Old 11-20-2017, 03:33 PM   #31
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I absolutely cannot wait to see what happens next! I’m honestly hoping he gets put in panties and tied up and then they whip out their phones and take pics lol
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Old 11-21-2017, 11:07 AM   #32
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Well, it’s not going to be exactly that, but I think you’ll enjoy it anyway

Just a heads-up: I’m visiting family for Thanksgiving, so I probably won’t be able to get the next part up until the weekend, but FYI... it’s gonna be good.
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Old 11-24-2017, 06:25 PM   #33
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Hope you enjoyed Thanksgiving. Looking forward to the next update.
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Old 11-25-2017, 08:28 AM   #34
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CHAPTER 17

“The boys I dominate tend to get pretty loud,” Shannon explained, holding out the ball gag in front of her and advancing toward Matt. “I find it’s best to keep them nice and muffled.”

Shannon fastened the ball gag around Matt’s mouth, cinching it tight enough that all he could do was grunt. There was no way he could object to whatever was going to happen next! All around, the audience of girls were clapping softly at the sight of his humiliation.

“Next is a little tradition of mine,” Shannon told him. “For the next few minutes, anyone her can touch you however they choose. All you need to do is stand still.”

As if Matt could shout in protest anyway.

Megan was the first girl up, her fingers light on Matt’s skin. He remembered how she looked, bottomless and confident, when she had interrupted his submission to Sam and forced him to eat her out. He’d cum in front of her that day. Now, she was smirking as she flicked his balls.

A couple of the girls he didn’t know came up together, focusing their attention on his cock and balls, looking too nervous to touch for long. They were followed by Ailie, a girl from his English class with brown hair and a thoroughly average body, who gave his cock a few vigorous strokes before kissing him on the cheek, reaching around, and spanking his ass. Then Theresa, a blonde girl with massive breasts who played the clarinet, devoted her time with him to sucking on his nipples. Matt had never seen his nipples as being particularly sensitive, but he couldn’t deny that Theresa was turning him on. Before she left, she squeezed the head of his penis, wiping up a drop of precum and smearing it on his chest.

Katy came next, the girl who had broken up with Matt two years ago and with whom he hadn’t done anything beyond kissing. She positioned herself right in front of him, standing on tiptoe so her crotch in jeans was just a couple of inches above his cock, and wrapped her arms around him. “Well, Matt,” she whispered, “this is something we never tried while we were together.” Her hands slid down his back until they cupped his ass. “I bet you always wanted to know what my body looked like. I’ll be honest, it’s good. And I wanted to fuck you then, too. All you had to do was ask, but you were too timid.”

Katy grabbed Matt’s hand and slid it up under her shirt. It came to rest atop one of her bra covered breasts, and it felt incredible. Katy lowered her crotch onto his dick, grinding on it gently. “You want me now, I’ll bet. But you missed your chance.” She pulled away, giving his cock a parting stroke.

Matt thought he’d blow his load just from that.

The next two girls he didn’t know, but they were cute, and together, they touched just about every inch of his body. After them came Kelly, a nerdy Asian girl from his orchestra with smaller curves. He took Statistics with her 2nd period every day, and now she was jerking him off! She shocked Matt by sinking to her knees and putting most of his cock inside her mouth. He could feel her tongue circle the edge of his manhood, and he shuddered, moaning through his gag. But he didn’t cum before Kelly pulled away, squeezing his testicles as she went.

Last, but not least, was Kim. “You thought I wasn’t worth dating when I was younger,” she said, hips swaying as she closed the distance between them. “Shannon’s invited me to a lot of these little sessions, but I’ve never looked forward to one as much as today’s.” She grabbed Matt’s cock and jerked it violently. Her polka dotted dress looked great on her, and she wrapped her bare calf around his ankles and started to drag it up the backs of his legs.

“Admit it, I’m a catch.” Kim waited for Matt to do something, and he finally nodded. She wasn’t as hot as Sarah, but there was something alluring about Kim. She kissed the ball of Matt’s gag as her calf reached the height of Matt’s ass. “You missed out, Matt, and let me tell you, it really upset me for a while. But this... this is helping.”

Kim winked— then stuck a finger inside Matt’s asshole!

