Jens Next Date
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Jen's Little Brother free porn video
Halloween Oct 31st 2011 – the Present
"Trick or treat," I said with a big smile when Jennifer answered the door. She had a cute 'little princess' costume on. In pink. With ruffles. And she had a wand in her hand. I couldn't help wondering if her panties were also pink and ruffled. I knew that I'd soon find out.
"And what are you doing here?" my big sister asked back. My costume, in spite of the mask, certainly hadn't fooled her! But the smile that had immediately lit up her face the second she'd recognized me belied her grumpy words.
"Cinderella?" I asked as my eyes moved over her sisterly curves.
"I'm sorry, I don't have any candy left for you little boy," she said as she pretended to close the door.
I put my foot out to stop it. "Not even one little candy kiss for your favorite brother?" Jen looked great. In fact she looked sweeter than any Halloween candy ever could to my hungry eyes. My real cock started to grow.
"I'm not lying," she said with a teasing grin. "Besides you don't get any candy without a trick. Does my funny little brother have a Halloween trick for the beautiful princess?" sis challenged as she waved her royal wand at me.
I laughed. Then I opened my overcoat. While pushing the button that triggered the erection. Ten inches of plastic penis jumped up towards her.
"You perv," she squealed as I closed my coat. I'd done the whole thing so quickly that I could tell she wasn't sure if she'd seen the real thing or not.
"So where's my treat? " I asked with an evil leer.
"You could get arrested going around the neighborhood like that. Dirty old teenager!"
"I'm wearing it to the party tomorrow," I told Jen as I flashed her again. This time I gave her enough time to recognize it for what it was.
"Yeah right. You're little high school sweetheart's mommy will be really happy to see her daughter escorted away by a plastic penis toting pervert."
"Rose's mom thinks I'm a wonderful boy," I answered. I left my 'dirty old man' coat open.
"Rose!" Jen spat out. Sis did not like my girlfriend very much.
"In fact I'm pretty sure Mrs. Cameron just might like to see her daughter's boyfriend's cock herself."
"If she's anything like her slut daughter she probably would," Jen agreed disdainfully.
"An all day lollipop for a hungry MILF," I added as I pushed the erection button again.
"Hah! All day? More like--"
"And I'm pretty sure my old, married sister would like to get her hands on her college freshman brother's cock too," I interrupted as I wiggled my hips.
"You're fresh all right! And stop that! And come inside before one of the neighbors sees you and calls the police," sis ordered as she grabbed the plastic appendage and pulled me through the door.
"So, don't you have any Halloween kisses left for your brother?"
"You're too late ... besides I told you, I've already given all my candy away."
"Have you?" I asked as I moved towards her until my plastic penis was pushing up against her stomach. I pushed the erection button again.
"Stop that." Ordered with a giggle. Then I pushed the other button on the dildo's controlling mechanism that I had hidden in my overcoat pocket and a stream of hand cream spurted out the end of the plastic cock.
"Yuck, that is soooooo gross," Jen said as she jumped backwards. She wasn't quick enough! "If that is what I think it is you are in big trouble mister," she said as she tentatively dipped a finger into a blob of the white stuff that had landed on her princess dress.
"Taste it," I invited with a leer.
"Yeah, as if I want to taste my little brother's yucky sperm," she answered. But there was a twinkle in her eyes.
"You never complained before." I watched as she brought the cream laden finger towards her mouth and nose. Watched as she sniffed at it. Watched as the tip of her tongue flicked out and tasted it.
"It's not really--" She left the words hanging. For a second I caught a small look of disappointment in her eyes.
"Of course it's not. What do you think? That your brother's some sort of pervert? So are you sure you don't even have one little kiss left for me?" I asked as I kicked the front door of sis's house shut.
"You are a pervert. And I don't have even one," my sister answered. "The little devils started coming around even before it got dark. I was out of all my candy by eight-thirty. I was just getting ready to put out the porch light and put everything away." It had been just minutes before nine when I'd rung her doorbell. I'd been hoping that the kiddie costume parade would be finished by the time I got there.
"I see one ... a kiss ... it's on the floor over there," I said as I pointed over her shoulder.
