Chapter 5
by Exphrases
What happens next?
Ted meets his new assistant.
Ted pushes his tongue deep into his boss's pussy, enjoying the taste and the sounds she makes above him. "Mmm, you're pretty good at this." she says, bringing both hands down onto the back of his head to push him in just that little bit deeper. "Your wife is a very lucky lady. At least I hope she is, you'd better not be the selfish type with a tongue like that." He shakes his head as much as he can, getting a giggle from Linda. "Good," she says as Ted moves his focus up to her clit. "Ah! Very good." she moans leaning her head back and running her fingers through Ted's hair.
However he's a little disappointed as her hands leave his head suddenly. He slows down a little and looks up to see her leaning over on her desk and typing something on her computer. She looks down at him and grins. "Oh don't mind me. Just getting something ready for you, that's all" she says and wraps her legs around his head and back, somewhat squishing his face between her thighs in the process. He continues licking and she continues typing, mouth open and panting not noticing, or not caring, about the little bit a saliva about to fall onto her desk. After a while of this she stops. Closing her eyes and squeezing her legs around him just a little more. "Oh fuck I'm gonna cum!" she moans easily loud enough for her secretary outside to hear. She sits up, grabbing his head again and holding him close as her body quivers and shakes until shes done and lets go of his head.
Ted pulls his head back as Linda lays down on her desk, the both of them gasping for breath. He licks his lips, savoring the taste on the outside and inside of his mouth of Linda's pussy. He stands up and becomes painfully aware of his erection. His cock, which wasn't exactly soft when he walked in anyway, is now rock-hard and sticking straight out of his boxers. He looks up to see his boss, still laying back on her desk catching her breath, and her legs still spread. Her painted on clothes are mostly faded or running from her sweat, making her "clothes" look like it's melting away. Ted's eyes focus in again on her pussy; exposed and soaking, perfectly on level with his crotch. It takes every bit of willpower he has to not just taker her right there.
She sits on her elbows and looks down at herself. "Tsk. I knew this was a bad idea." She rubs a hand across her chest, her "shirt" becoming a big grey smear across her breasts. "I told my husband this wouldn't last very long but nooo..." she says looking around the room. "Oh, there it is, can you hand me that?" she asks, pointing behind Ted. He turns around to see a "bookcase", though only the top few shelves have actual books with the rest being filled with various sexual instruments. Dildos, buttplugs, anal beads and strap-ons of various sizes, a small paddle, some rope. One shelf has a few framed pictures, some of Linda herself and some of people Ted doesn't recognize, all naked and either having sex or clearly just finished. Ted is surprised to find the bottom shelf filled with chastity devices like cock cages and chastity belts, along with a key-ring. On the shelf above those is one stacked with small towels. He grabs one and walks over to her desk.
"Thanks Teddy" she says with a wink before using the towel to clean the sweat off her face and as much of the paint off her body as she can, each swipe from left to right exposing more and more of her body before setting the towel down on the desk. "I think that's as good as it's gonna get without a shower" she sighs. Finally she looks up and sees Ted's erection staring her in the face. "Oh, I can see you liked that as much as I did." She scoots closer to the edge of the desk and extends her index finger just below his cock, collecting the leaking precum and bringing it up to the head of his cock. "I can tell you'll do well here, especially if you can accept fucking people other than your wife. And your wife fucking people other than you. And your kids fucking around at their school." Ted knew he shouldn't like what she's saying, but his cock certainly wasn't getting any softer, especially with her wet finger slowing sliding from his cockhead to his base.
However, when her finger does reach the base of his cock she roughly grabs his balls with her hand, not tight enough to cause pain but certainly tight enough to know she means business. "But you should know, Teddy, that this is still a business. Lots of companies, including this one, have had prudes join expecting a free pass to fuck all day and night without a care in the world," she says, squeezing his balls ever so slightly tighter. "but there's work to be done. Sometimes those are enough to get the point across" she says motioning over to the chastity belts, "but sometimes they aren't. Sometimes the only thing left to do is cut our loses and send them back. Even the ones that are super reserved when they come here don't like that very much." Finally she lets go and steps around her desk to her chair. "Fuck during work or on your time off, fuck during lunch, drag one of the interns under your desk and make em go to town. I don't care. But your performance will be evaluated just like everyone else. That's how the schools here do it and that's how the jobs here do it. Understand?"
