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  • Greg Tries a New Angle Ch. 01

Greg Tries a New Angle Ch. 01

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.

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