Dillon Jones turned to enter the Silver Oak Estates gated community; he always marveled at the massive stone arch between the two ancient oak trees flanking it.
This story is fiction and has Transgender related sexual situations. If this doesn't appeal to you, please stop here. If you're willing to keep an open mind and continue, please do and enjoy.
Beyond the Wall
Dillon Jones turned to enter the Silver Oak Estates gated community; he always marveled at the massive stone arch between the two ancient oak trees flanking it. The trees and arch stood outside the ten foot high wall surrounding the enormous housing development with its multi-million dollar homes, manicured drives and luxurious club house. The Halloween decorations adorning the facade were festive and reminded him of a medieval castle. It was truly a wealthy area beyond the wall. There were only 150 homes but with many on 1 acre lots and a few sprawling over 5 acres, the whole place covered a big piece of land.
Dillon stopped his Toyota pickup, rolling down the window at the guard shack where he saw Tony, a rotund security guard he’d known for a couple years now, step out to greet him. Dillon had been working for the same pool cleaning service since he was sixteen, always coming with an older coworker until his eighteenth birthday where he was now allowed to work solo. It was a fun job and he actually made decent money at it during the summer. But now that he graduated and didn’t have any plans for college just yet, he wanted to put some money away for when he did want to continue his education. Being that it was well into the fall, his ‘smaller’ clients didn’t need him coming by as regular but here at ‘The Oaks’, these rich people always had a need for his services.
“Hey DJ…You’re here bright and early,” Tony said, resting a thick forearm on his driver’s door.
“Got lots of pools today, Tony. Looks like everybody here is having some kinda party on Halloween and wanted everything looking sharp,” Dillon replied, flashing him a casual smile, “The curse of living in So. Cal.” Except for a couple clients and a teacher or two, everyone called him ‘DJ’ rather than Dillon especially if they knew him for a while.
“Well you better get to it, buddy,” Tony said as he reached for the button that opens the decorative wrought iron barrier, “There’s just over a week until Halloween.”
“Yes I know…No rest for the wicked,” he laughed, proceeding through the open gate.
DJ had a sly smile as he drove along the shaded streets, recalling each house he had to visit that day and the possibility of seeing some of the residents who often displayed themselves poolside as he worked. He found it humorous that if they saw him someplace other than here, they’d hardly give him a smile or even a glance. But in the privacy of their backyards, things were definitely different beyond the wall. The Oaks was filled with bored trophy wives, neglected MILFs and spoiled offspring looking for attention. DJ loved to watch them parade around in skimpy bathing suits or even half naked trying to get a reaction, which they usually did. He never had any physical encounters with his clients because, ‘it wouldn’t be good for business,’ according to his boss. The other reason was that Dillon was shy.
It was hard for most people to believe such a handsome young man could be so shy but DJ was just that. His slim athletic build, on his six foot frame, had been refined over many years on the swim team at school. He has an infectious smile and sandy blonde hair cropped close, also from his swimming career. Once he got to know someone, he was funny and charming but getting to know people was hard for him. He wasn’t outgoing, so most girls he liked would pass him by thinking he was aloof or even arrogant, which wasn’t true.
Pulling into the long stamped concrete drive of his first stop, the Taylor’s, DJ wondered if Mrs. Taylor, a fifty-two year old cougar would be up this early. He collected his gear and proceeded to the backyard to begin his day.
***
DJ saved the best for last. His final stop was at Ms. Michaels’ house. Mansion was a better de***********ion. The residence must have been over ten thousand square feet by his estimate and spread out across a 2 acre parcel was the lavish grounds. It also had the most amazing pool as far as DJ was concerned. The scalloped edges of the pool looked like flag stone surrounding a small lake that had a grotto at the far end. A huge hot tub was on top of an artificial peak with its water flowing out to create a waterfall over the entrance of the cave. The shrubs and trees around the pool gave it a real forested look. There was one of the monster oaks the neighborhood was named for at the back corner of the property, spreading its huge limbs over a large portion of the remaining yard.
It was well known Amanda Michaels lived alone. Although according to Tony, she had ‘frequent guests’ that stayed the night. The thirty-eight year old financial executive also threw epic parties for people other than the residents. DJ assumed that she was going to have a blowout Halloween party after seeing the decorations that were up all around the property and having him come and do his thing on her pool. He noticed her red Corvette in the driveway but hadn’t seen Amanda yet. She usually was out sun bathing when he showed up on weekends but it was a weekday afternoon so she may have just gotten home from work. He was disappointed he didn’t find her out on one of the chaise lounges but he held out hope she would make an appearance. With a sigh, he set about the task of taking care of her pool.
Lucky for him, many of these modern pools were controlled electronically. The owner could do most anything they wanted with a smart phone or tablet. DJ ran a diagnostic check with his work tablet since all his clients have to give him access so he knows what’s going on with the mechanisms. The only thing that looked like it needed his attention was one of the filters feeding the hot tub. He decided to do the cleaning of the pool itself and handle the filter last.
Given the size of the pool, it took nearly forty minutes to clean out leaves and other debris from the various skimmers and the surface of the water. There had been a loose grate in the hot tub that was hanging by a single screw that he re-attached as well. DJ had just finished checking one of the lights in the grotto that appeared to have a corroded bezel when Amanda walked out of the back sliding glass door. She still had on her work attire but that wasn’t disappointing at all to DJ.
He loved how she looked in one of her little bikinis. She was tall, about 5’-9” with legs that didn’t quit which seemed to make her swim suits look much smaller. Her body was toned but not overly muscular with a narrow waist and proportionally flared hips. Her ass was high and tight and her breasts appeared to be a modest D cup if he had to guess. Her long wavy blonde hair fell past her shoulders when it was down but today it was pulled back in a tight ponytail. The reason DJ didn’t mind seeing Amanda fully dressed that day was because of a fetish he had for nylons and pantyhose. She was wearing sheer smoke grey nylons with a pencil skirt and jacket that looked very expensive. His eyes focused on her silky legs and the towering stiletto heels she had on.
DJ watched as she advanced toward the grotto where he was kneeling then stopped to sit down at one of the tables bordering the poolside. She was on her cell phone and carrying a lap top which she opened as she talked. The splashing of the waterfall didn’t allow him to hear what she was saying but she seemed agitated. He walked out the rear entrance of the grotto to check the filter and determine if it needed replacing. He wanted to get another look at Amanda but he pulled the filter first. It was badly clogged with what looked like the bottoms of a bathing suit. It was too big to be one of Amanda’s but it may belong to one of her ‘friends’. The filter wasn’t damaged so he put it back in place then decided to show what he found to his client.
As he approached her, she was still talking on the phone with her back to him. DJ took a good long look at her crossed legs as she bounced her foot mindlessly. She turned to face her lap top and saw him coming.
“Listen Pam, you tell the caterer that they have to be here by 2 pm on the 29th to get set up and be out of here by six when the guest are supposed to arrive,” she said then gave DJ a wave, “I’ve got trusted servers for the evening so they don’t need to send any. Thanks…gotta go.” She ended the call and turned to face DJ. “Hello Dillon…what have you got there?”
He wasn’t sure why but every time she talked to him, he felt as if she was sizing him up for a meal. Her hazel eyes had this unique sparkle as she looked him over. He’d seen lust in the eyes of many of the women he came in contact with doing his job but she was different. It seemed almost predatory but he liked it.
“It looks like one of your guests lost a piece of their swimwear,” he said holding up the item, “This was in the primary filter for the hot tub. One of the grates had come off so I fixed it. I think that’s how this got in.”
She took the garment and inspected it then asked, “How do you know it’s not one of mine?”
