Chapter 13: A Different Perspective

Emily had sat down on her bed next to two bathroom towels. Reaching over to the larger of the two towels, and picking it up, she placed it over her lap. It was now lying half on her bare thighs and half over her short hip-hugging levi shorts. Satisfied with the placement, she patted her thigh, and said to her naked brother, “Ok, come here, over my lap.” Hearing the familiar request, he couldn’t help but protest, “Why? --- What did I do wrong this time?” He asks, staring apprehensively at the towel and then back up to her face.

“Nothing up to this point, other than you don’t seem to be following my orders very well.”

Tommy sighed, and resigned himself to the inevitable. He placed himself wearily on her thighs, thinking these spanking were starting to get old, and worse, this time he won’t be able to feel his cock on her bare thighs, not with that stupid towel being there.

Reaching over to the second smaller towel, she picks it up, and immediately drapes it over Tommy’s head, blocking him from seeing anything else, stipulating at the same time, “You keep that towel there, until I tell you otherwise.” When she had lifted that smaller towel, it had exposed another object. It was a latex glove which she had hid underneath. It was the same glove she had pilfered out of her science lab, that very afternoon. Picking up the glove, she begins to stretch it over her right hand, so it fit snugly. “Now this next lesson you may find a little distasteful, but remember this. Many women and men find it a large turn on.” Placing both her hands on his ass cheeks, she adds, “Including myself, by the way.”

Taking her two hands, she starts to spread his two ass cheeks apart, exposing his most private area. “What I’m talking about is the ass. --- Right here.” Placing her latex covered digit directly on his asshole, and starts to softly probe her brother’s little rectum. Immediately Tommy attempts to get off Emily’s lap, but she was already expecting that. There was a hard slap on his ass, followed by a, “You stay down there Tommy, or you’ll be feeling a belt across your ass for your next punishment session. --- Understand?”

“Yeah, I understand.” Tommy sighs as he settles back down, knowing by past experience that Emily didn’t make empty threats.

Placing her hands back on his ass, she spreading his ass cheeks apart once more, adding, “And you know Tommy, you really need to clean up a little better back here.”

“Sorry...” Tommy, feeling a blush coming on, and says embarrassingly, “ ... but how’d I know you would be going back there.”

“That’s no excuse Tommy. You never know when your woman will want to access you back there, so you should always be ready.”

Why in the hell should I be ready for that? Tommy, asks himself incredulously.

“Now today, I’m going to teach you how to please a woman through her backdoor.”

She was starting to press her finger more firmly on his little button. Not enough to penetrate yet, but just enough to start.

“Now don’t be afraid, I’ve done this many times before.”

That was a lie. Oh it was true that it was always something she wanted to do, she just never thought any of her boyfriends would go for it, and never, never, until now, had she the guts to order any boy to do it.

“So I thought the best way I can show you is to give you a little demonstration.” Widening the butt cleavage with both her hands, she leans her face directly over and drops a big hunk of her spittle right on top of his exit hole. “Yes, Tommy.” Placing her gloved finger back on the now wet hole. “You’re going to please my little asshole, somewhat, like I’ll be doing yours. Well almost like I’ll be doing yours.” Now working her spit slowly down in his asshole. “Instead of your fingers doing the nasty deed, your tongue will be.” She works the spit in slowly, forcing it in past his sphincter muscles a bit. Leaning over again, she again drops another gob of spit upon the puckered hole.

Tommy, feeling the finger start to play with his asshole, It was making him feel very uncomfortable, but for some reason, he didn’t want her to stop either. Directly on the opposite side, he could feel his penis start to expand, and as it did, he felt the terry cloth of the towel rub up against his cock.

Emily finally satisfied that she’d loosed his sphincter up to her satisfaction, takes her finger and plunges it deep inside Tommy, causing her shocked stepbrother to gasp and cry out loud, “Hey! What are you doing? I’m not gay!”

In a low growl, Emily says, “Are you implying that I’m a guy?”

When she didn’t get an answer she follows it up with a growing anger in her voice, “Answer me Tommy! You know how angry I get when you don’t answer me.”

“No. You’re not a guy!” Tommy bleats out in self defense.

Emily leans over to the side, toward his face, and tilting her head down to look into his eyes, she says triumphantly, “Then this is not necessarily gay thing. Is it?”

When no reply came, she asked again, louder this time, “IS IT!”

Tommy could only respond trepidatiously in a whisper, “No ... I guess not.”

Emily smiles at his capitulation, saying, “Very good.” And then, with that finger still embedded in his ass, she gives Tommy her next command, “Ok Tommy, I want you to slowly raise yourself up, but stay on your knees.”

Tommy slowly raises himself up, feeling really strange, as her digit was still completely up his butthole.

After Tommy’s weight had come off her waist, Emily works herself up out from under him, nice and careful like. This was harder to do then she expected, as she had to make sure her right forefinger stayed firmly in place the whole time. Emily finally was able to work her way out from under him, and she then positions herself directly behind him. Now picking up the large towel that had fallen off her lap, she places it back in place, right underneath him. Then placing her left hand on his neck, she starts to press it down. “Tommy, I want you to lean yourself down and place your head on the bed.” He bends over obediently, acquiescing to his true submissive spirit. It is at this point, seeing him bent over like this, head down and with his ass in the air, waiting for her to do whatever she wanted, it made her really wish she owned one of those strapon dildos. I’ll definitely have to get a hold of one of those. She says urgently to herself.

