The Journey of a Submissive Cuckold - Part 7

Click here to read the previous parts of the story.

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You woke up in an unfamiliar bedroom. Next to you was a woman you weren't married to. Annalise. The woman your wife had given you to while she was in New York with her lover.

You smiled as thoughts of your night of submission at the sex club filled your head. You ran your fingers over your ass and felt a touch of soreness from the beating Annalise had given you, a beating that had left her wet with excitement, which had led to you on your knees with your tongue tending to her desires.

She was on her side facing away from you. You were tempted to inch closer, to press your body against hers, to put your arm around her. It wasn't your place, though. You were, for all intents and purposes, her toy for the weekend. Your purpose was to do as you were told, not to pursue your pleasure without her consent.

You watched her sleep for a few minutes and then sought out your phone. You found it on the nightstand - next to the chastity cage you'd worn at the club and that Annalise had freed you from before bed - and checked for messages from your wife. You were delighted to see that she'd been in touch while you were asleep.

"I had a beautiful night, my love. We went to the most exquisite restaurant I've ever eaten at. He took me dancing afterwards. Then we adjourned to his apartment and he fucked me multiple times, giving me more orgasms than I could count and satisfying himself until he was fully spent. I fell asleep naked in his arms with his cum slowly dripping out of me. I slept as deeply as I ever have, though experiencing such thorough pleasure is a surefire way to bring about the most restful sleep," she'd texted a little after 5 a.m. your time (8 a.m. in New York).

You read the message a handful of times and felt both joy and jealousy, as any man in your situation would have. 

"I woke him this morning with my mouth," her next text began. "I sucked him slowly. I showed my appreciation for his generosity in welcoming me to his home, in treating me to the exquisite dresses and lingerie I bought prior to my arrival. I showed him my lust for him, too, my lust to make him feel good. I sucked his balls. I even licked his taint, which I've never done before. I think I would have licked his asshole had he lifted his legs and prompted me to do so. It shocked me to realize this, but it turns out that I've never been with a man as impressive as him and I find myself willing to go the extra mile to make him feel good."

You rested the phone on your chest as your hand moved between your legs. Your cock was engorged and you reached into your underwear and stroked yourself a few times, indulging in the pleasure of masturbation while you imagined your wife yearning to lick another man's asshole for his pleasure.

You knew better than to masturbate to a climax, though, so you pulled your hand free from your underwear and replied to your wife, telling her how much it turned you on to hear of her desire to please her lover. You offered details of your night with Annalise and suggested that you'd served as a good submissive to her, that you'd done everything you could to make sure she had a good night.

"I'm glad that Annalise proved a good match for you," your wife texted. "It's only fair that you get to have your fun while I have mine. I should also say that I've already been invited back next month, so I suspect this will become a regular thing. I never would have imagined myself in a situation like this - being a wealthy man's long distance lover that spends one weekend a month offering myself to him - and yet I'm already excited about my next visit and this one's nowhere near over."

You turned and looked at Annalise, who was still sound asleep. You imagined serving her each month. You imagined returning to the sex club. You imagined exploring the upper floor and the more hardcore activities that occurred there. Your pulse quickened and your balls tingled in a surprisingly pleasurable way.

"I love you," you texted your wife. "I miss you, too. I'm so glad you're having fun, though."

"I love you too," she replied. "We're going to shower together now. I imagine he'll fuck me and cum inside me. I'm already excited thinking about it. I'll call you later. Until then, be a good boy for Annalise."

You set your phone on the nightstand, turned to check on Annalise, and slipped out of bed when you found her still fast asleep. You quietly exited the bedroom and headed for her kitchen. It took a few minutes, but you found the supplies for making coffee and began brewing as you surveyed the breakfast options in her fridge.

Once the coffee was finished, you poured a cup and set it on a tray along with sugar and half and half you found in her fridge. You brought the tray to the bedroom and found Annalise sitting up in bed. She greeted you with a smile and you noted how flawlessly beautiful she was despite just having awakened.

"Good morning," you said.

"Good morning."

You moved to her side of the bed and set the tray on her nightstand.

"Sugar and cream," she said.