“That’s way too big to fit you like I’ve seen…” he stopped as she cocked an eye brow. Fearing he may have said the wrong thing, DJ rephrased his words, “I mean…it’s really not your style.”
“Oh? What is my style?” she asked, pivoting in the swivel chair and crossing her arms under her breasts, “Have you been paying that much attention to what I wear around the pool when you’re here?”
“Well no…it’s just…I’ve seen you when I’m working but…” his cheeks were burning as he fumble for the right thing to say, “I don’t think that’d look good on your tight…I mean, it’d be loose on you.” He was having trouble meeting her gaze, partly from embarrassment and partly from being distracted by her legs.
“I see…Well are you finished here today?” she asked once he was able to look her in the eye, “Did anything need replacing?” Amanda uncrossed her legs to sit forward and when she did his eyes went to her legs briefly.
“No…The bikini bottoms didn’t damage the filter or anything,” he swallowed looking at her face once more, “but one of the lights in the grotto has a bad bezel. It’s looking badly corroded. It should be replaced.”
“Okay…replace it.”
“I’ll have to see if we have any at the shop. If not I can order one for you.”
“How long will it take if you have to order it?” she asked with noticeable concern in her voice.
“A couple days…a week tops.”
“Shit, that’s cutting it mighty close. Can it wait until after my party on Saturday?”
“It could be an electrical hazard but if I shut the lights off to the grotto, someone is bound to take a fall.”
Amanda’s phone began to ring.
“Well then I’ve definitely gotta replace it. Let me know as soon as possible when you can do it.”
“Will do,” DJ answered and went to collect his gear.
***
Back at the shop, DJ wasn’t able to find a replacement bezel. He placed a call to one of their suppliers and found the part but it wouldn’t get to them until late Thursday. He called Amanda but only got her voice mail. He left a message and his number to see what she wanted him to do then called the supplier back and ordered the part just in case.
His phone rang as he came to a stop in his parent’s driveway. DJ looked at his phone but didn’t recognize the number. “Hello,” he said, stepping out of his truck.
“Hi Dillon, its Amanda Michaels.”
“Hello Ms. Michaels. Did you get my message?”
“Yes I did. You didn’t say when you could fix that light.”
“I’ve got a full schedule Friday. I could stop by after I’m done but it might be late,” he replied, hoping that wouldn’t be a problem.
“How late is late?” she asked.
“I should be there sometime after 5:00 barring any problems at my other stops.”
“That’d be great,” Amanda sounding relieved, “I’ll see you then. Bye!”
DJ walked into the house and up to his room. He saw a note on the door in his mother’s writing that read.
DJ,
Julie stopped by to drop off your costume and remind you about Friday and said don’t be late.
Mom
“Damn!”
He’d forgotten he was supposed to meet his girlfriend Friday evening to go out with friends to a costume party. It was going to be a casual gathering at one of their houses but she wanted him to pick her up at 6:00 pm that night. That would be cutting it awful close assuming everything went perfect at work on Friday. He snatched the note from the door and entered his room.
There was a bag on the bed with what he expected to be a wolf costume for the party. He was going to be the ‘Big Bad Wolf’ and Julie was going to be Red Riding Hood. What he found was a flesh tone ‘morph suit’, a blonde wig, a pair of gold spandex shorts and gold boots.
“What the hell is this?” he wondered aloud. DJ pulled out his phone and called Julie.
“Hey babe,” Julie said as she answered, “I dropped off your costume this afternoon.”
“So I see. What happened to the wolf costume?”
“Oh I had a change of plans. Becca and John are going as ‘The Big Bad Wolf and Red Riding Hood’. She showed me her costume and it was much more reveling than mine.”
“So?” DJ exclaimed, “What difference does that make?”
“I’m not going to a party dressed the same as one of my friends who is going to be showing off more skin than I am. I don’t need the competition.”
“Are you serious?” his annoyance very noticeable, “What the hell is this costume I’ve got supposed to be?”
“You’re gonna be Rocky from the Rocky Horror Picture Show. I just thought the morph suit would add some mystery,” she said as her voice dropped low and sexy, “And some sexiness too. I’ve even made some modifications to it. I’m going as a sexy Magenta.”
“What kind of modifications?” DJ was already uneasy about this costume but what had Julie done? He heard a beep.
“Ooh, Mandy is calling…I gotta go. See ya Friday,” and she was gone.
“Wait!...Shit!” he shouted in frustration knowing she’d be on the phone for a long time with Mandy. He hadn’t told her about his last minute repair job but figured he’d just get an earlier start and get done a bit earlier. At least that’s what he hoped.
DJ sat on his bed and pulled out the skin tight morph suit to give it a closer inspection. The first thing he noticed was an opening for his mouth. ‘At least I can eat and drink without taking this thing off my head,’ he thought. As he held the garment up, he saw the other ‘modification’. Julie had cut an opening at the crotch big enough for his cock and balls to hang out. She had also sewn a flesh colored, elongated spandex sack to cover his genitalia. It had small strips of Velcro to secure it in place. He was shocked. Knowing Julie, it was done for easy access once they were alone. He couldn’t believe that she wanted him to wear this in public, let alone around their friends. ‘Had she finally gone crazy?’ he wondered.
His relationship with Julie went back a long way. They’d grown up together; gone to the same grade school, middle school and high school. They didn’t date until their senior year and DJ lost his virginity to her as his 18th birthday present from Julie. She was a few months older than DJ and had dated one other guy prior to him. Once she broke up with that guy, she and DJ got together. From what he’d heard from others, the guy just used her for sex.
Julie liked to act very outrageous after that. Some would even say slutty but DJ knew that was just for show. When it came to sex with Julie she was anything but slutty. In fact she was more prudish than anything else. DJ just accepted the fact and didn’t knock it since he was at least getting sex from her. But he felt there was more out there. He stuffed the costume back in the bag, shaking his head and went to take a shower and jerk off to the thought of being with Amanda Michaels.
***
Friday was turning out to be hell. DJ had started extra early that day but it didn’t make any difference. Everything seemed to be fighting him. He had finished the last of his scheduled appointments and raced over to Ms. Michaels place. It was 5:30 when he got there and immediately went to work on the damaged light. He had to make several trips to his truck and do some creative modifications at one of the poolside tables before he was able to get the bezel to fit properly.
Amanda had been watching DJ from her kitchen window, admiring the young man’s efforts and his sexy body. She found him very attractive and had many a fantasy about taking him to bed. Even now she was getting aroused. To take her mind off her naughty thoughts, Amanda poured a tall glass of iced tea and took it out to DJ. As she passed the table he’d been working at, his phone began to vibrate. She looked toward the grotto but didn’t see DJ. Not knowing how important this call might be, she decided to answer it for him.
“Hello, this…” she began before being cut off.
“WHO IS THIS?” an angry female voice shouted, “WHERE’S DJ?”
“Well he’s here with me working…”
“WHAT THE FUCK! I should’ve known,” the call ended.
Amanda looked at the phone in shock and a bit of concern. She hoped she hadn’t made Dillon’s life more complicated. She turned to the grotto once more and saw Dillon approaching. He was sweaty and he looked tired as he carried a bucket with tools and an empty box toward her. He saw her holding his phone and the concerned look on her face.
“Is something wrong?” he asked, setting down the bucket.
“Ugh…I hope not,” she replied handing his phone to him, “It was ringing…and I answered it thinking it might be important…I’m sorry.”
DJ saw nearly a dozen missed calls all from the same number; Julie’s number. He hit dial and turned, walking away from Amanda. The phone rang four times before Julie picked up. Even from a few yards away, Amanda could hear the same female voice begin shouting at Dillon.
