Date: Wed, 29 Jan 2014 12:53:58 -0800 From: dude Subject: I Love Skinnydipping I Love Skinnydipping My best friend lived next door. He was one month older than I. We were best friends since we were both in the womb according to our moms. When we were little we would swim in a baby pool. The when we got older, in his back yard pool, then eventually, we were allowed to swim by ourselves. The third time we swam alone was after 7th grade. We had just had a pretty stupid sex ed class. Now we had compare dicks and boners before and had always changed together. "Let's swim naked," he suggested as we were in his room stripping. "Ok," I quickly agree. "What time's your mom coming home?" "Six or so." We were both now naked, looking at each other. We laughed and quickly raced outside and dove into the pool. It felt some much more fun naked. Feeling the water flowing past your junk. We just messed around as usual and when we got out for a rest realized we didn't bring any towels. We both just laid down on the warm cement. As we talked out sex ed, we both began to stiffen up. We got on our knees and compared again. He played with our own and finally he popped the big question. "Can you make sperm yet? I can." "No. Show me?" He laughed. "I'll jack, if you jack." We laid down pounding are dicks, watching each other. He only had a little clear stuff come out of the tip, but it was more than I had. Anyway, this became a pretty regular thing for us. Several times his mom caught us naked, but never made a big deal about it, so we got more and more casual about it. We would even skinny dip in the daytime when she was there. It was great. Then in the middle of summer, they moved away. I was so bummed mostly about losing my lifelong best friend, but I also missed the pool. Then a few weeks later a moving van pulled up. When the moving van was unloading, I was hanging out to see who was moving in. So I didn't see any kid stuff like bikes or anything, but I met the guy. His name was Pete and he don't have any kids and was divorced. He was staying in a motel and moving in tomorrow. So I tell my mom and the next day me and her go over there with food for lunch and stuff to leave for dinner. We meet him and he is 33 and been divorced for two years and works as a clothing store traveling manager (whatever that is). He also does photography and has his own darkroom. Anyway, over the next two weeks, he invites us all over for dinner and we have him to our house a couple of times. Also, I get the job of cleaning his pool every other day cause he is out of town a lot and too lazy when he is in town. He said I can swim there but only when he is in town cause he don't want me to drown. Well, school starts and it's basketball season and he comes to a game with my mom. Afterwards, he asks me if he can take pictures. So I say sure. So he shoots pictures of me and all the guys a couple of times. He also brings them back and gives them to everyone for free, so we all like him. We all even get to swim at his house after one of the games. Most guys change in the bathroom but a few of us have seen each other's before and we all change in the guest room together. He takes pictures of all us swimming and the coaches and parents too and later gives everybody pictures, so we all like him. I swim there a little, but it's not as much fun as when my friend lived there. He mostly doesn't swim, but comes out to keep me company. One day, he says his company is thinking about a new line of bathing suits and do I want to try them on and try them out so he can take some pictures and get my feedback. So I say sure and give him my size (28 inch waist, boys large, or mans small). About a week later, he says next time you come over to clean, you want to try the suits. So I say OK, I can do it now. While I was cleaning the pool and doing chemicals and stuff, he brings out a box. He also brings a screen from his house so I can change behind it, and all his camera stuff. First, he shows me about 12 suits. Some are board shorts, ones with built in underwear, a couple of Speedo style and some invisible ones. I mean there were not invisible, they looked normal, but he said you could get a suntan underneath like you were naked, but it totally covered you up and everything. Well, I wasn't too excited about the Speedos cause they show your dick totally, but I didn't say anything. So he said, you pick whatever order you want. He said I should do them in the order I liked them so he could give his buyers feedback. They also had tags, so we had to cut them off. I pick out three board shorts first cause that's what I usually wear. I try one on, but it's too big, so I go to the next one and bring the first one out. I say this was my favorite, but it was too big. So he says, ok we can try it on later cause he still wants to see how it looks. So he takes a couple of pictures, then asks me to jump in the pool so he can take some when I'm wet. So then I go on to the next one and the next one. And after about one