6 comments/ 36070 views/ 20 favorites Greg Tries a New Angle Ch. 01 By: kjherts It felt like I had flushed $199 down the toilet. For almost five months, I had been a paid member of an adult matchmaking site. Yet so far, I had only one meeting to show for it. When I divorced my wife six months ago, I promised myself that I would no longer suppress my bisexuality. Cocks of all shapes and sizes danced in my dreams those first few months after moving into my own apartment. I was elated envisioning all the action I would be getting after a sexless second half of marriage. But reality was proving much more unsatisfying. For starters, I wasn't really into the gay bar scene. I'm just not the type who is comfortable in such a social setting, as I prefer a more intimate meet. I also scrapped the free websites after being stood up on three occasions. They appeared to be filled with time wasters (and perhaps a few cops trolling for child predators). So I took the plunge and signed up for a full membership at the adult website. For awhile, browsing the profiles was better than any porn site for getting my rocks off. Here were real people looking for real sex, not actors feigning interest just to collect a paycheck. I spent time chatting with a few men who had suitable profiles, and sent plenty of messages to other bisexuals looking to hook up. But it was becoming obvious that the site was also filled with more voyeurs than doers. I could imagine most of these frustrated guys jerking off while fantasizing about sucking a real cock, all while their wife slept in the next room. These guys were proving to be all talk, very little walk. I should know, I was basically doing the same thing just a few months before. Last night I decided to try a different tactic. I updated my profile with a waist-down photo of myself in a pair of my wife's old panties. Although I've never really crossdressed, I had kept a few of them (unbeknownst to her) as I occasionally enjoyed wearing them while surfing porn. Rather than the feminine aspect, I wore them for the pleasant texture and easy ability to stroke myself without sitting naked on my office chair. They were pink, and slightly see through with a frilly edge around each of the leg holes and waist band. In the photo, you could see the outline of my half-stiff cock quite clearly, with a small wet spot around the tip where a bit of precum leaked as I surfed the site. My legs and stomach are naturally quite smooth, and they looked white porcelain from the flash. I wanted to see if my new photo might hook a different sort of clientele than the dry fishing I had been doing. Sure enough, I logged on the next morning to find 6 new messages. Most of these were pedestrian compliments from attached guys listing themselves as bisexual or bicurious. However, one message stood out. It was from "Drew9in" who listed himself as straight and single. Drew was one of those ebony statues that white bisexual men masturbate over, but rarely have much chance of meeting. He had four photos on his profile. His main photo was a picture of his ass from behind. It was sculpted from muscle, bulging out from a narrow waist -- and it looked delicious. His second photo showed him from the neck down, shirtless in just a pair of tight faded jeans, with clearly defined deep brown abs below a wide chest with scattered curly black hairs. His last two photos included a young, tiny blonde. In one, you could see his long dark cock half swallowed in her mouth (her eyes were blurred over). There was a massive vein protruding along its length. The other photo was a close-up of him parting her tight hairless pussy with his big dick. His message was right to the point: "You are going to suck me off, swallow my cum, and then I'm going to fuck your tranny ass. Send time and address." Wow, that got my attention. But I realized I had a problem. If he thought I was a transvestite, he would be sorely disappointed to find a 39 year old man with short hair wearing just a pair of old panties. I wanted him to find me sexy, too, and I had one card to play. "Susie, good morning, it's Greg. Are you around today? I really need your help." Susie was my old tennis partner back when I played in my 20s. We had slept together once after having too much to drink one night, before I was married. She was always more of a friend, though, and somebody I could trust. She knew of my post-divorce desire to explore my bisexuality. She said she would be over in an hour. It was now time to contact Drew. Would I be another timid fellow afraid to take the leap – just another time waster? Not a chance anymore. Life is lived once, and I already spent too many years going through the motions. I sent a simple note back to Drew. "Will do. Meet me after 2 pm." I included my address. Susie was over by noon. She brought her makeup kit, a wig of long black hair, and a satiny robe. "Greg, I didn't know this was your thing, but we're going to have some fun." She expertly applied rouge, eye shadow, mascara, and lipstick – a very burgundy lipstick that really stood out well I thought. The wig took some work, but we finally got it looking quite reasonable. I had to admit, I looked pretty good for a first-time dresser. I wore nothing other than my pink panties with Susie's white satin robe draped around my shoulders. It wasn't too long after she left that the doorbell rang at 2:09. He