Sal's Dilemma Pt. 01

[Authors note: This is an edit to correct a cut and paste error that occurred just prior to first publishing the story. My thanks to Literotica member "Fleshmaster100", some of the characters and scenarios in this story are based on his fantasies. When someone feeds the ideas, it makes fleshing out the story much easier. Thanks "Fleshmaster100". ]

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Sal had been married to Rosa for a few years and life with her had become boring. It seemed that they didn't have much in common and the spark that once was had been extinguished. They had tried every position they could imagine but, their sex life was still ho-hum. Sal was looking for more from Rosa and he let her know that he needed more. They discussed the problem, Sal suggested a threesome but Rosa wouldn't hear of it.

That night Sal tried a new tact. He pushed her down on the bed, propped her ass high on a pillow and pushed her knees apart and up against her chest. Her pussy and ass were on full display. He dove in with his mouth and tongue whipping up some pussy juice and as it leaked down the crack of her ass, he licked it and she responded enthusiastically as his tongue probed and circled her puckered hole. When her hole was wet and slippery with saliva and pussy juice, he slid a finger inside and worked it in and out. She was enjoying the attention and became more animated than she had been in months, hell maybe even in years.

Sal was energized, maybe life was going to get better. He added another finger and soon after some lube and a third. Rosa was really enjoying this new kind of attention. Without a word to her Sal pulled out his fingers and speared her ass with his big cock. She screamed with pain. Sal continues a slow but steady descent to the depths of her bowel. She tried to push him off but he didn't budge. With his cock impaling her the pain subsided and she was no longer pushing him away. Sal moved slowly back and forth in very short thrusts. She willingly opened herself to him and was soon urging him to go faster and harder. Her excitement was obvious her pussy was dripping wet and adding lubrication to sloppy union of cock and ass.

Sal plowed her ass for several minutes and when he felt his impending orgasm he rubbed his thumb over her clit a few slippery strokes and she came harder than Sal could ever remember her cumming before. The convulsive tightening of her body caused her sphincter to clutch and squeeze his cock causing him to have an explosive orgasm. His cock unloaded pulse after pulse of spurting cum into her ass. He pulled out almost all the way then back in a couple of times before letting his wilting cock slip from her hole. Thick white cum seeped from her ass and down her crack. Sal scooped some of it onto his finger and offered it to Rosa her lips parted and she sucked it from his finger and said "mmmm good". Sal thought, 'Fuck, she has never been willing to taste my cum before! Why now? Could it be because he fucked her ass or was it because he took charge and fucked her without giving her a choice?'

Rosa said it was because it was new, she never had it up the ass like that before and she had been really turned on and tasted it before she realized what she was doing. Sal decided to test his theory. The next time they had sex, Rosa laid on her back and spread her legs. Sal slid his cock into her pussy. There was nothing, no excitement and not very wet. She suggested, "Put it in my ass." To Sal it sounded more like an order given in Rosa's irritating whining voice that had always grated on Sal's nerves. He didn't say anything, just got some lube, lubed her ass and his cock, loosened her up a bit then mounted her.

It was enjoyable for both of them and she did get wet, but when Sal flipped his thumb over her clit she did not cum and she wouldn't taste his cum. This made Sal think that it was his aggressiveness that really turned her on the last time. He decided to put the theory to the test. The next night when they went to bed Sal looked her in the eyes and said "Rosa I am going to fuck you in the ass and I don't want to hear your shrill whining voice so keep your fucking mouth shut." He didn't want to hurt her so he lubed up her ass and his cock without much loosening of her sphincter. Sal lined up his cock with her hole and pushed in to the hilt.

Rosa screamed with pain but didn't say a word. Sal rode her hard and deep. Rosa's pain was soon gone and she was moaning with pleasure. She still didn't say a word. Her lips were squeezed tightly together. Sal slammed into her until he was on the verge of climax. He reached down and flicked her clit and she exploded into a massive orgasm. The spasms of her cunt pushed Sal over the edge. He pulled out while his cock still spurting cum. He grasped his cock at the base to keep his cum in and presented it to Rosa's lips. She willingly opened her mouth and Sal slipped the head between her lips. Rosa sucked up the rest of his cum and licked his cock clean. 'Fuck that was hot!' Sal thought.

