Chapter 23: Friday, July 2nd, 1943

ⁱFriday started off great. When I arrived at the compound Pete said that the Big Boss from Chicago was due in. I'd always thought Sal was the boss, but then, Pete said, there was a big meeting today, and I was to go home, as the Big Boss didn't like new faces. He gave me an envelope with my name scrawled on it.

I headed back home, but I stopped at the first corner out of sight and ripped it open. It held thirty-five dollars as I was promised.ⁱⁱ I tossed the envelope and stuffed the bills into my wallet.

I still wasn't ready to confront Ellie about her new status as a hooker, so I pointed the handlebars back home. Ellie needed some thought. She was my first girlfriend, and I was close to her first boyfriend. I knew I wasn't judging her by the same rules I was playing by. In my mind I was thinking her more of as a colleague than a lover, much as I did Vicki or Alfie.

And then there was Francine. I planned on stopping by the jewelry store around lunchtime. The lingerie store above Bond's offered me a chance to raise my intimacy level with Francine. I hoped to convince her in helping me buy a present for my girlfriend. Walking with her and discussing intimate apparel just might crack her tough skin.

My mom's recent love life was bothering me, too. Jennifer kept smashing their threesome in my face. I wanted her out of this kinky relationship as soon as possible. I rode across town barely watching the morning traffic as a plan germinated in my mind. A plan, that was complicated, but promised to shock my mother back to monogamy. I would need to manipulate some people, but I just needed the right incentives to get them into position.

The first stop in my day was Gloria and Jane's. I didn't want Jane seeing the woman-beater Larry again, so I wanted to keep close tabs on her. I let myself into Gloria's and found them sleeping together. They were naked as far as I could tell; sleeping back to back their round bellies making them look like a ball. Jane's bruises were purple and reminded me of the gun I had hidden in a coffee can in our garden. Larry's fate was still undecided.

I didn't want to wake them. Gloria, I knew would want me to play Marty again. She would also nag me about the pictures. I was pretty sure I could get them done at Amos Hardy's Rexall, but I wanted to be sure before I got her excited about it.

I was planning to visit Francine during her lunchtime at the jewelry store, but it wasn't yet ten, so I decided it was time to confront Ellie. One problem solved by having Ellie at Vicki's was getting through the Maginot Line of her parents. I peeked into their kitchen window since all looked quiet, I rapped on the back door. This stirred no one. Another louder rap was met with the same lack of movement inside. The doorknob turned easily, and I let myself inside

In Vicki's bedroom I saw her and a man under a sheet ripped from its anchors. He was older, rather plump and balding. He had to be a customer as his pecker was too small for Vicki to have done him for free. He was snoring—loudly.

I checked the other bedroom and saw two females—a blond and a brunette. The brunette's body I knew well enough to recognize as my girlfriend turned colleague. The other was Sallie, the bleached blond hooker from the mob party whose mouth was well remembered. The sheets on this bed were still anchored though the occupants were spooned, with Sallie cuddled behind Ellie. I wanted to talk to Ellie, but too many people were around for the honest exchange of ideas I was looking for. So I let myself out, to return later.

A ride through the park found Holly lazing under a large oak with another girl her age. They were lying back against the bark chatting when I walked up. She sat up when she saw me, and called out my name.

I dropped the bike by them and found a spot on the oak tree next to Holly, who said, "I've missed you, Cal. Your mom says you're working all the time." Her eyes told me too that she'd missed me. Holly loved my cock and I could see her trying to think up a way to get us naked.

"Yeah, this job I got out at the beach is keeping me busy. I'm a guard at this private home and just spend my days at a gate. I've missed you too."

Holly said flirtatiously, "Maybe I should come out some day and keep you company." She introduced her friend, "This is Diane."

I nodded at the pretty redhead. "I'm Cal."

She blushed and giggled, "I've heard about you."

"Good things I hope." She was trim with a petite figure, not as plush as Ellie, but very attractive.

Her face turned a bright scarlet, "Yes, Holly talks about you as much as about Carl."

"What does she tell you?" Holly had been telling tales, I knew.

"She said that you," She paused, "You were ... great."

"She went with us to the pond yesterday." Holly confessed.

"Holly," she spat out, "You weren't supposed to tell anyone that."

