My Older Sister—My Sex Educator—My Mistress* Frank and Donna

I’m not a big one on incest stories. Sure, I get turned on by the stories of some of them. Yes, I’ve dipped my wick in an older stepdaughter (future story) and have heard about a friend who gets gum jobs from an older relative (let me know on that one please), but there are chemical-physiological factors that usually discourage reproductive-age adults from fucking their blood relatives.

There are real life exceptions and I do have an interesting story that has developed over a lifetime with my older sister that I want to share in this space, to my readers, the ones I can tell everything to.

My sister Donna was born in the ‘50s, the oldest of 9, in an Irish/Italian Catholic family in the urban Midwest. She was more Italian than Irish in looks and temperament and she was short, had dark skin and black eyes. She was pretty, smart and angry, a perfect rebel for the ‘60s and oh yeah, early on, she had enormous tits that got everyone’s attention—from all of the boys and girls in the neighborhood and from her 6 brothers!

There were always young men “sniffing around,” as my dad would say and I’m not sure which one got her cherry, but I’m pretty sure it was my brother-in-law, who, years later, I would cuckold as I rolled his wife, my sister, over and fucked her hard from behind so she couldn’t watch me. I’m getting ahead of myself; let me get back to my story.

When I was around 10, I think, I shared a room (in separate beds) with two of my brothers, an older one, Jim, who was 12 and a younger one, Pete, who was 8. One night when I thought everyone was asleep, I was playing with my dick when my brother Jim leaned over and whispered, “Have you cum yet? I quickly dropped my young pecker and said, “What, come where?” Jim laughed and said, “The love juice that comes out of your dick when you’re beating off like you just were.” I half wondered, “Oh, you mean the weird pee?” Jim replied, “Exactly, it’s called cum, actually semen, my gym teacher told us in health class.” “Yes,” I replied, “a couple of times, it’s weird.” Jim chuckled, and said, you won’t think that for too much longer.”

With one mystery solved, Jim got out of bed and knelt next to mine to talk to me conspiratorially, “One of these days, our sister Donna is probably gonna come in here and ask you if you play with yourself. When she does, say ‘no, the church says it’s forbidden to touch yourself down there’ and I guarantee you you’ll get a nice treat. Just do what I say.”

My sister Donna is about eight years older than I and she had just barely graduated from Catholic girl’s school due to her “ratted” hair, white lipstick, short hemlines and most importantly, her sassy mouth, especially against Church teachings. There wasn’t anything she liked that came from the church. She was a rebel.

The summer after she graduated, I peeked down in the basement when she had six or seven friends over and everybody was making out under black light. My future brother-in-law was making out with another girl and my dear sister was also making out with another girl! Something I had never thought about until then, but really gave my little dick a jolt. She really was a rebel and a few weeks later she would set up housekeeping with these same friends during college. I can only wonder what things were like during those times of free love. Perhaps I’ll interview her someday about those times and I’ll share it in this space.

It was around this time that very late one night after Donna came home from a date, she quietly came in my room. She crawled on all fours between my bed and the wall and came up next to me by my pillow. Her head was close to mine when I noticed she was there, the faint smell of alcohol and cigarettes on her breath. She put her mouth next to my ear, and said, “Do you play with your penis?” I replied, “No, Father Paul says not to.” Her hot breath sighed.

“That is such bullshit!” Donna said, “Our bodies are a gift and can give us pleasure if we know what to do. I want to show you something.” She reached down and grabbed my very hard penis, nearly hairless, but anticipating the great treat my brother teased me with. She rubbed my tiny sack and balls and pulled the covers down and started to stroke my cock slowly. She brought her head over my dick like she was examining it. She took my hand and put it around my dick and stroked it a few times and whispered, “This is how you do it yourself.” Then she put my hand down and stroked me slowly for a minute and then rapidly for less than a minute and I quickly shot my load on my sister’s face and in her hand. She seemed pleased and I was surprised when she licked and sucked the cum off of my young cock, balls, belly and her fingers. She pulled a hankie out of her pocket and wiped her hands and face, as well as my shriveled dick. She held her index finger up to her mouth, making the “shhh” sign and mouthed “our secret,” blew me a kiss and snuck out of the room.

“How was it?” Jim asked me as we brushed our teeth the next morning. “Our sister’s treat?” he pushed and I played dumb. “I was up before you and kept my eyes barely open as slits. I also saw how nice she cleaned you up. She left me in a mess, when she gave me a hand job. I’ll bet she’s learning something from those guys that I heard Dad telling Mom he saw her follow into the woods. Mom called her a ‘whore.’ You got the treatment that a whore must give.” I just smiled.

