Nisan 13, 2024

Never Say Never Pt. 02

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Been awhile hasn’t it? Better late than never though, right? I’m sure many have been wondering how things have been going for Rachel and me. Rachel was, as you remember, really not interested in anal sex to say the least. Quoting from the original submission: -Anything that has an “in” capability, read mouth and pussy, has a year round open season sign attached. Anything with only an out capability, read rectum, is permanently closed for business.

Well, things have changed since our initial anal encounter. This entry is a recap of our second anal encounter. I know, I know, kind of a short story. However, it was a critical hurdle for Rachel. She made the transition from reluctant to willing very rapidly. I desperately wanted more and was afraid the first time was also the last time.

Rachel was subdued for several days and seemingly too embarrassed to talk openly about our first experience with anal intercourse. My assurances apparently weren’t reassuring enough. I gave her space and time to come to terms with her confusion, reservations, ambivalence and conflicting feelings.

When we made love, we fell immediately back into our usual pattern of oral sex and vaginal intercourse. Don’t get me wrong, our sex was as great and satisfying as always. While stimulating her vagina and clit orally, I would let my tongue roam briefly across her anus. She always moaned with pleasure, but would pull me away murmuring softly, “Not now. I’m not ready.”

Bummer. Close, but no cigar. Shut down.

Weeks later, after a particularly heavy day of outside work, I arrived home hot, sweaty and smelly. Rachel took one sniff, pointed toward our bedroom and said, “Hit the showers bub!”

Rachel walked in just as I was finishing up. I pushed the shower door open and started to thank Rachel as she handed me my towel, but hesitated in mid-breath when I noted the look of uncertainty on her face. “What’s wrong?” I asked with concern.

“I, uh, um,” Rachel stammered. “I’m kind of constipated again,” she blurted as she averted her eyes and stared at the floor.

I looked down and watched the toe of her right foot trace a dark vein of color running through floor’s stonework. My cock twitched involuntarily as I waited, silent, holding my breath, hoping this was an overture to what I desired.

“Would you, um, help me, ah, with another enema?” she asked sheepishly.

My cock was getting very heavy, engorging rapidly, it began to push against the towel I was holding between Rachel and myself. She was still staring at the floor and was unaware of the reaction I was having to her question.

I touched the undersurface of her chin with the index finger of my right hand, gently tilted her face up until her eyes met mine. “Of course. Do you want to do it now?” I asked.

“If you don’t mind.”

“Of course I don’t mind.”

“Well, I want to do it like we did before. In the shower so we don’t make a mess and we can both be clean when we’re done,” she said blushing furiously. “You wait here. I’ll get the enema bag. I’ll be right back.”

She stepped into the main part of the bathroom and almost immediately returned. “Strange. That didn’t take long,” I thought to myself.

“Here. You get it filled up while I undress,” she said as she handed the enema bag and the tube of KY jelly. “I’ll be right back.”

I tested the temperature of the water, very warm, but not uncomfortably so, filled and sealed the enema bag, and hung it on the shower door.

Rachel returned and stepped into the shower in all her naked and beautiful glory. “Are you sure you ‘re OK doing this?” she asked as she unsuccessfully tried to hide a sheepish grin.

I glanced at my stiff pole, smiled at her and canlı bahis şirketleri wryly said, “I hate to admit it, but I guess constipation seems to agree with me.”

“You’re so bad!” she chided as she pulled me firmly against her body, on her tip toes, her face turned up for a kiss, my cock trapped against her warm tummy, her breasts pressed firmly against my chest. “Um, you taste good,” she cooed after we parted from a passionate kiss.

She pulled away and knelt with her backside presented to me. “I’m ready for my treatment Dr. Jess,” she said with a little wiggle of her ass.

“Hmm,” I thought to myself with growing excitement. “Doesn’t seem very constipated to me. Seems kind of horny.”

I assumed a kneeling position, gently separated her ass cheeks and lightly touched her anus with the tip of my finger. The brown little ring of tissue winked tight in response.

“Ummm,” she literally purred.

My cock twitched involuntarily. “Yep, definitely horny,” I thought.

I opened the KY tube and coated the surface of the enema tip and her anus with the clear jelly. I placed the tip gently against her anus and slowly applied pressure. The puckered tissue slowly stretched, the fat tip overcame the resistance of the strong little muscle, and disappeared inside her rectum.

“Oh! Yes! OK. Umm.”

My cock was so rigidly hard it was painful. God I wanted to fuck her.

I released the clamp and let the water flow.

