Rachel's Butt

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First-time analyzed has a ripple effect.
4.2k words
4.43
322.4k
39

Part 1 of the 2 part series

Updated 09/22/2022
Created 04/17/2005
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With trembling fingers, Rachel slowly opened the final button of her pale-pink, silk blouse.

"That's a good girl." her husband, Jeff, said, as he fixed on her heaving breast, "Now take off your skirt."

Rachel reached back, fumbled with the clasp that held it in place, then worked down the zipper. With little effort, she eased the skirt over her hips, and let it drift to the floor.

Jeff's eyes darted over her. "Take off your panties."

Rachel hooked her thumbs in the waistband of her white, lace-trim, V-string panties and guided them over her slim hips, exposing her neatly trimmed pussy.

"Take off your blouse."

Obediently, Rachel shrugged the blouse from her shoulders. Her nipples grew firm, chilled by the breeze coming from the open window. She stood silent. Naked, except for her white stockings and black stiletto heels.

"Turn around. Spread your feet and bend over."

Her heart was pounding. Rachel slowly turned. Spread her feet and bent at the waist. She could feel the air caressing her exposed pussy. Her breasts swayed uncomfortably. She pressed her arms against them, to stay them. Her long blonde hair shrouded her face. She could feel herself begin to blush.

"Straighten up, turn around, and walk to the bedroom."

Rachel did as instructed. Jeff got up from his chair and followed her.

"Crawl onto the bed.

"Kneel on the towel.

"Now lean forward until your left cheek is resting on the bed."

Rachel swallowed hard, and got into position. Jeff placed the video camera he'd been operating on the tripod and fastened it in place. Rachel had never felt so naked. So exposed.

With the camera still running, Jeff picked up a tube of k-y jelly, walked to the bed and sat down; making sure not block the camera's view. He opened the tube and squeezed a generous amount onto his finger. Slowly; ever so slowly, he covered his lady's virgin hole with the jelly. Gently, he began to explore the outer rings of her puckered little hole.

"You have such a gorgeous ass." he said, "A true work of art! A twelve, on a scale of one to ten!"

The sensation of being touched, back there, as she had never been touched before, was both unsettling and erotic for Rachel. Although she had read many Literotica stories on anal sex, nothing had prepared her for the pleasurable foreplay she was now experiencing.

"You do know that. Don't you?"

"Mmmm hmmm."

Jeff coated his middle finger with more k-y, and slowly entered his darling's tight butthole. She jumped at the intrusion.

"You okay?"

"I think so." she said, "I just wasn't expecting you to do that so soon."

Jeff held still inside her, allowing her a moment or two to adjust to the feeling.

Rachel let out a slow breath and tried to relax.

Jeff withdrew his finger completely, then slipped it back inside her.

Again.

Again.

Again.

The slow finger-fuck had its desired effect, as an unexpected warmth began to grow. To Rachel's surprise, a small orgasm washed over her. A soft whimper eluded the fact. The small amount of cum that coated her outer lips confirmed it.

Jeff withdrew his finger from Rachel's wanton hole, walked over to the dresser and returned with a small box containing a mineral-oil enema. As before, he positioned himself so as not to block the camera's view. Rachel raised up to see what her lover was doing. Jeff frowned at her and shook his head.

"Resume the position."

She did; as he removed the orange protective shield from the enema.

"Ready?" he asked.

"Yes." she said softly.

Jeff placed the tip against her well-prepared bung, and gently eased it into her rectum.

Rachel trembled in both fear and excitement.

Jeff began to squeeze the bottle: forcing the liquid deep into her bowels. In no time, the bottle was completely empty. He left it in place for what seemed an eternity, before slipping it from her.

"Do not move until I tell you." he said sternly.

"Alright."

Jeff got off the bed and removed the video camera from the tripod. He walked all around the bed, filming his lover from every angle.

"Reach back and play with your pussy." he said.

Without saying a word, Rachel brought up her right hand and began to stroke her now-sticky outer lips. Jeff zoomed-in on her efforts. "Now hold yourself open. That's it. Now stroke your clit. Oh yeah!"

The urge building within was growing unbearable. "I think I've got to go." she said.

"You can hold on a while longer. Keep playing with your pussy."

"Please Jeff, I've got to go. Really."

"I told you, 'hold on a while longer'. I want you to keep playing with your pussy. I want you to make yourself cum. I want you to fuck yourself to orgasm."

Rachel's fingers were a blur. It was a race to see if she could reach orgasm before the other urge became too strong. Her attention was divided. Try as she might, she couldn't make herself cum.

"Please Jeff! I can't wait any longer!"

