First Time Dressing

Published 13 years ago

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine and then I went through to the bedroom to get changed. Paul followed me in and sat on the bed while I looked through the clothes to decide what to wear for the night. He complimented me on my wardrobe and then asked if  he could try on one of my tops! He is about my size so I said that he could of course. He tried on lots of tops first until he found one which suited him. I told him how well he looked and jokingly asked if he wanted a bust to go with it! He blushed and told me that he’d wanted to dress up for ages but his ex didn’t want him to. I found an old padded bra and some silicon push ups which gave him some cleavage under the top. I asked if he wanted to go the rest of the way and when he agreed I got out some stockings and skirts I thought would suit him. Luckily I had a pair of boots which were about his size as well, so I took the lot into the spare bedroom and left him to it. I choose some patterned stockings and a saucy black skirt myself and was sitting doing my makeup when he came in and for a second I thought it was somebody else who had come in the house. He’d chosen some sheer black stockings and a fairly short skirt to go with the boots and as he is very slim and feminine looking and has his hair quite long, he looked really good even without a wig. We had some more wine and I had lots of fun getting his face made up properly. He was really thrilled with himself and I had to get my camera and take some photos of him in various poses before he was happy. He didn’t want to go out dressed in town so we debated for a while and then decided to get a taxi to the city and go to a club there. We were both wrapped in long coats and the taxi driver didn’t notice a thing. Paul didn’t actually say much – I did most of the talking. I did notice that he flashed some leg at the taxi driver when we were leaving which seemed to cheer the taxi driver up a lot. Paul was really brilliant for his first time out and I could see a lot of guys (and girls) taking a closer look. We were pretty restrained in the club, danced together a few times and drank some more at the bar while Paul flashed some more leg and chatted to various people who passed by. It was clear he was having a brilliant time. In the taxi on the way back he flirted wildly with the driver who seemed pretty interested. Back home it was clear that John had been on a bit of a marathon session, we could hear the snores from the bedroom in the living room, even with both doors closed. We had some more wine on the couch and things began to get a bit out of hand. It started with Paul teasing me about being tarty and trying to look up my skirt to see if I was wearing any panties – he obviously had to! We ended up playing – I’ll show you mine if you show me yours and playing truth or dare. Material for another story there!