I had been wearing my sisters underwear and clothes for a few years without anyone knowing. I really wanted to dress for someone else but had never had the opportunity. I used to help our next door neighbour with his garden. He was a widow and had a huge garden and house and he often asked me to help him. After helping him one day we were in the kitchen having a drink when he asked if he could wank me. I let him but came very quickly as it was the first time I ahd let a man touch me. Over several months after I often went to help him and let him stroke and wank me.
One weekend my parents and my sister went away to see some friends and I was left at home. I decieded that this would be my opportunity to dress up. So I slipped into my sisters stockings, suspender belt, panties and bra. Wore her school uniform and got a wig from my mums room (she was into am dram and had lots of wigs etc). I carefully put on make up and jewellery and then went next door. The look of total surprise was fantastic. We chatted, had a drink and then we went upstairs to his bedroom where he sucked my cock and played with me for ages. I got to touch his cock for the first time and sucked him off then he put on some videos which got him hard again and then he very slowly and very gently took off my panties and fucked me. When he had finished he got me to fuck him with me still fully dressed except for my panties. I stayed the whole night and we both fucked again the following morning before I went home and carefully put all the clothes bakk.