Stepping Out Ch. 06

Story Info
Tina and Harold's story.
6k words
4.73
10.5k
4

Part 6 of the 8 part series

Updated 06/07/2023
Created 10/10/2015
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

"So, would you like to tell us more?" Kendall asked.

"Would you?" Tina questioned.

"I don't think we know each other well enough."

With a nod, Tina inquired, "Can we talk alone? Woman to woman."

Kendall glanced at Joseph for his opinion.

"I'm going to get another piece of cake," he informed them, and then left the table.

"I didn't want to ask this in front of Joseph in case you didn't want to answer it in front of him," Tina began. "But what I want to ask you is the kind of question I could only ask you—or Jackie."

"Ask away."

"Okay," Tina grinned nervously. "But I'm kind of uneasy about asking it for fear of what you might think."

Kendall could see the genuineness of the other girl's emotions. "I'm in no position to judge you or anyone, and for what it's worth, I'm about as open-minded as they come."

That seemed to put Tina at ease. She nodded. "Okay, well, here goes. Have you ever been attracted to your stepbrother sexually?"

Kendall had an inkling that this was where the conversation was headed. After all, she and Mark had almost instantly been attracted to each other, and Joseph and Jackie got together, so it wasn't a stretch that Tina and her stepbrother would be either. Kendall knew there were a number of directions she could go in here, but in these early stages, she decided to keep it simple. "Yes," she answered in an even tone.

"And did you ever act on it?"

And of course, that had to be the next question. As Kendall thought about how and whether she would answer, she realized that she had nothing to lose. She had the people who were most important to her in her life: Joseph; and though strained, Mark and Jackie, because she was certain the situation with them would be resolved. The point was, there was no one else she had to worry about alienating. "Yes."

Tina smiled her relief. "Oh, thank goodness."

"Of course, that begs the question, have you ever acted on it?" Kendall felt it necessary to ask.

"Yes. What about Joseph and Jackie?"

"They have also," Kendall didn't feel uncomfortable in saying. "And yes, so have Joseph and I, as have Mark and Jackie." But she stopped short of telling about their foursomes.

Tina's face lit up. "Wow. This is better than I expected."

"Glad I was able to brighten your day. I am curious how you and your stepbrother got started."

With a nervous nod, Tina said, "Okay, I guess that's a reasonable question. Harold and I have been together since we were ten years old. I think we mostly always got along. We had the expected sibling spats and that might have been fueled sometimes by our parents having disagreements about one child getting more than the other. But it was largely harmonious.

"We might have started noticing each other differently when we went through puberty and our bodies were changing. But I think we both really viewed each other as real siblings because we had been together so long, regardless of the fact that we weren't blood related, and I guess because of that, we weren't attracted to each other.

"But that changed during our senior year in high school. Harold was on the football team and the baseball team." Tina smiled warmly. "He wasn't very good and didn't get to play much, but his body really developed. We both turned 18 around the middle of the school year, and that's when I really started to see him differently. And then one day, I caught him jerking off." She paused to gauge Kendall's reaction.

"Go on," Kendall prompted. "Nothing to be ashamed of."

Hesitantly, Tina continued, "He had the most beautiful penis I had ever seen. Not too big, but nowhere near small."

"How many had you seen?"

She shrugged. "Not many real ones. I spied on my stepfather a few times. His was really nice. And that kind of prompted me to look on the internet, and that led to X-rated movies. Anyway, watching Harold stroke himself was pretty exciting. I wanted to burst in, but I didn't. I went back to my room and masturbated. And that started a trend. But he must have just been careless that day because I didn't get many more opportunities to watch him. Still, I had my memory. I hadn't really masturbated much before then, but I really got into after that. It made me feel good. Real good. And it made me feel like a woman."

"It is kind of exciting watching a guy jerk off," Kendall threw out to help put Tina more at ease because the latter still seemed stressed in telling her story.

That did relieve Tina and she thought, what the hell. So, she told her story no longer caring what Kendall thought. "I was really developing a crush on Harold. So, I started dressing differently hoping he would notice me. I even left cracks in my door hoping he would spy on me. It didn't seem like he did. Little did I know. Then, one day . . ."

* * *

"How was practice?" Tina asked when Harold arrived home one afternoon.

