Right or Left? Ch. 08

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Surprise Anal

Kylah bubbled with enthusiasm, she and Jeff were about to spend their first night together! And this time her mom and Jeff's sister were not invited, it would be just the two of them! The nervous excitement made her feel like a new bride. Just the idea of being Jeff's bride made the butterflies in her stomach take flight. Like a little new puppy, she followed Jeff into the bathroom off of his bedroom.

"There are extra toothbrushes in the second drawer," he motioned. Jeff lifted the lid of the toilet to take a pee, smiling as Kylah watched him.

Kylah noticed not even Jeff's hand could circle his cock as he emptied his bladder, he was that thick. She loved the way her pussy felt so full when he fucked her, and she hoped one day she would be able to master deep throat without gagging.

"So tomorrow is the big day," Jeff said as he made circles in the toilet while relieving himself, "Wendy will show you how to clean your ass before we practice.

Oh Fuck!, Kylah thought in a panic. Tomorrow Jeff would introduce her and her mom to anal sex. If she hadn't seen Jeff's sister take his cock up her ass, she wouldn't believe it was possible.

Right now, she was sure her mom Jasmine was upstairs with Jeff's sister, Wendy. Wendy liked to take control, and Jasmine was on the submissive side; something they had in common. It had been fun sharing the double dildo with Wendy tonight, and she couldn't wait to see the video Jeff took of them.

"Will it hurt?" she asked.

Jeff knew Kylah was referring to tomorrow's anal lessons. "You're nervous, aren't you?" he asked. "Don't worry, I would never hurt you, or your mom." He never wanted to hurt Kylah.

"I, I don't want to disappoint you." Kylah said as she looked at his massive cock, "my ass is so small, and your cock is, well, your cock is what it is."

"Until you learn to relax; we will use lube," he said reassuringly as his bladder continued to release.

Kylah looked at the size of Jeff's cock, and couldn't imagine even trying anal sex without lube. His sister was able to do it, but she must have had a lot of practice. "Okay," Kylah sighed with relief, "lots of lube please!"

Jeff shook the last few drops into the toilet bowl and washed his hands and cock. They brushed their teeth together, laughing and smiling, making faces at each other in the mirror as toothpaste dripped down off their chins onto the counter. Their laughter lightened the moment, and Jeff felt Kylah calm down.

"So girlfriend, anything special you want to do?" Jeff asked as he held the bed sheet up for Kylah to join him.

"I like it when you call me your girlfriend," Kylah beamed crawling onto the bed. "My pussy is a little sore, but if you want to fuck me, it's okay. Or I can suck you!" she quickly added, not wanting Jeff to think she was complaining.

"It's been a long day and evening, why don't we just cuddle in bed and see how we feel in the morning."

"Okay, but if you get horny in the night wake me up!" Kylah laughed. "That's what a girlfriend does!"

"Oh, is it?" Jeff laughed, "and I thought I was your first boyfriend," he teased.

Kylah blushed. "You know you're the only one I've been with, right?"

Jeff knew he was lucky to have Kylah in his life; she was the first girl who meant anything to him, sexually and emotionally. The sexual relationship he had with his sister, and Kylah's mom, was different. He enjoyed fucking Wendy and Jasmine, but it wasn't the same as when he fucked Kylah.

"Have you had a lot of girlfriends?" Kylah asked, not sure if she wanted to know or not.

"None as good as you," Jeff said as he pushed a lock of hair off her face. "But, yes, I have fucked a lot of girls."

Kylah cuddled into Jeff's chest. "Did you love any of them?"

As Jeff massaged Kylah's perky breast and nipple he reflected on the "girls" in his past life. The majority of them had been one-night stands or at most only a couple of weeks long. He loved the chase or the hunt, to coax a girl to do things with him, things she never dreamed of doing with any other man. It was all a big challenge, and he was very accomplished.

"No, I never loved any of them," he finally acknowledged. "I used their pussies, mouths, and of course you know I love a tight ass. But I loved fucking them."

"Do you want to use me right now?" Kylah asked hesitantly.

"Hmm, that would be nice. Why don't you suck my cock, go slow, I want to enjoy your mouth. Make love to my cock, and when I come, I want you to drink it all."

Kylah beamed. "Hmm, thank you, I was hoping you would let me!"

Jeff threw the covers off them, and Kylah nestled between his split legs in a fetal position as she commenced to pay homage to his cock.

"I love your cock," Kylah announced, "and I don't care that you fucked lots of other girls."

