They'll Never Now

"It's time, Myloe," Winter told him, "are you ready?"

Nervously he replied, "As ready as I'll ever be. Are you sure this will work, they'll never know?"

Reassuringly Winter told him, "As long as you do what we planned. Besides, imagine how humiliated you'd be if they found out. You would never be able to face them again."

For the four years they've been together, both Myloe and Winter knew he was bi-curious. He was up front about it in his dating profile. She hadn't known it, watching porn together with Myloe revealed Winter's desire to watch her man give a blowjob. Being the adventurous couple they were, and secure enough in their relationship, they decided to make it happen. For the last six months or so they worked out the plan, poked holes in it, and refined it until they were both confident it would work. During the planning phase, they discovered his humiliation fetish was more deeply rooted in his personality than either realized. That's why Winter decided Myloe would give blowjobs to three of his closest friends.

The plan was simple in theory. Myloe and Winter would plant the seeds with his friends, then work together to gently encourage each of them until all were on board and willing. Executing the plan took a little longer than they thought it would. I mean, who would have thought three single guys would hesitate to get a blowjob from one of Winter's hot friends? The story was that the friend was in town visiting, has a kinky side and always wanted to blow multiple men in one night, but never had the opportunity. Winter and Myloe told the group they could be her opportunity.

Sure, there were conditions. They would have to agree to be blindfolded and wear ear plugs so they would not be able to see her, or figure out who she was. And their hands would be cuffed behind their backs to ensure they didn't "accidentally" dislodge either, and could not reach out and feel her. But, for a blowjob, those requirements seemed acceptable to Myloe and Winter. To Drew, Jack, and Ronald they were a bit harder to accept. Rightfully so, knowing full well Myloe's sense of humor and propensity for pranks, they were nervous they were being set up.

The part of the plan Myloe and Winter were concerned about was having all three in the same room at the same time. Their house wasn't that big, they didn't have enough rooms to put one in each. Logistically, it wasn't reasonable to have them show up at staggered times, either. The solution they came up with was to have only one in the room with Myloe, while Winter stayed in another room with the other two.

The rest of the plan, including having Myloe wearing satin gloves so the guys wouldn't feel his rougher hands and a wig so some long hair would tickle their bellies and upper thighs. Given that Myloe was bald, that may have been a clue they didn't want to give had his head touched their stomachs. He even agreed to put on a little lipstick so they'd see some on themselves when he was done. Lastly, the story was that Myloe was out of town for business, but he knew what was going on and approved of it. Anything to help one of Winter's friends, he'd told them.

And so there he was, sitting in a chair in their spare bedroom waiting for Winter to bring in the first guy. They had agreed that the guys could pick the order and Myloe wouldn't know about it beforehand. Not that it would have mattered, but they both liked the idea of the additional surprise element. He was surprisingly calm, and not surprisingly excited for what was about to happen. He was wearing only the gloves, wig and lipstick, his free cock was pointing straight up, hard as a rock.

Winter opened the door and led Ronald in, and stood him in the middle of the room. She motioned for Myloe to be quiet, removed one of Ronald's ear plugs and told him, "She looks so fucking hot today, I wish you could see her." Myloe just shook his head at Winter's devious side coming out. And, Myloe noted, his heart both skipped a beat and was beating faster with Ronald in the room. As agreed upon, Ronald was naked from the waist down. Winter and Myloe didn't want there to be any issues with removing clothes.

Myloe noted that Ronald's cock was about the same size as his and he was circumcised. Until now, he hadn't given circumcised or uncircumcised a thought. He realized that in his fantasies, all the cocks were circumcised. Maybe just because that's how he was, and a lot of cocks he'd seen in porn were the same. Myloe noted Ronald was already hard. Winter slipped Ronald's ear plug back in and left the room, closing the door behind her. It was just him and Ronald in the room now.

Myloe gathered his thoughts, realizing he couldn't wait too long, moved out of the chair, kneeling on the pillow in front of Ronald. Reaching up with his gloved hand he touched another man's cock for the first time in his adult life. Wrapping his hand around he pointed it towards his mouth, leaned forward and took the head in. He didn't stop to think about how it felt in his hand, was it warm, harder but soft and spongy, or anything like that. He knew if he didn't just go for it he'd chicken out and probably never get the chance again. Slowly he started to swirl his tongue around. A contented sigh escaped Ronald's lips.