“Oh my. Umm. I forgot how this feels,” Rachel whispered.

I tightened the clamp. “You OK?” I asked.

“Yes, yes. Don’t stop. Let it flow. I’ll tell you when I’m full,” she panted.

I released the clamp and listened to the water rush through the tube into her body. The bag of liquid quickly flattened as the warm water flowed into her rectum and filled her bowels.

“Um, um,” she softly groaned. “Whew. You better stop.”

I clamped the tube. “Let me know when you’re ready for me to pull the tip out.”

“Hold on a second. I don’t want to make a mess in here.”

Her anus squeezed tightly around the shaft of the enema tip.

“OK. I’m ready. Take it out slowly.”

I watched her anus stretch as the bulbous end pulled against, stretched the wrinkled anal tissue, and suddenly slipped free of her rectum. Her anus snapped tight, only a few drops of liquid escaped and dripped to the shower floor. I helped her up and she stepped to the toilet. She sat and I heard the sound of the enema water squirting from her bum into the toilet.

“Again,” she ordered as she stepped back into the shower and assumed a kneeling position. I refilled the bag, rehung it on the door, put a dollop of lube on her anus and carefully reinserted the fat tip into her waiting ass. I unclamped the tube, the water flowed steadily into her bowels.

“Touch me!” Rachel said as she let her knees slide a bit more widely apart on the floor. Her pussy lips parted and exposed her swollen clit, the pink nub poking through its little hood.

I ran my fingers slowly between Rachel’s fat outer labial folds, well lubricated with the moisture oozing from he pussy. I teased the opening of her vagina and then slowly slid two fingers deeply inside her pussy.

“Mmm,” Rachel moaned. “Touch my clit. Rub my clit,” she pleaded.

She moaned and pressed back against the enema tip pressing it deeper into her ass as I followed her instructions. I slowly withdrew my fingers from her hot cunny, gooey wet from her excitement, then found, rubbed and stroked her hard little button.

“Yep,” I thought to myself. “Definitely horny. This is my lucky day.”

“That feels so good! I’m so turned on Jess. I’m so bad,” she whispered.

“You’re my kind canlı kaçak iddaa of bad babe,” I breathed huskily as I lightly flicked her clit with the tip of my finger.

“I don’t feel the water flowing. Let more water in.”

I turned and looked at the empty flat bag. “You took it all. It’s empty.”

“OK. Take it out.”

When I removed the enema tip, she quickly moved to the toilet and let the water whoosh out of her body.

She looked between her legs. “Nothing solid, but still yellow. Let’s do it again. Fill that bag as full as you can,” she ordered.

“Cool,” I thought. “Definitely not constipated. She wants it in the ass.”

I filled the bag until it was stretched tight and overflowed. I put a small another small dollop lube on my fingers, gently rubbed it over her pussy lips and then ran my slick finger gently over the pucker of her anus.

Rachel looked back at me, “What are you doing?” she asked.

“You’ll see,” I said as I reinserted the enema tip into her waiting ass and released the clamp.

I pressed the tip of my cock against her vaginal opening and slowly slid my aching swollen member deep into her hot tight pussy.

“Oh my god! Yes! Fuck me, fuck me, fuck me,” she growled as the water filled her bowels and my cock pressed into and filled her pussy.

I enjoyed watching my dick slide in and out of her beautiful vagina, beneath the enema tip and tube protruding from her anus. Her pussy was stretched tight around my hard shaft. I slowly thrust in and out of that wonderfully lubricated warm tunnel of pleasure. Her soft pink pussy tissue everted as I withdrew my long shaft, and inverted as I pushed back into her body. What a fucking turn on.

“Don’t you dare cum!” she ordered. “I want your cock in my ass! I want you to fuck my ass again.”

I pulled my cock out of her pussy, barely in time, panting with the effort.

“I can’t hold anymore. Hurry. Clamp it.”

I clamped the tube, but the bag was pretty much empty. I watched the delicate tissue of her anus stretch and contract around the exiting tip. Her muscles squeezed tight, holding the water inside. She got up, moved to the toilet and let the water rush from her body again. She looked between her legs and proudly announced, “Clear.”

“Constipated hmm?” I asked rhetorically as we showered off together. Rachel smiled shyly.

We toweled ourselves dry and rushed into the bedroom.

“I need you now Jess. I want your cock inside my bum. Please fuck my bum,” she said as she knelt on the bed.

I knelt behind her, pulled her ass cheeks apart and licked her anus.

“Oh Jess, that feels so good.”

