Brad Loses a Bet

Brad Loses a Bet Part Three

I thought about how to win for a few days. I analyzed everything I knew about her convoluted personality. Just which weakness would I exploit? I've seen her cum twice now and I figured she probably does her thinking with her sex organs just as much as I do.

She seemed really motivated by hugging and holding me. And she needed things to fit her idea of justice. These would be my keys to victory.

I hatched a plan to use a carrot and stick approach.

For days after I first came up with my plan I couldn't stop thinking about how it was going to play out, how she would react, and how I would gain access to her hot body. I needed her mouth and pussy. In fact, I couldn't stop thinking about Wanda all the time.

First I sent her a text on Thursday, "Sorry Wanda, but something's come up and I can't make it Saturday. Would Friday or Sunday work for you?" Anything to throw her off her game: disrupt her plans.

She texted back that she was looking forward to Sunday, and she included emojis of two pairs of lips.

On Sunday, Brad dropped me off with a final warning, "Pete, you heard what Liam and Devon said. How they were wrapped around the girls' fingers and couldn't escape. This is your last chance to run away. Your car's right there, just take it and go."

"Brad," I answered, "She's beaten me so far. I wanna win!"

"Well I bet she's gonna beat you. There's a good chance you end up sodomized by the end of the night."

"And I bet she won't. If I'm wrong I'll buy you a beer."

When Wanda opened the door she was wearing skin tight stretch pants, a snug workout top, and her delicate feet were bare. My heart leaped just once. She gave me a peck on the cheek, saying, "Oh I'm so sorry, Steffie's out right now. We're just gonna have to wait till she gets back. Would you like to play a game 'till then, maybe Cribbage?"

I couldn't let her keep control, I had to throw her off. I took her in my arms in a tight warm embrace and kissed her passionately on the lips for the first time. She melted in my arms and I knew I was on the right track.

While we were kissing she put her own arms around my neck, hugging me back. It was electric. It felt like my first prom dance with a long time crush. I melted too.

We kissed for a long time and when it ended I couldn't let go.

Then I did something off script and with no regard for my carefully made plans. Impulsively, I blurted out all the new thoughts and feelings I was having, "Wanda, We've done some hot stuff. I came here because you promised two sets of lips." She smiled at me devilishly. "And I've had a lot of fun with your contests." I saw that competitive spirit rising up in her."

"But I'm worried. I have this impulse to win. To beat you. But that's just not good for a relationship. I don't want to play the game anymore," Her smile faded. "I'm not gonna be satisfied with you and Stef putting your pretty lips on my cock. I don't want your mouth, or your pussy." Now she looked confused.

"I want you. I want to get to know the girl inside here" I laid my hand on her chest when I said it.

I was still holding her in my arms and she still had her arms wrapped around my neck. I spilled my heart out, gauging her face for a reaction. I could've been totally wrong and she just might've only wanted games.

I tightened my grip, "I don't want to compete with you. I want to be on your team. It'll be a brand new challenge - you and me against the world. Whaddya say?"

At first she didn't say anything. She just looked at my eyes, shifting her gaze from one to the other, then her voice came out all hoarse and weak, "Everyone's always wanted my body. I mean always. Everyone. You really want...me?"

"Yes! Yes! You're my equal. You push all the right buttons. Let's go for walks in the park. To dinner and the movies. Thanksgiving at two houses where we have to eat two dinners because our families cooked it. I want it all."

She squealed, "Me too! Let's start today. All that, and Roller Skating and trips to the beach." Then, playing with the button on my shirt, "But first I want you to do something for me that no one has ever done before." I was ready. I smiled from ear to ear waiting to hear what she wanted. Then the words came spilling out, "I want you to make love to me. Not just sex. And if you're tricking me...to beat me at the game...please make me believe it first before you pull the rug out."

She looked so vulnerable. I picked her up, explaining myself, "Honesty is really important to me. Even if I were still playing the game I would always be honest."

I carried her off to her bedroom where I made mad love to her. We kissed each other all over. I caressed her and she caressed me. When it was time I laid her on her back, placing the tip of my cock at her entrance, and slowly eased in. Watching her eyes go wide with the first penetration.

