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Sissy

"woman comes to visit her sis and bro-in-law, accidentally finds steamy videos"

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“SISSY!” Al roared as he wrapped Cindy up in a bear hug and lifted her off her feet. Planting a big kiss on her lips, he put her down. “You look great. How was your flight?”

Since Cindy’s dad had died, Al was the only person in the world that called her sissy. Cindy had known Al since he had first started dating her older sister Debby twenty years ago, and she had always loved Al. He had an outgoing, upbeat personality, winning smile, and tall, slim physique with killer abs.

Catching up as they walked to baggage claim, Al explained that Debby couldn’t get off work to pick up Cindy, so Al was going to take her to the house. He had to go back to work, but Cindy didn’t mind. She knew her way around their beautiful home, and was looking forward to her first sunshine since winter began at their backyard pool.

Once unpacked and settled in the guest room/office, she made a sandwich, then found a comfortable lounger poolside to sit and read her novel. The weather was ideal, as always, in their hilltop subdivision outside San Diego. After an hour of reading, she decided to take Debby’s terrier Butch for a walk to see what had changed in the neighborhood since Thanksgiving.

Debby got home around 5:30. Al usually worked pretty late, so they had plenty of time to catch up. Never was Cindy happier than when visiting her sister. Al and Debby tried to convince her to move to California every time she visited, but she had never really considered it. She had always lived in her small town and probably always would, but she did love visiting.

She still lived in the small Pennsylvania town where they had grown up. She had been involved in a committed relationship in her twenties and dated several of the local boys since. Though still young and good looking with a nice body, local pickings were slim and she had little interest in being part of the gossip mill anymore. She rarely got asked out anymore, and most of her high school classmates had already married, some more than once.

Al and Debby had moved to San Diego after college, and Cindy spent most of her vacation time visiting them, especially since her parents had died. This trip she was celebrating her thirty fifth birthday with a 10 day vacation. She always spent her birthdays with Al and Debby to escape the usually blustery March weather in Pennsylvania. Getting a reasonable price on a plane ticket had required her to fly on Wednesday. Debby had taken off the entire next week to spend with her little sister, but until Saturday she would be on her own.

Al got home early for him, around 7:30, and promptly donned his standard evening wear; plain white t-shirt with boxers. On chilly nights he’d wear long boxers. The girls typically wore bikinis while at the house during the daytime, cover-ups in the evening, and PJs at night. There was always a lot of flesh exposed and a lot of hugging and friendly flirting, but they were family. Of course, that didn’t stop Al from getting a hard-on occasionally, especially when the girl’s loose cover-ups or PJs allowed him a view of a nipple or two or when they hugged on him in their swimsuits. The girls teased him mercilessly when that happened, but he just grinned. It turned him on to be the only bull in the pasture with these two fine babes, and he genuinely loved his “little sissy”. His penis was always on high alert when sissy visited; not only because the girls spent their time scantily clad, but also because he didn’t get much relief while she was there. Debby was reluctant to have sex when visitors were staying over. Even though the guest room was down the hall, Debby just wasn’t comfortable doing it. On long stays, she would help Al get off once or twice, but Debby couldn’t relax enough to come.

After dinner, they got in the hot tub . As always, Al took off his suit once discretely beneath the bubbles. He loved being in the hot tub nude. On rare occasions the girls would take off their tops, but only if they were tipsy and giggly. After 45 minutes or so, Al put his suit back on and they all got out.

Cindy slept soundly until almost eight, and when she woke she had the house to herself. She puttered around for a while, then decided to take Butch for a jog. After her shower, she sat down at the computer in the guest room/office to check her emails and kill some time playing games. She played solitaire for a while, then got bored and started looking through the list of programs to see what new games Al might have. Seeing a colorful icon she didn’t recognize, she opened it up. A box opened up with a lot of options, one of which was PLAY PROJECT. Clicking on it, a window popped up and began playing a video.

“UGGHH,” Cindy thought to herself. “Porn”.

She quickly went to exit, but stopped when she recognized Al & Debby’s bedroom.

“What???” Cindy thought.

She watched curiously as Al began rubbing oil all over Debby, who was lying face down on the massage table that they kept folded up in the corner of her bedroom. They were both naked. Suddenly the camera angle changed, and Cindy got a full frontal view of an obviously very aroused Al. She quickly closed the program, jumped up and began pacing. Her mind was reeling and she was shaking. She felt like a kid caught doing something wrong. She hadn’t intentionally done anything, but she couldn’t stop shaking. She went back and shut down the computer, then took her book and went outside to read. It took her 20 minutes to calm down enough to think clearly.

