The Girl Nephew Ch. 02

The morning after fucking her nephew Anne Golith fulling expected to wake up with some level of shame. Instead, she woke up feeling excited to do more. She was in love with the fact that Jack had been so excited to be fucked by her, and how quickly passion overtook her and him and derailed her original plans. She rolled over and looked at her phone, not a word from her nephew. Anne decided to see if she could get a rise out of him later, and took a handful of pictures of her leg, and her perfectly manicured pink toes, and one showing just the tip of the bright pink cock. When they were at the breakfast table later her plan was to send one at a time to see how he reacted.

To her surprise Anne was the first one to go into the kitchen. She hadn't bothered to look at the time before, assuming that waking up as refreshed as she was that it must be well past seven. Instead, it was only five twenty. Her mother and father wouldn't be up for at least another hour. Sally was likely in the exact same boat. Anne set a timer on her phone for fifty minutes. She figured if she could wake up Jack they could have nearly a full hour and she could sneak back to her bedroom.

Once the timer was set Anne raced, first to her room where the harness went back on and her bra went off. Then to Jack's room. She quietly opened the door and saw her nephew still in the green dress. His thong was off and on the floor, the green dress was still hiked up over his waist and his cute cock was still on display, albeit now soft but so very inviting. Anne tip-toed to the camera and replaced both the memory card and the battery. She checked her watch, she still had forty eight minutes to go.

Anne lubed up her cock lightly, then mounted her nephew grinding the dildo onto his soft member. It started to get hard as she ground into him more, she leaned forward and kissed his ear. As he stirred beneath her he lightly moaned.

"Jacki, wake up, we have enough time for me to be really rough with you before anyone else is awake."

Jack opened his eyes and smiled at his aunt, he leaned forward to kiss her. His kisses were so soft and gentle, that of someone who hasn't been loved and hurt enough to be anything but overly timid. Anne absolutely loved how he tasted.

Anne rolled off of Jack and said "get on all fours, and start begging right now"

Jack didn't need any further prompting or instruction. He rapidly got onto all fours. The green dress began to bunch up more and he let it hang off of him.

"Aunty I'm such a little anal slut. Last night I touched myself after you left, I need your cock. Please Aunty, please fuck your little girl. I want to be treated like the slut you want me to be, I want you to breed my little boypussy"

Anne was soaked as Jack uttered the degrading phrases. She was also shocked to hear how much his begging tone laced all of his words. Jack hadn't sounded like this in the video.

"You are such a depraved little girl Jacki, I had absolutely no idea."

"Does it make you happy Aunty? I want to make you feel as good as you make me feel. Please fuck me Aunty I want you so badly."

Anne added more lube to her cock. Before positioning herself behind Jack she bent over and kissed him deeply. His kiss back started timid, his tongue barely grazing hers, to egg him on she pulled his hair and pushed his head forward, she drove her own tongue deeper into his mouth, finally he let loose. His tongue circled around hers, and she let out a moan. Knowing her time was limited Anne only let the kiss linger a bit more before biting jack's lip and breaking away.

"You like Aunty's cock?"

"Aunty I love your big cock it is more than I ever could have dreamed of please Aunty I need it."

Anne didn't wait for any more encouragement, she lined the cock head up with Jack's ass and violently thrust forward. Jack gripped the sheets hard and buried his head into mattress.

"FUCK thank fuck fuck Aunty it's so hard thank you fuck" came Jack's muffled screams.

Anne slapped his ass hard, then again, and again. Each time Jack moaned out louder than before. Anne knew this is what he wanted from watching the first video. After ten slaps on each cheek she grabbed his hips and started pounding into him harder than she had before. Back and forth Anne moved her hips unlike last night this time Anne would take all but her cock head out before thrusting all the way back in.

Jack was moaning the whole time. His hands continued to stay balled into fists gripping the sheets tight. Anne eventually slowed her thrusts and resumed hitting his ass.

"Jacki, you have such a great ass. I love how it thwaps against my hand! But Jacki you also are a dirty little fucking pervert aren't you?"

"Yes Aunty Anne I am. I just wish I was a sexy woman like and I'm so lucky you are fucking me with your sexy cock."

Anne hit Jack four more times before resuming the rough and rapid pace. Anne's hands gripped Jack's hips to the point where the poor boy's skin was nearly translucent white. Her hips continued to buck back and forth as Jack let out another round of pleading. The loud pounds of her body slapping into hers echoed off the room's walls.

"Aunty I love your cock fuck fuck fuck thank you Aunty I'm such a dirty little girl who doesn't deserve how good you are fucking her thank you oh fuck Aunty yes yes yes."

Anne hadn't intended to touch Jack's cock at all. She had intended to try and make him orgasm from just her dick. But suddenly she couldn't resist. She spit onto her hand and wrapped it around Jack's hard pulsing dick.

"Aunty fuck I can't stop myself from cumming if you touch me please."

"Jacki, at some point you're going to learn to control the orgasms out of your cute little girl cock, and if you don't I'm not going to touch it and instead I'm going to lock it up. But for today, because we don't have enough time, you can come just catch it in your hand like a good girl."

She had barely finished the r in girl when she felt his cock twitch three times and then one very hard pulse and Jack's grunting and moaning told her she had pushed him over the edge. Jack moved his hand out revealing a cupped hand full of white creamy cum.

Anne slapped his ass hard "eat it, eat it and then I'll let you eat me out."

Jack quickly complied, Anne watched him lift his head up and to the side and realized his forehead was covered in sweat. Anne was dripping wet and was pretty sure the lightest graze of his tongue was going to send her over the edge too. Anne unhooked the harness and left the cock buried in her nephew.

