6 comments/ 42167 views/ 5 favorites Be Careful What You Hope For Ch. 01 By: Craysee I grew up as a normal American boy.... Air Force brat, moved around a lot... finally settled in Atlanta. I played sports, liked and pursued girls, got into and out of trouble. Every once in a while though, I went through some gay sex fantasy phases. I'd think about it, masturbate to thoughts of it, and even played with my asshole while jerking off on occasion. But these phases would be short lived... a few days here and there throughout the year, all while I'd be in relationships with girlfriends and such. This went on through jr. and sr. high school, and through my two years in college. After college, I hung out in Atlanta for a few more years. And, the fantasies continued. One of my favorite things was to look at the local independent news paper- Creative Loafing. It had personal ads in the back for people to hook up. I'd read through them every week and have fantasies about the one that stuck out the most.... Ironically, it was about the ads of men claiming that their cock stuck out the most! As a young man in my early twenties, I always seemed to enjoy the thought of being with older men... older, well-endowed men. See, I'm not packin' a huge cock. It's about 5 ½ inches and average thickness. Ever since I saw my first porno, I envied the large penis. So, in my mind, I gravitated toward what I didn't have.... BIG cock. By this time, I'd already invested in a couple dongs and dildos for play. I'd cram them up my ass and fuck myself real good while jerking off. It was great, but I couldn't help but wonder what it would be like to be fucked by a man... someone else controlling the fucking.... Not my hands doing it. After a rather nasty break up with a girl,... OK, I got seriously dumped... heart broken and all, I didn't want much to do with chick for a little while. I resumed my gay fantasies after a pretty long hiatus. I grab and paper and glanced over the ads. Boy, did one sick out. SWM- 50 yrs old- WELL hung- seeking younger newbie to show the ropes- N. GA Mountains- BOB. It also listed his phone number- this was before the internet had come on full swing. So, after a couple nights of thinking about it, I decided to pick up the phone and call the number. I was so nervous. I didn't know what to say. He answered the phone and I weakly spoke: "Is this Bob? He replied, "uh, yes it is. Can I help you?" I said, "Hi. I'm calling about your ad in the paper, the personal ad?" I could tell that he knew I was nervous. He was very calm and patient with me. He assured me that I had nothing to be nervous about because nothing would happen that I didn't want to happen, in that conversation or beyond. He asked me why I was calling and I told him about my fantasies mainly involving thoughts of older men that were well hung. How I was primarily straight but was in between relationships and figured it might be a good time to act on some fantasy. I told him that his ad seemed sincere and that's what I needed.... He assured me that he would be nothing but kind, gentle, and patient with me. So, after a few more short phone conversations, I finally asked what I could expect in an encounter with him considering that I knew nothing about gay sex. Bob, then told me how me might introduce me. He said, "Well, I'd love for you to come up to my cabin here in the mountains. We could have a drink and chat, but I usually like to just get down to the fun. I'd like to initially just please you, and not ask much of you. Obviously if you wanted to do things to me, I'd be open to that, but most of the first- timers that I've been with have been so over-whelmed that it's better for me to lead. I'd probably start by undressing you, and rubbing my hands over your body. I'd be pretty quick to get my mouth on your cock. I'd certainly love to eat out your ass and then if you were up for it, I'd love to fuck you." "Wow" I said. "You make it sound so easy, and laid back. When can we meet?" He said, "What are you doing tonight?" I couldn't think of anything. I was off work the next day. I really had no reason to not do it other that fear.... And I wasn't going to let fear get in my way. So I told him that I'd come up there. He sounded thrilled with himself that he had not scared me off and that me was gonna possibly get some action that night. He told me that his cabin was a little off the beaten path and that he meet me at a gas station in a nearby town and let me follow him to his cabin. We planned on meeting at 8:00. I spent the rest of the day just dreaming about what the night might hold. I showered and was very careful to clean myself very thoroughly. I dressed fairly casual not thinking that we'd be out in public or anything. I grabbed a couple condoms from my drawer just incase he didn't have any, and just incase it actually went as far as him fucking me. When it was time, I hopped in my truck and headed up to the mountains. The whole way up, about a 80 minute drive, I was so nervous.... half way talking myself out of doing it, and then, remembering how long I'd been waiting to do something like this. I finally reached the town where I was to meet Bob and started looking for the gas station. As I approached it, I had one last mental freak out before telling myself, "You got this, and you're gonna love it!" I parked my truck and waited. With each approaching pair of headlights, I wondered if this was the one. Finally, Bob arrived, pulling up right next to me and smiling in a very understanding kind of way. He knew that this was a big step for me. He said, "Follow me. Once we get to my driveway, you can get into my truck and I'll drive us up to my cabin. It's really steep and with it being dark, it would be hard for anyone to manage the drive up." I nodded and off we went. It was about a 10 minute drive of a nerves roller coaster. After I got past the thoughts of "is this guy an axe murderer?", I couldn't help but wonder how big his cock really was. He described it as large and pleasing but didn't get into specifics. His break lights snapped me from my train of thought and we slowed down to his property. I took a deep breath, grabbed my back pack which had a change of clothes, and some toiletries and such in it, and got out of my car. I locked up and hopped in with Bob. It really was dark out there and I had no idea how he managed to get up that hill so quickly, all while rubbing my leg and then my crotch. I didn't even know that I was hard until his hand touch me. He said that he was glad to see that I was excited about being there. Once we got up to his place, we got out of the car and it seemed like in no time at all we were climbing up his stairs inside to his bedroom. I needed to use the restroom after the drive, and did but then