My First Day As A Cuckold

"Honey, I love you, but I met a man at the gym that I want to have sex with."

My wife uttered those words over three months ago, but the echo of her voice still singes at my soul and makes my body ache as if I was sucker punched in the gut. Since that day my wife and I have worked through a lot of issues, and she even delayed having that affair.

Until today.

Until now.

I am home staring wide-eyed at a broadcast from a nearby hotel room. An inviting but empty bed dominates my monitor. My wife is in the room, but not visible yet. He is there, too. They are naked. I know because my wife's bright red panties are on an armchair, tossed in a heap next to his boxers. I can hear them kissing and drinking wine. I turn the sound up so I can hear their conversation. My wife remarks on his huge penis. This is surreal. Partly exciting. Partly horrible. And I don't know which is making me tremble. It's about to happen. I feel like throwing up.

A little context before I go on.

Oct. 31, 2015.

My wife and I just got home from a Halloween party. She was taking off her cat-woman outfit and looking so cute in her frilly bright red bra and matching panties. It was shaping up to be a good end to a good day.

"Honey, I love you, but I met a man at the gym that I want to have sex with," my wife said softly. "I didn't plan for this, but I can't deny how badly my body craves him."

My body went limp and my knees wobbled as the words pounded into my gut, taking away my breath and voice. "How, why?" is all I could squeak out. "How could you."

"It just happened," she replied apologetically. "He is no one you know, just a guy I see almost every time I workout."

"Are we through?" I asked. "Is this how it ends after 6 years of marriage."

"That's up to you," my wife said matter-of-factly. "I like our life, but I need him. I will have him with or without your approval. But I'd much rather that you agree to this. I don't have any feelings for him. It is just for the sex."

"That's fuckin' awesome," I blurted sarcastically, shaking my head. "Just fuckin' awesome."

I slept on the couch for a few days, and we didn't hardly speak for the first week. But after the shock settled in, I started seriously thinking about if I could handle my wife with another guy. It's at this point I first learned what a "hotwife" was, and what it meant to be a "cuckold." And on a chat board I even found a more precise term, "wittol", which is a man that knowingly lets his wife "date." So my wife wanted to be a hotwife. Ouch. And wanted me to be a wittol. Double ouch.

I was hurt and skeptical, but I figured I could always bail out and leave her if I couldn't handle sharing her. But my wife and I have a great life, so I wanted to see if we could make it work. I had read enough online to know that many couples happily live the "hotwife" lifestyle, and seem to make it work positively for both of them. It was weird, but the possibility of doing this felt scary, sickening, and erotic all at the same time. But if I had anything to lose, it was already gone.

So over the next 6 weeks or so my wife and I started watching videos showing off the hotwife lifestyle. At first the videos were really hard for me to watch. But, I saw how much they turned my wife on, and every time we watched a cuckold video together, our follow-on sex sessions went on steroids.

Sometimes I watched videos by myself, and tried to pretend it was me watching my wife bang another guy. It was uncomfortable at first, but as long as I focused on how happy the wife was, and knowing I was going to get great sex as a result, I managed to stay mostly positive. I even practiced masturbating as I watched them, as I guess this is often what the cuckold does during the date. Over the weeks, I got used to the sinking feeling in my gut, and started focusing on the parts that felt erotic and dangerous. It was nice, as my wife and I talked openly about these feelings, and about how she felt as well.

I also found an active cuckold support website, and I chatted with other guys that had gone through the transition to cuckold. It was amazing to listen to their stories, and to find how closely they paralleled my own. It was kinda funny, but it seemed every one of the guys said the first encounter was hard, but by about the 5th time or so that they really started liking it. A few of the guys had wives that stopped doing the hotwife thing, and really missed it.

My wife and I became so close while we worked through this. She was very supportive and let me work through all my issues one at a time. After almost 2 months, I was feeling pretty confident I could handle at least a handful of dates. If it took 5 dates to figure this out, then that's what I would commit to. My wife and I came up with a few simple guidelines. First, there would be no intentional humiliation from her or her date. Second, at least the first 5 dates would be with the same guy. And finally, her guy would need a clean medical test to play without a condom. With that, we started putting together the plan for her first time. I was surprised how excited I was about it, but was still dragging my feet getting it going.

