My journey into giving a woman pleasure starts here.
I was 10 years old, a few months from turning 11. Every evening I would walk up to the diner at the top of the hill from where I lived for a burger. I would take the alley behind our house to the top of the hill, then cross the street into a vacant lot that was mostly woods. The path through the woods ended at the parking lot behind the diner. It was the last full week of summer vacation from school. My grandmother, who was raising me had taken me shopping for school supplies, so I was a little later than normal heading up the hill. This was 1961, and our neighborhood was a safe, and quiet one, no-one locked their doors. Although it was now dark, my grandmother surprised me by handing me a quarter for my burger. "Be back before 10 o'clock", she said as I walked out the back door. My uncle John was picking me up at 11o'clock to go night fishing. I was antsy to go, so I hurried up the alley.
I was a skinny kid, and walked light on my feet, an adult cousin had taught me this while deer hunting. The woods were almost pitch black when I got there. I stood there trying to decide whether to go through, or go around the gas station on the corner, when I heard a wimper, then a moan. I had heard a simular sound one time when I walked in on my oldest sister Marie, and her husband having sex. I entered the path, staying close to one side to avoid the tiny trickles of moonlight that shown onto the path. The entire path is only about a hundred feet long, and almost straight. About thirty feet in the sounds were getting close enough for me to figure out exactly where they were coming from. Several of the guys my age in the neighborhood had built a small fort about ten feet square in the woods. We had more rain than usual that August, so the ground was not dry enough for me to be heard moving closer.
Ahhheeee, umahhheee, ahaa ahaa ahaaaahhhhhhhhhhhAAAAAAHHHH. I was looking in through one of the gunports we built into the wall, straight at Sandy's pussy, with a guy who worked at the gas station's toungue attatched to it. Sandy, a high school girl who lived about a half of a block from me was pumping her pussy for all it was worth into Sonny's face. She had hold of her legs by the backs of her knees with the inside of her elbows, while Sonny was pinching her nipples, and licking away. I had never seen anything like that, so I took off down to the diner.
I must of been realy redfaced when I ran in through the door. Maggie, the waitress came running over grabbing me to see what was wrong. She knew that I had asthma, and thought I was having an attack. "Tommy, whats wrong with you boy? Betty, bring me a mug of root beer, we gotta get this boy cooled off, he's as hot as your grill back there. What happened?" Betty, the cook brought the frosted mug of rootbeer. They finally calmed down enough for me to tell them what I had seen. Maggie went out the back door, and was gone for fifteen minutes. When she came back I could barely hear what she was whispering to Betty. "Betty, my god that Sonny over at the shell station has a cock on him. Sandy down the street was giving him one hellofa blowjob. He kept begging to fuck her, but she kept shaking her head no, while at the same time jacking him off with BOTH hands, and not letting go of his cock with her mouth, her head a bobbing up and down like a piston, a slurping and squishing louder than his moaning. I couldn't take it any longer, I had to diddle myself, that one was a good one, the best I've done in a while, OOOH Betty. That Sonny sounds like he can eat some pussey too, I'm gonna have to strap him on one time, and I ain't gonna say no to anything." Betty, laughing, looked down at Maggie's legs and said loud enough for me to hear,"I bet you will, that damn sure must have been a good one, it's running down your leg like a river". I bent over to look at Maggie's legs, but she reached over and pushed my face back up. I had caught a glimpse of Maggie's panties when she got down to hold me when I first came in, they were now in her dress pocket. I looked at the clock, it was time for to get home. I heard Maggie say to Betty, "Oh shit Betty, I just gave that boy his first sniff of pussy". "How's that?" Betty asked. " when I pushed his grinning little face back away from me, I used the hand that I diddled with. I didn't care about him seeing anything running down my leg, but I took my panties off up there in the woods, and you know how this unform bulges out between the buttons sometimes, and that boy might have seen my pussy." So that is what that smell was I grinned to myself and was off back down the hill. They were gone when I walked back past the fort, which I immidiately renamed "Fort Diddle".
I was now more determaned than ever to figure this sex thing out. I had been playing touchy-feely with every girl in my neighborhood that would. Most did because they were just as curious as I was about sex. They had either heard their parents having sex, or like me caught someone. So when I asked one girl if I could lick her pussy, she slapped me and said that I was sick. I was going to have to figure something else out.
