CHAPTER 3:  Both Ladies do Anal

Rose and I spent as much time as we could together that day. We mostly talked, and laughed, touching, holding and worshiping each others bodies between bouts of kissing and cuddling.

About a half hour before I had to go, as we engaged in yet another round of passionate kissing and heavy petting, Rose caressed my semi-hard penis with her hand, and asked, “Would you like me to orally pleasure you?”

A loud chuckle burst out of me. Smiling gleefully, I said, “I’d prefer it if you sucked my cock.”

She frowned, closing her eyes and shaking her head in disapproval. Taking a deep breath she huffed it out. “What am I ever going to do with you, Harrison?”

Rose began kissing me on my chest, looking up at my face with her big brown eyes. She slowly kissed her way down my body, stroking my cock with her hand, and continued to stare into my eyes.

After her daughter’s ‘straight to the deepthroat’ brand of ‘oral pleasuring’ this was a bit too sedate for me.

I wanted to say, ‘Hey, stop staring at me. Just get down there and gobble that penis’, but I kept my mouth shut and tried to appear pleased.

Eventually, Rose got to my penis, and I actually started to get interested. She kissed all around it first, and I almost looked at my watch.

Finally, she lifted my cock up. Still staring up at me, she brought the tip to her mouth and, to my complete frustration, began kissing it.

I wanted to scream.

Instead, through clenched teeth, I said, “I want to feel my cock in your mouth, Rose. Do it! Please?”

Rose smiled, then opened that gorgeous, polite and refined southern bell accented mouth, and dropped it onto my cock.

A loud groan came out of me. Sure, it wasn’t anything too physically stimulating, just wet, and warm and nice, but most of the excitement I felt was mental.

Rose, my friend’s mother, and a conservative, refined Southern Baptist thirty-eight year-old lady, was sucking my eighteen year-old cock.

She did a lot better after that. No, she never took more than half my penis into her mouth. There was no dirty talk – actually no talk at all, and she pretty much stared up at me through the whole blowjob.

But despite all that, her short, head-bobbing strokes and the sight of her full, sexy lips all around my cock evoked an orgasm out of me in about five minutes.

“I’m gonna cum, Rose.”

For some reason, probably spoiled by her daughter’s hungry brand of cocksucking, I expected this to excite her, and maybe inspire her to attempt a deep throat.

Instead, Rose pulled her mouth off of me, and began stroking my cock vigorously with one hand.

She smiled up at me as I popped, and kept smiling and stroking, as I shot my cum all over her hand and onto my own stomach.

What a waste!

“There,” she said, “Did you enjoy that?” She reached over to her nightstand and plucked several tissues from the box.

She handed me some and sat up on the edge of her bed with her feet flat on the floor and in her stiff, straight posture, carefully cleaning my cum off her hands like she was knitting a sweater.

I almost expected her to put her reading glasses on for the task.

I said, “Why didn’t you just swallow it.”

“Harry!” She cried, putting a hand to her chest. “Good girls don’t do that. It’s disgusting.”

I mumbled, “Well, that sucks.”

Rose chuckled, shaking her head and poked me with her hand.

“No,” I said, “I really wanted you to drink my cum.”

She gave me a mock sad face, then smiled sweetly and said, “You can’t always get what you want, Harrison.”

“Why not?”

“Because life doesn’t work that way.”

I turned on my side, smiling, and propped my head on my hand. “I’ve had other girls drink my cum.”

“Well, good for you.”

“Have you ever done it?”

“Absolutely, not.”

“What’s so bad about it?”

Rose contemplated my question, she soon shook her head and said, “Nothing, I guess. I just find it vulgar and distasteful.”

“I love drinking your pussy juices.”

Her face beamed a wide-eyed smile, and she giggled, rocking toward me and planting a kiss on my lips. “That’s sweet,” she said, “Vulgar, but very sweet.”

“See! You like the idea, too.”

She looked perplexed. She said, “The idea?”

“Yes, the idea of me drinking your juices and loving it.”

She tilted her head, and nodded. “I suppose so.”

“‘Don’t you want to taste my cum?”

She sat up, laughed and shook her head. “No. Not in the least.”

“Really? Well, that sucks.”

She rubbed my arm, made that mock sad face of hers again, and said, “Poor, Baby. I’m sorry.”

“Would you do it for me anyway?” I said, smiling fiendishly.

Rose took a deep breath and pushed it out her nose. “You really are hung up on this, aren’t you?”

I nodded, still smiling.

“Well, I guess, at some point, in the future, but I’ll have to think about it.”

“How about the next time you orally pleasure me? How about then?”

