I am 48 now, but this story takes place when I was a teenager. It is autobiographical.
This story is intended only for readers 18 and older.
This is my first story, so feedback from readers would be greatly appreciated!
From Brother to Lover
Growing up in the 1960s and 1970s, I was a pretty normal, athletic kid. I was small for my age, always at the front of the line in school. My eldest brother, 4 years older than me, was much bigger and tougher. In spite of his bullying of me, I always admired him--maybe a bit too much.
I remember that when I was 6 or 7, we would sometimes go under the covers in his bed. He would hold me, we'd snuggle and hug--I think we even kissed once or twice. I never really thought much about it . . . till later. I always just did what Bill said. I wanted to please him, but I also feared him.
People always said that I looked just like my mother and women were always envious of my curly blonde hair. Those comments, combined with my small stature, may have played a role in my increasing interest in my mother's clothing, shoes, and lingerie as a child. When I turned 12, I remember becoming particularly fascinated with my mother's slips and hose. I began to try them on, along with her shiny black pumps, when no one else was home and fantasize about being kissed and fondled by my brother Bill or one of my friends. Nothing really happened and I dropped the game--concerned that my mother would notice my dried pre-cum on her pantyhose. However, I continued to be interested in my feminine side.
When I was just beginning high school, my brother left for college. Bill had always been very popular with the girls--I alternated between being envious of his success and popularity and envying the girls that got to make out with him. At college, it seemed like he once again hit it off immediately with the girls. When he came home for a weekend, I could see why--He seemed much more mature and debonair to me (I had already thought he was extremely handsome), even though he had been away only a few weeks. During his visit, I found myself asking him all kinds of questions about his college life and social relationships because I wanted to let him know how impressed I was with him--I realized at one point that it was kind of like I was flirting with him.
After that, I started borrowing my mother's slips and stockings again when I was home alone. The difference now was that my fantasy was always about seducing Bill and becoming his girl. I imagined him kissing and hugging me, and, as I masturbated, I imagined what it would be like to suck his cock. I would stick my finger up my ass and imagine Bill fucking me, with my stockinged legs up on his shoulders, as we kissed. I began writing Bill letters, telling him about my days at school and how much I missed him and was looking forward to him coming home for Christmas. Although I never "came out" to him, I thought the letters were very "girly." I really wanted him to begin to think of me that way. He didn't write back much, but I continued to write every day. My parents may have thought it was strange, but they seemed very happy that somebody was keeping him connected to home.
Finally, Bill's semester ended and he came home on December 12th--I still remember the date because I had looked forward to it for weeks! I fawned all over him and gave him a big, kind of lingering hug (and seemed to get away with it). By this point, I had worked myself up into a state of being head-over-heels in love with Bill and I just hung around him all evening (neglecting my homework), listening to him telling my parents about his experiences during his first semester of college. When Bill talked to me, he mainly asked about a girl that went to my high school that he had been involved with the previous summer. I went to bed very horny--hoping against hope that Bill would come into my room to talk. I wore only my pajama tops to bed (having shaved what little hair I had on my legs for him), but he never appeared. I heard his bedroom door close and it never re-opened, so I finally fell asleep.
I didn't see Bill the next morning--he slept in and I had school. I was very depressed and distracted the whole day, trying to think of subtle (Yeah, right!) ways I might reveal my true feelings to him and imagining how he would be likely to react (probably not well). As the school day ended, I was shocked to walk outside and see Bill there! My heart soared! Then I saw that he was talking to Sue (his former girlfriend)--rekindling for his month at home, no doubt. Nevertheless, I went up to them and gave Bill a very hearty greeting. He didn't seem happy and Sue didn't say anything to me. Bill said he was going to ride home with Sue. It was obvious that I wasn't being invited, so I said that I'd go and take my usual bus home and see him later.
I guess Sue was not as responsive as Bill would have liked (Thanks, Sue!) because while I was sitting on the bus waiting for it to pull out I saw him outside the bus looking for me. I tried to wave to tell him to get on. He didn't see me in time and the bus pulled away. I saw him start walking toward the corner and knew he was going to walk all the way home (over 2 miles). I got off at the very first stop and walked back to meet him. He seemed happy to see me and we started the long walk home together, having a nice conversation. Sue had told him she had a new boyfriend, leaving Bill with no good prospects for feminine companionship during his break. I was kind of bubbly, talking about the approaching holidays and how nice it was to get to walk home with Bill.
As we approached the wooded park we'd walk through on the way to our house, I decided to "Go for it"! I said, "You know, Bill, I've always admired you an awful lot, maybe even more than a brother should--since way back when we used to snuggle together under your covers."
He gave me a strange look; he probably didn't even remember it. "What do you mean?" Bill said.
