9th in Series, I Lost a Bet

Sunday rolled by, stuck doing things with my parents and finally after dinner Steve came over. We had just been goofing off shooting some hoops when he said I've been thinking of something, let's go take a little walk. I didn't know what he had in mind until he started heading towards the field leading to the woods, but I knew we really didn't have time to go get involved with something. But when we got to the street he said okay you just stand here and you wait for me to wave and then look really good and then I'll come back here and you tell me what you saw. I watched him walked up over the rise and back down and then could see him walking some more he finally stopped and turned around and waved his arms I didn't know what he was meaning but I could see him so I wave my arms back and he came back to me and he said okay what could you see? I didn't know what he was talking about and I asked him what do you mean I saw you. He said okay, but did you know it was me that you could see and recognize that it was me or could you just see me as a person. I thought about it a minute and said well I guess maybe a little bit of both. What are you getting at I asked and he said well what could you see? I said God what do you mean? He said obviously you could see me and saw me wave and I said yeah. He said how much of me could you see I thought for a second and I said well most of you probably everything from your knees up and he grin I said what are you talking about what's gotten into you? He grinned and he said I was standing in the same spot where you sucked me off last night so anybody that was out here could have seen us. I said yeah but it was dark and they would have had to been looking right at that spot. He said well yeah but no matter what somebody could have been walking their dog or something and they would have been seen able to see you sucking my dick. I said okay I get your point but nobody did and I really don't care because I'm glad I did it. He said yeah but would you have kept doing it if somebody was walking by and I thought for a second I said I don't know probably so because when I'm doing that to you it turns me on and I probably would have kept doing it hoping that maybe they would just stand there and watch. And he looked at me and said wow you would really let somebody watch you suck me? I thought about it for a moment and said well I probably couldn't do it in front of somebody we knew but if we were at some place and a complete stranger happened to come by and they just wanted to watch, I think I would be okay with that and he just looked at me kind of amazed and went Damn! After a moment he said my dad gave me some extra money for helping him pack stuff and move it to the storage unit and last night I noticed our shared pack was getting low so let's walk up to that little store where I'm pretty sure they'll let us buy a pack of cigarettes. I said okay and we started walking but when we got there they were already closed because everything around us closes early on a Sunday night and we had forgotten about the time and headed back home. After a little bit he said, last night as I was showering and getting ready for bed, I was thinking about everything especially because I am leaving in just two weeks I do want to continue experimenting. And as you said to try things we were curious about. I admit it, I was curious to know why you enjoyed sucking me and so I wanted to try it myself and did it and as you said once I done it I figure I'd gone that far and that's why I let you come in my mouth. I guess it will depend on my mood if I do it again or not. I said I'm totally cool with that, remember, I said whatever you are comfortable with. He stopped and he said I know you're curious to know what it's like but I'm sorry I just don't think I would be comfortable to let you fuck me and he looked at the ground a little bit ashamed or whatever it said I'm sorry I just don't think I could do it. I punched him in the arm and laughed and said, I basically knew that, that's why I never asked and to be quite honest I'm happy with the things have been going with just you fucking me and don't worry I won't ask or pressure you at all into anything you don't want to do it's all up to you decide what you are willing or want to do or curious about but it's your decision. We continued walking back to our houses and he said you know one thing that happens to me every time as I get ready to come inside you is that I just wish I had more of a dick to stick more inside you and I just feel like I can't even though I'm totally inside you. I wish I could get more inside of you and I'm not sure if that makes sense or not. I thought about it for a minute and said actually I think I do kind of know what you mean because the last two times as it has been getting really hot close to the end there I've kind of wished I had even more inside me. He turned and looked at me and he goes how much more I said I really don't know I just feel like I want more of you in me as we come I'm not quite sure how to explain it. He just nodded and didn't say anything. As we got near our houses while I still had the chance to talk openly, I said you know with our experimenting a lot of it I realized has been having you do things that I wanted you to do to me for things I was curious about. I know there's got to be something in your head that you are curious about or may want to try and I'm letting you know that unless it's totally freaky I'm willing to try it. So if there is something, think about it this way, with as much as we have done if there's something else go ahead and tell me, who knows maybe it would turn out to be something that we both enjoy but we would never know without trying it. He thought about it for a minute and as we got to our houses he said okay let me think about it. He changed the subject and asked if I had any plans tomorrow and I said I really didn't know what was going on whether my mom was going to have plans for me or not and I said I hadn't really thought about it cuz I didn't know if you had stuff to do or not and he just said okay we will see what happens tomorrow morning.