"Where?" she asked as she turned to look. I could always fool my sister!
"Right here," I answered when she turned back and my lips found hers.
"Don't, we agreed, we're not supposed to do that anymore," Jen gasped when our lips broke apart thirty seconds later.
"You can't give some poor teenager just one little kiss when he's got all dressed up in his best Halloween costume for you." My hands, cradling her bum, were definitely not going to let her escape.
"You're poking me with that thing," she complained even as she moved tighter up against me. Her eyes, staring up into mine from three inches away, were shining.
"You never complained when I poked you before," I teased.
"That was before," Jen answered. A second later her tongue was in my mouth. It had been over five weeks since the last time we'd kissed like this. Neither of us could hide the urgency of our need as our tongues dueled wetly. Jen's hand slipped down between our bodies. My hands squeezed her ass.
"It's in the way," my sister said, complaining again as she tried to negotiate her way to my penis. The belt holding the strap-on plastic penis in place almost completely covered the flesh colored thong which was all I had on under the trench coat.
"I'm sure you'll find a way," I said as I quickly bent and then lifted up her into my arms. A second later I was carrying her down the hallway leading to her bedroom.
"You're terrible," she said as her arms snaked around my neck. "A bad, bad boy," she added, then ran her tongue up my cheek and into my ear.
"Jesus," I groaned as I pushed her bedroom door open. One of her hands had slipped under the strap-on and found the real thing. And grabbed him.
Wouldn't you know it, baby Natalie started crying at about the same time that my sister's back landed on the bed.
"Oh no, not now!" Jen complained the second she heard her daughter's lusty yell.
"Do we have to go?" I asked as I quickly slipped both the strap-on and the thong down my legs. My cock, ready to go, popped up against my stomach.
"She's hungry. She won't stop until she's fed," sis said wistfully as she made to get up. Her eyes were locked on my cock. The real one.
"I'll go get her," I finally said resignedly after a moment's hesitation, then turned and started for the door. "You play with this while I'm gone," I told her as I tossed the strap-on into her lap.
"Don't go undressed like that, not naked, not in front of the baby," Jen squealed. Like a three and a half week old baby was going to be offended by seeing a naked man I thought to myself as I entered Natalie's room. My daughter stopped crying the second I lifted her up into my arms. She was the most beautiful baby in the world. Which I told her as I carried her back to her mother's room.
My sister had extricated herself from her costume and was sitting naked with her back up against the headboard of the bed when I returned to the bedroom with the real little princess in my arms. "Colin hates that," Jen said as she took her daughter from me. A millisecond later a pair of hungry lips had latched onto one of her mother's fat teats.
"Hates what?" I asked as I sat down on the bed next to her. Colin was Jen's husband.
"Not hates," Jen amended. "But it pisses him off that Natalie always stops crying the second you pick her up and she doesn't for him."
"She's smart. She knows who's important, knows who her real daddy is," I said as I gently caressed the little head that was suckling at her mother's breast. Natalie was not paying any attention to what we adults were saying. Instead she was concentrating on food. But it was true what Jen had said. Of all the family members who'd been in close contact with her since her birth, and that included Colin, her two sets of grandparents, Colin's sisters, and various other family members and friends, it was only her Uncle Jim who could calm her instantly.
"A crazy uncle who wanders around his married sister's house with an erection," Jen scoffed.
"And who caused the erection?" I asked back as I picked up my sisters free hand, the one that wasn't supporting her daughters head, and moved it so it was touching the tip of my cock.
"Not in front of Natalie!"
"He missed you," I answered as I continued to hold her hand against me.
"HAH! I'll bet you've been putting the poor thing in that slut Rose every night."
"He only loves you."
"So you say."
But it was true. For both my cock and myself. There was only one person in the world we truly loved. And she was sitting next to me on the bed. Naked. Feeding our daughter. And Jen knew it.
"You know Jen, I'm hungry too," I said as I released her hand. But instead of moving it away from my penis her fingers moved to circle it.
"Well you can't have any," she said as she squeezed my hardness.
