Author: wolfcub Title: Dear Diary Summary: A pre-teen boy is caught masturbating by his mother. Rather than getting in trouble, he discovers a host of new pleasures. Keywords: b-solo exhib bg 1st May 17th Today, Mom walked in on me while I was masturbating. That's the word she used. The guys at school call it whacking your wiener, but Mom says that's crude. Now that I'm eleven, Mom says I'm old enough to stay by myself after school. I usually get home about 3:30, and Mom's usually home from work by 4:00, so it's not that big of a deal, but today, school got out early, so I was home at 2:00. I didn't know she was getting off work early. When I know I'm going to have some privacy, I like to take off all my clothes, stretch out on my bed, and take my time. When I get close, I stop for a moment until the feeling starts to go away. That way, I can make it last a long time and really enjoy it. Today, Mom walked in on me while I was stroking it. I didn't know she was there until I heard her gasp and say, "Oh! Sorry!" I froze--with my hand still on my penis. (Mom says I'm getting too old to still be calling it a wiener.) We just stared at each other for a moment, then Mom suddenly turned around and started to hurry away. Then she came back and closed the door to my room. I jumped out of bed and put my clothes on as fast as I could. I didn't know what to do next, so I just stood there, wondering how much trouble I was in. It wasn't like I could deny it, or anything. She had gotten a real good look at me. Anyway, I figured it was the end of staying home alone. I don't know how long it was, but eventually, Mom came and knocked on my door. Usually, she just knocks then comes right in. This time, she asked, "Is it okay to come in?" and waited for me to answer. I thought, "No, it's really not okay," but what was I going to do? I'd have to face her eventually, so I squeaked out a weak, "Yeah." Surprisingly, Mom was really cool about it. She sat down on the bed and had me sit next to her. First, she told me I wasn't in any trouble. That was a big relief! She said that all boys masturbate, and that it was okay for me to. She just didn't know that I was old enough to have started. She said I was really growing up fast, but that she still thought of me as her little boy. I usually hate it when she calls me that, but I was too embarrassed to be bothered this time. She said I could do it anytime I wanted, but that it was a private thing, and I shouldn't do it where other people could see me. We talked for a long time. She asked me if I was ejaculating, yet, and explained about semen and sperm and how babies are made. I knew it had something to do with boys and girls getting naked and rubbing their parts together, but I didn't know about squirting into the girl! I thought that was kind of gross. Mom laughed and gave me a hug. She hasn't hugged me in a long time. It felt good. I told her nothing came out when I got the really good feeling, which she told me was called an orgasm, but she said she'd put a box of tissues in my room that I could use to clean up, when I started, which probably wouldn't be long from now. She also gave me this journal to write in. I like writing and often write stories. She said it might be good to write down my feelings as I'm growing up, and that I might find it interesting to go back and read when I got older. She promised she wouldn't read what I wrote, unless I wanted her to, and then she'd only read the parts I said were okay for her to read. Mom's real good at keeping her promises, so I decided to do it. I'm going to let her read this first entry, to see if I'm doing it right. Dear Son, I'm glad we were able to talk like we did, today. I hope we can continue to talk like this in the future. I love you very much. --Mom May 18th I didn't know Mom was going to write back! It was nice, though. When she got home from work, today, she asked me if I had masturbated. I was a little embarrassed, but nothing like I was yesterday. After I told her yes, she asked me if it was good, which made me a little more embarrassed, but I told her it was. It's kind of fun talking to my Mom about masturbating, and it's way more fun doing it without having to worry about getting caught and getting in trouble. Mom had a surprise for me. She made one of those Please Do Not Disturb signs like hang on the door knob in a hotel. She made it from a piece of poster board left over from one of my school projects. It looks real good! She said I could hang it on my door whenever I'm masturbating, and she wouldn't knock on my door or anything until I was finished. I thought that was really nice, but then I thought that the sign might as well say I'M MASTURBATING because that's really what it meant. Thinking about that made me feel funny. I'm starting to like the idea of my Mom knowing I'm masturbating. Weird, huh? May 19th Today, Mom asked me if I always get completely naked when I masturbate. I told her that I only do that when I think I'm going to be alone for a long time. She told me that before I started school, I liked to run around the house naked, especially after a bath. She also said I liked showing off whenever my penis got stiff. I didn't believe her, but she got out a photo album that I didn't even know we had and showed me some pictures. I couldn't believe