It began innocently enough. He was a typical sixteen-year-old young man, a good student, churchgoing, and an all-around athlete. But Tom had a secret, he jerked off twice a day looking at Playboy Magazines.

Back in the 1980’s porn magazines were kept behind the counter to prevent theft. And to keep young teens from fraying the pages. The old Italian man who owned the small Mom & Pop bodega-style store would always give him a knowing nod.

After school, Tom would race home, pull off two paper towels in the kitchen, go to his bedroom, lock the door, and get out one of his five hidden Playboy magazines. He would drop his jeans to his ankles, sit on the edge of his bed, and choke his chicken as he’d flip through the well-worn pages.

When he felt an orgasm approaching, he’d shoot his load into a paper towel, ball it up, and then milk out the remaining cum so he didn’t have jizz tracks in his underwear. His hard-core Catholic mother would be mortified if she found evidence of his self-pleasuring activities. He would repeat this routine after dinner while his parents watched television and read the newspaper, telling them he was finishing his homework.

After masturbating for several months Tom realized he was very attracted to the young women in lingerie, stockings, and high heels. Sure, their makeup was flawless, and the photography top-notch, but he found that he’d cum quicker to these photos.

Flash forward a dozen years and Tom had purchased a beautiful and sexy outfit for his bride on their wedding night. It was, of course, white with a lot of feminine lace, had white stockings, and his wife wore her heels from the wedding. He loved it. She, on the other hand, did it for him. While they had been sexually active for several years, she thought it was a bit stereotypical for their wedding night.

Over the years of their marriage, he would purchase other pieces of lingerie for his wife on special occasions: their anniversary, her birthday, Valentine’s Day, or long weekend trips to the coast. She’d wear the lingerie to please her husband, but it would end up in the back of the bottom drawer in her dresser. Tom would occasionally pull a piece out and ask his wife to wear it for him which she would reluctantly do.  

But he would also do nice romantic gestures in the bedroom like candles, chocolate-covered strawberries and whipped cream, red twinkle lights, give her massages, etc. He was a bit of a romantic guy who enjoyed sensual and erotic sex, not a guy who just wanted to pound his wife. Tom had also purchased a few vanilla sex toys, like a vibrator, and a fun sexy dice game with specific acts on each side. Just like the lingerie, they’d be used once, maybe twice, and disappear to the back of her drawer.

As they got older sex was happening less often due to kids, commuting, and job stress. It also became a robotic quickie of fifteen minutes. A few kisses, a quick blowjob to get him hard, she’d ride him in cowgirl until she climaxed, and then he’d finish shortly after her, usually in doggy.

Flash forward to 2015; Tom was now a single man in his early fifties. He had purchased a condo in a gated complex near the river and lake. He was also on several dating sites like Match, Bumble, and even Tinder. Being a former college football player, Tom kept in shape throughout his marriage by jogging and doing a mild weight routine at the gym. He was now fifty-three, stood six-foot-two, two-hundred and twenty-five pounds, with short buzzed brown hair, and brown eyes. Tom dressed well and his female friends and co-workers agreed that he would be very popular with the single ladies.

Tom was hanging out at a nearby craft beer and wine bar, making friends, and becoming one of the regulars, meeting with a group of guys three times a week. He’d have two beers, shoot the breeze with the boys, and head home to make dinner. That was basically his social life.

After a year and a half of many first dates, Tom took out a woman in the neighboring town, just six miles to the north. Their first date went great with happy hour cocktails rolling into a full dinner date as they talked effortlessly about their jobs, marriages, kids, hobbies, and even some innocent flirting. At the end of the date, he walked her to her car, gave her a hug, and a nice peck on the cheek.

A few days later they met again. This time at the end of the date he felt that she wanted to be kissed. He gave her a nice lip kiss and counted to himself to three. He moved back and saw the smile on her face. He kissed her again. This time he slowly parted her lips with his tongue. She was a very willing recipient. They kissed passionately for ten seconds.

“That was really nice,” he said. “I could do that all night long.”

