Jill's Rain Checks

Story Info
Jill honors rain checks giving extra service to her Johns.
3.5k words
3.55
37.6k
8
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
tawriter
tawriter
117 Followers

Jill honors her promises for rain checks giving extra services because her johns made her come multiple times.

Offered to take up the overflow in Mickie's scheduled tricks, Jill and Jack settle on a strategy of pricing to capture market share where the couple would charge $50 and the store a further $25 to provide a venue for the encounter. Further Jill and Jack set a time policy of 'fuck till you come." Most of the johns waiting impatiently for Mickie took the bargain offered by Jill and switched 'allegiance.'

One of the first of Jill's johns pressed Jack on the 'fuck till you come' offer. "What happens if I don't come but I make her orgasm twice before I am done?" The john bargained

"What do you suggest?" Jack temporized.

"I will take a rain check. I will come to your place and you let me have her for an all night all holes fuck session. ".

Despite Jack having two anal fuck sessions in the prior 90 minutes, the prospect of having to deliver his wife, scantily clad, to some guy who had already bought her gave him an almost painful erection. After swallowing nervously he said "I am sure she will agree to that."

Realizing he had won the negotiation, the john, we will call him Mike, pressed his dominance. "That is not all, if I get her to come three or more times before she finishes me, she will have to give me a weekend. She is to commit to doing anything anyone and anywhere I say, with the only proviso that her health will not be endangered." Mike paused and recognizing that Jack was not resisting, finished with: "Jill will be wearing a diamond slave collar all weekend and she is to bring the matching leash." "Diamonds are for Gangbangs."

At that moment Jill returned from satisfying her first trick. "Oh baby, that was quite a session, that stud screwed me thoroughly before I got him off. He really did a number on me. I came twice! "She happily gushed. Then seeing a strange look on Jack's face asked. "I hope you are not mad, because I want to do this. I am having fun."

"Jill the guys have a guarantee of performance which I agreed with Mike, and you better understand the implications." Jack said as he reviewed the performance guarantees that might commit Jill to weekends as a sex slave all around the Midwest while Jill's eyes grew wider and her imagination expanded the scope of the potential adventure ahead.

Later in their motel room Jack reviewed the "box score:"

Tom Made Jill come twice

Dick Made Jill come twice

Harry Made Jill come three Times

Mike Made Jill come four times

"Baby to you realize that every one of the john's you serviced are entitled to some sort of rain check? The first two guys can have you again all evening long and the next guy gets a weekend of service and Mike also get's a weekend but he will insist on deluxe diamond collar slave service whatever that means." Jack said. "I guess we can simply stiff these guys...."

"Not on your life!" Jill exclaimed. "I will not welsh out on promises we made to these guys. Besides I really can't see some truck driver traveling all the way to our home just for an evening of sex, so I do not believe that the situation will ever arise. If it does we will deal with it later." She calmly asserted with all of her accustomed aplomb.

****

Tom's Rain Check

Jill's 30th. Birthday passed serenely while the couple explored some of the scenic byways. The evenings included excellent dinning, Several glasses of good wine, strolls window shopping and passionate sex back in the motels along the way. Jack could not be happier at his wife's renewed sense of worth and personal self confidence. The 'tricks' in the bookstore were a spicy and fond memory. Jill had lived a fantasy and knew she was desirable and that she could hold her own in sexual encounters.

When they got home, the message light was blinking on their unlisted phone line. "Hi Jill, I hope you remember me, we met in that little store and I was the first....Uh ... Umm... well Jack called me 'Tom' .... Anyway I have a run up your way the middle of next month and would like to get together. See if you can free up the seventeenth but if not I can make either the sixteenth or eighteenth work. Call me on my cell phone ...."

"Well Shit! One assumption shot to hell! That guy is going to drive a couple of hundred miles to spend a night with you baby. Do you want to simply ignore his message and hope he will get discouraged...." Jack asked.

Jill rejected the idea she would welsh on a commitment so she promptly said "No Jack! We committed to this and I am going to go through with it! ....In fact the seventeenth looks ideal. Call "Tom" and suggest we meet at a motel near the interstate so he can park his rig nearby." Jill directed.

****

Jack came back with the plans. "Tom wants to meet at the SuperValu Truck Stop at the interstate exit 77. His rig has a sleeper, there won't be a record of having to take a room somewhere where you could be seen meeting him. I have a description of his truck and should have no problem locating it in the parking lot. Are you certain you are still willing to spend the night fucking this guy?" Jack finished.

