Charles and Diana Ch. 10

Charles crooked one of his eyebrows at her and said, "You think I'm being a teasing prick? Oh, I can do much better than that! Just watch..." With that, Charles braced his hands on the front of the bar, slowly backed his hips away from her and just started making short, slow thrusts half-way in and out of her pussy—not pulling out far enough so the head would brush her inner labia and the tip would rub her clit nor thrusting far enough in to stimulate that spot deep inside her. Diana was trying as hard as she could to use her legs to pull him deeper inside her, but his back, ass and thigh muscles were way stronger than hers and he was able to push against her harder than she could pull with her legs.

Finally, Diana got so frustrated with him, that she just dropped her arms and legs from around him and yelled, "Ohhhh, FUCK YOU, Mr. Richards!" with her eyes blazing as she breathed raggedly. Charles just loved pissing her off by frustrating her because she looked so damned sexy with her chest heaving and her eyes blazing in anger...it fueled his desire for her even further!

At that, Charles grasped her thighs raising them slightly so he could get even deeper into her, plunged his dick into her as hard as he could with a loud grunt, and then growled at her with his eyes blazing, "No...FUCK YOU, Mrs. Richards!" Then he proceeded to fuck her as hard, fast and deep as he could while she wrapped herself around him, both of them grunting and groaning loudly until they both came a few minutes later. As soon as they recovered from their orgasms, they noticed that they were both sweating slightly from their exertion.

They were able to grab a few napkins on the bar to stop any drips when they separated; Charles had to nudge his shoes off his feet so he could step out of his pants and shorts that were now down around his ankles, and then he pulled his socks off. He bent down and picked up his pants right away so they wouldn't get wrinkled and went to lay them folded sideways next to his jacket on the back of the loveseat, then removed his shirt and tie and lay them with his jacket. Then Charles helped Diana down from the bar and with removing her dress before they went into the bathroom to clean up a little more.

As they watched each other in the mirror while they cleaned themselves, Charles asked Diana if she was really ready for him to take her ass; she smiled and nodded, and then Charles tried to make it clearer what he was really asking her. "I know you WANT me to fuck your ass...what I'm trying to ask you is, are you...ready...you know...is the way clear?"

Then realization struck Diana, as she understood he was asking her if she'd been to the bathroom recently so she would be comfortable and he wouldn't encounter anything unpleasant! Diana smiled again and assured him that she had just "cleared the way" about an hour ago, just before she'd gone onstage. So Charles smiled with her as they thought about what a new experience this was going to be for both of them...it was like they were going to get to experience something as virgins on their honeymoon after all!

When they were through in the bathroom, Diana started to take off the diamond jewelry she was still wearing, but Charles asked her to leave it on; then she bent down to remove her shoes, but Charles stopped her again. He said huskily, "Please keep the shoes and the jewelry on; there's nothing sexier than an otherwise completely naked woman wearing sparkling diamonds and a pair of sexy, gold high-heels!" Diana smiled sexily at him, and then he bent down and scooped her up in his arms and carried her out to the bed.

He set her down in front of him beside the bed and asked her how she wanted him; he chuckled silently when she put her hand on his flaccid cock and said she wanted him hard. So he put his hands on her breasts and pinched her nipples and grinned as he asked her again through his clenched teeth how she wanted him! Diana grinned with him and then sat down on the side of the bed and grasped his hips to turn him around in front of her, putting his cock right in front of her face.

She told him to relax and spread his legs a little wider as she ran her hands up and down his muscular thighs and over his hard, shapely ass. She snorted a laugh when he planted his legs pretty wide and struck what she called a "Peter Pan" pose with his fists on his hips, flashing a wide grin at her—his dimple making a deep groove in his right cheek. Then she laughed harder when he thrust his hips toward her a few times making his cock and balls wriggle as they just dangled in the wide expanse between his thighs. Then she chuckled quietly and said, "Not that wide!" as she brought her right hand up to cup his balls, and then kept forcing her hand upward with a little more pressure until he had to bring his legs in and stand a little taller so his cock was in front of her mouth again.

