First Time With Another CD
If you've read my first post you'll know that while i'd started crossdressing when i was only 10, and had started buying my own lingerie and outfits when i was about 16, it wasn't until a couple of years later, when i was about 18, that i finally discovered i wasn't alone and there were in fact quite a lot of CD's and TV's in Southend. So after seeing a few adverts in local paper lonely hearts columns from other CD's, i decided to put my own advert in there. I don't know why, maybe because i was only 18, but i had a great response and had over a dozen replies. One in particular caught my eye, from Tracy (name changed), so we made arrangements and i went to visit her a few days later.
Like everyone in this first-time situation i was nervous as hell. This was very different to every time i'd been dressed with my next door neighbour. I'd known him all my life and he never crossdressed, he preferred to see me do it. But unlike many, i didn't chicken out. When she answered the door and invited me in, she then gave me the chance to have a good look at her. She was mid-50's, much taller than my paltry 5'6", very slim, dressed in a black top, red PVC min-skirt, black stockings and red high heels with 4" heel. She also wore a wig and makeup... the first time i had seen a CD in person wearing either (I'd seen photos of some but hadn't worn either myself). She looked a bit intimidating... and i thought she was breathtaking. It turned out she was a bit of a domme, but not an actual dominatrix or anything like that, more like she was very assertive. To this day that is something i really like in any men i meet up with.
Our meet was mainly social, which is what had been arranged since she knew i was new to all of this, but once i'd changed into the outfit i'd brought with me, i could feel that same sexually charged atmosphere that i felt with my neighbour. Compared to her, i dressed rather conservatively, black lace stockings, black heels (only 2" heel though) and red dress that felt like satin but wasn't. We spent the night chatting and i learned an awful lot about this amazing world i'd walked into. From the moment i saw her i knew this was who i am and what i wanted... oh and i absolutely wanted a pair of 4" heeled shoes!
As it got to the time when i had to reluctantly leave, she asked... no, she told me to stand up as she'd not really had a chance to look at my outfit closely. I did as she said but rather than just look, she walked around me... and used her hands as much as her eyes. Feeling her hands on my stockinged legs was a huge turn on... even more so when i felt her hands over my ass. She then told me to lift up my skirt so she could see my knickers. I immediately did as she said. My knickers were black and silky but not particularly sexy. She said they were nice, especially as they were failing to conceal my obvious intense arousal. She didn't have to pull hard on them and my rock hard cock sprang free. After looking at it for a short while she took hold of it while still standing beside me. She told me to watch as she began slowly wanking me. All of this, me being dressed with another CD i'd only met that night, both of us focused on my aching hard cock while she slowly wanked it and me holding up the skirt of my dress so that she could... and of course this being a first time for me with another CD... all meant it didn't even take a minute for me to shoot. I could hear from her reaction that she liked what she saw and she told me there was a lot more than that if i wanted to see her again.
Of course i wanted to see her again... and i did several times, but that first time will always be the one that sticks in my mind the longest. As well as her, i met several other CD's in pretty quick succession, but soon the desire to hook up with a man was becoming almost too much... so i put another advert in lonely hearts column, this time asking to hear from men only. That also got a good response... but that is for another time, if anyone wants to hear about it....
Tina xxx
Like everyone in this first-time situation i was nervous as hell. This was very different to every time i'd been dressed with my next door neighbour. I'd known him all my life and he never crossdressed, he preferred to see me do it. But unlike many, i didn't chicken out. When she answered the door and invited me in, she then gave me the chance to have a good look at her. She was mid-50's, much taller than my paltry 5'6", very slim, dressed in a black top, red PVC min-skirt, black stockings and red high heels with 4" heel. She also wore a wig and makeup... the first time i had seen a CD in person wearing either (I'd seen photos of some but hadn't worn either myself). She looked a bit intimidating... and i thought she was breathtaking. It turned out she was a bit of a domme, but not an actual dominatrix or anything like that, more like she was very assertive. To this day that is something i really like in any men i meet up with.
Our meet was mainly social, which is what had been arranged since she knew i was new to all of this, but once i'd changed into the outfit i'd brought with me, i could feel that same sexually charged atmosphere that i felt with my neighbour. Compared to her, i dressed rather conservatively, black lace stockings, black heels (only 2" heel though) and red dress that felt like satin but wasn't. We spent the night chatting and i learned an awful lot about this amazing world i'd walked into. From the moment i saw her i knew this was who i am and what i wanted... oh and i absolutely wanted a pair of 4" heeled shoes!
As it got to the time when i had to reluctantly leave, she asked... no, she told me to stand up as she'd not really had a chance to look at my outfit closely. I did as she said but rather than just look, she walked around me... and used her hands as much as her eyes. Feeling her hands on my stockinged legs was a huge turn on... even more so when i felt her hands over my ass. She then told me to lift up my skirt so she could see my knickers. I immediately did as she said. My knickers were black and silky but not particularly sexy. She said they were nice, especially as they were failing to conceal my obvious intense arousal. She didn't have to pull hard on them and my rock hard cock sprang free. After looking at it for a short while she took hold of it while still standing beside me. She told me to watch as she began slowly wanking me. All of this, me being dressed with another CD i'd only met that night, both of us focused on my aching hard cock while she slowly wanked it and me holding up the skirt of my dress so that she could... and of course this being a first time for me with another CD... all meant it didn't even take a minute for me to shoot. I could hear from her reaction that she liked what she saw and she told me there was a lot more than that if i wanted to see her again.
Of course i wanted to see her again... and i did several times, but that first time will always be the one that sticks in my mind the longest. As well as her, i met several other CD's in pretty quick succession, but soon the desire to hook up with a man was becoming almost too much... so i put another advert in lonely hearts column, this time asking to hear from men only. That also got a good response... but that is for another time, if anyone wants to hear about it....
Tina xxx
4 år sedan
