Cupid's Helpers

^^^February 7th^^^

"Hi, Jimmy," the voice on the phone said. "It's Peggy. Pam's sister."

"Oh, hi."

He sounded confused. He didn't know anyone named Peggy, and he wasn't sure who Pam was. He asked, "And Pam is..."

The voice on the phone said, "Pam is your brother's girlfriend."

She giggled like a teenager and said, "I'm sure you're wondering why I'm calling you. It's about St. Valentine's Day. Are you doing anything special?"

"Ah...Ah.." he stammered. The question surprised him.

She giggled and said, "That didn't come out right. I'm not asking you out on a date. My sister and your brother have been dating for eighteen months, and I'm afraid they may break up.

"I'd hate to see that happen. I think they are good for each other. Don't you?"

"I guess," he offered, being polite. He had no idea about the condition of his brother's relationship or the girl he was dating.

"They are at that point in a relationship where they get serious and commit to each other or break up. I'd hate to see them break up. They've invested a lot of time and effort, and with a little help from us, I think we can get them past this lull, remind them how happy they've been, and get them to commit and declare their undying love for one another."

"I see," he said. He chuckled at her audacity and asked, "What do you need from me?"

"Help me set up a super romantic St. Valentine's Evening for them. They will realize what a great match they are and live happily ever after."

"That's a tall order," Jimmy said. "Fairy tale endings rarely happen in real life."

"It'll be worth the effort when we see them march down the aisle as husband and wife. I'm walking toward your front door. Let's put our heads together and get this done."

Jimmy's phone went dead, and the doorbell rang.

"I guess there's no way out of this," he said. "I don't even like my brother."

He opened the door, and a cute, perky, young woman stuck her hand out and said, "Hi, Jimmy. I'm Peggy."

She grasped his hand firmly and pumped it up and down.

He looked at the young dark-haired, dark-eyed woman and asked, "Have we met?"

"No," she answered and walked into the house and headed toward the family room. She planted her small firm butt on the sofa and said, "Do you have any ideas?

"What? No. I just heard about this scheme seconds ago," he complained. "And my name is Jim, not Jimmy. I'm twenty-two, not twelve."

He sat on a chair across from her and said, "I'm not sure we should get involved in their love life."

"If not us, who? If not now, when?"

"Are you quoting JFK?"

She giggled and said, "Yes. That's a good get. We covered the Cuban Missile Crisis and his presidency recently in History class. I was impressed with the man and his words."

"History class? Are you in high school? How old are you?"

"I turned eighteen a couple of months ago and will be graduating high school in four months," she said proudly. She toyed with her ponytail.

"What makes you think that butting into your sister's love life is something you should be doing?"

"I love my sister. I want her to be happy."

"And you think my ne'er do well brother is the answer?"

"He's nice looking, and they have a lot in common."

"Does this mean your sister also is a heavy drinker and likes to party?"

"I don't know how much she drinks. I live at home, and she's at college. I know she likes to go out and dance and be with her friends."

"You seem like a good kid," Jim said. "Take it from someone a little older. People don't appreciate being messed with and manipulated. Since you like quotes here's one for you from the singer Doris Day, "Whatever will be, will be. The future's not ours to see".

He stood, signally their time together was over.

Peggy's hands balled up into fists, anger flashed in her eyes, and she said, "Don't treat me like a kid. The law says I'm an adult!"

She stood, got in his grill, and said, "If we won't look after our family, who will!"

Jim was stunned by her ferocity and stepped back.

She took a deep breath and said, "Sorry about that. You touched a nerve." She gently grabbed his hand and said, "Please hear me out."

Her hand was warm and soft. Jim looked at it and then at her and re-appraised her, thinking, "This young woman is fiery, passionate, and caring. She's spunky. I like spunky."

He sat and said, "Please, have a seat and tell me what you had in mind?"

They sat side-by-side on the sofa with their knees touching. She said softly, "I think they need a romantic night. Wine, a candlelight dinner, followed by a spa night or watching a good rom-com."

"That sounds nice."

"It wouldn't cost a lot. I can cook. We need a place..."

"We can do it here," Jim offered.

The love-struck teenager had won him over. He didn't want to be the one to tell her life isn't as she imagines and that Santa Claus and the Tooth Fairy are make-believe.

"My parents will be out of town," Jim said. "I'll help you, and then we can make ourselves scarce and let them have a romantic evening."