The next morning I woke to my mom knocking on the door and telling me it was about time for breakfast but it still felt like the middle of the night. I pulled on some shorts and went to the bathroom and then into the kitchen and realized the reason it seemed still nighttime was because it was all dark clouds and dreary and a little rainy, no wonder I still felt tired. After breakfast my mom asked if I had any plans and I said no not really it's so dreary out I figured maybe I just go back to bed for a little bit. She said well I don't have any plans for either of us today so go ahead. When I crawled back in bed I was kind of wondering if Steve had been thinking of anything special and I was wondering about how he had really gotten off imagining I was a girl. I don't know why then but something in the back of my head was telling me that he and I were going to be doing something about that soon as I drifted back to sleep.
I woke up maybe an hour later and it was still cloudy but only drizzling a little and I just didn't feel like doing anything when Steve called and said hey what's up? I said not much, weather sucks and he asked, do you want to come over and shoot some pool? I said yeah I guess we can do that. His parents had a nice furnished basement with a couch and a couple of chairs in case somebody wanted to watch something different than what was on the TV in the living room. But besides the TV they also had a pool table and a little bar area, it was a nice cozy room. After a little bit I went over there and his mom answered the door and said Steve's downstairs so I headed on down and he was just setting up the rack on the table. We played a few games and then his mom called down from the top of the steps that it seemed to be lightening up and wasn't raining anymore so she was going to run out to the store and did we need anything and Steve just called back nah I think we're good and she said okay and left as we finished the game we were on. I think I had won one and he had won two. He looked at me with his mischievous grin and said I think it's safe now and I asked safe for what? He said let's make the next game a little more interesting, care to make a little wager? I said well I guess so what are you betting? And he said how about this, if you win the next game I'll get down and suck you off and let you come in my mouth. I thought to myself after last night talking maybe he's willing to do it more and said okay that sounds reasonable. And then he said but if I win you have to bend over on the couch and get your ass oiled up and he hesitated and I'm starting to like where this is going when he walked over to the rack holding the cues, pulled one down and holding it in the middle started sliding the handle back and forth through the hole between his thumb and forefinger and said, I get to push this inside you. I went what are you crazy! And he said, no, aren't you just a little bit curious to see how much you can get inside you, you said you kind of wished you could get more of my cock inside you so I'm just wondering how much more you could take. I looked at him and said but with the pool cue? He said sure and unscrewed it and then handed me just the handle end and he said look it's nice and smooth and really it's not as big around as my dick and I bet once we put some oil on it and you it would slide right in. I looked down at the cue and realized it was one of the old ones they got when they first got the pool table, that we never used anymore because it was warped and it was just a basic one and didn't have any kind of nice handle or anything just plain smooth wood. Then he said, last night I looked around and I found some of that same mineral oil we can use it and if you really look at it, it's not as fat as my dick. So I’m curious, how much can you take in your ass and aren't you just a little bit curious also? I admit that I had wondered about that and he really had my mind going. So let me see if I've got this straight, if I win I get to lay down on the pool table and you will suck me off and let me come in your mouth and you will swallow it? And he nodded yes, and I said and if you win I have to bend over and you put this inside me to see how much I can take? He said, Yep, that’s the bet. I thought about it and knew I had beaten him playing pool before and he was making me really start to think about it, about how much would go inside me so I took a deep breath and said okay you're on. He grinned and said okay, and if you want we can make it even a little more interesting. I said my God how much more do you want? He just reached under the seat cushion and pulled out a porno mag or two and said, we both get nice and hard and then we play the game naked with hard ons, that'll make the shots more difficult and I'll tell you what, we’ll do this also, and I'm willing to do it, each time one of us sinks the ball they are going for, the other one has to suck us for 30 seconds. I looked at him and smiled and said as I told you yesterday I'm willing to try new things that either one of us are curious about and I admit I am curious to know how much will go inside me. Since you added the other things to it, here's my answer and I was naked in 2 seconds as I sat on the sofa and started to look at one of the