Exy And Shapely Whore Jeanine 07

Sexy, & Shapely Whore, Jeanine #07

Joey has his first date with Allison, the love of his life.

# # #

Sexy, & Shapely Whore, Jeanine rewritten and continued from #06:

"It's time to continue your sexual education," said Jeanine to her brother, Joey. "Now that I showed you how to physically pleasure women, I need to show you how to emotionally pleasure women, too."

Not bothering to get dressed, we both remained naked. Hard to wrap my head around, I couldn't believe that I was sitting on my sister's bed naked. Eagerly listening to her again, I sat ready for her instructions.

"Tell me what to do," I said.

She smiled.

"Don't play by her rules, you will never win. Play by your rules. She'll adapt to fit what you want her to do. If she's playing games, you must be willing to walk away. If she believes that you will leave her, and if she's interested in you enough, she'll do everything she can to please you to keep you," said my sister.

Jeanine smiled.

"I know that sounds weird, but that's how women are. Unlike men who are visual, everything we do is emotional. You cannot use logic to persuade us nor understand us. You must express your passion to make us want you," she said.

She laughed.

"In the way that men are horny and thinking about sex, women are horny and thinking about sex, too," she said. "We don't want men to know that women are whores. We've been fixed to hide our desires."

She laughed again.

"The older we get, the bigger whores we become," she said with a sexy laugh. "With men no longer paying us attention and complimenting us on our looks and on our clothes in the way that they used to and we expect, we become predators. With us horny and unsatisfied, we seduce our sons, our stepsons, husbands of our friends, and strangers that we meet."

'She gave me some thought provoking information about how women are from Venus and men are from Mars,' I thought.

"With us brought up to hide our wants and needs, while careful not to become pregnant, we've been taught that sex is wrong before marriage. In our family, we do not have limitations," laughed Jeanine. "No longer having false pretenses, shame, regrets, and embarrassment, we're free to explore our passions with one another."

# # #

Sexy, & Shapely Whore, Jeanine #07:

It was time to call Allison.

"Hello?"

I loved the sound of her voice.

"Hi, Allison, it's me, Joey," I said.

I heard her excitement over the phone.

"Joey! I've been thinking about you! What are you up to," she asked?

I laughed.

"Oh, about 6' 4," I said.

She laughed and when she did, I realized that I had come a long way because of my sister. Here I was talking to a woman that I had a huge crush on but also, I joked with her. I made her laugh.

"I was thinking about you and where you're going to take me Saturday."

She paused while waiting for my response and when I didn't, she continued.

"Really? Where are you taking me? I mean, what should I wear," she asked with excitement?

I laughed.

"I can't tell you, yet. I have a few surprises for you and don't want to spoil them," I said.

I paused while visualizing Allison wearing something sexy and revealing. I imagined her wearing a short skirt, and a low-cut blouse.

"Wear something comfortable with sneakers," I said.

Taking a risk, I said something that I hoped wouldn't offend her.

"Whatever you wear, you always look sexy to me," I said.

I wondered if she blushed at my comment.

"You know how to flatter a girl, Joey," she said. "You've changed since I saw you last. Well, I don't think you'll be disappointed with whatever I wear."

I laughed.

"That's true," I said."

She returned my laugh with her laugh.

# # #

"What have you been doing this week," I asked?

I smiled.

"The usual things while on summer break," she said. "Cleaning, shopping, and hanging out by the pool."

I didn't know her building had a pool.

"The pool? Really," I asked? "A pool must be nice on a hot, summer's day."

Then, I said something that I hoped she wouldn't take offense to me saying so prematurely in our hoped for relationship.

"I'll bet the guys stare at you in your bathing suit," I said.

I chuckled and she laughed.

"They love seeing me in my bikini. With you on the swim team, you have a swimmer's body. You have broad shoulders, a wide back, a toned waist, and muscular legs," she said. "You have lots of muscles."

She laughed.

"To be honest, and I'm embarrassed to confess," she said with a giggle. "The thing that caught my attention was the big bulge that you had in your bathing suit," she said with a dirty laugh.

I wondered if Jeanine told Allison that I had a big dick. Never thinking that Allison was a slut, I couldn't believe she had checked out my bulge. Yet, with my sister a whore, her friends are whores, too.

# # #

"People aren't interested in watching swim meets. They're more interested in wrestling or basketball," I said.