Matt’s grunt was of a higher pitch this time, more of a yelp. Kim was grinding against him now, only unlike Katy, it was just her panties over his cock, and he could feel the warmth beneath. Kim was horny, and Matt didn’t realize how horny until she flashed her breasts at him!

Matt’s eyes went wide, but a moment later, content in her teasing, Kim slid off him. He wouldn’t miss the finger in his ass, but he would miss the way it seemed like they were almost going to do it right then and there.

Shannon grinned. “Well, that was more fun than we usually have at the beginning,” she said. “Now things are going to get even better!”

Matt didn’t know how he hadn’t noticed what Shannon had been doing this whole time. While the other girls were fondling and fooling around with Matt, Shannon had been putting on a strap on!

TO BE CONTINUED...
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Old 11-26-2017, 10:20 AM   #35
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It was a good writing day, so you're going to get the next two chapters back to back!



CHAPTER 18

Matt’s eyes went wide at the sight of Shannon’s strap on. It was an eight inch purple dildo with a slight mushroom head, attached to Shannon’s crotch area with sturdy black cloth straps and metal buckles. Shannon stood there, hands on hips, and smirked at Matt’s terrified expression.

“Get on your knees,” she said in an authoritative tone, pointing to the floor.

Blushing furiously, Matt did as she asked. The tile of the restroom was cold on his bare knees, and he knew it would start to hurt eventually, but he was too embarrassed right now to do anything about it. Shannon leaned down and loosened his ball gag so that it hung around his neck like a collar. Matt was about to say something in protest, but Shannon put a finger to her lips and shook her head.

“Open wide,” she told him.

Matt reluctantly lowered his jaw, and a moment later, his mouth was filled with a rubbery purple imitation of male genitalia. The dildo was cool, and felt bizarre in his mouth, but Shannon just moved her hips further forward to get another couple of inches in.

And that was when the phones came out.

“Remember,” Shannon cautioned the ten girls in the audience, “these pictures are not for sharing. Keep them to yourselves, laugh with each other about them, but don’t put them online—not unless you want to be uninvited from all future engagements!”

Whether they shared the photos they were taking or not, the experience was still utterly humiliating for Matt. Ten girls now each had a picture of him, naked and on his knees, sucking a purple dildo and sporting a hard on!

Then things got even worse for Matt. Something about this situation was turning him on beyond rational thought. He knew he liked being seen, but this level of humiliation was pushing him into a new and reckless territory. Before he could stop himself, his right hand had grasped the shaft of his penis and started stroking. Oh my god, he thought. I’m masturbating in front of all these girls while pretending to suck a cock!

The girls were laughing at this, taking more pictures of the situation. He thought Megan was even getting a video! It took a few seconds for Shannon to realize what he was doing, and when she did, she shook her head. “Some boys just have no self control,” she chided. “Katy, could you give me a hand? Go ahead and reach through my bag until you find it.”

Matt’s ex-girlfriend went over to Shannon’s backpack of sex toys and kinky accessories and withdrew from it a sturdy length of white cord. Matt kept jerking his cock, though he willed his body to stop. Why couldn’t he control himself? Katy walked behind him with the cord, reached out, and wrenched his hands away from his manhood. The head of Matt’s cock gleamed with precum, and his whole body was begging for release, but it was not to be. Katy tied Matt’s hands together behind his back with a secure knot that seemed like something a boy scout would have dreamed up.

“This has been fun,” Shannon said. “But now we have to move on.” She took the fake cock out of Matt’s mouth—his jaw was sore now—and pulled him up to his feet. His erection pointed right at the dildo, and they nearly touched.

Then Shannon turned him around. “Most boys aren’t sure about this next step,” she said as Katy moved his ball gag back into position. “But I promise you, they all enjoy themselves in the end. If you knew the number of guys I’ve had in this position…” Her voice trailed off and she spun Matt around to face Katy. Katy gave his cock a cursory stroke and winked before walking off.

A moment later, Matt’s whole day changed.

TO BE CONTINUED...
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Old 11-26-2017, 10:22 AM   #36
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CHAPTER 19

Matt felt the tip of the dildo, cool and wet now, right at his asshole. He sucked in as much air as he could around the ball gag, but Shannon wasn’t done yet. She grabbed his bound wrists, using them as leverage to pull herself further forward—and sink the strap on further into Matt’s ass!