Ted stands up straight, trying to look as professional as he can. "Yes ma'am. I'll make sure business comes first. During working hours at least." he says. She grins at him.
"Good. Now I know you knew about all this before you came here but I have to ask. Are you bisexual? Because you're gonna have a rough time if you aren't."
"I am, but I've never actually done anything with another man yet." he said.
She furrows her brow at this. "Hmm. Well that might be an issue. There are some people here on the smaller side, but not many." She saunters over to the shelf of toys and grabs the buttplug furthest to the left, then opens one of the drawers and pulls out a small bottle of lube. "Here." she tosses them over to him. "That should at least help your ass get a bit used to it." She then grabs a small dildo with a suction cup base and hands it to him. "When you get the chance you should work on getting rid of your gag reflex. I'd suggest sticking that on your desk and working it a bit when your working. Now those are free, if you want something bigger though you'll have to buy it yourself. Or just ditch toys and get a person to help you train. You have a Son right?" she asks.
Ted barely had a moment to think about it before she let out a laugh. "Oh I'm kidding. Mostly. I know that's usually the biggest hurdle to get over. Usually. Your wife can peg you or you can get one of your neighbors to do it, I'm sure you don't need to me to explain this to you. For now just use that." Ted looks down at the plug. It was silver and the cap bore the company logo. It felt small in his hands. The truth was he had barely experimented with anal before. Just one finger when he masturbated sometimes. His wife Sally was receptive to it, sometimes sticking her finger in when he was on top of her. They talked about pegging before but nothing ever came of it. Though the plug looked small he knew things felt bigger in there.
He set the plug down on her desk and opened the bottle of lube. He squirted some of it onto his fingers and brought his hand to his ass. While he kept some stubble on his face and chest he preferred to stay shaved back there. Partly because Sally didn't like the look of it when she saw him from behind or the feeling when she fingered him, and partly because Ted just liked it that way. He smeared the lube around his anus before slipping a finger in, almost to the second knuckle. He wiggled the finger around and twisted his hand a little before pulling it back out and grabbing the plug. After covering the plug in lube he brought it to his ass as well and pushed. The tip went in just fine, but the base was a bit tougher. He pushed harder, grunting in pain and pleasure, until finally the widest part was in and the rest of it slid in, the cap resting between his cheeks. He let out a moan a bit higher pitched than he expected. He heard a giggle from Linda.
"Yeah I think the boys will like you. And the girls. Now, let me see." she said. Ted eagerly spun around, and turned his neck to try and catch a look himself. "Don't worry, it looks great." With no mirror he'll have to take her word for it. He turns again. It felt weird, and a little sore, but also undeniably arousing. Every shift on his legs or **** clench caused it to press into him just a little more. His cock stood out right ahead of him, each shift of the plug causing it to pulse a little.
"Looking for a way to finally get that settled?" she says, nodding at his erection. She checks the clock on her computer. "Well, sorry Ted but I can't help you with that right now. Again, there's work to be done. I have a meeting to catch and well..." she says looking down at her body, covered in half-smeared body paint. "I'm not really presentable as either a business woman or a slut. I'm gonna hit the showers." she says, grabbing another towel. "As for you, I've assigned you a personal assistant. Depending as how well you acclimate she may stay your PA for the foreseeable future. She'll get here soon to give you a tour of the place, introduce you to who you'll be working with and teach you some of the systems we use to get work done around here." she explains. "She'll report to me on how you did. If you don't disappoint, maybe we can have a bit more fun after hours." she says, giving Ted another wink.
"I won't disappoint you Linda." he says picking up his briefcase. She smiles, and stands up from her desk.
"Alright, enough talk." She says, putting a hand on Ted's shoulder and guiding him out of the office. "Your PA will meet you out here when she arrives. Trish can keep you company" she says, looking over at her secretary, who only rolls her eyes in response. Linda walks over to the elevator and presses the button. "Oh, and Ted" she says as the doors open. She points down at his unbuttoned boxers and shirt. "Even though 'skimpy' is the style here, there is a wrong way to do it. You might want to go shopping for clothes. Just sayin'." she says and heads into the elevator.
Ted stands in front of Trish's desk. His cock is still hard after all of Linda's teasing. He tries to look around the mostly empty room to distract himself from the barely dressed secretary. Even though sex is such an open thing Ted luckily, or unluckily, hasn't gone all the way with anyone yet. His boss's words came back to him. This is the world he lives in now. He and his family have to accept it. His wife is at home doing who knows what and his kids are at school surrounded by sex. These are things he thought he came to terms with already before they left home, but now that it's a reality it's all coming back to him. His twins could be having sex with someone right now. His twins could be having sex with each other right now for all he knows. He and his wife already talked about this and accepted that the both of them would probably 'cheat' on the other eventually.
