The Ultimate Date

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"You do that to me all the time. Kissing you, well it was almost too much."

"That's not me, that's you being eighteen years old and male!"

"Shhh. Of course it's you."

Leaning forward he brushed his mother's lips. Jillian raised a hand to her face, fingers tracing where he had just been, and he saw her struggle with her emotions for a moment before making a decision and, for the first time, taking the initiative.

The feel of her lipstick against his skin was so erotic Paul was sure he would cum if he wasn't careful. It wouldn't take him long, especially with his present company, to get hard again but somehow he knew if he blew his load his mother would leave and that thought alone was enough to take him back from the brink.

Instead he began to concentrate on the kiss and how it made him feel. The heat of her body next to his, the feel of her hair as it brushed his forehead, again the silkiness of the lipstick, all made a lasting impression on him. With a moan he ran a hand up onto her shoulder and moved so they were laying as close as they possibly could.

"Let me see you, mom, I want to touch your skin, kiss you, God, I want to make love to you, please."

The heat of the moment had gotten to him and Paul blurted out his desires. Fearfully he looked up but, to his delighted surprise, his mother didn't look at all annoyed or disgusted.

"You are so young, baby, why do you want to be with me? And what ... what would your dad say?"

"He doesn't ever have to know, I'm not gonna tell him or anyone else for that matter. As to why, that's easy. No one compares to you, mom ... Jillian, they never will. We ... we don't have to go all the way, I just want my first time to be with you."

The room was suddenly silent but the pressure seemed to push down on him as he waited for her response. Slowly she moved away, got to her feet, and his heart sank. Then, with a half smile, she spoke again.

"You can't touch me if I'm still wearing these clothes. If you help me take them off I'll do the same for you."

"Uhhh ... oh, fuck, God, I ... I mean yes ... yes, ma'am."

Scrabbling furiously he moved himself across the bed, almost falling at his mother's feet in his haste to do as he had been told.

Finally, standing next to her, he closed his eyes for a moment to ground himself and then, with shaking hands, reached out.

The buttons on her shirt seemed impossibly small or his fingers impossibly large but gradually he undid all of them. His mother, smiling sexily, shrugged her shoulders backwards and the shirt shimmied to the floor behind her. Her hands moved to the fastening of her bra but Paul moved too.

"No, please, for a while, leave it. I love the way you look with it on. So beautiful." He moved slightly and, with a deep breath, placed a tender kiss on each of the soft smooth globes before looking up to see nothing but love in her eyes. Her approval spurred him on and it was easy to find the clasp to his mother's skirt. In two smooth movements it too lay on the floor with the shirt and his mom stood before him naked except for matching bra, panties and stockings.

"My turn I think."

He stood, almost statue-like; apart from the shiver each time her fingers brushed across his shirt, and let his mother take all his clothes off. When he was totally naked he watched as she carefully removed her own stockings and panties before lying back on the bed.

They both knew they had reached a point of no return. If they carried on then things would change between them forever and for a moment Paul watched as, again, his mother thought through what they were doing. Finally he saw her take a deep breath and reach out to touch him gently before speaking.

"I can't believe I am going to do this, but please, Paul, I want you to touch me, kiss me again, even make love to me."

Everything seemed to move in slow motion as he climbed back onto the bed kneeling beside her as he was suddenly totally unsure what to do next.

"You can sit on me if you want, sweetheart, that way we can reach each other easily."

With a silent nod of his head Paul did as he was told and was almost instantly straddling his mother. He leant down, his hard cock now resting against her dark pubic hair, and kissed her again, gently at first but found he couldn't control himself and his kisses got more fervent. The tenderness of their previous embraces was gone, passion took over for them both and, as Jillian's fingers wove into his hair, Paul rubbed himself against his mother, enjoying the new sensations and trying to remember everything they were doing.

Gradually the kissing was replaced by tender touches as fingers explored the new bodies before them. Paul, feeling his mother trace the vertebrae of his spine, let out a moan, and shuddered.

"You always loved that as a baby, I could get you to fall off to sleep easily when I ran my fingers up and down your back."

"I remember. Now though it just makes me feel so good. Tell me where you like to be touched, I want to make you feel this way too."