porno Mags. Just a moment later he was naked and sitting next to me, looking at one also and after another minute or so we were both hard and slightly stroking. After a couple of minutes we were both super hard and he said, okay are you ready to take that bet? I said hell yes and we got up and started to play. We flipped a coin and he got to break and he dropped one ball in on the break and he turned to me and said remember the rules of the bet, now you've got to suck my dick for 30 seconds. I grinned him and said gladly as I got on my knees and started sucking him and just as I was really enjoying it he said okay time's up. It's your shot now I shot and missed and then he shot and missed and then I sank two in a row. I turned and looked at him and said, a bet’s a bet, that's two balls that's one minute of sucking me. He dropped to his knees and took my dick in his mouth and started to suck me and just as it was really starting to feel good he stopped and said Hey you're not watching the time, it's been over a minute. I apologized and said, what you were doing to me was feeling good and I forgot. He grinned and said okay. I was feeling cocky and said well you better just get used to sucking it anyway cuz I'm going to beat you. He turned and looked at me and said do you really think you can beat me? I said sure I've eaten you plenty of times. He grinned a little and said yeah but probably half of those times was because I let you. Remember this is my pool table and I bet I could beat you anytime I really wanted to. When he said that I thought about it for a second and realized he was right and that he set me up for this bet. I knew that in a very short bit I would be bent over taking that pool cue in my ass. It was his turn and he sank one ball but he had a really difficult lineup for the next shot and he couldn't quite bend over the table to make the shot because of his hard cock and he missed it. So I got on my knees and took his cock in my mouth and started a sucking him again for the 30 seconds but when I realized I had been sucking him for much longer than that I stopped and looked up and his eyes were closed and I said, Hey you weren't watching the time either! He looked down at me grinning and said turnabouts fair play. By this time I started to have some pre-cum leaking and I went to line up my shot and then I changed the angle just a bit so that when I hit my ball it would hit the eight ball and it rolled in and dropped into the pocket. I said damn I guess I lose. He said you did that on purpose and I said prove it, but a bet’s a bet, so I guess I have to go through with it, so how do you want to do this? He was grinning and said you're just a little too eager I think and laughed and I said so what's wrong with that and he laughed again. He was holding the pool cue handle, thought for a second, let's mark it to show the length of my dick and then we can and mark it when you can't take anymore. He looked around and found a pencil and held the cue up by his dick and marked the end of it. Then he reached around the side of the sofa and pulled out the bottle of mineral oil and I knew that he had been planning this all out in advance. He said sit there and I'll hold it and you get it all oiled up the way you want. He held it out in front of me and I drizzled some oil on it and then started stroking it and getting it oiled up, I guess I was just thinking about his dick and stopped when I got to the mark and he said you better oil down more I think you can take more than my dick inside you and I actually agreed with him so I kept oiling till there was about 9 inch of it oiled up. He said it's supposed to be tasteless. You like sucking my cock before it goes into your ass, let me see you suck the end and he had this gleam in his eye so. I realized he was enjoying this and was going to make me pay for losing the bet. I took it in my mouth and realized that yeah it really had no taste, just felt oily was all. He let me hold part of the shaft as he started working it in and out of my mouth and spinning it and twirling as he did and with my eyes closed I was actually getting more turned on even though it wasn't his dick or as thick when I moaned and he said I guess you're about ready for it. Turn around and stick your ass up for me. His voice had grown a little more husky and demanding and I quickly turned around on the sofa and presented him my ass. As he touched it to my ass I realize I hadn't been oiled up or been ready for it so I asked him before he went any further to get my ass a little oiled and I felt some drizzle on me and felt his fingers rubbing it around and then one finger push in side me slightly when he pulled his finger back and instantly the end of the pool cue was pushing at my hole. Since I really hadn't been loosened up yet I said, maybe I just need a little more oil on me and the cue. After he put a little more on the cue, he pushed an oily finger just inside me and stopped. A moment later he was pressing again and I was trying to relax but the end of the queue was pretty blunt and he said I know you really want this and he pushed in harder and it pushed inside me and I cried out, Stop Wait! He said, what's the matter there's only about an inch inside you. I groaned and said yeah but I really hadn't