it was his show. He was ready. He knew that I had never been with a man and was excited to get first crack at me. He slowly walked over to me and hugged me. He tried to kiss me but I shied away. I didn't really want to kiss... for me, that's for the ladies. He slowly removed my shirt and began rubbing my body. He licked my nipples and they were hard in an instant. I was shaking with nerves and excitement. He grabbed my belt buckle and unfastened it to free my shorts. As they dropped to the floor, he followed them. He tugged at my boxer shorts and my cock popped out to be greeted with a grin. I was shy about my smallish cock but he said, "this is perfect for sucking." And then in one foul swoop, he took it in his mouth to the base... It was right then that I knew that I was in for a treat. Be Careful What You Hope For Ch. 02 Bob slowly sucked on my cock, paying sweet attention to the underside of my shaft. He used his tongue to wrap up my cock and massage the head. His breath was hot and I could feel the tiny bit of stubble on his chin graze my balls. In a sudden finale to his preamble, he took my cock all the way into his mouth as far as it would go and while trying to swallow it down his throat, he licked my balls at the same time. I was in awe! And with one final Hoover like suck, he withdrew my cock and stood. "Come lay down on the bed." he said. I wanted to make sure that he was fully aware that I wanted to play safely, so I said, " I brought some condoms in case you don't have any." And he just grinned. He said, " I have more planned before we get to that, but, let me see them." So I grabbed my backpack and found the condoms and handed them to him. While I found them more than suitable for my average cock, I never really considered that they might not be suitable for him. So, I eagerly moved toward the bed and laid down, wondering what was next. Bob casually moved about the room, dimming lights and gathering supplies for his plan. He grabbed a towel, what looked a couple different bottles of lube, and then some other things that I didn't recognize. He crawled up onto the bed and motioned for me to move more to the center of the bed and sit up. He first asked if I liked to smoke weed, and I responded with a rousing "YES!" He pulled out a nice sized joint for two and lit it up then offering it to me. "This is some great bud that will certainly help take the edge off your nerves." I was already starting to calm down, realizing that this man was making a priority of getting me comfortable. He didn't just want to fuck me and that would be it. He truly seemed to enjoy sharing this moment with me.... teaching me. After a couple of drags off the joint, I was really getting loose. We were sitting Indian style facing each other on the bed. We chatted a bit about my fantasies, and my expectations and boundaries. He made it very clear that if I didn't like anything to tell him and he would stop. I told him that so far, everything was great and that I appreciated his patience and understanding. He gently put out the joint in an ashtray and asked me if I'd like a drink or anything. I said that I was fine and he took that as his cue to resume instruction. He started to rub my arms and shoulders. Then he moved his hands down to my legs and knees, just massaging me to get me used to his touch. He moved his hands to my crotch and gently started to tug on my cock, which was hard with anticipation. He held my cock in his hands and just gently squeezed it. Then he took one hand and cupped my balls, just feeling them. He seemed to really love this moment. He then gently pushed me back to lay down, my head on a pillow. At this point, I was pretty much ready for whatever this man wanted to do. I was so relaxed and comfortable... still a bit nervous but not distracted by it. He continued to rub my cock and balls as he shifted his body into position for his next moves. I just closed my eyes and let my senses do the work. I felt his breath moving around my belly and inner thighs, teasing me. I couldn't wait to feel his mouth on my cock again. Then I felt him shift toward my feet. I felt his tongue move over my toes and then in between them.... Slowly, he treated each toe to it's own mini blowjob. Then moving up my legs, licking behind my knees, and up my inner thighs, he finally reached my crotch again. He grabbed me calves and raised my legs up toward my body, completely exposing my cock, balls, and ass. He started to lick my balls, just under my balls, all around my balls. It was amazing. I just couldn't wait for him to put my cock in his mouth. Just as I thought he was going to move toward my cock, he went the other direction. His tongue moved slowly toward my asshole. Gently wiggling it across the hole, he teased me in a way that I'd never experienced. He started to lick my hole up and down, just like I'd do to a clitoris... flicking it with a stiff tongue. He then started to push the tip into my pucker every third or fourth swipe across my hole. By now, I was going crazy. I couldn't believe that this was happening to me. I was in heaven. I could feel how wet his mouth was getting my ass. His tongue was now darting in and out of my ass furiously, fucking my ass with his tongue, reaching as far as he could inside me. I then felt something else enter my ass. I soon realized that it was one of his fingers. Slowly he worked it in, massaging my opening and the inner walls beyond it. He then retreated his tongue to my taint and balls and let his fingers really start to work on my ass. I was amazed at his skills. He was rubbing what I now know is my prostate. I was suddenly caught off guard when I was getting wet on my chest and face. I opened my eyes and saw that my cock was spewing cum all over me as Bob was furiously finger fucking me. After this very different orgasm subsided, I looked to his face and he was glowing with accomplishment. He too knew that this all happened without him even touching my cock. He allowed me to regain my composure and asked how I enjoyed it. I could only muster a "Wow". Be Careful What You Hope For Ch. 03 I kind of dazed off for a little while, just trying to let what just happened soak in. Bob just laid there next to me and let me be quiet for a little bit. Finally, it occurred to me that I was being terribly rude. This man had done so much for me already and I had not even rubbed on him in any kind of way. I wasn't sure that I was ready to suck a cock or anything but I knew that I wanted him to get off. Shoot, I hadn't even seen his cock yet. I was eager to know how big it was. I finally spoke up, " I guess it's your turn now, right?" Bob asked, " What do you want to happen next?" I said," I want you to fuck me." Bob tried to remain cool, but it was obvious that he was