Ugly Duckling Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Obliging my Mother-in-Law seemed the familial thing to do, so I pressed passed her anus and into her rectum. I would have loved to spend a whole hour doing nothing except eating her delicious cunt and getting her off with some anal play. I thought Melinda wanted more. Standing up, I positioned my cock against her pussy and drove in with one stroke.

'Oh God,' she groaned loudly. I think that's what she said anyway. She went off even louder as I pushed more of the vibrator in and cranked it up. Melinda hit her orgasm instantly and that was only the beginning. With 4 inches of vibrator humming away in and out of her ass, my cock pounding away with full force and my free hand reaching around and strumming her clit, Melinda kept cumming and cumming.

She was thrashing and jerking around non-stop for several minutes before I noticed her hands had gone limp in her restraints. I cut the vibrator off and pulled it out with all care while reaching up under her sternum and taking as much of her weight as possible. I put the instrument aside next then, freed her from the wrist restraints and laid her down on her back.

Lastly I removed the gag. Melinda looked dazed for several seconds. Her eyes focused on my face, she worked some kinks out of her jaw and then gave me a fatigued punch in the gut.

"What kind of Jackass are you, trying to kill me like that?" she rasped.

"Don't be such a whiny prima donna," I teased. "One, or two, more times and that's going to be my big dick up your ass, not some little toy."

"I'm surprised you could figure out how to put the batteries in," she said after several seconds going over her possible responses.

"It has batteries?" I looked surprised. "I borrowed it from Celine. She likes it, so I figured you would too."

"You are a retarded reprobate with an undoubtedly long juvenile record ... and it is hard to breath in this damn thing," Melinda referred to her corset.

"But you look so fucking hot in it," I petulantly complained as I started massaging both of her nipples with two fingers each.

"I still can't believe I squeezed into the damn thing," she groaned - seeking some extra sympathy, no doubt.

"Oh, that reminds me," I furrowed my brow. "Roll on your side and give me your ass."

"What would possess me to do that?" she glared.

"If you don't, I won't let you suck my cock," I threatened.

"You can't negotiate for crap," Melinda sneered. "I imagine you had Celine get your home loan because you are clearly incapable of handling any decisions of importance." I stared down at her, she stared at me. Nearly a minute past before Melinda rolled onto her side and presented me with her buttock. I gave her proffered cheek a playful slap that caused her to jolt, jiggle and moan.

"That's a 'thank you' for not changing before coming over," I whispered.

"How I dress has nothing to do with you," she lied.

"Of course; all you rich girls dress to tease yet never deliver," I countered.

"Just you remember you had to tie me up to get this," she indicated her body.

I came back by pushing my cock to her lips. Melissa gave me a withering look though that didn't stop her from rocking gradually forward and wrapping her lips around my cockhead. She was quickly murmuring and running her tongue along my shaft. Once I believed her to be preoccupied, my left hand began running gently through her hair while my left caressed her shoulder, arm and corseted back.

Melissa, propped up on her left arm, moved her right hand to my butt and began pulling me in. It was fascinating to see my Mother-in-Law lavish me with such reverence and fervor. When I went from nasal breathing to open-mouth panting, Melinda pulled back, licked down my shaft and then kissed and licked my scrotum.

She shot me this look that fixed me with the suspicion she was certain she was doing for me what no other woman had ever done - and she was right. Melinda sucked in one testicle then the other and finally both at once. I was happy I held back for a whole minute.

"Jesus woman," I croaked, "please get me off now before I explode!"

"Beg my forgiveness for that stunt you pulled this morning," Melinda gave me smug look - then licked my shaft from base to helmet.

"Give it a rest damn it," I grunted.

"I guess I'm going home then," Melissa began to rise.

"Shit - damn," I growled. "Melissa."

"Mrs. Harmon," she corrected. The dichotomy of a woman making me use her last name while making me beg to have my dick sucked wasn't lost on me.

"Mrs. Harmon, I was a total bastard for tricking you so cruelly," I pleaded.

"Very good," Melissa gave a superior smile. "You are going to stop cheating on Celine."

I growled, refusing to relent despite my aching need.

"Oh joy," Melissa sighed. "Since you are clearly ruled by your brutal, savage instincts and neither common sense nor reason, I'll forgive your idiocy ... this one time." Yeah - right. Like she wasn't having as much fun as I was.

