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A New Lesson for Miss Ries [F25] [M41] [Female Friendly] [Romantic] [Spanking] [Blow Job] [Cream Pie] [First Anal]
Author Summary
ThisHappyPencil is a male in First Anal
Post Body

It had been six months since the snowstorm had sent Elly Ries, 25, middle school English teacher, on the biggest adventure of her life. The adventure she’d always wanted. She was now in a relationship with Andy, 41, father of Alice, one of her favorite and best students. Though it hadn’t been made official, she’d all but moved into Andy and Alice’s home. It was where she was happiest.

Elly was in love. In love with Andy most of all, but also in love with Alice and her new life.

When she’d told her parents about Andy and Alice, they were less than enthusiastic given the age difference. And how could their daughter, still so young herself, possibly be a mother figure to a 12-year-old?

But by the end of their second get-together, Andy had won them over and they’d completely fallen under Alice’s spell.

Though she was beyond happy with her relationship, she and Andy and Alice had agreed that it would be best to keep it under wraps around school until Alice started ninth grade at the nearby high school. Elly wouldn’t have minded her colleagues knowing about Andy, and she knew he wouldn’t have cared either. The secrecy was for Alice.

The last thing Alice — an unusually kind and empathetic child as middle schoolers went ؅— was getting teased because a teacher was dating her dad.

“You guys worry too much about me,” Alice had said when Andy and Elly explained the situation to her. “My real friends wouldn’t care, and everyone knows I already get all As anyway so it’s not like they could say I’m getting special treatment.”

“That’s all true,” Andy said. “Why don’t we just play it be ear? This is still new to all of us and maybe we’ll reach a point where it doesn’t make sense to keep it a secret.”

To which Elly added, “Besides, my family knows, and your family knows. All our friends, too, and that’s what counts.”

Alice laughed at this and said, “None of my friends know! And this is going to blow them away when I can finally tell them.”

“You never know,” Andy said, “maybe your beloved Miss Ries will trade me in for a younger model before you have a chance to tell anyone.”

Elly, who was nearly a foot shorter than Andy, reached up and pulled his head down to her and kissed him. “Not likely.”

Alice dramatically rolled her eyes and stuck her tongue out. “Knock it off, you two are so gross!”

Spurred on by her words, Andy and Elly grabbed Alice and began kissing her cheeks, causing each of them to melt into uncontrollable laughter.

After the kissing and laughter, the trio headed to the mall because Alice wanted to clothes shop with Elly.

“It’s so nice to have another girl around to help me pick stuff out,” she’d said to Andy. “You’re a good dad but you have terrible taste in clothes.”

When they got to the mall, Elly and Alice immediately began heading in and out of stores, taking clothes off racks to hold them up to each other. They were completely happy and at ease together. Initially, as Elly’s relationship with Andy grew closer, she’d hoped to become something of a big sister to Alice. But in the last couple of weeks, she’d accepted that she now loved Alice as if she was her own daughter.

Though she’d never press the issue, she suspected that Alice had already come to think of her as a mother.

When they headed into another store, Andy said he’d wait for them in the corridor.

As they shopped, Elly looked out at him. He was sitting on the bench, reading the book he’d tucked into his pocket as they left the house. She bit her lip as she looked at him. He was tall and in good shape; better shape than most men twenty years younger. His dark brown hair had flecks of silver and white along the sides, something that drove her wild.

She had given herself over to him completely. If he asked her to marry him, she’d say yes without hesitation and if he asked her to have his children, she’d just as eagerly say yes to that, too.

It occurred to her that in a world where so many men seemed content to be boys, she’d found an actual man.

After a bit more browsing, they left the store and headed toward Andy.

Alice held up her phone and said to her dad, “Bella asked me if I could sleep over at her house tonight for a pizza and movies.”

“It’s okay with me, kiddo,” Andy told her.

Alice then turned to Elly, “Is it okay with you, too?”