Mom had naked pictures of me! And not just baby pictures, either. There were a lot of pictures from when I was three and four! Fortunately, I didn't have a boner--erection--in any of them. Mom said if I wanted to go naked around the house that it was okay with her. I'm not sure what to think about that. May 20th Last night, after my bath, I thought about going naked, like Mom had suggested. I liked the idea, but I chickened out. Instead, I just put on some shorts. I'm usually fully dressed at home, so it was almost like being naked. Mom and I watched a movie. She even made popcorn, which she usually doesn't do unless I ask. We sat on the couch together, and she pulled me close to her, and I snuggled against her like I used to do when I was little. It felt really good! During the movie, Mom rubbed my bare chest and belly, which also felt really good. I got a boner--erection--but my shorts were baggy enough that I don't think Mom noticed. After I went to bed, I got the idea to try sleeping naked. I really like it! And, it makes it easier to play with myself! When I woke up, this morning, I kicked the sheet off and saw my erection sticking straight up, so I started rubbing it. I looked over and noticed that my bedroom door was open. I usually only close it when I'm getting dressed. I didn't want to get out of bed, so I just kept masturbating. It was fun to think that Mom might see me. I was getting close to having an orgasm when Mom really did walk in. Well, up to the doorway. She started to ask if I wanted pancakes, but then she saw what I was doing. Rather than getting all weird, like we had the other day, I just kept stroking, and Mom smiled and said, "When you're done, they'll be pancakes." It didn't take me long to finish. When I did, I thought again about going naked, but I chickened out again. This time, I just put on underwear. When I arrived in the kitchen, Mom eyed me from head to toe, but she didn't say anything about me just wearing underwear. I liked the way she looked at me. After breakfast, we went to the beach. When I was changing into my swimsuit, I left my bedroom door open. I was actually hoping Mom would come in while I was naked, but she didn't. When we got back from the beach, I took a shower. This time, I was brave enough to go naked. Mom smiled when she saw me and gave me a big hug. It felt really good to be hugged when I was naked! Mom rubbed my bare back and gave my bare butt a little squeeze! My penis went stiff while Mom was hugging me, but she didn't say anything. We made spaghetti for lunch. Actually, I made it! Mom told me how and let me do it all myself. It came out just like when she makes it! May 21st Last night, Mom and I watched another movie together. It was extra fun cuddling on the couch with her because I didn't have any clothes on. Mom rubbed my bare chest and belly, like she did the night before, but she also rubbed my bare legs, and in between, too! I had gone stiff while she was stroking the inside of my thighs. I wasn't embarrassed at all. Then she grabbed my nuts and gave them a little tug. I squirmed when she did that. She laughed and said that my "testicles" would be getting bigger, soon, and that they'd start to hang down away from my body. She then gave my penis a squeeze, pulled my foreskin back, and ran her finger over the tip. I squirmed, again, and Mom laughed, again. She told me I had a nice penis and that I'd make some girl happy some day. After the movie, I went into the bathroom and masturbated really hard and fast. I had a really good orgasm in record time! May 25th I've been going naked around the house all week! I touch my penis a lot and even stroke it on the couch while watching TV. Mom doesn't say anything. She just smiles. May 27th Boy, did I embarrass myself this morning! I was lying on the couch, watching cartoons, when the doorbell rang. It was Sierra. She's a girl who lives in the neighborhood. We play together a lot. We're not going together, or anything. We're just friends. She's really cool. She's not goofy like a lot of girls my age. We've been friends since third grade. Anyway, I forgot I was naked! I guess I got so used to being naked that I didn't think about it. I wasn't masturbating or playing with myself or anything, I was just watching cartoons. I invited Sierra in, but she just stood on the porch, looking down. I looked down to see what she was looking at and realized that she was staring at my penis! Good thing it wasn't stiff! I quickly covered myself with my hands, then I realized that the front door was wide open. I yelled at Sierra to come in. I guess I startled her because she hurried in, then I quickly closed the door behind her. I was still covering myself with my hands, and Sierra was trying not to look at me. "Sorry, I forgot I was naked," I said to her. "You go naked at home?" She asked. "Yeah, sometimes." I wanted to rush to my room and get dressed, but Sierra was blocking the way, so we both just stood there. It was really awkward. That's when Mom walked by. "Oh, hi, Sierra. How are...Kevin! Put some clothes on when you have guests!" I didn't wait for Sierra to move. I just scurried past her. When I did, my bare butt brushed her arm! In my bedroom, I pulled on the first pair of shorts I could find. I was in such a hurry that I didn't even put on any underwear