1. Crossdressers First Time


    Date: 9/30/2015, Categories: First Time, Gay Male, Shemales, Author: maninnylons, Rating: 100, Source: xHamster

    I was in my mid 40's and divorced and living a great life. I ran my own successful business from home and lived in a large house in its own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished. Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired business woman sexy and great in bed and Sarah was my age a nurse who loved sex and could use me all night. What I kept quiet and had since I was young was that I cross dressed. I now had a locked closet full of ladies, clothes, lingerie, shoes , wigs and make up. I would indulge myself and dress as my alter ego Paula at least once a month and enjoy time being a sexy lady. The dressing relaxed me and I had never really seen myself as gay or bi it was just my bit of fun. I had only ever been seen twice in ladies clothes. Once, shortly after my divorce, when I visited a dressing service as I knew I would be dressing more often and the other time I visited an e****t and wore panties and stockings when we had sex. The dressing service helped me look quite passable. I was only 5 feet 7 and slim and fairly hair free. I now kept myself completely waxed which I explained was due to the fact I did a lot of ...
    cycling (no lie). I had found myself drawn more to cross dresser porn and often fantasised about sex with men but apart from dressing cam sessions I had never had a sexual encounter with a man and saw myself as curious only. It was a December day and I had decided to be Paula for the day. I had put on white lace lingerie including lacy boy shorts. I had put on suspenders and cream stockings with black seams. I slipped on a short little black dress which showed off my slim legs and some black stilettos. I applied some discreet make up and my black bob wig. I was not worried about surprise visitors as the only way on to my property was through security gates and I had a sophisticated alarm system which would warn of intruders. I did some work during the day enjoying the thought of clients and my broker talking to me unaware that I was dressed up as (even though I say so myself) a sexy milf. By the afternoon I had done my work and logged onto my computer and started looking at some of my favourite porn sites and enjoyed the films of some hot cross dressers I stroked myself through my panties but held off cumming as I planned a long night of porn and cum as I was not expecting to see anyone that evening. Pre-cum oozed through the lace panties and I decided to stop for a while and get a drink and watch the news. Due to my location I rarely closed the curtains and I could see outside that snow was falling so I decided to pop out and get some logs for my wood burner. I slipped of my ...
«123»