Chapter 4 Penny has Her Big Night

Literotic asexstories – Chapter 4 Penny has Her Big Night by crazielife,crazielife
Gio put his computer down as I walked in. “Wow! You look amazing.”

I touched a finger to my ass and went, “Sssss.”

“We are going to be leaving shortly so you should get dressed.”

“Where are we going?”

“To the city. We’re going to stop at a club for a cocktail and then we’re going to ‘Daniel’ for dinner.”

“Really?”

“Sound good?”

“Yeah!”

“Oh, I almost forgot, this is for you. For tonight and pulled out a huge jeweled ass plug.”

Facetiously laughing I said, “For me? How thoughtful.”

We both dressed and I was surprised to see Gio in a suit with a black crew neck shirt underneath.

I stepped out and looked at myself in the mirror and was happy with what I saw.

“I thought you would enjoy being looked at.”

“Yes, it’s exciting.” As we walked out the door.

The plug was different as as we got in the car, I could feel it push deeper offering a constant reminder of its presence.

I looked down and saw it was nearly impossible to sit in this dress without being exposed.

I kept my knees together and Gio looked at me, put his hand on my knees, and rubbed my leg. I relaxed a little.

“So tell me, do you like Maya?”

“She’s really nice. Still a bit intimidating but yeah, I like her.”

“She texted me you know.”

“Oh?”

“She thinks you are hot.”

“Well, I think she’s hot too.”

Gio slid his hand between my legs and I parted them a little.

“Would you enjoy her tongue on you again?” As he flicked a finger on my still sensitive clit.

I made a little moan and put my head on his shoulder as I parted my legs more.

Gio pulled a jar from his pocket and put some of its contents on a finger. He put his hand back between my legs, and as soon as he touched me, it was cool and then warm. It made me moan again and spread my legs even more.

I was well aware of the driver and could see his eyes in the rearview mirror so I knew he could see. I didn’t care. It felt so good. Soothing.

As Gio took his hand away, he said “I have something else for you.” And pulled a decorative set of nipple clamps with a gold chain out of his pocket.

I gasped.

“Would you like to wear these?”

“Yes,” I said in a bit of a fog. The sensation in and around my labia was intoxicating.

Gio gently slid one breast out of my dress, put a little of the cream on my nipple, and rubbed it for a few seconds. He left me sitting there with my tit out and my nipple grew hard fast. When he attached the clamp, blood rushed from my nipple right to my groin and it made me want to cum. He then just as gently did the same thing to the other nipple and I reached between my legs to my exposed pussy and ran my finger over my slit. The sensations were overtaking my senses.

“Do you like that?”

“It feels so good Gio.”

Gio gently played with my slit and would occasionally turn the plug in my ass. I had scooted down on the seat and only wanted what I was feeling.

“May I cum Master?”

Gio began sliding his slippery finger ever so gently up and down my slit. I lost control and bucked hard with an intense orgasm.

We arrived.

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I hadn’t been to this club in a long time. I liked it here and I especially liked bringing subs here who craved attention. Penny was perfectly primed. As we stepped out I looked her over and realized you could see the clamps and chain inside her dress and I wondered if anyone would be able to detect the jeweled plug.

We went into the bar and we sat at the bar. I wanted her on display. She looked innocent and exquisite. I was tempted to bend her over and ass fuck her right there.

“They’re all men.” She said looking around.

All eyes were on her.

“Do you like that Penny?”

“I am so hot Gio. What are you doing to me?”

“You are hot Penny and desired by every man in this room.”

“You mean you want every man to look at me,” she said.

“I mean YOU want every man looking at YOU. Don’t you.”

She looked at me with lust in her eyes. “Yes”

Looking at her, “I’m going to change your name for tonight.” I said.

“Oh yeah? What’s that?” I like Lola as a better nickname for Penelope, it is Penelope isn’t it?”