first. Now that I had shorts on, I wasn't in such a panic. That's when it occurred to me that it had been really fun having Sierra see me naked. That's also when I decided to not put a shirt on. Sierra walked into my room, cautiously peaking around the corner from the hall, first. I apologized, again. She said it was okay because she was used to seeing Travis naked. That's her little brother. He's four. Sierra sat down on the edge of my bed. I did, too, but at the other end. It was still awkward, so neither one of us said anything. Sierra always goes barefoot, and she usually wears those really short, tight shorts that girls aren't allowed to wear at school. She's a fast runner and has really strong legs. She also wears those thin-strapped, short tops that leave her shoulders and tummy bare. Sitting on the bed next to her, I noticed how beautiful she is. I never thought of Sierra as beautiful before, but she really is. I looked at her face and saw that she was blushing and realized that I had been playing with myself through my shorts. I had gotten an erection, and without underwear, it was tenting out the front of my shorts. I covered my crotch with both hands and apologized, again. "That's okay," Sierra told me. "Travis does that too. A lot! Whenever he gets a stiffy, he comes running to me to show it off! It's really embarrassing. My dad thinks it's funny. My mom says I shouldn't tell Travis not to play with himself because there's nothing wrong with it, but he does it all the time!" I noticed that Sierra had her hands between her legs, and I could see that she was rubbing herself with one of them, so I said, "I didn't know girls did it, too." I don't know what made me say that. It just came out. Sierra turned really red. She grabbed one of my wrists and drug me out of my room while saying, "Let's go out and play." Sierra likes to run, and like I said, she's fast, so I had to take off after her. I forgot I wasn't wearing shoes until I got to the sidewalk. I'm not used to going barefoot, but it was too late to stop and go back into the house for shoes. Sierra already had two driveways on me. I caught her at the edge of the woods and wished I had gone back for my shoes. The twigs were sharp! I hobbled over to where she had thrown herself on the ground and laid down next to her. She looked me straight in the eyes then surprised me by asking, "Kevin, do you like me?" I was confused and said, "Sure!" "No, I mean do you like me like me? You know, like boyfriend/girlfriend like me?" I had never thought about Sierra in that way. There are a couple girls at school that I've had crushes on, but not Sierra. I guess Sierra got mad that I didn't answer because she acted really annoyed. Then she surprised me again by sitting up and demanding, "Show me your wiener, again!' I sat up, too. I was really shocked that she had said that! Suddenly, she didn't seem mad, anymore. She said, "I'll show you my kitty." Then she raised up on her knees and hooked her thumbs into the waistband of her shorts. She pulled them down about an inch but stopped, waiting for me. I thought for a moment, but then I quickly remembered what had just happened. I didn't want her to get mad, again, and change her mind, so I quickly got to my knees and dropped my shorts. Sierra pulled down both her shorts and panties at the same time. She stood up to take them off all the way, then knelt back down in front of me. I did the same. We stared at each other for a little bit, then Sierra reached forward and grabbed my nuts. I couldn't pull away without hurting myself. She rolled them around in her hand a little then gave my penis a few strokes and said, "You're a lot bigger than Travis. You're bigger than Martin, too." "Martin?" Martin is another boy in our class. "How do you know how big Martin is?" Sierra smiled and blushed. "None of your business!" She let go of my penis, then spread her knees apart, leaned back on her elbows, and said, "You can look, now. You can touch, too, if you want." I bent down and got real close. Her pussy was really soft. I noticed the crease, so I tried spreading it open. It wasn't what I expected! It was pink, and red, and shiny, and all wet. I got a good look, then touched one part and asked, "Is this where the penis goes?" Sierra pulled away, rolled her feet out from under herself and gave me a good shove with one foot on each of my shoulders. I fell back. As she stood up and put her shorts back on, she said, very firmly, "You're not sticking your wiener inside me!" I didn't know what to say or do, so I just got up and put my shorts back on. We played the rest of the morning, like we usually did. I want to ask Mom about what happened, but I don't think she'd like that I got naked with Sierra or that we touched each other. May 28th I'm a little sunburned from yesterday, on my front, back, and feet. Mom lectured me about sunscreen and said if I was going to run around the neighborhood "half naked," I'd had to work on my tan, first. She rubbed some lotion on me. It felt really good, and I got an erection. "Good thing you didn't burn that!" she said, which made us both laugh. May 31st Sierra stopped by right after school, today. I was in the middle of getting undressed when the doorbell rang. I remembered to put my shorts back on before I answered the door. Sierra