When she had finally caught her breath she said, "You seem pretty pleased with yourself." - "Oh I am. That was cool beyond anything I've ever read about or seen online." He replied with a huge grin on his face. She looked down at his lap and noticed a hard dick looking back at her. "I suppose I should return the favor. What would you like to try next?" Dennis looked down towards her crouch a moment and then back into her eyes. She smiled and thought, 'sore or not, he's earned it'. "Come here." She said raising her arms towards him. Dennis slowly began to crawl between her legs again.
***WARNING*** This chapter is a bit long at 8 typed pages. But I hope you enjoy it!
Saturday (Day 2)
Cindy watched her young lover climb between her legs and try to position his dick at the entrance of her pussy. He was being careful because while learning about fingering a woman she told him how painful it could be if he entered her dry. After rubbing around at her entrance for moment to get it wet, he slowly pushed the head inside her just a bit. When he looked up at her Cindy nodded and said, "Just go easy at first Dennis. I know I'm very wet, but I'm still a little sore from the last twelve hours of fun that we've had."
"Yes ma'am." He replied. Cindy watched him as he pushed his dick into a bit more. When a small gasp escaped her lips he paused, looking at her with surprise and concern. 'He is such a sweet boy,' she thought. "It's OK Dennis, you're doing fine. Please continue." She said. Dennis pushed his dick into her a little more, but once again hesitated when another small gasp escaped her. Cindy took a deep breath and nodded to him that it was OK. As Dennis pushed himself into Cindy bit her lower lip. She really wanted to reward him and didn't want to put him off simply because she was a little sore. She knew she'd pay for it later, but this young man deserved a little compensation for how much satisfaction he'd given her this morning. She knew, at least, it wouldn't be as bad as that stunt her ex-husband pulled one Friday night - even though she had ended up enjoying it, she could barely walk the following Monday.
Dennis was finally completely inside her and she could see by his breathing that he was eager to start. Cindy smiled at her young lover and enjoyed the feeling of him deep inside her. Dennis smiled back, but his eagerness to begin was plainly evident. Dennis was supporting his upper body on his extended arms with his hands placed on the floor on either side of her chest. This gave Cindy a clear view down between their bodies to where their groins met. After glancing down at where his pubic hair met her smoothy shaven mound she looked up at him and simply nodded.
Cindy watched him as he slowly pulled back a little and then carefully pushed back into her. Again he slowly pulled back just a little before slowly pushing back into. Cindy smiled to herself as she thought of how sensitive this young man was being. He was eager to please her, as evidenced by his earlier performance, but he was currently just as eager to find release for himself. And he was being particularly gentle as she had mentioned she was a bit sore. She looked down again and watched as his dick came into view and then disappeared again inside of her. It was a stimulating sight and she felt a tingle inside her as she watched. Looking up she found he was now looking down between them and obviously enjoying the view himself as he started to pull out a little further with each stroke. He was still being gentle each time he pushed back into her and she couldn't help wonder if he could come this way. After all, he had already shot his wad at least three times last night and once this morning. As she was mulling this over her thoughts were suddenly interrupted.
"DING DONG!" Dennis froze. Cindy looked up at him and then cocked her head as if to hear better. "DING DONG!"
Cindy suddenly gave Dennis a suspicious look and in very serious tone she asked, "Dennis, are you expecting anyone? Another of Bobby's friends, perhaps?"
Dennis went from a look of surprise at hearing the doorbell to one of shock. Cindy wasn't sure if his look was from being caught or at her accusation, but she was going to find out. "DING DONG!"
"Dennis you need to let me up, now." She said. Quickly Dennis pulled out of her and sat back. Cindy stood and stalked out of the den, down the hall and to the front door. 'If another of Bobby's friends is at the door then I'm going to be seriously pissed.' She thought. 'Maybe a little shock and awe was in order here.'
Flinging the door open she stood there for a second, before her face lost all color. At the curb was a delivery van and standing right in front of her, with a curious look on his face, was the delivery man himself. "Oh shit," She said as she quickly shut the door and just stood there a moment. When she'd recovered enough to fully realize what had just happened she opened the door just a crack and said, "I'll be right back," and shut the down again. She leaned against the wall next to the door for a long moment to collect her thoughts, before racing upstairs to get her bathrobe. Once back at the door she paused for moment, remembering to hold her robe close, before opening it. Still standing there was the delivery man with a bouquet of flowers in one hand and a digital clipboard in the other.