"Yes tell him we will be at the Supervalu at 8. I will have eaten. I will bring condoms lubricants and toys. Jack, you should pick me up at 8 AM and take all of us to breakfast." Jill decided.

Having settled the logistics, Jack and Jill faced the intervening six days alternating between euphoria and dread. Some days she was petrified she would be abducted and sold into slavery. Other days she was bubbling with anticipation of spending a night with a stud who made her come twice in a 35 minute encounter. Jack's attitude also swung between fear of exposure and loss of intimacy to pride and being married to a very hot woman and proven sex dynamo.

Anticipation fueled several intense evenings during which both Jack and Jill strove to impress their partner with love for each other and their lovemaking skills. They were far more open with each other as to what specific actions each most enjoyed and the couple pushed their personal bedroom boundaries out since they both realized Jill would not have control of her boundaries when "Tom" redeemed his rain check for sex.

Jill also shopped for sexier and frankly provocative clothing so she would be 'dressed to impress' on the 17th. Each evening she modeled the ensembles for Jack. Gauging his enthusiastic reactions. Jill also skipped wearing bras or panties to emphasize the salaciousness of her ensembles.

The unlisted phone line rang again on the 15th. "Hi it's Tom. Is everything set up for the 17th.?

Jack answered. "Yes we will be at SuperValu at 8PM and I will pick Jill up at 8 AM. That should satisfy our promise."

"It certainly does!" Tom replied. "If you don't mind, I would like to speak with Jill for a minute..."

Jack handed Jill the phone, and she listened for several minutes occasionally muttering her agreement. Once or twice Jack noted that Jill blushed crimson and took a deep breath before answering but always finally in the affirmative. She hung up and looked anxiously at Jack. "You know I will always love you and always come home to you and deny you nothing you ask of me in the future?" She asked in a quiet and subdued voice. "Because I must now ask something very difficult from you. Tom wants me to be completely shaved down there and there is no way I can get a wax job from the beauty parlor in time so can you help me with this?"

"Absolutely baby, I am getting hard just thinking about shaving your pussy." Jack offered.

"This is the hard part honey. Jill said in a tiny voice."Tom wants me horney as I can be so he asked me to not have sex tonight or tomorrow so I have to ask you to not fuck me until you come home from work after I satisfy my rain check responsibilities...." She trailed off miserably looking at the stricken expression on her husband's face.

"Don't be mad! I will really make it up to you over the weekend. I really want to be emotionally ready to fuck Tom enthusiastically all night long, so a bit of a pause in my sex life before I show up will get me as worked up as anything." She added gaining some confidence.

The intervening 36 hours was stressful for Jack and Jill. Jack was jealous, concerned about Jill's safety and health and they were getting frustrated. Jill had 'performance anxieties' being unsure how a very pleasant 'quick trick' might be very different from an overnight assignation, she was less worried about safety and health but increasingly concerned about Jack's attitudes and his insecurities. Because she agreed to forgo sex, the couple lacked one of the proven methods to foster the sense of unity and support each felt for the other.

Things were pretty ragged when it was finally time to drive to the truck stop.

Jill's cell phone rang while they were enroute. "Hello.....We are on the way..... What Changes?...... I am sure that will be OK , but I am not dressed for a fancy restaurant. ... I am sure that will be fine."

"Honey," Jill said. "Tom wants to buy you and I dinner at the truck stop. He is feeling guilty I guess because he wants to tell you how he will make certain I come to no harm. He also said you must be some king stud to let your lady spend time with another man, but I don't believe he wanted me to tell you that. Dinner is on him." She finished noting Jack sit up straighter behind the wheel.

At the truck stop Tom had a table already back in the corner of the dining area. There was a bouquet on the table. Tom rose to greet them and held his hand out to Jack. "I cannot tell you how much I envy you having such a beautiful sensuous and adventurous lady to share your life. I can only guess how your home life is spiced by these adventures. Frankly I doubt I will be able to maintain the pace you no doubt set in the sack, so I asked Jill to save it all for me. That was not cool. I am sorry. I hope you don't think the less of me."

Before Jack could reply he turned to Jill handing her the flowers. "I cannot tell you how I have looked forward to being with you and taking our time. I will try to do my best with no time pressures. Now my lady, what would you like to have for dinner. They do not have a liquor license here but I have mixers and liquor in the sleeper of my truck."

Jill responded quickly. "Wow Flowers! Tom you make me feel special and I think I can speak for Jack when I say that these adventures do make memories that spice up things around the house. Now let's eat so I have the nourishment to make more memories."