was wearing her usual shorts, but this time, she was wearing a bikini top. It was one of those string-tie ones that just had a couple of small triangles. I've seen her in a bikini before, but this time was different. After she came in, she said, "I thought you went around naked." I blushed and answered, "I was just getting undressed." There was another awkward silence, then Sierra said, "Well?" I realized that she wanted me to take my shorts off. I was a little embarrassed, but I did. When I walked back to my bedroom, Sierra followed. She sat on the edge of my bed. When I sat on the other end, she scooted over next to me. Without asking, she grabbed by nuts and started rolling them around like she had the other day. She wasn't being too rough, so I let her. Then she gave my penis a few strokes and said, "I like your wiener." I asked her if I could see her naked, again, and she said that she didn't want me to put my wiener inside her. I promised her I wouldn't, but she stayed dressed. She asked me when my mom was going to be home. I told her in about twenty minutes. She pushed me back on the bed, climbed on top of me and kissed me! Right on the lips! She was straddling my hips, so her crotch was right on top of my penis, which had gone stiff from her touching. She started rocking her hips and rubbing her crotch against my penis, then she kissed me again. This time, I felt her tongue push into my mouth. I know it sounds gross, but it was actually really nice! Sierra pulled her face away from mine, a little, and said, "You have to kiss me back." I figured she meant that I was supposed to stick my tongue in her mouth, so I did. After a while, we sort of started wrestling with our tongues, kind of like thumb wrestling, but wetter. Pretty soon, we were both laughing so hard that we had to stop. In between laughing, she said, "You have to learn how to do it without slobbering so much!" I said, "I need to practice," which got us both laughing even harder. Sierra looked up at the clock on my dresser. She hopped off me and headed out the door. Without looking back, she said, "My parents won't be home till five." I'm supposed to wait until Mom gets home before going out to play. She wants to make sure I got home alright. I was thinking about leaving her a note when she walked in. I wasted no time getting to Sierra's house. I had put a shirt and shorts on, but I decided to go barefoot. Of course, Sierra had me take my clothes off as soon as I got inside. She led me to her bedroom where she took off her bikini top. Sierra is as flat as a boy, but it was still nice feeling her bare chest against mine. She spent a few minutes teaching me how to kiss "the right way," then we really went at it. I used to think kissing girls was yucky, but kissing Sierra is not yucky! I was lying on my back, and Sierra was on top of me, like before. She was rubbing up against me like she had been, too. That felt really good! She was grinding against me really hard when I had an orgasm. I cried out kind of loud, which surprised both Sierra and myself, but then Sierra laughed. She lifted off me a little, looked between her legs, and said, "You've gone soft!" I blushed, and said, "It always goes soft after I have an orgasm." I couldn't believe Sierra didn't know that word, but then I only learned it recently. I felt really grown up explaining it to her, and the other stuff my mom had told me about semen and sperm. Sierra looked like she was a little grossed out, but she didn't stop me. She asked me why I didn't squirt any semen, and I told her that I wasn't old enough, yet. We went back to kissing, for a while. This time, it was slow and gentle, which was nice. Then I heard a beeping sound. Sierra jumped up off me and pressed a button on her watch, which she wore everywhere. "You gotta go before my parents get home." June 1st Sierra and I kissed again, after school, but her mom was home, so we just did it here for a little while. After my mom got home, I met Sierra in the woods, but Joey and Connor were there, so we just ended up playing regular games. June 2nd School's out!!! We got out early because it was the last day of school. Sierra says I kiss really good! She showed up today wearing her bikini. The bottoms have string ties, too, with just a little triangle in the front and a slightly larger one in the back that leaves half her butt showing. I never noticed, before, but Sierra has a really cute butt. Sierra kept the bottoms on, but they were so small that it was almost like she was naked. I put my hands on her butt and squeezed and rubbed and she let me! Then she did something amazing. She climbed off me, and I was afraid we were done, but she slid down my body and took my penis into her mouth! Then she started sucking on it! It's way better than masturbating! She kept going until I had an orgasm. It was the best one ever! Next, she took off her bikini bottoms. The she rolled onto her back, spread her legs, and said, "Now you do me!" In a stern voice, she added, "Don't even think about putting your wiener in me, or I'll kick you in the nuts so hard you'll never start squirting!" The threat really worried me, but the sight of Sierra naked, with her legs spread, really got me excited. I wasn't sure what to do, so I tried kissing. Sierra told me to try licking a little and