Chapter 54: Gimme a ‘V’ ... and a ‘V’ ... and a ‘V’!

December 31, 2001, Chicago, Illinois

🎤 Steve

I slept as late as I dared on Monday morning, knowing that Birgit would be waiting for cuddles, and taking into account the time I needed for breakfast, so that I could arrive at Kristy’s house as planned. I managed to ‘escape’ with just ten minutes of cuddling, then ate a quick breakfast which Kara had prepared, brushed my teeth, dressed, and hurried north on Woodlawn then right on 48th, and right once again on Kimbark to arrive at Kristy’s house. As we’d agreed, I walked past, stopping in front of the next house, and dialed Kristy’s number to guard against a last-minute change of plans by her parents.

“It’s Kristy! The coast is clear!” she exclaimed.

I hung up and walked back north, then up the walk to steps which I climbed to reach the porch. As I was about to ring the bell, Kristy, who was wearing her sexy cheer uniform, flung the door open and invited me in. I stepped inside, she closed the door, then threw her arms around my neck and kissed me fiercely. I returned the kiss, and our tongues danced for nearly a minute before she released me.

“The girls are in my room,” she said invitingly. “I’m half-tempted to take you to another room and go first, but the girls would kill me!”

“It is your house,” I replied, admiring her slim form and long legs.

“We all agreed to play the games, so I can’t!” she pouted. “Another kiss?”

I took off my hat, coat, and gloves, slipped off my shoes, and Kristy and I exchanged another fierce French kiss before she led me up a sweeping staircase to her large room where the other girls were waiting.

“Steve, this is Paige,” she said, indicating a gorgeous redhead who was about two inches shorter than me. “And this is Maya,” she said, indicating a compact, dark-haired Hispanic girl who was six or seven inches shorter than me. “Girls, he needs to see our test papers and our IDs.”

That last bit had been for my own peace of mind given what I’d discovered about Angelina after the fact. The girls all showed me clean tests, along with driver’s licenses which confirmed they were all seventeen. After I returned those, they each handed me a V-card - Kristy #6, Paige #11, and Maya #3. That would add to my previous collection of #1, #5, and #7, though not in that order. I put the cards in my pocket then waited for Kristy.

“I have a pair of dice and a list of what the numbers mean. The green die is what to do, and the red die is where to do it. If the body part is covered, then you uncover it. So, green die - 1 and 2 are kiss, 3 and 4 are lick, 5 and 6 are suck. The odd numbers are the girls acting, the even numbers are Steve acting. For the red die, 1 is lips, 2 is ears, 3 is the neck, 4 is the stomach, 5 is chest, 6 is between the legs. The time limit is thirty seconds, then the next girl goes. We’ll play five rounds, then move to the next game. First, though, each of us should kiss Steve! Two minutes. In V-card order!”

“Yes!” Maya exclaimed, pumping her fist.

I held out my arms and Maya quickly moved forward and we locked lips. Her arms tightened around me and she moaned softly into my mouth as our tongues twirled and swirled. Maya squirmed in my arms rubbing against me and when Kristy called time, she broke the kiss and put her lips near my ear.

“I can’t wait!” she whispered.

I decided then and there that if I had any way to control the outcome, she’d be the first, and get the most attention. I silently implored Loki for Maya to roll an endless string of fives and sixes for her ten rounds. I hoped that the contest that Kelly had suggested was how ‘first’ would be resolved, because I could easily ensure Maya won. Kristy was next, and we repeated the kiss we’d exchanged in the foyer. Paige went last, and her kiss was more tentative, but full of promise.

“Let’s go sit on the rug,” Kristy suggested. “Then we’ll roll to see what order.”

She picked up the dice and we went to sit on the rug between her queen-size bed and the couch. She shook her hand and rolled seven, then handed the dice to Paige who rolled five. Paige handed the dice to Maya who rolled eleven, which I hoped was a portent of things to come.