It had been over three weeks since my daughter had been born but up to that night I still hadn't tasted her mother's milk. I'd wanted to but the opportunity just hadn't presented itself. Colin had stayed really close to home during the last week of Jen's pregnancy and during her first couple of weeks home. And invariably someone else had been visiting whenever I'd dropped in.
Of course I'd seen Jen feeding her daughter although usually it had been with her using one of those privacy veil things. Only once had she given me the full show. A week earlier. When, while Jen was feeding Natalie, for just a couple of minutes Colin and his mom had gone out of the room and down to get something from their basement. Jen, her eyes never leaving mine, had lifted the veil and let me watch.
"They're beautiful ... you're beautiful," I'd intoned almost reverentially.
"I'm fat! And my breasts are huge," she complained as she cupped the one her daughter wasn't feasting on and lifted it up. No male in the world would describe my sister as fat. Or insinuate in any way that her breasts weren't perfect. Whether full of milk or not.
"I want some. Want to taste you," I'd whispered.
"I only have enough for Natalie," my sister had answered that night. And before I'd had a chance to argue the point I'd heard her husband coming back up the stairs. Jen had dropped the veil back in place. And I, who'd been sitting on the edge of my seat, slumped back into the soft upholstery of the chair. I'd had to put my hands in my lap to cover my erection.
Tonight, with Colin out of town on a three day business trip, his first since Jen's delivery, I'd decided that I was finally going to taste her. So, after yours truly had burped the sweet baby and when Jen had finally settled her daughter back in her bassinet, I approached my sister with a determination born of the long wait I'd endured.
She understood my intentions immediately. "You can't, I only have enough for Natalie," Jen instructed as she tried to sidle away from me.
"It's our anniversary!" I announced as I put my arm around her. Her bed was far too small for her to get away from me. "And you're wrong about not having enough. In fact," I told her as I cornered her against the headboard, "my experts tell me that the best possible thing to happen to any mother would for her to be regularly milked by a hungry man."
"Yeah! And who are your experts? Other pervy little brothers like yourself? Little boys who want to put their penises in their big sisters."
I just continued on. "They say that the more that gets sucked out of you the more you produce."
"That's not true." In fact, even though I was using the argument to buttress my case, it was true.
"I checked. On the Internet. In a book on proper lactation practices." I moved the hand I didn't have around my sister's shoulders onto her breast.
"You're making that up aren't you?" I cupped it. Gave it a gentle squeeze.
"Don't you want Natalie to have the freshest milk?" I asked as I watched a drop of milk form at the end of her nipple. My finger snatched it and caught it before it could fall. A second later my finger was in my mouth.
"My milk's fresh." Jen let out a soft moan as the words escaped her mouth.
"Doesn't Colin do it?" I asked as my hand returned to my sister's tit. "Doesn't he kiss and suck his wife's beautiful breasts?" Jen shook her head no.
"Hasn't he put his cock between them? Fucked their milky fullness?" I asked as I started to massage and caress her.
"Pleeease Jimmy," Jen pled as I moved my attention to her other breast.
Jen groaned out a long desperate, "ooooohhhhh" when my lips clamped down upon her straining teat. That first stream of a mother's milk, immediately released when my palm squeezed down on the breast I was suckling, splashed into my mouth in a torrent.
For a second I released her nipple. "Happy anniversary, I love you," I whispered, then reached up and kissed her lips. She tasted her own milk on my tongue. Seconds later I'd reattached myself to her teat. Sucked. Swallowed.
And the taste, the sweet aroma, released some hitherto unknown need deep inside my brain. My lips started to move urgently, instinctively remembering the proper moves from nineteen years earlier.
"Please baby ... Jimmy! Not so hard ... slower ... I can't..." My sister groaned. I wasn't listening. In fact I didn't even notice it when Jen's fingers slid down across my stomach and onto my cock. A straining cock! I was totally engrossed in stuffing as much breast and milk as I could into my mouth. Devouring them.
Eventually the urgent signals my penis was sending frantically to my brain finally registered. I released Jen's breast. Looked down. Her hand was going about a hundred miles an hour in my lap.