When she said that she stared at my bulge in my bathing suit, I imagined staring at her D cup breasts in her bikini.

"I don't swim as much as I used to, but I still swim to keep in shape," I said.

When we were at the mall and noticed me staring at her blouse clad breasts, she smiled.

"I preferred watching the guys swimming and diving instead. With them all having great bodies, the swimmers are so athletic. Watching them swim freestyle, doing the backstroke, and the butterfly is like watching gymnastics in the water," she said with a laugh.

I nodded my head in agreement.

"I used to love watching you doing your cheerleading at our school's sporting events. For you to make all of the moves that you made, you must have had gymnastics or dance training," I said. "I thought you were the best cheerleader in school."

Allison blushed.

"Thank you. That's sweet of you to say," she said. "I wasn't the best cheerleader but your sister helped me to be a better cheerleader."

She smiled.

"And like I said the other day at the mall, I certainly noticed you on the front row at all of our games!"

Having things to do to get ready for our date, I had to break our conversation short.

"I'd love to chat with you all day, Allison, but I have things to do. I'll pick you up at 10:00 Saturday morning. Be ready for a day of fun," I said with a little laugh.

She giggled.

"I can't wait to see you again, Joey," she said.

We hung up. I was pleased by how our conversation went. I was excited to see her again.

# # #

During our family dinner everyone talked about their day.

"Did you call Allison today," asked my mother?

I smiled. After seeing my mom naked last night, every time I looked at her, I imagined her without her clothes. I imagined her big D cup breasts and her blonde, trimmed pussy.

"Yes," I said. "I called her. It was good to hear her voice again. I'm seeing her Saturday morning."

If I wasn't excited enough to imagine seeing my mother without her clothes, every time I looked at my sister, I imagined her naked, too.

"I'm glad you confirmed your date with Allison," said Jeanine.

I looked from my mother to look at my sister. As if they were both sitting at the table naked, I couldn't stop imagining them without their nightgowns.

"I don't know what I should wear," I said.

My mother smiled.

"That depends on where you're going and what you're doing," she said.

I nodded my head.

"Wear one of the new outfits that you bought at the mall," said my sister.

I smiled over at my dad.

"May I borrow the car Saturday? My pickup truck would be hard for her to climb inside," I said with a little laugh.

I smiled at my dad.

"Let me think about it," he said.

Not dropping the subject, my mom touched my hand. Now that I saw her naked and now that she agreed to have threesome sex with her daughter and me, whenever she touched my hand, I imagined her touching my cock. I imagined her wrapping her manicured fingers around my stiff prick and stroking me. Then, I imagined her taking me in her mouth and sucking me.

"It depends on what you have planned. What do you have in mind on your first date with Allison," asked my mother?

In the way that I told my sister what I imagined doing on my date, I told my mother. I gave her an outline of our proposed activities. As did Jeanine, she suggested I wear one of the new outfits I bought the other day at the mall.

# # #

Jeanine and I retreated to the den after dinner to continue our discussions about how to talk to Allison.

"How did you feel after you called Allison," she asked?

In the way that my mother wore a short, sheer, low-cut nightgown without having the modesty to wear a robe over it, my sister wore a short, sheer low-cut nightgown, too. In the way that I saw my mother naked last night and now seeing her without her clothes every time I talked to her, whenever I talked to Jeanine, I imagined my sister without her clothes, too. Forget about undressing them with my eyes, I continually stripped them both naked.

"I thought it went very well," I replied. "We had a nice conversation. She said that she can't wait to see me. She's looking forward to our date."

Jeanine smiled.

"I hoped she would. I overheard some of your conversation. You impressed me how you took charge," she admitted. "I'm glad that you haven't reverted to your shy self. You've shown progress in such a short time," she said.

Our mom poked her head in the door. The bright light behind her lit her up as if she was a stripper on stage. I saw through her nightgown as if she was naked.

"I hope I'm not interrupting anything," she said.

We smiled to assure her that she wasn't interrupting anything.

"Your father and I discussed borrowing his car. We've decided to let you borrow my car instead."

Comparable to a Lincoln Town Car, her car was a classic. She had a silver over black, 1985 Cadillac Seville. According to car magazines when she bought it back then, it was the preferred choice for sophisticated women. Yet, with the Seville front wheel drive and the Town Car rear wheel drive, the ride in the Lincoln was not only better but also it handled better, too.