"You can hold on a while longer. Keep fucking yourself, babe."

"PLEASE!!!!!"

A small amount of the liquid seeped from her hole. Jeff relented. "Okay." he said.

Rachel scrambled from the bed and ran to the bathroom. The sound of her high heels on the ceramic tile gave testament to the urgency. She hurriedly pushed shut the bathroom door. Jeff turned off the camera and waited.

Minutes passed.

Rachel returned.

Jeff switched the camera on. "Back to the bed." he said.

Rachel hesitated. A light slap on the ass started her on her way. Seductively, she crawled onto the bed and resumed the position. Jeff set the camera back on the tripod and picked up a saline enema.

As before, he coated her dark hole with some k-y; removed the orange cap and administered the cleansing liquid.

"Do you want me to go back to playing with my pussy?" Rachel asked.

"No. I have something else in mind."

Jeff walked to the dresser, opened the top drawer and took out a monster dildo he had recently purchased for his lady. He walked back to the bed and sat down, making sure, as always, not to block the camera's view.

"What are you going to do with that?"

"Fuck your pussy with it."

"Please Jeff, NO! It's all I can do to take your beautiful cock. That thing will rip me in two!"

Jeff ignored her plea, placed the head of the dildo against her glistening lips and pressed it in.

"Please Jeff, NO! It hurts! Take it out! Please!"

Jeff eased the dildo back a bit, then pushed it back in.

"Noooooooo!"

Again.

"It hurts. Please take it out."

And again.

"Please."

With each stroke, the pain in her pussy eased. Slowly, the pain gave way to pleasure.

"Unghhh!"

"Still want me to stop. To take it out."

"No."

Jeff picked up the pace. An intense orgasm washed over Rachel. "Oh god: I'm cumming!" she cried. Jeff continued his assault. With each stroke some of the liquid escaped her ass.

"I can't take anymore!"

"Yes you can. And you will!"

Jeff left the dildo in place, got up and took the camera in hand. As before, he walked all around the bed, filming her from every angle. He zoomed-in on her ass and pussy. "Fuck yourself with that big cock."

Rachel reached back and began working the massive dildo in and out of her stretched pussy. In moments another wave of orgasm washed over her. "Ughhhhhhhhhhhhhhhhhhh!!!!!"

"That's my girl! Keep fucking yourself."

"I . . . I can't. I've got to go! Please?!"

"Just a little longer."

Rachel kept working the dildo in and out of her sopping wet pussy, hoping the waves of orgasm would divert her attention. No luck. "Please Jeff. Please!!!! I've got to go! Now!"

"Okay."

Rachel pulled the dildo from her pussy, scrambled from the bed and headed straight for the bathroom. As before, Jeff followed her movements with the camera. The door slammed. Jeff shut off the camera and got undressed.

Ten minutes passed.

Rachel returned to the bedroom. Jeff switched the camera back on and resumed filming. Rachel walked to the edge of the bed, and turned to face the camera. She stood with her feet together. Her hands folded over her pubes.

"Take off your stockings and heels." he said.

Rachel stepped out of her stilettos; put her right foot on the bed , slowly rolled down her stocking and slipped it from her foot. She repeated the process.

"Get on the bed."

Jeff put the camera back on the tripod and adjusted its position. He picked up the tube of k-y and sat down on the bed: squeezed out a generous amount and coated his lady's bung. Using his middle finger, he worked it inside her dark hole. He repeated the process twice more.

"You sure have a tight little ass." he said, "I can hardly wait to fuck it!"

"I don't know about this. Your finger makes me feel so, full. How am I going to take that beautiful cock of yours?"

"Just relax, baby. Your sweet asshole can take a lot more than you think. Like your pussy. You didn't think you could take that monster dildo, but you did."

Jeff applied more of the k-y, then inserted two fingers inside his lovers relenting hole. Slowly he finger-fucked her.

More jelly.

Three fingers found their way in. More of the slow fuck.

"Are you ready for the real thing?"

Rachel turned her head and stared at Jeff's throbbing cock. All ten inches of it. She tried to imagine how she was ever going to take his full length. "Yes." she said softly.

Jeff knelt behind his nervous wife. He placed the head of his cock against her beckoning hole and took hold of her hips. "Ease yourself back." he said.

Filled with a mix of fear and lusty anticipation, Rachel began to impale herself. Inch by inch she accepted him. Any pain gave way rapidly to pleasure. Bravely, in one swift motion, she drove her hips back, taking his last few inches, stopping only when she could feel his coarse pubic hair against her smooth cheeks.

