Chapter 2: Great Expectations
I tugged a pair of basketball shorts on over my hard member, doing my best to stuff it down the pant leg. I wished that I could at least wear boxes to keep things mildly contained, but rules were rules. The shorts did nothing to hide my stiff outline, but all the rest of my clothes were still boxed up—it was all that I had available. I grabbed a shirt and followed Lexi downstairs for dinner with house.
I walked into the dining room, which was already abuzz with chatter as nearly thirty women sat around large rectangular tables. To be honest, it was a little overwhelming, so I was grateful when I spied Stephanie waving for me. As I made my way over to her, heads turned towards me and I heard whispering that I could only barely make out:
“Oh shit” “You see that bulge?” “Is that his cock?”
I had hoped that my dick would have quieted by now, but the sleek thin material only stimulated me further, stunting any possibility of that and leaving little to the imagination. At least the ladies seemed to like what they were seeing. I hastily dropped into the seat next to Stephanie, my face reddening in embarrassment.
“Don’t mind them,” she said to me. She had changed out of her workout attire from earlier and now wore a pretty strapless floral summer dress.
“Thanks. I got … err … a little riled up earlier and am having some issues,” I replied sheepishly.
“That’s okay. I thought I saw Lexi coming down the stairs… Anyway, you’ll get used to it. Most of our live-ins even grow to enjoy the attention,” she encouraged with her characteristic positivity. “And we’re very happy to have you here.”
Despite the embarrassment, I could reply honestly, “I’m glad to be here.” And it wasn’t just to avoid homelessness. Nearly everyone I had met so far had been quite nice to me.
“Before we eat, I’m going to introduce you to everyone. I know there’s a few in here that weren’t around earlier when I was giving you the grand tour.”
“Yeah, that would be great.” I looked out at the crowd around us, many of whom were still pointedly glancing in my direction as they talked to their neighbors. I realized that I had never been the only man in such a large group of women and I had to admit that I enjoyed the attention. Maybe this wouldn’t be so bad after all. Not to mention, all the sisters were gorgeous—way out of my league under any normal circumstances.
“When I introduce you, I’ll go over the house schedule for the evening; you’re welcome to join us for any of it. But then remember you’re expected to be available by 9:00.”
I had forgotten about that requirement amidst everything. “Oh, yeah, that’s right. Available for what exactly?”
“You’ll have to wait and see,” she teased with a devilish grin.
A moment later, when the clock struck 6pm, she stood up and quieted everyone down. She seemed to generally be the one in charge of the house, apparently including the schedule.
Stephanie kindly introduced me to generous applause, and I was quite glad that my erection had subsided in the last few minutes when I was asked to stand up. She went over the schedule after dinner, which included options for watching Love is Blind in the living room, quiet study time in the library, or a walk around the grounds.
But the part that really sparked my interest was what she announced next: “Then, at 9pm. We will have our Deep Lipstick Derby in the basement for those that wish to enter. That will really give us a chance to get to know our new Live-In!”
This elicited great hooting and hollering from the crowd. What the fuck was a Lipstick Derby? And how would it help them to get to know me?
——————
As much as I wanted to socialize with some of the ladies, wasting all weekend finding and moving into a new place to live meant that I was quite behind on preparation for finals week. After nearly an hour of enjoying dinner and getting to know some of the women sitting near me, I opted to head to the house library and try to catch up before my 9pm commitment.
I was not the only one there, which was no surprise considering we were about to begin the last week of the school year. The ten or so other women were all paired off into twos and threes, grouped around the small tables in the cozy room, some better than others at maintaining the expectations of silence.
It wouldn’t have mattered though, because I couldn’t focus anyway—all I could think about was the Lipstick Derby. I tried to puzzle through what that could possibly entail and how I might be involved. I eventually settled on a guess that they were going to be embarrassing me by putting make-up on my face or something.
The closer we got to 9pm, the emptier the library became until it was 8:55 and I was the only one left. I ran upstairs to drop my laptop back in my room and headed down to the basement.
As I pattered down the stairs, I could hear the signature raucous din of a large group of excited women. I had to admit that I was rather nervous, wishing I knew what was in store for me when I reached the bottom step. I took a deep breath and descended.
An enormous cheer came from the crowd in front of me as I finally reached the dimly-lit basement. A crowd of two dozen gorgeous women stood before me, all barely dressed at all. Each of the sisters wore what had to be the smallest pieces of lingerie I’d ever seen and they looked incredibly fine. I tried not to have a heart attack as I felt my dick come to life inside the thin basketball shorts.