She quickly laid down in front of him and spread her legs. Jack didn't ask and instead just immediately put his tongue on her vagina. Jack had clearly never eaten a woman out before. His tongue mopped at the outside of Anne and then darted in, and while he clearly loved that feeling he had no idea what he was doing.

Anne glanced at her phone, she only had seven minutes "Jacki suck on my fucking clit" she said.

Jack immediately did as she commanded.

"Ohhhh fuck baby that's good just like that. Oh fuck yes. I'm going to teach you to eat my pussy really good next oh oh oh tiiiimmmmmme"

The orgasm crushed over her. Anne pulled Jack's hair and egged him on to keep going. Finally she pushed him away, panting and embarrassed to see she had left a giant wet spot on the sheets. Anne quickly stood up and dressed and withdrew the cock from her nephew's ass.

Anne gave him one more kiss and left the room.

Thirty minutes later Anne sat in the kitchen as Jack walked in. His mom was at the stove making everyone omelets. Jack looked freshly showered and Anne had to fight back the thought of what it would be like to fuck him in the shower.

Anne had been thinking about her next move since the night before, and this morning's rapid fuck had only confirmed for her that she wanted Jack all to herself for several days. The issue largely was how to get his mom to let him go for that long. Ever since her husband's death Sally had rarely let Jack out of her site for more than twenty four hours. It frankly explained why her handsome, fit, and smart nephew was so awkward and had never been with a woman. Well that, and the fact that Jack heavily fetishized both Sally and Anne... but no one else knew that besides her.

"Hey Sally, can I borrow Jack for a week sometime soon? I need to paint my house, I haven't had time to do so, and he looks like he could use an extra couple hundred bucks?"

Sally froze at the stove. Anne had no idea what she would think of this idea. But Anne knew what she wanted to do. She wanted Jack to paint all day, and then she would dress him up like a pretty doll at night and take him out on dates.

"Sure, actually if you do it the week after next it would be perfect. I'm out of town for a conference and then I don't have to worry about him starving at night while I'm gone."

Jack's eyes lit up when his mom said yes. Sally for her part sounded oddly relieved. Like she was legitimately worrying about her twenty year old son being left home alone.

The next several nights Anne spent most of her free time watching tv and researching what all her nephew would need to be the passable crossdresser she knew he deep down wanted to be. She sent him links to different breast forms and told him to pick out the size he wanted. She watched tutorials on Youtube for how to teach someone else to do makeup. She bought four different wigs in different styles for Jack to wear.

The next Sunday evening when she heard Jack's car in the driveway Anne raced to her front door. The excitement had been building in her for two straight weeks and she was feeling like a little kid again bracing for the week ahead. At the door before opening it she took three deep breaths to calm herself. The one thing made most clear from her and Jack's two times together so far was that she and he both expected her to take the lead and be more in charge.

Jack knocked on the door and after she counted to four Anne answered. Her nephew came in with just a small backpack for his clothes for the week. Anne had briefed him via text already that she would supply everything he was to wear. Anne reached forward and kissed him as she closed the door behind him. Jack kissed her back with the same kind of passion he had before, his tongue attacking hers and swirling around it, his hands caressing her back and roaming down to her ass. Anne thought about stopping him but honestly just loved the passion too much to do so.

For ten minutes the two stood in the entry way just like that embracing each others tongues, his hands running up and down her body, slowly the timidity of her nephew giving way and he tried to grab her from the front moving a hand to her left breast, she swiftly stopped him.

"Not yet baby." She said.

Anne broke off the kiss and led him up to her bedroom. On the bed she had laid out the four wigs, the outfit Jack was to wear today, and his new breast mold. Jack fingered each wig and started to tear up. He turned and hugged his aunt as a few solitary tears strolled down his face.

"I love them" he whispered into her neck.

Anne took him to the bathroom and drew a bath. Once it was warm she gently shaved his entire body leaving no hair of any kind and when he was smooth cleaned him thoroughly. After his bath was done Anne left him in the master bathroom and sat on her bed and spread her legs wide for him to see. She was soaking wet. Jack started to walk to her and she held up a hand.

"No, crawl to me."

Jack rapidly complied getting down on all fours and making his way across the room to her. Anne could see his reflection in the bathroom mirror and loved the way his very hard cock and sagging balls looked crawling to her. Jack knelt in front of his aunt and immediately stuck his tongue out to lick her. Anne quickly closed her legs off blocking his access but simultaneously trapping him in place.

"Jacki. One thing that needs to be made very clear is that for this week, I am completely in charge. Everything you do must be approved by me. If I want you to eat me out I will tell you to do so. Am I clear?"

"Yes Aunty you are Aunty." Jack replied in a subservient tone

Anne released her legs and Jack held his head exactly where it had been.

"Good boy. Now give me a foot massage."

Jack did exactly what he was told. Slowly he rubbed his aunt's heels, then moved up to the arch, and then to the balls of her feet. He worked methodically up her left foot taking his time, waiting until she seemed satisfied before moving onto the next section of the foot. When he finished her left he started her right. The whole time Jack stared at his aunt's toes. They were painted an electric pink today, and Anne could tell what he wanted more than anything else was to put his mouth on them.

"Do you like my toes Jacki?"

"Yes Aunty Anne they are very pretty."

Anne let him keep massaging for a few more moments before instructing him to worship her feet. Anne intentionally didn't tell him how, she wanted to see what he wanted, she wanted to feel worship as he felt it should be done, she could always train him better later.

