Kelly's Diary 010 - Teasing My Boyfriend's Brother - Cover

Kelly's Diary 010 - Teasing My Boyfriend's Brother

Copyright© 2024 by Kelly85

Chapter 3: Teasing Jim

Coming of Age Sex Story: Chapter 3: Teasing Jim - My incredible boyfriend Steve had picked me up to take me to a party but when he forgot his wallet we needed to go back to his house. While he hunted for it I had some fun teasing his younger brother. Jim got to see more of his brother's girlfriend than ever before and before it was over I even talked Steve into putting on a little show for him!

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   True Story   Exhibitionism   Facial   Masturbation   Oral Sex  

Before making my way to the living room, I checked myself over quickly in a mirror hanging in the entryway. Even though my blouse was already unbuttoned down past what little cleavage I had, I unfastened two more so now it was open well below my chest, allowing the black lace bra underneath to be visible directly. Heck, only two more buttons and I could’ve just taken it off and gotten it over with.

Out of force of habit more than anything I tried to straighten out my skirt but it was WAY too short to cover much of anything. Turning around I bent over just enough to check out my bottom which made me start to debate the thong. There wasn’t going to be a lot of time to tease Jim (or at least I hoped there wouldn’t be) so why be coy about it? I reached under my skirt and dropped the thong down to my ankles and stepped out of it. Tossing it onto the stairs with my foot, I wondered what Steve would think when he came back down and found it?

Looking back into the mirror one last time, I saw that my skirt was still covering my bare ass ... but just barely. All it took was to stand up on my tiptoes or lean over just a little to put my bare ass on display, not to mention my fuzzy brown pussy as well.

Actually, there was more to my decision to remove my underwear than just trying to be sexy. I LOVE the feel of running around bare bottomed. At home I prefer to hang around in a short T-shirt or one of my dad’s dress shirts without anything on underneath. Even in public I rarely wore panties under jeans or dresses. So long as a dress or skirt is long enough to keep me from getting arrested, I leave them at home and enjoy the feel of the cool air against my bare skin. Of course, the more public the location or formal the occasion, the hotter it makes me feel being with people who have no idea I’m naked underneath.

One of my ultimate turn-on’s comes when I’m at church, sitting in the pews without a stitch of clothing under my Sunday sundress. I get off imagining what the father next to me would say if he knew the “innocent” looking girl next to him had nothing between her ass and him but her short dress! It was usually enough to get me so horny that by the end of the service I couldn’t wait to get home to talk care of myself.

Taking a final deep breath, I ran my hands through my hair, gave it a toss, and was ready for action. Walking slowly and deliberately into the living room I wiggled my ass suggestively as I made my way across the room, taking a seat on the love seat across from his couch where he was watching some silly TV reality show. Once I was sitting down I crossed my legs, slowly and deliberately which allowed my skirt to ride up such that it was effectively out of the picture. I could feel the seat cushion against my bare butt under me so I knew there couldn’t be much hidden from his view down there.

“Hi Jim,” was all I said to him using the same indifferent tone of voice I typically reserved for him.

“Ummmmm, hi Kelly,” he stammered. I thought about it for a second and realized it was probably the first time we had ever been in a room together alone under ANY circumstances which probably accounted for his apparent nervousness.

Since the moment I had walked in his attention had shifted from the TV to my bare legs and ass. I was still wearing my jacket and it was plenty warm in their house as Steve’s mom was divorced so they didn’t have a thermostat Nazi in their house.

“Wow, it’s sure warm in here. You don’t mind if I take off my jacket, do you Jim?” I asked innocently. Yeah right, like he was going to complain if I took ANYTHING off.

He quickly shook his head so I unzipped my jacket and leaned forward to pull it off my arms. In doing so, any last chance the skirt had to cover my bare bottom was history and I knew my blouse was hanging open enough up to show off whatever part of my bra had been partially hidden from view before. Tossing my jacket to the side I laid back against the love seat with my legs still crossed, fully aware that he could see everything from my toes through the heels to my butt.

Jim stared but didn’t say a word so I figured it was time to turn things up a notch. I slowly ran my hands over my bare legs, running my fingertips up my thighs, feeling the smoothness of my freshly shaven skin. I pretending to try to pull my skirt down which was a useless gesture even if I’d really wanted to do it. Then I felt my warm upper thighs with my fingers, tracing my fingernails lightly over my silky smooth skin. My wandering fingers worked their way up until they touched my bare hips. As much as I love to play with my ass (I mean my butt, not my asshole!), having someone watch made it even more erotic. Reaching under me slightly, I squeezed my butt, causing a chill to run through me as I felt just a little bit of pride at the firmness of my ass.

“Do you like my legs Jim?” I asked him softly, “I’ve noticed you seem to be looking at them a lot lately.”

“I’m sorry,” he apologized immediately, his face turning beet red. He HAD to have known I knew he was watching me but I guess it wasn’t until I confronted him with it that he felt any supposed remorse over it.

“Oh no, that’s OK,” I reassured him. “Steve’s looking for his keys so I’m just waiting for him and I thought I would just relax in here. Is that OK?”

“Oh yeah!” he burst out and then, realizing how that must have appeared, tried to look serious and said, “I mean, of course you can.”

If he hadn’t looked so innocent and naive I probably would have just laughed at him and walked out. Instead, for some reason that same innocence seemed to be turning me on. I wondered if this wasn’t some of what drew Steve to me when we first started dating. Sure other boys had touched me before but so far as sex went, I was “innocent” as well.

