A Cuckold Story Ch. 49

Story Info
The departure of an old friend.
5.4k words
4.03
4.6k
4
0

Part 16 of the 20 part series

Updated 06/10/2023
Created 03/23/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 49

Once we returned from our England vacation, Cheryl didn't immediately resume her occasional dates with the Gym Guy and Brad. In fact, it was only a little more than a month following our return that I came home from work one day to find Cheryl in the bedroom on the phone to Brad. My wife hadn't had a date with Brad in some time and I wondered if something was awry, but I'd long ago vowed not to pry into Cheryl's relationships with other men.

Cheryl stayed on the phone with Brad for almost an hour and when she finally emerged from the bedroom, she came out ranting and raving that Brad was an idiot and he deserved everything he got. And when Cheryl eventually calmed down, she told me that Brad's wife Cindy had caught him cheating with one of their neighbors.

Cheryl had no problem with Brad having sex with other women, after all, my wife was hardly one to cast stones. But, now, Cindy was threatening divorce and Brad was looking at a possible second failed marriage. Cheryl was livid that Brad could be so careless, and she firmly declared, "I told him we're through! I'm not going to be a part of breaking up his marriage!"

I spent a good part of that night consoling Cheryl over losing her long-time lover. Although Brad and I never really clicked, Cheryl truly enjoyed his company in addition to his sexual prowess and I was oddly sad to see their relationship come to an end. That said, I was proud of Cheryl for taking the high ground. She clearly wanted to avoid any situation where she might be blamed for Brad's divorce. And with Brad now on a short leash, Cheryl wasn't about to risk being caught red-handed with Cindy's husband.

That evening as Cheryl and I talked things over, my wife eventually began to feel much better about breaking up with Brad. I reminded my wife that there were plenty of other guys who would love to have an affair with a woman as beautiful and sexy as her. And when I reminded Cheryl that she'd just recently enjoyed a torrid, short-term affair with Ian, a man twenty years her junior, she finally began to come around.

"You know, you're right, Brad is getting a little too old," laughed Cheryl after I extolled her ability to seduce a handsome young stud like Ian.

Cheryl then giggled, "I guess if I'm going to have a lover, they should at least be able to fuck a couple times a night, right?"

When I wholeheartedly agreed with my wife, Cheryl turned to me and said, "Thanks, Mike. I love that you always know how to cheer me up. You're the best."

My wife's words warmed my heart and that night after dinner, Cheryl and I made love. It wasn't my best effort, but neither was it my worst and after coming way too soon, I spent the next twenty minutes with my tongue between my wife's legs, eventually getting her off while she reminisced about her final night with Ian.

When it rains, it pours and it was no more than a month following Cheryl's break-up with Brad that she received some disappointed news from her other long-time lover, the Gym Guy. It seems that after losing his job in a corporate restructuring, he and his wife decided to return to his original hometown, Buffalo, New York.

Cheryl had been seeing, and fucking, the Gym Guy for well over twenty years and although their get-togethers were sometimes few and far between, my wife always returned home with a satisfied smile and a creamy pussy for her loving cuckold husband. And now, knowing that the Gym Guy was moving away, Cheryl suddenly realized how much he'd meant to her all these years and how he'd frequently been her "go-to" guy when she was feeling sexually deprived.

When Cheryl told me the Gym Guy was moving, I could tell she was genuinely sad to see him go. In fact, after all these years of hearing my wife solely refer to him as the Gym Guy, my wife finally told me his name was Dave.

As it turned out, Dave's wife was leaving a week before him and so for his final week in the Bay Area, Cheryl arranged to spend several nights with her long-time lover. My wife even went so far as to use some of my Hyatt points to reserve a room at the San Francisco Hyatt Regency where she and Dave could enjoy his final two nights together.

To be sure, it was not an easy week for me, but I resigned myself to making sure Cheryl had every opportunity to enjoy her last few get-togethers with Dave. It didn't help that my wife had, after a somewhat lengthy hiatus, insisted that I be locked in chastity for the duration of her week-long adventure with Dave. In fact, it was five days before Dave's wife left for Buffalo that Cheryl sat me down and essentially demanded that I don my pink plastic cage.

