Chapter 5

Carol was a bit jealous actually – she liked having Tommy all to herself and now she would have to share him. But at least he was keeping it in the family so she didn’t need to worry about him going off with someone else. And she knew she was still Tommy’s number one girl, so her position with him was secure.

Diane may be younger, but Carol still had her beat in the figure department as well as in the adventure department. She knew that Diane was a bit old-fashioned and traditional in her sexual tastes, liking straight sex, oral sex, and occasionally anal sex. Carol, on the other hand, liked to play around with different kinks and “experiment” more.

Far sooner than Carol would have liked, she had him hard as a railroad spike and he was ready to “indoctrinate” his little sister and bring her into the fold.

“All right Diane, are you ready to become one of ‘Tommy’s Girls’ like Mom is?” he asked.

Diane, still in her semi-lucid state, could only moan a weak response which Tommy took as a yes and he rolled her onto her stomach and pulled her hips up so she was on her knees with her face and chest on the mattress. The perfect position for taking her from behind and making her feel his dominance!

“Now slut, I want you to sit in your chair and watch as I take this little girl for my own. Watch as she feels my cock open her for the very first time and see the reaction on her face when she realizes just what she’s gotten herself into.

“Watch as she feels my cock burrow deep into her neglected pussy ... deeper than anything she has ever known before. Listen to her cry out when she thinks I’m splitting her in two and then listen to her moan her indescribable pleasure when she finally learns the power of my cock.

“You wanted to watch her first time with me, so I want you to sit there and take it all in. But do not play with that pussy of yours until I tell you you can. If I catch you touching yourself, there will be hell to pay, you hear me, slut?” he warned her.

“Yes, Sir.” Carol sat back down in her chair, spreading her legs wide so he could plainly see her shaved pussy. She put her arms on the arms of the chair and got a grip on the ends. She would need something firm to hold on to for this show!

With his mother in her front row seat to watch as he fucked his sister senseless, Tommy moved around behind the trembling young girl. Diane remembered all the things that her mother told her about Tommy’s abilities and she was both excited about what was going to happen and scared of it at the same time.

She had never seen Tommy naked since they were both very young so she had no idea just how big he was. Carol had told her he was well-endowed, but she hadn’t seen just how well endowed he was. But she was about to!

Tommy laid one hand on his sister’s upturned ass and Diane gasped in surprise. His other hand grasped the base of his cock and he moved closer so his cock shaft rubbed under her pussy, sliding between her wet puffy lips, teasing her with his cock.

“Ohhh...” she moaned softly.

“That’s right my sweet little sister ... your brother’s hard cock is knocking at your door. Are you going to let him in? Do you want to really feel this cock ... feel it buried so deep in your tight little sister pussy? Tell me what you want Diane. Beg for what you want,” he said.

“Please, Tommy, I want your cock ... inside me. Please fuck me ... fuck me with your hard cock and show me what you have shown Mom. Please, I want to be Tommy’s Girl too. Please fuck my tight wet pussy!” she whimpered needfully.

“What do you think, Mom – that wasn’t very good begging, even for a beginner. Do you think I should fuck our little bookworm or wait until she learns to beg better?” he said, looking at his mother.

Carol knew what he was doing – he wanted to get both of them superheated. He wanted Diane to beg harder and more desperately and he wanted his mother to get worked up herself sitting there watching them.

“Fuck her, Tommy, fuck her and show her why she needs to learn to beg! Maybe if she gets a taste of your amazing cock she’ll want it more ... she wants to beg for it – God knows I do! Show her what she’s missing, baby. Fuck her until she appreciates what you can do for her!” Carol said, squirming in her seat just thinking about it.

“Maybe you’re right ... maybe if she knew just how good my cock can make her feel, she’ll want to feel that way more often. Okay, Sis, get ready...” he said. Then he put the head of his cock at her opening, just inside her outer labia.

Once his cockhead was seated against her tunnel entrance he gathered himself and began to push into her. He went agonizingly slowly, opening her up just an inch at a time, teasing her as much as letting her feel every bump and ridge on his cockshaft.

At first, Diane thought it felt nice, but it wasn’t anything special – after all, she wasn’t completely ignorant of what it felt like to have a man inside her. But her limited experience had been with boys around her own age. And certainly, none of them had a cock like Tommy’s eight-inch sword!

Within moments, she realized that Tommy was not one of her schoolboy admirers. None of her past boyfriends ever had a cockhead that opened her like Tommy’s was now – and he wasn’t even all the way inside her yet!

Although Tommy couldn’t see her face from his position behind her, Diane’s face was a mask of shock, surprise, and awe. Her eyes were wide as dinner plates and her mouth had dropped open as her finger dug into the bed, gripping handfuls of the sheets until her knuckles turned white.

