted light pink. I had worn longer but I was not sure how long he liked, and I wanted to be able to do anything I needed to do to please him. Next, I put on a long pink and light blue Laura Ashley print dress and 3-inch heels. I finished it off with way too many rings on most joints on my fingers and dangly earrings. I thought I looked older than I was, but the perfect soccer mom dressed for date night with entirely too long nails. I hoped he he'd like it.
I prepared a quick meal of jambalaya and put out chips and dip for him. I was almost finished when he arrived. I met him at the door and meekly opened it and said, "Hello. It is so good to see you again, Charles. I am so happy you came over to watch football. I made Cajun for you, and I bought your favorite beer. I hope you will enjoy it."