Paul Likes Panties and Gets Pegged

Editor's note: this story contains scenes of incest or incest content.

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I guess I have a little crush on my older sister, Charlotte. It isn't my fault though, because she is hot. Charlotte has an olive skin tone, straight black hair, and green eyes. She has an angular face, with strong cheek bones. She is more of a sporty tomboy, running and playing volleyball when she can. She is fit, but her natural build leans heavy in the hips and ass. As a result, she has thick, strong legs and a phat, round ass. She has perky tits, although they are a little small.

I also have a crush on her best friend, Tammi. Tammi is a cute, blonde young woman with blue eyes. She gives off a very innocent vibe, but Charlotte has told me enough stories about Tammi's time at college that I know she isn't shy around men. She was barely five feet tall and a little chubby, but she had an pretty, elfish face. Plus, her weight seemed to sit on her hips, tits, and ass instead of her waist, so it rarely discouraged men from pursuing their interests.

When I was 18, I began the process of applying to colleges. Charlotte and Tammi were both 20 at that point, and were sophomores at our state's public university. They were living in an off-campus apartment with another girl, whom I had never met. Charlotte was studying chemistry, while Tammi was at school for public relations. Charlotte and I had were on good terms for siblings. I also ran track, so we had some common interests. We were both easy going enough that we rarely had arguments or fights, and would often hangout when we were both home. Because we got along and Tammi liked me, they both agreed to show me around campus one weekend. They would even let me stay at their apartment if I stayed out of their roommate's way.

After a three hour drive, I got to town a little stiff and hungry. Tammi greeted me at the door with a hug, and I made sure to graze her plump ass with my hand a bit. If she noticed, she didn't say anything.

"I missed you, Paul!" She said as she pulled me in closer to her tits in her low cut crop-top.

"I missed you, Tammi," I said.

"I don't remember you being this tall, or this strong," Tammi squeezed me.

I had grown a couple inches since my 18th birthday, and was now about 6 feet tall. I had also been lifting weights to improve my sprinting, and I was now lean and in shape, but not very bulky.

"You look good too, Tammi. Where's my sister?"

"In here!" I heard a call from the kitchen. I knew it was my sister, because Charlotte has this deep, silky, musical voice that is unmistakable. I took my bag to the couch I would be sleeping on, and hugged my sister, making sure to graze her ass too.

Tammi and Charlotte took me to lunch, and gave me a campus tour the rest of the day. It had already been one of my top picks, but I liked it even more than I thought I would. It didn't hurt that I got to make eyes at Tammi's ass and tits all day, and I caught her checking me out as well. We mostly made small talk about the track team and how school was going. I asked if I could go to a college party, but my sister had just laughed and told me to wait till I went here.

We got home late, and Tammi cooked us all a bunch of spaghetti. It had been a hot day, and after driving, walking the campus, and a heavy meal, I fell asleep on the couch just after dinner.

When I woke up from my nap, the apartment seemed empty. I stretched and got up from the couch. On the kitchen counter was a note saying "We went out to a party and didn't want to wake you. Be back late- Tammi and Charlotte." I was really all alone. I checked the kitchen clock. 10:30.

I sat on their couch a little bored, hoping for something to happen or someone to come home. I messed around on my phone a bit, but nothing grabbed my interest. Then, in the back of my head I had an idea. A few times recently, I had snuck into Charlotte's room and swiped her panties. I had started after my 18th birthday party, when her boobs had accidently popped out of her bikini. Seeing her 20 year old tits, with their perky nipples had cemented my crush, and I hadn't been able to resist. I don't think she had any idea though, as I always took the least distinctive pair I could find, and they were just pairs she had left behind while she was at college.

So, here I was alone in the home of three college girls, bored, and horny. There was nothing stopping me from going into their rooms and rifling through their underwear drawers like I do when Charlotte isn't home.

I stood up and went down the hall where the bedrooms were. Two of the three doors were cracked open, and they were all dark. I had seen Charlotte and Tammi go in and out of their rooms earlier, so I knew which room belonged to each girl.

First I went into Charlotte's room. It wasn't my first time in her panty drawer, so I knew what to expect. When I slid her drawer open, I was greeted with the sporty thongs that Charlotte liked to wear. I picked a black Nike thong, because it was one of four and I figured she wouldn't really notice. It was like Charlotte, the perfect blend of sexy and sporty. I slipped the thong I had picked into my pocket.