For as bad as he had been at eating her out the first time, he was amazing at worshipping her feet. Just like with the massage he started on her left foot. He kissed the heel covering every inch with his lips, and then he licked right behind where he had kissed. He worked his way up to her arch kissing and then licking up and down. Anne started drawing small circles on her clit, she wanted her nephew to realize how much she was enjoying this. He worked his way up just below her toes again kissing and licking. Then he kissed the bottoms of her toes before licking back down to her heel, and back up, and down, and back up. He did this until the entire bottoms of her foot were covered in his saliva. He looked up at her then.

"Aunty, can I suck your toes please?" he begged

Anne was somewhat caught off guard by this. He had ritualistically worshipped her so well and for him then to stop to ask permission was a very intriguing thing.

"Yes, Jacki be a really good girl and suck my toes one at a time first. Suck them like you sucked my big hard cock before."

Jack needed no further encouragement. He eagerly began to suck on her toes, starting first with her left pinky toe. He treated it just like making out with Anne, he swirled his tongue around the toe twice, and then sucked like he had on her clit. Anne was full moaning as he moved onward. He progressed taking his time on each digit.

"Oh my god yes, Jacki that's such a good boy keep sucking Aunty's toes keep sucking them like you do her big hard cock oh fuck yes Jacki make Aunty cum so hard with your tongue." Anne was moaning the words out, panting as she did so.

As Jack moved to her left big toe Anne stuck a finger inside of herself and rapidly gyrated it on her g-spot. In the mirror she could see Jack's cock twitch making a large and noticeable movement as it did so. Simultaneously she could see his ass and knew that it was aching for treatment of its own. Jack sucked furiously on his Aunt's toe. Jack's tongue swirled the toe, once, then twice, and on the third time Anne dropped backwards as an orgasm washed over her.

"That's it Jacki don't stop baby girl don't you dare fucking fuck fucking stop don't you dare oh fuck Jacki. Fuck fuck fuck that's my good girl making Aunty cum so fucking hard yes baby yes."

Jack kept going, this time moving his tongue to his Aunt's right foot. His tongue did the same dance as before but he started with the right big toe this time. Jack assumed that the best way to bring her to another orgasm was to start in a similar manner to how he left off. This time Jack sucked softly at first, slowly building up harder and harder. Anne's moans got louder again and he watched as a second and third finger worked their way into her dripping bald snatch. Anne's other hand was rubbing at her clit working harder and faster than before.

Jack started the tongue swirls and as he did so Anne's left foot moved up and caressed the back of his head, urging him on. Jack couldn't help himself at this point, he started stroking his own cock. His Aunt was thrashing on the bed, and as the second orgasm rushed over her she again cried out.

"Oh fuck yes Jacki my good girl you're so talented oh my good little fucking foot worshiper yes yes yeeessss Jacki fuck yes."

Anne panting sat up, Jack was so caught up in touching himself while sucking on the toes he had for so many years admired he didn't notice. He particularly didn't notice the look on Anne's face. Anne aggressively pulled her foot out of Jack's mouth. She leaned forward and slapped him across the face hard. Jack immediately removed his hand from his penis and put it to his sore face.

"No no, by all means Jacki go on. Finish yourself off. It is going to be a really good way to teach you a lesson about who is in charge."

Jack started stroking himself again. *Thwap* Anne's hand came down hard on his left ass cheek. *Thwap* again this time on his right. Jack jumped on the second hit, causing him to momentarily stop touching himself.

"I didn't tell you to fucking stop" Anne growled "keep fucking going. Make yourself cum. You are going to cum while I spank you. Then you are going to have your cock locked in a cage for the next twenty four hours."

Jack started again, harder than before. Thwap, thwap, thwap three more hits alternating cheeks again. Thwap, thwap, thwap. Jack was touching himself while being spanked by his Aunt, and was candidly in heaven. He kept going and as he did his Aunt spread his ass cheeks apart and spit right onto his ass. Thwap, thwap, thwap. The saliva slid between his cheeks. Thwap, thwap, thwap three more hits Jack was close. Suddenly has aunt was beneath him.

Anne positioned her vagina underneath her nephew "don't touch my pussy, don't enter my pussy, but you are going to cum onto it am I clear?"

"Yes Aunty oh fuck thank you thank you Aunty. I love your body. I'm sorry Aunty I can't help but touch myself to you. Oh oh ugggggggh" Jack moaned out.

His load shot thick and all across Anne's bald public mound. She was in awe of how much there was. This was the second time that she had felt his cum, and the second time she was absolutely shocked at how much his long cock could blow.

"Clean it off of me now." Anne whispered, in an aggressive but soothing tone.

Jack quickly did exactly as he was told. He licked the upper part of his Aunt's public mound, licking and feeling the bare flesh beneath his tongue. He worked his way down and to the left covering the outer edge of his Aunt's labia. He carefully went under the entrance to her very wet pussy. Jack let his mouth go over and to the right back to where he began. Jack looked at his Aunt's wet glistening cunt and realized that his cum had dripped onto her clit, and into her.

"Aunty am I allowed to keep cleaning you?" Jack asked unsure of what to do.

Anne nodded to him and shoved his head aggressively downward. Anne moaned as Jack's tongue went down her clit and inside of her.

"Oh fuck good girl." Anne said as she pulled him up and kissed him. Anne tasted their mixed cum on his tongue. With his tongue in her mouth Anne bit down lightly making Jack squirm.

Anne released Jack and stood him up. She knelt in front of him and kissed his softening cock three times. Then she swallowed the hole flaccid member down her throat and Jack moaned as he began to get hard again. Anne withdrew her head and then stood up and walked to her dresser. She came back with a hard steel cage.