You took that as an instruction and added both a teaspoon of sugar and a good amount of half and half to her coffee before handing it to her. Annalise took a sip, smiled, and then pulled the covers away from her feet.

"I'd like you to suck on my toes while I enjoy my coffee. If you do a good job - and by that, I mean if you convince me that you could someday be a good cocksucker - I'll let you between my legs to give me an orgasm."

You fell to your knees and moved towards the foot of the bed. You positioned yourself to easily take her toes in your mouth, but you showered them in kisses before doing so. Annalise sipped her coffee and watched intently as you parted your lips and took her big toe in your mouth.

"That's good," she said softly. "Make sure you use your tongue. A good blowjob includes lots of tongue action."

You thought of the blowjob you'd watch your wife give her lover in Las Vegas. Then you thought of her giving him a blowjob that morning, You thought of her lips around his balls, sucking gently. You thought of her licking his taint and feeling a touch of excitement at the idea that he might want her - your wife - to lick his asshole while her hand pleasured his cock.

You found yourself trying to mimic the blowjob you'd seen your wife give. You closed your eyes tightened your lips around Annalise's big toe. You moved your tongue around it. You sucked in hard as you pulled back.

When you opened your eyes you were greeted with a brilliant smile from the woman your wife had given you to.

"Lindsay liked you, you know," Annalise said, referring to her kinky friend you’d met up with at the club. The friend that had, in fact, fucked Annalise with a strapon while you watched. The friend that had given Annalise a massive orgasm with her strapon. "She said that you'd be easy to train into being a good submissive. She said she could help with that, either in person or by giving me things to try with you." Annalise wiggled her toe in your mouth. "She was the one who suggested I have you suck on my toes like you were sucking a cock."

Annalise pulled the covers from the rest of her body, revealing the light blue camisole and panties she'd changed into after riding your face in her bed the night before. Her nipples were hard and you could see her wetness soaking through the thin, soft material of her panties. She played with her breasts as you continued to fellate her toe, acting to please her despite knowing that she was training you - in a small way, at least - to be a cocksucker.

"I'm not entirely sure why, but I keep thinking about that moment when we walked in on those guys from the locker room. When the submissive one was getting fucked while sucking dick," she said. "I keep thinking about how the dominant one offered his cock for you to suck on. I keep thinking about how hot it would have been to make you get on your knees and give head to a man we'd only just met."

Annalise was massively turned on. Her panties were wetter than they were just a minute ago. That's why you were turned on as she talked about making you suck dick, or at least that's what you told yourself. You weren't a man that wanted to suck cock, but if Annalise told you to, if she told you that it would make her pussy wet, perhaps you were the kind of man that would find pleasure in doing so for her.

You moved to her other foot. This time, though, you took as many toes as you could into your mouth. You sucked with far greater vigor, too. Your lips were stretched wide enough for it to feel uncomfortable, but you didn't mind. In fact, you were lost in your submission and in thoughts of taking your submission to an even deeper level.

"It's a shame I only have you for a few more days," Annalise said. "There's so much fun we could have if I had more time."

"My wife will be seeing her lover more often," you informed her. "At least once a month. It seems that he's having a good time with her and has already invited her back next month."

She smiled. "And it seems that your wife is enjoying the pleasure of being fucked by a superior man than her husband."

Your cock throbbed in a way that made you a little uncomfortable. What she'd said felt like an undeniable truth, though. Your wife's lover was, in many ways, a superior man to you. Thankfully, he seemed uninterested in having your wife as anything other than a weekend guest, because you weren't sure you stood a chance at keeping her if he decided he wanted more.

"That makes me happy," Annalise said. "As does your skillful sucking. You've earned a reward, so why don't you crawl between my legs and worship my pussy while I enjoy my coffee. Once you make me cum, you can wash my body in the shower. Then we'll begin our day together."

You crawled between her legs. You kissed her thighs on the way up. You licked her pussy slowly, worshiping her as she desired. You knew she was just as early in her exploration of domination as you were in your exploration of submission and you wanted her to feel like a goddess. You wanted to boost her confidence, to play your part as well as you could in hopes that you'd encourage her to go further into her dominant side, thereby deepening the pleasure both of you felt.

