Three Dinner Dates

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

"Yes, of course. If you want to go home, I can take--" Simon jumped in.

"No... not that, Simon," Anna cut him off. "I was wondering if I could stay with you."

"What... here?" Simon replied. He was taken aback by the suggestion, but at the same time he couldn't imagine anything nicer than sharing his bed with Anna. He just wasn't expecting it to be so soon.

"Of course," Simon added, shuffling over to one side of the bed.

Anna climbed into the other side of the bed, feeling his warmth on the sheets. She moved in slightly but never crossed the imaginary centre line of the mattress.

Simon made sure to stay on his side of the bed too. He was so happy to have Anna here with him, but he didn't want to spoil the moment. If she just needed a bit of reassurance in a strange house, and wanted to sleep in the same room, then that was fine. If she wanted anything more, then that was also fine.

For a few minutes, they stayed this way, before Anna finally broke the silence.

"Wrap your arms around me, Simon. Hold me tight. Show me that you love me," she said.

The reaction was instant. As Simon moved across and wrapped an arm around her, Anna closed her eyes. She could feel the warmth of his bare chest against her back. She could sense his every breath on her bare shoulder. Her heart was beating fast. She had desire aching in her loins, but she told herself this was far enough. She wanted more but, in her mind, this was a test. She needed to know that Simon wanted her for who she was, and not because she was there and available.

* * * * * * * * * * * * * * * *

The next morning, Anna awoke to the sound of footsteps in the bedroom.

"Simon?" she asked, rubbing her eyes against the bright morning sun which was now coming in through an already open bi-fold door. "What time is it, Simon?"

"Breakfast time," an already dressed Simon replied, walking past the bed, carrying a full tray.

"Mmmm, smells nice," Anna replied, the wafting aroma of fresh coffee hitting her senses as Simon headed right out onto the balcony.

Simon returned to the bedroom and grabbed a dressing gown from behind the door.

"Here, pop this on," Simon suggested. "It's a wonderful day out there, but maybe still a little chilly for just a nightie. I hope you don't mind. You looked so sweet there, and I didn't want to wake you too early, so I took the liberty of choosing for you. I do hope there's something you like."

Anna smiled. Even if he'd picked everything she hated to eat, Anna wouldn't have complained. With Simon, it was becoming a sequence of firsts, and this was the latest. Nobody had ever cooked her breakfast before, unless you counted the various hotels she had stayed in on her travels, and most definitely nobody had brought it to her in bed, nor had offered her their own comfy gown to wear.

She slipped on the dressing gown, rolling the overlength sleeves up a little, and followed Simon out onto the balcony. To say this was the best breakfast ever, might not have been an understatement. The food was great. The view was sublime. The company was stealing her heart. If Anna had any doubts remaining, they had now well and truly been vanquished. She knew what she wanted to do, and it was her turn to be asking the question.

"Thank you, Simon," Anna said, putting a second empty coffee cup down on the table.

She paused for a few seconds, collected her thoughts, then continued.

"I've had a wonderful time, with a wonderful man. You called me a thief, you know... suggesting I was stealing your heart... but I know the truth... it is you Simon who are the thief... it is you with your plentiful charms who have stolen my heart. I thought I did before... but now I am sure..."

"Sure, of what, Anna?" Simon asked.

"Sure, I never want this feeling to end," Anna answered. "Sure, I want to see where we can go together. Sure..."

Anna paused for a moment.

"God, what am I saying," she blurted out, abandoning the attempt to wax lyrical. "You're drop dead gorgeous, Simon, and I'm falling in love."

This time it was Simon's turn to pause before responding.

"I'm not," he replied, taking Anna by surprise.

Anna glanced towards her would-be lover, wondering just what he meant.

"I'm not falling in love," Simon repeated. "I've fallen in love. I fell in love with the most beautiful woman in the world, the first time I ever met her."

Anna smiled.

Anna blushed at yet another compliment.

"I was wondering, Simon," Anna started, this time with a touch of nervous hesitancy in her voice. "Are you busy today? I don't want this moment to end, and I'd love to spend some more time with you."

"Not at all," Simon replied. "When I knew you were coming, I dropped everything."

Anna smiled again.

"Then, would you mind?" she asked.

"Mind what?" Simon replied, teasingly.

