Part 2
James pushed his plate away and sat back savoring the fine breakfast his aunt had prepared for him. She was in her room getting ready to go to the gallery even though it was after noon. He could still taste her on his lips. After the confusion of waking up in his own bed that morning, then getting an amazing blow job from Lisa, James made sure he showed her his oral skills before they both had a proper ‘morning’ meal. The feel of Lisa’s hand caressing his shoulder made James jump.
“I’m sorry, I didn’t mean to startle you,” Lisa said as she picked up his plate, “Were you daydreaming?”
“Just thinking about all that’s happened.”
“Not having any regrets I hope?” she replied, placing his dish in the sink.
“No…None at all!”
Lisa came back around the counter to stand in front of her nephew as he sat at the breakfast bar. She swiveled his chair so that he was facing her. Pressing her tiny body between his legs, she stood staring into his dark eyes for a moment. Lisa could feel his semi-hard cock pressing into her stomach. His playful smile made her heart flutter. She wanted him again, right there in the kitchen but she was running very late and wanted to get a few things settled between them before she left for work.
“We need to talk,” she started, trying to stay focused on what she wanted to say and not the growing dampness in her panties. “What we did last night…and this morning goes against everything we’ve been taught that should occur between an aunt and a nephew.” She paused, gauging his reaction, then continued. “But no matter how wrong it is, it felt so right. I just want to make sure you’re okay with what happened so we can figure out where we go from here.”
James clamped his thighs to Lisa’s hips and leaned in, pressing his lips firmly to hers. His arms encircled her as his tongue probed her mouth. When he pulled back enough to look her in the eye, his smile told her everything she wanted to know.
“Lisa I love you and I don’t regret anything that’s happened between us. You’re more than just an aunt to me. You’re a friend and lover too and I don’t want that to change but I’m getting the feeling you’re having some second thoughts.”
Her tiny hand caressed his cheek, “I’m not having second thoughts, in fact I want what we have to continue as long as you’re willing and we can keep it a secret.”
“I’m glad you feel the same way I do, so what’s next?” his smile growing.
James saw a seriousness appear in her eyes, “Well then we have to make sure we’re both on the same page about this relationship. First off, you have to understand I love you too but it doesn’t mean we’re going to run off to some place in the middle of nowhere and get married.” Again she paused to get his reaction, not seeing anything negative she continued, “You have your whole life ahead of you and I don’t want you throwing it away on the silly notion of running off with me, okay?” She wanted James to finish school, have a career and some girlfriends as well.
James nodded in reply. He had considered suggesting exactly that but he knew it was just a fantasy. He also knew his aunt wasn’t the type to get married, at least not yet. She was a free spirited woman and that’s one of the things he truly loved about her.
“So,” she continued, “If we’re agreed that we’re going to keep having fun with each other, then we have to make sure no one and I mean NO ONE finds out about us. You can’t tell anyone, not even your closest friends about this.”
James nodded again.
“At the house here, we can do whatever we want, whenever we want, as long as we’re alone but when we’re in public we have to be aunt and nephew. That means no groping one another even if we’re sure no one can see. No lingering hugs, no kissing except for maybe a quick peck on the cheek and no holding hands.”
“Wow…sounds kinda boring when we go out,” he pouted playfully.
“I’m serious-, Jimmy, we have to be careful. What we’re doing can get us both in a lot of trouble. I’m not too concerned about myself as much as I am about you. This is the kind of thing that could ruin your life and possibly your career if anyone finds out.”
“Now you sound like Mom.”
“Well she’s going to be the one we have to be the most careful around. If she even remotely suspects something is going on, she’ll get it out of one of us.”
James knew Lisa was right about that. His mother always could tell when he wasn’t being honest with her. It was like a sixth sense of hers. He guessed that’s why she was such a good lawyer. She could tell when a witness wasn’t being truthful and knew how to extract the truth in her questioning. James actually was afraid at that moment. Lisa could see the fear in his eyes.
“As long as we don’t give her any reason to suspect us, we’ll be fine. She knows we’re close so we should be able to pull it off as long as we’re careful.”
He seemed to relax at that. It was then he had an idea that could help Lisa in her dealings with that asshole Ray.
“I was thinking, you should talk to Mom about what’s going on with that Ray character,” James suggested.
“No, I don’t want to bother her with anymore of my problems,” Lisa replied, shaking her head, “Laura has enough frustrations with her job. She doesn’t need to be bailing out her little sister again.” She gave James a quick kiss on the lips and started to pull away, “I gotta get to the gallery.”
James held her and reciprocated with a much more passionate kiss that made Lisa weak in the knees. His hands slid down her back, squeezing her firm ass and eliciting a deep groan from his aunt. His cock now fully erect throbbed against her belly, demanding attention. Lisa reluctantly broke their kiss, stepping back.
“If I don’t stop now, I’m never going to make it to work,” she cooed.
“And the problem is…?” James left the question hanging with that same playful smile that melts her every time she sees it.
“Because, I have a lot of things to do today,” she replied, supporting herself on the counter while stepping into her heels, “Sandy and I are meeting with a bunch of the artists this evening to discuss our options should Ray drop his support of my gallery.” She quickly straightened her knee length skirt then looked back to her nephew, “I have to go over some numbers before that happens so I have to go.”
James was only half listening as he took in the view of his beautiful aunt. His eyes traveled from her 6” platform pumps, up her nylon encased legs, over her perky breast in that tight button up blouse to her angelic smiling face. It was then he realized she had stopped talking.
“Are you OK?” glancing to James’ cock, straining to break free of his shorts then back to his eyes, a lascivious smile spread across Lisa’s lips.
“Yeah…I’m fine,” feeling a bit embarrassed about being caught ogling her.
“If I didn’t have to meet with these people today…” her hand lightly caressing his bulging member then pulling back quickly, “BUT I do so we’ll have to wait. Take that big guy and find yourself a hottie to use it on tonight at your party. I’m sure there’ll be plenty there that wouldn’t mind giving him a ride.”
“It won’t be the same.”
“That’s the point;” kissing him quick then heading for the door, “enjoy the new experiences.” Lisa opened the front door then turned back to her nephew, “You’re staying at Mike’s tonight, right? I don’t want you drinking and driving. You shouldn’t be drinking anyway yet but I won’t tell if you do.”
James just nodded.
“Sandy and I will probably be having dinner with these people tonight so I won’t be home at the usual time. If you need to call, I have my cell. Bye!” she blew him a kiss and was gone.
With a sigh, James rose from his seat and went to his room to pack a few things before heading to his friend’s house. When he reached his room, his mind went back to Lisa and her problems with her partner. James fired off a quick text to his mother briefly describing the situation then packed to leave.
***
James arrived at Mike’s place shortly before three in the afternoon and it was already abuzz with activity. He walked through the front door and couldn’t believe his eyes. People hanging festive tropical decorations, coolers being filled with sodas and beer, food staged for hungry party goers; James was impressed as much as surprised at Mike’s elaborate setup.
“HEY bud! You’re early. Well what do ya think,” Mike clapped his hand on his friend’s shoulder while spinning him around to get the full view.
“Dude…What’s all this for?” James was still in shock, “I thought you said it was ‘just going to be a few buds,’ this is more like the set up for a rave!”
“Well you know how it goes, I told the guys I was going to have a get together to celebrate you being back in town and they told other people and…,” Mike took another look around himself, “It kinda snowballed from there.”
“I guess so.”
“Listen,” Mike pulled James close, “A guy I did a job for works at a modeling studio and he let some of the girls know about this party, so we’ll have some fine ladies here to hook-up with tonight.”
“What about Jen?”
“What about her? She’ll be here,” Mike replied nervously at the mention of his girlfriend’s name.
“If she’s here, you’d better not be ‘hooking-up’ with any of those models or she’ll kick your ass six ways to Sunday.”
James had always liked Jen but she was too much of a tomboy for him. She’s tall and lean with short blond hair and a beautiful face but she has a serious jealous streak when it comes to Mike. Her 5’9” frame is all muscle from playing volley ball and doing martial arts and even though Mike has a few inches on her and about 50 pounds, James’ money would be on Jen if things got physical. She adored Mike but he knew she wouldn’t put up with him fooling around on her.
“OK, what I meant to say was, you’ll have some fine ladies to hook-up with.”
“Where is Jen anyway? I haven’t seen her yet?” James asked as he looked around for Mike’s lady.
“She’ll be here…soon,” Mike’s voice hiding something from his friend.
“I figured she’d be here helping you decorate,” James pressed.
“She was but…”
“But what? C’mon Mike, spill it.”
“She’s picking up Dana,” Mike braced himself for what was to come.
“WHAT!” James shouted, “Why’d you invite her?”
“I didn’t, Jen did. They’re BFF’s so she told Dana about the party and…Hey man I’m sorry,” Mike tried to calm his friend, “Just stay away from her and …hopefully…she’ll stay away from you.”
“Yeah right,” James replied throwing up his hands in exasperation.
“Take your pack up stairs then come back down here and have a beer…or five,” Mike laughed hoping to take his friend’s mind off Dana.
James did as Mike suggested and tossed his bag on the bed in the guest room he was to occupy that night but he was still fuming over Dana being at the party. Dana was a beautiful young woman. If she was taller she could have been a model. Her long flowing chestnut hair and gorgeous ‘Girl next door’ features made her something to behold. But at 5’-4” she was a bit short to walk the runways. She had amazing breasts too. James loved to fondle her perfect C-cups every chance he’d gotten. He lost his virginity to her and the sex after that was unreal. They had dated through the last two years of high school but broke up just as the summer got under way. Dana was going to San Diego State in the fall and wanted James to go there too but his mind was set on MIT. That’s where the trouble started. They argued and the break up got ugly.
***
Returning down stairs, James was met by Mike with a huge smile and two beers in his hand. James decided to put Dana out of his mind by drowning her in beer. He took the bottle from his friend and downed nearly half the beer in one gulp. He gave his buddy a crooked smile then touched bottles with him.
“Feeling better?”
James nodded.
“OK then,” Mike raised his bottle, “Let’s PARTY!”