“Can I just go with this roll?” Maya asked.

“You wish!” Kristy exclaimed. “Roll again!”

Maya pouted, picked up the dice, and rolled a 6 and 5, indicating I was to suck on her breasts. She giggled and moved to my lap.

“Want to take off my sweater?”

“I do!”

I grasped the hem of her cheerleader sweater and she held up her arms so I could remove it. I pulled it over her head and off her arms, then unhooked her sports bra, revealing small breasts capped with light brown areolae and nipples. I lowered my head, opened my mouth, then closed it around her small breast. Maya moaned softly as I suckled her breast electing to use the entire thirty seconds without switching.

“Whew!” she gasped when I released her.

Maya moved from my lap and Kristy picked up the dice, rolled a 2 and a 1. which was her kissing me. She moved to my lap and we exchanged a French kiss. She moved from my lap and Paige rolled a four and a five. She happily helped me remove my rugby shirt and spent her thirty seconds licking my nipples.

Round two was relatively tame with Maya and I kissing, me sucking on Kristy’s earlobe, and Paige licking my stomach.

Round three was MUCH more fun, with Maya rolling boxcars, which meant I needed to remove her cheerleader panties. She stood in front of me, and I pulled them down, helping her step out of them. She lay down on the floor, and I moved between her legs, lifted her skirt, and pressed my mouth against her labia. With her skirt draped over my head, I pressed my tongue into Maya, savoring her spicy flavor. Maya moaned and bucked her hips, then groaned deeply when I tongued and sucked her clit. Time ran out far too soon, and I had to sit up.

“Do you want me to wash my face?” I asked.

“Uhm, yeah, probably,” Kristy said. “Let me get a washcloth.”

She left the room and came back with a damp washcloth which I used to wipe my face, but not before running my tongue over my lips and winking at Maya. Kristy rolled the dice and made a sour face when a 2 and 3 came up, and she spent thirty seconds kissing my neck. She had an even more sour look when Paige rolled a 2 and 6. I helped Paige remove her panties then simply kissed her labia, despite really wanting to press my tongue between them.

Round four started with Maya rolling a 5 and 6. I had been semi-hard before, but the thought of Maya’s sweet lips wrapped my shaft made me rock hard.

“Seriously?” Kristy groused.

“The dice rule!” Maya said gleefully. “Stand up, Steve!”

I did and she unbuckled my belt, unbuttoned my jeans, then pulled down the zipper. She pulled my jeans and briefs down together and helped me step out of them.

All three girls gasped and stared and my exposed erection.

“I’ve never done this,” Maya said. “How?”

“Like a Popsicle,” I replied.

She smiled, opened her mouth, then closed it around my glans. She bobbed slowly, taking me about halfway into her mouth and sliding her tongue around. I watched as I disappeared and appeared from her full lips, and groaned softly when time ran out and she released me. I sat down, wishing Maya could have continued, but knowing we were just a few minutes away from the next game. Kristy was much happier with her roll in round four which had me licking her nipples. Paige wasn’t, as she ended up with just a French kiss. Round five was positively boring, with Maya and I French kissing, me licking Kristy’s stomach, and Paige kissing my neck.

“Next is the blowjob contest! The winner is the one who makes Steve cum, and she gets fifteen uninterrupted minutes with Steve to do whatever she wants. Then the other two compete, with the winner getting her fifteen minutes. Then the last girl gets her fifteen. After that, I’ll roll for random things for each of us to do with Steve, then for the last hour he’s here, he does whatever he wants, though he needs to divide the time equally.”

That would work exactly as I had hoped, and because I was going to be able to control the outcome, Kristy would be frustrated, though I would absolutely provide her with maximum pleasure when it was her turn. Of course, after what would be five orgasms, I wasn’t sure there would be much left for the die rolling or ‘free’ playtime.

“Girls, take off everything except your cheer skirt,” Kristy said.