"I'm very, very sorry about that. It's just that I was in the middle of…something, and I thought you were someone else." Cindy couldn't help blushing as she said this.
As the delivery man handed her the digital clipboard for her signature he said, "It's quite alright, you'd be surprise how often it happens."
"So I'm not your first?" Cindy replied trying not to sound embarrassed as she felt. She handed the digital clipboard back to him.
Chuckling, he said. "No, I'm afraid you're not. But if I may be so bold, you are by far the best." Cindy smiled at him and said, "That is one of the best compliments I've had in a long time, thank you." Looking up and down the street she quickly opened her robe and flashed him, before closing it again.
"Yep, easily the best…by a long shot." He said as he watched a blush come back to her face. "And Miss, I don't know who sent those to you, but I sure hope they send you some more, real soon." Tipping his hat to her, he turned and walked back to his van.
Cindy looked up and down the two rows of houses to ensure no one had seen her before closing the door. She admired the lovely bouquet before looking at the card.
"Mom, I hope you have a great time with the house all to yourself while I'm gone. Love you, Bobby"
Cindy smiled a very warm smile. In the last twenty-four hours she'd had the best sex in several years, got one hell of an adrenalin rush flashing a delivery man, and had received flowers from her darling son. Life was good. She walked into the kitchen and placed the flowers in a vase with some water. And with a smile on her face she headed back to the den. On her way she remembered practically accusing Dennis of foul play and felt a jolt of guilt hit her.
Walking into the den she saw Dennis still sitting where she'd left him. She couldn't quite read his expression, but anxious came to mind. And what ever he was thinking didn't seem to affect what he was feeling, because he still had a pretty serious hard-on going. Of course she hadn't bothered to close her robe since placing Bobby's flowers in water, so she was only adding to the affect. Walking over she knelt down in front of him.
"Well, as it turns out that was not one of Bobby's other friends, which is a good thing for you mister." She said in a mock serious tone. "But I do owe you an apology for thinking you might be up to something when the doorbell rang, so how can I make it up to you?" She asked in as sexy a voice as could. She sat back on her heels, with her hands on the floor for support as she leaned back and thrust out her chest.
"Um, well I was wonder if we could try something new? Something we haven't tried yet?" He asked as he looked at her body being openly displayed before him.
"Something new it is then. Please kneel right here." She indicated a spot on the edge of the blanket. She watched as he got to his knees and move to where she had pointed. Once he was there Cindy got down on all fours in front of him and took his dick into her mouth. As she started sucking she felt him pull her robe off to one side, 'I guess he wants to look at my naked ass while I suck his dick.' She thought, feeling suddenly naughty.
Cindy pushed her mouth onto his dick a little at a time until soon she had the whole thing in her mouth and held it there a moment. She felt his body tremble slightly as the head of his dick touched the back of her mouth. Slowly she pulled her mouth back until the head of his dick was between her lips. She sucked and licked it a moment before sliding her lips down its length it hit the back of her throat again. Pretty soon she had a good rhythm going and she felt him place his hands gently on the back on her head.
After several minutes of her pushing her mouth onto her his dick she felt his hips slowly start to pump forward into her motion. As he started rocking his hips forward and back she stopped moving completely and allowed him to 'fuck' her mouth. Forward and back he pushed into her mouth before pulling back again. And just before his dick left her mouth he'd push forward again. Now he had a good rhythm going and Cindy just held still while he fucked her face. But it didn't take long before she was starting to get excited again. 'Time for something new,' she thought.
Cindy suddenly pulled her head back and off his dick. Dennis stopped rocking and just looked down at her. "Stay right where you are." She said as she got up on her knees. She quickly removed her bathrobe, turned and got back down on all fours again, this time facing away from him. Glancing to the side she noticed their reflection on the TV screen. There she was naked on all fours, 'like a bitch in heat' she thought, with Dennis kneeling naked behind her. His hard-on was standing almost straight up and his expression exquisite. Wonder, awe, and delight played across his face as he stared down at her naked, vulnerable ass. ‘I’m his for the taking now,’ she thought.