Slowly Myloe took more and more of Ronald's cock into his mouth, stopping just before he hit his gag reflex, and gently sucked on it before sliding his lips up the shaft, using his tongue to massage the underside of his cock the entire way. After the first couple of cycles of slowly bobbing on Ronald's cock Myloe sped up his pace. As he went faster he realized how much concentration it took to not scrape the cock with his teeth. Who knew giving a blow job could take concentration, that it's not just simply put it in your mouth and bob your head up and down? Fortunately for Myloe, Ronald didn't last that long. Within a couple minutes, during which Myloe varied his speed, and sometimes paused with just the head in his mouth, gently suckling it and using his tongue, Ronald's breath started to quicken and his hips instinctively thrust forward to meet Myloe's mouth. Myloe could taste the precum starting to flow. There wasn't much taste to it, just a slightly bitter flavor.

When Ronald thrust his hips forward and held them there Myloe knew he was about to cum. On the 'up stroke' Myloe stopped and kept just the tip of Ronald's cock in his mouth and continued to swirl his tongue around, paying more attention to the sensitive underside, spreading the precum that was still flowing. Soon that precum turned into a full on blast of cum. Ronald moaned and gasped just before his cock twitched and exploded in Myloe's mouth. Well, maybe exploded was the wrong word. There were a couple of relatively (compared to Jack and Drew as he'd soon find out) weak spurts of cum before the rest just flowed out. That didn't matter to Myloe. He was so focused on tasting another man's cum for the first time he didn't really analyze that part.

He'd waited for this moment for a long time, through two previous relationships in which he never felt comfortable enough to admit to and talk about his bi-curiosity. He'd fantasized about how it would go. Would he continue to bob on the cock and try to swallow on the up stroke? Would he swallow as quickly as possible or let it pool in his mouth? How would it taste? How would it feel having another man cum in his mouth? In the end he'd decided he'd just go with the flow and whatever felt right at the time is what he'd do. As the cum pooled in his mouth, coating his still swirling tongue he savored the taste. It was all he'd hoped for. Tasting only subtly different from his own, which he was quite familiar with from propping himself up on a wall and cumming in his own mouth and from licking if off and out of Winter's body.

At that moment Myloe was proud of himself, a contented feeling settled over him. He finally had the courage to explore, to push himself past traditional societal norms and the associated expectations he'd grown up with. Here he was with a cock in his mouth, his mouth full of cum. Smiling as best he could, Myloe swallowed his mouthful then let Ronald's cock slip from his mouth. Moving back to the chair, Myloe sent a text to Winter that he was done. Winter returned to the room, smiling at Myloe as she guided Ronald out and closed the door behind her. Her role was to lead Ronald out to get dressed and leave, then to blindfold and cuff the next person and lead them into the room. Myloe knew Winter was taking the opportunity to see what each of his friends were packing.

Next in was Jack. On his knees in front of Jack, Myloe took a little more time to analyze his cock. Having sucked Ronald off, confirming he loved the taste of cum, he knew he wouldn't chicken out this time and saw no reason to rush. Myloe noted that Jack was already hard, his cock a little longer and fatter than Myloe's and the veins were very noticeable. He was also circumcised. As soon as Myloe was kneeling in front of Jack, Winter left again.

Myloe slowly licked Jack's cock from the head, down the underside, to the junction where his cock and balls met. Gently, Myloe captured one of Jack's balls with his lips and sucked it into his mouth. Caressing the sack all the way around his ball. When he was done with that one he licked his way back up one side of Jack's shaft and back down the other, repeating the process with Jack's other ball, causing Jack to moan. Taking that as a good sign, Myloe alternated between sucking Jack's balls and licking the entire rest of his sack.

Making his way back to Jack's head, he slowly took the cook as far in his mouth as possible. Knowing today was all about Myloe, he wasn't worried about giving Jack the best blowjob he'd ever had. Instead, Myloe wanted to feel what it's like to have his mouth used. Making sure he was in the best position possible, directly in front of Jack with his mouth lined up with his cock he gently grabbed Jack's hips and moved them back and forth, fucking his mouth with Jack's cock. Jack got the message and started to fuck Myloe's mouth. Myloe kept suction on Jack's cock and did his best not to scrape his teeth. He was mostly successful, and gained a new appreciation for Winter when she talked about her jaw aching. Fortunately for Myloe, at least in this circumstance, is that Jack lived up to the name the rest of the group teased him with, a 'minute man.' Jack thrust his hips forward and kept them there. His spasming cock spewing his cum into the back of Myloe's throat. Myloe struggled to swallow it all, failing as some escaped around Jack's cock and dripped down his chin. Myloe continued to use his tongue and suck on Jack's rapidly softening cock until he couldn't take it anymore and pulled out. Myloe signaled Winter who stepped in and led Jack out. Jack thought about how quickly both of his friends had cum. He didn't know if that was normal or not, and tried to think how long he's lasted with Winter blowing him.

