On a New Year’s vacation to New York City, innocent, inexperienced Midwestern wife Olivia discovers that some men are blessed with far more between their legs than her husband Carter. Join this loving married couple on an erotic cuckolding journey as they explore their newfound sexual desires together and reach heights of pleasure they never imagined possible. This is the first part of their journey. If you want to read the rest, become a Patreon supporter at the stories tier.
“Oh my gosh!” Olivia said as she stared at the sex toys in the window display of one of the West Village’s few remaining sex shops. She looked at the New Yorkers rushing by her with confusion on her face, seemingly wondering why everyone wasn’t stopping to stare at the dildos, vibrators, and kinky outfits on display. She seemed confused, uncomfortable, and a little annoyed all at the same time.
“Can you believe this?” Olivia asked her husband, Carter, as she continued to stare at the sex toys in the window. “I mean, why would they be allowed to put this kind of stuff on display in public?” she said in a quiet voice meant only for Carter to hear.
Unsure of how to answer his wife, Carter simply offered, “This isn’t Minnesota, honey. New York is a different kind of place.”
“I know that,” Olivia said with a hint of annoyance in her voice. “I’m not a baby, Carter. It’s just, do people even use these kinds of things?” she asked pointing to the many toys on display in the window. “Why would they need them?”
Carter smiled at his wife’s innocence. To passersby she might have seemed like an overly conservative, reactionary rube, but he knew she was just a sheltered Midwestern girl. She grew up in a small Minnesota town, went to a small college, and married him shortly after they graduated. She just hadn’t seen much of the world. Going to New York City to celebrate New Year’s was the most adventurous thing she’d ever done.
Even though Carter didn’t have much more experience to boast about, he lacked his wife’s seeming desire to stay ignorant to the wider, sometimes weirder world of sexual pleasures. He’d never tell her, but he frequented PornHub on the occasions when he had time alone to enjoy a bit of solo pleasure.
“They make sex more fun for some people,” Carter said as he took Olivia’s hand in his. He pointed to one of the vibrators in the window and added, “Plus, some women use toys like that to have a little fun on their own.”
Olivia looked uncomfortable and Carter knew it was at the thought of a woman masturbating. He still had trouble believing his wife had never enjoyed a sexual fun on her own, but Olivia insisted that she’d never masturbated and she didn’t understand why any woman would.
“What about those? Those are ridiculous,” Olivia said as she pointed to a handful of boxes displaying rather large, lifelike dildos. “I mean, they say those are realistic but look at how big they are.” She leaned closer to Carter and whispered the last few words, seemingly embarrassed to be commenting on the size of a sex toy.
Carter sometimes forgot he was the first man his wife had ever been with. It took moments like this one to remind him that she’d been a virgin when they met and had shown no interest in exploring sex with other people before settling down. Marriage is what she craved and Carter had fallen head over heels in love with her and couldn’t wait to propose.
Carter was about to tell his wife that the sex toys, which were no more than nine inches long, were actually well within the bounds of realism when he was struck by an unexpected wave of insecurity. He was the only man Olivia had been with and given her relative innocence she just didn’t know that men came in all shapes and sizes.
“Those are actually realistic,” Carter said. “Not for most men, of course.”
Carter watched his wife to gauge her reaction, but her face betrayed very little. If anything she seemed a little confused by the new information.
“Well, I’m hungry,” she said after a long stretch of silence where she simply stared at the window of the sex shop.
They continued down the street towards their lunch destination and Carter smiled again at his wife’s utter fascination with a fairly tame selection of sex toys. He wondered what would have happened if they’d gone into the store and she’d been exposed to the kinds of things they can’t put in the windows.
That night in their small, lovely room on the 23rd floor of a Midtown Manhattan hotel, Carter found it difficult to stoke his wife’s interest in having sex. Despite her inexperience and relative innocence, Olivia was usually an eager, passionate lover.
She seemed distracted more than disinterested, but Carter couldn’t figure out how to win back her focus.