Jack drove home an hour later in a much more positive frame of mind.

Jill's anxieties were a dim memory and her adventure gene was in ascendant mode. In the truck stop rest room she removed her panties and tucked them into her small overnight bag that Tom was carrying. He led her to his rig and unlocked the sleeper door with a remote. Jill grinned to herself as she contemplated climbing into the truck wearing high heels and visualized the view her would see looking up her short denim skirt. "If this doesn't prime his pump I will be a very surprised 'lady of the evening.'" She thought.

Sure enough Tom scrambled up into the sleeper with a haste that reflected well on the sex appeal of his hooker. Once the sleeper compartment was closed off Tom beckoned for her to crawl over to him. Jill peeled off her tube top and skirt leaving her naked except for the incongruous high heels. With her 36 C cups hanging down and her brunette pony tail hanging over her right shoulder Jill made a erotic vision as she crawled toward the john. He started to reach to unfasten his trousers but she brushed his hands away and took the initiative in stripping Tom.

Jill had never undressed a man. Jack always stripped himself eagerly. This was new and a bit submissive and exciting. After the shoes shirt and trousers were off, Jill eased Tom's briefs down . "Oooo that is lovely Tom, I really didn't take the time to appreciate it in the bookstore." She said sincerely. "I guess all your girls say something like that but I really mean it." She added. Kneeling at his feet she stared mesmerized at his cock while she peeled his socks off one by one.

Almost geisha like, Jill carefully removed each article of Tom's clothing, and carefully folded the garments and placed them out of the way. Once her john was naked, Jill massaged his cock to a complete erection, and then put a condom over his cock. Tom was quickly laying on his back and Jill straddling him. She assured her vagina was well lubricated and guided Tom's cock into her pussy. "Now Lover you just relax and let your little whore fuck you senseless." Jill purred.

Sinking down along Tom's cock Jill experienced the pleasure of both a truly great cock filling her cunt and the thrill of the illicit nature of the sex with a stranger. "Tom baby I want you to screw me. I want that wonderful cock of yours to push all the way into me. I want to ride this pony until I come and I want you to fuck me harder than you've ever fucked another woman. I love the feeling of your cock in my vagina." Jill panted and groaned.

Jill worked more and more of Tom's cock up into her pussy. Finally she had taken all nine inches of Tom in. She smiled down at her john and consciously contracted her kegle muscles. When Tom flexed in reply a delighted expression covered both faces. "Damm Tom you have some educated tool there." Jill gushed delightedly

"So shut up and fuck!" Tom teased her back "You have a really talented cunt. Use it! Get to work and ride my shaft. Think of me as a live Sybian. Whore, bounce up and down my cock. I want to see your hair flying and your boobs bouncing. I want you to work up a real sweat servicing me.

Starting almost playfully Jill rocked slowly forward feeling Tom's cock slide out of her vagina. Before it was completely out she paused and watched Tom's face for signs of impatience then clamping her internal muscles she rocked back sliding the delightful shaft back into her in one controlled motion. The sensation was awesome! Tom was not that much bigger than her hubby but he had great control and let her set the pace. Rock forward again, but this time Jill didn't pause long. She wanted the meat buried in her cunt. She was the impatient one! On the next cycle the downward stroke a resounding slap of flesh hitting flesh was produced. Jill's cycles of rocking back and forth had picked up-tempo and speed. She crashed down plunging his cock into her cunt. Tom was no longer playing the passive. His hips began to rise to meet Jill's downward thrust and the slapping got louder.

That was not the only sound effect and Jill began to groan and mutter " Shit! Fuck! Damm!" With each stroke.

The pace increased; the erolalia became more vivid and intense. Jill was clearly moving more and more into a zone where the only activity she could focus on was to increase her sexual stimulation. Louder and faster Jill chanted "Oh.... Oh Fuck! Damn I want to come soooo much! Fuck me! Don't stop! Harder Tom harder! Fuck me forever! " Until she began to shudder and her whole body began to shake as an orgasm swept over her.

"Boy you know how to please a girl" Jill whispered to Tom, when suddenly her eyes popped open "You are still hard." She exclaimed in surprise.

"Yeah Baby you went off like a firecracker. You are one hell of a hot hooker, but your job isn't done yet. I guess it is my turn to be on top." He said rolling them over to a classic missionary position. Now Tom set the pace of in and out. The withdrawals were slow and sensuous and the ins were hard and fast. Jill, exhausted from her exertions on top, caught her breath and then found a second wind. She started by encouraging her john "Tom you have a wonderful cock and it feels soo good inside me.. Tom, you are so strong I feel like a rag doll when you drive that thing up my cunt. "Oh! Tom I love what you are doing so please don't' ever stop."