"Jesus Jen." It was my turn to groan. I finally had to abandon my meal. If I hadn't my cock, which Jen had been tugging at even harder than I'd been sucking her nipple, would have exploded. I wanted to deposit my first ejaculation, always the biggest one, inside her, not all over her hand and fingers. She was moist and open when I moved my finger down her slit. A second later my cock entered her.
And as my penis slid up her sheathe, as every inch of my hardness was swallowed by her welcoming cunt, both of us moaned out our pleasure. In spite of who we were, of what we were doing, it had been like this every time I'd pushed my cock inside my big sister. An instantaneous reaction from our bodies. An 'oh my gawd YES' feeling that echoed through both our brains.
My cock knew it was home. That it was in the place it had been made for. That there was no other vagina in the world in which he'd fit better or receive more pleasure.
And Jenifer's cunt knew that no other cock would ever give her more pleasure than the one that was in her. That no orgasm would be better than the one my cock was going to ignite in her. Siblings? So what? Our bodies didn't care.
"I've missed you so much," Jen said as I started to move inside her.
"Yeah but you sleep with Colin every night," I mock complained as I started to move my hips. We were in the standard missionary position.
"Colin and I haven't done it since the baby was born," Jen answered as she locked her legs around my back.
"Is he crazy?" I asked.
"He's worried that I'm not ready yet. That I'll still be sore from the baby. That my vagina will be too loose."
"Fits perfectly. Tight as a drum," I complimented as I continued to slide my cock in and out of her. "Mind you he isn't quite as big as your little brother."
"Little brother? You're huge tonight. Even bigger than usual."
"Complaining?"
"I love you," she answered, then found my lips with hers. It was a hard needy fuck. It had been far too long. She came quickly and easily. My penis anticipated her and was ready, spurting out a thick strand of hot cream just as her orgasm struck. Our timing was perfect as each of my cock's urgent outpourings was met by an orgasmic spasm that rippled down its length.
"Oh baby ... oh my beautiful little baby brother," she moaned out as our bodies quieted. But I was still hard even as the two of us panted out the denouement of our incestuous act.
"You can take him out now," Jen said when her breathing finally approached normal. I couldn't miss the challenge in her voice or the twinkle in her eyes. There was no away in the world she wanted him to leave. And she knew I wasn't planning on it anytime soon.
"As if you want me to," I said as pushed even deeper inside her. "Always taking advantage of your poor little brother. Taking his sperm."
"As if there was ever a shortage. I'm already full."
"I'll make you even fuller," I promised as I restarted my movements. It was slower the second time. Easy. Fun. Interspersed with kisses. Touches. Smiles. By now we knew every secret of the other's body. Every place to touch ... every word to say.
"He can't do that," she said after our second orgasms. I knew she was talking about her husband. Knew that Colin had never been able to come twice inside his wife without softening, without pulling out to recharge.
But what Jen and I had wasn't now or never had never been about Colin. We didn't ever really talk about him. He had nothing to do with our love. He wasn't part of our secret world. Never would be. And I knew that some day he wouldn't even be in it.
"So what do you think you're doing now?" Jen demanded as she looked up into my eyes. By then I was sitting lightly on her stomach, most of my weight being borne by my knees which flanked her body. My cock, sticky, semi hard, was resting between her tits.
"What would you like me to do?" I teased as I grabbed my penis and ran it up and down the sides of her breasts. I brought its sticky head to each of her nipples. Then put him back in her warm, breastly valley.
"Don't, please Jimmy, we've done enough already," she begged as I palmed each of her breasts in one on my hands and pressed them together, trapping my penis between them. I started to slowly move my hips, pushing my hardening shaft between them. Droplets of milk, first forming at her nipples and then sliding down into the valley, lubricated my shaft as I fucked her tits.
Minutes later, with my throbbing cock now covered in milk, I directed it to my sister's mouth. She opened her lips. "It's my turn to feed you, some sweet Halloween cream," I whispered as my penis started to spurt. Jennifer swallowed every single last drop.
"Are you staying?" I nodded yes. "All night?" I nodded again. "I love you," Jen whispered as I engulfed her in my arms.
