Jimmy and Winnie Pt. 02

Jimmy walked down for breakfast that morning, feeling that all eyes were on him and that everybody knew his secret. He sat down with his Father just as Winnie served them all breakfast. She sat down at the other end of the table with her meal. The Father always insisted that she ate meals with them at the table.

"So Jimmy," his father started speaking, "Winnie told me that you started running."

"Yes sir." Jimmy replied in a small voice. Not comfortable with the lie, certain that very soon he will be exposed.

"Did you enjoy it?"

"No, not really," Jimmy answered as he imagined he would feel had he really been running that morning, instead of getting a mind blowing head job from Winnie.

"I thought you told me you enjoyed it," Winnie uncharacteristically cut into the conversation, greatly enjoying the double meaning here comment implied. They both turned and looked at Winnie. It's not that she would not get involved in the conversation around the table, but it was usually about the daily schedule, or arrangements for dinner or shopping, not matter of parental discussions.

"Well I went just this once. This morning. Just to see what it's like." Jimmy stammered, not sure if Winnie was going to expose him in front of his Father, but her face did not display anything other than genuine interest in his run.

The Father turned back to Jimmy. "Well? Did you like it?"

Jimmy looked from Father to Winnie and back to his Father. "Yes, it was a bit scary at first, but in the end it was great." Jimmy decided to carry on with the double meaning and at the same time not having to have to lie to his Father.

"Scary?" his Father was a little perplexed but returned to his breakfast as Jimmy and Winnie exchanged knowing looks across the table.

"I had a friend at school," Winnie, unusually talkative this morning, continued her comments. "He trained for running. Every morning he would go for a run and every evening. But he had to asks permission if he could go. Every time he had to ask permission."

"That's a good point Winnie. I did not know where you were this morning. If it wasn't for Winnie telling me about your run I would have been concerned for you. Start a search. Maybe even call the police."

"Yes sir. Sorry sir. I will certainly ask next time." Jimmy took on that piece of information. Was he really invited to come back to her bedroom? When will he have to ask?

The rest of the day was the longest Jimmy ever experienced. Even at dinner time, when he was watching Winnie serve them dinner and then clean up afterwards, his memory of her kneeling in front of him kept distracting him from the conversation his Father was trying to have with him. He left for his bedroom soon after dinner, pretending to be tired. He was listening for Winnie to come up to her bedroom but it was almost ten when he finally heard her walking up the stairs and into her bedroom. As soon as the door closed, he opened his and made the few steps across to her door. He gently knocked. There was silence for some time and he was considering knocking again or retreating back to his room. Then he heard the gentle, "Come in." With blood rushing to his temples, he carefully opened the bedroom door and stepped in.

Winnie was sitting on her bed. Lot of the bravado and the confidence she displayed in front of his Father seemed to have evaporated. She looked as scared and as nervous as Jimmy felt.

"So there are some rules here," she started, her voice strict, but nowhere near as loud, or confident as it was this morning.

"First is the permission. You ask me. I ask you. We do not take each other for granted. You can not just walk in here whenever you feel like it. I keep house for your father. I am not your fuckbuddy! Understood!" The word burned Jimmy's ears as he almost recoiled at the vulgarity of her words. He quickly nodded his head in agreement. Frozen in space in the middle of her bedroom. Afraid to move forward or back.

"Next," she continued with the same commanding voice that was both scary and exciting to hear.

"Private matters between two consenting adults are just that. Private. I don't want to hear about this from anybody else. Not you friends, not your church and especially not your Father." Again Jimmy's head started to nod in agreement even before Winnie finished speaking.

"Ok," she continued a little more gently now.

"Finally, you need to learn to be cool. If you need to lie to your Father, lie to him. I will support your 'running' story, but you need to be a little more convincing. Always have a story ready for your Father. Always think of something safe to say about where you were and what you were doing. Maybe start running for real. At least a few times. That will be the best cover. But make sure you keep your cool. He is no fool and will be able to put two and two together very quickly. Especially if he suspects something."

