Kevin Date 1, Part 4: Kevin's Surprise

Mona

While Ophelia distracts Kevin, Mona works to finish up Kevin’s surprise. Eeeeeeh! This’ll be so hawt!

Winter is kneeling on the bed. The drow is dressed in a skimpy set of maid lingerie: a lacy black bra, lacy gloves, stark white stockings that hug lilac thighs, a mini-skirt so short that the deep purple jewel at the base of Winter’s anal plug can be seen from the angle Mona is currently at. The maid is already blindfolded, handcuffed, mouth lewdly open, waiting for the ball-gag to be applied.

“Ready for the last bits, Winter?”

The maid nods. “Yes, Mistress. Thank you. I hope he enjoys me.”

Winter’s tongue retracts as Mona places the ball gag in the maid’s mouth. She fumbles a little with the strap, but she manages it. “Did I get it too tight?”

Winter gives a no shake. “Okay,” Mona acknowledges, “You sure you want the earmuffs on?”

Winter gives a yes shake. “Okay,” Mona states. She slips the earmuffs on. There. Maximum sexiness. Time for Kevin to see his present!

Mona pokes her head back out from the bedroom. “Hey, Kevin. Ready for bed?”

Kevin pauses before he stands. “Sure, Mona. Time for a platonic friend sleepover thing.”

Mona gives him a nervous grin. Ophelia chortles and gives Kevin a wink. I hope he doesn’t think that Ophie was being too weird.

Kevin walks in, sees Winter trussed up just for him, and starts to turn. Mona grabs a sleeve, “Wait, Kevin! Surprise?”

He looks super mad, the maddest she’s ever seen him. He rumbles, “The fuck, Mona! You know that I’m gay. Why would you do this?”

“Winter asked me and then convinced me that you would enjoy it. Please, Winter risked a lot to ask for this. If you really don’t want it, I just ask you to check under Winter’s skirt first then pull the earmuffs off and tell your surprise yourself.”

Kevin, rigid with anger, almost has a Tegan-like stance as he approaches the maid. He lifts the skirt, then softens slightly. He still pulls the earmuffs off and starts to undo the gag, ignoring Mona’s pleas to just leave it.

Kevin snaps, “Mona, abstinence. That was the safe word, right? I’m not moving ahead without talking to... Winter? Okay, Winter, explain. Start with the weird language thing I’ve noticed.”

Winter mumbles, “Please, just use me. I don’t want to ruin the mood with my whole... thing.”

Kevin is still a little angry, but he is slowly calming down. “I’m not having my first time be like this, Winter. Please, explain. If I understand why you are... seriously, what is with the weird language thing? It’s like I try to think about this normally and the words just slip away.”

“An adult naming ceremony gift. People cannot conceive of me with gendered language. I’d rather people use awkward language about me than be able to realize that I’m... defective.”

Defective? Why would Winter think that Winter is defective? Winter seems really small down there, but it’s fine?

Kevin sits on the bed and wraps an arm around the bound maid. “You aren’t defective, Winter. I don’t get why you think like that, but you aren’t defective.”

Mona gingerly approaches the pair, feeling like she fucked up again. “I’m sorry, Kevin. I was just trying to do a nice thing.”

Kevin looks up at the gamer girl, “Did you ask Winter, at least?”

“Winter asked me in that letter. I saw Winter’s genitals. I figured it explained the flirting and the letter and just thought...”

Kevin nods, “That you’d get a hot sex scene to watch and I could get some points and Winter gets what Winter wants. Win/win/win. I get it. I still need to understand, Winter. Why would you want this... weirdness?”

“You need to understand some things. The Queen has access to her former male genetic material, but her ‘Y’ chromosome was severely damaged by the onslaught of transformations she underwent. My sister and I are sororal twins, not just siblings. Summer is normal. And I... I’m defective. I got the bad chromosome from the Queen. In the Queen’s nerd talk, and it’s talk that you should at least somewhat understand, Kevin, I lack the genes to start puberty properly. All the little GnRH receptors that should exist in my pituitary never developed. So, I’m like this. Defective. A too lithe adult with a tiny set of nethers that can’t even really get hard. I hope that, since you aren’t from here, you’d be willing to just accept me, Kevin. I know my moms love me and will do everything they can for me, but I want a husbando and maybe a waifu, dammit. And I will never find either of them among the natives here.”

