Life with Jenna
Introduction:
My amazing sexy sister
When we grew up she married twice and had one kid. Both her husbands were handsome, they both were charmers, I liked them both, but they both turned out to be cheaters. I was married only once, but I had two kids. My wife came from a family of heart disease victims, and she died very early. It took a while for me to get over it, but the kids helped. I knew I had to be there for them.
Jenna was through with men after her second marriage.
When I say that she was gorgeous, she was gorgeous. Not so much her face, but her body was perfect. She was an organic food fanatic, and she did yoga and a lot of aerobic exercise. She was fanatic about her looks. It showed. She turned men’s eyes, just walking down the street.
After I finished journalism school I got a job where I could be on my own. I would crank out three columns a week on my laptop reviewing the news of the Middle East . I just had to make sure I got my columns in before the deadlines. As the Internet grew, I could get all my sources online. It was tricky work — I had an exacting boss — but essentially my time was my own.
Jenna lived about 20 miles away. She had turned into quite an artist, and she was a natural on a sewing machine. After starting to make all her own clothing, she decided to turn it into a business. She would go down to Beverly Hills with a sketch pad, draw the dresses she saw in the windows of the fancy posh stores, and then crank out the same dresses on her sewing machine. And that’s how she made a living, and it was a pretty good living.
I visited about once a week and my sister always turned me on. We would go shopping and I made it a hobby to look at all the guys turning their heads to look at her. We would go swimming in her pool and afterward, I would dig into her back with my knuckles to get her relaxed. She worked very hard. Touching her turned me on. We never discussed it except once when I leaned up against her and she said, “Tommy, you’ve got a hard on.” It caught me by surprise and all I could manage to say was, “Well, look who’s turning me on.” And the subject matter was dropped.
It did not surprise me that she caught something bad because she worked so hard, but she caught pneumonia, and I brought clothing over to her place to stay and take care of her. Once the doctor pronounced her non-contagious, I started up her back massages, which she always loved, and which I loved giving her. I could feel her tense muscles slowly melting away and softening up. I could feel her getting tired, and sometimes I would sit down on the bed to rest and she would snuggle up against me, and fall asleep that way.
We were sitting at the supper table after she got well and I was ready to leave, and she said to me, “Tommy, stay here. It feels so good having you around. You wouldn’t have to put in much rent money. We’d both save. I’m going to open up a dress shop and I’ll need someone to help me get it together. You’d be perfect around here.” I couldn’t argue. I was thinking of it too. I didn’t have much by way of baggage. And so I moved in with Jenna.
And that evening, massage after supper and yoga and exercise became a standard part of the routine. One day I told her to take it all off. Her bra straps got in the way. Her panties got in the way. And she did. From then on, I could go up and down her back, right down her ass, and then continue down her legs. And that got to be part of the routine. She had bought a massage table and it was perfect, because she had a place to rest her chin and face. Once in while, as I leaned up against her to reach to the other side of her body and my hard cock touched her body, she would rub it for a second and say, “I’m glad you like me.”
One night, Jenna startled me. After her back rub she got on her bed and there in her gorgeous nudity she said, “Sit down, Tommy.” And continuing after I sat down, “You do so much for me without asking for anything back. I’m beginning to feel like a rat. You are so different from Donny and Mitch. They always wanted something. I always felt as if I was on the spot. With you, I feel as if you add to me instead of suck it away.
I practically fainted when she said the next thing. “Get your clothes off and fuck me. I know you’ve been wanting it. I’ve got news for you, little brother, I want it too.”
My brain was short-circuited. “But you’re my sister…”
“Get your clothes off.”
I really didn’t want to “fuck” her. I loved her. I wanted to make love to her. How could I explain? But I got my clothes off. And then, lying down next to her, as her arm circled around my back, caressing me, I nearly came then and there, and I had to fight it.
And then I got my sanity back. I knew what I wanted and I was going to get it. I got up on all fours and gently slipped the tip of her nipple into my mouth, and gently began sucking on it. One hand rested on her belly and began caressing it in a round motion. I could feel her body slowly dissolving into relaxation. Then, I lifted my head up to say, “I love you little sister, I have loved you since the day I was born, and I love you more this minute.” And my lips gently came to rest on hers. Involuntarily, her hand began rubbing my belly as our tongues intertwined. And when I lifted up my head, she said, “Why did it have to be Donny and Mitch? Why couldn’t it have been you?”
