Gerald's Second Time

Jessica and Gerald were a bit blown away as they got to Jade's house. It wasn't tremendously big but it certainly was a lot better than what they were living in. It had a decent sized yard and was about as close to campus as one could get which made it rather convenient. Trying to be polite Jade gave a little bit of a tour while talking about her history in it and with herself. It was well maintained and two stories with a really nice porch that surrounded three sides of the house including the front and back door. Jessica and Gerald tried to provide compliments about how nice the house looked but for once, the nice things they said seemed to fall on deaf ears. Eventually through conversation the siblings were able to learn that her dad worked for a Chinese export company and bought this house a little over 20 years ago when the company stationed him to live in the States for a while. Overseeing deliveries, negotiating deals, schmoozing politicians, and stuff like that on behalf of his bosses was his assignment. He was pretty good at his job too. In fact that when Jade was 12 the company decided to transfer him to Japan. Since her Chinese origins could have led to a great deal of bullying, and the fact that she would have had to learn a whole new language on top of normal difficulties of moving for a young child, Jade's parents decided their daughter might be better off staying in the US with a live-in nanny and tutors until she was old enough to care for herself. Her dad's position afforded him enough money that he provided Jade a comfortable living even if it was rather lonely. But as her parents spent less time in America their English got worse and Jade's Mandarin suffered as she wasn't speaking to her parents nearly as often. Now the few times they talked each year over the phone, the calls had to include an interpreter on the line. "I also think my dad kind of likes to keep me here just for prestige too. He thinks it sounds cool and impressive to tell his Japanese and Chinese business partners about his successful and brilliant daughter going to college in the US." By the end of the backstory Jade again stopped seeming so shy as her emotions took over. This sounded more like she was venting a little frustration and talking about some of her grievances seemed rather therapeutic for the woman so Jessica and Gerald just let her ramble to her heart's content. When most of the tour was done she finally brought her guests to show them the reason they came here.

Jade did look a bit apprehensive as she escorted the siblings to one of the bedrooms. Which seemed like it was nearly a third full with stacks of board games. Once again Jade was pleasantly surprised when the derision she expected never came. Jessica seemed a little intimidated and unsure but also impressed as she strolled around. Gerald on the other hand sounded legitimately impressed. When he turned to Jade he had a huge smile on his face, "Oh, this is so cool. It feels like I'm living in a big game store but I don't even have to pay for anything!"

Jade watched her guests as they slowly wandered around looking at row after row of box after box. Jessica decided if they don't decide on something quickly they could be here all night so her solution was short and simple. "Okay, each one of us pick a game and we can bring them home Let's make this a 10 minute time limit so we're not here all night. Sound like a plan?" Everyone agreed and even thought there were many captivating options and in the end Gerald decided to stick with Catan as his choice. Jessica had no idea what most of these games were like so she made her choice entirely based upon box art and went with something called Sherriff of Nottingham. As the two held their choices they looked at Jade who was looking happier by the second and they reminded her to pick a game. She hadn't even realized that when Jessica said for everyone to pick a game, everyone included her. "Hey, board games are only fun if everyone is having fun. Since you're nice enough to let us play your games you should get to pick at least one too right? I'm sure that there's one that comes to mind that you'd really love to play." After a few seconds of careful thought she smiled and ran around for a little bit before carrying something called, "Arkham Horror," under her arm.

As they began to leave Jade made a sudden nice and set her box down on the living room table and asked Jessica and Gerald to hold on for a moment. In a second the girl had ran off into the house before coming back with a set of loose black and white clothing under her arm. With an obvious excitement in her voice she asked the two if she could do something she never got to do as a little girl since she was horribly shy even then. "I know we just met and it might be a bit rude but, I never had a sleepover at a friend's house. Do you think it would be okay..."

Gerald interrupted and smiled, "Of course. Honestly you sleeping at our place just means we don't need to drive you back home in the middle of the night. Probably better all things considered. But you may want to grab a change of clothes so you can have something clean to wear tomorrow." After running back to her bedroom to grab some clean clothes for the morning and happier than she could ever remember being, Jade and her new friends left for their apartment.

