Chapter 05.1
Date Nights
It had been a couple of weeks since my little sister, Tabbie, had come home early and found me and our Mom, Maddie, en flagrante. Unbelievably, she didn't freak out. On the contrary, she got so turned on that she started masturbating, standing in the doorway. We all finished and then had a frank discussion on how it had come to pass. Later on that night, I made love to my sister with our mother's blessing. We all began a scorching and fun sexual relationship. Mom and I, Me and Tabbie, and even Mom and Tabbie slurping each other's cunts happily. Usually, we were all together in Maddie's and My bed. Maddie and I had become a couple that first week while Tabbie was away. Mother and Son, deeply in love.
Over the last couple of weeks, we have all been intimate every night and even a few days, primarily on weekends but a few times during the weekdays. I continued to go with Maddie to her photoshoots. We even started having Tabbie come along as her 'Makeup artist' and assistant. We grabbed lunch or dinner on both days before going home, depending on the shoot time and length.
The last time we were out in the evening, I realized I hadn't taken either woman on a regular date. So I brought that up to them. Both of them were very excited by the idea. Because I'm in love with and sleeping with Maddie, it was the smart move to take her out first. It was a very similar time to our dates when Tabbie was away at swim camp. When we returned home, the evening continued with just the two of us.
Tabbie greeted us at the door and was on her way out to spend the night at a gal pal's house to give us time alone. Before leaving, I texted her from the restaurant to let her know we were on our way. She did as I requested and lit several candles around the living room and in our bedroom to set a romantic mood. She gave us both a quick peck on the cheek and then took off in my truck for the night.
I led Maddie to the couch and got her comfortable before slipping my shoes off as I sat on the floor to massage her feet. First, I freed them from the stilettos she had worn out. I slowly worked them until she was cooing and giving soft moans of pleasure. No words were spoken. I just pleased my mother, my woman, in the simplest way I could. When I was done, she stared at me with the most incredible love in her eyes. I smiled and looked back the same way.
It was then I noticed there was a flush to my Maddie's face and upper chest. The obvious signs that she was also aroused as well. I gave her an evil smile then and began sliding my hands up the outside of her calves, kneading them slightly as I went before moving up to her creamy and silky thighs. I caught the edge of her sexy dress with my thumbs, sliding it upwards. She lifted her hips slightly to allow it to slide up around her waist, exposing her tiny panties. These came down with my hands, reversing their motion until the panties were on the floor. I then, with an even bigger smile, one filled with lust, pushed my face into Maddie's steaming hot center and began to feast.
I started by slurping at her already moist slit. I next moved to kiss her inner thighs and inner and outer lips, alternating sides and locations, keeping her guessing where I would land next. Occasionally, I would kiss her clit gently before moving back off elsewhere. I kept up the random assault while listening to her breathing get faster and faster. Finally, neither of us could wait any longer, and I buried my tongue into her love hole. Maddie moaned loudly, and I moaned into her sopping pussy at the wonderful taste of my woman. The woman I have loved all my life, my mother. And soon enough, the mother of my first child.
After lapping away until there were no more juices to slurp up, I moved to tenderly attack her inner lips and clit exclusively. Maddie's moans continued to get louder and longer. Her pleasure made my heart swell with love that I could give her this pleasure. It wasn't too long, and Maddie was pushing her pussy into my face and grabbing my head to pull me in harder. Her body began to tremble and shake as she had her first orgasm of the evening. When she crested and started the downhill slide, she eased up on my face and released my head. I backed off as well, just kissing her lightly all over again, showing her my love.
She pulled on my hands, and then I climbed up onto the couch with her. I cuddled her as I caressed her back and thighs while she burrowed into my shoulder. When her breath became more regular, I leaned in to kiss her deep, though tenderly.
"I love you, Maddie. You make me so happy."
She coos into my shoulder. "And I love you too, Tony Honey. My Big Boy and my best lover ever. The man of my dreams made real."
I flush at the over-the-top compliment. "It's easy to be a great lover to a gorgeous and caring woman like you, Maddie." I then pull back a bit, pulling her eyes up with a finger and a devious smile. "And that I get to have hot, incestuous sex with my own mother is a big benefit and major turn-on."