was prompt! When I answered the door, I couldn't believe how ruggedly handsome Drew looked in person. His head was shaved, with a bit of stubble revealing a receding hairline. The most striking feature was his wide chiseled jaw, with a light dusting of stubble suggesting he hadn't shaved today. He wore faded jeans and a simple dark t-shirt, which showed off his muscular forearms and wide shoulders. His accessories included a thin silver necklace, matched by a thick silver bracelet on one wrist and a silver watch on the other. The outfit was topped off by a pair of snakeskin cowboy boots. "Hello, it's nice to meet you, please come in" I said, trying not to leave the door open too long in my satin robe. He grunted thanks and stepped inside. "Can I get you a drink?" I asked. He declined and instead sat down and took his boots off. I tried to make a bit of small talk, but mostly received short responses in return. His eyes were dark and burning with intensity. He didn't seem the type for chit chat, at least not with me standing there looking my feminine best. Finally he interrupted me and said, "You better get started, I have things to do today." I didn't need to be told twice. I moved over to the couch as he peeled off his t-shirt to reveal almost black nipples sticking out of his pectoral muscles. He unbuckled his belt and lifted himself deftly while sliding his jeans to the floor. He now wore nothing but animal-print bikini-cut briefs, which showed his huge bulge beneath. I was hard as a nail looking at it, and ready to set to work. I teased his thick soft cock, running my fingers over his briefs. I alternated between light tugs and gentle pressure, and felt it starting to swell. Without further delay, I pulled both cock and balls out one side, and beheld the magnificent sight of his long, thick, and very dark cock. He was uncut, and a pinkish tip showed beneath the dark foreskin. I cupped his balls with one hand as I leaned over and placed the head between my burgundy lips. My mouth was salivating more than I can ever remember, and quickly his entire length gleamed with my saliva as I slowly bobbed up and down, relishing the sensation of his thickness becoming fuller. This was the most thrilling sensation I had ever felt. His cock soon became too large for me to take fully, and I wrapped my left hand tightly along his base while my mouth continued to bob gently up and down, swirling the underside of his penis with my tongue. I leaned back again to view it, while using both hands in a swirling motion as it stood proudly upwards with the gentlest curve towards me on his left. Playing with his foreskin was a new adventure for me, and I was enjoying it. He hadn't said or done anything yet, but as I fondled him, he moved his left hand up my back and gripped my neck. He firmly but slowly pushed my head back towards his dick. I got the message, and slid off the couch so I was now on my knees in front of him. I began sucking with more intensity as my hands were placed firmly on his thighs for balance. He was starting to rock a bit to my head bobbing. I glanced up and saw his head tilted back on the couch, eyes closed, with both hands twisting his own nipples. He sure looked to be enjoying himself, I thought. I continued bobbing faster and faster, nearly gagging more than once. I could tell by his quickening rhythm that he was now in face-fucking mode and going to get off soon. I shifted my weight a bit so that I could free one hand to stroke in unison with my bobbing. This was the added sensation he needed, and after a couple minutes he grunted, "Get ready to swallow." Seconds later I felt the first warm blast fill my mouth, followed by one and another as he let out a deep growl and gripped both my shoulders so hard that I noticed bruises later in the day. His cum was delicious and very thick. I slowly sucked on his manhood until it had receded, making sure I swallowed every drop as he wished. Once I had it all, I leaned back to see his black beauty, flopped to the left side with the briefs still pushed to the right. It was wet and one vein still protruded. I dare say it was the most beautiful cock I had ever seen, certainly the most beautiful I was ever likely to taste again. I got up and brought back two glasses of water. He still hadn't said anything, but drank it down while he looked around the room. I broke the silence by commenting on how wonderful he tasted. He thanked me and said it was great for him, too. I wasn't sure what was next but remembered his message – so far we were only two-thirds done. Suck his cock. Check. Swallow his cum. Check. Now to get my tranny ass fucked? That would definitely be a first. Unfortunately it was not to be this afternoon. He leaned over and grabbed his jeans and shirt and asked to use the restroom. After relieving himself, he returned dressed as if ready to go. He sat down and put his boots back on. "Hey listen," he said. "I have some things to do, but I'm not done with you. I'll be back here around 10 tonight. You best have some condoms and lube ready." With that, he thanked me again and was out the door. It took me fewer than 2 minutes after he left to soil my panties. I cleaned up and then was out the door headed to the store. I needed to buy condoms. Big ones. 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... ***** 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.