Playing With Aunt Judy

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.