His mother paused and Paul knew she was still having problems with what they were doing.

"Please, Jillian, let me do this, just once."

"I love to have my skin touched, just as I'm doing to you. Almost anywhere feels so good. I ... my ..." She took in a deep breath and Paul could almost hear her regulating her thoughts and giving herself permission to continue. "My nipples, lick and suck my nipples, baby, please."

The groan that left him was one of acute arousal and finally he reached forward to release the catch on the beautiful bra his mother was still wearing. Her breasts, so smooth and white, slipped from their restraints and he saw, for the first time, her large, dark nipples, already puckering before he had even reached out to caress them.

"Oh, God, mom, so beautiful, so sexy ... like this?" He took the left nipple into his mouth, sucking on it and running his tongue over the now rock hard nub.

"Yesss, baby, just like that. Ohhhh, harder, suck harder. Yesssss, ohhhhhh, yes." Jillian's back arched, raising her off the bed and Paul reached out to play with the unattended nipple. His mother's head thrashed on the bed, her hair already disarranged, as her breathing got heavier and movements more languid.

"Mmmmm, don't stop, please, don't stop, Paul, baby, love ... love it ... you, love you."

Her words, broken by heavy breathing spurred him on and Paul moved so that his now throbbing cock was against her hip. Pressing down he began to cant his own hips so the movement stimulated him.

"Kiss ... move across ... the other one, Paul, please, suck my other tit too."

Moving his head back just a little Paul began to place butterfly kisses across his mother's chest until he could take the other nipple into his mouth. As he once again began to suckle on her he felt her begin to stiffen.

"Mommy's gonna cum, baby, ohhh, god, find my pussy, Paul, touch me there, please, help me cum ... yes, oh yes."

His fingers had no sooner touched the silky soft skin between his mother's legs for the first time than they were soaked with juices. He kept suckling as he stroked her pussy lips feeling her shudder again before letting out a deep sigh and relaxing back into the mattress.

"Was ... did I do ok?" He knew his mother had cum but wasn't sure how much he'd had to do with it.

"Are you kidding? That was wonderful. Come here, darling, just lie with me for a minute or two. I'm not done yet."

For a while they said nothing, Paul rested his head on his mother's shoulder, kissing the skin beneath it before he changed position so, instead, his mother was leaning on him.

After both of them had caught their breath and looked at each other furtively a few times Paul moved away and grasped his mother's purse from the side of the bed. Passing it over he looked into her eyes and smiled.

"Could you put your lipstick on again?"

"Sure, honey, but why?"

For a moment he was quiet. He'd always liked girls who wore pretty shades of lipstick but now he'd kissed his mother when she was wearing it, it had become so much more than that.

"I liked the feel of it ... when you kissed me and ..." He paused, not sure if he should continue or not.

"And? Paul, I think we have probably got to the state in our relationship where we can pretty much talk about anything!"

"Yeah, I guess so." The atmosphere suddenly became totally relaxed and Paul shook his head and smiled before continuing. "I want to see what my cock looks like with your lipstick marks on it. And my nipples, and my ... and my ... my everywhere."

It was his mother's turn to smile and her dainty laugh filled the room before she took out a small mirror and the gold case her lipstick was kept in.

"Can't have me not kissing 'your everywhere', now can we?" Slowly, sensuously she applied the sexy gloss before carefully dropping everything back into her purse and placing it on the floor by her side of the bed.

"So, lipstick and bras. You had better explain, young man." The stern voice she used was similar to the one Paul had heard when he was young and left broccoli on his plate. Not at all fazed he nodded his head and, reaching for her hand, cleared his throat.

"You are the sexiest woman I've ever seen and the lipstick makes your lips look so ... so wonderful. The first time I thought about kissing you, touching you, making love to you, you were fast asleep in your underwear. I ... I could see your hair curling round the lacy panties and your nipples through the bra. It was so hot, so sexy. I wanted you to be like that just for me."

"You like the hair?" His mother touched her pussy as she spoke and he nodded.

"Oh yeah, I want to bury myself in it, to taste you, lick up your cum ... if you'd let me."

"You would eat me out?"

"Ummm, yeah, is that what it's called?"