Mona wraps Winter in a hug. Kevin does too. He tries to soothe the shaking drow, “I was so confused with your flirting, Winter. I saw what I guess I wanted to see and didn’t see you as you are. I’m sorry. Now that I know, I do find you cute. Are you okay with taking off most of the bondage stuff? I’d like my first time to be with somebody present.”

Winter beams, begging, “Take what you want off.”

Mona only half-watches as Kevin strips Winter bare. To be fair, she’s too busy taking off her bottom. Time to break in my plushie!

Tessa

If this is the free experience, the paid services must be divine!

Tessa is basking in the tail end of an instructional hot stone massage. Nimble yet strong fingers are working through a knot in her back that she wasn’t aware of. Pleasantly warmed stones rest on flannel patches placed on her shoulders, on her knees. From what Scarlet said, the stones cause burns if they are placed directly on the skin, which makes a certain amount of sense. The heat that felt like too much at the beginning has now turned her body into quite content jelly. Aaaah!

Gaia is purring contentedly on the massage table beside her. Scarlet is working directly on Gaia, showing a technique to the novice masseuses. The base of the tail is a tricky place to massage properly.

Too soon, the session is over. Both women feel like very happy, very limp noodles as they are **** to deal with gravity again. The novices assist them to a small scented bath. The water is warm. Gaia happily doesn’t complain about the bath being a waste of water. Tessa slips down to the bottom and relaxes. For the equivalent of a breath. Then, realizing just how irritating the scented oil is on her gills, bursts back up.

“Stop sloshing the water around, Teach.”

“Sorry,” Tessa stammers, finding a notch to rest her head. She stares at the odd pattern of stars painted on the ceiling. Looking to maybe have some small talk, she asks, “So, what all did you do today, Gaia?”

“Took a walk in the garden, Tegan **** fed me innocent animals, got Summer and Bella to help me teach Tegan how to use a dildo for her bounty. I think she’s a friend now? Then you saw dinner. You?”

“Morning with the mermaid kids in the pool. I had lunch pretty early, then I wandered a bit, looking for a date idea for tomorrow. I haven’t exactly had a date in a long while and, even back then, I didn’t have to plan it. Then I dragged Andromeda out of the library to do some clothes shopping over at Airika’s shop.”

“Oh, yeah, I barely see that girl. Why does she hole up in the library so much anyways?”

Does Gaia still not know? “Wait. No one has talked to you about the endgame yet? How were you convinced to come here?”

The pause Gaia provides indicates that she does not know. She sounds a little embarrassed, “Well, I just got word that my final **** row suspension appeal was rejected and Daphne asked if I wanted to live. I did. So, I followed the mermaid. I assume you were promised to be reunited with Tyalangan, right? What does that have to do with the endgame?”

“Not much,” Tessa admits, “but Andromeda and Kevin, to a lesser extent, were given indications that our world is in imminent danger. Andromeda has been maybe too focused on saving it.”

“Well, I want to save the planet. What do we know?”

Tessa proceeds to fill in Gaia about what they know, which is admittedly not that much. Gaia’s ears flatten and she shudders, “So, something is gonna pop up out of the ground and kill all the plants and funguses and animals? That’s horrible!”

The absence of people on that list is telling but at least Gaia seems willing to help.

The terrorist continues, “Is that why they made me get a combat cantrip thingy? So I can help save the world? Ooooh, the season name makes sense now! Thanks, Teach!”

Gaia is not that bright? At least she cares, in her way. “You’re welcome. So, any advice for me about dating Mona? I could use the help.”

“She’s a sweet, if horny, kid. Here’s what I got.”

They talk as they wrap up the bath and head back to the Summer Room. They plan some bedroom ideas. By the time curfew comes, they are cuddling in bed, whispering more ideas. Well, I at least have some ideas of what to do at the end. I just need some inspiration on what to do first.

Kevin

Kevin is looming over Winter. The drow is cute, legs spread, back on Mona’s bed, lower lip held down with a few teeth. The maid is drinking in Kevin’s bare torso, his throbbing cock, freed from the cage for the first time in a while; drops of milk land on Mona’s bedsheet every few seconds. It will probably be a mess soon. Mona is in Kevin’s periphery, already grinding lightly on the Josie plushie she got at the arcade; she can enjoy the show, but Winter needs his attention.