“Who gives a damn? That was then and this is now.” And my lips again gently came to rest on her magnificent erect nipple, and this time I began sucking in earnest, as my hand rubbed her belly in circles, reaching further and further down. Her breathing became deeper and more regular and sometimes, her body would quiver. That was exactly what I wanted. She couldn’t get it together to rub me, meaning that she was getting turned on hard.
And finally that hand began touching pubic hair, and it was wet. And lower, and her pussy was dripping wet. That was exactly what I wanted. My forefinger and middle finger slipped inside as my thumb came to rest on her clitoris. In the next half hour I got a lifetime’s worth of education.
The second my fingers were in her and my thumb on her clitoris, she began shivering. She lost all control. And she came. As I looked up to see what was happening I got a face full of her pee. And her shivering and jerking continued for the next minute until she began to quiet down.
But not for long. She was on her way to number two. I just got into a routine of putting my mouth where it made her shiver the most, while I squeezed inside and outside. And it took another minute for her to come again.
And this happened again and again. I realized then that I could kill her by not letting up. She would die of heart attack or exhaustion. I loved her so much I could hardly stand it. After about ten minutes I stopped.
It took a couple of minutes of quiet time, and she finally said, “Thanks. I needed a break. For God’s sake, stick it in. I can’t stand it with you outside me.”
I didn’t need an invitation. My cock must have been about eight inches hard and long, and it slid inside Jenna as if it belonged there. I didn’t want to move it. I wanted it to be in her as long as possible before I came and she caught on immediately. “Do you have any idea how many years I’ve wanted you to do this to me?” Before I could even answer she put a finger on my lips and continued. “When it was all over with Mitch, when he was fucking me I would imagine it was you. That was the only way I could come, and lots of times I didn’t. I knew that if I ever fucked you I wouldn’t be able to stop coming. And that’s exactly how it’s turned out.”
“Oh, sis, I wish I’d known.”
“You couldn’t have done anything. I had to get rid of him and get through hating men, and then figuring if I ever had a lover it would be someone I really loved. And it’s you. I love you, Tommy.”
And then I began feeling strange pulsation inside her as she planted her lips on mine and rubbed my back. She was squeezing inside and I can’t even describe how it felt, it was so powerful. Our tongues intertwined and she stuck hers as far inside my mouth as she could. Tingles ran up and down my back. Her fingers rested on my ass, and her middle finger dug into my hole. It was too much. My cock began pulsating with cum, over and over again, as I squirted my love deep into her. And then she lost it.
She began cumming all over again. I could feel her hot pee around my cock. Somehow, I hardened up again, and began moving it in and out. She couldn’t stop cumming. Somehow, after that first cum I found enough to cum a second time, and she came even harder.
It ended up with me cumming four times, and she never stopped, and her sheets became drenched with her pee. I think we could have gone on all night, but I would have ended up with a dead sister. An hour and a half was plenty.
She said, “Do we go into your bed?”
“No. We’d have to shower first.”
“We sleep here?”
“Yup. I won’t mind so long as I’m inside you.”
“You’re a crazy brother but I love you.”
And that’s how we spent the night, side by side with my cock stuck in her pussy. We were too tired to move. We woke up to a pretty smelly bed. The blankets and sheets could be washed, but the mattress was a goner. That pee had soaked way inside.
The next morning we showered together and it was all we could do to keep from going at it again. I worked hard all morning long and got my news items in early. In the afternoon we shopped for a mattress and rubber sheets. And my resourceful sister sewed the rubber sheets together so they fit a queen-sized bed, and under queen-sized blankets. And that night it was the same thing all over again, fucking like crazy and ending up wiped out, with me falling asleep with my cock inside her.
That was forty eight years ago. Sometimes one or the other caught a bad flu and we still fucked. We caught each other’s colds and we still fucked. Always the same routine. Wake up and throw the sheets into the washer. Get into the shower. Wash each other. Eat breakfast. And at night after supper it was yoga, exercise, and later we went to bed and fucked our brains out. I never came less than twice. As for Jenna, I could never tell how many times she came because it was all one single cum. It never stopped.
