The Story of Stephanie (Part 3)
I was at work when I got a text. It was from my mum. "There's a parcel here for you!" It read. My heart started pounding. I knew exactly what it was. My new, and first ever dildo! Thank god my mum wasn't a nosey bastard and opened it. I was excited. I couldn't wait to get home from work and see it. 5pm came and it was finally home time. Thankfully, no one was home when I got in. So no need to make excuses as to what it could be. I went straight up to my room and opened it. Holy shit! It was a lot bigger than I thought. It actually kind of scared me. But at the same time, I couldn't wait to try it. I knew I had to wait til later on to do so. When my mum has gone to bed.
After waiting what seemed like forever, she finally went to bed. Then, Stephanie came out to play! I got my dildo out and lay it on the bed. Sat the lube on my bedside table, and got changed into my lingerie and wig. I didn't want to go online that night. I wanted to try it out first. I mean, what if I didn't like it? I got the dildo and lubed it up. I put loads on. I put more on my hand and lubed up my asshole. I was ready to try it now. I was only ever used to my fingers, or the smooth, rounded end of a hairbrush. This thing was huge in comparison! At first it was hard to get in. The head part was stretching my ass to the limit. It hurt like hell and I pulled it out. I didn't know if I wanted to try again. But I did. I waited for the pain to subside. Take 2. This time it didn't hurt as much, and with a bit more of a push, the head was in and I let out a gasp. Fuck! I wasn't sure of the feeling at first, but, I went with it. Getting more used to it and pushing it in deeper. Actually, this was good! My cock was solid as a rock! This was amazing. I was fucking my ass and imagining it was a man fucking me with his real penis! This was such a turn on! I felt myself ready to cum. My asshole tightened round this b**st. And bang. Thee most intense, amazing, and explosive orgasm I've ever had.
I felt knackered! I lay there for a good five minutes recovering. Cum all over me and a big dildo in my ass. Then, it hit me! What the fuck have I just done? I panicked a bit. I got up, took the dildo out, took off all my lingerie and ran into the shower. I felt dirty. My asshole was all greasy from the lube. I didn't like this feeling. I got out the shower and went in to my bedroom. I just sat there staring into space. Why am I doing this? What is wrong with me? I'm not gay. But there I was at the time, fucking myself with a big dildo, dressed in women's lingerie and fantasising about a man fucking me! I'm a weirdo! No one must ever know about me! I got up, put my stuff in a bag, and threw it under the bed. I went to sleep that night telling myself I can't do this again.
The next day, I couldn't get it out of my head. Back and forth, I was telling myself it was wrong, but also telling myself it was amazing. But that night I decided not to try it again. After all, my ass was still sore from the night before. A few nights later, I went online. I was chatting to the man I'd been chatting to a few times in the weeks previous. I told him I'd bought the dildo. He wanted to see it. He seemed to get quite excited about it. He asked me to use it. So I did. Taking instructions from this man, imagining it was him inside me. Again, another unbelievable orgasm! I could get used to this. Now I was hooked. I was online every night. Showing off on cam to random strangers. I was also starting to build my wardrobe. More stockings, more basques, thongs, dresses. I even bought myself my first pair of heels. Stephanie was in full flow! But I still wasn't completely satisfied. I wanted to look better. I wanted to feel more feminine when I was dressed.
I wasn't a overly hairy guy, but I knew if I wanted to feel the full effects of my dressing and to feel feminine, I had to be smooth all over. So one night, I went for it. I was single so had no girlfriend to hide it from. I wasn't really sporty so it's not like any of my friends would see my legs. I shaved every inch of my legs, my ass and even my pubic hair. My chest was smooth anyway as I'd always shaved that part. So there I was, from the neck down, smooth as a baby's bottom! Wow! What a feeling that was. Right away I wanted to try my stockings over my newly smooth legs. I'll never forget that feeling. So soft, so silky and smooth. It felt so right. I dressed fully. Basque, thong, stockings, black dress and heels with my blonde wig. I stood there in front of the mirror. Even I fancied me. I felt so good. I actually, in that moment, felt like a real woman!
This felt so right.
Stephanie was who I wanted to be.
To be continued.......
After waiting what seemed like forever, she finally went to bed. Then, Stephanie came out to play! I got my dildo out and lay it on the bed. Sat the lube on my bedside table, and got changed into my lingerie and wig. I didn't want to go online that night. I wanted to try it out first. I mean, what if I didn't like it? I got the dildo and lubed it up. I put loads on. I put more on my hand and lubed up my asshole. I was ready to try it now. I was only ever used to my fingers, or the smooth, rounded end of a hairbrush. This thing was huge in comparison! At first it was hard to get in. The head part was stretching my ass to the limit. It hurt like hell and I pulled it out. I didn't know if I wanted to try again. But I did. I waited for the pain to subside. Take 2. This time it didn't hurt as much, and with a bit more of a push, the head was in and I let out a gasp. Fuck! I wasn't sure of the feeling at first, but, I went with it. Getting more used to it and pushing it in deeper. Actually, this was good! My cock was solid as a rock! This was amazing. I was fucking my ass and imagining it was a man fucking me with his real penis! This was such a turn on! I felt myself ready to cum. My asshole tightened round this b**st. And bang. Thee most intense, amazing, and explosive orgasm I've ever had.
I felt knackered! I lay there for a good five minutes recovering. Cum all over me and a big dildo in my ass. Then, it hit me! What the fuck have I just done? I panicked a bit. I got up, took the dildo out, took off all my lingerie and ran into the shower. I felt dirty. My asshole was all greasy from the lube. I didn't like this feeling. I got out the shower and went in to my bedroom. I just sat there staring into space. Why am I doing this? What is wrong with me? I'm not gay. But there I was at the time, fucking myself with a big dildo, dressed in women's lingerie and fantasising about a man fucking me! I'm a weirdo! No one must ever know about me! I got up, put my stuff in a bag, and threw it under the bed. I went to sleep that night telling myself I can't do this again.
The next day, I couldn't get it out of my head. Back and forth, I was telling myself it was wrong, but also telling myself it was amazing. But that night I decided not to try it again. After all, my ass was still sore from the night before. A few nights later, I went online. I was chatting to the man I'd been chatting to a few times in the weeks previous. I told him I'd bought the dildo. He wanted to see it. He seemed to get quite excited about it. He asked me to use it. So I did. Taking instructions from this man, imagining it was him inside me. Again, another unbelievable orgasm! I could get used to this. Now I was hooked. I was online every night. Showing off on cam to random strangers. I was also starting to build my wardrobe. More stockings, more basques, thongs, dresses. I even bought myself my first pair of heels. Stephanie was in full flow! But I still wasn't completely satisfied. I wanted to look better. I wanted to feel more feminine when I was dressed.
I wasn't a overly hairy guy, but I knew if I wanted to feel the full effects of my dressing and to feel feminine, I had to be smooth all over. So one night, I went for it. I was single so had no girlfriend to hide it from. I wasn't really sporty so it's not like any of my friends would see my legs. I shaved every inch of my legs, my ass and even my pubic hair. My chest was smooth anyway as I'd always shaved that part. So there I was, from the neck down, smooth as a baby's bottom! Wow! What a feeling that was. Right away I wanted to try my stockings over my newly smooth legs. I'll never forget that feeling. So soft, so silky and smooth. It felt so right. I dressed fully. Basque, thong, stockings, black dress and heels with my blonde wig. I stood there in front of the mirror. Even I fancied me. I felt so good. I actually, in that moment, felt like a real woman!
This felt so right.
Stephanie was who I wanted to be.
To be continued.......
5 years ago