We made love one final time before we broke apart exhausted, both of us drained. Then we fell asleep in each other's arms. Natalie, my lovely daughter, woke us just after three, hungry for another feeding. She definitely got fresh milk!
I fucked her mother again after my daughter had finished feeding.
The Past – Growing up together
So, when did it start you might ask. How is it that a nineteen year old teenage boy became the lover of his five years older sister? Why did a happily married bride let her brother impregnate her?
Or did it start before she'd married? Well...
There is a picture on the first page of one of our old family albums, the album in fact that my parents started on the day I was born, that shows a little girl, all dressed up in her finest dress, sitting in a chair in a hospital room and holding a baby in her arms.
Yes it was Jennifer and I! It was our first meeting. And looking at Jen's eyes in the picture it's clear even all these years later that it was love at first sight. A bond had been formed. What culminated eighteen years later started that very first day.
My mother has a hundred stories she tells about those early days. Amusing stories about Jen and me and the special relationship we had from day one. And there are the pictures from those first weeks and months. An endless series of shots. Jen changing my diapers. Holding me. Kissing me. An album full of them.
And mom always embarrasses Jen when she brings up the famous 'milk' story.
"I did not," sis always declaims when mom describes how her five year old daughter tried to emulate her mother and feed me. How mother had come into my room one day and found Jen holding baby Jimmy to her breast.
"He's hungry," the little girl had told her mother. Mom had started smiling. And then had told her daughter that someday she'd have her own baby to feed. Mom just didn't know then that it would still be me who'd be looking for Jen's milk!
In many ways I had two moms growing up. Certainly in the first six years or so of my existence. I followed Jen everywhere. She doted on me. I reciprocated by giving her my unconditional love.
Jennifer walked me to school on my first day of kindergarten. While holding onto my hand and giving me advice all the way. This after she'd tied my shoe laces and combed my hair before we'd left. She was waiting outside the schoolroom door when the bell rang at 11:45.
I combed my sister's hair for the first time on her eleventh birthday. May 5th 1999. Officially combed it I mean. Jennifer has beautiful hair! Always had. Even in the first picture of us together on the day I was born you can't miss the then four and a half year old girl's wondrous tresses. Rich, thick flowing hair that curled over her shoulders and then halfway down her back. Hair that literally danced with every step she took.
My mother had suggested the gift when I'd asked her what she thought I should get Jen for her birthday that year. "Her old hair brush is almost finished, she'll need a new one soon," mom had answered. So the two of us had gone out shopping for a new one. Mom figured we'd just get Jen one of those three dollar plastic ones.
First we'd gone to the local pharmacy. I wasn't impressed by the selection. "But honey," mom had said with a sigh as we'd stood in the hall lifting up brush after brush, "it's just a brush. Jen's only eleven."
"These aren't good enough for her," I'd answered, then asked her where you bought the best hair brushes in the world. Mom had laughed. But then, after minutes of begging on my part, she had led me to her hairdresser's salon down the block.
"I want to know who makes the best hair brush in the world and where can I get one?" I announced to the bemused owner after mom had introduced me.
"Mason Pearson brushes are the very best but they're very expensive young man," Matilda the owner had replied as she'd patted me on the head while smiling over it at mom. "But I've got some nicer ones that are cheaper," she offered. She didn't know me!
In the end I bought a Mason Pearson one. A long, ivory handled brush with the finest blend of boar bristle and nylon and especially designed for young girls with long hair like Jens, it cost me ninety-one dollars! It emptied out nearly every cent of my savings account, an account that had been laboriously built over the years with birthday and Christmas gift money from grandparents and aunts and uncles. But looking back now I can honestly say that I've never received as much pleasure and return from any item I've ever bought since.
"Ohhh my gawd!" I was engulfed in my sister's hug. "I love it. Love you," my sister squealed the second she'd opened my brightly wrapped birthday gift. Her hug made my day. The money I'd spent was immediately repaid. But it was just the first installment.
"Is it okay?" I was peering in through her doorway. It was hours later. The birthday party was long over. Jen was sitting at her vanity. Facing the mirror. I'd watched three or four strokes of the new brush before I'd said a word.
