Mark was in his late thirties. He was what some consider a late bloomer. During his teens and twenties he was shy, nerdy, and a little heavy. He didn't get much attention from girls. His only sexual experiences were post-college with two long-term relationships.
He was successful in his tech career. He exercised regularly and was no longer heavy. He was now more handsome, but he was still generally a shy, timid person.
His last relationship ended a year ago. He had not put much effort into dating yet, partly because he was so busy at work and partly because he was not that confident with women. Thus when his friends, Angie and Tom, invited him on a weeklong trip to Palm Springs, he accepted.
Angie had relatives with two properties in Palm Springs. They lived in one and used the other as a vacation rental. If the house was not rented they offered it to family members to use for free.
"Hey, Earl and Gwen, invited us over for dinner tomorrow." Angie said as they were lounging around the pool the first day. "And, Mark, you are welcome to come."
"Um, I don't know... I've never met them."
"Ah, come on" encouraged Angie. "I haven't seen them in a while. They're my mom's cousins, from the Canadian side of her family. They must be in their 60s by now. I think they're kinda conservative... Christians. You know, the church-going type. But I remember them being pretty outgoing and friendly."
"OK, since they are allowing us the use of the house, it's probably the polite thing to do... so count me in."
The next evening, Earl and Gwen greeted the three of them with enthusiastic hugs and smiles. Everyone was given a glass of champagne as Earl insisted on giving them a tour of the house. He made sure they saw the expensive cars in the garage. They lived in a very upscale seniors-only neighborhood.
Earl was 70. He was a retired engineer who had worked in the oil industry. He talked non-stop. Although he was friendly, he was arrogant and boorish.
Thus Mark was relieved to be seated next to Gwen at dinner at the opposite end from Earl. Gwen was 65 years old and energetic. She gesticulated dramatically as she talked. Her voice became louder with every sip of her wine.
She bragged about her many physical accomplishments such as her European bicycle tours and squash tournaments. She was quick to disparage her female acquaintances for not being in as good of shape as her.
As far as her male acquaintances, she implied there was sexual tension with all of them, regardless of any age difference. By her account, her dentist, accountant, and several neighbors were all in love with her.
Mark decided Gwen was just a rich conceited snob. Soon he was completely ignoring her words, nodding and smiling periodically. Maybe he was a little tipsy too, because he found her annoying yet a little hot.
She was slender and petite. She had thick straight gray hair with bangs that stopped just above her shoulders. She had high cheekbones and a slender nose. She maybe had a little botox, but she looked very natural with wrinkles in all the right places. Mark was certain she must have been a knockout in her youth.
She frequently leaned into him, brushing her bangs out of her face as she talked. She used every opportunity to make sexually charged jokes or innuendos. She probably flirts with every man she meets, he thought.
Mark had to hide his erection the rest of the evening as he mentally vetted different possible scenarios, all of which ended with him fucking her. He had never fantasized about having sex with a 65 year old before.
The next morning, Mark showed up unannounced at Gwen's house. He knew from the dinner conversation that Earl would be at a golfing tournament. He was hoping Gwen would be home and alone. He smiled when she opened the door.
"Uh... well...Hello Mark" she stammered, obviously surprised to see him. She was wearing a slim white athletic tank top and white capri linen pants. She had on white ankle socks and white sneakers.
She quickly regained her composure and defaulted to her usual flirtation. "Well, if I had known I was going to have company, I would have put on something a little more appropriate." she said playfully.
"Well, I think you look great in white!" he said as he nodded approvingly.
Gwen was not sure, but she suspected this was his attempt at flirting. "You'd better come in, I don't want my neighbors seeing me entertaining strange men while Earl's not home. Heaven knows what kind of reputation I'd have!"
Mark was already getting hard. He had hoped she would flirt with him. Things were going according to his plan as he laughed and walked into the living room.
"Thanks Gwen! Sorry to bother you, but I just wanted to take you up on the offer of getting a few grapefruits from your tree." He said innocently.
"Oh, Ok... if that's all, I suppose that's fine, too" She pouted and feigned disappointment. "But you can't blame a girl for hoping!"
"Actually, the grapefruits are for Angie and Tom. I like grapefruits, but they make my tongue itch. And my tongue is one of my best assets... so the women tell me." This was the cheesy line he had mentally rehearsed.
Gwen was surprised at the directness of his now obvious flirtation. He seemed innocent enough, but more importantly she did not want to be outwitted. She replied "Awww, if only I was as lucky as them."
Mark stepped forward and reached around her small waist and squeezed her ass. "Oh Gwen, today's your lucky day."
She gasped. "What are..." He silenced her with a finger to her lips. He brushed her gray bangs off her face, tucking them behind her ears. He placed his hands firmly on her hips and guided her backwards until she bumped into the couch.
She was stunned as she felt him unbutton her pants. "Um... um... but, Mark, I'm married." she stammered. He casually squatted down and calmly pulled off her sneakers one by one.
"I've... I've... never cheated on Earl before..." She paused, then almost whispered "I've only ever been with him."
He stood up and moved his mouth close to her ear and whispered "Well, that makes it even hotter." He slid his fingers under the waist band of her pants and panties. "If you want me to stop, just say the word, OK? Do you want me to stop?"
She was breathing hard now. She was speechless as she found herself shaking her head no.
He pushed her pants and panties down around her ankles. Then he pushed her backwards onto the couch. He dropped to his knees and eased her pants and panties completely off.
He spread her knees apart. His hands moved slowly along the inside of her thighs from her knees to her crotch. He leaned in between her legs.
Being rich and attractive, she was accustomed to being in charge, especially in interactions with men. But now she was a little scared being in this situation and not in charge.
For Mark, too, this was a role reversal. He was usually shy, especially with women. But now, clearly in command and full of confidence, his cock became completely hard.
He nuzzled her full bush with his nose before giving her pussy a slow long kiss. Her body quivered and she groaned softly the instant his lips made contact.
He looked up. "Oh Gwen, I don't think this pussy has been licked for a long time! Do you want me to lick your pussy, Gwen?"
Almost without thinking she blurted out "Earl's never done it... he thought it was dirty. We've only done it missionary." She instantly regretted her confession. But it was somehow cathartic. Suddenly she felt a little lighter and strangely happier.
The thought of him being her only second sex partner made him giddy. He was barely more experienced than her, but she did not know that. He mentally steadied himself to stay in character.
"Oh well, no biggie." He said flatly. "If it's not your cup of tea, that's fine. But if you want your pussy licked, you should ask me politely."
"Yes, please. Please lick my pussy."
Mark energetically kissed and licked her pussy. She was moist. Quickly she was wet, wetter than she had been in years. She closed her eyes and moaned softly as he sucked on her clit.
He looked up as he lifted both her legs over his shoulders. "Wow Gwen! You have a lovely pussy. Did you know that? It deserves a good licking." He dove into her again with his tongue exploring her inside and out. Her moans got louder.
One hand was under her ass squeezing her butt cheek while the other hand was hooked around her thigh rubbing her clit. The whole time he sucked, licked, and kissed her cunt.
Mark was not very experienced in the art of cunnilingus. But by the way he felt her body quiver, her thighs squeeze his head, and hearing her quickening rhythmic gasps, he knew he was on the right track.
He paused and looked up. "Do you like it or shall I stop?"
