Who's the Lucky Boy?

Story Info
Young ex-con arrives from England and eyes brother's wife.
3.6k words
4.27
29.6k
3
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Findlay (Finn) Regan arrived at Logan International in high spirits, having consumed five whiskies during the flight from Gatwick, England, and having patted the pretty Irish cabin attendant called Maeve on the butt to earn a huge smile and she made no attempt to move off quickly.

The cheeky-faced Finn was not long out of prison, jailed for 28-days for riding around recklessly in an abandoned car with two older friends who'd found with the motor still running and unaware it had been used in a bank robbery. When petrol was running low they abandoned the vehicle after in great hilarity the driver skidded to end their ride in the village duck pond, unwittingly destroying vital evidence.

The short jail term for being involved as an accessory in the unlawful taken of a stolen vehicle was deemed a minor offence after Finn. The American authorities agreed with that when appeared for an interview because of a criminal conviction but after a lecture about keeping on the straight and narrow he was given a visa entry into the US permitting him to stay for ninety days.

When at the exit disembarking Finn gave Maeve 'the look'. Her face colored, the smile was huge but she held up her finger and pointing to the engagement and wedding rings and whispered, "Sorry."

Finn was sorry as well.

Finn's older half-brother Frank and blonde wife Macy -- she almost forty and Frank was forty-five -- met him to take him to their home in central in Boston.

"Hi kid," the weary-faced Frank said, punching the twenty-six-year old on the shoulder and then hugging him. "How's mom and how's your dad?"

"Okay. Look Frank, I'm sorry at being an ex-con."

"Think nothing of it Buddy, I don't. Macy sure does and is itching to reform you."

"Don't take any notice of him sweetheart," Macy said, pushing in between them and kissing the new arrival. "Frank still has a touch of that Irish stupidity in him."

"I'm half Irish," Finn said bristling. "It's called humor. Don't you..."

"Kid, Macy has a wicked sense of humor."

"Oh I apologize for getting uptight Macy."

"It's okay sweetheart," Macy said kissing him again. "Welcome to America."

"You smell nice."

"Oh god, a compliment already and I've yet to cook for him."

"Macy is the sweetest smelling babe in these parts," Frank said but without much enthusiasm. "You remember Macy from the wedding don't you?"

"God yeah. I thought she was a Hollywood film star."

Frank roared in laughter and Macy smiled, looking at Finn curiously.

They drove to the town of Arlington, some six miles northwest of the Boston city center. The house was substantial, two and a half level. As they waited in the black SUV for the electronic-controlled gates to open Finn's said, 'Wow' and his jaw dropped. His brother appeared very pleased.

They ate supper in the kitchen. Although Macy had put on weight since the only other time Finn had seen her at the wedding in Kent, England, fourteen years ago when her grandparents lived; he could tell she was still well packaged. Twice as she flitted between the table, bench and refrigerator during the light meal -- it was almost 1l:00 -- she caught Finn looking at her ass and she stared back at him without expression.

Frank yawned and said he was off to bed because he would be leaving at 5:00.

"Welds in a bridge we built five years ago are failing and the principals of our subcontractors who did that job, a large company, are being sued for several million bucks and their principal is likely to go to jail for recruiting non-certificated welders. Remarkably I have been engaged by the local authority to supervise the remedial work because as the construction boss and chief engineer of my company I know the structure better than anyone and know which sections can be cut away safely to reach inner welds as light traffic is being permitted to use the bridge to avoid chaos."

"Jesus. Do you carry any blame?"

"My insurance company argues I'm not culpable and it appears the local authority doesn't think so otherwise I would not have been allowed back on site. These things happen from time to time in our business where short-cut tactics and questionable methods are rife."

"Tell him Frank. The local authority insisted on their engineers supervising the construction instead of Frank engaging independent engineers which is the normal practice."

"Finn doesn't need to know that. Finn listen to this will you. Roy and Gracie are away at boarding school and Macy is lonely being at home all day by herself with me gone in the mornings before she wakes and arriving home after dark. I want you to spend a lot of time with her, let her show you around Boston and beyond. That's the reason why I wrote mom asking you come here after you came out of the jug and completed probation."

"I'd be delighted to be hosted by your beautiful wife."

"Is that square Finn? I don't want you lying to me thinking she will bore you shitless and you end up giving Macy a hard time?"