A high pitched moan snuck its way out of the ball gag. Shannon adjusted herself, moving the few inches she had gotten into his ass out, then thrusting back in again, further than before. Matt grunted as Shannon began to establish a slow, but deliberate rhythm to fucking his asshole.

The cameras came out in force again, every girl wanting an image or two of Matt being pounded from behind by the smaller girl, his hands tied behind his back, his mouth gagged, his dick still senselessly hard. “Make sure you get a good angle!” Shannon told them, the strap on sliding in and out, in and out. “Maybe get a shot from above, or one with his face!”

Matt couldn’t believe he’d gotten himself into this situation, being taken by one girl as others swarmed around to get the best shots of his utter humiliation. But Shannon wasn’t done yet, and as she fucked him, she reached around with her right hand and started jerking him off! The sensation was almost too much for Matt to bear, and he didn’t know why, but he was actually beginning to enjoy it! There was something compelling and erotic about being taken in the ass and masturbated by the same person. And now—to his shame—Matt was in fact thrusting his hips backwards onto the dildo!

“Take note, girls,” Shannon said. “This is how it is with mosy guys. They hate the idea at first, but then they start to like how it feels. And the more aroused they become, the less they think for themselves. I mean, Matt here is basically an animal at this point, acting purely on instinct. He’ll do whatever I ask, as long as I don’t stop.” She leaned toward Matt’s ear and whispered, “Are you my bitch, Matt?”

Matt didn’t even hesitate. He nodded vigorously, as though nodding turned him on as much as what Shannon was doing to him.

“Do you want to cum, Matt?” Shannon asked.

Matt nodded again, moaning.

“Do you want me to keep fucking your ass? Do you want these girls to keep filming you?”

Nod. Nod. Matt knew he would regret this later, but he was too horny for regrets. Shannon was right. He was a creature of instinct, and he needed release. The fact that it was humiliating didn’t matter anymore. Neither did the presence of the other girls.

Then Kim squatted in front of him, her phone camera in front of his face to record his answer. “Will you submit to me privately sometime?” she asked.

And Matt nodded, though he knew that would probably lead to further humiliation and debasement.

“I think that’s enough,” Shannon said, eyeing Kim. “Okay, Matt. You will cum as soon as I reach zero. Do you understand?” She was still fucking him, still jerking him off, and he thought he would cry if he couldn’t cum soon.

“Ten, nine, eight…” Shannon began counting. Katy moved her phone to get a view of the dildo sliding in and out of Matt’s ass.

“Seven, six…” Theresa laughed as Matt moved himself up and down the dildo, faster than Shannon had been doing.

“Five, four…” Megan got a profile shot of Matt being pounded by Shannon.

“Three, two, one…” Kim got in position to record the cumshot.

“Zero.”

And Matt came. His moan could barely be contained by the ball gag, and his whole body shook. Shannon let go of him, and he slid right off the dildo. He would have fallen over if not for Kim reaching out and bracing him. She removed the ball gag as Katy untied his wrists.

Shannon slid her strap on down her legs, and by the time Matt turned around she had already put her panties back on. She was fast. “Well, what do you say?” she asked.

“Thank you,” Matt replied, blushing. Why had he said that? She’d just humiliated him in front of an ex, some acquaintances of his, and Kim—who would definitely be exploiting that later! Then again, it felt like bad form not to thank someone who had just given him an orgasm.

“Now put on your clothes,” Shannon told him. “We’re square. We both had our fun, so we can go home.” She moved right next to him as she fastened the clasp on her bra. “Unless, of course, you decide someday you want more.”

TO BE CONTINUED...
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Old 11-26-2017, 01:33 PM   #37
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Great updates! Glad he’s now at the mercy of a bunch more girls including an ex who might have a vendetta hehe
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Old 11-26-2017, 04:12 PM   #38
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amazing story!
dont think he'll have enough time to submit to everyone having pics now
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Old 11-27-2017, 07:17 AM   #39
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id submit to her as well
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Old 11-27-2017, 01:01 PM   #40
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CHAPTER 20

Finally, Saturday was upon Matt, and with it, the promise of losing his virginity. Well, not his anal virginity. He blushed as he remembered how Shannon had taken care of that! How had his life so suddenly gotten so out of hand? Just because he’d accidentally looked at a picture of a nearly naked Grace, his full body had been seen by hundreds of people, including well over a dozen people he actually knew!