Over the next hour, as if by Mike’s command, the house filled up with party goers. James kept an eye out for Dana in hopes of avoiding her. He visited with old friends, swapping college stories, picking up gossip and generally reconnecting with his former life prior to going to school on the other side of the country. It was while talking tech with one of his ‘geek’ buddies he saw her.
The medium height brunette was sitting on one of the couches in the living room, texting on her phone. She was beautiful. Long wavy hair, tight midriff top that showed off her perky breasts, Daisy Duke shorts but what really caught his eye was her legs. She wore black lace pattern tights with converse high tops. Although he’d have preferred some sort of heels, he wasn’t going to complain, she was the only woman he’d seen so far at the party in any kind of hosiery like that.
Filled with some liquid courage, James went over and sat down on the couch beside her. Just like he had no resistance to nylons, she had no immunity to James’ handsome looks and disarming smile. They quickly got to know each other over a few beers. James found out her name was Monica, she was in her second year in UCLA’s medical program, was originally from the Sacramento area and recently broke up with her boyfriend who’d she just texted to tell him she was going to block his number.
It wasn’t long before James and Monica were making out, chalk it up to the alcohol or the fact that they just seemed to click or both. Either way, the ardor was building between them. Monica’s hand caressed his cheek as his hand roamed up and down her silky thigh. His cock was bulging his shorts and James was about to ask her if she wanted to take their fun someplace more private when a familiar voice shattered his world.
“Has the pantyhose perv found another victim?” Dana’s words making him cringe. She was leaning over the back of the couch next to him so he was sure to hear her over the music filling the room.
Monica pulled back, looking between this intruder and James with concern on her face. “Is this your girlfriend?” she inquired, making ready to bolt. Her boyfriend had cheated on her with a woman at one of his frat parties and Monica didn’t want to be ‘that girl’ here.
“Ex-girlfriend,” James stated, turning to Dana, “What the fuck do you want?”
“Just wanted to say Hi to my favorite pantyhose perv,” Dana shifted her gaze to Monica, “You know all he’s interested in is fucking you in your nylons don’t you? Or didn’t he tell you about his little fetish?”
James felt his guts twisting as a look of shock crossed Monica’s face. She noticeably leaned away from him. His mind scrambled to repair the damage Dana had done with that bomb but her next salvo was devastating.
“He always wanted me to wear pantyhose, even when we fucked,” her vitriolic voice now loud enough that anyone could hear, “He was obsessed. He even wore them himself. Hey, are you going to wearing some for her? C’mon tell everybody how kinky you are!”
James watched in horror as Monica stood and made her escape. He could hear others laughing around him. It was true, he had worn pantyhose in the past but it was on a dare from Dana prior to them having sex on one occasion. It was all fun and games at the time and he never expecting it to be used against him like this. How could he explain that to all these people; to Monica? Dana had done it again, embarrassed him in front of friends and strangers because of her own selfish rejection issues. She couldn’t handle them breaking up then and obviously, she still hadn’t let it go.
James stood, trying to control his anger and embarrassment. He wanted to knock that smug smile off Dana’s face but punching her wasn’t the answer. It would just make things worse. He made an attempt to find Monica and explain but he couldn’t locate her amongst the ocean of bodies. In frustration, he went up to the guest room and locked the door. He needed to calm down but all he saw in his mind’s eye was the shock on Monica’s face and all the laughing people.
He wasn’t sure how long he’d sat there with his head in his hands but he knew it was time to go. The anger and adrenaline had killed the nice buzz he had going on prior to Dana’s appearance. James grabbed his pack and headed down stairs. He pushed past people, not wanting to meet their judgmental gaze. He threw his pack in the Jeep and drove toward Coast Highway. His phone buzzed in his pocket. He ignored it. He didn’t want to talk to anyone right now.
***
James could see an unfamiliar vehicle parked in his aunt’s driveway, blocking him from putting the Jeep in the garage. He made a U-turn and parked across the street. His phone buzzed for the third time since leaving the party. He pulled it out and looked at the caller ID. It was Mike again. He turned off his phone, collected his bag and walked across the street.
It was now just after 11 PM when James quietly let himself into the house. There was only a single candle left burning on the kitchen counter to light his way. He could see an open bottle of wine on the breakfast bar and another on the coffee table which led him to believe both were empty. ‘Lisa must be entertaining someone special tonight’ he thought. He then heard his aunt’s unmistakable giggle followed by a low moan he knew was hers as well. He wondered if she’d brought home one of the artists she had met with. For some reason he pictured a balding ‘hippie’ type with a stringy ponytail and scruffy beard.
He crept toward his room, placing his pack by the door. The door to his aunt’s room was open just an inch or two and dim light from inside illuminated the hall. The sounds he was hearing were definitely of a sexual nature. James felt a wave of jealousy wash over him as he quietly stepped closer to his aunt’s room. He wanted to see who she was with but at the same time, didn’t. She had made it quite clear that they were both to continue with relationships outside their own and he had even tried to get lucky this very night but couldn’t shake the uncomfortable feeling of Lisa with another man. He knelt, took a deep breath then peered through the crack.
The master bedroom was bathed in the soft golden light of a dozen candles placed around the room. James saw Lisa lying naked on her back with her head on a pillow. Her legs were spread, bent at the knee with her feet planted on the mattress. She clutched at her breasts while moaning in ecstasy, grinding her pussy into the face of her lover. It was then he got a sight that sent relief surging through him. The person Lisa was with was wearing thigh high stockings. ‘She’s with a woman,’ he exclaimed inwardly, but with his aunt’s legs up like they were, he couldn’t see the person’s face. James’ suspicions that his aunt was bisexual were confirmed. He tried to remember the names of the female artists he’d read on the pieces of art at the gallery but was coming up blank. Whoever it was, she was doing a good job pleasing Lisa. His aunt’s cries were getting louder and higher pitched: she was getting very close to orgasm.
“OH GOD, YES!” Lisa screamed as her pleasure peaked.
James watched his aunt buck and moan with unbridled release. He could see her partner holding Lisa’s thighs to continue pleasuring her as she thrashed violently. His cock was hard as a rock in his shorts watching the scene unfold in his aunt’s bed. It took several minutes for Lisa to come down from her euphoric high but when she did, she pushed her lover’s head from between her legs. That’s when James got his next surprise.
“Mmmmm…you’re so beautiful when you cum,” Sandy purred as she slithered up Lisa’s body, “And you taste even better than I imagined.”
“That’s not the first time I’ve been told that,” Lisa replied with a contented smile.
The two women kissed passionately for several moments all the while James stroked his cock, now free from the confines of his damp shorts. He could tell Lisa was definitely tipsy by the sound of her voice. Sandy finally broke their kiss and rolled off Lisa with her back to the door. James was practically drooling at the sight of Sandy’s firm round ass.
“Oooohhh, where are you going,” Lisa whined disappointedly.
“Roll over,” Sandy ordered pushing herself up into a sitting position.
“But I wanted to take care of you first.”
“You can do that later, right now it’s time to fuck.”
Lisa reluctantly rolled over onto her stomach then rose up on her hands and knees. At the same time, Sandy moved behind her boss and positioned herself between Lisa’s parted legs. James’ eyes nearly flew out of their sockets when Sandy took hold of a very stiff and slender cock, aiming it at Lisa’s dripping sex. It was probably 6” long and not as thick as his own but it was hard and leaking pre-cum and was definitely attached to Sandy. He released his own cock as if it was on fire. His mind was having trouble accepting what he was seeing.
‘Sandy has a cock? Why didn’t Lisa tell me?’ he thought, feeling betrayed by his aunt. ‘She could have said something before I…,’ he couldn’t finish that thought. He’d masturbated several times thinking about doing all kinds of sexual things with her…him. He was confused. But that was before he knew she was a guy. ‘There must be some mistake,’ he tried to rationalize the situation, ‘Maybe I’m still buzzed; not seeing straight.’ But he knew that wasn’t the case. Sandy had the body of a woman but instead of a vagina, she had a cock. That realization sent shockwaves through him. He began to worry about his own sexuality. ‘Does this make me gay?’ he pondered, ‘I’m not into guys but Sandy is…She’s gotta…He’s gotta cock. What the FUCK!’
Both women moaned as Sandy’s cock slid inside Lisa’s tight, wet pussy. Their moans brought James’ attention back to them. He watched as Sandy began slowly thrusting into his aunt, making her cry out with each impact of their bodies. She slowly ramped up the speed until there was a steady slapping of flesh mixed with the ever increasing moans and wails coming from both of them. Lisa lowered her shoulders to the mattress as her hands balled up into fists around the sheets, her voice rising in anticipation of her on rushing orgasm.
James couldn’t tear his eyes away from the two women on the bed. He felt very uneasy yet he couldn’t stop looking, his cock begging for attention. He wasn’t able to bring himself to touch his aching member. He heard Lisa let out a guttural groan and knew she was cumming again.
“Aaaaaaahhhhh….Yes…Yes…Fuck me! Fuck me hard, Jimmy!”
The room went absolutely silent as all three parties realized what had just been said. It felt as if time itself had stopped. James’ heart pounded in his ears as he waited for the aftermath of Lisa’s slip-of-the-tongue. Seconds seemed to pass at a glacial pace until Sandy made a move. She tossed Lisa onto her back then pounced on the tiny Asian woman. Sandy now lay nose to nose with her, covering Lisa’s body with her own to keep her from trying to escape.
“I KNEW IT!” she announced.
“Sandy I…,” Lisa began.
James was unsure what to do at that moment. He was already overwhelmed with the events so far but now this. He wanted to run and hide as if that would do any good. But what Sandy said next stopped him from doing anything.
“I knew you’re fantasizing about fucking your nephew! You horny little slut,” she laughed excitedly.
Both Lisa and James let out an internal sigh of relief after hearing that. Sandy assumed wrongly that Lisa only fantasized about James and had not realized they did actually have an active sexual relationship. James saw Sandy shift her hips forward and with the accompanying moan from his aunt, knew she had her cock back in Lisa’s pussy.
“That’s so fucking hot,” giving Lisa a quick peck on the lips.
“Sandy! I’m not supposed to have thoughts like that about Jimmy.”
“You’re a hot sexy woman; he’s a hot sexy stud, what’s the problem?”
