Nancy's Mid-life Awakening Ch. 23

"I want you to make love to me," she whispered in his ear. "I want to feel you filling my pussy with your hot cum."

"Mmmmm...," he replied just as quietly. "You feel so good around my cock."

"Do you want to feel your cock in my cherry ass?" she whispered hesitantly. Paul paused and looked in her eyes.

"I'd love to, but are you really ready for that right now?"

"Yes," she answered. "I even picked up lubricant to help you, but I have to get it first."

Paul continued to search her face for signs of hesitation or uncertainty, but she appeared completely resolved. He slipped out of her pussy and helped her stand up. Deb padded quietly out the door and down the hall. While he waited, Paul could hear the sounds of his wife and Kyle in the next room and they seemed to be enjoying themselves quite a bit. A minute later, Deb returned and quietly closed the door behind her. She went of to the bed and handed Paul a small tube of K-Y jelly.

"I think that will work, won't it?" she asked anxiously.

"It's perfect," he reassured her. "Come here and lay down again."

After she resumed her position, he leaned across her and kissed first her nipples and then her lips. "First, I'm just going to use my finger so that you can get used to it," he told her.

Paul helped her bend her knees up and spread her legs to let him access her tiny, tight back door. Next, he squeezed out a generous amount of K-Y jelly on two of his fingers and then used them to spread the cool gel around her brown pucker. Deb felt the sudden coldness of the gel as it touched her skin, but it quickly warmed until she didn't notice it at all. Meanwhile, Paul's forefinger was circling her asshole and started to press inward.

She felt his fingers moving lightly around one of the most sensitive areas on her body and her anus automatically clenched. However, the feeling coming from her ass was actually quite pleasant and she began to relax when it was apparent he wasn't going to just jam his finger inside her. "I just want to get you used to the feeling of me down here and let you see how sensitive and exciting it can be," he told her. His voice was quiet, unhurried, and soothing. "I'll tell you everything I get ready to do beforehand so that you won't be surprised."

Deb had a short, quiet intake of breath through her teeth as she mentally prepared herself for what she believed was going to be the point of no return for her. Paul's finger slipped inside her without any difficulty and penetrated as far as his middle knuckle before her sphincter tightened around his digit. Deb tried to categorize the sensation; it felt strange, but there was no pain. Paul told her that he was going to slowly work more of his finger inside her and let her adjust to the invasion, and she nodded her head in understanding. The strange feeling grew and she had a feeling of fullness in her ass. Paul used his thumb to caress and massage the area outside of her hole which felt good and helped her relax more.

"How does that feel?" he asked.

"Different, but not as bad as I thought it would be," Deb replied. Deb didn't tell him that during the previous week, she had fingered her own ass several times when she was in the shower just to see what it felt like and whether she really wanted to try anal sex. He started slowly working his finger in and out of her ass and it went smoother and smoother as her hole adjusted to the defiler. He kept the pace slow and watched as Deb began to move herself to assist with her ass-fucking. Paul leaned down to kiss and gently nibbled on the two hard points on her chest without pausing his hand's motion.

After she was fully relaxed and his finger was moving easily in and out of her ass, Paul worked in a second, and later a third finger. Deb could feel her ass stretching to accommodate the increasing size of the invasion and found it became easier and easier. Paul maintaining a slow and steady movement while he finger-fucked her ass and noted that Deb was no longer as tense and apprehensive as before.

"Are you ready?" he asked. She knew what he was asking and nodded her head. Her ass made a slight sucking noise and his fingers exited her ass and the seal around them. Her ass still felt like something was in it, but not as pronounced as earlier. Paul went to the shared bathroom and tried to wash his hands as quietly as possible, but he judged from the sounds in the next room, that Nancy and Kyle weren't paying attention to him.

Meanwhile, Deb thought back to the previous week when she watched Paul and another man fucked Ann in her ass and pussy at the same time. She tried to imagine how that would feel, but wasn't interested in finding out right away. She wondered how much different his dick would feel inside her ass compared to his fingers, but didn't get too far down that road before he returned from the bathroom.

Paul stood in front of her stroking his cock back to hardness and asked if she would prefer to be taken the way she was or from behind. Deb thought for a moment and decided she wanted to see his face. "If it's not much harder, this way would be fine."