Tammi's panty drawer was much more girly, with lots of lace and pastel colors. She had a few lacy pink thongs, so I slipped an older, more worn out one into my pocket. I felt ok that she would not miss it until I was long gone, as it blended in with the rest of her underwear nicely.

I went back in the hallway and stared at the final bedroom door. During the day I had learned that the other girl who lived here was named Tasha, and that she was a couple years older than my sister, i think about 23 years old. My sister said they had met because Tasha had been a TA in one of her Intro Chem classes, and they had instantly gotten along. Tammi said that Tasha was a little type A and was not thrilled that I was spending the night on the couch. I knew nothing about her besides that, other than I had been given specific instructions to stay out of her way.

I stood in the hallway, torn between the curious thrill of raiding a strange girls panty drawer, and the awkward shame of admitting to myself I was being a bit creepy for violating these girls' privacy. I decided that I was too horny and intrigued not to look. I opened the door carefully; not completely sure it was empty. It was dark, and nobody seemed to be in the room. I carefully stepped in from the hallway. I felt around on the wall and found a light switch.

Tammi and Charlotte's rooms had both been a little messy, with a pile of clothes here, and unmade bed, a little clutter on their desks. Tasha's room was impeccable, with every corner straightened perfectly. Tasha was in the largest room, so instead of a dresser next to her bed, she had a walk-in closet. I lightly walked to the closet, scared of disturbing the perfect room. Her closet was the same as her room, with all her clothes where just as they were supposed to be, organized by style and color. She had a stack of cabinets, and I gingerly opened the top one. Sure enough, I found underwear.

Tasha's underwear was as carefully organized as everything else, with different styles and colors separated. I began to suspect that Tasha would realize that there was something missing if I took a pair from this drawer. There was too much care placed into it.

I couldn't steal any, but I had to admire Tasha's underwear choses. Small sexy thongs, Calvin Klein panties, and even what appeared to be a latex g-string. I was starting to suspect that Tasha was very sexy.

I went to sneak out of the room. On my way out, I noticed a dirty laundry hamper tucked in the corner of the room. There were a decent amount of laundry, and a dirty pair of underwear sat on top. I couldn't resist. I walked over and started digging through, until I found a pair of everyday, light blue underwear towards the bottom of the hamper. I figured that by the time she did laundry she wouldn't even realize they were gone, and if she did hopefully nobody would connect it to me.

As I slipped the underwear into my pocket, someone cleared their throat in the hallway. I whipped around to see a woman standing there. She was a dark-skinned black woman, maybe a couple years older than Charlotte and Tammi. She had purple braids in her hair, and a beautiful face, with strong cheekbones, a pointed jaw, and dark sparkling eyes. She was wearing heeled boots, so it was difficult to say for sure, but she seemed about the same height as me, making her tall for a woman. She had a long and slender build and a natural strength exuded from her. I wasn't sure how much she had seen, but either way she had caught me in her room when I was not supposed to be there.

"Who the fuck are you?" she asked me, walking up close to me by the hamper. She moved quickly, and with a sense of command.

"Paul," I replied nervously before adding "Charlotte's brother."

"What the fuck are you doing in my room, Paul?" she asked with an icy demeanor. Definitely Tasha then.

I tried to think on my feet, "Just looking for the bathroom."

"It's not in my fucking dirty panties, pervert," she spat out. So, she had seen enough to know what I was doing and that I had just lied to her.

"Shit, I'm so sorry, I'll put them back," I felt my face turning red with embarrassment.

"What do you do with them anyways?" she asked, taking me by the hand and leading me to the center of the room. I think she was enjoying watching me squirm.

"What do you mean?" I asked, badly thrown off by her bluntness and her hand touching mine. I was a little intimidated. Standing next to me in her heels, she was a couple inches taller than me, and I had to look up at her a little bit.

"Do you wear these?" she asked, reaching smoothly into my pocket and pulling out all three pairs. She seemed surprised to find more than one pair in my pocket.

"No, I'm not a sissy," I was so uncomfortable that I was literally squirming. She paced a circle around me looking me up and down.