His date, Gina, giggled, and said, “Maybe on the next date.”

Tom and Gina saw each other again a few days later on Friday. Tom wanted to really impress her, so he picked her up at her house and took her to the best Italian restaurant in town. Their meals were delicious, and the bottle of wine went down easy with the salad, pasta, and yummy garlic bread.

Not wanting the evening to end he suggested they stop for a drink on their way home. “I have several bottles of wine at home. Let’s go back to my place,” said Gina.

“Great idea,” said Tom. He had visions of them making out on her couch all night. Since it was only their third date, he did not think Gina would be ready to get naked.

At age fifty-two, Gina was a beautiful woman. Five-foot-six inches tall, a slender size six dress, average 34C breasts, long brown hair with a few golden highlights, and brown bedroom eyes. She was a girly girl, so she curled her hair daily, wore fake eyelashes, and had cute fingernails. Gina was also very successful in her role as the Director of Marketing for a large regional bank.

Upon entering her home Gina gave him a quick tour, omitting the master bedroom. Returning to the kitchen she opened a bottle of wine and poured them each a glass as they sat at the large kitchen island. As they chatted Tom had put her hand in his, a move Gina noticed and gave him a smile. A few minutes later, he simply leaned into her and kissed her quickly on the lips.

“Sorry, I’ve been wanting to do that all night,” he told her.

“You’re such a gentleman,” she said. “I like that. And you haven’t been pushy about sex. Some guys just want to get laid.”

“Well, thanks. I appreciate the compliment,” Tom said, laughing. “Every guy wants a physical relationship, but I want more. Words like romance, sensual, and erotic come to mind. Most other guys just want to get naked and pound.”

Gina leaned in and kissed Tom softly on the lips. “Hold on, I’ll be back. I need to powder my nose.”

While Gina was gone Tom took the opportunity to use the hall bathroom too. When he returned to the kitchen, he was wondering what was taking Gina so long. He pulled out his phone and was scrolling through his email when he heard her footsteps down the hall.

“Tom, do you like my pajamas?” Gina asked from behind him.

He turned to see Gina standing fifteen feet away in the doorway. She was posed like a model with one leg in front of the other, just crossing the other foot, and with one hand on her hip. “Wow,” said Tom. “Uh, yes, I love your pj’s.”

Gina was wearing a black bra and thong set, black thigh-high back seam stockings, a sheer black short kimono-style robe, and the same red heels she wore to dinner. She looked stunning. She slowly walked across the kitchen and wrapped her arms around his shoulders and neck.

“That was a great dinner, but I want to have you for dessert. Would you like to go to my bedroom?” she whispered.

“Yes,” I said. “How did you know I love women in lingerie, stockings, and heels?”

“Oh, just a guess,” she laughed. “C’mon, follow me.”

Tom purposely held back just so he could walk behind Gina so he could check out her sweet ass. The black thong went up her ass crack and across her waist. “With that fine ass I’ll follow you anywhere,” he teased.

She already had soft music playing on a wireless speaker and several candles lit on the dresser and side tables. Her bed was untouched and full of pillows. Not surprisingly, there was a huge leopard print theme in her room with her pillows, a throw blanket on the bed, and lampshades on each side table.

Gina turned to face Tom and kissed him passionately. She slowly began unbuttoning his dress shirt and tossed it to the side. “Sit down,” she directed him. She then went to her knees and untied his leather shoes and took them off, as well as his socks. “Stand up,” she said. Looking directly into his eyes Gina started to unbuckle his belt and dropped his pants. She hooked her fingers in his elastic waistband and pulled down his boxer briefs revealing his nice six-inch semi-erect cock.

Tom stepped out of his pants as Gina took hold of his dick with one hand, held it up, and licked his balls and shaft in one, long, slow motion.

“Oh, fuck. That felt great, and looked even sexier,” he whispered.

Gina giggled, “If you liked that, you’re going to love the rest of the evening.”