"Yes, darling, that's what it's called. Your father won't do it, even though he knows I love it. I'm not going to stop you if you want to try."

He nodded his head and then forgot everything as he felt a warm hand touch his cock.

"I think I would like to play with this first though, if you'll let me."

"Ohhhh, God, yes, but slowly, don't want to cum yet. Don't let me cum yet, Jillian."

"Can you cum twice in an evening, baby?"

He nodded; not daring to believe his mother would want to let him do so.

"Then I'll make you cum this way first. Maybe taste you."

Paul let his head fall back against the pillow. His senses were already on overload, but now he had the chance to let his mother jerk him off and then wait for him to get hard again to do something more.

All thoughts left him as the fingers, grasping him firmly yet tenderly, began to move. Slowly at first they rose from the base of his cock up the eight inches until they were teasing at his hard, throbbing head and then, unbelievably everything stopped.

Moving his hips, trying to get his mother to carry on, had no effect and for a moment Paul raised his head to see what was happening. It was obviously what Jillian had been waiting for because immediately she lowered her head and, for the first time in his life, Paul felt the hot wet warmth of a mouth around his cock.

"Ohhhhhhhh."

"Shhhh, let me make you cum, baby. Just enjoy."

His hands began to play with his own nipples as his mother swirled her tongue around his hot prick. He pulled and twisted at them but stopped as suddenly he realised she was moving lower, taking him all into her mouth and then swallowing over his head. He felt her press her lips against his skin and as he looked down once again saw the lipstick stain around the base of his cock and knew he was lost.

"Ohhh, can't ... God, mom, can't ... fuck!" His body seemed to freeze and then suddenly he felt himself explode. Pulse after pulse of spunk shot into his mother's mouth until she moved back so the last shots landed on his curly pubic hair. Jillian licked her lips and reached down, running her finger into the white crème before taking it into her mouth, showing him her loaded tongue and swallowing.

"Ohhh, God. That was fantastic."

"Taste yourself, darling, then relax against me. If we are going to let his evening go all the way to the end, you'll need your strength for what I have in mind!"

He felt his mother begin to French kiss him again and for the first time his own cum rested against his tongue.

He had nothing to say; his mother had obviously decided to go for broke. Paul knew she would have difficulties with her decision later, but that could be dealt with then. For now he was more than willing to go along with whatever it was she wanted him to do.

~*~

The room had remained silent for quite a while although neither of them had been still. Paul had begun tracing lazy patterns on his mother's skin, knowing now how much she liked it. As she had lain looking at him he had gently drawn her face, running his fingers across eyebrows, cheeks and lips before leaning forward to kiss her once again.

In return she had, once again, run her fingers up and down his back, gradually working lower and lower until she was just dusting her fingers over the soft cheeks of his ass.

As the fingers finally began to dip in between the cheeks and towards his tight rosebud he began to moan again and she looked up.

"Your skin is so soft, Paul, I ... I want to lick it, kiss it, taste it all. Will you let me?"

He couldn't speak and so nodded his head, speechless once again. Jillian's fingers stopped moving and he watched as she moved closer and then her lips were against his own and the kissing began again.

His mother moved so she was leaning over him and then began to run her long nails over his nipples. The feeling as they grazed back and forwards was hard for Paul to describe but he knew he loved it. Just as he was about to reach out, to begin touching himself his mother moved again and suddenly his left nipple was being sucked and laved.

"Ohhhhh, that ... god, mom, so good." The warmth, the wetness made his other nipple desperate for some type of sensation and he began pulling on it himself, rolling it between his fingers, pressing tightly and relishing the feelings until his mother touched his hand with her own and he stopped.

"Let me, sweetheart, you have such sensitive nipples, I want to play with them, to make your cock hard and ready for me."

"Are ... you, you sure?"

"I wasn't, but yes, now I am. I want us to screw, Paul, fuck, make love, whatever you want to call it, I just want to do it."

"Screw, we can screw, or make love, I won't ever fuck you, mom, not ever."

Jillian smiled at him and once again Paul felt his heart swell with pride. His mother lowered her head and his right nipple was enveloped just as his left had been. The softness of Jillian's tongue and the nipping of her teeth tormenting Paul as he tried to reach down to pull at his cock, to take himself higher than he was already flying.