I said, "It's hard to explain, but, if you don't mind, we can find a private spot off the path and I'll show you." I took his hand. He gave me a strange look, but didn't resist. I led him into the woods (trying to walk with all the wiggle I could muster in my boy clothes and sneakers) until we found a small clearing hidden from both the path we'd left and the street outside the park. I stopped and faced him, still holding his hand, and said "I've always loved you as a brother, Bill, but for a long time now I've wished I could love you like your girlfriends do." I put my arms around his neck, stood on tiptoes and kissed him lightly on the cheek. I gave him a hug and was thrilled when he didn't recoil. Of course, he didn't hug back either.
Bill said, "I thought you were getting awfully girly! You know, I kind of like you like this. Go ahead and show me what you can do for me, sissy girl." I tilted my head up to look into his eyes and smiled in my most feminine manner. He said, "This is how I start with a REAL girl." I was shocked when he bent his head toward me and kissed me on the lips! (I realized in a flash he must have been left INCREDIBLY horny by Sue's rejection--he must have met her at school hoping to get some action. I had apparently picked the perfect time to make my move!)
My head was just swimming after our kiss--I felt like I might faint, but, not wanting to lose the moment, I moved my hand to the front of his jeans and felt his impressive erection. "Now I'll show you just how much I love you!" I dropped to my knees and immediately felt a little steadier on the ground, unzipped his zipper, and pulled his jeans down, exposing his tighty-whities. I rubbed my mouth and face against his underwear, feeling his growing erection through the thin fabric. I suddenly realized that my hands felt cold, so I looked up at him, blew on my hands, smiled, and slowly pulled his underwear down--taking care to lift the waistband over his cock. As it appeared, I immediately planted a soft kiss on the head and was rewarded with my first taste of another man's precum. I eased his underwear down to his ankles and stared lovingly at his cock, which was pointing straight at my mouth. I remember thinking that it was the most beautiful, perfect thing I had ever seen. It was much thicker and larger than mine. (I remember thinking that this showed that I really should be his girl, rather than his brother.) I grasped it gently with my left hand and looked up at him (seductively, I hoped) as I brought it to my mouth. I kissed the tip again, then pumped the shaft with my hand. A large bubble of precum appeared--I smeared it on my lips as I emitted a VERY happy "MMMMMMMM"!
I glanced up at Bill again as I tried to sexily take my first cock between my lips and into my mouth. The sensation of that velvety, soft smoothness was just incredible! I knew immediately I had to have more of this! I opened my mouth wide, being careful to cover my teeth, and began to slide Bill's cock further into my mouth, my tongue serving as the floor along which his cock slid, tasting him as each inch came in. When I had most of him in my mouth it felt so wonderful I just let out a full-mouthed "MMMMMM!" I thought, "Wow! I'm finally a cocksucker! I can't believe Bill is letting me do this!" I felt incredibly girlish and sexy--after all, the only pictures I had seen of oral sex involved beautiful women sucking manly studs.
I very quickly realized that I had better get back to the business of pleasing Bill. I backed my mouth off of his cock, trying to swirl my tongue around the shaft as it exited, until only the head remained inside my mouth. He took over now--shoving his manhood back into my mouth. I hung on to his hips for dear life, my eyes watering and my nose clogging, as he started a rhythm of fucking my mouth--forcing me to take him nearly into my throat on each thrust. Although I realized there was much about this process I needed to learn, I was pleased that Bill seemed so excited--his penis seemed much larger than when we'd started and he was saying things like "Take it, Baby! That's right, suck it little girl! Suck your man's big cock!" I loved having him talk dirty to me, especially since he referred to me as a girl!
It just occured to me that maybe I should be trying to touch or stroke his balls, when he said, "Take it, Bitch!" and began to cum. I was afraid I might be overwhelmed, but most of the first shots went straight down my throat. It was only when he finally loosened his grip on my head that I was able to back off a bit and taste his cum on my tongue. I LOVED it! I continued to suck and stroke his cock--I never wanted this incredibly sexy, intimate moment to end. I WAS BILL'S GIRL!!!
His attitude changed quickly after that. He pulled up his pants and said "Let's get out of here!", causing me to nearly fall over backwards. I caught my balance and was left kneeling on the ground. I hurriedly gathered my things and caught up with him. I wanted to take his hand again, but didn't dare. We walked in silence for a long time, but just before we reached the park entrance (near our home), Bill said "That really felt good. Thanks." I didn't say anything--just gave him what I hoped was my most feminine smile.
When we reached the house, we both acted completely normally. I tried not to catch his eye--because I knew that I could NEVER look at him in the same brotherly way again--he was my secret lover and, I hoped, my boyfriend!
I looked forward to going to bed and hoped I might finally have a visitor to my room that night.