On the other hand, without that, he couldn’t imagine a scenario where he was preparing to head over to Sarah’s house to have sex with her.

He made sure to comb his hair with a neat part, and he wore a collared button down shirt and a new pair of jeans that still looked good. Matt knew this wasn’t a date, but he still wanted to put his best foot forward. After all, Sarah could always decide she didn’t want to have sex with him at any time, but if he was there, she might have him humiliate himself again. Best to err on the side of caution.

Matt arrived at Sarah’s house right on time, more than a little nervous to boot. He wondered why. After all, it wasn’t as if she hadn’t seen him naked before. Or naked and cumming. His body didn’t hold any surprises for her, that was for sure.

Sarah answered the door in a purple dress that clung tantalizingly to her body, and Matt thought his jaw would drop through the floor. She’d put an effort into it. In his mind were two words, repeating nonstop: I’M IN. “Good to see you, Matt,” Sarah said, grinning.

“Good to see you too… um, Mistress Sarah,” Matt replied, scratching the back of his neck awkwardly.

“You have no idea how good it’s going to be for you,” Sarah told him, smirking. “But drop the Mistress bit. I don’t want tonight to be weird for you.”

She led him upstairs, allowing him to see her room for the first time. It wasn’t as imposing as Sam’s had been, and was pretty welcoming. Sarah had already stripped the comforter from her bed in preparation for what she had planned on happening tonight. She shut the door behind her, and a moment later, she pounced on him, throwing Matt onto the bed and climbing on top of him so that her legs were straddling his jean clad crotch.

Even with all he had experienced in recent weeks, it still surprised Matt how quickly he grew hard. Sarah grinned as she felt it against her, and she leaned down and planted a kiss on Matt’s lips. “Do you want to hear something brutally honest?” she asked.

“Sure,” Matt said, totally taken aback by this level of instant affection.

“Ever since I saw your cock,” Sarah whispered, “I couldn’t help but wonder what it would feel like inside me.” She ground her hips against Matt’s crotch and began to unbutton his shirt. “And you… you were so willing to do whatever I asked, and that was so fucking hot.” She undid the last button and threw his shirt open to reveal his bare torso. Sarah licked her lips.

“Do you want me to take off your clothes?” said Matt. Sarah nodded emphatically, and Matt reached down to grasp the hem of her skirt, which had ridden up to mid-thigh. He pulled his arms upward and the dress with it, which brought her fantastic body into view. She was wearing lingerie, a matching set of black lace bra and panties. The bra didn’t do anything to support her chest, and Matt was actually able to see her nipples through the material.

“Well?” asked Sarah. “How do I look?” But Matt was too dumbfounded to respond. Sarah slid down his legs until she was on her knees on the floor. She reached up and undid his belt, whipping it off like it was hot to the touch, then unbuttoning and zipping his now too tight jeans. She pulled down his jeans and his boxers in one fell swoop, leaving Matt lying there fully nude and fully erect. Sarah walked away with his pants, which allowed Matt to glimpse the back of her panties—which was a thong!

When Sarah returned, she yanked Matt to his feet and kissed him hard, giving his cock a couple of furtive strokes in the process. Matt felt his hands move as though of their own accord, sliding up her legs to grasp her ass cheeks. He squeezed them, and Sarah gasped, but did not stop making out with him. Then his hands moved to her back, where he found the clasp of her bra. With a speed that surprised even him, he undid it. Now her breasts were in the open air.

Matt moved his mouth away from hers to kiss them.

TO BE CONTINUED...
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Old 11-27-2017, 10:59 PM   #41
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CHAPTER 21

Sarah let out a soft moan, almost a whimper, as Matt’s lips alighted on her right nipple. The nipple stood to attention at once, and Matt responded in kind, sucking a little more of her breast into his mouth and giving it a little stimulating pressure. Then his tongue flicked out once, twice, onto the nipple, each time accompanied by a quiet gasp. Sarah, it turned out, was incredibly sensitive.

