Perverts 'R' Us

The Older Woman

By PlumpLover ( F/m, mast, oral )

I hope you enjoy this. If you get off while reading this, please let me know! If anyone has questions you can e-mail me at plumplvr <at> gmail.com. I welcome all correspondence.

The summer I was 14, about to be 15, and my mother had a good friend who was going through a divorce. She was planning on moving to be closer to some relatives. However, with no kids and no relatives living nearby, she needed a strong back to help her move boxes around, etc. So my mother volunteered my services for a week, for which I would receive a small payment.

Since she lived about an hour and a half away, it was agreed I'd stay with her for the time it took us to pack. I can't say I was particularly looking forward to it, but it turned out really great.

Charlotte was in her 30's I guess, about 5'8 in height with long curly black hair. She was a big woman, plump with a big butt and huge tits. I was afraid it was going to be awkward, but Charlotte was very outgoing, and I found myself becoming quite friendly and open with her before we even got back to her home.

We spent the day working hard, she made a great dinner and dessert for us, and then we spent the evening watching some TV. I was dressed in some shorts and a tank top, she had on an old t-shirt that stopped just below her chubby ass. I was under no illusions she was naked under it, and I'm sure my cock gave away my interest.

I really got caught by surprise though when she was saying goodnight. "By the way," Charlotte asked, "do you usually masturbate before you go to sleep?"

I guess I was stunned, and just sort of mumbled something. "Look, it's OK." she told me. "When I was your age I couldn't keep my fingers off my crotch, I bet you're the same way. And, like I had to, I bet you probably have to hide it, right?" I told her yes, I did.

"You know, that just hacks me off. Masturbation is such a natural healthy thing, everyone does it, hell I still do it. I can't understand why we have to hide it." She paused for a moment, and then went on. "You know, I always swore if I ever had kids I was going to let them be open and free about masturbation, to do it openly whenever they needed to. Well, you're not my kid, but if you'll promise to keep it between us, and I mean tell NO ONE, we'll pretend like you are, and we'll both get off to our heart's content. Promise?"

I did, you can be sure of that. She told me to wait a moment, and then came back with a small bottle of baby oil and a towel. Setting that down on the table beside the sofa, she said "Here let's get you something fun to watch." Charlotte had one of those huge fifteen foot satellite dishes that were popular at the time, and turned it to the sex satellite, as she called it. She showed me how to change channels among the wide variety of fuck films that were going.

"I guess that's about it, have a good night." she told me with a wink. I was pretty speechless, but very aroused as you might expect a horny 14-year-old to be. "Oh by the way," she said as she was exiting the room, "I sleep naked, it's so comfortable I just can't imagine sleeping any other way, so it's OK with me if you want to do the same. Oh, and if you get any... stuff on the blankets don't worry in the least about it. Perfectly natural, easy to wash, hell I get my sheets messy every night." With that she was gone.

Well, I eventually worked up my courage, got naked and had a great orgasm. The next morning it was as if nothing happened, we got up and spent the day packing and moving boxes out to her garage, where they were being staged.

That night we were once again on her sofa, I had on the same pair of shorts but had gotten courageous and left my shirt off. Charlotte was wearing a tank top that showed off her rather large, floppy tits and clung tightly to the rest of her body. "So, I bet you had some really nice orgasms last night judging from your towel?"

I guess I got embarrassed, and didn't say much, as she went on "Remember, we were going to be open and honest? I had five good cums myself, playing with my pussy. How about you?" I admitted to having two orgasms of my own, while watching the dirty movies on TV. She began asking me very intimate questions, how many times a day did I jerk off, how much did I shoot, how big was I, what experiences did I have with girls, etc. Charlotte had a way of making me comfortable, and soon I'd overcome any inhibitions and was answering her openly, honestly and, I might add, explicitly.