I thought that Maggie was a pretty hip person, and told her so several times. She never talked down to me when we had a serious conversation, like the time we talked about my oldest sister getting pregnant at sixteen. Maggie had tried to help me to understand that sometimes the body won't listen to the mind, and common sense. She told me that allot of what she was saying may not realy make any sense to me until I got a little older, and had experienced what it was like to be horny. So one day on my way home form school I ran into Maggie while she was getting gas. She seemed to have her mind somewhere else, and kept looking around the station. So finally I said to her, "he ain't here today". "Who ain't here" she answered. "Sonny, the guy you wanted to strap on, what ever that means" I said. She turned beet red, and said in an angry voice, as she looked around to see if anyone was close, "boy, get in that car, we need to talk". The tone of her voice, and the look on her face took me aback a little, so I silently did as I was told. "Have you said anything about any of this to ANYONE", she asked. I told her that no I had not. This calmed her down. "You want a rootbeer?" she asked with a smile. She got herself a coke, and me a rootbeer out of the pop machine, and pulled her car around back of the diner to where she always parked when she worked. "Tommy honny, your learning about this stuff way too fast, it'll all come soon enough, but if you are determaned to find out, be very careful who you talk to. I know that your grandparents won't talk to you about it. See if your uncle will, if he won't, talk to someone else that you can trust. And if you can't find anyone by the end of the month, I'll see what I can do. Now get your skinny little butt home", she said as she leand across me to open the door on my side, crushing me with her big titties, her nipples were like rocks.
My grandmother came from a large family, followed by a huge extended family. Whenever there was an emergency, or death in the family, she would go to wherever she was needed. So in the middle of September, she was off to her brothers home about two hundred miles away. He had been injured in an accident. Because I had just started back to school, I needed to stay home.
My oldest sister Maria had been seperated from her husband for about four months. She moved to within three blocks from where I lived. Where she lived was a block closer to the school, so that made her appartment the best place for me to stay while my grandmother was gone. My grandfather worked nights, so I couldn't stay there alone.
Maria, I call her Sis, is eight years older than I am. She is short, about five feet, and has a fantastic body. I didn't know her measurements, but her tits are nice size, not huge like Maggie's, nor like two fried eggs like Sandy's. Even though she had had a baby, her waist had trimmed back down to almost tiny, unlike our cousin Judy who never lost most of the fat she had gaind during pregnancy. Sis has a perfect set of legs, short, but perfect, topped by an ass that was better than most I had seen in uncle John's skin books. When she was still living with her husband, he was gone allot, working construction out of town. So I would stay with her often. Very early on, while she was still pregnant, she asked me to give her back rubs. By her being so small in stature, and her baby was a bit large, she had started getting pain in her back. She would get down on her knees, and then lay her head, and shoulders on the sofa, or chair. This way she would not be laying on her big belly. After she had the baby, she would lay flat on the bed, face down. I would always try to feel her up, but she always stopped me before I really touched anything I shouldent, saying,"alright, you better behave, or I'll slap you"
We went grocery shopping on Saturday. I played with the fifteen month old baby, while Sis shopped. Sis said that she was going to get us a pizza from a shop down the street for dinner after she put the groceries away. That was OK with me. Although Sis was eight years older than me, we were extremely close. She would often confide her inner feelings to me. I think this is why she only half heartedly scolded me for trying to feel her up all of the time. She never however allowed me to cross the line into anything really improper. I could talk to her as well, about anything, mostly silly kids stuff, but once in a while we would have some deep serious talks. One of those talks was after I had walked in on her, and her husband having sex. He thought it was funny, and crudely teased her. But after he left for work, she and I had a long talk. It centered mostly around respect, but she also explained a little bit about sex, and conception.
I was proud to walk along side of Sis, pushing the stroller. Every man in the neighborhood had oggled at her as we would walk by. She was hungry, and so was I, so we went for our pizza before she finished with the groceries. After we finished eating, she went into her bedroom and changed into shorts, and a halter top, then went back to her groceries. Several times Sis would bend over, and I could see some long hairs from her bush sticking out of the crotch of her shorts around her thighs. "Quit looking at me like that, and behave, I'm your sister, not one of those little girls you're sniffing around", was about all she would say. Sis's apartment was on the top floor of a three story building. She had no air conditioners, only a window fan, and it was still pretty hot in September. The halter top she was wearing was thin white cotton, and by the time she was finished with cleaning up after getting done with the groceries, it was soaked.
