Playing With Aunt Judy

Playing With Aunt Judy

Let me just start by saying that this is not going to be a typical story. I am a so-so writer on my best day, so I'm just going to attempt to tell the story the best I can. So in other words, don't expect any Hemingway-type stuff here. I'm just going to talk about what happened in plain terms. Deal? Deal.

So here we go. My name is Michael, by the way. It's actually not but let's just go with that. To get started, I was at a lake party in the summer, with various family and friends in attendance. Where and who with doesn't really matter, so I'm going to leave out a lot of boring details. One of the guests was my Aunt Judy. Description: She is 50 years old, but doesn't look it (younger). 5'3", maybe 120 lbs. Curly red hair that started graying prematurely, that she keeps somewhat short.

She is a librarian, which is probably the occupation you would have guessed by looking at her. Always conservatively dressed, with think black-framed glasses. Aunt Judy is a pretty straight arrow. Not stuck up or anything like that at all. Just.... well just quirky. Think Judy Greer, ironically. Always laughing and smiling. I don't think I have ever hear her utter a curse word, or discuss anything at all of an adult manner. I'm not even sure I had ever even seen her with an adult beverage in her hand until the day of this party.

It was a typical lake party. People were swimming, people were skiing, people were laying out by the pool. It was late afternoon at this point in the story, and I was coming in from the water. Judy was in the kitchen talking to some of the other women at the party. When I walked in, I heard one of the women say ".... oh no not me. I need a man to---" and then she stopped when she saw me.

"I'm sorry I didn't catch all that" I said, drawing giggles and some red faces. "Probably best you didn't" laughed Judy. She had a glass of wine in her hand, which I remember thinking was odd for her. The other woman said "Ok break time over, back in the water" and grabbed her friends and headed outside, leaving just me and Judy in the kitchen.

"So, what was that awkward conversation about Miss Librarian Aunt Judy?" I asked, with a teasing emphasis on 'librarian'.

"Oh it was nothing Michael. You know girls."

"I sort of do? What was it?"

"Lol. Girl talk. You get a glass of wine in a girl's hand and she starts saying all sorts of stuff!"

"Well that's what I want to hear! What were they saying?"

"Just talk about... stuff. You know. Boys."

"Ah, boys. You mean their husbands."

"Haha, yes. They were dishing on.... you know. Their personal lives let's just say."

"Wow! Steamy!"

"You wish! Nothing too crazy. Alright I'm gonna go get changed out of this suit. Catch up with you later?"

A couple of hours passed. I was feeling just about done at this point. Way too much sun and booze. The sun was down, and people were starting to leave. There were probably four or five total left, and I was about to pull up Uber options on my phone. I walked into the den and Judy was talking with one of the women from earlier in the kitchen. Judy had changed into a tank top and shorts. This was the first time I remembered thinking less than pure thoughts about my Aunt Judy, because the shirt she was wearing was a pink tank top, with, best I could tell, nothing on underneath. She had a bathing suit on earlier, and I suppose no bra with her, so it was either that or continue wearing a wet suit around the rest of the night.

Judy broke off her conversation and started over towards me. "Michael! You're still here." She rubbed my hair in an annyoing aunty way. "Yeah I'm pretty much done I think" I said. "Too much everything."

"No kidding. I had more wine today that I had in the last year combined."

"Well I'm about to catch an Uber. See you when I see you, Aunt Judy."

"Ok sounds good. I'm going to hang out here awhile longer before driving home."

"I think that just about everyone has left. You're going to stay in this house by yourself?"

"Yeah just for a few hours. I want to be alert enough to drive, lol."

"Oh well then I'll hang out with you. I don't have anywhere else to be."

"You certainly don't have to hang out with your old aunt, but I'd welcome the company!" she said as she playfully punched me on the shoulder. Again, very aunty like, with her favorite nephew. Ok fine her only nephew.

We went into the next room, which was sort of a mancave type room. A few different couches and a couple of huge tvs. We plopped down on one of the couches and I turned on some stupid movie showing on Comedy Central. "So you can't share any of that gossip you got earlier?" I asked.

"No goofball, nothing like that."

"Well y'all certainly shut up fast when I walked in, so I figured it was pretty juicy. Everyone is gone now, so spill it Aunt Judy."