He continued his aggressive behaviour with Rosa and indeed the more aggressive he was the more turned on she was. She had massive orgasms and wanted his cum as a tasty treat. Sex became exclusively anal, but it was still Rosa and soon it was boring and unexciting as it had been before. Sal started thinking there had to be more, sex shouldn't be boring. Maybe he needed to find a new pussy.

Sal looked to the internet and found some porn. The women were beautiful, the cocks were big, but the orgasms were fake. This wasn't it, then he clicked on a thumbnail with two men. The video started, the two very masculine men were kissing. Sal's cock twitched. The scene changed and one guy Jim, was blowing another guy named Al. Sal's cock started to fill and remained about half hard through the scene.

In the next scene, Al pushed Jim back onto the bed. He landed on his back his 6" cock slapping against his belly. Al was on him immediately grabbing a pillow and roughly shoving it under his ass then pushing his legs apart. Al dove in and rimmed Jim shining his ass up with saliva then spit a gob into his asshole. Without further preparation he mounted Jim. 'God!' Sal thought, 'he must be at least 8 inches.' Al's big cock penetrated Jim's ass. Jim screamed in pain.

Sal's cock instantly became rigid. He freed it from the confines of his briefs, the tip poking over his waist band. He unbuckled his belt and slipped his trousers down to his knees. Al was starting to pump into Jim who was still whimpering from the initial onslaught. As Al's strokes continued it was obvious that Jim was starting to relax. Soon he was encouraging Al to fuck him hard. Sal started stroking his throbbing cock.

Al was fucking Jim with long strokes slowly pulling out then slamming back into him. Jim was begging Al to give him more to keep going "Please keep going, don't stop, please keep going, oooh fuck I'm going to cum, keep going." Al's cock must have been pounding his prostate. Without any stimulation, Jim's cock pulsed and a huge load sprayed out coating his belly and Al's chest.

Jim's orgasm triggered Al's and he unloaded deep in Jim's ass. He kept fucking until his cock wouldn't work anymore and slipped limply from Jim's ass. His cum leaked down his crack, it looked like a pearl necklace slipping from his ass. Al scooped it up and mixed it with Jim's cum on his chest. He then licked up a mouthful and shared it with Jim in a hot post coital kiss. Sal lost it and shot a huge load all over his shirt with the final drools running down his cock and coating his hand.

Over the next few weeks Sal looked at more gay videos. He was really into dominant men and pictured himself in that role. He found other porn stars that were dominant, but none better than Al was. He had watched Al in several videos and many different positions. Al was always the top and in total control, fucking his partners hard and deep.

Sal began to fantasize about having sex with men. He wanted real men, not sissies, real masculine men. But he questioned whether men that would bottom were really masculine. Could masculinity and submissiveness be found in the same person? He decided to run an ad on craigslist in his local community.

[Dominant masculine top seeking submissive masculine bottom.]

He didn't have to wait long before he was getting replies, there were four in the first hour. He read the replies but didn't answer any of them right away. He was thinking 'this could really happen' and having second thoughts 'What if I get a disease? What if I get beat up?' His nerves were on edge he wanted it badly but he wasn't ready to come out. 'Will my friends and family still accept me?' So many questioned, so many doubts, what to do?

Sal didn't get much sleep that night. He was restless and excited and worried. When he checked his email the next morning there were five more replies. Sal decided he would spend some time reading the replies and respond to two or three of the best.

Reply 1

Yo man, let's fuck!

Reply 2

Married guy 40 yo 5'10" 175lb never been with a guy before. Have used dildo on my ass. Let's do this.

Reply 3

Would love to get fucked. Let's do it.

Reply 4

I have fantasies about doing this. I am a 36 year old virgin. Never been with a man or woman. I am scared but would love to try this.

Reply 5

34 yo masculine 6' HWP would love to bottom for you.

Reply 6

Hi, would love to meet you. I'm masculine, single and horny for cock. 38 yo 5'11" 175 lb.

Reply 7

Hey. I'm the guy you're looking for..

Reply 8

Please come to my place and fuck me.

Reply 9

Where you been, I been lookin for y'all.

Sal read all the replies and realized that none of them actually gave him much to go on. He decided to get back to #4 "I have fantasies about doing this. I am a 36 year old virgin. Never been with a man or woman. I am scared but would love to try this." And #2 "Married guy 40 yo 5'10" 175lb never been with a guy before. Have used dildo on my ass. Let's do this." His message to both said, "I liked your reply to my ad. You gave me some personal information. I would like to meet you. Please send a picture." Sal was nervous but excited.