Elly was taken aback by the question — the kind of question usually reserved only for parents. “Of course it is,” she finally said.

“It’s four now, and you two have a bit more shopping to do, so tell Bella we’ll have you there about seven,” Andy said.

While inside a shoe store, Elly looked out and saw that Andy wasn’t on the bench. Probably went to the bathroom she thought to herself, which also made her think about Andy’s cock, and that caused a pleasant ache between her legs.

It soon went from an ache to a hungry craving as she thought about how Andy licked her pussy in a way that always brought her to orgasm in just a few minutes.

Her pleasant thoughts were interrupted by her chirping phone telling her she had a text. It was from Andy.

 “Just confirming: 32B, correct?” the text read.

Elly had no idea where he was going with this, but she was only too happy to follow. “That’s right,” she replied. She also knew that Andy was fully aware that she was a 32B because he loved her breasts. Cuddling naked one night, she’d offhandedly said she wished they were a cup bigger, and Andy gently took them in his hands and pronounced them “perfect, any bigger, and they wouldn’t fit just right in my hands” He’d sent the text, she knew, to let her know that they wouldn’t just be falling asleep together tonight.

Elly’s phone alerted her to Andy’s response: “Good, I hope you’re ready to model something for me tonight … since we have the house to ourselves.”

At this, Elly’s pussy began soaking the crotch of her panties — panties that Andy had bought her and snuck into her bag a couple months ago.

In a few minutes, Andy caught up to his girls. Elly noticed he was carrying a Barnes & Noble bag. “Had to get a new book,” Andy said, holding the bag up. He winked at Elly and a new wave of wetness hit her pussy like a storm.

Shortly before six, Elly and Alice each had several bags of new clothes and were ready to go.

 “We better get you home so you can pack a little overnight bag,” Andy said to Alice.

When they pulled into the garage, Alice happily jumped out of the backseat and headed toward the door. Elly was about to do the same, but Andy gripped her arm. “Take this bag,” he said. “There’s more than a book in there. You’d better be wearing it when I get back.”

Elly gasped, excitedly. Andy grabbed the back of her head and pulled her to him. He kissed her hard and long. He finally broke the kiss and Elly got out of the car, struggling to walk for just a second because she was happily woozy from the kiss.

As Elly put the bags down in the kitchen, Alice came thumping down the stairs with her bag. “I’m outta here,” she yelled. She wrapped Elly — who at 5’2 and 100 pounds — was already smaller than Alice, in a hug. “See you tomorrow, Elly Belly!”

Elly watched the backdoor close as Alice headed back into the garage. This is love, she thought to herself.

As soon as she heard the garage door close, Elly opened the Barnes & Noble bag and saw a smaller bag from the mall’s lingerie store on the bottom. She looked into the bag and saw a lace, lavender bra. She took it out and saw a pair of matching lace bikini panties.

Clutching both in her hand, she practically ran upstairs to the bedroom — their bedroom.

She undressed in front of the huge mirror in the on-suite bathroom. Standing naked, she tried to see something more than the pretty, but not stunning woman, she considered herself. But she thought this way less and less, because of Andy, who couldn’t keep his hands off her.

She looked at herself through Andy’s eyes and thought about all the things he’d said to her while his cock was filling her, and he was kissing her neck and lips.

Now more than ever, Elly liked the way her face looked with her glasses, and she liked her shiny brown hair. She loved her petite, fit body. She’d even come to love her breasts, which, because of internet porn and beauty magazines, she’d for so long thought of as too small.

But it was true that Andy was able to completely cover each breast with one of his hands — his warm hands that had only ever touched her with love and desire.

“I have Andy-sized tits,” she said, and laughed to herself.

She looked at her thick, full bush. She kept it trimmed enough to prevent wildness but went no further than that. She’d asked Andy, after they’d been dating for a month or so, if he’d like her to shave it or wax it.