"I told you and grandma and grandpa's if you couldn't control yourself I would make it happen. So now you wear this unless I decide otherwise." Anne slipped the cock cage over her nephew and locked it in place. She showed Jack the key and put it on a necklace and over her head.

"I am sorry Aunty." Jack said with his head hanging low.

"I know you are. But without a punishment how will you learn? Don't worry I won't make you wear it home. Now, let's go watch a movie before bed!"

Anne showed Jack the bedtime outfit she had picked for him. First she helped him into the breast mold. Then she put on a satin top that showed off his new cleavage and short satin bottoms that left his ass cheeks hanging out. Then she surprised him with a matching set, but much like he wore his breast mold she wore her harness and dildo underneath her shorts. Anne gave Jack a peck on the cheek and the two watched a movie and went to bed.

The next morning Anne woke Jack up by rubbing his asshole. As he slowly stirred she took a well lubed middle finger and shoved it into him.

"Oh fuck Aunty thank you good morning fuck."

Anne fingered Jack and walked him through her plans.

"I have to work every day this week. I was serious about you painting my house, it legit needs it." she slid a second finger in "but when I get home we are going to have Aunty-Niece dates. Tonight we are going to go get matching mani-pedis, and you are going to learn how to do your makeup. My plan is that each night when I get home you will have changed into some sexy outfit for me take you out on a date, and then when we come home I am going to fucking absolutely have my way with you."

"Aunty that sounds so fucking amazing please yes ohhhh fuck. Aunty I don't think I can stop myself from cumming if you keep fingering my little boypussy."

Anne removed her fingers and slapped Jack hard on the ass.

"Okay, thanks for the honesty little girl!"

The two went downstairs and ate breakfast. Anne showed Jack where the paint was, and headed to her office while he spent the day painting. At 4:30 a text pinged on Jack's phone "on my way! The guest room closet has lots of outfits for you"

Jack went upstairs and looked through the closet. There were way more outfits than days in the week. Jack selected a blue blouse and a flowy black skirt that went down to his knees. He went back to his aunt's room and put on the breast mold, and a blonde wig and got dressed. He admired himself in the mirror and stroked at the skin of his cock through the pink panties and chastity cage. Jack heard the garage door opening and went downstairs to greet his aunt.

For the next hour Jack and Anne practiced his makeup. When they finished and Anne deemed him to have done a good enough job on the most recent run through Jack was shocked to look in the mirror. He didn't recognize himself, Anne barely recognized him. Jack had mastered the contour and highlighting slimmed down his typical masculine face, his eyeliner and shadow had made his eyes far more feminine. Jack's cock strained against the cage as he looked at himself.

Anne could sense how he was doing. She reached under the skirt and drug her nails across the skin of his tight member. She spat onto her other hand and stroked his cock over the cage. Tantalizing him, eliciting moans and then finally stopping.

"Jacki you are so pretty." Anne said

"Thank you Aunty. I feel so amazing right now"

They went to Anne's favorite nail salon. A trendy hip place that was more than a little accustomed to trans women and cross dressers. The technician said nothing as she worked on Jack's hands and feet. Anne looked on with tremendous passion as she watched him select an electric green color for his toes, and a matching set of squoval acrylic nails. As Jack admired his painted toes while they dried his cock again twinged aggressively against the cage.

While their nails dried Anne leaned over and whispered "You are such a cute little slut right now."

After getting their nails done they went out for dinner and then back to Anne's house. As soon as they walked in the door Anne stripped down to nothing. She reached under her nephew's skirt and pulled off his panties.

"So when we go out I'll probably let you wear these, but when we are at home I don't think you need anything under your skirts."

As Anne touched the panties she felt the massive wet precum spot that had been leaking out of her nephew since he dressed earlier.

"Jacki! You got these dirty that will not do."

Anne pulled Jack by his chastity cage to the couch in the living room. Anne bent him over her knee and began to spank him. In her mind, Anne knew that every night was going to be very similar, she would get her feet worshiped, she would fuck her nephew, and she would at some point punish him for some infraction, because she loved how he squirmed and moaned.

"How many spankings should I give you?" Anne asked in her sternest tone.

"Aunty I didn't know not too, and I didn't mean to I can't control it."

Anne struck him three times on each cheek in quick succession. After the sixth hit she ran her finger to his balls and stroked them.

"That wasn't an answer. And those six don't count."

"Ten Aunty" Jack paused "per side"

Anne bent over her nephew and kissed him gently on the neck.

"I like that answer."

Thwap, thwap, thwap. Anne came down hard three times on Jack's left ass cheek. Thwap, thwap. Two more this time on his right. Thwap, Thwap, Thwap. His left again. Thwap, only one to his right. Thwap, thwap, thwap, thwap. Anne finished off his left side with the tenth hit being the hardest. Jack cried out in pain and leapt slightly off of her knee. Anne eased him back down and slowly massaged the pink flesh.

"Jacki you did so good."

Jack sniffled "thank you Aunty."

Without warning Anne resumed on his right side. Seven quick thwaps in quick succession, Anne worked both hands into the mix her left coming hard followed by a sharp but softer hit from her right hand. Jack was openly sobbing at the end of the tenth hit. Anne helped him up and laid him across her chest. She ran circles on the exposed skin of his lower back and shushed him to calm down.

"Jacki I hope I don't have to do that again. But whether I do or not is really entirely up to you."

Anne stood up and left the room. Returning with her harness back on. She gestured Jack to the ground and he knelt in front of her. Anne spit on her dick and then wiped it across Jack's face.

"you are such a cute little girl. Tonight I'm going to have you worship my feet and ride my cock does that sound good?"