been loosened up and that round in just shoving inside me like that kind of hurt a little, just give me a moment to get used to it. After a moment he started wiggling it around and I think was actually spinning it. As I got more used to it I felt the pain receding and I said okay. He started to work it in and out of me like he does when we fuck and soon he said, okay you got as much in you as my dick. I kind of gasped and said don't stop but go slow. He said I'll just give you an inch at a time. Iheld still as he slowly pushed a little more and then wiggled it and then pushed a little more and then I could start feeling it up in my stomach it seemed like, when I felt it hit something inside me. I gasped and said, Stop and wait a second and then wiggle it and try again. He pulled it back a little and started wiggling it as he pushed slowly a little more and then I felt it hit that same spot again. I said stop, I think that's all my body will allow and he said yeah I can feel it kind of hitting something. He said, reach back and hold on to this so I can get the pencil to mark the spot of how far it's inside you. I reached back and was holding it and was wondering why it was taking so long to grab the pencil when I heard this click and a flash of light and then a little whirring sound and heard him kind of say to himself oh that will be good. I didn't know what had happened. Then he said I'm going to pull it out of you so we can measure it. I felt it slowly sliding back out of me until it was almost out and then he held it there and wiggled it in me for a minute making my hips jump a little. And then I heard that same click and flash and whir and it suddenly hit me that he'd taken some pictures with a Polaroid! And then he slowly finished sliding it out of me and when it was all the way out, he said, Damn you've got to see this! I stood up feeling slightly empty and looked down to where he had put the cue on the arm of the sofa and he pointed to the mark showing how long his dick was and then pointed at another mark almost twice again and he said that's how much you had inside you! I couldn't believe it but I could see the oil and see his mark. He said, wait a minute there's got to still be a ruler around here somewhere and he went looking in a side cabinet. Ah Hah, and he turned around with a ruler in his hand and he laid it down beside the cu and we measured that his cock was almost 7 inches and that I had basically had almost a foot inside of me as it was 11 and a half inches when he measured the mark. Then he said yep we got to get a picture of this also and he picked up a Polaroid camera from beside the sofa and aiming down took a picture of the end of the oily pool cue with the ruler right next to it and then said there it takes a couple of minutes for these to finish developing. And I said, You are an ass! You took a picture of that inside me? He said yeah but don't worry the way it is nobody would know. And I said and how do you know? And he picked up two pictures that had been laying face down and turned them over and said see. I looked and even though they still had not finished developing yet you could tell it was an ass with something in it but that was it and I said okay I guess so. I happened to notice that even though I was the one had had something in my ass, he was hard also and looked at him and I said so I guess that turned you on a little more than I thought it would and I reached over and was caressing his dick. He said yeah I didn't think it would but seeing it going inside you was turning me on. So what did it feel like having that much inside you like that? I just grinned and squirted a little oil on his cock and stroked him a couple times to get him hard and oiled and said I'm not quite sure, I think you better put your dick inside me so that I can compare and tell you the difference and got right back into the same position on the sofa. He was immediately behind me and he had one hand on my hip as he must have been holding his cock to my hole and slowly pushed and since we were both boiled up and I had already been loosened up the first couple of inches of his clock slid right inside me. He had one of those dicks that had a nice shaped head and then from there all the way back to his pubic area, his shaft got thicker and bigger so by the time he only had around two inches in me it was already thicker than the pool cue and as he pushed more I could feel him starting to stretch me open more and more and I moaned and he just slowly pushed more and more until he grunted as he shoved the last of his dick inside me, making me moan more. He just held still for a moment enjoying the feeling and then he slowly started working his hips fucking me slowly and he said okay, so tell me about it. Then holding still and holding my hips he started to pull me onto his cock and push off so that even though he was holding still he had me rocking back and forth on his dick and it was something about him taking control like that that made me moaned some more. He said, okay you've had two things inside your ass, but you seem to like my cock better, even though the cue was longer. I was enjoying the feeling of fucking or being fucked like this and it was kind of difficult to answer as he kept pulling me back