Aunt Penny "Baby-sits"

Story Info
A widowed aunt "babysits" her two nephews.
7.2k words
4.52
55.5k
64
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

Penny hurried around the house, straightening things and making sure everything was in order. She was off to the airport in a few minutes to pick up her sister, brother-in-law and her two nephews. It had been a long time since she had seen all four of them. Her sister was usually the only one to make the long trip from Florida; the boys hadn't visited her since they were 7 and 6 years old. Now they were - what - 19 and 18? They had grown up without her seeing them at all for over ten years, and now they were almost grown men. She was looking forward to seeing her sister again but was apprehensive about managing four visitors in her quiet house. More than that, she was very nervous about what she had agreed to - watching the two boys while her sister and brother-in-law went off to visit his family for four days. How was she supposed to entertain two older boys - no, young men - for four days?

Penny was just over forty but looked younger. She had kept the trim figure she had always had, with curves in the right places. She always thought her breasts were too large but had never had complaints. Her husband had certainly loved them until the day he died in a tragic auto accident. Now widowed for two years, Penny hadn't been able to start dating again yet, even though she missed the companionship and intimacy of marriage. She and her husband had a healthy sex life while he was alive; in fact, Penny thought she was just reaching her sexual peak in her late thirties, thoroughly enjoying sex. That ended abruptly with his death - ever since then her grief had overwhelmed any thoughts of sex.

Penny arrived early at the airport, making sure she was there to meet the family in case their flight was early. While she waited in the terminal, she noticed the stares of a number of men and wondered if she had dressed conservatively enough. Checking her watch, she darted into the ladies' room and looked at herself in the mirror. She realized that the short light summer dress she was wearing fit tightly around her curvy figure and the material was sheer enough to show the outline of the lingerie she wore underneath it. She was embarrassed but had no choice but to endure looks while she waited. She went back to the area outside the gates and sat in an isolated section of seats until the flight arrived.

When she saw her sister, she jumped up to meet the group. She kissed and hugged her sister Susan, did the same with Tom, her brother-in-law, and then walked over to greet her nephews. "Hi Nick, Tony," Penny said, extending her hand to shake theirs, "I'm your Aunt Penny - do you remember me?" The boys were definitely much larger than Penny remembered, especially Tony, who had grown to over six feet tall. Nick was shorter but thicker. Both were wearing jeans and tee shirts and looked very fit.

Tony ended up in the front seat of Penny's car on the ride home because of his long legs. Penny chatted with her sister while the boys and Tom were mostly quiet during the ride. Tony made her nervous for some strange reason, and that feeling only got worse when she looked over and found him staring at her long legs, her dress having ridden up as she drove. When they got to the house, Penny gave them a quick tour and the boys were particularly impressed by her pool. Penny led them up the stairs to show them their bedrooms and she could feel the boys' eyes watching her legs and full, round ass as she walked in front of them. Somehow she knew that they were trying to look up her short dress.

The next morning Penny woke early, determined to maintain as much of her routine as possible despite the visitors. She slipped out of her nightgown and into her favorite black two-piece swimsuit. She looked in the mirror as she arranged her long black hair - even though she was over forty she had a well-toned, firm body that most younger women would have envied. The black suit was a dramatic contrast to her fair skin. Cut high over her thighs it made her long legs look even longer. It even supported her best feature, her 38DD breasts, fairly well, although the skimpy top did little to hide them. But that normally wasn't a problem in the privacy of her own backyard. She enjoyed the feel of the cool water as she did her laps and felt awake and alive as she got out of the pool. As she dried herself she looked up and saw the curtains quickly close in one of the upstairs windows - someone had been watching her from above. Penny hurried inside to dress.

Later that morning she encouraged the two boys to take a swim, watching them through the dining room window. She reflected that she had expected them to be smaller, and she couldn't help but notice how tightly the suits fit on their young, trim bodies. Tony was very good-looking, tall and athletic. Nick might not have grown completely yet, but was still about 5 feet, 11 inches tall and stockier than Tony. Even from the window Penny could see that Tony enjoyed controlling his younger brother, and that he seemed to have a mean streak. Nick was quiet and withdrawn when Tony was around, while Tony was aggressive, especially when away from his parents. Penny had already felt Tony's eyes on her, almost undressing her when she walked by him.