"Ughhhhhh!" she cried: half pleasure/ half pain.

"You okay?" he asked.

She bit her lip and nodded.

Jeff shifted his grip on her hips and withdrew all but the head of his cock. Slowly; gently he fed back his full length.

Again.

Again.

Again.

With each stroke, he picked up the pace.

"Oooo. Oooo. Oooo!" The sounds escaping Rachel's lips seemed alien to her. A mix of primal; something, and pure desire.

"Play with your pussy. Make yourself cum!"

Rachel did not need to be told twice. Her fingers danced over her pussy's lips. She rubbed; pinched; teased her super-sensitive clit.

Jeff picked up the pace even more.

Rachel's breasts swayed violently.

"Rughh. Rughh. Rughh. Rughh." With each thrust, Jeff grunted his pleasure.

"Oooo. Oooo. Oooo!"

The room was filled with carnal noise.

"Oh god. Oh god. Oh god." The words slipped from Rachel's lips. Wave after wave of orgasm washed over her. She focused her attention on the intense feeling of Jeff's groin meeting her quivering ass-cheeks.

Without warning, he pulled from her. The first jet of his thick cum sprayed across her back and onto her hair. The second followed the first. As did the third. Jeff fisted his cock: milking it. A puddle of cum formed in the small of Rachel's back.

The heat warmed her skin.

She raised up. His hands moved to her breasts, kneading, pinching. His tongue traced the curve of her left ear. Tiny kisses trailed down her neck. "I have a present for you." he said.

"A present?'

Jeff got up from the bed and walked over to the dresser. He opened the top drawer and took out a rather large butt plug. "While you're still nice and loose, back there, I want to slip this in."

Rachel eyed the oddly shaped object. It was something she had not bargained for, but in her heated state, the idea seemed appealing. "Ready?" he asked. She nodded.

Jeff placed the diamond-shaped head of the soft, latex plug against Rachel's gaping hole and worked it in. As she relaxed, her sphincter closed around the recessed neck: drawing the base firmly against her butt, holding it securely in place.

"Time to get dressed." Jeff said, as he moved from the bed and turned off the camera, "No panties. No bra. No stockings. Just that white silk blouse I bought you for your birthday, your black miniskirt and the heels you had on. And be quick about it. I made lunch reservations at the Stone House Tavern. We have a half hour."

"Can I shower first? I mean, I smell of . . . sex."

"Sorry. No time. Now get dressed."

Reluctantly, Rachel did as she was told. Slowly, she buttoned the blouse. Her dark areolas showed through. She wanted to protest, but didn't. The skirt was next. It barely covered the curve of her ass. Although she was fully clothed, she felt completely naked. She slipped on her heels. Bare legs were not usually her style, but her golden tan made the look acceptable.

Jeff walked into the room wearing a polo shirt, dockers and his favorite pair of loafers. He took Rachel in his arms and kissed her deeply. His hand caressed her ass, making sure the plug was still in place.

"You ready?" he asked.

"Ready as I'll ever be. . ."

***********************

It had been a week since Rachel had made her film debut. In those seven days, she and Jeff had watched the tape three times; each, ending in a hot exchange of carnal desire. For that reason, a fourth, less private screening, was about to begin, with the sole purpose of helping Rachel's good friend Becky overcum her fear of anal sex.

"You sure you're okay with my letting Sam and Becky watch our tape?" Rachel asked.

"Hey. If you're okay with it," Jeff said, "then I am too. . ."

Despite the fact that neither Rachel nor Jeff were interested in having their tape appear anywhere for public viewing, they both agreed that if the sight of Rachel giving-up her little ass to Jeff's big cock would convince Becky to give it a try, it would be worthwhile.

"What time are they supposed to get here?" Jeff asked.

"In about fifteen minutes." Rachel replied.

"Then I guess you want me to make myself scarce?"

Rachel walked over and gave her love a long, wet kiss. "That would be nice." she said.

"How long do you want me to stay gone?"

"A couple hours. Take your cell. I'll give you a call. . ."

Although more than ten years separated them in age – Rachel: thirty two; Becky: forty five – the two ladies had a lot in common. Especially when it came to a lack of experience in the realm of sexual exploration. For both, the reasons were many, and mattered little. What was important, however, was the fact that the men they had cum to love, were both very adventurous (in all things carnal) and were more than willing to try something new, if it offered a promise of mutual satisfaction. For Sam, as it had for Jeff, anal sex held such promise. Becky, like Rachel, was not so sure, and need some convincing.

"Hi Beck, Sam. Come on in." Rachel said.

"We're not too early?" Becky asked, her nervousness showing.