“He’s my nephew! That makes it against the law, last time I checked.”
“I’m not saying you should rape him but you ARE both adults,” Sandy paused to kiss Lisa again, “So as long as you’re both willing...” She drove her cock in to Lisa as deep as it would go for emphasis.
Lisa bit her lip to keep from moaning again, then fixed Sandy with her gaze, “Society frowns on stuff like that.”
Sandy pushed herself up with her arms to look down on Lisa, “Society!” she spat, “Society has frowned on people like me forever. Fuck what society thinks. If you get a chance to bed that young man, I say go for it!” Sandy’s features softened as she lowered herself back down nose to nose with her boss, “If you do get a chance to fuck James, I’d love to watch.”
“SANDY!”
“What? Let a girl have her fantasies,” her hips began to make slow, grinding circles against Lisa’s.
Lisa let out a surprised gasp then closed her legs around Sandy’s narrow waist, “You’re so bad.”
“And you love it,” Sandy replied; now slowly thrusting.
James was visibly trembling from what he’d seen and heard. He had to get away from the door before he made his presence known. They had dodged a bullet with Sandy’s assumption but it wouldn’t be good if he was discovered. The idea of joining them right now was tempting but he and Lisa had to keep up appearances. Besides, he was still uncomfortable about what Sandy was and his feelings about that.
James quietly moved to the door to his room, retrieved his pack and closed the door behind him. He set his pack on the floor by the bed then sat down to ponder what he was feeling and all the events of this very troubling day. He could hear Lisa and Sandy in the next room enjoying themselves, making his cock ache even more. It was so hard it hurt and he wanted to relieve the pressure but the image of Sandy’s cock plunging in and out of his aunt haunted him. How could he be turned on after seeing that? He’d seen plenty of porno movies with guys fucking women before and the sight of the guy’s cock never bothered him. So why was Sandy’s penis giving him such trouble.
“Because she’s not supposed to have one,” he said out loud.
His aunt’s voice reached a new crescendo, returning James’ mind to the action next door. His throbbing dick needed release. He stripped and lay back on top of the cool sheets but he hesitated to touch himself. He tried to push the image of Sandy’s pretty face and erect cock from his mind. He focused his thoughts on Monica, her beautiful smile, perky tits and those luscious legs in nylon. He pictured her under him as he sank his cock deep into her tight pussy. His fist pumped up and down his stiff prick, he was almost there. His balls began to tighten from his impending release when he heard Sandy in the throes of orgasm and her face immediately replaced Monica’s in his fantasy. His cock exploded, shooting a fountain of cum skyward again and again. When the last tremors had subsided, he felt as if he had done something unnatural. He quickly mopped up the remnants of his ejaculation with some tissues from the nightstand.
James fell into a fitful sleep. Images from the party flashed before him. Monica’s shocked face, Dana’s malicious smirk and the people laughing at him, all rushed back. Then he saw Lisa and Sandy standing in the crowd naked. He could see Sandy’s cock standing erect, dripping pre-cum. He noticed he was naked too, his cock at attention. He could hear Sandy asking him something but couldn’t quite make it out. When she asked him again, the people in the crowd started jeering and making homophobic slurs aimed at him. He wanted to run but Sandy held him in place by his cock as she kissed him passionately to the crowd’s enjoyment.
James bolted upright in bed, covered in sweat, heart pounding and feeling as if he’d just closed his eyes a moment ago. He settled back onto his pillow, taking deep breathes to calm himself. It was early morning and the sun had just begun to lighten the sky. He drifted back to sleep. He was awakened again sometime later by the clicking of high heels on the hallway floor. It was lighter outside now but he hadn’t rolled over to look at the clock. The footsteps stopped at his room. There was a faint tapping on the door before it slowly opened. He closed his eyes, feigning sleep. Lisa poked her head in.
“Jimmy…Are you awake,” she asked softly.
He didn’t move. After a few moments, the door closed and he could hear the clicking of his aunt’s heels heading for the kitchen. She obviously knew he came home last night and probably wanted to know why and when. He wasn’t ready to talk to her about any of it yet. There were things he had to work out for himself first. James was still feeling betrayed by her for not filling him in about Sandy. ‘Maybe she didn’t know until last night herself,’ he wondered but dismissed the thought as improbable since she was Sandy’s boss, she must have known. They had always vowed never to keep secrets from each other but it looked to him as if things had changed.
The situation at the party was a whole other issue he had to deal with. How could he face his friends again after that embarrassing show? He knew he should talk to Mike but wasn’t sure what to say. The sound of the front door opening and closing caught his attention, followed shortly by Lisa’s car starting and pulling out of the driveway. Confident she was gone for the day, James got up and showered.
James found the note Lisa left on the breakfast bar when he got to the kitchen to get something to eat. She was concerned that he came home, wondering what was wrong. She wanted to talk once she got home from the gallery that evening. He wanted to square things away with Mike first so he could focus on what he wanted to say to his aunt.
Mike and James met for lunch at the Ruby’s restaurant on the Huntington Beach pier. Mike profusely apologized for what happened, telling James he made Dana leave the party once he found out what she had done. Jen even texted him an apology during their meal, letting him know that she and Dana were not going to be speaking for a while. Their conversation ended with Mike assuring James that he’d make sure everyone knew that Dana was out of line and probably on drugs for what she’d said. James felt better but he was still disappointed about not getting to explain things to Monica.
***
Lisa arrived home around 6 PM to find James watching TV in the family room. He seemed focused on his show, only giving her the minimal of greetings. She knew something was bothering him and was determined to find out what it was. She grabbed a bottle of wine and two glasses then joined her nephew on the couch.
“How’re things going,” she asked as bubbly as she could be.
“Okay I guess,” he replied with a shrug but not looking at her.
“Wine?” she offered.
“Not right now, thanks.”
“I noticed you came home last night. I thought you were gonna stay at Mike’s place.”
“Plans changed.”
“What changed them?”
James let out a long sigh, knowing he’d have to talk to Lisa eventually but his emotions were in turmoil and he was hoping he didn’t say something that would upset her. Turning to face his aunt, “My ex-girlfriend showed up and…Well let’s just say she caused a scene.” James went on to fill her in on the details, including his conversation with Mike earlier today.
“Don’t worry, I’ll never make fun of your love of pantyhose,” she said, rubbing her nylon encased legs together and smiling seductively, “I think it’s hot.”
James gave a half hearted grin a then looked away. That’s when Lisa realized Jimmy had hardly even looked at her. Usually he’s undressing her with his eyes the minute she walks through the door. He barely gave her legs a second glance just then. The sheer nude hose she had on usually made him drool. There was something else wrong, but what? Lisa pondered that then came up with a possible answer.
“Are you upset I had someone over last night?”
“You mean Sandy? No,” he replied, not looking at her.
“You heard us then,” Lisa sipped her wine then set it on the end table, “Sorry if we kept you up.”
“I heard you and saw you too.”
“How much did you see?” Lisa leaned closer to him, concern now present in her voice.
James met her gaze, “Enough.”
There was a long uncomfortable pause as they both gauged what to say next.
“Why didn’t you tell me Sandy was a guy?” his words laced with anger.
“She’s not ‘a guy,’ she’s transgender,” Lisa reached for her glass and took a quick draw on it before continuing, “And she swore me to secrecy.”
“How long have you known she had a…,” James was struggling not to lose his cool, “She’s a he?”
“SHE told me about a week after I hired her,” Lisa drained her glass and set it down, “She didn’t want any uncomfortable surprises to come up between us. That’s when she asked me to keep it between us.”
“You could’ve told me she had a…HE was a guy in drag,” James’ voice elevated with tension.
Lisa’s eyes narrowed and her brow furrowed as she leaned toward her agitated nephew. She was clearly upset with him, her gaze burning into his.
“Excuse me, what have you done with my intelligent, open minded nephew who I taught not to judge what a person was on the outside but what’s in here,” Lisa pointed at her heart, “You’re sounding like a narrow minded, bigoted asshole!”
James lowered his eyes in shame after that pointed assault. He didn’t like upsetting Lisa but he was in turmoil over this situation. Lisa let her words settle in before going on.
“Do you have something against gays or lesbians? So what’s the problem with transgendered people?” she was irritated with his attitude and wanted him to think before he spoke again then added, “I’m bisexual. Do you have a problem with that?”
He shook his head, not wanting to look at his angry aunt. It was then the answer dawned on her.
“You were attracted to her,” Lisa’s tone softened, “And if my guess is right, you still are.”
James opened his mouth to deny it but she was right. His cheeks flushed and she knew what was bothering him.
“It doesn’t make you gay to be attracted to her.”
James looked into Lisa’s eyes to verify she truly believed what she was saying. She could see he wasn’t buying it. So it was time to convince him.
“Are you attracted to guys? Do you want a guy to suck your cock or fuck you in the ass? Maybe you want to fuck a guy in the ass or suck his cock, is that it?”
“NO, no…what are you talking about? Why would you ask me that?” James was rattled by that line of questioning.
“Well if you’d have answered yes then I’d say you WERE gay but clearly by your reaction you aren’t. Sandy isn’t a guy, she’s a woman.”
“But he’s got,” Lisa’s eyes narrowed again making him revise his statement, “Sandy has a cock and from all the biology classes I’ve had, that makes Sandy…male.”
“Jimmy…You’re right. The plumbing down between her legs doesn’t match the definition of a woman,” James was surprised at Lisa’s admission then she went on, “But, everything else about her is all female. She looks like a woman, she feels like a woman, she kisses like a woman; she’s even emotional like a woman. Remember what I taught you; judge a person by what’s inside, not just what you can see outside.”
James was beginning to see his aunt’s point of view. Up until the other night, there was no doubt in his mind that Sandy was anything but a woman. Every time he’d been around her where they talked and even flirted, he would’ve never guessed there was anything unusual about her. It wasn’t like he found out about her secret as they were about to have sex. Although he had some lingering concerns about his feeling toward her now, he decided to change the subject to shift the focus off him.
“So why didn’t you tell her about us?” he asked.
“Because we agreed to keep that OUR secret.”
