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Saving Benny
I don't know what made me go a different way that day, but everything changed because of it. I was something of a loner and most people in my small town high school left me alone. I was 18, with longish dark hair and a toned, muscular body. I usually wore a leather biker jacket and engineer boots and played in a rock band in my spare time. Because my house wasn't too far away, I sometimes walked home from school, even though it was my senior year and I did have a car. It was just one of my eccentricities that people had gotten used to. That day instead of the normal route, I took a little-known path through the woods thinking I'd enjoy the solitary time with my thoughts. Instead I was surprised to hear yelling and sounds of distress.
"I'm gonna give you something to scream about you little faggot piece of shit"
I saw Jason, a punk who dressed like a thug and always had a nasty comment for everyone, holding someone in some sort of headlock. He then pushed him down to the ground and kicked him. As I got closer I saw it was Benny, and he was screaming for help. I knew him in passing from an art class we had had together even though he was only a freshman and he seemed like a nice guy. He was also very obviously 100% gay and gorillas like Jason usually gave him trouble. Some people might think it wasn't their problem and just walk away, but I wasn't about to stand for it.
"Leave him alone, asshole," I told Jason, "he didn't do anything to you".
"What do you care if this little queer gets the shit beat out of him?" He responded. "Just get the fuck out of here or I'll..."
"You'll what?" I asked as I lifted him off the ground and shoved him into a tree. "I think you'd better get out of here unless you want more of the same."
He ran as quickly as he could, coughing because the breath had been knocked out of him and trying to curse me as he went. I extended my hand to help Benny up and asked him if he was alright.
"Yeah, thanks to you," he said, as he brushed his shoulder length blonde curls out of his face and brushed leaves off his clothes. He had tears in his eyes, which were bright blue with long lashes like a girl. "But you shouldn't have done that. Now they'll think you're a queer too and you'll never hear the end of it".
"I don't care," I told him as we walked together farther into the forest. "I'd like to see them try to attack me. Most of his kind are afraid of me anyway. I broke his friend Tommy's nose when he tried to give me shit about taking art classes. He was so ashamed he didn't even tell anyone how he broke it. By the way, you're paintings are beautiful. I've always wanted to tell you that and have never gotten a chance before."
His eyes lit up, there is no other word for it, and we discussed art and music for so long we wandered onto a side path and ended up at the top of a hill where we had a great view of our neighborhood beneath and of the road the school was on on the other. I found out that he had gone to all of my band's shows and was a big admirer of our music. I watched him talking about us and looking at me and I became conscious that the look in his eyes was the same one I've gotten from some of our female fans before. Even the way he stands and walks with his hips swaying is the same. I started to get aroused looking at him in his tight skinny jeans and even tighter low-cut shirt. He was only about 5 foot 2, and slender without any prominent muscles. His face was completely hairless and he wore a fruity cologne or perfume of some sort. We were about to go home and he thanked me again for helping him, hugged me and gave me a kiss on the cheek.
"I'm sorry" he said as he nervously stepped back. He then took off through the woods and went home.
Over the next few weeks we ran into each other occasionally and were friendly but rarely got a chance to talk. Then one day he came to a concert where my band was playing and I invited him to join us for the after party at a friend's house. There were several very hot girls there but somehow I was too caught up in talking to Benny to notice that each of them was hooking up with my band mates or other guys. By the time everyone went home or went to bed, only Benny and I were left alone and feeling slightly drunk. We headed back to the room where I was staying and kept talking and joking for a while. Benny laughed at a joke I made and fell back to lean against me. The sweet smell of his silky blonde hair hit me and I unconsciously put my arm around him. I looked closely at his face, and he was wearing some light makeup and a little glitter. He smiled and I found my cock getting hard as I wondered what he would look like naked. Just then, he leaned forward and kissed me softly on the lips.
"Oh my God, I'm so sorry!" he said as he jumped up and stepped away from me.
"Don't be" I said as I pulled him closer. I then took it all one step further and kissed him full on the lips. He let out a startled little gasp and hugged me closer so I could feel his hard cock through his pants. I pulled off his shirt and discovered that his chest and back were just as smooth as his face. I caressed his smooth skin, my curiosity increased. Even at my young age, I had already learned to enjoy anal sex with girls, and on two separate occasions, I'd experienced awkward blowjobs from guys. But this pretty blonde boy was something new for me and I really wanted to explore his body. I stripped to my jeans and he tantalizingly slipped out of his pants to reveal long, smooth legs and an ass to die for, covered only in thong underwear. He smiled and made come here motions at me, a look of longing in his eyes.
I took him in my arms and kissed him again, exploring his mouth with my tongue as I explored his body with my eager hands, caressing the smooth, soft skin of his ass. It was round and very feminine in shape, even though the rest of his body had fewer curves than I was used to. I kissed his neck and licked my way down to his erect nipples, exploring his flat chest and running my fingers into the cleft between his ass cheeks while he sighed with pleasure. I was curious but also alarmed at what I was doing, yet I couldn't stop myself. I knew I had to take it all yet another step further or I'd regret it for the rest of my life. I gently laid him down on the bed and stripped out of my jeans and underwear.