Reaching back under him with her free left hand, Emily wraps her fingers around Tommy’s cock and starts to squeeze and re-squeeze the penis with her free hand. Feeling the cock start to harden up, she comments, “You like this Tommy. Don’t you?” Then feeling the cock get nice and hard as she now begins to softly stroke it, up and down. She leans down to his face, looking into his eyes. “You like my finger in your little asshole? Come on Tommy admit it. You do. Don’t you?”

“Yeah, a little.” Tommy, had to uncomfortably admit. Not knowing if it was because of the actual feel of her finger in his ass, or if it was because of the left hand on his cock, or was it just due to the fact that she was, again taking complete control, and humiliating him again. Maybe it was because of all these reasons.

“Well you just wait a little bit. I got a feeling you’ll like it even better in a second. What I want you to do now, is to reach back and spread those ass cheeks of yours nice and wide for me.” When Tommy doesn’t obey promptly, she says, “You heard me now. Don’t make me wait.`` and as she said this, her left hand had moved down to his testicles and starts to give them a squeeze. Not too hard to be painful yet, but just enough to give Tommy the message that he better obey her, and obey her now.

The message is conveyed as Tommy’s hands quickly come back and the cheeks are spread out wide. She probably didn’t need Tommy to do this as his cheeks were spread pretty wide already, given his head down position, but she liked to push his boundaries as much as she could. It was good to get the practice in now, as it will mean it will be all the much easier to apply these new skills for on that boy she intended to seek out. Now making good use of the spread out buttocks, she removes her finger from his ass just so the tip was still penetrating and then leans over to spit two more times down on it between the ass cheeks, lubricating the finger once more. “Now let me see if I find that prostate of yours.” Emily plunges her finger back in, eliciting a gasp from her brother. Finger now in search of it.

Emily didn’t have much to go by except some text descriptions on where it was located and what to feel for, and then how best to stimulate it once it was found. She soon felt a slight bump and was wondering if this was what they were describing. Exploring the area further, she pressed her finger down on the bump, causing an involuntary groan to be emitted from Tommy. Face breaking into a grin at her recent discovery she announces, “Ah, there it is. Right where I thought it’ll be.” She then begins in earnest now. She starts to move her finger over and over Tommy’s prostate, applying more and more pressure down in that area.

Tommy starts to grunt uncontrollably, “Ugh, ugh, ugh, ugh...” as his mouth emits in little gasps.

“Looks like my Bro does like that.” With her left hand she starts to stroke his dick again.

“Here, help me out Tommy.” Emily takes her left hand off his dick and uses it to grab his left wrist off his butt cheek and she moves the adjoining hand back toward his penis, then coaxes that hand to start jerking himself off. Tommy needs no further encouragement and starts to beat off with his hand, all the while continuing to moan away as he felt Emily’s finger goes about violating his ass.

Now that her left hand was free, she was able to place it on his left ass cheek, giving her right hand much more leverage, and this allows her to really quicken the pommeling of his asshole and apply even more pressure on his prostate. “You like me finger fucking your ass, Tommy, don’t’ you?” She cheerfully asks him.

“What comes out of Tommy’s mouth is a strained, “Ahh ... kind of.” This whole sensation felt extremely weird to Tommy. His dick no longer that hard, but he was feeling very stimulated in some other kind of way, but at the same time he was feeling very uncomfortable. What was she doing to him? He wondered. All the while, his left hand was still stroking his semi-hard cock. This went on for a minute or two. Tommy then felt it, and he found his breaths getting more and more shallow and they started to become in a quick succession. He found as this feeling was coursing through him, that it was something he was completely unfamiliar with. And it was getting stronger and stronger. Finally, before he even realized it, it seemed to peak, but it didn’t culminate with his usual euphoric climax, like he had been expecting, and was definitely use to. Instead, when he came, the pleasure was one of a satisfying release. Like something that had been building up was he was finally able to let go. And when Tommy forced his eyes open to witness what was happening to him underneath. What he saw was a penis that had started to spill its warm cum contents out onto that towel that was so strategically placed below him. Spill being the operative word here. Not shoot or ejactualte, but spill. And seeing this pitiful ejactuallation, made Tommy’s humiliation all the worst, and, for him at least, a bit more erotically pleasurable.

Emily’s face erupted in a big smile as she saw her brother’s seaman spill out onto the towell. I did it! I actually milked my first boy! She exclaimed excitedly to herself. The first of many she hoped. Still feeling the euphoria and sense of accomplishment, she tried to get herself back under control. Although she knew she had not yet able to wipe that shit-faced grin off her lips. She worked her finger slowly out of Tommy’s ass saying, “Very good Tommy. Now let’s wipe you off a bit, and then we’ll move on to the next part of the lesson.” Emily strips the glove off her hand and places it on the towel that had covered Tommy’s face before. Then with the other towel, now containing a pool of Tommy’s cum, she folds it in half, over the spent cum, before picking it up to wipe his dick down, Wiping away the residual that was still continuing to seep out. And finally taking that same towel, starts to wipe up and down his crack. Wiping off any her wet spittle that still remained. All throughout Tommy just stayed there, docile as a little baby, but a baby who happened to have his head down and ass up in the air, and who was still trying to understand what had just happened to him.