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James and Sherrie first met at a business luncheon. The conference was boring but the lunch was definitely going to be worth it this time.
“Who has the Caesar Salad?” asked the waiter. James and Sherrie responded with a “Me!” at the same time.
“You take it,” insisted Sherrie.
“Ladies, first!” said James, persistently.
James was a handsome man in his late forties. He had kind looking eyes and a nice smile. She liked his muscular but average build and salt and pepper hair. He was dressed in a tailored grey suit and royal blue tie which augmented the color of his eyes.
Both, James and Sherrie exchanged sexual glimpses, knowing that it wasn’t just the salad that they wanted from each other.
After the usual business pleasantries were exchanged, lunch was finished, the conference culminated, James and Sherrie exchanged small talk. “Would you like to get together some time, Sherrie?” asked James.
“Maybe. Keep in touch,” suggested Sherrie.
“But …” James stuttered nervously. “I don’t have your telephone number.”
“Look it up,” playfully said Sherrie. “Just Google me!” said Sherrie as she walked away with a grin on her face thinking how erotic James could probably be in bed.
Sherrie was going to take this relationship slowly. She was so sick of middle-aged men who never learned how to give a woman a decent orgasm, if any or more than one at a sex session. Even when she re-dated an old college boyfriend who had been married for over twenty years, he still didn’t know how to give an orgasm just like the problem in college. ‘No wonder he got divorced,’ Sherrie reminisced.
James did mysteriously find out Sherrie’s phone number. He called her company for it the day there was a temp by saying he needed to talk to her about a proposal. The temp didn’t know the difference or didn’t care.
After a few phone calls to each other, Sherrie finally agreed to go out to dinner with James. She was hesitant at first because she was afraid they might run into each other at future business functions.
When plans were finally discussed, James suggested they should go out to dinner (He hinted at going to a hotel afterwards but Sherrie didn’t acknowledge the topic and tried to be coy). But, she knew, since neither one of them had a place to bring someone back to for entertaining … with kids and such; she probably would agree if the topic came up again.
Housing was one of the drawbacks of being divorced. Sherrie tried to be demure, which wasn’t one of her strong points, but she knew James probably had his choice of women and didn’t want to discourage him too much.
Sherrie was looking forward to seeing James again. She was really looking ahead to being with such an agreeable man and the feelings about having sex again were alluring and glamorous.
On Friday morning, before James and Sherrie were supposed to date, Sherrie received a phone call from James. “Sherrie, I have to change our plans,” said James.
Sherrie was immediately disappointed and disenchanted. James continued unrelenting, “My son got in an accident with my car in Santa Barbara, so I don’t have a car for a few days. How about it if you meet me at the Renaissance Hotel in Newport,” asked James?
Sherrie hemmed and hawed over the idea of meeting James for the first time at a hotel but then she finally agreed to get together later that evening. “What about dinner?” she asked.
“We’ll order room service,” recommended James.
Sherrie was already hungry.
As Sherrie was driving towards Newport Beach where James lived, she started to feel nervous and panicky.
I’ve only seen James once, Sherrie thought to herself. I’m not sure I’m ready for a man yet. Sherrie was out of practice from dating and she was trying to justify defeat without admitting it to herself. Sherrie was 41 and James was 48. However, Sherrie looked about 31 years young. She hadn’t dated anyone new since her divorce two years earlier.
As Sherrie got off the exit from the 405 freeway, she couldn’t see the hotel. She called James on her cell phone. “Where is it?” she asked. As James gave directions, she pendik escort could then see a large white building ahead of her on the other side of the freeway.
“Okay, I see it. How about if you meet me at the bar first?” asked Sherrie.
“Just come on upstairs, Sherrie. I’m not going to bite you!” James insisted. “I’ve chilled a bottle of wine and I have a loaf of bread with smoked salmon.”
“I thought we were going to…” and then she stopped talking. “I’ll be right there James.”
Well, Sherrie thought to herself. She would carry through with her plans like a big girl. “Okay, I’ll be right there but have my glass of wine on ice because I’m thirsty,” Sherrie demanded.
“Don’t worry. I’ll be waiting for you with open arms.” James knew Sherrie was jumpy and tense. He planned on relieve her stress as quickly as possible and promptly.
As Sherrie got out of the car, she grabbed her overnight bag which had a few surprises in it. Although she felt foolish, she took out the bag of stick-on bows she had bought, a video and some lingerie.
As Sherrie knocked on the door of Room 969 with herself covered in stick-on bows to match her purple dress, she said, “Hello. I’ve come gift-wrapped James.”
James opened the door, and laughed hysterically as he grabbed her hand and pulled her immediately into the strange hotel room. “I need you Sherrie and you won’t need any ornaments when I’m done with you,” James jested. “I’ve been thinking about having my way with you since you argued with me over the Caesar Salad at our first business luncheon.