Since she had been pregnant, her nipples had gotten darker. I had seen her a few times coming out of the bathroom when she still lived with us, she was about fourteen, or fifteen then. Her nipples then were puffy, and a light pink. It wasn't until that evening that I noticed how much darker her nipples seemed to be. She could see me looking at them, but said nothing, just shook her head. Just then I noticed that there was something wet running down her thigh. That reminded me of Maggie, then I remembered her saying to talk to someone I realy trusted about sex.
So I asked her. "Sis, what is eating pussy, blowjobs, and diddling yourself all about, and what runs down your leg when you do?" She was so taken aback by my question that she just flopped down onto a footstool near her. She got this bewildered look on her face, then it turned angry. "What the hell is the matter with you? You've been gawking at me all day with that look in your eye. I'm your sister, you have no business looking at me like some tramp. Why would you even think to ask me a question like that?" , she yelled. I was almost to tears, but I managed to tell her about everything, including what Maggie said about trusting the person I talked to. She just looked at me for a moment. Sis has a terrific sweet disposition, but when she gets mad, she's a terror. After a minute of unbearable silence, I just said, "Sis, you are the only one who will be honest, and I can't figure out why everything is such a secret, and everyone gets pissed off if I ask anything" She calmed down allot quicker than I thought she would. Sis just cocked her head to the side a little, and looked at me out of the corner of her eye. It was by then going on eight o'clock, so when she finally spoke again, she told me to go get my bath while she put the baby to bed. After I finished my bath, Sis took hers. She was in there for almost an hour.
I was watching television when she came out of the bathroom. I couldn't beleive what she was wearing. Sis had on a white v-neck t-shirt that had been her husband's. It only came down a few inches on her thigh, and had the sleeves cut off. She went around the house and closed all of the blinds, and curtans. "Go get ready for bed, I'll be in there in a minute", was all that she said. I could hear her digging through some papers in the hall closet, five minutes later she came into the bedroom. "Are you ready to give me my backrub Buster?", she asked as she came in. "Yep" I said, releived that she was not mad at me.
This time however, when Sis laid down on the bed, she lay on top of the sheets. She would usually be under them, and pulled the sheets up enough to cover her awsome ass. The only light on in the house was the small table lamp on her nitestand. When she got into bed, I could see through the V-neck that she was completely naked under the shirt. I started just like I always did by pushing her long brown hair to the side away from me. Then I would massage her neck, then move to her shoulders. She always liked me to use allot of pressure on her shoulders. She was laying with her face toward me, with her hands, and elbows under her pillow. As I moved my hand down along her underarm, my fingertips slid into the sleeve opening. My fingertips slid down far enough that I thought I could feel the side of her nipple. "Thats far enough kiddo, finish the rest of my back, then it's time for us to have a loooong talk" she said. I continued working my way down her back, and as I did her legs parted slightly, exposing her ass, and her pussey enough for me to see the layers of folds outlining her slit. It looked moist. Just as I started to rub her now bare ass, she stopped me, and got up and went into the front room. Before this, she would always stop me when I reached the sheets that covered her from the waist down.
Sis came back carrying two small pamphlets, one light blue, and one light pink. She then started to adjust the swing arm reading light that was mounted to the wall above the headboard. As she was doing this, she told me to go get the pillows from the sofa; I did. I noticed that Sis was growing increasingly nervous as she was figiting around with the light, then the pillows. Several times she walked over to the windows to check, and recheck them to make sure that they were completely covered. Finally Sis crawled into the middle of the bed where she had arranged the pillows against the headboard for us to lean against. As she scooted over, and settled in, her shirt had worked it's way up to her waist. Sis just looked down at her bare pussy, then at me with a nervous grin, and reached over and picked up the light blue book, turning the small lamp off as she picked up the book. She reached up and made one final adjustment to the reading light, then scooted over close enough for bare ass to be tight against me.