We embraced while making love. A first for her, and never better for me.

I came in a torrential flood and a moment later she came, rubbing her clit with me still buried deep.

We lay together, not disengaging, until my penis shrank and fell out naturally.

I felt like I could never let go, rather than getting up or rolling over we shifted to maintain our hug in a different position.

Afterwards we lay in each other's arms. Her clinging to me, and me holding her tight. Her voice was so soft I almost didn't hear, "Papi never hugged me, and mom was gone." She looked up at my face with her head on my chest. I waited for her to tell me more about her pain, but instead she said, "You know Brad and Steffie want to get together?"

I nodded. "We could set them up, but there's no guarantee it'll work."

"We could... but hang on to that thought for a minute." She sat up in bed to look straight at me. "I think Brad really likes the idea of a man sucking his cock." I wondered where she was going with this. "I bet he would enjoy going to a glory hole to have an anonymous man do it."

Then she changed course, "And Stef has never given her mouth to a man for the sheer pleasure of giving herself like that. She's always on a date or something where there's a payoff. I bet if she had the opportunity to suck a cock, for no reason other than that the guy would like it, she would."

I suddenly saw where she was going with this.

"Maybe." I replied. "But would it be right to manipulate them like that?"

"No one ever does what they don't want to do in my projects. And there's always a parachute. I never lie or bring out something that isn't already there."

"Ok, but how does her blowing him through a glory hole when he thinks it's a guy get them together?"

"It's all about insight. First Stef needs to know that she's not a selfish bitch. She thinks she is - but I know her better than that." That was a revelation to me. But I trusted her opinion.

"And Brad?" I asked.

"He thinks he's only interested in conquering women and physical hedonism. But he's a lot deeper." I had to agree.

"Trust me. It'll work and they'll both come out on the other side better for it."

"Ok, let's think up a plan. We should scope out some glory holes too, and while we're there you can watch me suck a couple cocks.

"Oh, but it's a lot more than thinking and scoping." She tossed me my car keys while grabbing a notebook.

On the drive she showed me flowcharts and sections in her notebook for back up plans. The effort she put into her plans was beyond me.

"I take it back. I'm not your equal. You're definitely my superior."

"Oh Pete. That's not true at all. You're the only one to try to game the game. And I have no doubt you could've beaten me. But then, you were the only one to see past the game to what's real. I could never do that, I was trapped in it. You're the superior one here."

"I guess we'll have to agree to disagree." I told her, squeezing her hand in mine.

I looked at the notebook of charts, "So you made one of these for Stef?"

"That's right. I've been trying to work on her for years now. But she's a tough nut to crack, it's her insecurity. Remember when you were gonna swap in for Brad? Well, when I defended you I said 'If a girl wants to swap in the name of love I can't stand against that kind of selflessness.' I was nudging Stef to come to Brad's rescue herself."

Next I asked, "I suppose I'm in there too? Did you plan for me to fall head over heels?"

For a moment she was speechless, "You love me?" She leaned over, snuggling up next to me while driving. "You make me feel like the most special girl in the world. But Pete, I've never been in love. I don't think I know how."

I pulled her body tightly next to mine, "You are special. And we'll figure it out. Don't you worry about that." Sitting there side by side my arm was wrapped around her. She positioned herself intentionally so my hand cupped her perfect boob.

Then she went on to answer my question, "Actually, I only planned for you to learn that you were generous and kind and loyal. I didn't know you would see me and want me. I never thought anyone would want me. I'm pretty fucked up, ya know."

"I'm broken too. My uncle did the same to me." I'd never told a living soul before. To admit what he did would be to admit I'd sucked cock. But Wanda already knew that. Then I shared the rest, "And it was years before I learned how to love."

She didn't need to say anything, and actually she changed the topic, "I can't wait to see you suck cock through the glory hole! But you know there's no pressure. Only if you want to."

I reassured her that I wanted to, "I wanna see your face when I do it. So far I've only listened to you talk. Not that I don't love the talking. It seems like you share the most intimate parts of your soul then."

She was silent for a long time. Then she said, "I didn't know that about myself. And yea, it's hard to open up." She craned her head back to look me in the eyes, "But it's easier with you than it's ever been."

