This follows "My First Experience With Josh" and "Someone to Talk to"
More Continuing Explorations
For the next month after that first time with Ryan we hung out a lot more. He was still dating someone and I was in the closet, but we enjoyed each other’s company and remained friends. We would often hang out with a bunch of people from school and it seemed like they were accepting Ryan more and more. It made everything else okay to be able to have a friend I could talk to about anything. I wasn’t nearly as worried about Josh and his girlfriends (The first one broke up with him after another week). I was happy to be who I was and didn’t want a thing to change. One thing that I was glad hadn’t changed was the fact that Ryan’s boyfriend still didn’t want to have sex. So about once or twice a week Ryan and I would find some way to relieve a lot of our sexual tension. We wouldn’t have anal sex every time, but we always got each other off. It was a nice way for both of us to escape the world and relax without another thought.
This time was probably one of the best because we had both had hard weeks. He worked in landscaping and his coworkers decided that they would start to make fun of his sexuality. It got really personal and he needed to let off some steam. My bad week came from a different source. I delivered pizzas just about every night and that night had been one of the worst nights on record. I got stiffed on money twice and was given a fake address on another. Instead of gaining fifty or sixty bucks on tips, I lost money. The world was cruel and we were both realizing this. When Ryan had gotten through that last Friday of work and remembered that his family was gone for the night he knew he had to call me. I had an earlier shift that night and got off at eight. I was more then happy to enjoy his company that night. When I got to his place we decided we could take it slow we just watched some TV for a bit. Not much was on so we decided to talk and maybe blow off a little steam that way.
“I think I made a mistake by coming out when I did,” said Ryan after a bit, “the world is too cruel to gays right now.”
“Don’t base that statement on this last week at work after all the guys from school don’t seem to really care anymore,” I reassured.
“That’s true, but that is a rarity. Most of the world acts like the guys from work. They think we are disgusting and against nature. I was just trying to tell my brother the same thing.” He had a fourteen year old brother, but I never thought they were close enough to talk about deep stuff like this.
“Why were you talking to him about this; he seems kind of young to really care?” I asked.
“He told me not to tell yet, but I know I can trust you. He told me that he thought he was gay, too. He was telling me about how he was thinking of coming out. I advised against it because of all that had been happening, but he didn’t seem to care about that.”
“Why does he want to come out so bad? He is still kind of young to sure of his sexuality?”
“Oh, he is old enough,” replied Ryan sternly, “Or at least he thinks so. He told me that he wanted to come out because there was no way he was going to be able to experience gay sex if he didn’t. I guess he is really horny but who wasn’t at fourteen.”
“Wow, I never would have pegged him as gay. Maybe you should tell him that I have found a way to have sex without coming out.” I said as I moved in for a kiss. The kiss was wonderful all the stress from the night of work seemed to slip out my lips and float away. That is until he broke it suddenly.
“He wouldn’t believe me if I told him you were gay, but if it came from you he might. It would be a real big help; I don’t want my little brother to have to go through the same crap I am going through now. He is too innocent I don’t think he could handle it.”
“I would be happy to help him out, he is a sweet kid.”
With the conversation ended we went to it with great passion. I sank my tongue into his mouth and took in his flavor. I loved it and became really horny very quickly. We moved our makeout session up to his room and fell on his bed. After a little while longer he put some music on and decided to do a little strip tease for me. First he pulled off his t-shirt leaving a tight wife-beater on. It clung to his chest nicely and I loved the shape his pecs made in it. He danced around for a bit like that swinging his tight ass in my face. His jeans were the next to go. He continued strutting around making sure to show off his well toned bare legs and even better looking ass. His bulge was growing as well and it looked as enormous as ever. He slowly peeled off the wife beater revealing his tiny nipples as they started to harden with the cold. This image of him was gorgeous and I was already close to cumming. He wasted no time with his boxer-briefs and just dropped them to the floor revealing that eight inch beast. I guess he was being controlled by that beast because he started pulling my clothes off as soon as he hit the bed. As soon as I too was naked he crawled up to my face and kissed me again and then wispered, “How do you want to do it tonight?”
“I am so horny, just fuck me and I’ll probably cum, no problem.” He obliged. He grabbed my butt and gave each cheek a nice little squeeze before lining up and plunging in. It felt so incredible and I was so horny that I came on his entrance. He didn’t slow down for me though he just kept going and so did my pleasure. I think I may have had a double orgasm from his pumping it felt amazing. I felt every inch of my butt filled with each thrust and my prostate was treated to a lot of intense pressure. It was amazing Unfortunately he was very horny as well and came not long after I had. I didn’t care. It was an amazing experience and I had completely forgotten about my awful night at work. “That was amazing Ryan, thanks.”
