MilaOceanMilaOcean
NattashaRomanovNattashaRomanov
CarlaNicholsCarlaNichols
ElenaStoneElenaStone
TiffanyCardiTiffanyCardi
MerllinMerllin
CuteCloverCuteClover
Swipe to see who's online now!

Billy and Mrs. Anderson

Story Info
Billy does Mrs. Anderson, two girls, then his Mom.
24.3k words
4.62
133.7k
287
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

WARNING: This story involves scenes of graphic sex including domination, breastfeeding, seduction, adultery, oral, incest and anal. If that is not what you are looking for don't read on. All sexual acts depicted in the story are committed by adults over eighteen years old.

Hi, my name is Will, Will Michelson. I just recently turned eighteen and graduated high-school. My friends, classmates and teachers called me Billy since third grade. It was in third grade that Mike and I became best friends. He was held back in third grade so he is almost nineteen.

We were always hanging out. His Mom and my Mom was just 'Mom' as we spent so much time together. We were always together, best friends, as close as brothers. Both Moms raised us, fed us and trained us up to be caring sons and gentlemen. We were a tag team in all the sports and completions throughout school. We double dated the pretty and the smart girls throughout school but Mike had a new strong sense of confidence starting senior year and his relationship with the senior girls seemed different. It was as if they sought him out. I was his wing-man and benefited from the really popular girls wanting to be close to him.

Mike's mother gave birth to a baby girl just before senior year ended. My mom told me she had a change of life baby. Since my dad died on an oil rig explosion my mom and I have been very close and talk about all things. She explained that a 'change of life baby' happened to older women who thought their body was done making babies but 'accidents happen' she said laughing.

I was eighteen now and we had talked about how babies were made and she told me to be careful and always protected. "You don't want an unexpected child and wife this close to graduation," she warned me. Mom and I were totally open to discussing sex and girls and relations. I told her she didn't have anything to worry about as dates with girls hadn't gone that far.

She shocked me a bit when she got a sad look in her eyes then pulled me in for a kiss on her lips. She had never done that! She then gave me an even longer kiss that made my cock start to get hard. Softly she told me, "Now that you are eighteen you'll soon experience being intimate with females. Just be smart and don't hurt them emotionally and don't use them just to get your cock wet!"

When she said 'cock' I got rock hard! The guys in the gym classes and team shower called me 'sausage' to tease me. Like all guys I measured. I am eight fat inches long. Maybe the guys told their girl friends who told their girl friends that "Billy is packing meat so stay away!" So backseat make out never went very far. Mike never talked about his experiences with his steady girls and I never asked.

Anyway, as I said I stayed over Mike's house a lot growing up. Mrs. Anderson was just Mom until recently. Ever since turning eighteen I was always looking at her and her mature body. Her breasts got larger once Alice was born and she was always breastfeeding. I saw her feeding Alice many times and she would smile at me and not cover up. Mrs. Anderson's breasts were the first real female breasts I had seen and I saw them at least once a day.

I memorized their shape and fullness and how they sat upon her chest. I memorized the dark fullness of her nipples as she left them exposed while feeding Alice. I watched drops of milk leak out her full dark nipples and drip onto her belly. She knew I was watching and always smiled at me not making me feel guilty about looking at her boobs. After the first few times she would have me sit opposite her while she switched Alice from boob to boob and would laugh some times at how red I turned.

Seeing her huge milk filled boobs always got my cock hard and I would go in the bathroom and dig down in her hamper and get a pair of her used panties. I would smell the gusset and breathe in her fragrant scent. I would then jerk off and coat her gusset with my hot thick white cum. I'd cum a lot then wipe off on her panties and bury them deep in the hamper again. I'd think about fucking Mrs. Anderson all the time since turning eighteen.

Back on my eighteen birthday Mike and Mrs. Anderson had a cake for me. She had just fed Alice from her wonderful breasts and leaned over to serve my piece of cake and her boobs fell out of her unbuttoned blouse. My eyes shot wide open! Her dark circles on her tits held her fat long nipples which each had a tiny drop of milk. One fell on my wrist and I slowly licked it off. I was frozen in lust having a mature woman's boobs this close to me.