As the next few days went by, and Tom and Susan's departure grew nearer, Tony became even more aggressive with the looks he gave Penny. He also seemed to seek opportunities to brush up against her or touch her. On Friday afternoon she was at the kitchen sink preparing snacks when he silently came up behind her and placed his hands on the countertop on each side of her, virtually locking her in place. "My parents are leaving tomorrow,' Tony whispered into her ear. "And I'm truly looking forward to being alone with you." He placed his hands on Penny's hips and pulled her back against his crotch, deliberately rubbing his hardened cock between her round ass cheeks. Penny was shocked by the contact and completely flustered. Should she say something to her sister? In the end she decided to handle it herself, confident in her ability to deal with what she considered a young boy.

The next day, she watched as her sister and Tom packed a rental car and drove off. Penny and the boys went back into the house and she turned to them. "I'm sure we can have a great time together if we all cooperate with the chores," she told the boys. "You're free to use the pool whenever you like, and we can go to the movies or mall while your parents are away." The two young men seemed to react positively to her little speech and Penny was encouraged. The evening was peaceful enough, and she had a nice chat with them at dinner. Penny still didn't trust Tony completely but had to admit that he seemed to be behaving himself.

It was late when Tony said "I'm going to make some hot chocolate for me and Nick. Can I make some for you too?" Penny appreciated the offer and happily accepted. They all sat in the family room sipping hot chocolate and watching television until the boys got up to go to bed. Minutes after the boys had left, Penny felt a bit light-headed and tired herself. Afraid that she would fall asleep on the couch, she decided to go up to her bedroom. When she stood, she felt dizzy and she stumbled on the stairs, wondering what was happening to her. In the bedroom she thought of the sleeping pills in her medicine cabinet and wondered about them, just before dropping down on her bed and passing out.

She fell into a deep restless sleep, filled with erotic images of past lovers and sexual encounters. Penny could feel her jeans being pulled over her hips by her dream lover and her nipples hardened in anticipation. Her blouse was unbuttoned and she felt strong hands massaging her breasts while he kissed her neck. Her lover's mouth trailed down her chest to suckle her breasts through her lacy bra. "Yes, suck my nipples," she murmured in her sleep. Her thighs opened invitingly as the kisses moved lower. It had been several years since Penny had last had sex and there was an ache in her neglected pussy. Her panties were pulled aside, enabling a finger to enter her wetness, and she felt her lover's tongue working its way through the dark thatch at her pussy. Her hips arched toward it, and even in her semi-conscious state she exploded in an orgasm as the tongue slid over her clit.

"Please take me now," Penny moaned. "I need you inside me!"

She felt her panties sliding down her long legs, instinctively spreading them to receive her lover's cock. Penny kissed the warm mouth pressing against hers as he entered her, gasping and begging, "More, I need more." Her hips pumped into her lover furiously, feeling his length moving in her with each stroke. As the haze of her sleep began to clear, she opened her eyes and was shocked to be staring into Tony's dark, lust-filled eyes.

"No, Tony," Penny protested, suddenly aware of what was actually happening but unable to stop him from hammering his stiff cock into her. Tony grinned at her and asked, "Who are you kidding Aunt Penny? You need a good fucking - you even said so - you begged me to fuck you." Penny couldn't deny what she had said, or the reaction of her body to Tony's movements. Even as she tried to clear her head, her hips were willingly returning each thrust from Tony. "Yes, like that," Penny urged him in her confusion, giving in to her arousal and raising her hips so he could penetrate more deeply. Tony knew she was beyond stopping, so he pulled out of her and brought her to a sitting position so he could remove her blouse and bra. Penny was as limp as a rag doll as he stripped her clothes off and laid her back on the bed, now naked.

