His Hot Aunt Pt. 02

"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.