Mrs. Anderson looked down and laughed and took each breast in her hand and slipped them back into her blouse. "I guess you got a birthday treat Billy," she said laughing and mussed my hair. She leaned in and kissed me on my lips as her tits pushed against me. Ever since then my eyes devoured Mrs. Anderson and she knew I watched her. It seemed she called me into the den to ask me something every time she was feeding Alice. I got to memorize each beautiful breast and hard dripping nipple.

My cock got hard each time I watched and pushed out my pants or shorts or climbed down my thigh. She smiled and watched me fidget moving my cock to ease the tightness. It was like she liked me watching her and was not upset with my cock getting hard each time I was near her. She started giving me lip kisses when I came over, at bed time if I stayed over and whenever I left their house. I was getting more confident around her and soon kissed her back. Mrs. Anderson would purr when I kissed her and smile then muss my hair.

This time I was staying over Mrs. Anderson's house as we were preparing to go up to their lake house and open it up for the summer. Mr. Anderson always went up that first week but a last minute business trip came up. He was already gone to the airport. Since Mike was nineteen we all still decided to go. Mrs. Anderson, baby Alice, Mike and I would leave in the morning so preparations and planning were being made.

It was after dinner and I was sitting in the kitchen watching Mike's mother, Mrs. Anderson, move about. She always smiled at me and ruffled my hair when she caught me staring at her long hair, her body, her boobs or her ass. I thought more and more that Mrs. Anderson was hot, hot for her age, just a hot older woman! Her panties were getting filled with my cum every time I was over Mike's house.

Tonight she opened the fridge and the light shone through her thin house dress. I could see her long legs and the shape of her huge boobs from the side. She was going to breastfeed Alice as usual so her boobs were big, full of milk, and tonight I watched them hang down when she bent over. I don't think she had a bra on so they wiggled as she moved. I didn't see panty lines when she bent over and I got horny thinking about that and I had to move my cock in my pants.

She turned to look at me and smiled when she saw me readjust my cock. She squatted to reach something low and in the back of the fridge and her thin dress slid down towards her waist showing all off her firm thigh that was facing me. She was squatting like a catcher and when she turned to face me I could see right between her thighs all the way down! She had long black hair so what was between her thighs was the same black colour. For what I could see I saw my first real pussy - not internet video.

Mrs. Anderson stayed squatting almost as if she was letting me see her privates for as long as I wanted to look. I looked up and she was still smiling then she shocked me and ran her fingers through her pussy and trembled. She did that several times even opening herself so I could see a wet pinkness. My cock was throbbing and I absently stroked it. She sighed and dropped to her knees and the night dress came down ending the show.

She stood and her boobs jiggled as she walked over to me and I was sure I was gonna get slapped and scolded. Instead she put those fragrant fingers under my chin and lifted my face until I could see her smiling down at me. Her wet fingers then moved slowly across my lips as my tongue tip came out and I licked. I tasted a woman for the first time! I tried to suck her fingers but she laughed and tussled my blonde hair then kissed me like my mom had done just recently. She then kissed me longer letting her tongue tip touch mine.

"Aren't you an inquisitive young man," she said softly and kissed me again. She stood close beside me and I could smell her perfume but then a stronger scent. I sat frozen as she slowly lifted her dress and let me see her dark haired pussy lips. She made no move to cover herself as I breathed deeply. I turned red hot in my face as Mrs. Anderson ran her fingers through her pussy lips again. Her dark haired lips were wet with that strong fragrance as were also on her fingers.

She dropped her dress and brought her fingers to my lips and I tasted her yet again. Her moistness was sweet and tangy like honey and vinegar. She let me lick her fingers clean until I was done then I kissed them. She ran her hand through my hair then softly told me I'd better go get washed up and changed into my pjs as were leaving early in the morning. I was frozen in my seat as Mrs. Anderson leaned down and kissed me deeply then ran her hands tenderly down my cheeks.