“Why am I being so stupid. I didn’t do anything wrong,” she thought to herself. “And anyway, it’s not like anyone knows I saw that video. God, why would they take that video anyway?”

Just then, Cindy remembered Debby talking years ago about Al always hounding her to take steamy pictures of her nude, or in skimpy clothes. Al was a good photographer. He had all the equipment to take exceptional pictures, and their walls were full of artistic photos Al had taken. And for indoor shots, she knew that Al had various soft lighting umbrellas and other paraphernalia. He had always been the one to take pictures at any of their family get-togethers.

Finally calming down enough to hold her book, Cindy decided to put on her suit and lay outside in the sun to read. Picking a strapless bikini that would allow her to get the most sun on her body, she applied lotion, poured some iced tea and went outside. Lying in the sun felt great, but she just couldn’t concentrate on her book. After reading and re-reading the same paragraph five times, she put down the book and closed her eyes.

“The camera angle changed,” she thought. “That meant that either there was a person manning the camera, or Al must have had multiple cameras that he could mix. Debby would never go for another person in the room while she was nude. Al must have some sort of video recording tools.”

Cindy couldn’t get the image of Al’s nude body out of her mind. As she relaxed in the sun and replayed the video in her mind, she began to get very aroused.

Cindy was drawn to that computer like a moth is drawn to a flame. She denied her feelings for a while, telling herself that she was no pervert. But she couldn’t resist. Checking to make sure the doors were locked and convincing herself she’d hear any cars pull up, she rebooted the computer and went back to the video mixing program that she had stumbled upon. Hitting PLAY PROJECT, she watched as Al gave Debby a full body massage while sporting a huge erection. Every once in a while, Debby would reach up and gave his boner a nice squeeze.

After finishing her lower body and feet, he turned Debby over on her back and continued working up her legs. Then he lifted her buttocks and gently pulled her down toward the edge of the table and set her butt onto a pad at the foot of the table. Holding the back of her thighs, he lifted and spread her legs wide, laying them over his shoulders, and began licking Debby’s slit. Reaching up to play with Debby’s hard nipples, he continued licking her over and over. Debby was really getting into the licking, and Cindy was really getting into the video. Her pussy ached to have the treatment that Debby was getting. Finally, Debby had an intense orgasm, moaning and grunting while clenching the sides of the table.

After the video ended, Cindy clicked on the FILE button and saw that there were dozens of projects. Every project was a different sex scene with Al and Debby. Two hours passed quickly as she watched videos. Worrying that someone might come home early. She turned off the computer and went back outside. Lying in the sun, she replayed every scene over and over in her mind, especially the scene of Al’s butt driving in and out as he penetrated Debby in the missionary position. Cindy never had known that Al had such cute dimples on his tight butt. She was becoming a very horny girl, with no relief forthcoming. She had never had an orgasm with a boy before, and she almost never masturbated. Whether it was her upbringing or her experience with sex, she rarely had a desire strong enough to bring herself to play with herself.

She definitely wouldn’t be able to for over a week, because she would never be able to do so while staying at Debby’s. Debby had an orgasm in almost every one of those videos, often with the aid of a vibrating dildo that she used while Al was taking her from behind or after he had already cum and dismounted her. Cindy was intrigued by the vibrators, as she had never seen one before. She was beginning to realize how clumsy the boys she had been with were, and how ignorant she had been.

Sleep didn’t come easily that night for Cindy. She squeezed a pillow between her thighs while fantasizing that she was the one being ravished by Al. Tossing and turning until almost one AM, she finally got to sleep and didn’t wake up until nine o’clock. While getting her morning coffee, she resolved to not look at any more of the videos; it was just plain wrong of her to violate their privacy.

The more she thought about those videos, the hornier she got. The hornier she got, the more that resolve began to crack. She looked into the garage to make sure both cars were gone, and through the house and outside to make certain she was alone. Then she made sure the doors were locked and turned on the computer. There were still dozens of videos that she hadn’t watched. They must have recorded themselves every time they had sex for years. The quality of the lighting and video, and the placement of the camera angles were amazing. It was like she was in the room. Cindy still couldn’t understand why they would want to watch themselves having sex.

“Were they selling them? No way, Debby wouldn’t allow that”.

She really didn’t even understand why she wanted to watch them have sex. She felt dirty and ashamed, and would have been humiliated if caught, but she couldn’t make herself stop. She watched them for several hours, working herself up to a sexual frenzy.