The silence following her lecture hung in the air, Jimmy unsure of what to do next continued standing in the middle of her bedroom. What could he get away with? Could he touch her? He was not sure, but he felt he should do something.

He took an awkward step towards her then stopped. This time, she took the initiative and responded. She stood up and quickly closed the distance between them. They kissed. Gently. On the mouth. Just with the lips. Her sexual confidence of this morning hiding.

Winnie spend the entire day deciding if she should go through with her plan. There were many things that she knew could go wrong here and all of them were catastrophic for her job, for her life and for her future, but none of those were foremost in her mind. Her primary concern and the key decision she was mulling over in her head was letting him see her naked.

All her sexual liaisons of the past were in the dark, or at least in very low light. Both parties wanting the freedom to indulge in their own private fantasy of what their partner could look like behind the anonymity of the dark, but this was different. She wanted to see Jimmy. See him make love to her. He was very handsome. Maybe not in the traditional sense, but to her he was very handsome. She also realised that she would need to show her body to him. This was the point that frightened her the most. On one hand she wanted to show her body to him. He seemed genuinely interested in seeing her naked this morning. Even the sight of her in her pyjamas made him aroused. Even in her pyjamas! Will he be equally excited when she shows him the real her. Her naked self. To see all her deformities. Her crooked pelvis, her blotchy skin and birthmarks and awkwardly shaped, drooping breasts and...

She was not sure, but she wanted to find out. She needed to find out. But she was also terrified. What if he does not find her attractive? That fear was eating away at her confidence. It was making her doubt her decision now.

"Can I ask for one more request," her voice different now. No longer demanding. Now the fear and uncertainty she felt was clearly showing, but Jimmy did not notice. He again started nodding in agreement even before she made her request. She smiled at his easy compliance but placed a finger on his lips to calm him. To stop him. To make him wait for her to state her request.

"Just this time, will you promise to keep your pants on? Just today. Just this one time. Please just keep your pants on." Jimmy was looking into her eyes as he was getting ready to nod his head in agreement, but then his mind realised what she just asked and his heart sank. Not because he realised that he will not be able to stick his cock inside her. He still remembered the mind blowing head job that Winnie performed on him this morning and that memory kept him exhilarated still. That was not the root of his disappointment. Somehow he connected her request with her keeping her pants on as well and that idea disappointed him. Still, he nodded his acceptance of her condition. She did say that it was just this one time, and hopefully there will be a next time. So this time he will at least get to see her naked breasts. She saw him nod to accept her condition and the relief on her face was obvious even to Jimmy.

Winnie wanted to ask Jimmy for one more favour, but was afraid to. This close to the end, her courage deserted her and she wanted to ask him to turn out the lights, but she saw Jimmy's face when she asked him to keep his pants on and now she was afraid that she would push him too far. That she might make him walk out of her bedroom rather than carrying on with her crazy demands. And she really wanted him. Wanted him to stay and wanted him to pleasure her.

She reached up and started unbuttoning her shirt, but after the second button, as the immense cleavage and her sizable breasts tightly packed in the constraints of her sensible bra came into view, she stopped. Some of the mischief returned to her eye as she leaned in a little and whispered, "Would you rather undress me yourself?"

Jimmy's hand shook as he nervously reade out and started unbuttoning her shirt and the rest of her buttons.

"Now pull the shirt out of my pants," Winnie suggested as he blindly followed her instructions. She was aware that her birth marks and her patchy brown skin will also become visible and she was carefully monitoring his face for any signs of disgust or repulsion, but instead his eyes opened up to take in the view of her breasts, tightly packed in her sensible and protective bra. His eye riveted at the lumps her large nipples were making in the material of the bra cups.

"Now my pants," she suggested as she saw his face light up as he eagerly reached for the buttons of her jeans and instead touched the skin of her waist.Moving his hand away, he smiled awkwardly, afraid that touching her skin too early might spoil his success with her, but instead she reached down and unbuttoned her jeans.

