First time

Was a short boy and very into crossdressing. For a few short years, my step-sister who was older and I were about the same size. It was wrong to do without her permission, but I loved wearing her skirts and panties and did so any chance I could secretly. I didn't want anyone knowing I preferred wearing girl's clothes, and was too afraid to ask for some of my own.

My favorite times were the days she had practice and was gone for a few hours. I had her clothes all to myself and could dress up completely in them and sometimes also wear her makeup and perfume. I got also quite good at walking in her heels. My favorite outfit to wear was a sleeveless turtleneck and pleated skirt. With some padding and makeup, I would pretend I was a real girl and wondered if I looked pretty.

Soon I began not only dressing up but masturbating as well. Had some weird fantasies. Sometimes, while I was dressed up, I'd jack off while fantasizing about being a real girl being fucked by a cute guy while dressed as a girl.

Curious about anal and used her tampons anally sometimes in a darker fantasy that I was being taken by an unknown stranger who takes my virginity and leaves pregnant.

Would sometimes wear pads in the panties, so could masturbate and have it catch the mess. I'd crouch down and masturbate myself to orgasm.

I found a shorter skirt to wear of hers. As she was getting wider hips and bigger ass, her panties became looser on me, but I still loved them.

I crouched down to masturbate in the pad and her dog started becoming interested. He jumped on my back and went crazy. For a moment I was shocked, but felt naughty and let him. He had a tight grip and I could feel his prick through the panties stabbing around and hitting at my asshole. I was enjoying it and let it happen protected by her panties. He moved around and worked himself until he was finally able to get his prick up one of the loose leg openings and inside me. As soon as he was in, he started fucking me hard. He wasn't gentle at all, so it hurt at first, but soon was feeling okay. He didn't feel big, and I was curious was getting fucked was like from my fantasies, so I relaxed and let him fuck me. His warm prick sliding inside me started feeling really good, much better than her cold tampon. I'd have to let him do this again.

I felt strange like I was stuffed, and he stopped and relaxed his grip. I thought he was finished, but instead of pulling out and dismounting, he only stepped off my back and turned and I felt something turning inside me as he was turning.

We were stuck together! His prick was still inside me and felt huge. I tried to push him out, but he was locked in solidly. I then remembered hearing dogs got stuck together sometimes when they fucked, and I was his bitch that day.

He shifted and whined. The knot inside me pulsed and I felt warmth. He was coming inside me. He kept pulling and moving and coming and it was feeling good even though I hadn't even gotten to masturbate yet.

Finally, I felt myself building up to something as his knot rubbed my insides. I was unprepared when it finally happened and moaned as I felt my ass clamp down on his prick as I had a huge orgasm. It made me feel all warm inside and felt wonderful. My other orgasms from masturbating my own prick didn't compare to what her dog had given me by fucking me. He had given me an orgasm anally. Before we separated, he gave me another big orgasm, but when it came, I also blew my load in the pad soaking it with a smaller orgasm.

When he finally was small enough to pull out, I was weak-kneed. I saw his wonderful prick. It looked about the size of the tampon starting out, but was bigger than mine. I was a mess with his come leaking out of me. Having been stuck together for so long, my hole felt sore.

It hit me that I'd had just had sex for the first time and was still on a high with the feeling from those strong orgasms that lasted a long time. Masturbating was okay, but getting fucked to those strong orgasms felt much better, and I wanted to feel those again.

I let her dog fuck me many times after that trying missionary, but preferring getting mounted with him on my back. When dressed up in my favorite outfit, I was a complete whore for her dog's prick.

Her dog was still out fucking bitches in addition to fucking me, but thankfully none had any diseases that I know of, so avoided having to explain to the doctor why I had a dog only STI back there.

I still miss him sometimes.