“Thank you for offering to help my brother. He won’t talk about it when my parents are in the house so I’ll let you know the next time they will be out.”
“Yeah, no problem, like I said before I like the kid, I don’t want him to suffer.”
I left that night completely satisfied and eagerly awaited the next time he would call me up for some sex. A call came the following Tuesday and I was hoping it was for sex, but his voice sounded different, sadder, “I feel really bad about this Dan, but we can’t have sex anymore,” I was devastated, “Matt, my boyfriend, finally gave in to sex. I kind of feel like I would be cheating on him if I did it with anyone else now that he himself is willing to do it. I didn’t mean to use you; I just want to go about this the best way possible.”
I was pretty low after that, but I knew Ryan pretty well and knew that he didn’t do it on purpose and that he had no intention of hurting me. “I understand, Ry, I may not like it, but I can accept it. Have you figured out a time for me to talk to your brother?”
“Well, yeah, if you are still willing to. I feel like a jerk after what I just did to you. I wasn’t really expecting you to follow through after that. Yeah this weekend my parents are gonna be in Albequerque for a conference so anytime after six on Friday and before five on Sunday.” His parents were very successful small business owners and often went around speaking about their success to different conferences and conventions.
“Yeah, I will probably stop by Friday night, maybe we can do something.”
“Yeah, maybe. Well thanks for understanding, Dan. I will see you Friday.”
So after another long day at work on Friday I decided to head over to Ryan’s house to talk with his brother and hang out for a while. I like Ryan even if he isn’t letting me have sex with him so I figured it would still be a fun night. I show up at his house and his little brother, Caleb, answered the door, “Hey, Dan, Ryan’s not here right now.”
Caleb is a really nice guy. He is a perfect gentleman and always respects his elders. Unfortunately he always seemed really sad. Even at times when he probably was happy his face still had this deeper sadness to it. I don’t really know how to describe it, but he always seemed to be in pain. He had just turned fourteen in April and looked it. Like his brother he, too was thin and athletic, but he lacked the muscle tone. He looked a little scrawny with very thin arms. Despite looking weak he was actually fairly strong for his age. He was still very boyish looking, but you could tell he was getting ready to make the transition any time to manhood. He had nice blue eyes that really brought out his look of pain. He had straight dirty blonde hair that was always just long enough as to not hide his eyes completely. He was a cute kid and had the makings to be even more attractive then his brother.
“He’s not? I guess that’s okay, I was going to talk to you a bit as well. Do you mind if I come in?” I responded.
“No, I guess not.” Caleb still went to my high school so we were somewhat acquainted from that and had gotten to know each other a little better since Ryan and I had been hanging out so much. It probably still seemed weird to him that I would want to talk to him specifically. “What’s this about?” He asked as we headed toward the coach in the living room.
“Well, actually your brother wanted me to talk to you about something. I am not really sure how to begin.”
“What’s it about?”
“You see, your brother told me that you were gay...”
“That bastard,” he interrupted, “I told him not to fuckin’ tell anyone. Especially not someone from school. Now everyone will fuckin’ know about it and I don’t even know for sure if I really am gay. I could fuckin’ kill him. Why the fuck would he tell you?”
I was shocked at his language because he was usually very quiet. “Well that’s what he wanted me to talk to you about. He said that you were thinking about coming out.”
“What? No, I had no intention of coming out. My shit of a brother decided that he would fuckin’ out me to his friends. Now, I am gonna have to move schools like my brother did. This is so fuckin’ stupid.”
“Don’t worry about being outed. I am the only person he told and I don’t plan on letting anyone else know. I...”
“Why should I believe you?” he asked as he started to calm down.
“Because I am gay, too. Your brother got the impression that you were going to come out and he didn’t want you to have to deal with all the crap yet and asked me to try to convince you otherwise. I am closeted and I am very grateful for that. I think Ryan regrets his decision to come out. He is tormented all the time by somebody or another. He gets depressed about it. He asked me to come and try to talk you out of coming out. You don’t have to worry about me outing you since now you could just do the same to me.” I was finally able to explain.
“How do I know that you are telling me the truth?”
“Your brother wondered at first too, but I was able to convince him,” I said smiling as I thought of the kiss it took to make Ryan believe.
“Well, since you already know I guess it can’t hurt to talk to you a bit.”