Penny chuckled, “Lola, huh? Don’t you think that’s a bit…maybe like Lolita?”

“Well, Penny is just too unsophisticated. Look at you. You’re a beautiful woman.

“How about Ella? I’ve always liked that name.” She said.

“Ella….I like that name for you. Is that good for you?”

“Sure, I like that,” she said with a big gracious smile.

I’d like you to walk to the lady’s room and come back please.” She gave me a look like I know exactly what you are doing.

As she slid off the bar stool, her dress rode up her backside exposing her rear. I couldn’t see but I know if her rear was exposed, her pussy was on display. If no one saw the butt plug before, they sure saw it now. She quickly pulled her dress down and walked across the room. The ankle restraints were an interesting touch.

I watched her walk across the floor and all eyes were on her. About 5 minutes later she reappeared and I noticed her lipstick wasn’t quite right but I thought it was an amazing improvement. She had applied more but as best I can describe it, it was childlike. Not smeared but not neat. It was so hot because now she looked like she did something naughty with her mouth and was indecently exposed.

When she sat, she downed her martini and asked for another.

“Was that hard for you? Walking through a room of men?”

“You remember us talking about a gangbang?”

“Yes”, I said.

“Gio I think I was wrong about understanding gangbangs.”

“Tell me.”

“Walking across this room with all these wealthy, well-dressed, good-looking men staring at me? I am so horny, I would let you all gangbang me right here on this floor.”

I chuckled, “I’ll have to remember that. But you would ruin your beautiful new dress.”

“I’d take it off.”

“Oh, and your hair and makeup.”

“I think I’d look better drenched in all your cum,” then turning and looking me right in the eyes, “don’t you think? There’s even some silver foxes here I’d fuck.”

“It’s an incredible vision. One I will not likely ever forget,” I said, “But tonight I have other plans for you. I promise you will enjoy the evening.” And I finished my drink.

Ella downed her second in a big gulp and I knew she was tipsy already. I had seriously thought about some Molly for her, but she didn’t need it. This girl was so hot I thought I might need a fire hose to put out her fire.

“Let’s go,” I said as she again allowed her dress to ride up as she got down off the bar stool. And with one hand on my arm, she slowly adjusted herself as we walked. We should think about a labia piercing if we’re going to do this again I thought and made a mental note.

We got back into our waiting car and arrived at the restaurant, where Ella’s appearance made quite the stir. I had requested a booth when it was booked and was accommodated.

For the most part, the dinner was exquisite and both Ella and I got off on exposing her to whoever came to the table. The water boy was especially fun because he kept coming back. I don’t think Ella could complete a single sip of water without him hovering over her.

“Do you want to give him something to talk about?”

Ella laughed.

“Pull your dress up to your waist.” She did and when he came back she looked him in the eyes as she spread her legs. Water went everywhere. The maitre ‘d was particularly annoyed until Ella stood as they were replacing our tablecloth. She never pulled her dress down until after standing.

She was tipsy and we both had a good laugh.

“That was lovely Gio. Thank you so much. I have never had such a wonderful day in my entire life.”

“I’m glad Ella. That’s what I wanted for you. Did you enjoy being exposed?”

“Oh, it was fun. At the club, I was positively randy!”

As we drove, I said, “Let’s get that dress off.”

“OK” without a concern as she leaned forward so I could help her get out of it. The nipple clamps were not very forceful but when I removed them she sucked air through her teeth. She laid with her head on my lap and I was gently stroking her from her chest to her legs.

“When I’m with you, I feel comfortable and safe. I am enjoying this experience without worrying about being put in danger or being asked to do something that would hurt me in some way,” Penny said.

“Good. That’s what I want for you.”

“Why are you being so good to me?”

“Because I like you and I think you are worth the investment in time to be a great sub.”

“I want to be. For you.”

“Tell me about what happened today with Maya. I got a sense something changed.”

“You are perceptive Gio. Yes, I got to know her. But I guess more importantly I felt like she accepted me.”

