Book Club Pt. 03: The Bet

This is the third in my book club series. The book club is the same but the characters are different. All characters are over the age of eighteen.

*

My name is Rita. Holly and I have been friends for ten years. Like the others in the book club, we are both recent empty nesters in our mid-forties. Holly and I are good friends but have very different personalities. Holly is very outgoing and very adventurous. I would be what most would call a follower. I am quiet and shy.

Just like several others in the club Holly and I would get together and discuss the books before the monthly club meeting.

"What did you think Rita, did you get a little embarrassed reading the book?"

"Holly please, I'm not that big of a prude. I loved the book; it was very hot. I'm sure for someone like you it was tame. I knew you would make fun of me that I would never in a million years do any of the stuff in the book."

"Stop, I'm just messing with you. There is some of that 'stuff', as you put it, I haven't done either and wouldn't do."

"Really, the way you tell it. You've done everything in the world sexually and continually make fun of me for being so reserved, as you put it."

"Come on Rita, I'm just trying to have fun with you."

"Okay, give it up. Tell me what you have done that was in that book and what you wouldn't do."

Holly looked at me with a sly look. "I've had a few threesomes with and without Don. Don and I have had a couple of foursomes but they and the threesomes were when we were much younger. I think we are probably past those days."

"Don didn't mind you having sex with another man and you didn't mind him having sex with another woman?" Rita asked puzzled.

"Oh honey, it was just sex. Just think of some of the guys you fucked before you met Chris. You didn't love them, you just fucked them." Rita put her head down. "Oh God, is Chris the only man you've been with?"

"What and that makes me a bad person because I was a virgin before I met Chris?" Rita said with venom her voice.

"Oh God no, I'm sorry. I didn't mean it that way."

Rita looked at Holly and laughed, "No, you did mean it that way. You think I'm a goodie two shoes. Well, you're right, I am. I have no problem with you doing a three or foursome. If Chris came to me asking me to try something like that, I would tell him no."

"You don't say that all that convincing. I'm not so sure."

"Am I curious? Yes, but I could never admit that to Chris. He would think I'm the biggest slut in the world to even suggest that I'm curious about such things. So, those things are not going to happen."

"Well honey, you would love a good threesome or foursome if you tried it. I wonder if you might identify with the wife in the book that seduced a younger guy, that is very hot too."

"Okay, that was hot, but I could never do such a thing," Rita said. "Are you saying you have?" Holly smiled lowering her head. "Oh my God, you have. Give me details so I know you aren't lying."

"Fine, I'll tell you:

The summer before Matt went to college, he had a sleepover with a group of guys on his lacrosse team. Don was out of town, so I oversaw getting the food and keeping the boys in line. There was one kid who kept asking me if I needed help and hanging around me. I don't know if you remember Noland Johnson but he was in the same class as Matt. Tall, cute but very shy.

I overheard the other guys were giving him a hard time because he had just had his eighteenth birthday and had not had a girlfriend. I felt sorry for him so I gave him a little extra attention and let him help with the dishes. Apparently, the boys were hazing him because they said he had to sleep in our guest room because he didn't bring a sleeping bag. About two I found him in the hall looking for the bathroom, our hall bathroom was being remodeled and not available. I startled him pulling him into our bedroom. I told him to use the Master bathroom. When he came out, I told him to sit on the bed with me. I told him I wanted to talk to him.

He tried to beg off but I insisted. He seemed embarrassed to be sitting on my bed in just his boxers but his eyes wouldn't leave my cleavage. I had on a little nightshirt with a deep V cut. We talked about him not having a girlfriend and how shy he is around girls. "I'm going to give you a little advice Noland. When you talk to a girl, look them in the eyes. Don't stare at her tits like you have with mine. I'm flattered you want to look at them."

"Oh God, I'm sorry Mrs. King. I didn't mean to."

"Don't lie about it and don't apologize. Do you like them?" Noland nodded staring at them again. I got up and locked the bedroom door. "Can you keep a secret?" He again nodded. "If you say anything my husband will kill you, understand." Noland had a very nervous look as he nodded a third time.

I pulled my little top off giving Noland an unobscured view of my tits. He sat next to me with his mouth open, eyes glued to my tits but not moving. I grabbed his hands placing them on my tits. "Just squeeze them gently Noland. I like that." Noland had been fondling my tits for a few moments when I noticed that his cock was hard sticking out of his boxers.