She laughed, and slapped my leg. “Harrison, you’re incorrigible. Now, it’s late. You need to go.”

Rose leaned into me and we kissed.

I got up, gathered my clothes from the floor all the way out to the kitchen, dressed and kissed Rose goodbye again. This time I gave her gorgeous ass I nice hard squeeze and a smack to end our kiss, and left.

I ended up being late for work.

As I got dressed, Rose had asked me to come back the next morning, but I had suggested a tap on her window for later that night.

She loved the idea.

I tapped on her widow at around 11:30 PM, and our affair resumed right where it left off.

There were no words spoken. The pure physical need for each other consumed us both.

As soon as I stepped through her porch window, we eagerly kissed each other. All Rose had on was her silky soft fuzzy robe.

I pulled it open as we kissed, and then we sank down and fucked right there on the floor.

We both came fast and hard. It was primal, full of passion and so intense.

After we recovered from our orgasms, Rose smiled and said, “Well, hello to you, too!”

I snickered at her charm, and helped her up off the floor.

We got completely undressed, climbed onto her bed and lit up.

We lay there smoking in the dark as we talked.

“You really did just impregnate me, you know,” she said. “You just cummed inside me while I was having one of the best orgasms of my life. That’s twice today, and that’s how you make a baby. I will be pregnant, Harrison.”

I kissed her cheek and rubbed her belly.

“Good,” I said.

“Not good.” She took a long drag of her cigarette. “How do I explain this? My kids are going to freak out.”

“Let them wonder. Don’t tell them anythig. It’s none of their business.”

“What? An immaculate conception?”

“You were just yelling, Oh God,” I said, chuckling. “So, yeah. Tell them it was Him.”

She frowned. “Blasphemer.” She grimaced. “Was I that loud? I hope no one heard me.” She shook her head and brought her cigarette to her mouth.

She savored a long drag from her cigarette, then spun over and propped herself up on her elbows, facing me as I laid on my back on her bed.

She was laying on her belly, completely naked, propped up on her elbows and hugging her pillow under her chest as she looked into my eyes.

“And how did you get so good at eating pussy?” She asked, squinting and pointing her cig at me. “Earlier you did some things with that tongue… What other older lady have you been with? She taught you to eat a very good pussy, whoever she was. You really are amazing at that, and I’ve been meaning to ask you. Who taught you?”

I shrugged, flicking my ash in the tray. “A young girl, actually.”

She pulled her head back and grimaced. “Not likely. What young girl?”

I couldn’t tell her it was her own daughter.

I said, “Just a girl… at school.”

“Really,” she put her hand on my cheek. “Tell me all about her. What was her name?”

“Actually, it doesn’t matter. I ate your pussy so good because I wanted to eat it so bad.”

She smiled. Stubbed her cigarette out, looking pleased with my answer, but said, “Tell me about this little girlfriend of yours. I’m curious.”

I looked her in the eye, smiled and shook my head. “Nope. Ask me no questions and I’ll tell you no lies.”

She smiled, nodding. “Hmm, that’s the most mature thing you have ever said to me.”

“I have something even more mature to ask.”

“Go ahead. Ask away.”

“Can I fuck you in your beautiful ass?”

She yanked her hand away from my cheek and grimaced in disgust, like I had just asked her if I could take a dump in her mouth.

“No!” she said, “Absolutely not. Why would you even want to do such a filthy thing? Are you a homosexual?”

“Because I want to fuck you in your ass. That’s why. Because it’s gorgeous. Because it’s so incredibly sexy that I want to fuck it and I want to cum inside it… deep inside it.”

She looked absolutely stunned by my response. Her eyes closed and she shook her head.

“Anal sex, sodomy, is a mortal sin against God, Harrison.”

“What’s God got to do with us? I don’t want to fuck God’s ass I want to fuck yours.”

She winced, and grimaced. Keeping her eyes closed, Rose shook her head and said, “Why must you say everything with such vulgar words?”

“How should I ask you to let me fuck your ass?”

Rose laughed, and said, “I don’t know, but let me try to rephrase it.”

She wondered about it for a moment. Her eyes searching the ceiling.

“Okay, I think I have the perfect wording.” She propped herself up on an elbow, stared into my eyes and said, “I love you, Rose, and would never ask you to do anything that you find morally repugnant, or that might cause you excruciating pain, but I am obsessed with your posterior. So, please, would you consider allowing me to sodomize you?” She laughed, and slapped my chest, amused at her own monologue.

I grimaced, and shook my head. “Now that sounds gay.”

“Wait! I have more,” she said, amused with this role play.