"I don't have to read this whole thing to you, I can just show you, and axplain everything to you" she said as she opened the book. " The book is called The Male Reproduction System, I'll show you the important stuff, then you can read the rest on your own." There were no pictures, only drawings, so Sis pointed to the drawing as she read off an explaination. As she was doing this she raised her left knee and placed her foot next to her right knee. She was to my left, so I had a great view. The illistration was a cutaway, side view, so when she tried to tell me about the sensitive part on the underside of the head, I didn't quite understand. Sis just sat there for a few moments, and I could tell that she was getting more, and more nervous. Finally she said, "now listen, I've been letting you see my pussy, and titties all evening, and I've been doing it on purpose just to see if you get a boner. Because until you start getting hard-on's, you won't really understand the pleasure part of sex, how it feels to cum." The same thing that Maggie said I thought as Sis continued. " Now you have got to promis me that you will never tell a soul about this little talk, because if you do, I can get into allot of trouble, bad, bad trouble. Do you promis?" I answered yes, then asked her how she could get into trouble. "Well first off, you're ten, and I'm eighteen, and that's called carnal knowledge with a minor, the law calls kids minor's. Second, I'm your sister, and that's incest, even if I don't let you touch me, and I'm not going to either." I nodded my head just as a nervous shudder went over Sis. "There just ain't no other way to do this I guess." she whispered, more to herself I think, than to me. "Are you sure you promis?" I said, "on my scouts honor, cross my heart." "OK then, take your PJ's and your underwear off." Shocked, I nervously undressed, and as I did I heard her whisper again. " This is insane, I've got to draw the line, I've got to. But if I don't do this, some pervert will get ahold of him, then who know's what will happen. I just can't let him touch me, I've got to control myself, I've got to."
Sis reached over and wrapped her right hand around my dick. She just sat there holding it for a few moments, squeezing every now and then. She watched her hand closely as she gently started to stroke my dick. What she did next amazed me. She peeled the forskin back, and as she was doing this, she licked the fingers on her left hand, and started rubbing the underside of my dick head with them. My dick started to stiffen a tiny bit, but it did not get hard. Sis stopped, looked over at me with a smile and said, "I have to stop, or you'll pee all over us. When a boy is not quite old enough to cum, but all the nerves that causes him to get aroused are starting to work, it causes him to pee instead of cum. But did that feel good though? You asked me about a blowjob, well, when a woman puts a dick in her mouth, she sucks on it, and uses her tongue to rub it like I did with my fingers. In other words, she uses her mouth to make him cum." She laid the blue book back on the nitestand, and got the pink one. As she leaned over she laid her left leg back down flat, and lifted her right one to balance herself completely exposing her crotch. When she did this, I could see that her pussy was all wet, and there was a wet spot on the bed.
Sis sat there looking through the book for a few minutes before she said anything. Another shudder went through her. I asked her if she was cold or something. She hugged me, and said, "no, it's just that I have to be careful. I wasn't supposed to touch you like I did, and I definitely am not letting you touch me. It's been five monthe, and this can get out of control quick, real quick." Not sure what she was talkig about, I just reached over and took her other hand. When I did this I brushed her nipple, which shot up like a rocket. "Mmmmmmmmmm" she sighed as she laid my hand back to my side. My hand was now between us. I was rubbing her bare leg gently with my knuckles. Sis took a deep breath, and blew hard as she released it.
"OK, women have more special spots than men do, but the most sensitive one is this one, it's called a clit." Sis pointed it out on the drawing. "You asked me about diddling, well, that's really called masterbation. Men do it like I just did you, only they keep going until they cum. When women do it they play with their nipples while the rub their clit, and they sometimes stick their fingers in their pussy." "How can you do all that at once?", I asked. Sis burst out laughing, an almost eery kind of nervous laugh. " It ain't easy, but it can be done," she said. "Why do you play with your nipples?", I then asked. " That helps to get a woman's pussy wet so a man can get his dick in it easier. That wet stuff is what runs down a womans leg when she gets too wet." she answered.
Sis just sat there for a moment without saying anything, but while she did, she moved her ass in tiny circles. Then she closed her eyes, and got a tense look on her face. I asked her if she was OK, "close" was all that she said.