“But she seemed to be all for it,” James was now facing his aunt again, “If there was anyone you could share it with; she seems the most likely candidate.”
Lisa cocked her head, taking in her nephew with a curious eye, “Where are you going with this? Do you want her to know for some reason?”
“I don’t know…She said she wanted to watch and well…”
“That turns you on? Being watched?’ Lisa studied his reaction, “Or being watched by Sandy?”
James’ cheeks burned and he fidgeted anxiously beside her.
“You don’t have to be embarrassed; I’m not gonna judge you. Personally I like being watched. I think if I’d known you were watching Sandy and me last night, it would’ve had me really turned on.”
“I think having her watch would be hot. I don’t know why but …” he couldn’t finish that thought, “Do you think we can trust her not to tell anyone else?”
“I’m willing to trust her. She trusted me with her secret. She didn’t have to tell me she was transgender. Besides you know her secret now too and I don’t think she’s the malicious type.”
“When should we have her over and tell…I mean show her?”
Lisa could see James was still nervous but the bulge in his pants told a story of its own. She was elated he was willing to explore new things. It was turning her on as well. Her instinct was to call Sandy right there and then but she decided to hold off and increase the anticipation. She had other reasons to postpone their ménage a trois, because she wanted to enjoy Jimmy tonight by herself. It hadn’t been that long since he was in her bed, fucking her senseless, but she wanted more of that tonight.
“Well she’s probably home by now so let’s plan to have her over one night this week after work. I’ll make something up to get her to come over then we’ll go from there,” Lisa moved closer to Jimmy and ran her hand over his concealed, rampant cock, “But tonight, you’re all mine.”
Lisa stood and stepped in front of her nephew, using her knees to close his legs. The feel of her silky nylons on his bare skin made him shiver. She bent at the waist to undo his shorts. James was looking right down her blouse as it hung open, revealing her cream colored half bra and her perky breasts spilling out of the sheer garment. Her skirt rode up her parted thighs giving him a tantalizing glimpse of her bald pussy through her seamless hose. Stepping back, Lisa pulled off his shorts, tossing them aside. His hard cock sprang up, leaking a steady stream of pre-cum. James quickly removed his tank top as he waited to see what Lisa did next.
She trapped his legs between hers again as she unbuttoned her blouse then laid it across the back of the couch. Her bright pink nipples poked out over the top of her bra, erect and in need of attention. Her bra came off and joined her blouse on the couch. Lisa knelt on the cushions, straddling her nephew’s thighs. His hands immediately went to her breasts, cupping the firm globes while rolling the rock hard nipples between his fingers. Lisa let out a shuddering gasp then kissed him passionately; her tongue stabbing into his mouth in search of his. Her hips began to grind her stiff clit against James’ throbbing cock; it was his turn to gasp. The warm wetness of her labia gliding along his shaft with only a thin layer of nylon separating them was mind blowing.
Lisa broke their smoldering kiss to stare into Jimmy’s eyes. She was on fire; she wanted…No, needed him now. She didn’t care if he’d cum right away, she wanted to be fucked. Every thrust of her hips shot bolts of toe curling electricity through her trembling body. She was so turned on right then that his masterful manipulations of her tits threatened to send her over the edge.
“I want you to fuck me, right now!” her voice no more than an inhuman growl, eyes blazing with lust.
James pulled her to the right, laying her down on the couch as he scrambled to position himself over her glistening body. He kissed her again, their tongues wrestling for several moments then to her surprise, he didn’t rip open her hose and start fucking her. Instead he kissed his way down her body, lingering only briefly at her breasts until he reached her drooling sex. His tongue flattened, sliding up her slick cleft to her angry bud then back down.
“OH…MY…Fucking…GOD!” Lisa exclaimed as her body went stiff.
Her fingers laced into his hair to secure his mouth in place while she was being ravaged by waves of orgasmic pleasure. James never stopped sucking and licking her spasming pussy throughout her entire release. As Lisa’s orgasm began to ramp down, James used his teeth to tear through the flimsy barrier keeping his tongue from penetrating her inner folds then stabbed it in as far as it would reach. This set off another round of tremors rolling through Lisa’s body. He quickly fastened his lips to her aching clit sucking it in and allowing his tongue to flutter over it. Her outcries were guttural and filled with unintelligible obscenities as her body thrashed about on the couch. Lisa reluctantly stopped Jimmy by pulling his mouth from her quivering sex by his hair.
“I want you to fuck me, now!” she growled.
“Yes ma’am,” James replied then kissed her again while maneuvering himself into position.
Lowering his hips, his steely cock came into contact with Lisa’s sensitive clit, making her gasp. He rocked side to side over her then drew back, dragging the entire length of his hard member over her aching bud until the tip of his cock dropped into her wet valley. He stared deep into her onyx eyes as he sank into her warm vaginal grasp. James didn’t rush, savoring the feeling of being engulfed by his aunt’s body. He watched her eyes roll back into her head then felt the vice like grip of her legs around his waist trying to force him deeper. When he finally bottomed out, she came again.
Lisa’s body stiffened then her hips made frantic thrusts against James’ stationary phallus. He held still while she fucked herself on his ridged rod. The tremendous force she was applying with her legs made him feel as if she would cut him in two. She bucked violently under him and it was all he could do to keep from falling to the floor. Without warning, her legs opened wide as her convulsions rolled on, allowing James to slip out of her gushing hole. He sat back, grabbed her ankles to put her legs against his chest, and then buried himself back in her silky embrace. He leaned in and kissed her hungrily.
James thrust fast and hard into Lisa, driving his cock in and out like a piston on a runaway steam engine. He wasn’t going to last long like this with her velvety canal contracting around him like it was but he didn’t care. He wanted to cum for her. His sperm filled, pendulous balls slapped against her firm ass with each powerful thrust, bringing him closer and closer to a monumental release. He broke their kiss to find his aunt staring lovingly if not lustfully into his eyes.
“That’s it Jimmy fuck me good,” she purred, “I want to look into your eyes as you empty those big balls inside me.”
“I’m close,” he hissed between clenched teeth.
“Yes baby, that’s it. Cum for me…cum for me…cum for me,” she chanted.
The chant worked. James made one last savage thrust then let out a primal scream as his cock belched the first of many hot geysers of semen deep into his aunt’s clenching cunt.
“OH YES! I feel it…fill me up. Give it all to me baby.”
Lisa began to tremble again as she came with James, their orgasms mingled in euphoric bliss until both of them were spent. James released Lisa’s legs before collapsing on her. Her legs returned to his waist, holding him in her tightly. They lay there panting for several minutes, their sweat slick bodies glowed with perspiration.
“Mmmmmmm…That’s just what I needed,” Lisa breathed a contented sigh.
“That was…incredible! I thought…your pussy was gonna…suck my balls…right through my cock,” James panted, trying to catch his breath.
“I wouldn’t want that to happen,” she reached around to tickle his sack, “I like them just where they are.”
“That makes two of us,” he replied, feeling his cock begin to soften, he moved to withdraw himself from his aunt’s cum filled pussy.
Her legs suddenly tightened about his waist as she purred, “Don’t pull out yet. I want to keep you inside as long as possible.”
He relaxed back down and kissed her passionately once more. As their tongues danced, Lisa’s legs caressed his sides and back, giving him more reason to stay put. It wasn’t long before James felt Lisa’s tiny hand gently touch his face. He broke their kiss and stared down into her smiling face.
“I don’t want this to end but before we make an even bigger mess on this nice leather, we’d better get cleaned up,” her words filled with reluctance.
She opened her legs to release him and as soon as he was out of the way, she covered herself and rolled off the couch to keep from leaking their combined fluids all over the furniture. Lisa stood and with her free hand took his and led him to her bathroom.
James turned on the water while Lisa let her hair down from its high pony tail. As she reached to lower her ruined hose, James yanked her into the shower.
“HEY! I’ve gotta take these…,” he cut her off with a tonsil swabbing kiss.
She melted into his arms and could feel his freshly revived cock pressed against her belly. She let him do what he wanted, content to just enjoy the ride. James pulled back from her then quickly spun her around to face away from him. Lisa leaned forward placing her hands on the cool tile in front of her and lifted her right foot to the stone bench beside her. James cupped her breasts from behind, massaging the soft flesh while rolling her tight nipples between his fingers. Lisa gasped, flattening herself to his chest. His lips kissed their way from her ear, down her neck to her shoulder. His tongue flicked out on the way to taste her silky skin and send small shivers running through her.
James bent his knees allowing his cock to slide down through the cleft of her tight nylon covered ass until the tip found the opening he made and pressed into her sopping folds. His hands went to her hips as he straightened his legs, impaling her once more on his turgid member. He fucked her hard and fast to another quaking orgasm before unloading himself deep within her clenching pussy.
They eventually did clean up and exit the shower before all the hot water was gone. The pair decided to order Chinese and spend the rest of the evening in front of the TV. It was relaxing for both of them, especially James. He felt at ease with himself and his feelings towards Sandy. He also managed to forget about the incident at the party. Lisa had a very calming effect on him and he loved her for that, amongst other things. When they retired for the night, they only cuddled until sleep finally overtook them.
***
The next couple of days were very busy for Lisa. The issues brought about between her and Ray made for some minor chaos at the gallery. She was meeting with artists and prospective investors on top of her normal responsibilities. With Lisa tied up outside the gallery more, Sandy had to step up her efforts in sales and customer relations as well as training a part time worker to help her around the shop. It made for very long days for both Lisa and Sandy, leaving them burned out by the time they got home at night.
Even with her hectic schedule, Lisa hadn’t forgotten about the plan to have Sandy ‘watch’ her and Jimmy fuck. She was hoping Jimmy would allow Sandy to join in but she wasn’t going to push the issue, just let things happen. She didn’t want to spook her nephew or cause an uncomfortable situation to occur. She was going to leave it up to the heat of the moment to direct their path. Regardless, she had a plan to get them all together.