His thought then turned to the woman in front of him; Trish, Linda's secretary. An Asian woman in her early twenties with black hair done up in a bun. She's only wearing a black lingerie one piece, similar to a leotard in shape from her crotch to her neck, with a short frill around the waist resembling a skirt. It didn't do much to hide her body, her nipples visible through the lace pattern. What stood out to him was her face. Like everyone else he's met since he arrived she's the definition of beautiful, but even then her lips were large and despite her uncaring attitude she clearly put a lot of effort into her makeup, especially around her eyes. Ted then looked back down at himself and realized yes, even in just his unbuttoned boxers he looked quite out of place. He quickly took them off as well, leaving his entire bottom half exposed aside from the dress shoes. He then made his way over to Trish.
She was clicking away at something on her screen, resting her chin in her other hand. She only glanced at Ted when he stopped next to her. Before he can even ask for anything from her, she moves her free hand to his cock. She starts jerking him off slowly. Too slowly for Ted right now. "Could you use your mouth instead?" he asked. She looked at him for a moment. She had a look of annoyance when she looked Ted in the eyes, but when she drifted down to his cock her stern look softened. She licked her big lips as she stroked him before letting go and quickly typing something on her keyboard.
"Alright, here's the deal" she starts as she spins her chair to face him. "I'll get you off, but we do it the way I like." she says.
"And which way is that?" Ted asks.
She reaches to his sides and grabs his wrists, bringing them to the sides of her head. "Rough. I don't like giving blowjobs, I like getting my face fucked. Got it?" Ted just stares at her for a second.
"Yeah I think I can do that." he says before grabbing her head and pulling her mouth onto his cock. Ted's cock is quite long and thick but she's clearly experienced at this, taking the whole thing without gagging. He holds her there for a second, enjoying the feeling of her lips at the base of his dick before pulling her back. She moves her tongue as much as she can and Ted can tell she has multiple piercings. He picks up the pace, properly fucking her face like a toy. True to her word she seems to be enjoying it. Despite little coughs here and there her hands stay in her lap and her eyes are half closed, the previous look of annoyance replaced with one of pure ecstasy. Her mascara is starting to run and her pink lipstick starts to smear on Ted's cock. Ted silently apologizes to his wife but he had to admit to himself that this was the best head he'd ever gotten. So far, at least.
The room was filled with the sounds of Ted's moans and Trish **** on his dick. Then a loud ding rang out. Trish either didn't notice or care, probably both, but Ted looked over to the elevator. The doors opened and out walked a pale woman with long black hair and blue eyes behind a pair of thin glasses. She had lips almost as big as Trish coated in dark red lipstick. Around her neck was what looked like the collar of a suit with a tie, but that was it. The tie was long and thin, resting between her large breasts. Her nipples and areola are about as pale as the rest of her body, causing them to blend in. Or at least they would were it not for the piercings, each pale nipple pierced with a black barbell piercing. Her waist was small and her navel was also pierced with a black stud matching her nipples. She had a black lace garter connected to matching stockings, but no panties leaving her pussy and the small patch of black pubic hair above it as exposed as the rest of her body. She walked in dark red high heels, each step slightly swaying her hips. She approached Ted with a big smile as he facefucked Trish.
"Hi, you must be Mister Arton." she said in a slight British accent. Since his cock was busy she instead reached around and groped his ass.
He did the same to her. "That's right, and you're my PA?" he said in between moans.
"Yes sir, my names Miranda. Nice to meet you. I'll be showing you around the place for a while, introducing you to your coworkers and generally giving you any advice I can to help you get settled. When your done here, that is." she said and moved her own hands to Trish's head. Ted moved his own out of the way as Miranda pushed her all the way down again, only this time moving one of her hands to Trish's nose, squeezing it shut. Trish's eyes widen but she still keeps her hands in her lap making no attempt to stop it. Meanwhile Ted was in heaven. Trish was moving her tongue much faster now and the head of his cock was firmly in her throat which was loosening up and then tightening again and again.