"Maybe take my shoes off first," she again suggested as she sat down on the edge of her bed and Jimmy now knelt in front of her. She wore sneakers in the house to make it easier to go in and out of the house. Now Jimmy pulled on the bow of her shoelaces and tried to pull her shoes off. It was too tight and he started to loosen the individual loops. Now the first shoe slipped off, soon followed by the other. He looked up and saw her watching him kneeling in front of her. His face was met with the bra encased breasts and the two nipples protruding even more than before through the bra material.

"Socks?" she again suggested and he complied. Her naked feet. She saw them as knobbly and not very pretty, but to him, they presented another part of her exposed skin and a new source of his arousal. He suddenly realised how difficult it will be for him to keep his pants on tonight. The pressure and the strain in his pants becoming uncomfortable. They both stood up. She unzipped her pants and started to wiggled her ass out of them. He adjusted his hard cock starting to show a bulge in his pants. Half way down her ass, she invited Jimmy to try to pull down her jeans. Reaching out, he placed his hand on her hips and hooking his thumbs around the waist of the jeans, he pulled down. First gently, but that was not enough to clear her hips. She tried to help him a little by wiggling her bottom. He then tried again, much harder and this time the jeans yielded, but he also hooked in her underwear that now descended halfway down her thighs as the jeans now dropped down to the floor. Jimmy froze. Did he go too far. Did he overstep the boundary. No. Winny just laughed it off.

"Wow, you are eager," she commented, glad that the awkward moment of waiting to expose her pussy to him was over.

"Sorry," he apologies, but was mesmerised by the thick mat of dark curly hair that covered the main target of his desires. At least he managed to remove her pants and she did not stop him.

Now the view changed. No longer were the pubic hair on display. In front of his eyes bobbed the two lobes of her bottom. Not that Jimmy had much to compare them to, but he was certain that by far, her bottom was the best he ever witnessed and the thought of kissing it made him realise that the ass kissing phrase may not always has such negative connotations he always thought.

"Could you do my bra as well," she again suggested looking down at Jimmy kneeling behind her, admiring her ass. She kicked off her jeans and panties as he stood up and clumsily unhooked the four metal hooks of her supportive bra. . She leaned a little forward a little to release her breasts from their daily confinement and to let the bra fall down. She then quickly climbed up on her bed and turning around she sat down high up on the bed, her back leaning against her pillow and the wall behind her. Sitting a little stiff, but stark naked, she was nervously showing her body to him in the full light of her room.

"What do you think?" She could not stop herself. She needed to know what he thought of her. What he thought of her body, but Jimmy was not able to speak. His eye attached themselves to her breasts. They were large and drooping down. Her dark areolas and the large fat nipples that proudly projected from her breasts were now pointing down and out. If Jimmy had the presence of mind, he would observe that they were slightly different in size. That one of the nipples pointed more out than the other. That the skin was not uniform but a little blotchy and the stretch marks on the sides a testimony to the rapid growth of the breasts during her teenage maturing period. But Jimmy did not notice any of it. All he saw were the breasts, the nipples and the giant desire for him to kiss them, to lick them and to suck them.

"Would you like to kiss me?" she asked, this time a little uncertain, comfortable with the thought that he was still extremely aroused by her body and was not disturbed or disgusted by any of the obvious physical flaws that always controlled her life.

Jimmy stepped forward, but instead of kissing her mouth, he leaned over. Unable to resist, he kissed her breasts. Her nipples. Then, ever so gently, he lifted one of the breasts to his lips and took her nipple into his mouth. His lips felt on fire as he gently sucked on it and rolled it between his lips. For the first time tonight, Winny felt she was losing control of the situation. She felt her arousal when she watched him drink the sight of her with his eyes, but she was not expecting the feeling of him taking her breasts into his mouth. He was so gentle, so sweet, yet so deliciously naughty, as he played and teased with her nipple, that she felt the beginnings of an orgasm originate deep inside her belly.

Her nipples were always very sensitive and she always played with them when she pleasured herself at night, but this was different. There was no contact with her clit and yet just the gentle nibbling on her nipple was enough to stir up an orgasm. An orgasm, which was never too far below the surface with her.

"Wait," she pulled his head off her breast before she lost total control of herself. She was afraid that she will anyway. This was like no previous sexual encounter she ever experienced. He was so gentle and attentive. He was so handsome. And most importantly, he was aroused by the sight of her naked body.