hour, I have only done five and he says want to take a break, so I say sure. I just leave on the one I have which is red and orange with a drawstring and built in underwear. I put on a shirt and we go to get drinks from his house. He said I'm a good model and did I ever think about it professionally. So I say no. He says we'll ask your mom. I think you would enjoy it and it pays pretty good too. Anyway we go back to work. I feel kind of stupid in the Speedos and worry that I might get a boner. I mean I get a semi when I try them on and so when I come out, I just jump in the water to swim around till it goes back down. He says, hey wait, and I say, sorry. I get out and it's gone but you can still see totally everything of my dick. He don't say anything. So I dry off and go behind to change again and get another semi. So I don't come out. I wait hoping it will go down. He finally says, are you alive. I say, yeah, but I have to wait a minute. He comes over and I am standing there with my hand over my semi so he can't see it. He says, I think I understand; you got wood? I am very embarrassed and just nod my head yes. He says, don't worry; just jump in the pool and swim around. So I do. He probably sees it a little when I run past him and jump in. When I get out and stand there for pictures, he starts telling me boners are no big deal and not to worry and stuff like that. Well, I wish he would stop talking about it cause I was getting another one, so I jumped in the pool again. He said, well maybe we should do the Speedos another day. I say OK. So I still have to do the ones that were too big, so I change into some cool board shorts from Quicksilver and kind of hold them up with my hand on my hip. Then I get in the pool to get wet. When I'm getting out of the pool, they come down a little and my hair totally shows. Pete laughs and says, well maybe we won't use that picture. I say, yeah. And I laugh too. So he says, Richie I have a suggestion for tomorrow before we finish with the Speedos pictures, but it's kind of a embarrassing suggestion. I say, OK what. He says maybe you should masturbate a few times so you will be less inclined to get a erection. He says that's what the professional models sometimes do. So boy, I'm sure I get real red and am too embarrassed to say anything, so I just nod. I mean, I never talked about that stuff with a grownup. With my friends sometimes but not anyone else. Anyway, I jack off twice before coming over to his house the next day. I still have four suits to try on. When I get there, I think he is going to ask me about jacking, but he don't, he just says, ready? So I do them all and sort of get a little semi on the first one, but it goes away. So I finish. He says thanks and a few days later, he shows me all the pictures. I mean, you can totally see my dick on the just getting out of the water pictures in the Speedos and you also see my hair on that one board short picture. He says, don't worry, he won't turn those in. So I say ok. One week later, he invites me and my mom and sister over for dinner. He shows my mom some of the good pictures and say he has a professional photographer friend who would like to use me to do some modeling. She ask me if I want and I say yeah sure. He says it pays $200 per day. Wow! But my mom says that will go into my college fund. Whatever. Anyway, a few days later, he picks up me and my mom and we go to the studio. She signs a bunch a papers and I meet the photographer. And he also has a helper. So his helper gives me a whole box of suits and they are all Speedos. Shit. That's kind of embarrassing in front of my mom and everything. I mean she sees me in underwear all the time but that's all. So I ask her if she will sit far away so I can concentrate. I don't tell her it's cause I will be embarrassed. So she says ok like it's no big deal and sits way across the room. When I come out wearing the first one, I don't have a boner; in fact it's kind of shriveled. The photographer is upset cause I look too white and gives me a tube of makeup and tells me to put it on. Pete comes into the dressing room to help me. I have to put it everywhere. Pete helps me. I am getting a boner when he is doing the backs of my legs and I am doing the front. I know he can totally see it. He smiles and says don't worry, Richie. I say, well what the hell am I supposed to do. He says after we finish the makeup, he will leave and I can wait till it goes away then come out. Then he says, did you do it before you came here today. I know he means jack off so I nod yes. He says, ok then it shouldn't take long. After he leaves, I think about jacking off, but decide that would be a bad idea. After a few minutes, my mom knocks on the door and I open it and she says everything ok. Well, that sure makes it go away, so I am ready to go out. I say, yeah I was just finishing. So when I got out, Pete has to help me go over a few areas we missed in the dressing room but it don't give me a boner. So it takes five hours just