told me where. I guess I did it right because she started moaning and groaning, really loud. After a while, she cried out like I had done when I had my orgasm, then she told me to stop. I was stiff, again, and I really wanted to see what it was like to stick my penis in her, but I remembered her threat, so I didn't even ask. Instead, I just started masturbating. Sierra watched me with an amused look on her face. She even giggled a few times, but I kept stroking. When I had my orgasm, I lost my balance and fell forward just a little bit, toward Sierra, who still had her legs spread. She put a foot on my crotch and pushed me back. Mostly, she pushed against my hand, which was still on my penis, but she put enough pressure on my balls for me to notice. I complained, but Sierra just laughed and repeated that I wasn't allowed to put my penis inside her, only she said, "Wiener." I laid down next to her, and she took my hand, which was nice. We laid there for a long time, just holding hands. After a while, she rolled over onto her side, sat up a little, and started rubbing my chest and belly. I got stiff, again, pretty quickly. When I did, she straddled my hips again, only this time, it was her bare pussy against my bare penis. Boy, did that ever feel great! She put her hands on my chest and sat up as she rubbed her pussy against my penis. She warned me, again, too, "Don't try to put it inside!" "I won't!" A couple of times, the top of my penis caught on her pussy, and I felt skin spread apart a little. Each time, Sierra said, "Stop trying to put it inside!" "I'm not! You're doing it!" She smiled, and I realized she was doing it on purpose! When I started trying to help make it go in, she climbed off me, gave me a dirty look, and swatted the inside of my thigh, just missing my nuts. "Stop it!" she said sternly, then climbed back on top of me. I don't understand why she got mad when I tried, when she was trying to make it go inside, herself, but I laid there and let her do what she wanted. Again, the tip of my penis got caught a few times, and again, Sierra told me to stop it, but this time, she smiled when she said it. After a while, she stopped and leaned forward to give me a kiss. Her chest and belly were pressed against mine, and she wiggled her pussy against my penis. Then, she wiggled her pussy a little more and pushed. I felt the tip of my penis pop past a tight ring. Sierra pulled her face a little ways away from mine and smiled. "You've got it inside me, don't you?" she accused. I was too stunned to reply. I felt a strong urge to push, but I was confused about what Sierra wanted me to do, and I didn't want to get kicked in the nuts, so I just laid there. Sierra kissed me, again, then climbed off me and got dressed. "Gotta go! Your mom's gonna be home, soon." Despite having already had two orgasms, I masturbated really fast and had another. June 3rd I guess I fell asleep after Sierra left, yesterday, because I woke up to the smell of Mom making dinner. She joked about me wearing myself out masturbating. I was relieved that she didn't suspect that I had been with Sierra. She gave me a hug, a pat on the butt, and a kiss on top of the head. Mom used to hug me a lot when I was little, and I used to cuddle with her a lot, too. I don't know when that stopped, but I'm glad she's doing it, again. I really get a warm feeling inside when she does it. Today, Mom took Sierra, Joey, Connor, and me to the beach. Sierra wore her string bikini, and I spent most of the time we were out of the water trying to hide the tent in my boardies. When we left, I didn't put my shirt on. Most of the guys I know wear shirts when they go swimming. I never have, but I do wear a shirt everywhere else, even at home, at least I did until I started going naked. The only boy I know who goes shirtless a lot is Kyle. He even took his shirt off at school when we played water games at our end-of-the-year party! Mom grilled hotdogs and hamburgers for us in our back yard. Joey and Connor didn't say anything about me being shirtless. I think I'm going to try going shirtless all summer. That night, I was lying on the couch, watching TV, when Mom came in. I was hogging the whole couch, but rather than asking me to move, she just sat sideways on the edge and started rubbing my neck and shoulders. She gave me a real massage, starting with my neck and working her way down my back and legs. She even rubbed my butt, which felt really nice! Next, she had me roll over. I was a little embarrassed because my penis was stiff. I wasn't embarrassed that it was stiff. I was embarrassed because it was stiff because of Mom. Mom just smiled and rubbed my feet. She worked her way up my legs, then massaged my chest and belly. I was nervous and excited about what she was going to do next, but she just gave my stiff penis a firm squeeze, and said, "I'll let you do this last part, yourself." She sat back and watched me with a smile on her face as I masturbated to a really good orgasm. After that, I snuggled next to her, and we watched TV together. June 4th I woke up, this morning, with a stiff penis. That's been happening a lot, recently. Instead of masturbating, I went into the kitchen because I smelled Mom cooking breakfast. I sat on a stool in the kitchen and masturbated there, where Mom could watch me. She