"Sorry," Jimmy again quick to apologies, feeling that he overstepped some limit.

"Don't apologies," she jokingly berated him as she realised that he was completely unaware of the effect he was having on her. She hugged him, pulling his body onto her naked chest. Feeling his slender body under his clothing. "Here, take your shirt off," she instructed him again. She kissed him before she released him to stand up and take off his shirt. She again watched him as he adjusted his rock hard cock, straining his pants to a slightly more comfortable position. She enjoyed that. The control she knew she had over him made her feel even more aroused. As his shirt came off, she was eating the view of his body up with her eyes. Now he came back to her. The feel of his naked skin. His eyes still so hungry for the sight of her naked flesh. They kissed again.

"Do you want to taste me know?" she asked, little fires dancing in her eyes. The excitement of the anticipated pleasure making her tummy hum. The pleasure of watching him eagerly agree making her arousal that much greater. The need for release rapidly building inside her.

"Let me show you what to do," she announced as she shifted a little to the side, trying to open her legs, to give Jimmy better access to lick her pussy. As keen as he was to explore every single inch of her body, his mind was focused somewhere else. Instead of eating out her pussy, he turned around and return his attention to her nipples. From her right breast he now shifted his attention to her left nipple. His assault a little rougher as his own excitement made him less concerned about his own lack of confidence and awkwardness. Now all pretence of control were gone. Jenny squirmed under the renewed attack on the second nipple as she just gave into the pleasure his licking and sucking was causing her.

It was not entire accurate to say that the pleasure within Winnie climaxed suddenly. The truth was, she was building up to her climax since she took Jimmy's cock into her mouth this morning. Now, that he was using his mouth to pleasure her nipple, the climax made her forget all pretence of control or embarrassment. She was not sure how it happened, but she managed to wrap her legs around Jimmy's naked torso. Her wet pussy lips and her beading moisture on her pubic hair pressing against Jimmy's flat abdomen. Her left hand was now firmly planted on the back of his Jimmy's head, providing increased pressure on her nipples. Her right hand providing that very same pressure and attention to her right nipple. She was no longer caring about how she looked, and how deformed her breasts were as her fingers pulled and squeezed the skin in every direction.

Jimmy knew that his mouth was pleasing Winnie, but that was not sure why he wanted to continue sucking it in favour of her pussy. He returned to her breast simply because he enjoyed the feeling of it in his mouth. His cock was hard to bursting point and he hoped that while sucking on the nipple, he may be able to rub his cock through his pants. The tightness in his balls, the hardness of his cock and the desire for release were almost making him go insane. He was certain that he will not be able to keep his pants on much longer unless he can get some release, but the events did not work out as well as he had hoped.

Winnie had her legs now securely wrapped around his torso. Her hand pressing on the back of his head, providing the increased pressure her growing arousal demanded. The pressure from her hand making him bury his nose and mouth deep into the soft welcoming breast as more of the breast and nipple pushed into his mouth, making it hard for him to breath. His left hand, trying to reach his cock for some desperate release, was pinned along his body by her thighs in a vice like squeeze. He was surprised just how strong her thighs were and preventing any possible escape. He was also becoming aware of her sex, now pressed against his abdomen. First it was the heat of her pussy that he felt on his body. Then the roughness of her pubic hair rubbing against his skin. Then the moisture. He heard boys at school talking about girls getting wet, but he always thought it was a euphemism. Now he knew that the expression was completely accurate because as Winnie approached her climax, she continued to rub more and more of her juices on his belly.

Jimmy did not know what exactly to expect. He realised that he will have to stop sucking on her nipple, because he was starting to see stars in front of his eyes, as he was unable to take a proper breath. He was starting to worry that Winnie may have peed herself, with the amount of wetness her pussy was now smearing all over his belly. With his right hand, the only hand that was free to move, he was able to reach around her body in an awkward attempt to hug her body. His touching the small of her back, that curvature of her spine just above her ass that was also extremely sensitive for Winnie.