"Yes Aunty it really does, please let your little girl ride your big thick cock."

"Tomorrow, you'll worship my feet and I'm going to throat fuck you with my cock."

Anne sat down and offered her foot to Jack. Jack impressed Anne by not doing the exact same thing as the night before. This time he started with her right big toe. Instead of licking and swirling his tongue he immediately went to sucking on it, and then after a few minutes eased back into the swirls of his tongue. He finally withdrew his mouth entirely from it and then licked just the bottom, before sucking on it again.

Anne's hand had immediately gone to her clit. Jack did not leave any slow build up this time and instead went immediately to the action that left her soaked through.

"Oh fuck Jacki you are so impressive baby girl. Fuck fuck fuck."

Jack continued using this as a sign to move to her next toe this time Jack took both her middle two toes into his mouth at once. He sucked both toes hard, and then while sucking them ran his tongue between the toes. Anne completely melted when he did this.

"Fuck baby yes. Do that fuuuuuck"

Jack did it again. And again. He started to work a pattern, two strokes from the top one from the bottom and then a harder suck before repeating. Anne could barely stop the orgasm from coming as he did it a fifth time.

"Stop sucking and get on my fucking dick now." Anne yelled at him.

She wanted to cum hard, and she knew that meant depriving herself a little bit longer. Jack greedily let his Aunt's foot go and straddled her. Anne lubed the cock and directed it just beneath Jack's ass.

"Jacki have you ever ridden your hairbrush before?"

"No oh fuck" Jack gasped as Anne teased his hole with the dildo.

"Well, you have to set the pace a lot with this okay, so you get to decide how this goes, but if you don't ride me well enough for me to cum then I'm going to have to take over."

Jack slowly eased the cock head passed his asshole. "OH FUCK Aunty, god I love this cock."

Jack hovered momentarily getting used to the head inside of him again. It was harder to stuff in when he was in control. He slowly eased himself farther down. Anne slapped his ass to encourage him to go faster. Jack did not understand the hint and instead eased up thinking she liked what he was doing so far.

"baby, no you need" Anne grabbed Jack's hips as she spoke and shoved him hard "to take" another push had Jack's ass fully engulfing the cock "it all!"

"Oh fuck fuck fuck Yes Aunty make me take it all please god"

Anne let Jack lift up slightly and then pushed him down. Slowly they got into a rhythm. When Jack didn't move hard enough or fast enough Anne would buck her hips upward and into him. Each time she did Jack moaned out. After fifteen minutes Anne came and hard. As she did so she grabbed her nephews back and clawed into him.

"Fuck Jacki harder baby girl harder fucking harder get Aunty to cum more fuuuuuck."

She bit down on his shoulder eliciting a deep moan from him.

"Aunty I want to cum can I please fuck please?"

"You're going to cum just from Aunty's dick? Your caged little girl cock can do that huh?"

"Oh fuck yes it can Aunty this is so fucking perfect your big hard oh oh oh fuck your big oh god fucking hard dick is too much Aunty please."

"Jacki I'm going to count down from ten, if you make it then you can cum and I'll take the cage off for all of tomorrow."

"One, two" Anne thrust up into Jack slapping his ass at the same time.

"oh aunty please faster fuck"

"three" Anne picked up the pace of her hip thrust "four" she now was going two thrusts per count.

"Aunty no oh god fuck not that faster fuuuck Aunty please please count faster oh myyyyy gooooood"

Jack almost came but held it back. "five" three more thrust "six" two more "seven" four more "eight" three more thrusts faster than before "nine"

"Aunty please I can't hold it please I just need to cum please oh fuck fuck fuck" Jack pulled his skirt up careful not to cum on it.

Anne leaned back "ten, on my stomach and tits Jacki fucking coat your Aunty"

"Gooodddd yes please yesssss thank youuuuu"

Jack's load was large. Bigger than the night before. A thick wet streak blasted out of her nephew's cock hitting her belly button, and just below her tits. It also caught in the cage leaking out of it. Anne took the necklace off and unhooked Jack's cage. She made him lick it clean first. As he climbed off of her cum continued to dribble out of him. This time onto the floor. Without instruction Jack got on all fours and licked the floor clean.

"Aunty may I please clean you now."

"Good girl, yes you may. I am so impressed with that load."

Jack began to clean his aunt. He did so diligently and slowly. First starting below her belly button he licked up and down and around it. Anne was amazed that the load had been so massive that it virtually no place was Jack able to run his tongue over her once and get it all. For several minutes he licked her stomach before moving beneath her breasts. As his tongue moved around and under her perky C cup tits Anne moaned out. She clutched Jacks head and moved it to her breast itself.

"Suck my fucking tits." she cradled him in her arms as she said it.

Jack eagerly sucked and licked at his aunt's breasts, first one, then the other. He was amazed to see his fake boobs pressed against her and realized his were bigger than hers. For fifteen minutes they continued like this. Finally Anne broke his contact with her. She kissed him tasting his sweet and salty cum still on his lips and tongue. She let her hand roam down to his cock and lightly played with it. While it was an inch or two shorter than hers and far thinner Anne loved the way it felt in her hand, especially when soft.

Anne led her nephew up to bed. He practically collapsed into her when she moved to let him cuddle her.

"Am I really a good girl Aunty?" Jack asked in the most innocent voice Anne had ever heard.

"You are a really good, and really slutty girl Jacki and I love every aspect of those things."

The next morning Anne awoke and saw Jack laying on his stomach. The two had slept naked the night before too exhausted to put on any clothing. Anne spread his ass cheeks and began lapping at her nephew's ass. Jack moaned and raised his head.