They did, then Kristy asked me to sit on the couch.

“Two minutes each,” Kristy said. “You can do anything with your mouth or hands. Steve, I take it you can last at least six minutes?”

“I can.”

“I’m going first, then Maya, then Paige.”

“May I suggest a minor tweak?” I asked.

“What?”

“That before each girl sucks me, I lick them for two minutes.”

“Yes!” she exclaimed. “Girls?”

“Oh, God yes!” Paige exclaimed.

“Absolutely,” Maya agreed.

All three girls moved to the couch and I moved between Kristy’s legs and put my head under her skirt. She jumped slightly when my lips touched her labia, and gasped as I pressed my tongue between them. She had a slightly musky, slightly coppery flavor, and I pleasured her for two minutes before we changed places. Kristy knelt in front of me and took me into her mouth. She clearly hadn’t ever given a blowjob, as she tried to take me all the way into her mouth and gagged, quickly pulled back, and releasing me.

“Sorry,” she said.

“Just relax and don’t try to swallow me!”

“I thought guys wanted to be deep throated!” she said.

“Walk before you run,” I said gently. “Just use your hand to stroke me and only take me a few inches in. And you have your full two minutes from when you start.”

She smiled and began again, this time doing a much better job. When her time ran out, I got up and moved off the couch and between Maya’s legs. Maya put her hand on the back of my head and caressed me as I pleasured her. As I probed, I discovered a ring of flesh which appeared to have survived the stress of cheerleading, though the opening was likely large enough that I could penetrate it without tearing it, as I felt it would stretch.

When we switched places, there were no other words to use other than to say that Maya made love to my dick. I caressed her hair as she had mine, and looked forward to helping her win. Her time expired and after she released me she planted a soft kiss on my glans before we exchanged places and I moved to kneel between Paige’s legs.

I took a few seconds to nuzzle my nose in her soft, trimmed red pubic hair, then pleasured her for two minutes, before switching places. She winked, then grasped my shaft. She parted her lips, took my glans into her mouth, then slowly slid down my shaft until her lips touched the bare skin around the base of my dick.

“Showoff!” Kristy groused.

Paige ignored Kristy’s comment and bobbed up and down, each time taking me completely into her mouth. When her time was up, she released me.

“Not bad for a first time,” she smirked.

Not bad for a tenth time, either, I thought as I got up so I could move between Kristy’s legs for the second round, which was nearly identical to the first, though Paige had an orgasm from my tongue and mouth. During round three, both Maya and Paige had orgasms, which made me feel bad for Kristy, so when round four began, I made an effort to bring her off, which I accomplished by going nearly three minutes past the limit.

When it was Maya’s turn, I was determined to cum, and used my hand to encourage her to move faster and suck harder, hoping I didn’t give anything away to the other girls. With about fifteen seconds to go, I felt the twinge, and just before time expired I groaned and erupted into her mouth. She continued bobbing and sucking until I finished, then released me, and showed both Kristy and Paige my cum in her mouth before she swallowed it. I helped her into my lap and surprised her with a French kiss.

“I need some time to recover,” I said. “It’s not right to start the fifteen minutes until I’m ready to go.”

“So what do we do until then?” Kristy asked.

“Unless you three object, I’ll lick you each to orgasm.”

They all agreed giddily and I started with Kristy, as she was the most difficult one to bring off. When I achieved my goal, I moved to Paige, then finally moved between Maya’s legs and did my best to make love to her with my lips and tongue, just as she had to me with hers. By the time she had her orgasm, I was rock hard.

I stood up, took Maya’s hand, and led her to the bed. I pulled down the bedspread and blanket, and we climbed in. I sat cross-legged and helped Maya into my lap, facing me. She put her legs around me and her arms around my neck. We kissed a few times while she rubbed her nipples against my chest, then I broke the kiss.

“Ready?” I asked.

“Oh, yes!” Maya breathed.