It started with the successful meetings Lisa had on Wednesday where she secured two investors who were also artists and had no love for Ray. She would tell Sandy that the two of them would go out to celebrate the new found financing. Sandy was to pick Lisa up at her house, Friday evening after she had changed, to go out to dinner then some ‘Clubbing’. However, Lisa would change plans once Sandy had arrived by making dinner for them and Jimmy. Once the wine started to flow, she and Jimmy would share their secret with her and see what would happen next. ‘It’s gonna be perfect,’ Lisa thought, ‘Sandy and I will be dressed to the nines so Jimmy will have lots of eye candy to get him nicely worked up and hopefully less inhibited with all the hormones flowing.’ She just hoped Sandy would be willing to go through with this planned encounter once she found out the whole story. Lisa texted Jimmy the basics of her plan.
James and Mike were off the coast of Catalina Island, fishing on a buddy’s boat and were planning to be back by Friday around noon. James replied to his aunt’s text and was filled with excitement and a bit of apprehension. He was still having some disconcerting thoughts about his masculinity as well as his sexuality but when they popped up in his mind, he’d remember his conversation with Lisa on the subject and things would seem to feel more acceptable.
When their boat finally docked on Friday, James was buzzing with anticipation of what that evening would hold. He said his goodbye’s to his friends and made a bee line back to Lisa’s house. He put the fillets he had in the fridge and went to clean up. After showering and shaving, James set his alarm for 5 pm and took a short nap. He refrained from masturbating so he’d have plenty of cum for his aunt.
The shrieking alarm woke James from a restful slumber. He got up and picked out what he was going to wear. He stood in front of the open closet, scanning the choices before him. It struck him as funny that he was putting so much thought in what to wear when he’d probably be spending the majority of the night naked. He pulled out some khaki shorts and a button down shirt with a subdued leaf pattern on it. He got dressed then went to the family room to watch some TV before Lisa arrived home.
It was after 7 pm when Lisa pulled into the driveway. James was starting to get concerned their rendezvous with Sandy might have to be postponed for some reason. Lisa rushed in and placed several bags of groceries on the bar then hurried off toward her bedroom.
“Hey sweetie. Could you put those away for me? I’ve gotta pee really bad,” and she was gone.
James did as he was asked and a few minutes later, Lisa reappeared but she still seemed to be rushed.
“I’ve gotta get changed before Sandy gets here,” she said as she set a few items on the counter to prep for dinner.
James looked his beautiful aunt up and down then commented, “You look amazing. Why do you need to change?”
“I gotta get dressed to go clubbing,” she replied, setting a pot to boil on the stove.
“Clubbing? I thought…” he started.
“Trust me;” kissing him as she moved past him, “It’s all part of the plan. When the water boils, put the pasta in, then could you dice up that onion and peppers for me?”
“Okay…Should I turn the oven on to make some garlic bread?”
“That’d be great! Use the sourdough,” and she was gone again.
James knew his way around a kitchen thanks to his Mom who taught him to cook for himself so he wouldn’t have to eat only fast food and pizza while at school, and his aunt had shown him a few things as well. He had everything ready for Lisa to make one of her signature pasta sauces when she finally returned to the kitchen. He nearly dropped the colander full of mushrooms he’d just washed when he saw his aunt’s outfit.
She wore a figure hugging long sleeves red and black spandex dress with horizontal slashes down each arm from shoulder to wrist. The hem stopped mid thigh revealing her firm sexy legs incased in nylons that had a metallic sheen to them. She balanced her tiny frame on towering 6” black, studded leather pumps that looked as if they’d come straight out of a dominatrix’s closet. Her hair fell in gently curling waves down her back like black velvet. James was in awe.
“WOW!” he exclaimed followed by a wolf whistle, “You look incredible!”
“You’re so sweet,” she purred, kissing him on the cheek.
Lisa donned a white chef’s coat to protect her outfit and went to work. It was fortunate that James didn’t have to concentrate on prepping anything else for dinner because he could do little more than stare at Lisa’s curvy hose covered legs and drool. All the blood had left his brain in a mad rush south. His dick was straining to break out of his shorts as he sat at the bar and watched his sexy aunt work. The only thing that tore his attention away from her was the doorbell ringing. He started to rise but Lisa beat him to the punch.
“C’mon in, the door’s open,” she shouted, pulling the finished sauce from the burner.
“Hey Lisa. Are you ready…What’s this? I thought we’re goin’ out for dinner?” Sandy inquired with a confused look on her face.
“Change of plans. Jimmy’s home from his trip so I thought we’d have dinner here.”
“Okay, works for me,” shrugging then walking in to join James at the bar.
Once again James was stunned. He’d seen Sandy in full business attire a couple of times but he’d never seen her dressed to kill. She had on a pink silk shirt which appeared to be tailored for her with blousy long sleeves. It fit snug to her chest and narrowed down to her waist. The thin material showed off her breasts which James could now tell were a generous B-cup. The burgundy skirt she wore had a high waist, fine pleats and flared out down to an inch or so above her knees. The hosiery that covered her muscular legs was sheer black and created the illusion they were wet with how they shined in the brightly lit kitchen. To finish off her outfit, her shoes were strappy 5” sandal heels that matched her skirts color perfectly. He’d never seen her in anything higher than 3” heels in the past. She was now slightly taller than him as he stood to greet her.
“How’s it goin’ James?” hugging the stupefied teen before taking a seat next to him.
“I’m…I’m fine…” he finally managed with a nervous laugh.
“Well you’re looking pretty FINE tonight, gotta date?” Sandy’s eyes roamed up and down his body.
“No I’m ah…here…staying in tonight,” his eyes glued to Sandy’s legs.
She slowly uncrossed her legs then re-crossed them as she watched him. It took him a moment to realize he was staring then met Sandy’s gaze. His cheeks felt hot as he blushed from being caught.
“See anything you like?” her voice low and sexy then she smiled and gave him a wink. Her flirtatious words just made the color on his face deeper. He wanted to hide, feeling childish and embarrassed. “He’s so cute when he blushes,” Sandy commented and then turned to Lisa, “Well, where’s the wine?”
“Here ya go,” placing a glass of Cabernet in front of her friend then looking to her nervous nephew, “He is cute. I think you surprised him with that outfit. You look amazing.”
“Thank you…You’re looking pretty fucking hot yourself.”
“This old thing?” Lisa took a dramatic stance then yanked open her chef’s coat, “What do ya think of what’s under it?”
Sandy clapped and whistled; “Now that’s more like it!”
That broke the tension James was feeling after being put on the spot. He tried to hide the prominent bulge in his shorts but it was too late. He knew Sandy had seen it, she just hadn’t commented on it yet. He tried to avoid her eyes but that just meant his focus shifted back to her leg which wasn’t much better for the given situation. James decided to sit down until he was needed.
Dinner was served and the trio enjoyed Lisa’s magnificent cooking. The conversation was lighthearted throughout the meal, avoiding anything about work except a brief mention of the new investors. James’ fishing trip was the highlight of the evening as both Sandy and Lisa seemed very interested in the happenings that occurred. He assured them that there was nothing more than fishing and drinking with the occasional girl watching when parked in Avalon.
Lisa kept the wine flowing that night as well, having Jimmy open a second bottle during dinner after she and Sandy had polished off the first. About the time she was going to have Jimmy clear the table and move their little gathering to the family room, Sandy asked about the party Jimmy had attended last weekend. There was a pregnant pause as he tried to figure out how to answer that with the minimal amount of embarrassment. To his surprise Lisa jumped in to field the question.
“He met a girl he was interested in,” Lisa began.
“Did ya get lucky?” Sandy asked, now staring intently at James.
He could tell the wine was affecting both women as their questioning and openness was becoming more and more sexually orientated. He was blushing again but tried to hide it by heading to the sink with his empty plate.
“Well I…” he didn’t get to finish.
“NO! His bitch of an ex-girlfriend showed up and ruined everything for him,” Lisa replied now sounding angry.
“Well that sucks. What’d she do?”
“She walked up as Jimmy was makin’ out with this girl,” Lisa could see her nephew shaking his head, trying to stop her narration but she went on as he picked up Sandy’s plate, “and proceeded to tell this girl, and everyone in earshot about his pantyhose fetish.”
Sandy turned and faced James with a knowing look in her eye and a seductive smile on her face. James grimaced at his Aunt’s unbidden revelation. His tension level skyrocketed at that moment. He quickly retrieved Lisa’s plate and went back to the sink. This wasn’t how he pictured this evening going. All his most intimate secrets were being laid bare. He could feel Sandy’s eyes on him as he rinsed the dishes then placed them in the dishwasher.
“I had a feeling you’re into nylons.”
“Was I that obvious?” he asked rhetorically, not meeting her gaze.
“The way you’re staring at my legs when I arrived was a dead giveaway,” slowly crossing her legs, so James could hear the hiss of her nylon clad thighs rubbing together, “I’m glad you didn’t trip over your tongue when you sat down.”
James wanted to shrink away to nothing at her words but the seductive whisper of her legs gliding over each other reflexively drew his eyes to her. He couldn’t help himself; it was his Pavlovian bell she was ringing. He diverted his eyes to his Aunt who was also staring at him. His cock was once again painfully hard and forming a noticeable stain in the front of his Khaki’s.
“I think it’s sexy when I know how to turn a man on,” Sandy said in a silky voice, “I love knowing he finds me attractive no matter the reason.”
It was then James realized what Lisa was doing. She wanted him to see Sandy wasn’t judgmental either but more importantly she wanted him to see Sandy as a beautiful, sexy woman and NOT a guy in drag. It was working. The voice in the back of his mind that had been protesting so loudly, ‘she has a cock,’ was rapidly fading into the background now that his more base instincts were kicking in. She was HOT and if it wasn’t for him catching her with his aunt last weekend, he would’ve never imagined the person sitting just a few feet away from him was anything but a genetic female. There was another long pause before Lisa spoke.
“Jimmy, why don’t you get out that lovely Muscat I’ve got chilling in the fridge and some fresh glasses and we can get comfortable in the family room?” she asked, rising from her chair.
“Are we still planning on going out?” Sandy questioned, also leaving her seat.
“We’ll see,” Lisa replied, taking Sandy’s hand and leading her to the couch, “But first we need to have a little talk.”
James could see the unstable sway both women had as they made their way to the family room. He pulled the cork on the bottle of dessert wine and poured three glasses. He put a stopper in the bottle and returned it to the fridge before joining the ladies. He offered them each a glass then was about to sit down across from them when Lisa motioned to him.