Matt repeated the process with the left breast, taking a little longer there than he had with the right one and kneading it with his hand as he sucked. It was clear that Sarah was really enjoying this, so Matt thought it was strange when her hands grabbed him by the chin and gently pushed him up and away from her breasts. She looked him in the eyes, hungry, wanting.

“Move down,” she whispered, more of an entreaty than an outright order, and kissed him.

As soon as the kiss ended, Matt did just that, sinking to his knees until his face was right in front of her lace panties—revealing in front, but nonexistent in the back. He tried to pretend this didn’t remind him of the way Shannon had forced him to kneel and give her strap on a blowjob, but he couldn’t shake the memory.

Thankfully, Sarah hadn’t been there for that, because he couldn’t imagine her wanting him tonight if she had seen the way he had been fucked in the ass.

Matt reached out and found the waistband of Sarah’s panties, sliding a thumb underneath each side and stretching it out a bit. Those fresh glimpses of her bare hips were almost enough to drive Matt mad on his own… and then he started to pull them down!

Sarah’s pussy was pretty. There was no way around it. He’d never thought of a girl’s privates in that way before, but there it was. An aesthetically pleasing vagina (although he immediately thought this was the least erotic phrase he could have possibly used). Her shaved mound, the way her whole body seemed to curve to frame her lips, the slight glistening hint of arousal peeking out from within—all of it contributed to the heightened nature of the moment.

And then Matt poked out his tongue and began to lick.

She tasted fantastic, perhaps even better than her juices had tasted in isolation the other day, and Matt luxuriated in exploring the folds and contours of her sex. His tongue found her clit—brushed past, more like—and Sarah moaned and grabbed his head to keep him right there. She let him keep it up for a couple of minutes before letting him go, yanking him to a standing position and kissing him more fiercely than she had thus far.

“Fuck me, Matt,” she whispered.

Sarah lay down on the bed, propped up on her elbows, her legs parted, ready, and Matt fumbled around, pulling out the wrapped condom he had brought with him in his pants pocket. He’d put one on before, but only to get a feel for how it worked so he wouldn’t waste too much time when he got around to having sex. He was grateful for the practice now, and he rolled the latex sleeve down the length of his shaft in seconds.

An instant later, he had joined Sarah in the bed, and he was on top of her… and then inside her.

For a few minutes, they fucked in the missionary position. Matt was gentle at first, slow, but Sarah grabbed him by the ass and pulled him forward more forcefully into her. He took the hint and picked up his pace, and he could tell it was driving her wild. “Oh yes,” she moaned, “that’s the angle, yes, fuck me, Matt!”

But before either one of them had a chance to cum, Sarah did something Matt didn’t expect. Wrapping her legs around his bare backside, she flipped the pair of them over on the bed. Now, Matt was on the bottom, and Sarah was on the top. “My turn,” she said.

Sarah seemed to enjoy driving the sex, cowgirl style, even more than she’d enjoyed the missionary, and Matt had to agree with her. She practically bounced atop his cock, taking advantage of the full length of him at an even faster pace than they had been going at before. And the way her breasts wobbled in time with her movements, dangling just above Matt’s face, was incredible.

It didn’t take long for Sarah to cum, letting out a wail of delight as she did so, her blonde hair draping down into Matt’s face. She had worked up a sweat, and Matt was tempted to give her a moment to gather herself, but she shook her head when he started to slow down. “Don’t you dare,” she warned. “I want another!”

She was still feeling the aftershocks of her first orgasm, and that built up into a second within a couple of minutes. Matt was having trouble holding his own orgasm back, and Sarah could tell he was in desperate need of release. She grinned. “I want you to cum, Matt,” she whispered, her flushed face an inch away from his, her breath warming his skin.

And that was all it took. Matt let out a wild grunt, thrust his hips so far upward that Sarah’s knees left the bed, and filled his condom.

For the next minute or so, Sarah lay on top of Matt as they caught their breath, Matt still inside her but beginning to wilt. He’d had some high expectations of sex, but he hadn’t expected it to feel this GREAT. He and Sarah made eye contact, and they both let out some awkward laughter. “So, um, that happened,” Matt said.