"Thank you!" she shouted. She leaped into him. He felt her soft arms around his neck, her young firm breasts pressed against his chest, and her lips on his cheek as she kissed him.

^^^

Over the next couple of days, Peggy shared her vision of the perfect romantic night.

"I have been in touch with Johnny's and Pam's roommates. They are helping. I have them putting love notes in her purse and his knapsack and other places they will find them. The notes express their love and say that a special St. Valentine's evening is being prepared for them.

"Each thinks the other is planning it, and that they are supposed to be at your house at eight o'clock."

Jim said. "You are a wonderful sister. A wonderful person."

Jim was swept up by her enthusiasm, and he didn't have much else going on in his life. He bought flowers, scented candles, and a bath bomb. He washed the sheets and towels and cleaned the house after his parents left.

He and Peggy spoke every day. Jim looked forward to their chats. He found her giggle and zest for life cute and intoxicating.

On Friday, February 13th, Peggy came over. Jim opened the door and found her holding a casserole dish covered in tin foil. As usual, she was perky and smiling.

"Hi, Jim," she said warmly. She had on medium-high heels, a short jean skirt, and a denim bustier. The tapered top showed off her little waist and pushed her breast up.

She was showing more skin than usual.

Jim ogled her shapely legs and ample bosom.

"Wow!" Jim thought. "That's not the body of a kid."

He dismissed the thought and said, "Hello, Peggy. Let me give you a hand."

He took the dish from her hands, carried it into the kitchen, and put it in the fridge.

She said, "I made chicken cordon bleu. It's Pam's favorite dish. We can put a note on the door about the wine in the refrigerator and dinner in the oven. I'll set the table now, and everything will be ready for their special night."

They set the table and checked on Johnny's bedroom.

"This is great," Peggy said. "I love the flowers in the bedroom."

She playfully punched him in the arm and said, "You do have a romantic bone in your body, after all."

They laughed.

"The house is set," Jim said. "How about we celebrate by getting a bite to eat?"

"Sure."

"Pizza or seafood?"

"Definitely seafood."

Jim decided to treat the young woman, and they went to an upscale restaurant where they had a fine meal and enjoyable conversation.

Jim learned that Peggy wasn't a dopey kid. She was mature for her age and a caring person. She learned that he wasn't a boring old stick in the mud, and he wasn't dating anyone since a nasty break-up six months ago where the girl cheated on him, and he had a job he enjoyed.

After dinner, Jim walked her to her car and said, "I had a nice time tonight."

"Me too," she said with a smile.

They paused and looked at each other for a beat. She leaned forward.

At the same moment, he turned to go to his car.

"Oh," Jim said when he realized she wanted to kiss. He reversed direction and moved toward her.

By then, Peggy was getting in her car. Her face was red, and she said, "Oh, God. I'm so embarrassed."

He said, "I'm sorry."

She sat in the car, looking forward, and said, "Please let me go home." Tears rolled down her cheeks.

Jim stepped back, and she drove off.

"You dummy!" Jim said as he watched her car drive away.

^^^

While Jim and Peggy were preparing the house and enjoying their seafood dinner, Pam and Johnny were doing their regular pre-party routine, drinking and smoking weed.

When they showed up at the party, they were high and drunk. They jumped onto the dance floor and boogied.

After a couple of songs, they split up.

Pam stayed and danced with friends and strangers. Johnny went looking for tequila.

Terrance danced with Pam. Their fly dance moves degenerated into them grinding on each other.

Terrance got handsy. He grabbed her tits, squeezed too hard, and pissed her off. She marched out of the room, looking for her boyfriend.

Tinsley and Johnny shared a bottle of cheap tequila. Just as the song says, "Tequila Makes Her Clothes Fall Off". Before the bottle was half empty, they were naked and sixty-nining.

She struggled to perform, not because he was big, but because she loved his tongue on her clit. She spent most of the time screaming.

"Ohhh, Baby! Yes! Eat my pussy!"

Johnny flicked her bean and fingered her pussy. He took a slick digit and shoved it up her ass.

"OHH! That's a nice surprise," the dirty girl said. "Do you want to fuck my ass?"

"Hell, yes!"

"You bastard! You promised to stop cheating on me!" Pam screamed.

She kicked her boyfriend in the side.

"Owe."

Pam eye-balled Tinsley, who at the moment had Jonny's cock in her hands, and shouted, "Skank! He's all yours. I'm through with him."

She marched out of the room, found Terrance, and French kissed him.

