Ann and Will were an older couple that enjoyed sex and exploring their fantasies. Since meeting on Lush several years ago, they had gone from being cyber-lovers to physical lovers. As they became physically connected, they had found many ways to enjoy each other. They never failed to try something new in their relationship if one or the other wanted to try it. This had broadened their sexual appetites in many ways and found them always stretching the boundaries of what each other would do.
Will had been gone working for a few weeks and Ann had to stay behind for a change. She had a few doctor’s appointments and also needed to be around to take delivery of some furniture they had bought. She was bummed out over being forced to stay behind. Will as normal had just rolled with the bunches of it all, which had irritated Ann to no end.
Sex while traveling with Will was such an almost everyday thing, so she was feeling just a bit over-horny for his cock. Although since meeting Will, she had started experiencing new and more exciting aspects of sex, her masturbation still came down to mostly her fingering herself and teasing her clit until she would explode in orgasm. Will had bought her a few vibrators and dildos but she never got comfortable using them. She just had never had them to get comfortable with before.
So, Ann figured if she had to be horny, the least she could do was keep Will as horny while he was gone. She would send him IMs at all times of the day with GIFS attached or sexy postings. She was relentless and for his part, Will was being a good sport and sending her things in reply. The thing he didn’t know was how horny Ann had gotten without him there or not being with him traveling.
Will could tell by the end of his two weeks away Ann had become a horny mess. She was sending him a nonstop stream of postings, pictures, and GIFS of all kinds of sex acts and innuendo. Trying to consider what to about her was another matter though. He didn’t want to let her off the hook for all the teasing she had done to him.
After considerable thought and a small amount of planning, he decided she needed to be teased until she could stand no more. So, Will settled on his course of action and he happily let her send away with her messages teasing him.
Will got into town about two in the afternoon but didn’t run home right away. Instead, he called Ann and told her he would be home at four-thirty sharp and that she needed to be dressed to go to dinner, they had reservations for five at her favorite Italian place a town over. Ann moaned and groaned about wanting to stay home since Will had just got home after two weeks.
Will didn’t budge and told her that he had been craving Italian all week. So, she changed her attempt at persuasion to get out of dinner by asking if he didn’t need to shower first? Will was all set for this and told her no, he would shower at work and change into his nice clothes he carried with him for emergencies. Dejected, Ann finally gave and told him she’d be ready. She just didn’t say for what!
Will arrived home exactly at four thirty. Ann had been watching for him and set her plan in motion. She ran over to Will’s favorite chair in the living room and sat down.
Will came through the back door and called, “You ready to go Ann? We need to get moving!”
“I’m in the living room, come here I need your opinion on what I’m wearing,” She replied.
Will stepped into the living room and saw Ann sitting there in a sexy babydoll outfit in his chair. He studied her for a minute and his resolve weakened in his plan of action but after taking her in for a few heartbeats stiffened his resolve.
“I love what you’re wearing but the restaurant might frown upon it.” Turning away from her, he looked back and said, “I’m going to go through my mail while you get dressed but be quick so we are not late.”
As he disappeared back into the kitchen to look at his mail and hide his raging hard-on, he heard her say, “Fuck, double fuck!”
Then he heard her get up and move towards the bedroom. He was sitting at the table sorting his mail when she came back out about five minutes later dressed in a medium blue dress that came down just above her knees. He hated to tell her but she was sexier now than sitting there in the baby doll outfit. It might have something to do with the natural flush in her cheeks from being pissed off because he ignored her in the chair.
“You ready to go?” Ann hissed at Will.
“Sure, babe!”
They headed out the door and since Will’s pick up was parked behind the car he went to it and opened the passenger door for Ann. She wasn’t thrilled about taking his truck either since there was no way to reach him with the large center console. Ann didn’t know it but that was part of Will’s plan too. He was doing his best to deny her any chance at physical contact that could lead to other more intimate things.
After closing Ann’s door and going around to get in, Will leaned across and caught Ann by the chin and gave her a tongue dancing kiss. As soon as he felt her lean in and try to make more of it he pulled away and straightened up in his seat leaving her still leaning over the console. Starting the truck, he backed out of the driveway quickly leaving Ann looking at him pouting.