"No, you're too tall and fit to really be a very good sissy. Too handsome. What do you do with them then, Paul?" She was really going to make me say it.

"Rub them on myself when I jerk off," I said, feeling aroused by my own shame. It was hard to tell, but it seemed like Tasha was a little turned on as well. I had seen pornos where a man was "punished" for panty theft with sex, and I was hoping that it was about to happen to me. My whole body just felt hot and tingly. She stopped circling in front of me, and stood only a few inches away.

"How old are you, Paul?"

"I'm 18."

Her hand came down and grabbed my ass. She pulled me towards her, and whispered in my ear "Take your clothes of, and lie down in my bed. I have a surprise for you."

She let go of me and walked into her closet. I did as she said, getting naked and into her bed in record time.

"Did you look for my underwear anywhere else?" She asked from the closet, where I could not see her.

"Yes. In the top compartment in there. It was too organized though, you would have realized something was wrong," I replied honestly. It just felt like she would know if I was lying. I glanced at the alarm clock by her bed. 11:33. I wondered when Charlotte and Tammi would be home.

"Good thing you didn't look one compartment lower. It would have ruined your surprise." Tasha stepped out of the closet. She was completely naked. Well, almost naked. She was still wearing her knee-high heeled boots. She was also wearing some sort of harness over her hips. Her tits were almost nothing on her slender frame. Her arms were behind her back, holding something I couldn't see. "Lay on your stomach, face in the pillows."

I did as she told me. I was completely at the mercy of this dominant beauty. She walked up to the bed. I felt her soft but surprisingly strong hands run up and down my back before settling on my ass, where they massaged a bit. There was a squirting bottle noise, and something cool and oily splattered across my ass.

"What was that?" I asked.

"Astroglide. Lube."

"Why?"

"Paul, I'm going to peg you. Do you know what pegging is?" Tasha asked me.

"No, I don't think so."

"Oh, ok. Pegging is when a woman uses a strap-on dildo to penetrate a man's ass. I'm about to loosen you up with my fingers and then ass-fuck you with a plastic cock."

I felt a sense of panic. "But why though? I'm not gay, I don't want that!"

"Of course you're not gay, Paul. I am a woman, and there is never anything gay about a man having sex with a woman. And as for why, I like to be in charge and on top. I caught you in a weak position, so I am about to exert my control over the situation. Plus, I like to watch boys squirm as they take it up their asses. They usually end up cumming a ton because it stimulates their prostates."

"You do this a lot? Won't it hurt though?" I asked. I tried to roll over off my stomach, but a surprisingly strong arm held me down.

"Yes I do this a lot, and yes it can hurt at first. That's why I use lube. That's why I loosen boys up with fingers. Paul, please trust me and I think we will both have lots of fun."

"Ok, I guess," secretly I was a growing a little curious and aroused by my own vulnerability.

"Ok, good. Now just relax Paul," and with those words she stuck her first two fingers in my virgin ass.

At first, it was uncomfortable. The fingers slid in easily enough, as they and my ass were well lubricated. Even so, my ass had never had anything in it before, and there was some new stretching as she pushed her fingers in.

She whispered to me, "You're doing great, Paul. I'm glad you're letting me do this. Your ass is very tight, and very shapely too. I'm very excited about this. You're one of the cuter boys I'll have pegged. Here's your prostate."

She wiggled her fingers in my ass, and a wave of tingles ran up and down my body. Her fingers slid out, relieving the odd sense of pressure filling my ass. Suddenly they slid back in, stinging a little more than before. "Just adding a finger so that you're all warmed up. Then a little bit with my thin dildo, and then its show time."

My whole body felt hot, with arousal and shame and surprise and excitement all at once. After a several more minutes of my ass being stretched by her fingers, I felt them slide out. My ass was a little stinging and raw, but it hurt less than expected. Tasha had been right, having something in my ass had felt great. I heard the cap of the lube bottle open, and heard the bottle squirt again.

"Relax and breathe deeply," Tasha instructed. I did as I was told, and I felt something push against and slide into my ass. It was a lot harder than the fingers had been. It was a little wider, and seemed to reach inside of me more deeply.

"This is my warm up dildo. It's smaller that the one I'll peg you with. Should loosen you up nicely though. Once this whole thing is comfortably up your ass, then you'll be ready."