I looked up “whore” in the dictionary and I didn’t like it. I didn’t think it applied to my sister then and I don’t think it applies now. But I did wonder what my sister did in the woods and in our basement with her friends.

Soon, we had some answers when my brother shared a book of X-rated “Sex stories” with me. It was all words with no pictures, the pre-internet forerunner of this site. I read the book voraciously, beating my cock off hundreds of times to the story of “Babs” and her seduction of men and women all over the country. We hid it in a secret crack under the sink in the vanity cabinet. Only my brother and I knew where it was—I thought.

One day I pulled the book out and in between the pages was a Polaroid picture of my sister Donna nude, squatting in heels, her back erect, her large tits with their giant dark areolas sticking straight out. Her nipples were hard. Her black pussy hair was thick and shaggy, completely covering her sex, a faint line of hair heading to her navel. Her long, straight black hair was in a ponytail and pulled back around, the end resting on her left tit. She looked right into the camera. I jerked off my cock and came quickly. I stared at the picture, examining every detail. I was thrilled and ashamed. My young cock was soon hard again and I blew a load remembering my first hand job. I licked the cum off of my fingers and put the picture back in the book and stashed it. I learned many things from that book and occasionally jacked off to my sister’s beautiful body, trying not to look at her face.

During the next four years I lost my innocence in the usual stages, kissing, necking, petting, feeling up, sucking tits, fingering a pussy and finally fucking a girl. A nice church girl, Rose, in the woods near our neighborhood. I was 14 and skinny and a good kisser. She was 13, had a nice smile, a good tan and big thighs and smallish tits. We lay on a blanket and kissed for a long time as I fingered her young pussy. I didn’t know what a clit felt like and I never knew if I touched hers. I remember her more as a girl than a woman and the folds of her virgin pussy were soft and pure. I have had the pleasure of ending the virginity of women and girls between the ages of 13 and 30 and it’s always special. We were both scared.

When I rolled up from the side of Rose and got up on my hands over her, I asked, “Are you ready?”She smiled sweetly and nodded yes. She barely spread her legs and I guided my rigid dick into her tender and unmolested pussy lips. She just laid there motionless as I clumsily entered her virgin hole, pushing past her hymen, she gave a little grunt and she asked, “Was that my cherry?” I didn’t know and I don’t remember what I said, I just knew I finally lost my cherry with a “woman,” Fucking her slowly at first, I quickly blew my load on her bush and belly after 15 or so thrusts in her sweet young pussy when I pulled my squirting dick out as I had promised I would. We lie on the ground for a few minutes awkwardly and then cleaned up the semen and bit of blood from Rose’s cherry.

Rose and I had sex a few more times, with her always on her back, spreading her tan, plump thighs slightly for me and receiving me as the polite, Catholic girl she was, with a smile and a thank you. Soon we moved on, something I am writing more about in another story about the summer of sex a group of us enjoyed in those same woods.

Back to my sister, by the time I was about to turn 18 she had finished college and medical school and was about begin her residency out of town. She took the time to attend the big family reunion camping trip and we had a few talks, catching up. I barely knew her, she had been living away from home for school for a long time, but we got along easily and I tried to get the image of her naked body that I had beat my meat to so many times out of my head.

We were on a hike in the dense woods, miles away from the campground, when she began asking me about high school and how I was doing with the girls. Being coy, I just said, “Alright.” But of course she pressed me for details and I let her know that I had “Gotten it on with a few girls, but no one special.” I told her I would be heading to college without any attachments.

A few minutes later when we were resting on a log my dear sister asked, “Have you had a blow job from a chick—or should I say—a good blow job where you are actually forced to blow a load of semen into somebody’s mouth?”

Remembering my brother’s advice from years earlier to not admit to anything and thinking of the couple of bad attempts at blow jobs that local girls had attempted and the only really great blow job I received was from an older man who had offered me money in the park late one night to suck me off, but gave me the best head I received for years for free, I said, “No,” not actually lying.