giddy with excitement. He got up from the bed and walked around to my side and stood before me. He took off his t-shirt and let it fall to the floor. Then the next thirty seconds seem like a slow motion movie. He unbuckled his belt and then un-snapped his shorts. He slowly pulled his shorts down. He was wearing boxer briefs and was sporting a pretty massive bulge in the front. I could see an outline of his cock, shaft and head. He wasn't fully erect at all though. I couldn't help but wonder how big it was going to get. He then took hold of the waistband of his underwear and pulled them down and stepped out of them. When he stood back up, I was jaw dropped. His flaccid, un-cut cock was hanging there like a big chunk of meat. It must've weighed pounds. I thought that he was semi hard or something in his underwear, creating that bulge and shape. Nope. He was just being contained by his boxers briefs! And then he let the monster out. I'd be lying if I said I wasn't nervous. That thing was a one-eyed beast staring at me. But I figured, that the worst that could happen for me is that it was a little painful and we quit. I figured I'd leave it up to him. After all, he was my new teacher. He climbed on the bed and moved between my legs. He started to rub my cock again and I grew hard. He swung his legs around to engage in a 69. He sucked my cock into his mouth and got to work. He edged his hips closer to my face in hopes of me doing something with his dick. I reached up with my hand and gently touched his hardening cock. It twitched with delight. I wrapped my fingers around the shaft and couldn't believe that this man carried this thing around with him everyday. It was really starting to take shape at this point. I started to jerk him off, using his ample foreskin. I knew that he really wanted me to put his cock in my mouth.... So I did. I opened my mouth as wide as I could and let his cock in. It had a taste that I never encountered before. I wondered if my cock tasted the same way. I did my best for a few minutes but I knew that I wasn't really getting it done. I did manage to get him to a fully erect sate. I estimated that he was a full 10 inches. Not an exaggerated 8 inches.. a full 10 inches. His cock was easily 2 inches in diameter. As far as a blowjob was concerned, my first blowjob, I was way overwhelmed. But I was pretty sure that I could manage to get that into my ass. So, I asked him.... "Are you ready?" He sat up and said " I'm going to do my best to make this the most pleasurable time you've ever had" He reached over to his nightstand and open the drawer. He pulled out a little plastic container that was sealed with plastic wrap. He also pulled out a little glass bottle that looked like medicine or something. I asked what those were. He said, " well, this is a big boy condom. No offense, but I'd have a hard time getting the rubber you brought on my cock without worrying about bustin' it. This is built big and strong. And these are poppers... another little something to take the edge off." He explained poppers a little bit more and I was sold. He asked if I would like to put his rubber on for him. I was more than happy to oblige. I stroked his cock a little bit more and then opened the little plastic container. I pulled out a sloppy wet balloon of a rubber. This thing was the Cadillac of rubbers. I slowly unrolled it down his monstrous cock. I asked him how he'd like to take me and he said that he wanted to look into my eyes while fucking me, so I laid back. He then grabbed a bottle of lube and then proceeded to get me all sorts of slick, prying my ass open a bit more with his fingers. Once I was ready, he grabbed the bottle of poppers and took a whiff, then offered it to me. I inhaled deeply and laid back again. He started to rub his cock head against my asshole, applying gentle pressure. His cockhead felt massive compared to any of the toys I had used before. He started to push in harder and told me to push back against him like I was trying to shit. So I went with it and his cock started to manage it's way in. I took another whiff of the poppers as I adjusted to the size of his huge cockhead. It was a bit painful at first. He waited for a few moments and then proceeded to push more. It was this crazy mixture of pain and pleasure at first. He was staring into my eyes, reading my every response to his movements and size. He knew he was huge, he loved that he was huge, and he loved sharing that we me. As he was holding my legs up, working his cock into me, I started to relax. He then started to fuck me... short strokes at first... gradually getting longer. I still had no idea how much of his cock he had gotten into me. I asked him and he said that we had a ways to go. He continued to fuck me and gradually went deeper and deeper. He was a master.... Each time he went a little deeper it hurt but then the pain was soon replaced with pleasure. Then he'd go deeper for more. I started drifting off in to the most amazing zone of pleasure. I loved what was happening to me. I loved Bob's cock. I wanted as much of it as I could take. I'm usually pretty quiet in bed but not this night. "Come on, Bob. Fuck me. Fuck me. Oh, God, yes! " He really turned it on then. He started fucking me furiously. I then realized that his balls were slapping my body with each thrust. I was actually taking his whole, monstrous cock. Every once in a while I'd get this crazy jolt run through my body from his cock bumping my back bone or something. I was in heaven when he asked, "Are you ready to come again?" I didn't really know what he meant. I was loving getting my ass fucked but hadn't touched my cock at all, and neither had he. He then changed up his angle and really started working my prostate over with his huge pecker. I was in utter disbelief that something could feel so good. He was fucking me so good. I just totally gave in and let him do his thing. I started squeezing his cock with my ass which drove him crazy. He started yelling, "Oh, God! Oh, yes! I'm gonna cum! Keep squeezing my cock with that ass! I'm gonna cum!" And in seconds, I felt his cock swell larger! My own cock started to jerk and spew cum all over my chest. He froze and I could feel his cock pulse and spasm. I could feel a warm spot in my ass where the condom was filling with his warm seed. I clinched his cock with all of my anal might! He collapsed on top of me and I wrapped my arms and legs around him. His huge cock was still impaled in my ass. We just laid there like that for a while..... Be Careful What You Hope For Ch. 04 I could feel his cock soften a bit, but even then I was still filled to capacity. Certainly at this point, my ass had gotten to that sweet point of comfort where pain was totally out of the question and it just felt