"Good morning Aunty" he whispered

Anne didn't say a word merely kept licking his ass. Finally she stopped slapped his cheeks still pinkish from the night before and laid on top of him grinding her pubic mound against his ass.

"Good morning little girl. Tonight we are going out to dinner. Have you ever worn a butt plug before?"

"No Aunty. I've only had your fingers, my fingers, a hair brush and your cock inside of me."

"Well. Tonight we fix that!"

Jack spent the day painting. This time he wore his breast mold, a pink blouse, and short shorts the whole day. That night when she got home Anne again tongue fucked his asshole, before lubing up and inserting a small plug into his ass.

Jack grunted "Oh I like that feeling"

"Good. Because you're wearing it until my cock is back inside of you."

Before going to dinner Anne changed him into a skirt. She liked the accessibility of the free flow as opposed to his cute shorts.

On the way home from the restaurant after Jack got himself buckled into the car Anne slid a Hitachi wand under his balls, and turned it on.

"I really liked how you were in the chastity cage Jacki. It was so fantastically feminine. So I really want you back in it. You're going to have to try really really hard for me not to lock you back up. Especially since I know my cock can make you cum. So let's see if you can make it the whole way home without blowing your load."

Anne made the drive home painstakingly long. She let other drives go through intersections first. She avoided the faster roads and took a much slower scenic route. The whole way Jack was squirming. Two miles from her house Anne started teasing Jack, letting her hand rest on his very erect cock and occasionally rubbing it.

"I'm really impressed Jacki. I thought between the plug in your ass and the vibrator and the silky smooth black panties you have on you would have blown your load a long time ago."

"Fuck Aunty. It is really really hard not to. But I want to be good for you. Please can we drive faster."

Instead Anne slowed down, intentionally getting stuck at a yellow and then red light. At the light she put the car in park and leaned over and softly kissed his cock head through his panties. When she sat back in her seat she told him what else was in store.

"I'm not sure I'll penetrate you tonight. But maybe I will. Tomorrow night I'm taking you out with a few of my friends, I want to see how passable you are. Then Thursday, our last night together, I am going to fuck you rougher than you could ever imagine. I'm going to tie you up. I'm going to pound your ass as long and as hard as I possibly can. I'm going to send you home to mommy having been used so..."

Anne was cut off by Jack's moan "oh fuuuuck Aunty Aunty fuck I'm cummmming Aunty fuck me it's too much I can't stop."

Anne watched the skirt bob up and down as Jack's cock pulsed. She watched the black panties dampen leaving a tremendous and obvious wet spot. She saw the cum spill out onto Jack's creamy thighs.

The vibrator stayed on until they got to the house, Jack whimpered with each bump they hit. Once inside Anne stripped Jack's bottoms away. He was coated in his own cum. First Anne shoved his panties in his mouth.

"Fucking lick them clean you dirty little girl. Look how fucking drenched these are. You perverted little girl, this stain is never coming out. You're going to look at this each time you're over as a reminder of how bad you are at controlling your orgasms."

When the panties were soaked from Jack's saliva instead of his cum Annie wiped them on his face. When finished she scooped cum up from his legs into her fingers and shoved two fingers into Jack's mouth.

"And it is fucking everywhere Jacki. I'm impressed at how good of a little cum monster you are but come on girl. I can't get this all off of you. Upstairs to the shower NOW".

Anne slapped Jack's ass hard and he quickly moved upstairs. She smiled to herself, excited for what was next.

In the shower Anne put her harness on and made Jack get on his knees. She told him to give her the best blow job of her life. To his credit he started off strong. Jack had been practice on something, she did not know what, since the first time he had her dick in his mouth. After a few minutes watching his head bob up and down on her cock Anne gave her first thrust forward. Jack was in the process of pulling back and Anne had decided it was time to get rougher. Each time Jack moved his head back he was immediately met with a forward thrust from his Aunt. Anne looked down and saw that his cock was twitching again.

Eventually Jack started to put up resistance, he put his hands on his aunt's thighs, trying to push her back from the thrusting. He was in turn met with her hands on his head and a rough series of thrusts forward.

"No way you're stopping me baby girl. Your pretty little throat is just as much my property as your ass."

Anne began to throat fuck Jack, slowly easing him so that his head was against the wall. Jack no longer had to, nor could move to suck the cock, it was all up to his aunt. Back and forth she thrust, Jack eventually stopped putting his hands on the front of her legs and instead grabbed her ass, pulling her into his mouth to try and stop the roughness of the fucking. After several minutes Anne let go, and Jack collapsed forward onto all fours.

"Aunty, I love your cock thank you for letting me suck it."

"You look so pretty with a cock in your mouth, maybe tomorrow you can suck a real one."

Jack didn't answer and instead just looked on. Anne wasn't sure what look she was seeing on his face and decided not to push it. Instead she slid off the strap one and let her nephew eat her out again. Much like with her cock in his mouth Anne was still far more assertive than she had been before. Jack's tongue was out and she moved his head up and down her pussy. When she would stop in one spot for a moment Jack would immediately begin making circles with his tongue, or darting it in and out of his aunt.

Anne was impressed at how much better he was this time around compared to the first time.

"Jacki keep going baby girl, keep eating me baby yes. Yes. YES!" Anne screamed as the orgasm rushed over her. She sat down on the shower floor with her nephew, and pulled him to her. Jack cuddled against her chest as the water pulsed down across them. Anne looked and saw her nephew's hard cock and contemplated what the next night might bring for it. In her mind, she wanted to force him to be with another man, she thought it would be so sexy. But he didn't seem ready for that yet. So instead, Anne decided to lock him up after the shower, to leave him locked up the next day, and to then fuck him before dinner.