After they got home they ordered some pizza and a salad for Jade (apparently she'd found the vegetarian diet more appealing for the past day or so and decided to try it our) and with some good food and drinks. Gerald thought it was so cute that Jade changed into her pajama-sweats before the food even arrived. Apparently the sleepover thing is something she had wanted to do for a long time. Since she was the one providing the entertainment, the three started playing and decided to go with Jade's game first. Neither of them had ever even played a cooperative board game before so the idea of everyone just exploring, working together, and planning to accomplish a common goal while just surviving the dangers of the creepy mansion was cool and something they were totally unprepared for but in a good way. Talking together and trying to work out a strategy as a team was also great. At least until two tuns after Gerald decided to give Jessica a knife that he found before she went to explore the basement by herself and both of the siblings were introduced to the concept of a "traitor mechanic." It turned out Jessica's character was actually a werewolf that wanted to lure Jade and Gerald into the mansion so it could have victims to feed off of. So within seconds the game went from everyone working together, to Jade and Gerald trying to survive the sister's evil clutches as she tried to take them down. In the end Gerald was knocked out cold and it was only a lucky roll that allowed Jade to find a revolver to overcome the monstrous she-beast across the table from her. As Jessica pouted a little bit after thinking she was going to win, they all smiled and thanked Jade for bringing the game over so they could play.

"Wow, some of these games go a lot deeper than the typical stuff like Monopoly or Scrabble don't they?" Jessica said as they put everything back together and made sure nothing was lost. "I can see why you wanted to play that one, that was fun!"

Gerald smiled as he helped, "And the way so much of it comes together randomly means the next game could be completely different. And you've got the different character options to add flavor and playing styles."

As happy as those two were it was nothing to be said of Jade who was a kid in a candy store. For so long she had wanted to play one of her games with actual friends and she was finally getting the chance. After packing up Arkham Asylum, Jade asked where the restroom was. She wanted to pop in for a potty break and deal with some other issues. Obviously she didn't tell the others but her chest had been feeling a little weird for the past hour or two. It was about two minutes after she went in that Gerald and Jessica's discussion about which game to try next was interrupted by a rather loud and sudden squeaking shriek.

Both Gerald and Jessica ran over to the bathroom to make sure nothing was wrong. After a couple of knocks and no answer Gerald started getting rather worried and began talking about breaking the door down. Hearing that finally convinced Jade to say that she was okay. After a few more awkward moments Jade asked Gerald to go back to the living room and asked Jessica to help her with something. Understanding that since the alarm came while Jade was in the bathroom and it could be a 'woman body' issue, Gerald told his sister to call if they need anything and left. If Jade had started her period or something and forgot her preferred method of control at home or something like that, he didn't need to know and understood that the girl wanted to keep it private. A couple seconds after Jessica let Jade know her brother was gone, Jade unlocked the door.

Jessica had been having enough fun with the board game and just getting to know Jade that stage two of her Random Remote path had largely escaped Jessica's conscious mind until she walked into the bathroom and saw the worried expression on Jade's face as a small trail of white fluid dropped from one of the girl's nipples.

Jessica had to summon every ounce of willpower in her body and soul to avoid saying or doing anything pervy as her sexual arousal shot through the roof while she began to imagine all the games that they could play now that this had started. Mental images of her and Gerald quickly began to form in her mind as she remembered what the Random Remote had done to her. Jessica didn't do a very good job hiding her desire though as she stood with her mouth slack as she shamelessly stared at the girl's lactating boobs. Lucky for her Jade was too busy staring down at her spontaneously milky boobs to notice. The emotions on her face cycled through confusion, worry, and embarrassment. She looked up at Jessica with a combined look of confusion and panic, not sure what to do and at this point she seemed to be looking to her friend for any sort of suggestion or explanation. Jessica meanwhile was trying to remember exactly what the Random Remote had said were the attributes of this stage and how to use it to get what she wanted. In an attempt to come across as clinical and serious, she asked Jade how it felt. If there was any pain or unpleasantness.

"It feels, stuffed. Like, like when you eat a little too much food or something. It doesn't hurt but they feel kind of, umm, stretched? Right now it's just annoying and unpleasant but it's been slowly getting worse while we were playing Arkham Horror." She tried to squeeze the breast or pull at the small, dark nipple on her chest but very little of the fluid came out.

It was apparent that the more she tried, the more the girl was becoming frustrated and upset. Hoping that the girl wouldn't freak out Jessica tentatively reached her hands out and locked eyes with Jade while stopping as her hands got close. Before making contact she wanted to get the girl's permission. "May I?" Jade hesitated for a few seconds and slightly nodded her head after an assurance that Jessica just wanted to help the girl who wasn't sure what to do herself.

