Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun...

Added 12 May 2013 | Category Crossdressing | Votes 14 | Avg Score 4.43 | Views 2,482 | 4 Comments

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you....

Added 05 May 2013 | Category Crossdressing | Votes 14 | Avg Score 4.79 | Views 2,402 | 7 Comments

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on. First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It...

Added 11 Jan 2013 | Category Crossdressing | Votes 13 | Avg Score 4.38 | Views 4,627 | 7 Comments

A few months after having my first date, I was feeling kind of anxious about not really allowing myself to go further. I had plenty of guys interested, but I wasn't really ready to make that move. I had been talking to this sexy college boy for a few weeks, but we couldn't set up anything solid. We finally nailed down a date, but he had some last minute issue come up, and had to cancel. I...

Added 02 Jan 2013 | Category Crossdressing | Votes 23 | Avg Score 4.67 | Views 4,573 | 8 Comments

This is a memoir of my first time meeting a man. I'd been crossdressing for many years. I had many fun nights dressing up and playing with my toys but I wanted something more. I liked to get on the phone with guys and play around. I had my favorite toys to use, especially my eight inch dildo and my butt plug. I really got into my phone sessions, but I felt like I wanted to go further. ...

Added 02 Jan 2013 | Category Crossdressing | Votes 13 | Avg Score 4.62 | Views 2,848 | 8 Comments