Kneeling between Tom’s legs she began with a slow sensual blowjob. Long licks of his shaft, sucking his balls and teasing the tip of his helmet with her tongue. Her ruby red lipstick made the experience even hotter as Tom watched every second of the five-minute oral experience.

“Ohhhhh, Gina, you better stop or I’m going to cum,” Tom said. “Why don’t you let me return the pleasure.”

He helped her up off of her knees and kissed her passionately. With one hand he reached behind her and unclasped her bra exposing her perfectly shaped breasts. He admired her medium brown areolas and her dark nipples. Tom kissed his way down her neck and soon was kissing, licking, and sucking on Gina’s breasts.

“Yes,” she whispered. “Keep doing that, it gets me so wet.”

Tom grinned and continued as he led her to the mattress, and both lay down. He went back to her mouth and played tongue hockey as he was rubbing her pussy over the small triangle of sheer fabric. He could feel her warmth and wetness.

“Eat me. Make me cum,” begged Gina.

He quickly pulled down her thong and moved between her legs. Gina’s “vajayjay” was impeccably groomed with a long thin landing strip above her clit. Tom noted her engorged clit as became intoxicated with her musky aroma.

Just as he did minutes before, Tom started low near her starfish and licked upwards in an ultra-slow manner, allowing the velvet texture of his tongue to drag across her lady bits. After making contact with her pleasure nub, he flicked her clit several times.

“Oh fuck!” moaned Gina.

He flicked it again to tease her and then started to suck on her little tic-tac. This drove her crazy, causing Gina to squirm as she pushed his head into her honey pot.

“YES!” shouted Gina out of nowhere. “I’m about to cum. Keep sucking, baby!”

Tom felt her legs wrap around his head and shoulders, her body started to shake, and her pussy was like a river flooding his mouth with her sweet nectar.

“Oh… Oh… Ohhhhhhh fuck!” yelled Gina. “Oh my god! Yes! I’m cumming!”

Tom reached up and pinched one of her nipples.

“Yes! God, I love that!” shouted Gina.

He pinched her other nipple as he laughed while looking up at her face.

Gina was in another zone, unleashing her sex demon. “Fuck me. Give me that big cock. I need to be fucked, now!”

Tom was more than ready, with his semi-erect six inches now about seven and a half inches at full strength. He moved up and slapped his crown on her clit, then rubbed the head along her wet slit causing Gina to moan lightly. Tom pushed his cock into her pussy and was happy to feel her tightness.

“Fuck, you’re so tight,” mumbled Tom.

In between her moans, “I do Kegels,” admitted Gina.

The pair fucked in missionary for several minutes before she climaxed for the second time. Tom could feel her pussy spasm around his dick, but this was nowhere near the explosive orgasm Gina had earlier. When finished she unwrapped her stocking-clad legs and stiletto-wearing feet from around Tom’s waist.

“Ride me,” stated Tom. “I want to suck your tits as I fuck you.” He rolled over on his back and Gina mounted his big hard cock.

As they started in a slow rhythmic fuck Tom pulled her close so he could savor her breasts. Kissing, licking, and sucking her milk melons caused Gina to moan once more.

Tom’s loins were starting to tingle, his ball sack tighten, sure signs of an approaching orgasm. He began bucking his hips and thrusting deep into her pink cave. Suddenly, he yelled, “On your back! Get on your back!”

Gina did as directed, and Tom stood on the side of the bed and started to stroke his cock.

“Yes, shoot your spunk on me!” she said.

As the first rope of cum shot from his cock Tom laughed, aiming his pearl spunk for Gina’s red heel. His white jizz landed right on her stiletto and the second blast on her black stockings. A few globs went on the sheets, but Tom milked his dick of the remaining cum onto her other red heel.

“Oh, you freak! Cumming on my heels and stockings, huh?” she said. Gina took off her heels and seductively licked his cum off her red Jimmy Choo’s.

Tom confessed to Gina, “I’ve had a stockings and stilettos fetish since my teens. It’s all Hugh Hefner’s fault.”