Daring Dabbs Pt. 02

Story Info
Dabbs gives her former teacher one final dare.
5.9k words
4.8
16.2k
26

Part 2 of the 2 part series

Updated 06/10/2023
Created 10/16/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
Daphne123
Daphne123
2,255 Followers

The following story is fiction and does not describe any real person or situation in particular. All characters are at least eighteen. Daring Dabbs was originally conceived as a one part story, but really positive feedback from the original encouraged me to do a sequel. It gets a little intense compared to my usual submissions but if you enjoyed the first part then you should really enjoy what happens here. Remember, the story is FICTION and just a FANTASY so just have fun reading. -- xoxo Daphne

"Oh my goodness," I thought to myself as I opened the elegant envelope with Dabbs' name written in script on the front, "she's getting married."

It had been two years since my former student and I fucked each other in a hotel room on a trip to Munich. Actually, it would be more accurate to say that she had fucked me. Dabbs had tied me to a chair while I was sleeping off the German beer she encouraged me to have that evening. Then, dressed as an eighteen year old schoolgirl, she teased me mercilessly, sucked my cock with unbelievable suction, had me watch her masturbate, and then fucked the daylights out of me. All of this because she knew that I wanted it deep down, but wouldn't allow myself to fuck a former student half my age, even if she was okay with it.

Over the course of the next year, Dabbs and I would meet occasionally for dinner or coffee. We talked about everything going on in our lives and enjoyed each other's company, just as we had done before our trip together. The difference was that afterwards, Dabbs would take me to her discretely parked car, get down on her knees, and suck my cock completely dry.

Sometimes, Dabbs would tease my shaft relentlessly with her tongue, playing with my mind and turning me into a quivering mess as I begged her to let me come, which she would...eventually. Other times, Dabbs would go at a steady pace, bobbing her head gently and looking up at me with the most beautifully submissive eyes as if she was still my student trying to convince me not to tell her parents that she had forgotten her homework. Still, on other occasions, Dabbs would grip my shaft firmly with both hands and milk my cock relentlessly until she was ready to finish me off. Then, she would take my entire length down her throat and literally pull the orgasm out of me.

Her oral skills were amazing, and she knew it too.

A few months later, Dabbs took a new job in the city. We kept in contact but didn't get to see each other for a while. Our experiences together, though, helped give me the confidence to start dating again. Over the next several months, I had some wonderful sensual experiences with different women the same age as me.

All thanks to my former student in her mid 20s.

Now, as I read the wedding invitation, it had been about a year since Dabbs and I had last seen each other. She had actually started dating one of her old friends from high school. Apparently, things had gotten really serious and Dabbs became pregnant. When she had her baby girl a few months ago, she sent me some beautiful pictures of mother and daughter together. It made me smile, and she seemed very happy.

It appeared that the two parents were now getting married, and it felt lovely to be invited. I did notice that with the RSVP card, there was a small handwritten note from Dabbs that read:

"I hope you can come. It would mean a lot to me if you could give me away." - Dabbs

Of course, I signed the RSVP letting her know I would be there, adding a note back to her:

"I wouldn't miss it for the world."

***

A month or so later, the weekend of Dabbs' wedding arrived. The location she chose was a lovely Georgian style house in the countryside surrounded by large full trees. The ceremony was being held on the lawn, with the reception inside the banquet room of the house.

That night before the event, I got a text from Dabbs:

"Hey there, can you swing by tomorrow morning a few hours before the ceremony?"

I responded:

"Sure, anything wrong?"

Her reply came a minute or so later.

"Oh no, there's nothing wrong, I just want to see you before everyone arrives...say 11am?"

I always felt stupid as a middle-aged man texting a "thumbs up" emoji, so I just typed back:

"I'll be there."

***

The following morning I showered, had breakfast, and got into my classic black tuxedo. As I drove to the wedding location about an hour away, I thought about all the wonderful memories I had experienced with my former student. I had stimulated her interest in history when she was in my class, inspired her to go into the same profession, watched her grow into a beautiful young lady, shared so many personal things with her, traveled abroad with her, fantasized about her...

Ever since she fucked me though, my thoughts would always come back to the image of Dabbs on her knees with her hair in pigtails and her beautiful eyes staring up into mine as she sucked on my cock in so many wonderfully perverted ways. That mental picture was as clear as when it happened, and would be with me forever.

As I arrived at the estate, I pulled into the parking area designated for attendees. I recognized Dabbs' car immediately. Hers was the only vehicle in the lot. The wedding wasn't until 4pm, and I couldn't help but wonder why Dabbs wanted me there so early.