Then she ran her hands to his inner thighs and stroked him up and down, pausing to caress and massage his balls for a few seconds on each upward stroke. She watched in fascination as his cock began to lengthen and thicken slightly as she stroked and caressed his thighs and his sac. When he was about half hard, she leaned forward and began to lick up and down his shaft from tip to base, until she lifted his cock to lick the underside from his balls all the way up to the tip. She marveled at how each lick took longer as his cock grew slightly with each firm, wet stroke of her tongue. She loved listening to the sound of his deep, heavy breathing as his excitement grew at the same rate as his cock!

When he was almost fully hard, she wrapped her mouth completely around the head of his cock and sucked as much of his shaft into her mouth as she could, taking a deep breath through her nose as soon as she felt the head of his cock at the back of her mouth to help keep from gagging. Then she slowly backed her lips and tongue off his shaft, applying pressure to the underside of his cock with her tongue; Charles sucked in a breath and groaned deeply as his head fell back. By the time she completely released him from her mouth, his dick was fully erect, rock-hard and standing 8 glorious inches straight out from his body, looking like a big, juicy sausage!

Diana moaned as she stared at and softly caressed his beautiful long, hard cock with her finger tips; then she couldn't stop herself from grasping it again as she began to run her tongue all up and down his shaft and wrap her lips around the head to swirl her tongue all over it...she couldn't stop what happened next, either! She felt her excitement from looking at, touching, licking and sucking on his cock shoot between her legs as her pussy throbbed and flooded with wetness—she could even feel her clit aching to be touched! As she continued to suck on the head of his cock with her left hand grasping the base of his shaft, she reached down between her legs with her right hand and started stroking her clit.

Charles had looked down to watch her when she started licking all over his shaft again, and he held his breath as he watched her excitement grow. Then, when he saw her put her right hand down to her pussy and start rubbing her clit as she moaned loudly on the head of his cock, he released the breath he'd been holding and just took deep slow breaths as he watched her and encouraged her—his own excitement being held at bay.

He put his right hand down and gently caressed her left cheek with the backs of his fingers as she licked around the head of his dick and he said deeply, "That's it, pretty lady. Stroke yourself if you need to...you must really like sucking my cock! If it turns you on this much, you're welcome to suck on me whenever you want! But if you still want me to fuck your ass with my nice, big cock, then you'd better hurry up and cum before you make me cum in your mouth! Then you'll have to start all over again...or is that what you're hoping for! To keep sucking on my cock so you can watch me get hard again...is that what turns you on? Watching my cock get all long and hard and knowing that you did that to me with your luscious lips and tongue? Yes, pretty lady, I love the way you lick and suck on my cock..."

Suddenly, Diana released his cock from her mouth as her back arched and her head fell backward and she groaned loudly, "Oh, God, YES!" as her hips gyrated on the edge of the bed while she continued to tap her clit with her middle finger, and her left hand still tightly gripping the base of Charles' shaft.

Charles was, once again, treated to sight of her beautiful face during an orgasm; he stroked her flushed cheeks with the backs of his fingers and ran his thumbs gently over her full, parted lips, still picturing the way they look wrapped around his hard cock. He closed his eyes as he tried to calm his excitement from watching her because he wanted to fuck her ass. The pressure from her hand wrapped around the base of his dick also helped to prevent him from getting to orgasm while he watched her.

When Diana's orgasm finally stopped, she smiled sexily up at him when she realized he was still rock-hard, as her left hand was still firmly wrapped around the base of his shaft. Charles asked her quietly if she had any idea how much it excited him and turned him on to watch her bring herself to orgasm, and that he hoped his talking to her had helped instead of distracting her. She told him with a soft moan that his talking to her had definitely given her the boost she needed to get herself off!