to do six suits. Jeez. So Pete takes us to McDonald's on the way home to celebrate. I am going to get a check for $200 in a few weeks. Next time I am doing his pool, Pete asks me if I enjoyed modeling. I say, yeah it was ok but it sure takes a long time. He says, yeah it does. He says what are you going to do with the money. I say I am pissed because I don't get any; it's all going into my college fund. He says, well that's too bad. He says he will see what he can come up with. I say OK. So next day, he calls me to come over. He says he knows some people who will pay for the pictures he took of me that we didn't use for real. The ones getting out of the pool with my Speedos showing off my dick and the hair showing pictures if I want. I say, sure go for it. I mean, I don't care. The next day when I clean his pool, he gives me $50 in cash. He says that's what he got from the people he knows. I say cool. I say, do they want some more? He says, yeah sure. So I say, when. He says, want to take them now? I say sure. So he goes inside and brings out photography stuff and the suits. I say, where can I change? He says, oh yeah and we bring out the screen for me to change behind so I don't have to go in the house every time. The first one is a red and black Speedo. I don't get a boner; maybe I'm getting used to them. Anyway, he takes some and then I have to get out of the pool like 20 times so he can take getting out of the pool pictures. I think his friends like those cause they show my dick the most. I also do some laying on the chair getting a tan pictures. I do an all yellow Speedo that is almost see-through. He asks me if I will do the too big board shorts cause they like it when I showed a little hair. So I say, sure why not. Well, twice when I pulled up and out, I think it showed even a little dick, but he didn't say anything and I wasn't sure. Three days later, he says that his friends like the pictures and gives me $100 in cash. I say, wow thanks. I say tell me when they want some more. He says, ok he will. He says, did you tell your mom about this. I say. hell no cause she will take the money away. He says ok. A few days later, he says tell me when you're ready for some more pictures. I say, cash ones? He says, yes. I say, I'm ready now. He says, ok. So we get the screen and his stuff and the suits. Well, they are even skimpier than the Speedos. Like a girl's bikini. I wonder if my dick will even fit. He says, well Richie if you don't want to, then don't; it's no big deal. So I think, well what the hell; who really cares anyway. So I say I will try them. He says good. So I put the first one on. It is black and most of my butt hangs out. Also I get a boner, so I just go straight in the pool. He smiles and says, boner problem? I finally have the courage to answer and I say yeah. He says, don't worry about it. He says, they might even like it better. I say, they probably would but I don't want to. He says, yeah I don't blame you. He says, you ready? I say, yeah I guess so. I get out a bunch and change into the next one. And each time. I get a boner or a semi and have to go in the pool and swim 'til it goes away. Well, I also lay on the pool chair for suntan pictures and start to get a semi. I say, stop Pete; hang on a second, and jump back in the pool. He says, boners again? I say yes. He laughs. When I get out and lay down wet, I know it's almost a semi but it starts to go down so I don't worry about it. He says, ok with you if we take some hair showing pictures in these suits? So I say ok. So I put back on one of the smaller ones and pull it down a little in front so when I get out of the pool, it shows some of my pubes. No big deal. Oh yeah, he also started taking pictures from my back to show off my butt I guess. He says, how do you feel about your butt crack. I say, feel about it? He says, yeah want to show a little. I think they will like that. So I say sure and when I'm doing it, I say, do you think they will give extra money? He says, yeah he thinks so. So I'm glad I decided to do it. A few days later he shows me some of the pictures. I look pretty cool. A few make it look like I have a boner even when I only almost had a semi. He says they really liked those. He says they liked them all especially the pubes and butt crack to. So I say did they give any extra for that he says yep and gives me 5 twenty dollar bills: $100!!!! Wow! I said well it looks like they liked those a lot. He said yeah. He says also they wanted me to ask you something. I say about more pictures? He says yes. I say what. He says well if I want to say no it's no big deal and he doesn't want me to get mad at him cause he's just asking for them. So I think he is going to ask me to pose naked but he doesn't. He says they would like to see some skinny dipping pictures. I say naked totally in the water? He says yes that's what they want but I don't have to do it if I don't want to. He says he's just passing along the opportunity. I say how much? He says he don't know