Within an hour he heard back from #2 the married guy. "Sorry, can't send a picture. Have to protect my identity. I'm married and can't risk losing my family. I just want to get fucked, so if you want to meet I am available 4 or 5 evenings a week. Let me know." Sal's heart was beating and he could hardly breathe. He went to his bar and poured himself a stiff drink. 'Fuck,' he thought, 'this is really happening.' He replied, "OK, I understand about the picture. Can we meet Tuesday or Wednesday around 7:30pm at Robin's on First St."

Meanwhile he had received a message from #4 the virgin. Sal really wanted this guy to be the right fit. He could imagine being the first to invade his ass. The message said "I'm very nervous about this but I really want to do it. I live alone and often work from home so I'm available almost any time. I have attached a picture." Sal was impressed until he opened the attachment. It was a picture of an asshole with a huge dildo stuck in it. Sal was impressed with the size of the dildo but, being his first was somehow less appealing. He doubted there would be any pressure on his cock while fucking that ass. Would either of them be able to feel it? Sal wrote him off for now.

Before bedtime he had an answer from the married guy, "Sounds good let's meet on Tuesday. I'll be wearing a Red Wings cap and a brown jacket."

Sal was feeling a little better now less nervous and more confident. "Tuesday it is. I have a Black Hawks cap and a black jacket. The hockey theme is a natural ice breaker. Look forward to meeting you."

Sal was at the coffee shop five minutes early but no one wearing a Red Wings cap ever showed up. "So much for round one, back to the drawing board,' thought Sal as he left the shop at 8:00pm.

Sal went back to his the other responses. Reply #6 "Hi, would love to meet you. I'm masculine, single and horny for cock. 38 yo 5'11" 175 lb." appealed to him. It was friendly and a single guy would be more likely to show up. Sal's message, "Thanks for responding to my ad. I would like to meet you too. I am 37 years old about the same height and weight as you are. My cock is 7" thick and hard. If you are still interested in meeting, when would be good for you?"

Sal's nerves were still on edge, the first two attempts failed. Would this guy prove to be the one? How would he feel if and when they met?

As he was thinking about the possibility he got an email. "Hi my name is John, you sound perfect to me and I do want to meet you and that thick juicy cock. I live alone in a private secure building so meeting up is no problem. I work until 5:00 Monday to Friday and weekends off, so suggest a time that works for you and it probably will work for me. Pic attached."

Wow, Sal thought this guy is good looking and very open. He had a good feeling about this guy. He replied, "I'm impressed with your message and you're nice a looking guy. Can we meet tomorrow evening, just send an address and time we can meet."

The next morning there was a reply. "Sure tomorrow is fine about 7:30 would be great. My address is 2450 Pine Avenue, Apt. 22. A see your then."

SaI was thrilled about this guy, good looking, toned body, definitely masculine, it was going to be a long day. Sal went to work, but his heart wasn't in it. John was so sexy he could imagine pushing him down on the bed, holding his hips and sliding his cock into his asshole. The day plodded on and finally it was quitting time. He went home, hurried through supper, said hi to Rosa and then into the shower. Paying special attention to his cock and balls, he was getting hard, he started stroking his cock, he was getting close to orgasm, it felt so fucking good. `Ooh fuck' he thought as he blew his load. Then, 'oh well I will last longer when I fuck John.' He thought.

"I have to go out for a while the boss wants me to interview a guy for a contract at work," be lied to Rosa. Then off he went to Pine Avenue.

It was 7:15, he was early. He was pacing back and forth in the hall outside John's apartment. 'Should I knock,' he wondered. He didn't want to come off as too eager. The door opened and John stepped out into the hall. "Sal?"

"Yeah, yeah, I'm Sal. John how are you?"

"Horny," said John.

"Yeah, me too." Sal said.

"Ok then, come on in," said John.