She began to rub my dick through my shorts and said, “Remember the lesson I gave you years ago?” I nodded yes and she continued, “You’re going to school and you will probably get a lot of these. I want to give you a standard to measure them by…”

She then pulled my quickly stiffening dick out of my shorts and put her head in my lap and began to expertly lick and suck my hairy cock and balls. She stopped for a moment and looked at me with a smile and said “You’re all grown up! Your penis is lovely! As a medical professional, my sister always called body parts by their correct names, this along with my adult sister trying to suck me off didn’t really make my dick the hardest, so my sister laid me out in the grass and whispered, “Close your eyes and relax and pretend I’m the prettiest girl who WOULDN’T suck your dick and is now doing it…”

She began to work on my balls and sack and soon enough I was rock hard as her warm tongue worked my pulsing shaft up and down. She popped my purple head between her full, soft lips and began to gently suck it, pulling out the pre-cum. Then, slowly, at first, she began to swallow my cock whole and work it as a piston in her eager mouth hole, my sister’s big lips reminded me of Rose’s puffy virgin pussy lips from years before, and a unique feature of having my dear sister suck me off.

Lost in my thoughts, I came in my sister’s mouth with no warning, she deep-throated my cock and swallowed every drop, licking my cock and balls clean. I reached down and grabbed the hot cocksucker’s head and when I felt the short ‘Page Boy’ hair cut my sister wore for easy maintenance since she began med school, I was momentarily confused on who just swallowed my big load of cum, one of my sissy boyfriends who occasionally sucked me off for weed, or the pretty Jewish girl it took me all Senior year to get in her jeans and fuck her sweet, virgin pussy. “Susan” would never blow me, thinking my uncircumcised cock was only good enough to take in her virgin pussy, while she only sucked off circumcised boys at her temple, in order to maintain a good reputation with her future marriage prospects.

Still, when I came back down to Earth, I quickly saw it was my older sister wiping the cum off her lips and smiling at me as I quickly got up and pulled up my shorts, my face burning. “Donna, I can’t believe you just did that to me!” I stammered. “I did, you can and you liked it you little shit!” She smirked, “and I was happy to help you out baby brother, because judging by the size of the load you just gave me, you haven’t gotten off in awhile!”

I was embarrassed and ashamed as I had jacked off in the camp shower hours before, but still worked up a big load of jiz for my sister’s hot mouth from the great blow job she had just given my young dick. “It feels all wrong,” I whined. “Sisters and brothers can’t be lovers.” My sister soothed me, “We’re not, I’m teaching you the way an older sister should, the things I’ve had to learn first because I’m the oldest.”

Donna continued, “I love to suck dick and I’m good at it. For a long time, the only guy I let fuck me was Jerry, my first boyfriend and the man I will soon marry. As dad knew, I went into the woods with a lot of guys, but that was mainly to smoke pot. I would give a guy a blow job to smoke pot and he thought he had power. But what I quickly learned is that a great cocksucker—a special cocksucker– has a special power to keep men coming back. With ‘things’ and only their continued silence, I would suck a guy off for stuff, my school books, my rent, a haircut, a tank full of gas, but only if they kept their mouth shut. Jerry caught me a couple of times and he understands and loves to fuck me while I’m blowing one or two of his friends. I have sucked the penises and swallowed the semen of most of the guys in our neighborhood, many of them multiple times and you haven’t heard about it, have you? You’ll understand better when you get to college.”

I was stunned. Maybe my sister was a whore, but she was right, this was the first I heard of it. To this day, I beat off to the image of faceless strangers, lined up with her squatting in her heels taking cock after hard, long cock expertly in her mouth and sucking them off until the men collapse at her knees, her drinking all of their cum without spilling a drop, licking her big soft lips and smirking, knowing her power.

Fast forward several decades, my sister has been a successful surgeon. She’s never had kids. She’s worked hard and is rich. She’s in great shape and still quite beautiful, working out with a young personal trainer several times a week and swimming daily in her indoor pool. She is semi-retired and I see her several times a month at our mom’s. We are cordial. My kids are grown and out of the house. She is a generous and doting aunt.

When my job transfers me nearer to her more exclusive part of town, she invites me over for dinner when my wife is traveling for her work one week. I agree and show up at 530 on an autumn evening. Maria, her housekeeper has already left, but has prepared a nice dinner for us. She hands me a Jack Daniels and water and pours herself a Chivas on the rocks.

“Where’s Jerry?” I ask. “On one of his ‘business trips’ which I think are more about golfing, than business.” Donna said, with exasperation. “We haven’t had intercourse in months, he licks me and rims me, but he can’t get it up like he used to and he’s too proud to let me write him a scrip for Viagra or Cialis or to see his own doctor. I don’t really need his licking, Maria is great at that and she has an amazing pussy that I like to munch on occasionally. Same old Donna, more discrete, but with more resources. Her pretty Mexican maid could cook, clean and share her bed when she wanted her. I’m sure she paid her well.

