Jerry and Jenny Ch. 01: Pinky Promise

This is my fourth submission in this particular area of Literotica, and is quite different from many of my other stories.

I would like to thank those who have offered comments and constructive criticism on my previous stories, and those who have patiently waited for this addition to the story.

And now, the disclaimers:

For those who want to say this or that would never happen, remember this is my universe, a place where nearly anything can, and often does, happen. At least on paper... In addition:

1. Characters in this story may participate in one or more of the following: Smoking, consumption of adult (meaning, alcoholic) beverages, utterance of profanities.
2. All sexual activity is between consenting adults 18 years of age or older.
3. Statements or views uttered by the fictional characters in this story do not necessarily reflect the views or opinions of the author.

Please refer to my profile for more on my personal policy regarding comments, feedback, follows, etc. (Yes, I DO moderate comments) And please remember, this is a work of fiction, not a docu-drama...

...

September 2073:

I hate funerals. Always have and always will. This funeral, though, is the absolute worse. Hopefully, it will be the last funeral I ever attend next to my own. The reason is simple. The woman in the casket being laid into the ground is -- or was -- the love of my life.

Her name was Jennifer Conrad, but she went by Jenny. She was my best friend, my loyal confidant, the woman who made life worth living. She was also my twin sister. Me? I'm Gerald Conrad, but everyone calls me Jerry or Jer.

I shed hot tears as her casket was lowered. A part of me wished I could trade places with her. After all, I thought, she deserved to live far more than I. Don't get me wrong -- this was expected, and both of us knew this would happen sooner rather than later. Still, it hurt like hell to witness it, knowing the rest of my life would be empty. No more laughter. No more smiles. No more kisses. No more... anything.

For the last year or so, she had fought off one malady after another. I guess that happens when you get to be our age. The final straw was the day she was diagnosed with a rare form of pancreatic cancer. The doctors all told us there was no cure -- nothing to do but wait and try to stave off the pain. So they put her into a hospice, and that, as they say, was that.

I spent every waking moment in her room. I read to her, held her hand, watched television with her, cuddled up in bed with her. I generally did my best to make her final days as happy and comfortable as humanly possible. Even though she was in pain the whole time, she never complained.

The service was lovely, and everyone offered their condolences as they left. Exhausted, I sat down on a nearby bench, and pastor Bob sat down next to me after everyone had left.

"I hate funerals," he said quietly. I looked at him, surprised.

"I was thinking the same thing myself," I told him. He chuckled at that.

"You know, when you go to school to be a pastor, they teach you all these fancy things to say at times like these. To tell you the truth, I don't think there's anything anyone can say to ease the pain of a lost loved one," he said. "Sometimes, I think it's better to just say nothing."

"I think you're right," I said quietly.

"You two were together a long time," he said. "What, 50 years?"

"Fifty-two years, four months, 17 days," I said. "But who's counting?"

"That's six years longer than I've been alive," he said. "You and your sister must've really loved each other to stay together that long." I looked at him, surprised that he knew. As far as most everyone in the church knew, we were married. No one ever asked, and we never said otherwise.

"You knew?" I asked. He nodded his head.

"Yeah," he said. "I saw the way you two interacted. I saw the love, respect, and devotion the two of you had for each other. Figured it wasn't my place to judge. You were both happy, so who was I to say anything." That was one of the reasons Jenny and I started going to this church 20 years ago. We had heard the people there were very friendly, open-minded, and non-judgmental.

"You going to be okay?" Bob asked after a few silent moments. I shook my head.

"I don't think I'll ever be okay again," I said.

"You loved her with all your heart," he said. "That's normal. Just know that we all loved Jenny. And we all love you as well. If you need anything -- anything at all -- even if it's just sweeping the floor -- you call me. Got it?" I nodded my head. He handed me a card.

"What's this?" I asked.

"It's a group that gets together a couple times a month at the church. Widows, widowers, others who have lost loved ones. A good chance to grieve with others," he said. "They get together, have a small meal, socialize, reminisce. Cry on each other's shoulders. That sort of thing. Better than moping around the house by yourself all the time."

"Thanks, I'll consider it," I said.