"Jacki, you need to get soft so Aunty can cage you back up. We're going to finish in here soon and when we are done you're going to go to bed. I have a plan for tomorrow already!"

Jack kissed his aunt, it was entirely unexpected. It was soft and sweet and so innocent especially depraved for what she had just been thinking. Jack eventually went soft again and was locked back up. The two went to bed with Jack redressed in his pretty pajamas.

The next evening when Anne was on her way home she texted Jack "I want you laying on your back on my bed with your legs up when I get home."

Anne walked in and saw exactly what she wanted. Jack had changed into a cute school girl look. Anne walked over fast and climbed on top of her nephew. She positioned her cock at his asshole and leaned into kiss him deeply.

"God you are such a good girl"

Anne slipped in as the words left her mouth. She nearly orgasmed immediately watching his girl cock twitch and strain and pulse inside of the cage.

"Thank you Aunty. I love your cock. I love you fucking my boypussy while my girl cock is locked up."

"Do you want me to lock you up the rest of your trip little girl? Should I lock you up when I see you at grandma and grandpa's?"

"Yes please plea..."

His pleading and begging drove Anne over the edge, she started forcing herself in and out of him faster. Simultaneously she leaned in and kissed him deeply. As she did so he let his legs relax and slipped them behind her waist. He then wrapped his arms around her back, completely engulfing her into him. This just encouraged Anne to go faster, but despite the pacing it was far gentler than any but their first time had been.

Anne had been concerned that last night was too much. She loved the power she felt in all of this, she loved how readily her nephew was submissive to her. But she was scared of pushing him too far and away from her. She also may secretly have been scared that he would become independent in his sexuality, that if he did then he wouldn't need her as much.

Anne whispered into Jack's ear "you're such a good girl Jacki. Cum for Aunty. Aunty will have such a hard orgasm when you do."

Anne wasn't sure if it was the edging the night before, his own feeling of anticipation today, or just the command but Jack came hard again. As he did so Anne did too.

"Jacki yes that is my sweet good girl fuck ooh ooh fuuuuuck"

After her orgasm Anne cleaned Jack for a change. She licked his hips where cum had shot. She licked the caged cock eliciting more moans and grunts as her tongue hit the bits of his skin poking out of the cage. After he was clean Anne helped him fix his make up and gave him a kiss.

"Tonight will be fun sweetie, and tonight when we come home just you and me, I'll get to cuddle you to sleep one last time."

That night they went out with Anne's friends. It was a mixed group of men and women. Anne loved that at least two of her guy friends couldn't keep their eyes off of Jack. Two of the women knew Jack was crossdressing. Neither would have guessed it but for being told. Anne wanted them to touch him. One did when she and Jack went to the bathroom together, she slipped a hand up Jack's skirt and squeezed his ass. When she did so she grazed his balls. Jack's moan made the woman lean in and kiss him deeply.

"If your Aunty ever wants a play mate I'd be happy to join in." She said as she broke the kiss.

As the night ended the woman slipped Jack her number with a note "I'm Becca, just keep this number just in case." Jack showed the note to Anne who encouraged him to add it to his phone.

"Becca is wild, and sometime that may be exactly what you want."

Secretly Becca had just validated the fears Anne had before. There weren't that many female fish in the sea who wanted to be with a guy like Jack, but there were enough and that was troubling.

The next night Anne didn't text Jack on the way home. At 4:15 Jack went and changed into a short denim skirt and a tight white button up blouse. He slipped into high heeled open toed shoes and admired himself in the mirror. When he heard the garage door going up he hustled down and knelt outside of the door. Anne walked in and offered a leg to Jack.

"Take off my shoes baby."

Jack unhooked the straps on her heels and slid them off. When he was finished Anne leaned down and kissed him.

"Stand up little girl. Let's go have some fun."

Anne led Jack to the bedroom. When inside she sat down on her chaise with her legs spread wide. She gestured Jack over and as he began to kneel she stopped him. As she did to she engulfed his caged cock into her mouth deep throating the entire thing. For five minutes she blew her nephew and at the same time teased his asshole, running her fingers up and down and then making circles in a pattern on him. Finally she roughly shoved one finger inside of him with no additional lubricant. To Jack's credit other than a grunt of pain he stayed up right.

"Aunty that hurts but thank you I love your fingers in me. I'm your little girl and you can use my boypussy however you want."

Anne removed her mouth.

"You are damn right I can. And believe me little girl, tonight I'm going to use it a lot."

Jack bit his lower lip. The look was so adorable that Anne removed her finger from inside of him, and pulled him down to kiss him.

"Jacki you are such a cute little girl. If you need me to stop anything at anytime just say uncle okay?"

Jack nodded his head. Anne grabbed him by the neck and moved him an inch away from her bald, glistening pussy.

"Jacki you get to taste me. You get the greatest pleasure any man ever can get with the taste of these wet lips. But first you are going to repeat back to me how to make me stop."

"If I need you to stop I say uncle." Jack said while looking straight at Anne's clit.

Anne simultaneously moved her hips forward and his head forward forcing his full mouth onto her.

"Eat me out, make me cum so I can fuck you like a little slut."

Jack immediately began to comply. He started by licking where Anne's hips and pubis met. He would lick up once down once and then suck on that area. Each time Anne moaned when he got to the sucking portion. Anne ran her hands through his redhead wig and encouraged him each time. Ten times per side led Anne to be literally aching for him to just lick her fucking clit. Jack however was taking his time. Again he worked inward more. He licked her pussy lips just the outsides, not going further slowly he worked circles around her. Anne could feel him inching closer to her clit.