During the course of our conversation she had turned on some dirty movies, asking me what I thought of various women, positions, etc. "Well..." she finally said, "I can't take it anymore, I'm going to bed and masturbate. Have fun..." As she walked away from me, Charlotte had taken no more than three steps when she reached down and peeled off her tank top, letting me see her naked body from behind. Her big, glorious ass wiggled as she walked, and I nearly came right then. I got a glimpse of her breasts and plump belly as she went into the bedroom. Finally I noticed she didn't bother to close her bedroom door, which allowed me to clearly hear her moans and groans as she played with herself.

The next morning she woke me up, I was naked under the thin sheet, a cum-soaked towel on the floor attesting to the three orgasms I'd had last night. She was wearing a thin bathrobe, with snaps on the front. "Looks like you had a good time last night, fell asleep with the TV going, too." I noticed a porn movie was still going on the TV.

In the spirit of openness, I admitted to having my three cums, and then asked about her. She smiled and admitted to having several herself. "By the way, I asked you a lot of questions last night, but you didn't get to ask me any. Is there anything you'd like to know? Anything at all?"

I started out with some simple things, how many times a day, etc, and went on to more intimate things like technique, did she taste herself (she did) and more. I noticed she had her hand between her legs, and was openly rubbing herself, but not to where I could see anything. Finally I told her "Um, you know how you said we should be honest if we had a need right?"

Charlotte smiled and told me "Yes, go ahead."

I told her I was really horny and in need. Smiling, she said she was too. "Look, I think we trust each other, right?" I nodded in agreement, and she continued "Well, if you don't mind some nudity, I think it'd be alright if we did it together. BUT, you have to promise no touching. Touching would be crossing the line. Agreed?" I did, quickly. "OK, then, I'm going to trust you."

Charlotte stood, and quickly popped open her nightgown, letting it fall to the floor. It was my first really good sight of a naked woman, and I drank it in. Big tits with huge nipples, plump belly, hairy pussy, and that sexy ass. Wow. Before I could move she reached down and jerked the sheet off of me, revealing my young hard prick.

She sat back down and without another comment began to finger herself. I watched for a few minutes, and then began pumping my penis. She was sucking her tits while her hand flickered furiously over her twat. Her body soon convulsed and shook as she had a massive orgasm. Calming down she looked over at me and said "Your turn sport, go for it."

With her watching, I began stroking for all I was worth. As I got close to orgasm, I reached for the towel to catch the mess. Charlotte stopped me, jerking the towel out of my hand. "Don't worry about the mess baby, let it fly. That's when it feels the best, doesn't it?" I agreed that it did. "Well then let it fly, sex is the best when it's messiest, come on shoot your cum everywhere!" She began to encourage me, practically yelling "come on, shoot your cock, make it cum!"

I blew a huge load of spunk that morning, as I was pumping wildly it flew everywhere. When I finally opened my eyes Charlotte was giving me a huge smile. "Didn't that feel great?" It did, I quickly agreed.

"Sex, or masturbation," she told me, "is best when you can let all your inhibitions go. Do whatever feels good to your body. If you think it would feel good to play with your balls, do it. Pinch your nipples? Go for it. Let yourself go. "

I asked her how she let herself go. "Well, sucking my own tits, rubbing my butt, tasting my own juices. My biggest rule is I do it whenever and where ever I feel the urge. If it's during lunch, I don't hesitate to play with my pussy at the kitchen table. Take a mid afternoon break, in the bathroom, wherever."

I asked her what would be the biggest thing that someone might consider to be an inhibition, and she replied "Probably the mess. My biggest rule is not to worry about a mess. It's just body fluids, cleans up easily, but if you spend all your time worrying about a mess, you don't get as good of an orgasm. Look at yourself, when you let it fly, wasn't it much better than having to grab a towel at the last minute?"

"Definitely" I had to agree.

"Well then, don't worry about it, at least while you're in my house. Frankly, I've already sold the place, and since it was back to my ex, you can make all the mess you want!" I noticed she threw in a little evil laugh afterward.