Once a week like clockwork she insisted I cum down her throat. She swore it gave her nutrients she couldn’t get anywhere else. I had a big problem with it. She liked it literally rammed down her throat, and she was obviously choking. But she insisted, and she would always put a finger into my asshole, and that turned me on too hard, and I would cum into her throat. My belly was up against her face and she didn’t care. She always wanted me to finish it with a lot of pee, which she gulped down, but I couldn’t stand pissing more than a little bit down her throat. She swore my pee gave her beautiful skin. For that matter, sleeping in her pee for years did things to my skin. Around my middle my skin was smoother. No blemishes.
Jenna and I fucked every night of our lives since our first time. We never got tired of it. We had a gay neighbor, Joe, who used to come over a couple times a week. He didn’t pretend. He asked me why I wouldn’t let him fuck me while I was fucking Jenna. We were polite. The answer was no. That is…
Until it struck Jenna that if I had more than a finger up my ass I would cum harder and maybe be more willing to pee down her throat. That’s when she brought up the idea of Joe fucking me while I was giving her the weekly meal of cum and pee.
The next week, we invited Joe over. I wouldn’t get nude, and Jenna didn’t need to undress. Joe and I both took our pants and undershorts down. And then, self-consciously, I put my cock in Jenna’s mouth. I was nervous. Jenna asked Joe if he were ready. The answer, a cock shoved into my ass, and it felt big. But wait — that was just the tip. Suddenly my ass felt as if it was being ripped apart and a giant rod was being shoved into my cock, as I suddenly was jammed against Jenna’s face. The pain! It was too much for me to even scream. I could feel my cock being jammed down Jenna’s throat and I thought somehow that I must have come. And then Joe began shoving his cock in and out of my ass. I suddenly felt myself squirting something down Jenna’s throat, and it seemed to never stop. I realized it was pee. Meantime, Joe seemed to be getting bigger inside me, and it didn’t feel so bad. No doubt, that was because he was leaking and it lubricated me. And then Joe came. I had to secretly admit, I liked it. I squeezed tight on him and that seemed to make it stronger. It got me hot inside Jenna’s mouth, and I began going in and out. I realized that she was loving it, because every time I shoved it in she pulled my hips toward her, as if to bury my belly up against her face. How could she breathe? And then I came again. At least this time I knew I was coming. And I enjoyed it. Wave after wave of love cum squirting right down Jenna’s throat.
Joe asked politely if he could have another one, and I didn’t mind. That giant cock filled my ass up again, and started going in and out, and I nearly wanted to cum myself. It was then that I realized I might be bi. Jenna caught on and wrapped her mouth around my cock, licking and sucking. When Joe came in me the second time, this time I squeezed like crazy, as if to squeeze out the last drop of his cum inside me. I felt myself wishing I could have his baby. Crazy thought. His lips wrapped around one of my ears, and he bit lightly, saying, “Oh, Tom, this is heaven.”
When he left, Jenna dived at me and in no time had my shirt unbuttoned. Off came my shirt and undershirt. In a flash off came her clothing, all of it. And she pulled me down to the bed with her. And we just hugged and kissed and hugged and kissed. And of course my cock happened to slip inside her.
“Tommy, this is what I have been wanting all along. You must have poured a glass of pee down my throat. I can’t get enough of it.”
“You’re crazy. I don’t want to make you sick.”
“I’m telling you, it helps to beautify my skin.”
There was no use talking Jenna out of it because she had to have her weekly cum and pee meal. When Joe finally got a boyfriend and moved, I was pretty comfortable with it. From then on I would wait after my cum until the pee came and let Jenna suck it down.
It also had a questionable benefit. I would always get up to pee two or three times a night. One night, Jemma was awake and said, “Don’t go to the bathroom. Do it inside me.”
“Hon, it’s not good for you.”
“Let me be the judge of that.” She pulled on my cock and squirmed around so it was in her mouth. Gently stroking my back, she said, “Let go. Let it all come out inside me.” And I thought fuck it, she will just hassle me for it. And I let it loose. It really felt good coming out, and she drank it all down. Then she came up to kiss me and fussed till she put my cock inside her vagina. I had a little more pee left and just pissed it in there.
Such was life with my very unusual sister. I tried drinking her pee from a glass once, and I decided that this was definitely not for me.
She died three years ago. It was a nerve disease, and the doc had done all he could. Her kid Jojo and the grandkids, and the great-grandkids were there, in her house — she would never accept staying in a hospital — and she insisted that they all leave the room and shut the door — she had to talk to me. When they were gone, she said, “Tommy, you have to be inside me fucking when I leave here. I can’t stand the idea of dying without you in me when I’m ready to go.”