I'd just arrived home from work and after greeting Cheryl, I headed up to our bedroom to change out of my suit. Uncharacteristically, however, my wife followed me upstairs and as I was taking off my clothes, she opened her dresser drawer and removing my chastity cage, she said, "Mike, I want you to wear this until Dave leaves for New York."

The way Cheryl phrased her request, I knew there was no arguing with her. There are times when my wife makes up her mind about something and there's no changing it. This appeared to be one of those times. And although I had been looking forward to numerous impassioned masturbation sessions while Cheryl and the Gym Guy enjoyed their last few moments together, I resigned myself to a chaste existence for the next couple of weeks.

As I was dutifully sliding the pink sleeve over my penis and attaching the rings that held it in place, Cheryl explained that she really wanted to focus all her attention on Dave before he left and that with me in chastity she knew I'd be a "good boy."

When I reminded my wife that I was always a "good boy", she laughed and said, "Yeah, I know, you are, Sweetie. But I just want to be focused on Dave. I don't want to have to worry about you playing with yourself. And besides, you know the rules, it's not like you and I are going to have sex until Dave leaves anyway. So, it's not really a big deal."

Cheryl had some good points and as I snapped the lock shut on my chastity device, I handed her the key for safekeeping. "There. That's not going to be so bad, will it?" giggled my wife as she retrieved her purse and placed my key in her pocketbook.

That night, and for the remainder of the next five days for that matter, Cheryl teased me incessantly about her plans for Dave. My wife was going to give him a send-off that most men could only dream about and as Cheryl described all the naughty adventures she had planned, I realized that my wife was right, had I not been locked in chastity, I probably would have been pestering her to allow me to masturbate.

All week long my wife had me running various errands to assist in her naughty plans. She had me picking up a couple pairs of new stockings at Victoria's Secret on Tuesday. And on Wednesday she made sure I stopped by the liquor store to purchase a bottle of French Champagne so that she and Dave could toast their long running relationship. And finally, on Friday evening, Cheryl asked me to pick up some lube and an enema kit at the drug store as she planned on letting Dave enjoy one last chance to fuck her tight little behind.

Dave's wife was leaving on Saturday morning and after he dropped her off at the airport, he planned to head straight home where Cheryl would meet him that afternoon. And that morning I found myself waiting patiently for my wife to return home from the hairdressers and the nail salon so that I could help her get ready for her visit to Dave's.

When Cheryl finally arrived home, I was surprised to see that she'd had her hairdresser color her hair an even lighter blonde than she'd ever done. My wife had originally been a brunette but with age, she'd gradually gone more and more blonde and as she walked in the door she asked, "How do you like my hair?"

I truthfully told Cheryl that it looked sexy and she beamed at my compliment as she said, "I hope Dave thinks so too." My wife then showed me her nails and she'd had her fingernails and toenails painted a bright, hot pink. "I'm going for the California blonde look. I want Dave to know what he'll be missing," laughed Cheryl as she then had me join her in the bedroom to help her prepare for her date.

Before she'd left that morning, Cheryl had asked me to pick out some clothes that she might want to take to Dave's. My wife wasn't sure how long she'd be gone, but she said that at least four outfits would probably be good.

Having me help choose her clothes is something that Cheryl occasionally likes me to do and although she always has final veto power, she has commented more than once that I "know what men like." It's always a thrill to rummage through my wife's closet selecting sexy outfits and shoes knowing that the goal is to make my wife as enticing as possible to another man. And for my wife's stay with Dave, I'd laid out several different dresses, skirts, tops and assorted panties, bras, garter belts and stockings. And, of course, I had several pairs of high heel shoes carefully arranged by the side of the bed.

When Cheryl and I entered the bedroom, my wife immediately insisted that I strip off my clothes. My wife knows that I relish helping her prep for her dates and she loves to playfully tease me knowing that when she's gone, I'll be buzzing from our interactions for hours. And for years now. one of Cheryl's favorite tricks to putting me in the cuckold mindset is to insist that I be naked while helping her ready herself for another man.

That day, Cheryl seemed in a particularly mischievous mood and when I was naked except for my chastity cage, she moved to me and reached down to tickle my balls, cooing, "Did you pick out some sexy clothes for me to wear with Dave?" When I replied that I thought I did, my wife then strolled over to the bed and began sorting through my selections, tossing out several of my choices but for the most part liking the sexy clothes and lingerie I'd selected. Cheryl then told me what she wanted to wear that day and to put everything else in the suitcase.