“Come here and join us on the couch,” she said, sliding closer to Sandy and patting the cushion beside her, “There’s plenty of room next to me.”
He sat down next to his Aunt with his right hand going to the back of the couch while his left held his glass. His attention however was focused on two pairs of shimmering legs close at hand. James looked up to see both Lisa and Sandy smiling at him. He took a long draw on his glass. Lisa leaned over, setting her glass on the coffee table and as she sat back, let her fingers glide up Sandy’s calf to her knee. Sandy jumped slightly, not expecting her boss to get so ‘touchy feely’ with James right there. She got even more of a shock with what Lisa did next.
“I had an incredible time Saturday night with you,” leaning in to kiss Sandy briefly on the lips.
Sandy was stunned Lisa would be so candid about their tryst in front of her nephew. ‘Maybe it’s all the wine,’ she thought as she held Lisa’s gaze. She too was noticing the effects of all the alcohol she’d consumed, feeling a little light headed and extremely horny. Drinking always did that to her as far as making her randy but that wasn’t the only reason she was turned on. Having James lustful eyes on her was also fueling the fire.
Lisa pulled Jimmy’s hand off the back of the couch and put it under her arm and on her right breast. She felt him tense up for a moment and then relax, as she held his hand in place. ‘It’s now or never,’ she thought, leaning back into Jimmy.
“There’s something I need to tell you,” watching Sandy’s reaction, “Jimmy came home Saturday night rather than spending it at his friends house. He showed up around the time you and I were…fucking.” The look on Sandy’s face went from shock to concern in a blink of an eye. She looked from her boss to James then back again before Lisa continued. “He saw everything.”
“Okay…Umm…Well I…” Sandy was stumbling for words but Lisa rescued her distraught friend.
“I wasn’t totally honest with you that night,” pausing for effect, “I was fantasizing about Jimmy but Jimmy and I had slept together the night before. And when I say slept, I mean fucked.”
Sandy’s mouth opened as if to say something but no words came.
Lisa went on, “The reason I…we had you over tonight was to ask if you’d like to watch us fuck? He heard that too.”
Aunt and nephew watched Sandy absorb the information then process it. It took several moments but eventually a smile crept across her lips and she simply nodded. Without a word, Lisa stood, pulling James to his feet. She retrieved her glass and offered her free hand to Sandy, helping her to stand then led her around the couch toward the hall. James was frozen in place, coming to the realization this was about to happen.
“C’mon stud…The show’s about to start,” his aunt said seductively, snapping him back to reality. He drained his glass and left it on the coffee table as he sheepishly followed.
In the bedroom, Lisa took Sandy’s glass and set it on the night stand with her own. When James approached she took him in her arms and kissed him deeply. It only took a moment before he was kissing back with equal passion. Hands roamed with James’ coming to rest on Lisa’s firm ass, kneading the resilient fleshy orbs. Lisa’s hands moved up and down her nephew’s back then traveled down his sides until they reached his waist. The intensity of the kiss increased until both had to separate and catch their breath.
Lisa unbuttoned James’ shirt then shifting to his shorts to get at the throbbing beast inside. He let his shirt fall away but became nervous when his Aunt yanked down his khakis. Looking to their guest, James could see Sandy was enjoying the show, especially now that he was completely naked in front of her. Deciding he wasn’t going to be the only exposed individual in the room, he lifted the hem of Lisa’s dress up until it reached her bare breasts then he worked it the rest of the way over her head and tossed it on the floor.
Lisa maneuvered James to the bed, pushing him down onto his back before turning to Sandy. She kissed her full on the lips then began unbuttoning her shirt. James watched in total fascination as his aunt undressed her friend. His cock ached for attention but he wasn’t about to touch it and take the chance of an early discharge. Once Lisa had Sandy’s shirt off, she kissed her again as she ran down the zipper of her skirt. It settled to the floor with the rest of the clothing, leaving Sandy in nothing but her sheer black suspender pantyhose, black silk panties and burgundy heels. James could see the bulge in her panties and the circular wet spot just below the waistband.
James stifled a moan as he looked at the two nylon clad women before him. He was still nervous but very excited. He watched Lisa kiss Sandy again then climbed onto the bed with him, moving him to the middle of the king sized mattress before straddling his chest in a 69 position. His hands immediately went to her silky legs, gently caressing them. That’s when he noticed her nylons were missing their gusset.
“Get those panties off and come join us,” Lisa patted the bed.
Sandy lowered her underwear then walked around to the other side of the bed before lying down next to the pair in the same orientation as her boss so she had a perfect view of James’ cock when it went into Lisa’s mouth. She propped herself up on an elbow and bent her knee, brining her leg into contact with Lisa’s and shielding her rampant erection at the same time. She seemed nervous around James, in her current state of arousal and undress. Feeling the warmth of Sandy’s leg, Lisa gave her a sexy smile then scooted back, positioning her dripping sex above her nephew’s waiting mouth. Taking a hold of the base of his rigid dick, she pointed it straight at the ceiling.
“Let’s show Sandy how we get ready to fuck,” Lisa purred, lowing her pussy to James’ face.
James went into action, drawing his tongue along her dewy petals. Lisa gasped then slowly circled her tongue around the crown of his cock before sucking it into her mouth. He let out a low groan and increased his oral assault on his aunt’s delicious cunt. His hands went back to caressing her ass and thighs while his tongue probed deep into her wet valley. Lisa now slowly swallowed James’ cock, releasing her grip so her lips left a ring of lipstick around the base. As she lifted off, her hand encircled him, following her mouth to the peak then leading it back down.
Lisa bobbed slowly at first on the steely member, gradually increasing her speed. James kept pace with her in their race to orgasm. The steady hum of their muffled moans let Sandy know they were both headed to the finish line.
As his stroke reached the bottom of his aunt’s thigh, James made contact with Sandy’s calf and momentarily froze. The texture of her nylons was slicker than the velvety consistency of Lisa’s. His hand lingered then glided along Sandy’s calf before returning to Lisa’s leg. He began caressing both legs each time his hand came down, sending a shiver through Sandy with every pass. That minor change in stimulation made him focus more on Lisa’s drooling sex. His lips closed on her stiff clit while his tongue lashed it without mercy.
Lisa crossed the finish line first, removing James from her mouth and crying out while grinding her pussy into his face, “Oh YES! YES! AAAAAAHHHHHHH!” She then made low growl and went back to her nephew’s throbbing cock.
His face was slick with his aunt’s juices but he wasn’t ready to let go of her clit. He removed his right hand from her leg and found her jiggling breast. He cupped it at first then focused on the firm nub at its peak. This made Lisa moan around his cock, sending wonderful vibrations along its length. He then heard a soft moan coming from his left, that’s when he realized his left hand was now continuously stroking Sandy’s calf.
Sandy was transfixed by the show she was witnessing. Watching her boss sucking her nephew off like it was her only mission in life was just too arousing to describe. The two of them moaning and slurping at one another was HOT! They were both on the verge of orgasm but when she saw Lisa release James and cry out in ecstasy, she nearly came herself. She was enjoying James’ casual stroking of her leg as well but once his Aunt began to cum, his hand stayed on Sandy’s calf, increasing her stimulation. Her cock was leaking a stream of clear liquid onto the sheets. She heard a low groan coming from James as his body stiffened with his release, making her mouth water for a taste of his spewing cock.
Lisa vacuumed up every thick rope of cum James gave her, swallowing it with ease. As his spurts began to slacken, she held the remnants in her mouth until she was sure he was finished. She leaned toward Sandy, bringing her lips into contact with hers. Her tongue probed Sandy’s lips and when her mouth opened, she gave her a special present of her nephew’s seed.
Sandy wasn’t expecting the kiss Lisa gave her nor the mouth full of cum but she hungrily accepted it and feverously kissed back. They made out for a few minutes, ending with Sandy licking around Lisa’s lips to make sure she hadn’t missed a drop of her generous gift.
Lisa’s pussy was pulled from James when she kissed Sandy, giving James a view of their make-out session. His hand hadn’t left Sandy’s silky leg; in fact it was gripping firmly. The intensity of their kissing was having an effect on him as well. His cock never lost its stiffness and was throbbing again. Both women noticed this too.
“It looks like someone is ready for more,” Lisa teased.
“I can see that. Is he always this quick to bounce back?”
“Pretty much, yes. Ah youth, what a wonderful thing!” They both giggled at that.
James felt his cheeks warm at the comments from the ladies. He wasn’t sure why he blushed but he couldn’t help it. Lisa dexterously spun around to straddle him once again. His hands went to her breasts like they had a mind of their own, squeezing and kneading them skillfully. Her hands covered his as Lisa leaned slightly forward.
“Why don’t you put that nice hard cock into my wet pussy,” Lisa purred.
But when James looked up at her she wasn’t facing him. She was looking at Sandy who was now sitting up next to them. His heart pounded in his chest at what his aunt had said. Sandy too looked momentarily stunned by the request but quickly recovered and moved closer to help. James could now see her cock uncomfortably close. It was slightly shorter than his and noticeably slimmer but every bit as stiff.
He jumped when Sandy’s warm hand closed around his shaft and maneuvered it to Lisa’s waiting pussy. He felt her slowly stroking him before pushing the head of his aching member into his aunt’s slippery folds. As Lisa slowly lowered herself down his length, Sandy reluctantly released him.
Lisa moved her hands to the bed, flanking James’ shoulders, freeing his to resume their work. Sandy had lain down on her side facing him, once again propped up on her elbow. As before her leg rested against his aunt’s but now he had a clear view of her rigid dick. His hands moved to Lisa’s hips, helping her bounce on his hard cock. He focused on her jiggling breast and sensuous nylons to take his mind off the stiff penis less than a foot and a half away. His left hand made its way down her thigh and eventually ran into Sandy’s calf. Again he froze, glancing at Sandy. She gave him a sexy smile, moving her leg up to give him more access to her.
