Adventures of Penelope - Fictional Story

Helccat95

Penelope was an average woman in her early 20's. She was a beautiful brunette with hair past her shoulders, ample peach colored breasts, a small amount of padding in the hips and voluptuous in build. She was the epitomy of a repressed. She never got in trouble and had only a few partners of the vanilla variety in her list of lovers. But she often felt trapped and had an itch she couldn't scratch. She loved to watch films and documentaries about sexual escapades beyond missionary. When she moved out of her home town to start a new job and life she craved something more.


One night she saw a commercial for a chat line to meet singles. She was excited. She called in and created a mundane profile. Her voice and message screamed repressed. She immediately got men that started to message her about how big their dicks were or how horny they were. This all seemed boring and she was about to hand up until she heard his voice. He left a message simply saying "Are you bored little girl?" At first she was angry someone would say that but she knew deep down she was intrigued and some part of her screamed to be set free by his voice. She messaged him back in a haughty tone, " What makes you think I am a little girl or that I am bored?"


The message she got back was laughter and his phone number if she wished to talk. He was then gone before she could message him back. As we all know she wrote that number down but should she call him back. His voice profile said he was older than her too. But that confidence and his voice... She couldn't deny she was beyond intrigued.


She called him and did not know what to expect. They talked for a long time about their lives and mundane things. He was intelligent and mature compared to the boys she had slept with. He also seemed experienced even though no one broached this subject as of yet. That night he bid her good night and was every bit the gentleman, but for some reason Penny could not sleep and kept wondering what he would be like in bed. If he would be as commanding as his voice seemed. She wanted to know more but was too chicken to ask. They spoke a few more times like this until Penny started to get short in their conversations.


By the fifth conversation Penny lost her cool and asked him, "Why did you ask me if I was bored in our first conversation and seem to allude to sex and then turn out so polite in our talks?" She knew she had been played when he laughed in a sultry voice. " Why I was waiting for you my dear. I wanted you to be comfortable enough with me to discuss such things. Are you ready to truly discuss what you are longing for?"Penny was about to argue but she bit her tongue when she knew he was right. She simply said in a low voice" Yes."


"Then answer me this little girl, have you ever been tied up, leaned over a chair and had your butt soundly beat to the point your body dripped from pleasure and need?" Penny softly said, "No."


"Then you have not been with a real man. You have not had your needs met. I could hear the hunger in your voice on that dating site. Your words seem to speak the opposite of your voice. Would you like to explore your needs? Would you like your fantasies fulfilled? "Penny moaned and eagerly said, "Yes!"


From that point on their conversations became more carnal and graphic. Penny told him all her dark lustful dreams. She touched herself and cried out in their conversations. When she felt comfortable with him, she made arrangements for him to meet at her home that weekend.


She went to the mall to find he perfect outfit. She bought a white button up shirt and a short pleated skirt. She put the outfit on with a lacy thong. She tied the shirt at her waist but did not button it. She wore no bra either. She debated wearing thigh highs but decided to skip them. She curled her hair and put it in two pigtails at the base of her neck. She lined her beautiful eyes in a charcoal liner to make them stand out and wore bright red lip stick. She sat nervously on her couch waiting for him. She tried different poses and then gave up realizing she would have to answer the door. She knew by his description he was tall and would be handsome but she wondered if her would like her ample figure. She started to pace the floor until her door bell rang. She stopped mid-pace. Ran to her room and threw on a robe to answer the door.


What greeted her she would never have imagined. He was tall with salt and pepper hair and a trimmed beard. He had the most beautiful chocolate brown eyes and a kind smile. She just stood there gaping and he asked if he could come in. She shook her head and stepped out of his way. He sat down on her couch and patted the spot beside him. She sat down next to him and he chatted with her for a few minutes. She began to relax and leaned into the arm he threw over the back of her couch. He placed one finger on the inside of her robe and pulled it slightly out as if to look at what lay inside. He asked" What do we have here?"


Feeling foolish she stood, and slowly pulled the robe off to reveal he taught nipples showing through the white shirt and the very short skirt. He smiled and crooked a finger at her. She slowly walked toward him and her pulled her onto his lap straddling him. He looked at her hungrily and said, "God your gorgeous, why didn't you tell me how creamy your skin was and large your nipples were. He cupped her breasts in his hands and kissed each nipple through the fabric. Penny jumped up and said she had to go to the bathroom. She ran into the bathroom and leaned against the door to control her breathing. She wanted him badly but was she ready to give him the signal? They had decided if she wanted him she would hand him her panties. She took a deep breath, pulled them off and immediately plopped them in his hand before she chickened out.