“WHERE THE FUCK ARE YOU!”
“I’m finishing a job,” DJ replied trying to keep his voice low in hopes Julie would do the same.
“DON’T LIE TO ME! WHO’S THE WOMAN THAT ANSWERED YOUR PHONE?” Julie was coming unglued.
“Hey! Stop yelling. She’s a client. She answered…”
“OH BULLSHIT SHE’S A CLIENT. YOU’RE PROBABLY FUCKING THAT BITCH!”
“Julie, calm down. I’m not…” he tried to explain.
“FUCK YOU AND YOUR WHORE! I DON’T WANNA SPEAK TO YOU EVER AGAIN!” the line went dead.
DJ tried to keep his cool but he kicked the bucket of tools, sending the contents flying everywhere, including the pool. “Shit!” he exclaimed then saw Amanda looking at him. “I’m sorry about that,” he started, setting his phone down and picking up the scattered tools, “I didn’t mean for this…”
“It’s okay. Can I help you?” she asked, squatting to pick up a roll of tape at her feet.
“No…I’ve got this,” he replied as he knelt and refilled the bucket.
“Alright then…What do I owe you Dillon?”
He pulled an invoice from the cardboard box and handed it to her. She looked at the paper briefly then back to the despondent youth.
She nodded then said, “I’ll be right back.”
He watched her turn and head back to the house. She was again in a work outfit. His eyes focused on her firm calves incased in sheer nude nylon. Even though he was upset about the situation between him and Julie, his cock was rapidly coming to attention as she walked away. When Amanda was out of sight, DJ stood and looked into the pool at the hand full of tools on the bottom. He sighed as he stripped off his shirt and shoes then dove in to the cool shimmering water.
Amanda returned to see Dillon climbing out of her pool with a wrench and three screw drivers that had taken the plunge. She was struck as to how sexy his body was and how horny it was making her seeing the water running off it. His swim trunks clung to him, showing the distinct outline of his cock. It appeared to be fully erect and that made Amanda even hotter. He dropped the tools in the bucket and sat down to put his shoes back on.
“Can I get you a towel Dillon?” she asked as she stood before him.
“I’m not cold,” he assured her, “It actually felt good to jump in.” His half hearted smile did little to conceal his anguish.
Amanda sat down and placed a check for the amount on the invoice next to his wallet along with a one hundred dollar bill. He picked up the check and the money then gave her a questioning look.
“What’s this for?” he asked, holding up the hundred.
“It’s for doing a good job on such short notice.”
“Ms. Michaels you don’t have to…”
“Dillon…Please, take it. You earned it.”
He sighed then said, “Thank you Ms. Michaels. Ya know...you can call me DJ like everyone else.”
“Okay DJ,” she began, patting him on the knee, “and you can call me Amanda.”
He wrote ‘Paid’ on the invoice and gave her a copy then folded the check with his copy and put it in the box. He put the tip in his wallet and went back to tying his shoe.
“I’m sorry about your girlfriend. I hope I didn’t cause that. Would you like me to call her and explain…?”
“Don’t worry about it. It wasn’t your fault. She’s just…I don’t know,” he looked to Amanda, “Maybe this was a good thing.”
She cocked her head and leaned forward, “Sounds like you weren’t happy in your relationship.”
He shrugged and cast his eyes downward. She couldn’t tell if he was looking at her cleavage or her legs but when she sat back and crossed her legs Amanda saw his cock twitch. She could see he was reacting to something.
“Would you like to talk about it?” she asked, watching his features, “I’m a good listener.”
His cheeks flushed as DJ felt uncomfortable and embarrassed discussing his relationship with one of his clients. Especially this one since he’d jerked off to her a lot lately.
“I don’t know…I should probably get going…” he said as he started to rise. Amanda’s hand returned to his knee stopping him.
“They say it’s good to talk to someone when you have a break-up,” she stated in a soothing voice, “It’ll help you cope with the emotions you’re feeling.”
He wasn’t sure if it was her genuine concern, her sensual tone or just the fact he didn’t mind being around this sexy woman but he suppressed his shyness and began to think he could open up to her. He was about to speak when his phone buzzed once. He picked it up and looked at the text that Julie had just sent. It was a picture of her in her very revealing Magenta costume, flashing her bald pussy and giving him the finger. There was a single line that read, “Your lose ASSHOLE!” He just shook his head with a slight chuckle.
“What is it?” Amanda asked with a worried look. DJ handed her his phone. “Wow that’s a pretty risqué outfit. Are you sure you don’t want me to explain to her what happened? I’d hate to be the reason you lose such a sexy lady.”
“It’s all for show.”
“I can see that,” she replied studying the picture closely.
“No I mean it’s not for me it’s for her friends.”
“Okay…I’m not following,” offering his phone back.
DJ took his phone and set it on the table, inhaled deep then began, “She dresses sexy and acts…” he pondered how to put it, “slutty in front of her friends when we’re together but when we’re alone she’s totally different.” The confused look on Amanda’s face made him continue, “She is like a total prude.”
“How do you mean? She doesn’t let you have sex with her?”
“We have sex…it’s just…” the embarrassment was back, “She only wants to do it missionary, with the lights off. She hardly makes a sound then she wants to leave the minute we’re done.”
“That’s odd. Did you ask her to try other positions?”
“Ya…Of course but she doesn’t want to and I don’t push her.”
“Hmm…Does she like it when you go down on her?”
He rolled his eyes at that.
“What?”
“She thinks that’s ‘gross’ and we only tried it once. I’d barely touched her pussy with my tongue and…” he felt his cheeks burning at his graphic de***********ion, hoping it wouldn’t offend Amanda.
“Go on,” Amanda encouraged, apparently un-phased by his language.
“Well she freaked…and had me brush my teeth and wash my face like I was contaminated with something toxic.”
“Did she ever give you a blow job?”
He dropped his eyes again and shook his head.
“Is she your first girlfriend?”
DJ nodded, not wanting to meet Amanda’s gaze. She realized he probably never had a blow job in his life. Maybe it was her horniness driving her actions or having a handsome, neglected young man in front of her but she knew she had to try and cheer him up. Scooting her chair closer to his, she ran her hands up his thighs to the bulge in his trunks. He gasped, sitting up straight with shock and embarrassment in his eyes.
“Ms. Michaels…what…what are you doing?” his voice trembling.
“I want to show you what you’re missing. Just relax and trust me,” she said then added, “It’s Amanda, remember?” Her right hand caressed his stiff member as her left unfastened his shorts.
“I…I…don’t think we should be doing this,” he said unconvincingly.
She released his cock and used both hands to pull down his trunks, dragging his ass closer to the edge of his seat in the process. His cock sprang free and slapped his tight abs making them both freeze. DJ didn’t move because he was in shock at being naked in front of Amanda with a raging hard-on. She was paralyzed by the sight of his beautiful cock.
The tip was bright purple, pulsating with each beat of his heart and slick with pre cum. It was a nice length, maybe seven inches or so with a substantial girth. Veins ran up and down the steely shaft with one looking like a bunch of Z’s strung together. Amanda’s mouth was watering. DJ’s on the other hand, was dry as a desert. She moved closer pushing her nylon clad legs between his knees and forcing them apart. The feel of her silky pantyhose on his skin made him groan at the same time her hand returned to his erect cock.