Then her directions became briefer and more pointed "Oh don't stop doing that. Damm I love you're fucking! Your cock feels like a pile driver. Tom Please Fuck me harder."

As Jill wrapped her legs around Tom's torso and used her heels to drive is pelvis down on his inward thrusts the erolalia became louder and more explicit "Fuck Me! Do It Harder! Fuck my whore pussy! Drive it home! Damm! Fuck! Oh Damm."

Tom was now controlling the pace of the encounter and so he was able to escalate Jill's sexual arousal while damping his own automatic responses. As a consequence she was being maintained a level of arousal just below the climax and became increasingly wild as she tried to get Tom to push her over the mountain top. Jill's heels drummed on his buttocks, her pelvis lifted to receive each thrust her head thrashed from side to side.

Jill was now on the brink --she had never experience of primitive wild sex where few women could maintain any control at all of their responses. She thrashed and bucked groaned incomprehensibly and began clawing Tom's back as her erotic ululations increased in volume. Tom had long since given up pacing to stretch the encounter out. This woman's body had driven him to the point where all he wanted was to come in her cunt and feel his own release. He did manage to get Jill loudly to come before his release.

The couple dozed for a time and woke up again after 11PM. "Do you want to get cleaned up Baby?" Tom Asked. "We can shower in the Truck Stop and then come back here for another round." He said handing her a robe and slippers/

"Sounds delightful." Jill answered. "I have never been back in a truck stop shower."

In the main building Tom hit a problem. The private showers were being cleaned but no one was using the open showers behind the locker room, so the couple took a chance, and walked into the open shower hanging robes on hooks near the door. The chance to fool around with each other delayed the usual wet-soap-rinse quick wash sequence so they were still soaping each others' privates when the shower door opened and two more truck drivers walked in.

Tom was going to chase them out but Jill told him to let them watch, while she finished soaping and rinsing suds of her john. She also made no effort to cover herself while she took a final rinse and stepped out of the shower to dry herself off. The exposure gave both a real jolt. Walking back to the truck, Jill upped the ante by handed Tom her robe and climbing into his rig bare assed.

The rest, wash and exposure really recharged Tom's batteries and gave Jill all the stimulation she needed to initiate another round of enthusiastic sex.

For the rest of the night, the cycle of Fuck - Public Shower - Fuck again was repeated until the sun woke the couple a few minutes before Jack was to pick Jill up. For his part Tom had rarely had a more successful 'professional encounter' and slipped a fresh $100 bill into Jill's purse before handing her over to her obviously relieved husband.

On the ride back home Jill dozed exhausted but was jolted awake at Jack's comment that a voice message from "Harry " had been left on their unlisted phone line.......

To be continued....

tawriter
tawriter
117 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
26thNC26thNCabout 3 years ago
Despite

Despite Lickey's griping about the truth, this story really does suck.

betrayedbylovebetrayedbyloveover 9 years ago
Damn

I'll tell you what happens. She catches an std then gives it to her husband. He gets pissed when he finds out and leaves. No divorce. No trial separation. He takes off. She gets so distraught she attempts suicide and fails.

That's as far as I go. I don't give a fuck what happens after.

EgoTrixiEgoTrixiover 9 years ago
...to be continued..

...lool...when is that supposed to happen? Do you know how it goes?

AnonymousAnonymousabout 11 years ago
Yes the sickos love this

Great story.

LickideesplitLickideesplitabout 11 years ago
Anons...you want to bitch about sick?

This is technically an LW story. I think the pay2play aspect is stretching the definition a lot, however! I don't understand why the lady's pleasure (usually feigned, I am sure) obligates her to confer extra time and benefit! The John is willing to pay, the Sheila is willing to screw for that pay.

Moralists...go to the Incest category. You will find 'really socially unacceptable' behavior to grinch about! This story was pretty competently done, all things considered, within this genre!

Show More
Share this Story

Similar Stories

All For Her Husband Soccer mom's truck stop secrets.in Loving Wives
Hubby Wanted To See My Inner Slut Housewife gets sexy and has sex.in Loving Wives
Dirty Girl Tales from April's promiscuous past lead to sloppy-seconds.in Loving Wives
My Wife's Only Gangbang It was just supposed to be dinner.in Loving Wives
A Cuckold Made Hung lodger seduces wife and cuckolds a willing husband.in Loving Wives
More Stories