Jeanine had a huge smile on her face.

"That's wonderful," she said. "I've always thought it was such a beautiful car and still is. I wished that someone would have picked me up in such a car. I'm jealous," she said with a laugh.

I couldn't help but smile at my sister. Jeanine was envious that Allison would be chauffeured in such an elegant car.

"Thanks Mom, you're the best," I said.

I stood and hugged her. Squishing her big breasts against my chest, while I poked my erect cock against her tummy, I gave my mom a full body hug. She returned to the living room with our dad to watch TV, and I was alone again with Jeanine.

# # #

"Now, where were we," I asked with a laugh? "Oh yeah, we were talking about my phone call and my date with Allison."

I smiled at my big sister.

"I'm proud of you, Joey. I can't wait to hear how your date goes. Is there anything more you'd like to learn?"

Not sure what else she could teach me that she hasn't taught me already, I shook my head.

"Taking it slow, not wanting to ruin things by rushing things, my plans are to enjoy the date and not expect anything," I replied. "I'm as excited as I'm nervous."

I smiled at my sister.

"My first date," I said. "I don't want to mess it up by pressuring her for sex or even by trying to kiss me."

Jeanine squeezed my knee.

"Don't worry. You won't mess it up. Don' be nervous" said Jeanine. "You'll do fine."

I smiled at her.

"I hope so. I fear that I may fall back into my nerdy self," I said.

My sister nodded her head to show me that she understood.

"Don't pressure yourself. Relax and have a good time," she said.

She squeezed my hand.

"Would you teach me more about the subtle signs that I need to look for, and how best to react to them," I asked?

She smiled.

"Of course, I will. I'm here to help you with your first date in any way that I can," she said.

# # #

We continued talking about situations that may happen during my date. Then, she said something that immediately hardened my cock.

"If you'd come to my bedroom tonight, we can practice more of what you learned when having sex with me," she said.

I smiled and nodded my head.

"I'd love to eat you again, Jeanine. I'd love to make love to you," I said.

She smiled.

"And I'd love to suck you again, Joey," she said.

She reached her hand and fondled my growing erection through my pajama bottoms.

"Let's wait until everyone goes to sleep," I said.

# # #

Around midnight, I walked to Jeanine's room. Her bedroom door was open. Instead of leaving it open, I closed her door behind me. She was checking her phone while waiting for me. A sight to behold, she was naked.

I stripped off my pajamas and climbed into bed with her. One of my favorite things to do was making out with her while fondling her breasts and fingering her nipples. We made out while I felt her tits, pulled her nipples, and she stroked my cock.

I moved down between her legs. I fingered her pussy while licking her pussy. I reached up my horny hand to feel her breasts and finger her nipples while eating her. Not taking her long to cum, she seemed just as horny as me.

"Joey. Joey," she whispered. "That feels so good. Rub my clit harder. Lick me faster. That's it. Right there. Oh, my God, I'm cumming, Joey. I'm cumming," she said.

She arched her back, stiffened her legs, and fell silent.

"Oh, Joey, you've learned how to eat my pussy better than I expected," she gasped.

She didn't enjoy the afterglow of sex for long.

"I want to show you a different position," she said.

She moved her knees up to her shoulders and pulled me on top of her in a modified missionary position. My cock easily slipped inside of her.

Not bothering to make love to me, we fucked. She fucked me and I fucked her. Then, as soon as I ejaculated inside of her, she stopped.

Again, not resting long, she moved halfway down the bed. She took me in her hand and stroked me while staring up at me and smiling. Then, she took me in her mouth. My sister blew me again. She sucked my cock.

She didn't stop stroking and sucking me until I ejaculated a load of cum in her mouth. My cum splashed against the back of her throat and she swallowed my load. Then, she moved up to me.

"Your cock is perfect for me to deep throat you," she said with a smile.

We held each other while kissing until we fell asleep. Sometime around three am, I climbed out of her bed and returned to my room. I was exhausted.

# # #

Saturday morning after breakfast, and after exercising, I called Allison. I felt different. After having had sex with my sister last night, my morning erection felt stiffer than usual. I felt good.

With Jeanine quietly listening in, I nervously called Allison.

"Good morning, Allison. How are you," I asked?

She seemed happy to hear my voice.