“Is everything okay?” Carter asked in a casual but concerned tone as he ran his fingers over her the smooth skin of her stomach.
Olivia sighed. Carter could see the frustration on her face. “Are those…things from the store window…are they really realistic?” she asked.
“What things?” Carter asked.
Olivia looked sheepish as she turned and rested her head against Carter’s chest. “You know, those toys,” she said in a soft whisper.
Carter was genuinely stunned that his wife was still thinking about the sex toys they spotted earlier that day.
“Oh, well, yeah,” he said haltingly.
Olivia said nothing as she ran her fingers through the sparse hair on Carter’s chest and stomach. He desperately wanted to know what was going on in her head but couldn’t bring himself to ask.
Finally, she spoke up. “So, there are guys out there that are,” she hesitated for a moment before saying, “really big?”
When Carter looked down all he could see was the top of his wife’s head. He wished he could see her face to try and gauge what she was getting at. He wasn’t sure how much she really wanted to know and he worried that the wrong answer could upset her in an unexpected way.
“Yes,” Carter said. “Lots of them, in fact.” He silently scolded himself for adding the last part. He wasn’t sure why he felt the need to inform his wife that lots of guys were blessed with more between the legs than he had to offer.
Carter was surprised when Olivia gently moved her hand into his boxer shorts. She stroked him casually, like she was doing it absentmindedly instead of with the purpose of arousing him for sex. It felt good regardless.
“Do you think you could show me?” Olivia asked.
Carter was befuddled. “What?” he asked.
“Could you show me what it looks like when someone, you know, big, has sex?” Olivia said in a quiet, shy voice.
Carter felt like he was in uncharted waters with his wife. “You mean, like in a porn video?” he asked, hoping he wasn’t totally off base.
Olivia’s slow stroking had given Carter an erection and the idea that his wife wanted to watch a big cock porn video only excited him further.
Carter swore he felt her smile before she answered, “Yes.”
He hesitated. They’d never talked about porn before and he wasn’t sure it was wise to admit to Olivia that he’d watched it. Carter felt like she might be furious if she knew that he occasionally watched and masturbated to porn.
“Well, I guess I could try and find something,” he finally said.
“It’s okay, honey,” Olivia said as she sat up and release Carter’s cock from her soft grip. “I know men watch porn. I’m not an idiot.”
“I know,” Carter said. “I’m sorry.”
He reached for his phone and opened an incognito browser session as Olivia snuggled up next to him. Feeling deeply self-conscious, Carter typed in pornhub.com and tried to act like he wasn’t intimately familiar with how to navigate the site on his phone.
Without looking, he tried to gauge Olivia’s reaction to the hardcore thumbnails on the main page before clicking the search button and typing ‘big cock amateur sex.’
“Amateur?” Olivia asked.
“You don’t want the professional stuff,” Carter said. He regretted showing a little too much familiarity with porn.
Olivia didn’t seem put off by it. “Why?” she asked.
Carter suddenly felt like the shy one. He wasn’t sure it was wise to share his thoughts on professional versus amateur porn with Olivia, who he felt certain had never watched this kind of thing before.
“It’s mostly bad sex in uncomfortable positions, honestly,” Carter said, keeping his thoughts concise.
“Oh,” was all Olivia said as Carter swiped upwards on his quest for an ideal video.
“What about that one,” Olivia said in a surprisingly eager voice as a thumbnail showing a girl riding a rather large cock in POV appeared on Carter’s phone.
Carter smiled as he considered the absurdity of the situation he found himself in. He never imagined he’d be sitting in bed browsing porn with his wife, and yet here he was, and Olivia was the one making the selection.
Carter tapped the thumbnail and brought up the video. As it started playing he tapped the full screen button and turned his phone horizontally to watch an amateur porn video with his wife. Again he smiled at the sheer absurdity of it all. He couldn’t help but get turned on, too.