Cindy watched in utter fascination as Dennis surveyed her naked body, but kept returning his gaze to her ass. She decided to up the ante a bit to see what he'd do. Reaching forward, she grabbed the pillow in front of her and pulled it to her. Then she slowly, seductively lowered her head until the side of her face was on the pillow and her breasts were on the blanket. From this position she had an excellent view of the whole scene.
Cindy watched as Dennis finally snapped out of his daze, moved forward and gazed down at her vulnerable body. He placed both hands on her ass cheeks and began to slowly caress them. Grabbing her hips on either side he gently pulled her the last few inches to his waiting dick. When he finally made contact with her the head of his touched the spot between her pussy and ass hole. She froze as he held them together just like that.
A sudden jolt of adrenalin shot through her as she felt him press his dick a little harder against her in this position. She saw him looking straight down as if he were trying to make up his mind. She was so excited at watching the scene that she hadn’t fully considered what options lay before him. And in this position his options were becoming only too obvious.
Suddenly he let go with one hand and grabbed his dick. Then he moved his other hand between the top of her ass and the small of her back. He began rubbing the head of his dick between her wet pussy lips. She watched him smile at the sudden gasp this caused her. He slowly rubbed his dick up and down the length of her slit, at one point rubbing it over her clit, and then all the way up until it almost touched her asshole. And then back down again until he reached her clit. She gasped again when he rubbed over her sensitive clit. Then back up again, parting her pussy lips until he slid past them and barely touched her ass hole. She held her breath until he began to slide his dick back down her slit. Several more times he repeated this pattern, each time lingering a little longer at the entrance to her ass before sliding his dick back down.
After a several more times of this she figured out by the expressions on his face that he realized the affect this was having on her. His grin got wider every time he brushed his dick over her clit or ass hole. Her breathing had begun to deepen again in anticipation of what was to come. She watched as he looked up from her ass and towards her head and got a big shit eating grin on his face. Suddenly, without warning he shoved his dick into her in one smooth motion.
Cindy cried out as his dick thrust deep into her eager pussy. Pressing down on her lower back he held her in place as he pushed himself fully inside her in one, slow stroke. He then placed both hands on her hips and held her tightly against him. She was so turned on that her breath had deepened further and he hadn’t even moved yet. Maybe it was because he had already caused her some much pleasure that her body was tingling with excited. Or maybe because of the forceful way he had held her as he entered her from behind. Either way her body was responding to this eager young man. As shiver moved through her Dennis pulled back slowly, before thrusting back into her. Then he pulled slowly back again, and again thrust back inside her. As he continued this pattern Cindy began to breath even deeper, and with a little more force. His pace was steady but she knew the passion was building within her.
Memories of passion from her past came to mind. The last time she had come this much in such a short time was the weekend her ex-husband had brought some buddies home after a night on the town. As she started to remember the events of that weekend her whole body began to tremble.
Her breath was now coming in deep gasps, her body continued to tremble and Dennis began to fuck her with harder strokes. She felt herself begin to push back against him as her body began to shake from her need to climax. He picked up his pace in response to her movements and started really driving his dick into her hard. Suddenly she lost it as her body began shaking with the passion coursing through her. Again and again the waves of pleasure hit as she shook in response. After a few moments her slumped down further into the pillow and relaxed. Dennis slowed his pace, but he didn’t stop fucking her. With his hands holding firmly onto her hips he continued to drive himself into her.
Cindy hadn’t realized she had closed her eyes until she opened them again. In the TV’s reflection she saw Dennis taking his thumb out of his mouth and bringing it down to her ass. Suddenly she pushed herself off the pillow onto all fours again began pushing her ass back against him as his wet thumb began rubbing her overly sensitive ass hole. Again and again she thrust backwards onto his dick as he kept rubbing her tender ass hole. Dennis thrusting into her, her thrusting back against him, his thumb rubbing her sensitive ass hole, and her watching the whole scene through the reflection on the TV screen was finally too much. She started gasping out a moan of passion and another orgasm struck her. Once again her body was hit wave after wave of passion. She shook, grunted, moaned and practically threw herself back against his thrusting hips. Once again she collapsed back onto her pillow from pure pleasure. She realized he had stopped moving as her mind began to drift on a euphoric cloud.