"Mind if we spent the day together? Mind if I bought you lunch? Mind if I stayed a second night?" Anna fired off suggestions, each spoken as a question, waiting for an answer.

Simon didn't reply, well not in words. The smile on his face gave an affirmative response, and the way he kissed Anna, soft and sensually, just reinforced the same.

Bidding Simon farewell, Anna went to change. She emerged a little later wearing a pair of flattering figure-hugging black jeans and a plain grey cotton tee-shirt. They were smart. They were comfortable. They were intentionally hiding a little surprise underneath, one which hadn't come cheap, but she hoped would be worth every penny.

The surprise... that was for later.

* * * * * * * * * * * * * * * *

Yet again, Simon had been true to his agreement, other than letting Anna pay for lunch. As day became night, and a little earlier than on Friday, Anna suggested it might be time to turn in.

"It's been a long day, Simon. You must be tired... I know I am," Anna announced.

"We can call it a night, if you want," Simon replied. "Where would you like to sleep tonight?"

"With you, of course," Anna instantly replied. "That's if it's okay for you."

Anna didn't wait for a response. She gave Simon a quick kiss on the lips, then headed off towards the guest bedroom. As far as Simon was concerned, she was getting ready for bed, and getting ready for a good night's sleep.

Anna, though, had no intention of sleeping just yet. She was set on saying thank you for a wonderful weekend, and there was only one thing on her mind. Anna was intent on surprising her lover and, hopefully, in a most enjoyable way. First though, there was something she needed, and that was still stashed in her handbag.

"Thank you, Chloe," Anna whispered as she grabbed the small package and stuffed it into the pocket of her jeans. It was a far cry from the contempt she had shown Chloe back in the coffee shop, but now it seemed so right.

A few minutes later, and still fully clothed, Anna headed to the master bedroom. This time the door was open, so Anna simply walked in rather than knocking. Simon was already in bed waiting for her. A look of confusion spread over his face as he saw Anna standing there in her daytime outfit.

"Is something wrong, Anna. Have you changed you mind about turning in early?" Simon asked.

"No... no..." Anna replied, barely hiding her smile as she thought about jumping into bed with her lover once more.

"Then are you going to sleep in those?" Simon asked.

"Don't be silly," Anna quipped, nudging the bedroom door closed with her foot as if looking for an added security that she wouldn't be watched. "Of course, I'm going to take them off before I come to bed."

Any response that Simon might have had, was soon lost. Anna had been serious in saying she would take them off. What Simon was never expecting was that she would do it standing there in his bedroom, and with the sort of swagger that could only be described as sultry and seductive. Whatever her intention, Simon's eyes were now transfixed on the young blonde as she eased her tee-shirt out of her jeans.

Anna pulled the soft grey cotton top upwards, exposing an inch or two of bare flesh. She stopped for a moment, glanced down at Simon to make sure she had an audience, and blew him a soft kiss. Her pulse was racing. She was struggling to contain her breathing, nerves taking over.

There was no going back now.

Her mind was set.

Over and over, Anna had considered what she would do, and now she was doing it. All the time, Anna hoped Simon would still like her. There was only one way to find out.

Anna returned to her top, easing it up higher and higher. Her cute belly button came into view first, followed by the bottom edge of her bra. This was the surprise. Anna had promised herself she would look good for him, whatever it took. Inch by inch the sexy garment came into view, black leafy lace on top of a deep red mesh. Her breasts were never the largest, but what she had was pulled temptingly together by the plunge cups of the bra, revealing an appealing glimpse of cleavage. And then the top was gone, pulled over her head and dropped to the floor.

As Simon stared, Anna turned her attention to the jeans. She undid the button and eased the zipper down. The black denim fell open at the front, revealing a view of strappy black trim, and a tiny glimpse of similar red-black fabric.

That was where Anna stopped. Instead of pulling the jeans down and revealing her matching knickers, Anna turned her back on her lover. She gave a little wiggle of her denim clad ass. She looked back over her shoulder. Anna gave a seductive wink to Simon when she saw the way he was staring.

Then, one side after the other, she inched the black denim down. A thin black strap came first into view, clinging tightly just above her hips, followed by the tiniest triangle of black mesh fabric, and a plentiful view of bare flesh. The knickers, thong in design, quickly disappeared between Anna's firm ass cheeks, only becoming visible once more, between her legs, as she bent at the waist to ease the jeans further down.