He’d said no. “First of all, it’s your pussy, I just borrow it from time to time,” he’d added, making her laugh so loudly she was worried it might wake Alice up.

“And second of all,” Andy said. “I love this hairy bush.”

He’d then rubbed his fingers through it, before putting his whole face in the hair, rubbing it around. And, as if that wasn’t enough for Elly, he’d kissed her bush all over, seemingly not missing a single hair.

Checking the clock, she put on her new lingerie and got on top of the bed. She was on fire for Andy. She knew she should wait, but she couldn’t. She began rubbing her clit and pussy through the lace of her new panties.

It felt like an eternity before she heard the garage door going up. By this point, her new panties were soaking wet and she’d created a puddle on the sheet. She heard Andy’s key fob hit the kitchen island and then heard him running up the stairs.

She got on her knees and put her hands behind her head so that Andy could see her little body in the lingerie he’d just bought her.

Andy stopped at the door and took in the scene. “I don’t have words for how beautiful you are,” he said.

“I don’t have words for how much I love you,” Elly replied.

“It smells like you got a head start,” Andy said, his eyes twinkling.

“I guess I was a little naughty.”

“Naughty girls need punishment,” Andy said.

Elly let out a low moan and Andy moved toward her. He grabbed her and maneuvered her over his lap. “Look at this tiny little ass … this perfect little ass,” he said, bringing a hand down onto her lace covered cheeks.

“Yessssss,” Elly groaned.

Andy smacked his favorite ass until it was red.

“I need your cock in my mouth, right now,” Elly said.

She pushed herself off Andy’s lap and began pawing at his clothes.

Elly never looked at Andy’s clothes while she undressed him, she did it all by feel, because they were too busy looking into each other’s eyes and smiling.

When she finally had Andy naked, Elly didn’t waste any time. She wrapped her lips around his hard cock and maneuvered her mouth down the shaft, feeling the head go down her throat. In the time she’d been with Andy, any gag reflex she’d had previously had evaporated. She could now deep throat Andy’s big, thick cock with ease.

Taking his hardness out of her mouth, she spent a minute licking the entire thing, up and down and all around. She took each of his balls in her mouth and sucked on them gently while swirling her tongue over them. Seeing precum on the head, she immediately licked it up and returned his cock to her throat.

She slurped and bobbed, savoring Andy’s audible and physical reaction. She knew he was about to explode in her mouth, something she was usually excited for because she loved the taste and feel of his huge loads of cum and relished the way they felt going down her throat — but she needed something, right now.

With his cock still in her mouth, she said, “Will you cum inside me, please, Andy?”

He looked at her, lovingly, but slightly confused. “Of course,” he said.

She jumped on top of him and immediately slid down his cock. Because of her blow job skills, Andy came almost instantly. He grabbed her hips and held her down against him and shot what she thought might have been his biggest load of cum yet, into her eager pussy.

Elly wiggled off him and put her head against his chest with his arm around her. Surprising even herself, she began to cry, not hard, but enough for Andy to notice.

“Hey, hey, hey, what’s wrong?” he said, moving them both on to their sides so he could look into her eyes. “Did I do something wrong?”

Elly smiled. “Just the opposite,” she said. “I have everything I want. I just love you so much it scares me sometimes. When you cum inside me like that, it makes me feel like you’re mine.”

Andy smiled so warmly his eyes danced. “I am yours. After Mallory died, I figured that was probably it. I didn’t expect another chance, but I have one because of you. I’m yours for as long as you’ll have me.”

They stayed that way for several minutes, kissing, laughing, and touching. Andy began exploring Elly’s body with his fingertips. “I love the way your skin feels,” he said. He began rubbing her clit and she shut her eyes and moaned softly.

Kissing her neck and giving each nipple turns between his lips, he began to work his way down her tummy toward her pussy, but she put her hands on his head and stopped him.

“Not right now,” she said.

