I was sixteen when I saw my first naked woman. It was Mrs. Oliver, the lady next door and she was sunning herself out on her patio one summer afternoon when I was out back watering plants that were part of my summer chores.
Some soft music drifted over the fence and, being curious, I went to the fence and looked over. There she was, our sexy-looking next-door neighbor, stretched out on a lounge chair totally naked. I did what any guy my age would do, I took out my dick and I started jacking off.
Somehow, she must have sensed that she was being watched because her head snapped in my direction and she saw me.
"Nathan, you come over here this instant," she barked.
Omigod, I thought, I was caught. I quickly put my dick away and went around out our yard and into her backyard. She'd pulled a towel up over herself and I slowly, reluctantly walked over to her.
"Well, young man, you certainly got an eyeful. How would you like me to tell your mother about this?"
"Oh, please don't. I just heard some music and kind of looked, that's all."
"You looked for quite a while from what I saw. I have a good idea what you were doing on the other side of the fence, Nathan. You were masturbating, weren't you?"
How did she know, I wondered as I told her, "Um, I wasn't, I swear."
"Yes, you were. I know how boys are. Do you want me to tell your mother?"
"No, please don't do that, she'll really be upset about it."
"Well, Nathan, I might not, if you do something for me, okay?"
"Yes, I'll do anything, just don't tell my mom."
"First, you have to tell me the truth about what you were doing."
"Um, well, I was, um, doing what you said."
"I thought so. I know how boys are. Well, if you don't want me to tell your mother, then you'll have to finish what you were doing. Right here while I watch you."
Omigod, that meant that I would have to show her my dick. That was bad enough but I also knew that it was small, I'd measured it after some guys I knew were talking at school about how big their dicks were, you know, like six, seven, eight inches, and I went home and got my ruler and some hand lotion and, well, as hard as I tried, it wouldn't top five and a quarter inches.
So, not only would I have to get my dick out, she would see what a wimpy one I had. That was even worse.
"Do I have to?" I begged.
"Yes, Nathan, you were spying on me, trying to see me naked, over there behind the fence masturbating. Now, you have to do it right here. While I watch."
"But that means I have to ... um, take out my..."
"Yes, Nathan, it means you have to take your clothes off and masturbate."
"My clothes? All of them?"
"Yes, Nathan, all of them."
I didn't know what else to do, so I pulled off my teeshirt, then pulled my shorts down and stood there in my navy briefs. As scared as I was, they were embarrassingly poked-out.
"Go, ahead, Nathan, I've seen a penis before. Do it, Nathan. Do it now."
I pulled down my briefs, she handed me the suntan lotion, asking if I needed it, and I dribbled some on my hand and started.
"Come closer, Nathan, get right over here. Do it, Nathan, do it, do it now," she said as I slowly stroked up and down.
"Does it feel good, Nathan, tell me how it feels, I want to know?"
"Yeah, really good."
"Come on, Nathan, tell me more about how it feels. Be more descriptive."
"Um," I stalled, trying to think exactly what she might want from me, "um, it makes the end feel all tingly when I rub it like this. Like my whole middle feels good."
"Does this help?" she asked as she pulled the towel down showing me her breasts.
Now, Mrs. Oliver was maybe somewhere in her thirties, like medium-height, with a nice, slim body. Her boobs were really nice, even flat on her back, they stood up nice, a lot like the girls in Playboy. They were like the size of grapefruits, nice and round and full with wide, pink nipples, the centers all hard and poked-out.
"You're really pretty, Mrs. Oliver, yes, it does help."
"Tell me what you see, Nathan, tell me what you like about what I'm showing you."
"They're really pretty," I told her awkwardly.
"And? What else, Nathan? What would you like to do with my breasts?"
She had her hand under the towel and I could tell that her knees were now spread wider, she must be rubbing her pussy or putting a finger in it.
I was getting more used to this, a little more relaxed, so I told her, "I'd love to feel them, see how they feel in my hands."
"Would you like to suck them? Suck on my nipples?"
"Yeah that would be cool. Do you think I could?"
Hell, I had little to lose and this seemed to be going better than I'd first thought.
"We'll see, Nathan, we'll see how you do with this first. Let's see how you shoot your cum. You must be a very horny young man. Are you liking this?"
"Oh, I'm loving this, it's incredible and you're so pretty to look at while I do this," I gushed.
"Maybe this will help even more, Nathan," she said, smiling up at me as I masturbated standing there. She pulled the towel off and dropped it on the concrete, then dropped her feet off the lounge chair onto the patio showing me her wide-open pussy.
It was shaved clean, plump and pink with a dewy slit along the middle which she began rubbing with her finger up and down.
"Cum, Nathan, see if you can get it right here, right on my pussy."
I moved a little closer, I'd never really used my dick for target practice but I was going to try.
"I'm pretty close, this has really got me going good," I moaned, then I felt that wonderful feeling of release and I pushed my hips out so arcs of cum went flying out of me, more than I think I'd ever seen before, some of it landing on her stomach, some on her leg, some on the concrete below me but, there it was, a couple of globs right on her pussy.
