Innocent Milf

Chapter 17

We reconvened in the library, where extra seats had been placed. A couple of the red-vested staff stood off to the side of the room. Four chairs had been set up near the front of the room. The rest of the group filtered in, their faces eager and displaying various levels of horniness. The party had clearly achieved the intended effect of getting everybody ready for a night of hot sex and swapping, as a lot of gazes lingered on us as we entered the room.

"Welcome to the Tiebreaker!" Ty announced. Everybody cheered. Cary, Carla, Dan, and I were ushered up front.

Nancy pointed to four padded office chairs. "You four sit there. The name of the game is Never Have I Ever."

The other ten partiers started laughing knowingly. Cary looked as nervous as I felt. Carla looked confident. Dan was unreadable. I shrugged. At the end of the day, what I had said to Cary earlier in the evening was the truth--I already had a car, and I was less invested in getting a new one than in getting to a hotel with her. This crowd had me acutely aware of how sheltered my life had been by comparison, so I was not confident of coming out on top in a "never have I ever" contest.

"Here's how this will work," Nancy said, reading from a notecard. "It's more or less Truth or Dare. I have a list of sexy statements. For example: 'Never have I ever gone a whole day without wearing underwear.' If you haven't gone a day without wearing underwear--that is, if you

agree

with the statement, then you have to lose a piece of clothing. Once you have lost all of your clothes, you are eliminated. But you can keep a piece of clothing by saying 'Challenge' and performing a random naughty act on one of our lucky audience as dictated by these sexy dice!" She held a pair of large oversized novelty dice up in the air, to the

oohs

and

aaahs

of the group. "None of these go all the way to penetration, and you can only challenge three times!"

"And even though we assume people will be telling the truth about this, we'll go around and confirm details," Ty clarified. "Be honest!"

My heart sank. I could pretty much kiss that Aston Martin goodbye now. I was hardly a virgin, but this crowd almost certainly had me beat for sexual adventures and experience.

"First statement: never have I ever had sex in a public place!"

I hesitated. Did the park on Solstice night constitute a public place? Certainly it was public land. I crossed my arms and waited. I wondered what public place Cary had been in, since she wasn't taking any clothes off. The group laughed, and Nancy shook her head. "Okay, that was a gimme. Details, people!"

In order as she pointed to us: park, airplane, theater, bathroom. The last one was Cary, who flushed, but held her head up defiantly as she said it. I wondered what the story was there. My curiosity about Cary's past grew with every new revelation.

Next one: Never have I ever had a foursome or more.

I kicked off my shoes, as did Dan. Cary kept her hands folded, as did Carla. I stared at Cary in surprise, and she colored, not meeting my eyes.

Carla smiled: "Our last party! Some of you remember." The group nodded and laughed.

Cary hesitated. She was deathly pale. After a long moment and some encouragement from the crowd, she almost whispered, "Honeymoon."

The room exploded, and Cary buried her face in her hands. Shouts of "Yeah, girl!" and "No way!" echoed through the library.

Dan leaned over to me. "Did you know she was married, dude?"

"Separated," I managed, fighting a raging hard-on.

Dan looked as if he was about to say something else, but Nancy held up her hand to quiet the room. "Next one: never have I ever cheated on a partner."

I pulled off my socks and threw them on top of my shoes. Cary kicked off her heels, as did Carla. Dan looked guilty, but removed no clothing.

"Spill it, dude," Ty demanded, as the crowd obligingly made "Oooooh" noises, like a class full of kids whose classmate has just been called to the principal's office. This was like an Old West melodrama.

Dan squared his shoulders. "First girlfriend in high school. I was a little shit."

"Never have I ever bought something from a sex shop."

I was dying. I pulled off my tie and threw it into the pile. I'd never even been

into

a sex shop. Dan looked pensive, as if trying to decide whether something he'd thought of counted or not, but finally pulled his socks off. Carla and Cary gave each other a look and broke into chuckles.

"Do you want the whole list?" Carla asked. The group chuckled appreciatively.

"Lingerie," Cary answered primly.