natural to have a cock in my ass. He had fucked me so well. I was riding this full body high. I actually even enjoyed holding him there between my legs and rubbing his back. His arms were wrapped under me and his hands were resting under my head with his head next to mine facing down. His breathing was just starting to settle when he took that one deep breath that we take when catching our breath. He gently pushed up and looked at me with a look of appreciation. He grabbed his cock, carefully holding on to the end of the condom, and withdrew his cock from my ass. It felt so good sliding out, making my ass crave it more. He carefully removed the condom and then showed me the prize. I was amazed at the amount of cum that he was holding. It could have easily filled up a small shot glass. I wondered what that cum would have felt like erupting in my ass but I was happy with my decision to play safe for the time being. I rolled over onto my belly and wiggled around loving the lasting sensations of having my ass plowed just moments before. I reached over and grabbed the joint that was left unfinished and sparked it up. He just smiled and stretched his body out a little bit. I handed him the joint and got up and went to the bathroom. I found a washcloth and soaked it with warm water and wrung it out. I returned to Bob and knelt before him and slowly wrapped his cock in the warm, moist washcloth. Taking my time, I bathed his penis and balls, carefully sliding back his abundant foreskin to clean him completely. Neither of us had said a word. We were both just soaking in this amazing time we were sharing. I then returned the washcloth to the bathroom and while I was in there I glanced at myself in the mirror. I was caught off guard by what I saw. I saw a different "me" than I had ever seen before. I had just been fucked. I had just been fuck well. I had just been fuck so well that my face was rosy and I had this glow to my face that I was happy with. I rinsed out the washcloth and then wiped myself down a bit. I wasn't sure what the rest of the night would hold but was content if that was all. Inside, though, I hoped that we were just getting started. I walked back into the room where Bob was laid back on the bed, leaning against some pillows on the headboard of his bed. His cock was starting to show some life again. I guess he enjoyed the towel bath. He took another drag off the joint and offered it back to me. I said. " Actually, if it's okay with you, I'd like to put something else in my mouth." I then crawled up on the bed, psyched to attempt my second blowjob ever. I really wanted to please my teacher. He had treated me so nicely so far. Bob spread his legs and slid down the bed a little bit to lay back more. I rubbed his legs up and down lightly as I crawled into position. I was very excited to get a hold of his cock now. Earlier, positioned in a sideways 69, I wasn't able to really get a good angle on his massive cock. This time, I had free range to move about however I needed to explore cock sucking. As eager as I was, I made myself slow down. I thought back to conversation that I had with a girlfriend of mine that loved to give head. She said she always approached it like it was a performance. As I worked my hand up to Bob's upper thighs, I looked into Bob's eyes. Again, he knew this was a big moment for me. For the first time ever, I was in "control". But we both knew that at the end of the day, his cock was in control of me. "Thank you, Bob, for being so great to me." I said. "This has been a spectacular first experience with a man. I really couldn't have asked for a nicer person to explore my fantasies with." "It's really my pleasure." Bob said. With that said, I moved my hands to his cock. I took a few moments to really just look at it and feel it. It was so warm and perfectly hard and soft at the same time. I lightly grazed my hand up and down his ten-inch shaft. I stopped at the bulbous head to feel of it and give it a light squeeze, sliding his foreskin down. I took one hand and cupped his big balls hanging loosely below, lifting them up and rolling them gently in my fingers. I then lowered my head slowly. I could sense his excitement and anticipation. I stuck out my tongue and dove deep to his special taint under his sack. I lifted up his balls with my tongue. He moaned with appreciation. As his balls hung split to each side of my tongue, I lightly flicked the crease of his body. He raised his knees up more to expose himself. I took one of his balls into my mouth and gently sucked on it all while licking it. Switching to the other, I lightly bumped his asshole with my tongue. He flinched with encouragement. I sucked on his other ball for a moment while giving my next move some thought. I really hadn't ever considered eating out some dude's ass before, or anyone's for that matter. I really hadn't considered that it would happen to me. But here I was. It had happened to me and I had the opportunity to do it. I went back to licking Bob's taint, teasing him with some downward strokes. With some more moans, Bob convinced me to dive in. I stuck my tongue out and pushed it against his ass hole and just held it there for a few seconds. "Oh, God, yeah." he whispered. With firm pressure, I started to work circles around his pucker, feeling the complex ring of wrinkles. I started to lick at it as my saliva was running toward the tip of my tongue. I started to make long licking strokes from the back of this hole, over his hole, and then up to his ball sack. This was driving Bob crazy. I finally went in with my tongue to pierce his entry. I pressed my way in to his slobber soaked ass. "YES! Just like that!", Bob cried. I started to fuck his ass with my tongue faster and faster. I was starting to get deeper in and feeling other textures of his opening. The smooth walls beyond his tight pucker were so inviting. The thought then occurred to me that he may like to get fucked too. Most of what I understood about man sex was that there was typically a giver and a receiver or a top and a bottom. We had talked mainly about what I wanted but, actually, very little about what he desired. After darting my tongue in and out of his ass to the point of my tongues exhaustion, I licked my way back up to his balls and nuzzled them once again. His cock was throbbing and hard as a rock. I looked at his cock head and it was oozing with pre-cum. I then started at the base of his shaft and slowly licked up to just under the head. I started to just flick my tongue under the edges of his head. I worked my tongue up each side of his cock from the base to the head. This was a lot of ground to cover considering how big his dick was. I knew how much I loved getting hands free head from girls so I figured that