Last was Drew. Winter led him in. Saving her surprise for last, when Myloe started to move into position she stopped him. Leaning down and whispering in his ear, "I told him that my friend told me when I was getting Jack that she wanted to taste her pussy on a cock. So, I guess we need to make that happen. Oh, and this will satisfy one of your other fantasies as well, to taste my pussy on another man's cock." As she finished saying that she lifted her skirt up to her waist, revealing she wasn't wearing panties. Myloe was stunned. This was not part of the plan, he had no idea Winter was planning on fucking one of his friends, and voiced his concern to Winter.

"I'm not going to fuck him, Myloe. I'm just going to bury his cock in my pussy once," she replied with a wink. Myloe was still stunned as Winter stepped in front of Drew and bent over. Looking at Myloe she raised her eyebrow. This was her asking if Myloe would be OK with this. Not really having time to think, Myloe's cock drove his answer. He just nodded at Winter.

"He needs to feel your gloved hand, not my skin. Come over here and hold it so I can slip it in." Still off balance, Myloe did as he was directed. Grabbing Drew's cock he pointed it out straight. Using her hand on Myloe's, Winter felt Drew's head on her lips and adjusted his tip slightly to ensure it was lined up. Slowly she slid back until Drew's cock was fully buried in her pussy. She whispered to Myloe, "He's so big." She ground her ass against Drew before leaning forward, sliding his cock out. Standing up she let her skirt fall, told Myloe to enjoy and went and sat in the chair. Myloe looked at her quizzically. Looking at him she told him that she wanted to watch this one. Again she raised her eyebrow. Myloe nodded again and moved in front of Drew.

Myloe wasn't sure he wanted Winter to watch but figured he'd already sucked two cocks, why not do the third with her in the room. Licking his lips Myloe could see Winter's wetness glistening on Drew's cock. Without using his hands Myloe gently took Drew's head in his mouth. It was a whole different mental experience tasting Winter's pussy on him. Immediately he knew he'd made the right choice, well his other head had, in letting Winter take him in once. Myloe noted that Drew had the biggest cock, both girth and length of the three. He couldn't help but wonder if Winter had him go last for a reason. He wouldn't put it past her, but didn't know how she'd know how big he was. He didn't take too much time to think about that.

Myloe used his tongue again, trying to lick all Winter's juice off Drew's cock. He suckled the head before following his pattern with Jack, licking up and down Drew's cock. As he was doing this he looked over and made eye contact with Winter. He could see the excitement on her face and noticed she had hiked her skirt back up and had her finger buried in her pussy.

Myloe turned his attention back to Drew. Sliding his cock further into his mouth, Myloe tried to get every last bit of Winter's wetness from his cock. Something mentally was going on, too. Having fantasized this scenario, and sharing it with Winter during some of their more heated sexual escapades, he appreciated Winter for making it come true. Not just the last part, but all of it. Not thinking about that too much, Myloe turned his attention back to Drew.

Myloe continued to work Drew's cock with his mouth until he was getting close. Both he and Winter recognized the signs, and while Myloe intensified his efforts, wanting to take his third load of another man's cum, Winter lowered herself behind him. "It would be so hot to watch you take him on your face." Myloe turned his head slightly to look at her. Out of the corner of his eye he could just see her smiling face. And he decided he'd give her what she wanted. After all, she'd given him this night.

As Drew started to cum, Myloe moved him out of his mouth and pointed Drew's cock towards his forehead. Drew spurted multiple times, each one landing on Myloe's face, with the last couple of less powerful blasts landing on Myloe's nose and lips. Myloe took Drew's cock back in his mouth and nursed the remaining cum from him. As he slipped the cock from his lips, Winter turned his face towards her and kissed him, her tongue searching his mouth for any remnants. Pulling away, she whispered that she needed to lead Drew out, then she was going to come back and finish what she started.

When she came back into the room, Myloe was sitting in the chair with the gloves and wig removed, his cock still hard. Straddling his lap, Winter lowered herself down, guiding his cock into her. Sighing, she leaned forward and licked some of the cum from Myloe's face, parting his lips with her tongue she kissed him. Winter wrapped her arms around Myloe's neck and rode him until he filled her with his cum. Looking into Myloe's eyes she asked, "Do you want one more today, or did you already swallow enough?"

"You know the answer to that," he replied, lifting Winter off him and laying her on her back. Winter spread her knees as Myloe leaned in, gently lapping at her pussy lips. Diving his tongue into her folds lapping away at his cum leaking out of her. When he sensed Winter getting close he latched onto her clit, sucking gently and bathing it with his tongue. It took Winter over the edge as it always did.

After they'd cleaned up, sitting at the table enjoying a drink, Myloe thanked Winter for helping to make his fantasy come true. He did admit to her he was surprised and a little taken aback when she took Drew into her, but as soon as he tasted her on him, he was more than OK. Winter smiled devilishly and said, "I was OK too, he felt so good."