Former Playmates Pt. 09: Tiffanie's True Desire

She didn't flirt with them. She didn't touch them at all. She talked and laughed with them. Some were shy, some were outgoing, but Tiffanie could tell, all of them wanted her.

She and Tom made eye contact several times. He was on the other side of the pool chatting with a friend and his girlfriend. Eventually she caught Tom watching her, watching the guys around her. She gave him a sweet wave, hoping this suggestion was having some sort of effect on him.

It did. Later that night, Tom was in her bed, watching a movie with her. He wasn't speaking much, but knocked on her door, came inside, telling her he figured he would hang out a bit. Tiffanie had no idea if he was jealous or wanted to spend time with her that night to make up for not being able to at the pool.

"Cuddle?" Tiffanie asked, a large towel still wrapped around her body after her shower.

"Sure, I guess," Tom shrugged again, extending his arm for his mother. Tiffanie didn't watch the movie, instead laid against Tom, breathing in his scent, enjoying his warmth.

When the movie ended she asked him to stay with her for the night. He declined. "Please?" she asked.

"Nah. Maybe tomorrow," Tom said.

"Ok. I'm proud of you by the way. Very, very proud of you. You were taking all those advanced classes and now you're done!" Tiffanie said, giving him a hug and a kiss on the lips, taking him by surprise.

"Yeah. Thanks," Tom said, still withholding information from her about his cross-country college acceptance.

"Remember tomorrow night," Tiffanie said, smiling as her son left her room, closing her door.

"Ok. Tomorrow night."

She undid the towel, letting it fall to her feet, standing nude, "Good. I'll be waiting for you," she whispered.

Chapter 5

"I sleep in the nude," Tiffanie told Tom the next night as soon as he entered her room, closing the door.

"What?" he said backing away.

"No," Tiffanie said, pinning him against the door, preventing his escape. "You aren't leaving. I want to spend as much time with you as possible. If you feel uncomfortable with my nudity, you can get naked yourself, or sleep outside the covers."

"Fine," Tom said. "Let me know when you're in the bed and covered up."

"You're safe," Tiffanie said, lying on her side, propped up on her elbow. "You sure you don't want to lose those pajamas? It's quite comfortable feeling bare skin against the sheets."

"No thanks," Tom quickly replied, hoping she'd drop it. Tiffanie giggled, moving closer to Tom. He pulled a blanket over his legs.

"Hold me?" his mother asked. Tom rolled his eyes. "Relax, my skin won't be touching yours. I'm under the covers, remember?"

Tom sighed, "Alright. Fine."

She turned off the lamp next to the bed, part of her breast coming exposed from her stretching. Tom didn't notice.

Her arms and upper back exposed, she snuggled against Tom. Pulling his face toward hers, kissing his lips, she said goodnight. "You're the only man for me. I realize that now. Goodnight."

Tom, confused by her statement, simply replied with a "goodnight" of his own. Tiffanie lay in his arms, wide awake, pretending he was under the covers and naked with her after a steamy lovemaking session.

Her wet pussy giving her courage, she waited until Tom was asleep. Tiffanie sat up, the sheet coming off her body, revealing her breasts. She looked at her sleeping son, smiling seductively.

In the low lit room, she pulled his blanket back, careful not to disturb him. "Just a peek. That's all," She whispered.

Her heart racing, she held her breath, slowly, gently tugging at his pajama pants and boxer shorts. Tiffanie stopped, getting an idea. She hopped off the bed, put her shoulder-length hair in a pony tail, found a flash light on the bedside table, and got back on the bed.

"There. Let's get a good look at you," She grinned. Resting on her elbow, hovering over Tom's midsection, she tugged his pajama pants and underwear down once more.

"Oh baby, oh baby," she whispered, mouth trembling, the flashlight illuminating Tom's tuft of pubic hair and flaccid penis.

Tiffanie lowered her head, inhaling his scent, "Wow," she whispered.

She wanted to devour it, to bring it to life, suck it dry. "I'm going to have you inside me. I'm going to drink from you," she told his sleeping cock.

Turning off the flash light, she leaned in close to Tom. "I'm going to take care you, Tom," she whispered in his ear. "Mmmm," she moaned, "I'm going to fuck you so good."

Tiffanie had to remove herself from the room. She hopped off the bed again, rushed down the hall, and stepped out onto her back deck in the hot, humid, night air. "This is where it began," she said. "This is where I saw a mother and son together."

She was slowly rubbing her clit, pacing around the deck, the full moon providing all the light she needed. "Tom. Yes."