Annalise set her coffee aside, put a hand on the back of your head, and let the orgasm wash over her. It seemed to build slowly and pour out of her at a delicate pace. Her legs closed around your head for a few moments and kicked open as she unleashed a long, low moan. Her nipples were rock hard and her chest was soon flushed red. It seemed that you'd done a wondrous job of pleasing her and you took great pride in that.

True to her word, Annalise led you to her bathroom, stripped with you, and stepped into the shower with you close behind her. You washed her from head to toe, taking your time and using your hands to spread relaxation and pleasure through her body. She was more than happy to have you spend extra time washing her breasts and she didn't seem to mind that your cock remained erect throughout the shower.

"It was a pleasure to wash you," you said after drying off. "Thank you."

"You're welcome," she replied with a smile.

You prepared breakfast while Annalise did her hair and makeup and she entered the kitchen in leggings and a cropped t-shirt. She set her phone on the table as you served two plates of eggs, bacon, and toast along with two cups of coffee. She tapped her phone and the distinct sounds of sex filled her kitchen.

"Take your cock out," she said. "Masturbate."

You looked at her and then at her phone.

"Fuck me, baby. Fuck me!"

It was your wife. She'd sent Annalise an audio recording of the sex she'd had with her lover.

"Harder. Fuck me harder!"

You pulled out your cock. You masturbated. Annalise lifted her t-shirt and grasped her bare breasts. She slipped a hand down the front of her leggings and masturbated. You weren't sure if she was doing it for you or because she was turned on listening to your wife get fucked, but her arousal seemed undeniable.

"Cum in me!" your wife cried out. "Fuck! Cum in my pussy!"

The sex got louder. Harder.

"Cum in your coffee," Annalise demanded.

You moved the mug under your cock. Your wife moaned wildly. You came in your coffee. You watched the thick ropes of semen float to the top and begin to dissolve in the hot, dark liquid. It was strangely arousing to cum in something you knew you'd be made to drink.

Annalise came with you, her second orgasm of the day. You wondered if the fun you'd had in the shower had turned her on to the point that she needed to get off again. Whatever the source of her arousal, you were pleased to have brought her some amount of pleasure once more.

"I'm cumming!" your wife's lover cried out.

She came with him. You listened to them cum together and in your post-orgasmic state you couldn't help but feel jealous, almost overwhelmingly so. Annalise must have seen it on your face because she stood up, tucked your cock back into your pants, and kissed you softly on the lips, drawing your attention to her as the sounds of pleasure echoed in the background.

"Thank you," you said.

She smiled. "You're welcome. Now let's have breakfast, and of course I expect you to drink all of your coffee and without the aid of half and half or sugar. Just black coffee with cum for you."

You couldn't help but return her smile. "Of course."

You sat and sipped your coffee. It was awful, but drinking it felt as though it built a bond of sorts with Annalise, a bond that you very much liked the idea of building.

"So, do you have any plans today that you can tell me about?" you asked.

"As nice as those boys were in giving you a chastity cage, I was thinking that we could go and find one that fits you perfectly," she said. "Lindsay suggested a butt plug, too, so we'll see about that. I definitely want to buy a toy so you can practice your cocksucking and I might buy a strapon harness, too, as I have a feeling I'd very much enjoy seeing you on your knees in front of me with those pretty lips of yours wrapped around my cock."

You understood that your excitement was dampened because you'd just cum, but there was no question that Annalise was thrilled. Her smile was bright and genuine. She was practically bouncing in her chair. Either she was riding high on the novelty of playing with a submissive man for the first time or she was genuinely the kind of woman that was born to be a domme, because she was having the time of her life despite her two orgasms that morning likely having diminished her arousal.

"That all sounds exciting," you said. "Truly. A little scary, too, if I'm being honest."

"I asked your wife about all of it. I wanted to make sure she was okay with me taking things further than expected. She told me that she'd gone further with her lover than she'd expected, so there was no reason for you not to do the same with your domme."