onto his cock practically burying it in me each time. Finally he said teasingly, come on, tell me or I'm going to pull out of you and stop and I groaned no no don't! So tell me, what's the difference and kept fucking me. I managed to say I think it’s a couple of things, yeah the cue felt good in the beginning but after that because it's not as thick as your cock is and it’s so smooth it was just sliding in me. It just didn't feel the same not as intense and also not hot feeling inside me like your cock does because sometimes it just feels so hot inside me. And I think the other thing is it's totally smooth and the same thickness from one end to the other whereas when your dick gets hard your veins stick out and the longer you stay hard they get a little bigger and so as your dick is sliding in and out of me it's not totally smooth and depending on how fast or how slow or how deep you push inside me, your veins feel like little ridges and they just kind of set my nerves all tingling and since you're cock grows thicker towards the base each time your thrusting in and out of me it's different thicknesses sliding in and out of me and oh my God what you're doing to me right now is driving me fucking crazy. But I think the primary thing is it was an inanimate object inside me where now it's your hot hard cock fucking me. Now let me shut up and enjoy your dick fucking me. I was really loving the feel of his cock sliding in and out of me as he was fucking me when it suddenly popped into my head. I said take a couple more pictures. He said What? I said yeah take one showing your cock inside me and maybe another one with just they head barely inside of me and then another one buried all the way into me. He wiggled around a little bit I guess trying to reach the camera and then I heard the click and flashes as he took a couple of pictures and then I grunted as he thrust all the way inside me and held it there and I heard him take two more pictures and in my head the thought of having somebody take pictures of their cock fucking my ass did something to me exciting. I started humping back on his dick when he told me to hold still so he could get the picture of his dick just barely inside me I was trying to hold still but everything going on was really getting to me and I knew that shortly I would be coming on his cock. The feel of just his cockhead very barely inside me was really getting to me because I wanted him back inside me. When you’re done having fun taking pictures you better put it back inside me and fuck me. He said, like this and just shoved and buried his cock inside me and I grunted and moaned and said Oh my fucking God yes just like that! I don't know if it was the pool cue or taking the pictures or what, but something turned him on and in no time he was just pounding my ass, making my cock bounce and leak precum. Again I didn't dare touch myself for fear of coming too soon and was just loving and going crazy by the feel of his cock just fucking me harder and faster. I happened to look down and see that some of my pre-cum had leaked out and there were little wet spots on the couch cushion. I moaned and told him that I couldn't wait to feel him coming in me and make me come but that if I did I would be coming on the couch. He kept fucking me and go ahead and cum, it's fine, we'll wipe it off and flip the cushion and no one will know, we're not taking the sofa with us we're giving it away. I could hear his grunting and hear his thighs slapping against me ass. He kept thrusting into me harder and faster driving me to the point where my whole body was tingling and wanting to come and I didn't know how much longer I could last. I felt him lean over me and thought he was ready to come when I realized he had grabbed the camera again and my brain was spinning thinking no no no I need it now when all the sudden he just grunted and shoved into me hard and I felt his jerking as he started coming inside me. I couldn't control it and reached down to stroke my cock and I moaned when I felt him pull all the way out of me. I gasped telling him to put it back in. I could feel his cock rubbing on my asshole shoot a couple of more times and then he pressed his dick between my ass cheeks and finish coming on my back as I finished coming myself. He push his dick back inside me and he moved inside me a couple of more times and then pulled out part way and I heard the camera again. I didn't care anymore as he finally slid back inside me and we stayed that way for a little bit until unfortunately again, he finally softened up and slid out of me and then he said oh fuck just a couple more and he said reach back and hold your cheeks open I could barely hold myself up but did as he asked and then I heard the camera again and heard him kind of moan fuck these are going to be so hot to see when they finally develop as he collapsed on the sofa next to me. I could feel my legs tire from bending over like this and since his come was already covering my ass and back, I just turned around and set next to him, my ass in my own cum and sat there for a moment wiggling my hips and knowing that I was truly coated with cum back there now. We sat there for a couple of minutes catching our breath and I guess I can use the term, basking in the afterglow