Paul grinned. "It's just as easy either way." It took him another minute to get himself ready; after getting hard again, he covered his cock with more of the K-Y jelly and moved in between her bent knees. Once more, he took her legs and raised them up to rest on his shoulders and in doing so, lifted her butt up from the mattress enough to make it an easier target. Her hole was still slightly open from his earlier fingering and when he pressed the soft tip of his cock into it, he watched her sphincter expand and allow the head of his penis to disappear inside her.

Deb gave a quick gasp, but not from pain. Before he could react, she lied and said, "That feels so good." In truth, it didn't feel good or bad -- it just felt like her butt was stuffed. He eased himself in as far as he could which took almost a minute. When he started pulling back, the sensation became more pleasant to Deb. Her ass was squeezing tightly around his cock which slowed how fast he could plunge into her, but it became easier to speed up once her ass expanded sufficiently.

After two minutes of his initial penetration, he was rocking in and out of her ass as fast and hard as he had done to her pussy. Deb was beginning to understand why many women (and men) enjoyed getting their ass fucked by a nice cock. Her legs had fallen from his shoulders which changed the angle of his insertion, but he was also able to kiss her and play with her breasts while he fucked her. Paul was able to continue for less than five minutes before he came inside her ass with a shuddering spasm. Deb thought she could feel his cock twitching as it squirted his cream in two large loads.

When he finished, Paul was breathing hard and Deb was already considering the next time she took a man in her backside. She wondered about her husband and whether he would want to try it with her or not. He had always been the more conservative partner in their sex life and while she loved him with all her heart, she still yearned for new sexual experiences that he didn't appear to be interested in trying with her. That was the biggest reason she wanted to get involved in a swing group, but not if it was going to jeopardize her marital relationship.

Paul's cock softened quickly and Deb found herself playing around to use her pelvic muscles to push him out of her ass. He fell out of her and then collapsed on the bed next to her still form. She turned her head and looked at him with a smile. "I really liked that," she whispered. "Thank you."

"Are you kidding?" he said after catching his breath. "I was just concerned you weren't going to like it or you'd find it painful."

"It didn't hurt a bit, but my ass still feels like it's completely stuffed with something," she giggled. Before he could reply, they both heard a loud voice from the neighboring room crying out, "Oh fuck!"

Paul and Deb looked at each other and tried to stifle their laughter. "I guess Kyle's enjoying himself," Deb said between fits of giggling.

"Yeah," Paul responded. "Nancy can do that to a man." They laughed together and spent the next several minutes caressing and fondling one another. Paul tried to politely inquire about Deb's other sexual desires or fantasies, but she kept shaking her head and telling him she really didn't know. In truth, she did harbor some secret desires, but felt embarrassed about telling her new lover in case he thought she was a whacko. She turned the question around to him and he thought long and hard before replying.

"I really don't know. I think I've already experienced all the fantasies I used to have when I was younger, especially since Nancy and I became involved with the others in our group. I know that some of the members are involved in sex play that we never see and I sometimes wonder about all they do in private or with others who are into the same things."

"Like what," Deb prodded.

"Well, we know that Steve and Dana have a dominant-submissive relationship that carries into sex play that we don't ever see. We also know another couple who are both bi-sexual and I'm sure they get involved with members of their own sex fairly regularly. Some people are into role-playing and I'm sure that can lead to some pretty different kinds of encounters. James and Ann like having sex in public because of the added excitement from the possibility of being caught or seen," he answered.

"Really?" she said with raised eyebrows. "I thought you were talking about something really strange and kinky."

Paul laughed. "We probably know people who are into something kinkier than those things, but I'm too naïve to imagine what kind of behavior that would be."

Changing the topic slightly, Paul asked, "What things turn you on? Obviously you enjoy what most of us consider normal foreplay, but is there some other activity that gets you hot?"

Still not wanting to embarrass herself in front of Paul, Deb continued to play dumb. "I don't know. Like what?"

"Well, for instance, do you enjoy looking at porn or watching other people have sex?"

He could see the answer right away. Her face went red and her eyes automatically dropped from his. She tried to downplay it by responding, "I saw a couple of porn films years ago, but I've never bought or rented any for myself. That would be too weird."

Paul decided to put her on the spot and try to break down her reticence at being honest about her sexual desires. "That's not answering the question. I asked if you enjoyed watching others have sex and I think that you do. When we were at Ann's, you were a lot more aroused when you were in her bedroom watching her with all the men. I bet you were thinking what it would be like to be in her place?"

