I was looking for a certain chat room and pressed the wrong one. I ended up in one called "In Her Panties". The one I was looking for was a golf chat room. I waited for a second wondering what was this about when I got a chat from a woman name Randi saying "hello", I sent back a "hello" and she began talking to me by chat in a way I had never heard of before. It basically went like this, She said "I would like to meet you sometime". I asked her if she played golf and she replied that she loved to play golf. I told her I had never played golf with a lady but it sounded like it might be fun. As the chat progressed I learned that she lived just a mile form my house. Before I could say much she asked me if I would care to meet for dinner the next week. Of course I said yes, we made plans to meet on Friday after work at a place she liked and I agreed.
We met at the bar and grill, I knew her because she told me that she would be wearing a black skirt and red blouse. After we met we went to our table which she asked the waiter to seat us in a private spot as we had business to discuss. I thought that was strange, because she had not mentioned business before. I was thinking she was in sales and was going to try to sell me something. After we were seated we talked and soon ordered our food. Randi was a lot of fun and we spent about two hours talking about our lives and word. When we left the restaurant she kissed me on the cheek and said good bye. Believe me I was taken by her she was beautiful and something about he made me feel good about her.
We dated for about two weeks and one afternoon at a restaurant as we sat taking she put her hand into her purse and then under the table and put something soft in my hand and she looked deep into my eyes and said "make me happy go into the restroom and put these on and bring me yours." I held the object tight in my hand and went to the restroom and into a stall and looked at a pair of very sexy panties, I blushed big time, I waited and thought for a long second. I remembered as a teen stealing a pair of my neighbor's daughters panties from a hamper once and when I got home I not only put them on but sniffed them. It was one of my best times as a teen and long remembered. I hid them in a wall space in my closet and when we moved I forgot them there. I decided to put them on but not before a little sniff, they were defiantly been worn lately. I put them on and went back to the table and slipped my briefs to her under the table. The conversation quickly went to how did I like the feel of them. I turned flaming red as I said they felt good. Randi said she would like to play golf on Saturday and that I was to wear the red panties that she had given me as she said was a gift to her pretty friend.
We met on Saturday at the club she belonged to, when we met she said she was waiting for a couple of friends. As we waited she directed me to a private area and asked if I would show her the panties? I blushed as I unzipped my pants and slide them down just a bit so she could see I had them on. She looked at me and them kissed me like I had never been kissed before.
Her two girl friends arrived and I learned that they would be playing along with us. On the first hole I met Debby and Cathy, Randi suggested that we play their normal game for truth or dares. Debby and Cathy laughed and said that would be fine and they all looked at me. I asked what that meant. Randi explained that the person with the highest strokes played for that hole would be given either a question that they had to answer with the truth or given a dare. I did not know what I let my self in for but said "OK".
On the first hole Debby was the highest and she drew from a cup a tag that said dare on it, she had to get a dare from the lowest which was Cathy. Cathy dared Debby to let me touch her nipples, I was shocked, but gladly went along with the game. I touched her lightly on her nipple, but was told I had to really feel her up. I looked to Randi and she said I was to do it like a man. I did feel her up good. The next hole I was highest and I was also afraid of what I would have to do. I drew the word truth. Randi was the lowest and said I had to tell about my first time wearing panties, needless to say I was really blushing and they all pointed out how red I was. I had to tell, them in detail about the stealing of my neighbors daughter's panties and what I did with them. They all laughed and Cathy asked me if I liked that experience, I answered "yes".
The whole game went on with some really dirty and some very sexy things going on. But on the last hole I lost big time they said that I had to do everything that the winner told me to do because I was the loser. I really did not want to do this but the game and the dares and truths had made me hot and I was not thinking with my up-stairs brain. Randi being the winner told me to meet her and the others at her house. As I drove to Randi's place I thought back to how I got here in the beginning with the pushing the wrong chat room and meeting Randi and doing the wearing of the panty thing. I stopped off at my house to get a clean pair of underwear. It took a few minutes.
When I got to her place no one was there yet but there was a note on the door to go on in and wait. It went on to say they would be right back. I went in to the house and to the living room. Her home was very nice and clean as a pen. I looked at the pictures on the walls and sat down to wait. I then saw a envelope on the coffee table. Looking closer I saw it had my name on it. I opened it and the note told me to go to the second bedroom on the right and look in the top drawer and pick out a pair of panties and put them on. I walked to the room and looked in the drawer and found a lot of sexy panties, I picked through them and found a pair of pink rumba panties they looked so sexy. I undressed and slid them on, just as I did I heard the front door open and the girls burst into the room before I could pull my pants up. There was the flashing of cell phone cameras. I almost ran but thought they would think I was stupid or not manly. Don't ask me why I thought that it would not be manly I just did.
Randi came to me and hugged me and said how pretty I looked. I felt a weakness come over me as she and the other said I was so cute in them. They told me to model them so they could see how pretty I was. They showed me how to model for them. In hind sight I don't know why I went along with them because it was not like me to be led by others. I was very strong person and a top leader at work and in my life. Suddenly I felt like I had a big weight lifted off my mind. Randi comforted me with hugs and the others told me it was OK to be soft at times and this was one of them. They helped me remove my other male things and before long I was dressed in a very fem outfit but not stupid looking. They put some kind of bra on me that had built in boobs and a sexy pair of stockings and garters, and a very nice satin dress. They kept on telling me that I was so pretty and that I was doing the right thing.
Before I knew it was standing in front of three women dressed sexier than they were. Randi said that they should all get dressed up and we all should go to the restaurant that Randi and I had met. I started to protest but did not for what ever reason. We soon were in the car with Cathy driving and off to the restaurant. When we arrived the woman who seated us said how sexy we all looked and what was the occasion? Randi whispered in her ear and she looked at me and smiled. I knew that she was told that I was a man in women's clothes, again I blushed and she came and hugged me and whispered in my ear that I was so pretty.
To make the story short I have spent a lot of weekends being their boy toy. I have worn bikini's to the beach and dressed in female garments and a lot of other outfits to please my Mistresses. I am setting here now dressed as a baby girl for Debby. Yes, diaper and all I am glad I found my new life with Randi and Debby and also Cathy.