Her hand slowly pumped up and down making DJ shiver. Amanda’s eyes were fixed on the bulbous tip as it leaked more slippery liquid. Holding him at the base, she angled his cock straight up and lightly flicked the tip with her tongue. She felt a tremor run through his body that made her nipples hard as diamonds. She swabbed the opening at the top and brought her tongue back to savor his taste. ‘Sweet as candy,’ she thought. Lowering her head again, she encircled the entire head with her ruby lips while her tongue fluttered over it.
“Oh God!” he gasped feeling her warm wet mouth slowly engulfing him. It was far better than he ever imagined.
Amanda removed her hand and swallowed DJ whole. Her tongue coiled and caressed his shaft on the way down. Her cheeks hollowed as she applied suction before withdrawing back to the tip. Amanda repeated her torturously slow bobbing, savoring the moment and his incredible cock. She could have kept it up for hours but she wanted to make him cum. She wanted to taste him as he exploded in her mouth. With the way he was already shaking, she knew it wouldn’t be long before he cut loose.
DJ had his eyes pinched shut and he gripped the arms of his chair like his life depending on it. Seeing this, Amanda placed her hands over his to make him relax. When he did, she moved them to her breasts. His eyes popped open when he felt her firm boobs in his hands. Her mouth never left his cock as she did this. He tentatively squeezed her breasts through her silk blouse and lacey bra, exploring the resilience of her flesh. Amanda returned to the task at hand, making this sexy young man cum.
Amanda’s mouth devoured the youthful cock like there was no tomorrow. Her right hand returned to his shaft, following her lips up and down. Her left hand fondled his heavy balls. She extended a finger to caress his perineum and his puckered anus and she noticed his whole body tense up when she did this. He was now on the verge of exploding and Amanda was about to push the final button to that detonation.
With one final throat filling plunge, Amanda pressed her finger firmly against DJ asshole. His body went stiff as he unleashed a torrent of hot semen into her mouth. He let out a guttural groan each time his body spasmed, shooting more cum down Amanda’s throat. She was surprised by the force and volume of his ejaculation and nearly choked on the first spurt but being a seasoned cock sucker, she recovered quickly and drank his seed gracefully.
Amanda eased her oral assault but continued to suck and lick DJ’s twitching member even after he was spent. His body jerked and trembled as he struggled to catch his breath, coming down from a tremendous euphoric high. When Amanda finally removed her mouth from his cock and licked her lips in triumph, it was as if he’d been doused with a bucket of cold water; the realization of what had just occurred shocked him back to reality.
DJ shot to his feet, sending his chair skidding backward. He stumbled back then quickly yanked his shorts up as he tried not to look at Amanda sitting before him. She had a satisfied smile on her face. DJ was panicking. ‘What have I done?’ he thought. He stood there for a moment then hastily began collecting his things.
“What’s the matter?” Amanda asked with growing concern, “You didn’t do anything wrong.”
“I’ve gotta…I’ve gotta go…I’m sorry Ms. Mich…I mean…I’ve gotta go,” he stammered then grabbed the bucket of tools and bolted for the side gate.
“DJ…Wait. You don’t have to leave,” calling after him as she stood but he didn’t stop.
In his panicked flight down the side yard, DJ knocked over one of Amanda’s recycle bins, sending papers and plastic bottles flying. He stopped and tried to quickly clean the mess, hoping she wasn’t following. Grabbing handfuls of paper, he tossed them back into the bin when one caught his eye. It had images of people in all forms of costume and many without costumes at all. He noticed a couple more of them in the bin that looked like something had been spilled on them. DJ shoved the one he held into his pocket then collected the last of the empty bottles, returning them to the bin. He picked up his things once more and dashed to his truck. He drove through the streets of the tract like he was being pursued by the Devil himself but once out onto the city street, he slowed. ‘What have I done?’ the question continued to repeat in his head.
***
Sitting on his bed, DJ was trying to come to grips with what had happened that evening. He was confused, embarrassed, upset and strangely curious about why Amanda had done what she did. He knew why Julie had flipped out but he wasn’t all that concerned about their relationship anymore. He replayed the events in his head again and again. Each time he saw the text from Julie, it made him mad that she didn’t want to know why he was late and then assumed he was cheating on her. His conversation with Amanda made him uncomfortable. He couldn’t believe he told her all those personal things. And then she…He felt his cheeks burning as he relived the most intensely pleasurable thing he’d ever experienced in his life to that point. ‘Why am I embarrassed?’ he wondered. Then he pictured himself cumming in Amanda’s mouth. How her finger against his ass set him off. Another wave of embarrassment washed over him. ‘Was that normal? Am I gay? Straight guys don’t cum if their ass is touched do they?’ The questions kept repeating as did the concern and mortification. The feelings she gave him made him feel so good yet he felt such shame; why? He shook his head then placed his hands on the bed to stand when he felt something in his pocket. It was the paper he found at Amanda’s.
DJ removed the soggy paper from his damp pocket and straightened the crumpled sheet. It was an invitation to Amanda’s Halloween Party tomorrow night. It was about 5”x7” and printed on heavy bond paper. Looking closer he noticed the lower right corner had a stain of some kind like the others he saw in the bin. She must have thrown it away because it was ruined.
He turned his attention to the collage of images on the front. The people in the pictures were dressed in a variety of costumes, most of them very revealing. Some of the people, both men and women, were displaying much more of themselves than others. He saw one picture of four people dressed as ‘sexy cops’. One of the four was definitely a man by the uniform he wore and his bared chest but the three remaining were all in scandalously short skirts and high heels showing off their nether regions. That’s when he noticed two of them had cocks. They didn’t look like men in any other respect however. They were both very attractive with massive boobs bulging from their tops but they had large penises between their legs. He was shocked. He scanned the other pictures and saw women kissing women, men kissing men, men and women engaging in various sexual acts. It blew his mind and was making him hard too.
He wanted to see more but that was all the images on the invitation. He flipped it over and saw the date and time along with the address and was about to turn it back over when he read ‘The Rules’ printed on the lower half. ‘The party had rules?’ he wondered reading on.
Number one: All attendee’s must be in costume when they arrive. After that…clothing is optional.
Number two: All attendee’s must wear a mask concealing their identity at all times.
Number three: There are no couples allowed at this event. Bring your partner/spouse/significant other but they won’t be bound by any commitment of fidelity this night.
Number four: Enjoy yourselves to the fullest!
DJ was intrigued. He wanted to see this party first hand but how? The bottom of the invitation was smeared but he also read that the invitation was to be presented at the door. That was assuredly to keep out the uninvited. For a moment he thought he might be able to use the one he had to get in but decided against it with the deplorable condition it was in. He had to find a way to see what happens at one of Amanda’s parties. He thought about flying his drone over head but he wouldn’t be able to get past the main gate easily and parking out front in his Toyota truck would be suspicious. He knew he could hike up the creek bed behind the wall to where Amanda’s house sat but there were too many trees around to safely fly it, not to mention the people would hear it and he’d have to high-tail it outta there before security found him.
“Wait a minute,” he said out loud as an idea struck him, “The trees.”
He actually meant ‘the tree’ referring to the huge oak in the back corner of her lot. Its massive branches over hung both sides of the wall. He was confident he could climb it and get over the fence and into Amanda’s yard. Then how would he get back out? He decided to leave a concealed rope so he could go back over the way he’d come. It was very dense back in that part of her yard so it easily would go unnoticed. There was no way he could sneak out the front gate with all the security lights and a guard on duty.