“Oh, she wants to accept you all right.”

“What do you mean.”

“She thinks you are incredibly hot and wants to fuck you again.”

“Mmmm” That was nice.”

“Would you like that?”

“I’ve never, ever thought about being with another woman but I would definitely not mind being her plaything.”

“Interesting you put it that way.”

“What?”

“Not as an equal but a plaything.”

“I like my role.” I went to say something and Ella interrupted, “Will you fuck me in the ass tonight? I am so hot for your cock and I’m not sure my pussy can take it yet.”

“I don’t know Ella. I’m not sure you are ready.”

Ella abruptly sat up and spun around on her knees and reached around and pulled her plug out. “My ass hole needs you, Master.” She said smiling at me.

“Maybe.”

“Eeee!!” I can’t wait.

Penny fell asleep and I probably dozed as well. When we arrived I scooped her up and carried her naked body into the house. Maya was there as she and I had previously discussed. I brought her into my room and put her on the bed and she woke and saw Maya.

“Maya.”

“Hi honey,” she said as she stripped.

“Maya, what are you doing?” Still groggy.

Maya climbed on the bed as I was taking my clothes off. “Come over here and suck on my clit little one.”

Penny was on her knees and I seriously considered doing her ass. But I wanted to wait until tomorrow. I had a special day planned for her. I pulled Penny’s plug out and slid my cock up and down over her ass hole making her moan. She stopped sucking on Maya’s clit to say, “Ohhh, Please fuck my ass..” I put the head of my cock there and she pushed against it. I pulled back and did it again teasing her. She moaned loudly. I drove into her pussy. She was sopping wet. I felt her clench around my cock. It was incredible.

I saw her reach under herself and every time she touched herself her body would flinch. This made her suck and lick Maya more. Maya was now on one elbow holding Penny’s head to her mound and moaning as I was fucking her. Every time she touched herself and flinched it made my cock slide in and out. I just stopped moving and watched her and Maya’s erotic display as I was being fucked by this hot little thing. She was fucking me.

I was building and took her hips. This made her more excited and was licking and sucking harder making Maya groan and moan now while thrusting at Penny’s mouth. I pushed deep into her which made her moan into Maya, making her cum violently. She squirted all over Penny’s face again.

With my cock still in her, she got up on her knees and pressed her back to my chest and was still fucking my cock as best she could in that position.

Maya moved fast. She spun around and got on her back and said, “Give me that hot little cunt.”

Penny repositioned over her mouth and I could tell the sensitivity of her healing pussy and the softness of Maya’s mouth were intense. I pushed back into her and she exploded thrusting at my cock and slamming her mound into Maya’s face.

I wasn’t through. I took her hips again and pushed her down on Maya as I pounded her. Her body was limp. I came deep in her making her moan and coo. As she rolled off and Maya gasped for air, I looked at the two of them and was amazed at their beauty.

Maya knew me well. She took my cock in her hands and played with me for a few minutes and I was hard again. She smiled as she pushed me over on my back and mounted me. I could see Penny watching as Maya used me. She knew I wasn’t coming any time soon so she had her way with me.

Then to my surprise, she said, “Get over here slut, and lick my cunt while I fuck your Master.”

I didn’t expect it nor did I know where it came from. Penny whimpered and climbed between my legs and was tonging her and me as best she could. “Lick my ass slut.” She said.

Penny spread her cheeks and was tongue fucking her ass without hesitation and was cooing the entire time. This put Maya over the edge and she exploded violently again. She was moaning loudly from the assault even after she had cum. She had to roll off of me to get away it was so intense.

Maya grabbed Penny by her hair, dragged her body over mine, and said, “Make your Master cum.”

“I’m so sore,” She whined and Maya surprisingly slapped her face. I was shocked. But I was watching Penny. She was wanton. There was no reaction except to obey.