"Take me," she said again, leaning back on the rail, just like her older sister Diane did that fateful night.

"Yes!" she pretended Tom was there, holding her legs, slamming his cock into her as hard as he could. Tiffanie picked up the pace, furiously rubbing her clit. "Yes! Yes!"

"Harder!" She imagined her son gritting his teeth, working up a sweat, just like she was.

"Yes! Yes! Noooooooo!" Tiffanie fell over the railing, landing with a thud, six feet below on the wet grass. She erupted into laughter after discovering no injuries. She wasn't done though.

Not caring if the neighbors heard or saw her, she kept masturbating in her back yard. Rolling around on the ground, pretending Tom was with her, she made it to the middle of the yard. She was on all fours now, reaching past her stomach, rubbing her clit, dipping her fingers in her cunt, and rubbing some more. In her mind Tom was behind her; owning her.

Like a wolf howling at the moon, Tiffanie cried out into the night, as the most powerful orgasm she ever had over took her. Not caring if she woke the neighbors or Tom, she collapsed on the ground, breathing heavily.

When she calmed down, she laughed at herself, climbed over the railing of the deck with some difficulty, planting her foot on the floor of the deck, and pulling herself up and over. She went inside discovering Tom was still asleep.

After a shower to clean off the dirt and grass, she stood, naked in the bathroom doorway, the light behind her silhouetting her body, watching Tom sleep, grinning devilishly. She wondered if this taboo and perverse desire was genetic. Perhaps it was why all her sisters were sleeping with their sons. She didn't know and didn't care. All she knew she was fully embracing it, her true desire, and would very soon cross that line with Tom.

Chapter 6

Tiffanie sat next to Tom on the plane ride to the Bahamas. She held his hand, thinking back to the last time they were on a plane. It was in November and it was to the very same destination. Tiffanie was in the bathroom getting fucked by the friend she brought along. This time, however, she was sitting next to her son, holding his hand, and thinking of all the wonderful and beautiful things she wanted to do to him. She was going to make things right.

They rode a shuttle bus from the airport to the resort. Tiffanie curled up in Tom's arm, ignoring the annoyed look on his face. Last time they were there, Tiffanie was curled up in her friend's arm, squeezing and tugging at his erection through his shorts, hoping her son would look over and see it; see that his mother wasn't an incestuous sicko like his aunts.

But now she was. Tiffanie fully embraced her taboo urges, no longer running from them -- from Tom. She pulled his face to hers, kissing his lips.

Tom pulled away, "Mom, geez."

Tiffanie smiled, wiping his lips with her thumb, "I love you."

Tom looked around the bus, nodding to his mother, "Love you too."

Tiffanie couldn't wipe the smile off her face. He was so shy. All that would change by the end of the trip.

There was an issue with getting the same villa as last time. The front desk manager who checked them in informed Tiffanie of their blunder.

"It's ok. This is a new trip, so a new room is fine," She said.

The employee looked at Tiffanie and Tom, "Is he your son?"

"Yes."

"I think I have the perfect room for you two," the employee smiled, giving Tiffanie a wink before printing off their paperwork.

*********

"Oh wow, this is amazing, Tom!" Tiffanie placed her bag on the bed, and checked out the bathroom. The shower was huge. Her first thought was that it could easily fit her and Tom in there.

"Look out here! Oh my..." Tiffanie looked into the small courtyard, noticing the hot tub. Tom stood next to her, looking around.

"Maybe later tonight, I can have some wine delivered, we can get in there," Tiffanie turned around and tickled her son, "we can have fun!"

Tom flinched, "Yeah, sure." He shrugged.

Tiffanie went back to her bag, leaving Tom behind to look around. "I'm changing into my bikini and then we'll hit the beach."

A few moments later, Tiffanie emerged from the bathroom wearing a brand new bikini. It was a tiny, black, string bikini, leaving little to the imagination.

"Well do you like it?" She asked her son, laughing as he looked away embarrassed. She approached him, grabbing his hands and placing them on her waist.

"Do you think it's sexy?" she asked.

"Mom, I -- "

"Hey, It's ok. As a woman, do you think I'm sexy?"

Tom sighed and shrugged.

"Hey, look at me," Tiffanie pulled his face to her smiling face. She smiled, looking down at her cleavage. "Do you think I'm sexy?"

"I, I guess," Tom stammered.

"Good," Tiffanie grabbed her bag. "I suggest you relax and don't think of me as a mother, but a friend, a woman you're on vacation with. A vacation needed for both of us to reconnect, this time as adults."

