My mother need to go away for the weekend and our neighbour in his 60s said he'd keep an eye on me.
When I came home from college on the Friday afternoon my mother was just leaveing, and gave me some last minite instructions as she left. Our Neighbour whosn name was Jon, was also present, and as my mother drove off in the Taxi, he said to me that if I wanted to I could let him take me out for a meal, to which I agreed, and told him I'd come over to his place after I'd showered and changed, to which he agreed, smileing at me and adding that we should be in for a great weekend.!!
I got showered, and changed, and was soon at Jons place. Once inside he offered me a Drink of Brandy, saying, he hoped I'd not tell my mother that he was encourageing me to Drink. I laughted and he placed his arm around my sholder saying that I laughted very much like my mother. I smiled, and felt Jons arm slightly tighten, as he said may be he'd find out how much more I was like her later on, but now we must leave for a meal.
Jon had found a nice little wine bar, which wasnt over crowded and we found a table at the back but in a position where we could see all, with out being sceen. He orderd for us both and came back with a bottle of White House wine. Soon we where chatting away, especialy about my likes and dislikes and what we could do for the rest of the weekend. As we chatted I noticed as well as Jon did, that two women one about 50 the other in her 20's sitting together not far from us, and being rather intermit, as they siped their wine. Jon whispered to me that he hoped that I wasnt getitng to hot watching them. I smiled and blushed as I replied no, but I could if I was and liked to be the younger one receiving all that attention from the atractive older woman.
Jon smiled saying one never knows what one may end up doing or being, as our conversation turned to Womens cloths and how I liked Twenty (Charlston) Style frocks and Fur coats, Teddys, as well as Ball gowns. Jon became mor intrested and asked me if I'd ever dressed up in Womens cloths, ans when I admitted that I had on two occasions, he wanted to know more. I told him the first time was when after I played a Princess in a college play, and was still in costume when I was chatted up backstage at the cast party buy a friends uncle, who thought I made a very nice girl, and asked me if he could drive me home, and may be stop at his place for a coffee. I agreed, as he said I didn't need to change, as I could remove my make up etc, and wash it off at his place. Once in his car we drove to his House and parked in the drive, He lent over put his arm around me saying I was now his nice little girl as he kissed me. I relaxed as I felt his hand exploring me all over, becomming excited as I' allways fantacised about being with another man, dressed as a gir, lever since I was twelve years old and had been with an older man along the river bank in the long grass.
He helped me out of the car and soon he was giving me a glass of wine, after hed gone up stairs and brought down a full length fur coat for me to wear over my strapless gown which he admired. Soon we where dancing very close and after a third glass of wine, he had me down on the couch, as he was now naked was rubbing against the fur and slowly makeing me submit to his hard manhood as he told me I was such a devine woman..Jon was now touching m, as he asked how I felt and did I like it. I told him yes, He smiled as he squeesed my now hard cock, saying perhaps I could dress up for him every time we meet. I again blushed and said I'd like to do that especialy for him. as he convinced his devine cock up into my waiting boy hole.
[By now John was kissing me as he finished giving me my first propper ass fuck, which had made me excited and cry with the first intense pain, as he said I was live a virgin girl being fucked for her first time, as he skillfully rode me again and again, saying that he was thinkg I was my mother wich made him so excited as as he couldnt fuck her fucking her son was just as good. As he shot his massive cum load up in me soothing any pain he called out my mothers name, then turning me over he sucked my willing cock till I filled his mouth with my boy cum.
John then said that he had wanted me ever since he saw me and my mother together and now he wanted us both together in his bed and he hoped my Mother was a s good a fuck as her son.