They got to the restaurant and Will parked. Before he could get out to open the door and help Ann out, she was already walking towards the restaurant doors. He knew she was pissed at him but also knew she would get over it eventually.
They got inside and the young hostess seated them in one of the romantic little booths along the walls. Ann slid in with Will right behind her. At first, she kept a little distance between them. Her way of saying, ‘I am mad at you,’ but as they settled in and ordered drinks and an appetizer she scooted closer to Will. She finally gave in and snuggled against him as they sipped their wine and shared the appetizer.
Will decided this was the perfect time for some of the payback on the teasing front he had been getting from her over the past two weeks. He slipped his hand down to her left knee and gave it a gentle squeeze. As he did that, Ann snuggled tighter to him. He slowly worked his hand up from her knee until he was massaging the top of her thigh. He slowly worked his around until he had slid it under her dress and was on her bare inner thigh, just inches from her pussy. He could swear it felt like a furnace heating up she was so horny.
Ann spread her legs a little bit further apart to give Will access to her thigh. She wasn’t worried about being seen, knowing the table had a floor length tablecloth on it. She tried to place her hand on Will’s thigh but he moved away slightly. Not sure what he was playing at, she decided to just enjoy what he was doing to her.
Will continued to work for his hand along her thigh. He slid it all the way around until his fingers were curled underneath, but he’d stop just short of reaching her pussy each time. Ann was scooting herself down in the seat trying to get him to play with her pussy. He kept getting agonizingly close but never touching her.
On a few occasions, he would graze just the very outer edge of her sex. Ann was going mad by the time dinner arrived. Will kept up his teasing of her all through dinner and even though Ann loves the dessert there, she declined dessert trying to get Will out of there and home.
Will continuing his teasing ways that evening ordered a huge slice of cheesecake and ice cream to enjoy. He slowly ate it all the while taking the time to continue rubbing Ann’s thigh every so often. Never quite reaching her very hot, almost smoldering pussy.
Finally finishing his dessert, under the glaring eyes of Ann, he asked, “Are you ready to head home, love?”
Ann looked over at me and just her eyes said, ‘Are you really fucking asking dickhead?’ But she really replied, “Yes, I’m ready to head home and fuck your brains out!” Sweetly smiling the whole time.
They went out and got in Will’s truck. Will helping Ann up in the truck as he usually does, couldn’t resist rubbing her ass as he boosted her in. This earned him an evil glare from Ann, whom he expected was reaching the end of her tolerance with his teasing.
Pulling out of the parking lot of the restaurant, Will looked over at Ann and asked, “Are you horny enough to fuck anywhere?”
“Just pull over and you’ll find out,” Ann replied.
Will didn’t say anything to her in reply but instead kept driving towards home. He came to a stretch in the road where it had a small side road paralleling the main road. He took a cut off over to the smaller road. Ann just looked over at him wondering where he was going.
Will kept going until he reached a little pull off that was ideal for what he had in mind. It was surrounded on three sides almost to the road by trees and open at the front towards the side road and the main road. Pulling in, he swung the truck around so it was facing the roadway and deep enough in the pull of so you couldn’t see the rear of the truck without being right on top of it.
Looking over at Ann, he said, “I’ve pulled over and I’m ready to find out!”
Ann’s eyes went wide with that. “You got to be kidding? This along a public road for god’s sake!” Ann was almost yelling as she was speaking to Will.
Will, being the patient guy, he is, just sat there until she wound down before speaking again. “You’ve teased me for the last two weeks unmercifully. I’m not going tease you for two weeks but I am going to call your bluff. So, put up or as the saying goes, shut up!” With that, Will open his door and got out of the truck.
Ann just sat there for a minute, simmering somewhere between being pissed off and being so damn horny she could’ve fucked for a week. Finally, being horny won out. She opened her door and slid out of the truck walking towards the back. As she rounded the corner, she could see Will had dropped the tailgate and there was a couple of blankets laid put on it. He was reclining against it waiting on her. She realized exactly how serious he was about this. He truly intended to fuck her here along the roadway.