"Diane, Cal's the one that first took us all out there." She batted her eyes, "I've no secrets from Cal."

"Holly, it's just,, I don't want it to get around..." She sounded nervous.

I knelt by her, "Don't worry, Diane, we're a tight group here. We don't talk about anything to others. If I'd been there and saw your lovely body, your secret would be safe with me."

Diane relaxed, "Good. I mean, I didn't do anything, but skinny dip. Not like some other girls."

Holly looked around and said in a low voice, "She watched me and Ellie do Carl."

Diane blushed furiously. "She's right, I only watched."

"So Diane, if you did watch what did you see?"

"I, uh ... Holly, I can't say it." Diane stuttered.

Holly's glowed. "Carl fucked me while I went down on Ellie. Diane watched."

I dropped to the ground facing them; I casually put my hand on Holly's bare shin. "Nothing wrong with watching." I started caressing her tanned skin. Diane's bright blue eyes watched this closely.

Still bright red she said, "I've never seen anything like that. I didn't know more than two people could do it together. I'd never seen two girls do it."

I let my left hand drop to Diane's shin. She didn't protest so I paralleled my caress. "There's a lot three people can do together."

Holly picked up her purse and pulled out a pack of Marlboro's. She handed one to Diane and me. I shook my head, "My hands are too busy, maybe in a little while." Holly lit them both off one match. Her legs relaxed and my hand slowly worked up to the hem of her pedal pusher. My fingers lightly stroked. Holly glanced over at Diane and saw her friend close her eyes.

"Cal, why don't we run down to the pond?" Holly suggested. "I'm dying to show Diane your dick."

Diane's eyes opened in alarm, but I lied, "I have to go fix some lights at Gloria's at noon."

Holly's disappointment was apparent. "What about your house? Your mom works doesn't she?"

"My house is fine." I stood up and offered two hands to the sitting girls. Holly snatched mine and was up in a second. Diane took it slower and I pulled her to her feet.

Diane's eyes darted between us. "Maybe I should stay here."

Holly said, "No, come along." She took Diane's hand. "You can just watch like yesterday. You won't believe what you're going to see."

Diane looked over at the ball diamond. "But what about Carl?"

Holly's face darkened, "Fuck him. He decided to get into some ball game with us over here with nothing to do." She dropped her cigarette and crushed it out with her tennis shoe. "Come on, Diane, let's go have a little fun."

"Oh, I don't know." She hung back.

"Suit yourself." Holly took my hand, "Let's go."

We'd gone three steps when Diane said, "Wait." She came up to us. "I can just watch?"

I squeezed her arm. "You're not going to be attacked or anything. Just watch. It's fine with us." I smiled to reassure her. "You know Holly likes to be watched and I'm more than happy to do Holly. She's something else."

Holly beamed and tugged on my hand. "Let's go, Cal. I'm wet."

Diane blushed and nodded. "Okay, I'll come along."

We took only a couple of minutes to reach my back door. I looked around hoping not to see any neighbors out. Mom didn't need to know I would be entertaining two girls this morning.

Once in my room I offered Diane the chair in front of my desk, and sat down on the bed. Holly straddled me and kissed me. The kiss rapidly heated up and my hands found Holly's smooth ass covered with her tight pedal pushers. I could feel the seams of her panties through the thin cloth. Diane was watching intently as my hands pressed into her friend's ass.

Holly pulled back and untied the knot in the tail of her blouse and rapidly unbuttoned it. She flung it on the floor and returned to kissing me. She wore a simple white cotton bra. My hands roved from her ass up her back to massaging her shoulders. Diane still watched her eyes moving to follow my hands on Holly's body. I winked at her, and she blushed.

Holly was grinding her pussy on my hard lump. My hands covered her round bottom and pulled her tighter. She whipped her hands behind her back and unfastened the bra, dropping it on the blouse.

I leaned her back, bringing her pert little breasts to my mouth. I sucked her rigid little nipple and looked over at Diane who was beginning to perspire.

Holly tugged at my tee shirt, pulling it over my head. Our mouths left each other only long enough to get the shirt off. Then she pressed her little titties into my chest and our tongues boogied. My hands moved up Holly's bare back squeezing her skin. She had no tan lines—a testament to hours naked at the pond.