When I stood my long fat hard cock was pushing out the leg of my jeans and she looked down and took in a quick breath. Her hand softly touched my cock over my jeans. She turned me and swatted my ass and told me to 'get!' I was surprised I could walk! I washed up, brushed my teeth and changed into my pjs. I dug out another of her panties and came quickly on her soft gusset. So much cum came out as I trembled as her soft panties rode my hard cock.

I went to my spare room and climbed into bed but tossed and turned sleeping in broken segments. I finally got up all sweaty my cock hard from prurient dreams of Mrs. Anderson. I was dreaming of touching her naked boobs and sucking her milk and getting my face and cock between her wet curly black hairs. My cock was rock hard and throbbing when I got up.

I walked to the kitchen for some coke when I saw the light on in the den. I heard baby Alice cooing and gurgling. I knew Mrs. Anderson was feeding Alice her milk. Like a zombie I turned and walked into the den to see Mrs. Anderson's naked tits outside her night gown. She was rocking Alice under those tits and just smiled at me. She motioned for me to sit opposite her. She made no move to cover herself as I watched her milk drip from her dark extended nipples.

I was seeing Mrs. Anderson, Amy, in a new light. I said she was middle aged, just double Mike's age, just before forty. She had long black hair and shy blue eyes and a bright smile. She was in great shape having been a soccer and sports mom for her son Mike and I all through grade and high-school. I had never used the term out of respect and yes love but our buddies had called her a MILF.

Now to her boobs! She had dark circles covering the bottom slope of her breasts. Her aureoles were coffee cup sized capped by dark chocolate tootsie roll nipples. Alice must have nursed them out to their current large size. Tiny drops of milk dripped out onto the towel over the baby. Amy smiled at me as she rocked Alice back to sleep. She stood and walked out of the room and I thought the show was over but my hard fat cock was throbbing. Mrs. Anderson returned and sat in the same place her nightie around her waist her huge breasts still on display.

"What's the matter Billy? Why are you up at this dark hour?" she asked sweetly.

I told her, just like an eight year old, that my tummy felt funny and I felt heated. I told her I had bad dreams and was all sweaty. She smiled and patted the sofa and told me to lie down here as she could take care of my problem. She maneuvered me until my head was on her lap and my cheeks were against her belly.

"Do you like my breasts Billy? I see you looking at them all the time. Do you really like how large they are? They got large when Alice was born and my milk came in. I'll give you some milk to settle your tummy if you tell me you like my tits," Mrs. Anderson teased me.

"Yes Mrs. Anderson I love looking at your breasts. When I'm over visiting Mike I'm always hoping you'll be feeding Alice and I can sneak a look," I whispered.

She told me I didn't have to sneak a look at her boobs as she liked me watching her feed Alice. She held one large breast in her hand and moved her distended nipple against my lips. Her warm sweet milk dripped across my lips and tongue as she softly told me to suck her milk. I latched on and pulled her large nipple and part of her aureole into my mouth and sucked. I trembled from my having now felt Mrs. Anderson's tits in my mouth. My cock throbbed.

Her milk flowed across my tongue and I swallowed; sucking and swallowing as she hummed a soft tune. When her milk stopped I licked her fat nipple softly biting her breast flesh. She told me I was being naughty as she ran her hand through my blonde hair then moved me to her other breast. I moaned when her other nipple slid past my lips and more milk flowed.

I was now on her further breast so I started playing with the other. My hand held her globe tenderly squeezing and flipping her nipple. When I pinched her tootsie roll she moaned. My stomach tensed when I felt her hand lift my pj top and lay upon my abs. I sucked too hard and she pulled my hair chiding me to go easy as she had to nurse Alice again in the morning and didn't want her nipples to hurt. I couldn't believe she wanted me to suck on her tits.

I softly pulled her milk into my belly until that orb went dry. My tongue worshiped her breast licking the full underslope, the crinkly aureole and the firm fat nipple. Her hand popped the button on my pj pants and my long fat cock was released. I heard her moan as her hand moved tenderly to grip my cock. She moved up and down my fat cockshaft painting my cockhead with my leaking pre-cum. She brought her palm to her mouth and licked off my white syrup.

