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Speedo High: Part 16 (high school)
I was finally alone. Mom and dad had gone over to a neighbor's house for a New Year's Eve party, and Luke had gone over to Miguel's house to bring in the new year with his football buddies.
First, I put on my new Shark speedo and my favorite black track suit. Then, I began to plan the evening. I wanted this night to be perfect. When there was a knock at the door, I practically ran to answer it. It was Bob, and he looked as cute as ever. His curly hair was a mess, and he was wearing a black Adidas track suit just like mine. All of the guys on the swim team had one. He was also carrying a small overnight bag.
"Come on in buddy," I said. "I've been looking forward to hanging out with you all day."
"So have I," Bob said. "I can't believe we're wearing exactly the same clothes."
"Are you wearing your new Shark Speedo underneath?" I asked.
"I sure am," Bob replied pulling down his pants to show me.
"Awesome," I replied. "Let's go put your bag in my bedroom."
Once we put his bag down, I put my plan in action. "So, would you like to play poker again like we did last Friday night?" I asked sitting on my bed.
"You mean strip poker?" Bob asked taking off his shoes and sitting on the bed across from me.
"That sounds good to me," I replied and dealt us both five cards. "The game is called five card stud. You have to make the best poker hand from the five cards you're dealt."
"I've got three threes," Bob said. "Can you beat that?"
"All I've got is a pair of twos," I said taking off my pants.
"Dude, are you already hard?" Bob asked pointing at the shark on the front of my Speedo.
"Dude, I've had a hard on most of the day anytime I have thought about tonight," I admitted.
"Yea, so have I," Bob said.
"Well, let me see it. It's not nice to keep a fellow waiting," I said.
"Not just yet," Bob replied.
"What do you mean 'not just yet'?" I asked. "I don't think I can wait another minute." I took off my jacket and dove for Bob who was still wearing his track suit. The two of us began wrestling on my bed. Cards were flying everywhere. I managed to yank his pants off, but had a much harder time tugging the jacket off. Finally, Bob gave in and took the jacket off himself. Then we started wrestling again. After a few minutes he had me pinned down on my back, the two us wearing only the small black Speedos. We were both obviously hard. I made a sudden move and had Bob on his back with my body probe upon him, cock to cock. It felt so good.
I looked into his green eyes and knew exactly what I wanted to do. I knew that it was what he wanted too, so I kissed him. While are tongues wrestled with one another, he massaged my ass cheeks through my swimsuit while we grinded our hard cocks together. The only thing separating them was the thin nylon material. This grinding and kissing and massaging went on for so long that the fronts of our speedos were wet with precum and our lips were red and swollen. Damn we were horny.
When we finally took a break and lay on my twin-sized bed side to side, we held hands. "Wow, that was intense," Bob said.
"Yea, I saw stars and all of the planets shining brightly," I replied. I turned and looked at him, "Bob, you turn me on so much. I like everything about you, and I cannot wait to take your cherry. Do you want to get naked?"
"I sure do, but first there's something I need to talk to you about," Bob replied.
My heart sank. I had a feeling this was not going to be good. "What is it?"
"Ever since I lost the bet Friday night, I have been thinking about you fucking me," he said.
"So have I," I replied. I reached inside my Speedo and massaged my balls while he spoke.
"You know that you are my best friend, and I like messing around with you," Bob said.
"I feel the same way about you," I replied.
"It's just that I do not want to get fucked," he said. "Don't take this the wrong way, Matt, but I don't think I'm as gay as you are. Kissing and sucking is awesome. But, the idea of getting fucked does not turn me on at all. I don't think it ever will. Don't be mad. I don't want to spoil the fun, and I hate backing out of the bet, but I had to tell you how I feel."
"I'm glad you told me. Really. It's just that we are so much alike that I thought you wanted what I wanted," I said.
"So did I," Bob said. "But my family hung out at the Worleys' house today, and Jackie was there."
"You mean the same Jackie that you and I put our money together to buy a gift for in the third grade?" I asked.
"Yea," Bob said. "Except that she isn't a third grader anymore. She is so pretty, and I like her a lot."
"I see," I replied. "You realized that you still like girls. Did talking to her make your dick get hard?" I asked.
"It sure did," Bob replied. "Just as hard as it gets when I think about you."
