Greg Tries a New Angle Ch. 02

In part 1, Greg posts a selfie in his ex-wife's panties to lure a man's man on an adult dating site. To his delight, he meets Drew, who talks lightly but carries a big stick. Earlier in the afternoon, Drew unloaded in Greg's mouth, with the promise to return that evening to take care of unfinished business...

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It was approaching 10 pm and three candles flickered in Greg's living room. The serenity masked his nervous anticipation for Drew's return. Following their afternoon rendezvous, Greg's whimsical plunge into crossdressing had taken a very interesting turn as Susie introduced him to fashion stores he never knew existed. Watching the clock tick slowly, Greg now sported both a new look and a new attitude.

Gone were the white robe and pink panties, replaced with black fishnet stockings, deep-V black panties, and a black corset with shoulder straps and black bow. Shiny black boots with 3-inch platform heels ran up to just below his knees. To complete the look, he wore a new wig with jet-black hair - shiny and straight, down to his middle back with short cropped bangs. His lipstick was dark red and Susie had dolled him up with more rouge and eye shadow than earlier in the day. Greg loved the look and hoped that Drew would, too.

He was about to find out.

At precisely 10:07, a car door slammed shut outside. Seconds later the doorbell rang. Greg opened the door to again see his ebony dream. He didn't think it possible for Drew to look any more rugged and sexy than earlier, but his chiseled features and dark eyes glowed fiercely in the candlelight.

"Well, what do we have here," Drew admired as he looked his date up and down.

"It's good to see you again, honey" Greg said as he gave Drew a peck on the cheek and ushered him inside.

Greg offered Drew a drink, and went to the kitchen to get a beer and a glass of wine as Drew took off his boots and sat down on the couch. Wearing the same faded jeans as before, Drew now had a button-down white shirt rolled up at the sleeves, which contrasted against his dark skin and the stubble on his wide chin. He still wore his silver necklace, silver bracelet, and silver watch. His bald dome was now freshly shaven and smelled of aftershave.

Despite Drew's masculinity, the tables were a bit turned now, as Greg felt more in control than earlier in the day. He was enjoying the feeling of power his outfit gave him, and he knew Drew's eyes were following every sway of his hips as he strutted back across the room.

"I never did get your name," Drew said as he took the beer bottle.

Greg was ready for this question, as he and Susie had spent some time discussing it earlier. "It's Ginger, babe," he said as he sat down and crossed his legs. Their white smoothness protruded from the top of his stockings while his black boot dangled below. He took a sip of red wine.

"So Ginger, how long have you been dressing?" Drew asked as he took a swig of beer and leaned back.

"Just since last night, to be honest," Greg giggled. "And how long have you been interested in 'tranny ass'?"

"Long enough to know one I like," Drew replied in an even tone.

"Well, sweetie, do you like this one?" teased Greg.

Drew leaned over and placed his right hand on Greg's thigh. With a firm squeeze he huskily said, "I'm not sure, I haven't seen it yet."

Greg instinctively placed his hands on Drew's face and leaned forward for a deep passionate kiss. Their mouths were already hot from desire and their tongues furiously probed each other. Greg whispered in Drew's ear, "You will soon, baby."

They continued to kiss for several more minutes, as Greg's hands caressed Drew's shoulders and arms while Drew's hand squeezed his thigh. Greg suggested they would be more comfortable in his bedroom and led the way.

Standing at the foot of the double bed with two candles already burning on the dresser, Greg unbuttoned Drew's shirt, again revealing his wide chest with its dark nipples and curly black hairs above his toned belly. He tossed the shirt aside and unfastened the belt, then loosened his jeans. Again they deeply kissed as Greg's hands explored Drew's chest before finding his crotch. Drew cupped his ass cheeks firmly.

"Do you still want to fuck my tranny ass?" Greg whispered into Drew's ear as his tongue probed in and out. As he licked, he felt Drew's manhood rising in his hands, giving him all the answer he needed.

Spinning around, he pushed Drew down on the bed. He laid back as Greg pulled his jeans and socks off, leaving him naked but for the tent of his bikini briefs. Greg knelt on the bed between his legs, running his hands along Drew's thick thighs, kneading the bulging muscles and admiring the protruding veins. He lowered his head and mouthed the briefs, enjoying the sweaty taste as Drew's cock strained beneath. With the briefs still on, Greg ran his tongue beneath them, gently tickling Drew's black balls and traversing the length of his stiffness.

After teasing Drew for several minutes, he slid the briefs off. Drew's thick black cock stood upwards, with the foreskin partially cloaking its terminal pinkness. Greg let a wad of saliva slowly drip from his lips and run down the length of the cock. With one finger he swirled the spit around, then gently stroked up and down with his index finger and thumb. He did this for several minutes until he saw the first glistening drop of precum. He gently licked the beautiful bead before running his tongue slowly up and down Drew's shaft, licking around the foreskin, and over and under his balls.

Drew was growing more excited and more precum oozed from his pink tip. Greg crawled up and placed both his knees on Drew's thighs. He still wore his stockings, panties, boots, and corset as he hovered over Drew. He placed his weight on him, then ran his hands along Drew's face down to his neck. At first lightly, then ever so forcefully, he squeezed around Drew's neck.

"You are so beautiful, baby, I want to feel you inside me," Greg said as he slipped out of his panties, letting his much thinner cock and smooth balls dangle between them. Although he had condoms, he wanted nothing other than Drew's cock against his own flesh. He reached over for the lube on the nightstand, trying his best to coat his anus and generously covering Drew's cock in the goopy slime.

He got back on top of Drew, with one hand squeezing his neck tightly and the other stroking his cock until Drew began rocking in unison, Greg then commanded, "Fuck me, baby, fuck my tranny ass just like you wanted. Oh please fuck it now." He then rolled over.

Drew deftly assumed the position on his knees, and clutched Greg's legs in his arms as he pulled them high. He rubbed his well lubed cock against Greg's virgin hole, before gently pushing the head slowly in, one centimeter at a time. Pain and delight shot through Greg's body as Drew continued to probe deeper and still deeper.

"Oh Drew, make me your bitch. I want to be your whore tonight."

Drew began to pump a bit more aggressively, finally pinning Greg with his legs back. Greg squealed slightly from the pain but Drew roughly covered his mouth with his hand and began pumping even faster. For the first time in his life, Greg was being properly fucked and loving every second of it, not just in spite of the pain but because of it.

With hand still clamped over his mouth, Greg's muffled cries continued, Mmmmmm, oooohh, yesssssss!

Drew's arms were now pressed against the bed for support as he furiously pumped away while Greg screamed, "Oh god, yes! Cum in me, baby! Please cum in me! Oh, I want you to cum in me!"

Finally, Drew tensed and thrust forward, spurting his seed deep in Greg's ass. "Oooooohhhh, yessssss!" Greg exclaimed.

It took a few minutes to return to his senses. When he did, Drew was in the bathroom getting cleaned up and dressed.

His only words before he left were "Thanks, Ginger."

Alone, Greg licked up the cum that had oozed back onto the bed before he pleasured himself and came on his own stockings. He knew it wouldn't be the last time he came on his stockings.

Not a bad first day as a tranny, he thought.