She kissed my pee slit, circled my penis edge with her tongue then smiled up at me once more.

"Promise me you will keep it in your pants around everyone else and I'll allow this indiscretion to pass unmentioned," she purred.

"As long as you know that I'm going to screw you every chance I get," I insisted.

"Keep believing that," she licked my lollipop. "I'm buying a stun gun as soon as I leave this place. You are welcome to come by and have me show you how it works."

"Get to sucking, damn you," I grumbled. Surprisingly, Melissa stopped busting my chops and went back to administering a fellatio for the record books.

She took exquisite pleasure in getting me close then pinching the base of my penis to hold back my ejaculation. My glans was swallowed, encircled by her tongue then passed down her tonsils as she slowly engulfed every inch. It was ten minutes of heavenly hell only cut short by a co-worker coming back into the storage area.

We froze in place until the person left. Melissa went from nearly petrified to highly aroused in seconds over this near discovery. Like Mother, like Daughter/Wife it appeared. She did manage to let me cum this time and I paid her back by shot-gunning my seed down her throat. Melissa sputtered, gasped and gulped like mad, yet still some leaked out.

Melissa sat up in the Loveseat and I crashed down beside her. We were both panting.

"What would you have done if that person saw us?" she whispered.

"Claim you were a high class call girl I was doing a special install with," I panted.

"Do you really believe I could be confused with a prostitute?" she mocked me.

"A really expensive one," I reiterated. I ran my finger between her tits, flicked the bow there then ran my hands all the way down to her stocking-clad thigh.

"You are a terrible liar," she looked away. "You also clearly can't appreciate quality when you see it."

I snickered, reached down to my pants and retrieved my wallet. A moment of introspection later, I pulled out two twenties, waved them in Melissa's face and followed that up by stuffing them into the corset between her breasts.

"What the hell is that about?" she glared.

"You came here about the money, right?" I taunted her. "Congratulations, you earned a few bucks. Aren't you pleased this trip wasn't a total waste?"

"Ah - ah - you are the most vile, reprehensible, villainous sub-human being I've ever met," she declared balefully.

Then she started humming a happy tune while she got dressed. She didn't throw my money back in my face either, damn it. That was my lunch money for the week. After I got my clothes on, I made sure the coast was clear and snuck Melissa back to my office.

"You don't need you to come by Wednesday," she enlightened me. "I'm going to spend the day sunning by the pool," she added in an off-handed manner.

"I didn't know you liked sunbathing," I mused.

"You are hardly the person I would confide anything to," she sneered.

"French cut, or thong?" I persisted.

"Since you are not coming by, you'll never know," she said snootily as she stood to leave. I found it amusing she had to tuck her shirt in tightly because it had no buttons. She made a noisy display of departing from there, leaving my office mates somewhat confused of how she arrived in the first place.

[...]

My sex life that night was eye-opening and exciting. Celine insisted on authenticity so we had to figure a way to tie her up. We had no chain link fence, or even a poster bed. In the end, I latched onto the idea of using the top kitchen cabinets to secure the loops. I was worried that Celine would get overly energetic and tear the doors off the cabinets. She promised to be good.

Or, I think that is what she promised through her gag. I taunted her that the vibrator rimming her anus had so very recently been up her Mom's ass (I'd cleaned it, of course).

"Yeah, Baby," I teased, "she moaned just like that. Do you like that? Do you think Melissa felt the same way?" She nodded vigorously, made a choking noise then hit her orgasm.

To keep to the script, I had to push my dick into her pussy while she was still spasming. That drove her into an even greater frenzy. I pulled Celine's head back by the hair.

"That's right, Melissa," I adlibbed, "Tonight while you are going to bed, I want you to think about me doing the exact same thing to your little girl; hammering all her holes with the same passion I'm showing you right now."

Celine sobbed and trembled.

"What do you think about that, Melissa?" I turned the screws on my wife. "Do you think her ass will be on fire as much as yours is? Do you think her pussy will throb in the exact same way? Do you think your daughter will cream when I 'accidently' call out your name as I pump my seed into her?"

Celine kept whimpering something over and over again. I pulled down the gag to hear what it was.

"Have mercy," she whispered. "Have mercy, I can't take it anymore."

"Has your husband made you happy, Honey?" I asked as I wrapped my arms around her.