"Haha!" she laughed, nudging me with her shoulder. "You're so bad, and you're trying to get me in trouble with my friends. No dice!"

"Oh come on, I offered to stay with you. And we've got, what, three hours? C'mon, let me have something good to hear."

"Sorry buddy, no can do. Scout's honor" Judy said, doing the little 'zipping up the mouth' maneuver with her hand.

And this is where the story is about to start to take a left turn. I had an idea, but I wasn't quite sure what to do with it or where it was going. So I just said "Ok then if you can't tell something about your friends, then how about something about yourself?"

She looked a little surprised. "Myself? I'm afraid I don't have any good gossip for you there either pal."

"Oh come on. Nothing? Nothing juicy at all you could share with your favorite nephew?"

"Only nephew, dummy."

"Still, your favorite nephew. Well make something up then."

"Ha! You really are desperate. Let me think about it. I'll let you know.... maybe 20 years from now because that's not happening" she laughed.

I thought I'd try something else. I was forming an idea in my head and it felt very... well... exciting. And wrong. Completely wrong. But here's the thing. Judy is pristine, almost childlike. I had never in my life heard her talk about anything involving men. I had never heard her cuss. Nothing like that. So in my head, my initial idea was to try to get her to say something dirty. I know, it was wrong. But I had three hours to spare, and sounded like a great idea at the time. That's all I was thinking, get Judy to divulge something about herself. Maybe her likes... I don't know. Something like that. So I pressed on.

"Well in the kitchen, it sounded like Sandy was talking about what she liked from a man. Like, what she liked men to... you know... do."

"Haha! And Michael, good try, but I already told you I can't blab about that. She'd kill me."

Here we go. "So what about what you like? Maybe you could share something about what you like from men. You know."

She howled at this suggestion. "Oh wow goofball! I'm afraid not" she said, while giving me another playful shove.

I pressed further. "What about if I guess it."

"Guess what?"

"Guess what... you know. Something you like."

She had a look of genuine confusion, but still had that big Aunt Judy smile on her face. "You can guess all you want mister, but that's your thing."

Here goes. "Ok... you like to be kissed? Touched? Anything like that you would like to share."

More howling from Aunt Judy. "Again, nice try!"

So far it was a dead end on that front. But, looking at Judy sitting on the couch next to me, in that tight pink tank top that barely covered her belly, got me thinking. I wasn't even at that point thinking of anything physical. But what was turning me on was the thought, what if I am just as playful as her? How far could I take some teasing and messing with her, and how far would she let it go? I had no idea, but I wanted to find out. It was just so very hot, thinking about this pristine librarian, being messed with by her nephew in this way, and wondering her reaction would be.

I scooted a little closer to her on the couch. "Ok then let me try it this way. Are you ticklish?" I asked, as I went to her armpit.

"Yes a little!" she squealed. Hmm, an avenue, I thought. I then brought my other hand up to her other armpit and gently tickled her there too. "So is that something you like? I'm going to find it eventually".

I thought for a moment I had overplayed my hand and risked ending my little game prematurely. But she was still laughing. "No I don't like being tickled there, you dummy! Cut it out!".

"Oh well maybe here" I said, as my hands moved to her belly. In her attempt to free herself from my tickle assault, she had sort of fallen back into the couch, where she was essentially laying down on her back, with her head propped up on a pillow.

Perfect, I thought. As I was tickling the area around her belly button, I had moved to a position where I was practically straddling her. Her protests had died down some, as she was apparently not quite as ticklish there in that spot. I let my hands stay there, and gently rubbed the area around her belly button, letting my fingers extend just under the hem of her tank top.

I was beginning to get extremely turned on. Here I was basically on top of my prudish aunt, with my hands on her bare belly. And that thought was still with me, how far would she let this go? "Oh come on, you can't give up that easily" I said. "I think I know it. A kiss on your belly button. Like a zerbert."

More howling. "No don't you dare mister!". I slowly lowered my head down, then very tenderly kissed her belly button. She laughed. I kissed a few more times around the same area. Still just laughing. "I guess that answers that question then" I said, bringing myself back up. My next thought was either going to be fantastic, or put an end to this pretty quickly. "A lot of women like being kissed on the neck, and behind the ear." I said it not as a question.

