When Losing is Winning

I remember Andy asking me, "Why are you hanging out with the little runt, Bennie?" And I assumed Andy was talking, at that time, about me making bad choices because I had been doing reps with Bennie on the bench and then dead lifts and coaching Bennie to push himself, and he could do better and stick it out, and then Bennie did. He dead lifted 150 pounds. Congratulations little man.

And now I was sitting and stretching my legs spread eagle in Bennie's living room, drinking his beer, listening to his stereo and also hearing Bennie's squeaky chatter in the background, but all the focus was on Bennie's wife, Clarissa, who was organizing books on a shelf pretending she was doing her own thing.

The tension was not mine alone. I saw how she cast a side glance like she didn't see me, and she squatted and looked at me in the reflection of the glass panel. Then she straightened her legs while still bent at the waist, presenting that beautiful butt with her legs split for my view.

So, Andy, if you want to know why, that's why! I had answered Andy there in the gym, "Looks stupid, doesn't it? Me hanging out with the little runt, helping each other put weights on the bar, spotting each other as much as he could spot anyone, trading pointers. Have you seen his wife, Clarissa?"

"Clarissa?" Andy repeated. "Is that the one with the ponytail and the little pink wrist bands, and she does a lot of the jazzercise or whatever that dance stuff is in the back?"

"No, I'm not sure who you're talking about there. Clarissa is the tall blonde, I think she's taller than Bennie. Go figure. And she's not a natural blonde but she frosts the top layer of her hair. You might catch her once or twice a week. She's not here that often. Usually she's on the stair stepper or she likes to hang out on the leg machines over there talking to Kyle. Do you know Kyle?"

"No, can't say I do."

It was the briefest thing, when Clarissa turned her head, still bent to show me her ass, and she looked under her arm at me to make sure I was watching. Her facial features were not refined or delicate but pleasantly plump and her skin was smooth. She left her books on the shelf and strutted into the kitchen.

When she came out of the kitchen I set down my beer on the side and stretched for my toes but I gave a low groan, almost a growl. I said to her, "Clarissa, babe, what I really need is a partner to help me stretch, you know to put their feet on my thighs and push my legs wider."

Clarissa walked over right next to me and pushed her hip out creating a luscious S curve to her frame with big tits hanging almost literally over my head. She asked, "You feel like you should have a girlfriend? You don't have a girlfriend?"

"No, I'm a lone wolf," I told her. "Probably the right girlfriend would keep me in line, straighten out my chi and all that."

"It's not everything in the world," she smirked.

Cha-ching. Bennie dropped his face and looked at the floor like his woman just kicked him in the nuts in front of his new buddy.

Bennie had finished his bench press, 140 pounds. Most unimpressive. I had to grab the bar from him and move it to the rack to be sure Bennie didn't drop it on his head. Bennie stayed laying back on the bench with his hands on his face in exhaustion. When he relented I reached a hand and pulled him to standing.

Bennie said, "You really help my game. I mean, I can feel myself getting stronger and lifting more weight because you push me. By the time I'm done my workout, I'm spent but inside I'm psyched up and like I can tackle anything."

"That's how the physical routine should fit into your life," I directed him. "Sometimes you take a step forward in your workout and it helps your job performance, or you learn in your relationship and it'll seem like a step back but it motivates your workout. No pain, no gain, right?"

"That bouncing can rip your ligaments," Clarissa interrupted me. I regained my focus to those luscious knockers above me. Bouncing. That was a good word for it. She said, "When you have someone pushing your legs, it can rip you the same way if you go too hard or too fast."

"You know how to do it right, though, like going slowly with the right pressure?"

Clarissa twitched her lips. Stepping behind me, she squatted, placing her hands on my shoulders. "Yes, slowly like this." She pushed my shoulders to propel my back forward and stretch my legs, but slowly, letting the burn simmer in my tendons.

"Did you go to the kitchen for a beer?" I asked her.

"No, do you need one?" She lifted my can and shook it to ascertain there was still half.

"I thought for yourself," I said.

"You've got enough here for the two of us," she answered, and took a swig of my beer.

I wished I could have seen her face behind me and how she relished the taste. Instead I had to endure Bennie's simpering grievance.

Andy had asked me, "When you say she hangs out with Kyle, is he one of these steroid meatheads where women try to close their fingers around the biceps or his thigh?"