Maria, who had introduced herself to me at dinner as the “Special Activities Chair,” grabbed my arm excitedly and pulled me up towards the stage. The feisty Latina wore a navy blue sheer lace lingerie set, complete with garter belt and stockings. Her large tan boobs were spilling out of the frilly material trying to contain them.
A hush fell over the crowd as we reached the front. “Our guest of honor has arrived!” Maria called as another round of hooting, whistling, and cheering rose up. “Jack, we have a special ‘welcome to the house’ organized for you tonight. We call it our Deep Lipstick Derby.”
“Our contestants have chosen a particular color of lipstick to wear tonight. They will each have 60 seconds to deep throat you. The one who places gets their lipstick furthest down your cock is our winner!” I looked out to see that there was indeed myriad colors of lipstick worn by the frenzied women in front of me, mostly matching the sexy lingerie sets they were wearing. My cock took another jump in my shorts while I tried to keep it under control.
“A couple of caveats,” Maria went on. “First, ladies are only allowed to touch you with their their mouths. Second, if you orgasm before we are through all of our contestants, you must go down on the woman that serviced you until you’re hard again.” I was immediately grateful to have a generally short refractory period. “And third, the winner will get to enjoy you for the rest of the night as they please. Does that sound good to you, Jack?”
The entire situation finally came into clarity. I was brought here to serve as the sorority’s boy toy in exchange for room and board. Did it sound good? Dear Jesus, it was a fucking dream come true.
I tried to control my drool as I replied, “Absolutely!”
“Wonderful! Then let’s introduce our contestants. We have seven tonight!”
Seven beautiful sorority sisters in a whole spectrum of color emerged from the crowd as Maria called their names, each receiving a raucous round of cheers as they joined us on stage. I was particularly excited that all three members of my interview committee had decided to participate.
“One thing left to do now … get him naked and hard!” An enormous clamor arose from the women, the loudest of the night so far. “That will be my honor,” Maria said to me more quietly, helping me out of my shirt. “Ready?”
I nodded eagerly as she turned us sideways to the crowd and dropped to her knees on a soft pad that had emerged from somewhere. The din grew to ear-piercing volume when Maria gripped the waistband of my basketball shorts and pulled down.
The arousal of the scene before me clashed with the nerves I had been feeling, leaving my cock at a pleasant half mast. Nothing to be ashamed of while not seeming too eager. I was proud of my guy.
I looked down at Maria’s devilish brown eyes, noticing that she was not wearing any lipstick. I suppose that she would have an advantage as the “warm up act” if she was competing. She smiled at me as she took the tip of my dick into her mouth and reached up to massage my balls. She did not take me in very far past the head, but her tongue stimulated my frenulum in the most delightful way. Within a couple of minutes, I was fully hard and Maria’s job was unfortunately done.
“Long, cut cock ready for action!” she announced lewdly as she stood up. The crowd roared in response. “First up, Nicole!”
Nicole was gorgeous. Short blonde hair and pert small tits suited her petite frame well. I could glimpse pink gumdrop nipples through her forest green lingerie set. She lined up in front of me, her lips caked in matching lipstick.
“Ready! Set! Go!” Maria shouted as she started a large clock-shot style timer that everyone could see. Knowing that she had virtually no chance at making me come in sixty seconds, Nicole was not wasting her time. She pushed her lips my length, smearing her green lipstick along the way. Her first attempt only made it down maybe three or four inches, but even with her disregard for technique, it felt good.
Her second try she was able to get a couple more inches, but her eyes started to water as she gagged. I felt the tip of my dick hit the back of her throat before she ejected me from her mouth, coughing up spittle and pre-cum while her mascara ran down her cheeks. She gave it one more attempt but barely got further than her first try, seemingly defeated.
“Time’s up!” Maria called and Nicole slid her mouth off of me. I looked down at my dick to see streaks of forest green running up and down the top half of its length, a firm green lipstick print identifying the furthest the poor girl had gotten.
“Next … Kaveri!” Maria announced. A lovely Indian woman stepped forward. An ornate purple corset and matching high-wasted thong accented her generous curves beautifully. I was jealous of the women that had a better view of her ass than I did.
“Annnnnnd go!” Maria shouted. Kaveri was taking a more sensual approach than Nicole had and was gradually working her tongue down my shaft after taking my tip into her purple-lipped mouth. She kept eye contact as she slithered her way down my length and I couldn’t help but be wrapped up in her gaze.