"My what a nice big fat cock you have Billy. I bet you have to jerk off several times a day to empty those big balls hanging under that big cock. I wonder what you do when you stay over my house being with Mike so many times. I wonder what you use to catch all your thick white cum when it shoots out of your fat cockhead. Do you pump your cock thinking about me and cum while you're over my house like a naughty boy, Billy? Do you have naughty thoughts about your other mother and her huge tits Billy?"

Mrs. Anderson interrogated me while her hand moved up and down my cock and tickled my balls with her finger tips. I was too busted to answer her. Did she find her cum soaked panties? Did she think I did that and not Mike? My cock throbbed in her warm hand as she added some milk on my cockhead. She told me there was a price to pay for her sweet milk in my mouth and on my cock.

I said, "Amy, I'll pay anything."

She laughed and said, "Amy is it now just because I'm holding this young man's wonderful long fat cock?"

She told me to sit up and pull my pjs to my feet and slide my ass to the edge of the cushion. I thought I'd let her push her whole arm up my ass if she wanted to. But instead she rolled to kneel on the floor between my wide open thighs. She took my cock in both her hands with my fat mushroom crowning the top. She moved her hands up and down my cockshaft pulling globs of pre-cum out the top. Each glob got licked away as Amy moaned, my moans matching hers.

My head rolled back against the sofa and my cock almost exploded when she took my fat cockhead and several inches into her hot wet mouth. I had to dig my fingernails into my palms to keep from cumming just then and ending my first time with extreme embarrassment. I started panting from the excitement.

"Easy Billy, relax, Mommy will make you feel real good. There is no need to rush. I want to give my inquisitive young man all the pleasure he can take," she said as she squeezed the base of my cockshaft over and over until the desire to blow my cum load dissipated.

"Am I the first woman to take this huge cock in her mouth? Is Billy gonna loose his oral virginity to this old woman? Is the mother of your best friend gonna be the first to swallow your hot thick cum as your cock explodes in my mouth? Don't you care that I'm an old woman with flabby tits and a big ass or do you only care that I'm sucking your fat cock?" she tormented me.

"No Mrs. Anderson you're not old and flabby. I think you're beautiful; always have. I love watching your body move near me. I love watching your boobs and ass move under your dresses or tight yoga outfits. I have sinful thoughts about things I wanna do to your body, and then I'm ashamed. I never thought there would come a day where we would be intimate. You're my shinning queen; my unattainable goddess. I am not worthy..." I mumbled on.

She laughed then pushed my long cock against my abs and licked my heavy balls. I had two apricots to go with the 'sausage' and she licked each one. Tenderly she sucked on each one pulling them into her mouth and caressing them with her wet tongue. She let the second one out then licked my taint and my crinkly anus. I groaned when the tip of her wet tongue pushed against my dark ring.

"Always keep yourself clean back here Billy. Some girls and women like to play back there hoping you would return the pleasure on their special places. Now think about baseball," she said as her pointed tongue pushed into my ass. I groaned as her hot wet tongue moved in and out my assring. "Let me know when you are about to cum in my mouth and I'll give you unexpected pleasures that will make your cock explode."

She moved off my ass and licked up the underside of my long fat cock. She licked across that knot under the cockhead and caused my thighs to tremble. She turned her mouth and took that sensitive flesh between her lips and sucked causing it to swell and run me up a flag pole. I trembled and hissed then she took my cockhead into her mouth and sucked. She took my cock deep tapping her throat then moving back to my crown.

Her hands moved up and down my cock driving me crazy. She slid off my cock then held it against her fat nipple. She let milk leak out onto the shaft then did the same with the other. She spit on my cockhead then buried my cockshaft between the cleavage of her large mommy milk jug tits. She spit and dripped saliva between her tits as I got the first huge tit fuck of my life. Her fingers came up dripping her pussy juices and she coated her cleavage and my cockshaft adding to the lubrication and my pleasure.