As I was carefully packing my wife's suitcase, I couldn't help but feel my penis attempt to swell in my chastity device as I pictured Cheryl in all these sexy clothes and shoes. And when my wife handed me her toiletry bag, she reached down to cup my balls while teasing, "Are you going to be a good little hubby while I'm gone?"

I immediately answered in the affirmative and my wife then giggled, "Yeah, I know you will. I'll bet you wish you could play with yourself though, huh?"

i couldn't help but groan, "Yeah."

Cheryl just smiled mischievously at my frustrated response as she cooed, "You'll just have wait, Baby. Your naughty wife needs to go see her boyfriend first. You don't mind, do you?"

Cheryl was in full-on tease mode and I couldn't help but groan in frustration as she was pushing all my buttons. To an outsider, my wife's playful comments would probably sound cruel, but in fact, I was loving every minute of it and when she finally said, "Okay Baby, time to get me ready for my date," I sprang into action.

First, I performed my standard task of shaving my wife's pussy and as I carefully ran the razor around her soft folds, Cheryl chatted away excitedly. And as my wife began telling me how she couldn't wait to have Dave for longer than the typical two or three hours they usually managed, I couldn't help but wonder if this is what she'd talked about with her hairdresser and manicurist earlier. I hoped not, but that thought was enough to have my penis twitching wildly in its cage.

Next, my wife showered, careful not to wet her hair, but wanting to be fresh and clean for her lover. And while Cheryl showered, I carefully laid out the clothes she'd chosen to wear that day. My wife was planning to wear a tight jean miniskirt, a black tank top and a pair of black high heel sandals. That was it, no underwear of any kind to get in Dave's way. I was sure that meant Cheryl was headed straight from our house to Dave's bed and I had to admit to a touch of envy that he, and not I, would be enjoying my wife over the next several days.

When Cheryl emerged from the shower, I was waiting with a fluffy dry towel and I spent several minutes toweling her off before applying perfumed oil to my wife's entire body. The whole time, Cheryl chattered away in nervous anticipation and I could tell that my wife was definitely looking forward to enjoying several lusty days and nights with her long-time lover. And when I finished applying oil to my wife, I knelt before her, sliding her pretty feet into her high heel sandals while Cheryl complimented me on picking out such perfect shoes to show off her new pink toenails.

I don't know whether it was her intention to tease me, but Cheryl didn't bother to put on her skirt or top while she did her makeup and put on her jewelry. And so, as I stood there watching my wife get ready for her date, I was treated to the mouth-watering sight of Cheryl parading around the bedroom wearing nothing more than her high heel sandals. If I hadn't been locked in chastity, this vision would have served to inspire my inevitable masturbation sessions, but with my penis vainly attempting to harden in its plastic sleeve, instead, it only served to add to my building sexual frustration.

Eventually Cheryl put on her skirt and top and as she was posing in front of the full-length mirror, making she sure looked as alluring as possible, my wife's phone chimed with an incoming text. Snatching the phone off her dresser, Cheryl squealed with delight as she announced that Dave had just left the airport and would be home in about a half hour. Wanting to maximize the time with her lover, my wife had me throw on a pair of jeans and a t-shirt while instructing me to place her suitcase in the trunk of her car.

With her suitcase safely stowed away, my wife was anxious to leave and after hurriedly reciting several chores she wanted completed while she was gone, Cheryl was soon on her way.

Although her exit had been rushed, I knew that Cheryl wasn't purposely snubbing me. My wife was caught up in the anticipation of being with the Gym Guy, or as I now knew him, Dave, and I felt certain that within the hour, Cheryl would be welcoming Dave between her legs, her sexy pink toenails and high heel sandals jiggling with each thrust of her lover's thick cock. And if Cheryl and Dave's long history together was any indication, my wife would be enjoying a series of orgasms as her lover fucked her senseless.

If I hadn't been in chastity, I have no doubt I would have masturbated then and there. Watching my wife primping for her date had been excruciatingly erotic and there would have been no way for me to resist pleasuring myself. But with my penis securely locked in chastity, I didn't have that option and so instead, I decided to go for a long hike both to clear my head but also to avoid dwelling on what Cheryl was doing at that particular moment.