The scene began with a POV blowjob where cute young blonde in a ponytail crawled between her man’s legs and took his exceptionally big cock into her mouth. Her big blue eyes stared into the camera as she swallowed as much of his dick as she could without gagging. He groaned and she pulled off his cock and stroked him while smiling. “Do you like that, baby?” she said to the camera?
“Wow,” Olivia said.
Carter wondered what amazed Olivia the most. Was it the size of the guy’s cock – which must have been nine inches long and was thick enough that the blonde girl couldn’t wrap her fingers all the way around it – or was it the fact that the girl was giving such an eager blowjob. Olivia didn’t really go down on him all that often. She mostly seemed to find it unpleasant and Carter couldn’t bring himself to pressure her for more oral sex.
Again the girl took the big cock in her mouth and this time she nearly swallowed the whole thing while her man gently gripped her ponytail.
“Oh, wow,” Olivia said, this time with a hint of lust in her voice.
Carter couldn’t help but get a little turned on at Olivia’s reaction. It was totally unexpected. He figured she’d be horrified at the whole thing, but instead she seemed fascinated and perhaps a little aroused.
When the big cock emerged from the blonde girl’s mouth it was soaked with her spit. She smiled at the camera, stroked him a few times, and then moved to straddle her man. She rubbed the head of the cock along her shaved pussy, which was noticeably wet, and then slowly sat down on him.
His cock was thick enough that it genuinely looked like her pussy was having to stretch out around him. A long, low moan escaped the girl’s lips as she sank all the way down on her man’s cock and kept him inside her while grinding back and forth.
Carter was equally thrilled and surprised when Olivia pushed her hand under the waistband of his boxer shorts and wrapped her fingers around his stiff cock. It blew his mind that he was watching porn with his wife and she seemed turned on enough to play with his dick.
A quiet, seemingly involuntary moan escaped Olivia’s lips as she watched the girl in the porn start to ride her man’s cock. The camera work was surprisingly good as he maintained a steady view of her pussy rising off of and then swallowing the full length of his erection over and over.
Carter luxuriated in the rising sense of arousal that coursed through him. The porn video was unquestionably sexy and Olivia’s stroking felt even better than usual. He ran his hand over her lower back and into her panties to squeeze Olivia’s tight ass, eliciting another moan of pleasure. She pressed her body tighter against Carter’s in response, seemingly urging him to let his hands roam further.
Olivia was close enough that Carter could reach her pussy with his fingers and he was delighted to find her exceptionally wet when he did. He slipped two fingers inside her and they emerged soaked with her juices. He found her clit soon after and gently rubbed it in the hope of offering his wife the same sort of pleasure she was giving him with her skillful stroking.
Carter thought he’d made a mistake when Olivia suddenly grabbed the phone out of his hand and tossed it aside. When she swiftly pulled off his boxer shorts and her panties in succession he was thrilled to be wrong. She wasn’t mad; she was horny.
Olivia straddled him just as the girl in the video had done and took Carter’s cock inside her. He couldn’t help but notice how much smaller he looked than the guy in the porn had. That didn’t stop his wife’s pussy from feeling absolutely perfect.
He groaned as Olivia sank down on him and began to grind and ride. It felt like she was emulating the girl in the video. Carter looked up to see her eyes closed as she concentrated on the pleasures of sex that emanated from her loins.
“I’m going to cum, Carter,” Olivia said less than a minute after he’d entered her. It usually took her a lot longer to reach her orgasm.
“Cum for me,” Carter said. “Cum on my cock.”
Olivia cried out and collapsed on top of him as her body literally trembled as the pleasure of an intense climax radiated from her pussy. He ran his hands over her back and through her dark hair and savored the feeling of her wetness and warmth around his cock.
It took longer than usual for Olivia to recover from her orgasm and lift her head off Carter’s chest. There was a blissful smile on her face when she did.
“I really enjoyed that,” she said in a slightly sheepish tone, as if she was a touch embarrassed at having had such a strong orgasm so quickly.