He caressed her hand and smiled wickedly. "Oh baby girl I have a surprise for you. I want you to slowly remove your top in front of me, then walk into your bedroom, get on your bed with your back facing the edge, put your hands behind your back and spread your knees apart."Penelope slowly untied the know in her top and slipped it off her shoulders. She stood there for a minute to let him look her over. She then slowly walked into her room, climbed up on the bed and did as he asked. Her back was facing the door and she heard him come in. She heard a zipper open and something being pulled out of a bag. He purred, " I have brought a treat for you."


He pulled some ropes around just above her breasts and started to tie and intricate set of knots with the rope that both lifted her breasts and pinned her hands behind her back. Through the whole process he kept asking how she was doing even though she never used the safe word to stop. She never once felt fear, only overwhelming lust and hunger. She began to fidgit her legs and the cum slowly pulled just outside her pussy and dripped down her legs. She was soo turned on. Once he was done tieing the rope, he inspected his handy work and slowly undressed at the side of the bed for her viewing pleasure. As soon as his boxers came off she gasped. There stood the longest and girthiest cock she had ever seen. She had no freaking idea how she was going to take that. She looked at him in shock and fear with her mouth wide open. She knew he understood what the look had meant. She had told him about how tight she was and most of her partners had complained because it was so hard to fit in her. He smiled and calmly said, "It's ok baby girl, it will fit and you will enjoy it. When I am done with you, you will be so wet that I will just slide right into you."


Penny gulped but nodded in consent. He then stroked himself a few times and climbed onto the bed in front of her. He played with each breast, weighing it and lightly slapping them. He them pinched her nipples and she moaned. He grabbed them and pressed them together harder. She bucked slightly as the sensation of pain and pleasure shot through her very core. He squeezed one breast while making circles down her tummy and slightly biting her ear and neck. She bucked and tried to squirm to get his hand closer to her pussy. He only chuckled and he abruptly stopped and got off the bed. Penny cried in frustration and tried to follow him as he walked behind her. He squeezed both her breasts and leaned his cock into her back. He whispered in her ear, "Only naughty girls pout when they don't get their way. I am going to show you what happens to naughty girls who act this way."


He swung around and sat down on the bed. he grabbed her torso and pulled her over his lap so her stomach touched his thighs and her as was exposed from under her skirt. She felt the cool air caress her butt and pussy. One loud crack broke the silence as his hand firmly landed on her ass. She cried out in pleasure and pain. She tried to wriggle away but he held her firmly and spanked her two more times. Just as she was about to protest, his fingers gently rubbed her ass and then plunged into her wet pussy. She cried out in pleasure and began to moan ad he slowly pulled his fingers in and out of her. Just as she was about to cum, he pulled his fingers out and spanked her three more times. He kept doing this until Penny thought she would explode from want. She was so desperately horny she could do nothing but hump his lap trying to find release. He chuckled again and slightly spanked her. He asked, " Are you ready to be fucked?"


She nodded eagerly and he helped her stand since her hands were still bound. He kneeled him in front of her and said, " Then show daddy these sucking skills you have. Help me get hard so I can fuck you senseless." Penny eagerly took him deep in her throat and sucked as hard as she could. She barely ran her teeth across his dick and licked the head like she was caressing her lovers mouth. He moaned out and started to look impatient himself. He helped her stand and went to untie the ropes. Penny squeeked, "Nooo."


He stopped and tensed, "I am trying to undo your hands baby so you can relax them and then I was going to fuck you in the ways you said you wanted to be."She shook her head no. " I want you to fuck me while I am tied up. These ropes are turning me on and I don't want them undone. Please leave them on for now and fuck me hard." He smiled and pushed her down on the bed on her side. He lifted her leg and entered her hard as she had commanded. Penny felt like she was going to tear in two. The pain was overwhelming and she was o full but it the pain quickly faded into a frenzied lust. She bucked against him encouraging him to go harder. He fucked her faster until she screamed out in pleasure and went blind from the orgasm. He pumped in her slowly riding her orgasm. He then slowed to let her catch her breath. She begged him to untie her and he did. She then rolled him on his back and straddled him. She rubbed her pussy against his hard dick until he began to squirm with need and she could not take the build up anymore. She angled his cock head in her and slammed down on him. She grabbed the headboard and road him hard and fast. He began to moan as she started to have multiple orgasms in a row. They began to keep building until the final one made her scream out his name and he released his hot cum in her. She dropped to his chest and giggled. "You are fucking amazing."


He smiled and told her how amazing she was in whispers as he kissed her forehead and rubbed her back. They stayed in-twined in each other's arms. As Penelope began to doze off, she knew vanilla would never satisfy her again.

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