“I promise to be gentle, and to let you be in complete control the whole time. Please, Rose, sacrifice everything you believe in, your soul, your mental health, your emotional stability and your body, so you can be in pain and so I can fulfill my homosexual fantasies and bugger your behind.”

We both laughed. She much louder and longer than I.

I took a deep breath. “Well,” I said, “When you put it that way it sounds absolutely horrible.”

“Because it is horrible.”

“I don’t think so. A man and woman were made to do anything they want with each other, including that. Otherwise, it wouldn’t be possible. Are you saying God made a mistake?”

Rose grimaced. “No, of course not, but God allows us to sin. It’s called free will.”

“Well, my free will wants your gorgeous ass all around my cock.”

That answer evoked a pleased smile. She shrugged and made a quick, ‘Oh well’, expression.

The smile grew and lingered.

Despite all her reservations, she seemed to enjoy the intensity of my desire.

I moved my hand onto her behind, squeezing it and caressing it. We kissed a long passionate kiss as she let my hand explore her posterior. I made sure to stay a couple inches away from her butt hole always.

Breaking from our kiss, in an urgent tone through clenched teeth, I whispered, “I want to fuck your ass so bad, Rose.”

She huffed out a breath and propped up on an elbow, turning her ass out of reach.

“Really, Harrison? First the request for me to drink your semen earlier today, and now this?”

I grimaced and shrugged.

“Neither of the men I’ve been with in my life have ever asked me to do either of those things.”

“Well, then, they were idiots.”

She scoffed and shook her head. “No. We were Southern Baptists in Maryland. Sodomy is a mortal sin. Plus, only homosexuals want to do that… that sort of debauchery.”

I chuckled. “I’m no homo, and every time I look at your gorgeous ass I want to fuck it. So why not… just let me?”

“Stop using such crass language, potty mouth. It’s unbecoming and I won’t abide it.”

I sat up, reached out and put my hand on her bare ass cheek, squeezing it.

The silky soft, pale white skin was so inviting that it made my mouth go dry, and my whole body tense up.

“The real sin would be not fucking that– I mean… not having that amazing… behind… of yours… all around my co — all around me.” I frowned at my own awkwardness, and then shrugged it off.

“I want it, Rose. I want it so bad. Just give it to me.” I smiled at her as I continued rubbing and squeezing her ass.

She followed my gaze, then shifted her body to better see her own behind, studying how it looked as I massaged it.

Looking back at me, she gave a little shrug, sighed loudly and said, “I don’t know why you’re so obsessed. It’s a lot fatter and a lot less firm than it used to be, before my five kids.”

“Can I, at least… lick it?”

Her eyebrows arched. She got an amused look on her face, and asked, “Lick it? Really? You want to lick my ass?”

“So badly it hurts.”

“Just the cheeks?”

I shook my head.

“My bum hole?” She asked, looking stunned, but a mischievous and guilty smile growing until she beamed.

I nodded in excitement, a literal shit eating grin on my face.

She tilted her head and shrugged. “I guess there’s no sin in that. Go down there and lick my bum hole if that’s what you really want.”

She shook her head, looking mystified, but she chuckled as she laid down on her stomach and spread her legs.

I hopped over her leg, and spread both her legs wider aside as I landed between them.

Rose smiled back at me. “I have got to see this,” she said, an amused look on her face.

First, like she had done to me during her oral pleasure session, I began kissing the small of her back and staring up into her eyes.

She looked fascinated, her eyes widening at every kiss that went closer toward her asshole.

I also cupped her pussy in my hand and massaged it gently as I worked.

Rose let out a soft moan and said, “That is not fair, young man.”

I continued kissing, and letting my tongue dart out, paying attention to everything but her butt hole.

As I licked the top of her butt crack, I slid two fingers into her wet vagina.

I felt Rose quiver, and she turned her head away, lifting her pelvis ever so slightly.

I licked deeper down her ass crack, and used my thumb to massage her clit.

I pushed my fingers deeper into her pussy, spinning them and pulling on her clit and vagina in a long, soft pinching motion.

She whimpered and I felt her body tremble.

I fucked her pussy with my fingers in a slow, soft, but deliberate motion.

Rose let out a louder moan of delight.

Then, spreading her soft, full cheeks aside, with my free hand, I extended my tongue and I slowly licked her whole ass crack, from taint to the top of her cheeks.

As soon as my tongue came in contact with her butt hole, Rose shivered and gasped very loudly.

Her head whipped around to look at me, almost a look of horror on her face.

I licked over her butt hole again, looking up at her as I did it, and using my fingers and thumb to massage her clit.