We got up and ate breakfast, still nude, then cleaned up and went about the business of packing. I was feeling braver and a lot more comfortable, so after lunch told Charlotte, "I had the urge". She told me she forgot how horny 14-year-old boys can be, and told me to drop my shorts and have a go. I did, and sitting on the edge of the kitchen chair had my first real exhibitionistic experience, jerking off while she watched, fully clothed. I shot my cum onto the kitchen floor. I noticed she didn't bother to clean it up when we got up to go back to work.

When bedtime rolled around that night, she told me it was silly for me to have to sleep on the couch since we'd seen each other naked. I was welcome to sleep with her in her California King sized bed. She reminded though of the "no touching" rule.

In bed, she asked if I'd ever seen a dildo being used, and when I honestly replied no she got out this long, thick pink dildo from her box and showed me in intimate detail how she got off on it. After her noisy orgasm, it was my turn.

When I leaned back and started to stroke, she asked me if I ever did it other ways. I told her not really, and Charlotte told me it was time to explore some other avenues of my sexuality. She had me roll over, and begin to hump her bed. She put a pillow between her own legs, rolled over and began to hump in unison with me.

"Doesn't it feel good, like you're fucking a woman?" she asked. I told her it did, and she urged me to keep it up until I came. I humped and pumped, both of us wildly bucking our hips against the bed until we came.

As I was trembling, she snuggled up to me (violating her own no touch rule) and said "Wasn't that awesome?" I couldn't answer very well, so she went on "Rub your cock around in it." I felt a gentle pressure on my ass as her hand forced my dick even deeper into its own cummy mess. "There you go, enjoy your orgasm fully. Feel how wonderful your own body fluids can be." We lay there quietly before she gave me a peck on the cheek and said good night as she rolled over. We were both fast asleep in no time.

The next morning I woke up first, in need of a piss, and when I came back to bed had quite a morning woody. Charlotte was lying there, asleep on her back and I couldn't help but admire her body. I carefully knelt on the bed beside her, and began stroking my dick. I guess I wasn't as careful as I'd hoped, as she woke up.

"Oh, hi there." she said with a sleepy smile.

"Sorry, I didn't mean to wake you, I just saw you lying here and well couldn't help but touch myself."

"That's OK, keep going, I don't mind."

I stroked for a few more minutes, and then said "I'm getting close. Do you want me to move so I don't get it on you?"

"Silly boy." Charlotte giggled. "I told you that you could cum anywhere, and my fat body is certainly anywhere! I don't mind in the least, it's just cum. Go ahead, why don't you shoot on my boobs, isn't that what guys like to do cum all over women's titties?" Her hot invitation was all I needed. In mere seconds, I was unleashing jizz all over her big breasts.

When I was done, she looked down and said "My, what a messy boy you've become. I'm proud of you." She then picked up one of her tits and brought it to her mouth, licking my spunk. She let out a low moan, and then using her other hand reached between her spread legs and began fingering her pussy.

I'd never seen a woman lick cum like that before, well at least in person, and it was so exciting it kept me stiff as a brick. I moved between her legs to get a good show and kept on pumping my dick. She gave me a great show too, licking her cummy tits and rubbing her clit. I kept on pounding away at my dick, my cum from before acting as lube. When she came I did too, spraying my semen all over her pussy and belly.

She told me how impressed she was with my stamina, and then said we'd better get going before we spent the day in bed. Like the day before, we sat down to the breakfast table still naked and messy. Over her bowl of "Boo-Berry" cereal, Charlotte told me it seemed silly to get dressed, and suggested we just stay naked.

Being naked also made it easy to take "masturbation breaks". Sometimes it was my suggestion, sometimes hers, but several times during the day we stopped for a "quickie". This pattern pretty much repeated itself for the rest of the week, being naked, masturbating together, shooting my cum everywhere and her leaking everywhere (she was a very wet woman, left big puddles where ever she sat or laid). I shot my cum in every room of the house, letting it fly on the floor mostly, while she leaked her copious amounts of pussy juice everywhere.