Then Diana asked Charles if he was ready to fuck her ass and if he knew any of the techniques to help make her ass ready to be penetrated. He told her that he'd read a book that had described all the physical "do's and don'ts" about anal sex, including the emotional and psychological implications involved in such a taboo act. He described what he considered the more intimate ways of stimulating the anal area using his fingers, lips and tongue—which he remembered she said she'd already experienced...he wondered briefly with whom? He shook his head slightly to dispel the image that tried to creep into his mind because he knew who that someone was in her mind; the big man—John Wayne.

Then he asked her what position she wanted to be in when he entered her ass for the first time, and she told him that she wanted him to take her from behind while she was on her hands and knees. He knew that meant that she must trust him, because that was one of the more vulnerable positions for her—he could hurt her if he lost control in that position, so he vowed to himself that he would remain under her control; he would not make a move unless she told him to.

He was a little disappointed because he had really hoped to be able to see her face the first time he put his dick in her ass. Then he had an idea; the dresser mirror faced the side of the bed—if they turned toward the mirror he would be able to see her face! He told her he that he wanted to do that, and she smiled and said she would like to see his face as well. So, they crawled onto the bed and Diana grabbed a few pillows to prop her head and chest on while she put her ass high in the air so Charles could crouch behind her and use his fingers and tongue to stimulate her pussy and ass until she told him she was ready.

Charles used his tongue on her pussy for a couple minutes at first, just because he wanted to taste her again. Then he dragged his tongue up to her puckered pinkish brown asshole and just took several soft, slow licks as Diana moaned deeply and told him how good that felt. He gradually made his tongue licks on her asshole firmer as he felt the flesh around it start to soften and relax; he was also using the fingers on his right hand to stroke in and out of her pussy and her moans began to get louder.

Then Charles asked Diana if she was ready for him to start penetrating her ass with his fingers, and she moaned yes, so he took his fingers that he'd been stroking in her dripping pussy and brought them up to her ass and carefully started to insert his index finger. It easily slid all the way into her ass and Diana moaned that she wanted more, so he added his middle finger and stroked both of them in and out of her several times as she moaned loudly, "Oh, YES! More...give me more!"

Charles paused for a moment trying to figure out how he was going to make his dick slick enough to put in her ass, then he thought, "Same as your fingers...put your dick in her dripping pussy and coat it with her slick juices...just don't put it back in her pussy once it's been in her ass!" He did remember that part of the "do's and don'ts!" So, Charles rose up on his knees and told Diana he was going stroke his dick in her pussy a few times to get it nice and slick for her ass, and while he did that, he continued to pump the 3 middle fingers of his right hand in and out of her, now very relaxed, ass.

Diana was about to explode from pleasure and excitement, and when she felt she couldn't stand the anticipation any longer, she braced herself on her hands staring at Charles in the mirror behind her and told him she wanted his dick up her ass...now! Charles' eyes flashed with fear and lust at the same time; he was remembering with fear how his ex-wife had screamed in pain when he'd shoved his dick in her ass, but he didn't want to cause Diana any pain! But then he realized that he'd been preparing Diana's ass and she was pretty loosened up, where his ex-wife had not expected nor been prepared for that kind of penetration.

Charles pulled his dripping, hard cock out of Diana's pussy and placed the head at her asshole and hesitated for a couple seconds as he stared at her in the mirror again. Diana's eyes flashed with lust and desire and she growled demandingly, "DO IT!" Charles gritted his teeth, grasped her hips firmly and thrust his dick all the way into her ass with a low grunt as they still stared at each other.

As soon as his dick was buried all the way up her ass, Charles and Diana both threw back their heads and half-groaned and half-growled in lust as both of their backs arched in pleasure. The initial wincing frown of pain that came over Diana's face from that sudden, deep invasion of her ass was instantly replaced by a relaxed, open-mouthed mask of pleasure as her ass became accustomed to being stretched open and penetrated so deeply. She realized that the feeling of fullness from Charles' dick in her ass reminded her of how the big man's thick cock had felt in her pussy...she was going to get the best of both worlds with Charles!

