It has been nearly two years since my sisters caught me dressing up. Since then my mother had put me on a strict diet and gave me pills to make me into a girl. I have been transitioning slowly and now have a girly figure. I love my round ass and small soft breasts.

I now have my own wardrobe with many sexy clothes that I just love wearing. Mom has also made sure that my sisters look after me every once in a while, and they had all been really good to me.

It was just after my eighteenth birthday and Jessica decided it was a good idea if I was a true girl and had sex. Not me fucking a girl, but a big guy fucking me. I wasn’t really opposed to the idea, it, in fact, turned me on. Jessica said she has a few bisexual guy friends that would love to fuck me, but first I would have to dress more girly than I have ever dressed before.

Jessica took me to her bedroom where Tina and Haley were waiting. I loved my sisters and I had now been naked in front of them many times. Since they had caught me two years ago I have been naked or dressed up in front of them many times. I had even slept with them in the biblical sense a few times.

I was told to strip and Haley giggled when she saw how hard I was in front of them.

“Nat,” as my name was now. “I want you to wear these sexy leopard print bra and panties, I got them especially for you.”

Haley held out a small packet and handed it to me. The panties were a thong and after tucking my cock between my legs as I had done every day for the past two years, felt the string go up the crack of my ass. The bra fit perfectly, cupping my small breasts and making them look bigger than they were. My sisters all looked at me with approval.

Tina stood up and took my hand. She lifted a black lace dress that left plenty to see. She helped me step into the dress and zipped up the back. My body was clearly seen underneath the dress and the leopard print underwear looked amazing through the dress. I did look fine and I have to say that would have fucked the girl looking back at me in the mirror.

Jessica gave me a pair of shiny black heels to finish off my outfit. The whole outfit together looked amazing and I felt proud of wearing it all.

Led me by the hand to the toilet, my other sisters followed. She took out her makeup bag and laid out the contents. She spent the best part of half an hour doing my makeup, it was flawless. I looked more feminine than I already did, making my cock twitch against its flimsy covering.

Tina stood behind me and pulled all my long hair into her hand. I watched in the mirror as she deftly braided my hair into a thick braid. It looked stylish as well as sexy, it was similar to Angelina Jolie’s braid in Tomb Raider.

All three of my sisters seemed pretty pleased with the way they had dressed me up. I was pleased too and knew that whoever it was that Jessica had arranged for me to be with would love me.

The front doorbell rang, and Jessica jumped and pulled me close to her.

“That will be Jason. He’s a really cute guy but also very effeminate. He is bisexual so if you want to do anything to him, he will let. Just remember, this for you to explore your sexuality with him. Don’t be shy and if you want to take charge, just remember he’s a big guy so don’t try hitting or anything like that, because if he hits you back, he’ll knock you out.”

We all trooped downstairs, Jessica leading me by the hand. I was told to answer the door, but mom had already beaten me to it. I think Jason felt a bit uncomfortable telling mom that he was there to fuck her son, but mom always knew how to put people at ease.

Jason was tall, about six feet one. He wasn’t fat, but by no means skinny. He had muscles and at the same time, he was soft and almost ladylike. He wore loose fitting clothes and, in an attempt, to look manlier he had a Mohawk. He was pretty, and he seemed to shift when he saw me. He drawled slightly that made my cock twitch. I walked over to him and in front of my sisters and mother gave him a peck on the lips.

Mom seemed to usher my sisters out the room and I knew at least Jessica would be back to watch. As my mind wandered, Jason’s hands roamed my body and he seemed to find my treasure between my legs.

Without thinking or asking Jason pulled my cock free and wrapped his lips around it. It was the first time a guy touched me, let alone sucked me. It felt amazing and he seemed to grip my ass as he sucked and slurped on my dick. I slid my hand through his hair and started to move my ass. He seemed to like it and moaned his approval. I heard the door creak and saw Jessica sneak in. She gave me the thumbs up sign and took a seat in the corner of the room.

I started to lift my dress, but Jason took my hands away.

“Keep it on, you look so sexy all dressed up.”

I smiled and kissed him. He pulled me close and held me in his bearlike grip. He let go of me and stripped off. He had shaven his whole body and his cock, which wasn’t that big was bald. I took my seat on the couch and wrapped my hand around his hard cock. I could feel the blood pumping through his cock and I measured it in my hand.