I parked next to Dabbs' vehicle in the corner of the lot next to the wooded area. No sooner had I gotten out of my car and closed the door that I heard a voice.

"Woohoo! Lookin' good there!" Dabbs' slightly southern accent was unmistakable.

I smiled at her comment and turned around.

That's when my jaw dropped.

Dabbs stood on the other side of the parking lot closest to the house in her full wedding attire. She had shifted her weight to one side and had her hands on her hips, flashing the most beautiful smile.

The dress...ohmygod the dress...

Dabbs' wedding dress was a pure shimmery white with beautiful lace embroidery. Below the waist, the dress flared out down to her calves, leaving her legs bare about eight inches above the ankle. From the waist up, Dabbs' top fit snugly around her mid and lower back with a long vertical zipper that went all the way down her back to just below her waist. Her shoulders and upper back were completely bare while her top was holding her large breasts firmly in place.

If that wasn't enough to drive any man crazy, her gorgeous brunette hair was caressing her upper back with a small but elegant white headpiece clipped off to the side.

The final detail that sent my cock into overdrive were the crimson red high heels Dabbs was wearing as she sauntered towards me, carrying a small matching bouquet of roses.

"Mygod, Dabbs," I finally managed to say, still gaping, "you look unbelievable."

My former student tilted her head cutely to one side and smiled.

"You're looking pretty darn fine yourself," she replied, gently placing her hand under my chin to close my gaping mouth.

I just couldn't believe how beautiful she looked.

"I'm sorry it's been a while since we've seen each other," Dabbs spoke softly, "life just gets in the way."

I shrugged. "It's okay. New job, new baby, new fiancee. I really appreciate you keeping in touch with what's going on in your life, though. That baby girl is adorable, and your figure is fantastic!"

"Isn't she though?" Dabbs replied, glancing down at her breasts, "she's still nursing too, and my breasts have gotten massive."

I cleared my throat. I wasn't going to mention it, but I had noticed a significant size increase in her breasts since the last time I saw her. I loved how casually she would talk to me about things like that.

"So, why did you want me to come so early today?"

Dabbs smiled cutely as she playfully straightened my bowtie.

"Why do you think?"

I stared at Dabbs intently.

"You tell me."

With a coquettish look, Dabbs gently took my hand and leaned close to whisper in my ear.

"One last fuck?"

My eyes widened in shock. "Dabbs!?! On your wedding day?!?"

My former student nodded.

"But..." I started to say something.

"Come on," Dabbs interrupted, leading me by the hand towards the wooded area next to the parking lot, her crimson high heels clicking on the concrete. "The ceremony isn't until late this afternoon. I'm still a single girl until then."

"A single mom, you mean," I insisted...although I noticed I was still following her into the woods.

Dabbs rolled her eyes.

"The key word is 'single'," she replied, looking back over her shoulder and flashing me a flirty smile.

I swallowed hard as Dabbs led me deeper into the trees.

"I want to get fucked hard before I get married...really hard," Dabbs said so casually it almost sounded strange, "and I want you to be the one to fuck me."

I raised my eyebrows. "Is that a dare?"

"Mmm hmm," my former student nodded.

Deep into the wooded area was a small clearing where Dabbs had placed a large picnic blanket on the ground. My former student led me to the center of the blanket, gently placing her bouquet on the corner.

"Dabbs," I said as she turned to face me, "are you sure you want to do this?"

"Oh, I'm sure," Dabbs replied immediately, dropping to her knees and undoing my trousers.

"Um!" I jumped slightly as the bride-to-be took hold of my cock and pulled it gently out of my pants.

It was as hard as steel.

"Well hey there," Dabbs began talking to my staff, "looks like you missed me."

Immediately, Dabbs whipped her hair back and took the full length of my shaft in her warm wet mouth.

"Ummm..." I moaned as she began gently bobbing her head back and forth, her beautiful eyes staring up at me lovingly.

Those eyes...those gorgeous eyes always told me how much she loved me.

"Oh Dabbs..." I sighed in bliss as I felt my former student's tongue swirling around the head of my cock, her slurping noises mixing with the sounds of rustling leaves.

She was amazing, and watching her do it while wearing her wedding dress was unbelievably hot.

Once the future bride had gotten my dick sensitive enough, she pulled back and turned around on all fours to face away from me. Smiling over her shoulder in my direction, Dabbs slowly hiked her dress up over her hips...inch by inch...revealing her shapely legs, and then her marvelously large ass wearing white lace thong panties.

"Oh...my...fucking...gawd," I said to myself as I took in the sight before me. My twenty-something former student was on all fours in her wedding dress with her skirt pulled up over her hips ready for me to fuck her.