He merely glanced at her as he headed for the kitchen for a bottle of water. "Good."

The next day, she timed her shower to coincide with his arrival home from practice walking from the bathroom to her bedroom in only a towel loosely wrapped around her.

"Hey," was all he said, barely even noticing her, it seemed.

Tina was almost to the point of realizing she was on a fool's errand when the strangest thing of all happened. Not trying to get his attention, she actually got his attention when he appeared before her bright and early Saturday morning when, still in the shorts and tank top he slept in, his gorgeous biceps on full display, with circumstantial evidence that his morning wood had not yet subsided, he sat on the living room sofa beside her. It nearly frightened her when he spoke.

"I've got a big test in English on Monday and I'm not doing too well in that class. If I fail this test I'll be kicked off the team. You're good in English, aren't you?"

"Yes," Tina answered hesitantly.

"The problem is, I haven't really been keeping up with the class, and, well, I need help."

"And you need me to give you that help?"

"In a word, yes. My dad and your mom don't know and I know they're going to be gone all day, so I thought this was a good time—if you don't have any other plans, that is."

Trying not to let her shock show, Tina knew she had to help him because he was showing her some attention . . . such as it was. "Ooookay," she said slowly. "Well, fortunately, I'm taking the same class with a different teacher, and I don't really have any plans today, so let's get started."

Over the next several hours, Tina was able to cram a semester's worth of English into a very short time. Harold didn't seem shy to ask questions about things he didn't understand or to have her re-explain other things. Surprisingly, he really appeared to pay attention and take an interest, and of course, she was just happy spending the time with him. But as the afternoon came around, he seemed to start taking an interest in her, leaning against her, touching her arm here, leg there, brushing hair out of her face. She even caught him staring at her a few times.

Finally, after one of those times, she had to ask, "What?"

Harold grinned. "I knew you were smart, but I had no idea you were this smart. It's intimidating."

"Is that why you rarely give me the time of day?"

Looking stunned, he asked, "Do I do that?"

"That's how it seems," she answered honestly, fearful that she would turn him away.

"I'm sorry. I never intended to do that."

"Okay. If you say so."

"You don't believe me? I'm serious. And I really appreciate you taking the time with me. If there's anything I can do to make it up."

"You could just not ignore me so much."

"I promise. But I really am intimidated by your intelligence."

"Yeah, well I'm intimidated by your good looks and great body."

"Don't sell yourself short. You're pretty hot yourself. I have noticed that."

"Hey, you don't have to butter me up. I'm already helping you."

"I'm not. I truly mean it. You're as hot as any of the girls I date."

"Well, none of the guys I date look like you."

He couldn't top that, and so, they found themselves staring at each other. Even she was at a loss for words. But neither seemed to be able to resist allowing their faces to drift closer, nor did they quickly draw back when their lips made contact. On the contrary, the kiss steamily escalated as though the tea kettle was finally beginning to whistle. Tina did not stop Harold's arm from wrapping around her.

When their kiss broke, their foreheads still touching, he again brushed hair away from her face. The motion of his hand accidentally swept the strap of her tank top off of her shoulder and he was slow to remove his hand from the bare skin. Likewise, she couldn't prevent her palm from touching his pectoral muscle. Both gestures were easy stimulus for their lips to meet again.

After another pause, Harold's hand dropped, allowing her covered breast to fill his palm. He smiled over the delicate touch; she smiled her approval. Another round of lip-licking kisses followed, and then he gently peeled the material away from her right breast exposing its well-roundedness. Her grin widening, she rotated her left shoulder to encourage him to strip away that side. Eagerly responding, he fondled both breasts as their lips joined again.

A soft cry-like moan escaped Tina's lips.

Harold then quickly pulled off his shirt and pulled his stepsister to him. He reveled over the stimulating sensation of skin against skin.

Her arousal level having reached an all-time high, Tina reached down to palm the bulge in her stepbrother's pants. She had never touched a real penis before and loved the feel of it—even though covered—in her hand.