"Let me down and I'll show you, Way," Celine promised. I released each arm in turn, allowing her to turn around in my arms. Our embrace lasted several minutes and I was enjoying the calm comfort of her arms around me and her breath on my neck when Celine suddenly began pushing me to the floor.

She grabbed something from around the stove before moving over me. Pouring the cooking oil over my cock was a surprise.

"Honey?" I questioned.

"I can't wait," Celine blazed with lust. Well ... okay then.

Celine put the oil aside, stood astride me and began lowering her bottom onto me. Her smile matched mine as she grasped my cock, stroked the oil over it a few time them raised it up so she could impale herself. My wife rubbing my cockhead against her anus was a bonus. She tilted her bottom left and right, working my dick past her anus and into her rectum.

"I am so grateful, Way," Celine moaned. "I know you've been honest with me about you and Mom and this has to be terribly confusing."

"I'm not confused," I grunted as she worked more of me inside her and her muscles tightened up. "I love you. Yours is the only opinion that matters to me."

"Sure, I like Melissa a whole lot more now than I used to, but you and I are partners, 'C'," I continued to comfort her.

"Do you like her, or making love to her?" Celine teased out breathlessly.

"I like the parts of her personality that remind me of you," I stated.

"And her body does nothing for you?" she teased me some more. With the way I described Melissa, Celine had no doubt that I desired her Mother. I looked away. "Has my Hubby developed a cougar fetish?" she pursued the truth.

"Are you a cougar?" I panted.

Celine shook her head.

"Nope. All I have is a 'Smoking Hot Wife' fetish, but you knew about that one."

"There - is - nothing - you - like about - her?" Celine gasped as she now bounced with my full length in her. "Not her ass? Her big boobs?"

"Don't forget her pussy," I ground my teeth. I was enjoying this interplay so much I didn't want to ejaculate until we were done. "Oh, and how her butt jiggles when - I spank it."

"Are you - saying - my butt - is too - firm, tight - and round - for you?" Celine pouted.

"Ah, shit-damn," I cried out. The pout and the vision of Celine's perfect ass kicked me over the edge. Jet after jet of my spunk shot into my wife.

"Baby!" she howled. Celine started trembling, rising to a crescendo as her second orgasm took her.

I was enraptured with the image of her gyrating above me, her hair whipping around as she grunted and moaned. She finished up by tilting forward and placing her arms outstretched, resting her palms on my chest.

"I can tell you one thing for sure," she gave a blissful smile.

"What's that, Honey?" I murmured happily.

"We are not going to get pregnant this way," she giggled. I spanked her thigh for her impudence. Celine wiggled her butt on my still semi-rigid rod and kept giggling.

(WEDNESDAY)

No one answered when I rang the bell at Melissa's place. I opened the door (I knew the security system after all) and called out in a level voice. A quick search of the mansion revealed Melissa by the pool in a pale yellow one-piece bathing suit. She was reclining on a full-length pool lounger with her broad straw hat shielding her from the mid-morning Sun.

"Werner, what are you doing here?" Melissa regarded me from rim of her hat. "I thought I made it clear you weren't needed, or wanted, today?"

"You mature wealthy women often forget what you need, so I decided to stop by anyway," I obviously surveyed her reclining form as I straightened my dick through my jeans.

"Can you be any more overtly sexual?" she mocked me. I put down my two work bags, strode over to Melissa's chair and knelt beside her at chest level.

"What do you want?" she intoned icily.

"A 'good morning' kiss would be nice," I suggested.

"How impudent," Melissa snapped. "I see I'll have to put you to work simply to keep your mind preoccupied."

"Have it your way," I leered. I leaned forward and kissed her - on her left breast. Even with the intervening fabric, my kiss excited her nipple to push out noticeably.

Melissa didn't try to push me away, or even raise a protest. Instead she stretched her arm under the chair to the towel beneath. Her hand came back up with a stun gun.

"I warned you," Melissa informed me smugly. The device crackled alive. I gazed up from my suckling yet refused to stop. A second later I suctioned on the nipple with renewed effort.

"Christ," she grumbled, "you are impossible. How much pain do I have to inflict on you make you keep your hormones in check?"

"Give me two minutes with this tit and I'll get right to work," I requested. I didn't know what that work she wanted me to do and I really didn't care.