By the end of the week, despite the many breaks we'd gotten everything done. I was sad to see the week end. That's when Charlotte gave me one of the nicest surprises I've ever gotten. "I know we're done" she said that Friday night. "But I called your folks and said I needed you an extra few days. You've been so helpful, and we've had so much fun I want to give you a nice reward. For the rest of the weekend we're just going to stay naked and masturbate. No packing, no work, just the two of us exploring our bodies. Sound like fun?"

I told her no, that I wanted to go home immediately.

Psych! No, dear reader, I was quite thrilled. We had taken most of the bedroom apart, and the living room was empty except for the TV, so we pulled her top mattress out to the living room so we could enjoy porn flicks. The next 48 hours was bliss, just one orgasm after another, fuck films going on the TV at a noisy volume, and us being even noisier.

We did clean up to go out for a late dinner Saturday night. Since the restaurant was nearly deserted, we were able to continue our sexual conversation with little risk of being overheard. Charlotte told me about her past partners, including some girls. She also gave me what to this day I thought was good advice. "Always be open to new experiences." she told me, "it doesn't matter if it's a girl or boy, or what age, just do what feels good for both of you."

On the drive back home we continued the sex talk, and I asked if there'd been any girls recently. Not real recent, she said, a few years but there was another gal she knew that had joined her in bed, mostly for sixty-nine, plus some dildo humping. I asked if there was anyone now she was attracted to, and she sort of blushed and said "Well, yeah". I asked if it was someone I knew, and she nodded, in the dim street light I could tell she was a bit embarrassed.

"Openness and honesty, remember?" I told her. "OK," she admitted. "I uh, well your mom is really hot." I sort of suspected it; my mom did have huge tits. I was a bit "weirded out" as they say, but because I could see the effect it was having, proceeded to describe what my mom looked like naked (mom wasn't very shy around us). I also told her about the sex toys and dirty mags I'd found in their dresser, which really got Charlotte worked up.

Seeing how hot she was, I reached over and began fondling her tits. "You really shouldn't be doing that." she said, but made no effort to stop me. I slid my hand under her shirt and played with them more through her bra. We were deep in the country at this point (Charlotte lived out in the boonies). Pulling up to a stop sign she said "wait a sec..." Leaning forward she unbuttoned her blouse, and then took it off. Her bra came off next, then she slid her shirt back on, leaving it unbuttoned and open.

As she drove I continued to play with her big tits, her right hand reached over to grab my crotch. Emboldened, I reached my hand between her legs, sliding up the loose leg of her shorts. Pantiless, her pussy was moist to my touch. "Take off your pants." she ordered. "Let's see some skin from you." I did, pulling them off entirely. I then, with a little wiggling, managed to get her shorts off. Fortunately we were close to her home by this point, naked from the waist down we probably wouldn't have made it far.

Instead of parking in the driveway, she drove around the back of her house where it was secluded. The engine was barely off before she was attacking me, pushing my seat back and sitting on my lap. He blouse got lost on the way to my side of the car, and she frantically pulled my shirt off to get maximum skin to skin contact. My young cock quickly found its way into her wet pussy. Leaning forward she held me tight and growled "I'm in so much deep shit if anyone finds out about this..."

We fucked, there's no other word for it. Pure lust, we just fucked. Right there in the front seat of her car, in her back yard. I know it couldn't have been five minutes before she was exploding, cumming all over us and moaning with pleasure. Naturally this set me off and I exploded, blasting my jizz into her hungry snatch.

While our orgasms died down, we kissed some, then she opened the car door and stepped out, naked, so I followed, leaving our clothes in the car. She let us in the back door and we went straight to the mattress in the living room. Laying me down, and without a word she began sucking my cock. I hadn't had a lot of experience with blowjobs at that point, and Charlotte's talented mouth was far better than what I'd had before. The entire time she was licking and sucking me, her eyes were looking up at me with this intense lust in them.