Not giving her any more time to think, Will reached out pulled her into his arms, kissing her hard and deep, slipping his tongue between her lips to dance with hers. Ann responded in kind letting her tongue dance with his. Will’s hands slid from her waist until he was cupping her ass. He lifted her up and sat her on the pickup’s tailgate. As they continued to kiss Will was letting his hands roam over her breasts, kneading them through her dress, teasing the nipples. This was leaving Ann moaning in pleasure that was building into a fire of need in her core.
Will, tiring of the dress, reached behind Ann and slipped the zipper down her back. Ann in her state of arousal never protested as he pulled the dress off her until it was bunched at her waist leaving Ann naked from the waist up. Will wasted no time taking advantage of her bare breasts. Leaning forward he sucked one nipple and then the other into his mouth. He continued alternating between them, taking his time to twirl his tongue around each nipple. He would pull back and lick across each nipple before returning to sucking them. Ann had her head tilted back moaning in ecstasy as she held onto Will’s shoulders to steady herself.
Will started working his way down Ann’s tummy until he slipped his hands around her hips, pulling her ass closer to the edge of the tailgate. Having her where he wanted her, he kissed along her tummy until he was just above the bunched-up edges of her dress. Needing to get it out if the way, he grasped the bunched-up material and gave it a hard tug. Ann realizing what he wanted, lifted her ass off the blanket and Will pulled her dress completely off, tossing into the bed of the truck. Now Ann was left sitting there completely nude for anybody to see.
After tossing the dress onto the bed, Will wasted no time going after what he wanted. Reaching for Ann’s legs, he lifted and parted them causing her to lay back on the blankets. He placed a leg over each shoulder and lowered his mouth to her glistening wet pussy. Will ran his tongue over her glistening slit, tasting her, enjoying the tangy flavor. He slowly worked his tongue over her lips from top to bottom and back, letting it part her ever so slightly. On one pass, he flattened his tongue out and lapped her clit like a dog drinking water.
Ann was now withering on the blankets in the ecstasy of Will’s actions. She could’ve cared less if she had been on a stage in the middle of the road at this point.
She just needed more and wanted to cum so bad she was pleading with Will, “Please make me cum baby, please!”
Will heard her pleas but wasn’t going to let her reach that point until he was good and ready. He worked his tongue deep into her pussy, running it over her sensitive flesh each time. Using one hand he started to rub her clit back forth, feeling it swell even more under his touch. He continued to tongue fuck her as deep as he could, but Ann was whimpering so bad, it was taking a lot effort to hold her hips still to continue eating her pussy.
Deciding it was time to let her cum, Will slipped several fingers into her pussy, pumping them hard and fast. He replaced his fingers on her clit with his lips, sucking and licking it in time to his fingers pounding in and out of her pussy. He could feel her orgasm approach and it was all he could do to hold her still as she was almost bouncing off the bed of the truck in her excitement.
Ann finally tensed and arched her back, forcing Will’s fingers deep as she started cumming. Will felt her juices run over his hand and he pulled his mouth away from her clit. He tasted her on his lips. Looking at her, he could see the well of need emptying from her body. Finally spent, she just collapsed on the blankets breathing heavily.
Although Ann’s needs had been met for the moment, Will’s had not. He slipped his pants down freeing his hard cook. It was then he realized he couldn’t fuck Ann laying the bed of the truck. He decided that was no problem. He reached out grabbed her legs pulled her to him until she was standing unsteadily on the ground in her heels and nothing else.
Will kissed her and said, “It’s my turn!”
With that, he turned her around and bent her over the tailgate. It bent her over at just the right angle for Will to step up behind her. He rubbed his cock along her ass and between her legs enjoying the feel of her skin on his hard cock.
Ann feeling this knew she was about to be fucked hard in her favorite position. She always liked to be taken from behind and when Will was more forcible about it, the better it felt. She knew it wasn’t going to be gentle here and now.