"I thought you were mad at me,' he said.

"Stop thinking and start fucking me."

They stripped in the middle of the main room of the house. She sucked his cock, guided him to the floor, and quickly mounted him.

The others in the room cheered them on.

Her breasts jiggled and shook as she rode him hard.

"Ohh," Terrance cried out and came quickly.

Pam looked around the room and said, "I need more dick. Who's next?"

Two guys came forward. One was Johnny's best friend, Bert.

"Get your dicks out!"

The young men dropped their drawers. Pam grabbed their penises and took turns sucking and stroking them.

It didn't take the men long to get hard.

She pulled Bert to the ground and mounted him. She fucked him fiercely while pulling on and sucking the other cock.

The men came simultaneously.

One shot his load on her face and tits. Bert filled her with cum.

"MORE!"

"No," Samantha hollered. She was a friend of Pam's and went to her.

The boys scrambled to get to Pam and to get their cocks out. Samantha pushed them away and said, "Get out of here. This party is over."

Sam and a woman who didn't know Pam helped the distraught woman to stand. The stranger gathered up Pam's clothes and the women went to the bathroom.

Pam sat on the toilet, peed, and cried.

The women washed, comforted, and dressed her.

Sam took her home.

Pam's gangbang was the talk of the party. Word reached Johnny, and he said, "I don't care how many guys she screwed. She's not with me. We broke up."

He didn't want to face his friends and explain why his girlfriend was having sex with everyone in sight. He went to his home instead of his dorm.

Jim was up and greeted him. He said, "Hi, Johnny. All set for your special date tomorrow with Pam?"

"We broke up. She humiliated me by pulling a train in front of everyone!"

"Woah! That's harsh."

^^^February 14th^^^

It was Saturday morning. Jim didn't have to go to work; he was hanging out downstairs.

His brother stumbled into the kitchen around eleven o'clock.

"Hey," Jim said.

"Hey."

Johnny went to the coffee maker and got a cup. He sat at the kitchen table and took a long sip.

"You look like hell," Jim said.

His brother grunted and drank more coffee.

"Did you break up with Pam?"

"We're done."

"I liked her."

"She's a whore."

"Oh. I guess your big romantic date tonight is off."

"Fucking right."

^^^

Jim called Peggy.

"Hi."

"Hi," Peggy responded. Her voice was warm and friendly.

"Have you talked to your sister recently?"

"No."

"Johnny probably did something stupid. He says they broke up because she had sex with a couple of guys."

"That doesn't sound like Pam. I'm calling her right now. Bye.

Fifteen minutes later, Peggy was back on the phone with Jim.

"I couldn't speak to my sister. She's hungover and still in bed. Her friend, Samantha, gave me the story.

"My sister caught Johnny red-handed cheating on her. She got mad and got even. She had sex with three guys in front of their friends. They're done."

"Wow!"

"Yes, wow!"

"I'm sorry for your sister. My brother isn't a good guy. I'm sure it was all his fault. I apologize to you too. You love your sister and put in a lot of effort for a special night for her."

"It's not your fault," Peggy said.

"It would be a shame if all our efforts were wasted. Why don't you come over? I hear there is a delicious meal and some fine wine in the refrigerator."

"I don't know."

"I understand you're worried about your sister, but she's at college, right? Her friends are with her, looking after her. She will probably be very embarrassed telling you about what she did."

The phone was silent.

Jim said, "I would enjoy spending the evening with you."

"You would?"

"Yes."

"I'd like to see you again."

"Great. Shall I pick you up?"

"No." She chuckled and said, "Let's save meeting my parents for another day."

"Okay. See you at eight. Dress up. This is a fancy affair."

She giggled and said, "Okay."

^^^

Jim informed his brother that he needed to be out of the house that night. His brother told him, no problem, he had plans.

At eight, Jim was dressed nicely and everything, from the lighting to the music to the wine, was ready.

The doorbell rang. Jim answered it. It was Peggy.

"Wow! You look great. No ponytail."

She smiled shyly and said, "You said this was a formal affair."

She was in heels and a short cocktail dress. She was showing plenty of legs. The girls were on display and unrestrained by a bra. She had taken a curling iron to her long dark hair. Waves of curls fell loosely over her shoulders and down her back,

"Come in. Would you like some wine? I have some decanting."

"Yes."

He escorted her to the couch and got two glasses of wine.

She took a sip, made a face, and said, "This isn't as sweet as the wine coolers I'm used to."

