The fourth part of the story, finally!
David and Rob walked in quickly, “Did anyone see you?” Hilary asked. “No, that prying cow from next door was looking out the window, so we had to walk past your house once, but she didn’t see us come in this time.” “Good, so this must be Rob. Hello Rob” “Hi.” Rob replied timidly.
Rob was the only person who David had confided to about Hilary. Robert had seen Hilary a few times, ‘a true milf’ was how he’d described her and once David told him that he’d fucked her, he had not stopped asking if he could fuck her as well. David was unsure at first, but Rob was on old friend of his, and not being as handsome as David Rob had chatted up many ugly girls just so David could talk to their hot friends, so he figured he owed him one. Hilary was also hesitant at first, but agreed on the condition that David joined them, Rob was fine with this and they agreed to meet at midday on Wednesday.
Rob looked shy and lost for words so Hilary, not one for wasting time, said “Shall we go upstairs and get started then?” As she turned and walked off David laughed at Rob’s shocked expression. “Told ya she wouldn’t mess us around!” She was already half undressed when the boys entered her room and Rob practically ran to her to try and kiss her. She stopped him, “Not yet! You can stand next to David.” Rob did as he was told and Hilary lay on the bed, taking off her bra, then her panties, she lay on the bed and gave her big breasts a little jiggle. “Okay boys, let me see your cocks.” The boys looked at each other and pulled their trousers and pants down simultaneously. They’d both seen each other’s cock before, Rob was nowhere near as big as David, he must have been less than average, around four and a half inches long. Hilary didn’t mind, she knew that size didn’t matter. It looked tiny stood next to David’s fully erect nine incher. Hilary examined both the boys and slid a finger into her pussy, finding her pleasure button and flicking it playfully. “I want to see you masturbate for me, will you do that?” she asked. She needn’t had bothered, as both lads were furiously pumping at their stiff dicks, as this older lady dipped her fingers into her slit, and alternated her free hand across her double-D breasts.
She closed her eyes and thought about how often she had used to lay in bed, satisfying herself, as her husband had been unable to for years. It wasn’t that he didn’t try. He’d always had problems with premature ejaculation. Hilary didn’t blame him, she had only slept with one man who had lasted longer than fifteen minutes but he was married and was so guilty about betraying his wife he never spoke to Hilary again. She met Mr Johnston when she was young and never imagined that his swiftness in bed would be a problem, but every night she would be frustrated but her husbands excuses and would spend the next morning with her hands between her legs, wishing she could have someone inside her who wouldn’t leave until she had had her orgasm. She found that with David. She wanted that now. Opening her eyes she could see both boys had slowed down, each one not wanting to cum before the other. She winked at Rob, “Do you need me to show you where to put it?” “No ma’am!” he said, rushing to the bed, still with his shirt and trousers on, she was waiting, holding her vaginal lips open, ready for the little penis which was ready to invade her tight hole. He plunged straight in, moaning deeply as Hilary’s warm lovebox surrounded his hard cock. He wasn’t as composed as David had been and his David was trying not to laugh as he watched his friend fuck his ‘milf’ without thinking about whether the ‘milf’ was enjoying herself. Short, stuttering thrusts, his hands only on her nipples, leaving masses of her chest unattended. Hilary was being polite though, “Oh Rob, you’re so BIG Rob, so GOOD!” David nearly laughed again as Hilary faked an orgasm. He knew it was fake as he’d seen Hilary have so many real ones. Just as Hilary finished her ‘orgasm,’ a full two and a half minutes after he’d began, “Oh fuck!” Rob shouted. He thrusted his little cock deep into Hilary’s slit and groaned as he spilled his spunk into her. He lay there for a few seconds and pulled out, lay next to her and began to pull his pants back up. It reminded Hilary of how her husband used to be, but this time she wasn’t frustrated, Rob was just the starter, her main course had undressed and was crawling up her body. “Get on top.” David told her. She did as she was told. David wanted to show his friend how he should have fucked his ‘milf’. He was going to give Rob a real show. Hilary lay flat across her lover and as David eased his cock into her she whispered in his ear, “Please give me a real orgasm this time!” He chuckled and slid his meat balls deep into the older lady’s cunt, making her whimper into his ears. Rob had been sitting on the chair across the room and looked on in admiration as his friend sunk all nine inches in. David made a couple of thrusts before Hilary sat upright, her hands on his chest, and began to lift her hips up and down, sliding her wetness all over the big rod between her legs. David grazed his hands across her flat stomach and drifted them to the large tits in front of him, bouncing like basketballs, he gripped each one and ran his nails along the underside of them before finding the erect nipples and flicking and twisting them. It was all too much for Hilary, the anticipation and wait she had to endure, the cock which felt like a thick twelve inches in her small, tight pussy, the expert hands all over her boobs, she couldn’t hold back, she let her head fall back and growled deeply, “Yes, that’s it, fuck me, you stud, I’m going to cum!” David kept his tempo as his lover jerked and writhed on top of him. David knew this was a real orgasm, he could feel her cunt tighten, but he held back, not wanting to cum just yet.