It was too much for him and Miranda could tell. She smiled at him and nodded. With another moan Ted shot a spurt of cum down Trish's throat. This made it even harder for her to breath, but right as she finally started to move her hands Miranda let go of her nose and head. Trish pulled her head off of Ted's cock and gasped for air while the rest of Ted's orgasm coated her face and gaping mouth in cum. Miranda started slowly jerking him off to squeeze out the last few drops, some of which shot out to Trish's chest and some simply ran down to Miranda's fingers. When she was she done she licked her fingers clean.
Trish is a mess in her chair; hair disheveled, makeup running and face and chest covered in cum. Ted opens his mouth wanting to both apologize and thank her, but Miranda brings one now-clean finger to his lips. He looks at her as she begins to make her way to the elevator, beckoning him to follow her and adding a bit of sway in her steps, showing off her hips and ass. Ted, already feeling his cock coming back to life, grabs his briefcase and follows her in.
When the elevator doors close she speaks up. "Sorry about that. Trish is really into that kinda stuff though. No asking for permission, no 'sorry' or 'thank you', just using her like a toy to get off and moving on with your day." she says.
Ted's a little shocked. "Really? She seemed so serious and 'no-nonsense' when I first got here."
Miranda laughs. "Oh yeah. She probably started masturbating right when we left. She likes to start the day looking professional but end the day look totally ruined." she shrugs. "That's just her thing."
Ted, trying and probably failing to hide his ogling, asks "Do you have a 'thing'?"
She giggles. "Wouldn't you like to know. I might, I might not, but wheres the fun in just saying it? You and I might be together for a while. Maybe you'll find out one of these days." She finally presses a button marked as 'B'. "Before any of that though I'm going to take you to engineering. We'll start the tour there and work our way up. Any questions?" she asks.
Ted pays as much attention as he can with his erection. "No, I don't think so. Other than... do you mind if I..." he says, eyeing her chest.
She smiles at him. "Sir, even though it's not a kink of mine or anything like Trish, I'm your assistant, you don't need to ask for that kind of stuff." she says putting her hands behind her back and thrusting out her chest.
"I'll keep that in mind" he says and starts groping her, squeezing her breasts together. He leans down to one and wraps his mouth on it, dragging his tongue against her warm nipple and the cold metal on either side.
She gasps, but keeps her hands behind her back. "Do you like them Sir?" she asks.
Ted sucks on the nipple before letting go with a pop. "I do. You have a great body. In fact why don't you turn around and bend over." he says, stroking his erection.
"Yes Sir" she says, turning around and putting her hands on the elevator wall and spreading her legs. Ted first gives her behind the same treatment as the front, feeling her ass in his hands. He lightly spanks one cheek and watches it jiggle, then spreads them apart. Her asshole is a pale as the rest of her and her pussy is soaked. Ted, taking her advice, stands up and lines his cock up with her wet cunt. Thanks to her arousal and him still being covered in Trish's saliva he slides it in to the hilt with ease.
She looks back at him. "Oh god, you're so big Sir!" Ted grabs her by the hips and starts fucking her, the elevator filled with the sounds of both of them moaning. He reaches around her to grope at her chest again as he thrusts into her, teasing her nipples before bringing his hands down to her narrow waist.
Just then the elevator stopped, and with a ding the doors opened again. Ted looked out to see a black man and a blonde woman. The man's physique was amazing, with broad shoulders and well defined pecs and abs, and a cock that was about as long as Ted's, maybe a centimeter shorter, but much thicker. All he had on were white socks, plain dress shoes and what looked like a wedding ring.
The blonde had the look of what was, from Ted's world at least, the stereotypical 'bimbo'. Her blonde hair was long enough to reach her back and her makeup was heavy, her thick lips covered in dark purple lipstick. Her skin was lightly tanned. She was wearing a skimpy schoolgirl outfit, was a very short skirt that did nothing to hide her vagina or her thin streak of brunette pubic hair. Her 'shirt' was tied from the front, a little too tightly by the look of her cleavage that looked ready to escape at a moments notice.
"Hey~ Miranda." The blonde says stepping into the elevator. Miranda looks back at her as best she can while Ted continues to fuck her, albeit a bit slower than before.
"Oh, hey Ashley" she says, almost out of breath. "Ted, this is Ashley and Nick. Guys, this is Ted. He's new here but I'm teaching him the ropes" she says, arching her back and giving Ted a wink.