but probably $100 like before. So I say and I just stay in the water and swim around naked. He says yeah that's all. So I figure why not. I say yes. I say when. He says whenever. I say let's do it now. So when he is bringing out his stuff I strip and get in the pool. It's not so bad, you really can't see too much. So he comes out and we shoot like a million pictures. Especially me swimming backwards so they can sort of see my dick. Also he gives me a snorkel and mask and I swim around like that for a little. He says ready for a break? I say yeah. So he holds up a big towel for me. At first I'm a little scared but then I figure he's been looking at my dick for the last hour so it's no big deal so I get out and he can see it. So I wear the towel and we go in and get some Dr Peppers. As we head back out he says how about some diving in pictures just from the back. So I say ok. So I dive in like 20 times. I mean he can totally see mine when I get out but he only takes pictures when my back is turned and I am diving in. So he says do you want to do any suntan pictures only lying on your stomach. I say and show my naked butt. He says yes if you want. So I say sure no big deal. So I lay out a towel and again he can totally see me but he don't care so I don't care and I lay down. So he takes a bunch and I almost fall asleep. While he is packing up he says are you sleeping I say no but I almost was he says ok I think were done. He says feel free to swim if you want. So I do and stay naked I mean why not I been naked all day. So he comes out and sits while I swim I say you coming in he says no he better not. I say I'll put on my suit if you want. He smiles and says no that's ok. He says maybe some other time. I say ok. So he sees me when I get out and dry off and change. He says I think they will like these pictures. I say yeah I hope they like them a lot and rub my fingers together like money. Well they did like them cause they gave him $150. I'm getting rich. He shows me the pictures. Shit I'm surprised cause on the diving in pictures you can kind of see my dick hanging down. He said yeah that's why they gave so much money. And you can see my dick in the water but no to good cause its blurry. He says they think you are cute. Well, no chicks in the 8th grade ever said I was cute. But hey I'm glad people think I'm cute. And I'm glad for the money. So I say what's next. He says what do you mean? I say do they want more pictures? He says yes, but we pretty much showed them everything. I say except my dick. He says except your dick. I say what do you think? He says well if it was him he probably wouldn't show his dick cause he's not as good looking as me and his dick is ugly compared to mine and he says he's shy and he says you sure aren't shy. I say no I guess not. I say I never knew I wasn't shy. I say Maybe I'm just greedy. He says yeah well it's up to me. He says show, don't show or show whatever you feel comfortable with. He says you know, the more you show and do the more they will pay. I say do? He says yes do. I say really how much? He says he don't know. So I say would you ask them? He says sure no problem. He says want to swim I say sure so we swim together. Not naked in case you were wondering. Later he tells me they have a price list and if the pictures are good they will pay me $200 for naked pictures showing my dick and everything, $250 if I show my boner, and $300 if I will jack off with pictures. Shit. That's intense I say. Pete says yeah I didn't think you would do it, he says I sure wouldn't. I say why not. He says cause his dick is not cute and his ass is ugly. I say really? He says yeah. I say you ever posed naked he says no. I say I will take your pictures if you want. He thinks about it, get up, goes in the kitchen, brings us Dr Peppers and says ok. I say you want to pose naked? He says sure he will try. So he teaches me how to use his camera and we go outside. He strips and jumps in the pool and I don't see it except in the pool. I mean he's seen mine a million times he should show his right? But I don't say anything. So I take pictures of him in the pool and stuff. When it's time for a break I see his when he gets out. I take pictures of him when he's getting out too. It looks pretty normal. I mean I only seen my dad's a few times but looks about the same. He's pretty damn hairy. Anyway he puts on the towel. He says so what did you decide. I said I'm not sure but naked is sure ok. So I start to strip he says no wait they would like stripping pictures. So he gets it all set up and I strip and he takes lots of pictures and wants me to strip slowly only showing a little part at a time. Then I go home and get different clothes and strip again. Then I put on some suits and strip them off. Finally I lay on the chair and get a sun tan with him taking pictures. I put on a towel when we go in for a break. So we are drinking and eating Fritos naked except for our towels! He has to go to the bathroom and I just go out and lay down with