I pulled his hands off my tits. "Noland, what's going on down there?" Pointing to the head of his cock poking out of his boxers.

"I'm sorry Mrs. King." Noland started to walk to the door but I still had hold of his hands.

"You're not going anywhere. Stand up and pull your boxers down." Slowly Noland stood up and pulled his underwear down. "I guess I'm going to have to punish you. Put your hands behind your back and close your eyes." When he closed his eyes, I reached out and grasped his cock. After a few strokes, I pulled it to my lips. With my lips around his dick, I watched as he opened his eyes to see me sucking his cock. Logan moaned as I took him deeper into my mouth. The way he was moaning I thought he was going to cum, so I pulled his dick from my mouth looking up at him.

"Logan, do you think you've been punished enough?"

I bewildered Logan looked at me strangely with his dick pointing to the ceiling. "I guess."

"You're wrong, lay on the bed." Once he was on his back, I slipped my panties off climbing on top of him. "Remember, this never happened." With a squish my pussy enveloped his dick, riding him till he shot his load inside me.

Once he calmed down, I told him to go back to the guest room and not say a word about what we did.

I had been holding my hand over my mouth the entire time Holly told her story. "Holy crap, I can't believe you did that. Weren't you afraid you would be caught?"

Holly laughed, "Eighteen-year-old boys will do anything for pussy, including keeping their mouth shut. Not to mention the threat of me claiming rape sealed his lips. Shit I am getting a little turned on thinking about it."

I had to admit to herself that there was some wetness between her legs after hearing her friend's conquest but I wasn't going to tell her. "You're just more adventurous than I am. I couldn't get a young man to look at me much less get up the courage to seduce him."

"That is so not true. Look at you, you have a great body with great tits. Almost as good as mine. You could seduce anyone you wanted, you just choose not to or you're to chicken too."

I was taken back by what my friend said. "You think I'm chicken? I'm not chicken, I just have morals." I was a little pissed that she thought I was chicken.

"Oh please, you just told me how hot those stories in the book were and I bet if I checked your little kitty I would I'd find it nice and moist. Tell me I'm wrong."

My blushing said everything, I knew I couldn't hide it. "Fine, I got a little turned on but I could never seduce a kid."

"Wait right there, Logan was eighteen years old. He was a man and I just helped him with his manhood. I didn't seduce a kid. If anything, I did him a service. He was a shy young man who knew nothing about how to act with a woman. I helped him. If along the way I got some enjoyment out of it, is that bad?"

"I'm not judging you. I'll admit it, it sounded hot how you helped Logan with his manhood as you put it. I just can't ever imagine I could do that."

"Right because you're chicken. I will bet you right now that you would chicken out. A hundred bucks on the line."

"Look I'm not going to do so I'm not betting but if I wanted to, I wouldn't chicken out." I was getting pissed again.

"Alright, a different bet then. You don't have to seduce anyone. You just have to get a young man to show you his dick. We'll take the sex out of it; you don't have to have sex but him. If you can get your conquest to show you his dick, you win." I hesitated. "See chicken."

"I'm not chicken, you want to bet. Fine, I'll do it, but no sex and no cheating on my husband. Just get him to show me his dick and I win right?" Holly nodded. "I have to say I don't know where I will find such person or conquest as you call it."

"It's a bet then. Finding someone is easy. We have a target rich environment very close and they deliver." I looked at her perplexed and nervous. "There is a cute boy, young man, who just started at the grocery store as a sacker and he is a delivery guy. You're going to call in an order for delivery. My friend is the assistant manager who schedules the deliveries. I will make sure they send him at the end of his shift. All you have to do is get him to show you his dick and you win."

"That's all I have to do right? No touching it or having sex and I win, right?"

"Right, the bets on then." Holly knew she had played me. She knew my weakness has always been my competitiveness. I'm sure in her mind she had just won regardless how the bet turned out.

"Oh God, what have I done?" I thought to myself. I was consumed with not be chicken and winning a stupid bet. In my mind I could win the bet and not to cross any lines that would damage my marriage.

Chris was going to be out of town on a hunting trip the upcoming weekend so I decided that I would win the bet while he was gone and take no chance to have him walk in on me. My problem was that I couldn't come up with a plan to get the delivery guy to show me his dick. Several different ideas popped in my head but I dismissed them just as quickly.

