Long Distance Cuckolding - A Diary - Part 1 (Patreon)

Five days ago my wife Piper got on a plane and flew to California. She's going to spend the bulk of the next four months living and working in San Francisco while I'm back home in New Hampshire (at the southern tip, so sometimes it feels like we live in Massachussetts).

If you're wondering, she's a corporate consultant. And no, I couldn't really tell you what that means or what exactly she does. I'm not sure Piper could really explain it, but I'm pretty sure that's kind of the point of that whole field of work. If it's all a little vague and difficult to understand that makes it easy to work more hours and charge more to your clients.

Piper's part of a team working with a large-but-struggling company that's looking to revamp their business. They bring in the consultants, they get recommendations, and then they put some or all of those recommendations into action. If things go wrong, the consultants get blamed and the CEO might get to keep his job. If things go well, the CEO takes all the credit. Either way, the consulting firm gets paid a whole lot of money.

Piper isn't yet at a place where she gets a big chunk of the money her team earns for the company. She's only been there a few years. That's why she took the gig in San Francisco, though. She wants to show that she's the kind of team member that's worth promoting. That's why we're going to spend the next four months apart from each other - outside of the occasional weekend visit - which is basically four months longer than we've spent apart since we first met a little over seven years ago during our senior year at Boston College.

I'm not trying to bore you, though. I mention all of that as a bit of background before I delve into the real reason I'm writing. You see, Piper's four month job assignment on the West Coast offers a unique opportunity for us to explore something I've long fantasized about.

It's a long shot as Piper has never expressed any real interest in it, but I think there's a chance she'll use her time away to cuckold me. It's entirely possible that I'm delusional, that when I say there's a chance what I really mean is that I'm lost in my fantasy and I'm just hoping against hope that she'll cuckold me.

I don't think it's entirely a fantasy, though, and I'll tell you why. We have to rewind to the night before she left, though. So, six days ago at this point. Before I get into the details of that night, though, it's important to know that Piper is well-aware of my cuckold fantasy. We've talked about it countless times and on a handful of occasions she's indulged in a bit of dirty talk and/or mild roleplay about it. She's never come close to hooking up with another guy, though. The closest she ever got was a few minutes of dancing with someone else while we were on vacation. It's never gone further than that, though.

I understand why, too. We live in a fairly small town and Piper fears the repercussions of someone discovering that we're into hotwife/cuckold play. She's probably not wrong, either. People in small towns tend to be way more sexually conservative than you might think. It's also possible she just uses that as an excuse because she has no actual interest in cuckolding me. Who knows?

Back to four days ago. The night before she left. We'd spent the whole day together and we’d tried to make it special. It was basically a daylong date. We went to the beach during the day, had incredible lobster rolls for lunch, had way more fun than you might imagine at a mini golf and go-karts place and then came back home and went to dinner at our favorite restaurant. None of that is particularly important for this story, though. What matters is what happened once we got home.

First, I poured us two big glasses of wine and we cuddled up on the couch. Piper had changed out of her dress and into a pair of leggings and a sweater, which is a combination I happen to love.

We sipped our wine, talked, and touched and kissed each other in that gentle, deeply intimate way that really only happens with couples that have been together for a while. It felt like a long preamble to the sex we were undoubtedly going to have once we took things to the bedroom and it succeeded in keeping me in a low level state of desire for the entire time we were on the couch.

It was that desire - and the gentle sense of drunkenness the wine provided - that led me down a particular conversational path, though it started innocently enough.

"So, what will you do on the weekends?" I asked.

"People go out," Piper replied.

It was a vague answer, though I couldn't tell if that was purposeful. "Go out?"

She looked up at me and smiled and I marveled at how beautiful she was. "Yeah. To restaurants. Clubs. Bars. That sort of stuff. I mean, just about everyone on the team is under thirty and most of them are single, actually, so they tend to go out to places where other single people gather."

I got excited. I couldn't help it. I'm sure just about any other would-be cuckold would get excited too. I mean, I couldn't help but imagine her going to the sorts of places where single people go and getting hit on by all kinds of guys, which in my mind would inevitably lead to her cuckolding me. Yeah, it was pure fantasy stuff, but my mind was in a place where the fantasy felt so good.

"So, you said that people go out, but will you go out with them?" I asked.

Piper sipped her wine, smiled, and nodded. "I think four months might be kind of unbearable if I'm not having some fun on the weekends, you know? I like everyone on the team and we do actually have fun together, so yeah, I'll go out with them."

"To bars, and restaurants, and clubs?" I asked.

Piper nodded again.

"The kinds of places where single people go."