We both chuckle at the truth of our relationship and the beautiful love we share in all ways. A few minutes later, I sit her up, stand up, pull her after me, and walk her into our bedroom. Arriving moments later, we slowly undress each other a piece at a time, kissing between items. When we are both naked, the kissing continues as we stand there for a few minutes before we slip into our bed. Before continuing to make love to Maddie, I grab the remote to the Bose music station in the en suite bathroom to put on some romantic music.
We return to kissing, now getting more and more passionate. Before long, I slip inside Maddie's still-soaked pussy and sink in to the hilt. She moans loudly and appreciatively before saying, "I love your giant cock, Tony. That you fill me up perfectly and make me feel both so full and wanted is amazing."
"It's the same for me, Maddie. You feel so good, like a warm, wet, silken glove that fits me perfectly. I plan on doing this as long as you let me, for the rest of our lives together. You're my wife in all but a legal sense." I grin again before continuing, "You are in name practically since you are Missus Turley already." We giggle again before returning to the hot kissing as I continue to stroke with a gentle passion.
I keep this pace until both of us come, Maddie having cum already gently four times, her big one building until we both go over together in a massive shared orgasm and creampie for her. When we both come down off the ceiling, we carefully maneuver until I am spooning Maddie while my cock stays plugged into her slightly oozing cunt.
We stay like that until Maddie says, "I'm ready for you to pound me from back there, Big Tony." She then giggles after referring to me by my nickname.
Kissing the back of her shoulder in acknowledgment, I begin stroking again to sloppy, squelching sounds from her cum-filled hole. I make sure to push all the way in and kiss her cervix with the head of my cock to new moans of pleasure from Maddie. Soon, though, I pause to move us into a doggy-style position and return to stroking in earnest. Quickly, I build to a fast pace before going all out and as requested, pound Maddie into the bed.
Her moans get loud fast, and in short order, she huskily shouts, "Fuck Yes! Pound Me, Tony! I want that big fat cock filling me forever! Oooohhh!"
Just to give it to her that much deeper and harder, I reach forward from her hips and grab her tits in my large hands and use them as handles. I pound her so hard that the bed shakes and groans with the motions. With the extra depth and power Maddie cums again, this time squirting all over both of us with a strangled, "Aaaaaaaaahhhhhhhh!" As her pussy clamps down, I fill her again, buried full depth inside her. My cock pushed right up to her cervix. If she weren't already pregnant, that would have blasted her womb full and completed the deed.
We fall flat to the bed when we cum. As soon as I can, I slip from over her prone form and lay beside her, rubbing her back and calming her breathing while I concentrate on bringing mine down, too.
"My God, Tony, You can really fuck, Baby. I'm so glad only Tabbie and I are the only ones to know that from now on." She slips over to kiss me, and I gladly return the loving kiss. We lay there staring into each other's eyes as I just smiled and nodded.
Eventually, we climb out of the ruined sheets and slip into the shower for a slow, gentle wash and rub down. Once we're clean, Maddie gets down and finishes deflating my cock with another spectacular blowjob. After our shower, we dry each other off and return to the bedroom. We change the sheets quickly. Then, we get into bed to sleep wrapped up in each other's arms. Before nodding off, I rub and kiss Maddie's belly, where our child grows. She coos at the loving gesture and rubs my hand, too. We are asleep in a few moments.
Tabbie comes home early the following afternoon. To thank her, I take her to the couch and make out with her for a good twenty minutes. Towards the end, Maddie gets in on the action, getting turned on while watching us. When I let Tabbie go, she sat there stunned for a few minutes, gathering her wits after the loving display.
"Je-Jesus, I should spend the night away more often if I get that kind of return reception." Tabbie murmurs. Maddie and I chuckle.
"We just wanted to thank you for our romantic time together, little sister. But it's your turn next time. Plan on it for next weekend." I kiss my little sister one more time, and so does Maddie, with a gentle stroke to her daughter's cheek. Tabbie smiles and blushes slightly.
The weekend continues with love and fun for us all between the pool and the sex amongst us all. The following week is also relatively normal. Maddie is modeling lingerie at this week's photoshoot, and I have to chase off some little creep again. He gets the lift and choke treatment the first fake agent received. He did piss himself, and the crew laughed as he scurried off.
Maddie was incredibly hot in the stuff she wore throughout the photoshoot. Since she looked so hot in it, they gave her everything from the shoot. Tabbie and I took her home, skipping food, and we ravaged Maddie throughout the rest of the afternoon. I filled both women twice, once in each orifice. Tabbie is getting just as good at swallowing my load as Maddie with her instruction. I continue to tease Tabbie with the threat of tossing her birth control pills and knocking her up before college, and she cums so hard. Maddie just giggles like a fool. We all retreat to the shower when the afternoon wanes.