“Lift up,” I instructed.

Maya raised herself and I grasped my shaft, rubbed my glans against her labia, coating it with her juices, then held it in the correct position.

“Sit down slowly,” I said, putting one hand under her butt to guide her.

Maya nodded and I felt gentle pressure as she lowered herself. My glans parted her labia, and slowly entered her. Once I was partway in, I moved my other hand to Maya’s butt and squeezed gently. As she slid down, the ring of flesh stretched to accept me, then gripped my shaft as she sank down until I was completely inside her.

“«¡Dios mío!»” Maya whispered breathlessly.

“You feel really good,” I whispered into her ear. “Just move however feels good.”

We kissed and Maya began gently moving her hips forward and back. I kept both hands on her firm butt cheeks, and helped her when she moved up and down, the ring of flesh gripping me as she did so. She figured out the right movements to give herself an orgasm, and after the spasms subsided, she broke our kiss.

“I could do this forever,” she whispered, then kissed me again.

She continued moving and I thoroughly enjoyed our ‘adulting’ keeping an eye on the clock while savoring the pleasure of her motions. Maya was small and light, so when there are about three minutes to go, I maneuvered us so that she was underneath me. She instinctively wrapped her arms and legs around me and I began thrusting in and out, working myself towards my own release. I needed an extra minute to get there, and when I came, Maya tensed all her muscles, squeezing my shaft tightly with her silky walls. After a couple of spurts, Maya shuddered, groaned, and had a tremendous orgasm which milked the remaining cum from me.

“«¡Dios mío!»” she whispered breathlessly.

“You were fantastic,” I replied.

Maya whimpered when I withdrew, I kissed her, then got out of bed. I got the washcloth to clean up, then went to the couch. Maya stayed in bed and turned on her side to watch while Kristy and Paige competed for the next turn. Paige easily won with her ability to deep throat me, and Kristy looked very annoyed. Paige got up and moved towards the bed, while Maya got up.

“I need a bit of time to recover,” I said.

I realized I’d actually treated Kristy very badly, and decided to give her some extra attention.

“Fifteen minutes of oral pleasure,” I said. “And when it’s your turn, you get thirty minutes of the best possible sex I know how to give.”

I got between Kristy’s legs and used every bit of skill and experience I had to provide maximum pleasure, and succeeded in giving her two very good orgasms before I was ready to go again. I quickly washed my face, then moved over to the bed and got in next to Paige. I wanted to make sure she was sufficiently wet, so I suckled each breast for a bit, then moved between her legs and teased her clit, which had the desired effect. I moved on top of her, lodged my glans against her labia, then kissed her.

“Slow and gentle,” she whispered when I broke the kiss.

I nodded, and lowered my mouth to hers. As my tongue entered her mouth, I pushed my hips forward, parting her labia with my glans, and entering her in one slow, smooth motion. Paige wrapped her legs loosely around my thighs, put one arm on my back, and caressed my head with the other, and I began sliding slowly in and out of her warm, wet pussy. After a few strokes, Paige began moving her hips.

A few minutes after we began, Paige had the first of several small orgasms, and I wondered if, after all the sex I’d had in the past twenty-four hours, if I’d actually be able to cum within the time limit, and did something I rarely ever did - focused on achieving my orgasm, rather than giving Paige maximum pleasure. Paige’s request for ‘slow and gentle’, with no indication she wanted me to be more forceful, made that a challenge, but I achieved my goal. After I came, I moved down and licked Paige to a final orgasm, then moved up to kiss her.

“That was perfect,” she sighed after we broke our kiss.

I helped her out of bed, washed my face and groin with the washcloth, then went over to Kristy and led her to the bed. We got in and after a few kisses, I moved down to her breasts, then between her legs. I gave her two good orgasms, but didn’t feel the usual twinges, so I coached Kristy into a sixty-nine position, and through the combination of her taste and smell, and her sucking and licking, I became hard.