At first, the surprise of what was happening took her voice – even though her mouth was open, no sound came out. Then she found her voice and she used it!

“Oh my GOD, Tommy! Oh, fuck your cock is opening me so wide! Oh, I don’t know ... I don’t think I can take it all! Oh fuck, it’s sooo big...” she moaned loudly.

“Just relax Sis, we’re only getting started here!” he said. Just about then his cockhead finally disappeared inside her with a little pop. “There, my cockhead just slipped inside you. The hard part is over now.”

Tommy stopped for a few moments to let her get accustomed to his size. He didn’t want to hurt her – she was his sister after all. He wanted to make this whole experience something she’d enjoy and want more of. He knew he wouldn’t mind having her, in addition to his mother, whenever he wanted to have a little fun in the bedroom!

Diane Walker was a very attractive young eighteen-year-old girl. While she didn’t (yet) have her mother’s stunning figure, she was still a looker in her own right with brown hair and green eyes, a warm smile that she never minded sharing with everyone and a very respectable 32C-24-34 body that was the envy of many of her fellow classmates.

In fact, Diane could have been one of the most popular girls in school had it not been for what her father did to the family. His cheating on her mother, then running off with his new playtoy, soured Diane on any kind of romantic relationship.

She didn’t want to feel the pain that her mother had ... the same pain that she heard the other girls in school felt after being similarly cast aside.

No, her books never cheated on her ... they never left her for another. They were always there ready to comfort and entertain her whenever she needed them. But books for all they did for Diane, could not keep her warm at night. They could not give her the love she so wanted. And they could satisfy that other need ... the one that Tommy was now addressing quite adequately.

“Oh God, Tommy! Oh fuck, you are so deep ... I can feel you in my belly! Oh God, how much more...” she cried.

“Easy Sis, I’m just over halfway in ... you are doing fine. Just relax and let this happen ... it’s okay...” he said encouraging her.

“You’re only halfway in? Oh God!” she said dismayed.

“You’re okay, Diane. Just relax ... I know what I’m doing. Remember, babies come out of here and I’m far from the size of a baby!” he said, stroking her back. He realized that Diane was concerned about whether this was such a good idea after all.

She needed something to take her mind off what he was doing to her ... a distraction that would make her concentrate on something besides his cock burrowing into her. He reached over and grabbed the same purple vibrator that he had used on her earlier and clicked it on.

He reached around with one hand and put it on her clit once again. And once again it lit her up like the Rockefeller Center Christmas Tree!

“TOMMY! OH MY GOD! Please ... not the vibrator! Oh, fuck Tommy! Ohhh...” she squealed the moment it touched her already tortured clit.

“That’s right, my dirty little sister ... after seeing how much fun you had with it before, I just knew you’d like to spend some more time with Mom’s buzzing little friend!” he laughed evilly.

“Please, Tommy! Oh please ... you’re gonna make me cum again!” she cried out squirming and twisting as the demon vibrator spun her world out of control.

“Well, we can’t have you cumming so quickly now can we? No, we need to make this little party last awhile!” he said, pulling the vibrator away after a few trying moments. So shall we go back to opening up that tight little pussy some more?” he asked grinning.

Diane, out of breath from the vibrator, could only pant an answer. Tommy took it as a yes since she didn’t say no and he pushed in a bit further. He was now about three-quarters in her pussy and he was completely enjoying the tight fit his sister’s deserted pussy provided.

He glanced up at his mother. She was sitting slumped back in her chair, her head resting on the back, her face a mask of lustful want. She was so engrossed and aroused by what she was witnessing that she was barely able to stay in her seat. Her pussy was leaking like an overfilled bathtub and she moaned incomprehensibly as she rocked her head back and forth.

He took note of his mother’s condition. He would reconcile with her later, but first, he would use her debility to bring her deeper under his control.

“Look mother, look at your little girl ... her ass stuck up in the air with your son’s cock buried deep in her dripping pussy, moaning like some street corner whore! She’s a slut just like you, isn’t she! Say it ... Say my daughter is a slut just like me!” he ordered her.

“My daughter is a slut just like me!” Carol repeated.

“That was pathetic! Now say it again and make me believe it!” he said, louder this time.

“My daughter is a slut just like me ... a dirty filthy fuckslut ... we are your fucksluts, Tommy baby ... we belong to you!” she said, more impassioned now.

“That’s right. Now watch as I turn your sweet little darling into the same begging, cum-hungry, cockwhore, I made you! Watch as I drive my cock into her tight young pussy until she gives up her last ounce of willpower and resistance and surrenders everything to me!”

It was big talk, sure – he knew that. But that’s just the kind of cock-sure braggadocio that had turned his mother into jelly and kept her panties wet whenever he spoke to her! The girls in this family were used to the nice, polite, Tommy – the one they had raised and grown up with.