"Relax Finn. I can understand you being uptight with so much on your mind. What if she wants me to pet her?"

Frank laughed. "You'd be lucky. Let's just say if she wants you to pet her and she says so, then do it. If you don't I'll kick your ass. But dream on buddy."

Frank hugged them both goodnight at left the room grinning.

"Just as we thought," Macy laughed. "Frank is showing signs of relaxing already. As you can understand he's working in an atmosphere of simmering hostility, although it's calmer now that he's broke a belligerent foreman's jaw and the guy is back on site and the bad blood between them has gone. Frank has wanted a safe pal who understands him -- I mean a buddy other than me. Did he used to call you buddy in England?"

"No, never although we go along very well."

"He's called you buddy several times since your arrival at the airport."

Finn replied yes and now he understood the situation and would be happy to help lighten their loads.

Macy said goodnight and left without touching him.

* * *

Finn awoke to hear birds singing. He heard noise in the kitchen and after a shave and shower dressed and went to find Macy.

She was wearing only her nightdress.

"Hi," she said brightly, raising her lips and was kissed.

"Oooh, you smell manly."

"After-shave and talc," Finn said squirming. "Um, ought you to have more clothes on when I'm around?"

"I'm like this until after breakfast when Frank and the children are around. Is mommy embarrassing you?"

"No it's just..."

"It's just what darling?"

"Um, your body. Y-you are a woman."

"Ohmigod really?"

She laughed and patted his shoulder. "Don't worry about seeing my like this. It will be normal to you within the hour. Have you caught up on your quota of women after getting out of jail?"

"Only sluts. We live in a fair-sized village and the real women wanted nothing to go with me."

"Perhaps I can find someone for you?"

"No, you are fine."

"Excuse me?"

"Just looking at you is enough."

"Finn really, I'll turn forty near the end of this year."

"So?"

Macy turned and caught the first omelet before it really burned. That gave Finn time to adjust his dick without being seen. It had risen into a fierce boner and had been bent over. As he sat back he knew where that boner ought to be, exercising.

As they ate Macy smiled. "It was ass you were looking at last night and now it appears to be breasts."

"I like both. In both instances you are great."

Macy looked down. "These hang far too low when not restrained."

"I love heavy-hangers."

She dropped her fork and omelet fell on to the table.

They grinned.

"If you talk sexy to me that's what's you'll get back from me, otherwise I'll only look and brood but you will be safe."

"Okay but what if I don't want to be safe?"

"You won't want to be bothered by a young guy like me, an ex-crim."

"Oh yeah?" she said, face flaming.

"What should we do today?"

Macy grinned and said visit the town center and to allow her lovely guest to get directional bearings. "You can use my car just be asking if it's available.

Frank arrived home an hour earlier than usual, according to Macy. It was still light.

Although looking tired he came in smiling.

"Want to go to Walt's Bar, I checked it out when Macy and I roamed the town center."

Frank beamed. "Get your glad rags on Macy, we are going drinking."

"Perhaps Friday night darling," she said kissing him. "You boys go... you'll have so much to talk about it will only bore the pants off me."

"There you go buddy, isn't she intelligent as well as a hot number?"

"Yeah, you are very lucky to have her methinks."

"After a few friendly beers I'll have her tonight for sure," Frank beamed, looking at his now pink-faced wife.

The next day looking at the shops in Boston, Finn conscious that Macy had taken his arm and kept it pressed against her tit, eventually said, "Did you get it last night?"

"Didn't you hear the noise?"

"No."

"Liar." she giggled. "Thanks for helping make that happen. It's been almost a month. He's been rather stressed."

"I'll assist by helping him to relax."

"You're such a good boy," Macy said, stopping, turning and kissing him full on the lips.

"Wow."

"You are welcome to kiss me fully whenever you wish."

They walked on in silence, Frank experiencing his first boner walking down an American street.

Finally Macy broke the silence. "What are you thinking?"

Finn hesitated and then, "Wondering if you really will fuck me."

"I'm thinking about it but in this instance excuse me for being a slow thinker. Let's come into this china store, one of my favorite stores in all of Boston."

That night Frank and Finn taught Macy the card game euchre.

"Our mom taught all her seven kids and three husbands this game," Frank said proudly.