my towel on and catch some sun. He finally comes out with a Hustler magazine and gives it to me. He hands it to me and says only if you want. I say ok. He says ok just play with it under your towel and slowly look around to make sure no one is watching and them slowly pull the towel open. So I do. It's kind of fun and horny making. So he says you better play with it less or you will come in like a few seconds. So I slow down. And he is telling me what to do. I finally start to jack and he says don't come too fast, Richie; try to make it last so we get lots of pictures. So I finally tell him I'm about to come. He says put down the magazine and close your eyes and enjoy it. Man, I shoot like almost to my head. He says just lie there and relax, don't clean it up. And takes more pictures. Oh yeah I can see he's got wood under his towel. Hehe. Finally he says ok just jump in the pool and clean up there. He goes in to put stuff away and when he comes out I say you going to swim. He says sure and pulls off his towel and he gots a semi I think. So we swim naked together. I say I saw you had a boner when I was jacking. He says yeah sorry. I say it's cool. No big deal. I say I had a boner too. We both laugh our asses off. So when he shows me the pictures it makes me horny again. I mean whoever thought looking at pictures of yourself jacking off can make you want to jack off? Weird! So I say haha these pictures of me make me horny. He laughs and says he thinks they will make a lot of people horny, He says I will take these to my friends. And I say and bring me back my money? He says of course. And he does and it is $300. I am so rich now. So I don't see him for a while but when he's home about a week later I ask him if they want any more pictures. He says sure, but they can't pay as much money now cause they paid a lot. I say well how much. He says $100 if I go all the way. So I say OK I'll do it. I mean imagine getting $100 just for jacking off! So he says ok go outside and get ready so I get naked and put a towel on. And I do it. He takes pictures. He is dressed but I can see he has a boner. So after I finish and am swimming I say when are you gonna jack off your boner. He says yeah I thought you might see that. I say yeah well it's pretty obvious. He says yes. So I say do you want me to take your pictures jacking. He says no he's not that brave. When he comes out in a towel I am swimming. He gets in and has a boner. I see it and say I guess you didn't jack it off yet, he says no not yet. So we swim a little. I get out and put on a towel and lay out. After I get bored I get the Penthouse cause it is still out here. He also gets out and lays down next to me. He says you going to jack again? I say yeah if it's ok. He says sure. I say, are you? He says he might if I don't mind. I say it don't bother me. So when I open my towel and start jacking hard, he does too. I look. His is bigger and fatter than mine. So I finish and he is still jacking. So I give him the magazine when I get in the pool to clean up. But he is not looking at the magazine, he is looking at me. Hehe. I think he likes looking at me naked. I watch him till he comes and gets in the pool to clean up. While we are swimming I say will they want more pictures. He says yeah probably. He says would any of your friends like to pose with you? I say naked? He says bathing suits, naked, whatever. I say Maybe. I haven't told anybody about this and wasn't sure I wanted to. But I got a new cool BMX bike and Matt wanted to know how I could afford it cause it was more than $700. I told him I got the money from cleaning pools but I don't think he believed me. I told my mom it was only $100. So I show Matt the pictures the real photographer took of me in the Speedos at the studio. He was making fun of me till I told him I got $200 for posing. He was surprised that I got so much. I said yeah they pay a lot. I said want me to see if I can get you a job too. He said hell yeah his bike was a piece of shit and he wanted one like mine. I said well I did a lot of pictures to earn that but I didn't tell him the details. So I asked Pete and he said he could get us both jobs as underwear models at the photographers studio. So me and my mom and Matt and his mom all went there following Pete. We shared a dressing room so we got to see each other's dick. His was cool about like mine maybe a little bigger cause he was a little bigger. He also had way more hair under his arms. I only had a little. Anyway we did like six boxers each. Then we had to do whitey tighteys and colored ones too. We laughed our asses off about that. It was fun with Matt. And I don't think he was shy. I mean he was even braver than me I think. We went to Pete's a few days later so Pete could show us the pictures. Also Pete asked him if he liked it and wanted to model some more. He said they got some speedos and other bathing suits they need pool models for. I said yeah it's cool man. So we agreed to come the next day. So he already had the