Jim laughed gently and said, "I remember drinking those when I was your age. The hangovers were terrible!"

"Yes!"

"It's all the sugar they put in them."

He lifted his glass and said, "This is the culmination of time, skill, and expertise. A simple grape is transformed into this rich, complex nectar without a lot of chemicals and additives.

"If you don't enjoy this one, there are hundreds, thousands of others to explore: reds, whites, sparking..."

"Like Champagne? I love the bubbles."

"I have a bottle," he said. He stood and fetched it.

He removed the top. There was the customary loud 'Pop', followed by laughter.

Jim poured it into flutes. He raised his glass and said, "To love. It's what brought us together."

Peggy blushed, raised her glass, and said, "To love."

They clinked glasses and drank.

Peggy giggled and said, "The bubbles are tickling my nose!"

They laughed.

They drank champagne, ate the chicken cordon bleu, and talked. They laughed a lot.

Jim learned Peggy was genuinely as nice and as good a person as he suspected. She was also smart, lively, and pretty.

Peggy learned that Jim was a thoughtful, kind man. He had a job he enjoyed and a plan for his life.

"So," she asked, "someday you'll get married and have kids."

"Yes. I'm not ready financially."

He laughed and added, "It might help if I were dating. When I find the right person..." He didn't finish his sentence. He looked into her eyes.

She stared back at him.

Each tried to read the other person.

"Do you have a list of must-have qualities?" she asked. "Any deal killers?"

"She has to be nice. Can you imagine spending your life with someone selfish, mean, or immature?"

"I want my husband to be my best friend."

"Exactly! Someone you love, trust, and respect. Did I mention adore?"

"Is there an age requirement?"

"Yes. She has to be of age. She can't be so old that we can't have children."

Jim paused. He had answered honestly and so quickly that he hadn't seen the meaning behind her question. It suddenly dawned on him that she wondered if he thought she was too young.

He gave her an earnest look and added, "I imagine my wife will be around my age, plus or minus four years."

Peggy beamed.

They cleared the table and loaded the dishwasher.

"What would you like to do now?" Jim asked.

"Well," she said as she came to him and rubbed against him. "I'd like to live out the date I planned for my sister."

"The rom-com is on the DVR."

"We drank champagne and ate the meal. I heard there's a romantic spa experience." She fluttered her eyelashes.

"We did buy the candles."

She looped her arm in his and guided him to the stairs.

They went to his parent's master bathroom. Inside was a large soaking tub surrounded by bouquets of flowers and scented candles.

Peggy stood in front of him. She looked nervous.

He sensed it and said, "We don't have to do this. We don't have to do anything."

She jumped into him, wrapped her arms around him, and planted a kiss on his lips.

He was startled and didn't respond.

She slid off him, cried, and said, "Sorry. I ruined everything." She turned to leave.

"Wait," Jim said. He caught her and said, "You surprised me. You surprise me a lot. That's one of the things I like about you. What happened wasn't how I envisioned our first kiss."

She dried her tears, looked at him, and said, "You have thought about us kissing?"

"Yes. In my dream, it happens this way."

He placed his hands on her face, looked deep into her eyes, and kissed her.

"Mmm," she moaned.

It was a long tender kiss.

When he pulled back, she said, "That was wonderful. That was as special as I hoped it would be."

He grinned and teased her, "In my dream, it was followed by another kiss."

"Yeah. In mine too."

They smiled and came together for another great kiss. They made out for several minutes, standing in the center of the room.

"What happened next in your dream?" Jim asked her.

"Everything."

She undid the hooks on her cocktail dress and let it slide to the floor. She stood there topless in a pair of skimpy underwear. Her breasts were lovely.

He stared.

She blushed; her pink nipples got hard.

He reached out and caressed a boob. He cupped it and gently squeezed her feminine flesh.

"They're beautiful. You're beautiful."

"Thanks. Are you going to join me in the tub?"

"Ah. Yes. Sure."

He kicked off his shoes and undressed.

He stood before her naked. His cock was hard and thick.

She stared at it.

He grinned and let her look.

She blushed and said, "I'm sorry I'm staring. I've never seen one..." She forced her eyes to look at his face and said, "Of course, I've seen a penis before on the internet. I've never got a good look at a real one. When you're fumbling around in the backseat of a car..."

Her voice trailed off and her eyes focused on his manhood.

"Take your time. Have a good look," Jim said. He smirked and said, "While you are looking at me, I am looking at you."