"Good aim, Nathan. Now, let's see you lick that off me," she said grinning up at me as I knelt down next to her as she dropped her left knee sideways so I could lick my cum off.
"Take your time, Nathan, make sure you get me as clean as you can, there's no rush," she said as I moved my tongue down to get it into her slit.
"Mmm, that's lovely, Nathan, yes, I don't think I'll tell your mother about you spying on me, I'm rather glad you did, you naughty boy. You have to do what I tell you to do from now on, Nathan. Do you understand that, Nathan? You belong to me now, you do what I say, what I tell you to do. Now, lick me until I cum."
I'd heard guys talk about eating girl's pussies, though it always sounded weird to me because you really didn't eat them, you licked and sucked and tongued. Nobody talked about guys getting their dicks eaten, it just seemed like an odd thing to call it.
But, there was nothing odd about doing it, I was loving it. She was so smooth down there, the groove between her legs tasted a little salty but nice and she sure was liking it; I could tell by her soft moans and how it made her squirm and writhe.
Her hands came down as I was licking her and her fingertips pulled her pussy open.
"In there, Nathan, lick me up in there while I hold myself open," she panted.
I could now get up into the hole that went up inside her and when I rubbed my tongue around, I knew it felt really good as she was groaning a lot now.
"Oh, yes, mmm, right in there, omigod, Nathan, yes, right there. Don't stop, make me cum, Nathan, make me cum."
I kept licking and tonguing up into her while she held herself open for me and soon she started shaking and bucking her hips against my mouth, trying to keep her cries of joy from bellowing across the neighborhood.
"Oh, oh, Nathan, omigod, you've made me feel so good, come up here and kiss me, give me a hug," she said and I leaned over to kiss her as her left hand dropped down to take hold of my dick.
"You're mine, now, Nathan, you'll do whatever I want you to do, right?"
"Yes, Mrs. Oliver, whatever you want," I told her.
I wasn't particularly afraid now, no, it was more that I wanted to do whatever she wanted me to do. It was my first sexual experience and I just knew that there would be a lot more if I went along with her in whatever she wanted.
"The first thing is, you can call me Gwen when we're together. Now, call me that."
"Yes, Gwen," I said.
"Tell me how much you liked giving me an orgasm and anything else you want to tell me."
"I loved doing that. It's the first time I've ever done it but I really liked doing it. See? See what that does to me?" I told her lifting it up so she could see how hard my cock was.
"Well, Nathan, you'll just have to masturbate that again while I watch. I rather enjoy watching you do that, you know. Come on, get up here, squirt it on my boobs this time," she said as I took the lotion again and began jacking off. She lifted her knee away so I could see her pussy better and said I could play with her boobs if it helped me get off.
She saw me looking down, then asked, "You like looking at my pussy, don't you, Nathan?"
"Yeah, it's really sexy to look at and I really liked what I did to clean you up from my, you know, my sperm."
"Your cum, Nathan, on my pussy, you can say these words, after all I've heard them all before," she laughed, "go ahead, say it the way you would to the boys at school. Do it, Nathan, tell me."
"I think looking at your pussy is so hot and I loved licking my cum off your pussy, especially when I got you off."
"Good boy, now lets make that nice dick of yours cum all over me again."
I was happily stroking away, thinking about how neat it was to be naked like this, jacking-off over a hot-looking naked woman and that it was looking like this might just become a regular thing.
Even though I'd thought that my dick was on the smallish side, she never said anything, so maybe it wasn't so bad. Anyway, standing there, stroking up and down sure did feel good.
"You look happy, Nathan. Are you liking what we're doing? Would you like to do this every day?"
"Every day, you really mean it?"
"Yes, Nathan, you can come see me every day and you can masturbate for me. I want you to, Nathan, and you do what I want, don't you?"
"Yes, Mrs. Oliver."
"It's Gwen, we discussed that, right, Nathan?"
"Yes, Gwen, I'll masturbate for you every day. I really like doing it," I got out right when I started cumming again.
"Yes, you certainly like doing it Nathan. Just like I enjoy watching you. I want you to lick my pussy again, Nathan, do it, now, Nathan, or maybe we won't be able to do this every day like you want."
Well, you know what I did, right? I got down in front of her and gave her oral sex again. That was when she showed me where her clit was. It was on the outside near the top, not up inside her where I'd guessed it might be. She showed me how to rub it with my fingers and my tongue and when it got bigger, how to softly suck on it to make her go crazy.
After I got her off, she told me to get dressed so I could be home when my parents got home from work. She stayed naked, kissing me goodbye as I went out her back door to go home, changed forever.
She had told me just to come in her back gate the next morning and then into her house through the back slider and she'd be waiting for me.
So, I waited nervously until nine o'clock, went through her back gate and into her house.
"Mrs. Oliv ... um, Gwen, I'm here. It's Nathan," I called out.