"No shit," I said. "You're right, bro. I'm way gayer than you are. No girl as ever made me feel that way. I guess I'm more like a girl than you are."
"What do you mean that you are more like a girl than I am?" Bob asked smiling. He gently ran his fingers through my long hair. "You sure are as pretty as a girl."
"I am looking forward to feeling you inside me. There's nothing that I want more. I want to lie on my back and have you play with my hole until it's ready. Then, I want you to push your cock inside me and make love to me. And, while you are fucking me, I want to look deep into your eyes and feel the two of us connect."
"Damn, Matt, the way you talk makes me want you so much," Bob replied.
"As much as you want Jackie?" I asked.
"No. More. Way more. I don't love Jackie yet, but I love you. You are my best friend, and, if you're cool with being on the receiving end, I really want to fuck you," Bob said.
"I'm cool with it. In fact, I'm starting to understand that I'm pretty much a bottom," I said.
"I guess that makes me a top," Bob replied. "I thought you were going to get mad at me for breaking the bet."
"No way, bro. I would never force you to do anything you don't want to do. That's not cool at all," I said.
"I am so glad you understand," Bob said. "Now let's get this party started. Are you ready?"
"I'm so ready," I replied. "Are you ready to get naked?"
"I sure am Matt," Bob said. He knelt up in my bed facing me. I carefully pulled his tight black Speedo off of him and especially liked watching all six hard inches spring from the confines of the nylon material. I immediate bent down and licked the drooling tip.
"Wait a minute," Bob said. "Let's get you naked too."
So I lat flat on my back. He got out of the bed and gently pulled the tight Speedo over my hard cock. Like his, it immediately sprang free and pointed straight up at my belly button. Then he bent down and took the whole thing in his mouth and started sucking. I immediately saw fireworks it felt so good.
Without missing a beat, Bob positioned himself on his side next to me in my bed so that his cock was right in front of my face. I started licking his smooth balls and the underside of his hard dick. It was hard to think straight. His sucking felt so good. Finally, I took his entire cock into my mouth until my nose was against the place where his pubes used to be before he shaved them off for swimming. I swallowed his cock into my throat and started bobbing my head up and down on it. He was moaning and sucking my dick at the same time. It felt amazing. When he slid a finger inside my hole and started finger fucking me, I stopped sucking his dick. I could not focus on both things at the same time. The haze of sex took over and all I wanted to do was cum. Next he stopped sucking and let his saliva drool into my boy pussy. Then, he gently pushed two fingers inside of me and started finger fucking me hard and fast. As soon as he took the head of my dick back into his mouth I knew I was very close. The combination of his soft wet lips on my cock and his fingers hitting my prostrate were too much for me. Without warning him, I started firing volley after volley of warm boy goo into his hungry mouth, and he didn't stop finger fucking, sucking, and swallowing until I fired my last load.
Once my orgasm ended, Bob got out of bed and repositioned himself so that the two of could spoon as I came down from my sexual high. He kissed the back of my neck and began to slide his hard oozing cock up and down my crack. His nearness to me felt amazing. "Matt," he said, "I want to fuck you so bad. There is nothing that I've ever wanted more. Are you ready?"
" You know it," I said rolling over onto my back and sliding over to the middle of my bed. I pulled my knees up to my chest and began to finger my hole making sure it was good and loose, "Look into that drawer," I said pointing to my bedside table. There's some lube inside of it."
"You mean this stuff called Astroglide," he asked.
"Yea, that's it," I said. At this point I had worked three fingers into my pussy. I was so ready. "Now use it to coat my hole." Bob squeezed the lube onto two of his fingers and slid them gently into my boy pussy coating the walls of my hole. I then took some and squeezed it into my hand and coated his hard throbbing cock with it.
"Careful bro," he said. "You'll have me shooting cum before I even put it inside of you."
"No way man. I don't want that to happen. I've waited too long for this," I replied.
"Okay, here goes," he said after giving himself a minute to regain control. "I don't want to hurt you. Tell me to stop at any time." He grabbed the base of his hard dick with his right hand and positioned the head at the entrance to my pussy. Then, he pushed and the head of his cut cock slid past the sphincter, and it hurt like hell. So I closed my eyes and relaxed even though tears dripped from my eyes.
When Bob saw that I was crying, he stopped pushing. "Am I hurting you?" he asked.