Now his only concern was could he go through with his plan? The other party goers would be very uninhibited unlike himself. He looked at the invitation again. How could he mingle with people that had no problem showing off their genitalia in front of others? His face was glowing red at the thought of doing that and it would be worse if he was actually there. He could see the masks most of the people had on in the pictures. They looked very Victorian, covering their eyes and nose but leaving the rest of their face exposed. He’d stand out like a sore thumb then he remembered the bag at the foot of his bed with the costume Julie had given him. The morph suit covered his head and face completely except for the slit she made for his mouth. ‘This could work.’ Fortunately he’d already arranged to have the weekend off so first thing in the morning he’d set his plan in motion.
***
Standing by the wall adjacent to Amanda’s property, he could hear music playing as he looked at his watch; 7:10 pm. DJ sized up how to climb over the formidable barrier. One of the two foot diameter branches that hung over to his side of the wall dipped down to nearly ground level so he figured that would be his way over. He wore his costume under a blue long sleeve coverall, from last year’s Michael Meyers costume, and had some gloves to protect his hands. He also had on the gold boots, hoping he didn’t damage them in the climb, and a small backpack.
With some difficulty, DJ managed to get up the limb to the point it crossed the wall. There was about five feet for him to drop to the wall itself then the remaining ten feet to the ground. He pulled a length of rope from his pack, looping it around the sturdy branch. He let the rope dangle to the ground on Amanda’s side and carefully lowered himself to the wall. Once on the ground in the darkness of the tree, DJ prepared to remove the coverall but he heard voices and froze.
Two women walked along a concrete path to a bench that sat just under the canopy of the mighty oak. They were talking and giggling and totally unaware they were being watched. DJ slowly crouched in the deep shadows as the pair stopped at the bench and sat down. One was dressed as a slutty Little Bo Peep in a white mid thigh length dress, white stockings and six inch clear platform heels. Her friend had on a sheer tan body stocking with tufts of white cottony material strategically covering her nipples, a shaggy skirt that matched the length of Bo Peep’s and more cotton at her wrists and ankles. She had on ballet slippers to cover her feet and a lamb’s cowl with ears on her head.
The two began kissing, gently at first but it soon turned into a passionate make-out session. All DJ could do was watch. If he moved, they’d surely hear him. Despite being afraid of discovery, he was getting very turned on by what he was witnessing. After a few minutes of tongue wrestling, Bo Peep knelt on the ground between the lamb’s legs and it wasn’t long before the lamb was moaning. The bench faced away from him but he knew what was happening, Bo Peep was eating her sheep. Just when DJ expected the sheep to cum, she pushed Bo Peep back and stood up, pulling Bo to her feet and having her bend over the bench. It was then he saw that the sheep was a ram, sporting a sizable cock that she drove into Bo’s waiting pussy.
The two moaned and cried out as they fucked. DJ was in shock. He could clearly see the lamb and she didn’t look like a man in that costume, she appeared to be all woman. It disturbed him yet he had a raging hard on as he continued to watch. It took a few minutes but the lamb made several hard thrusts as she came in Bo Peep’s pussy. The two sat again on the bench, catching their breath then went back to the party as if nothing had happened. DJ began to question his decision to crash this party. He needed to do something before someone else showed up.
Taking a deep breath, he removed his coverall and gloves and put them in his pack. He took out his wig and got it in place then hid the pack under some leaves at the base of the wall. Quietly he walked to the path then made one last check of himself before heading toward the house. As he neared the back side of the pool and grotto, he could see people already in the hot tub wearing nothing but masks. Some were kissing while others appeared to be having sex. ‘Holy shit, what have I gotten myself into,’ he wondered.
“Hey Rocky, nice costume,” someone shouted from a group near the pool. DJ just waved in that general direction.
He passed more party goers as he made his way toward the house. There must have been a hundred people or more just around the pool area in a mind boggling variety of different costumes. He couldn’t imagine how many more might be inside, let alone still to arrive. Some he passed complimented him on his costume; others gave him wanton looks, both men and women. His doubt was growing as to the intelligence of his decision to be there and then a young woman in a Playboy bunny outfit offered him a drink. He couldn’t very well pass as everyone else was drinking and he definitely couldn’t say he was under age so he asked for a beer and thanked her. She continued on passing out beverages as DJ took his first sip of beer for the evening.
DJ bumped into Bo Peep at one of the buffet tables loaded with food. He was nervous at first but remembered she hadn’t seen him watching her so he apologized. “Sorry about that,” he said, trying to hide the bulge in his gold Speedo’s.
“That’s alright,” she replied as she turned to face him, “Nice outfit Rocky.”
“Th…Thanks,” he managed as he looked at her smiling face hidden behind a lacy mask.
He could tell she was pretty and her sexy costume really showed off her chest. He took another drink of beer to help stay calm as Bo stepped closer. He wasn’t sure what he was supposed to do, keep chatting, give her a kiss, ask to fuck her or what. Just as he felt like running, the lamb showed up. He was struck as to how pretty she was with only her eyes and the top of her head hidden by her cowl. He looked down at her round breasts with their cotton ball covers and tried not to be obvious but neither of them could see his eyes so he was safe at the moment. He still couldn’t believe she had a cock.
“I thanked Amanda for inviting us,” the lamb told Bo, “Who’s your friend?”
“Can’t you tell it’s Rocky?”
“I can see how he’s dressed,” looking him up and down, “Are you two going somewhere to play? If so, can I watch?”
“No we weren’t…I mean I just bumped into her,” he said, trying to be cool.
The lamb chuckled and with a wink said, “So did I, just a little while ago!” Bo Peep acted shocked then a naughty smile appeared on her lips.
“Actually I was looking for Amanda,” DJ recovered, “Where did you say she was?”
The lamb raised a finger to her lips, “Remember, no names. I slipped myself. The Feline Queen is in the kitchen making sure the food gets out and the drinks are being refreshed.”
“Oh…Right I forgot, no names. I’ll go look for her there. Thanks,” DJ replied backing away.
“If you change your mind,” the lamb began, running her hand under Bo’s skirt making her shiver, “come find us.”
“Ya…Thanks…Maybe later…Okay…bye” he felt like an idiot but thankfully was out of that situation.
As DJ walked toward the back sliding door and the kitchen it dawned on him, ‘What am I doing? I can’t walk up to Amanda and say Hi its DJ.’ Just then Amanda and another woman dressed as a sailor came out onto the patio. DJ was in awe. Amanda was dressed as a cat woman, not like the movies but a female cat. Her hair was teased out into a wild mane with streaks of black and brown and russet shot through it. She had a black head band with ears and her eye liner drew back to her temples. Luminous green cat eye contacts made her appearance look even more primal. It was then he realized she didn’t have a mask on. Her body was sheathed in a sheer black, long sleeve body stocking that did nothing to hide her magnificent breasts and rock hard nipples. She had on a skirt made of animal print material and foe fur that barely concealed her crotch with a tail attached to the back that hung down between her legs. On her feet were leopard print pumps with at least 5” heels. DJ felt as if his dick would explode at the sight of her.
“Make sure the bunnies keep making the rounds,” she said to the sailor, “I don’t want them just hanging out once their trays are empty.”
“I’ll see to it,” the sailor replied and made her way toward the bar.
“Well hello Rocky,” Amanda said as she slowly walked around DJ inspecting his outfit, “Nice job on the costume. It looks good on you Trevor.”
She thought he was someone else. That was good but she might get suspicious if he didn’t say something, “I thought we weren’t supposed to be using names?”
“Oh…Ya, sorry…My bad, you’re not Trevor are you?” she said as she looked him up and down once more.
“And I thought we had to keep our masks on all night?”
“Aren’t you the rules lawyer tonight,” she stepped in close and whispered, “It’s called hostess privilege.”