"No, he's not especially pumped. But he told me he fucked her."

"He fucked Clarissa?"

"Yeah, he said she was a great piece of ass and knows how to move around and shit."

"Does that make you want her? Dip your wick in the sticky cum bucket?"

"That's very disrespectful. If she's comfortable and assertive, then more power to her. Yeah, I'd tap that all day. In fact, I'm going to tap that. You'll see."

Clarissa gave me another push on the shoulders. "Uhhh," she groaned. "You are tight. Probably too much power lifting. You guys with all the muscles forget to extend through the full range of motion. You probably can't even do a sit up, right?"

"No, you've got that all wrong. Do you want to make a bet?"

"OK, let's see you do 30 sit-ups in one minute. And what do I win?"

"What do you want?"

"I won't be too hard on you. You can clean the dirty dishes in the sink."

I had to laugh. Some women get a kick from making men do the menial chores. Like they're going to feminize you. I bet Bennie does a lot of toilet cleaning.

I told her, "OK, I won't be too hard on you either. If I win, then you have to come down in my split stretch and help me."

"You're on. I'll bring the clock over and you can see it's legit."

Clarissa fetched her watch from the bedroom and laid it on the carpet next to me. She said, "You start yourself when the second hand reaches the 12."

"Legs bent or flat?"

"Your choice."

When the second hand hit the 12, I had my knees bent and set to my sit-ups quickly. Hitting 30 sit-ups is not difficult, but I banged out 20 sit-ups in twenty seconds and Clarissa had a wry smile as the result sunk in.

She said, "OK, you won that round." She sat down in a split before me, untied her sneaks and removed her socks, and pressed her bare feet into my calves to push my legs wider. Her toes crinkled on my muscles to tickle. I reached for her hands and leaned back to pull her towards me.

When Kyle was on the leg press, Clarissa showed off her athleticism by kicking her foot up over her head and setting it on the weight stack. That brought her crotch near his face and she pulsed in her stretch, pulsing her pussy right at his face. She didn't mind bouncing then. I heard her say something like see if you can lift that, or swing that and laughing but unrelenting. I could only imagine, as I saw from behind, how her pussy lips might look in that stretchy leotard and without underwear as far I could tell.

As Clarissa pulled me back over, I tried to angle our hands towards her groin but she pulled with her shoulders and arms to extend my hands up outside her knees.

On the next pull to my side, I asked her, "Double or nothing?"

"I'm not sure, what's the nothing? I'm already giving you a stretch, so I don't owe you anything."

"OK, do you want to up the stakes for round two?"

She laughed. "I'd have to come up with something real grimy for you to clean. Like maybe scour the oven?"

"Oh, that does sound nasty. Bennie should buy you a self-cleaning oven."

"What nasty do I give if I lose?"

"I'd be more motivated for this stretch if you were naked."

"Oh, you wish."

"Hey," Bennie spoke up. "Why are you hitting on my wife?"

"Oh, Bennie," Clarissa scolded him. "It's no big deal. He's already seenS my tits."

"I did?" I don't remember seeing her tits but I'd like to.

"Yes," Clarissa insisted. "At Tina's pool party one of the guys pulled my top off while we were playing volleyball."

"Oh, I sort of remember that. A lot of commotion and I heard about it but I didn't get to see. You should take your top off now as a make good."

"If you win, I'll take my top off."

"No, it has to be the shorts. After all, you strip your top off all the time in front of your friends."

"The shorts are worth more than cleaning. If I bet my shorts, you have to put up your shorts."

"That's fair. I'll let you choose the challenge."

"It won't be sit-ups again. We'll have to go head to head on burpees. One minute, whoever does more."

"OK, you're on."

Clarissa stood up and positioned her watch on the floor between us. I was confident although she was very fit. Already she was dancing on her toes, tensing her thighs and calves. She swung her arms in circles and then in and out from her body. She looked at the bulge in my shorts, quite evident because I had no underwear, and she grinned.

She said, "Count them out loud as you go and no cheating."

We both watched the second hand approach the 12 and I let her start to be fair. She wasted no time. Clarissa fired off five burpees like a firecracker and I was struggling to catch up. By thirty seconds she slowed down and I drew even. I was probably too focused on her legs and arms pumping in and out. But what did I have to lose?