Again time seemed to stand still as he relished the new sensations his mother was showing him, and then, with regret, he watched as she sat up.

"Mom?"

"You said you wanted me to teach you, was that just a ploy to get me into bed or can I really show you what I like?"

"No, please, show me, I really do want to learn, but only so I can pleasure you." Paul felt a blush as it rushed up his chest and face but saw no condemnation in his mother's beautiful face and felt his confidence returning once again.

"I want you to eat me, push your tongue in my pussy, taste me, but I want you to do it while I am sucking your cock."

The room regained its silence but for a moment it was an uncomfortable one.

"Mom?"

"Baby, I want this now, maybe as much as you do, but it isn't something we are going to be doing again so I want to live out some of my fantasies as well as yours. Do you mind?"

"No ... no, of course not. Tell me though, tell me what it is you fantasize about; I want to make this as hot for you as it is for me."

Paul ran a hand through his hair, trying to take in all that was happening. His mother seemed to be speaking the truth and he had no intention of doing anything to dissuade her from the course of action she had chosen.

"A 69, I want to try a 69 with you, baby, please."

Paul realized in that moment just how naive he really was.

"Um, ok."

The relaxed light laugh of his mom breezed past him and he waited.

"Stay just as you are, I'll do the technical bits, ok?"

Nodding his head and wondering what he was getting himself into Paul watched as his mother moved up the bed and then straddled him in a similar fashion to the way he had done with her earlier.

"A 69 means we can both do the same thing at the same time. Just think about the figures."

With that his mom lowered her already dripping pussy towards his lips and with a moan that seemed to emanate in the depths of his soul Paul reached up to grasp her hips as his tongue began to lick slowly over the silky skin.

At the same moment he felt his cock being enveloped once again and the moan lengthened and deepened even more.

The taste of his mother was wonderful, Paul could feel her juices as they coated his tongue and the undulation she seemed to be able to make her muscles do only increased his pleasure.

He realized he had been thrusting his hips upwards and listened as his mother gagged on the head of his cock. For a moment Paul paused his movements but she didn't seem to be in any distress and, unable to remain still, he began to push into her once more.

Soft fingers ran over his balls and onto the sensitive skin behind them and Paul increased the speed of his own movements as he began to recognize signs which meant his mother was about to cum again.

Lifting her head off his cock Jillian began to moan loudly. She pressed harder over Paul's face but he had no intention of stopping.

"Oh, yes, yesssss, Paul, just like ... just like that. God, ohhhh, god, cumming, gonna cum, baby." The words stopped and Paul felt his mother's finger nails as they dug into his hips. Still unable to breathe he sucked and licked until suddenly his mouth was flooded with juices and his mom raised herself up as she cried his name once more and then flopped over to the side and lay next to him.

If Paul had thought his mother was in need of a rest he was mistaken. As soon as she had caught her breath Jillian raised herself up and began to French kiss her son, her tongue invading every corner of his mouth as he surrendered to her.

"Mmmm, so long since I've tasted myself that way. Thank you, darling, that was wonderful."

"Good, I ... I loved you sucking me, but you were choking, I would have stopped."

"No, no, it is so exciting to feel you do that to me. I was gagging on your hard cock and loving it. Now though I want to do something else with that hard cock, are you ready?"

For a moment he was confused but then Paul realized his mother wanted him to slide his rock hard dick inside her.

"Ohhh, yes, I am so ready, mom, but I ... I don't want to disappoint you ... dad, he's done this for so much longer ..."

His mother's soft finger rested against his lips.

"Shhhh, your inexperience is part of why I'm so turned on. Let me do what you wanted and be your first, ok?"

For an answer Paul reached out and moved his mother closer to him. His lips latched on to the beautiful breast swinging just above him and he began to suckle. His hands grasped at her soft butt cheeks, kneading them as he listened to her breathing rate increase again and heard her begin to moan.

"Let me get ready, baby."

The soft tit meat moved away from his hungry lips and Paul watched dreamily as Jillian picked up her lipstick, applying it quickly before she leant down to capture his cock, and he felt himself harden even more as the marks he so wanted to see appeared on his shaft.