would be a great way to start out with his cock in my mouth. So I finally reached the tip of his dick again and very slowly let him in. I softly closed my mouth around the meaty head and just held it there for a moment. I started to slide my tongue around it while it was in my mouth and could taste his pre-cum. My mouth was gushing saliva and it was running down his shaft. I had my hands on his hips, right wear his pockets would be, holding him down just a little. I slowly lowered my mouth down his shaft, his cock head rubbing along the roof of my mouth toward my throat. I started to move my mouth up and down on his prick, trying my best to not let my teeth get him. He was just so big. Each time I went down I pushed a little further. Because his cock curves a bit back toward his body, I had some trouble getting passed a certain point. I wanted more though. I then moved my body and threw a leg over his chest so my ass was basically in his face. I wasn't really going for anything but a better angle on his cock. I took his cock back into my mouth and it was an amazing difference. His cock just curved with my tongue and contours of my mouth and I was able to really get to work. As I sucked on his cock, I found myself able to go further and further down his shaft. I pushed myself and got the head into my throat. My hands found their way under his ass and I was able to then pull my head down, forcing his cock into my mouth and throat further. "Oh, yes! You're doing great, baby! Suck that big cock!" Bob moaned. I closed my eyes and sunk into a rhythm. It was fascinating. I was sucking cock. And from what I could gather from Bob's response, I was sucking cock well! He was moaning and squirming like crazy. He was reaching up over my back to my neck and was starting to push my head down. I opened my eyes and saw how close my nose was to his balls. I was deep throating this man's cock. I sucked furiously and I watched as his balls began to tighten up to his body. I knew he was close to cumming. "Shit! This is amazing! Keep sucking! I'm gonna cum!" And within moments, as he held my head in place for a moment, streams of Bob's hot cum were shooting into my mouth and down my throat. I did my best to swallow it all but some leaked out of the side of my mouth and down his shaft. I kept working on his cock until his orgasm subsided. As his cock began to soften in my mouth, I continued to suck up the remaining cum and juices. I let his cock slide out and rested my head on him. As I lay there catching my breath, I was pleased. I had done well. I had sucked that big cock to completion. I closed my eyes as Bob's hands started to rub my back and shoulders in appreciation. "That was phenomenal. Are you sure you've never done this?" he asked. "First time." I said as I felt his tongue slide up my ass crack... Be Careful What You Hope For Ch. 05 It seems that my blowjob performance sparked a hunger in Bob. As I laid on top of him in the 69, just after sucking his huge cock to completion, he started to eat my ass furiously. He was licking on the backs of my balls that were sticking out from between my crotch and his chest. He'd toy with my balls and then take a long swipe of his tongue up the length of my crack, playing with my hole along the way. He let his tongue hover over my taint and apply pressure in a massaging kind of way. His hands were grabbing and squeezing my ass, pushing my cheeks together with his tongue and nose in between them nearly suffocating him self in my flesh. My cock was straining to harden while pinned between us but it would not be denied. He felt this happening and help me lift up a bit so he had access to my cock. He pulled it back to his mouth and wasted no time playing with it. "Fuck my lips! Fuck my mouth!" Bob demanded. I started to rock my hips up and down, forcing my cock in as far as it would go. Bob held me in deep and massaged my cock with his swallowing throat for a while before releasing me so that he could suck on my cock head. Flicking my entire length with his tongue, I was going crazy. I then felt his fingers finding their way to my ass hole. Still sopping wet from his tongue lashing moments before, his fingers sunk right in. I was fucking his mouth and his fingers were fucking my ass. I was squirming all about, rubbing his legs and thighs. "Give me your cum!" Bob cried with my cock in his mouth. I couldn't help but oblige. I sped up my pace and Bob increased the suction. It wasn't long before I was at the point of no return. Bob knew it and pulled me in as far as I could go and then worked my ass with his fingers. "Oh, God! Here it comes!" I warned him. My orgasm crushed me. It was my first cum that night that wasn't purely prostate massage induced so the contact attention to my cock was so intense. My body seized and I must have cum buckets as Bob struggled to keep up. He was determined to drink every drop of my seed. I shook in ecstasy as my orgasm through my body. I could feel this one in the tips of my toes. As I regained composure I opened my eyes to see that I had nearly clawed the skin off of Bob's thighs. I had no idea. There were a couple of scratch marks where I even drew a little blood. "Oh my God, Bob. I'm so sorry. Look what I did to you." "That was so hot! And you were enjoying yourself so much that it didn't even bother me. You'll just have to help me take care of my wounds." Bob said with a grin. "I wouldn't have it any other way. Maybe we should take a shower and get cleaned up." I said as I pried myself off of Bob and sat on the bed. "I have a better idea. Right behind my cabin, there runs a crystal clear creek. I have a little landing built with lights and comfy chairs right on the water. Lets go dip in the creek and relax for a bit under the moon." Bob suggested. "Sounds great to me! Tonight just keeps getting better!" We got up and Bob grabbed a few towels. I was still amazed at the size of his cock as it hung between his legs like an elephants trunk. I had a huge sense of accomplishment run through me. I had taken that thing on and done well. Bob saw me looking at his penis and spoke up. "I really hope you get used to this thing hanging around!" he laughed. "I hope so to. " I smiled. We went downstairs and I finally got to see his crib. He had done well in life. His place was very well put together with nice furniture and a nice kitchen. "What would you like to drink? I have some great wines and beer." Bob offered. "On second thought, allow me to make the selection. We have some celebrating to do!" Bob said as he opened up a large wine cooling cabinet. He grabbed what looked like champagne and a couple glasses and off we went. He had a very cool lit path that split the woods for about an eighth of a mile to the water. It was beautiful. The sound