“And that was your first time?” Sarah asked. Matt nodded and a mischievous gleam entered her eye. “Well, then, that means you’re only going to get better. And you… heh… you have a pretty solid foundation there.” She actually seemed a little nervous, as though she was unsure if she’d jumped into things a little too quickly with him.

“Hey,” Matt said. “For what it’s worth, we don’t have to define this right now. I mean, there doesn’t need to be a ‘this’. We’re still friends, aren’t we?”

Sarah’s eyes shot up. “Then we’re going to be the kind of friends who fuck,” she told him. “I have a lot more positions I’d like to run past you…”

TO BE CONTINUED...
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Old 11-29-2017, 04:04 PM   #42
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Glad he got a little reward for what he’s been through, but I still can’t wait to see him embarrassed and humiliated again
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Old 11-29-2017, 05:23 PM   #43
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Oh, don't worry, there's still humiliation to be had .
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Old 11-30-2017, 03:30 PM   #44
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CHAPTER 22

Matt’s phone was ringing as he lay on his bed. He pulled it out of his pocket and looked at the screen. It was Grace. Great, he thought. That’ll be another afternoon’s humiliation.

When he answered it, however, Grace sounded different.

“Hey, Matt,” she said, her tone awkward, almost apologetic. “Are you busy? I can call back later.”

“I’m not busy,” Matt replied, then remembered to add, “Mistress.”

He heard Grace wince on the other end of the line. “Yeah, it’s about that,” she said. “Listen, I’ve been thinking about it, and… don’t get me wrong, it was a lot of fun at first, and we had some great times and all. It’s just…”

“You want to stop?” Matt asked.

“I really do. You’ve been so good about it, and I feel like I’ve been, you know, exploiting you for a while over an honest mistake. And then bringing in the other people… the whole webcam bit…” She gulped. “Sam told me a while back she didn’t need to do it anymore, and Sarah… well, she told me about last weekend, and she seemed pretty pleased with herself.”

Matt chuckled, remembering every moment of fun he and Sarah had shared, and he started to get hard again.

“So anyway,” Grace went on, “she doesn’t want to dominate you anymore. At least, not outside a one-on-one basis. And if it’s just me… don’t take this the wrong way, Matt, but it feels weird seeing my friend naked and jerking off.”

“Makes sense,” said Matt. To be honest, though—and this surprised him—he felt a little disappointed. After all the weeks of humiliation, all those intense experiences, he was going out without a bang.

“But, uh… no hard feelings, right?” Grace asked. “No pun intended.”

“Of course not,” Matt told her. “I kinda enjoyed it more than I thought I would.”

“Enough more that you’d be comfortable with Sam keeping the pics and videos? She said she’d really like to keep them.”

Matt blushed, even though neither Grace nor Sam was in the room. They still had a certain power with him. “Sure,” he said. “Why not? I mean, she’s already seen it live.”

Grace laughed. “I guess that’s true. Okay, well, all in favor of just moving on and pretending this never happened?”

“Aye,” Matt replied.

“The ayes have it. Thanks for being cool about this, Matt. See you at school tomorrow.”

And they hung up, although neither one had any intention of forgetting the past few weeks. Matt set the phone down beside him on the bed and sighed, looking up at the ceiling.

A moment later, his hands started to move of their own accord, sliding down his chest to the fly of his jeans. He unbuttoned and unzipped them, and in a flash, he had both his pants and his underwear down around his ankles. His erect cock was in the open air, and he wasted no time before stroking it. Matt closed his eyes, imagining that Sarah was there—or Grace—or Sam—or any one of the hundreds of people who had seen him undressed. Maybe they would cheer him on. Maybe one of the girls would straddle his face and make him eat her out. There were so many possibilities. And now that he was free of any obligations to Grace, he could explore his kinks how he chose. He guessed Sarah would be willing to help him.

Yes—Sarah. Sarah with her blonde hair. Sarah with her perfect tits. Sarah, who had ridden his cock until he had no option but to have an orgasm. Matt started to jerk himself off faster, and he let out a soft, low moan.

He was so close to cumming. Just another thirty seconds, and he would blow his load. He was sure of it. He could sense it building up within him.

Then the phone rang again.

Sighing in frustration, Matt picked it up.

“Hello there, Matt. I hope you’re not busy.”

It was Megan!

TO BE CONTINUED...
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