After the shower, we get into clean house clothes. We work together to put some food on the grill and then eat dinner outside on the patio. All of us enjoyed Iced Tea to replenish our fluids. The evening is spent in front of the TV with Netflix, chilling and making out during commercials. At the end of the second movie, Maddie and I head to bed with Tabbie tucking us in with kisses like she is the mom. We chuckle together and wish her good night. She kills the light, and we are asleep before she closes the door.
That Friday, I was getting ready in my old bedroom where my clothes were still kept. Maddie came to me to suggest a fitting and complimentary outfit to what Tabbie would wear. As it turned out, she was right, as usual. I put on my Black silk shirt, pink tie, Dark Grey cotton-blend pants, and my usual black loafers. I topped that with a stylish match Grey vest in lieu of a jacket. My grandfather's pocket watch was in the vest pocket, and the chain looped appropriately.
Tabbie showed up looking stunning. She wore an elegant yet youthful black dress. The top was a near-matching Black silk camisole-like top with a fluffy layered lace bottom trimmed with pink piping down to her knees. She reminded me of an adult Disney character, right down to the Black choker with a hanging pearl droplet. With a tiny tiara and a large Pink bow at the nape of her neck. Her makeup was flawless, and Maddie had undoubtedly helped. Her feet had Black stilettos with 4" heels, and her legs were encased in nearly nude stockings. She was the very picture of our mother in her youth.
"You look fantastic, Tabitha. I'm a lucky man to have such a gorgeous date tonight.
Maddie let us use her BMW and we headed to a nice restaurant a few towns over. I wanted to treat Tabitha to a proper boyfriend-girlfriend date. We arrived a few minutes ahead of our reservation and were given a beeper and offered the bar to wait. We went in, and I ordered us two red wines. The bartender knew me and didn't bat an eye, and I asked to add it to the table tab. He just nodded and moved on. We sipped lightly at our wine as we waited.
Soon, we were seated, and I seated Tabbie like a proper lady and gentleman, as I had the first time the three of us had gone out when I reminded her to wait to be seated. Tabbie blushed at my gentlemanly treatment, especially after I gave her a peck on the cheek before taking my chair next to hers. We each reviewed the menus and ordered concisely when our waitress arrived. I ordered a significant amount of protein to be ready for later that night, having a steak and loaded baked potato. Tabbie had a lady-like meal of mostly salad, a grilled chicken salad with vinaigrette dressing.
The conversation was light and fun, mostly about college and what Tabbie could expect. I joked about boys hitting on the beautiful new freshman. We shared our meals like the lovers we have become, making older couples around us smile fondly. We continued with a shared slice of Apple pie ala mode. I paid the tab, and we strolled out happily, arm in arm. We went for a stroll around the park here, like I have with Maddie back home. We even sat on a bench for a bit. I held her in my lap as we stared at the scenery, especially the stars overhead. We eventually started kissing tenderly, and this went on for many minutes. When Tabbie started shivering, we walked out of the park, back to the car and home.
We arrived home to a romantic setting. Soft music played, and the lights were turned down to a low level. The ambiance was fitting for a date. We were holding hands the moment we left the car, and I tugged Tabbie onto the couch. I sat down and pulled her gently back into my lap. We returned to kissing gently, my large hands slowly and softly stroking her back, shoulders, and outer thigh. Tabbie's hand roved up and down my chest and across my shoulder and the back of my neck.
As our passion builds, Tabbie unbuttons my vest then shirt after removing my tie. I slowly work the zipper down on her dress before moving under her dress to tug her panties off but find none. Tabbie grins at me, that knowing smile at surprising me by being undercover naughty. We return to kissing, the passion ratcheting higher with our increased access. Tabbie ran her fingers through my chest hair, occasionally tweaking a nipple. I rubbed her nearly bare back, and my other hand cupped her hairless pussy, rubbing lightly.
When we couldn't take it anymore, I carried my little sister, my girlfriend, for all intense purposes, to her bed. I sat her on the edge and first helped her remove her heels and then massaged her feet briefly. She cooed her appreciation. I then took to my knees after removing my loafers. I pushed her lightly to her back, but she stopped back on her elbows.