of the creek was like a symphony of nature and the light from the moon was perfect. There was a little house adjacent to the landing. I asked what was in there. "Its' a just a bathhouse with some storage. It was a pain for any lady friends to have to hike back up to the house when they needed to go to the bathroom. We guys have it nice in that regard." He went inside and grabbed a couple cushions for the chairs that were on the landing. He threw one at me and I situated it on one of the chairs. I grabbed the other one from him and he started opening the bubbly. He poured two generous glasses and handed one to me. "Here's to a fabulous evening so far. I think it's clear as that creek that we click sexually. I really hope that we can continue to explore our chemistry." Bob said as he raised his glass. "Here, here!" I exclaimed as I raised my glass. I also felt that I needed to say something to acknowledge my appreciation for the time that Bob was sharing with me. "I can't thank you enough for everything that you've shared with me. I showed up here tonight not knowing what to expect. Actually, I expected to have a very awkward attempt at getting it on with a guy that would end with some form of disappointment. So far the only disappointing thing is the fact that I will have to leave at some point. I figured that bigger was probably better and really hoped that it would live up to that notion but I had no idea that things that happened tonight were possible. You made me cum twice without even touching my cock. I'm in awe and now certain that I'll forever crave your massive cock." Bob grinned and as he lead me toward the water, he said, "Be careful what you hope for." Be Careful What You Hope For Ch. 06 A month had passed since my first encounter with Bob and I couldn't get my mind off of him. After an amazing night of sex in his house, we adjourned to his dock on a creek behind his house to enjoy some champagne. We celebrated me, as he put it. I certainly was up for that. I had just had the best few hours of my life. We slugged down a couple bottles of bubbly and talked a lot. We didn't know much about each other before the night began but seemed to immediately bond. I really didn't want the night to end but I knew it had to. We walked back up to his house and I gathered my things. I thanked him again for treating me to such a wonderful evening. And then I left. The entire drive home was full of thoughts of delight, amazement, and extended curiosity. I couldn't help but wonder how much further we could go. If it was that amazing for our "awkward first time", how amazing could it get if we got more and more comfortable with each other. I could only hope that I'd have the opportunity to find out. Bob had mentioned that he was about to do some traveling for the next couple weeks and that he'd be hard to reach. I had a busy stretch ahead of me at my job and we just settled on touching base in a few weeks. I told him I'd leave it up to him to call me when he was back home. Boy did time seem to creep by. Work kept me pretty busy and all but I was full of anticipation for the next time I'd see him. The crazy thing is, I wasn't at all interested in him romantically. But, I was in love with his cock and the way that he used it. He was a friggin' maestro in the sack. He knew just what to do and just when to do it. And I couldn't wait to ride that roller coaster again. Finally, the day came that my phone rang and it was him. I answered eagerly only to find out that he was not back home yet. His trip had taken a detour, something about a great deal on an ad-on itinerary. He asked what I was doing that weekend and as I had nothing going on in hopes of being with him, he invited me to come meet him. He just said to pack a light bag and head to the airport and a ticket would be waiting for me. I couldn't believe it. I asked him where he was and he said it was a surprise and I'd find out at the airport. The next 36 hours until I had to be at the airport drug by. But, I did do my best to tidy up my body and tried to refrain from jerking off too much in anticipation. Friday afternoon came, and as work ended I hopped in the car and headed to the airport. I went to the ticket counter as instructed and learned that I was flying to the Bahamas. HOW CRAZY! I had never been there before. It was a quick flight of two and a half hours. I walked off the plane to find a person holding a sign with my name on it. I went up to him and he said that he'd be taking me to my final destination. I was completely blown away... this seemed straight out of a movie or something. But for some reason, I never felt nervous. I just went along with it. The car ride was 15-20 minutes through non-touristy Bahama. We ended up in what seemed like a residential neighborhood. It was nearly dark so it was hard to tell where I was going. But finally the car pulled into a driveway of a rather large house. The driver grabbed my bag and led me to the door. Bob opened the door as we approached and he looked so happy that I was there. He gave me a big hug and welcomed me to his "home away from home." I couldn't help but just blurt out, "who the fuck are you?", when I started to look around his home in the Bahamas. He just laughed and said that he'd been fortunate in some of the business decisions that he'd made in his life. "No kidding. This place is amazing." I said. It was obvious that I was standing in a man's home. There were no signs of a female presence there whatsoever. And, I don't mean that in a messy, bachelor kind of way. The place was very neat, simple, and classy. "What can I get you to drink?" Bob asked. "I'd love a Cuba Libre." I said just testing his drink knowledge. "Coming right up... and help your self to the box on the coffee table." he said as he headed into what I guessed was the kitchen. I sat down on a very beautiful leather couch and took a deep breath of island air. The windows were open and I could hear the ocean gently crashing nearby. I reached over and opened a very cool hand made wood box. To my delight it hosted a small pipe and a few small bags of amazing looking bud. I examined them and chose the one I thought would be cool to try. I lit up a small hit not knowing the potency of this weed and inhaled not only the smoke from the pipe but a familiar breath of anticipation. Bob came back into the room with a perfectly mad rum and coke with a wedge of lime and sat down next to me. "I hope this isn't too stiff." Bob said. "Is there such a thing?" I said gently moving my hand to his crotch. Bob laughed. "I was a bit nervous about inviting you here. We really don't know each other all that well. Our only time together was one night a month ago. But that was such a special night that I wanted to thank you with a