Shortly after, we pulled into the bookstore parking lot and ran inside like the two overexcited lovers we were.

Inside we were fascinated by the outfits, movie titles, and toys. We both loved the adventure of it all. She held up a big black rubber dong that must've been two feet long, "If a cock like this came through the hole what would you do?"

"I'd have to try it," I told her. Then I pointed to an elaborate system of restraints, "Would you try that?"

She touched it cautiously, "Something like this was always past my limits. I could never take the risk." She picked up the cuffs and held them next to her wrists as if she were mentally trying them on. Then she said, "I could never do trust falls either, or sleep in the same room as another person. But my birthday's in two weeks."

We went to the counter to get change for the arcades. As the guy was handing the bills to me she put her lips right up next to my ear cheerfully, "You realize, this is going to be our first date."

I was dumbfounded. Putting my hands on her shoulders I told her, "That's not right." Then she nodded almost imperceptibly. "Well," I continued, "we're coming right back after ice cream."

Forty-five minutes later we were seated in a dirty booth, watching a blowjob movie, while waiting for a cock to come through the hole.

When one finally did, it was spectacular. The guy on the other side of the wall asked, "Which one of you is gonna do it?"

Wanda said, "He is, mostly." Then I started.

I lifted up the specimen, examining it all over and delighting in the wrinkles and veins. Wanda said, "Imagine you're Steffie. What would you be feeling and thinking right now?"

I kissed the tip. "It's beautiful. The guy on the other side needs me. He can't do it without me. I'm privileged to be sitting here. He trusted me with his most prized possession and he's trusting me to help him out.

Wanda was awestruck, "There's that trust again. I've never thought about it in those terms. Go on."

He wants to get off. But he's sad. Sad that his wife doesn't help him. He's even angry that he has to come here. I can make that go away, if just for a short while."

I leaned up to the hole, talking through it instead of sucking the cock, "It's a nice cock. Let me make you happy. I wanna help you."

That's too much for a Steffie. She doesn't know yet that she wants to help. She's gotta take a baby step first. What's she gonna do?"

I changed my approach, still talking through the hole, "Your cock is so big and manly." I ran my fingers all over it. "It's full of power and magic. I'm going to take it into me. Give me your essence." Then I slipped the crown into my mouth, sucking deliciously on just the end."

Wanda started whispering in my ear, "Steffie, you're beautiful with that grand cock between your lips. He's gonna give it to you. Suck it good. Make it feel good for the man who trusted you to help him. You can't wait for him to give you his cum. The more and the slimier the better."

I sucked wildly desperate to get him off. I needed my reward and I wanted him to feel good. When my forehead hit the wall I knew I was as deep as I could push myself.

A minute later the owner groaned, bucking up against the wall himself, "Oh man you're the best ever!" He shot streams of jiz into my mouth and I craved it like never before. When I swallowed I felt content.

I turned to Wanda, "Wow! What you said was amazing. Let's do it again. I never got to see your face while I did it."

"Hold on," she said, "first go around to the other side of this wall. You be Brad and I'll be Steffie."

"I can't do that," I told her.

When she asked why, I explained, "I've been dreaming of our first blowjob for two weeks and I don't want it to be through a hole in the wall in a filthy booth. I want to look into your beautiful eyes so I can feel the connection."

About then the video ran out, but we just sat on the bench and talked.

"Oh, right." She answered, "Yea, that makes perfect sense. I've been dreaming of my lips on you for months and I want us to look into each other's eyes too."

I was blown away by how she described it, "That sounds like a perfect blowjob, us looking into each other's eyes."

Then the implication of her exact words dawned on me, "Um, months?"

"Yep, ever since that first time you hand delivered some paperwork to my boss. I remember sitting at my desk when you handed it to me. You were handsome with a runner's build, and the way you carried yourself spoke volumes about who you are. I had a brief daydream of sucking your cock. But you were also gruff and curt and told me I better not lose the papers or you'd get me fired. I didn't lose them, but my boss hated the idea and tabled it. And then you did try to get me fired. I'm just glad you failed.

"Shit! I was a monumental jerk. I'm sorry. I don't even remember it. And that impressed you how?"