Trying not to seem obvious I stroked his cock, measuring its length in my hand. Then I took his cock into my mouth as I wrapped my hand around my own cock. I made it seem like I was sucking him off and jerking because I was horny. I was horny, but really, I couldn’t resist comparing how large our cocks were, mine was bigger.

I sucked on his cock as best as I could, rolling my tongue around his bulbous head. He seemed to groan loudly, digging his finger into my braided hair and holding my head. He seemed to really enjoy me sucking him off and he started saying naughty things to me that really turned me on.

He pushed my head away and made me get onto all fours on the couch. He pulled my panties right down and buried his face in my ass. His tongue lapped at my butthole, making me squirm. As he licked my ass he jerked my cock.

I felt him move and take up position behind me when Jessica stopped him.

“Oh no, not like that Jason. If you’re going to fuck her, you’re going to wear a condom. No condom, no ass.”

Jason gave a sort of grunt as Jessica handed him a small red packet. I watched as Jason ripped it open and pulled out the condom from inside. I watched as he pulled it on and took up position once more.

I felt him spread my ass and slowly push his cock up my butt. Since I started dressing up I had been experimenting with putting things up my ass, but I never had a real cock up my ass before. He wrapped his arms around my waist as he started to slowly fuck me. I could feel his chest against my back as his cock seemed to slide easily in and out my butt.

He slowly started to pick up speed, slamming his cock as deep as he could. His grunts and whimpers turned me on so much that I had to jerk myself off. He seemed to pause, then grunted loudly as I felt the condom expand in my ass. I was a bit disappointed as he pulled out his cock and pulled off the used condom.

He sat back exhausted and I was left slightly unsatisfied.

“Okay, my turn.”

He looked at me like I was mad, but I wasn’t having any of it. I turned him over and spread his ass. Once again Jessica interjected. She held a condom in her hand and lovingly rolled it onto my cock. She kissed me on the cheek and gave me a pat on the ass.

Jason lay back on the couch, his legs spread, his ass open for me. I pushed my cock into his ass slowly, him being the first guy I ever had sex with. He grunted as I slid my cock in as deep as I could. It was warm and tight, like I was his first guy too. I held the back of his thighs as I started to build up a rhythm. His ass felt so good that I was soon pounding him as hard and fast as I could. His grunts and groans only made me try to fuck him harder.

Jason pushed me back, making my cock fall out his ass. I watched him get on all fours, shaking his ass at me. I took up position behind him and pushed my cock back in his ass. I grabbed his hips and started to slam my cock inside him as hard as I could. He grunted loudly, making me fuck him harder. I groaned loudly as I fucked him, knowing I wouldn’t last long.

I felt a hand on my ass and Jessica seemed to force to slow down.

“Relax, Nat. If you feel like you are going to cum, pull your cock out and take off the condom, then cum all over Jason’s ass. I want to see you cream all over his butt.”

I giggled and continued to fuck him as hard as I could. I knew I was close, but I it felt so good that I couldn’t pull out. At the last second, I pulled my cock out and pulled off the condom quickly. I pulled it off just in time as my cock seemed to explode, shooting cum all over Jason’s ass and back. I couldn’t stop cumming as my cock twitched and my body shook.

I fell onto the floor, panting and trying to catch my breath. Jason seemed to enjoy it and turned around and gave me a peck on the lips.

“Thanks cutie, that was amazing. Maybe I can come by again and we can have another round?”

I blushed, and Jessica seemed to interject once again.

“Thanks, Jason. If you want a shower there is a bathroom down the hall. For now, I need to take Nat to get washed and cleaned up.”

Jessica took me by the hand and led me upstairs. She led me into the bathroom when she helped me strip off. She stripped off too and made me stand still as she untied my hair.

She led me into the shower where she turned on the water and started to wash me down. She took care to wash my every crevice. Her finger penetrated my ass as she stroked my cock, making me quiver all over again. She knew what she was doing and soon have me Cummings all over her hand.

She washed me thoroughly, making sure every inch of my body was clean. After our shower, she dried me off and pulled me close and gave me a peck on the lips.

“Nat, you are now my little sister and as the youngest, I have to look out for you. That means only the boys I pick for you are good enough, and I know there are many girls, including our sisters that would love to sleep with you. I just want to make sure you aren’t taken advantage of.”

She gave me a pat on the butt and told me to go to my room. Once in my room, I saw Haley lying there on my bed, naked. She gave me a wicked grin and patter the bed next to her.