"Do that," he said. "And yes, whether you want to believe it or not, you'll be okay. C'mon, let me walk you to your car." I got up, and he walked with me to my car, a 1975 Trans Am I had restored several years before.

It was white with a sky-blue interior and sported a 400 cubic inch engine. It was a rare find these days, what with everyone driving electric or hybrid cars. I didn't take it out often, but there were times I just felt the need to open her up and let the wind whip through what was left of my hair. Jenny bought it for me as a present over 30 years ago. At the time, it needed a lot of work, but I enjoyed putting it back together. I'll never forget the first time she rode in it with me. But that's another story for another time.

"I can't believe you're still driving this old thing," he said. "It must be what, 100 years old?"

"Almost," I said.

"Must cost a small fortune in gas," he said.

"I don't drive it every day, but I do like to take it out now and then. It gets me around," I said. He chuckled.

"I'll bet it does," he said. We said our goodbyes, and I headed home, Credence Clearwater Revival emanating from the speakers as tears fell down my face. I pulled into the garage and shut the door before wiping my face. Going inside, I couldn't help but notice how quiet the old place was. It was rather... eerie. I almost expected to see Jenny rattling around in the kitchen, but of course, she wasn't.

I made a pot of coffee and went to the living room, where I sat down and looked around. I had lived here my whole life. My parents passed it down to us when they died, and we just never had the desire to sell it. Besides, the last thing either of us wanted was a mortgage, so it worked out in the long run.

I turned on the television to have some background noise and pulled out an old photo album that Jenny and I used to keep our more "intimate" memories. Grabbing the pipe she gave me for my birthday ten years ago, I filled it with tobacco and lit up before opening the album. I couldn't help but think back to the beginning of our long love story.

...

Although Jenny and I are twins, her birthday was technically December 31, 1995, while I was born on January 1, 1996. How is that possible, you might ask. Easy. She came into the world at 11:50 pm on New Year's Eve, and I emerged 15 minutes later, at five minutes after midnight. I've since Googled that and found that the average time between the first and second twin in vaginal births is about 17 minutes.

Still, Jenny liked to tease me about being born first and often referred to herself as my "big sister." I didn't mind, as I knew she meant it in a good-natured way. We had a relatively normal upbringing and generally got along quite well. Sure, we squabbled from time to time as all siblings do, but we always made up afterward.

Even though we were pretty close growing up, we were complete opposites in terms of personality. Jenny was always outgoing, feisty, and playful, and I suppose one could call her a "tease." I was always a bit more reserved and quiet.

We always shared secrets with each other. As we grew older, our conversations became more mature without being explicit. We started talking about the people we liked and dated in school, and some of those conversations were quite... interesting.

Being my "big sister," Jenny would sometimes give me advice on treating the girls I dated. Things like, what to notice when I picked my date up, what kinds of things to complement. I found her suggestions worked quite well, and I also found myself highly sought after by the girls in our class. Seems I had developed a reputation as someone who knew how to treat a girl right.

Jenny wasn't exactly a wallflower and always had guys lining up to date her. Of course, they had to pass the "brother test," and I made sure the guys all knew they would have to answer to me if they ever disrespected my sister.

I lost my virginity to Brenda Harris about two months after my 18th birthday. I remember coming home from that date and meeting Jenny in the hallway between our bedrooms. She had just returned from her date and was getting ready for bed. I'll never forget that night.

"I hope you used some protection," she said quietly. I looked at her, shocked. How could she know? Then I saw the look of sadness on her face.

"Protection?" I stupidly asked.

"Yeah. You know -- a rubber," Jenny said.

"Of course," I said.

"Good," she said. "I'm glad." For a moment, I thought she was going to start crying.

"Are you alright?" I asked. "How was your date?"

"I'm fine," she said quietly. "Date was okay. It's just... my little brother is growing up." She kissed my cheek and headed for her room. "Good night," she said before she closed her door. What's eating her? I asked myself. I knew better than to press the issue, so I headed into my room and went to bed.

Things changed after that night. Jenny was her usual outgoing, flirty self, but I noticed something about her. It seemed that she had blossomed almost overnight. In addition to being a bit of a tease, Jenny became something of an exhibitionist. She got a kick out of flashing as much skin as she could possibly get away with, especially around me. And our conversations began to get a bit more... explicit.