The time was quickly approaching Saturday night. I put in my delivery then tried to figure out what to wear. I knew I would have to put on something that showed off my tits but I didn't want to show too much. A push-up bra and a low-cut top would do the trick with some tight jeans.

I looked up at the to see the hands of the clock were half-past six. He should be here any minute and I still had no idea how to win my bet. I jumped when the doorbell rang. Standing at my door was a tall skinny kid who had bags in his hands. "Mrs. Wilson? I'm Jed from the store, you had a delivery?"

"Yes, come on in, put the bags on the table."

"Yes mam, I have a couple more bags so I will have to make a second trip."

I still hadn't come up with a plan till Jed walked back in. A plan presented itself without my doing. Jed dropped a bottle of soda on the floor. The cap broke causing it to spew all over. I quickly grabbed it allowing it to continue spewing, even increasing the spray by squeezing the bottle. The soda covered both me and Jed before I got it in the sink.

Jed was apologizing profusely as I grabbed a towel wiping us off. Now I had a plan. I patted his chest before moving to his legs, even patting his crotch area. "Accidents happen, it is not your fault. We need to get you cleaned up quickly or your pretty work shirt will be stained permanently. I couldn't stand you going back to work like this." I grabbed Jed by the hand dragging him upstairs to the laundry room.

When we got to the laundry room, I started pulling Jed's shirt off. "Mrs. Wilson you don't have to do that, you are my last stop. I don't have to go back to work."

"That's good, but I'm still not letting you go home a mess."

Before he realized what I was doing, I had Jed down to his boxers and socks. I tossed his clothes in the washer. He stood practically naked in front me putting his hands over his crotch when he figured out his clothes were off. I smiled at him then proceeded to strip down to my bra and panties. Jed's eyes were dancing between my eyes and my tits. I grabbed a washcloth rubbing his bare chest.

"Did I get all the soda?" I asked rubbing his chest down to his waist. Jed didn't say anything he just let out a moan as my washcloth moved closer to his waist. I gasped when I looked down at his boxers. The outline of his cock was unmistakable in his boxers. Between me being in my panties and bra and rubbing his chest, Jed was obviously hard. The more I looked at his crotch I lusted for it. My plan had been just to get him to show me his cock but now I want to touch it and feel it and maybe more. I knew it was wrong but I really wanted to see and touch it.

I put my hand on his boxers patting his cock inside them. I looked up at Jed as I grabbed the waistband of his boxers. "I think I need to wash these too." Jed couldn't get a word out as I pulled his boxers off throwing them in the washer. Jed stood there shocked with his cock pointing at me. I had won the bet. Jed was standing in front of me with his cock standing at attention. My head was telling me to stop, I had gone far enough.

I just stood there staring at his cock. I don't know how long but it seemed like an eternity. Finally, I made my decision. Looking at him I smiled. "I think I have some more soda on me too." Just a quickly I pulled my bra and panties off throwing them in the washer.

We stood about a foot apart naked with Jed's dick pointing to the ceiling, Jed put his hands back covering his dick. "Jed, I'm sorry I've embarrassed you. You don't need to be embarrassed, you're very handsome."

Slowly Jed pulled his hands away from his dick keeping his eyes dancing between my tits and my crotch. "Jed, have you seen many women naked in person and I don't mean porn." He shook his head no still not saying anything. I leaned in close letting my hand brush his cock. "Jed, I let you in on a secret. You only the second naked man I've been this close to who has been excited if you know what I mean."

Jed smiled looking at my tits. "Are you excited looking at me naked?"

"Oh God yes, Mrs. Wilson."

I smiled, "Jed I want to ask you something and I want you to say no if you are not comfortable with it." Jed nodded. "Would you let me touch it? Could I feel it?"

Jed looked at me and smiled, "Oh God, please."

With all the courage I could muster I took Jed by the hand guiding him to our bedroom. I sat down on the bed next to him slowly tracing the outside of his cock. I ran my hand the length of his shaft gripping hit gaging his length and girth. Jed moaned as I felt him and stroked.

I stroked him a couple of long slow stokes when I leaned over to his ear. "Jed, are you a virgin?"

He shyly looked over to me. "I'm sorry, yes."

I kissed him on the cheek, "Oh God, don't be sorry. There is nothing to be ashamed of for being a virgin." I leaned in close to his ear squeezing his dick. "I will understand if you are saving yourself but I want to give you the opportunity not to be a virgin anymore."

