Note: If you offended by gay, male sexual situations, please avoid the following story.
Hoop Dreams - Part 2 by Underboy
As Rudy and I lay together on the couch and rested, I softly caressed his brown tits and lightly kissed his neck. He had just performed oral sex for the first time in his life and I was his first. He succumbed to his building lust due to my arousing massage and my oral service upon him which opened the door to his suppressed homosexuality. Rudy thoroughly enjoyed his initial encounter with another man and simply sat with me in awe of his experience. I wanted to complete Rudy's virginal coronation and I decided to make my next bold offer.
"Rudy, would you want to try something else with me?" I asked. "What do you mean?" he responded with uncertainty. "Do you want to try getting fucked?" I offered.
He quickly raised his eyebrows at the idea. "Fucked? In the ass?" he asked in astonishment. "Yeah, how else?" "No way, man. I can't do that," Rudy answered firmly. "Why not?" I challenged. "Why not? Because I'm a guy, that's why." "How would that change?" "Because getting it in the ass--I would really be a fag then. I mean gay--I'm sorry. I didn't mean to offend you. I'm a curious guy but I don't know if I want to go that far." "But you just were intimate with me, another man, and you're still a guy," I reasoned. "This is different," he asserted. "How?" "Well, first of all, I don't think I could live with myself afterward. And second, it would hurt way too much. I mean--look at the size of that thing. I can't imagine it... inside my ass." "Look, you said yourself, you're very curious. Don't you think you'll try it eventually." "Maybe--I guess. I don't know, David." "But haven't you ever thought about it?" I asked. "Well, yes. But thinking about it and going through with it are two different things." "If you've thought about it, why not try it, just once?" I posed. "I don't think so. I am curious but I don't think I'm ready for that. It's kind of heavy duty. I mean, this has been really great with you and I know I want to do it again. But I'm just not sure about doing that." "Haven't you ever wondered what it would be like? How it would feel to be with another guy in that way?" "Of course. And I have fantasized about it. But I'm still a guy," he argued. "I'm a guy, too. That won't change. It's just a different sexual expression. Look, you just sucked dick for the first time, right? How did that feel? Pretty good, huh?" "Yes, David. But--getting fucked--I don't know." "I realize it's a big leap and I understand how you feel. It was hard for me, too. But it felt totally great. I know you'll like it, Rudy." "That's a big step right now. I mean, first you're giving me a massage and next I'm sucking your cock. Now you want to fuck me?" "Look, Rudy. I think you're really sweet and I know you have all these confusing feelings that are coming out right now. I can help you through them and I'd be willing to show you the ropes without hurting you. How about this? How about if I take it real slow and gentle? Then you can do me afterward? I'll do whatever you want." "You would do that?" he asked "Rudy, you're a really beautiful guy. And I admit it, I really want to do this with you. But I know you'll like it."
Rudy paused for a second, almost giving in.
"And if I didn't like it, you'd stop, right?" he searched for assurance. "Of course. I'm not going to hurt you, Rudy. Look, I know it seems kinda' scary and I don't want to pressure you. If you say no, that's fine. But it's not as bad as you think." "I'm not sure. This is going too fast. Maybe I should wait." "Wait for what, Rudy? Say you wait for someone else to be your first. You get the nerve to go out, maybe get drunk and then you give in to someone because of bad judgment and have a really bad experience. Then you'll really feel bad and hate yourself. Meanwhile, here I am. You've had a good time so far, right? Why not go all the way? Am I so terrible?" "No, not at all. I think you're really handsome, David. I just don't know." "I think you know. I can tell you're kind of intrigued by the idea," I said as I saw his cock beginning to swell.
Rudy paused to think about my proposition once more before deciding. I could tell his protestation was eroding. His fear of pain and humiliation was slowly overtaken by his youthful libido and sexual curiosity. His mind raced with questions:
"Should I do it? Should I do it? Man, getting fucked in the ass! Me, Rudy. I've always been the stud with the girls--the guy they were all after. The guy who fucked them. Now I would be the one getting fucked. Can I handle that? I just had sex with another man for the first time. But I'm still afraid. Just the idea of that big cock of his pushing up my ass is painful. But part of me really wants to do it. I'm really hot for this guy right now and I'm really curious about trying it. Geez, if it's anything close to what we just did, I know it will be good. What if it hurts too much? He said he would go slow. Who is this guy anyway? He could be some psycho! Then again, if he wanted to hurt me, he could have done it by now. No. I think he's okay. Besides I already sucked his dick. I never thought I would do that. I wanted to do it. I can still taste his cum in my mouth. He sucked my dick, too. He kissed me and made me feel like no one else ever has. What would everyone think? Dammit, I'm an adult. I'm 24 years old. I know what I'm doing. I've always wanted this. But getting fucked? Up my ass? How will I feel afterward? Wouldn't I be gay for sure then? Or am I now? C'mon, Rudy. Deep down, you know you want it. You want to try getting fucked at least once. Just thinking about it turns you on. You've gone this far. Why not go the whole way? This guy is really cute and he really knows how to push your buttons. He also knows what I'm going through. He knows what it's like to come out of the closet. He can help you through it. Get real, Rudy. He just wants to pop your cherry. So what? You want it, too. It's just sex. But now it's with a man. He said I could do him afterward. And if I don't like it, I'll just tell him to stop. It'll be okay, Rudy. Just do it."