The look on her face as she watched them had James questioning what Sandy was thinking at that moment. ‘I can’t tell if she wants to be fucking Lisa right now or riding my cock like Lisa is or…’ his thought trailed off there, with him not wanting to explore the final obvious option available. He felt frustrated with the conflicting emotions he was feeling toward Sandy. His gaze traveled down her form, taking in every detail. Her pretty face, her supple bouncing tits, her flat stomach and trim waist all conflicted with the six inch pulsating cock pointing at him from between her sexy legs. And yet he moved his hand over her firm calf like she was any other woman.
“OH FUCK! I’m cumming again!” Lisa announced, snapping him out of his pondering.
Lisa’s shook violently as she was consumed by her orgasm. James could feel her pussy clamping down on his cock while she ground herself against him. He was thrusting up at her to help keep her pleasure going but he wasn’t in the best position for driving into her spasming sex. Lisa collapsed forward but continued her hip gyrations. She wasn’t through cumming yet.
James wrapped his arms around Lisa and rolled to his right, putting him on top and letting him pump into her more vigorously.
“Yeah baby, fuck me…fuck me good! Oh yes…Yes…YES!”
Lisa’s velvety legs closed around his waist as he took over, pounding her harder and faster. James looked over at Sandy. She was watching intently, biting her lower lip as her hand slowly stroked her own cock; another conflicting image that he couldn’t ignore. He shifted his attention back to fucking his Aunt, hammering into her like a mad man. Lisa came again but his powerful strokes continued.
“FUCK YES!” she screamed trying to meet his thrusts with her own.
When her orgasm began to subside, she opened her legs and pushed James back with her hands. Lisa rolled from under him and nearly onto the floor. She clambered to her hands and knees in front of James, ready for more.
“C’mon baby, fuck me like this,” she purred, “Show Sandy how you can fill my cunt with your cream.”
James positioned his cock and stabbed it back into his Aunt’s wet tunnel. He buried himself to the hilt, holding her ass tight against his hips. They both moaned in pleasure. Lisa dropped her shoulders to the mattress as James began slowly fucking her from behind. She thrust back into him as he drove forward. He picked up the pace and soon was slamming into her pussy at a blinding rate. The sound of their bodies colliding echoed through the room. The wet slaps of each impact and the snug grip of his Aunt’s tight pussy pushed James closer and closer to a powerful release. He wanted to cum. He wanted Sandy to see him cum in Lisa. He wasn’t sure why it was important but that’s what he wanted. Lisa cried out again and the vice like grip she held him in was all he needed.
“AAAAHHHHHH,” he cried as he emptied his balls into Lisa’s convulsing pussy.
He made several more erratic thrusts before he finally laid over Lisa’s back panting for air. Her pussy continued to milk him for every last drop of his sperm. He could feel Sandy’s eyes on him but he didn’t want to look at her, suddenly feeling embarrassed about his actions. He eventually tipped to his right, taking his Aunt with him. They were both trying to catch their breath. He had his eyes close and his back to Sandy, holding Lisa close to him; his cock still embedded in her warm wet depths.
It took several minutes for his breathing to return to normal. His cock had gradually deflated and was about to slip out of Lisa’s pussy when he felt Sandy shift on the bed behind him. Her warm breath was on his ear and he felt her hand glide along his hip. As she leaned closer her erect nipples poked into his skin and he felt something hot and wet touch the small of his back.
“That was so sexy to watch,” Sandy’s voice a sultry whisper, “Thank you for asking me to join you.”
James rolled to his back causing Sandy to shift back slightly. His cock pulled free of Lisa and she let out a disappointed groan but didn’t move. He hoped to protect his back side from any unwanted intrusions however once he was settled; Sandy placed her leg over his and her arm across his chest. This put her hard cock firmly against his hip and her breasts against his chest; once again in his mind, another conflicting situation. Her warm breasts pressed against him and her silky leg sliding over his felt amazing but her stiff prick jabbing him in the hip was a serious distraction.
“Um…I’m glad you…Um enjoyed it,” he replied nervously not looking her in the eye.
“I liked having you caress my leg,” she moved her leg over his as she said that. “It made me feel like I was part of the fun.”
James smiled and gave a shrug not wanting to meet her gaze.
“Lisa doesn’t seem to mind your pantyhose fetish.”
This brought color to his face.
“You’re not embarrassed are you? I think it’s sexy,” she said placing his hand on her thigh.
“Well I…You know I…”
“I kinda have a pantyhose fetish myself…I love wearing them. Have you ever worn them?”
“NO!” he lowered his voice, “I mean no…not really. Not in public or anything. Just once… with my girlfriend…Ex-girlfriend. It was her idea…well a dare actually but I…” James realized he was rambling. Sandy was just smiling at him.
“I’m not judging you, I was just curious. Lighten up. It doesn’t make you any less a man for doing it, especially if you’re having fun.”
James was silent.
“Are you okay? You seem uncomfortable. Am I making you nervous or something?”
Again James shrugged and removed his hand from her leg; not wanting to look at her.
“It doesn’t make you gay ya’ know?”
“I know. She and I were just having fun…”
“I’m not talking about that. I’m talking about you being attracted to me.”
James’ eyes suddenly found hers. She continued.
“I’ve seen how you looked at me before. I thought it was the whole pantyhose thing at first but then tonight when I got here you seemed different. You didn’t want to look at me and when you did it was rarely in the eye. It was like you knew something that bothered you. Then when Lisa mentioned you saw us the other night, it all made sense.”
“I’m sorry; I just didn’t realize…You know…it was a surprise…”
“I bet it was but that’s why I’m telling you this: It doesn’t make you gay.”
“But you’re…You’ve got a…”
“Cock,” she finished, “Yes, I was born with a cock just like you but I never felt like a boy. I always felt outta place. I wanted to wear dresses, tights, makeup like other girls but I was told it wasn’t right. When I graduated high school I decided to change all that. I started hormone therapy and went to college as a woman. I’ve never looked back.”
“So you are a woman in a man’s body?”
“I guess that’s the simple explanation.”
James gave her a confused look.
“I guess you’d say I’m bisexual but maybe not necessarily by the standard definition. I like both men and women but I take on different roles with each. When I’m with a woman…like your Aunt, I take the more masculine role. I want to be the one doing the penetrating, I like being ‘the top’ if you will.”
James had heard the term ‘Top’ before but never understood the meaning when referring to sex.
“I love fucking women, feeling my cock sliding in and out of their pussies is amazing, right?”
James nodded and continued to listen.
“But when I’m with a man, I want him to treat me like a woman, kiss me like a woman, and fuck me like a woman because that’s what I am. Deep down inside, I’m a woman. Just because I don’t have the right plumbing doesn’t change that, at least not to me.” There was a long pause as Sandy let James absorbed that.
“Have you…dated many straight guys or just gay ones?” James finally asked.
“Gay men aren’t interested in women like me. They are attracted to guys…like you. Now do you mean dated as in ‘dinner and a movie’ or dated as in had sex with?”
“Both I guess.”
“Most of the men I’ve dated that were straight, once they found out about my ‘secret’ never went any farther than dinner and a movie. I’ve only had sex with one straight man since I started life as a woman. I’ve dated and had sex with a hand full of bisexual men over the years but I actually prefer women.”
“So you’ve never fucked a man with…I mean stuck your…” James asked nervously.
“I didn’t say that. That only happened a couple times and only with the bi-guys. Is that what’s bothering you? You think I’m going to bend you over and fuck you in the ass?”
“Well I don’t…I’m not sure how that works and I’m not into that.”
“Listen, I’m not into forcing people to do things they don’t want to do and remember what I said before: when I’m with a man, I want HIM to be the man.”
That seemed to put James at ease. Lisa kind of explained this to him but hearing it from Sandy brought it into perspective. He wasn’t attracted to guys in the least but he found Sandy very attractive because she looked like a woman, sounded like a woman, feels like a woman and for all intent and purposes is a woman except for the hard cock she had digging into his side. And he was willing to overlook that with her current clarification of her sexual feelings and motivations.
They laid in silence for several minutes. Sandy resumed sliding her leg up and down James as she caressed his chest with her slim fingers. Sandy looked at James as he pondered all that he heard. She couldn’t help but find him attractive and knowing he found her attractive, at least prior to finding out her secret, turned her on immensely. She was now nervous looking at the young man and decided she needed to act now or she would lose her nerve.
“Can I ask you to do something for me?” her voice softer than before.
James let the initial wave of uncertainty pass as unwarranted fears of what she may ask raced through his mind.
“Sure,” he replied.
She leaned in close. Close enough he could see the fine gold flecks sprinkled across her bright green irises. Her heart pounded yet she had to ask.
“Will you kiss me…Like you did Lisa?”
There was uncertainty and apprehension in his mind even as he nodded his head. A sexy smile spread across Sandy’s face as she closed her eyes and pressed her lips to his. They were much softer than he had expected, that just added to the many things placed in the female column as it referred to her. She pulled back to see his reaction and when she felt he wasn’t repulsed, she kissed him with more passion. Her tongue lightly traced his lips and when they parted and met his tongue the heat of the moment jumped. His tongue sank into her mouth and a wrestling match ensued. They kissed passionately for many minutes with their hands exploring each other’s bodies more assertively. His hands ended up on her tight ass cheeks, squeezing the firm flesh like he had Lisa’s. Sandy’s hand made its way down his chest and across his abdomen to his newly revived cock. Her fingers closed around his steely shaft eliciting a soft moan from James.
They broke their kiss but their hands stayed in place. Sandy was looking into his eyes as she started to slowly stroke his cock. Her hand was every bit as soft as Lisa’s although larger and he couldn’t deny he enjoyed what she was doing. ‘Another mark for female,’ he thought. He didn’t pull away or give a negative reaction so Sandy decided to go for broke.
“Can I ask you to do something else for me?”
“Name it,” his hesitation now being overrode by his animal instinct.
“Will you fuck me like you did Lisa?”
“Yes.”
With a huge smile she kissed him then reached for the nightstand. Sandy removed a bottle of lube from the drawer and returned to straddle James at his thighs. She poured some lube in her hand and applied it to his rampant cock, coating it completely. She poured more in her hand and leaned forward to coat her ass. She plunged one then two fingers inside her tight sphincter so she’d be ready for his thick tool. She wiped the excess on her own throbbing cock before setting the bottle aside. James looked nervous again but also very excited. He’d never had anal sex with any of his past girlfriends so he was ready for the new experience. He looked over at Lisa. She was passed out, breathing slow and steady. ‘She must have had more wine than I thought,’ James surmised as he looked at his sleeping aunt.