"Never have I ever sent nude pictures to somebody."

My jacket went into the pile. Dan's tie followed. Carla appeared to think, and then pulled off her pantyhose and threw them next to her shoes. Cary smirked and stayed sitting. I almost laughed out loud, realizing that she was thinking of her fake affair photos.

The small crowd was really revving Cary up, now. She looked embarrassed, but said, "Professionally-taken pictures for my now-ex-husband." Her words had started to slide together--the drinks and the late night were taking their toll.

"Never have I ever gone to a strip club."

Dan and I looked at each other and shrugged. My cummerbund joined his jacket. I wasn't feeling quite so inexperienced, now. At least Dan was only slightly ahead of me. Cary sat coolly back in her seat, and I envisioned Eric dragging her into a strip club, to her embarrassment. Carla started to unzip her dress, but stopped as she saw Cary wasn't removing clothing, and said, "Challenge."

Everybody cheered and Ty rolled the dice. Consulting a printed table, he announced "Titjob." He pointed to Alan. "Agent Hardrock."

Carla didn't hesitate. Walking slightly unsteadily over to Alan, she popped her breasts out of her dress with practiced ease and unzipped his tuxedo trousers. The rest of the group cheered, but I could suddenly see Cary's resolve wavering. So far, all of the sexually explicit acts in this game had been in private--or at least somewhat private. The idea of doing something like this in front of thirteen other people appeared to have made her nervous.

Ty counted off time on a stopwatch, and then called time. Carla wiggled her boobs back in, blew a kiss to Miles, and pranced back to her seat. Nancy turned to Cary. "Details."

Cary rolled her eyes. "Taken by girlfriends the week after my separation." I nearly choked--that was so recent! The next several questions went by as we all tossed varying amounts of clothing into the pile--as with the other games, this one was clearly intended to get us naked as quickly as possible, or to get the other folks riled up hearing about sexy adventures.

Never have I ever done phone sex. Never have I ever made out with somebody of the same sex. Never have I ever had sex in water. Never have I ever flashed somebody in public. Never have I ever done the "walk of shame." Cary had to have that one explained to her, but then did not take any clothes off and said, "After Valentine's Day." By the time Cary had shed her stockings, dress, and bustier, things were getting heated. Carla had challenged once more and was down to her bra and panties.

I was sitting in my boxers, wondering if I should challenge. Dan was faring only a little better--he still had his undershirt on.

"Never have I ever hooked up with more than one person in a single day," Nancy's voice carried. "Our parties here don't count."

My heart beat faster. What the hell. "Challenge," Cary and I said simultaneously.

Ty rolled the dice and consulted his table. "Body shots!" he announced. Cary's eyebrows drew down momentarily, and didn't rise much after Nancy whispered an explanation in her ear. One of the red-vested attendees opened a desk drawer and asked for our liquor preference. I wasn't very experienced with liquor--hell, I wasn't supposed to be drinking at all. I would be useless for driving after this.

"Rum," I answered. Cary thought about it and echoed my choice.

I was pointed towards Anne--"Lottie Sechs"--who was already pulling down her dress and lying on the sofa as others cleared room for her. The red-vested "dealer" walked up with a shot glass full of light-brown liquid and offered it to Anne. She shook her head. "Pour it in my belly button," she said.

I could hear laughter coming from where Cary was walking towards her assigned partner--Anne's tousle-haired boyfriend Scott. But I was concentrating. The dealer poured liquor on Anne's belly, and I knelt down to suck it out. It burned my throat a little--although not as much as the bourbon had done at the beginning of the party.

"You missed some," Anne grinned as I lifted my head. She put her hands in my hair and kept face down until I had licked her entire belly clean.

As I stood up, grinning like a dummy, I saw Cary on her knees with her hands behind her back. She was leaning forward, her head moving towards "Agent Swelling's" erection. I blanched, and then realized that he had squeezed the shot glass between his thighs just below his testicles. Cary's forehead brushed his dick and balls as she leaned forward, blushing furiously.