Her chest was almost touching his as she looked where his eyes should be. Her hand suddenly found his throbbing cock and that seemed to surprise both of them; DJ, because he wasn’t expecting her to grope him and Amanda at finding a nice hard cock ready for action. A seductive smile spread across her face as she maintained her hold on the solid member she had found. She pressed into DJ, moving her lips to his ear.
“Is this for me?” she purred.
DJ thought fast and replied, “Hostess privilege.”
She cocked her head and her smile broadened. There was something familiar about Rocky’s voice; she just couldn’t put her finger on it.
“I like the sound of that,” she said as her free hand moved to the back of his head and she brought her lips to his for a passionate kiss.
DJ was quick to accept her tongue into his mouth and soon they were dueling for control. His hands found her hips but he wasn’t sure if he should grab her ass or her breasts. His hesitation made him miss the opportunity for feeling either as Amanda broke their kiss and stepped back to look him over again. He could tell she was considering something but wasn’t sure what it might be. He didn’t have long to wait to find out.
“Fuck it! I’ve been so horny all week, I might as well get this party started,” she said but he didn’t think she was talking to him.
Taking his hand, Amanda led DJ through the kitchen and dining room, which were full of people, to the stairs leading to the second floor. There were people still coming into the foyer as they ascended and others on the stairs themselves. When she reached the landing with DJ in tow, she turned right and a man also dressed as a cat removed a velvet rope and ushered DJ past. The hall erupted in cat calls, whistles and cheers. He could hear people saying, “Lucky guy,” and “Wish that was me,” as she walked him to a pair of large double doors. She opened them and followed him in. Before closing them, she hung a ‘do not disturb’ sign on the outside.
DJ was standing in the master suite or in this case the Mistress’ suite. Everything about it was huge, especially the bed. It was the biggest he’d ever seen. One would practically need a step ladder to get in the enormous four poster with its satin sheets, fluffy comforter and mountain of pillows. He was still looking around in wonderment when Amanda called him to her.
Again a hand went to his stiff dick as she tried to stab her tongue down his throat. He was kissing back now with much more confidence and she was getting even more turned on by that. This time he found the courage to let his hands wonder to her full breasts, squeezing the firm mounds and rolling her erect nipples between his fingers. She moaned into his mouth as she maneuvered him to the side of the bed. This time when they separated Amanda was panting. Her eyes went to his gold shorts hiding his rampant cock. She knelt and prepared to yank them down.
“Let’s get these off,” removing the Speedo in one smooth move, “What have we here?” Amanda was surprised by the fitted spandex sheath covering his steely member and pendulous balls. “Get on the bed,” she ordered without taking her eyes off his groin. She put a couple pillows on the floor and knelt before DJ, still fascinated by what was concealing his cock. She pushed him back onto the bed and spread his legs wide. When she found the Velcro closures she smiled then removed the sheath. She let out a gasp at the sight of his throbbing cock.
Amanda loved cock but some were just more beautiful than others. This one in front of her was definitely top shelf. Her hand closed around the shaft as she gave it a gentle stroke. When she leaned in to get her first taste, she noticed the veins running along its length. One in particular caught her eye, appearing to be a wavy line of “Z’s”. She knew this cock but how could it be here? Not wanting to alert DJ to her revelation, she began kissing and licking the head while trying to decide how to proceed.
It had been just over twenty-four hours since she had this cock in her mouth and Amanda couldn’t stop thinking about it. She wanted it again; she wanted DJ so badly after last night and now here he was. What she didn’t want was for him to run off again. ‘First things first,’ she thought, ‘I’m gonna have another taste of his creamy load.’
Her lips made a tight seal around the crown of DJ’s cock, bringing a satisfied groan from the young man. Amanda’s tongue went to work, swabbing and probing the pulsating penis in her mouth. She slowly swallowed him to the base, keeping him in her throat as long as she could until the need for oxygen became critical. She took him down again, holding out as long as possible then coming up for air. She licked his length then concentrated on his velvety sack; sucking first one then both of his balls into her mouth to be toyed with by her tongue. When her mouth left his balls to return to his cock, her left hand took over fondling them. Her right gripped his shaft, stroking and twisting in time with the movements of her mouth.
DJ was in heaven. Amanda kept bringing him to the edge of release then would back off long enough for him to regain control. She kept this sensual torture going, driving DJ to the point of begging her to let him cum. She knew she had him. It was time to get her treat. Amanda slowly ramped up the stimulation once more but this time the middle finger of her left hand moved toward his ass. It circled with just the lightest touch on his sensitive sphincter. Then as she was about to swallow him whole, the pad of her finger pressed firmly at his back door.
DJ’s body arched off the bed when his cock erupted. He let out a hoarse scream that even startled Amanda. With each pulse he cried out and she synchronized the pressure on his anus in time with his ejaculation. Amanda sucked and swallowed for all she was worth, not wanting to lose a drop of his tasty seed. When DJ was finally spent, she ran her thumb up the underside of his twitching shaft to push out the last of his cum.
Her belly now filled with his warm cream, Amanda let out a satisfied purr as she sat back on her calves. It was now time to see if she could determine DJ’s limits. He was so shy and yet had the courage to crash her party and come to her room thinking his identity was still secret. Would it be possible for her to expand his horizons? There was only one way to find out but she felt she needed to reveal she knew his secret. She climbed onto the bed next to the teenager with her back to the pile of pillows. Throwing a leg over his nearest thigh, she pressed her lips to his. His hand caressed her left breast as they kissed.
“Mmmm…That was as delicious as the last time I sucked you off,” she cooed, rubbing her stomach, “Your cum tastes so good.”
“Ugh…What do you mean? I’ve never…I mean…This was…”
Amanda’s hand came to rest on his slowly shrinking member. Her finger traced the zigzag vein toward the tip, making his cock jump. She knew it wouldn’t be long before he was hard and ready for action once more but she wanted to take things slow for the moment.
“DJ, I know it’s you. I never forget a beautiful cock and there aren’t many as I’ve see as gorgeous as yours,” she said continuing to follow the distinct identifier with the tip of her finger, “You see this cute little feature on your cock gave it away.”
“I…umm…I just wanted…” he stammered nervously.
“I’m not mad…A little surprised but I’m not angry,” she assured him.
“You’re…You’re not?” turning to face her.
The way his suit muted his features was becoming distracting, “Can you take off your mask so I can see your handsome face?”
There was a moment of hesitation then he reached back and lowered the zipper a few inches so he could pull the mask forward over his head. Amanda smiled seeing his flushed cheeks. She kissed him quickly then pulled back to take in his features. He was so handsome she just wanted to eat him up. She could feel his cock stiffening under her touch so she began to slowly stroke him.
“I hope my guests didn’t shock you too much with their lewd behavior,” she smiled, cocking her head.
“Well I guess not. They seem to be a very…open bunch of people.”
“That’s putting it mildly,” she chuckled. Amanda could see he wanted to say more, “Are you sure nothing you saw bothered you?”
He took a deep breath then said, “When I first got here I saw two women together. They were kissing and touching each other.”
“Did that turn you on?”
“Well yes…” there was a long pause.
“But?” she asked.
“But then they started to have sex and one of them had a cock,” he blushed again.
“There are some men here that are dressed like women.”
“She looked like a woman except for the cock between her legs.”
“And that bothered you?”
“Well it was pretty hot until I saw that, then…I don’t know, it was weird,” he confessed.
Amanda could see his uncertainty and embarrassment over what he saw. She could tell something about that might be drawing into question his own masculinity and possibly his orientation so she decided to change the subject in hopes of easing his tension.
“How did you enjoy your second blow job?”
“It was…intense, like the first time…” he trailed off like he was hiding something.