“Yeah, whether you believe me or not I am open to listen and give you a little advice. That is why Ryan wanted me to stop by tonight. We were gonna hang out afterwards, but I have a feeling he is with his boyfriend.”
“Yep, he goes out with Matt just about every night now. I think its getting serious,” he said this and then seemed to shut everything else out. He went back to his quiet closed up personality. I realized that I was going to have to find some way to earn his trust.
“So it seems like your brother got your situation a little mixed up. Do you want to explain it to me a little more? He said you were thinking of coming out, but you said you never were. How did he get so mixed up?”
“He didn’t,” he replied while looking down at the floor, “I was thinking of coming out, but what he said changed my mind.”
“That’s good, but you just told em you weren’t sure if you were even gay. Why would you want to come out if that is the case?” I asked try to get him to open up.
“I decided that the only way to truly discover if I was gay would be to see if I liked it and the only way I would find that out is if other gay guys knew I was gay.”
“I see, but why didn’t you just try dating some girls to see if you liked that?
“I have no interest in the girls I know, but I am not sure if I will have much interest in guys either. I needed a chance to experiment.”
“Your brother said that you wanted to experience sex, is that true?” I asked.
“Not really sex, per say. Just a romantic relationship. I am not sure if I am ready for sex yet.”
“That is probably a good idea. My advice to you would be to remain closeted and just search inside you to decide fully your sexuality. One huge indicator of sexuality is attraction. Are you attracted to anyone male or female?”
“Well, one,” he replied and then seemed to close up again. I thought I had finally got him to trust me, but I guess it was just getting to personal.
“If you don’t tell me its okay. I was just trying to give you an example of how to determine your sexuality.”
“If that is the indicator, then I am gay. I think I have a crush on you, Dan.” I didn’t really know what to say. I wasn’t expecting that response at all. He must have gotten nervous when I didn’t respond because he began to ramble, “It doesn’t really have to be anything. I mean unless you want it to. I just thought you should know. It is probably just childish anyway.”
“Listen,” I interrupted, “You’re a great guy and I like you, but you are three years younger then me and my best friend’s brother. Plus we are both in the closet which means it would have to be entirely secret. It just seems too complicated to work.”
“I guess it is complicated, but can’t we at least try it out tonight while we are both here alone. We can watch a movie and cuddle. I wanna at least feel what its like to be in another guy’s arms and to have him in mine,” Caleb replied with a look in his that I just couldn’t turn down.
“Alright, but when Ryan gets home we should stop, I don’t know how he’d react.” With that he flipped on a movie and settled on the couch next to me. He was so sweet, he scooted right up next to me. It seemed only natural that I put my arm around him. It wasn’t long before he got so comfortable that he fell asleep with his head resting on my chest. He was adorable and it made me want to try secretly dating him even if he was three years younger. It was so nice to have him there in my arms that I too fell asleep. I woke up at about ten and couldn’t help myself, I kissed Caleb’s head and ran my fingers through his hair. He woke up when I did that and looked up into my eyes. I felt like this could be a special moment for him so I leaned down and gently kissed his lips. I knew I would probably have to teach him the process so I pushed my tongue through his lips and played with his tongue. Our tongues intertwined a gently wrestled each other. It was a wonderful kiss. It was so innocent and so pure. We broke off the kiss and he smiled, “I think I love you, Dan.”
In the passion and heat of the moment all I could do was reply, “I think I love you, too.” He leaned up and began making out with me. This time it was different he kissed with more of a need He wanted something more. I returned the kiss and tightened my arm around his lower back pulling him in closer. He pushed me so that I was lying on the couch and lay on top of me. I began to want him more then anything else and knew that he wanted me, but I was the elder and I thought that I should do the responsible thing so I broke the kiss and said, “Caleb, this is absolutely wonderful, but this is going to go a lot further and I want to be sure that you are ready for it.” He just smiled and continued kissing me. I was sure of what he wanted now so I let my hands drop down to his ass and massaged each cheek gently. He moaned quietly and began running his hands all over my chest. He started to pull my shirt up and we broke our kiss so that he could pull it over my head. After he got that off I figured that it was my turn to take control and show him how things were done. I rolled over so that I was on top and kissed him once again as I pulled his shirt up over his head. His abdomen was revealed to me for the first time and I adored it. You could just see muscle tone forming around the pecs and his stomach was beautifully flat. He had tiny little nipples that were beginning to stick out. I flicked each one with my tongue and he moaned with pleasure. I sucked on one while I played with the other and he was absolutely loving it. I was having a lot of fun, but I could tell from his moans that he was close to cumming so I figured that I had better stop. Reluctantly I pulled up from his chest and kissed him quickly on the lips.