After a moment of a gurgling sound and some lapping, she straightened up, looking determined. The dealer retrieved the glass and turned it upside for inspection. A tiny, slow-moving drop of liquor clung to the edge of the glass, but otherwise Cary had emptied it.

We tottered back to our seats for the next question. It seemed like these challenges were easier for the guys than the girls--not that I was complaining. I decided to use all my challenges if it kept me in the running.

Our next challenge after "Never have I ever tried to seduce a coworker, teacher, or professor" was dry humping. We were still clothed, but only barely. Luckily for us, our partners were still in their full tuxedo or evening gown. I gave Cary a questioning look as we took careful steps towards our assigned partners--me to 'Cassidy Rider' and Cary to 'Agent Standup' who had been sort of at the periphery most of the time. Cary nodded at me once, nearly overbalancing herself as she did so.

'Cassidy' looked me up and down as I approached, and smiled slowly. "Back for more, eh?" She lay back on the same desk that Anne had been on for body shots and raised one leg up, her rucked sapphire dress falling away from her knee. I placed my hands on her hips nervously--as if I were about to get caught shoplifting or something. Cary had reached her partner and sat in his lap, back towards him and facing me. We'd already done some of this, but in front of everybody else, it seemed extra intimate.

"And... start!" I could hear the soft

beep

as Ty hit the timer button on his watch. Keeping my eyes locked on Cary, I started slowly grinding against Heather. She moved back against me, and I could feel the tip of my trouser-shrouded dick bumping right against lips through her thin panties. She moaned a little and rolled her pelvis.

Cary was slowly rocking back and forth. Her position made it easier to keep a little bit of fabric between her and 'Standup's' obvious tented crotch. Still, she had to be feeling something, moving like that. Her tongue flicked over lips once as she held my gaze. Alex was helping her move back and forth, pushing on her hips.

"Thirty seconds!" Ty announced. "Speed up!"

I increased my rhythm, trying to keep longer motions. Cassidy breathed a little harder, and I could see her pulling her neckline down in my lower peripheral vision. A hand snaked out and pulled one of my hands to her breast. My eyes widened, as did Cary's. I gritted my teeth and thought of the complex chord changes in a mandolin piece I had been working on.

Across from me, Cary had also sped up. 'Standup' had moved one of his hands to her belly and the other to her lower back, and was rocking her back and forth that way now. Cary's gray eyes bored into me, and I could almost imagine that it was her beneath me, and my hand creeping up her belly towards her chest.

"Time!" Ty called, and Cary trapped Alex's wandering fingers just before they had a chance to pull down her bra cups. Cary nearly leaped off of his lap, stumbling towards me. I caught her in my arms and backed away from Cassidy, pulling her towards me. The rest of the room laughed.

"That rum will go straight to your head!" Miles called. I couldn't have agreed more. Cary and I leaned lightly on each other on the way back to our respective seats, and kissed quickly before sitting back down. I let my hand trail along her belly and flank as I stepped away.

Nancy gave us both a look. "Ready to continue? Need a minute to clear your heads?" The rest of the room laughed again. Nancy cleared her throat. "Never have I ever had sex while talking on the phone with somebody else."

"Challenge," I said. My last one.

"Oral," announced Ty after rolling the dice.

I hesitated. "Pass," I answered. "I forfeit."

"Really, dude?" Ty looked disappointed, but then glanced at Cary, who was beaming at me with undisguised adoration. "Okay, you got it. Good job, Agents! The winner is Agent Woody! Congratulations, Dan!"

I turned and shook Dan's hand. "Well done, man," I said.

He shook his head. "I feel like I won by default."

"Nah," I said. "You were luckier this time! And you've clearly had a more sexually adventurous life than me. Makes me feel like I need to catch up." As we climbed back into our clothes, Ty waved us away, and indicated we should sit in the peanut gallery with the rest of the group.

"Last couple of questions for our Dolls," Nancy announced. "Never have I ever swallowed!"