when all of a sudden we heard his mom's car pull back into the driveway and we both panicked. He quickly jumped up and yanked on his clothes real fast but I was just kind of sitting there frozen not knowing what to do because of the come all over my ass and back. He looked at me and he said, What are you doing, get moving! I pushed myself up and when I did I felt some more of his cum dribbling out of me and I turned my back to him and said and what the fuck am I supposed to do about all of this? He laughed and ran into the laundry room and I'm just standing there when I heard the back door open and I must have been frozen like a deer in headlights as his mom called down and asked, Are you boys still down there? He came back out of the laundry room with a towel and said, yeah Mom. She asked if he could come up and help her with the groceries and he said, Yeah I'll be up in just a second as he was wiping my back and ass with the towel. He said to me softly so she couldn't hear, finish getting cleaned off flipped the couch cushion and shove the rest of the stuff under the other cushion and then come on up. By that time we should have the groceries in and after saying hi to my mom we can come back down and put everything away and he turned and went up the steps. I went into the laundry room and squatted over the towel trying to squeeze some more of his cum out of me and looked around and saw the paper towels and the little sink and quickly washed myself down and quickly put my clothes back on. Once I had that taken care of, I flipped the sofa cushion and then grabed the pictures and the pool cue and the ruler and shoved them under the other sofa cushion and making sure the cap was on tight on the oil slid it underneath the sofa and then put the camera up on one of the shelves and went upstairs just as the two of them were coming back through the back door with the last of the groceries. His mom turned to me and said hi there, have you guys been having fun and I said well sort of we've been shooting some pool but he keeps beating me. She said, yes he's been getting quite good, lately he's been beating his father more and more. I said well he just beat the pants off me this time and Steve almost started laughing out loud. After the paper bags were loaded on the kitchen table, she turned to us and say now run along now you know I like to put things away a certain way. So we said okay and went back downstairs. Steve set the pool table up for another game and said come on one more game no bet this time and I'll even play with opposite hand to give you a chance to beat me. We played the game and even with opposite hand he still beat me. Then he said, okay let's make sure everything's put away and I'm dying to see how the pictures came out. When he picked up the pool cue he said, Wow it seemed to have absorbed the oil and it's really not sticky now but it's not the same color anymore, somebody's going to know something happened. I said just put oil on the rest of it. He said okay where's the oil and I reached under the couch and pulled it out and handed it to him he squirted a little oil on it and worked it around to the whole thing was coated and then leaned it up in a corner and said that should be fine for now, I'll come back in a couple of hours and wipe it down put it back together and put it on the rack and probably nobody will even know, except for us of course and laughed. Then he said now I want to see how those pictures turned out and scooped them up and said damn they're out of order. Does it really matter I said, let me see and he pulled away and said no they got to be in the right order so they tell a story. He started going through them rearranging them and putting them face down into two piles on the pool table and then when he was done he picked up a pile and handed it to me and said here these are yours and I asked him what did he mean and he giggled and said he took two of everything so that we could each have one. I thought about it for just a second and then put the ones he handed me into my pocket. What you're not going to look at them? I said why I was there when the pictures were being taken laughing. He said, well okay your choice but when you do decide to look at them make sure you're alone because I'm willing to bet you're going to get hard and horny again. He said let's head outside, it’s stopped raining and the sun's almost coming out. When we got to the top of the stairs his mom said do you boys want some lunch? I can make some sandwiches for you. We hadn't even realized that it was actually lunch time and he turned and grinned it me and said yeah I think so, beating the pants off him like that made me hungry.

Now for you followers that keep asking if I fucked him, no, sorry to disappoint you.

And to answer a couple of other questions, I've tried to write this in basically the same time frame as when we did these things, and Yes, it is 95% true. At this part of the story, we only had about a week and a half left before they were going to be gone. So yes of course there is still much more erotic things to still tell you. And Yes, you will know when the story is complete.

Again, thank you for following along in my sexual awakening adventure.
And thank you for your comments, they are appreciated!