I drooled saliva on her anus and gently pressed my index finger against the natural resistance of her anal sphincter. Rachel pressed against my hand. I could feel her strain against my finger. My finger stretched the tight muscle and slipped inside her slippery hot rectum. The rectal tissue was soft, spongy and warm to the touch of my probing finger.

“Ummm. Do it Jess. Do it.”

I squeezed some KY onto my fingers. I slowly stretched her anus and slipped another finger into her ass, gently widening the opening for my cock.

“Jess, do it, stick your cock in my ass. I want to feel you inside me,” Rachel pleaded.

I removed my fingers and quickly pressed the head of my cock against her still slightly opened anus. My glans overcame the resistance of the tight muscle as I pressed firmly against her ass and and popped through the anal ring. Heaven. I was inside Rachel’s ass again.

“Yes! Yes! All the way in. I want all of you inside of me!”

After applying more KY on my shaft, I pressed firmly and watched my cock slowly disappear inch canlı kaçak bahis by inch inside her bum. I luxuriated in the wonderful sensations of the tight spongy tissue of her rectum as it parted and accepted the penetration of my rigid cock.

“Oh god Rachel,” I exclaimed as she squeezed and messaged my cock with her ass muscles. “Fuck, that feels good.”

“You like that big boy?” she asked as she tightly squeezed and released my cock with her ass. “I can take it Jess. Fuck me. Do it.”

I started slowly. I watched my shaft pull against and pucker her anus taught as I my shaft slid out, then invert and disappear inside her rectum as I thrust and reentered her body over and over.


I pumped faster, stroke after stroke. I withdrew and my glans popped free, her anus gaped and remained open. The pinkish-red and wrinkly surface of her rectal tissue was visible. Its surface glistened with moisture. I quickly inserted my tongue through the gaping hole and licked at the warm tissue inside her ass. I reached up and messaged her clit as I explored her rectum with my tongue.

“God that feels good,” Rachel moaned.

Her anus slowly closed and contracted around my tongue. She grunted, I felt her press down, her anus opened and my tongue slid back inside. Rachel’s anus squeezed tight again, clamped around my probing tongue and pushed me out. I heard Rachel grunt and strain again. Her anus slowly dilated open and allowed my tongue to resume probing and exploring her rectum.

“Ummm, sooo, good,” she purred with pleasure. “I’m going to cum Jess. I want your big cock inside when I cum.”

I positioned myself behind her ass, ready to insert my finger to help ready her anus for my cock. She strained just a bit and her anus slowly opened without the aid of my finger. Surprised, I immediately pressed my swollen purple glans against her open hole. Her anus snugged around and trapped my glans just inside her rectum.

Rachel’s hand was between her legs. She was masturbating her clit. “Fuck my ass Jess. I’m going to cum soon. I want to feel your cock deep inside me. Fuck me.”

I applied more lube to my shaft and then very slowly pushed deep inside Rachel relishing the spongy grip of her rectum as my cock penetrated her ass. My pubic bone pressed firmly against the soft curve of her ass. I pulled back and then watched my hard dick disappear through her stretched anus as I slowly impaled her ass once more.

Rachel screamed, “Oh fuck I’m cumming! I’m cumming!”

Her ass muscles contracted around my cock with incredible force. Contraction after contraction flowed the length of my shaft. I couldn’t hold off my orgasm any longer. I humped her ass, and then with one last thrust, I exploded inside her. My cock contracted time after time inside her rectum and pumped my sperm into her bowels.

“Oh god Jess! You feel so big. Cum inside of me,” she moaned as she clamped her ass tightly around my contracting cock. “It feels so good.”

We collapsed forward onto the bed together. My cock still twitching inside her rectum and my balls were nestled comfortably between her butt cheeks.

“Jess, that was unbelievably incredible.”

“I was afraid you never wanted to do it again.”

“I have been working up to it. It is still so embarrassing. I’m so afraid I’ll smell bad. That you’ll think I’m a slut. That you won’t love me anymore. But, I liked it so much the first time. I wanted to try again. I finally worked up the nerve,” she said quietly.

“Thank god. I love doing it. I love everything about it. That was the best orgasm I’ve ever had.”

“Oh Jess. Me too. It was so intense. There is something special about you being in my bum, my anus stretched so wide open and my rectum filled with your cock. It somehow intensifies my orgasm.”



“I’ll give you an enema anytime you want. Please don’t ever be afraid or hesitate to ask for whatever you want. OK?”

“OK. I’ll try.”

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