She weighed the stun gun in her hand, switching her gaze from the weapon to me.

"Get it over with," she sighed in expectation. "I need you to fix the pool lighting when you've sated your addiction."

Now she considered her body to be my addiction - interesting. I started off my appreciation of her sacrificial morsel by slipping the upper strap of her swim suit off her shoulder and pulling it down to her elbow.

"What do you ...," she got out as the strap came down. She stopped in mid-question as I pulled the upper part of the suit down to fully expose her breast to my ogling. I made eye contact with Melissa as I put my lips to her protruding teat. As my tongue circled the sensitive tissue, Melissa looked away. I didn't focus solely on the nipple though.

I kissed and licked the entire breast, lifting up under the sagging mammary and tasting the freshly powdered scent there. My right hand cupped the breast, creating a fleshy mound for my mouth to suction up. My left palm began rubbing circles over her clothed stomach. When I tried to migrate further South, Melissa cleared her throat.

"Just the breast," she stated firmly, with a hint of passion. She was going to allow me her pudgy stomach - not her snatch. I could live with that for now. My right hand released the breast and began stroking her sternum leading up to the neck, jawline and finally caressing her ear. Melissa's pulse was quickening and her chest was rising and falling with an ever increasing tempo.

We were well past the two minute mark when my left hand slipped between her right breast and arm. Melissa gave no sign that she was aware of my movements even when I flipped a finger under her right strap and slowly pulled it down her arm. My left hand peeled the swimsuit from her right breast. I leaned farther across her body and began devoting the same intensity to that teat, areola and mammary.

When Melissa raised her right leg until the heel was opposite her left knee then let it fall open I knew I was given permission to explorer further. I didn't rush anything. I coasted my left hand along her right side, over her hip and onto her thigh. Melissa moaned softly. My fingers walked from her outer thigh to the inner side, then traced a wavy line down to her covered pussy, stopping right before contact.

I retraced my steps along her inner thigh, came back down then hopped my fingertips to the opposite thigh and rubbed that spot right above the crux of her thighs. My Mother-in-Law put the stun gun down and ran her hand along her stomach to the top of her pubic mount where it fluttered there with indecision.

That appeared to me to be a green light to play. With my left hand, I stroked her hand, lingering on her fingernails then pressing down lightly on her pubic mound until it dipped down to her vulva. I repeated the process six times before Melissa's hand followed my lead. We interlocked our fingers and began petting her tender sexy bits through the suit.

Her tell-tale quickening of the breath indicated to me Melissa was past caring about limitations and boundaries. Soon her left hand was rubbing my back and shoulders with repeated sojourns up my neck to stroke my hair. Her right hand was slowly nudging my fingers on her covered snatch farther and farther down.

No words were spoken yet the message was clear - 'play with my ass'. I made a few passes over her lower expanse ~ her ass was too large and the fabric too tight for me to give Melissa much stimulation. I work two fingers under the suit at the perineum, got them slick with her pussy fluids then slid back to her sphincter.

Her back passage was clenched tight when I got there. One slow circuit caused her to forcibly relax and let my middle finger in.

"Aaahhh," she moaned. The lack of a verbal retort reminded me of how far Melissa and I had traveled sexually. Her anal muscles clenched and unclenched with a steady pulse.

I matched her reactions by slowly twisting my finger deeper with each relaxation. Melissa's exhalation became a steady expression of pleasure.

"Filthy, filthy," she murmured. There we were - the 'old' Melissa. Her chastisement didn't stop the 'new' Melissa from wedging her hand in beside mine and push the suit's crotch fully aside.

As two of Melissa's fingers began making, wet squelching noises as they pumped her vagina, I decided to play-bite her breasts and pluck her nipples with my teeth. Her fingers on my upper back started clawing my skin through my shirt. The harder I bit and worried her teats, the harder she dug in.

I was caught in the emotional vortex of my Mother-in-Law and my wife. Sure, the sharpened fingernails hurt, but the sensual joy my wife would rain upon me as I retold this tale would more than make up for it. This was magnified by the sheer tension Melissa was putting herself through as she fought off her orgasm.

The withdrawal of my finger from her rectum brought forth a whimper from Melissa as she thrust her hips down, trying to recapture my digit. She didn't have to go far; I pushed two fingers in and I wasn't gentle.