Meanwhile, Harold was inching his hand up her leg, caressing her thigh as he did so. She was delighted to be touched like this. However, when his fingers pushed the loose-fitting legs of her shorts up, exposing her cotton panties, Tina was at once embarrassed to be wearing such an ordinary undergarment and not some fancy, sexy bikini panties. However, that was quickly forgotten as Harold's fingers danced over her pussy, hitting all of the right spots. He accompanied this with tender sucking of her nipple. These were the most glorious feelings, Tina had ever experienced.

Nearing delirium, Tina quickly lifted her tank top off and pulled her shorts down and off, leaving her only in her underpants. Grinning at the sight of her with so little on, Harold lifted her left leg over his right thigh, which spread her appendages even wider, allowing his fingers to reconnect with the sweet spot between her legs. However, this was no longer enough, so he closed her knees together so he could remove her drawers. Extending her legs again, her gaping pussy was bared before him. He'd seen and touched vaginas before, but somehow, this one was a completely different experience.

Harold's fingers explored her vulva, hole and clit, all the while driving her insane. They had to kiss again and she had to pinch her own nipples to not only make certain this was real but for the added pleasure it provided, not that her overwhelmed mind needed more pleasure. It was simply a drug she had to have, and have more of.

And the more she had to have now was him. Her hand returned to the bulge in his shorts, squeezing, caressing . . . but still, she had to have more. Her palm snaked under his waistband, making contact, its pulsing made her eyes widen . . . but she had to have even more. She tugged at his shorts and he assisted by lifting his rear and pushing his pants down.

The sight of it caused her to gasp. Sure, she had glimpsed it before through slits in doorways, but up close, it was . . . it was . . . massive came to mind, but what she really meant was magnificent. Seeing pictures of penises on the internet was exciting, but the real thing . . . within grasp . . .

Her hand darted for it, grabbing both his balls and the base of his rod. It took her breath away.

For his part, Harold's cock had been handled by other girls, but his stepsister's fingers wrapped around and gliding up and down was truly unique.

As though she knew what she was doing, guided only by what she saw in movies, but definitely driven by desire, Tina bent her head and took the crown of his cock in her mouth. She had no concept of what she expected it to taste like, but it didn't taste bad. After a couple of bobs it was all saliva anyway. It did make her feel powerful; particularly with the whimpering sounds coming from him. Having watched so many movies of blowjobs and wondering what the thrill was, why a girl would want to suck on a hunk of skin, she now knew. There was something mesmerizing about it, positively something erotic, and perhaps because it was her stepbrother that added another stimulating dimension.

Tina actually sucked the head and foreskin, and jerked the lower part with her fist. Then as an afterthought, she licked the entire shaft like it was a Popsicle or something.

Her concentration was disrupted when she felt her body being maneuvered. But she was so transfixed by what she was doing that she could not re-focus on what was happening. It wasn't until she felt something wet touch her pussy that she stopped short. However, after a couple of seconds, she realized that Harold had moved them into a 69 position and he was tonguing her clit. It felt marvelous and she let out a deep sigh of contentment as she went back to the penis in her hand.

Again from the influence of movies, Tina felt desperate to want to deep throat Harold. Even though she had kind of practiced with her dildo, she'd never quite got it down. Perhaps a real cock would go easier. Her sudden gagging told her it would not. Harold raised her up merely shaking his head.

He then sat on the sofa and manipulated Tina to sit on his lap facing him. With his hands on her hips he positioned her over his rod. "You want me to keep going?"

"You better not stop."

Using one hand, he guided his cock into her hot and wet pussy, marveling over how easily it slid in.

They both let out moans as overwhelming feelings pervaded them.

Having seen this position many times, Tina immediately started bouncing up and down and occasionally pivoting back and forth and rotating around. He filled her much more completely than anything else she had ever stuck inside her, and the divine feeling that came from it was much more than the cold metal or dull plastic dildos she could compare it to. She was breathing heavily, and for a moment, thought she might actually hyperventilate, so she tried to keep her breathing under control. But this incredible experience made it extremely difficult. She only knew that if she just achieved a reasonable orgasm, she could die happily.

A fleeting thought occurred to her and went just as fast as it came, and that was that her stepbrother really seemed to know what he was doing; particularly when he rolled her onto her back, his magnificent cock never leaving the warm and snug confine of her tight pussy and finished her with long, powerful and purposeful strokes. She was so glad they were alone because she let out a screech when her mind and body exploded in a fit of pleasure like none she had never known. She closed her eyes hard and concentrated intensely, wanting it to last forever. That might have bought her a few extra seconds, but it was also superseded by the feeling of warmth on her abdomen.