Jeff was suddenly feeling melancholy. "Do you want to hear about how it all started?" he asked.

Kylah wasn't sure if she wanted or needed to know about the girls he had fucked, but she sensed Jeff wanted to talk. "Okay, if you want to," she said.

Jeff thought back to his school days. "I guess it all started when one of my buddies in high school bragged to his girlfriend about how big my cock was. His girlfriend kept pestering me to fuck her; she was my first. My sex life snowballed from there," he confessed more to himself than Kylah. "After I fucked that girl she recommend me to all her friends. Sex became a game to me, and girls turned into playthings, to use as I wanted."

Jeff paused to see Kylah was looking at him with the thick helmet of his cock in her mouth. He lightly touched Kylah's face as he disclosed the beginnings of his sexual zealousness.

"They were naïve, young girls, Kylah, willing to give me their mouths and pussies in return for the chance to brag that I had fucked them. I became a status symbol in school, and all the popular girls needed to prove they were part of that group. Even the 'ordinary' girls sought me out, hoping to cash in on my notoriety."

Kylah kept eye contact with Jeff. She pictured Jeff fucking all those girls, and she sucked harder on his cock, using her tongue on the underside. It was the same when she watched him fuck his sister or her mom, just watching his cock slide in and out was mesmerizing. She could understand how all those young girls felt, Jeff's cock is special.

Jeff stared at Kylah for a long time, enjoying the attention she was giving his cock. "Do you want me to continue?" he asked. When Kylah nodded, he started again.

"My first 'woman' was the mom of a school girl. We were in this girl's bedroom, and I had her leaning over the bed while I was fucking her pussy hard from behind."

Jeff paused, thinking about the memory.

"I think the girl's name was Julie or Jane. Anyway, I noticed the bedroom door slowly opened and the girl's mom stood there watching us. She didn't scream like I expected her to. I don't know where I got the courage from, but I felt a strange power. I pulled my cock out and showed it to her mom and motioned with a finger on my lips for her to be quiet. Then I pushed my cock back in and fucked her daughter as we stared at each other. When I was ready to come, I grabbed her daughter by the hair and twisted her around, and forced my cock into her mouth. The girl was gagging on my cock as I came. The mom had her hand in her tight yoga pants, frigging herself. I made her daughter keep sucking my cock until her mom came. It was an amazing day. But that wasn't the end."

"Fuck!" Kylah said as she released his cock from her mouth, "I don't know why, but my pussy is leaking like crazy!"

"Keep sucking, and I will tell you what happened next."

"I can't believe I'm getting turned on listening to your story," Kylah said then swirled her tongue around the head of his cock.

"The girl was pissed that I roughly gagged her and yelled for me to get out of her house," Jeff laughed. "After I dressed I went looking for her mom. I found her in the kitchen, leaning on the counter looking out to the backyard. She was young-looking but had to be in her mid-thirties. I asked her if she enjoyed watching her daughter get fucked. She tried to slap my face, but I caught her hand and then kissed her on the mouth. The mom went wild on me, kissing me, sucking my tongue, hugging me tightly while she grabbed my ass."

Kylah gave up sucking his cock giving it long licks as she kept eye contact with Jeff. "Did you fuck her?"

"The mom was worried her daughter would find us, so she took me to the basement. We could hear the water running upstairs, so we knew her daughter was in the shower. The mom rushed to get her clothes off and even helped me with mine. As soon as she saw my cock again, she went nuts. She fell to her knees and sucked me so hard it hurt. She kept moaning and sucking and telling me how beautiful my cock was. When she couldn't take it anymore, she begged me to fuck her."

"She was your first woman?"

"Yes, but I made her earn it," he said, "I told her I wanted to fuck her ass first. I didn't think she would but she quickly leaned over the couch and spread her ass cheeks for me. She said her husband liked to fuck her ass and she was used to it." Jeff laughed at the recollection of the mom's second thoughts. "I guess her husband wasn't as big as me, though, because once I forced my cock in her ass she kept screaming for me to take it out!"

Kylah licked Jeff's cock from his balls to the tip. "You didn't stop, did you."

"No. She was my first anal fuck and it felt like heaven. I did give her some relief as I switched to her hairy cunt for lube then back to her ass. Her screams attracted her daughter who came in and found us and commenced to yell at me to leave her mom alone." Jeff chuckled. "The mom tried to get up, but I wouldn't let her. I told Jane or Julie or whatever her name was to stop yelling or I would tell her dad they were both horny sluts. The daughter watched me fuck her mom's ass."