She nodded once more, but this time there was a smile to go along with it.

"Where single people go because they're looking to meet someone. To hook up," I said.

"Yes, but I'm not single," Piper replied, cutting me off at the pass.

"No, but you're married to a man that wouldn't mind if you acted like you were single while you were away," I said without a moment's hesitation.

She studied my face for what felt like ages - though it was probably just a few seconds - and then asked, "Have you been thinking about that? About your fantasy?"

I nodded. It felt a little embarrassing to admit it, like I was somehow letting her down by being so predictable, but there was little point in lying. "Sorry, I can't help it."

For a moment I thought I'd ruined the night, but then Piper leaned in and kissed my neck. "It's okay," she said. "There's nothing wrong with having a fantasy and to be honest, I like that your fantasy involves me. I'm not sure that's all that common, as I think most men tend to fantasize about other women."

She cuddled up next to me and I pulled her close as a comfortable silence settled over the room. I wanted to push the conversation. I was turned on and a little bit drunk and the notion of Piper acting like she was single for the next four months was a huge turn on. It felt risky, though, so I stayed silent as I attempted to find the perfect way to bring it up again.

"So, if I went out to a club and I ended up dancing with a guy, that really wouldn't bother you?" she asked.

She was thinking about it. She was considering it. That's all I could think about in that moment and it was so fucking exciting. I tried my best to contain that excitement, but I damn sure felt it.

"I'd be the opposite of bothered," I answered. "I know that seems kind of crazy and hard to believe, but it's true. I'd be genuinely thrilled if we talked on a Saturday morning and you told me that you'd gone to a club the night before and danced with a guy. I'd be even more excited if you told me he touched you - even in a really subtle way - and even more excited if you told me you couldn't help but let him kiss you."

For a few seconds, Piper didn't say a word. I couldn't see her face - she was leaning against my body - and I felt my heart pounding as my mind ran through various panicked scenarios. See, despite knowing about my fantasy I'd never really gotten the impression that Piper understood it. In fact, I think she thought it was strange - at best - and perhaps a little bit screwed up at worst.

"What if I met a guy and he asked me on a date?" she asked. "Not necessarily in a club or anything. Just, you know, if I met someone while in San Francisco."

The question was related to what we were talking about, but it felt like a sudden change of subject. It was still exciting, though. I mean, how could it not be?

"You mean, how would I feel about you being asked out? Or how would I feel about you going on a date with a guy?"

"Both," she answered.

"Both would excite me," I replied. "Actually, I think the idea of you dating someone out there would be...I don't know, I think that would be really, really exciting. I guess I never really thought about it that way - about you actually dating a guy or having a boyfriend out there - but there's something really pretty hot about that."

She pulled away a little to turn and look at me.

"I mean, my heart's actually kind of pounding just thinking about it," I said.

Piper reached up and rested her hand on my chest. A moment later she leaned in and pressed her ear where her hand had been. "It is pounding," she said with a gentle sense of wonder in her voice. "I guess you're not lying."

"No, I'm not," I replied.

She lifted her head, smiled, and looked away before cuddling up against me once more. I put my arm around her, pulled her close, and kissed the top of her head as my fingers moved over the impossible softness of her sweater.

"It would be strange to date someone else," she said. "To have a...well, a boyfriend I guess."

I was thinking the opposite. In the moment, I couldn't imagine anything hotter than my wife dating another man for four months and doing so while we were 3,000 miles away from each other.

"It probably would have to be that, though," Piper said. "I mean, I could hook up with a guy at a club, but then everyone else on the team would think I was cheating on you and I don't really want that to be what they know me for."

Was she actually considering it? Was she just a little drunk and rambling? Was she initiating a roleplay? I had no idea. I was so turned on, though.

"That makes sense," I said as I let my fingers wander just a little, brushing against the side of her breast for a moment before I moved back to gently caressing her arm. "You could be a little more discrete if you had a boyfriend. You could go to his place to...well, to have fun instead of the corporate apartment complex where you're all staying. Plus, the sex would probably be better."

"You're probably right," Piper replied, filling me with lust. "For me, at least, sex is always better in a relationship."

Again a comfortable silence fell over the room. I sipped my wine and Piper did the same. She was still cuddled up next to me and I let my hand wander as far as it could in that position, though I tried to be subtle about it.

"It's been a long time since I dated someone," she said.

I still couldn't tell if she was genuinely considering it, if she was trying to turn me on, or if she was just rambling a bit because she'd had a few glasses of wine that night. No matter the reason, I was turned on.

"It's exciting though, isn't it? Dating someone new. I mean, if it's good," I said.