By the week before Christmas it was becoming clear to me that I couldn't delay her affair for much longer. She was texting her boy a lot, and she was bugging me nearly every day about when she could tell him she was available to meet. It was time for me to get serious about making this happen! After watching a few more cuckolding videos, my wife and I decided that it would be less stressful for both of us if she and her date shagged at a local hotel while I watched them remotely. So, for Christmas we got ourselves "couples gifts" - - a huge new 32" Mac desktop system for my office, and a new i-pad for her. With these, she could set up her i-pad in the hotel, and I could watch and hear what they were doing from my home office. Plus, we wanted to record the sessions so she and I could watch them later, as well.

We spent the day after Christmas checking out about a dozen hotels close to our house. We checked out rates and tested each hotel's Internet speed to make sure my live feed would not be jerky. We also checked out rooms, and tested the beds and pillows in each. My wife kept a log of her impressions of all the hotels and the "sex factor" for their bed. She considered several aspects for the bed, like bounciness, quality of sheets, and type of headboard. But I found it really interesting that she also wanted a bed that made some noise. She liked the idea of hearing the bed squeak while she was being pounded, but more importantly she thought it would be fun for me to hear it as well.

December 31, 2015.

For New Years Eve, my wife and I went to dinner at one of the nicer of those local hotels. They had a great package deal for dinner, live music, and a room. We went back to the room just before midnight.

"Of all the hotels we checked out," my wife said as we hugged, "this one had the best bed for sex."

"Why is that?" I asked.

"The bed has a really soft top, but still has a lot of spring to it," she said. "And it makes just the right amount of squeak when you bounce hard on it. And the headboard has vertical metal spokes that I can grip to keep from slipping around if he gets pounding really hard, which I think he will."

"And the room has some nice chairs and a bench for variety," I replied. "This could be a fun room for you and your friend."

"I already showed him a picture of the room last week," she said softly. "He liked it a lot, and is ready to meet anytime we are ready."

"How is he holding up?" I asked, not really having any idea what to say.

"I promised him our first time together would be worth the wait," she replied.

"Let's give the bed a test run," I said. "Maybe I can make it squeak for you."

"Let's leave the lights on," she said with excitement. "Just like my friend and I will do when you are watching us from home."

We had sex, and I managed to make the bed squeak a little during missionary. She got on top of me and got into a great rhythm that ended up making more bed-noise than I did! We both had a great time, although I could tell she was half with me, half in her date fantasy. It felt weird and sexy and bad and good all at the same time.

January 1, 2016.

"Let's set up your date," I said with surprise confidence as I woke up. "I'm ready to make this happen for you. Let's bring in your 2016 with a bang." We were still in bed at the hotel. I don't know if it was from the idea of her dating, or just regular morning wood, but I was super hard.

"That's fantastic," my wife said with honest enthusiasm as she reached under the sheet and started to give me a steady "thank you" handjob. "I know you will end up loving this!!"

"I am going to give it my all," I said. "And I really look forward to our post-date love making!"

"We've already agreed that you will not be present for the festivities," she said as her stroking slowed to a stop. "But with you watching remotely, that leaves a problem."

"What's that?" I asked. "After he finishes, I'll quickly pop over to the hotel and you can do me too! I can be in you within 10 minutes after his last spurt!"

"I am concerned you will masturbate at your desk as you watch us, just like you do when you watch the videos," she said calmly as she moved her hand off me. "It would be better for both of us if you wait for me before ejaculating."

"I won't jack off," I said firmly. "Having great post-date sex with you is the main driver for me doing this."

She got up and got her purse, and then came back to bed.

"I know you will try, but we can't take the risk of your cumming into your hand," she said as she handed me a small box from her purse. "I got this a few weeks ago anticipating this talk. You need to wear this while I am on my date."