She realized he was still deep within her when he moved as if he was leaning over her. The feeling of his hard dick adjusting its position within her caused another shudder to course through her body. As she looked at the reflection in the TV it looked like he had reached for something on her other side. Turning her head on the pillow all she saw was her robe lying next to her and the couch a little further away. He couldn’t have reached the couch and she could not imagine why he would have reached for her bathrobe. She turned back to the reflection as Dennis had just straightened up. With one hand on one of her hips he placed his thumb back on her ass hole and began to rub.
Cindy’s whole body stiffened as his thumb continued to rub against her ass hole. Her breathing once again grew deep, quick and loud. Suddenly she was on all fours again thrusting back onto his hard dick. As she continued thrusting back she felt his thumb start to press itself into her ass. A momentary jolt of panic struck her as she felt her puckered anus began to stretch and a slight, yet sharp pain hit her. But as she felt his hard dick stroking deep inside her pussy the mix of pleasure and pain gave way to acceptance. She thrust even harder against him as his thumb pressed further into her. She began to cry out in passion as he began to thrust his hips forward in time with his thumb in her ass and matching her own thrusts. Again and again he pushed both his dick and thumb into her until both were buried deep within her with each thrust. Cindy’s backwards thrusts started to falter as her whole body began to shake and convulse in passion again. She was reaching the point of exhaustion, but she didn’t want him to stop. The slight pain for his anal intrusion had transformed into stimulation that now fueled her passion. She continued to thrust backwards against him until her body stopped shaking and her orgasm ebbed completely. And once again she collapsed onto the pillow.
Cindy woke to Dennis moving his thumb within her ass. His dick was still hard, and still deep inside her, but it was only his thumb moving in her now. She gently started moving her hips back and forth on his dick without rising to all fours again. It was not forceful like before, but it still felt pleasant. It was still tight, but it didn’t hurt. In fact it felt good. She had forgotten that butt sex could feel good if the man took his time, and Dennis was being both gently and unhurried.
As her started enjoying the feeling his thumb ‘fucking’ her ass, she reached back between her legs and began to rub her clit. As she began rubbing her breath picked up a little. She was taking her time as she wanted to let it build up before she pushed herself over the edge yet again. Dennis hadn’t started fucking her pussy again, but he was rock hard and still inside her. As the feeling in her ass started feeling even better she began to rub her clit even harder. Her breath was starting to speed up and was coming she long shuddering gasps again.
Suddenly he pulled his dick out of her pussy. She looked back at their reflection and saw him push the head of his dick back towards her, just before she felt it touch her labia again. She then watched, and felt as he slowly pushed it back inside of her, the whole time still ‘fucking’ her ass with his thumb. She watched as he pulled out of her again, only to push back into her. The hand on her pussy slowed as she waited for him to begin fucking with more speed and force, like he did earlier. After few more times he pulled out of her and she watched as he picked something up beside them. She couldn’t tell what it was, but after he passed it over his dick a couple of times he put it back down and began to slowly stroke his dick. He stopped working his thumb in and out of her ass. With his thumb still as deep in her ass as it could reach, he spread the remaining fingers of that hand over her ass cheek. He then placed his other hand over the opposite hip, and with both hands gently pushed her hips lower to the blanket. When she was positioned where he wanted her he began to pull and push his thumb out and back into her ass very slowly.
Cindy was captivated by the sight, but was still rubbing her clit slowly. He began to pull his thumb out until only the tip was still pressed against her puckered hole, before pushing it gently back in. As he began to finger-fuck her ass again she began to pick up the pace on her clit. As he continued to pull his thumb completely out, before pushing it back inside her, he adjusted his knees to the point of pressing her legs just a little further apart. Then he took his free hand and grabbed his dick and she lost sight if its head as he positioned it between her ass cheeks. Mesmerized by what she was watching she suddenly realized what he was doing as replaced his thumb with the head of his dick and slowly pushed it into her ass.