"I did not," she replied without much conviction.

"Sure you did. It was obvious and I think every other woman there felt the same way. I know Nancy did. And just so you know, it's okay to enjoy watching others have sex. It's one of Nancy's biggest turn-ons."

Deb looked down again still blushing and suddenly uncomfortable with the discussion. However, Paul continued to press her for more. "What other things do you think about or enjoy that you aren't telling me? There's no reason to be shy about it and I won't judge you. Neither will anyone else, for that matter."

She finally relented. "It's so embarrassing. I don't know if I should tell you." She went silent for a minute while making up her mind. When she looked up and began to speak, Paul could see her eyes pleading for understanding and acceptance. "I think about all kinds of things. I've never had much variety in my sex life and for the past few years, I've thought about different things that I've heard about or seen on the internet. I've wondered how it would feel to have sex with more than one man, or sex with a woman, or even a man and a woman. I've seen some video clips of bondage and part of me wants to be tied down and made helpless for a man to use me as is sex slave. I've also thought about having a man as my sex slave. I already told you about wanting to try anal sex, and I'm so glad you helped me experience it. It was different that I expected, but I would do it again." She paused and then said, "There is one other thing that I've been doing that I enjoy and that's going online and having cybersex with strangers. I love the dirty flirting and watching them beg me to get naked for them. I can get them to do almost anything just for a view of my boobs or pussy. The guys are always showing off their cocks and they always jerk off and cum when they watch me play with myself."

Paul smiled at her confession. "Nothing wrong with any of that," he replied. "Nancy and I have done that, too. She can't believe how desperate some of the guys are to see her naked. She loves teasing them, but unless the guy is a real jerk, she always shows herself. We also like to trade ideas with other online couples of things to try."

Deb became visibly more relaxed at Paul's response and acceptance of her desires. "But don't tell Kyle," she asked. "He doesn't know about my cybersex stuff or any of the other things I just told you."

"Why not?" Paul asked. "He should be the first person you talk to about those things."

"He wouldn't understand," Deb said sadly. "He has a pretty limited view of what sex should entail, and frankly, I'm surprised that he agreed to doing this."

"Not to pry too much, but what did you guys talk about before we came over? Did you tell him why you want to have sex with other men?"

"We talked about how we both felt after going to a couple parties and even though we both were uncomfortable with having sex with other people in the room, I could tell it bothered him more. He did say he was okay with trying out different things, but I think he really is just agreeing to make me happy."

"I don't know," Paul responded slowly. "When he and I talked earlier, I got the impression he was enjoying it, but was more concerned about making you jealous or resentful if he seemed to like it too much."

"That's ridiculous," Deb shot back.

"I'm only telling you what he told me. Maybe you two should have another talk. It's okay to want to be considerate of your spouse's feelings, but when you're talking about something that could impact your relationship as much as this, you have to be completely open and honest. If your marriage can't survive that kind of discussion, you have bigger problems than just how to have sex."

They both grew silent while Deb pondered Paul's suggestion. When she looked back up, she whispered, "They're awful quiet in there, now? Do you think they're done?"

"There's one way to find out," Paul said as he swung his legs over the side of the bed to get up.

"Where are you going?" she hissed in alarm.

"If you really want to know if they're done, I'll knock on the door and ask. Otherwise, we can go get something to drink. I'm suddenly very thirsty," he told her.

"Don't knock on the door!" she exclaimed and then quickly rose out of bed behind Paul. She pulled a large heavy robe from the back of the door.

"You're right," he said. "We should just walk right in on them." Deb was getting ready to grab and stop him from doing anything before seeing the smile on his face and realizing that he was yanking her chain.

"You bastard!" she said with a laugh as she gave him a light slap on his bare butt. When they headed out of their room Deb was wearing her robe, but Paul was still nude and unconcerned. He looked back at the other bedroom door and noticed it was ajar. He headed back to peek inside while Deb unsuccessfully tugged to keep him away.

"They're gone," Paul whispered back. They hurried back down the hall to the main part of the house and found Nancy and Kyle sitting together under a small soft blanket on the sofa.

"It's about time you two came out," Nancy called loudly. "We were just wondering if we were going to have to check and see if you were still alive."