Will slipped his cock into her pussy and pushed hard and deep in the first stroke, pinning Ann to the tailgate. He pulled his cock from her pussy and repeated the hard entry over and over, pounding Ann hard against the tailgate with each thrust. Ann loved it and the feeling was pushing her to another orgasm quickly.
Will was not slowing his assault on Ann’s pussy at all, but he wanted her to feel how horny she had made him. He slipped a finger along her pussy gathering her juices on it. He started rubbing it along her anus that was nicely exposed with her bent over this way. He rubbed it around the rim of her opening, teasing it. As his finger would dry he would re-wet it with her juices and continue to tease her anus until he finally slipped his finger into her. Giving it a little pressure, he slipped it into the first knuckle.
This set Ann off onto another hard orgasm. She stiffened and her pussy tightened on Will’s cock. Will could feel her juices running out along his balls and down their thighs together.
Will, knowing he wasn’t going to last much longer, wanted this night to end in a special way. Pulling his cock from Ann’s pussy and his finger from her asshole, he positioned the head of his cock at her tight hole. He pushed against her causing Ann to gasp. They had been building towards anal sex for a while, but Ann would have never guessed her first time would be alongside a busy road in plain sight.
Will kept pushing until he had got past the outer ring of Ann’s anus but knew the harder part would be to get beyond the inner ring. Ann grunted and let out a little cry of pain. Will kept applying pressure until he felt the tighter inner ring give way. Ann cried out again but never asked him to stop.
Taking his fingers, he gathered up some of Ann’s juices and rubbed it along his cock as he continued to push into her tight asshole. Ann was whimpering, but he could feel her pushing back against him as well. Will finally had his entire cock buried in Ann’s asshole. His balls were resting against her. He held still, letting Ann recover from the entry.
After giving Ann a few moments of recovery, he started to slowly work his cock back forth in short easy strokes. This set Ann off moaning again, but this time in a pleasure filled way. She lifted up against Will to work her hand to her pussy. She slid her fingers around her clit and started stroking it in time to Will’s motion.
Will was slowly increasing both the speed and length of his strokes in Ann’s asshole. He was pulling almost three-quarters of the way out before sliding back in deep with each stroke. The feel of Ann’s asshole hugging his cock brought him to the edge. Each thrust was heaven to Will.
Finally, unable to hold out any longer, Will let out a grunt and slammed his cock into Ann’s asshole letting loose of his built-up load of cum. His cock pulsed as he emptied himself deep into her. He held onto her hips holding himself in her.
This was too much for Ann. Pinching her clit in her fingers another orgasm ripped through her as she felt Will’s cum fill her ass. With Will holding her she couldn’t do much more than tremble as her third orgasm of the evening ripped through her body. When it finally subsided she just laid over the tailgate totally spent, hoping Will was too. She didn’t know if she had any more left.
Will, finally regaining his composure, slowly pulled his cock from Ann’s asshole. Ann moaned a little as he was doing it. As it slipped out, a small trail of cum came with it. Looking at it, he knew there was more in her ass than that. Stepping back, he pulled Ann up and turned her around to face him. He could see her makeup was a wreck, but she had the look of a well-fucked woman on her face too. He pulled her into him and hugged her, then gave her a long lingering kiss but not one of need but of passion and love.
After the long kiss, he asked, “Are you okay? I didn’t hurt you, did I?”
“No silly, I’m just fine. Maybe a bit sore but that was to be expected. I do think we need to head home though. I feel like I need a good hot shower.”
Ann turned to look for her dress and saw it was all the way up in the front of the bed by the cab.
Will, seeing what she was looking for, grabbed the bottom blanket and wrapped it around her. “This will get you home.”
Will took a moment to pull his own pants up then led Ann around the truck and helped her get in. He went back around to the tailgate, tossing the other blanket further up in the bed before shutting it. It was then that Will saw the car parked at the front edge of their pull off. Thinking to himself, ‘I wonder how long they have been there?’
Seeing him looking their way the car quickly took off. Will shrugged and went on around to the driver’s side and got in. He looked over at Ann and she had her head back and looked asleep. Starting the truck, he slipped it in gear and pulled out smiling to himself. It had been a good night.