With permission, Jessica put her hands on Jade's swollen chest and it was very hard for her to stifle the sexual moans that began to work there way through Jessica's system. They were so soft and smooth. Jessica of course had her own to play with but she decided fairly quickly that handling another woman's was felt far better in the hand. Especially when they were as big, round, and heavy as Jade's had become. With one hand firmly grabbing on to one of Jade's breasts, Jessica gave them each a light squeeze and waited to see her reaction. It was supposed to be intense sexual pleasure but she wanted to see how much. As she gave them each a good, solid, long squeeze. Jade began to moan loudly in unrestrained passion. Jessica maintained a firm grasp letting more hot milk roll out of the nipple while Jade made some very sexual and lustful moans as she was fondled and didn't stop until Jessica had to let go of the girl's chest and catch her as Jade's legs buckled and she began to fall down. Through a combination of a new smell and the large wet spot leaking down the sides of Jade's pajama pants it was apparent that the girl had already reached an orgasm. Jessica was surprised as the sexual pleasure from milking was supposed to be intense but she didn't think that just one groping would cause her to have a massive squirting orgasm as intense as the one that Jade appeared to have gone through. Jessica was kind of glad it did as that was insanely hot to make the girl cum just by playing with her boobies. From the horny, glazed-over look in Jade's eyes, Jessica was certain the cow on her floor wasn't anywhere near done or ready to quit. After carefully helping her friend down to the floor, Jessica placed her hands on the girl's chest again, this time very lightly and began teasing her. The Random Remote also said milking would cause her to get turned on so hopefully after that orgasm and the first pull, lightly rubbing a finger along the girl's chest this way would encourage her to continue. Attempting to sound like a concerned friend, which wasn't hard since she still cared about the girl but also required a little bit of acting since she knew the question she was about to ask was total bullshit. "I-is it okay? Does it hurt? Do you want me to stop?"

Jade meanwhile remained on the bathroom floor totally shook up and out of breath at the feelings that Jessica had just caused by squeezing her chest. She had experimented sexually in the past. She had brought herself to orgasm a few times. But she had never experienced anything nearly that powerful. But in addition to the orgasm being the most intense of her life, Jessica's actions had caused a slight release in the discomfort she had been feeling. Not just tonight. It seemed like a lot of the shyness she had felt her entire life was clearing as her mind felt a bit cloudy and slow. Combine all that with a strong wave of horniness that was sweeping over her, Jade just looked at her friend meekly and with a pleading tone to her voice asked her to do it again. Part of her felt bad for putting her friend in this kind of an awkward position but she couldn't resist. It had felt too damn good and she was already too horny, especially since Jessica had already showed a willingness to help her.

Trying to keep the lust out of her own voice Jessica suggested they get those pants off of Jade before going any further and Jessica almost had a small, alarmed screech of her own as she stopped staring at Jade's tits long enough to notice her ass. Which now had a white cow tail wagging around above it. For a moment Jessica thought how weird the randomness of the Random Remote could be. Suddenly having a tail she didn't have ten minutes ago seemed to go unnoticed but the leaking milk thing is something she is alarmed by. But with Jade's assistance they got the girl's pants off and got into position and soon started slowly squeezing and lightly tugging Jade's chest and nipples, letting the milk flow out and onto the tile floor beneath them.

Jessica was somewhat glad to see that Jade didn't cum every time she squeezed Jade's tits though. While in one way that'd be amazingly sexy, it'd leave the girl too worn out and tired to deal with what Jessica really wanted to see happen. She guessed Jade's initial reaction was because she wasn't expecting how good it would feel, or it being a first time, or her being particularly backed up (or some combination of the three). But slowly the two drained Jade's chest. Just to help her plans come to fruition, every time Jade looked like she was about to cum, Jessica would back off and slow down a little. This resulted in the girl just getting hornier and hornier without any relief. With the reduced intelligence that this milking caused, soon the girl was just vacantly looking forward with her tongue out and adding her drool to the bodily fluids on the floor with a big, dumb, happy, horny smile on her face. When she was pretty sure Jade was ready Jessica went for her goal. "You know, I bet if my pervert of a brother Gerald saw you like this, him being the freak he is, he wouldn't be able to resist sticking his cock deep into that soaking pussy of yours."

While Jade's thoughts had been slowed and fogged over for a while, what Jessica had just said did manage to bring a level of clarity to her head. Not much of it, but some all the same. Jessica was about to ask if Jade wanted that but didn't get the chance. The brain-addled cow slut on the floor didn't have much left in her mind but she did remember the name Gerald and she remembered how to yell, "Gerald! Gerald! Need you! You! Please!"