"I have heard that, yes" Judy said, composing herself, straightening her shirt back over her belly, and raising herself up on her elbows.

"What if I tried that?". Dangerous territory.

She laughed. "Buddy, this is all you. I'm just watching you act like a jackass. But it is entertaining!"

Judy had just finished with what my ears heard as a definite not 'no'. I wasn't quite sure how to go about it, now that I was in the position. Well, I told her what I was going to do, so here goes. I lowered myself down towards her and braced myself on my hands, right next to hers. They made contact, and I left them there like that. My lips found her neck, and I kissed her very gently. Once, twice, three times. On the right side of her neck. I worked my way up until I reached her ear, and began to nibble there.

I was out of my mind at this point. I couldn't believe it was still going on. But no response from Judy. When I pulled myself back up after about 20 seconds of necking on my aunt, she didn't have much of a reaction. "You about done big guy?" she said, ruffling my hair again. Still with a big smile on her pretty face. I had an urge to kiss her on the lips. Just a quick peck wouldn't hurt right? I leaned in quickly and she equally quickly squealed in laughter and playfully pushed my head away. "Not there either mister!"

I was very worked up now, and had reached a point where I had to find out how much she would let me get away with. Just to recap, I'm practically straddling my aunt's waist as she's laying on the couch underneath me. She has yet to try to get me to move, or to get off the couch. She's just having a fun time with her nephew. I needed to push the envelope.

"Ok, let me try this then. And I'll just tell you what I'm going to do. I'm going to start kissing at your shoulder, and work my way up to your neck and ear. Then I'm going to do the other side. After I've sucked on your ear, I'm going to kiss your cheek, and then I'm going to kiss you on the lips."

I don't know about her, but I was stunned. I couldn't believe this was happening and that I had said those words to my aunt. She laughed, and rolled her eyes. I don't think she believed me. I again lowered myself down, this time to her right shoulder. I had an idea: Move the strap. So I took her tank top strap on her shoulder, rolled it between my fingers briefly, and then pulled it down off her shoulder. She squealed, but made no effort to stop me. I briefly had the thought that with a little more effort on the other side, I could.... no don't think about that now.

I began kissing her shoulder, and then moved up her neck to her ear, and then to her cheek, which I gave a quick peck. "Awww!" she said. I then moved to her other side, and did the exact same thing. I took her other strap, and pulled it down off her shoulder, down her arm. I took a second to take a quick peak of my aunt laying on her back, with her tank top straps halfway down her arms. Again, with just a quick pull now, that little shirt would..... nope, not the time for something like that.

So I moved back down and kissed her shoulder, up her neck and ear, and then gave her a kiss on the cheek on that side. It was time for her lips now. She had pushed me away the first time I tried. What I did next turned me on so much it's actually hard to describe. She had her black-rimmed glasses on, as always. I don't think I had ever seen her without them. I took the ends between my fingers, and slowly pulled her glasses off the ridge of her nose. When they were all the way off, I pushed them up and put them on her head, buried in her curly red/gray hair.

Having only seen her in glasses, the act of removing them was extremely hot. It was like an unmasking. Sitting on top of my aunt with her shirt halfway off, and stripping off her glasses. Beyond imagination.

Again, how much would she let me do? We were about to find out. I took her chin in my right hand. I slowly moved in, until my lips were right above hers. No movement on her end. Still a little smile on her face. I moved in closer, until my lips made contact with hers. I gave her a quick peck, and then another. Then another. Another. I was kissing my librarian aunt on the lips, and she was letting me do it.

The next kiss was longer. I briefly opened my mouth and let my tongue explore, before coming to my senses and breaking it off. I looked at her and she looked back, not sure what to say.

"Well that was something!". She looked to her left and right at her shirt straps that had been pulled down her arms. I was afraid she might try to adjust herself, so I put my hands on her arms, essentially pinning her down. This caused more laughter. "Hey bozo cut it out!" she squealed. All the moving around only increased the friction on her shirt. Her tits looked like they were about to pop out of that thing, with her back arched like that and bouncing around. I wasn't sure how much more of this I could take.

What now? I wondered to myself. I had an idea, but it was another of those "this could kill the moment" ideas. But I had just kissed her on the lips and gotten away with it, so I figured it was worth a try. Still holding her by the arms, I asked "When you changed earlier, did you change out of your swimsuit bottoms? I only ask because I noticed you changed out of your top."