My six inches of thick, hard uncut cock sprang to attention as I looked at him with desire. He licked his lips as he took my manhood in his hands and pulled me down to the bed with him. When I looked down at his beautiful, feminine face and all those blonde locks spread out on the pillow, I was determined to have this boy and fuck him until we were both exhausted. I kissed him passionately one more time and then sat back to remove his thong and see him in all his naked glory. As I slipped it off, I received a shock when a huge uncut dick at least eight inches long was revealed. There was something extremely erotic about the soft girlish face, androgynous body, and massive hard cock all combined in one individual. I caressed it till it was not only hard but gleaming with precum and then I fell back on top of him, kissing him furiously as we masturbated each other and our bodies rubbed together. Our cocks touched and we started fucking into each other, slowly and sensuously, while our tongues danced together and my fingers explored his ass. I reached for the bag I had carelessly tossed on the bed and got some lube on my fingers. I then penetrated his most secret place with first one and then two fingers while he rubbed our dicks together with both hands and moaned and kissed me. Our movements grew more and more fevered until I could hold back no longer and exploded in a wonderful orgasm that I could feel through my whole body. Just then, I felt his ass clench and unclench on my fingers and he let out a little scream as hot semen spurted from his shaft onto my cock, balls, thighs and stomach.
"That was amazing", he said in a husky voice, "But I only find myself wanting you even more. I want to taste you."
I decided to give him what he wanted but with a twist. I changed positions so each of us had the other's cock at mouth level. He licked the hot cum off of my and made me shudder with pleasure as his tongue massaged my balls. I awkwardly did the same for him but had no experience and probably wasn't as good. I still found I deeply enjoyed it and as his cock came back to life I found myself very eager to lick every inch of him and take as much of his monster dick into my mouth as I could. I could only fit about half of it in comfortably but sucked it for all I was worth while I fingered his ass again and he sucked me all the way into his mouth. I was so lost in the pleasure I barely noticed when he lubed up his fingers and pushed one into my ass. The feeling was surprisingly good and a whole new form of pleasure. He managed to get two fingers into me and I had three in him when I felt him coming and tried to swallow all I could of his seed. I only lasted a second longer before I shot my load down his throat as well.
We collapsed into each other's arms, holding and kissing each other. He told me that he had made out with three other guys before and had given blowjobs to two of them, but that was all.
"In other words", he said, "I guess what I'm trying to say is I'm still a virgin. I would love to give myself to you but I'm not sure if I can really offer you what you want since I don't have a pussy."
"The way I see it," I told him as I slipped my fingers back inside his ass, "you do have one that I'd very much love to be inside."
He smiled with relief and longing and soon was on his knees in front of me asking me to be gentle. I didn't have any condoms but decided it was safe since he was a virgin. I lathered a lot of lube on my cock and his ass and he teasingly squeezed my manhood between his cheeks while he moaned and writhed. He then pushed back on the head of my cock and we both gasped with pleasure as I first entered him. He moaned and I slowly pushed in all the way until my balls slapped against his, a new and very pleasant sensation. I pulled out and thrust again, gradually speeding up. It had been understood all along that he would be the girl, and this was some of the best sex I had ever had. His ass was tighter than any pussy and he was very much into it. I reached around and touched his huge, beautiful cock, which was hard again. I started stroking it and before long he screamed and pumped his third load of cum into my hand. I pulled out and he turned around to kiss me hungrily. He then threw me down on the bed and jumped on top of me, straddling my throbbing cock and lowering his delicious ass onto it. He started rocking back and forth and gyrating his hips, giving me more pleasure than I'd ever felt. His cock remained semi-soft and bounced up and down as he rode my dick. I caressed his balls and fucked him more and more urgently. I could feel the ecstasy building but managed to hold back a little longer. He moaned a little longer and his semi-erect cock erupted for the fourth time that night. I couldn't take it anymore. I pounded his ass three more times and filled his ass with cum. It was the best orgasm of my life so far.
We fell asleep in each other's arms that night and when we woke up we could hear voices of people who were already awake in the house. He shyly asked what things were like between us.
"Why it's obvious, isn't it?" I answered, "You're my girlfriend now, if you want to be"
He walked into the bathroom with a smile and I got dressed in the bedroom, waiting for him. When he came back , his hair was perfect again, he was wearing make up, and was dressed in a tank top, sneakers and a skirt that reached about halfway to his knees. He smiled and I reached for his hand. He looked not like a girl, but rather like a pretty boy in female clothing. I have not given up girls, but I'm happy and willing to try a relationship with this boy for now. The opinions of others have never concerned me. I can take care of myself. I opened the door and we walked hand in hand to greet the world