Keeping her lips on mine she stood up and shoved down her pedal pushers. I could smell her arousal and my hand quickly confirmed it when I rubbed the wet crotch of her cotton panties. She unzipped my pants and I lifted my ass to help her get them down. She leaped into my lap again and pulled us tight together. With only two damp layers of cotton separating our union. I could feel her moisten our underwear. Diane was leaning over trying to see between us better.

"You might want to sit at the head of the bed," I suggested to her.

"Would that be okay?" she panted.

Holly turned to look at her, "Sure, just lean back against the head board. You can see fine there."

Diane tentatively rose and moved to her new vantage point. She leaned back and pulled up one leg and wrapped her arms around the knee. I leaned Holly back again and suckled her little boobs. She moaned and humped against me. Diane's eyes glittered.

Holly looked at her friend, "Wanna see it?"

Diane's eyes rounded and her head nodded.

"It's so fucking big, Diane, you're not gonna believe it." Holly slipped to the floor and tugged on my briefs. "Come on big boy, Diane wants to see it."

I lifted up and Holly stripped me naked. My dick was rock hard and stood straight up. Diane gasped and Holly gave her a broad smile, "See, he's got a monster cock. I told you so." Diane nodded looking more like she was on a fast fun house ride. She looked a little green.

When Holly leaned over and took the head into her mouth, Diane said, "How can you do that? Isn't he Ellie's boyfriend?"

Holly let me slip, "I've had a little practice. Ellie's not greedy with it." She went back to sucking me. Diane's head bobbed in sync with Holly's watching my cock slip in and out of her tight lips.

Diane was squeezing her knee as she watched her friend blow me. I could see she was getting very aroused, but didn't want to push her into anything. I was content satisfying myself with Holly and leaving Diane to her own invention.

Holly picked up my pants. "Do you have a rubber?" I took them from her and pulled one from my wallet. I didn't want her seeing I was carrying around sixty dollars. This was an unimaginable amount for a guy my age to be carrying around. I plucked the packet from it as Holly stripped off her panties.

Diane groaned, "You're gonna put that inside you?"

"Oh yeah, I can take it all." Holly said. "I've had it in me before, and it's so fucking incredible."

"I don't believe it."

Holly straddled me and pushed me back on the bed leaving my cock pointing skyward. "You just watch." She ripped the packet with her teeth and rolled the rubber on with ease.

When Holly moved over me Diane decided she couldn't see well enough and moved to the floor behind Holly. "He's huge, Holly. You'll never do it."

"Watch!" Holly moaned as she rubbed me around her opening gathering her juices to ease the penetration.

"Oh My God!" Diane gasped as Holly's lips opened and admitted my cock to her wet interior.

I looked down and saw her take about three inches. I could see Diane's hand slip into her pedal pushers and begin to masturbate. I'm sure she didn't know I could see her do this, but my view only lasted until Holly took me all inside her.

"I don't fucking believe you can be that deep, Holly," she groaned.

"You should try him, Diane. He's fucking incredible," Holly shot back.

"Oh, he'd kill me," Diane panted.

"Cal, Diane's still a virgin."

"Holly!! Don't tell him that."

"Oh, Diane, if you hang around us, you won't be for long!" Holly moaned.

Holly rose and fell on me. Even through the rubber I could feel her pussy twitching as I stretched the tight walls. Over the past few days of being with older women, the feel of a pussy with like-new mileage on it was electrifying. Holly grunted when I hit bottom with the long strokes she took. As she lifted up I could see Diane's hand humping her pussy. I was wondering if the hair on her pussy matched her red-haired head, but I still was going to let her take this experience at her pace.

Holly leaned back and I pinched her little nipples rolling the pink nubs roughly between my thumb and index fingers. "Oh Fuck Cal!" She slipped into second gear and rode me faster. Now I had a stroboscopic view of Diane pleasuring herself. She'd pushed down her pants and I saw in rapid flickers that she did have red pussy hair, and it was wet, plastered to her pale white skin.

My right hand left Holly's nipple and found her clit. I was getting close and I wanted her to climax before I did. My strokes on her little clit shifted her hips into third gear. Her pussy leaked lubrication on my pistoning cock.