Intentionally, and for just a little longer than was necessary, Anna held that pose, with her jeans lowered to knee height. She knew the view she would be giving her lover, that teasing thigh gap covered in skimpy black fabric, and she so hoped Simon was enjoying the show. Finally, Anna stepped out of the jeans, and stood up once more. With a flick of her foot, Anna nudged the jeans towards the edge of the bed--they would be needed later if she had her way--and turned back towards Simon.

"How do I look?" she said, running her hands over her hips, waist, and up towards her bra.

"You look..."

Simon's words tailed off as he watched Anna reach behind her back and unclasp the bra. She released her grip and let the sexy garment slide down her arms, releasing her breasts as it fell to the floor. Her nipples were already hard, such was the excitement of stripping off for her lover.

"...angelic... simply angelic," Simon answered.

"Well..." Anna responded, teasingly working her knickers down to the floor. "Is there room for an angel in that bed of yours?"

As Simon pulled back the duvet, Anna slid underneath. She shuffled up to her lover, placed a kiss on his lips, then turned her attention to his soft earlobe. Amid a mix of kissing and nibbling, Anna whispered to Simon.

"Do you like me, Simon?" she asked.

"Of course," he replied.

"I mean..." Anna clarified. "I mean... do you like me like this?"

"Oh yes," Simon responded. "I told you... I liked you the minute I met you... and with every minute we spend together, I like you more and more."

"Shall we see?" Anna asked, taking Simon by surprise as she moved her hand down, her fingers nudging against his lounge pants.

"What's this, Simon?" Anna whispered, a huge smile across her face.

Simon didn't know what to do, nor what to say. He was hoping to keep the bulge in his pants hidden, never expecting the love of his life would go looking for a reaction. What was he going to do now, or more to the point, what was Anna going to do in the knowledge that he had gotten all excited at watching her strip off?

"I'm sorry," Simon apologised. "It's... well... you are so beautiful... and I just couldn't help..."

"I meant... this," Anna responded, pulling at the fabric of his lounge pants. "Don't you think you should take it off?"

"Take it off?" Simon asked.

"Well... if you want to, that is," Anna teased. "I know I do."

Without any further hesitation, Simon removed his lounge pants.

"These too," Anna whispered, her hand tugging at the boxers underneath.

Simon took the boxers off and tossed them out of the bed. He rolled over and embraced Anna. For the first time, the two lovers felt the true warmth between them. They kissed, lips melded together, tongues entwined. As they squirmed in a passionate embrace, Anna would gasp from time to time, either as her now hard nipples rubbed against his bare chest, or as his rampant cock nudged up against her apex.

All it did was fuel her fires.

The tingle was back in her lips.

The ache in her loins couldn't be ignored.

The nervous anticipation was setting her pulse racing.

"I love you, Simon," Anna whispered between kisses.

"Love you too, Anna," Simon replied.

Still, they embraced. Still, they rocked from side to side, pulling each other closer and closer, their movements increasing in passion by the minute.

For the first time, Anna reached down and took hold of his erection. Being a novice when it came to the other sex, Anna didn't quite know what to expect. She was scared he would be too long, but actually her vibrator was a good inch longer. She was scared he would be too thick, and to be honest his girth was wider, but not excessively.

What Anna found though filled her with excitement. He was warm to the touch, and he was hard, so hard, so very hard. As Anna started to work her hand along his length, feeling his skin slide against the enclosed rod of steel, she started to imagine taking him inside. How would it feel? Would it be just the same as her fingers, or even that trusty vibrator?

There was something predictable about masturbating in that she was in control. She could manage the speed. She could apply pressure just where she wanted it. She could anticipate every movement. Here though... here, she would be at his mercy... and that was what Anna wanted more than anything.

"Mmmm... so big... so hard... so..." Anna commented, as she ran her hand up and down his shaft.

If it wasn't made up already, Anna's mind soon was. Releasing her grip on his manhood, Anna wrapped her top leg over Simon's thighs, intent on getting closer still. As Anna inched towards Simon, he moved his upper leg between hers and pulled her on to him. The response from Anna was instant and audible.

"Mmmm... Simon!" Anna gasped.