"What's this?" I asked as I pulled a metal contraption out of the box. "Looks like a small vegetable strainer. But with a padlock"

"It's a penis cage," she half chuckling. "I lock your limp penis in it before I leave for my date and take the key with me to the hotel. When you come to the hotel after I am done, I take off the lock so we can have sex. It is super small and bent sharply downward, so you cannot get erect or ejaculate while you wear it. It guarantees no whacking."

"Does it work?" I asked.

"Let's do a test," she said with a smile.

She unlocked and opened up the cage and I pushed the sheet down to fully expose myself. By now I was starting to go limp, but my head was glimmering with precum. She put the contraption's metal loop around my balls, and then stuffed my mostly-limp penis into the little wire basket. It became fully limp as she scratched it against the metal wire. It was a tight fit, but she managed to lock the two pieces together, and then tossed the key onto the bed stand. She looked at her handy work and smiled at me. She rolled over on top of me, straddling my waist. I instinctively reached to caress her gorgeous perky boobs.

"Oh fuck that hurts," I groaned as my penis expanded into the sharp metal ribs of the cage. "It's trying to get hard, but it can't."

"It works!" she said excitedly as she lowered to suck on my nipples. "You have to take all the stimulation I can dish out without getting hard. No masturbating for you!"

"What are you doing?" I asked as she sat up and fiddled with her phone.

"I'm letting my guy know I am ready to date him," she said as she continued to type. She silently read his response. "He has to travel for a couple weeks, but he's up for Saturday January 23rd. Really really up."

"Oh, that's only a couple weeks away," I replied. "Even though it's a Saturday, you should still get a room reservation."

"I already texted him that you and I agree this is the best hotel," my wife said. "He's going to make the reservation right now. But we don't want you to know the room we will be using."

The phone beeped again. "Oh fuck," she moaned. "Take a look at this." My wife held the phone up for me.

"Holy crap," I gasped as I looked at her friend's penis. "That is huge. And uncircumcised."

"And he's not even hard yet," she said breathlessly. "Even soft it is enormous. I hope I can handle all that."

Her phone beeped again. "O-M-G," she gasped as she held her phone for me to see. "He's super hard now. And he has it next to a plastic water bottle."

"Shit that's big," I sighed. "He's nearly as thick as the bottle, and longer."

She put the phone down and continued teasing me, but with increased intensity. She was touching me, but thinking of him.

Although she had already proven her point, she left the cage on for the next hour as she teased me. Finally, she handed me the key and I took it off. Almost instantly I was rock hard, and she was so turned on that she just jumped on top of me and started pumping. Even with just an hour being locked up, the after-locked sex was incredible. More sensitivity. More sensation. And lots more cum. We both loved it. But we decided that we would use the cage only on her date nights to keep it special.

The little ache came back as I realized that the next time my wife fucked in this hotel, I would be at home watching.

January 2, 2016

The next day I drove about an hour away from our house to an adult bookstore. I quickly found the dildo section, but I had no idea that they came in such a wide variety of lengths, thickness, and colors. It took about 20 minutes, but I finally selected a long and girthy realistic one for her that I thought might be close to the size of her date. It was firm but flexible, and very real looking! It was $125, so it better be good! I got home and washed it with soap and water and dried it.

"Hey Honey, look what I got you," I said as I handed it to her, balls first. "I figured it would be good for you to get comfortable with a big penis before your big night."

"Oh my god, that is perfect!" she exclaimed. "And it looks to be the same size as he is!!"

She grabbed a water bottle from the frig and held it next to the dildo. "Yep," she said smiling. "Looks just like his dick. I can't believe in a couple weeks I will be experiencing a real penis this big."

She quickly set it on the kitchen table and bent over from the waist until her mouth was on the head. It took some work, but she was eventually able to get her mouth around the whole head and rim. But she could only go down the shaft less than and inch.

"Damn, that is tiring on my mouth," she said with disappointment after just a few seconds. "I am going to have to practice a ton if I want to give him decent head."

So for the next three weeks, she practiced her oral skills on the dildo three times a day, and spent more time going down on me as well. She also masterbated with it a few times to get used to something that big going in and out of her.