"Lick my clit Jacki, Aunty is so close to coming. I'm going to fucking explode baby girl."

Jack took the encouragement as an order and immediately began to lick his aunt's clit. Within thirty seconds of his tongue drawing circles around her she orgasmed.

"Jaaccki fuck little girl oh god your tongue is doing so good. Lick my clit Jacki suck it like oh fuck suck it like a cock make Aunty cuuummmm more oh god."

Jack latched on at suck it. Then when she said suck it like a cock he moaned. And as he moaned and sucked Anne began to cum harder than she ever had before. She shoved two fingers around Jack's head and into her slit. As she worked them in and out rubbing her G-spot the third orgasm came, Jack still sucking away and Anne started to squirt. As she did so Jack almost instinctively jerked back. Anne roughly shoved him to the ground and mounted him.

"Stick that fucking tongue out" she grunted.

Jack quickly complied and Anne began to grind up and down his face. She used his chin, his nose, and his tongue all as pressure points working her way back and forth on him.

"Oh fuck Jacki oh my god girl oh fuck keep that tongue oh god oh shit shit shit yes keep your fucking tongue out."

Anne started grinding harder and hard. She worked her way faster up and down the momentum and finally a fourth orgasm hit her.

"FUCK yes Jacki my little fucking niece god you are such a good little sex toy oh fuck fuck fuck Jacki yes swallow my fucking juices. OHHHH FUCK"

Anne collapsed onto the ground next to Jack shaking. She rolled closer to him and kissed him deeply.

"I have never had orgasms like that before. I'm going to fuck your asshole so hard for this, you are getting the best reward Aunty can give."

It took Anne five minutes and several deep breaths to regain her composure to sit up. She stood and resumed her position on the chaise.

"Get my harness and put it on me."

Jack complied, with his denim skirt rumpled and part way up his hips he walked to the bedside and got the harness. He knelt back down in front of his Aunt, and taking a liberty she let him get away with, kissed her legs. He lifted one foot and slid it into the harness and then did the same with the other. Jack started at the cock as he helped slide it up to his aunt's hips. She stood up and he slid it the rest of the way. Then without being told he tightened the straps around her legs and gave the cock a kiss.

Anne bent over and lowered her voice. She whispered into Jack's ear in the most forceful, most incredible tone that she had ever used "bend over the god damn chaise and spread those cute little ass cheeks."

Jack immediately did as he was told. Within seconds a thick glob of lube had hit his ass. Suddenly two fingers were inside of him. Jack was not expecting this. The fingering went fast and aggressive it was more than ever had happened before. For three or four minutes the fingers came in and out, and then another glob of lube hit him. The fingers came out and Jack felt the big thick head against his ass.

"Yes Aunty fuck me please please fuck my little boypussy I need your huge cock please please fuck me."

With a singular thrust and grunt Jack's ass gave way to Anne's thick pink cock. Anne then proceeded to aggressively fuck Jack. She had never moved her hips as hard and as fast as she did then. She grabbed his hips with both hands and began to work. Interspersed with the thrusting was a series of spanks. Their bodies quickly fell into rhythm, the slapping of their bodies slap slap thwap mixed with the spanking.

"Oh fuck Aunty thank you oh god yes fuck me like I'm a slut god I need this fuck fuck fuck."

"Are you a slut Jacki, do you want to be readily fucked by others? What if my friend Becca came in and ask fro a turn could I turn you over to her?"

"Oh my fucking god yes please oh oh oh oh god Aunty anything you want oh fuck."

Slap slap slap thwap slap slap slap thwap. Anne bent over and bit Jack's ear lightly.

She whispered to him "what about my friend Eric? He was checking you out all of last night should he fuck you?"

"Aunty I oh oh fuck Aunty god yes, I want to suck a real cock and have him explode in my mouth please oh god please."

Slap slap slap thwap slap slap slap thwap Slap slap slap thwap slap slap slap thwap thwap thwap.

"You can cum whenever you want now Jacki. Blow your big load for aunty."

Jack started grunting and as he did so Anne picked up the pace, forcing her to abandon the spanking. The constant slapping of their bodies together was starting to leave red marks on her thighs, she could see the same marks forming on the back of Jack's legs.

"Oh my god yes, Jacki you are such a good little cock slut. You do such a good ugh oh fuck yes ugh job taking Aunty's big dick."

Anne was about to cum again herself. She watched Jack's hamstring muscles tighten.

"oohhhhh fuck Aunty please harder harder please I'm so oh fucking close."

Anne increased the speed, moving her hands from his hips to his shoulders and bending herself over him. The cock was now only coming an inch or two out at a time but the thrusting was getting more and more aggressive. Jack screamed out as his whole body tensed up in one moment and then he exploded. It coated his skirt, and his legs, and the chaise, and was leaking out of his cage still.

Anne didn't stop for a few more seconds, she loved the sound of him whimpering now that the had cum and was being drilled further. Finally she stopped and watched as without instruction Jack cleaned off her leather chaise with his tongue. He then cleaned the mess on his skirt and started at her knowing what was next. Anne unhooked the cage and forcibly shoved it down his throat. When she removed it there was not a drop of Jack's cum left on it.

"I really hope you keep your little asshole trained like it has been for me sweetheart. Because this was so much fun, and in two weeks when we are at grandma and grandpa's again I intend to make you take my cock, and then each and every visit after you're doing the same. How does that sound."

Jack hugged his aunt and while squeezing her said "that sounds so perfect Aunty. I only wish I could dress for you more often."