Diane's moans grew in volume as Holly's voice rose to a scream. She shuddered and her pussy clamped down hard on me. "Oh Cal," her wail filled my small bedroom. I heard a thud and looked around Holly to see Diane lying on the floor flailing at her ruby pussy with her pants tight around her knees and her cotton panties stretched around her thighs as she climaxed. I lay back down and my cock began to fire its load into the empty tip of the rubber.

Holly rolled to a stop. "Oh God, you are so good, Cal."

I sat up to see Diane frantically pulling up her pedal pushers, blushing at me as I watched her cover her pussy.

Holly pulled off and removed the filled rubber. She hopped to the floor and dashed out in the hall. Diane sat up. "So, how was watching?" I said.

"I didn't know ... It was so ... exciting ... I never let ... anyone ... see me do that," she stuttered.

I heard the toilet flush and Holly returned without the rubber. She stood naked over Diane. "Didn't I tell you how big he was?"

She nodded still dazed. "He's bigger than Carl. I've never seen another one." Her eyes were on my cock as it now lay limp on my stomach. She sat up and slowly approached me. Holly watched with a smirk on her face as her friend moved between my legs and stared at it.

She turned her head up to Holly. "We better go. I'm afraid of this." She stood, "Please Holly, let's go."

I nodded to Holly and she began to put her clothes on. I sat up and picked up my pants to get a smoke. I didn't bother to dress as I stood and lit the cigarette. I walked naked to the back door with the two girls. Holly gave me a wet kiss, "Thanks, Cal. It was great." I turned to Diane and lightly kissed her lips. She didn't offer her tongue, so I didn't offer mine.

They left giggling and whispering to each other. I realized our little group was growing. I'm sure Diane would be at the pond next time I went and I was curious if she'd be more adventuresome with Holly and Ellie with the examples of their behavior.

I washed up thinking about Diane's red-haired pussy. I was drawn to her and hoped to pop her cherry before Cal got to her. For lunch with Francine I put on my Bond Clothing Store outfit. She's seen it before, but I hoped she wouldn't notice. I needed to give Frank a visit to expand my wardrobe.

ⁱⁱⁱI parked the bike down the block from the jewelry store just moments before Francine was to hang out the "Out To Lunch" sign. I met her at the door. "Francine! I'm glad I caught you. Would you have lunch with me?"

"Well, Jason, I suppose. I was just going to the Lake Inn for some toast and coffee." She hung up the sign.

"Could we make a stop first? I need your help in buying a present," I said shyly.

"Certainly, what sort of present do you need? I've got some more nylons in stock if you would like them," she paused.

"No, I gave her a pair of nylons, but she wants something nicer to hold them up." I tried to sound uncertain.

"Your sister-in-law wants you to buy her a garter belt? Jason, that's a little intimate, don't you think?" Francine's face showed shock as she locked the door.

"Francine, my sister-in-law doesn't want the garter belt, my girl friend does." I confessed weakly.

"Your girlfriend? I didn't know you had one, Jason." She smiled.

"We've been ... well for a couple of years."

"How sweet, why haven't you ever mentioned her?" I directed her down the street to Bond's Clothing Store and the lingerie shop on the second floor.

I shrug. "She's not the usual sort of girl friend. I'm not sure how to describe her. She's a bit older than me."

Francine's step faltered, "How old is she?"

I stopped. I leaned to her ear and whispered, "She's fifty-four."

Francine's voice carried down the street, "Fifty four! Oh Jason, she's old enough to be my mother. How could you be doing this?"

"It just sort of happened." I meekly shrug. "It's a big secret. My mom would die if she knew her best friend and I..."

"Her best friend!! Oh, Jason, you're getting yourself in very deep for a young man your age." Francine's face was scarlet.

"Francine, I've tried to stop. Whenever I hint at a girl my age she gets very jealous. She's threatened to kill herself!"

"Oh, Jason. How did this ever start?"

"I was in the bathroom drying off from a bath when she walked in without knocking." I tried to appear pained in telling my story.

"So? Didn't she just say excuse me and leave?"

I paused. "Well, she started to ... then she stopped and stared at me."

Francine's eyes locked onto mine. "Well, why was she staring?"

"Well, I'm not sure how to explain this, but I'm rather ... large. This is so embarrassing, Francine."

"Large? You mean your... ?" She said nervously.

"Yes. She stood there and stared. You see I'd been ... and it was ... you know ... big?"

"Oh my God, Jason. She just stood there staring at it?"