"Not at all." Rachel said.

"Where's Jeff?" Sam asked.

Rachel closed and locked the door. "At the Y. He's playing in some basketball tournament."

Becky and Sam walked into the living room and sat down on the couch, opposite the TV.

"Here's the deal." Rachel said, "The tape is in the VCR and ready to go. All you have to do is turn the TV on and press play. Sam, here's the remote. I'm going in the bedroom and leave you two alone. Beck? When you've made up your mind, come in and I'll get you ready. Okay?"

Sam and Becky nodded. Rachel went into the bedroom and closed the door. She heard the music Jeff had dubbed in begin to play. Checked her watch. The video was a little over forty minutes long. She wondered if Becky would watch the whole thing before deciding to cave.

To while away the time, Rachel finished getting everything ready. First, she folded back the blanket and top sheet and removed them from the bed. Next, she spread out the turquoise beach towel that had served her so well. Lastly, she took out the k-y jelly, and mineral-oil enema and laid them on the bed. She studied the scene. Images of her starring role in her first adult film flashed in her mind. It was funny, less than a month earlier, she could not have imagined herself starring in her own X rated movie. It wasn't that she had anything against the concept, quite the contrary, it was just that she had never given it much thought. That was until Jeff broached the subject. Now, she was glad she had consented, and truly hoped that her performance would have its desired effect.

Rachel checked her watch. The video was less than one quarter over. She picked up one of Jeff's Playboy magazines, settled back in her chaise lounge and began flipping through. It was now a waiting game.

A little less than an hour later, a gentle rapping at the bedroom door told her it was over.

"Come on in."

The door opened. Becky stepped inside and quickly closed it behind.

"Did you enjoy doing it as much as you seemed?" Becky asked.

Rachel nodded. "I was a little scared at first, but once I started to relax, I really got into it."

"How many times did you cum?"

"At least six."

"Six?!"

"Do you want to give it a try."

Becky thought for a long moment. "Yes."

"Then get undressed and we'll get started."

With shaking hands, Becky began to do as Rachel had asked. First, she stepped out of her slides. Next, she unbuttoned her capris pants and pushed them to the floor. To Rachel's surprise, her protege had on no panties. To her further surprise, Becky's pussy was clean shaven.

Next, Becky took of her blouse, and lastly her bra.

Rachel's eyes darted over Becky's body. More from curiosity, than anything else.

Becky was about five foot six, and about one hundred sixty pounds. Her breasts were large, and capped with silver-dollar sized areolas. Her nipples were thick and stood out a good inch. Her legs were long, and her butt nicely shaped. Rachel could understand why Sam wanted to fuck her; back there.

"Now what?" Becky asked.

"Lay on the towel. On your left side. Pull your right knee to your chest."

Rachel had considered having Becky kneel, the way Jeff had done with her, but decided that oh so vulnerable position would be too much for Becky to bear, and chose this more modest position instead.

"Now what?"

"Try to relax."

Rachel opened the tube of k-y jelly and squeezed some out. Using her left hand, as gently as she could, she spread Becky's butt cheeks and began to coat her rose-bud hole. The cool jelly against her hot asshole made Becky jump. Rachel backed off.

"Sorry. You just caught me off guard."

"You sure?"

"Yeah."

Rachel removed the orange cap from the syringe and inserted it in Becky's rectum. Gently she pushed until it was all the way in. With even pressure, she emptied the contents into Becky's bowels.

"Hold it as long as you can." she said, "I found playing with my pussy helped take my mind off the need to go."

"You want me to masturbate? In front of you?"

Rachel got off the bed and walked around to the other side and sat down. She lightly caressed her friend's shoulder. "Listen Beck. In less than a half hour, Sam's going to be fucking your ass for all he's worth. I don't know about you, but it takes me a while to get turned on, and warmed up. If you want to enjoy the feeling of his gorgeous cock sliding in and out of your ass, you're going to have to do what I tell you.

"If it would help, I could lend you my vibrator."

Becky nodded. Rachel opened the drawer to the night stand, took out a long, thin vibrator, switched it on, and handed it to Becky.

"Close your eyes." Rachel said, "Imagine your favorite scenario."

Becky did as instructed, then slid the quivering little toy inside her pussy and nestled it against her clit. To her surprise, within seconds her first orgasm arrived. "Oh god! I can't believe I'm cumming already!"

"I told you."

Becky kept working the vibrator in and out of her pussy. Slowly, her second orgasm began to build; as did her need to rid herself of the enema. The later won out. With little time to spare, she made it to the bathroom. When she returned, Rachel had the saline one ready.

12