We enjoyed our dinner and gossiped about family. After dinner we walked the property and looked at the leaves changing and then went in for a brandy by the indoor pool.

Looking at my sister, I didn’t feel the same way about her. I didn’t feel strange about touching her any more like I did when I was a young man. I asked her about the things she did to me when I was young. “I felt strongly I needed to help you guys to grow up enjoying your own bodies and women or men if that’s what you were into.” I replied, “I like both, like you, but more women and I’m glad you did it. I’ve never forgotten, all of these years and I think of you often, if you know what I mean.” She had been listening intently. We were both a little drunk.

My sister Donna got up and said, “Whew, I need to cool off” and she pulled her dress over her head and jumped in the pool in her bra and panties. I took the cue and stripped down to my underwear and jumped in. I swam underwater to Donna and popped up in front of her, “What are you doing baby brother?” My heart pounding, I grabbed her around the waist and kissed her deeply, I was thrilled that her big lips were wide to receive my darting tongue as I plunged it in her mouth. “Oh God, I’ve wanted to kiss you for so long” Donna gasped as she grabbed my throbbing cock through my underwear.

I pried my hand into her panties and dug around for her clit, which I quickly found and began to work side to side as my sweet sister moaned and began kissing my neck roughly. She pulled my underwear off and began stroking my now fully hard cock as we again began deeply kissing. I touched her tits for the very first time. I took her bra off and moved her to the corner of the pool where there were steps that I lay her down on and took off her underwear.

The pool house was dark as I ran my hands over my sister’s smooth, svelte and beautiful body. Her tits were large and still firm, the large dark areolas sprouting hard tight nipples, she wasn’t skinny, she seemed more muscular and her pussy hair was now neatly trimmed. She still kept her hair short for easy maintenance and as I looked at her I didn’t see so much my sister, but a rich, powerful woman who I wanted to fuck and subjugate with my body and cock.

As I rose up on my arms and got over Donna like I first did Rose so many years before, this time Donna spread her legs high and wide and said, “I need a cock in me. Fuck me!” I put my hard dick in a little and then plunged in to the hilt, pumping a few times then bending my cock hard against Donna’s clit drawing a long scream and her first orgasm. She grabbed me hard and pulled me to her, digging her short “surgeon’s nails” into my back as she tipped her ass hard into my thrusting cock. She came again and pushed me off. “You are not cumming in my pool, let’s shower and go somewhere else.”

The pool house had a shower she started and warmed and then put me under as she soaped my body and washed my hair. Then she kneeled in front of me and gave me a long, slow luxurious blow job, starting with a gentle sucking of each of my balls and long strokes along the shaft, finishing with giant slurping sucks. She stopped and made me bathe her and then dry her off.

Donna was definitely into control. When she got me into her bedroom she put a robe on and kept me naked ordering me to get her a drink.

When I came back in the room with the drink, she was in a big chair in the corner, bundled in a robe, her hair slicked back. She took the drink and had a sip and as I headed to the bed, she barked “Back here boy!” My whole body went limp as I recognized the tone of an old “master” who “owned” me for a month when I lost a card game in college to a brutal senior in my frat house.

I went back to my sister’s chair and she ordered me to stand at attention and after eyeing me up and down, she ordered me to turn around slowly and said, “You’re still in good shape and you did well on your try out. I choose you to serve as my lover when I want you. Now, get down on your knees and service my pussy and asshole with your tongue and lips.” Her voice and language had changed. It had slowed down and she sounded harsher and less clinical. My sister still had her doctor’s “God complex,” but now it came from her powerful mouth and pussy and not from her brain and scalpel.

I got down on my knees as she ordered and crawled to her on all fours. This seemed to please her as she opened her robe and spread her legs for my head. As I raised my head I licked her smooth inner thigh with my tongue and as I did it she gave me a quick, hard slap to the head and shouted, “My asshole first and then my cunt if I let you, you stupid bitch!” My dick was completely limp and I was probably too drunk, but as a nicely humiliated slave, I did what I was told, secretly hoping someone was watching (see my other story about Teenaged Boys Swimming With Hard-ons) so I could be further humiliated.

I plunged my tongue into my sister’s puckered asshole and proceeded to rim her like I never rimmed anyone before, I so wanted to please her. I lapped her smooth asshole like a dog in heat until she moaned and stroked my hair like I was a favorite puppy.