Tony stared at his voluptuous aunt, thrilled at knowing he could do whatever he wanted with her. From the first moment he had seen her, he knew the first thing he wanted to do. "We're going to have a great time, Aunt Penny," he whispered as he straddled her chest, placing his rock-hard cock between her beautiful big tits. He took one in each hand and smothered his cock, pumping it back and forth, enjoying the sensation of her soft flesh on his cock. He pushed forward while pinching her nipples, bringing his cock head within inches of her red lips. "Open your mouth and suck my cock," he ordered. At this point Penny was aroused enough to do whatever he wanted. The cock disappeared between her breasts and then reappeared, just out of reach of her lips. "Don't tease me," she moaned. "Let me have it." Having never had a blowjob from a woman like his aunt, Tony was eager to give her what she asked for. He moved closer to her face and was astounded when she grabbed his ass and pulled him into her mouth. She worked on his shaft like a sex-starved slut, stroking whatever was outside her mouth with one hand and caressing his balls with the other. Tony was on the verge of cumming, but wanted his first load to be in her pussy. He quickly jumped off her and rolled Penny onto her stomach. Getting between her legs, he lifted her ass up to him and slammed his cock into her as hard and deep as he could. Penny let out a scream of pleasure and pain and fucked back at him. "Yes, Tony, take me," she gasped as her ass pushed back at him. Gripping her hips firmly, he pounded at her until he filled her with hot cum. The feel of his heat bathing her vagina triggered Penny's orgasm as well and she lost consciousness as she climaxed.

The next morning Penny awoke to find that she had overslept. She heard the boys outside in the pool and tried to remember everything that had happened the night before. Her headache and aching pussy confirmed that Tony had been in her room and done the things she remembered as if they happened in a dream. As she showered, Penny resolved to act as normally as possible until she had a chance to talk to Tony privately. She had to set things straight - make him understand that what he had done was terribly wrong.

The first chance came late in the afternoon when Nick was upstairs, playing a game on his phone. She walked into the family room where Tony was sitting, an arrogant grin on his face.

"Tony, I know what you did to me last night, and it was very wrong. If you promise to behave yourself, I won't tell your parents, but I will not tolerate it again!"

Tony was unfazed by this and quickly replied. "It's you that should be worried about me telling my parents."

This caught Penny off-guard. "You put something into my drink and basically raped me Tony!"

"You seemed to enjoy it," he snapped back. Just then they both heard Nick moving around upstairs. "We can't talk about this now, Nick might hear us," Penny said softly.

"Fine, I'll come to your room after he goes to sleep tonight and we can talk then," Tony answered, and walked out of the room.

The evening was quiet, with Tony seemingly on his best behavior and only occasionally making her feel uncomfortable with his glances. Penny had dressed in a sweatsuit to hide her figure, hoping to discourage Tony. As bedtime approached Penny's nervousness grew and she could feel her pulse increase. Her nipples hardened and her pussy moistened as she heard the boys prepare for bed and she cursed her body's reactions. Wanting to avoid the danger of meeting Tony in her bedroom, she decided she would wait for him in the family room. The boys had been in bed for almost an hour; Penny could feel her heart pounding with fear and excitement. She had drunk two glasses of wine hoping it would give her the courage to deal with Tony properly. She finally heard Tony's footsteps on the stairs; he saw her in the darkened family room and angrily said, "I thought I said we would meet in your bedroom."

Penny whispered her response, "I decided that wasn't a good idea. We can talk here just as well."

Tony grinned at her nervousness. "OK, if that makes you feel more comfortable." He sat next to her on the couch - a little too close in Penny's mind.

Unsure how to start, Penny hesitated, but Tony spoke first. "So, how long had it been since you last had sex, Aunt Penny?" he asked. "Because you sure were hot for it last night." Penny reacted furiously. "You need to stop talking to me like that," she insisted. "I'm going to have to call your parents back here if you don't treat me with respect."

"I don't think you're going to be doing that," Tony said with a grin. He pulled his phone out of his pocket and pressed a few buttons. Penny heard her own voice come out of the phone: "Yes, Tony, fuck me!"

"That doesn't sound much like rape to me," he leered at her. "It sounds more like an aunt seducing her nephew."

Shocked, Penny knew she was beaten. "What do you want from me?" she asked.

"For starters," Tony said with anticipation, "You can get out of that dumpy outfit you have on. A body like yours should be shown off, not hidden."

"Please, don't make me do that," Penny pleaded.

"Do it - now!" he ordered.

Penny didn't see where she had a choice, but she tried to bargain with him. "If I do this, will you promise not to touch me - that this will end?" His throbbing cock knew differently, but Tony lied to get her to cooperate. "Of course, Aunt Penny. I just want to see your body one more time."