Finn was pleased Frank consumed only two bottles of beer, as he did. He understood some people under stress became heavy drinkers. Laughing seemed to be the thing that helped Frank to lighten up. Finn with huge apologies to Macy began reciting prison jokes, some so foul they'd even turn up the toes of the Bishop's mother-in-law. As they continued Macy's initial polite laughter became as raucous as the men's, and she had only had two wines before she stopped drinking.

Later Finn was seated dressed on his bed studying a map of Greater Boston when Macy came in after knocking. "Frank had a great night and he's asleep already. Thank you darling."

They kissed until Finn felt Macy's mouth open. He pulled away and yawned.

"Better not let Frank wake and catch you in here."

"My thinking is he wouldn't mind but only if it were you."

"Well let's not test that theory eh?"

Macy smacked his ass and left.

Next morning Macy pulled her nightdress off a shoulder and holding out a breast and said to Finn, "Kiss this."

"If I do that I'll have to skive off for a wank."

"Whatever. A lovely kiss please."

Finn kissed it and they watched the big nipple firm and then watched as he dribbled down the mound. As he bent over to tongue the dribble over the nipple Macy dug her fingers into his hair and moaned and then groaned when Finn asked, "What would you like to do today?"

Big-eyed Macy sighed and said he should decide.

"Let's make a full day of it visiting outlying places of great historical interest."

"Yes, well you go and jerk off and I'll get ready."

"I'll be fine. You just hurry up, I'm ready to go."

"Okay, then let's have breakfast on the way to Deerfield, which is 90 miles from here. I promise you a very interesting day."

Well it was an interesting day apart from all the fucking tourists, thought Finn, forgetting he was one and had a guide with him adding to the numbers.

During the day he caught Macy looking at him deeply a couple of times, and when her dress hitched up in the car she made no effort to pull it down and during breakfast had asked him brazenly, "What were you thinking when sucking my boob?"

"I was wondering what you were thinking."

"Liar," she said, eyes twinkling.

Several times during the day he caught a flash of her red cami and once she asked, "Do you like my legs -- you look at them a great deal."

"I'm thinking sex," he choked.

She laughed and took his arm and she said they should move on. She then pushed his arm in harder against her breast.

They arrived home an hour before Frank was due home although he might arrive earlier to be with Finn.

"Would you like me to relief the pressure... you've had a boner for most of the day."

Finn swallowed and she grinned and knelt in front of him and unzipped him, hauling it out.

"God, it looks very familiar," she giggled.

"W-what about F-Frank arriving?"

Macy said they'd hear the vehicle. Her tongue flicked around the head of his cock.

Finn closed his eyes and kept brushing her hair from her face and he imagined his cock thrusting behind those saggy tits and he groaned.

At that she grabbed his balls and squeezed lightly.

Before Finn realized where he was and what he was doing her was ejaculating.

He looked down to find she was hosing him over her dress top.

They heard the vehicle arriving.

"F-Frank," he choked.

"Tell him I'm in the shower and act normally," Macy said, kissing him and then patting his very red cheek.

As she left Finn zipped up and washed his hot face in the kitchen sink, using cold water.

He was sitting at the table with two beers ready when Frank walked in and sailed, "You know how to please a guy. Where's my babe."

"Showering."

"Oh good. I might be a while. She usually gets sexy when she's in the shower."

"I'll remember that," Finn said, and bit his tongue.

Frank grinned and said, "Sorry pal, she wouldn't be that interested in you."

Finn began to relax.

"But then again..."

He looked up and met Frank's gaze.

"Finn, I'm serious. If she wants it, give it to her. My girl has had a rough few months and perhaps a young dick will make her day."

"Frank, I don't..."

"Shut up and have your beer. Be a pal man, in fact be a man."

Finn grinned when he heard muffled screams from the master-bedroom bathroom upstairs, knowing Frank would be pumping and Macy would be screaming with Frank's hand over her mouth as she was ending her climax.

They both came down in dressing gowns for dinner with embarrassed grins.

* * *

Next morning Macy appeared almost shy of Finn and the kiss was more than a peck and she had the table between them before he had time to grope. Finn could only assume Frank had told her to fuck her guest.

They ate almost in silence and that obliged Finn to say, "When are you going to fuck me?"