Cary opened her mouth, closed it, and looked over the sea of eager faces. Making a decision, she unsnapped her bra and tossed it into the pile and sat with her arms crossed over her breasts. I wondered if she had been spooked by the oral challenge. Carla smirked as she answered, "If the occasion calls for it." The room hooted and clapped appreciatively.

"Never have I ever faked an orgasm during actual sex," Nancy read.

Now it was Cary's turn to smirk. "All the time with my ex-husband," she said sardonically.

Carla looked at Cary's pile of clothing, and shrugged. "Guess I've been lucky. Not me. Challenge."

"One minute role-play," Ty read from his card. "With Agent Swelling."

Carla stood up and sauntered towards the surfer-looking guy whose tuxedo was now rather rumpled with all the removal and re-dressing it had seen in the past few hours. Full body on display, she leaned forward, dangling her large breasts in front of him as she placed a hand on either shoulder. "Oh, Mr. Swelling," she cooed, "I'm so sorry I didn't get my homework in on time. I

really

need those points for my grade. Isn't there...

anything

I could do to get them back?"

The next minute demonstrated that both players had not been in Drama class in school, but that they at least had no compunctions about feeling each other up and deep kissing.

"Last question," Nancy announced. "If we still have a tie after this... I don't know. We'll think of something. Maybe rock-paper-scissors?" The audience chuckled. She read over the card and shook her head disbelievingly "Never have I ever had sex on video."

Neither Carla nor Cary moved to take off their last article of clothing. My heart was racing. I arched an eyebrow as I looked at Cary, who buried her face in her hands and wouldn't meet my eyes. If she had had sex on video before, why had she been so shy about taking semi-nude pictures? Nancy smiled and folded her arms. "Okay, how about professionally?"

Carla laughed. "You mean, was it ever sold?" She shook her head. "Nope. We just wanted to see what we looked like making love." She blew a kiss to Miles. "The answer was 'pretty great.'" She made as if to roll down her panties. She looked over at Cary, clearly expecting her to do the same.

Cary hesitated, very pale. She stuttered and gave me a terrified glance. "Um... I'm not sure. It was Valentine's Day. I was drunk." Her face twisted and she waved Ty over. She whispered something in his ear, and he straightened, a surprised look on his face. "Uh... I'm not sure. Let me confer with Nancy."

I stared at Cary incredulously. What could possibly be in question? Whatever it was, I felt certain it had something to do with Eric. Her loser ex-husband seemed to have no end to his depravity. But she had been involved in a foursome on her wedding night as well. Just how much was Cary Bernham hiding? My half-drunk mind raced with bleary images of Cary fresh out of college, broke, and looking to make rent. Was there some guy out there with a basement full of old Betamax tapes watching younger Cary getting pounded by an 80's porn star with a bad mustache right now?

Even mostly inebriated, I knew that I would need to ask about Valentine's Day at some point. It sounded like it had been either a really wild night or a disaster. Or both. I wondered if it had something to do with why Cary was so shy.

Ty talked for a moment with Nancy while the room buzzed. After a moment, they waved over the red-vested attendants and began to speak. Clearly, this tie-breaker needed a tie-breaker. As waited, a couple of guys leaned over and jostled my arm. "Dude, your chick was in porn? That's so hot!" I smiled woodenly, not certain what to think. Except that if it were true, I would be trying to track down that tape as soon as I could.

Cary was white as a sheet as Ty cleared his throat. "We left it to the staff here as disinterested parties, and they've decided to count it!" he said. "We have a winner! Kitty Bristol! Congratulations Jane!"

The room cheered. Carla pouted briefly, but her expression cleared. She leaned over and whispered something to Cary, who shook her head vigorously. Carla shrugged, and opened her arms for a hug. Cary hesitated, but opened her own arms and hugged her back. Carla gave her a squeeze, and I found myself staring at their bare breasts pressing together. Cary said something and giggled a little too loudly, and Carla waggled her eyebrows suggestively.

All I knew was that this dreamlike erotic party had finally come to an end for us. Cary had won the vacation to Puerto Vallarta. Now it was time for us to have our first night together.