weekend away." "I'm amazed to be here." I said. "I've loved thinking about our night together and about being with you again. You really blew me away. I didn't know sensations like that were possible." "I'm so glad that you had a good time. I really don't consider myself that kind of a sexual master. I just really care for the men that I'm with and treat them with the attention that I hope to receive." Bob then continued to talk nervously. I wasn't really sure why he was nervous. It seemed kind of a first date kind of nervous but I decided to calm his nerves right away. I moved right through his rambling to the floor between his knees. I reached up and unbuttoned his shorts and he slowly unfinished whatever sentence he was in the middle of. I pulled out his cock which was just a smidgen more firm than flaccid. I admired it once again and took a moment to relish in Bob's presence. I gently stroked his cock with one hand while I packed him a bowl of that righteous weed with the other. I handed him the bowl and a lighter and said, "Just sit back and enjoy sir. I've been waiting for this moment for too long." I then tugged on his shorts and he raised his butt a little so I could get them off. He took a pull off the bowl and laid his head back into the couch. I slowly stroked his cock with my right hand while gently rubbing his belly and chest with my left. I leaned my mouth in and began to lick his balls... just massaging them around and over. His moans were as if he'd been waiting for this too. I snuck my tongue under his sack and reached for his taint. He squirmed a bit in joy. Over the many days prior, I had wondered what it would be like to taste his pucker again. I was weary of the obvious concerns to a un-experienced person. I kind of did that test sniff... like you'd do to a chick before licking her snatch. I honestly was surprised at how clean he smelled. I figured that there was no time like the present to explore this new skill. So I wriggled my tongue slow down his taint... painfully slow. So slow that I could feel his wonderment at if I was going to do it or not. Finally, I answered his question. I gently grazed his hole, just wanting to tease at first. By this point his cock was rock hard in my hand. I continued to stroke him as I worked more on his asshole. I worked in small circles getting bigger and then back to small focusing on the center of his hole without even the slightest bit of penetration. After I could tell that he was beyond any more teasing, I began to lap at his hole making sure to leave behind plenty of saliva. Every third or forth cross, I gently began to dart my tongue in a bit. This was driving him crazy. I also would take some longer strokes with my tongue from his hole up to his balls again. After a little while of this, I wanted more. I wanted to taste his cock. I could feel his pre-cum on my hand that was stroking him and I wanted to have that in my mouth. I slowly worked back up to his balls and lower shaft. I began to lick slowly up his shaft, teasing with the notion of reaching his cock head but not getting that far. Bob was absolutely a mess at this point. I could tell that he was ready to explode. I grabbed his sack in my left hand with my thumb and fore finger acting as a sack ring, separating his nuts from his body, hoping to slow down his explosion. With long warm breath, I slowly moved my mouth over his cock head. I initially took in as much as I comfortably could knowing that I wanted to just hold his cock in my mouth for a few moments and feel his warmth. I could actually feel his pulse on my tongue as I wrapped it around the underside of his shaft. I began to suck gently and work my mouth up ad down his cock. I felt his scrotum battling my hand in hopes of releasing his seed. He wanted too and I wanted it. I continued to work long slow strokes, never removing his cock from my mouth. As I held his sack, I began to tickle his balls that were straining against his skin. I felt his cock swell even more in my mouth and begin to throb. I knew it was coming and I knew it would be huge. I sped up my work on his cock and slowly released his balls to do their magic. I worked hard to take his cock as far as I could down my throat on each stroke but when I could tell that he was about to explode I created a reservoir in my mouth to collect his load. He then gently grabbed my head to let me know that it was time. I furiously worked his cock with my tongue and it came. The most amazing rush of cum I could have ever imagined. Burst after burst of hot semen blasted from his cock into my mouth and throat. I swallowed what I could but some escaped from the sides of my mouth. Bob sat there in a daze. His cock had slowly begun to soften in my mouth. I licked it clean and continued to rub his belly and chest while I did. I then reached behind me and took a decent tug off of my half melted drink. "It's perfectly stiff, thanks!" Be Careful What You Hope For Ch. 07 Bob slowly regained his faculties while I finished my drink. I asked if I could get him a towel or something to that effect, not knowing what he had planned for us. "Sure. You can grab a clean dishcloth from the kitchen while you're getting us some refills.", Bob said jokingly trying to imply some dominance. "Well... yes, Masta!" I played along. He smacked me on the ass while I got up and headed away from him toward the kitchen. If I wasn't wearing shorts, it probably would have stung pretty good. Up until that point, I had never really thought highly of pain involved with sex. I was quietly hoping that Bob wasn't "into" that. While I totally trusted that Bob would never cause real harm to me, I really hoped that his deeper interest sexually wouldn't clash with mine. While we had already had a great time together before, it was all pretty vanilla sex. Other than being man on man sex, there wasn't a lot of kink about it. I got our drinks and a towel and headed back into the room we were in to find him no longer there. A door was flung open to the outside and I headed in that direction. Bob was laying buck naked on an outdoor lounger. His cock glistening in the moon light caught my eye immediately. I still was amazed that he carried that thing with him all the time. It really was magnificently huge. I handed him his drink and sat down next to him. "So, what do you have planned for us this weekend?" I asked. "Well....I was hoping to pick up where we left off last time." Bob replied. "Well, of course. Obviously, I want that too." I said while I could still taste his cum in my mouth. Bob continued, "I was hoping to show you one my toys." "What kind of toy?" I asked expecting some type of dildo or plug or something. "Well, it's kind of a harness...something to keep you from getting away." he said with a