It didn't take Gerald long to get there as he had remained standing and waiting in case he was needed for anything. Jessica had closed the door behind her so he hadn't heard much until Jade yelled for him so he had no idea what to expect. He was certainly not prepared for what he saw. Jade was lying nude on the floor of the bathroom, copious amounts of sexual fluid dripping from her pussy and milk dripped from her nipples as the floor was covered in a significant amount of both. He was immediately fully erect and couldn't resist staring at the young, beautiful naked woman on the floor. As he stood there staring, the girl just smiled warmly and looked at him saying one word, "Fuck."

He looked over at his sister who was taking in his reaction with an unrestrained, perverted smile. "What did you do? This has something to do with that Random Remote thing doesn't it?"

The perverted smile didn't leave completely but it did diminish as she also took on a tone of seriousness. "I did use it on her but all it did was add the cow stuff. The desire to be with you was already there. Remember when she ran away from us crying earlier today at school? When I ran after her she told me that after you cried talking about Dr. Who and saw your sensitive side, she realized she had a crush on you and was worried that you would never like her that way."

Gerald looked back at Jade as his sister spoke. Even if the Random Remote made her want him it probably wouldn't have stopped Gerald from taking advantage of it as he took a moment to think about it. She wanted him either way and Gerald was too turned on by her body to say no, especially when she looked so damn **** for it. But he wanted to hear her say it. Both because it made him feel good deep down, and watching her wiggle that cute tail-adorned ass and pussy around was such a glorious vision that he knew it was going to be burned into his mind forever. Not even caring that his sister was still in the room, Gerald pulled his pants and underwear down in one swift movement before casually tossing them into the living room. Deciding any attempts at hiding his own perverted smiles were pointless he leered down at the girl, grabbed his cock, and began waving it around. "So Jade, do you want it?"

Jade's response was just to remain on all fours and back up a little bit so her pussy pressed up against Gerald's leg before moving it up and down. The girl was so horny she was literally humping his leg continuing to just say "fuck, fuck, fuck" with increasing need and desperation. Gerald didn't make the **** woman wait very long before he dropped to his knees and tried to slowly inch his way into Jade. Jade on the other hand didn't seem to be interested in a slow entry and with a loud yell pushed herself backwards until she couldn't get any more of Gerald into her. She didn't talk much but Jade made it crystal clear that she wanted Gerald to go at her hard and without mercy. He was only too happy to oblige.

Shortly after they got started Jessica did her best to sneak around her brother who was taking up a good portion of the doorway since he didn't really move after coming in to the room and it wasn't like the bathroom was all that big to begin with. He assumed she was planning to leave them alone to do their thing but turned out to be wrong as within a minute his sister was coming back into the room naked with a dildo in one hand and a bottle of lubricant in the other. "Not sure I'll need any of this stuff with as wet as you two beasts are making me, but having a little extra just in case can't hurt right? The dildo she carried had a suction cup on the end and with no shame or hesitation the girl made sure it was firmly attached to the floor before sinking down onto it, grinding her cunt and moaning loud as she watched Jade's eyes cross and her mouth open ai a slight scream as she came on Gerald's dick.

The first time Gerald came in Jade, both brother and sister were alarmed by the sound the girl made. She made a loud, strong visceral noise that sounded part like she was saying, "moo," and kind of like she was saying, "more." She did get a little bit upset when Gerald finished cumming and responded by quickly pulling out of her. At that point her moo/more cry became louder and more insistent until Gerald grabbed her by the waist, turned her over, and lied on top of her. With his dick beginning to slide right back into Jade, Gerald began kneading her tits as milk began to flow out to very appreciative moans by Jade that were quickly muted as Gerald's lips descended upon hers. He got so wrapped up in his passionate, intense time with Jade that he forgot his sister was there watching and masturbating until Jade came for around the forth time since Gerald took over her pleasure. Gerald had came several times as well but Jade kept asking for more and didn't stop until she passed out. Sleeping on the floor with a dopey, contented smile on her face. He eased out of her sweating and dirty but very satisfied. Finally paying attention to things in the world other than the girl on his cock, he saw his sister was no longer riding her rubber cock but was still watching and smiling in a way that almost seemed motherly and proud. She even whispered a, "Good boy," to her brother as he slowly got to his feet and looked down at the state Jade's body was in.

As he stood there his sister actually carefully walked around the prone Jade after removing her sex toy from the floor and stood next to her brother. Both naked she leaned against him lightly and sighed, "God damn that was a good show. You two should do it more often."