She watched as I put my face into her steaming center and began nibbling her inner thighs and outer pussy lips, touching nothing else for now. When her breathing began to ramp up, I added a lick up her moist slit with a flick to her clit every few times. At the next stage, I also added nibbling on her inner lips. Before long, Tabbie flopped back, and her breathing was in gasps. I finally penetrated her womanhood with my tongue, and she came explosively. She grabbed my hair and ground her quivering cunt into my face and lips. I licked, sucked, and nibbled with abandon, continuing to penetrate her as well.
She screamed out as she came, "Oh, Tony!! EAT ME, BIG BROTHER!! Aaaaaahhhhh!!!"
When she finally let go of my hair, I dove in and slurped from her center and drank every bit of her juices I could get. I even attacked her little brown pucker both for juices and to give her that little bit more pleasure. She moaned again, "Jesus Christ, that's so hot and kinky. I love it."
While she recovered, I stood and completed getting undressed. I ended up standing there with my giant cock swinging in the open air when Tabbie's eyes finally opened, and they locked onto my cock. I helped her stand carefully and peeled the beautiful dress from her lithe frame. She stood in a barely there shelf bra putting her small tits on fabulous display.
I leaned in, kissed her hard, and popped the bra in a practiced move. As the bra came away in my hands, I tossed it on the floor and attacked her tits, especially her distended nipples. I pinched and rolled the one not in my mouth. That one got nibbled and licked and sucked hard, eliciting squeals of delight from Tabbie. My other hand slipped to her ass and squeezed that firm bubble of flesh to more moans from her. I switched off regularly for nearly ten minutes or so. When Tabbie's knees began to give out, I slipped her back to the bed, slipping her into the sheets before sliding between her muscular thighs.
I placed my large cock on her mound and began rubbing across her clit with the underside. Tabbie shivered at the added sensation. When a new dollop of her juices slipped out, I knew she was ready and put my cock head at her entrance. I pulled back from her tits to look Tabbie in the eye. When her eyes popped open, wondering why I stopped, she saw me smiling with love at and for my little sister. She moaned and pushed her pelvis up to me, encouraging me to push in. I smiled harder and pushed in, slowly penetrating my little sister, my girlfriend, to pure lusty moans of pleasure.
I bottomed out to more moans from her and a groan from me. Her tightness is still an exquisite feeling, I know I am one of only four men to plumb her depths. According to Tabbie, her only Man to do so, the others were merely boys. When she opens her eyes again, the look tells me she is ready for me. I begin pumping ever so slowly, trying to stretch out the pleasure for us both. Very soon, she moans again, and occasionally, she says my name in a husky voice. More often, just nonsense sounds of passion come from her throat.
I make love to Tabbie for at least twenty minutes and bring her to two more gentle orgasms. Her back arches each time, nearly dislodging me, but I keep pumping slowly each time, extending her orgasm. When she cums the second time, she pleads for a break, saying she has something else for me. When she can stand steady enough, she slips into her walk-in closet. There are a few minutes of shuffling, and before she returns, she calls out, "Close your eyes, Big Tony."
I comply and tell her, "Ready, sweetheart."
She steps out after peaking to make sure my eyes are closed. Tabbie stands before me and says, "Okay, open your eyes, Tony."
She stands there again in a new version of the 'Kitten-wear' from before. She still has those cute ears but has added a few new things. The nights earlier choker is replaced with the collar. Instead of the bustier from before, she is in less but just as kitten-sexy. She replaced the bustier with a simple gold chain around her waist. The kitten slippers are complimented with wrist and anklet bands of lace and pink ribbon. As a final touch, a matching garter on her left thigh, like a bride would wear for her wedding. The effect is dramatic and erotic, to say the least.
"My God, Tabbie! If I didn't already have a hard-on, I would immediately upon seeing this outfit. Christ, that's so sexy."
Tabbie giggles and blushes slightly before saying, "So you like your new 'Tabbie-cat?'"
"Definitely."
"Good, because it's time to 'breed' your kitten and give me a litter of my own." She giggles again before turning a little to show me the accompanying tail. It takes me a minute to notice it doesn't have a belt, and it's not attached to the chain, either.
Then it hits me. "Is that tail a buttplug, Tabs?"
She giggles and nods. "It adds a little something, huh?" She shakes her 'tail' at me.