“You sure did cum hard when my finger touched your ass,” she said with a huge smile. That’s when she noticed the color deepening on his face. “Is there something wrong, DJ?”
“No! It was incredible it’s just…Is that normal?” he looked away.
“What do ya mean?”
“Do guys normally cum hard if you touch their ass? I’m just wondering because…” he trailed off again but Amanda had a feeling she knew where he was going.
“If you’re worried it ‘makes you gay’ for some reason, it doesn’t. If you enjoy pleasurable sensations connected with ass play then just enjoy them. Don’t read anything more into it than that,” she could see he was still not completely sold, “Listen DJ I’m not going to judge you because you enjoyed having your anus touched. In fact I’d like to show you how I can make you cum harder than you ever imagined.”
“Really? How would you do that?” his interest was piqued.
“By massaging your G-spot.”
“I thought only women had a G-spot?”
“They do but men have one too. It’s called the prostate.”
DJ had heard of the prostate before, usually connected to cancer or aging male issues that cause sexual and urinary problems. He had no idea it was a source of pleasure or how that could be achieved. His cock was once again erect but he thought it was just from Amanda’s attention. However he jumped when her finger touched his ass again.
“What are you doing?” he asked nervously, scooting further onto the bed.
“I’m going to massage your prostate,” she said as she sat up and removed a bottle of lube from the night stand drawer.
“I…I don’t think I’m ready for that…”
Amanda’s brow furrowed as she looked at the retreating youth, “Didn’t you complain about your girlfriend not being willing to try new things?”
“Ya but…”
“Don’t be like her. I’m gonna open a whole new world of pleasure up to you,” she stated as she moved closer to the nervous young man, “Trust me DJ…If you don’t like it, I’ll stop.”
“Okay…What do you want me to do?”
“Well this’ll be easier and more comfortable for you if you’re on your hands and knees,” she told him as she shifted position.
DJ rolled over and pushed himself up onto his hands and knees. Amanda maneuvered him toward the center of the bed then pulled a pillow from the pile for him to rest his head if he wanted.
“Spread your knees apart a little further,” she patted his thigh and he complied, “That’s it. Now you need to relax and breathe easy.”
Amanda moved behind DJ and sat on her heels as she lubed up her fingers. She drizzled some lube into the cleft of his ass making him jump again. She applied some pressure with her middle finger to his puckered ass and he reflexively clenched.
“Relax,” she tried again with the same result.
Reaching under him, Amanda began to stroke his cock with her free hand while making small circles around the rim of his ass. When she felt him finally relax his sphincter, she pushed her finger in just past the first knuckle. DJ clenched tight and grunted. Even though he seemed to be resisting, his cock had become very hard.
“Are you okay?” she asked in a soothing voice.
“It stings,” he replied.
“Take some deep breathes and relax. It’ll pass.”
The tension around her finger lessened and she pushed further in. Each time he relaxed she drove deeper until her entire finger was buried in his ass. She slowly withdrew and poured a little more lube on it then pushed back in. DJ was getting use to her invading digit and he lowered his head to the pillow. Amanda removed her finger about half way then applied downward pressure on DJ’s prostate. A tremor ran through him accompanied by a deep groan. She circled his G-spot while maintaining the same pressure. The hand that was stroking his cock was now slick with his pre cum.
“Feeling better?” she asked.
DJ just nodded. She could tell he was concentrating on staying relaxed. She added a second finger. It went in much easier than the first so she worked both fingers around his prostate. His body began to tremble each time they passed over it. She released his cock and focused on his ass.
“Are you doin’ okay?” as she added a third finger to the mix.
“Yes,” he gasped, “I’m good.”
“Are you ready for more?”
He nodded with his eyes closed and his head down. He felt Amanda shift slightly behind him then he felt more lube running down his crack. She shifted again as her fingers left his ass. He stifled a disappointed moan then felt something hot and firm but resilient being pushed into his ass. At first he thought it was some kind of toy then her hands were on his hips and she moaned. He pushed himself up and looked over his shoulder in time to see the last of her cock sinking into his butt. Before he could say or do anything else, her hips began to sway side to side causing her cock to glide back and forth over his special spot. His arms turned to jell-o and he collapsed into the pillow.
“What the fuck Amanda?” his voice muffled.
“I’m sorry DJ but I couldn’t help it. I had to have you and I was afraid to tell you I’m a transgender woman.”
DJ was stunned. He would have never guessed Amanda was transgender. Part of him wanted to run away in disgust but the other part was so caught up in the intense pleasure she was giving him that he couldn’t move.
“We’ve gotta stop…” he gasped.
“Am I hurting you?”
“NO…It’s just…It’s…Oh GOD!”
Amanda knew he was on the brink once more so she stopped rocking her hips and leaned over his back to whisper in his ear.
“You’re so fucking hot DJ. I just want to make you feel good,” nibbling at his lobe.
“I can’t believe I’m doing this,” he moaned.
“Are you gonna to cum for me baby? You’ve got me so turned on I’m gonna cum for you,” Amanda said as she rose back up, “I’m gonna fuck you ‘til we both cum.”
DJ was unable to process what was happening. His mind was telling him this wasn’t the way things were supposed to go but his body had completely given into Amanda and what she was doing to him. He was in turmoil when he felt Amanda’s cock sliding out of him until only the tip remained then slowly impaling him again. She felt huge inside him but her cock was roughly the same size as his, just not as thick from what he could tell. Her long slow pace began to increase in speed then her strokes shortened when she changed the angle of penetration. The head of her cock was poking his prostate with rhythmic efficiency now, driving him to a powerful release. Her sexy talk and increasing moans were adding to the intoxicating mix of sensations.
“Oh God Amanda…I’m getting close…You’re gonna make me cum.”
“That’s it baby, cum for me and I’ll cum for you,” she purred, thrusting faster.
Her words and the increased speed of her driving hips sent him over the edge.
“OH FUCK!” he shouted, sending jets of cum spraying onto the comforter beneath him.
His ass contracted in concert with his pulsating cock giving Amanda intense pleasure. She was close and returned to long deep strokes. DJ’s clenching ass finally set her off and she came too.
“OH Baby I’m cumming for you!”
In the haze of his own orgasm, DJ felt a warm sensation filling his insides from Amanda’s cock throbbed and pumped her cum into his rectum. It was an odd feeling but pleasurable. She held her hips tight to his ass until she had shot the last of her load then pulled him over onto his side to cuddle with her. They managed an awkward kiss as they lay panting, both their cocks still twitching with the last remnants of orgasm. There was an uneasy silence, making Amanda feel as if this may not have been a good idea then her cock slipped from his ass, DJ rolled toward her for a more passionate kiss. She melted in his arms enjoying the moment.
She could feel his cock against her thigh and looked down. It had diminished a little but it was still hard. He cupped her breast and they kissed again briefly.
“I hope you’re not having regrets about what we did?” she asked staring into his eyes.
“I’m not sure how I feel. I was seriously scared for a bit then I came so hard I almost passed out,” he admitted softly, “It’ll take some time to get use to this whole thing but it was incredible.”
She smiled at that and the feel of his cock poking her leg. She wanted him to fuck her but felt timid about asking. It was unusual for her to be timid with a sexual partner but DJ was special. She didn’t want to scare him off because he truly aroused her. She sat up, kicked off her heels and tossed her skirt onto the floor then slid off the bed. She kept looking at his beautiful cock throbbing against his abdomen.
“I want you to spend the night with me,” she said hoping he wouldn’t reject her.
“Really? Okay on one condition,” he sat up.
“What’s that?”
“I get to make love to you while you wear that sexy outfit,” he replied with a sly smile.