Cindy was back up on all fours as she felt his dick enter her ass hole. She held her breath as she felt it stretch to the point of pain, but the tightness relaxed slightly when she realized that he wasn’t about to just shove it into her. Her whole body shook as her arms, back and legs locked up for a second before she forced herself to relax. She quickly turned her head and saw that he was watching her and obviously waiting. As she again willed her ass muscles to relax she saw his head turn and look at her through the reflection on the TV screen. As their eyes locked she realized he was waiting for her. When she finally got over her initial fear she felt her body begin to relax. Slowly, she nodded her head ever so slightly to him. Grabbing both of her hips he gently pushed forward. Her sudden intake of breath caused him to pause as they continued to look at each other through the reflection. As she felt her body begin to relax a little more she nodded again. With a firm grip on her hips her pushed a little more before pausing to let her body relax again.
She was now at a point where she couldn’t move. As patient and gentle as he was being, and as much as she wanted to return the pleasure he had given her, she couldn’t bring herself to nod again. She knew he wasn’t half-way in her yet and fear gripped her body. She put her head down to fight back the tears of frustration. Part of her wanted him to continue, but another part screamed for him to stop. As she knelt there on all fours she felt his body shift and tightened up fearing the worst. But then she felt one of his hands reach underneath her and slide over her stomach to her crouch. Then she felt his fingers gently fumble around her pussy lips until her located and began to rub her clit. A shuddering gasp escaped her lips as he began to stimulate her pussy even more. She felt her breath deepen as she started to feel her body respond. As the feelings got stronger she had the overwhelming desire to push back onto his hard dick. Suddenly she did.
Her back and arms tightened at the slight pain, but she forced herself not to pull away. As his fingers continued to rub her overly sensitive clit she pushed back a little more. Again she felt pain, but this seemed it only fueled her desire. As a wave a pleasure shot through her body she steeled herself and pushed back again. Her whole body locked up as she slid the rest of the way onto his dick. The sting of pain she felt was overridden by the jolt of pleasure that shot from her tail bone up her back and caused her shoulders to shake. When she finally got control of her muscles she breathing was coming in deep, hard gasps. As his fingers began to press harder on her clit she began to rock back and forth on his dick. Suddenly her whole body began to shake a huge wave of passion hit her and washed over her entire body, to be quickly followed by another, and another. It seemed to go on for several minutes before she collapsed back onto the pillow. She pussy went through several smaller spasms before she laid still again, his dick still hard within her. After a moment she realized he had stopped rubbing her clit, but was holding onto her hips. When she finally caught her breath she looked back at him in the reflection. When she saw him looking back at her she nodded.
Then Cindy watched Dennis began his conquest of her last hole. She watched as he slowly pulled back a little before pushing back into her, but with each stroke he pulled out a little further. Soon he was pulling back to the point where only the head of his dick was left within her ass, but before pushing back in again. As Cindy watched she saw his face begin to change expressions and she heard his breathing deepen and become forceful. Suddenly she reached between her legs and began to rub her clit again. And as his breath grew louder she rubbed even harder. Before she even realized it her body was shaking with the orgasm coursing through it. She gasped and groaned and shook all over as it crashed through her. Her arms gave out and she dropped to the pillow, but before her body could come down from its high she felt him start thrust harder into her and realized he was coming within her ass. She was once again the first woman to give him yet a new pleasure, and that thought set off another wave of passion within her as another, albeit smaller, orgasm shook through her body. She finally collapsed from pure exhaustion as she felt him shove himself into her ass just a few more strokes before he too collapsed on top of her.
As she lay there she couldn’t believe how satisfied she felt. His body, hot from exertion, lay onto of her with his chest pressed against her back and her chest pressed against the blanket. His dick was beginning to softening, but was still inside her ass. His hot breath and caressing her neck as he began to place soft kisses on her hot skin. In just over half a day she had fucked him, sucked him, taught him to finger-bang and eat pussy, and taken him up her ass all for the first time, his first time. She had taken his virginity every way she could think of, and they still had the evening to look forward to. ‘It was going to be a great summer,’ she thought again!