I leaned back and smiled at him as I grabbed his shorts and pulled them off. He was wearing boxer briefs and I could see his bulge trying to break through. I kissed the tip of his covered dick and his waist right above the band. I moved him to a sitting position and got on the floor in front of him. I pulled his briefs down and off. I slowly kissed my way up his legs, starting at the calves and moving all the way to his thigh. I could tell he was ready to explode so when I wrapped my mouth around his five inch dick I made sure to go slowly so that he could really enjoy the experience. He went wild with excitement on the first few strokes and wrapped his legs around my back pulling me in tight. He began to slide off the couch so he grabbed the back of it to support himself. I worked my tongue all along the underside of his dick as I sucked on it. In just a few strokes Caleb began to cum. His semen tasted almost sweet as it cascaded into my mouth it was like nothing I had ever tasted before, very different from either Josh or Ryan. I loved it.
I thought he might need a break after that excitement so I sat down next to him on the couch and shut my eyes. However he was a very energetic guy and began sliding my own shorts off. He had barely pulled my underwear past my knees before he began sucking my dick. He must have been really looking forward to tasting a dick. He was inexperienced and mimicked a lot of what I did to him, but it was still fantastic. He licked my slit rapidly to start which brought me close to orgasm very quickly. His lips slid easily up and down my shaft as he sucked and sucked. His tongue continued to work as he went and I grabbed his head and began to force more of it down his throat. He tried to take it all in, but couldn’t quite do it. I loosened my grip a bit so he could breath, but then tightened it again as I sent my sperm into his mouth. He tried to swallow it all, but began to choke and spit my dick out so the last couple of shots hit his mouth and face. I pulled up to the couch with me and began to clean his face. When I finished I kissed him sharing what was left of my cum with him. We continued to make out for a few minutes before he broke the kiss and said, “Dan, I want to fuck you.”
He had gotten hard again so I smiled at him and laid on my back with my legs spread wide. “Just line it up and push,” I advised him. He didn’t need much advise after that as the passion took over. He pushed it in cautiously, not knowing what he was doing, but once he felt the tightness he began lunging in and out. The tempo was quick and it felt great. He was moaning wildly and so was I. It was something about the way he moved that seemed to stretch me more then I had been stretched before. It was as if he was opening up a new passage that was ten times more pleasurable then his brother or Josh had found. I was very hot and getting very hard again, but his inexperience got the best of him and he came in a few hard bursts that went deep inside me. He collapsed on top of me and I kissed him.
I told him to get on his hands and knees. He complied reluctantly as he was exhausted. I knew he would really enjoy what I was about to do even if he was tired. I spit on his asshole a few times to lube him up so that it wouldn’t be too painful. His hole was very tiny and I knew it was going to hurt him a bit. I lined up with the hole and slowly pushed. The initial pressure made him cry out in pain, but I pushed anyway. Once I got the head in I stopped and told him to relax. He whimpered a bit, but I felt his hole loosen slightly so I pushed a little further. Once again he cried out in pain. Once I got half way in I stopped again and reassured him that I was almost in and that it would stop hurting soon. I decided to put the last few inches in a lot faster to minimize the length of his pain, like ripping off a band-aid. I pushed in the whole way and he screamed and I mean screamed in pain. I stopped and leaned forward hugging him and kissing his neck and whispering that it would feel better in a little bit. He turned his head to the side to look at me and there were tears in them. I felt so bad that I had hurt him so much, but through all that pain he didn’t once tell me to stop. We stayed in this position for a while until I could tell the pain had died down a bit. I slowly pulled out most of the way and moved back in very slowly. I could tell that it still hurt him, but it wasn’t as bad this time. I continued very slowly thoroughly enjoying his tight hole. It squeezed my dick in ways I couldn’t believe possible. I thought for a second that it might have been too tight and that his cries of pain would not stop, but as soon as I had thought it. His groans turned to moans and he started loving it. He began to rock back into my thrust so I started speeding up. Before too long I was ramming him hard and fast. Soon he told me to stop because he was going to cum all over the couch. At first I couldn’t believe that he had a third load in him, but his moans grew louder so I thought he must have. I roll us both over and spun him around so that he was on top facing me. He started doing all the work bouncing up and down. This change of position brought me to an unexpected orgasm and I shot my load hard into him. Feeling my cock pulse and sperm shoot out pushed him over the edge as well and he came all over my chest.
He fell on top of me completely exhausted and whispered, “I am pretty sure that I am gay.” We laughed and then dosed off right there on their couch.