I reach out and grab her by the waist and hips. I pull her back into my lap with her straddling my crotch and pushing my cock up to my belly with her little pussy. She immediately begins grinding on me, and the added benefit is that she's grinding right on her clit. She moans loudly and increases her speed and pressure.
I put my hands on her ass cheeks and helped to push her harder into my steel-hard cock, and her moans grew even louder. I then move one hand, grasp her tail, and tug on it repeatedly. Her asshole bludges slightly, and her moans turn to screams of ecstasy. She cums hard, squirting all over my lap. Before she really comes down from her orgasm, I slip her back on my lap and line up my cock with her tight hole. I pull her towards me slowly, impaling her on my rigid member until I completely fill her to more lusty moans.
I begin sliding her back and forth slowly, picking up speed as her eyes open to look me in the eyes. She then moves her feet to the sides of my thighs, squatting on my cock. She begins to bounce up and down, taking over fucking me and herself. It doesn't take her long before she is pounding herself down on my fuckstick. I begin to match her thrusts, and her eyes go wild and big as I tap her cervix each time. In a few more minutes, she cums again, and this time I go off, too.
I tell her, "My 'Kitten' is gonna be bred well tonight. We will have a litter growing in her belly before morning." She moans deeply, and her pussy pulses again as another wave washes through her. I unload inside my little sister and now my girlfriend. She keens out her pleasure in a cat-like yowl. When she finishes cumming she slumps into me, her arms around my neck, holding herself up. I encircle her body with my strong arms, gently stroking her back to calm her.
When our breathing returned to normal, Tabbie leaned back, still encircling my neck with her arms. We look into each other's eyes, and we smile broadly before leaning into a passionate kiss. After a minute, the kiss breaks. I slowly lay back, bringing Tabbie with me, my hard cock still buried in Tabbie's kitten pussy. We lay there with Tabbie's head tucked into the crook of my neck, her breath tickling my skin. I continue to 'pet' my 'Kitten' sister. Playing it up, she begins to purr in contented warmth. I murmur, "A litter of kittens soon," over and over--her purring increases.
Staying impaled on my cock Tabbie stretches her legs back along mine, working out stiffness in her hips. Keeping Tabbie on my cock, I sit and then stand us up before turning around to lay Tabbie back on the bed. I slip from her slick and messy pussy. I watch as my first load begins to slither from her slightly gaped pussy before it closes back up.
I note the tail is still firmly in place and ask her, "Tabbie, are you preparing for anal sex?"
She smiles a smile like that infamous cat, and in her 'Kitten' persona, it fits very well.
"I want you to take my Anal virginity, Tony. I wish now I had given you my first virginity, too, but it's too late for that. So, for our next date night, I want you to take it from me and allow me to give you this gift of my love." She says this last with a look of the purest love.
"It would be my honor, Tabs. But I should probably take Maddie that way first, unless we do it all together as a family. What do you think?"
"That sounds good for another time, but I want to give this to you as just us. My boyfriend completing my sexual indoctrination." She grins at the end. I grin back and nod.
"Well, for tonight's activities, we should continue that education and practice accordingly. On your stomach, Tabbie-girl. I'm gonna take my beautiful and sexy 'Kitten' from behind and make her howl like a dog."
Tabbie giggles at the imagery and quickly moves to her hands and knees, then drops to her elbows. "Get over here and breed me some more, Big Brother. Your kitten needs that litter of kittens. Then I will be your Tabbie-cat for real, a momma cat."
I climb onto the bed behind her and lift her tail, tugging slightly to light yowls. I slip back into Tabbie's silky pussy, already filled with my cum and about to be filled again. I pump slowly for a minute before increasing the pace incrementally over the next few minutes. When I reach a good fast pace, Tabbie moans out, "Uh, uh, uh," each time I slam home. Holding one hip in one hand, I reach forward and return to fondling Tabbie's lovely breasts. I pinch and tug on her nipples randomly while groping each breast, switching regularly.
I soon feel Tabbie's pussy begin to pulse and spasm around my cock. I let the incredible sensation pull me along. When Tabbie's crescendo hits, I follow her into ecstasy as I fill her again, forcing some of the original load out around my rod. When we finish, I fall forward over Tabbie, catching myself on my arms. I lean down slightly and kiss across Tabbie's sex-sweat-covered back, and she shivers in delight, purring her pleasure.
I slip us to our side, staying buried inside her so that we are spooning. I hold her snugly against me, and she folds her arms over mine, covering my large hands with her small ones.