The more he thought about it, the more he seemed to trust me to lead his curiosity down a safe path. He finally succumbed to his strong, natural desire. He just needed a little assurance.
"Look, David. This is really new for me. I know we just met, but I feel you're someone I can trust. Please don't take advantage of the situation." "I wouldn't do that, Rudy," I assured him. "Part of me tells me not to do this. But another part really wants to try it. I guess I'm kind of horny right now and I'm ready to experiment with you some more. I guess I've been holding back these feelings all my life and now they want to come out. I think you're very attractive and it's been really good so far."
Rudy paused to gather himself.
"You'll go really slow, right?" Rudy repeated. "Absolutely." "And you won't hurt me?" "I'll be as careful as possible. You'll feel nothing but pleasure, Rudy." "And I can do you afterward?" "Yes." "Well, okay, David. I'll do it. But you can't tell my friends, okay." "This is just between us," I promised.
Rudy took a deep breath as he crossed the great divide of his life. "I can't believe I'm going through with this. What do I do first?" he asked.
Wow! Just the question I wanted to hear. His capitulation really turned me on. This incredible looking stud went from "no way" to "what do I do first?" in a matter of minutes. I was about to take this beautiful boy's virginity in the most profound way. I would be his teacher and he my pupil. What a position to be in! I really liked Rudy and I wanted him to come back for more. I had to make his first experience really special even though we were complete strangers. I love having sex but making love is even better. I decided to come as close to the latter as possible.
"Come on," I said.
I took Rudy's hand and led him into my bedroom. We sat on my bed and we began to kiss. I slowly leaned him against the soft pillows as our lips touched passionately. As I climbed on top of him, he began to release his inhibition and trust my direction. Now that he had decided to this, he would not hold back. Our youthful bodies pressed together as we held each other tightly and pressed our lips together. I could feel Rudy's gentle touch as he caressed my back and ass passionately. As our throbbing cocks slid together we felt the passionate call of our yearning bodies. Our sensitive foreplay continued for several minutes until our heightened arousal poised us both for the next step.
Rudy looked at me and his innocent eyes acknowledged that he was ready. I kissed him passionately as if to say that everything would be okay. I felt trust in his embrace and I wanted to give him the kind of sincere, caring experience he would never forget.
As our warm bodies wound together in sinuous rhythm, I reached to my nightstand for a tube of K-Y jelly and spread some on my hand. I reached between his long, firm legs and slowly slid my fingers along Rudy's dark crack and spread it between his spongy cheeks. I rose to my knees, slowly spreading his legs apart as I bent them up and positioned myself before his slick ass. With his knees resting against my sides, I gently eased the lubricant around the edge of his pristine hole to which he uttered a subtle moan. I slid my index finger around the brown bud feeling his puckered wrinkles as my fingertip circled the point of entry. I could tell Rudy loved the feeling of my slippery hand probing around his ass by his ecstatic expression.
Rudy slowly jacked his hardened meat and watched me intently as I prepared him for his maiden voyage. I lifted his legs higher in the air and pulled him closer as I applied plenty of the lubricant on my rock-hard cock to make the penetration as smooth as possible. I waved my penile wand up and down Rudy's burgeoning ass so he could get accustomed to the foreign feeling of my piercing organ. He responded with pleasurable moans as I aroused sensations in places where he had never been touched.
"Now just relax and loosen your muscles," I told him. "Okay," he agreed.
I placed the swollen head of my bursting cock right at Rudy's untouched hole and slowly swirled it around his puckering bud to arouse his eager senses. "Okay, here goes." I slowly eased my cock head inside of Rudy's virgin hole and it began to give way. As I began to penetrate his untouched anus, Rudy grew slightly anxious due to the initial discomfort. "Ahhh. Wait. Wait. That stings," he groaned. "Just relax. Don't tense your body," I said as I continued pushing.