As James began kissing her, Sherrie became wet and James pulled out one voluptuous breast from her dress and began sucking on Sherrie’s nipple. His tongue felt as arousing as he swirled it around her erect and protruding and stiff nipple.
Sherrie was getting wetter and slippery. It had been a long while since she had made love to a man, since she had been touched tenderly, since she had enjoyed being fondled with a mutual fondness. It had been over a year since she was even interested in a man or sex.
“Take your clothes off,” commanded James.
Ignoring James’ directive ness, Sherrie replied by saying, “Let’s have a glass of wine first!” As James opened the bottle of fine chardonnay wine she loved, he kept kissing Sherrie. It seemed like eternity before she finally got a sip of wine between the lusts the two of them were feeling. As James continued kissing her, they both put their glasses of wine down on the nightstand without further distraction.
First, James lifted up one leg of Sherrie’s and unbuckled her sandals. He laid her back on the bed and pulled her stockings and panties down in a rushed manner as he spread her legs wide open, and he started to go down on her just like she desired and needed so desperately.
It had been a long time since Sherrie had a tongue licking and it felt great. As she began to spasm and jolt her body towards James up and down, the bed buckled in the middle sliding them both swiftly to the floor. She was cumming hard as they both landed on the floor. She laughed as their passion dissipated.
“That’s never happened to me before,” said James.
“Me either,” said Sherrie but she wasn’t talking about the bed. James had casually stuck his tongue in her ass. It felt erotic and Sherrie was ashamed to admit to herself how good his tongue in her ass felt and that she wanted more.
Luckily there was another bed in the hotel room. They both took off the rest of their clothes and as Sherrie dropped hers to the floor, James climbed on top of her inserting his hard, erect cock in Sherrie’s hot pussy. His strong cock felt so good. He was thick and just the right size for her.
Anything may have felt good after the years of monotonous sex she had with her ex-husband. He wasn’t the worst lover, just not very enthralled in anything but getting off himself.
James stroked her steadily, aiming the head of his cock at her g-spot. Sherrie came hard, unable to control herself. As James pulled out, she asked if anything was wrong. He hadn’t come yet.
“There’s no guarantee that a guy will stay hard, escort pendik Sherrie. I’m just testing the waters,” he laughed.
“Wells run deep, don’t they?” she giggled.
James and Sherrie relaxed as they sipped their glasses of wine. The conversation was short but the lust was strong. “I forgot this booby,” James said as he began suckling Sherrie’s forgotten breast.
Sherrie was aroused and as James knelt down inserting his hard cock into her mouth, while absorbing his delicious cock deep into her mouth he hardened and sighed.
The lovemaking made Sherrie feel delirious with delight. She had forgotten how much she loved grand sex. She had forgotten that she could feel passionate and living again. As James continued making love to her, stroking his cock on her lips and into her mouth, Sherrie was in ecstasy as James came firmly and promptly. She wanted to swallow him but she just couldn’t.
As Sherrie kept talking, James put his finger across her mouth. “Let’s go to sleep,” he said as they both dosed off in each other’s arms until morning. Sherrie had selfishly received so much pleasure from James, forgetting to take better care of his needs. “Good night James,” Sherrie said as she closed her content eyelids.
Sherrie fell asleep quickly and slept soundly. As she and James both awakened early, James began kissing Sherrie. From kissing her mouth, he went down to her pussy, tickling her clit with a moist tongue, taking his time and making her cum again quickly.
“Well, good morning to you, too!” said Sherrie.
James and Sherrie continued to make love. As the sun rose, so did Jim several times.
James said he was going to take a shower.
“Can I join you?” asked Sherrie. James grabbed Sherrie’s hand and led her into the shower. “You know how sexy you are, don’t you Sherrie?”
Sherrie didn’t want to seem too eager to please Jim. She knew he was a womanizer and she wanted to keep this one close to her chest and treasure the moment.
Sherrie smiled and grabbed the soap. “That’s my job!” she insisted as she began lathering up James’s cock. “You do have a lot of strength,” Sherrie laughed nervously again looking at James upright cock.
As James and Sherrie were making love in the shower, James turned off the water and led Sherrie back to bed as he dried her off. “You have a great ass!” he whispered.
James opened up a little toy he had bought her and surprised her nonetheless again. “The gal is the store said you’re going to love this one!” insisted James. As he placed the toy on her clit and inserted a finger up her ass, Sherrie came again and she couldn’t believe how quickly she reacted to the ass stimulation.
James was twirling his finger just inside Sherrie’s sphincter muscles, causing gentle, shunting motions in and out of her anus. ‘Is this rimming?’ She wondered to herself. Lubrication didn’t seem to be a problem between her wetness and James’ tongue all over her pussy and asshole with a toy doing wondrous things to all parts of her.
