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Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert. He said to me, “A true sissy...
Added 17 Oct 2013 | Category Crossdressing
| Votes 13 | Avg Score 4.31
| Views 6,210
| 3 Comments
As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...
Added 26 Jul 2013 | Category Crossdressing
| Votes 8 | Avg Score 4.88
| Views 3,459
| 4 Comments
Greg and I had resumed our relationship as normal after my experience at Mistress Amber's. I was enjoying being his girlfriend. He treated me so nicely, and we enjoyed our time together. It was the most intense sex life I had ever had with anyone. For the most part he enjoyed being the dominant one, and he was happy to make me his little fucktoy after a nice night out. But it was that line...
Added 15 Jun 2013 | Category Crossdressing
| Votes 7 | Avg Score 4.71
| Views 5,808
| 2 Comments
It had been a while since I started the hormones, and I couldn't have been happier. I was looking and feeling more womanly than I ever thought possible. It brought me a new confidence when I was in public, and made me feel so much sexier, and girly when I was in the bedroom. My breasts weren't that big, but they were growing over time. I had a nice handful, and Greg said he loved to suck on...
Added 20 May 2013 | Category Crossdressing
| Votes 13 | Avg Score 4.69
| Views 7,025
| 5 Comments
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 13 May 2013 | Category Crossdressing
| Votes 19 | Avg Score 4.47
| Views 6,528
| 5 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 18 | Avg Score 4.72
| Views 5,125
| 10 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 14 Jan 2013 | Category Crossdressing
| Votes 13 | Avg Score 4.38
| Views 6,038
| 6 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 03 Jan 2013 | Category Crossdressing
| Votes 28 | Avg Score 4.58
| Views 6,733
| 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 15 | Avg Score 4.47
| Views 4,467
| 8 Comments
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