"Yeah, I didn't know what to do. I was so afraid my mom would walk in." I shrugged my shoulders. "So I just stood there with it so ... uh ... excited."

"Here's the place, Francine." The hand-painted sign on the glass door read: Maria's Fine Lingerie--Upstairs.

She said, "I've heard about this place. Jason, it's supposed to be very expensive."

I opened the door for Francine. She entered the dark stairway. I let her start up and walked a step behind her. Francine turned her head and said, "So what happened, Jason." She headed up the steps as I followed. Francine had a lovely ass; the tight skirt gave it a pear-shaped appearance. I wondered if she wore a girdle.

"This is really embarrassing ... Are you sure you want to hear this?" I asked.

"I've never heard of a woman her age staring at you. I would think she would have the manners to leave."

"She did say please," I smiled.

"Please?"

"She asked if she could please ... touch it. She said, she'd never seen one that big."

Francine stopped on the stairs. "You're just a boy." Her eyes looked into my eyes nervously. "How big is it?"

I lifted my hands and positioned my index fingers eleven inches apart.

Francine blushed as she stared at my fingers. She slowly turned and continued up the stairs.

I caught up and decided to change the subject. "She gave me a hundred dollars to spend."

"Jason, you can by a lot of garter belts for a hundred dollars." Francine said quietly.

"Could you help me spend the money?" I stopped her at the first landing. "I could even get you something. She'd never know."

"Jason, you can't. It would be so inappropriate. I'm engaged remember." She whispered.

"Who would know? Your finance must know you like fine things. I would love to buy you something. It would help me forget about this awful situation I've gotten into." I wanted to sound nervous.

"Jason, even going into this store with you will cause the employees to think we've been intimate." Francine turned to face me.

"Can't we tell them I'm your younger brother or something?" I didn't want to lose her so close to the door.

"Jason, a boy's sister doesn't go with him to buy underwear like this. It's very sensual apparel, Jason. It's more for married couples and lovers."

"Please, Francine, just help me this one time. Just to buy a garter belt." I pleaded.

She looked into my eyes. I held her gaze. I could see her deflate. "Alright, Jason, just this one time."

I gave her a warm smile, "Thank you. I really do need your help."

We continued up the steps, a small bell tinkled when we opened the door to the shop. A short chubby Italian woman met us. I assumed this was Frank's wife, Maria.

"May I help you?" She said in slightly accented English.

I tried to look confident. "I'm Jason Henderson and this is my ... uh ... friend, Francine."

She nodded. "I am Maria, I am the store owner."

As if I did this everyday I said, "I need a garter belt."

Maria looked surprised, "Do you know the size and style?" She gave me a condescending look that said, "How old are you, kid?"

I glanced to Francine and said, "Her size and something very French."

Francine gave me a dark look, but said nothing.

Maria turned toward the rear of the shop, "Follow me." Francine poked me in the ribs. I grinned at her leading her to smile back.

We stopped at a small table. She indicated some French-styled garter belts. "Would you need help in your selection?"

I said, "No, we'll make our selection and let you know."

Maria bowed, "The dressing room is just in the corner."

"Thank you." I bowed also. She moved to the other end of the shop giving us privacy.

"Jason, that was so outrageous, making her think it was for me." Her eyes blazed, but there was an undercurrent of insincerity to her tone. I held her stare until she giggled, "You are something, Jason."

"Thank you, Francine." I picked up a silky embroidered garter belt. "What do you think of this?"

She took it from me examining it closely. "It's amazing. Such stitching. It's a work of art." Her fingers didn't want to let it go.

"Try it on, Francine, what could it hurt."

She gazed into my eyes and to the exquisite item in her hand. I gave her back a firm push. "Okay, I will." She said. She took the garter belt and entered the dressing room.

She appeared shortly smiling. "Well I have it on. What do you think?"

"You look the same to me." I said.

"I don't know what you were expecting you can't see a garter belt." She seemed pleased with her little joke.

"But, Francine, I really need to see how it looks." I stood waiting. I took out a pack of Luckies and lit one. "I'm waiting, Francine."

She glanced at the front of the store and pulled up her skirt. She stopped well short of her waist, but I could see the straps holding up her nylons. "Very lovely, Francine." I say softly. "You have fabulous legs."