Kevin: +6 XP (Full Frontal Nudity for Mistress)

“Kevin, please, when you’re ready.”

After applying a heavy dose of lube to himself, Kevin carefully removes the plug from Winter’s ass. The drow gapes. Kevin quickly adds some lube to Winter and swirls it around the maid’s escape tunnel. The drow gasps from the cold.

“Sorry?”

“It’s okay, Kevin. I might look like it, but I’m not a delicate flower. A little cold lube isn’t going to bother me. I’m slippery enough. Please, I’m aching for you to fill me.”

Winter’s legs wrap around Kevin’s waist. Kevin is pushed forward. He lines himself into Winter’s gaping hole just in time. Winter’s legs hug him. And, just like that, Kevin is half-way into the drow. Winter is squeezing on him so tightly. The dribbles of milk starts to flow a little quicker.

“Ooooh, that feels warm. Ready to start going deeper, Kevin?”

Winter definitely looks ready. Kevin starts to push deeper, slowly. Learning how to take that dildo last night taught him to take it slow. Let Winter get used to it. The drow whimpers, nethers giving a single, half-hearted twitch, as Kevin keeps slowly bottoming out. The maid’s legs squeeze tighter around Kevin’s waist, trying to get him to go faster.

“No, Winter. I set the pace. I’m not going to hurt you.”

The drow whimpers again, but complies; the legs around Kevin’s waist slacken. Kevin is most of the way inside. Mona is moaning (Heh!), the Josie plushie under her squelching slightly. Again, Kevin is focusing on Winter below him. The drow is squirming, wanting him to go harder, but he won’t hurt the maid. He finishes pressing down. Winter’s nethers touch his pubis. He did it; he’s completely inside.

“So fucking hawt!” Mona moans from his side.

“Please... start thrusting. More...” Winter moans from below.

So, Kevin starts to thrust. Slow, even, steady. Winter whimpers, Mona moans. Being inside the drow feels really fucking good, if Kevin says so, especially now that he is moving a bit faster. His milk keeps the lube inside moist, if not adding to the slickness. Winter squeezes tightly along Kevin’s length, the maid’s genitals trying to harden, but can’t quite get there.

“Harder... Kevin... I’m tough... I can... take it”

Kevin’s seen enough porn with Mona to have a decent idea what to do to help Winter. He gently takes a thumb and pointer finger and starts to stroke off Winter. The drow is too delicate and small for a full grip; Kevin is enjoying the sight of Winter between his fingers like this. The maid groans loud enough to startle him. “You sexy bull bastard. Keep going!”

Kevin picks up the paces, both of them. Winter is mewling like a cat; the power Kevin has over the drow is a little intoxicating. Winter squeezes even tighter on him, thrusting into his fingers faster.

“I’m close... I’m so fucking close... Fuck, Kevin! So close! Can’t remember the last time I’ve cummed. Please...”

Mona sounds close, too. He remembers that lesson from last night. He pulls back just far enough to be able to focus on grinding into Winter’s prostate. Neither of them last long after that. Mona finishes herself off a few moments later; Kevin watches her, just in case he needs to for Mona’s weekly “no orgasms without a witness” weekly thing.

Kevin: +40 XP (Anal Sex, x4 bonus [First Time Both Participants])

Kevin: -40 XP (But The Other Participant was Neither Mona nor a Contestant...)

Kevin: Point of Information (She DID get off watching...)

Kevin: +8 XP (Provided Live Masturbatory Material for Mistress, x4 bonus [First Time Both Participants])

“Okay,” Mona pants, recovering first, “This plushie is soooo good. Thanks for winning it for me, Kevin.”

Kevin finishes pulling out, watching his milk and cum leak out of Winter’s still gaping ass. Fuck, that’s hot. He sees Winter’s thin love juices on his hand, too. Should I lick it off?

Winter leans up to lick Kevin’s hand clean. “You snooze, you lose, my sexy bull. Mistress, do you mind if I sleep here tonight? I want to get some cuddles in.”

“Shower first. Both of us,” Kevin orders.

“Yes, sir, Husbando, sir. Carry me? Still, Mistress, do I get cuddle time with my sexy bull?”

“Sure, Winter, if Kevin doesn’t mind.”

He answers with a grunt and scooping up the drow maid. His seed drips on the floor as he carries the maid to the showers. Let’s clean up and get ready for bed.