was busy with cooking, but she did look at me a few times and smile. Breakfast was ready before I had my orgasm, so I stopped masturbating to eat. After eating, I helped Mom clean up. She asked me what I was going to do for the summer. Last summer, I was in a day camp when Mom worked. I had gotten used to being home alone, and I was hoping Mom was going to continue that for the summer, but I knew that being alone all day was different from being alone for half an hour or so after school. Mom must have known what I was thinking because she said, "I think maybe you're too old to be left alone by yourself all day." At first, I thought she meant "too young," but then she explained. "If you're already masturbating, it's only a matter of time before you start getting interested in girls. I'm not sure that I want my horny little boy running around by himself when there's a pretty girl in a skimpy bikini in the neighborhood." That made me blush! I guess Mom didn't know what Sierra and I had been doing, but she did suspect me of thinking about it. I didn't know what to say, so I just stayed quiet. Again, Mom must have read my mind. "Don't think I didn't notice you at the beach, yesterday. I saw the effect that bikini had on your boy parts." I couldn't help laughing. Mom had said that I was too old to be calling my penis a wiener, but "boy parts" is what she used to call my penis and nuts--testicles--when I was little. "Do you like Sierra?" I blushed, again. "So, I see. If I leave you alone, you'll have Sierra in your bedroom all summer, right?" My face was so hot that I could tell it was bright red. Mom didn't let up, but I knew that she was teasing me more than accusing me. However, she would have been right to accuse me because that was just what I had been planning. "Remember what I said about how babies are made? I don't want you putting a bump on Sierra's belly!" "Mom!" "Well, that's where those little sperm go after you squirt them up inside a girl! They swim up deep inside her in search of an egg, and if they find one, they start a baby." I thought I was going to die! After Mom had her fun teasing me, she sat me down for a serious sex talk. She told me about how she got pregnant with me when she was sixteen. She had had sex with my father over the summer, which was why she was worried about me having sex with Sierra. She said she loved me and that she wouldn't give me up for anything, but she wished she had had me when she was a little older and married. I've never met my father. The only time Mom's talked about him before is when I'd ask, and even then, she's never said much. This time, she talked about how it would have been a lot better if she had a husband and I had a dad. I told her she was doing just fine by herself, but she still said it would have been better if she had waited to get pregnant with me. I knew the sex talk was over when Mom started teasing me, again. She started talking about Sierra's cute butt and wondering when she was going to start sprouting breasts. I attacked her, and we wrestled until we were both laughing too hard to continue. It was really fun wrestling naked with my mother, even though she was wearing shorts and a t-shirt. A few times, I got a look down her shirt and saw the tops of her breasts because she wasn't wearing a bra. Mom told me she would try letting me stay home by myself, this week. I had a big smile on my face until she told me that Sierra was going to be spending the week at her grandparents' house. I was disappointed that Sierra wasn't going to be around, but I was also upset that Sierra hadn't told me that she wasn't going to be around. I knew she visited her grandparents every summer, but I didn't know it was going to be this week. June 5th I did it again, only this time it was with Joey and Connor. Their pounding on my front door woke me up. Still half asleep, I answered the door naked. Joey laughed, and Connor just said, "Dude! You're naked!' I was too sleepy to be embarrassed, so I just grumbled, "So?" and walked back into the house with Joey and Connor following me into the kitchen. I made a bowl of cereal and was half way through it before Joey asked me why I was naked. I told him that he woke me up, and that I sleep naked. That second part made him giggle. June 9th Every day this week, Joey and Connor have woken me up pounding on my door, and every day I've answered the door naked and eaten breakfast in front of them naked. I don't know why they can't let me sleep in. Kids are supposed to sleep in during the summer. Joey's grandmother stays with him during the week, and Connor's mom drops him off at Joey's on the way to work, so I guess they figure since they're up, I should be up, too. I've also gone out of the house in nothing but a pair of shorts all week. On Tuesday, Connor said something about it. I told him I was too grown up to be scared of having people see me bare-chested. That earned an immediate attack from both Connor and Joey. They always team up against me, and without Sierra to help me, it's hopeless. They spent the rest of the day razzing me about being "grown up," but on Wednesday, Connor showed up without a shirt on, though he was wearing shoes. I didn't say anything, and neither did Joey, but I imagine Joey must have said something to Connor at his house. I'm sure Connor