I looked into his green eyes and I lied, "No way man. It feels amazing. Just take it slow." It hurt more than anything I had ever felt before, but I didn't want him to stop. I had not realized how big around his dick was. It must have been way bigger that the one-inch in diameter Colt anal trainer I had used to stretch my hole.
"You are so tight," Bob said. "I know what you mean. This does feel amazing." Little by little he began to push in and pull back out, pushing in a little further each time.
It hurt so much, my cock, which was nearly always hard, was as soft as ever. I closed my eyes, tilted my head back and I moaned.
Bob took my moan of pure agony to mean that I was feeling good, so he made one final push and buried all six inches inside of me. Oh my God. My ass was on fire and it felt like he had shoved a two-by-four inside of me. I wrapped my legs around his back and held him there, tears flowing from my eyes.
Believing that they were tears of joy, Bob said, "I can see how happy I've made you. I'm so glad that I'm your first." Then he licked my tears and started kissing me. The kiss was long and passionate. And, the longer we kissed, the more my hole adjusted to this foreign invader. I relaxed the hold my legs had on his back and pulled them back until my knees were near my ears. We were both sweaty and lost in this fog of pain and pleasure. Bob pulled all the way out until only the head of his cock was inside of me. Then, he slowly pushed it in again. Even though it still hurt, I was starting to like it. He began to establish a slow but steady rhythm sliding back and forth over my prostrate. This mixture of pain and pleasure was something that I had never experienced before.
"How does it feel, baby?" Bob asked. He had never called my baby before. I liked it.
"It feels like nothing I've ever felt before," I replied. "I love having you inside of me."
"I know what you mean. This is way better than anything I've ever felt before," he said while slowly pushing in and pulling out. "The inside of you is soft like velvet and the tightest thing I've ever felt," Bob said.
"Kiss me again," I said. As he forced his tongue into my eager mouth, he forced his cock all of the way back inside of me, and he began to fuck me hard making the head of the bed hit the wall over and over again.
The pain subsided a little more as I became more and more lost in the place between reality and pure bliss. In the midst of the pain and the pleasure, I reached down to feel my dick. It surprised me to discover that it was rock hard, so I started beating off. At the same time I started squeezing the muscles inside my ass relishing the burning and the paid and the unbelievable pleasure that was radiating from inside of me.
"I don't know what you just did," Bob said, "but it felt incredible." He threw his head back with his eyes closed, every tendon in his neck stretched to the limit, and he fucked me. He was all man and all power and all lust. He was a tiger in the bed and he assaulted my hole over and over moaning loudly.
Underneath him I was writhing in this otherworldly place of pure animal longing and physical pleasure. It was amazing. While there was still this undertone of pain, the pleasure and all of the other sensations I was experiencing had me feeling like I was demon possessed. I never wanted this to end. I stroked my cock harder and harder, faster and faster. I squeezed my ass muscles harder and harder, and I kissed my lover, forcing my tongue deeper and deeper inside of him, and then it got even better.
Suddenly, without warning, my cock started firing molten bolts of hot lava between us and Bob screamed out, "Oh my God!" He fucked me harder and harder as load after load of his seed flowed out of him and into me. He was a beast and his pleasure was immense, thrusting in and out of me seemingly without ever stopping, and then it ended and he fell on top of me, his heart beating wildly within his chest, his lungs aching for air, and his body covered in sweat and cum.
As we began to regain our senses, and to remember who we were and where we were, we both began to kiss one another again, even though we were totally limp. The kisses were soft and loving.
Bob's soft cock slipped out of me and cum oozed from my hole. His hot hard wet body was prone upon mine, and it felt so nice. I had never felt more connected to anyone than I did to Bob at this moment in time. Neither one of us moved as the reality of what we had just experienced washed over us. This was one of those moments that we would never ever forget. It was our first time and it was real.
Bob looked into my blues eyes and sighed, "Baby boy, that was so amazing. I never thought sex could be this good." Then, as if he had suddenly become aware that he had fucked this tender virgin like a rampant stallion without mercy, fear filled his eyes. "Matt, I am so sorry. I got so lost in the sex that I went crazy. Did I hurt you? Are you okay?"
"I am great. It was the most intense experience of my life, and I am so glad it was with you," I said. "But, I'm not going going to lie. I don't think I'll be able to walk the same for the next few days. You are a beast."