Debby often got off a little early on Friday’s, so by 3:30 Cindy and Debby had donned their suits and were in the backyard engaged in their favorite activities; sunning, reading, chatting, applying toenail polish on each other, gossiping and generally just enjoying each other’s company. Debby was only three years older than Cindy, and they had always been really close. Their faces and hair looked almost like identical twins, but their bodies couldn’t be more different. Debby was tall with long legs and small breasts. Cindy had shorter legs, but very nice C cup tits.

By the time Al got home, the girls were mixing their second batch of margaritas. He changed into his swimsuit and jumped in the pool to cool off, then grabbed a margarita. They all played in the pool for a while, then Al fired up the grill for a steak dinner. A big salad and a crusty loaf of French bread completed the menu.

“So what’s on the agenda for tomorrow?” Al asked.

“Well, we thought we’d go into town and shop, and that you could carry our bags. Then, you could take us out to lunch, and we could all catch a chick flick at the theater,” Debby joked.

“Yeah, that’ll happen. I’m going to get the yard work early. Tony’s got a tee time over in La Jolla at noon”.

“Then I guess we’ll just hang out here by the pool. We do want to go out to dinner tomorrow night, so be home by six or so. We’ll want to go out at around seven”.

“I’ll try, but it might be a little later than that”.

After dinner, Al needed to finish a report he’d begun a few days earlier, so he got on the computer while the girls cleaned up the dishes. When he clicked on the START button, he was shocked to see the recent programs list showed that his video editing software had been run. He deleted it from that list each and every time he used it, so that it wouldn’t accidentally be opened by visitors using his computer, like Cindy.

Opening the program and clicking on FILE, he saw that the recent project list included four older videos he’d produced that he hadn’t recently opened. That meant that Cindy had not only opened the software, she had definitely watched at least four of them.

“Oh, SHIT,” Al thought. “Debby is going to kill me. Should I tell her? What if I don’t and Cindy says something. Damn. Debby’s sure to make me delete all these videos permanently.”

He’d burned a couple dozen onto DVDs, but he doubted Debby would give him the chance to capture the rest before insisting he delete the whole collection”.

That night while Debby was getting ready for bed, Al decided to come clean and tell her.

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It had taken a lot of persuasion to get Debby to agree to the first video. When she realized how horny she got watching it, it became an integral part of their foreplay. That made it easier to get her to agree to a second, and then more. Now they watched them often, and it always got her in the mood. After tiring of seeing the same ones over and over, Al would just burn a few more on a DVD and they’d have fresh material. He’d recorded all sorts of lovemaking sessions over the last three years, so there was no shortage of new material.

“I’ve got something to tell you, Babe,” Al began. “Cindy found my video production software and the videos we recorded. I don’t know how many she’s watched, but I’m certain she watched some.”

Debby was stunned. She just stood silently with a blank expression on her face, not knowing what to say.

“How can you be so sure? Cindy doesn’t know her way around a computer very well. Did you leave it open in plain sight for her to find?”

That was just like Debby. Whenever she got unpleasant news, the first impulse was denial, the second was to blame Al.

“No, I didn’t leave it in plain sight. And yes, I’m certain. The question is, what do you want me to do?”

“I don’t know, I’ll have to think. I don’t want you to say a word about this to my sister.”

“Oh, like I would do that? Of course I won’t. She’s my little sister too,” said Al.

“Well then, why did you leave that pornography where she could find it. I don’t even know why you have to record that stuff in the first place.”

Al could tell that this was going nowhere productive, so he just said “I’m sorry,” and went to bed.

At least she hadn’t said anything about destroying the videos; at least not yet. Debby seemed to remember that she had mentioned something to Cindy about the videos or nude photos or something. She couldn’t remember exactly what she’d said, but she felt partly to blame for this. Not that she would mention that to Al. Cindy wasn’t going to be alone in the house anymore, since Debby had taken the next week off, so she had time to think about what to do about the videos on their computer.

By the time the girls got up the next morning, Al was halfway done with the yard work. The girls sat outside by the pool drinking coffee in their PJs and watched as Al finished. Shirtless, with sweat glistening, he looked nice.

“Thanks for the help,” he said as he came over to get a glass of water he’d left in the shade.

“No problem,” Debby said. “Do you want me to make lunch for you before you leave”.

“That’s ok. I can grab a sandwich at the course. I want to get there early to hit some balls and putt for a while”.

After putting away the equipment and bagging the debris, Al showered and dressed.

Sticking his head out the patio door, Al joked, “You guys have fun, but don’t work too hard”.

