MILF Chronicles Ch. 09

Story Info
Sherry is pushed to her sexual limits, and beyond.
6.8k words
4.31
90.9k
18
0

Part 9 of the 14 part series

Updated 10/24/2022
Created 09/21/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 9: Sherry Humiliated

Part 3 of Sherry's account begins here.

“Can anybody join this party?” I heard a new voice ask. I opened my eyes to the sight of a young woman standing nearby. She was cute, about five-seven with long copper-brown hair and B-cup sized tits. I know this because she had her shirt lifted up and was playing with a nipple while her other hand was down her shorts.

“Hey Sam.” Tara sighed contentedly. “Sure, you can play with our new toy too.”

I had thought that Sam was a man, but obviously 'Sam' it was short for Samantha.

She offered me her hand, the one that had been down her pants I noticed. “Then come with me toy, I want to have some fun too.”

I tried to get up, but my legs were numb and I could hardly feel them. Sam, with surprising strength, pulled me to my feet.

"Got the post cum wobblies, do we?" She observed.

"Actually I'm surprised she can stand after that." Tara opined. "She really is a slut."

"No, she's a super-slut." Chad interjected. "Super-slut Sherry!" Everybody got a good laugh at my expense. I was just trying to keep from falling down.

"Come on, time to see if that's true." Samantha said and led me by the hand down the short hallway and into the bedroom. She pushed me down onto the large bed and started pulling her clothes off. Then she rummaged around in the closet, just out of sight. When she reemerged she was wearing a leather harness with a fake cock sticking out. I knew what a strap-on was, of course, but up until then had never actually seen one. She climbed up on the bed near my head and pushed the plastic penis into my face.

"Suck my dick." She commanded. "I want it warm and wet before I fuck you with it."

I allowed her to put the fake cock into my mouth and I started sucking on it as if it were real. This wasn't actually all that strange to me since I always warmed up my own dildos at home the same way before using them. Putting a cold dildo into your snatch is not generally a pleasurable experience.

After her rubber erection was sufficiently wet and warm, Samantha repositioned herself between my legs and slowly penetrated me with it. She knew just how to make it feel good and soon I was pushing my hips up and meeting her thrusts. Apparently the dildo was stimulating her clit as well because she was moaning in pleasure with me.

I don't know exactly when they entered the room, but I noticed that the men were there watching us. Chad was working the video camera (damn that camera), and Tommy was slowly stroking his still-hard cock. Then Tara appeared in my peripheral vision and when I turned to look at her I saw that she too was wearing a strap-on. Her fake cock was longer, but smaller in diameter than the one Samantha was using.

Tara was rubbing some lube onto her rubber dick. "Hey Sam, let's DP this bitch. Get on the bottom, I want her ass."

Samantha climbed off and laid down next to me. I straddled her and reinserted her dildo into my pussy. Tara pushed me forward until I was laying flat on top of Samantha, my tits mashed into hers. I have to admit that felt kind of sexy. When I felt a finger wiggling into my butt I knew what was coming next.

I tried to relax my rectal muscles as Tara pushed a second finger into my bum. When she withdrew them I tried to remain calm and relaxed. I could feel her weight shifting on the bed as she tried to find the right angle and balance. Then I felt the tip of her plastic prick press against my butt hole. To her credit, she eased it in slowly, stopping every inch or so to let me adjust. Once it was all the way in she paused briefly and then withdrew. She pushed it back in using one long continuous stroke. It still hurt a little, but the pain was manageable.

Tara started a steady in-out rhythm and Samantha joined her. When Tara pulled the dildo out of my ass, Samantha would push hers into my pussy, and vice versa. I had been DP'ed before, but the fact that this was two women made it very different. My emotions were all over the map, but my ass and pussy agreed that this felt really good. Samantha began kissing me and it all felt so sensuous that I just couldn't help kissing her back. I decided that women are generally better kissers than men.

After a couple of minutes of this Samantha had a big orgasm, but Tara just kept thrusting through it. When she recovered, Samantha starting fucking my pussy with her fake cock again. After a few more minutes of this I unbelievably felt my own climax building once more. Maybe I was a slut; surely no ordinary woman could enjoy this much sex!