Macy jumped up and left the room, bouncing off the doorframe. She poked her head around the door seconds later and said, "Finn Regan, you have no right to talk to me like that."

He blew her a kiss and she went off muttering; he thought it sounded like very bad language. Fucking women. They were so complex. He didn't know how to handle this impasse.

Macy came down thirty minutes later and told him to amuse himself, that she was off to the mall.

"Can I come with you?"

"I suppose so."

Wow, grumpy. He thought perhaps a little humor would help. "Promise to keep your hands off me?"

He gave her what he considered was his irresistible grin. She smiled and said, "Christ you are a little devil."

Finn held out his arms and she came into them and they kissed and then hugged. He made no effort to fondle her, sensing she was well short of wanting that behavior from him.

They strolled through the mall and then did the supermarket shopping.

"I'm so grateful to have you pushing the trolley," she said, patting his cheek.

"Did Frank say it would be okay to have sex with me?"

Macy held his gaze. "He said to have sex with you, delivered like an order."

"We don't need to have sex."

"I know that and I know I should say that to you... b-but I can't."

"Wow, don't say anything more. Let's shop."

Macy asked Finn to drive and sat attentively ready to tell him to keep to the right side of the road. But he kept his speed down, drove very competently and never once appeared to want to drive on the left-hand side.

He drove in and closed the garage door. They sat without talking for a moment and Finn could hear Macy's breathing rate increasing.

They met at the trunk of her small car and Finn kissed her. Macy kissed him hungrily and slowly he turned her around and bent her back over the car. He pulled her skirt up high and to him the sound of his zip going down appeared deafening.

"Yes," she groaned. "Don't shoot inside me."

Finn got it in with little problem because she was wet. Macy virtually lay still while he pumped but wriggled out a breast for him to grope and she licked it, raising his passion when he saw that.

He pulled out just in time and squirted over her chest, face and hair and on to the rear window.

"Ohmigod," she laughed and opening her mouth caught a little of the next and more reduced flow.

They cleaned up, unloaded the shopping to the kitchen and then Macy grabbed Finn's hand and raced him to his bed saying this time they'd do it with plenty of action. She kept her skirt and panties on but removed her top and bra and lifted aside her panties and as soon as Finn slipped inside she acted as she were on fire. Each time he went to fire she took him into her mouth and made such a show of it Finn figured she thought she was acting like a whore.

He loved it and could tell so did she.

"Do you take it in the butt?"

She nodded and said she'd get condoms and lube tomorrow.

"God you can fuck better than your brother."

Finn placed a finger over her lips. "Please don't make comparisons and try not to think about them. It won't serve any useful purpose."

She pushed his finger away saying it still smelt of cunt juice. "What you just said is sensible. I'm off for a bath and then we'll go somewhere for late lunch."

Sipping wine Finn asked, "Tell me about all the guys you have fucked."

They had an entertaining time. Macy gave it to him complete with disgusting phrases and descriptions.

When Macy finished she said, "You probably won't like me now. I sound like such a slut."

"No I think you are adorable and know those incidents are spread over many years. I have to admit though in comparison I would sound like a choir boy."

* * *

Frank ended his contract just before the school break began and they had a lovely time with the kids. After the children returned to their schools Frank announced to Macy and Finn they were hitting the road to show Finn something of the country. That took almost a month and before long they were only booking one room and spending half the night making whoopee as a threesome, or a foursome on nights when Finn struck it lucky with a woman who also agreed to a groupie.

Then Frank's company won a big contract in Canada and Frank's partners convinced Frank he should spend nine months in Vancouver heading the project.

Frank and Macy looked at Finn grinning when he was considering a job offer that if Finn returned to England for a break he was assured of being allowed into Canada for the duration of the project.

"The Canadian immigration officer I spoke to was very interested that you were a computer systems engineer, saying there is a bit of a shortage of them in her country and you'd almost definitely be considered as a preferential immigration candidate."

"That's good and thanks, yes, I'll accept your job offer. But why are you two grinning?"

"We were itching to hear you accept. Macy has a half-sister just a couple of years older than you who lives in Calgary and is presently going through divorced trauma. There are no kids and she'll be a wealthy lady after the carve up of assets."

"I think you'll be a really lucky guy Finn," Macy said pressing her tit into Frank's arm. "Shannon is even bigger into sex than I am."

12