Charles' initial loud groan and growl gradually became a low, throaty moan of, "Oh, My God...!" as he felt the head of his cock resting in virgin territory deep within Diana's ass. They slowly opened their eyes as they just savored the new sensations. Then Charles flashed a look of pure lust at Diana in the mirror and asked as he groaned, "So, Mrs. Richards, do you like the way my dick feels up your ass?"

Diana slowly grinned lustfully at him and then said, "You bet your ass, I do! So, Mr. Richards, don't you want to find out how it feels to fuck my ass?"

Charles grinned wolfishly at her and replied sexily, "You bet your ass, I do!" as he slowly withdrew his dick from her ass all the way, leaving the tip poised at her soft opening, then slowly slid all the way into her ass again. They both groaned at the slow sensations of her ass being filled completely as his dick burrowed into the soft, warm tightness. It was a completely different sensation for Diana from having her pussy filled, but for Charles, her ass felt very similar to her pussy—just as soft, tight and warm, but not quite as wet.

For Charles, the excitement came more from the knowledge that he was the only man that Diana ever trusted enough to let him put his dick in her ass. Which made him wonder again—if Diana had actually had an affair with John Wayne, the big man, why hadn't she let him fuck her ass? If Diana loved him as much as she said she did, she was bound to have trusted him, so why wouldn't she have let HIM take her ass—or had she lied to Charles because she just wanted him to believe that he was the first man to have his dick in her ass?

Then a thought struck him; she's always called Wayne big man; did that endearment have more meaning to it other than the fact that he was a "big man"—a big, important movie star, and a tall and physically large man? Was he "big" in another way as well? Did he have such a huge cock that Diana was afraid to let him take her ass? He had his eyes closed and he started to frown slightly as these thoughts swirled through his mind while he was slowly thrusting in and out of Diana's ass. Then he opened his eyes when he heard her voice moan; "Hey, sexy man...what's going on in your head? Is something bothering you?"

Charles stared at her in the mirror and started to thrust harder into her ass, and he asked her slowly, "Diana...you swore to me that you'd never had any other dicks up your ass! If you were so in love with John Wayne, the big man, why didn't you let him fuck your ass?"

Diana was starting to groan from his harder thrusts as she could feel him stimulating that same spot inside her that makes her ejaculate when she orgasms; it was just a slightly different angle. She couldn't concentrate on what he was saying until she heard him say something about the big man, then her eyes flew open when she realized he was asking her why she hadn't let John Wayne fuck her ass! Oh, God...what should she tell him? Then a look of shock came over her face as Charles started slamming his dick into her ass as he tried to figure out the answer.

"Is the reason you call him 'big man' because he's got a big dick? Is it so huge that you were afraid to let him put it in your ass? Is that it, Diana? Is that why you don't want me asking any questions about what happened between you and the 'big man?' Because you don't want to tell me how big his dick is and how good he made you feel?" Charles' voice had started as a low rumble and gradually turned into a loud growl as his jealousy flared when he thought that she had probably been telling him the truth all along and this was exactly why she didn't want to give him any details.

Diana couldn't answer him; his hard thrusts deep in her ass and the jealous growl of his voice were quickly bringing her to orgasm. She was groaning loudly with each hard thrust, and she collapsed off her hands as she started to thrust her ass back against Charles; then she reached her right hand down and started rubbing her clit furiously as she felt it aching. As soon as she slid a couple fingers into her pussy, Charles said something that drove her over the edge as she screamed, her pussy throbbed and liquid squirted onto her right hand as her hips convulsed:

"Oh, God...I wish I could fuck your pussy and your ass at the same time! Would you like that, pretty lady...to have dicks fuckin' your pussy and ass at the same time? Oh, yeah...I can tell you like the thought of that! Oh, God...your ass just squeezed my dick...that feels so fuckin' good... Aaaaahhhh, yeaaahhh...!" Charles moaned, his head falling back as his dick started shooting cum into her ass. He slowed his thrusts and then finally stopped after the last pulse of his orgasm, then he grinned sexily as he thought to himself, "At last...I got to take my real dream girl's virginity...even if it was her ASS!"