My first as a Tranny

by Angie K

10 Oct 2015 5010 readers Score 8.0 (50 votes) PDF Mobi ePub Txt


My name is Angie. I am 35 yrs old. I am 5'6", slender, with wide hips. Several girls I had dated said they wished they had hips like mine. I have long brown hair and green eyes. I have always had very little body hair.  I have a small cock that grows to 5 inches when erect. I had my testicles removed when I was 23.

On the night, we graduated High school, My friend (and soon to be lover), Dave, and I went to an adult theatre. We watched several videos. I noticed we both seemed to really like the Tranny videos. Dave thought fucking a tranny would be really fun. I agreed, but I was thinking I would like to be fucked like the tranny.

Dave's 19th birthday was coming up soon. His folks and mine were going to be out of town for a couple of weeks, then. I asked if he wanted to come over to my house and celebrate.

I spent the next few days picking out sexy clothes, high heels, and jewelry. I also learned how to apply lipstick and make-up. I also rented some tranny DVDs.

When he arrived, I told him I needed to clean up and then we would party. I also suggested he put on a DVD. I then went up to my room to get ready.

After about 20 minutes, I came downstairs. His back was to me, but I could see him stroking his cock. I nearly turned around when I saw his cock: it was longer and thicker than mine. I didn't know how I could take it!

I decide to go ahead and stepped around the couch. His jaw nearly dropped to the floor. He asked, "Andrew?" I replied, I'm Angie, and I want you." I sat across his lap and proceeded to give him a passionate kiss. He wrapped his arms around me and pulled me closer. he pulled my top down and started fondling my nipple. I moaned softly. He then put his mouth on it and started kissing and nibbling. I held his head against my breast and moaned louder.

He stopped and told me how hot I looked and that he wanted to fuck me. I replied, "that's the idea!" I then got on my knees and started sucking his cock. I couldn't get it in far. He quickly dumped his load in my mouth, spilling some on my face. I looked up at him and used my fingers to clean my face and licked his cum off them.

He had an embarrassed look on his face and apologized for coming so soon. I said, "Don't worry. Keep watching the DVD." I went back down on him and sucked him until got hard again. "Now it's time to fuck me!" I said.

I turned around and face the TV so we could both watch. I felt his fingers lubing my asshole. I felt his cock pushing against my tight hole. I knew it was going to hurt, but I didn't expect it to hurt as much as it did. Dave was starting to pull out, but I hollered, " No! Keep pushing!" I whimpered as he continued fucking. He grabbed my hips and started pumping harder as his orgasm neared. He came after a few minutes. After he pulled out, I reached behind me and gathered some of his cum on my fingers and then licked tem clean.

He apologized for hurting me, but I noticed he still had a hard-on. I asked how he liked his birthday present. He said it was the best present he had ever received. I Replied, "it's not over yet!" I turned around and presented my ass to him said, I want you to fuck me until you are completely drained!"

The second time still hurt, but not as badly. He fucked me three more times that night and  several times daily over the next couple of weeks.

We stayed together for a couple of years, but he wasn't the boyfriend I thought I knew and wanted.

Till next time,

Angie