The girls went to put on their “sunning” bikinis. Those were the ones too skimpy to wear in public, but perfect for getting the best tan. All afternoon they alternated lying on the loungers, then floating in the pool when they got too warm. Cindy felt like she was in heaven, as it had been a really harsh winter at home, with no end in sight. She was lying on her back on a float in the pool with a visor and sunglasses. She had her eyes closed and was replaying the videos in her mind, imagining Al driving into her while she held his tight butt. It felt like all the energy of the sun was focused on her pussy as her mental images got increasingly graphic.

She imagined squatting down on Al’s erect dick, as she had seen Debby do in one of the videos. She pictured herself bending over the bed while Al stood behind her, pushing his dick into her until it was completely buried, then slowly pulling it out until only the head was inside her. She imagined herself on the massage table, with Al licking her over and over until she squirmed and moaned as Debby had. She spread her legs apart on the float and felt the sun pouring on her pussy, heating it even more than it already was. It felt like her pussy was throbbing. She had never been so horny in her life. She was floating between sleep and consciousness, but if she was asleep she was still dreaming of Al using her over and over again.

“Want a margarita?” Debby asked, startling her back to the present.

“No, I think I’ll have a beer.”

Paddling herself over to the edge, Cindy got out of the pool, dried herself off and went in the house with Debby to get a beer and pee. Debby grabbed a beer too, then they went back outside. Debby took some crackers and cheese, tuna salad, chips and some fruit out to the patio table and they snacked as they drank first one, then another beer.

“You look like you’re getting burned,” said Debby.

“I’ll put more sunscreen on. I haven’t seen much sun so far this year.”

“Why do you still stay in Pennsylvania?” asked Debby. “Why don’t you consider moving out here. You could live with us until you’re settled or as long as you want, and you know the job market is tons better here. The weather is like this all year long. You don’t have anything there to stay for, do you?”

“I don’t know,” said Debby, ending the discussion.

After their snack, the girls reapplied lotion and went back into the sun. Alternating between their fronts and their backs on the floats and on the loungers, they blissfully lolled away the day. Debby made a blender full of margaritas at 4:30 and they each had a couple of margaritas over the next hour. Then she made another small batch as they began picking up their stuff and carrying it inside. By six, the girls were in the shower and getting ready. They were going to Dee Dee’s, a really good steak and seafood place just three miles or so from their house. It was Cindy’s favorite, and Al and Debby loved it too. They went there at least once every time Cindy was in town.

At 6:45, Debby said “OK, let’s go get on the wait list. Al called and said he’d meet us there”.

When told the wait would be 30 – 40 minutes, Debby called Al and told him he’d have time to go home and shower if he wanted to, as long as he was quick about it. Then the girls went into the bar and got a glass of wine while they waited. Al arrived twenty minutes later, cleaned and pressed.

“Wow, you girls look sweet. Are you here alone?” Al said as he walked up from behind them and put an arm around each one’s waist.”

Debby gave him a big hug and kiss, and asked him about his golf game.

“Well, I only lost $50. Considering the sharks I play against, that’s not too bad”.

The table was ready before Al could order a drink from the bar, so they were seated. The girls ordered another round of white wine, and Al ordered a glass of red. It didn’t take long for Al to notice that the girls had been drinking, so the first time they got up to go to the bathroom, he fished Debby’s keys out of her purse and pocketed them.

They were halfway home, with Al driving, before Debby remembered, “Hey. What about your truck?”.

“Boy, nothing gets by you, does it,” joked Al. “I wanted to ride with you guys so you wouldn’t talk behind my back. I’ll jog back up to Dee Dee’s in the morning and get my truck”.

Later, as Debby was in the bathroom getting ready for bed and Al was lying on the bed in his boxers, reading a golf magazine, Cindy came up to the door and said, “Knock, knock. Are you decent?”

“Yeah, but come on in anyway. It won’t take me long to get indecent,” Al said, laughing.

“I need a hair tie. Does Debby have one I can use?”

“Look on her nightstand,” said Al.

As Cindy entered the room, Al noticed she was wearing a sleeveless teddy. It was see-through enough that he could tell she was wearing no panties.

“WOW! Do you have a date tonight?” joked Al.

“Very funny. I got fried today, and everything else I tried hurt to wear.”

“Come here and let me see,” Al said. “Man, you did get burned. You girls! You’re gonna look like a pair of alligators when you’re 50, if you don’t cut down on the sun”. Shouting into the bathroom, he said “Debby, where is that Aloe Vera lotion?”

Debby entered with the lotion and said, “Here it is, why?”

“Because little sissy got roasted, and she needs it.”

“Oooh, I’m sorry Cindy, you did get burnt. Here you go”.