Penny dropped her very sore dripping swollen cunt on my cock again and was yelping, screaming, and thrashing. I knew it would be a while before I came. Maya took Penny’s body and slammed her onto my cock over and over. Penny was in another world. Maya was in complete control of Penny’s body and was using her cunt to fuck me. I never came.

She took her by the hair, pulled her off, and said, “suck.”

Penny was in a state. She took my cock so deeply down her throat I could feel her lips grasping at the base of my cock for more. Over and over, horsely choking herself on me. This made me cum. My balls ached as she rolled off and climbed close to Maya.

I woke early and rolled out of bed to find both girls asleep with Maya’s nipple in Penny’s mouth. I just watched them for quite a while. Any time either of them would stir, Penny would suckle. It was making me hard. I thought better of it, got up, and decided to make them both breakfast.

I had the table set and had food on the table and when I walked back into the bedroom. Penny was straddling Maya and they were in the throws of licking each other to orgasm. They didn’t know I was there although I don’t think they cared. They both came together. Well, I think Maya came and that made Penny cum. Anyway, I said, “Breakfast is ready girls.”

I went in and poured the coffee and Maya walked in nude stretching and said, “Mmm, smells good.”

I looked behind her and saw Penny was crawling. Maya looked at me and smiled.

“May I sit at the table Master?” Penny asked.

Later that morning:

“See you next week Gio,” Maya said as she walked out.

Penny looked at me.

“Friday used to be her day,” I explained.

She just nodded and then gave me a devious look.

I went to her and we kissed deeply as she grabbed my cock.

I picked her up and lay her on the table sliding dishes and glasses out of the way. As one crashed to the floor, we both giggled as she was humping at the air to get my cock in her.

“Oof!” As I entered her. She clawed at my back.

I pounded that raw pussy. She yelped and howled. I was unrelenting. When I pulled out, we both looked down at my pulsing cock, knowing I’d be ready instantly. I rode her for a good 20 minutes and she orgasmed twice before I unloaded in her. I lay on top of her and we were both breathing pretty heavily.

“I need to shower,” she said patting my back to get off of her.

I bit her nipple. “Ouch!” Damn, that hurt!” As I lifted off her she gave me a playful slap.

We both spent the next hour or so grooming and I found Penny curled up on the sofa.

“Do you like to play with toys?” I asked as I picked up my photo journal.

“Yes, I have a few.” She shared.

I use the journal for a couple of reasons, one is to get a sense of which photos illicit a response, and secondarily, slaves typically get an endorphin release from looking at the images. It’s the lowest level of play I use. It’s mental foreplay. All of the photos are high-quality artistic photographs using light and shadow to accentuate the subjects.

I sat next to her and she put her head on my lap.

“What’s that?”

“Pictures. Take a look.”

Penny started studying the images. Very slowly. I watched her response. I knew it by heart but could see which ones she was looking at. Her facial expression as well as her body told me which ones excited her the most. These are what she saw in this order:

Man nude from chest to pubes showing 6 pack and lower belly only

Man with a hard-on in underwear

Woman in arms of man being fucked

A woman on the floor looking up at a man standing, with his cock in her mouth.

A woman with a black man having sex.

Girl eating girl from rear vantage point showing pussy and ass.

Woman in cuffs, behind back and collar watching another woman suck my cock.

A woman spread tied to a table.

Naked woman covered in multiple masculine hands.

Close-up of woman’s hands in wrist restraints.

A woman tied with ropes strung from the ceiling.

A woman tied to a table in a bar with legs spread and men’s hands all over her.

Woman in pain, strung up with weighted nipple clamps

Woman with red marks and welts from being whipped

Bound girl triple penetration photo

Girl on leash, hands bound, cock in her ass in a public setting with other people around watching.

I slid out from under her and she didn’t break focus until I started inserting a lush egg vibrator into her.

She looked and said, “Oh…I’ve always wanted to try one of those,” She cooed.

