Little Sister Ch. 07

The next afternoon Denise told Jean that it was time to start learning how take a cock in his tight little butt pussy. First, she told him that he needed to be sure he was a clean as a whistle. There should be no hair any where on his butt and his cock hole should be well scrubbed. After seeing to external cleanliness he should do some internal work starting with an enema as near as possible to having sex. Then she told him to follow this up with a douche using a nicely scented wash. Denise told Jean that he should also use a tube of vaginal lubricant applied with an applicator so that it was well distributed up in his cock hole. Finally, she took him by the hand and led him into his bathroom and showed him where all the necessary devices and supplies were stored. "When you're finished getting ready," she told him, "just put on a slip and come to my bedroom for the real instruction." With that Denise left Jean in the bathroom and went to the kitchen for a cup of coffee while she waited for him to complete his chores.

After finishing her cup of coffee, Denise went into her bedroom and took a box down from a shelf in her clothes closet. In the box was a strap on L shaped dildo, a jar of Super Slick Sex Lube and some latex finger sheaths. She sat these on the bed as she heard Jean entering the room. She turned and watched Jean wearing a navy blue slip glide across the room to the bed with mincing steps that gave his gait a sexy sway. "My, my pretty girl you look ready for a good fucking," said Denise with a big smile on her face. "Get your cute ass over here and sit it on the bed while I get ready for you." With that Denise slipped out of her satin ecru pajama bottoms and matching panties. She picked up the dildo, opened the jar of lube and applied lube to one of the shafts. With legs bowed, Denise began working the shaft of the dildo up into her pussy. When the shaft fully penetrated her and had reached the oval platform that divided the two shafts from one another she stopped. There was a look of pleasure and anticipation on her face. Denise pulled the straps up an around her waist and secured the dildo in place. The second shaft now protruded straight out from her crotch looking every bit like an erect cock. Denise grinned at Jean and said, "Get some of the lube in the jar there and grease up my dick." Jean complied while never taking his eyes off the dildo jutting out at him.

Denise said, "OK Little Sister its time to find out what it feels like to be fucked like a woman. I want you to hike that slip up around your waist and lean over the bed face down. Pull your big girlie boy clit up under your belly so it doesn't detract from the appearance of you butt pussy." Jean did as he was instructed. Denise then put a finger sheath on and lubed it up. Next she told Jean, "Reach back with your hands and spread your ass cheeks for me." Jean did as he was told. Denise then inserted her finger into Jean's butt pussy and slowly pressed her finger in as deep as it would go. Next she began to slide the finger slowly out and then in again. Jean moaned and appeared to be enjoying Denise's probing finger. "Don't think this is all there is to it," said Denise. You are no where near to taking an erect cock up that hole."

"I know," said Jean. "Your finger feels good but I'm afraid the dildo will hurt me. It looks so big."

"It isn't all that big," replied Denise. "It is about average for a hard cock and it won't hurt, if you do exactly as I tell you."

"OK," answered Jean with a slight quiver in his voice.

"The secret to taking a cock up the ass without a lot of pain is to push out as it is going in. This actually relaxes the anal muscles and allows your cock hole to expand to accommodate the penetrating dick," explained Denise as she positioned the head of the dildo at the entrance to Jean's cock hole. "Now, gently push as if you were trying to expel something. Imagine that you're a woman trying to push out a baby" With that Denise began to push the dildo into Jean's slick cock hole and the muscles expanded as Jean pushed out allowing the dildo to slide deeper into his hole. Jean groaned a little as most of the dildo penetrated him. Denise said, "Don't stop pushing. You don't have to push hard but do push enough to keep the muscle from contracting. If they contract it will hurt as the shaft will prevent them from returning to their normal position."

Jean maintained a gentle push outward and was soon fully penetrated by the dildo. "Take a few deep breaths and just lay there and get used to the feel of being filled up," directed Denise. After a minute Denise said, "OK, girlie boy now I'm going to fuck you." With that Denise began to pull the dildo out and then push it back in with a slow rhythmical half-stroke. As she fucked Jean the dildo shaft anchored in her pussy was pushed and pulled about inside of her and she became very aroused by this action. Until now the whole event had been somewhat mechanical but she was getting turned on now and began fucking Jean with some relish. Jean kept pushing and felt impaled on the dildo, which he thought would split him in half. While Denise kept up her strokes, friction was applied to Jean erect cock pinned between his stomach and the satin comforter on Denise's bed. As he heard Denise begin to gasp with pleasure as the gyrating dildo in her pussy brought her to a climax, his own arousal reached a peak and he felt his cock spasm with pleasure as it shot hot cum from its tip and coated his stomach. Jean heard a plopping sound as Denise withdrew the dildo and slid to the floor and leaned against the bed with her eyes closed and breathing heavily. With the dildo withdrawn, Jean was able to stop pushing and fully relax.

Shortly, Denise got up from the floor and asked, "Are you OK Little Sister?"

"Yes, I'm fine."

"You did good," said Denise. "I could tell you stuck with the technique. How was it?"

"It felt strange at first, but then I started to get aroused and all I wanted was for you to keep fucking me until I climaxed," said Jean.

"Well, that Little Sister is what fucking is all about. If you liked that you'll really like it when a man with real cock fucks you and shoots you full of cum. You're a natural for this business. Let's get cleaned up and have some lunch sweetie."

When Jean stood up and Denise saw the cum stains on her bed she exclaimed, "Wow, you did have a climax didn't you. Wipe down that comforter and strip it from the bed so we can take it to the cleaners. You'll find another in the closet over there to replace it with. I'm going to leave the dildo in the bathroom for you to clean up and store away. I'll get some clothes on and go see what we can have for lunch."

"Alright," said Jean. "I'll take care of things and be along in a few minutes and Denise thanks for showing me how to take cock. I couldn't have managed it without your instructions."

"My pleasure, literally," replied Denise with a satisfied grin "first time I ever fucked a girlie boy. It was fun. Maybe it would appeal to Ralph as a movie idea." With a big smile she turned and headed for the bathroom.

To be continued...