Turned Into A Sissy Boi - Sex Stories

Turned Into A Sissy Boi

It started innocently enough. I was spending another weekend with my girlfriend and we were in bed late one Saturday night. She had just cum and I was rapidly on my way there. I was on top pumping in and out of her. She snaked her hand back and started lightly brushing her fingertips around my butt-hole. I let out one moan, then another, and on the third one, I shot my load inside her. It was one of the best orgasms of my life! “Oh, you liked when I played around with your backdoor, huh?” she said a moment later with a teasing smile. “I sure did! It was great!” I responded. Looking back on it, little did I realize exactly where this was going to lead! My girlfriend Jenny was about 5’ 10” tall (one inch shorter than me when she didn’t wear heels), shoulder length dark brown hair, B-cup boobs and a killer ass! She was very pretty, and I thought myself quite lucky to be dating her. She was also four years older than I was. I’m 5’ 11”, thin, not much facial or body hair, and have a 5” cock. I was a little worried about the size of my penis, as I really wanted to please Jenny in bed. She always told me not to worry about it, as she was satisfied. Each time we made love after that one night, she always diddled with my asshole. First it was only around the rim. Then, she started putting a finger inside my ass, and then two. And, we were making love more often. I was in heaven! I’d make sure she would cum, and then she’d reach back and start playing with my eager hole. Always within ...

... a minute of her fingers penetrating my pucker, I’d explode. It was great! Jenny started insisting on my having an enema before bedtime. I didn’t argue that much. Besides, as the warm soapy water flowed up my fanny, she would gently stroke my erection. She was great at keeping me on the edge. Between her hands and the nozzle up my butt, I came close to cumming a couple of time. She would also tease me by moving the nozzle in and out. I would be moaning by the time the bag was empty and literally did anything she told me too once the water was expelled and she led me by the dick into the bedroom. Little did I know what was in store. I got to her place one evening, and she opened the door wearing a push-up bra, garter-belt, stockings, and a wicked grin. “I have an interesting evening planned for us, baby” she said. I just stared at her with a stupid grin on my face. She gave me a passionate kiss, then brought me into the living room, and stripped me. Grabbing my throbbing member, she led me into the bathroom. I immediately dropped to my hands and knees, naked butt held high in the air. “My, but you’re such a good boy”, she said with a chuckle. She smacked my bottom a couple of times before she lubed my asshole. I arched my back and pressed back against her finger as she slid it up in me. “You really like it when I fuck your ass with my finger, don’t you?” she said with a smile. “Oh yeah” I sighed. “I love everything you do to me honey!” “Good. Let’s clean out this nasty ass of ...