"Come upstairs, Nathan, I'm up here."
I went to the stairs and bounded up, knowing that there would be more sex, I had not jacked-off since I last did it for her yesterday afternoon, I was saving it for Gwen.
I ran down the hall to the end and there she was, propped up in bed, naked, waiting for me with her legs wide apart.
"Come here, Nathan, and kiss my pussy hello," she commanded, "but first get your clothes off," and I quickly stripped and got up on her bed and bent down and kissed it.
"No, more, Nathan, lick it, then we'll go use my computer."
I bent back down to lick her pussy some more, then after a few minutes, she said we were going into another room, her office, and use the computer so we got up and went into the next room where she had a desk and files and stuff with a computer set-up.
"Here, let's get this up," she said typing away and a video came up on the screen. "Yes, this is it," she said and started it. She scooted back in her chair and had me sit on the edge between her legs as we watched. Her hands came around onto my lap as she began playing with my dick and rubbing her boobs on my back.
"Do you like watching this? Is it making you really horny?"
I told her it did, it was a video of a girl sucking off her boyfriend and it was really close-up, you could see the veins standing out in his dick and her wet lips were sliding back and forth across the crown, leaving it slick and glistening with each suck.
"Doesn't it look good to have your dick sucked like that, Nathan?"
"Oh, it sure does, it looks great," I panted, now getting pretty excited.
"It sure makes you hard, Nathan, your cock is really hard, isn't it?" she asked as the girl's lips slid back and forth on him.
"Yeah, really hard, like I could cum," I gasped as she paused the video and slowed down the play with my dick.
"Oh, not yet, Nathan, I won't let you cum yet, we'll watch some more but you can't cum. We're saving that up, Nathan," she whispered in my ear as she began playing the video again. Then, she started playing with me as we looked at the girl licking along the length of her boyfriend's dick.
"Does that look good, Nathan, having your cock licked like that? Maybe it feels like this?" she said as she wet her fingers in her mouth and then dragged them up and down my dick. "Nice, is that good?"
"Umm, yeah," I groaned as she played with me while we watched more. Her hands kept touching me, then leaving me alone, just keeping me excited as we watched until the girl had a mouthful of cum, which she proudly displayed as her boyfriend videoed it all.
Then Gwen started another video of a guy on his back with his dick being kissed and licked and sucked by three naked Japanese girls who were all very pretty.
"Look, Nathan, three sexy women all loving his cock. I'll bet you'd love that, wouldn't you?" she asked me as her left hand held my dick and the fingers of her right rubbed circles around the tip in the slippery cum slowly oozing up from me.
"You love this don't you, Nathan. You love me teasing your dick, making it leak out your cum like this, keeping you hard and excited, just making you go crazy."
"You are making me go crazy, but I love it, I just love it," I groaned as she continued playing with me while we watched the lucky fellow on the video.
"Look how they're all licking the end of his hard cock. You'd love that wouldn't you, Nathan? Look, look, his cum is spurting out all over their faces," she said gleefully.
"Get up, Nathan, let me lick the cum that's oozing up out of your dick, come, face me, yes," she said as her head dropped down and I felt her soft, wet tongue lap across the swollen tip of my dick. Oh, did that feel so good.
"Now sit down again," she said as she put another video on the screen, this one of a guy, a young guy, eating out a woman, an older woman.
"Look, Nathan, does that give you any ideas? That nice boy is making her very happy, isn't he?"
"Yeah, that's pretty hot. You can see his tongue, that's so hot," I told her as she began playing with my dick again.
"You need to watch carefully, Nathan, so you can lick my pussy like that boy does hers. See how he flicks his tongue about. That's what I want, Nathan, just like that. You can do it now, Nathan," she said as she paused the video and I knelt down in front of her chair and used my fingertips to pull her open, then started flicking and flipping my tongue around up inside her juicy opening. There was a small hole up inside that I just had fun with as she squirmed and moaned.
"Ohh, faster, Nathan, do it faster. Be a good boy and I'll give you a nice suck on your cock," she moaned. "Make me cum, Nathan, make my pussy cum."
I was licking and flicking my tongue around as fast as I could, trying to get up as far inside as I could.
"Mmm, yes, Nathan, oh, right there, fast, Nathan, I'm cumming, Nathan, oh, uh, AYYE, AYYE, UHH, uhh, umm, mmm, oh, Nathan, you're getting good, Nathan, you're getting good on my pussy. Keep licking, it feels nice. Do I taste good to you?"
I grunted in the affirmative and kept on licking away the juices that kept coming out of her as I felt her shudder and quake and groan.
"That's good, Nathan, you did a good job and now, I'm going to suck you. Bring your dick up here, Nathan. Have you ever been sucked before?"
I'd heard so many stories about how good blow jobs are and it was really exciting that it was looking like I was going to get my first one ever.
"No, but everybody talks about how good they feel. I've got two friends who have girlfriends that do it to them and they say it's just the best," I told her eagerly as she had me stand up in front of her.