The Story of Stephanie (Part 2)
So there I was. Kind of at a crossroads. I didn't know what to do with myself. The months previous, anytime I had free time on my own, I was crossdressing and going on cam getting a thrill out of men watching me. Men! That was just strange. But I didn't know what to do with myself. I really did get excitement from it. But, I knew I had to stop. I couldn't risk getting caught. So I did what I could to get it out of my mind.
Then, one fine day, things changed. My girlfriend and I were at a weird stage in our relationship. We were on and off, on and off. We didn't know what we wanted. I was only just turning 20 years old and I wasn't sure I wanted to settle down with her. I felt I had some wild oats to sow. But I kept the relationship going because I did love her.
We had been talking about our sex life, which was always good, but was certainly missing something. So my girlfriend that night decided to dress up in her best lingerie, red basque and thong set with black stockings and heels. We had unbelievable sex. Afterwards, as we were lying in bed, I asked her what it felt like wearing stockings. She said she loved how they felt on her skin. So soft and smooth. Then, out of the blue, she asked me, "D'you want to try them on?" Stunned I think is the best word to describe how I felt. "Ok" I said, almost too enthusiastically. She was about to take hers off when I said, "No, keep them on. I'll wear a different pair." So I did. I got out a pair of red hold ups. I tried to make it seem like I didn't know how to put them on, when I was practically a professional. But they were on. The whole time my penis was rock hard. I was so turned on, and even better, so was she. That was the most intense sexual experience either of us had ever had. Like I said, it was always good, but nothing compared to that. But rather that make our sex life, and relationship better, it became more of a hindrance. I wanted to do it like this every time. She started to feel like I was more turned on by this than I was of her, which to be honest, I was. It was getting to the stage were I was going off her rapidly. We'd been together since I was 16. I was coming up to my 21st birthday. I was too young for all that settling down stuff. And apart from the sex, there was nothing else to keep us from breaking up. We stayed together a while longer, then soon after my 21st birthday, it was over. I was single.
I started to live a wee bit wilder. Going out on a Friday and not coming home till Sunday. Going to parties, drinking, doing d**gs. Everything I felt I'd missed out on in my late teens. I was free! But not having someone meant I had a lot of free time on my hands, and, I missed dressing. But I had nothing. No stockings, no tights, nothing. But I decided to return to TVChix. I wanted to start again. But this time I wanted it to be different. I didn't want to be seen as some daft wee boy dressing up in his girlfriends panties. I wanted to be desired, and seen as a woman. I wanted men to want me. I decided on a name. Pretty simple, the female version of my own name. Stephanie!
I went online and had a shopping spree. Stockings, tights, a basque, a thong and a wig. I always remembered back to that episode of red shoe diaries. The woman with blonde hair. I remember how sexy she was. I wanted to look like her. So, I bought a blonde wig. I got them sent to the house, which was my mums. Trying to make up excuses for what was in the packages wasn't easy, but I was able to get away with it. Thank god for discreet packaging!
That night, I was back online, on the chat rooms, webcams and TVChix. I was dressed up in all my lingerie and I had my wig on. I felt so sexy! Like I said, I wanted to be wanted. I loved how I made men feel, but I had no thoughts in my head about ever meeting one. I wasn't interested. After all, I like women. I'm a straight man with a weird secret. A fetish! I had lots of offers though. I was inundated with them. But I didn't want to. The thought scared me! I kept thinking, "What if I do?" "What if I like it?" "What if I turn gay?" or "What if someone finds out?" So I decided, no, I'm keeping it a secret, and staying firmly in my room!
One night though, my thoughts changed. I was on cam with a guy. I was watching him watching me! He wasn't like the others. He wasn't sitting there with his cock out wanking over me. He was just watching and telling me what to do. I liked it. He asked me to do something I hadn't done before, or even thought of. He wanted me to play with my ass. And by play, I mean put things in it. My initial thoughts were "Fuck That!" Nothing goes in! I'd showed my ass off before on cam and in my pics. But he wanted me to go to the next level. Eventually, he twisted my arm. I tried it. A finger to start with. One finger in my bum as I played with my cock. It felt very weird, but it wasn't the worst feeling in the world. I started having regular chats with this man. And he kept asking me to do the same thing. Moving from one finger, to two. Then three. And getting in deeper. I was actually loving it. It felt so good. But I always felt so guilty afterwards. I felt like this was so very wrong. But I kept coming back for more.
One night, the man asked me if I had any toys. I assumed he didn't mean the He-Man figures I had as a c***d, so, no was my answer to that. I knew what he meant, but I didn't have any such thing. Why would I? But he wanted to see me using something other than my fingers. Like what though? I looked around to see what I could see. Nothing, until something caught my eye. A hairbrush. I know what your thinking! And no, not that part of it. But the handle was smooth and rounded and long. Seemed like and idea. So I went for it. He seemed pleased with it. It was very strange. I spat all over it to lubricate it and made my asshole wet and in it went. I wasn't sure at first, but after a few minutes, I started to relax and it started to feel good. Better than my fingers.
I could see he was enjoying watching. He asked me to fuck my ass with it. Harder and deeper. I was loving this. Eventually I wanked so hard I came all over the place. That was intense. It became a regular prop when I cammed at night. Not just with this man, but with others too. I loved using it. It felt so wrong, but made me so excited. But I knew I wanted more. Something I felt I should be using. I wanted a proper toy. So I went for it. Shopped online and found something. A realistic looking dildo. 8 inches long. It excited the life outta me. I bought lube to go with it. I couldn't wait for it to be delivered. I couldn't wait to show it off on cam and use it.