Nick presses one of the buttons and approaches Ted. "I can see that. Nice to meet you Ted." he says, sliding his hand down from Ted's shoulder down to his ass and giving one of his cheeks a nice squeeze, the plug peaking out. Ted grabs Nick's cock in kind and give him a few strokes.
"Nice to meet you too, Nick." Ted says. Before he can say anything else though Nick grabs the back of Ted's head and pulls him in for a kiss. Ted closes his eyes for what is a surprisingly sensual kiss. While Nick pushes his tongue into Ted's mouth he also uses his hand to caress the side of Ted's neck, his other hand still groping his ass. Ted, meanwhile, is still slowly jerking him off while the two of them make out, his momentum with Miranda grounded almost to a halt as she slowly grinds her hips into Ted's crotch.
The men's kiss is interrupted when Ted feels Ashley press her huge tits into his other side with an exaggerated 'ahem' sound. Ted turns to her and grabs one of her breasts. "Sorry about that. Nice to meat you too Ashley." She smiles and leans into him for her kiss, bringing her hand down to his balls.
Nick continues to play with Ted's ass until he spreads it apart to see the plug. He presses it slightly with a finger sending a jolt up Ted's spine. "This is pretty small. One of the boss's training plugs, right?" he asks.
"Yeah, the smallest size she had. I haven't done much back there." Ted says.
Nick gets a disappointed look on his face. He glances at the number above the door slowly approaching his and Ashley's floor. "Well that's a shame. You got a nice ass but I don't really have to time to break you in. Maybe we can meet up once you're a bit looser back here." He says giving Ted one last grope.
"Yeah, maybe" is all Ted can say. Ashley speaks up this time.
"Aaand~ maybe next time you won't be so busy" she says, grabbing Miranda's ass and giving it a little shake. With another ding the two of them make their way back out of the elevator leaving Ted and Miranda alone again. Only now does he realize he pretty much stopped moving his hips when the door opened.
"Sorry about that. Took me little off guard is all." he says.
She looks back at him and smiles again. "No need to apologize Sir. You can fuck me at your pace, not mine."
Ted pulls out of her. "Alright, let's change the pace a bit then. Turn around." he says, and she obeys quickly. He then picks her up by the legs and hoists her up against the wall. She then reaches down and guides him back inside her. Just like that he's fucking her again, her tits pressed up against his chest and her moaning face right in front of his own. He leans in and kisses her, their tongues intertwining in each-others mouths. Ted starts to feel his climax building. He breaks the kiss. "I'm about to cum" he barely gets out.
Miranda lets out a squeal. "I'm cumming too sir" The two of them keep up that pace until Ted starts thrusting slower but harder. She's made it clear he can do what he wants with her, and he uses that by thrusting as deep as he can go when he finally cums, shooting his sperm as deep as he can. Miranda tightens around him, legs shaking as she comes down from her own orgasm. After a few moments of the two of them panting without saying a word, Ted finally lets go of her legs and pulls out, some of his cum following a moment later. Miranda leans her head back against the wall to catch her breath. "If you turn out to be as good at catching as you are pitching I think you're going to be very popular here Sir." she says.
Ted chuckles at that, but his eyes are locked on her groin, his sperm trickling out slowly onto the elevator floor. "That's not gonna be a problem is it?"
She looks down at herself. "Oh no Sir, we have quite a lot of control over that here. Unless you want there to be a problem with it, I can take a fertility pill if you want." Ted's eyes widen at that.
"No no no. No, really. I have a pair of twins and right now they're more than enough for me." She gives him a coy look and laughs.
"Haha, of course Sir." she says, but he could tell she was at least a little bit serious about it. As she fixes her hair she looks at the current floor. "We're almost there now. Now I'm going to assume, per how fast you got your erection back after Trish, that you've been taking the vitamins you've been prescribed."
"Oh yeah, I've been careful about it, don't worry." For someone coming into the Sexworld it can be difficult to keep up. The food here will naturally help with that for most, but Ted wasn't a spry youngin anymore, so most adults switching over are prescribed medicine to help with their stamina.
"Well that's good, because you're probably going to need to be ready to have sex if you're coming down here. Moreso than usual I mean." Ted gave her a confused look as the doors opened.
What happens in engineering?
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Moving to the Sexworld
Adventures in a Sexy Alternate Universe
An ordinary family immigrates to an alternate reality without sexual taboos
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Updated on Jun 6, 2025
by Shendude
Created on Dec 19, 2010
by Shendude
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