As Simon pulled Anna on to him, the head of his cock grazed against her slit. It had taken her by surprise but, oh my god, it felt so good, and before long Anna found herself grinding slightly, enjoying every movement against her sensitive labia. Simon soon cottoned on to what was happening, and took matters into his own hands, rocking gently as he worked his cock against her sex.

With excitement taking over, Anna was soon pushing back against his every movement, making his cock rub forcefully against her folds rather than simply graze her sensitive slit. That ache in her loins was becoming a desire-fuelled fire. Every movement was pushing her onwards. As he worked her, Anna could feel her arousal come to the fore. Her outer lips were already puffy, and as they spread slightly, Anna felt the touch of his head against her soft inner folds.

She clamped her arms around Simon, pressing her breasts against his manly chest.

She continued to grind back against his rocking motion.

She moaned softly as he teased at her aching sex with the tip of his cock.

She gasped loudly as he grazed against her now swollen clit.

"Simon," Anna called out. "That feels so good, Simon."

With the verbal encouragement, Simon rubbed his cock even harder against Anna's sex, and she groaned.

"I want you, Simon... I want you inside..." Anna called out, pulling back from the embrace, and lying on her back under the covers.

"Are you sure?" Simon responded, rolling onto his side, and propping himself up on his elbow.

"Never surer," Anna replied, smiling, then placing a kiss on his lips. She took hold of his free hand, and brought it across her naked body, resting his fingers over her left breast.

Simon smiled back. He leaned forward and reciprocated the kiss. Then, softly at first, but all the time increasing in intensity, he started to work Anna's breasts, massaging the soft flesh, and teasing at her hard nipples. Noticing the reaction from his lover--her breathing had quickened once more--Simon brought his hand downwards. His fingers traced lines across Anna's flat stomach, through her soft bush, all the way until they touched against her apex.

Anna stiffened for a moment, then relaxed. As she relaxed, she spread her legs slightly, and felt Simon move his fingers down between. Gently, Simon toyed with her puffy lips, easing them apart, feeling the slick juices within.

"You're so wet, Anna," he whispered, a single finger tracing the inner line of her slit.

"So wet... and so ready..." Anna responded. "I want you to come on top, Simon... but..."

"But what, Anna?" Simon asked.

"But I've never done it before," Anna replied, "and I'm not... well... I don't want a baby yet."

Simon laughed. If truth be known he'd never done it before either, so this was a first for him. What's more, he wasn't ready to become a father yet either. Reluctantly, he was resigned to waiting for the time to be right.

"It's okay, Anna," Simon said. "We don't need to rush."

"No... no... Simon," Anna responded. "I want you tonight. You'll find what you need in the pocket of my jeans. Be quick... and be gentle."

Simon pulled the duvet back, climbed off the bed, then rummaged in the pocket of her jeans. He returned with a smile on his face. Simon knelt on the bed, between Anna's outstretched legs and glanced down at her waiting sex. God, everywhere he looked, she was truly an angel.

"Looks like somebody came prepared," Simon teased, as he slipped the condom over his hardness.

"Now, are you still sure?" Simon asked, all the time starting to change position.

Anna nodded. The smile on her face had become a little more pensive. Nerves were starting to take over as she watched Simon move towards her. She wanted this moment more than ever, yet she suddenly felt scared at the thought of having him impale his shaft into her virginal flesh.

Before long, Simon was lying on top of Anna, his weight propped up on his elbows. She could feel his hard manhood nudging against her sensitive sex. She waited for him to press against her labia, to sink into her soft folds, to seek her tight opening, but it didn't come. Their lips did meet, but it was in the most passionate of kisses. For a moment they held that sensual caress, lips melded together, tongues toying with each other. Anna closed her eyes and dreamed of what was about to come.

'Do it... do it now, Simon... I'm all yours, Simon... take me, Simon...' Anna ran the words over and over in her mind.

It was like he could hear what she was only thinking. As they kissed, Simon moved his hand down under his hips. Carefully he positioned himself, rubbing the tip of his cock against her slick folds as he sought her opening. Then, ever so slowly, he leaned forward.

Anna groaned.

Anna stiffened as he widened out in her opening.

Then, with an audible gasp, Anna felt his head pass beyond. Inch by inch he sank deeper into her tight pussy, filling her walls like never before. Finally, Simon lay there, on top of his lover, their bodies joined in love, their lips once more melded together.