When I finally exploded in her mouth, she swallowed every drop and kept on going, keeping me hard. Finally she said, "there, now you'll last a while". Sliding up she rode my cock some more, then proceeded to teach me all sorts of neat positions like doggy and missionary. (I had fucked a girl missionary before, but it was my first doggy).

We kept on for what seemed like hours (but was probably wasn't) before I came for the third time of the night. Fucking missionary, I unloaded, pumping my cum into her pussy while she held me tightly against her body, twitching from her own orgasm. Rolling to our sides, we fell asleep holding each other.

When I woke up the next morning, I was quite confused, as Charlotte was lying there, crying. Yes, reader, I know this isn't very sexy, but this is a true story and not some made-up penthouse romp, despite what it may seem like.

Charlotte was apologetic, saying she'd gone too far, let her lusts get the best of her, had been too long, and so on. At 14 I really wasn't very good at dealing with women's emotions, and frankly at 41 I'm not much better at it. But I tried, assuring her I was fine. I also reminded her of her words from the night before, saying she was the one who said we should enjoy ourselves, go for the pleasure, be open to new things, etc.

Eventually (and it took a while) I calmed her down and made her feel better. She told me it was very sweet of me to work so hard to make her feel better, and felt bad about putting a downer when this was supposed to be some reward time. Charlotte then grabbed the oil and soaked my crotch in it, proceeding to give me a wicked hand job. Her hands were incredible, bringing me to the edge, then letting me back down until I couldn't take it any more and said so.

Noticing the scene on the movie was a guy standing, shooting all over a woman, Charlotte told me to stand, and sat between my legs. She resumed her hand job, only this time she didn't stop until I was having a massive cum, blasting her face, tits, and hair with my youthful load of cum. She was soaked, and never looked prettier (and I said so too!).

We sat and talked for an hour or two, Charlotte with cum dripping off of her as it dried, until our stomachs started to growl. She made us a big brunch, which we ate naked, she (at my insistence) sitting in my lap.

I knew we would have to go soon, but her naked bod wiggling on my ass, plus the porn flick we were watching while eating, got me hard again. I asked if we had time for one more orgasm.

"Sure sweetie, but remember I'm not so sure it's a good idea that we fuck." I asked if we could hump the bed together, like we had the first night we'd slept together. "Sounds like fun!" she agreed.

This time she laid pillows under both our crotches, and we laid side by side, our bare skin touching. Our hands groped each other's bottoms as we humped away. As we got close, we twisted slightly and began to kiss, a wild tongue thrusting passion-filled kiss. We somehow managed to orgasm together, pumping our sex fluids onto her pillows.

I don't know what came over me, but when we rolled off I grabbed her pillow and rubbed my face in it, smearing its wetness on me. Charlotte laughed and said "what the fuck". Grabbed my pillow and did the same, her open mouth and tongue lapping up what wasn't smeared on her pretty face.

Afterward we showered together - oddly enough, it was the first time we shared one. We were both sexually exhausted, so even though we did some kissing and touching, it wasn't that sexual. It was a good lesson in intimacy though, which I enjoyed. We didn't exit the shower until the supply of hot water was exhausted.

Before we left we shared one last deep, intimate kiss, then she made me promise not to tell anyone, which I haven't until this day, and even now I haven't spoken her true name. It wasn't until she'd dropped me off that I realized she never did give me the fifty bucks, but I didn't mind. She gave me so much more.

Charlotte taught me masturbation is healthy, normal, and enjoyable, and there's nothing wrong with it. She taught me how to try new things, explore my boundaries, and be open to new experiences. She taught me some new ways to masturbate, different ways to hold myself, and the technique of mattress / pillow humping, which I enjoy to this very day.

I never saw her again after that, she moved the very next week. But I still think of her from time to time, when I'm pleasuring myself. I hope one day she reads this and knows how much she meant to me.