Meanwhile, Rob had his cock back out and was stroking it fast. He had watched plenty of porno films but this was better than all of them! He watched David’s cock disappear and reappear from Mrs Johnston’s pussy and was amazed at how he could have such a sexy woman riding him yet not cum as soon as he had done while fucking her. He knew he was quick, but he didn’t care. Of course, he would like to last longer, but how could he? His biggest fantasy was to have sex with a milf, and Hilary was the perfect milf. A body women her age would kill for, perfect breasts above a flat stomach, her neat, trimmed pubic hairs framing the best pussy his little dick had ever been in. An arse which looked so good rising and falling around his friend’s cock, and long legs which felt great when they were wrapped around him, pulling him in deeper. It was probably the best two and a half minutes Rob would ever have, unless David’s stories about Hilary’s blowjobs were as good as he said.
He didn’t want to interrupt this scene which had been going on for about twenty minutes now in front of him, Hilary had been having orgasm after orgasm, and even Rob knew that you should never stop a woman half-way through an orgasm, but his throbbing cock just could not wait. “Hey David, do her from behind so she can give me one of those blowjobs you told me about.” The two lovers slowed down and Hilary sighed as the cock slid from between her legs, she quickly turn on all fours and the large beast slid back in, bringing back the smile to her face, she licked her lips in anticipation of the oral sex she was about to give to the little cock presented to her. She took the penis into her mouth and took it all in, up to the balls and Rob’s head fell back as he groaned. David was pumping at Hilary’s pussy and smiled as he remembered how his first blowjob from Hilary felt. He wasn’t sure if he preferred her cunt to her mouth. While the cunt was tight and warm, her mouth was so skilled at what it did and she took great care in giving blowjobs. He glanced down at his cock descending into her hole and saw her arsehole, he wondered what that would feel like, tighter than her cunt? No way. Another time, perhaps. Hilary’s tongue was circling Rob’s cock sending the youngster to heights of pleasure he had never experienced through oral sex. Hilary was really getting into it as well. Using a spare hand to rub and caress his bulging balls and groaning and sighing all over the meat in her mouth. These moans weren’t fake, and it wasn’t just the big cock in her pussy that was making Hilary feel so good.
Hilary was 16 when she gave her first blowjob. The guy was her older sister’s boyfriend, Carl. Hilary adored Carl, he was 19, the same age as her sister and Hilary fancied him since the day her sister brought him home. Unlike Hilary, her sister had never enjoyed sex. Even now, when Hilary went round to meet her sister, she could see how sexually frustrated her husband was, always giving longing looks to Hilary, staring longingly at her chest. It was a shame. Most men would have looked elsewhere for sex, but her husband had stayed loyal, unlike Carl. He would come round to the house when he knew Hilary would be alone, talking to her, complimenting her, it was only a matter of time before she gave in to her feelings. She didn’t know that Carl only used her for sex, she thought it was special, what she had with Carl, and that’s why when Carl pulled his pants down and asked Hilary to put his penis in her mouth, she duly obliged. She wasn’t sure what to do with it at first, she opened her mouth and put it in slowly, kissing it and sucking it softly. It was the first time she’d even seen a cock but what she lacked in experience she mad up for in enthusiasm, quickly learning that when Carl moaned, she was doing something right. She grew to love the feeling of control she had when a man put his cock in her mouth and it wasn’t long before she would do nearly anything to give oral sex, whether it was on a bus, in class, or even with people she really shouldn’t have been sucking off, like teachers. Well, with all this oral sex, how else was she supposed to get an A? She learnt all she needed to learn about sucking cock from Carl, she lost count of the number of time he spilt his sperm into her throat. She would frequently visit his house for sex sessions that would always end with Hilary getting on her knees and take a shot of spunk in the mouth, sometimes of course, Carl would cum quicker than expected and spray his load all over Hilary’s chest which she hated. She soon learned though that men loved the visual delight of ‘marking his woman’ with his sperm. Which is what she thought Rob was just about to do.
She felt his balls tighten and constricted her mouth around his cock, speeding up the momentum of her head bobbing up and down on him, he grunted and dumped his hot load into Hilary’s waiting mouth, she swallowed it all, she loved the taste, and licked the young man clean before he sat back in the chair, content. The sight of his best friend having his second orgasm in an hour was too much for David, he grabbed both of the arse cheeks in front of him and rammed Hilary’s cunt for all it was worth, making her buck forward, it didn’t take long before David grabbed her swinging breasts, lent forward while holding her tight, grunted deeply and erupted inside her. He brushed the hair on her shoulders aside and kissed her neck and left ear as she melted into his shoulder. He pulled his long cock out and it made a delicious slurping noise as Hilary’s sweet juices dripped down it.