Jed stammered again, "You mean like us have sex now?

"Only if you want to."

"Oh God, are you serious? You are so hot; anyone would kill to fuck you. Oh, I'm sorry, was that too crude?"

"No Jed, you're not being crude. I'm asking you if you want to fuck me. I want to feel this beautiful cock go in its first pussy, my pussy."

"Oh God, I hope you're not pranking me. Yes, I so want to have sex with you. If you are being serious, I need to tell you something. I don't know how to do it. I mean I've seen porn so I know how it works but I know where to put but I'm just afraid I won't know what I'm doing."

I grabbed on his hands placing it on my tit. "Jed, it is okay. That is what being a virgin is all about, not know how to do it. You got the first part done, your cock hard and my pussy is wet. All you have to do it put it in and move it around. I'm going to lay on my back spreading my legs. You get between my legs and put it in. Just go slow and enjoy yourself. I'll guide you."

Once on my back, Jed crawled over me putting his cock at the opening of my pussy. When I said I was wet, that was an understatement. I couldn't remember the last time I was this turned on. The two of us both moaned loudly when his cock head pushed past my pussy lips.

Jed inched his cock into my pussy till it was fully inserted. "Oh God, you're bigger than Chris."

Jed stopped for a moment, "What did you say?"

Shit I didn't mean for that to come out. "Nothing Jed, just start slowly moving you dick in and out. Does it feel good in my pussy?"

"This is awesome, better than I ever thought it would be. Am I doing it right?"

"You're doing great Jed. Just start pumping my pussy however it feels good to you. When you feel like you are going to cum, just let it go. Don't try to hold back."

"Oh, shit I don't have a condom on."

"That's okay honey, I'm on birth control. I want to feel you fill me up."

Jed pumped a few more times before letting out a loud grunt. Jed stopped moving, he was having his first orgasm inside a woman. "Mrs. Wilson, I think I came."

"I know you did honey. Slide off me and I will go clean up the mess you made and check the laundry."

Damn, he came a lot. There was cum dripping down my leg by the time I got to the bathroom. I cleaned up his cum before switching our clothes to the dryer. Jed was still on the bed next to the wet spot on the bed.

"Jed, your clothes won't be dry for another forty-five minutes. I hope I'm not going to make you late for something."

"No, I can stay as long as it takes. Is there something we can do while we wait?"

"Hmm, you're no longer a virgin. I think you need to try eating some pussy and God, I need to cum. Come over here and have a taste." Jed quickly moved over between my legs. With my guidance he started licking and fingering my pussy. "That's it, keep going I'm getting close to cumming." Jed was smart enough to know to go faster. Quickly I was moaning and pulling his head into my pussy shaking with my own orgasm.

"Whew, you did a nice job your first-time eating pussy. Looks like we got some more time your clothes are dry. I think with just a little encouragement your cock will be ready for another round. May I?"

Jed smiled moving his legs apart for me. His cock was mostly hard when he finished eating me but when I told him about another round it sprang to attention. I had never been one to suck my husband's dick but eagerly took Jed's dick in my mouth. After just a minute of sucking I released him getting on my hands and knees on the bed. "Jed, come around behind me and fuck me doggie."

Without a word, he moved behind me easing his cock back inside me. "Oh yeah, that's it. Now fuck me Jed." Jed's hands slid off my shoulders to cup my breasts. His strong hands felt great squeezing my tits while his cock was assaulting my pussy. I was starting to get close to another orgasm when Jed grabbed my tits hard and shoving my cock in me as far as he could. Damn, I could feel my pussy filling with his cum. He silently pulled out laying on the bed next to me.

I rolled over watching the cum ooze out. "I can't believe you had that much in you on your second round."

"Oh, I'm sorry. Did I do something wrong?"

"No, you did great. Did you enjoy yourself?"

"God yes, it was awesome. Mrs. Wilson, can I ask you a favor?"

"Of course."

"Can I kiss you? I feel like such a loser that I've only had two dates and only kissed one girl."

It hadn't dawned on me that with all the sex we had that we hadn't kissed. I sat Jed up next to me leaning in to meet his lips. We kissed for just a few moments before I pushed my tongue into his mouth. Our tongues were dancing while his hand started fondling my tits. I was getting horny again but didn't think that Jed would be up for a third round. I was wrong. My hand that was massaging Jed's chest slid down t his crotch. His cock was at full attention. Damn, youth has advantages.