I couldn't hold back any longer, and got down on my knees directly behind the future bride.

"Fuck me hard, baby," Dabbs said as if she were giving me an order.

As my former student braced herself, I grabbed the thinnest strap of her thong panties with both hands and yanked hard enough to break the fabric.

(rip)

"OH!" Dabbs jumped slightly with a girly yelp as she felt her panties being taken.

"Nice, Dabbs," I said placing her tiny thong in my coat pocket.

"What the fuck?!?" Dabbs exclaimed. "Did you just tear my panties?!?"

In response, I spanked her large round ass...hard.

(SMACK!)

"OH!!" Dabbs yelped. "Fuck! What was that for?"

"Just to let you know who's in charge this time," I answered, spanking her again.

(SMACK!)

"OH!!!" Dabbs yelped a second time, this one at a higher pitch.

My former student glared back at me over her shoulder. I knew that look. She was pretending to be angry, but her eyes were actually telling me that she wanted more.

She wanted it rough...

...so I spanked her harder...

(SMACK!!!)

"OH!!! FUCK!!!" Dabbs threw her head back as she yelled at the sky above us.

Another hard slap...

(SMACK!!!!!)

"OH!!!!! MOTHER FUCKER!!!!!"

"You watch your language, young lady!" I chastised her as if she was still my student.

(SMACK!!!!!)

"OH!!!!!" Dabbs nodded her head. "Y-YES SIR!!!"

I lined up my cock with the entrance to Dabbs' pussy, placing the head between the swollen lips of her labia. Dabbs moaned in lust as she felt my rock hard staff getting ready to violate her.

Grabbing my former student by her hips, I violently thrust the entire length of my hard shaft into her all at once.

"OOOHHH!!!!!!!" The sudden invasion of her depths made Dabbs' entire body lock in tension. Her eyes widened, her mouth opened in shock. She had never been impaled by a cock so deeply before.

"OH SHIT!!" Dabbs cried out as her soaked pussy enveloped my shaft from all directions. "THAT'S SO FUCKING FAR INSIDE ME!"

(SMACK!!!!!)

"OH!!!!!" Dabbs yelped as I slapped her ass really hard.

"I told you to watch your language, young lady."

"Y-yes, s-sir," my student nodded again, trying desperately to adjust to having such a large cock thrust so suddenly that far up her cunt.

"I'm afraid I'm going to have to teach you some manners," I said grabbing Dabbs' ass with both hands and slamming my cock hard into her.

"OH!!!" The future bride cried out in lust as she felt her pussy being suddenly and violently stuffed with my powerful rod.

My student closed her eyes and bit her lip in tension as she felt the full length of my dick sliding back out of her cunt, only to be rammed inside her depths again...

...as hard as I could.

"OOHH!!!!!!!" Dabbs screamed as she felt my cock force its way deeper into her, my former student's pussy walls parted to allow the invading shaft to penetrate her further.

"OH!!!!!!! FUCK!!!!! FUCK!!!!! FUCK!!!!!"

(SMACK!)

I spanked her ass hard as I continued to slam into her depths over and over again.

"DAMMIT!!!" Dabbs swore like a sailor as I pummeled her with my large cock, spanking her ass every time she cried out with a word inappropriate for a student of mine.

(SMACK!)

"OH!!! FUCK!!!!!"

(SMACK!)

"OH!!!!! DAMMIT!!! YOU'RE BANGING THE DAYLIGHTS OUT OF ME YOU MOTHER FUCKER!!!!!"

(SMACK!!! SMACK!!!! SMACK!!!!!)

I fucked her hard...really hard, violently slamming into her cunt over and over, while she screamed obscenities every time she felt my dick thrust deep inside her.

"OH FUCK!!! OH SHIT!!!! FUCK THAT'S DEEP!!!!!"

(SMACK!!! SMACK!!!! SMACK!!!!!)

Dabbs felt the orgasm building as each slam into her pussy stroked her sensitive g-spot.

"Come on, Dabbs, you bad bad girl!" I said sternly as I pummeled her relentlessly.

"OOOHHH!!!!!!!" Dabbs' eyes widened as she felt a massive orgasm overtaking her. Her entire body began to shake as she came hard, her pussy gripping my shaft tightly and milking it with its contractions.

"OH FUCK!!!!!" Dabbs cried out as she felt my cock about to explode. "COME INSIDE ME! COME INSIDE ME!!!!"

Grabbing Dabbs by her bare shoulders, I pulled her towards me while simultaneously thrusting hard and deep into her cunt.

"OHMYGOD!!! OOOOHHHHH!!!!!!!"