Penny stood and stepped away from the couch. Tony fought to keep from jumping up and grabbing her as she pulled the baggy sweatshirt over her head, exposing a sheer, black lace bra filled by her generous breasts. "The sweatpants too," he encouraged her as Penny hesitated. Penny took off the pants and stood in front of Tony, knowing he was becoming more aroused by the second. His eyes were shifting from her breasts to the sheer panties and back again. "Turn around," he said hoarsely. "I want to see your ass."

Penny resented Tony's manipulation, but at the same time a submissive part of her was stirred by the obvious lust she created in him. The wine had made her more pliable and she was excited by the way he looked at her. Penny turned away from Tony and instinctively spread her legs. Her hands slid down to her waist, down her thighs and all the way to her ankles, knowing the pose would expose her ass and pussy to him through the sheer panties. Tony marveled at the display and Penny's reluctant cooperation.

"You're getting into this, aren't you Aunt Penny? Do you like showing yourself to me?"

Without answering, Penny straightened and turned to face him. "Take off the bra so I can see those beautiful tits," he told her. Penny silently reached behind her back to unclasp her bra. Without a word, she slid the straps off her shoulders and slowly let it fall to the floor, leaving her breasts fully exposed to him. Her arousal at being dominated like this surprised her "Yes, Tony," she admitted softly. "You make me feel very sexy."

Tony saw that she was aroused, so he unbuckled his belt and opened his jeans, reaching in to pull out his engorged cock. In a hoarse voice he said, "Come over here and show me how sexy you feel." Almost trancelike, Penny dropped to her knees and moved to his cock, licking the shaft from the base to the tip. Tony's hands went to her breasts, his palms brushing over her sensitive nipples. Penny took his shaft into her mouth and both of them gasped as Tony squeezed her breasts in response. As much as he enjoyed the feel of her beautiful tits, Tony wanted to touch her in other places as well. "Kneel up here on the couch and suck me," he told her. Penny moved quickly to comply, guessing what he had in mind. Her mouth returned to his cock as his hand slid under her, rubbing her now-wet panties against her opening. She squirmed at his touch but wanted more. "Touch me," she moaned around his cock. Tony pushed her panties to one side and began lightly teasing her inflamed cunt. His fingers grazed her exposed clit, and Penny spread her legs wider, offering herself to him.

Tony penetrated her tight pussy and almost immediately Penny's gasps told him she was coming. He stroked her through the climax and started her toward another. "I need you to fuck me now," Penny said breathlessly as she sat up. She climbed off the couch, pulled his jeans off, and straddled him. He marveled at the change in her as she reached down and gripped his cock, guiding it to her sopping cunt. "Fuck me Tony - fuck me with that lovely cock," she begged. Penny gasped as he lifted into her and she rode him hard while Tony bucked his cock into her, her mouth fastened to his, her breasts in his hands. She had a string of orgasms as he fucked her and pinched her ultra-sensitive nipples. Then she heard his breathing quicken; Penny pumped him even faster, wanting to make him cum. She felt the hot gush of his orgasm inside her as he groaned into her breast, climaxing.

Penny waited until Tony's cock began to soften and gingerly climbed off him. She reached down and ran her hand over his cock, pleased with the satisfied smile on his face and knowing that it would soon be hard for her again. Leaning over, she purred into his ear, "Why don't you come upstairs and fuck your Aunt Penny some more?"

Tony watched as the naked raven-haired beauty that was his aunt walked away from him, intentionally rolling her hips to tease him. He spent the night in her bed, fucking her pussy in every position imaginable. Penny finally pleaded that she was too sore to continue and resorted to a blowjob to cap the evening. Tony was thrilled at finally getting to cum into her mouth, his cock sliding between her lips as she sucked the cum out of him. Just before he finished he pulled out and shot the final bursts of cum on his aunt's beautiful face, fulfilling another of his fantasies. What shocked him was her reaction.

"Yes! Cum on my face! I love it Tony...mark me!"

As daylight broke, Tony woke and reluctantly dressed to return to his own room. Penny rolled over to watch and asked, "Are you coming back tonight?"

"You couldn't keep me away," Tony responded as he leaned over and kissed her. "But tonight, why don't you wear something sexy for me, like I see in catalogues or skin magazines? Something with nylons and a garter belt - I'd really like that. And if you shave your pussy I can eat you better."

12