"Do you like my mommy tits squeezing your long fat cock Billy? Did you ever dream of your cock sliding between my mommy tits? Did you go on the internet looking for 'mommy tits' then watch a cock slide between them hoping the mature women was really Mrs. Anderson, your second mother, and that was your cock, Billy?"

I groaned with that image burning into my brain. Yes I did watch mature internet porn and every mature woman was Mrs. Anderson and I told her so. She pushed my ball sack against the bottom of her tits as her rubbing nipples leaked milk onto my balls. Each time she drove her tits down my cockshaft she took my fat cockhead into her mouth and sucked my pre-cum across her tongue. I was thinking the history of my baseball stats through the four years of high-school, anything to get my mind off the exquisite pleasure Amy's mouth and tits were causing on my cock.

"Okay young man time to blow your hopefully huge load of cum down Mommy's throat. Mommy needs Billy's thick white strong cum down her throat to make her milk rich for Alice. Give me all you got Billy, filling Mommy's mouth with your thick white cum. Thick white cum like you shoot onto Mommy Amy's spoiled panties from the hamper. Your cum tasted sweet when I licked it all off and swallowed it all."



sshh aahh yeah fuck me spank me bitchbought her dress sex story no bra voyeurCheating my husband with my houseboy litericalyricsmaster knocked uploveseat litererotica"lingam massage"litoraticaenki's puzzle 29Daughter in hot pants incest stories"erotic stories"tall sophie literotica Litetrica mistress submitslierotica guadeloupepleasuring my son taboo sexstoriesAshley Makes a Deal Ch. 6the preacher wife asstrHarley quinn pornos cumdumpsterliterotica selling wife in auctioncamping with sis nonconsentual sex confessionallison heut sexfighterBig huge ass ssbbw mother-in-law Literoticaliterotica.com - matured: with kisses, with hands and fingers, with mouth, lips and tongue i worshiped her bodylyricsmaster family pregnant"naked on stage"free adult stories gay loving bbcsmutty.com"incest porn stories""daddy dom""brother sister incest story"straight boss gay revenge story loteroticaliterotica ashley sissy yoga girlfriend gymaliterotica+"her mother's clit" +"suck me back to life"Sex Story BlackMailing My Church choir mistress To Become My Slutwattpad incest threesome vacation"literotica search"sex story huge cock incest sister “cum bloated”Princess Fairpeach Meets the Goblin he had three mothers and he had all three taboo sexstorieslost luggage humiliation naked sex story aunt"literotica .com"centaur "masterbate" storyasstr School skirt knickers"gay rape porn"Thugs sex stories incest lapsLITEROTICA CORRIES GAY STORIES.COMmaking mom mine Literoticasteffinheels/s/through-the-side-door-pt-04"literotica slave"KinkyWriter22hot arrogant attitude wife git fucked hard lerotica stories"literotica alien"literotica crossdressing eyelinerDaughters anal slave ch 2lyricsmaster family taboolyricsmaster sister caught mom and brother Sleepwalker impregnation erotic storieshow i met your mother litero"cfnm stories"tabubruch literoticaShooting precum in barber's chair"stories sex"Literortica -MOTHER WANTS SON LONG DICK TO FUCK & SATISFIEDHER HER PUSSY IN BEDLiterotica/VanessEvans"nude beach stories"black gardener rape her ass sexstoriesliterotica selling wife in auctionliterticacaramelbbw"taboo incest stories"a tight spot sex storyMY SISTER MY SECRETARY INCEST STORIESliteroticacom/tags/corporatefuckliterotica stories trapped"literotica loving wives"litoratica"taboo incest stories""sister in law sex stories"camping gone wrong forced to sit on son lap huge cock forced incest stories"wife creampie"Son put handcuff and shackles on his mother bondage literticababysitter takes advantage taboo sex story"lesbian twins"rape audios reddit glass elevatorBADASS CHAPTER 02 BY DIONYSOSK/s/mom-and-sons-valentines-day-sex-ch-01www.literotica.com /my teen virgin girlfriendkeralabottom97"literotica daddy"stud nephew conquered my cunt sex story"bdsm stories"Genie let's man spank her and lifeguard