would have put an abrupt end to any teasing. Connor and Joey are inseparable, but Connor doesn't let Joey get away with anything he doesn't want him to. June 10th I didn't think there could be anything more embarrassing than the sex talk that Mom had with me last week, but I was wrong. This morning, she came home from grocery shopping with a box of condoms! I got upset, and Mom complained that she went to a lot of trouble to find ones that would fit a penis my size. So embarrassing! Mom said that all boys, and men, worry about the size of their penises, but that although mine was just the right size for my age, it wasn't as big as a man's, yet. The box said "Snugger Fit" on the front. I thought I was going to die! I argued that I wasn't even squirting, yet, but she said that I could start at any time. After a bit of a fight, I told her I'd take them even though I wouldn't be needing them. She insisted on teaching me how to put them on right! That started the fight all over, again. I told her I'd figure it out for myself, but she wanted to be sure. The most embarrassing part was that my penis wouldn't get stiff, no matter how much I rubbed it. Mom even rubbed it some, for me, and it still wouldn't get stiff. I sat in my room and sulked for a long time. Eventually, Mom came in and sat on my bed. She pulled me close to her and hugged me. I tried to pull away, but Mom's still too big for me. Actually, it felt really good having her hug me. I don't fight with Mom very often, but when I do, I always feel really bad, afterwards. "Kevin," she said, "You've been masturbating in front of me for a few weeks, now. I didn't think there was anything left to be embarrassed about. Most boys would be mortified to be caught masturbating by their mothers. I thought we had a special relationship where we could talk to each other." I hate it when Mom says stuff like that. It makes me want to cry because I feel bad about how I've acted. "Tell me the truth. You've been thinking about Sierra as something more than a friend, haven't you? Don't worry, you won't be in trouble. I won't be mad." I nodded yes. "That's okay. It's perfectly normal. If you haven't already, you're going to start wanting to have sex with her. Maybe you won't realize that's what you want. You'll probably start out doing something else, but eventually, you're going to try to put your penis in her, and she just might let you." Back to embarrassing! Mom usually has a lot of patience, but when she runs out, you don't want to mess with her. "Here's the deal," she said, in a tone that told me she was done trying to convince me. "You learn how to use these, or I put you in day camp for the rest of the summer." I almost said, "So? I'll see Sierra on the weekends," but the part of my brain that keeps me from cracking my skull open stopped me. I still couldn't get an erection, so Mom let it go. By evening, we were both feeling better, and I finally got stiff. Mom put the first condom on, for me. It was really weird having her touch me like that, but it felt kind of good, too. I tried the second one, but I messed it up. I got frustrated and lost my erection. Mom cuddled with me and teased me, saying that she'd bet I wouldn't have any trouble getting stiff for Sierra. That did it! She put another one on for me. I messed up the next two, but Mom's teasing had gotten me really worked up. I struggled with the next two, but I did get them on. I put the next three on properly, with no problems! Mom was convinced that I knew how to use them right and told me I should masturbate with that last condom still on. Afterwards, she told me that it was important to pull out of the girl and remove the condom while my penis was still stiff. I asked her if I could stay home by myself. She said I could. "I think it would be best if you waited to have sex, but if you're going to, you have to promise me that you'll use those condoms." Mom actually made me promise by saying all the words, not just "I promise." June 12th I don't know why, but Joey and Connor didn't wake me up this morning. Sierra did come by just before noon. I thought she'd want to kiss and stuff, but we just sat on the couch watching TV while she told me all about her stay with her grandparents. I was naked, and she was wearing her string bikini, but I had masturbated when I woke up, so I didn't get stiff sitting next to her. I didn't dare tell her about the condoms! I didn't want her to know that I was even thinking about it! Mom got lunch meat so I could make sandwiches for myself. I offered to make one for Sierra, but she said that she wanted a hotdog, instead. I started to tell her that I didn't have any hotdogs when she knelt in front of me and took my penis into her mouth. It went stiff right away. After I had my orgasm, Sierra had me lick her pussy. That's actually a lot of fun. I like all the noises Sierra makes when I do that to her! After lunch, I laid down on the couch, and Sierra laid on top of me and did that thing where she rubs her pussy against my stiff penis. She also did that thing where she pretends that I'm trying to stick it in her, but she's the one who's trying to get it inside her. Once again, I felt the tip of my penis pop through a tight ring, and Sierra got really still. She smiled at me then started laughing, claiming that I was being