“Me too,” Carter said.
“You didn’t cum though, did you?” Olivia asked as a look of concern crossed her face.
“No, but that’s okay. It was actually really hot watching you cum like that,” Carter said as he brought her lips to his for a soft, slow kiss.
Olivia surprised him by eagerly pushing her tongue into his mouth and slowly riding his cock with her soaked pussy. Clearly it wasn’t okay for her. She was going to make him cum.
Carter grabbed her ass with both hands and began thrusting upwards to meet the movements of her hips. If she wanted him to cum he wasn’t going to disappoint his wife. He knew it wouldn’t take long.
A minute later he cried out and had the orgasm Olivia seemed so desperate to give him. He came inside her while she urged him to do so. Now it was Carter’s turn to close his eyes and enjoy the blissful feeling of the immediate aftermath of a great orgasm.
Olivia grabbed his boxer shorts and held them between her legs as she pulled off of Carter’s cock. His cum dripped out of her and into them as she rolled onto the bed next to him.
“Thank you for all of that,” Olivia said. “That was…illuminating.”
“My pleasure,” Carter said as he smiled. It felt like something had changed for the better, like their sex life had gotten a great deal more interesting after three years of marriage, which wasn’t typically how things went for couples.
It seemed to Carter that the trip to New York had unlocked something in Olivia. They’d been back in Minnesota for three weeks and despite being immersed in the everyday stresses of work their sex life had gotten far more interesting.
They’d had plenty of sex before, but it tended to be contained to the bedroom and mostly missionary with a little bit of girl on top. Since returning from New York they’d watched porn together a few more times and had enjoyed each other in almost every room of the house and in all manner of positions. Olivia had even gone down on Carter a handful of times, each time seemingly determined to get better at it.
It was because things had been so good that Carter was so crestfallen when he came home one day to what sounded distinctly like Olivia having sex. An impending blizzard had led his boss to dismiss everyone a few hours early and Carter figured he’d surprise his wife and they could enjoy a little fun together before dinner.
Her moans reached his ears before he even opened the door to the house. A sense of dread filled him immediately. For the briefest second he considered getting back in the car and parking down the street for a few hours to avoid having to discover what seemed certain to be a heartbreaking betrayal.
The moans grew louder as Carter walked down the hallway towards the bedroom. His mind filled with horrific images of another man between Olivia’s legs giving her the kind of fantastic fucking that would elicit such loud, lusty sounds of pleasure.
The sense of dread became nearly overpowering as he neared the bedroom door. It was open, so he was just a few feet away from seeing his whole world come crashing down.
At first, what Carter saw was confusing, mostly because he’d been expecting to see a man on top of Olivia. Instead, he saw his wife alone and plunging a long, thick, lifelike dildo into her pussy. Her eyes were closed and she was naked with one hand working the toy while the other played with her nipples.
All Carter could do was stare at the near-pornographic scene playing out in front of him. Olivia was clearly lost in the throes of self-driven passion and it was so intensely arousing he couldn’t tear his eyes away or announce his presence.
It seemed like a small eternity, but it was just a handful of seconds before Olivia opened her eyes and saw Carter staring at her.
“Oh my God! Carter!” she screamed before quickly pulling the toy out of her and scrambling out of the bed and to the floor on the far side. It was as if she thought she could hide from Carter and he’d never have discovered the solo play she clearly intended to hide from him.
For a moment Carter was amused at her panicked attempt at an escape, but then he heard choked sobs coming from the other side of the bed and rushed to his wife’s side.
He found Olivia curled into a ball and crying uncontrollably. Carter sat next to her and pulled his sobbing wife into his arms.
“I’m sorry,” Olivia said as she buried her face into his chest. “I’m so sorry.”
Carter softly kissed the top of her head and ran his hands through her long, soft hair as he tried to calm Olivia down. “It’s okay,” he said. “It’s okay. I promise.”
After a few minutes of crying Olivia had calmed down enough to unfurl her tightly curled body and talk to Carter.