grin. "Umm.. I've never really been into the whole domination/pain thing. I'm not going anywhere so you don't have to keep me captive." I explained. "I don't want you to misread what I'm telling you. It's really just a way to allow you to totally let go. It's nothing crazy, I promise. But we'll get to that later. Why don't you get more comfortable?" suggesting that I join him in the nude. I stood up and slowly undressed. While I wasn't playing into the whole strip tease thing, he was certainly enjoying the show. I could tell he loved my younger body. I made sure to turn around and bend over real good to show my ass as I was pulling down my shorts. My semi hard cock sprang forth and bounced as I stood back up and turned around. He motioned for me to come over to him and I obliged. I straddled the lounger that he was lying on and presented him with my cock at about his face level. My cock paled in comparison to his but he didn't seem to mind it at all. The breeze off the ocean was just perfect. The temperature was perfect. The time was perfect. "This is going to be a great weekend!" Bob said. And without saying another word, Bob opened his mouth and took my cock in down to the hilt. It totally caught me off guard. He just jumped right on it. He applied a gentle but constant sucking on my cock as my cock head bumped the back of his throat. He slowly backed off of it resting his head on the lounger. He reached behind me grabbing my ass and pulled me toward him I grabbed hold of the top of his chair and he started to lick my balls. He washed me thoroughly. "I want you to fuck my face." he demanded. As I held the chair, I moved my cock to his lips. I started to push through as he closed his eyes. He created this amazing hole in his face with his mouth for me to fuck. I worked into it slowly, totally savoring the moment. As I reached the end and started to withdraw my penis, he stuck his tongue out to caress my balls. That drove me absolutely wild. I picked up my pace and started to drive in and out... in and out. He manipulated his sucking around my thrusts. He started guiding my rhythm with his groping hands on my ass, pulling me back in as my cock head had just exited his lips. I grabbed his hands and held them back above his head against the chair. This way, I was in control of the rhythm. He seemed to love that I recognized this and just gave in to my thrusts. I started fucking his face harder and harder. I had just about reached the point of exploding when I had an idea. I knew he would be responsive. I slowly withdrew my cock from his mouth and turned my body around, straddling Bob in the lounger with my ass in his face. I presented him with my pucker as I bent down and took his revitalized cock into my mouth. He knew what I wanted and was eager to please. He dove right in like he was ass starved, lapping away at my ass, darting his tongue in and out. Somehow he knew that I wanted to ride his cock. He wanted me to ride his cock. He got my asshole ready. I was just toying with his cock, enjoying his tongue and fingers in my ass. Finally, I felt ready. I turned back around and straddled him again facing him. He was prepared in the fact that the little table next to the loungers had some supplies in the drawer. He pulled out a bottle of lube and a condom. "Bob?" I asked. "Yes?" he answered. "Are you totally free of std's?" I inquired. "Clean as a whistle. But I'm fine with playing safe." he answered. "I'm clean too. I really want to feel your bare cock in my ass but I'm scared of getting something." "I totally understand. I'm clean. I believe that you are too. And I respect whatever decision you make." I grabbed the bottle of lube from him and squirted some into my hand. I rubbed it up and down his long, thick cock. I then put some on my asshole. I grabbed his cock and slowly lowered my self onto him, his cock head resting on my loosened pucker. I pressed down a bit and knew right away that this would be a strain. I was afraid of the initial pain. I gently rocked up and down using his cock to loosen me, to relax me. He took my hard cock in his hand and massaged me while I worked my way onto his tool. I kept working down a little bit further. It seemed to take forever but I knew that if I rushed it, that it could possibly ruin the experience. Eventually, I felt confident in my readiness. I pushed down further and his cock head slipped into my ass. Wow! It popped right in beyond my sphincter. It hurt a little but I knew I was in good shape. I slowly started to work my way up and down his cock taking more and more in as we went. He continued to play with my cock which help with the little bit of pain. I worked up and down and next thing I knew, I was flush with his hips and his balls were touching my ass cheeks. His whole monstrous cock was inside me. It felt so wonderful. I just rested there for a moment, feeling his member stretch me to comfort. "God, this is good." I said. "It really doesn't get any better." Bob agreed. And with that, I started to ride his cock, up an down. It felt so good. I started to squeeze his cock with each thrust. He began pushing upward to meet my downward stride. Now that we were in full swing, I could initiate my idea. We got into a rhythm where I'd ride his cock for a minute or so and then I'd stand up and fuck his mouth. It was amazing to ride such a magnificent cock and then shove my cock into his mouth and fuck his face. Just as I'd get close to exploding, I'd pull out and pounce on his cock again and just as he was getting close to creaming my hole, I'd pull off and be ready to fuck his mouth some more. This went on for quite a while under the island moon. We were lost in the moment and really couldn't have cared if we had an audience of a thousand people. We were just loving being with each other again. "Please finish me" he begged. I accepted the challenge. I got down on that cock. I started to ride that thing so hard, squeezing him for all I was worth. I leaned back some to get an angle on my prostate. He loved that I was loving his cock. I felt so full... so fulfilled. "I'm gonna cum!" said Bob. I rode him steadfastly, his cock swelling in my ass. I could feel him throbbing and then it happened. He flooded my ass with his seed. It was so warm. It was heavenly. He held me on his cock.... totally impaled on his pulsing cock. This feeling pushed me over the edge and I stood up and slammed my cock in Bob's mouth. Only a couple of thrusts later I was experiencing one of the best orgasms I'd ever felt, shooting my cum down his throat. His tongue massaging my shaft the whole time. After my orgasm subsided, I collapsed on the lounger next to Bob's. I could still feel his warm cum deep in my ass. My cock was tingling with satisfaction. I was truly in paradise!