sneaky and tricking her into putting my penis inside her. I told her that she was the one causing the trouble and gave her a playful swat on the butt. She jumped when I did that, causing my penis to pop free. Then she attacked me. Sierra may be a girl, but she's really strong. We ended up on the floor, rolling around, each trying to gain the advantage on the other. Eventually, I ended up on top of her with her arms pinned above her head. We both stopped fighting as we realized that the tip of my penis was just sticking inside her enough to spread her pussy open. We stayed like that, frozen, staring each other in the eye. It was like she was daring me to try it, and I was threatening that I would, but neither one of us said a word. Her look changed to a smug "I knew you wouldn't." I pushed forward just a little bit, and I felt the tip of my penis push through that ring, again. Sierra's look changed to surprise, and worry. I no longer felt challenged by her, so I relaxed. When I did, my body lowered against hers, and my penis slid into a very warm, wet, and slippery place! It felt wonderful! Sierra gasped, and I held very still. My penis started throbbing. I thought I'd better pull out before Sierra got mad. I started lifting up, but then Sierra wrapped her legs around me tightly and pulled me back in. My penis started pulsing with an incredible orgasm. I laid on top of Sierra, enjoying the wonderful sensation of being so close to her. Shortly, my penis went soft and slipped out of her. She told me I was getting heavy, so I got off her and sat on the couch. Sierra sat next to me. Neither one of us said anything for a long time. Eventually, Sierra said she had to go. She put on her bikini and left without another word. What I did with Sierra was really nice, but I'm a little upset because I didn't use a condom like I promised Mom I would. June 13th Joey and Connor woke me up, again, only this time, Sierra was with them. They both looked shocked when I didn't flinch at being naked in front of Sierra, and Sierra acted like there was nothing unusual. Finally, Joey couldn't take it anymore. "Hey, Sierra, notice anything special about Kevin?" "Not really." The puzzled look on Joey's face made me laugh. "Ah, come on! He's naked!" "So? I've seen naked boys, before. I see Travis naked all the time." Joey looked really disappointed. Connor just looked confused. I grabbed a pair of shorts before we went out. When I put them on, I noticed that something was in the pocket. It was a condom! I checked all the shorts in my drawer. Mom had put a condom in the pocket of every pair of shorts I had! I couldn't see Sierra wanting to do anything in front of Joey and Connor, and I certainly didn't, but I left the condom in the pocket. Joey was silent until we got to the woods, then he said, "What's with you, two? Sierra, how come you don't care that Kevin was naked? And Kevin, how come you don't care about Sierra seeing you naked?" Sierra answered for us, "I guess we're just more mature than you are, Joey." Connor smiled, which got him a punch in the arm from Joey. No one said anything more about it for the rest of the day. It was just a normal day, like before Sierra and I had started fooling around. In the afternoon, Connor had to go somewhere with his mom, and Joey was complaining about the heat and went home. Sierra came back to my house. Once we got inside, she pulled my pants down and tripped me up. Holding my shorts, she noticed something in the pocket and took out the condom. I was surprised that she didn't know what it was! I told her about the whole deal with Mom. She was upset, at first, because she thought I had told my mom about us, but when I explained the whole story, she calmed down and got a mischievous grin on her face. "Want to try one out?" I was so excited that I had a little trouble getting it on, but eventually I did. Sierra kept giggling. I climbed on top of her like I had yesterday. This time, I couldn't seem to find the right place, which got Sierra giggling even more. Eventually, she used her hands to guide me in. It was still nice, but I didn't feel that wet sensation like I did without the condom. It was still warm and tight, just not wet. Anyway, it was nice enough that I didn't mind. Actually, it was fantastic! When Mom got home from work, she found the condom wrapper on the floor. I had buried the used condom deep in the kitchen garbage, but I had completely forgotten about the wrapper. "Good thing I got these, huh?" I was going to lie and say that I was just practicing putting it on, but it hurts when I lie to Mom, so I told her everything. Everything! Even the part about Sierra being upset when she thought I had told. Mom promised she wouldn't say anything to Sierra, and she was proud of me for using the condom. She even told me that it was okay that I hadn't used one that first time, since I wasn't ejaculating, but she made me promise that I'd be more careful. She took me out to dinner to celebrate my first time having sex with a girl. That night, we cuddled on the couch and watched a movie. She rubbed my chest and belly, and even played with my penis a little! ----- If you enjoyed this story (or any of my other stories), I would appreciate a quick comment. Thanks! https://secure.asstr.org/cgi-bin/ah_feedback.cgi?id=KYKADDHQSDHAFCAVRWRM