“That’s alright, it’s not that bad,” said Cindy.

As Debby went back in her bathroom, Al said, “Lie down, and let me put it on you”.

Cindy lay down on their bed and Al began rubbing the lotion all over her body. It seemed there wasn’t any place on her body that wasn’t red, and her skin felt hot.

“Well, you did a great job of burning. I don’t see any place you didn’t burn. I hope you don’t peel, that’ll be uncomfortable. You need to put this stuff on several times a day for a few days.”

As he rubbed it on her tummy, his hand brushed up against her titties and Al began to get an erection. Working on her upper chest and sides, he was getting very turned on.

When Debby came into the room, she said, “Hey. It looks like you’re enjoying that far too much. You’d better let me do that”.

Cindy looked down at Al’s crotch to see what Debby was talking about, and saw that Al was at full mast, creating quite a strain on his boxers. She could feel herself beginning to flush as she saw the object of her fantasies over the last couple of days. Turning over to hide her embarrassment, she buried her face in a pillow as Al rubbed lotion on her legs and Debby took over on her back. As Al rubbed her legs, she began fantasizing that she was getting the erotic massage that she had seen Al giving Debby.

Between all the drinks she’d had, and the pent up sexual tension of the last few days, she couldn’t think of anything except Al licking her pussy, then driving his dick in and out of her. As Al worked closer and closer to her upper thighs, she began to arch her back and lift her butt, giving Al a view up her loose teddy shorts of her pantyless crotch. When Al got almost to the top of her thighs, Cindy raised her butt to give him access, and when he moved his hand back down toward her knees she lowered her butt. She wasn’t even conscious she was doing it. She was so horny she was almost panting.

The next time his hand approached her butt, she raised her butt and moved it toward Al’s hand. Startled, Al jerked his hand away from her and looked at Debby. Debby looked back and shrugged, as if to say “I don’t know”. Moving back to her legs, he continued to rub the lotion in. This time, when Al’s hand approached the top her thigh, Cindy lifted her butt and plopped her pussy right on Al’s hand.

“Aaaahhhmmm,” Cindy moaned involuntarily as she humped Al’s hand.

She couldn’t have helped herself if she’d tried.

Al thought, “What the hell”, and squeezed her pussy with the palm of his hand.

Neither Al nor Debby could believe what was happening, but Cindy’s desires were extremely clear; she wanted her pussy rubbed, and didn’t seem to be shy about it. She was obviously pretty drunk. Cindy’s butt was raised up in the air, providing full access to her pussy, and she moaned loudly when Al squeezed her.

Putting more lotion on his hand, he slid it under her shorts and began slowly rubbing her pussy, while Debby watched, stunned. Al slipped his thumb into her pussy and worked her slit with the side of his index finger, gently rubbing her clit. Cindy began bucking and moaning, and Al reached his free hand under her top and began tweaking a nipple.

“Aaah, Aaah, Ahhh”.

Cindy WAS panting now, as her butt humped Al’s hand. It took Cindy less than a minute to climax to an earth shattering orgasm, the first she’d ever had with another person in the same room.

“UuuuUUUUUUMMMMMMM,” she cried at the peak.

Her pussy was squeezing Al’s thumb in contractions that seemed to go on for a full minute. When the waves had finished washing over her body, she slumped into the bed and was motionless. Al looked at Debby in shock; neither one of them could believe what had just happened, but Al knew one thing for sure. Somebody was going to get it tonight; he’d never been hornier. Turning off the lamp, he walked around to the other side of the bed in the dark, taking off his boxers and flipping them on the bed. Grabbing Debby, he started pulling down her panties.

“We can’t,” Debby whispered in his ear.

“I’m gonna,” he whispered back.

“OK, but you gotta be real quiet,” she whispered, as if modesty was called for after the show Cindy had just put on.

But whispering “OK” to Debby, Al lay down on the bed and rubbed Debby’s pussy with the lotion, then entered her from behind.

Debby was just as worked up as Al, after watching the display Cindy had put on. She quietly retrieved her vibrator from her nightstand, and as Al slid in and out of her from behind, she worked on her clit with the vibrator. Al lasted only a couple of minutes, Debby was close behind. They grunted as quietly as they could and lay together, interlocked at the crotch.

Remembering they had no towel, Al grabbed his boxers off the bed where he had tossed them and Debby wiped up. Cindy hadn’t even noticed that her sister and brother in law were copulating right next to her. The intense sexual release and alcohol had relaxed her to sleep almost immediately.

to be continued

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Written by Sweetdreemz
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