Tiffanie winked at the 18-year-old, gesturing him to follow her. They locked the door and headed to the beach, Tiffanie holding Tom's hand.

*********

They were inseparable, much to Tiffanie's delight. Unlike last time, in November, they spent the day together. They didn't talk much. Thoughts of making love to Tom, to giving herself to him, filled her mind -- but she remained calm and quiet, enjoying the sun, sand, and her son.

She dragged him into the water, straddled him, held him, and looked into his eyes, occasionally giving him kisses on the cheek and lips. She was savoring every moment.

Tom didn't protest too much, Tiffanie wondered if deep down he didn't mind her large breasts, barely covered by a bikini top, mashing against his chest.

That night they went to dinner. She wore a nice sundress, no underwear. There was a candle in the middle of the table; she held his hand, sitting across from him.

Moments later, slow dancing with a few of the older couples at the resort, "Did you notice something about our room?"

"What?"

"It only has one bed. Are you ok with that?" Tiffanie asked.

"Yeah, I guess. Sure."

"Are you going to be ok with me sleeping naked?"

"Uh, well -- "

"Tom?" she put her hands on his face, "you don't have to be uncomfortable around me."

"I know, it's just a little weird. I'll sleep outside the covers again."

"Ok," She smiled, accepting that compromise once again.

Back at the room, Tom emerged from the bathroom in pajamas. Tiffanie started undressing, glancing at Tom while she did, seeing him avert his eyes, too bashful to look.

Just like the other night, Tom held her covered nude body against his. After a long day of travel, Tiffanie was too tired to wait for Tom to go to sleep. As she drifted off, she thought back to the previous trip. She climaxing over and over again the first night, while Tom was outside or across the villa, his room shut. This time, she was doing things the right way. She was in his bed, in his arms, right where she belonged.

Chapter 7

"What? What is it?" Tom asked his mother the next day after breakfast. They were in a nearby pool; she was once again, straddling him staring at his face, quiet.

"Nothing. Just admiring the view."

"You're funny," Tom said.

"You look a little like my father," Tiffanie said, referring to her biological father, Bob.

"Really? I never saw that resemblance."

"When he was younger, yes," Tiffanie thought back to the day she learned of Bob's true identity, seeing pictures of the college age Bob with his mother, Tiffanie's mother.

"I love you," Tiffanie said once again.

"Mom, are you sure you ok? I mean I know you want to make up for not being around much in the past year or so, but you just seem so different now."

"I'm more than ok, Tom. I'm perfect. I feel great, I feel like everything is working out wonderfully."

Tom thought of telling her about college. She thought he'd be attending a nearby community college for a couple years, getting his core classes out of the way, and then transferring to a four year school to finish. Seeing her happy face looking at him made him hesitate once more.

"Things are going to be changing for us," Tiffanie said. "They will be changing for the better. I can't go into it just yet, but on this trip, you'll know what I mean by the time we leave. Please just go with it, let me change our relationship for the better."

"What are you talking about?"

"You'll see, just go with it. I promise you everything will be perfect."

The rest of the day was more of the same -- quiet closeness between mother and son, Tom gradually loosening up a bit, not flinching when she kissed him. Sometimes he'd rest his hands on her waist while she gave him a longer-than-normal kiss on the lips.

That evening was another romantic meal, followed by a walk under the stars, with Tiffanie's hand holding Tom's arm.

*********

Tom awoke the next morning hard as a rock -- more so than normal. He felt a warm, soft body resting against his. His hand glided up a bare back, feeling the silk skin. He moaned, feeling a heavy mass against his side -- two large breasts.

His eyes shot open upon realizing the body belonged to his mother.

"Hi," she said, smiling at him. "Sorry, I got hot under the covers. I figured this blanket you were using would be better. But then I got chilly, so I snuggled up to you. Now I'm just right."

"Uh, ok," Tom said.

Tiffanie rose up, kissing his cheek, her tits dragging across his chest. Tom looked away, not seeing his mother crawl out of bed. He kept his eyes closed, hearing fabric of her bikini thong slide against her legs. He quickly opened and shut his eyes. In that split second he saw his mother, back to him, looking for the bikini top. He could see the sides of her breasts from behind.

"Get dressed. Let's go," Tiffanie said, pulling the blanket away from Tom. Moaning inwardly when she saw his tented pajama bottoms.

"Looks like someone else is ready to go," Tiffanie smiled, glancing at his bulge, sitting next to Tom on the bed. She ran her hand over his chest.

"Mom, I'm sorry, I -- "

"Got excited from holding a naked woman in your arms?" Tiffanie asked. Tom's eyes darted from side-to-side, thoroughly embarrassed.