It was a ritual I'd seen Jen perform many times before. However I'd always been an observer, never a participant. Jen caught my eyes in the mirror. "It's perfect. Would you like to try?" she invited, then spun her chair around and offered me the brush.
"I wouldn't know what to do," I said nervously even as my fingers accepted the brush.
"Then it's time you learned. Now that I'm eleven I'm going to need someone to help me with my hair. It's a big job you know."
I tentatively ran the brush slowly through the bottom of her long mane. "Longer strokes, from the top," Jen instructed as she reached back and guided my hand.
"I don't want to hurt you," I answered without taking my eyes off the brush. I took a few more tentative strokes. "Was that okay?" I asked as I lifted my head and found Jen's eyes in the mirror. "The lady at the store said it was the very best brush you can buy," I said as I resumed combing.
"You're my very, very favorite brother you know."
I looked up again. Jen was smiling. "I'm your only brother."
"I love you." I blushed. Then continued combing.
"Does that mean you'll marry me some day?' I finally asked shyly.
"You know maybe I will," Jen answered. Jen was eleven that day. I was six and a half years old. I can remember that night as if it was yesterday.
The hair combing became something of a routine for the two of us after that night. I didn't do it every night of course but at least once every week or ten days I'd end up in her bedroom combing her hair. And as I did we talked. About everything and nothing. Secrets. Our lives. We developed an intimacy in our conversations extraordinary for two siblings so far apart in age. Somehow the act of combing allowed us to transcend the incongruity of our words.
My father and my mother separated that year. And the night we were told I spent half the night brushing my sister's hair. At various times that night both of us had tears on our cheeks. I'd comfort her and then seconds later I'd start sobbing. Then she'd comfort me.
At the time both Jen and I blamed dad. He'd left us. For another woman. Deserted mom. Deserted Jen. Now, at nineteen, I have a somewhat different view of my father. I'd refused at first, as had Jen, of having anything to do with him. But slowly over the years we've reestablished contact and if I don't even now have total respect for him I do love him in the ways every son loves his father. Seeing him in the stands cheering me on at my various ball games, talking to me afterwards with his hand around my shoulder, tossing the ball with me on a Sunday morning had slowly chipped away at my hostility. And mom, understanding the needs of young boys had not only allowed it but had somewhat encouraged it.
But while I had allowed him into my life Jen never had during her high school years. Any rapprochement would have to wait until she was much older.
Of course I must have become a real pest to Jen at some point or another. All boys are. And I'd been a typical nine and ten and eleven year old boy. Wild, rambunctious, always getting into trouble ... a hellraiser ... a continual trial for both my mother and Jen. Except somehow I never was for sis. And I can't remember her ever getting really angry at me. The hair brushing bull sessions seemed to always ease away any and every problem between us.
I was almost twelve, in Middle School, and Jen was sixteen years old and a High School sophomore when perhaps one of the most important events in our relationship occurred. It was the first precursor of what was eventually to come. Not that we knew it at the time. It was a Friday night. Relatively late – I was already in bed and had been asleep. I awoke, my sleep interrupted by a door opening and closing loudly.
And it was only because I'd had to pee upon awakening that I heard her. Jen. Crying. I heard the sobs as I started to walk back towards my bedroom from the can.
"Jen?" Whispered after a gentle tap.
"Go away," came back. A hissed order.
Of course I opened the door anyway. No one, and I mean no one was going to make my sister cry without me finding out why.
"What is it? What happened," I asked as I penetrated the gloom of her darkened room.
"I'm okay," whispered back. I flicked on the bedside lamp. Tears were cascading down Jen's cheeks. I sat down next to her and put my arm around her. She didn't say anything for about twenty minutes. Somehow, even at that age, I knew enough to not say a word. I just held her.
"I'm okay," she finally said as she wiped the tears off her cheeks. I gave her the quick 'are you sure' look.
"Promise ... and thanks," she said softly, then gave me a hug and quick kiss on the cheek. I was being dismissed. Nicely of course but still dismissed.
"You know I could comb your hair," I offered as I stood tentatively between her bed and the door. I instinctively sensed that I should stay.
Louise
- 16.03.2021
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