Her dresses and skirts got a bit shorter, and her cutoffs became more daring. More than once, I would see her wearing a short t-shirt and knew she wasn't wearing a bra, and I could easily see her nipples threatening to poke holes in her shirt. The thing is, she knew what her displays were doing to me. I knew it's not right to perv on your own sister, but damn...

We graduated from high school and prepared for college. I was going for a degree in information technology, and she wanted to be a registered nurse. Her college was in the southern part of the state, so we would be separated for the first time in our young lives. My school was right here in town, so I could stay at home.

Mom and Dad took us out for dinner the night before she left, and we had a good time celebrating. Mom and Dad went to bed after we got home, so I went into my room. A few minutes later, Jenny tapped on the door and pulled a deck of cards she always kept in her purse. We frequently played cards, so this wasn't anything out of the ordinary. She closed the door and came into my room.

I pulled the card table around as she sat on my bed, grabbed my desk chair, and sat down across from her. That's when I got the shock of my life. She was still wearing the short summer dress she wore to the restaurant, and when she sat cross-legged on my bed, I could see... everything. She had no panties on, and I could clearly see her open pussy and her thin, dark pubic hair.

"What's the matter?" she coyly asked with her trademark mischievous smile.

"You're trying to distract me," I said, glancing at her sex, which was visibly wet.

"What, this?" she asked, lifting up her skirt.

"Jenny!" I exclaimed. She gave me one of her flirty laughs as she unbuttoned the first three buttons on her dress. That's when I noticed she wasn't wearing a bra.

"You're just now noticing?" she asked. "I thought I trained you better than that. I took my panties off before we left the restaurant, and I wanted to give you something to remember me by." She reached into her purse and handed me something. I looked and saw it was a tiny pair of lacy panties. "A souvenir."

We played several hands of cards -- mostly spades and gin rummy. I had a terrible time concentrating on my hands, as Jenny kept her legs spread and would periodically reach up to unbutton her dress even further.

More than once, she reached down and stroked her pussy with one hand, causing me even more discomfort. Her B-cup breasts were entirely on display by the end of our fourth hand, and her nipples were hard.

"Well, it's getting late, and I need to get up early," she said after our sixth game. By now, she was topless, and her dress was almost completely unbuttoned. She got up off the bed and let her dress fall to the floor, and I'm pretty sure it was deliberate. "Oops," she said as she stood in front of me, totally naked. She stepped out of the dress and walked right up to me, pressing her bare breasts into my chest. She gave me a scorching hot tongue kiss as she rubbed my crotch.

"I guess my little brother isn't so little anymore," she said with a sly smile. "How big is that thing?"

"I... don't know," I stammered. This was the first time Jenny had ever done anything like this. The truth was, though, seeing her naked had a profound effect on me, and I was harder than I could ever recall. "I've never measured it." She reached into my jeans and grasped my hard cock.

"That's got to be at least eight inches," she said as she slowly stroked it. "No wonder all the girls you date are so happy. You know, if you weren't my little brother, I'd fuck your brains out right here and right now. Maybe I will anyway," she added with a smile.

"Jennifer," I hissed. She laughed and gave me another kiss as she continued to stroke my hard cock. I felt drops of precum at the head of my cock, and she wiped it with her hand, then raised it to her lips, licking it off while looking me in the eye.

"Yumm-oh," she whispered.

"You're so naughty," I said.

"You have no idea. Never forget, little brother. No one loves you more than I do," she said, giving me another kiss. "Good night." She stepped back, picked her dress up off the floor, grabbed her purse, and went into her room without bothering to cover up. She smiled and blew me a kiss when she closed her door.

Here I was left with the worst case of blue balls in history -- caused by my own sister. Damn, I thought. This just wasn't right. I dreamed of Jenny, naked, riding my hard cock to orgasm that night.

I helped her load her things the next day, and we said our goodbyes. Mom and Dad had tears in their eyes watching their daughter prepare to leave. After a tearful farewell, I walked her to her car, and I knelt by her door after she got in.