“Wow. That was incredible!” Rob said, he was amazed, he knew David was something of a stud, but to see him in action, how he made Hilary buck and moan, it was amazing. The two lovers lay next to each other on the bed. Rob could see a mix of David and Hilary’s cum dribbling down the inside of her thigh. Rob knew when he was younger that because of his smaller cock, he would have to work harder on other aspects of his sexual performance. He had spent plenty of time between the legs of previous girl friends finding out what made them tick, so that he could most of the work orally, this meant he could spend less time with his cock, which worked for him as he could never last as long as he would need to. The sight of Hilary’s freshly fucked vagina was very empting to Rob, he crawled up on the bed and pushed apart her thighs just enough to fit his head in, he slowly poked his tongue out and ran it around Hilary’s inside thigh, licking up all the juices, they tasted great, he’d never tasted another man’s cum before, but mixed with a woman’s it wasn’t as bad as he thought it might have been. His tongue followed the trail to Hilary’s moist vaginal lips and he dragged his tongue along the edges, making her quiver in delight. Rob couldn’t see her face, but she was smiling contently, enjoying the anticipation of the oral attention she was about the receive. With two fingers, Rob opened her glistening lips and thrust his tongue in, enjoying the strong taste of her. He moved up to the bulging clit and worked on it, while sliding two fingers deep into her little fuck hole. She began responding to this, groaning softly and moving her hips to meet his thrusts. David was enjoying what he was seeing as well, and as his cock began to grow, he positioned himself so he could slide it into Hilary’s open mouth, as her eyes were closed, she didn’t expect the large rod to enter her mouth, but she knew exactly what to do once it had, clamping her mouth on it and sliding her tongue around it with the new energy she was getting from the good oral sex she was receiving from the man between her legs. The three lovers were all in ecstasy, moaning and groaning, when suddenly Hilary took the cock out of her mouth and said something which shocked both the boys:
“How do you guys feel about double penetration?”
The two boys looked at each other and smiled, double penetration was something they’d always thought about, but they’d never found a woman willing enough to even talk about it.
“Well, is that a yes?” Hilary asked impatiently.
“Sure!” The two boys said together excitedly. David knew where his cock wanted to go, straight in that arse that had been so inviting all the time he had seen Hilary naked. As he started to sit upright, Hilary put her hands on his chest and pushed him down.
“Where do you think you’re going?”
“I…I wanted to come in your backdoor…” David said.
“Oh no, not today, fitting that thing in my little bottom is something you and I will have to work on together. Alone.”
David sighed, but he understood, he lay down and held his cock up straight as Hilary slid down on it. She gasped as she took it all in, and whispered softly in his ear,
“Don’t be sad, dear, we’ll arrange a meeting soon, just you and I, and you can plunge that thing into my arse as much as you wish.” David smiled and watched the smirk on Hilary’s face disappear as she scrunched her face up. Rob was sliding his stiff cock into her tight arse.
“Oh my, David, you will not believe how good this feels!” said Rob as he got balls deep into Hilary’s rear end. She now had two rock hard cocks inside her, it hurt a little more than she had imagined, but as the two young men built up a gentle rhythm, her whimpers of pain turned into gasps of pleasure as her arse and her cunt gradually adjusted to the stiff rods inside them, and the two young men were enjoying themselves as well, Rob showing the self control and confidence most men have after cumming twice in a short period of time, and David enjoying the sensation of Hilary’s tight pussy around his dick so much he nearly forgot why he wanted to fuck her in the arse. Hilary felt like a porn star, sandwiched between these two young studs, having orgasm after orgasm, it felt incredible, just to think, it was only a few weeks ago that Hilary was laying in bed alone wishing she had a nice hard cock, and now she had two! She suddenly felt the urge to be the best porn star she could be, she bucked her hips as best she could and groaned her way through another orgasm, before looking at David, then Rob as she said,
“I want you both to cum all over my chest.”
This nearly sent Rob over the edge, he still was not used to a woman of Hilary’s age using the type of language he would see in dirty movies. David, however, was quite used to this, and replied,
“Sure, lay on the bed.”
She did this, and smiled as the two boys fisted their meat over her, their eyes wide as they took in the sight of the beautiful woman in front of them. David was the first to cum, which was a surprise to Hilary, she had her eyes on Rob as she thought he would shoot first, and was only aware of David’s orgasm as the first beads of cum hit her right in the middle of her chest, the next few shots were not as accurate, splattering across her nipples and dripping down onto her stomach. Rob was frantically masturbating, chasing his orgasm as if his life depended on it, Hilary licked her lips in anticipation, and shook her breasts softly from side to side, carefully rubbing David’s cum into them. She kept eye contact with Rob as he came, even as he closed his eyes while big gobs of cum sprayed all over Hilary’s large chest, and even her chin. He had to lay down, next to David, exhausted, while Hilary rubbed the two stud’s cream into her chest. She looked at them and grinned.
“Hubby’s gonna be home any minute, I think you guys should get home now. I hope you both enjoyed yourselves.”
“Yes Ma’am!” They both said as they began to get dressed.
As they were leaving, Hilary grabbed David by the shoulders and whispered,
“I’ll see you soon, lover.”