I finished one burpee behind her. Clarissa jumped up like she had thrown a Hail Mary pass for a last second victory. She jumped side to side, pumping her fists in the air.

"Woo hoo!" she screamed over and over.

"I give you credit for squeaking a win. It was basically a tie."

"A win's a win," she announced. She pointed at my waist. "Lose the shorts."

I smirked as I pushed my thumbs inside the elastic on the sides of my shorts. I pushed them down very slowly, like a striptease. Her eyes were growing wider as the shorts lowered. My dick was not fully erect, but it was on the way. The edge of the shorts rubbing down the front and holding it back let my dick bounce free when the shorts passed and dropped to the floor.

Clarissa's eyes dilated again and she formed an O with her mouth. That's right. Take a look at the monster. A lot more than you're getting from Bennie.

I told her, "OK, let's finish the stretching." I sat down in my split stretch with my hands outraised to her.

"You lost that round," she protested.

"Yeah, but the whole idea was motivation for stretching. You still have to finish the stretching."

Clarissa flashed a slight disapproval but sat down again in the stretch and took my hands. I was more successful in forcing our hands towards her groin as she pulled me over and my knuckles brushed up her thighs.

I said, "It should be more than your shorts for the third round, the rubber game of the match."

I pulled back to my side and she worked with me to direct our hands up the inside of my legs. She let go of my hands and placed her fingers on my thighs. Clarissa tickled up and down towards by groin. That made my dick stand tall.

"Will we make it to another round?" Clarissa asked.

After letting go of her hands, I extended my arms behind me, leaning back with locked elbows, and taking it all in. Clarissa was drawing the backs of her fingernails up my skin and watching my dick jump as she got closer. Each time my dick popped she'd lock eyes with me and smile.

I said to her, "I guess losing is winning."

"What's that?" she cooed.

"I lost the shorts but I won."

"I won," she answered. She reached up and grabbed my dick in both her hands. She started to pump my dick slowly.

"That's not right!" Bennie finally argued. He got up from his chair and came to stand next to us.

"Oh, Bennie," Clarissa stopped him. "You're not really going to complain now, are you?"

"Why do you have to hit on my friends?" Bennie whined to her. He looked pitiful in the cowering slump of his body and the way he covered the top of his head with his hand like he was blocking himself from watching.

"Bennie, we've had this talk before," Clarissa corrected him. "There are as many reasons to enjoy ourselves among the friends we know and trust, as to find some stranger we'll never see again."

Then Clarissa returned her attention to my face and ran her tongue around her lips. She drew the fingers of one hand elongated up the sensitive underside of my prick as she licked and slobbered on her other hand. She brought the frothy hand to my dick and lathered my shaft to help her hands glide.

Bennie gave a final foot stomp and left toward the kitchen. I didn't turn my head to see where.

I told Clarissa, "He seems upset."

"Don't worry about Bennie. It's not like he hasn't seen me have sex with other people before."

Clarissa rubbed one hand up my dick with a circular motion, her thumb hitting the sensitive chord on the underside, and then at the crown she gave an extra twist to rub across the tender spot right at the V underneath. The fingers of her other hand reached down to tickle my balls.

"You go girl," I moaned to her.

"I think I will," she answered. She showed me how limber she was by leaning all the way over and planting her mouth on my cock.

If I thought her hand job was nice, she blew me away with her mouth. She continued the hand motions but twisted her lips on the crown and licked around, hitting the nerves. She tickled under the crown with the tip of her tongue and then she plunged down to suck deeply on my cock.

As Clarissa took more of my cock in her mouth, she steadied my dick with a circle of thumb and forefinger at the base. She planted the other hand on my thigh to steady herself as she pumped her lips faster up and down my shaft. Then she couldn't help it and moved that hand from my thigh down between her legs to finger herself.

"Wow, you know how to please a man," I encouraged her.

She came up for air, stood and took my hand to pull me to a stand. She pushed me backwards to the couch and made me fall on the cushion. By straddling her knees to either side of my thighs, she brought her crotch down to my dick.

One of her hands held the seam of her shorts to the side. The other hand pushed the head of my cock to her hole. When the helmet head of my dick seated within the lips of her cunt, she popped up and down, like her hungry, furry mouth was nibbling on my cock. All at once she dropped her weight and impaled herself on my pole. She shifted her weight side to side, seating herself more firmly on top of me and rubbing her mound to my pelvis.