“This isn’t something you need to apologize for,” Carter said. “It’s not like you were cheating. It’s just a sex toy.”
Carter could see his words weren’t having the desired effect though. It still seemed like Olivia felt bad and he thought he knew why.
Carter pulled Olivia into his lap and stood with her in his arms. He kissed her softly and laid his still-naked wife in the bed. She looked confused when he leaned down and picked up the toy, which was remarkably lifelike. He handed the dildo to Olivia and she reluctantly reached out and took it before setting it on the bed next to her.
For a moment, it looked like she was going to burst into tears again. When Carter began to strip, those emotions washed away and were replaced by confusion.
“Can I watch?” Carter said as he pulled off his underwear and climbed into bed. His cock was already half hard from the brief show he’d enjoyed earlier.
“What?” Olivia asked. She seemed genuinely shocked by the turn of events.
Carter gently kissed his wife’s neck before whispering, “It would really turn me on to watch you play with your toy.” He kissed her neck again and Olivia moaned quietly. Carter confidently moved down her neck and chest before reaching her perky B cup breasts and taking a hard nipple into his mouth.
Olivia moaned louder as he ran his tongue back and forth over the erect flesh. He spread the precum dripping from his cock over the tip and stroked until he was rock hard. “Please, Olivia. I want to watch,” he said.
Olivia hesitated, but when Carter again took her nipple into his mouth she couldn’t resist. She picked up the dildo and rubbed it around her pussy lips before gently pushing it inside. A low, sensual moan escaped her lips as she filled herself.
“That’s so hot,” Carter whispered as he fixed his gaze between her legs and masturbated.
He meant it, too. He didn’t really understand why, but he found it incredibly hot to watch the lifelike dildo disappear into his wife’s pussy. She clearly loved fucking it, too, as her whole body seemed to react to the pleasure of the dildo filling her.
Carter kissed Olivia’s neck in the spot that always made her moan before whispering, “Does it feel good?” His cock throbbed with desire as he masturbated.
“Yes,” Olivia moaned.
She was clearly enjoying having the toy inside her again, but she still seemed hesitant to Carter. She wasn’t letting herself go like when he walked in on her. He wanted Olivia to unleash her lust. He needed it.
Acting on instinct, he went a little further with his dirty talk. “Does that big cock feel good inside you?” he asked.
Olivia closed her eyes and moaned. Her hips pushed upwards as if she was meeting the thrust of a man between her legs.
“Do you like fucking that big cock?” Carter asked as he stroked his throbbing cock.
Again Olivia moaned, this time taking her breast in her hand and gently twisting a nipple between her fingers.
Carter felt aroused in a way that surprised him. It felt so good to get lost in the pleasure of watching his wife fuck a dildo that was shaped exactly like a cock, and a much bigger cock than his. He both wanted to cum immediately and for this particular type of pleasure to last forever.
He wanted more, too. That’s why he pushed the dirty talk even further.
“Is his big cock going to make you cum?” Carter asked.
Olivia’s eyes shot open and she looked at Carter before saying, “Yes, his big cock is going to make me cum,” in a lusty voice. “He’s going to make me cum so hard!”
“Cum on his cock,” Carter encouraged her, getting completely lost in the moment. He felt an unfamiliar, entirely pleasing tingling sensation spread through his pelvis.
“Oh fuck!” Olivia screamed as her body convulsed. “I’m cumming. I’m cumming on his big cock!”
Carter pushed himself over the edge and joined his wife in cumming. He too convulsed as the pure joy of a great orgasm overtook his body for a handful of seconds.
For a few minutes they rested silently in bed. They wanted to bask in what felt like a perfect pair of orgasms for just a little while.
Finally, Carter sat up and looked at the dildo Olivia still held in her hand. “So, when did he arrive in our lives?” he asked.
“A week ago,” she said. “I’m sorry. I should have said something.”
“Why didn’t you?” Carter asked as he admired what seemed like an exceptionally high quality dildo.