January 21, 2016

Her date was in two days, so she practiced her oral on the dildo a final time. It was the last time as she didn't want her mouth to be tired for the real thing. She proudly demonstrated her improvements to me, and she could now comfortably do several minutes of full mouth stroking on it, and was able to keep her lips locked to the shaft for about ⅔ its length (about 6 inches). And I noticed recently that she was also generating a ton more suction.

"How's that?" she asked proudly as she lifted her mouth off the dildo with a sexy suction sound. "Ya think that is gonna be good head for him?"

"Fuck yeah," I stammered. It was hard to breath as it felt like I had been punched in the gut. "He is in for one hell of a blowjob."

January 22, 2016

Her date was tomorrow, and we decide that it will be more intense for her if we didn't have sex until after her friend finished. I also got the cage from my cabinet in the bathroom, and she locked me up so I would not ejaculate until I was with her tomorrow evening. We jumped in the shower together, and I carefully shaved her thighs and pelvic area.

"You are super smooth!" I said proudly as I ran my hand around her groin. "No stubble to scuff up his tender penis head."

"If he did scuff it up I would just have to kiss it and make it all better," she said with a laugh. "Although I do plan to kiss his penis a lot tomorrow even if it's not scuffed."

"You are really very proud of your new super-sized oral skills," I said flatly. "And rightfully so. I know how hard you worked at it."

"He told me that he seldom gets blowjobs because he is too big," she said. "So I told him that I have been practicing for weeks and was going to suck him good and long tomorrow. He got very excited."

"Are you getting something in return?" I asked.

"I told him for our first time I just wanted him to put me on my back and give me a good solid pounding," she said with growing excitement. "I told him I wanted that bed to be squawking up a storm when he was on top."

We both fall asleep thinking about tomorrow.

January 23, 2016

The day for her first date finally arrived. I am not sure which one of us was more excited. We went shopping for a new bra and panty set for her, and we found a really cute red matching set, and also picked up a really cute blue dress that had a back-side zipper close. I was surprised how excited shopping for her "date" clothes made me, considering it was someone else that would be taking them off her. At about 4 pm I dropped her off at home so she could shower. I continued on to our local drugstore and bought her a travel-size bottle of good water-based lube and a box of 12 magnum condoms. When I got home, she was naked, sitting on the bed, just smiling. And dreaming. About him.

"12 extra large?" she laughed as she saw the condom box. "I'm just having my first date today and already you're planning for my next 11!"

"I assume you'll be doing this guy quite a few times," I replied softly. "And if you find another guy or two, you'll be through all of them in no time. And I assume you will continue to look for big boners that will fill these up."

"Good point," she replied. "And yes, I think "big boner" will be a requirement for all future dates!"

I opened the box of condoms and sat down next to her. Her breasts looked amazing. He was going to enjoy them.

"How many condoms should you take along," I asked as I separated the individual packages. "We don't want you to run out."

"Two should be enough for tonight," she replied with a chuckle. "We probably will just do it once this first time, but If he somehow manages to cum two times in an hour, and is still horny, I can always give him a good safe handjob." I put two condoms in the front pocket of her purse. I took a third package and opened it up and started to unroll it.

"Holy shit this thing is huge," I said with astonishment. "I had no idea magnums were this much bigger than the ones I used."

"But you saw his dick," she said grinning. "He is going to stretch that out and fill it up when he is erect."

"And fill your pussy, too," I said with a dry smile.

"And fill my mouth as well," she replied with a full grin.

I blew into it and filled it with air, tied a knot in the end, and tossed it on the bed. It was hard to believe a penis could fill that thing up.

We started to get her ready at about 5, as she was meeting him at 7. I had shaved her the night before, so there was no need to do that again, but to be safe I checked that she was still super smooth. I was now almost 24 hours in the cage, so I was really feeling the pressure. It would likely be at least 4 more hours before she was done with him and could unlocked me.

She did her makeup and hair, and I helped her into her new bra and panties, and then held the dress as she stepped into it. I moved her long hair to the side as I zipped it up. She slipped on her heels, and then twirled around for me.