Jeff lightly stroked Kylah's face.

"After I came in the mom's ass I cleaned my cock on the mom's panties and order them to take turns sucking me. When I got hard again, I put them in a sixty-nine position and fucked the daughter's ass. We spent the rest of the afternoon fucking on the basement couch and floor. The next day at school, Jane or Julie, whatever her name was, begged me to come back to fuck her and her mom together again."

Jeff focused on Kylah's eyes; she looked so innocent to him.

"I did go back, many times. At first, it was shocking to see a mom and daughter make out with each other, but also exciting at the same time. The mom taught her daughter how to clean her ass, and they loved to take turns sucking my cock clean from each other's back hole."

"So, my mom and I aren't the first, then?"

"No," Jeff said, "are you disappointed?"

"A little, but I love how much you care for my mom."

"You know I do," Jeff exclaimed. "You all mean the world to me."

"Do it!" Kylah blurted out with enthusiasm. "I want you to feel your cock in my ass tonight. I promise not to scream or tell you to stop. I want you to know I'm yours willing to please you in every way."

Jeff reached down and pulled Kylah up until she was lying face to face with him. "I won't lie; it will hurt."

"I don't care; it hurts me knowing how important anal sex is to you, and I haven't given you my ass yet!"

Jeff could see Kylah needed this as much as he did.

"In the night table, bottom drawer, that's where I keep some lube."

Kylah knelt on the floor and opened the drawer; she moved some socks around until she found the lube. With shaking hands, she presented it to Jeff.

"How do you want me?" she asked suddenly unsure of her newfound bravery.

"Squeeze some lube on my cock and use your hand to coat it completely," Jeff said. "When you think it's good enough we can start."

Jeff silently smirked at the amount of lube Kylah squirted on his cock; it looked like she used half the tube. The softness of her slick hands twisting on his cock was having the desired effect. It didn't take long until he was fully hard. The combination of watching Kylah prepare him, and the knowledge he would be taking her virgin ass did the trick.

"Okay, I think that's good," she said, looking up at Jeff. Her wide-eyed expression amplified how scared she was.

Jeff noticed there was still a profuse amount of lube on her hands.

"Reach back and push some lube in your ass," Jeff stated.

Nervously Kylah reached between her legs, but it was too hard to finger her ass. She knelt on the bed, and this time reached behind. Her slippery fingers pushed the lube up her ass repeatedly. Her thoughts were if some were good, then more would be better. She saw Jeff was watching her, smiling with his eyes and mouth, and she relaxed a bit.

"Go get a towel from the bathroom for your hands," he chuckled, "you may have used a touch too much."

When Kylah walked stiff-legged to the bathroom, Jeff couldn't control his laughter, and he wondered what her walk would be like after his cock took her virgin ass.

"Stop laughing!" Kylah smirked as she returned to the bed, "I didn't want to lose any of the lube!" Despite being terrified, she joined in, and soon she was laughing just as hard as him.

Kylah knelt on the bed on all fours, just like she watched Jeff's sister do. The touch of Jeff's hand on her ass made her jump, and she couldn't control the tremors in her body. She tried to relax as Jeff rubbed her back, but her nerves wouldn't let her.

"You're not ready yet for full-on hard anal sex. Why don't you lie down on your side and I will spoon you from behind," Jeff coaxed. "That way, I can control the depth better. The last thing I want is for you to have a bad first experience."

"Like this?" she asked, assuming the fetal position.

Jeff was rock hard at the thought of taking Kylah's virgin ass. He had put her young body through so much already; now this would be her final subjugation. She had disarmed him with her beauty, body, and submissiveness; to the point where he felt guilty about fucking other women. Her mixed-race white-black body tempted him beyond belief. Jeff wasn't sure if this would cause her pain or pleasure. He hoped Kylah found pleasure.

"Shh, babe, I won't hurt you. I promise." Jeff spooned Kylah from behind. "Lift your top leg towards your chest."

"I can't stop shaking."

"We have all night; I'll go as slow as you want."

Jeff reached down and slid his cock between her legs. He wasn't trying to penetrate either of her openings; he wanted her to relax first. He pulled her body tight against his, massaging her breast and kissing her exposed neck. His slippery cock was almost friction-free from the excessive amount of lube on him and Kylah.

"I love you," Kylah moaned. "Do it, Jeff! Fuck my ass."

He scooted back a bit and lined up his cock with her virgin hole. The tip of his cock was at least three fingers wide, and he knew the initial stretch would hurt the most.