As Rudy winced I pushed forward and was able to fit the entire head inside of him. I paused so he could get used to the unusual feeling. "Are you okay?" I asked. "Yeah, I think so. Keep going," he responded.
I pushed forward once more and I felt Rudy's body jerk with pain as his tight hole resisted my entry.
"AHHH! Hold on. Wait. I don't know about this. Maybe we shouldn't--," he said with second thoughts. "Take it easy, Rudy. It'll get easier. Just relax," I assured him as he agreed. I removed my pulsing prick and lubed it thoroughly once more. "Here I go again," I warned him.
I shoved my solid erection inside of Rudy once more and managed to penetrate him deeper. When I got about a third inside and saw that Rudy was still okay. I slowly thrust myself inside of him even further and felt his virgin tunnel begin to give way. He winced and moaned once more but then relaxed his anal muscles. When I got about halfway in, I slowly pulled back and then pushed forward as far as I could go. I could see Rudy becoming comfortable as I slid my long, thick tool completely inside his youthful hole.
"I'm all the way in, Rudy. Are you okay?" I asked. "Yeah, yeah. That feels okay. Keep going," he prompted me. I slid my inflated member in and out of Rudy's virgin hole with a slow groove and I could see the pleasure on his face begin to increase. I pushed against his prostate gland and he began to feel the tingling feeling of my penile massage. "How's that?" I asked again. "Good. It feels good. Don't stop," he requested.
I moved Rudy's legs over my shoulders and leaned above him as I increased the rate of my thrusts. I felt my pelvis press against Rudy's firm ass as I pumped into him faster. He looked at me with a completely content expression as I began to fuck his virgin ass with wild abandon. I knew that he was now really enjoying this new experience and I could almost hear his thoughts:
"Oh, man. I cannot believe this. I'm actually getting fucked-- in the ass. And it feels so could. I never thought it would be like this. It feels kind of strange being in this position--lying on my back with my legs in the air. It's kind of degrading, but it really turns me on. His dick feels huge sliding inside my ass. It feels weird but it's really exciting. He really knows exactly what he's doing and how to hit all my right spots. I never thought I would like getting fucked this much but his dick is really massaging my ass. I'm so glad I gave in to him. I kind of feel like a girl in this position but I feel so fucking hot right now. His ass is really plowing me good. I wish I could get this on video. I feel so close to him right now. I just want to hold him against me while he fucks my ass. Just saying it in my mind is such a turn on. I can barely stop myself from saying it out loud. I don't know how long I can hold off from cumming. This feels so fucking incredible. Why did I put up such a fight? Right now I just want to enjoy this. I'm really getting fucked!"
As I thrusted harder and harder, I moved his legs with his knees against my hips and leaned on top of his chest. I kissed him hard as my ass undulated intensely. Rudy finally felt the pure pleasure of my fucking motion as he clasped his rubbery legs around my waist and sealed the intercourse. He squeezed the cheeks of my bouncing ass as I pumped into him even faster. Rudy's refilled boner pressed against his firm stomach as I pounded into his untouched ass.
"Do you like it now, Rudy?" I asked as I slid in and out of his ass. "Uggh, uggh," he smiled. "Your big dick feels so good up my ass, David."
Rudy was now in the throws of ecstasy as I fucked his tight virgin hole which never knew such utter pleasure. His tingling prostate gland supplied a heightened arousal which was completely new to him. In his euphoric stupor he simply lie back with his legs in the air and absorbed my pelvic thrusts.
"Oooh, oooh. Fuck me. Fuck me harder," Rudy demanded.
This gorgeous young virgin who was so hesitant about his first fuck was now taking my dick like a pro and enjoying every second of his homosexual initiation. The feeling of my slick cock sliding in and out of his tight ass drove Rudy crazy as he dug his fingers into my back and held me tightly while I pumped his gorgeous Latino ass. My bed shook wildly as we fucked for an eternity. Our bodies meshed into a harmonious union of mutual desire. I could tell Rudy was getting close to his climax and so I stopped and switched positions. "What's wrong? Why did you stop?" Rudy asked. "Nothing. I want to try something different. Get on your hands and knees," I asked. "Okay," he complied.
Rudy innocently obliged as he turned over and assumed the position on all fours. "Like this?" he asked as his ass waited eagerly for another pounding. "Perfect," I responded with approval.
As I lubed my throbbing cock again, the entropy of Rudy's thoughts was evident on his face:
"This is so incredible. Here I am on my hands and knees waiting for him to fuck me some more. But it feels so great. I feel humiliated and excited at the same time. It's such a turn on. This guy has me so aroused I would do just about anything he asked right now. Now I'm just waiting for him to fuck my ass from behind. Like a fucking dog. But I love it."