She watched intently as I slipped it in her and she went back to the photos. There are at least 200 photos in my album with each becoming more intense as you progress through them.

I sat in the armchair opposite her and turned it on at a very low constant setting for 30 minutes.

She jumped briefly, looked at me, and went back to the book. I just watched her. When she started flaring her nostrils I knew she was at the level I wanted her. This is as far as she got before her eyes closed, and she dropped the book on the floor.

I took her by the hand to my dungeon and lay her on my table. I put wrist and ankle restraints on her which she willingly allowed. Then I began securing her to the table.

“What are you doing?” she asked in a very sensual voice knowing exactly what I was doing.

“Shhh.” Putting my finger to my lips. I watched her face as I changed the program to waves.

“Oh God.” She moaned. I could see her stomach muscles tensing. What a sexy little six-pack she had I thought.

“You are not allowed to cum. Do you understand?”

“Yes, Master.”

“If you feel like you are going to cum you must tell me. You do NOT cum.”

“Oh shit! Her hips were already gyrating and she was now wiggling around.

I stopped the toy.

“Mmmm, that was so good, may I have more?”

I squeezed a tit and slapped it. “No talking!”

I reached over and took a nipple clamp and attached it to the tit I just hit.

“Ohhhh! Ahh!”

“Quiet or I will gag you.”

I have a program I created for the vibrator that allows it to run and then turn off in cycles of 5 seconds each. I have another programed for 10 and another for 15. I used the 5 second one. The vibrator is on the second to highest setting. I know from experience, the feeling for a woman is pretty intense.

I took the clamp off and started the program.

The vibrator made her jump around like a bound snake. The second it stopped I reapplied the clamp.

When the vibrator started again, I immediately took it off. I repeated this action for 1 minute watching the clock.

Then I switched to the 10-second interval. Again each time it went on she was wild. But this time I used a heavier strength clamp and stood over her putting them on each nipple at the same time.

Off they came when the vibrator started. Watching the clock for a minute.

When I got to the 15-second interval she was moaning and whimpering pretty loudly but there were no objections. During my 15-second interval, I applied a chain to the clamps and tugged on it during the vibration. I then left them on and pulled the chain harder, stretching her nipples upward when the vibrator stopped.

She was so loud I had to ball gag her. She looked a little frightened at first but I put my face close to hers and made eye contact and asked, “Are you ok?”

“Mmmf” nodding yes.

I continued for the full minute tugging harder on the chain each time.

Every time I pulled the chain she would thrust just as hard as when her lush toy went off.

Her moans were luscious. She was near losing control. I could feel it.

I took the clamps off and of course, her body reacted.

I pulled the vibrator out of her and she groaned.

She saw me put the vaginal pump on her and banged her head back a few times.

As it was expanding drawing blood into her vaginal area, she shook her head no.

“Do you want me to stop?”

She moaned loudly and her head shook no again.

“It’ll only be a couple of minutes your first time,” I said.

I watched the clock as I took a spark rod and touched her on her sides and around her breasts to distract her while she was pumping up. I could see her swelling nicely. While waiting, I released her wrists. “Don’t you dare move your arms.” She kept them over her head.

I released the pump and she moaned loudly and again whimpered. She was nicely engorged.

I reapplied the clamps and chain back on her nipples. She moaned loudly and thrust her pelvis in the air.

I took a magic vibrator wand from my table and gently applied it to her clit. She went wild. I continued applying and denying. She was thrashing her head and her body was lunging for the vibrator each time.

I heard her try to mouth ‘please’.

I looked at her and whispered, “Not yet.”

Deep groan and now moaning constantly.

I looked at the clock and continued my assault for a full five minutes. Every time she was right at the edge I’d take it away.

I saw tears forming in the corners of her eyes. Begging me with her eyes for release.