“Well, then I guess you don’t mind if I make myself comfortable,” I teased him gently.

Without waiting for a reply, I twisted around on the love seat to position myself such that I was laying on my back lengthwise, my back propped up against one end of the love seat with my bare legs stretched out flat in front of me. Then, keeping my knees tight together, I slowly bent them upwards until my heels were flat on the cushion. Oh well, so much for keeping your shoes off the furniture! Reaching down to my ankles, I ran my hands from my ankles to the top of my thighs, gently massaging myself like that for several minutes. When I leaned forward to reach the bottom of my legs, my skirt would ride up practically to my waist. With my legs being held together though, seeing me from the side he must have been wondering if I was wearing any panties.

For several minutes I rocked forward and backward like this slowly, enjoying the feel of my hands and fingers as they caressed my bare legs. Then I turned my head quickly and caught Jim staring at me like I was some alien from outer space! His eyes were like saucers, testifying that he’d been enjoying the show. If any final confirmation was needed, all I had to do was look between his legs. He may have been barely a teenager but he must have been packing quite a package for his age considering the tent poking up from the crotch of his jeans. Seeing him get erect because of me didn’t bother me, if anything quite the opposite. To be honest, I would’ve been VERY disappointed if he hadn’t! Naturally, I wasn’t going to tell him that so instead I teased him a bit.

“Now Jim, just what do you think you’re looking at?” I teased him, smiling to try and take the edge off my question.

Jim was still blushing like crazy but if anything, that just encouraged me all the more.

“Oh c’mon, you can speak up Jim,” I teased him as he just sat there stammering. Running my hands over my legs yet again, I turned back to him and said, “Mmmmmmm, what do you say let’s start by you telling me what you think of my legs.”

Jim was still blushing as be blurted out, “Wow Kelly, they’re great!”

Figuring that which was about all he was going to get out. I flashed him my most sexy and devilish grin. “Cool, I’m glad you like them ... do you want to take a closer look?”

At first it was like he couldn’t move, frozen in place by my offer. Then Jim nodded slightly. I waited patiently, or at least as patiently as I could under the circumstances and he finally responded, “Yeah but what will Steve say? I thought you were supposed to be his girlfriend? You know, I thought he was going to kill me the other day just for peeking.”

It was obviously up to me if anything was going to happen so I got off the love seat and slowly moved over to the couch where Jim was now sitting up. As I walked provocatively towards him, I maintained eye contact with him saying, “Let me worry about Steve; he’s going to get all he can handle later. I’ve seen you looking at me before Jim. Don’t you want me now?”

Standing directly in front of him, I slowly raised one leg and planted my foot on the cushion alongside his leg. As my leg came up so did my skirt and from the way he was concentrating on my crotch I knew he was waiting for my thong or panties to be exposed at any moment. Well, he didn’t have to wait long. God, the look on his face when he realized that I wasn’t wearing anything under my skirt was absolutely precious!

“Oh I’m sorry Jim,” I said, trying to sound as if something was MY fault, “I just assumed that you wanted to see ALL of me. Are you sure this is OK?”

Jim just sat there staring between my legs. He didn’t even blink, as if he was afraid if he closed his eyes I might not be there when he reopened them. Odds were he’d never even SEEN a real pussy before except in a porn magazine or movie. Even though I had absolutely NO intention of doing anything but tease him, it still made me feel hot and horny knowing he would remember this moment for the rest of his life.

My pussy was getting warmer by the minute as I started to get off from him watching me so intently. I rocked on my heels, rubbing my raised thigh with my hands. Then I moved one hand up to my crotch, covering it with my palm. I ran the soft fuzzy pubic hair though my fingers as I started rubbing myself. Oh it was partly to tease Jim but right now I needed to touch myself badly as I felt myself getting hotter and hornier.

“Do you know what makes me really hot Jim?” I whispered to him. He looked up at me and I could tell he probably had a dozen fantasies but in truth, had no real idea how to answer.

“Well, I love it when a guy watches me when I play with myself,” I said in a low, husky voice. “It’s so much better than just watching myself in the mirror. Will you be my mirror Jim?”

Actually while I may have been teasing him, that was a 100% true statement. Steve may have been the first to actually fuck me but I was teasing my share of horny boys long before then. Even when I was a virgin it got me off to expose myself to a boy and play with myself, seeing him get so frustrated because he could only watch me and not touch, at least not with his hard dick. It also turns me on to think about how they probably masturbate later when they fantasize about having sex with me.

“So tell me Jim - and I want you to be completely honest with me,” I said more sternly, looking down at him to make eye contact. “When you jerk off, do you ever think about me?”

It was a shot in the dark but somehow or another I was pretty confident of the answer. Jim’s face flushed bright red again which told me all I needed to know. Well, he was REALLY going to have something to masturbate to after I was done with him!

Putting my fingers in my mouth to wet them, I then used them to pull my pussy lips to the side so I could twirl my finger around my exposed clit. My breathing grew heavier as I closed my eyes and stretched my head back. Using my other hand I inserted a finger into what was now a soaking wet pussy and shoved it up inside of me as far as I could. With both hands now moving faster and faster I started moaning softly.

When I opened my eyes I saw Jim staring at my pussy as he watched the job I was doing to myself with my hands. His expression was the perfect image of a deer in the headlights - eyes wide open and staring with his mouth hanging open like a fish out of water! Suddenly I stiffened and a gasp escaped from my lips. I knew that I was right on the verge of an awesome orgasm!

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