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How To Ask A Girl Out (To Prom)
She was a Volleyball player and we became good friends. I had no steady girlfriend and she was a little on the heavy side. I ask here if we could go to the Prom as just friends and she accepted. We arrived sat with some friends her and I went for a walk around the hotel. As we sat on a bench we begin to passionately kiss one another. And then back into the ballroom. We headed home and went for a drive. On a dark secluded road know as a scary road we drove a while and kissed passionately yet again. Then we drove to her house where the passionate kissing continued. As I walked her to the door we settled on another date. Before long we were a steady item. But deep in me was a desire for cross dressing and unbeknown to me she was a lesbian at heart. As we dated and thing really heated up we decided to get married. We both were repressing our true desires without the other knowing. One night she came home and found me asleep with her lingerie on, black silk panties and a black bra. Her reaction was far from what I had expected. Instead of her being angry she was quite happy. She told me of her desire for women and how I dressing as a female for her would satisfy her desire for now anyway. She said we would go shopping over the weekend and but me some lingerie of my own. She measured me and was able to determine my size. She went to the closet and tried on some of my clothing and it fit her. She had me use depilatory cream all over my body. She began to make plans for a date night for us only with a twist I would be the girl she would be the guy. As the weekend arrived she found me a nice mid-length wig blonde of course. A black dress and we purchased several panties silky and lacy of course with BRA's to match. Found me some shoes and bought me some slacks and a blouse. We went home first. She had called a glamour studio that would makeover women and take pictures. We enter with me in full male attire and she told the young lady that I was her subject gave her the wig and told her to do the makeover and get plenty of pictures. So glamour pictures were taken and I was to redress with the new dress we had purchased and the lingerie. Black panties, a matching bra, garter strap and stockings. Then the 3" heels along with the professional makeup and a look in the mirror and I had been transformed into a beautiful young woman. While all that was happening my wife was getting a suit for herself and a man's haircut. As the season was completed she came in and selected the pictures she liked and purchased a package. All my things were changed into a purse and the clothes I had worn in were handed to her as she grabbed my hand and we walked to our car. She opened the door for me and helped me in like a lady. She then went to the driver's side and off we went. I ask where were headed and she said that Cheale is a surprise. We drove to the opposite side of town to our favorite steakhouse. Gave the hostess our name and we were seated. The waiter called me madam all night and my wife was sir. I of course ordered a petite steak instead of my usual and she ordered my usual. We finished dinner and she drove us to the next place. A dance hall that was quite popular. Before we entered she said now you may dance with any of the guys you please. When they ask and she was going to dance with the girls. As we entered I was asked by a middle aged man to dance. I said of course and he led me to the dance floor. Holding me tight he grabbed my arse and said nice. He ask me to go the parking lot with him our maybe he could take me home I said I don't think my husband would like that. He led me to her and asked him if he could take me home. She said well this lady is going home with me why not take her with you. I looked at her and she said well just to the parking lot. He led me out and pushed me to my knees told me to unzip his trousers. I did as instructed and a 9" cock popped out. By now my wife had arrived with her date as she said well go ahead Cheale suck it good. I didn't want to but she leaned downed and whispered if you want me tonight you'll do what I tell you. I leaned forwarded and begin kissing and sucking his cock as he grabbed my head and pulled me all the way on his erect shaft. I begin moving up and down sucking and rolling my tongue until he exploded in my mouth. He then handed my wife a fifty and said just as good as you said it would be. He looked at me and said thanks slut. As he walked off my wife led me to the car and we went home. Arriving at home she begin to strip me down then pushed me face down on the bed. My arse up in the air as I felt a sudden pain as my wife began to thrust with a large strap on. She begin fucking my manhole harder and harder. As we begin to move together in a nice rhythm. She then turned me over my own cock hard and with her now moist she slid on me. Riding up and down as I begin to breathe hard and she felt my cock getting to the state of Cumming she climbed off reached for a glass as she continued to stroke with her hand until I spew warm cum into the cup. She then wiped my cum on her strap on and made me suck it off. Saying that is a good cum slut Cheale we will do this again sometime.
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