What was happening to me?
Why was I feeling like this?
To this day, I still don't know!
To be continued..........
Then, one fine day, things changed. My girlfriend and I were at a weird stage in our relationship. We were on and off, on and off. We didn't know what we wanted. I was only just turning 20 years old and I wasn't sure I wanted to settle down with her. I felt I had some wild oats to sow. But I kept the relationship going because I did love her.
We had been talking about our sex life, which was always good, but was certainly missing something. So my girlfriend that night decided to dress up in her best lingerie, red basque and thong set with black stockings and heels. We had unbelievable sex. Afterwards, as we were lying in bed, I asked her what it felt like wearing stockings. She said she loved how they felt on her skin. So soft and smooth. Then, out of the blue, she asked me, "D'you want to try them on?" Stunned I think is the best word to describe how I felt. "Ok" I said, almost too enthusiastically. She was about to take hers off when I said, "No, keep them on. I'll wear a different pair." So I did. I got out a pair of red hold ups. I tried to make it seem like I didn't know how to put them on, when I was practically a professional. But they were on. The whole time my penis was rock hard. I was so turned on, and even better, so was she. That was the most intense sexual experience either of us had ever had. Like I said, it was always good, but nothing compared to that. But rather that make our sex life, and relationship better, it became more of a hindrance. I wanted to do it like this every time. She started to feel like I was more turned on by this than I was of her, which to be honest, I was. It was getting to the stage were I was going off her rapidly. We'd been together since I was 16. I was coming up to my 21st birthday. I was too young for all that settling down stuff. And apart from the sex, there was nothing else to keep us from breaking up. We stayed together a while longer, then soon after my 21st birthday, it was over. I was single.
I started to live a wee bit wilder. Going out on a Friday and not coming home till Sunday. Going to parties, drinking, doing d**gs. Everything I felt I'd missed out on in my late teens. I was free! But not having someone meant I had a lot of free time on my hands, and, I missed dressing. But I had nothing. No stockings, no tights, nothing. But I decided to return to TVChix. I wanted to start again. But this time I wanted it to be different. I didn't want to be seen as some daft wee boy dressing up in his girlfriends panties. I wanted to be desired, and seen as a woman. I wanted men to want me. I decided on a name. Pretty simple, the female version of my own name. Stephanie!
I went online and had a shopping spree. Stockings, tights, a basque, a thong and a wig. I always remembered back to that episode of red shoe diaries. The woman with blonde hair. I remember how sexy she was. I wanted to look like her. So, I bought a blonde wig. I got them sent to the house, which was my mums. Trying to make up excuses for what was in the packages wasn't easy, but I was able to get away with it. Thank god for discreet packaging!
That night, I was back online, on the chat rooms, webcams and TVChix. I was dressed up in all my lingerie and I had my wig on. I felt so sexy! Like I said, I wanted to be wanted. I loved how I made men feel, but I had no thoughts in my head about ever meeting one. I wasn't interested. After all, I like women. I'm a straight man with a weird secret. A fetish! I had lots of offers though. I was inundated with them. But I didn't want to. The thought scared me! I kept thinking, "What if I do?" "What if I like it?" "What if I turn gay?" or "What if someone finds out?" So I decided, no, I'm keeping it a secret, and staying firmly in my room!
One night though, my thoughts changed. I was on cam with a guy. I was watching him watching me! He wasn't like the others. He wasn't sitting there with his cock out wanking over me. He was just watching and telling me what to do. I liked it. He asked me to do something I hadn't done before, or even thought of. He wanted me to play with my ass. And by play, I mean put things in it. My initial thoughts were "Fuck That!" Nothing goes in! I'd showed my ass off before on cam and in my pics. But he wanted me to go to the next level. Eventually, he twisted my arm. I tried it. A finger to start with. One finger in my bum as I played with my cock. It felt very weird, but it wasn't the worst feeling in the world. I started having regular chats with this man. And he kept asking me to do the same thing. Moving from one finger, to two. Then three. And getting in deeper. I was actually loving it. It felt so good. But I always felt so guilty afterwards. I felt like this was so very wrong. But I kept coming back for more.
One night, the man asked me if I had any toys. I assumed he didn't mean the He-Man figures I had as a c***d, so, no was my answer to that. I knew what he meant, but I didn't have any such thing. Why would I? But he wanted to see me using something other than my fingers. Like what though? I looked around to see what I could see. Nothing, until something caught my eye. A hairbrush. I know what your thinking! And no, not that part of it. But the handle was smooth and rounded and long. Seemed like and idea. So I went for it. He seemed pleased with it. It was very strange. I spat all over it to lubricate it and made my asshole wet and in it went. I wasn't sure at first, but after a few minutes, I started to relax and it started to feel good. Better than my fingers.
I could see he was enjoying watching. He asked me to fuck my ass with it. Harder and deeper. I was loving this. Eventually I wanked so hard I came all over the place. That was intense. It became a regular prop when I cammed at night. Not just with this man, but with others too. I loved using it. It felt so wrong, but made me so excited. But I knew I wanted more. Something I felt I should be using. I wanted a proper toy. So I went for it. Shopped online and found something. A realistic looking dildo. 8 inches long. It excited the life outta me. I bought lube to go with it. I couldn't wait for it to be delivered. I couldn't wait to show it off on cam and use it.
What was happening to me?
Why was I feeling like this?
To this day, I still don't know!
To be continued..........
5 years ago