"Oh you did, did you?" she said. "No I'm still wearing them underneath my shorts."

"Are you now...." I said, my right hand drifting to her shorts. "Well let's just see about that." Here I took a big risk. "Maybe having your underwear inspected is the answer I've been looking for?"

She laughed, of course. "Everyone here saw my swimsuit bottoms today, silly!".

My hands met around her waist, and quickly found her button, which was then unbuttoned. Then down to her zipper. In the quiet house you could hear my aunt's shorts being unzipped. I looked down and saw her blue suit peeking through. "Lift up" I said, and she did, ever so slightly. I pulled her shorts down, inch by inch, until they were at her knees. And then they were all the way off and laying on the floor.

I should mention at this point that I was incredibly hard. It was just too much.

Looking down at my aunt under me, essentially just wearing panties and a shirt that was half down her arms, with her nipples trying to poke through the fabric. I wanted to feel them under me.

"I'm going to try that kiss, just one more time..." I said, lowering myself back down. This time I let most of my body down with me, enough that our chests and pelvic areas were in contact. As our lips made contact, I could feel her nipples poking through the shirt on my chest. And as much as I tried to avoid it, my erect penis in my shorts was rubbing against her swimsuit bottoms. I figured this was the end game, because it was just so hot. I lifted myself up slightly so I wouldn't be grinding up against her. That might scare her off.

We continued kissing. More like, I continued kissing her. I didn't get much of a reaction from my prude aunt. I lifted up and looked in her eyes, and she chuckled. "I'd say you failed in your little game, bub! But thanks for the kiss! That was sweet."

Undeterred, I lowered myself slightly, and began to kiss just under her chin. I slowly moved down to where I was kissing her upper chest. I took the top of her shirt in my hands, and ever so slightly began to push it down, as I continued kissing her chest. Maybe a quarter inch at a time. I wanted it to be imperceptible. After a minute or so of this I looked down and the top of her tank top was just below the swell of her breasts. It looked like about maybe an inch until her nipples would come into view.

"Maybe I'll try the tummy kiss one more time" I said, as I licked her belly button. As I did this, I did the opposite to the bottom of her tank top. I began to push it up. Same way, very slowly, as I licked every inch of her stomach, and up to her rib cage.

When I pulled myself back up to take inventory, honestly, I almost came in my shorts. Her tank top had been reduced to a fairly small strip of material covering her breasts. Most of them, anyway. You could see the swell of them up top, and a small amount underneath. I openly stared. She looked down at what was left of her shirt covering her tits. Not much.

I decided it was time to push my luck a bit farther. "Ok how about this.... a lot of women get really turned on by.... well, you know" I said, my attention going to her bottoms.

"You know, what, mister?" she giggled. "Aren't we about done here?"

"I don't know, maybe having their underwear played with? Something like that." I was twirling the material that tied the right side between my fingers. "That's not my underwear, silly" she said.

"Close enough" I replied, while slowly pulling on the tie. I pulled harder, and it came undone. She squealed. I moved my hand to the other side, and did the same with the other. I was in VERY uncharted waters now. Both sides of my aunt's swimsuit bottoms had been untied, by her nephew, and there wasn't much holding the rest in place. I openly stared, as I caressed the area where the ties had been undone. "Careful buddy!" she said. "Your old aunt is pretty modest."

"Oh yeah?" I asked, as my hands snaked up her sides, toward her top, now with a specific goal in mind. "Like I said, maybe some girls like being..... you know."

"No, what?" she asked.

"Being stripped" I said, playing with the material of her top between my fingers. I stared at her and let the words hang in the air. Being stripped.

I leaned down and kissed her passionately on the lips. My hands were on fire, and I moved them up her sides, to where I was feeling the sides of her tits. I slowly moved them around to the front, and grabbed the hem of her shirt. I broke off the kiss. "Like I said, some girls like being stripped". I slowly began to push the shirt upwards. I stopped briefly, took her hands in mine, and moved them above her head. And then I kissed her again for good measure, before returning to her shirt. I whispered in her ear, as I teased the base of her breasts with my fingertips, "Do you like being stripped". Silence. "Do you like the feeling of being exposed? Do you want me to find out?" Silence.