screen and stuff set up when we came. Matt was laughing his ass off about the speedos and the even smaller ones. I said we could quit he said hell no. So we went behind the screen to strip naked together. I had a semi and he made fun of me. I was embarrassed cause his was just hanging down. Anyway I went out even with my semi and it went down when we started posing. Then we jumped in the pool and he took a few then a bunch of us getting out. Then us laying down. Then we went to change. I had a semi again. He said I dare you to go out with a boner. I said no way, but I really wanted to. Plus if I did I would be able to dare him. I played with it and Pete just laughed and said why don't you guys swim for a minute till that monster goes away. So I dared Matt to get out of the pool with a boner when we did the getting out of the pool shots and he did. Only it wasn't a full boner only a semi. Pete didn't say anything but when Matt was jumping back in the pool gave me a thumbs up. So I figured Matt was cool for some dares and stuff maybe naked stuff I hoped. So during the break when Pete went in to get drinks and snacks I dared Matt to skinny dip he said no so I called him chicken and pulled off my speedos. So then he did it to. After a minute he said what about Pete? I said he will take our pictures if we want and give us even more money. He said naked in the pool. I said yeah it's fun. He said ok if you're sure it's ok. I said yeah I'm sure. So Pete came out and was surprised. He asked if we were ready for pictures I said yes, we are ready for skinny dipping pictures. He asked Matt and he said sure. So we took a bunch. Then when we were finished I got out totally naked so Pete and Matt saw and put on my towel. Matt waited till Pete took stuff in and then he got out and put on his towel. So I was afraid to dare him anything else. So we dressed. Four days later we went to Pete's to see the pictures and get our money. We each got $100 and then later Pete gave me another $50! So Matt was glad and so was Pete and so was I. Later Pete asked me if Matt wanted to do more. I said maybe. He said well make sure. So I had Matt over for a sleepover. So we hung out and were going to sleep in the tent in my back yard. I did that so we could have privacy in case he wanted to do stuff. So after we watched tv in the house and went out there it was already late at night. So while we were getting set up before we got undressed I asked him if he wanted to skinny dip in Pete's pool. He said does Pete care I said no I can use it as long as he isn't out of town. Well, I never snuck over at night but I didn't think he would care. So we are in are boxers and going to the fence and I say let's leave our clothes here and go over totally naked. He don't say anything, just pulls off his boxers and throws them back with the tent stuff. So I do too. So we climb on a chair and go over the fence naked. Hehe. We slip in the pool as quiet as we can. We swim quietly. It's cool. Then the sliding door opens and Pete turns on the lights. I say it's just us. Me and Matt. He says ok just wanted to make sure. He turns on the pool light and goes back in. So now we still have to be quiet cause I don't want my mom to hear us and check on us. But we don't have any towels. So I run up on Pete's porch and get some from earlier in the day where he hangs them up to dry. We dry off and lay on the pool chairs. I open the little cabinet and pull out the Hustler. Matt likes it. So we are looking at it and I know we both got boners so I say want to jack? He says here. I say yeah, we can turn off the light. He says yeah ok. So I get up and turn off the porch light but leave to pool light on so we can see the magazine and I can see his dick. I never seen his boner before. Well. he pulls open his towel even before me so I do it too. I can't see it too good, but I like what I see. I am hoping he will do it tomorrow in the light and with pictures. So we come and get in to clean up. After we dry off again he says let's borrow the magazine. So we jump back over the fence naked and get in the tent. We just pull the sheet over us and stay naked. We got a good flashlight lantern and look at the magazine some more. He says I need to jack again, Richie. I say me too and pull off my sheet. We both jack. This time I can see him real good. I like it. While we are jacking, I say want to see if Pete wants to take pictures. He says no. So I say ok. After I see him come and I do too, I say let's sleep naked ok? He says sure cool. In the morning I say want to swim naked again. He says yeah so we put on our clothes and go over and just go around back. We strip and get in the water. Pete comes out and we say we just want to swim if that's ok. He says sure. He stays and watches. Finally he goes in and we sit out on the chairs naked with towels. I pull open the magazine and start to jack mine under the towel. I say don't worry he's not taking pictures. We end up jacking off in the daytime and I get to see his real good.