I noticed that Tara's thrusts became irregular and out of sync with Samantha. I looked over my shoulder and saw that Tommy was fucking Tara from behind as she fucked me. I turned back and looked at Samantha. She must have noticed the look on my face.

"Yeah, isn't it hot watching Tommy fuck his own sister?" She whispered in my ear. "It's just so wicked, don't you think?"

"But it's so wrong." I hissed back in her ear.

"Yes, but it's also so fucking hot." She cooed back. "Just imagine what it's like to fuck your own brother."

"Oh god, oh god." I moaned loudly. "I'm cumming!" And yet another strong orgasm ripped through me. If this kept up I was going to be too weak to move before this day was over.

I think my climax triggered Chad and Tara to cum again as well, and soon we were all laying on the bed, a sweaty but satisfied mess. The women took off their harnesses and dropped them on the floor. I think they weren't that comfortable.

"I don't know about the rest of you, but I'm taking a shower." Tara announced and got off the bed.

I was still too exhausted to move. Samantha rolled over and started caressing my hair. She didn't say anything to me, but kissed me tenderly on my cheek and neck, like my husband does after we have finished making love. It was a soft side of her that I had not seen yet, nor expected.

Then I felt the bed move and looked to see Tommy climbing between Samantha's legs. She laid back flat for him as he guided his still-hard cock into her. This guy was truly amazing; I'd never seen anything like it. I guess he did have a gift.

He was moving slowly, making love to her, not just fucking. She pulled my head to her and we kissed softly for a while before she pushed my face down the her breasts. I suckled her gently while Tommy slowly stroked his massive organ in and out making soft squishing noises.

Eventually Samantha had a quiet, but obviously very pleasant orgasm. After it was over with she pushed me and Tommy off of her and stood up.

"Come on," she said, taking my hand, "it's time we showered too."

I got up off the bed and followed her to the bathroom. The shower was not large, but it had enough room for two if you didn't mind being cozy. At that point I didn't mind; it was nice to be treated tenderly after all the demanding sex that had been forced on me.

Samantha soaped me up, lingering on the 'naughty bits' while avoiding the tattoo. After she rinsed me off and washed my hair, I did the same for her. When we were finished we dried off and brushed out each others hair. As we exited the bathroom I almost felt human again.

We were greeted by the smell of pizza. Samantha didn't bother getting dressed and led me directly out into the kitchenette area nude. Apparently they were all comfortable being naked around each other. It didn't bother me as much as I thought it would.

"There you are." Chad commented. "We ordered some pizza if you are hungry."

Actually I was famished.

"Too bad you were in the shower when it was delivered; I wanted to have you tip the delivery boy." Tara said as she looked directly at me. "We told him he'd have to take an IOU and that maybe we could hook up with him later."

I was hoping the opposite, but if I knew these two they would put some effort into finding him before the day was out. I wolfed down a couple of pieces of pizza and slurped down a diet soda. After we were done eating Chad announced that it was time to go, so everybody got dressed except me; I couldn't find that damn bikini.

"I think before we give Sherry her bikini back that we should tag her." Chad said.

"That sounds like fun." Samantha replied. "I'll get the marker."

When she returned she handed a black magic marker to Chad. "You should start since it's your idea."

Chad was the first, but they all took turns writing messages on my body. When they were done they stood me in front of a mirror and showed me what they had written and where they had written it. Just above my left nipple were the words “suck me” with an arrow pointing at the nipple. Above my right nipple were the words “bite me”, again with an arrow pointing at the nipple. Just above my slit on my lower abdomen was written “taste me!”. On my left butt cheek was the word “SLUT” on the right “WHORE”. The bikini would hide almost none of it. I was mortified; how could I go back into public with this obscene writing all over me? But that's exactly what they intended.

So there I was, once again walking down the street in that damn bikini, but this time I also had writing on my body which was attracting even more attention, although I didn't think that was possible. Everybody we passed gawked at me, craning their necks in an attempt to read it all, which was difficult because some of it was partially covered by the bikini, but that didn't stop some of them from trying. I was feeling so humiliated, especially because of the words on my exposed ass cheeks.

We took a different route back to Chad and Tara's apartment. As far as I could tell we were going around the old factory that we went through before. This took us past more store fronts and regular people. Fortunately there didn't seem to be any children in this part of town. In fact, I hadn't seen many women either.