She easily passed Nicole’s effort and pushed about an inch beyond her sister’s green mark, purple now becoming the primary color of my cock as her lipstick smeared down my member. She stopped at her limit, clearly aware of how much she could take and focused on pleasuring me without the theatrics of Nicole’s attempt. I felt every swirl of her tongue and considered that it probably wouldn’t take her much longer than 60 seconds to get me off if she was given the opportunity.
However, her time was called and she released me from her mouth, much to my dismay. “We have a new leader!” Maria announced to the pleasure of the crowd. I looked down to see a lovely mixture of purple and green until a Kaveri’s purple shade took over for an extra inch or so. I wondered how many more women I could last through until I blew.
“And now Melanie!” I recognized her as the blond that had been using my shower when Stephanie had first shown me my new room. She wore a baby blue bodysuit that really pushed up her large tits and drew my eye towards her toned, round bottom. I felt my dick pulse and found myself hoping that she would win.
However, despite her best efforts, she could not best Kaveri and her blue lipstick line settled in between Nicole’s now-fading green and Kaveri’s deep purple. Although not the deepest so far, she was clearly quite skilled with her mouth and I looked forward to getting to know her better eventually. Time was called just as I could feel myself growing close to orgasm.
“Next up … Lexi!” Lexi strutted forward, yellow lips and lingerie on full display. Her big tits and thick ass made to look even juicier by the set she was wearing. I knew right then that she was going to be the one to make me come.
She dropped to her knees and stared up at me hungrily. Maria yelled, “Go!” but before taking my shaft in her mouth, Lexi planted a kiss on my shaved pubic area, marking me with her golden lipstick. Then, she moved underneath my shaft and set her lips on my scrotum, taking one of my balls into her mouth just as she had earlier in the evening. My cock visibly throbbed as I felt the sensation pleasurably wash over me. It felt so good.
She took her time with my testicles before setting on my dick. Her mouth glided down my cock past the marks of Nicole and Melanie before she stopped. I got the sense that she could have passed Kaveri as well if she had the desire, but she was focused on one thing now — making me come. She sucked hard as her tongue danced along the underside of my shaft.
I felt that familiar tightness in my balls and tried to hold off my climax, but I was powerless. “Fuck! I’m gonna come!” I groaned. This only egged her on as the gleam in her eyes intensified along with power of her suction.
I couldn’t hold it in any longer and I started to blow. I unconsciously pushed myself deeper into her mouth as I launched rope after rope of cum into her yellow-rimmed mouth. At first, she took it all like a champ, never breaking eye contact, but then as the flow kept coming, she was overwhelmed by it. Driblets of cum started to leak out the sides of her mouth as her eyes watered until my cock stopped spurting into her and began to soften.
She pulled off of me and stood up, faced the crowd, and opened her mouth, showing off the load that I had just deposited. The ladies went berserk as Lexi took a theatrical bow and swallowed.
“Lexi’s done it!” Maria called. “She made him come! And now it’s her turn! How do you want him, Lexi?”
“The chair,” she said simply, and immediately a plush recliner was rolled up onto the stage. Lexi whipped off her yellow g-string, sat down, and looked at me. “Time for you to get to work,” she said with a seductive grin.
“My pleasure,” I replied, now falling to my knees in the same way all the women had before. As I brought my face close to her shaved crotch it was evident how wet she already was, her brown folds moist and dripping. Somewhere behind me I heard Maria call for a couple of girls to come help stroke me and get me going again, but I was focused now.
I teased her to start with, nibbling on the insides of her thighs and kissing around her most sensitive areas. She let me go on like this for a minute, but quickly lost patience, grabbing my head and pulling it against her leaking pussy. I ran my tongue up along her dark pink slit while I felt Maria’s volunteers reach around me and start fondling my dick. It wasn’t going to take me long to bounce back whatsoever with all this stimulation.
My lips found Lexi’s clit and she moaned. I sucked lightly as I swirled my tongue around her little button, which was bulging with arousal. ”Fuuuuck, that’s good,” she groaned, her hands still on the back of my head.
I continued working her, responding to her sounds of approval. I tasted even more wetness coming from her pussy as she began humping my face, yelping with each stroke of my tongue. I was already hard again, but I wanted to finish the job now.
Lexi yelled, “You’re gonna MAKE ME—“ Before she could finish, her orgasm ripped through her and she bucked her hips violently up into my mouth. Her legs clenched around my head as I felt her pussy pulse against my lips.
