Hopefully this will help.
For weeks I after I had met up with Jeremy and Jeff, I would fantasized about our night together. I’d find myself drifting off during the day in school thinking about it and all I could do was hide my erection until I went home to masturbate furiously. Even later in the evenings, I would masturbate again thinking about it all. I’d sit in my shower for long periods, trying to imagine them both standing next to me as I sat on the edge of the tub and tugged away. I was discovering something in my life. Something that I knew that when I craved it, the only thing that would save me from acting out again was to masturbate and clear my head. Even after a while, I began wondering what it would be like to be fucked. I wasn’t clueless, I knew what gay guys did during sex, well before I ever had any experiences, but I wasn’t sure.
I would try out a putting in a finger while masturbating and though it felt good, I knew their cocks weren’t the size of my fingers. If I had my dad’s sausage fingers, maybe I’d know, but at that age, I had skinny teenager fingers. Little by little I would try out different sizes of things I found around the house that I knew wouldn’t hurt. I even stole some of my step-moms carrots she would buy from the store. Anything I could find to slowly help out my virgin ass to the size of their cocks, I wanted to try out. I did a lot of research online about beginners to anal and what precautions to take, so I was getting wise to the ways of anal masturbation and safety.
All of this came to one day I found some cucumbers in the fridge. I remember standing there with the refrigerator door open staring at them in the clear plastic drawer. They were thick like a silver dollar, long with a slight curve, and about nine inches in length. I snuck it up stares and pulled out my hidden supplies of KY and lotion.
It was late at night and everyone was asleep, but there I was in the bathroom, shower running hot and me standing there naked looking at this cucumber. I felt a feeling of emptiness in my ass and it craved to be filled. Almost like an itch that needed to be scratched. I took out some KY and lathered my asshole, rubbing it gently and working my star in small circles. On my back, I pressed in one finger until I felt comfort and then slid in another slowly stretching myself open. I looked at the cucumber and knew my fingers could only prepare me so much, so I decided to give it a try.
I got up to my knees and grabbed the cucumber and stroked it up and down imaging it was a big beautiful warm cock, spreading KY all over it. I began to reach between my legs as I was there on both knees in front of my shower. My hand brushed my hard dick and I totally forgot all about it while I was prepping my ass for invasion. Holding it on the ground at its’ base, I slowly began the decent to the tip of the cucumber that would soon be breaching an area that never had something so big inside of it. I pressed down and my asshole wrapped around it, hugging it tight as it gave way. The size of it was pressing against the walls of my ass and it hurt. I reared up and started over. Ever so softly, I worked my way down on to it again and again, gaining ground each time. By this time, the pain had subsided and I could feel my prostate being massaged greatly, more so than ever before.
Still taking it slow and easy, I was inching in little by little. I had only worked in about three inches or so, before I was alerted… my phone signaled a text message. It was from Jeff! (We had all given each other our numbers after that night). I was so horny and his timing couldn’t have been more perfect. He was asking me what I was doing and my fingers without hesitation typed, “Fucking a cucumber”. He was surprised! Hell, I was surprised myself when I hit the ’SEND’ button so quickly. I told him what I had been doing since our last meet up and he loved hearing it. He invited me over saying, “Jeremy’s out. We can see how much you’ve progressed”. I quickly wrapped up my supplies in my towel, shut off the running shower, and ran to my room to get dressed.
My way to his house was quick. I was barely stopping at the stop signs as I sped through the neighborhood streets. I was eager, excited, but still a little nervous all at the same time. It was different being in my bathroom doing this all by myself, but here I was, speeding to the house of a man for him to partake in the act as well, but not with cucumbers, but with his nice, warm, thick cock.
He greeted me at the door, opening it before I was even to it to knock. I walked in and asked how things were going and where Jeremy was off to. He told me things were going well and about to get better and that Jeremy was “still out”. The lights in the house were off, save for the lamps in the living room. As we walked back to his room, I noticed the TV was on and right there on the couch… was Jeremy. Was was laid out on his back with a blanket over him, head perched on a pillow pressed against the arm rest. It all came together and I said to Jeff in a whisper, “You said he was ‘out’… you mean passed out?” He only smiled and grabbed my hand and led me into a guest bedroom. The lights were turned off and I could barely see anything. Everything was a shade of dark gray to black. The only light that was in the room was the dim light from the lamps outside in the living room and it wasn’t helping much. I sat on the edge of the bed and thoughts were racing through my head. My ass was getting that feeling that it needed to be filled, my lips craved to be around a cock, my stomach got was filled with butterflies, and I didn’t know how to proceed.
I looked to my left and could see through the partially closed door Jeremy laying down asleep peacefully. I could hear Jeff walking around and softly talking, but I zoned out with my mind in a million different places. I snapped back to reality when Jeff stepped in front of me and pulled my head to his cock. I opened my mouth and took it in.
I sat there on the edge of the bed in my swim trunks, shirt and flip flops, sucking Jeff’s cock with both hands holding the sides of his thighs in the darkness of this guest bedroom. I tried my best to not be too loud as I looked over to still see Jeremy on the couch. Taking my hand up, I began working his shaft as I moistened his dick with my mouth. I could hear him quietly sigh and he placed his hand on the back of my head, reconnecting me to the moment and my actions. I began to worship his beautiful man staff as if it held the answers I was looking for and the cure for my aching desires.
I looked up at him as I continued pleasuring him and I could see his eyes were closed, knowing that every move I made with my hands, every lick I lapped at his balls, and every slurp that came from my lips only made me more of his toy.
He reached down and lifted my shirt over my head, only briefly stopping me from my tasks at his love muscle. As soon as the shirt was off, I went right back to my duties, what in that moment, I was meant to do. He eased me off him and told me to lay back and I did. He grabbed my shorts and pulled them off, springing my penis out uncovered in the darkness, but he paid no mind.
“How did those cucumbers work out for you?” I remember him asking.
“They didn’t give me what I really want”
He pulled open a drawer and presented a bottle of lube which he squirted onto my asshole and slowly massaged it with his fingers. He looked at me as he noticed my ass was already gaping and waiting. He walked up holding my right leg in the air and my left lay spread to the side. He grasped his cock in his hand and flopped it on my leg, looking at me.
I didn’t know if he was waiting for me to say anything as I laid there clutching the blankets in anticipation. I stumbled on my words and arched my head back and looked through the door to see Jeremy. I wanted to ask him if he would wake up, but then I felt it. He pressed his pulsating cock into my ass! I took in a deep gasp as my eyes were locked onto Jeremy as he still slept soundly on the couch. His dick was thicker than the cucumber and immediately I could tell a difference. It was a connection I had never felt before and his warm cock was the key to locking it tight. I looked back at him, my eyes fixated on him as I became infatuated with what was happening. My lust for a cock in my ass all these weeks was finally happening as he slowly moved back and forth, inching his way past every reservation I may have had with every subtle thrust.