“What? I want to, I love it,” Andy said.

“I know you do, and I love it too, and you’re really good at it,” Elly replied. “I mean like really good at it.”

“Then?”

“I don’t like it after you’ve already cum in me,” Elly said.

“What? That doesn’t bother me,” Andy said. “Fair is fair too … give and get!”

“Every lady is entitled to some prerogatives,” Elly said.

“You sound like a Jane Austen novel,” Andy said.

They both lost themselves to laughter.

“Well, at least I got a blow job from a hot teacher,” Andy said. “My teenage self would be very proud of me.”

Elly slapped him playfully. “I love sucking your cock.”

For nearly an hour, they stayed on their sides, facing each other. They kissed. They touched. They talked about Alice. They talked about the future — their future. There was no modesty or embarrassment about being naked. They were completely comfortable with each other. There were no hang ups about what they liked sexually because they trusted each other, and each was more driven to satisfy the other than they were driven to satisfy themselves.

Finally, Andy began kissing her with more urgency, a sign that he was eager for more. She welcomed it. She always welcomed it. As he kissed her, he began playing with her ass. “God, this little ass is so perfect,” he said.

She swooned at that.

As they kissed and Andy caressed her ass, Elly felt the tip of one of his fingers rub against her asshole. She reached back and grabbed his wrist, holding his hand in place, which kept his fingertip against her asshole. The sensation felt incredible. “I like that,” she said.

And the timing couldn’t have been better because something had been on her mind for a while, something she wasn’t sure how to bring up to Andy. Now the moment seemed right.

She broke free from Andy, found her small bag on her bedside table, reached in, and took something out. She then placed a small bottle in Andy’s hand.

He looked down and saw that it was a bottle of KY.

“This is something I’ve wanted to try for a long time but have never been able to,” Elly explained. “I’ve never been with anyone I could trust enough before. But it’s a fantasy — my biggest fantasy. I just want to try everything with you.”

“You should have told me months ago,” Andy said. “There isn’t anything I wouldn’t do for you — or to you.”

That line made her roll her eyes at him, lovingly. “I know, but it’s just that it’s … taboo. I don’t even think a lot of married couples do it. Only one of my friends does it.”

“And she likes it?” Andy said.

“She loves it,” Elly said. “She says the orgasm is incredible.”

Andy smiled at her — at his Elly. “Well, let’s get started.”

They embraced again and began making out like teenagers. In no time, Andy was hard, and Elly’s pussy was dripping. He began kissing her neck and exploring her ass, finally working the tip of his index finger into her asshole. Elly caught her breath and tensed. It hurt, but only slightly and only briefly. And the pain soon gave way to pleasure.

“Ready?” Andy said, finally.

“Ready.”

He got up and maneuvered himself toward her feet. She positioned herself with her face on the pillow and her little ass high in the air.

“Whoa, check out that ass,” Andy said.

Elly laughed and wiggled her butt.

Andy opened the bottle of KY and lubed his cock before squirting some on Elly’s asshole. He then pressed the head of his cock against it. He rubbed the head around her hole, teasing her.

“Please,” she said.

Andy slowly pushed the head in, and Elly was instantly overwhelmed. This was nothing like his finger. She knew he had a big cock, but it had never been so clear as it was now.

It hurt, but she knew it would at first. She began to take deep breaths, centering herself. She forced her body to relax. As with Andy’s finger, the pain began to subside and was replaced with pleasure.

Andy pushed more cock into her tight asshole. “Is that enough for the first time? I don’t want to hurt you,” he said.

“You won’t hurt me, sweetie,” she said. “I want all of it in me.”

Slowly but steadily, Andy pushed more of his hard cock into Elly’s virgin asshole. She could feel herself stretching to allow him in. Even though she was getting fucked in the ass, her pussy dripped and ached happily. Each passing second seemed to turn something on inside her. Her brain’s pleasure center was burning brighter and brighter.