Piper looked up at me, smiled, and kissed my neck softly. "It is. It can be really exciting, in fact. Trying to find something to wear that he'll like. Deciding whether he might see my underwear and then figuring out how hot I want to look if that happens. Trying to get my hair and makeup just right so I look good for him without looking slutty. Deciding on how high a heel I should wear. Feeling that thrill of seeing him as I arrive at the restaurant. Feeling that excitement when he takes me in his arms and kisses me before we go inside. Feeling that even greater excitement of going home with him."

It really seemed like she was thinking about it, like she was truly and genuinely considering the notion of dating someone else while she was in San Francisco. I was astounded and cautiously optimistic about it actually happening.

"Did you pack the sort of heels you'd wear on a date? Or the sort of clothes you'd wear to look good for your boyfriend?" I asked, figuring I might as well push it a little. I mean, why not, right?

Piper sat up, drank the rest of her wine, and set the glass on the table. She looked at me, offered a smile that looked just a little bit naughty, and said, "No, I didn't. Maybe I should, though."

She didn't seem to be joking. "I think you should," I replied. "I mean, it would be nice to have options just in case, right?"

Piper stood, plucked my wine glass from my hand, and drank the rest of it. She set the glass on the coffee table, took my hand, and helped me to my feet. "Come on. You can help me."

We were playing. We were definitely playing. She was just trying to create a memory for me. She just wanted to leave me with a feeling of deep satisfaction before she left for four months. That was all that was happening. Nothing else made sense.

"Get in the bed," she said. "I'll model some clothes for you."

Piper pushed me into the bed with a smile and headed for closet. I piled up a few pillows and leaned against them with a smile on my face and a sense of giddiness coursing through me. Part of me wanted to believe that there was actually a chance she was going to pack as if she intended on dating another man while in San Francisco. I mean, what would be hotter than that?

She emerged from the closet in a red and white sundress with spaghetti straps. It was short, too, reaching the middle of her thighs and leaving plenty of skin exposed. She'd taken off her bra and I could see her nipples poking through the thin material of the dress, which she hadn't worn in years.

"Wow," I said.

Piper spun around and the bottom of the dress floated up, revealing her black lace panties. "Do you like it?"

I nodded and stared dumbly. She looked so beautiful and there was a genuine sense of joy emanating from her that I found irresistible.

"Will he like it?" Piper asked.

It was so hot to hear her say that. So hot that my cock instantly started tingling as I imagined my wife wearing that dress for another man, for a boyfriend. "The guy you'll be dating, you mean?"

Piper nodded.

"Yes, he'll like it. In fact, when he sees you in it he'll think he's the luckiest man in the world to have met a woman so beautiful," I said.

She smiled, spun around, and looked over her shoulder in a flirty, irresistible way. "Is that how you feel?"

"Yes, that's absolutely how I feel," I replied. "You're stunning, Piper."

She flipped up the back of the dress and then pulled it over her head, folded it neatly, and set it at the foot of the bed. I thought for sure she was going to climb on top of me and we'd begin the sexual portion of the evening, but instead she said, "I'm going to need a bigger suitcase if I'm going to pack extra clothes and shoes. The bigger one is in the spare bedroom closet. Will you grab it for me?"

I was stunned. Was she actually going to pack an entirely different suitcase? Was she going to fill it with outfits she'd really only wear on dates? I didn't matter if it was true or if she was just playing with me. I was turned on and Piper was absolutely into it, so I hurried to the guest bedroom and found the bigger suitcase.

When I returned, Piper was wearing a classic little black dress - this one was low cut and showed off her breasts in a hugely enticing manner - and a pair of strappy three inch heels. I stopped in the doorway and stared as she turned from side to side, showing off how good her body looked in the dress.

"He'll love that," I said. "It's classy but sexy and your legs look amazing in those heels."

"Thank you," Piper replied. "And I think you're right. This dress is perfect for a date at a nice restaurant, or perhaps at some sort of corporate event. His job, not mine."

It's a small thing, but the fact that she was thinking about perhaps attending a work event with her fake boyfriend was such a turn on. It made me feel like she was actually considering the notion of dating someone, even though I had no idea of knowing if that was true.

"Here, bring me the suitcase," she said.

I wheeled the suitcase over and Piper set it on the ground and opened it up. She reached for the much smaller suitcase she'd already packed and I said, "I can do that. Transfer your stuff, I mean."

She smiled. "Yeah?"

I nodded. "I'll do that while you try on something else."