She couldn’t believe her ears. He said ‘make love’ not fuck. She was shocked. He truly was special.
“Take those boots and silly suit off first.”
He ran the zipper all the way down and peeled the clingy spandex down to his shoes. He untied the laces and kicked them off along with the morph suit. Once he was naked, Amanda crawled up onto the bed, lay down with her head on the pillows, spreading her legs wide for him. He had a funny look on his face and then it hit her.
“I know…missionary is the position Julie always wanted to do but I want to be able to kiss you and hold you when you make love to me,” choking up on her own words, “Don’t worry, we’ll change positions before we’re finished.”
DJ smiled and reached for the lube. He coated his cock and ran his slippery fingers into Amanda’s waiting hole. She shivered while holding her legs wide open with her knees at her chest. She could see that DJ was shaking as he positioned himself. The first contact between her ass and his cock made Amanda gasp. He was gentle, slowly pushing into her.
“That’s it, go slow so I can get use to that fat thing,” she cooed.
“You’re so tight,” he commented as his hips touched her ass.
When he was all the way in, Amanda closed her silky legs around his waist and drew him down for a long wet kiss. DJ hips thrust his cock in and out with a slow steady pace. He kissed her nipples through the body stocking, switching back and forth between them. Her cock was growing stiff, making its presence known, trapped between their bodies. Amanda was moaning loud and giving him encouragement as he ramped up the pace. She pulled him down for another kiss then gave him a seductive smile.
“Time to switch,” she said and rolled to her right, taking DJ with her.
She now straddled his hips while making a slow rolling motion with her hips. Only half of his cock was inside her but she seemed to be in a blissful state riding him. DJ now had a good look at her cock and his estimation of its size wasn’t far off. She was equal in length to him but not as thick. He was transfixed by the stream of clear liquid leaking from the tip as she bounced up and down. He moved his hands to her jiggling boobs, squeezing the firm globes while tweaking her nipples.
“That feels so good, don’t stop playing with my tits,” she moaned.
DJ was thrilled at her reaction to his attempts to please her. Her lustful cries and sexy words were making him very aroused and her tight clenching ass was pushing him closer to another orgasm. Her vigorous bouncing made her cock slap against his belly, smearing more of her pre cum on his abs. His eyes focused on her beautiful face, contorted in pleasure. They traveled downward to her nice, round breasts, veiled in nylon and captured in his hands. When they reached her cock once more he no longer cared that Amanda wasn’t born a woman. She was as much a woman as any he knew.
“I love your amazing cock, DJ,” she panted, “You’re gonna make me cum again.”
She leaned back and rode him faster. He placed his hands on her hips and helped guide her up and down. Her breathing was coming faster now and he could feel her ass sporadically tightening. DJ wanted her to cum. He wanted to feel it happen then she lunged forward, her hands now on his chest.
“OH FUCK YES!” she screamed, her body quaking.
A stream of hot pearly cum splashed onto his chest followed by another then another. Amanda was grinding herself into his hips making her spasming cock shoot ropes of cum all over him. When her hips finally stopped moving, her head bowed surrounding his with her flowing hair. Her eyes were closed at first as she sat there panting. When they opened, she saw DJ grinning at her. A warm smile crossed her lips then she leaned down and kissed him. It was soft and gentle, devoid of urgency. Their lips lingered together for a moment before she sat up. She saw DJ covered in cum and giggled.
“Oops! Looks like I made a mess,” she giggled again then began to lick him clean.
It was the most erotic thing DJ had ever experienced. Her warm tongue and supple lips moving over his skin and removing her spunk really struck a chord with him. She paid extra attention to his nipples even though they had been missed by the majority of her release. She just wanted to tease him a little. She sat up again with a satisfied smile on her face.
“There, all clean,” she pronounced, “Now it’s time for you to cum.”
She crawled off DJ reluctantly and knelt beside him. Amanda dropped to her elbows, keeping her ass high in the air. She looked over at DJ and gave her butt a seductive wiggle.
“Come and get it big boy,” in a sultry voice.
DJ didn’t need to be asked twice. He was behind her in a flash. He eased himself in fully then leaned over her back for a quick kiss. He rose up and hammered away at Amanda. She was driving back into him, meeting his thrusts with equal force.
“Oh God DJ, FUCK ME…Fuck me good with that gorgeous cock!”
He pounded away, enjoying her tight ass pulling at his cock. He was rapidly approaching his own blissful precipice. Knowing he wouldn’t last much longer, DJ wanted to see if he could make Amanda cum again too. Holding her velvety hips, he changed the angle he was driving into her along with shortening his strokes. He tried to mimic what she had done to him. His efforts were met with approval.
“OH YES BABY! Right there…Right there!” she cried bucking her hips violently.
“Amanda…I’m gonna cum,” he announced with a groan.
“Cum for me DJ…Cum for me…Yes…Yes…YES!”
As DJ’s balls emptied their contents into Amanda, he could feel her sphincter rhythmically contracting too. She wasn’t cumming as hard as she did before but she was enjoying the pleasure he was giving her. When he was finished, DJ collapsed onto the bed next to Amanda. The two lay there for several minutes catching their breath.
Amanda finally rolled on her side to face the young man who had rocked her world. He was staring at the ceiling with a gratified smile. He was sweaty and looked tired but fully satisfied.
“I need to get back to the party,” she said somberly, “I’d rather stay curled up with you right here.”
“I understand, you’ve got a lot of guests down there,” he turned to her, “Do you still want me to spend the night?”
“Absolutely! You better not run off again,” she said in a commanding tone, then softened, “But I can’t let you come back down to the party. If anybody found out you’re under age with all the alcohol, it’d be my ass.”
“And such a sexy ass it is,” giving it a playful smack.
“I’m serious DJ; you need to stay outta sight.”
Her tone let him know she wasn’t kidding, “I don’t mind hanging out up here. I’ll take a shower and be waiting for you to come to bed.”
His charming smile made her heart melt. She was falling for this kid and she didn’t seem to mind.
“I’ll tell you what. You get cleaned up and put your costume back on and I’ll send up some food and a special treat…but you have to leave your costume on the whole time.”
“Okay…What kind of treat?”
“You’ll see,” grinning wickedly.
Amanda kissed him deeply then slid out of bed, pulling the stained comforter with her. She put on her skirt and heels and went to the bathroom to fix her make-up. DJ gathered his costume and followed her into the bathroom to shower. He was washing his hair when Amanda was about to leave. She told him not to stay in too long as she would be sending up what she’d promised in a few minutes. He finished rinsing then stepped from the shower. He dried himself with one of the softest towels he’d ever felt.
DJ was pulling on his boots when there was a knock at the bedroom door. He looked in the mirror to make sure his wig was on straight and nothing was out of place then went to the door. He opened it expecting to see Amanda or one of the Playboy bunnies delivering his snacks but what he saw made him gasp. It was Bo Peep and her lamb carrying a tray of sandwiches and chips along with a two liter bottle of Coke.
“Hi Rocky…” they said in unison.
Bo stepped through the door followed by her lamb and set the food and drinks on a nearby table. The lamb pressed her body to his, bringing her lips to his ear.
“Amanda said…I mean, the Feline Queen said we were your treat,” her voice low and husky then gave him a brief passionate kiss. As soon as she pulled back, Bo Peep kissed him deeply then loosened her dress and let it fall to the floor.
The two ladies took the stunned young man’s hands and led him to the bed.
“Are you ready for your treat?” they asked together.
Less than two hours earlier, he felt aroused and disturbed by these two. Now he just felt aroused. His experience beyond the wall was just beginning.