Gerald smiled and laughed a little bit at the humor but definitely wasn't opposed to the idea. But leaving her lying on the cold bathroom floor wasn't something he was willing to do so he sighed as he asked his sister to move so he could pick her up. "I'll put her on my bed and sleep on the couch I guess."

Jessica heard that and afterwards the only sound in the apartment for the next several seconds was the rubber phallus she was holding hitting the ground at her feet. She knew he wasn't watching and she was doing it only for her own minor amusement but after her brother said that all she did was slowly move her head so she was looking at him. But she did it in a deliberately slow, comically and over-the-top overdramatic fashion. That part was just an overacted joke for her own amusement. But the ice cold, angry look that Gerald saw when his sister didn't move or say anything was completely genuine. He actually got a little worried when he looked down and saw that look as it was genuinely frightening for some reason. "What? Did I say something wrong? I'm giving her the bed. Isn't that a gentlemanly and nice thing to do?"

Jessica's expression only hardened at that. There was serious venom in her voice as she spoke. She knew her brother was an idiot and didn't know any better but still, it got to her. "Think about it. Do you see how shy she was since we met her? Do you think that there's any chance in Hell that you weren't her first?"

Gerald hadn't really given it any thought as he was a bit caught off guard by everything but after Jessica mentioned it and he gave it some thought, she was probably right. Unfortunately that didn't help Gerald out who started blankly at his sister who sighed as her head sank slowly against her fingertips in frustration. "Her first time. That's supposed to be a special thing right? Let me tell you what's going to happen tonight. In a few hours she is going to wake up. Not because she wants to, but because she moved the wrong way in bed and it'll hurt, or maybe her sticky and sweaty skin feels weird, or she smells some of the business you two did, or something like that. She will wake up in a bed she doesn't recognize and in a room she doesn't know. And she will wake up sore and in pain after what you did. She will feel messy and dirty with all the sweat, milk, cum, and whatever else that's covering her. One of two things will happen, she will wake up in that state alone or with someone that cares about her and she cares about. Which do you think she would prefer?"

Gerald thought about what his sister said but was still a bit worried. "Makes sense but I guess I feel kind of uncomfortable with it. Seems a bit forward doesn't it?"

To that Jessica looked at him with a look of total exasperation, "Forward? Forward?!" She reached down and wiped a little bit of the cum that covered Jade's body and brought it up to Gerald's face. "Doing this to her isn't too forward but sleeping in the same bed afterwards isn't?"

"But I mean, she was asking for it. If I could ask and she said she was fine with it that's okay. She's asleep so I can't really ask if she's okay wi---"

At that point Jessica put her other hand up to his face to silence him and was about to facepalm again but realized Gerald's cum was on that hand. She had become a bit more of a shameless pervert but wiping her bro's jizz on her face was still a little too far. "For a real first time with someone you like, there is nothing better than the post-fuck cuddle. Here's what's going to happen tonight. You are going to lay the girl down on your bed and you are going to sleep next to her. She's going to wake up in a couple hours and you will be there lying next to her. At which point she will see your handsome face and that big dumb sexy body of yours, remember everything that happened, smile, and try to scoot closer with a big smile on her face. If you wake up at all when she does, drop a subtle hint to let her know that you're okay with it so she can go back to sleep and feel even better as she lies in your arms. Now pick her up, I'll pull back the blankets so you can get her tucked in nice and snug. Okay?"

As Jessica turned and left the bathroom Gerald just sighed as he thought about it and delicately picked Jade off the floor. Jessica knew more both about girls and romance than he did. He wasn't sure if he was in love with Jade or anything but he could definitely see a serious relationship developing between the two of them given enough time. He decided Jessica was probably right so he did his best to carefully lie her in bed as his sister watched on and he got a nod of approval when he kissed her forehead. And a little less than four hours later Jade woke up as her legs rubbed together in a way that caused a bit of an unfamiliar, unpleasant odor to reach her nose. It took her a moment to remember why she smelled and felt the way she did and when she remembered it all, she felt around and it didn't take her long to realize what the bit, hard lump resting next to her was. A tear rolled down her eye again but this time it was out of happiness. For a moment as she scooted back to get closer to Gerald, she felt like a worthwhile person. The kind of person people might WANT to be around. With a touch of boldness she reached for Gerald's hand and pulled it so his arm was lightly wrapped around her body. Still asleep and unaware he unconsciously pulled her a little tighter to her and his hand squeezed her stomach a little which triggered a tiny giggle. With a little wiggle and pillow readjustment Jade drifted back to sleep firmly tucked under Gerald's embrace.