After a moment, she slowly released her legs from around my ears, awakening me to the incredible clamor coming from the rest of the sorority sisters behind me. “That was fucking good,” Lexi said through a wide grin as she looked down, her feet sliding back down to the floor.
She stood up and announced, “I can confirm that his tongue is just as nice as his cock, ladies!” The women laughed in response as they continued cheering.
“And it looks like he’s ready to continue,” Maria jumped in. “Shall we?” she asked me as Lexi’s chair got rolled back away. I nodded affirmatively and eagerly as I realized that I was indeed back at full attention, a rainbow of color smeared along my length.
“Wonderful! Next up, Courtney!”
Courtney was dressed in a sexy red one-piece that seemed to be made of some sort of see-through mesh, leaving nothing to the imagination. Her large areolae peeked through the material as her generous boobs pushed up against it. Cherry red lipstick adorned her mouth.
Courtney put in a good effort, but Kaveri’s purple lipstick remained the mark to beat once she was done.
“And now for our final contestant,” Maria went on. “Stephanie!” Stephanie wore an ornate pink set (I wondered if she even owned any other colors) that boosted up her boobs beautifully.
She slunk to the ground and looked up at me. “Ready to have your mind blown?” she asked with a devilish smirk.
“Show me what you’ve got.”
Maria started the timer and Stephanie easily took me deep into her mouth, her short brown hair curtained around her focused face. At first, she effortlessly matched Kaveri’s mark as she slithered her tongue along the underside of my shaft. She looked up at me and winked as she swirled my cock around in her mouth. Was she toying with me?
She slid off of me momentarily before slamming my dick into the back of her throat in one smooth motion. Her lips gripped the base of my shaft, nearly touching my balls as she aggressively sucked on me. It was definitely the deepest anyone had ever taken me orally, and it felt fucking amazing. As her pink lipstick imprinted on me, clearly much further down than Kaveri’s, the ladies watching applauded in exuberant support.
Stephanie played with me a moment longer until her time was up when she grabbed the tip of my dick and presented it to the audience, joyously showing off her handiwork. Her pink mark was at least two inches further than the purple. When I first met the bubbly Stephanie I wouldn’t have guessed that she had this hidden talent, but boy was I glad for it.
“It looks like we have a winner!” Maria called. “Unless there are any late entrants…?”
A moment of heavy silence hung in the air for a moment, and then a voice echoed from the back of the group.
“Fuck it. I think I can do better,” Danni announced as she split the crowd. Her web of black lingerie matched the collage of tattoos on her pale skin. Heavy black mascara and black lipstick completed her goth look.
“I was wondering if our two-time winner was going to enter!” Maria said excitedly. “Whenever you’re ready Danni!”
She dropped to her knees in front of me, a look of boredom etched on her face as she looked up at me and rolled her eyes dismissively.
My dick parted her painted lips as she moved down my length. Unlike Stephanie, it took a few pumps to get her used to my size, but soon enough she had nearly matched the pink mark. Then, with a final push, she pressed her lips into my pubic bone on the skin around the base of my shaft, her lower lip imprinting on my sack.
She looked up at me with watering eyes, and then bit down. Not hard enough to break skin, but it did hurt enough that the surprise of it made me jump and pull back.
She laughed and choked simultaneously at my quick exit. Her time wasn’t up, but she was clearly finished.
The cheers were definitely quieter now than they were for Stephanie as Maria announced, “Well it looks like she’s a three-time winner now! Our repeat-champion …. Danni!” Her black lipstick over-shadowed all the other shades on my member, edging out Stephanie by about a centimeter.
Maria produced a plastic tiara that was emblazoned with “Cock Queen” on the front. Danni took it with another eye roll as Maria lifted her hand in the air like a heavyweight champion. I wondered why she entered the competition at all if she was so apparently uninterested .
“Any big plans with our Live-In tonight?” Maria asked.
Danni retorted quickly, “Nope. In fact, somebody else can have him. I don’t want him.”
The crowd of ladies seemed shocked for a moment as rare silence overtook the room. I was well aware Danni didn’t seem to like me, but damn, this definitely was a blow to the ego. It hurt.
“Well, okay then,” Maria said, taken aback. “I guess he goes to Stephanie then. If she wants him, that is.”
“Yes! I want him!” Stephanie replied immediately, as if impatiently awaiting Maria’s offer. Her pink lipstick was now slightly smeared on her face and she looked hungry. “I very much want him.”
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