"When I was younger I had a horrible temper. If someone slighted me I'd fly off the handle and get revenge. It was a bad way to live life. My younger self would have destroyed your car. Now when someone does something like that to me I look deep to find the best quality they have, but aren't expressing well. That's when I put you in my notebook.

Let me get this straight, your notebook is a book of people who've hurt you, that you want to help?" She smiled, confirming what I'd asked. "That's the craziest and most endearing thing I've ever heard of. You're an, an angel. How could I not love you even more."

So here we had driven forty-five minutes to role play being Brad and Stef but we were gonna have to leave and come back tomorrow.

"We haven't planned this very well." She lamented. "In fact, we haven't planned our relationship very well at all - I mean, our first date was going to start at a porn shop, and we can't even finish what we started.

"It's been one day and we've got plenty of time to do it right. It's not like we can plan every detail." She looked at me kind of oddly like I was speaking another language. "Besides, as much as I want to be a part of your angelic quest, I'd much rather go home.

"Home?" She looked lost. "I'm not ready for that."

"Oh, I just misspoke. Of course."

"No, let me explain. Growing up it was me and my brothers growing up under the thumb of my papi. It wasn't a home, just a house we all survived in.

When I do make a home with a guy, you, I want to be in love first...so it could be a while, if ever." She truly doubted her capacity for love.

"One more thing. I've always dreamed of having a real home, in a real relationship, but when mom ran out I knew that I would never move in with a guy unless I was married.

I clarified what she was saying, "So it's love, marriage, and then moving in?"

"That sounds perfect. Just give me time." Her lip quivered.

"You've got all the time you need, angel. It sounds pretty perfect to me too."

By then we forgot about blowing the next cock that would come through. Though it never did. She touched my face softly, and said, "Let's go back to my apartment and look into each other's eyes."

"Yea that sounds great!" Then it dawned on me what she was saying. "Oh, right, 'look into each other's eyes', I thought you just meant looking into each other's eyes."

We ran out to my car, hand in hand, well, I ran, she skipped. And just when we were about to leave the parking lot I saw Brad's car there.

"So honey, remember when you suggested that Brad might want to go to a bookstore to get sucked off by a guy?"

She remembered and I finished my thought, "Well, I think you were right on the money. I just saw his car."

Wanda got upset, "Crap! That could ruin everything. Go back."

I didn't see what she saw but she hurriedly explained it. "Brad thinks of himself as a player. Out for his own pleasure alone. But he's really a lot deeper than that. If he goes in there and has a fantastic blowjob, he'll never look for anything more. He's got to have a blowjob that's just good enough for him to come back and feed Steffie, but bad enough that he won't get addicted to random hookups with men. It's my fault, I arranged for him to get his first male blowjob from you. I need to fix it."

I wasn't so sure. It was like playing God. "That seems like a tall order. Are we up to it?"

"You betcha!"

We crept back inside the bookstore, being careful not to be seen by Brad if he was not in a booth.

We started going into empty booths, peeking through the holes to see if Brad was on the other side.

We just came out of a booth when I caught a glimpse of him going into a corner cubicle.

Quickly we nabbed the booth next to his. "Ok, follow my lead." She whispered to me. "We don't have time to discuss it."

Put your finger through the hole and beckon him to put his cock through. I did. And Brad started talking to me through the opening. "Are there two of you there?"

"Disguise your voice." She told me. Then she fed lines into my ear. "Yea, just a couple of cocksuckers."

"Great!" Said Brad. "That's what I'm looking for. Two, you say? A friend of mine should be getting blown by two sets of lips right about now. I guess he's not the only lucky one."

She whispered in my ear again and I repeated what she said, "How big is your cock?"

"Eight inches and thick as a beer can." Is what he told us. We exchanged glances because we both knew he was lying. He was an average six.

Under her tutelage I responded, "cool. Anything under seven isn't worth sucking." She explained that making him feel inadequate would sour his experience. "Feed us. We're hungry." The goal here was to show that we were only interested in our own pleasure and not his.

Brad stuck his cock through the hole. It wasn't yet hard. Wanda reached out and grabbed his cock firmly. She told me that he would think he loved being grabbed, but deep down he knew he craved a more gentle loving caress.