Shortly after my mother passed away, my younger sister came to live with me. I was only twenty-one and just starting out myself, juggling a job, adult school and so many bills I barely managed to make ends meet. I'd given sis the chance to just live with our aunt, who had a nice home and plenty of everything. But she insisted on living with her big brother and so I wasn't going to tell her she couldn't.
In the end I was kind of glad she did. Just the thought of mom being gone made the world seem emptier. It was nice knowing I wasn't alone in it.
Sis and I shared a little 1-bedroom apartment. I tried to give her the bedroom, but she refused it and crashed in the living room every night. Sometimes her friends would visit. She had some pretty interesting pals from school. I got along ok with all of them.
Her best friend was a pretty blonde girl named Drew. They seemed to be inseperable and Drew spent a lot of time at the apartment. Sometimes even if sis wasn't home, Drew would come by and just wait for her.
I have to admit, I thought Drew was kind of hot. Although whenever I checked her out I felt like a dirty old man. Drew was my sister's age, sixteen.
I didn't have a dining room table, so I used the apartment's tiny dining room area for my weight bench and I'd work out there, lifting weights and listening to music. I guess Drew liked me a little too, cause I'd catch her checking me out all the time. Everytime I'd catch her, she'd blush and turn away a shy smile on her face.
Eventually a day came when I was really horny and maybe my little head got the best of my big head because I really started flirting with Drew. She flushed and smiled and flirted back, and before I knew it I was tickling her on the couch and she was giggling and curling up. She was in skinny jeans and a top that only covered her small chest, exposing her toned tummy and belly ring. The playful tickling led to my kissing her.
Drew looked up at me and smiled the prettiest smile I'd ever seen, her clear blue eyes fairly sparkling. She kissed me back and that's all it took. We lay there on the couch making out with everything we had. I got so hard, my cock throbbed. I wanted her so bad. So I sat up and unzipped my jeans and pulled my cock out. Drew stared at it, and complimented its thickness and size. Ran one slim hand up and down the shaft.
I asked her for a blowjob and so she got on her knees in front of me on the couch and gave me head, my right hand clutching a handful of corn silk blonde hair as my cock slid in and out of her mouth, her skilled tongue sending indescribable sensations through me. I blew a load in her mouth and she swallowed. No sooner had we finished, then my sister got home from the library. Drew and I pretended nothing had happened.
Our secret makeout sessions continued off and on for about a month. Eventually I wanted to fuck her. She kept putting me off, and I got more and more frustrated eventually blowing up and telling her to just forget about us. So she relented.
That's when I found out, Drew had been a boy all along. Drew was a young transsexual who identified as female. Standing naked before me I could see a long, lean body with a flat chest, toned belly and a smallish cock and balls, clean shaven.
I'm not sure which of us was more surprised by the fact that I didn't care. I made love to Drew anyway. We lay in my bed and kissed, our hands exploring each others bodies and eventually I lubed up and entered him from behind, riding him gently because it was his first time and then filling him with my cum while he jacked himself off furiously.
Drew and I continued to have sex and see one another secretly for a few more months (because we both knew my sister wouldn't approve - she was jealous of her friends and would have hated the fact that I had become closer to Drew than she was) and then, just like that he was gone. Just another teen with his first driver's license, hitting the road a little before he was fully prepared. I didn't hold anything against the lady that collided with him. By all reports, he was the one who pulled out into traffic too soon. But I miss him.
I'm just glad for a few months we were happy together.