"Okay, I need you to listen to me. Push out from the inside, like you would on the toilet. That will open your ass for my cock."

Jeff could feel the tip of his cock against her ass, opening slightly before slamming shut. "Keep doing that babe, off and on. Try to hold it open longer and longer each time."

Her shattered nerves kept her body from obeying. She tried doing what Jeff instructed, but all she could envision was pain from his monster cock, and she would clench up. His cock waited at her backdoor. He wasn't pushing, only keeping skin contact until she was ready. She appreciated how gentle he was with her; a feeling of love surrounded her body. She wanted this to happen.

"Push, push gently," she said.

"Soon," he said. "Keep pushing out; I can feel your body relaxing."

Jeff was right; she was relaxing. He would never hurt her, and if she said stop, he would. His other arm was under her, and she pulled his hand to her mouth. She sucked on his thumb like she did his cock, and it relaxed her a bit more.

Somewhere between loving thoughts, Jeff's cock entered her virgin ass. She sucked his thumb harder, almost biting down. The sudden pain was too much.

Her ass was being stretched too wide! She clenched down tight in panic and almost asked him to stop. It took all her willpower to not say stop, and Jeff pushed a little deeper. Thank goodness for the lube, but still, the pain was unbelievable. Slowly Jeff see-sawed back and forth inside her last virgin hole. No matter how much pain she endured tonight, she was truly his now.

"Hmm, that feels good girlfriend," Jeff moaned. "Your ass was made for my cock. If you play with your pussy, you will relax even more," he said.

Kylah reached down and rubbed her clit. It helped to touch herself there. She wanted to be brave for him. "Go a little deeper," she said. "Wait! Oh, god! It feels like you have your fist in there!"

Jeff stopped to let Kylah adjust again. He knew slow was the best way to make sure she would enjoy this today and in the future.

"Take deep breaths," he whispered into her ear. "You're incredible, just like your ass. Where's my cock?"

"Oh, fuck! You're in my ass! Your giant cock is in my tiny ass!"

"I love your beautiful tight brown ass!" Jeff moaned. "You're my girlfriend now; this makes it official."

"Yes, I am!" Kylah whimpered in excitement, but mostly pain.

It felt like heaven in her ass. Kylah was different than all the other girls he had fucked. He wanted her to feel as much pleasure as he did.

"Your mom is going to be so jealous of you!" he laughed.

Kylah gave a nervous laugh along with him. "I know, and Wendy too!" She felt so lucky to be with Jeff. He was handsome, caring, and so fucking sexy. But, her ass was burning. "I love you!" she whimpered, resolving to be strong.

"I love you too," Jeff said, surprised at his revelation. He sucked on her ear lobe as he picked up the pace. Kylah's ass tension was still there, but she had given herself to him freely, lovingly. He kept the depth of his cock to a minimum, the girth of his cock was enough for her to accept at this time.

Jeff's cock felt huge in her ass, and her anxiety hadn't lessened to the point where she could feel a tiny bit of pleasure. Her fingers were working her clit over hard, trying to take away the pain. Jeff loved her; he said it out loud. No matter what he wanted her to do, she couldn't refuse him. If he wanted to fuck her ass she had to let him.

Jeff had fucked so many women in the ass he lost count. His skill and knowledge had progressed significantly from his original fumbling in the dark with eager young girls. He wanted to teach Kylah that anal sex didn't need to be painful.

For now, he would have Kylah concentrate on abolishing the psychological and physiological negative connotations of anal sex. He would go slow until Kylah developed relaxation muscle control, like his sister Wendy possessed.

He wanted her to feel safe in his arms during their sex play. With conditioning, she will find the stimulus of anal sex just as pleasurable as any other type of sex. His role tonight was to leave her with a positive memory so she would embrace having her ass fucked the next time.

"You're doing great; I'm so proud of you!"

The thickness of Jeff's cock stretched her hole obscenely. Jeff's gentleness didn't help alleviate the pain. She closed her eyes and dreamed of a life with Jeff, imagining his big cock pleasing her. If Jeff's plans worked out, then his sister and mom would also be a part of their group sex life. She focused on the positive, trying not to let the pain interfere with her vision of the future.

Jeff couldn't help himself; Kylah's virgin ass felt so good. His thrusts were deeper and harder now. The slippery lube was doing its job, letting his cock penetrate from the shallows to her deep end. He knew it was heedless and irresponsible to be indifferent to her pain, but his cock had a mind of its own. He reached depths he never intended to find for Kylah's first time.