She gave me a kiss - a long, lingering, hugely arousing kiss that brought my cock to a half-erect state - and then headed for the closet as I grabbed her suitcase, laid it down, and opened it up to begin transferring her clothes. She'd packed smartly and sparingly with a mixture of skirts, pants, blouses and jackets that could be combined to form dozens of different looks without needing to bring dozens of different outfits. I transferred everything to the bigger suitcase and looked up to see Piper emerge from the closet in a stunningly sexy, dark blue floor length gown with a slit up one of her thighs.

"Holy shit," I said from my knees.

"A girl needs at least one total knockout of a dress," she said with a smile. "The kinds of dress that makes everyone else jealous of my boyfriend. The kind of dress that makes him want to skip whatever event we're going to do so he can take me back to his place.

To fuck you, I thought. So he can take you back to his place, pull up the bottom of that dress, and fuck you with wild abandon until you both cum.

"I love that dress," I said. "I remember when you wore it to that party your company had a few years back. You looked incredible that night. You had everyone's attention, too."

Piper stepped closer and I craned my neck to look up at her. "I certainly had your attention," she said. "If I remember correctly, you couldn't keep your hands off of me. You were especially fond of how good my ass felt in the dress."

I nodded, reached out, and ran my fingers up her exposed leg. Piper smiled and I kept going until I reached her crotch. I figured I'd find her panties, but instead I felt her labia. I felt her wetness. She moaned and closed her eyes as I slipped a finger inside her. I couldn't believe how hot and wet her pussy felt.

"I fucked you in this dress," I said as the memory of that night filled my head. "Or, I suppose, you fucked me. We didn't even get past the kitchen. I sat in one of the chairs, you straddled me, and we had incredible sex, if I remember correctly."

"You have a good memory," Piper replied with a smile. A moment later she unleashed another moan, this one deeper and longer as I rubbed her clit faster. "I came especially hard that night."

"You know, if you had a boyfriend in San Francisco and you wore this dress for him, he'd definitely want to fuck you," I said.

She looked down at me. "You think so?"

I nodded and desperately hoped Piper was actually entertaining the idea of wearing the dress for another man, for a boyfriend.

"How do you think he'd fuck me?" she asked.

She was building a fantasy for me. She had to have been. It was the only thing that made any sense. It was insanely generous of her and there was no question she'd leave me feeling a deep sense of lust and love before departing for nearly a month before we were scheduled to see each other for a weekend visit.

"I think...I think he'd want you the moment you walked into his apartment. I think he'd pick you up and put you on his kitchen counter...I think he'd pull the dress up and spread your legs. I think he'd take you right then and there," I said as my cock reached a state of such hardness that it actually hurt a little.

I slipped a second finger inside Piper and reached for her g-spot, offering gentle stimulation while rubbing her clit. I saw her thighs tremble as she closed her eyes and I couldn't help but hope that she was picturing herself sitting on another man's kitchen counter while he fucked her.

Then she stepped back, opened her eyes, and looked down at me. "I think you're right," she said with a smile. "Though I think he might also want to bend me over his kitchen counter and take me from behind."

The image filled my head and for it struck me as astoundingly hot. The fact that Piper had said it - that she'd put the idea in my head - made it so much hotter, too. "Is that something you'd enjoy?" I asked.

Again she smiled, but instead of answering Piper pushed the straps of the dress from her shoulders and let it fall to the floor, leaving her naked except for her heels. I stared at her pussy - she was really wet - and then turned my attention to her perky tits and rock hard nipples. She turned and walked into the closet, giving me a great view of her ass, which looked even hotter thanks to the heels.

I picked up her dress, folded it neatly, and set it in the suitcase as I waited to see what else Piper thought another man might enjoy seeing her in. She emerged from the closet in a short leather skirt - one I hadn't seen on her in half a decade - and a semi-sheer long sleeve top that clearly showed the bra she'd put on. It was the kind of outfit a woman wore when she absolutely, positively wanted to be noticed, when she wanted everyone to look at her.

"Wow," was all I could manage to say. "Piper...you look...you look so fucking hot."

"I know," she replied with a smile. "This one's probably not for going out in, mostly because I don't think we'd make it out of his apartment if I showed up in this. He'd definitely have to have me, don't you think?"

I nodded.

"Then I should probably bring it, shouldn't I? I mean, every girl needs to have a few outfits that will turn her boyfriend on so much that he absolutely, positively has to have her the moment he sees her, right?" she asked.

I nodded again. "Yes, you should bring that. You should definitely bring that."

She unzipped the skirt, took off the top, and handed them both to me along with her bra. Then she smiled, blew me a kiss, and headed right back into the closet as I set her clothes in the suitcase and adjusted my boner so it wasn't causing me so much pain.