“That’s all of it,” Andy said. He leaned down and kissed her on the back of her neck and between her shoulder blades.

They stayed like that for several seconds, allowing Elly to get used to having Andy’s entire cock in her ass.

“Baby,” she said. “Please fuck my ass.”

Andy didn’t need any more encouragement. He gripped Elly’s slender hips, holding her in place, so he could fuck her beautiful ass. He began thrusting his hips, allowing much of his cock to come out of Elly’s ass before plunging it back in. With each thrust, her asshole made more room for him.

Elly’s face was in the pillow, and she was half moaning and half screaming. She hammered her fists down onto the mattress. “I’m going to cry now,” she said. “But happy cry. Good cry. And if you stop, I’ll fucking kill you.”

Andy almost had to stop because he was laughing. But he soldiered on.

After a few minutes of increasingly aggressive anal, Elly’s entire body stiffened, and she screamed — actually screamed — “OH JESUS OH MY GOD … ANDY, I LOVE YOU.” She orgasmed so hard that it almost seemed like a seizure. Her pussy exploded with liquid and her eyes rolled back into her head.

“I should stop,” Andy said.

“Don’t you dare!” Elly said through her labored breathing. “I need to feel your cum in my ass.”

Andy began pumping again. Elly knew his body well enough to know that he was still a handful of minutes away, so she settled in to enjoy herself. She forgot about her body and began contemplating Andy’s. She adored his cock, especially because she knew he’d never let anyone other than her have it. She wondered what her asshole felt like to Andy’s cock.

She sighed contentedly and smiled when Andy picked up his pace and she could feel his balls banging against her. More than anything, she felt satisfied to be in this bed with a man who made her happy and who made her feel beautiful and who erased any need for her to feel inhibited.

Now she could feel him getting closer. She loved the way he breathed and sounded when he was about to cum.

“I love you Elly,” he said.

She was in heaven.

“You’re the love of my life,” she replied. “Now shut up and cum in my ass.”

He did. The sensation of having her tight asshole filled with hot, sticky cum was incredible. Better than she could have imagined. Losing her anal virginity to Andy had surpassed even her wildest fantasies.

Andy collapsed on top of her with his cock still in her ass. “I love you to death, but you can’t fall asleep on top of me,” Elly said. “I’m little and you’re big.”

He smiled and began tickling her on the spot on her left hip that sent her into hysterics. As he tickled her, she squealed with laughter. “Andy! I’m starting to pee, stop!”

Andy stopped as their laughter bounced off the walls. Elly playfully slapped his chest, but he was already on the edge of the bed, and it was enough to push him off. Elly tried to catch him, but she lost her balance too.

They fell onto the floor in a pile, hard enough that it knocked Andy’s small bedside table onto its side. The drawer opened and books fell onto the floor. But what the books were covering also fell onto the floor.

Before Andy could grab it, Elly saw that it was a ring box. She caught her breath.

“Is that a … is that for me?” she said.

Andy chuckled. “I had a whole plan. I was going to take you out to that French place downtown. I was going to do it right. But you just had to get fucked in the ass and ruin everything.”

Elly shrieked and covered her mouth with her hand. She stared at Andy. She had no idea what to say or do.

Andy picked up the box and opened it. Elly immediately recognized that it was the ring she had noticed one day while shopping alone with Alice. “That’s the ring I want if I ever get married,” she’d said at the time.

Alice had remembered and told her father.

Andy held the open ring box out to her. “Okay, Miss Reis, what do you say?”

“You know what my answer is, you dummy,” Elly said. She kissed him. She wanted to kiss him forever. As Andy slid the ring onto her finger, she said, “I’ve loved you since that first night, since that blizzard sent me home with you.”

Andy gently pushed hair off Elly’s forehead. He looked into her eyes and smiled.

“Well,” he said. “I guess we’re not going to be able to keep this a secret at school anymore.”

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