I leaned over her torso holding her down and pressed the wand firmly on her clit with one hand and I reached up and ripped her nipple clamps off with the other hand. Even gagged her screams were piercing. She came so hard that I had a hard time holding her down. She grabbed her nipples and was pulling them, stretching them upward so hard I thought she’d injure herself while thrashing on the table.

As I climbed off of her, she pulled the gag out of her mouth somewhat delirious.

“Cock!” She yelled as she reached down frantically unclipping her ankle restraints hurriedly, shaking badly. The way it came out it was almost comical. She was pretty out of control.

She dropped to the floor hard and clawed to get to me and inhaled my raging hard-on.

She sucked my cock so hard, that later, I noticed the head was black and blue. She gave me a hickey on the head of my cock! Not only that, but when I came, which didn’t take very long by the way, she literally sucked the cum out of me giving me pretty powerful blue balls. My legs went weak for a moment. She collapsed at my feet.

“I never knew…I never came… so hard….never…” Lying on the floor her body still squirming, heaving for air.

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Gio just left me there and walked away. The after-burn was giving me stomach knots. I had to lie there for a long time. I was encouraging myself to join the living and to get up when Gio walked in.

“We’re not through.” He said. My heart fluttered.

He helped me stand. “Over here,” he said as he guided me by an arm. My body was on fire.

I could feel myself trying to put one foot in front of the other. I wasn’t sure I could take any more. There was a floor-to-ceiling mirror leaning against a wall and I saw myself in the mirror as we walked by. I stopped and stared at the image.

“Gio, I’m a mess. My nipples are black and blue. My pussy….Oh, my poor pussy.” I said near crying with a little laugh.

He started applying a cream to my nipples as I watched. I pulled away at first, “This will make it feel better fast,” he said and I relaxed.

As Gio worked on me, I realized he was dressed. He asked, “Are you clean?”

I nodded, “Yes.” I knew what he meant. Was I finally going to get what I wanted?

He walked to a cross frame and I followed. Mechanically, I picked an arm up to have my cuff latched. And then the other. I looked down and spread my legs so he could latch my ankle cuffs as well.

“You will like this Penny.” I saw him lubing up a butt plug. I moaned as I watched him and could see him slide it in me when I turned my head to the mirror. He then took the pink vibrating egg, my new friend, and put it in my pussy.

When Gio took his phone out, at first, felt the anal plug vibrate. Then I felt the Lush egg turn on. My legs started shaking. Gio played with his phone and the strength on the plug increased dramatically and the Lush stopped. The power from the plug was intense. It made the muscles in my ass and stomach cramp. Then he switched to the Lush and that made me do uncontrollable pelvic thrusts.

I was moaning so loudly I was hoarse. I could feel the orgasm building and I knew it would be intense. Without me saying a word, he stroked the side of my head putting my hair behind my ear, and said, “Not yet.”

Then they both went on at a very high level for a few seconds and stopped.

I could see Gio lubing his cock. He pulled the plug out of my ass, turned the lush on low, and slowly pushed into me. The mixture of pain and pleasure was not something I could have ever understood without experiencing it.

My body was flailing. I could barely breathe let alone make a noise. I just shuddered so hard I could feel the wrist and ankle straps cutting into me. My body went limp. I had no strength to hold myself up. The toy was still going in me and he was now in full stride slicing in and out of my ass. I was flopping around with no control when Gio took my hips and pounded my ass until he came.

That was it. My orgasm ripped through me. Wave after wave, after wave.

He was yelling and I was screaming.

“Gio, Please…. no more!”

Immediately, I was turned off and he unclasped my wrists first and I collapsed. He quickly removed my ankle straps, picked me up, and carried me to his bed.

It was dark out but I had no idea what time it was. And then nothing.

“Penny…Penny…Time to get up.” I looked at Gio and said, “What time is it?” I could see it was light out.

“It’s 11 am. Time to get cleaned up and get back to school. I want you to eat before you go. You had no dinner,” he said.

“OK”, I said as the past two days flashed through my mind.