Suddenly she shook her self back to reality, saying that she almost forgot that I was there. "If I show you what happens when my nipples are touched, you can't tell a soul, OK?" I nodded. I almost fell over when she pulled the shirt over her head. Looking at me, setting there naked, she said, "well hell, it ain't like you've not seen all this, you've been looking at it all night." Sis turned to me, her right nipple was now just inches from my face. Without saying anything, I moved my head forward, and kissed her nipple, then jerked back quickly. Sis let out a long sigh, then put her arm around me, and pulled me to her breast. "Suck on it, gently at first. Mmmmmmmm this feels sooo good. MmmmHmmmm that's it, now a little harder, just right mmmmmmmmmm." Still holding my head, Sis scooted down a little, then she lay her right leg over my lap. She began to move her hips more now, still in a circular motion, lifting her left knee up so that her left foot was against her ass.
"Now this one, see how nice and hard they are getting?", she said as she gently moved me to her other nipple. I fondled her breast with both hands as I worked on her nipple with my tongue, following her instructions. After what seem like an hour, minutes really, I was going for it. She was so lost in pleasure I thought, that she would not notice me moving my hand to her pussy. My nervous fingers found her sopping wet, and incrediblelly hot pussy. Finding her clit was easy, it was as hard, but a little bit bigger, and longer than an eraser on pencil. She opened her legs more, and kissed me on the forhead, saying, "I wondered how long it would take you to get the idea,." Her pussy was so wet that her juices were pooling in my hand. Panting, she said, "inside me, fuck me with your fingers you horny little shit, do it fassssst, rub my clit with your thumb as you fuck me." She's almost flat on her back now, her pussy thrusting back at my hand like a machine. "Fuck meeeeeeeeeeeeeee, now, yes nowwwwww, here it is, godddd I'm cumming, cummmmmmiiiinnnggg". She lifted her ass about two feet off of the bed, as she gushed like a fire hydrent.
Sis lay there afterwards with her eyes closed for a minute or two, gently stroking my now simi hard cock. She rolled over, and took my cock into her mouth, and started giving me my first blowjob. She stopped after about five minutes, saying, "you're almost there, no more than six months or so you'll be squirting cum everywhere you little shit, anyway, that was what a blowjob is." She moved up beside me, facing me, she pulled me against her naked body. I kissed her on the lips, then just held her. I looked her in the eye after a few minutes, then I asked her, " Sis, can I lick your pussy?" She looked at me for at least two or three minutes with a puzzled look on her face. After another smile broke on her face, she got up out of the bed. I took this to mean no. But she took the extra pillows and placed them on the floor next to the bed on her side. "Come around here and get on your knees on these pillows." she said. As I was moveing over to where she wanted me, she sat down on the edge of the bed right in front of my face.
" Remember how you used your tongue on my nipples, do the same thing on my clit." She opened her pussy to me. Then she took hold of her legs at the knees, letting them slide into her armpits. This lifted her pussy right to my lips. I licked her pussy up and down several times, then went straight for her clit. As soon as I put my lips to it, it started to get hard. I gently sucked, and to my surprise, it started to get even bigger than before. Sis was panting loudly now, and moaning. Her pussy was quivering beneith my lips. She wasn't moving her hips as much as she did when I fingered her, but she was moving some. Suddenly, Sis started to yell out to me, "suck my clitty, suck it good, you're gonna make me cum again, and it's coming quick. OH FUCK, I neeeed this, suck it sweety, suck it. Ohohoho, ohohoho ohhhhaaaaaaaaaaaa, close, verrrrry close, fuck me with your fingers, while you suck my pussy. Gettinggggg closer. Now, now, here it comes baby, AAAAAAAAAAHHHHHHHHHoooooooooooooooo. oh god I can't take any more, aaaahhhh, there's another one, ohooooooooo." With that, the dam broke, I was completely soaked. Sis pulled herself away from me, and lay spred out across the bed. "I can't beleive this shit, a ten yoer old boy just gave me my first multable orgasm ever, my own fucking little brother no less, and not even old enough to fuck yet. What a night, what an orgasm." Then looking at me, she said, "well I guess that now you know what eating pussy is all about, and that stuff that was running down that woman's leg you asked about? Well it's dripping off of your eyebrows. "
We went into the bathroom, and took a bath together. She wanted to make sure that every drop of her juice was washed off so no-one would suspect any thing.
After that night, we never fooled around again, until she was thirty one, and I was twenty three.