A hike was just what the doctor ordered and when I finally arrived back home it was almost five-o-clock. Since it was still early, I decided to start in on my chores, first cleaning the bathrooms and then moving on to the kitchen. I suppose I should have resented the fact that I was spending my weekend cleaning the house while my wife fucked her boyfriend, but I wasn't bitter in the slightest. Cheryl needed this and if I could help facilitate it, then that's what a loving cuckold husband should do.

Sunday was much like Saturday in that I took a hike to start the day and then worked on various chores around the house for the remainder of the day. Throughout the day I would flash on what my wife and her lover might be doing and by the time I headed to bed that evening I was starting to think that it was going to be a long week knowing that Cheryl wasn't planning on unlocking me until next Saturday. In fact, Monday morning I was happy to head to work just to take my mind off my wife's escapades.

All day Monday I wondered when I would next see Cheryl. Not that I expected it, but my wife hadn't called and when she'd left to see Dave, she hadn't been certain how long she'd be gone. I knew that Dave's movers were coming on Wednesday so at the very least Cheryl would probably be home then, and I also knew she was planning to spend Thursday and Friday night in San Francisco with Dave so her return home might be short-lived.

This has always been one of the toughest parts of being a cuckold. Never knowing when my wife might opt to spend the night with another man or when she might return home can be nerve wracking at times, but I've learned to live with it. And since my wife was with the Gym Guy, a man she had fucked countless times before, I didn't have to worry for her safety and instead could just look forward to hearing all the naughty details later.

Monday night as I headed to bed I was almost certain I wouldn't see Cheryl until Tuesday night at the earliest and as I drifted off to sleep I decided I'd better pick up some food for dinner just in case my wife arrived home in time. However, at around midnight I was awakened by the sound of the garage door opening and a couple of minutes later I heard my wife's heels clicking on the floor as she made her way upstairs to our bedroom.

"Hi Honey, are you awake?" whispered Cheryl as she entered the bedroom.

"Yes," I replied before asking, "Is everything okay? I didn't think you'd be home so soon."

"Everything's fine. Dave's golfing with a friend of his tomorrow morning and I just thought I should come home and spend the night with my hubby," explained Cheryl as she took off her blouse and then lowered her shorts, leaving her standing beside the bed in nothing more than her panties and high heel slides.

After having been locked in chastity for a week, I felt my penis swelling in my plastic sleeve but I knew that Cheryl wasn't planning to grant me my freedom until Saturday and so I did the next best thing. Reaching out, I pulled my wife onto the bed and then buried my face in her crotch.

"Ooh, you're a naughty boy," giggled Cheryl as I pulled her panties to the side and began frantically licking and sucking her pussy. It was obvious that my wife had just come from her lover's bed and as I worked my tongue into her well-fucked opening, I was rewarded with a large dollop of Dave's come sliding out and into my mouth. I kept licking Cheryl's pussy for a good fifteen minutes until it became obvious that she had already enjoyed all the orgasms she was going to have that night.

When I raised my face up from between my wife's thighs, I was treated to the sight of my wife looking down on me with the most beautiful smile ever. And although I was feeling guilty about not having given Cheryl a climax, I couldn't help but return her smile, softly whispering, "I love you," before lifting myself off the bed and heading to the bathroom to wash up. Cheryl joined me soon thereafter and as we prepared for bed, I repeated my earlier expression of love for my beautiful wife.

That night my wife and I slept entwined together and although I had been awakened in the middle of the night, I felt refreshed and invigorated the next morning as I prepared to go to the office. Cheryl slept in and so she and I didn't get a chance to talk until that evening where she gave me a brief recap of her time with Dave telling me she'd wait until Saturday to give me all the naughty details.

The next two days were just what I needed. To have Cheryl all to myself was heaven itself and although I was locked in chastity the entire time, I realized that this brief interlude helped to lessen my angst and to more fully appreciate how lucky I was to be married to a woman as beautiful and exciting as Cheryl.

Although my wife wasn't sharing the details of the previous nights with Dave, she was keeping my arousal at a fever pitch by teasing me incessantly about her upcoming two nights in San Francisco with her lover. In fact, on Wednesday evening she performed one of her sexy fashion shows and as I sat on the bed wearing nothing but my chastity device, my wife modeled all the sexy outfits she was planning to bring to San Francisco.

12