A few of men we passed asked me how much I charged for sex, but Chad either told them I wasn't for sale or that they couldn't afford me. And everywhere it seemed that people had cameras, either little compact pocket units or in their cell phones. I was losing hope that I could keep this day a secret; surely some of these pictures would wind up on the Internet. The only thing I had going for me was that the way I was dressed I didn't really look like myself, so maybe nobody would recognize me. If someone did I could always deny it. Still, this could come back to haunt me.

We came upon a pizza place and Tara had us stop so she could “duck in for a second”. She came back out in less than a minute and said that “he” would meet us in the alley. I was concerned about what was going on, but Tara led us into an alley the ran between the pizza place and the next store front. As we walked down the alley, a side door opened about twenty feet ahead and a geeky looking boy in a dirty apron stepped out. He looked to be about 18 or 19 years old, thin and generally kind of “rumpled”.

“Time to tip our pizza delivery guy. Gotta pay off that IOU.” Tara gloated. “What did we promise you, a blow job?” She asked him.

He nodded his head up and down slowly, probably still not believing what was happening. Tara looked at me and I knew what I had to do. I knelt down in front of him and lowered his zipper. His legs were trembling; I didn't know if from fear or excitement. I reached into his pants and pulled out his cock. It was on the small side and very hard. I took the whole thing into my mouth easily. His crotch smelled like he hadn't bathed in a couple of days and I almost gagged. I began licking the underside of his dick as I bobbed up and down on him. I don't think he lasted more than thirty seconds before he was groaning and shooting his semen into my mouth.

I got to my feet and he fell to his knees. This day had been a train wreck of ironies.

“That was the best thing I've ever felt.” The boy stammered.

“Lots better than your hand, huh?” Tara teased and turned around to leave.

I followed her out of the alley; the delivery boy still on his knees as far as I knew. We continued on our trip back to their apartment. The attention from the men we passed did not abate, even a few of the women took pictures and whistled at me. For some reason that was even more embarrassing than when the men propositioned me.

We were, I had judged, over the half-way point in our trip back when we came upon an unexpected sight. There was a space between the older buildings on this street that looked like it had been cleared of an entire building. In this space there was a small park, complete with a small fountain and some stone benches. The grass and landscaping was surprisingly well maintained making this park a strange, but welcome oasis in the middle of an urban area. As Tara and Chad led me into the peaceful little park I noticed a plaque that dedicated the park to the people of the city by some rich benefactor; probably the original land owner, but I didn't get to finish reading it because Chad dragged me away to the far side of the fountain.

Chad and Tara silently removed the little bikini, and once again I was stark naked outside, but this was the most public place yet. I was instructed to lay down on a stone bench where I was completely shielded from the street by the stone base of the fountain. The stone felt warm against my back as the early summer sun beat down on my front side.

“You know what would be really fun?” Tara asked her partner. “If we were to just leave her here like that while we hid somewhere nearby so that we could still record whatever happened.”

“Oh, shit!” I thought. “She can't be serious.”

“Yeah that would be hot.” Chad responded.

I waited for one of them to speak up and denounce this terrible idea. I wanted to scream a them, “No! You can't do that!” As the fear rose in my mind.

“But I don't think we can. Things could too easily get out of our control and we can't risk that.” Chad finally decided. I let out a breath I didn't realize I was holding.

“Oh pooh.” Tara exclaimed. “I'd like to try that sometime.”

“Maybe, but it would have to be planned ahead of time better.” Chad remarked.

I wasn't quite sure what they were talking about, but I didn't really care either. I was just happy they weren't planning on leaving me here to be mob raped, which is what I was sure would happen if they did. Instead Chad and Tara sat down on another stone bench about ten or fifteen feet from where I lay.

At first we were undisturbed. I could hear the traffic occasionally going by on the unseen street and the mummer of voices as people walked past the little park on the nearby sidewalk. I kept expecting someone to join us by the fountain and notice me laying there nude, but as the minutes ticked by and nobody entered the park I began to relax. Maybe it just wasn't used that much by the locals, I thought. Maybe they are so used to it they don't even notice it anymore.