Opening her eyes, Tina saw that Harold had pulled out of her and was spraying her belly with scalding semen—lots and lots of burning love. She wished she had been paying attention. She would have told him to come inside her since she was protected. She had wanted that experience also. Maybe there would be a next time.

She also noticed the extreme engrossment on his face and realized it was no less intense for him. As a few dribbles still spurted from his cock, Tina reached up and cupped his balls, tenderly caressing them in her palm. The gestured provided a couple more squirts before he fell back onto the opposite arm of the sofa, his dick still in his hand.

Harold grinned when he saw his stepsister scoop a glob of his pearly white cream with her forefinger and touch it to her lips. Tasting it with a swipe of her tongue, her eyebrows shot up and her mouth formed a smile. She enjoyed a couple more fingers full.

Afterward, once their breathing and what they thought was normalcy had returned, realizing the implication of what they had done, Harold was bristling with apologies.

"I'm so sorry. I let that get out of hand. My . . . my . . . I shouldn't have lost control. I—"

"I don't remember complaining," Tina said softly. "Or telling you to stop. In fact, I told you not to."

"I know, but we shouldn't have done that. We're brother and sister."

"I know we think of ourselves that way, but this might be one of those instances where what we really are factors in."

"Still . . ."

"You didn't enjoy it?" Tina asked, feigning disappointment.

"Of course, I did."

"Then don't ruin it. That was my first time and I want to remember it positively, not as something I did that was wrong."

"Your first time?" he repeated, absolutely floored. "Why didn't you tell me? I would have been gentler."

"Again, you didn't hear me complain. You were fine. And there really wasn't an opportune moment to mention it."

"I—"

"Please, just let it go for now," Tina pleaded. "Let's just see how it goes for a few days."

"Okay," Harold conceded. "But the folks can't know."

"Duh! You think I'd really tell them?"

But on Monday afternoon, Tina paced nervously, waiting for her stepbrother to come home from practice to find out how he did on the test; just as Harold eagerly rushed home, skipping practice, to tell her.

She was hardly surprised when he arrived much earlier than she expected, but definitely thrilled, and even more so when he announced that he had aced the test. Of course, their natural response to the victory was to hug, but that quickly escalated into a steamy kiss, and the heat from that graduated it to extreme passion.

Pulling back and breathing heavily, Tina huffed, "Your room or mine?"

There was definite lust in his eyes that instantly morphed into distress from her question. Taken aback, he merely shook his head and went to his room.

Tina was actually stunned. Saturday evening and all day Sunday Harold had become the ideal stepbrother, polite, attentive, still not real talkative, but then he never was. She thought surely a change was in the air. But now, he had returned to his usual aloofness. Perhaps it had been too much to hope for that after their "study" session on Saturday he would show her more such affection, even though he had attempted to apologize again yesterday. Obviously, he still thought what they had done was wrong; even more obviously, he was not quite ready to do it again.

It was kind of ironic, Tina thought. Usually, it was the guy who was the sex hound. Here was a guy who had a girl who was more than willing, but because she was his stepsister, he was not interested. It was useless to try to discuss it with him. She could have a deeper conversation with their pet dog. Maybe he would come around.

And as the days wore on there was evidence of that.

She actually noticed him spying on her. It began one morning when she was dressing for school. He passed by her bedroom door, which was open about an inch, and though she was facing away, she could see him through her dresser mirror. A day later, in her room after school, she was changing into more casual clothes and was sitting on the edge of her bed in bra and panties only checking herself out in the mirror. Once again, she detected him lingering outside her door and decided to give him a show. Still facing her mirror away from the door, she cupped her breasts, squeezed them together and moved them around as though adjusting her bra. She then shoved her hand inside her panties (she was now wearing sexier under things since that Saturday) and played with her pussy. She had intended only to tease him a little with it, but knowing he was watching her actually got her going and she brought herself to orgasm. She could see him rubbing his cock through his pants, and as soon as she finished, he darted off toward his bedroom, no doubt to finish jerking off. It made her smile to know that she had that effect on him.

12