"Remember what I told you last night," she said. "I love you, and I always will."

"I love you too," I told her. We gave each other a kiss. "Be safe. Take care of yourself, okay?"

"I will," she said. I had tears in my eyes as I watched her pull out and head for school. We stayed in touch all through college. Email and instant messaging made it pretty easy to do. I never did get the image of her naked out of my head.

We dated other people during college and told each other about our dates and experiences. She continued giving me advice, which I readily accepted. We had a terrific time catching up when she came home for the holidays.

We never repeated that night before she left for college, which was probably a good thing, as we probably would've ended up sleeping together if we had. But we had a lot of extraordinarily frank and explicit discussions about the people we dated. And it turned out that Jenny had become even more of an exhibitionist in college.

Our schedule was such that we could never take spring break together, but we always sent each other videos of our adventures. One year, Jenny sent me a video. She participated in an explicit contest that involved the "intimate" use of beer bottles.

I was shocked to see my sister get completely naked in front of an entire group of people, and I was even more shocked when I saw that she had shaved her pussy completely bare. Then I watched as she spread her legs and let herself get fucked with a beer bottle. When the guy holding the bottle stopped, she grabbed it from him and began fucking herself with it until she squirted all over the bottle, causing those around her to applaud wildly.

"That's for my little brother," she said when she pulled the bottle out of her dripping pussy. She smiled and blew a kiss into the camera. I knew this was for me, and I nearly came just watching.

"You are such a naughty girl," I told her in an email.

"I have not yet begun to get naughty," she responded with several emojis. Sure enough, I got an email from her a couple of months later with another video.

"Enjoy," the email said with smiley-face emojis. This time, Jenny and a friend, Alexis Johnson, had gone to a park not far from a local freeway. The video started with Jenny introducing her friend, who turned the camera around. Alexis smiled into the camera and waved.

"Hey, Jerry," she said. "Good to meet you." She turned the camera back to Jenny, who smiled before she spoke.

"It was such a nice warm day out that we decided to come here for a bit of fun," she said as she put a large blanket on the ground. "Actually, I got a bit horny, so I told Alexis I wanted to fuck myself outside. But only if she would make a video for you." She held up a penis-shaped dildo with a large base.

"It's not quite as big as you, but I think it'll do the job," she said in the video before setting the thing down. Then she started taking her clothes off. Her t-shirt was the first to go, then her tiny denim shorts. Then she pulled her panties off, and I could see she was still shaved.

"How big is his dick?" Alexis asked.

"At least eight inches," Jenny said.

"Wow! I'd love to try that one of these days," Alexis said, causing Jenny to laugh. "So, is this guy your boyfriend or something?" Alexis asked.

"My little brother," Jenny said.

"Your brother? You're getting naked to fuck yourself in public for your brother? Ooh, that's kinky, girl," Alexis said, laughing. Jenny laughed with her then turned back to the camera.

"You know, I like to be completely naked when I fuck myself," she said with a smile. She pulled her shoes off and knelt down next to the dildo. She picked it up and licked it, just like she might a real cock, then set it back down. "Watch this," she said as she positioned herself over it.

I was shocked to see her actually fuck that dildo, right there in the park, where anyone could very easily see her. Her long, dark hair bounced as she went up and down on that thing. She moaned as she fucked herself.

"Go ahead, Jer," she said. "Whip out that big dick of yours and stroke it for me. Do it. This feels so fucking good." Watching her, totally naked, fucking herself on that big dildo got me excited. I have to admit, it was the sexiest thing I had ever witnessed. I did as she suggested and climaxed at the same time she did in the video.

She climbed off the dildo and looked around at the cars zipping by on the freeway. Jenny laughed at something Alexis said and held up the dildo. Alexis zoomed in on it, and I could see her juices covering the thing.

"That was so much fun," Jenny said. "We ought to do this together someday. Talk to you later. Love you!" She smiled and blew a kiss at the camera before the video faded to black. I sat there, stunned. I couldn't believe I just watched my sister do that, right there in public. Moreover, I couldn't believe I just jacked off to a video of her publicly fucking a dildo. We talked about it the next time she called.