“I guess I was afraid,” Olivia said as she stared up at the bedroom ceiling.
Carter reached out and took her hand in his. “Afraid of what?” he asked.
Olivia turned to him, her eyes full of warmth and love, and said, “I was afraid you’d be hurt.”
At first, Carter was confused. Then it dawned on him why she’d be worried about his feelings. “Because it’s bigger. You were afraid I’d be hurt because it’s a lot bigger than I am, right?”
Olivia nodded and rested her head on his chest, as if she couldn’t stand to look at him for fear that the hurt she was afraid of inflicting would be reflected in his eyes. “I’m sorry,” she said again.
“Hey,” Carter said as he rolled Olivia onto her back so he could force her to make eye contact with him. “You’re incredibly sweet, really, and I can understand why you would have been worried about that. I’m sure there are guys that would get really insulted if their wife bought a big dildo without telling them. Heck, maybe I’m supposed to be insulted too.” He smiled at her before saying, “But I think we both know I wasn’t hurt. I mean, there’s no denying how much I enjoyed watching that.”
Olivia smiled and kissed Carter softly on the lips. “I guess that’s true. You might have cum even harder than I did,” she said before a laugh escaped.
Carter couldn’t help but smile. She might have been right. It was an orgasm unlike any he’d ever had.
He kissed Olivia and ran his hands over her stomach and thighs, enjoying how smooth her skin felt beneath his fingers.
He couldn’t help but ask a question he’d been dying to know the answer to since he first walked in on her, “Does it feel different? Having something bigger inside you, I mean?”
“Are you sure you want to know?” Olivia asked.
“The short answer is yes, it does feel different. I’m not sure I could explain it to someone that doesn’t have a vagina, but it’s different,” she said.
“Is it better?” Carter asked, knowing that he was potentially playing with fire.
“I love having sex with you Carter,” Olivia said as she caressed his face and kissed him. “I really do.”
He smiled. “I know you do, but that’s not really an answer, is it?”
“In some ways, yes, it’s better. In other ways, it’s not,” she said. Olivia paused as she stared into Carter’s eyes. He could tell she was looking to see if her answer had hurt him in the way she suspected it might. “Like I said, I can’t really explain it, but I really love the sensation of being filled and stretched that the toy provides, I guess.”
Carter was still mostly erect, so he picked up the toy and held it next to his cock. There was no question it was bigger than him. It looked more than twice as thick and just about twice as long. The contrast was really kind of remarkable.
“Well, there’s really no comparison, is there. It’s just a lot bigger,” Carter said. The direct comparison and his wife’s admission made him feel a little insecure, but he was still riding high on the pleasure of his orgasm and it was a fleeting emotion.
With the dildo still in his hand Carter turned to Olivia and asked, “Have you been using it a lot?”
Olivia’s face reddened a little. Her apparent embarrassment made Carter smile. “Every day,” she said sheepishly.
Again Carter was hit with a wave of insecurity. There was a little part of him that worried he’d been replaced in the bedroom, but then he remembered that they’d had sex several times since the dildo had arrived, so that clearly wasn’t the case.
“Will you let me watch again?” he asked.
Olivia smiled and kissed him, this time with surprising vigor and a little bit of tongue. “Absolutely.”
To Carter’s surprise, Olivia rubbed the dildo around her pussy lips and pushed the thick head inside. She closed her eyes and moaned. “How about now?” she asked.
“Absolutely,” Carter said as he wrapped his fingers around his cock and took Olivia’s nipple into his mouth.
She moaned and once again plunged the toy into her pussy, kicking off another round of lusty mutual masturbation for the couple.
As Carter’s cock returned to its erect state he marveled at how quickly things had changed in their sex life. He wondered what sort of fun they’d have next.
The remaining parts of Size Matters will be published on my Patreon page over the first few weeks of January 2019. Become a supporter today and read the rest of this cuckold story along with dozens more guaranteed to thrill you.