Dabbs' scream, as I came inside her, was primal and beautiful. Her entire body orgasmed with mine as I fired everything I had into her. The warm sensations of my cock filling her pussy sent her into a series of orgasms that steamrolled her into oblivion.

Tears were streaming down Dabbs' cheeks as I continued pumping until my cock had finished with her.

Exhausted, Dabbs lowered her head and gasped for air as the waves of pleasure began to subside. I pulled my cock out of her, causing Dabbs to convulse as tiny remnants of her massive orgasms jolted her overly sensitive pussy.

My former student looked back over her shoulder at me in astonishment at what I had just done to her. She had never come like that before, and her glazed eyes were filled with a loving gratitude. We stared at each other in silence for a few moments, and then both started laughing.

"Well, YOU'VE certainly gotten more confident," Dabbs smiled cutely.

I nodded. "Thanks to you."

"That was fucking amazing," Dabbs commented.

(SMACK!!!)

"HEY!" Dabbs objected as I spanked her ass again. "What the fuck?!?"

(SMACK!!!)

"I told you to watch your language, little lady," I explained. "I see you still haven't learned your lesson yet. I'm afraid I'm going to have to fuck that ass of yours as well."

Dabbs' mouth fell open in disbelief at what she was hearing.

"What?!?"

I removed one of her crimson high heeled shoes and grabbed her ass with both hands.

"If you didn't want it rough, you shouldn't have dared me," I said, placing the heel of the shoe between the cheeks of her large ass.

"Wait a minute! Can't we talk about this?" Dabbs tried to bargain with me as I began to insert the heel into my student's forbidden opening.

"Ohmygod! What are you doooaaAAAAHHHH!" Dabbs' protest was interrupted as the heel pushed slowly through her outer defenses followed by several inches of penetration up her ass.

"AAAHHHH!!!!" Dabbs screamed to the sky as she felt the heel of her crimson shoe being inserted into her her tiny opening. To my former student, the sensation was completely obscene, and it made her feel unbelievably submissive that her former teacher was doing this to her...on her wedding day.

"OH FUCK!" Dabbs gripped the blanket firmly with her hands as she felt the invading heel being worked into her ass and expanding her opening.

(SMACK!!!)

"OH!!!" Dabbs jumped as I spanked her again, a reminder that right now, I owned her pussy...her ass...her tits...her entire body.

After a few minutes of working Dabbs' opening, I removed the heel, causing my student to exhale in relief.

"Ohgod," Dabbs gasped, "what are you doing to me?"

I surveyed my progress...

"Let's see," I said, purposely thinking out loud so Dabbs could hear, "if I'm going to fuck you up the ass we're going to need something bigger..."

"What?!?" Dabbs' eyes went wide.

"Ah, perfect," I said, placing her crimson shoe back on and reaching for Dabbs' bridal bouquet.

Placing the handle in front of her face, I gently tapped her lips.

"Open wide."

"Not a chance," Dabbs fired back.

"Dabbs," I said sternly, "I'm shoving this handle up your ass whether you want it or not. How easily it goes in depends on you."

Dabbs glared at me, absolutely fuming. She couldn't believe how assertive I had become, and that she was the one who had given me the confidence to take control. I was dominating her now, and as her pussy soaked itself, she realized how horny it was making her.

With submissive eyes, the future bride opened her mouth and began sucking violently on the handle of her own bouquet, her head bobbing back and forth as fast and as wet as she could. The sight of my former student on all fours, in her wedding dress, going down on her own bridal bouquet with the most degrading slurping sounds, was an unbelievable turn on for me.

Fucking my student's ass so soon after unloading inside her pussy was definitely not going to be a problem.

When Dabbs had completely soaked her bouquet handle, I took it out of her mouth and placed it between the cheeks of her amazing ass.

"OH!" Dabbs' eyes widened as I began pushing the handle of the bouquet into her.

"Ohmygod!!" Dabbs laid her head back as she prepared to have her ass violated again.

Slowly, very slowly, the handle began stretching her opening.

"OH FUCK!!! IT'S TOO BIG!!! FUCK!!!"

(SMACK!!!)

"OH!!!" Dabbs was in tears as I spanked her hard. There was nothing she could do to defend herself other than to tense up. I pressed a little firmer, the tip of the handle beginning to penetrate deeper.

"No..." Dabbs whimpered softly, her quivering muscles gripping down on the invading staff. I pressed on, pushing more of the handle into my student's most forbidden of openings.

"AAAAHHH!!!" Dabbs cried out as she felt her ass being violated one inch at a time.

I pulled back, causing Dabbs to exhale deeply before forcing the bouquet handle back inside her once again, this time deeper than before.

Daphne123
Daphne123
2,255 Followers
12