Sandy leaned in close and whispered in his ear, “We’ll try not to disturb her, even though she might want to watch.”
She gave him a wink and supported herself with one hand on his chest. The other gave his cock a few more strokes then he felt the tip touch her tight opening. He started to thrust upward and she moved forward avoiding being prematurely impaled.
“Easy stud. We have to take this slow. You’re the biggest thing I’ve had in me for a long time,” she squeezed his cock for emphasis, “I need to get use to this thick pole before you go pounding away at me, okay?”
He nodded.
“I’ll let you know when I’m ready for you to fuck me.”
With that said she moved back and put the tip of his cock at her rose bud, swirling it around the opening to help her relax. James just lay there taking in the whole thing. She held his cock in place and pushed down. Her sphincter yielded and the head of his cock popped inside. He felt her tight ring of muscle clamp down on his shaft just below the head of his cock. He’d never felt anything that tight before, not even his aunt’s well trained pussy was this tight. He wasn’t sure how long he’d last if he hadn’t already cum twice this evening. Neither of them moved for a minute or so while Sandy allowed herself to adjust to the girth of the intruder now in her tight ass.
“Wow, that’s thick,” she breathed, “Now I know why Lisa loves your cock so much.”
James smiled at the compliment but remained still. He did gently caress Sandy’s hips and thighs in hopes of helping her relax. A soft moan told him his efforts were not in vain. He then felt the tightness ease and she lowered herself farther onto his cock. Gradually she worked her way down until she was sitting on his lap. She remained there for a moment then withdrew him to the tip then eased him back in again. When he was about halfway in, he felt her tense as she let out a small gasp.
“Am I hurting you?” a look of concern on his face.
“Mmmmm…No, not at all. You just hit my g-spot.” She could see the confusion on his face so Sandy explained. “Your cock just pushed against my prostate and it feels really good. It’s known as the ‘male g-spot’ and your cock hits mine real nice.”
After a few more strokes, Sandy leaned down and kissed James firmly on the lips. Their tongues dueled briefly then she pulled back.
“I think I’m ready for you now.”
James rolled to his left putting Sandy under him. He could see the surprised look in her eyes but that quickly changed to ecstasy and lust as he slowly withdrew then slid back inside her. He made long, slow strokes at first, making sure he buried himself balls deep each time before pulling out again. He could see Sandy biting her lower lip to keep from making too much noise but her guttural groans conveyed the pleasure she was experiencing with each powerful lunge.
His speed quickly ramped up and Sandy was doing everything she could to keep from screaming. James was fucking her good and hard, just the way she liked it. She could feel herself beginning to climb up to the peak of ecstasy. It wouldn’t be long if he kept pounding her like this.
James was also feeling the effects of Sandy’s tight ass pulling at him. He may have cum twice but he could feel the early tingle that preceded an orgasm already building in his loins. He loved hearing her moan and could tell she was enjoying herself too. That was very gratifying in itself. When he thought she was getting close to orgasm he suddenly pulled out. She had a desperate look on her face mixed with concern.
“Is there…something wrong? You can…cum inside me…if you want, it’s okay,” she managed between gasps.
James pulled back and flipped Sandy onto her stomach. He pulled her hips up and back until his cock was wedged between her ass cheeks. Lying over her back, he brought his lips to her ear.
“I thought you wanted me to fuck you like I did my aunt?” he whispered, rocking his hips to make his cock slide along her crack.
“I do…I do,” she breathed.
James rose up and positioned his slick cock at her tight opening. With one fluid motion, he sank his entire length into her bowels.
“Oh FUCK!” she hissed as her hands balling up into fists.
James new she was enjoying his more aggressive thrusts by the way she drove her hips back into him with each stroke. He jack hammered her ass hard and fast and once again they were both rapidly building to a monumental release but the alcohol and all the previous exertion was taking its toll on James. Sandy felt his speed slowing and the force of his thrusts began to diminish; she decided it was time for her to take over. She moved forward, pulling free of his cock then turning to face him.
“You’re getting tired. Why don’t you let me finish us both off?” rolling to her side and patting the bed.
James was panting and sweating profusely but wasn’t about to argue. He flopped onto his back and no sooner than he was there, Sandy was straddling him once again. She kissed him briefly then guided his thick cock back into her ass. Her silky feet began to glide along his shins as she slowly rode him. This time she didn’t take all of his length, only enough to stimulate her special spot. She tightened and relaxed her sphincter rhythmically to increase James’ pleasure along with her own. It seemed to be working. James began moaning, trying to thrust his hips and her cock was leaking a large quantity of pre-cum onto his belly.
“What you’re doing feels so good, I’m getting really close,” James panted.
“Mmmmm…That’s good, baby me too. I want to feel you cum nice and hard. Fill my ass,” she purred.
Her hip movements became more urgent as her impending orgasm loomed, it wouldn’t be long now. James was also on the brink as his hands went to her waist. The silky feel of her nylon clad hips and feet were the last straw for him. He thrust upward as the first jet of hot semen blasted into Sandy. The hot geyser of cum spraying her prostate prior to the insistent rubbing of his cock head sent her over the edge a moment later.
James felt the spasm of his cock then a contraction in Sandy’s ass then her warm seed splashing onto his stomach. It was a strange yet pleasant feeling as his orgasm ran its course. After half a dozen spasms, he was spent but Sandy had a few more before collapsing on top of him. They kissed between gasps for air until both had regained their composure. His cock shrank and eventually slipped from her ass. He held Sandy for several minutes before she pushed herself up. She was smiling down at him and the sticky mess they had made.
“We need to get cleaned up,” she said, taking his hand and leading him to the bathroom.
***
James woke feeling his cock being slowly stroked. His eyes fluttered open, expecting to see Sandy playing with his penis but it was Lisa fondling him. She was in a sports bra and yoga pants which seemed odd to him since the room was still dark for the most part. She didn’t notice he was awake yet, seemingly transfixed by a pearl of pre-cum forming at the tip of his stiff member. He made his cock pulse in her hand and that’s when she turned and saw him smiling at her.
“Good morning sleepy head,” she said then kissed the tip of his prick. She licked her lips, savoring his flavor.
“Where’s Sandy?” he asked, not seeing her in bed.
“She left a while ago to go home and change before opening the gallery.”
“What time is it?” he asked stretching like a big cat.
“Honey, it’s almost noon,” she replied crawling up to kiss him on the lips, “I’m taking the day off today. I’ve had breakfast, done my yoga and I was about to jump in the shower when I saw this big thing tenting the sheets.” She tapped his stiff cock before rolling out of bed.
“I guess I was really tired.”
“I guess so. Did you and Sandy have fun?” she asked with a stern yet mischievous grin as she removed her sports bra.
“Um…What do ya mean?”
“Did you enjoy fucking her after you got done with me?”
James felt a bit of embarrassment and uncertainty at that question. Her tone seemed to be a bit irritated. He wasn’t sure if his aunt was truly curious or possibly upset with him.
“I thought you passed out when we finished?”
“I did but I felt you two moving around and it woke me up then I heard you fucking…” she kept her gaze on him while lowering her yoga pants, waiting for his answer.
“Well…yes. I mean we both came…and it was my first time doing…you know, anal sex and all…” he lowered his eyes.
“You let her fuck you in the ass?” she sounded shocked while trying to keep a straight face.
“No she didn’t do that to me! I…I was the one doing the fucking…not her,” his voice filled with anxiety.
She could see he was uncomfortable but it was fun teasing him. She climbed back on the bed and knelt next to James, smiling down at him. His cheeks were rosy from embarrassment. She decided to let him off the hook and leaned down to kiss him full on the lips.
“I’m so proud of you. You didn’t let social pressures and stigmas keep you from enjoying yourself with a wonderful person.”
“So you were awake the whole time? Why didn’t you say anything?”
“I didn’t want to cause either of you any problems. I figured if you two thought I was passed out, there wouldn’t be any added stress, it being your first time with a transgender woman and all,” she poked him teasingly.
James flinched back as Lisa’s finger nail tickled his rib.
“Was her ass nice and tight,” she poked him again, giggling.
“Yes!” he exclaimed trying to move away from her.
“Was it better than fucking my pussy?” another poke.
“Yes,” he was now giggling too, but still trying to escape.
“WHAT!” she poked him more vigorously.
“I mean no...Hey!...It was different…stop it!” James squealed, struggling to answer and avoid more of her jabs.
He decided the best defense was to go on offense, knowing his aunt was very ticklish too. The two of them wrestled and rolled, each trying to get the upper hand and make the other cry uncle as they maneuvered on the bed. James’ size gave him the advantage and soon Lisa was trying to escape. She started to crawl to the end of the bed when he caught her ankle and dragged her back. He was about to tickle her again when she grabbed his stiff cock and gave it a hard squeeze. This made him release her for a moment and she scrambled away. He quickly snatched her ankle again and yanked her back, getting a hold on her hips he kept her from rolling away. She still clawed at the sheets, trying to get away but his grip on her was too strong. He lifted her as he pulled back causing his hard cock to lodge in the cleft of her ass.
The roughhousing had both Lisa and her nephew turned on but when she felt his cock sandwiched in her butt cheeks she gasped. He froze too as he felt the wetness of her pussy and the heat of her ass against the underside of his dick. His urges took over; shifting his hips he speared her pussy with his ridged cock. They both moaned while he held her against his body, enjoying her tight, wet tunnel gripping his shaft. He withdrew slowly then slammed into her with a loud clap of flesh on flesh.
“OH Fuck!” she cried.
He withdrew and did it again.
“Uhhh,” she grunted and lowered her chest to the sheets, “Fuck me, Jimmy. Fuck me good.”
He steadied himself to fuck her in earnest, his hands gripping her waist tightly.
“WHAT THE HELL ARE YOU DOING WITH MY SON?”
They both turned to see Laura standing in the doorway, hands on her hips with a look of shock and anger on her face.
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