Sal stepped into the apartment. It was a great place, well decorated, nothing sissy about this guy. Sal's cock was getting hard in a hurry. He turned and extended his hand. John grasped it. Firm masculine handshake, Sal was going to enjoy this evening. He tugged on John's hand, pulling him into a hug. John hugged him back and brought his lips to Sal's mouth. Sal thought it was a little forward, Sal returned the kiss

Sal had never kissed a man before and he kind of liked it. He pushed John backward toward the sofa. His hands were all over John, he cupped John's crotch' John's cock was hard as a rock and a pretty good size too. John moaned and opened his mouth. Sal slid his tongue into John's mouth and their tongues fought for position. Sal thought, `This doesn't feel like he is submissive.'

Sal broke the kiss and pulled John to his feet. "Where's the bedroom?"

John pointed down the hall and to the left. Sal almost carried him and pushed him roughly on the bed. Sal pulled his shoes off and unbuckled his belt, pulled off his parts and underwear in one pull. John's cock was big about 7½ inches and thick. He pried John's legs apart and looked at his puckered hole. Sal was rock solid, he stripped and got on the bed. John had a bottle of lube and condoms on the nightstand. Sal grabbed a condom, put it on his cock and lubed both his cock and John's ass.

He aimed his cock at John's ass and pushed. He felt his cockhead penetrate John's ass. John tensed up and his sphincter clenched around Sal's cock. John groaned in pain. Sal gave him a few seconds to adjust and relax. John told him to go slowly deeper. Sal didn't listen he started fucking him hard. It was very painful. John was a strong man. He threw Sal off of him and shouted "What the fuck is wrong with you man. Yes, I am a bottom and I am submissive but sex is to enjoy not to hurt or be hurt. You are hurting me. Get your fucking clothes on and get out of here!"

"Whoa, you knew that I am dominant." Said Sal.

"Yeah, I get that, but just because you are dominant doesn't mean you have to be a fucking predator and go around hurting people. You came in here and grabbed me, pushed me around. The kiss wasn't bad so I let you get me to the bed. But driving your cock into my ass without preparation and then fucking me hard while it was still painful after I asked you to go slow is a deal breaker. You're not dominant you're a fucking predator. Now GO! Get the fuck out!"

Sal got dressed and left thinking, 'Is he right? Was I acting like a predator?' Then it occurred to him that the bottoms he had seen in porn movies were enjoying being fucked. Rosa had enjoyed it, but Sal had never been as rough with her like he was with John. 'Fuck' he thought 'maybe he was "the one" and I screwed up.' He was mad at himself thinking he would never get another chance with John.

Sal decided to move on and learn from his mistakes. He contacted #5 "34 yo masculine 6' HWP would love to bottom for you." Sal wrote, "Sorry for the delay in getting back to you. If you are still interested so am I, let me know if you want to hook up."

The reply came back almost immediately. "Sorry been getting it from another guy for a few days now. I kind of like him. Maybe if this doesn't work out."

Sal wasn't going to wait around for anyone, but the rest of the replies he got were so lame. Oh well he would reply to them and see what happened. He wrote the following and sent the message to #1, #3, #7 #8, and #9. "Your reply to my ad was very short on detail. I'm not sure I want to meet you, but please tell me more about yourself and we can go from there. If we do meet I want to play the dominant role but there will be no pain or torture."

Sal received only one reply to this message. It came from #7 'Hey. I'm the guy you're looking for..' "Hi, I'm Tom, I am shy, some people think I am a little introverted, but once I get to know people I can kick back and have fun. This is all new to me. I had a girlfriend but something seemed off. I started to realize that I was more comfortable with guys than girls. Sometimes I wish I had been born a girl. Then I could be with a guy. I recently broke it off with her and realized I want a man and I want to be the girl in the relationship."

Sal read the message and was astonished at how much this guy had opened up. He replied, "Hi Tom. I'm Sal. I want to meet you. My work hours are quite flexible when would be a good time for you?"

Sal felt good about this guy, he realized that giving up the predatory attitude may have made it possible for shy Tom to open up to him. Now he had to make sure he didn't fuck things up.

Sal didn't hear from Tom for two days, he was pretty sure that he would never reply but late that evening he got a message. "Hi Sal, I was really busy at work yesterday and ended up working overtime very late. Today was back to normal and I'm home now. If you can make it tonight I am here and would love to get together."

Sal answered immediately, "Where do you want to meet?"

The reply came in less than 5 minutes, "Do you know Robin's on First St.? My apartment is near there. "

"Yes I can be there in 15 minutes. Going to wear a Black Hawks cap and a black jacket."

"Look forward to meeting you. See you there. Blue jacket and red cap."