Rudy was now my toy to play with however I wanted. I climbed behind him and squeezed the perfectly round orbs of his bended ass. Then I slowly shoved my stiff rod inside of Rudy's hole once more and began to pound him again. I braced myself on his firm shoulders and pumped hard into his round ass as he knelt on all fours. His hair flew in the air and his body shook abruptly as I hit his ass repeatedly with my thrusting hips. He grabbed my shaking ass pulling me deeper inside his body. I was now pushing hard into this virgin, Latino stud as I fucked him doggie style. I could see Rudy's mind buzzing again with a million thoughts:
"This is fucking amazing. I can feel my ass jolt forward every time he pounds into me. It feels so cool. Every time he pushes forward, I feel like I'm gonna cum. I can't believe I'm in the middle of my first fuck. And it's so great. Here I thought I was so macho. So studly. I was the guy all the girls were after. I was the jock who had them at my beck and
call. Now I'm the one getting fucked and pleading for more. How many girls had I fucked just like I'm getting fucked now? I'm getting fucked up the ass and enjoying it like a fucking fag. But I guess I am one. I never thought in a million years that I could go through with this. But here I am getting totally fucked like a dog by another man. My dick is bouncing in the air and my body is rocking forward like a rag doll. I'm so excited. Oh God, I love getting fucked. I don't want it to end."
"You like getting fucked like a dog, don't you, Rudy?" "Ohh, oohh. Don't stop, David. Fuck my ass. Fuck me some more." "You love my cock up your ass, eh?" "Fuck me! Fuck me like a dog!" Rudy cried.
Rudy was totally into the action as he raised his ass high in the air to meet my intense thrusts. I took his throbbing rod into my fist and stoked it firmly as I fucked his ass while he moaned with increased pleasure. His hands slid forward to grasp the sheets as he fell to the bed and his face pushed into the pillows. Rudy's brown ass stuck higher in the air to take my stiff cock in his tight tunnel. I fucked Rudy harder and harder until we both could withstand no more.
I lifted Rudy up and pulled his back against my chest as I pumped him with my final thrusts. I removed my solid spear from Rudy's ass and jerked it wildly as he turned his body to face my nearing climax. I felt the orgasmic tingle in my balls as I jerked my hard flesh in Rudy's face. I cocked my head back as my climactic juices boiled and exploded directly into Rudy's inviting mouth. Shot after warm shot spewed between Rudy's open lips, landing on his tongue and teeth. He sloshed the warm, thick liquid inside his cheeks and swallowed my creamy load. More of my white juice shot across his boyish face and dripped down his skin. Rudy then sunk his mouth upon my expended cock and squeezed out what remained of my tasty explosion.
The unique taste of my hot fluid pushed Rudy over the edge as he knelt up and jerked his swollen prick intensely. His head shook intensely as his body convulsed and finally burst with energy. He pushed my head down to face his spurting cock as he released endless hot streams upon my glistening skin. This young boy could sure shoot a huge load as ropes of his cum pierced my face. He shoved his pulsing tool inside my mouth and released his virginal load between my taking lips. How delicious his young juice tasted as it shot profusely on my scooping tongue. I savored his salty cream as I swallowed gulp after gulp of his virginal explosion.
As Rudy's first experience culminated, we both stood on our knees and kissed passionately as we tasted each other's orgasmic honey. Exasperated, we collapsed side by side on the bed and caught our breath.
"Oh, man. That was awesome. I can't believe it. You were incredible," Rudy said gasping for air. "You took it great for your first time. You have a great ass, Rudy." "I can't believe how great that felt. I'm so glad I listened to you. You made my first time better than I ever thought it could be." "So, you liked getting fucked, Rudy?" I asked. "Wow. I can't even explain it. I loved getting fucked. Just saying it turns me on. I never thought I'd like it, but I loved it." "I told you it would feel great. You're a natural bottom and you didn't even know it." "I do now. I know you said I could do you. But I can't wait for you to fuck me again." "You don't have to ask me twice. Besides, we have plenty of time. Especially if you spend the night with me, Rudy." "I'd love to, David. I just need a little rest then I'll be ready." "Ready for what?" I asked. "You know--your end of the deal. I get to fuck you now." "Oh, I wasn't serious about that. I just wanted to get you into bed," I smiled. "Yeah, right," Rudy said as he began to wrestle me down. "Okay, okay. I'm kidding. I wouldn't make a promise I didn't plan to keep." "That's what I thought," said Rudy smiling as he released me. "You better rest up, too. It's payback time for you."
As Rudy and I rested side by side after our heated encounter, I looked forward to fulfilling my promise and give Rudy the same pleasure he had given me.