"Thank you, Jason." She slowly lowered her skirt. "I should take this off. Are you going to buy it for your ... lover?"

"Yes, I am."

When she came out I'd picked up a pair of loose fitting French panties. She stopped silently by me. "What do you think of these?"

Francine's fingers slid over the smooth silk. "Very nice, Jason, and very expensive. They're so beautiful. Any woman would love these next to her."

"Try them on and they're yours, Francine."

She hardly hesitated. Maria was up front, sorting items that I was sure didn't need sorting; she was pointedly ignoring us. Francine stepped out of the dressing room. I moved between her and Maria and lifted an eyebrow.

This time she turned away from me and lifted her skirt to her waist. Her round bottom filled the panties perfectly. The loose legs made me want to get on my knees and see heaven. She looked over her shoulder smiling and dropped the skirt.

"So, Jason. Are they mine?"

"Yes, Francine, they're yours." I smiled.

"Thank you, Jason." She hooked her arm in mine. "I need to get back to work."

I left her to browse as I caught Maria's eye to pay. I handed her the tag from the panties and said, "She decided to wear them home, and I want two of the garter belts in separate bags." Maria had replaced the "how old are you kid" look with a nod to a valued customer. She totaled up my purchase to thirty-one dollars. I gave her forty and she made change as Francine walked up.

Maria smiled at her. "You will love how they feel."

"I love them already," Francine said as she took my arm.

"Thank you, Sir." Maria handed me the bags. Francine didn't notice the extra bag.

"You're welcome. I shall come back here again." I gave her a parting smile.

As the door closed behind us, Francine giggled, "My god the things you got me to do in there." Her arm was still hooked though mine. "I really need to get back to the store, Jason."

She held my arm down the stairs before stopping at the door to the street. She turned to me, leaned in and kissed me. Her lips were closed but she nibbled at mine. I dropped my purchases, took her in my arms and pulled her tight. My erection pressed against her. I saw her closed eyes open widely. She wiggled against me. Then her hand came between us. She lightly touched me. Her fingers lightly measured my size. Her lips brushed my ear. "Now, I believe you."

Then her hand left mine and both arms came around my neck. Her mouth opened and we kissed deeply. My hands moved down to her ass—caressing it as she pressed into my hardness.

"I have to get back to work. And you, Mister, need to calm down." She opened the door and strode quickly away. I couldn't follow, as my cock was completely engorged and not suitable for displaying in public.

She might have gotten away at that moment, but I knew she was hooked. All that was left was reeling her in.

^ivI went back to Vicki's after this with a quick stop at my house to change back into my "Cal" clothes. Francine's kiss and embrace had left me in need. Perhaps visiting Ellie with such a fire burning in me was not wise. I plucked one of the Maria's bags from the handlebars of my bike and rapped on the back door. Vicki opened the door dressed in a halter-top summer dress.

"Cal, it's been a while." She let me in. The house smelled of cigarettes and sex, nothing unusual.

Ellie strode out of her bedroom wearing just a pair of panties. "Cal!" she shrieked and jumped into my arms. Her lips found mine, and her tongue deeply invaded my mouth. My hands cupped her ass cheeks as her amazing enthusiasm cooled my anger. She trapped me with her legs tight around my waist.

Vicki picked up the shopping bag I dropped. "What's this?" She peeked inside.

Ellie dropped to the floor, "Is that for me?" grabbing the bag from her sister. She pulled out the garter belt. "Shit! It's amazing."

Vicki looked at the bag, "Maria's." She showed it to Ellie. "Cal, you bought this at Maria's? That place costs a fortune!"

Ellie put the belt around her waist. She cinched it up a bit. "You look so good in that," I said.

"It's the most beautiful thing I've ever owned," She glowed. "Wait!" She dashed off to her room.

Vicki said, "Well, I think you're in with her again."

"She's very sexy in it." I looked into Vicki's eyes. "So why is she here?" I lied and said, "I stopped by her house, and her mother said she was here."

"She wasn't kidnapped, she ran off with the guy. When Mom and Dad heard that, they threw her out. They're sure she's pregnant. So she's staying with me."

"You think she's pregnant?"

Vicki waved her hand. "Who, knows. She's had enough spunk put in her this month to have six kids. We'll know in a few days. She's due for her monthly."