“Ok baby, do my pussy now,” my sister Donna’s voice softened. I moved up to my sweet sister’s clit and began to gently suck it and she came almost immediately with a moan. I began to lick and suck her dripping labia and plunged three fingers into her gaping, well-fucked cunt-hole. I began to lap her clit and hand fuck her with my thumb up her ass and she came again with a yelp and by now my cock was rock hard again. My sister moaned an order, “stop.”

I stayed kneeling and she took me to her bosom and rested for a few moments. I wondered if she was done with me—tonight or forever—because I didn’t want it to end. I was drunk and confused. I stared at her tit. A tit I had beat off to as a boy hundreds of times and felt ashamed. Now I could lick and suck it, but I was scared to as I didn’t want to be slapped again. Did she really want a slave? I didn’t mind the role occasionally, but I wanted to seduce her, control her, make her beg to be fucked and be thrilled to get on her knees and blow me and any friends I wanted to share her terrific mouth with.

After what seemed like an hour, she softly said, “Carry me to bed baby brother.” I did as I was told, even in my drunken state, taking her robe off, evening up the control tables a bit by making her naked. I laid her out in her bed and kissed her on the lips and she threw her arms around me, her longing, gasping mouth and slithering tongue covering and filling my mouth. I was startled and could feel the tide turn. She was a weak mistress. I sobered up a little and stood up straight and fed my drunken sister my hard cock in her mouth. At first, I had to force her lips open but when she knew it was me she opened up and started to give me a decent blow job, kind of like a drunk whore in an alley, the way I was viewing her now, that I could feel rising in my loins. I began treating my dear sister and earliest sex teacher the same way. I spun her around so her head was over the side of the bed and leaned down to her pussy and started to lick and suck her pussy as my cock straddled her face.

As she got into my eating her out, I stuck my rigid cock between her big, thick trembling lips. She sucked it greedily and then with her neck bent over the edge of the bed and her at the height of another orgasm, I jammed my whole seven inch, fully hard cock completely down her perfectly straight throat, She gagged loudly and I stood straight up and grabbed her by the hair, rolled her over and violently mouth fucked her as she spit up and I blew a load of cum in her mouth and on her face and tits. I roughly smeared the mess of spit and cum all over her face and tits, slapping both as I rubbed them. “Who’s the baby now? I asked, meanly. “I am Frank, your obedient sister.” she cried softly. I rolled her back over roughly and I planted my asshole on her face and after a moment felt her tongue rimming me and penetrating my tight ass. After I was satisfied that I had fully subjugated her, I shoved four dirty fingers down her throat and slapped her face. I walked into the attached bathroom and cleaned myself up in the shower and I was now pretty sober. I threw Donna a towel to clean up with and she threw the covers back to welcome me into bed. She looked grateful and scared. I crawled in, spent and dozed off.

Several hours later I awoke to a freshly bathed Donna sucking my growing cock in the candle lit bedroom. As my cock got hard, I pulled Donna’s hair and ordered her to “ride on my cock.” As I saw my sweet sister happily riding my, again, hard dick, my sober mind began to feel a little weird again. My older sister was fucking me and loving it! I rolled her on her back and she thrust her legs in the air, her dripping pussy ready for my hard, bouncing cock. I dove right into her cunt, fucking her hard and fast. She came as I pressed on her hard and she was panting like a dog.

It was hard to see her like this and I rolled her over on all fours and held her hips hard as I shoved my rod all the way in her pussy and she came again after a couple of strokes. I had my thumb up her asshole and I had been lubing it with spit when I pulled my cock out of her pussy and put the head of my dick in my sister’s ass, she yelled, “No! Never in my ass! At that moment my cock was halfway in and as she began to cry I had my cock in all the way and as the rhythmic slapping of my hips against her firm ass cheeks began to be drowned out by her increasingly loud moans of pleasure as I pounded her beautiful, tight asshole into anal submission. She was mine in all of her sweet holes. I had turned the tables on my first teacher. I blew another load of cum right into her sweet tight ass as she fingered her clit to orgasm.

I collapsed on top of Donna and as my cock shriveled out of her ass, we slept.

Donna and I fuck regularly now as she works less and our “Service” relationship shifts and changes, as well as her willingness to take dick in the ass. I broke her anal cherry that night. She had only taken small dildos in her ass before, but she got into it that night.

I’ll write more about our adventures and her past if you like. She is my main squeeze these days as I had shared my wife with a black friend and now she seems to only like getting black cock from him and his buddy. So I cuckold and am a cuckold.

Frank Mills writes real sex stories about real people for real people. Please feel free to comment.

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