Clarissa was twitching her eyes and lips in unison with the pelvic gyrations, as if to say, "Isn't that fun?"

She crossed her arms over her waist to grab her shirt and lift it off. She dropped the shirt on the couch next to us. Her hands went up her back as she rocked slowly on me, and the bra came off in a flash. Luscious tits right in my face.

Clarissa grabbed the back of my head and pulled my nose into the split of her tits. She slapped her tits back and forth across my face. Finally she let me have her right tit. The nipple engorged and became hard in my teeth. When it was hard, she gave me the left. I spanned my hands on her back to press her body on my face, and yet it was only an emotional gesture. She wasn't going to release her clutch of my head.

She was sliding slowly up and down but her internal muscles were gripping my cock in waves. It was an interesting feeling to be massaged by her warm, gushy quim.

"Wow, are you a professional?" I asked.

"Meaning what?"

"You have such great technique, I thought you must do this for a living."

"I've been paid a couple of times. Flattering, you know."

"What did they pay for? Was it something special?"

"Yeah, they paid me to take care of their satisfaction instead of my own."

"You keep going and we'll both be happy. Should we use a condom?"

"Don't worry, I'm on the pill. You can give me your best shot."

"What are you talking about?" I heard Bennie scream from behind her. "You're not on birth control and you promised not to let men cum inside you."

Clarissa looked over her shoulder but kept rocking on me. Her hair seemed to shimmer in a dance around her shoulders and her face looked young and bright as she answered in a frolicking tone. "Promised? I don't remember making any promises."

"You were fucking Aaron and you said, 'Don't worry, I don't let them cum in me.'"

"I don't remember Aaron," Clarissa mused. "Was he the one from the bar? I don't let strangers cum in me but it doesn't mean I don't enjoy a natural finale. If you're worried about it, why don't you fetch me a condom? And my hairband, too."

Then Clarissa leaned in to kiss my ear. She whispered, "Sorry for that rude interruption. Where were we?"

She pumped that pussy on me and I forgot the past. Her pussy was milking my penis and she had the control. I answered, "I heard tell of reaching a natural conclusion."

"Let's not be too hasty." She slowed to emphasize, but then she started popping up and down furiously, and then slowed down again like she enjoyed teasing me. "I think Bennie wants to watch."

"Obviously Bennie can't satisfy you. You should be my woman."

"And you will? You will satisfy me where Bennie can't?" Clarissa slapped my face with her tits again and pursed her lips. I had a sneaking suspicion she would teach me a lesson before we were through.

Bennie appeared again and stood next to us, a condom and hairband in his outstretched hand. "I couldn't find your hairband."

Clarissa took the hairband but not the condom. She sat still on me as she wrapped her hair up behind by twisting the band repeatedly. Then she stood up and dropped her shorts, letting me see the curve of her hips and the tender pussy I craved.

Clarissa dropped to her knees and pushed my knees apart. She grabbed my cock and licked its length. Soft, tender licks before sucking hard. Back to light, tickling kisses and then she sucked hard and deep throated my cock. When she came up, she grabbed my dick in her fist but traced the tip of her tongue down the center of my shaft, down to my balls and flicked underneath. She teased under my balls as she stroked my cock in her hand and sent me to a nirvana I never knew before.

It all stopped and Clarissa was whispering in my ear. "What would you pay to have me lick your balls until you came?"

"What would it cost?" I stammered.

"More than you want to give," she laughed.

Clarissa turned around, straddled my legs and slid down my torso to bring her pussy back on top of my cock. She stopped at that point, with her pussy caressing the top of my cock.

Clarissa asked Bennie, "Do you want to put a condom on him, so he doesn't fill my pussy with his cum?"

"No, don't make me do that," Bennie whined.

"Give it to me," Clarissa snapped. She ripped open the package and as she released my cock she rolled the rubber down on my pole. Those fucking regular sized condoms are so tight. It felt like she had tied a string around the base of my cock. My cock was hard like a rock and I thought it might take me forever to cum.

Clarissa spit on her hand once to make the rubber wet and then she replanted herself on my dick, facing away from me. By leaning back against my chest, Clarissa could fuck herself on my dick with a slow roll of her hips. I was pinned beneath her and she enjoyed setting the pace. Her little sighs and moans were believable. But she reached down to finger her clit and heighten her pleasure.