I could feel her hands pressing it in deeper, mixing the sharp tingles with the stretching and the pain. I let out a moan, and then whimpered a little. Tasha laughed, clearly enjoying herself. I couldn't see the dildo, but I could tell that it had a head on it that was girthier than the rest. My cock was semi-hard. I was aroused, but still intimidated and out of my element.

After several minutes, or what felt like it with my face pressed into a pillow, I felt something press against my ass cheek. "What a natural. The dildo just went hilt deep. I think you're ready."

Tasha placed her hands on my hips, and positioned me so that my back was arched, my ass was in the air, and my head down on the pillow. My face was turned to the side now, facing the empty doorway. I could still see more than when I was facing downwards. My arms were by my head, helping to prop me up, and my knees were pressed into the bed. I think she had turned my head sideways on purpose, because she walked into my field of view.

She slid a dildo into her hip harness. I'm not good at guessing length, but it was slightly longer and girthier then my cock. My dick is un-cut, 6.5 inches, and a little skinny. I've never had any complaints though.

"It looks big."

"It's my smallest one that fits the harness. Just relax, keep breathing." Tasha squirted lube in her hand, and started rubbing her dildo with it, as if she were jerking off. She giggled a little, and slapped it against my face a couple times.

"You'll be gentle though, right?" I was nervous again.

"No, that doesn't sound like fun to me," Tasha said, moving behind me. She grabbed my hips, which were still sticking in the air, and gave my ass a firm smack. A shiver of anticipation ran down my spine. I felt something rubbing on the outside of my ass, gently pushing against my hole. My cock started to get harder.

"Here we go," Tasha said. I felt a push, and a pop. A feeling of pressure pushed deeper and deeper into my ass. The dildo stretched me out, and I felt her hips pull back, push forward, pull back, push forward.

She spent a few minutes building a rhythm, pushing harder and deeper, but at a steady pace. I was moaning loudly, confused by the pain and pleasure. Suddenly there was a deep push, and I felt Tasha's hips hit my ass cheeks. She was all the way in.

Once she had it all the way, there was suddenly no sense of mercy in her strokes. She had eased her way in, but now her hips swiveled and pounded, smacking against my ass, pushing me forward. "Don't run from my cock, push back."

I couldn't even reply, instead I just whimpered. I tried reaching back a hand towards her hips, hoping to gain some control over the pounding Tasha was delivering. She quickly grabbed my arm and forced it back down. Suddenly a booted foot was placed by my face. Tasha had readjusted positions and was now pounding me deeper and harder and faster. I was completely owned, completely at her mercy. I could feel her long braids rubbing against my back. My cock was rock solid. It hurt, but I was enjoying it.

"You like being fucked!" Tasha teased me. "You're very excited about taking this girl cock! Say it, tell me you like my girl-cock. "

All I could do was moan. My arched back ached, as it felt like she was trying to snap me in half. She sped up, and I screamed a little. She held pace, driving me harder. "Push back!"

I tried to push back, but her hip thrust shoved me forward, and hurt. I yelped. She laughed. Her arms hooked around my torso, and she leaned forwards. I could feel her tiny tits and dark, perky nipples rubbing my back each time she stroked. She had stamina, as her strokes maintained their steady rhythm. One arm stayed wrapped around my waist, while her other reached and grabbed my hair. She pulled by head up from the pillow.

I was being demolished. She had me bent at the waist, arched back, her foot by my face, full control of my head, and ass up in the air and full of girl cock. Stuck in this position, I heard a voice come from the hallway through the open doorway. It was my sister's voice, but I couldn't see around the boot in my face, and Tasha was pulling my head so that I couldn't control my neck.

"What in the fuck is going on? Tasha, is that my brother?"

"Yes. I caught him," Tasha pushed her dildo in, and sat there hips against my ass.

"Caught him?"

"Stealing those," Tasha let go of my head and pointed at the panties on the ground.

"Those are mine! And those are Charlotte's!" Tammi's voice.

The boot was pulled back, and I could see Tammi and Charlotte. They were standing in Tasha's room now, wearing short, tight dresses. It seemed like they had been drinking, but they were not drunk. They were dressed up to go out. Charlotte looked flustered, but not as angry as I was expecting. Tammi seemed aroused by the sight of me being dominated.