"Joey! Good morning. I'm good," Allison cheerfully answered. "How are you doing today?"

I smiled at her over the phone.

"I'm doing great," I answered. "I hope you're ready for a day you'll never forget," I said with a laugh.

She returned my laugh with her laugh.

"Oh, I'm excited," she said. "I never thought I'd be going on a date with you!"

I wasn't sure how to take that remark.

"What do you mean," I asked?

She giggled.

"I never thought you'd be so nice," she said. "I can't put my finger on it, but there's something different about you. You're not like the way that I remember you."

Appreciating her compliment, I smiled.

"Thank you," I said. "I've been working on myself to be a better person."

She laughed.

"Whatever you're doing, you have my attention," she said.

# # #

She paused.

"So, what are we doing today," she asked?

I smiled at her over the phone.

"I've got several things planned for us to do," I said.

She laughed.

"Tell me. I can't wait to hear," she said excitedly.

I paused.

"We'll be going to the carnival downtown. They have rides and games," I explained. "Wear something comfortable. After the carnival, I plan on taking you to dinner. You may want to change your clothes afterwards before I take you to dinner. I'll drive you home for you to do that," I said.

She smiled.

"What about you," she asked?

I returned her smile with my smile.

"I'll bring a change of clothes and change in the car," I said. "I'd like to try out that new Italian place. If that doesn't suit your taste, we can eat Mexican."

Allison smiled.

"I've heard about that new Italian place. I hear it's very nice although a bit expensive," she said.

I laughed.

"Don't worry about that," I said.

She smiled.

"You're such a gentleman," she said. "What's next after dinner," she asked.

I laughed.

"Oh, it's a surprise," I said with a grin. "I'll pick you up tomorrow morning at 10:00. I can't wait."

I smiled.

"Neither can I," Allison exclaimed.

We said our goodbyes and hung up the phone. I looked at Jeanine and smiled.

"What do you think? How did I do?"

She hugged me.

"Oh, Joey, that was great," she said. "You didn't even sound nervous!"

I smiled and thanked her.

# # #

Getting ready, I took a shower, washed my hair, and shaved. I remembered something Jeanine told me in one of our lessons about manscaping. Even though I wasn't planning on having sex tonight, just in case we did, I asked Jeanine if she'd help me.

"Jeanine, unable to see down there, and needing three hands, would you trim my pubic hair," I asked?

She smiled.

"It would be my pleasure," she said with a dirty laugh.

I got out my pubic hair shaver. Jeanine thought I'd look better with a shaved cock and balls, saying it will make me appear larger than to be hidden in the forest of undergrowth. We both stripped and got back into the shower.

"Why are you getting naked, too," I asked?

She grinned.

"As long as I'm giving you your first manscaping, I figured you could return the favor, and give me a ladyscape, too," she said with a laugh.

Having never trimmed a woman's pubic hair before, I gave her a shocked look.

"Don't worry," she said with a laugh. "I'll show you how."

Shaving her pussy was a delicate operation. I had never seen a vagina up close before, well, not in broad daylight anyways. After I shaved her vulva, her pussy felt so smooth. I couldn't resist giving her a tongue bath. Even though we were having fun slathering each other with soap, saving that for Allison, I didn't want to have an orgasm.

Good thing we were in the shower, I practiced some of the oral techniques that I learned. She stroked my engorged cock and fondled my testicles, when she felt I was close to cumming, she stopped before repeating the process. Able to prolong cumming, I managed to avoid having an orgasm.

"That's called edging," she said. "Holding yourself from cumming, every time you get closer, when you finally cum, your orgasm will be better than ever."

# # #

We rinsed off and dried each other. After our shower, I picked out the clothes that I planned to wear today and this evening. For the carnival, I chose a pair of blue jeans, a polo shirt, sneakers, and a light jacket. For dinner and the concert later, I picked out one of my new black slacks, a light blue, button down shirt that complimented my blue eyes, and a darker blue sports jacket.

I wore shiny black, dress shoes. Ready for everything, I brought along an overcoat in case it got chilly, and an umbrella in case it rained. I put them in a garment bag and placed it in the trunk of mom's car.

Even though I had eaten a big breakfast that morning, I had a snack before leaving. My dad wished me luck, and slipped a couple of condoms into my hand. Mom walked me to her car whereupon she handed me the keys, and parted my lips with her tongue while cupping my crotch.