She seemed delighted to refer to herself as your domme, but you were mostly caught up in wondering what your wife meant by going further with her lover. Was she talking about the taint licking? Had she done something the night before she hadn't expected to do? You wanted to text her, but she'd been clear that she would initiate any messaging with the two of you while she was out of town.

"Are you thinking about her?" Annalise asked.

You nodded. "About the going further thing. She texted this morning to say that she'd almost given him a rimjob and absolutely would have if he'd been in the mood for it, but she didn't mention anything else."

Annalise considered you for a few seconds and then put her hand on yours and gave it a gentle squeeze. "It's kind of scary, isn't it? Her all the way across the country with another man."

"With a better man."

"Better at some things, but not at others, I'm sure. I'd imagine he’d be absolute shit at being a husband, and from what I can tell, you're quite good at that, which I'm pretty sure is the most important thing to a married woman. In some ways, letting her visit him for the weekend is the ultimate act of love that very few men would engage in."

You smiled. "And her letting me visit you - in a manner of speaking - for the weekend is an act of love on her part."

Annalise nodded.

"Thank you," you said. "You're very kind, Annalise."

She laughed softly. "I don't get told that very often because I'm pretty sure I'm not that kind. I think I might just like you more than I like most people."

You felt yourself blush a little as Annalise's affection sent you into a deeply self-conscious place. You met her gaze, though, and she squeezed your hand once more.

"Did you enjoy watching me get fucked last night?" she asked.

"I did. Very much so."

"You know, Lindsay said she came while she fucked me. She said that almost never happens to her but there was something about the way I offered myself to her that really turned her on."

You remember Lindsay's orgasm. Annalise was face down on a spanking bench and taking a vigorous pounding so it's not surprising she missed her friend's orgasm, but you remember it well because Lindsay took such pleasure in fucking Annalise that you couldn't help but feel a desire to be the cause of that kind of pleasure, to be the one on the receiving end of a fucking, especially from a beautiful woman. It was an unusual feeling and one that you tucked away for fear of painful judgment should anyone discover your desire. Perhaps there was no need to hide it, though.

"I know. I saw her orgasm," you said.

"Yeah?"

You nodded.

"Well, she said she'd love to fuck me again and it doesn't have to be at the club. It's maybe a little bit weird to have strapon sex with my friend while outside the kinky confines of a sex club, but I was thinking about getting in touch with her today or tomorrow...and I was thinking that you could come, that she could teach me about using a strapon, about how to confidently wield it to put someone in a submissive headspace."

Her fingers moved up your arm and then traveled to your lips. You opened your mouth and she entered you with three fingers, pushing onto your tongue as you close your lips around them.

"Suck for me," she said.

You sucked her fingers as instructed. She moved them in and out of your mouth and the look of utter fascination and delight on her face made it clear that she really was interested in seeing you suck her strapon, which also meant you were now deeply interested in being on your knees with her dick in your mouth.

She pulled her fingers free and said, "I know I'm your domme for the weekend, but we don't know each other that well yet, so I want to make sure you'd be okay going to visit Lindsay with me and being a good test subject while she taught me some of the joys of using a strapon."

You wanted to ask if you'd get fucked - which you didn't feel ready for - but you refrained from doing so. Instead, you offered your enthusiastic support and Annalise rewarded you with a kiss. It felt good, though you felt a little guilty, too. There hadn't been any rules about not kissing her, but it still felt a bit wrong to do so.

"Let's go get you caged and plugged," she said. "Lindsay recommended a local place where she likes to shop for this kind of stuff. She said they have some clothes I might really enjoy, too, so who knows, I might be walking out of that store as a latex-clad goddess."

"That would be amazing," you replied.

She stood and you cleared away the dishes. When you'd finished cleaning up, you headed out for a day of kinky adventure with Annalise while your wife spent her day satisfying the sexual needs of her lover and taking load after load of his thick seed into her pussy and mouth. You were on opposite coasts, but you were both enjoying the gifts you'd given each other and growing into your respective roles in the new version of your marriage.

Neither of you fully understood just how deep you'd go before finding your equilibrium, but your journeys had just begun and you couldn't wait to explore the many pleasures ahead of you.