Rose was gasping in short breaths, her eyes and mouth still wide as she watched.

Then I smiled at her, stuck out my tongue as stiff as efficient and pushed it into her butt hole. Just the tip of my tongue penetrated her tight little hole.

She gasped loudly and in her refined southern drawl, exclaimed, “Oh… my… Lord!”

Her pelvis began to sway as I fucked her ass with my tongue, and her pussy with my fingers.

I said, “Does my tongue in your ass feel like a sin?” I quickly stuck it in again.

Rose cried out with airy moans of delight. Her eyebrows knitted up as she looked back at me in disapproval, but with her pelvis moving faster.

I pushed my tongue in deeper, feeling her butt hole opening up for me.

In an airy growling gasp of a voice, she said, “How dare you!”

Her head flew back and she pushed her ass harder into my probing tongue and fingers.

She cried out, “You dirty, dirty boy!”

I climbed up her back, kissing and licking up to her neck. I whispered in her ear, “I am a dirty boy, and you’re my dirty girl. Let me fuck your ass, Rose. Let me.”

I spit on my hand, wet my cock and put it in her ass crack, sliding it up and down between her silky cheeks.

Her back arched and she put her head in the nook of my neck and shoulder as I fucked her ass cleavage.

“No,” she whispered. “It’s wrong. We can’t.”

“Let me in,” I said, kissing her neck and fucking her ass crack faster.

“Let me in, Rose. I’m begging you, Baby. Let me in.”

She let out a whimper, arching her back more, and lifted her butt to press harder against my sliding cock.

“Okay, Harry,” she whispered, barely audible. “I’ll let you do it… but… but don’t cum in me, Sweetheart. Just… whatever happens, don’t cum in my ass.”

I kissed her neck in gratitude. Then I spit in my hand and rubbed it on the head of my now raging boner.

Rose buried her face in her pillow, grabbed the top of her headboard with both hands, and waited for me to begin.

This was not my first anal experience. It was my second. That first one, however, took a lot less effort to initiate.

About three weeks before, only three bedrooms away, l spooned with Cindy, Rose’s eighteen year-old very pregnant daughter.

We had just had sex about a half hour earlier, and were laying in her twin bed.

“Have you ever done anal?” She asked.

“No.”

“Kool,” she said, “Do you want to try it?”

I shrugged. “Sure.”

“Okay, first off, we need something for lube. You always need lube for anal.”

Cindy jumped up and grabbed a bottle of baby oil from her dresser. She was completely naked and I looked at her ass.

It looked nothing like her mom’s slender, but still curvaceous, popping out behind her in two protruding and glorious orbs of luscious perfection.

Cindy’s ass was much wider, and larger in every way. It didn’t look toned, like her mom’s, but it did have it’s own very feminine appeal.

It looked soft, milky white and had a great shape to it.

She handed me the bottle of baby oil, hopped onto her bed on all fours with her ass in my face, and said, “Lube up.”

I poured the baby old on my cock and gasped at the cold shock it gave me.

Cindy giggled, looking back at me. “You should pour it in your palm first.” She rolled her eyes, and spun around to a sitting position. “Here. Let me show you.”

Yanking the bottle out of my hand she poured a generous amount of oil in hers, put the bottle on the bed and rubbed her hands together.

Then, still smiling excitedly, she grabbed my limp cock in both hands and stroked my penis aggressively. Her slippery hands worked quickly, and my cock responded.

As it rose and hardened from her flurry of pulling strokes, Cindy lost her smile, and said, “I love this fucking dick.”

She practically folded in half, lunging down to take my erect penis in her mouth.

Both her hands and her mouth worked my cock. I laid back, thrust my hips up to give her the whole shaft, and enjoyed the unexpected, but enthusiastic combo blowjob and handjob.

Cindy paused a moment, picked up the baby oil and squirted it in her mouth.

She slobbered it all over my dick, giving it only three or four more strokes with her mouth. Then she jumped up, and spun around onto her knees.

She dropped her head and shoulders onto the bed, spread her ass cheeks with both hands, looked back at me and said, “Go ahead, but go easy at first, Harry. Come on. Let’s do this. Fuck my ass.”

I got up into a kneeling position, pointed my dick at her asshole, and pushed the head into it.

I felt her butt hole open up around the head, and Cindy’s whole body spasmed.

“Easy!” Cindy said, hissing in a breath. “Stay there. Stay right there.” She panted for air, her pale skin suddenly covered in a sheen of sweat. “You have to… You have to wait for a girl’s asshole to adjust. Be patient.”