“I like this toy!” exclaimed Sherrie. “These sheets smell like…” Sheri chuckled again trying to change the subject.
“…Like sex, you innocent little vixen you?” James chortled. “Stay still,” James requested as he kept using the toy.
“Is that the same toy?” asked Sherrie.
“Maybe, it is, maybe it isn’t,” laughed James. The intensity kept changing, like the flicker of a tongue, to an intense orgasm giving thrust in Sherrie’s already tired pussy. James was giving Sherrie one orgasm after the next.
“Ever try anal sex, Sherrie?” James asked.
“Not really,” Sherrie said as she remembered the one time she and her ex-husband tried. “It’s not very comfortable.” she said apprehensively but curious and recalling James analingus.
“Anal sex was always taboo to this Catholic girl,” said Sherrie. But, she enjoyed the anal play and she was wondering if she was missing out remembering her mother say over and over again, “Your aunt Marylou liked it in the ass all the time.” Sherrie was always grossed out by hearing her mother talk that way and wanted to say to her, “Maybe you should have tried it! Maybe, pendik escort bayan you would have seen another side to sex and actually feeling pleasured.” Sherrie would never debate with her mom about a subject she was so naïve about and it would only cause her mom to lose faith.
But anal stimulation with James was very pleasurable to Sherrie. Sherrie was embarrassed about anal sex, but she’d wanted to try it with a loving man for a long time. Likewise, James seemed extremely eager to experiment. There was a whole world of great sex out there she was convinced feeling starved and stifled by the poor sex life she had had with her ex-husband.
Would you be willing to experiment sexually with me, Sheri?” James asked.
“Well, yeah, sure… as long as we both enjoy it,” alleged Sherrie.
James positioned Sherrie on her hands and knees. He gently rubbed lube around the rim of her asshole, sliding his finger inside and pushed a lot of lube into her rectum. Then he placed the head of his cock on her anus opening and said, “Push out while I push in.” She could feel the crown of his cock pop into her ass, stretching her almost to the point of pain. “Buzz the toy on your clit,” he instructed. It helped distract her.
After a few moments she felt comfortable to her surprise and delight. “More please,” she begged. James slowly slid his cock deep in her ass until she felt his balls touch her pussy lips. Then he started stroking. Sherrie felt her cunt and ass tighten as she burst into orgasm, uncontrollably and unconsciously.
James kept steadily pumping her ass and Sherrie came again. He postponed her like a fucking machine and she came over and over again until the orgasm was continuous and beyond eroticism. She felt delirious when he finally erupted and pumped her ass full of his cum.
Sherrie didn’t want the lovemaking to end but she was afraid she wasn’t going to be able to walk a straight line after all the orgasms James imposed on her and the multiple orgasms weakened her at the knees and organs when James had persistently bestowed on her with ‘their’ new little toy.
“I’m feeling selfish,” Sherri stated.
That’s okay,” said James. “I was selfish, too. You’re a heavenly ass-fuck.”
“I’m a what?” innocently asked Sherrie.
“I’ll go pay the bill and you get dressed,” James said as he got out of bed and pulling up his pants. James sure did look handsome in clothes and even better without them, Sheri thought to herself.
“I’ll be right back,” said James. “You know, we never did have dinner.”
“Or, breakfast …” reminded Sherrie.
“WOW!” she said to herself as she heard the door close. Sherrie never noticed that they went without and food. I’m starved; she thought to herself but so satisfied. The two of them had acted like two animals in heat, two children at play and new two lovers about to embark into a path of ecstasy and elation.
As Sherrie waited for James to return, she thought about the orgasms she had just experienced in the last 24 hours.
I came with a cock stroking my ass? It was so much better and different from cunt sex or oral sex?
I guess I am a truly anally erotic woman. The process of penetration was a blur. I am a woman who starts to cum when my sphincter is stretched open and I didn’t care about what was happening as the most potent orgasm was taking over my entire body and weakening it beyond human belief.
James had exquisite control over my pussy. I don’t think he ever had anal sex before but obviously he had been thinking it through in his mind. He prepared my ass so perfectly, lubing it well, and slowly, very slowly pushing his way inside my asshole, my very stimulated asshole. . And just when James had his head in my tight hole, I vibed my clit as it started to build and cum and James remained motionless.
AH, she thought to herself, when a woman has cum in her ass a few times, she’ll relax her ring and then the man can fuck her properly.
This was a feeling Sherrie could have never described before.
She hoped, for James that the quaking cumming in her tight ass was his sheer heaven. Filling her ass with his cum was the most erotic experience she had ever felt.
There was no conversation after that act.
“Well, you were knocked out,” mocked James.
“Excuse me; are we ready to go James? playfully asked Sherrie.
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