Piper stepped out of the closet in a tight black lace bodysuit with a plunging neckline. She'd paired it with black lace top stockings and the same strappy heels and my jaw dropped as she put her hands on her hips and smiled.

"Guys like it when their girlfriends wear lingerie for them, don't they?" she asked.

I hadn't even considered lingerie. I really hadn't. I was so caught up in the dresses and sexy outfits that I didn't even think about lingerie, but of course it made sense. Was it possible that Piper was really thinking about it? That she was at least going to open herself to the possibility of dating someone else while in San Francisco? It felt impossible that it could be true, and yet I couldn't help but hope for it.

"Guys love it when their girlfriends wear lingerie, especially lingerie like that," I said.

"I have lots of lingerie," Piper replied. "And it doesn't really take up any space in a suitcase, so I should probably pack lots of it, shouldn't I? That way, I can have always something new and naughty to wear for my boyfriend."

I stood. I reached out and Piper offered her hand. I pulled her close. We kissed as I moved my hands down her back and grabbed her ass. She moaned and parted her lips so our tongues could dance.

"I have to have you, Piper," I whispered.

She smiled and helped me out of my pants as I took off my shirt. She yanked my underwear down and pushed me towards the bed until I was on my back with the soft comforter beneath me. Piper crawled on top and straddled me with my stiff cock pressed against the thin fabric of her bodysuit. She leaned down and kissed me as I ran my hands over every part of her body I could reach while gently thrusting my hips and generating a touch of blissful friction.

"It really turns you on to think about me dating another guy, doesn't it?" she asked.

It should have been obvious - and I'm sure it was - but I could understand her asking. She still didn't understand the fantasy - how could she, really - so she wanted further confirmation.

"It really does," I replied. "More than just about anything...so thank you, Piper, for indulging the fantasy a little bit tonight."

She sat up, pulled aside the lace covering her pussy, and took me inside her. "Who says I'm indulging a fantasy?" she asked. "Who says I'm not going to date someone else while I'm in San Francisco? Who says I'm not going to spend the next four months being another man's girlfriend and indulging in all kinds of incredibly hot sex?"

She rested her hands on my chest and rode me, alternating between bouncing on my cock and grinding back and forth over my crotch. She was wet and her pussy was incredibly hot, all of which spoke to genuine arousal. I wanted to believe it was more than a fantasy, that she really was going to bring all those extra clothes and lingerie and find herself a boyfriend while she was away for work.

"I want you to," I said. "I want you to find a boyfriend, to go on great dates, to kiss him, to think about him constantly, to text with him, to talk to him all the time, to have lots of great sex."

She leaned down, kissed my neck, and moaned while riding me faster. "I know you do, baby. And I think that having a boyfriend in San Francisco would make the next four months so much more exciting. I think it would be incredible. I think I'd love to find someone that I wanted to spend lots of time with, that I thought about all the time, that made my pussy as wet as it is right now, that I wanted to fuck all the time."

She bounced faster and harder on my dick and I got perilously close to a climax.

"Piper, I'm almost there. I'm close," I said.

She leaned back, put her hands on my chest, and rolled her hips back and forth, grinding her clit into my pelvic bone and bathing my cock in her intense heat and wetness.

"Maybe another man will utter those same words to me, Joel. Maybe my boyfriend will tell me he's close to cumming. Maybe I really will date someone else while I'm in San Francisco," she said.

That was it for me. I came and I came hard. Before I closed my eyes to let loose, I saw a smile on Piper's face. A look of total delight. She liked that she was making me cum so hard, that playing into my fantasy had gotten me off.

She came too. A split second after I did, which honestly made my orgasm better. A lot better, even. Knowing that it wasn't just for me, that the sex was good for her too, made it so hot.

She collapsed on top of me after we'd both cum. I wrapped my arms around her and listened to her heavy breathing alongside mine. I kissed her neck and cheek and she did the same to me.

After a few minutes she sat up, looked down at me, and said, "I don’t think I could never date another man."

"I know," I replied, though I did feel just a touch of disappointment. I knew it wasn't likely she would actually pursue a relationship while in San Francisco, but the fantasy sure was exciting.

That being said, it was the big suitcase I loaded into the car the next morning, and it was full. I didn't see everything she packed, but I checked her closet after dropping her off at the airport and the stuff she'd tried on for me wasn't there and it looked like there was quite a bit of other stuff missing, too, including most of her lingerie.

Maybe Piper was being truthful and would never date another man. Maybe, though, she took all those extra clothes because she wanted to be prepared just in case she decided to change her mind.

I'll be sure to update you if it turns out that Piper does, in fact, change her mind. We'll talk soon :)