I could feel the whispering breeze caressing my body, especially the parts that are normally covered up. This caused my nipples to harden slightly and cooled my pussy due to the copious amounts of moisture between my slightly spread legs. Despite the unyielding stone beneath me and the very public nature of my perch, I was beginning to feel quite comfortable. I could almost believe that this park was our private little sanctuary and that I was safe from prying eyes here.

My illusion was shattered by the the sound of male voices and polyurethane wheels rolling across concrete. I felt the tension in my body rising as the sounds came nearer, but I kept my eyes tightly shut. The crash of fiberglass and steel against brick and mortar brought an abrupt end to the sounds and for a brief moment silence again reigned. My hands tightened uncontrollably on the edges of the stone bench, once again aware of how exposed I was.

“Holy shit.” A male voice whispered.

“What the fuck?” A different male voice exclaimed.

I couldn't help but open my eyes. I was looking up into the faces of two young men, not more than eighteen or nineteen years old. They were holding skate boards and were wearing the typical baggy shorts and shirts of skate-boarders. They were also staring at my naked body lustfully. An involuntary shudder ran down my spine.

“Hey, check out the writing, bro.” The first skater boy said to the other.

“Instructions dude, gotta like it.” The second skater boy responded.

That was when they noticed Chad and Tara. “Hey, is she for real?” The first boy asked them.

“Absolutely. Just follow the instructions and have fun, but if it's not written, you can't do it.” Chad answered. “Understand?”

“Sure dude, no problem.” Skater boy number two acknowledged.

“This one's mine.” The first one proclaimed as he quickly bent down and latched onto my right tit with his mouth. Following the written instructions he playfully started chewing on the nipple.

“That's OK, dude, I've got something else in mind.” Number two said as he moved between my thighs and leaned down over my crotch. He inhaled deeply of my aroma and smiled. Then I lost sight of him as the first boy who was nibbling on my right nipple leaned over me and started licking my left nipple. But then I didn't need to see what the second skater boy was doing because I could feel his tongue exploring my wet slit. My clit was so sensitive now that every time he flicked it I flinched, causing my hips to jump.

“Shit is she wet and ready.” Skater boy two announced. “Let's get Ned and Tammy.”

The first boy broke off, leaving my nipples wet with his saliva. “Yeah, we should share this with Ned.” He agreed. “And who knows, maybe Tammy will be interested too.” He looked at me. “Don't go anywhere now.”

They retrieved their boards and set off, presumably in search of their friends. Chad and Tara made no move to leave, so I guessed that they were planning on waiting for the return of the skate board gang. I wondered how long they would wait though, thinking that we would be late getting back to Marc if we delayed here too much longer. As I waited I tried to relax again, but I couldn't regain that feeling that I had before the skater boys arrived. The hard stone bench now brought only discomfort, and the scorching sun hurt my eyes. The cool breeze across my nipples evaporated the saliva, but also kept them hard. I'm sure the moisture coating my inner thighs and the entire surface of my sex must have been glistened in the bright afternoon sun. I imagined that I looked like a total wanton slut laying naked in the little idyllic inner-city park, but then that was the point.

My thoughts were interrupted by the sounds of voices and skateboards wheels. It sounded like there were more than two this time. The first two must have found their friends. My pulse, which had slowed some, shot back up.

“She's right over here, man.” I heard a familiar voice say. It sounded like skater boy number one.

“This better not be a joke man or I'll kick your ass.” Warned someone else with a voice I didn't recognize. Was this Ned?

I turned my head in the direction of the fountain and the voices. I saw them coming around the big stone base just as the first skater boy responded.

“No joke...see?”

They all skidded to a stop just a few feet from me. “Holy shit!” The new skater exclaimed. He looked to be a bit older than the others, maybe 25. He was obviously trying to hold onto his youth as he was dressed the same as the others and had at least three days worth of facial hair making him look kind of scruffy. The other skater was a girl judging by her fine features and full lips, and the fact that the first two had said they were bringing back “Ned and Tammy”. Otherwise she seemed to be hiding her femininity with short hair and a loose top that hid her breasts.

“You weren't lying Skid.” Ned said as he addressed the first skater boy, which I now knew was named “Skid”. It seemed like a strange name, but then again given my situation, who was I to judge?

12