"Aww, it's ok," Tiffanie said, throwing her leg over Tom, climbing on him, straddling him. He looked on in shock when his mother lowered her crotch on top of his.

"See? No big deal," She said, fighting a burning desire to rip his pajama pants off and shove his cock inside her hungry pussy. "Actually, it kinda is a big deal."

Tom's face turned red, picking up on his mother innuendo. "Um."

"Come on, let's get going," Tiffanie said, climbing off her son, giving his tenting pajamas a look and a smile.

The rest of the day was noticeably more uncomfortable for Tom. Tiffanie thought nothing of it, spending all her time with her true desire -- her son and enjoying every hug, kiss, and caress she gave him.

That night she went to bed, undressing once more, climbing on the bed under the same blanket Tom was under. He didn't protest this time.

"You going to fondle me in my sleep?" Tiffanie joked.

"What? No, no way," Tom said.

"You can if you want to," Tiffanie said, lying in his arms. "I wouldn't mind being woken up by a man running his hands all over my naked body."

Tom shook his head, closing his eyes, feeling more uncomfortable.

"I love being held like this," his mother said, placing his hand on her waist.

A moment passed, Tom was incredibly tense. "Tom?" Tiffanie asked rising up on her elbow. "Are you a virgin?"

"Mom!"

"Sweetie, don't be shy. You can tell me anything."

"Ugh."

"Well?"

He hesitated more. "I had a girlfriend but it never got to that point."

"Sex?"

"Yeah. OK? Is that what you wanted to know?"

"What did you two do?"

"We kissed some and, well," Tom paused.

Tiffanie kissed at his cheek, jaw, neck, whispering in his ear, "Did she suck your dick?"

"Ah geez," Tom said, attempting to sit up, to leave, but his naked mother pinned him down.

"No, no, you're not going anywhere," She said, straddling him, Tom looking away from her tits. "Did she?"

Tom nodded his head, yes.

Tiffanie leaned down, her breasts coming to rest on his chest, "Was it good?"

Tom shook his head, no.

"And why not?" She whispered, peppering his face with slow sensual kisses.

"Teeth," Tom spit out.

"Ah yes. Her teeth raked across your cock. Probably didn't feel good," Tiffanie was continuously kissing at his cheeks and neck now. "I had that problem too when I first started pleasuring men with my mouth. I learned a few tricks to help with it."

Tom gulped again, his breathing heavy, he wanted to run, but was too scared to grab her naked body and throw her off him.

"Now that I've mastered it, a penis easily goes into my mouth, no teeth raking across the shaft," Tiffanie paused a moment, kissing his lips slowly. "I love the feeling of doing it."

She was looking directly in Tom's eyes now, "I love it when a man ejaculates in my mouth. I love the taste of semen, sloshing it around in my mouth before I swallow it."

She kissed his lips once more, "Every last drop."

Tom panicked, "Ok get off me. Get off me!"

"Tom?"

"Please! Just move," Tom said, sitting up, his mother sliding off him on to the mattress. He rushed out the door, saying over his shoulder, "Going for a walk."

Tiffanie smiled, getting off the bed, walking to the hot tub in the back court yard area.

"We're going to the nude beach tomorrow Tom," she said aloud, letting the jets of the tub, massage her body, while she rubbed her clit.

Two hours later, Tom returned, finding his mother in the bed on her side facing away from him. He pulled the blanket over him, rolled over, and tried to go to sleep.

Chapter 8

Tom woke the next morning finding his mother already dressed, not in a bikini, but in a thin, spaghetti-strapped tank top, her large, full breasts busting at the seams to get out, and tiny, white shorts.

"Hurry! We have to make the ferry on time," Tiffanie pulling Tom out of the bed.

"Ferry?"

"Yes!" She said, pulling his t-shirt up over his head, running her hands over his body before pulling at his pajama pants.

"Whoa, whoa, I can remove these," Tom said, heading to the bathroom to change in to a new shirt and swim trunks.

They had a quick breakfast, Tom trying to forget about last night, his questions about where they were headed in the ferry unanswered by his mother.

The ferry was actually a small boat, large enough for about ten people, all sitting in rows of benches. Tom saw they were headed for an island not far off the coast. Apparently it was owned by the resort and this boat shuttled people back and forth from it all day.

When they arrived Tiffanie stood, waiting to get off. Wake from a passing boat hit their boat causing Tiffanie to stumble. She raised her hands to stop her fall. One hand went Tom's thigh, the other, to his crotch.