“Okay hon.” I was crying.
“Now, Tommy. I need it now.”
I got my pants off and got in the bed.
“Tommy, take it all off.” Oh oh. That meant…I took it all off, got under the sheets, and stuck it in. Sideways, next to her in the bed. She couldn’t take my weight on top of her.
The second I got it in she began cumming. Shivering and cumming. A skinny hand reached around me and a skinny finger jammed itself into my asshole. And our tongues intertwined as I pushed in and out. That finger in my asshole began doing a number inside me. I came in her just like the old days. Wave after wave of cum. And she shivered and came. “Oh Tom, thank you, thank you, thank you.” Her finger relaxed and slipped out of my asshole. She was gone. I hugged my dead sister and cried and cried.
It took fortitude to get up, wash up and get dressed, but I did, and announced to the kids that in the middle of our conversation she passed away. And then it was Jojo’s time to cry and stay with her, while I went into the kitchen and brewed up some coffee.
A while later Jojo came up to me and said, “I need to talk to you.”
“What about?”
“It’s private. Let’s go outside.”
You didn’t want to get into private conversations with Jojo because she always said what was on her mind and screw the politeness, but what could I do? We went outside.
“Did you and mom ever fuck?”
“For God’s sake Jo, she’s my sister!”
“You guys never went out with anyone else.”
“Jojo, we worked our tails off to make a living.”
“Did you ever fuck?”
“No. Never.” I put all my force into it. Jo apparently believed me because her face fell.
“Goddammit, I wish to hell you had. I never trusted Mitch.”
“You’re Donny’s kid. Naturally you wouldn’t trust Mitch. He’s not your father.”
“Mom didn’t like him either after a while. She always trusted you. You guys could have fucked a storm together.”
“Jojo, I’m your uncle. Knock off this conversation.”
“She peed like I do when she came. She told me.”
“Stop it.”
When the kids left, the four walls closed in on me, and I just cried. Burying Jenna was horrible. Sometimes I wished I could be lying there next to her.
Weeks later, Jojo came by. “Hey unc, I never saw you looking this way. You look terrible.”
“I know. I miss my sister. This place feels so empty.”
“Unc, just cool it while I say this. I know you and mom fucked. When I looked her over when I was alone with her after she died, she had pee all over her. She came just before she died. You’re a good unc.”
“Jojo, she had a urinary incontinence problem.”
“Unc, shut up.” Jojo held my hand. “You’re missing her something terrible. If you ever need to keep from going crazy, I’m available. We won’t discuss this with Robbie and the kids. I kinda think I’d like fucking you. You look as if you need it, unc.” I could not stop my tears and she hugged me, before she left. That offer helped to put me together, but I never took her up on it. She would come by every few weeks, and we would end up hugging and kissing and she would make her offer, and it felt good, but I never took her up on it. Somehow, if I did, I knew I would spill the beans and blab about her mother.
A few weeks later I started going to dances to break the solitude. That was where I met Alice, about a year after Jenna died, and we started dating. And yes, we finally made it into bed and she was a lot different from Jenna, but it was nice to have a nude woman to make love to. She did cum. She never let loose a single drop of pee. She was fussy about washing her hands. She had been a nurse. And it was okay, cumming in her, but she wondered why I had a problem with it and I explained that with a previous sex partner I was used to her putting a finger inside me. I could see the light in Alice’s eye when I said that.
Our next time in bed, Alice came with finger cots. She put one on and when I stuck my cock in her, she jammed a finger up my asshole, with finger cot. I said, “Doc, I like that examination you’re giving me,” and that night I came twice. With Alice it got to be a twice a week routine, and after a year of dating me, she moved in. She was a cleanliness fussbudget, but I took advantage of it. I pointed out that if we showered together I could wash parts of her better than she could and vice versa. That’s how we started showering together.
I knew that Alice cared for me when, after I came in her, she said, “Don’t take it out. Let’s fall asleep this way.” And we did. After that she told me, “You know, Tommy, when I’m asleep I don’t like being woken up, but if you need to get in, do it, and leave it in. And I did that too.
I live with Alice to this very day. I think my family must be highly sexed. Alice needs it a lot less, but she accommodates me. If I want it she is there for me. It is not that all-enveloping love Jenna and I had for each other, but Alice is okay. She won’t let my cock go hungry for lack of a pussy.