Not What We Planned Ch. 03

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A couple finds a new life as a cuckoldress and sissy.
3.9k words
4.47
23.7k
40

Part 3 of the 4 part series

Updated 06/10/2023
Created 05/29/2020
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KinkyDirty
KinkyDirty
206 Followers

Abby was up early the next morning. I had tossed and turned all night, but finally seemed to be knocked out, and she didn't want to wake me, so she got out of bed and headed to the kitchen. She hadn't slept well either, but neither of us discussed any part of the evening when we got in bed that night. She knew this would be the second awkward morning in a row. In any many ways, last night was even crazier than the first. They went to the swingers' club with the general idea that they might hook up with another couple. But Abby could have never expected that last night would end with her husband having a 7-inch black dildo in his ass and having what seemed to be his most intense orgasm ever because of it. She knew the first night had been humiliating for him, but she didn't know what to think about the previous evening. Would he be humiliated again? Embarrassed? What if he loved it? What did that mean for the future? Abby did not consider herself a dominate person. While she was fascinated by Sam taking control of the room and surprised by what other areas of Anthony's body incurred pleasure from, Abby felt like she didn't know anything about this type of play. Last but not least, she couldn't help but wonder why Reggie had organized this whole thing.

As she was sitting on the couch deep in thought, her phone buzzed and startled her back to reality. "Speak of the devil" she thought to herself as she picked up her phone.

"Hey girl, it's Reggie. Sounds like last night was interesting at your place. How we move forward from here is complicated. I only play if I make the rules. I'm not trying to be an asshole, I'm just stating the facts. I know you enjoyed the experience Friday night, and I'm sure you want that again, but the ego of most husbands gets in the way. Last night was about taking that ego down a notch, but also teaching him that there is still pleasure that comes from not being in control. At this point you have to decide if you are on board. The opportunity is there for both you and Anthony to experience pleasure like you've never had, but it's going to take effort on your part to steer the ship. Husbands typically don't just hop on. Hit me back and LMK. If not, I wish you luck in your future escapades."

Abby's reaction towards Reggie's assertiveness was completely different than Anthony's. She was drawn to it. She immediately got butterflies in her stomach and Friday nights feelings rushed back over her. She had never had sexual pleasure on that level. While she still felt a small twinge of guilt admitting that he was right. She did want him again. Reggie was the best fuck of her life. She had seen the other attendees at the club that night. No one had sparked her interest at all. She knew if she and Anthony tried again, she would never find another man that could make her cum like that.

Reggie's ultimatum had her mind racing. He knew exactly what he was doing by planning the previous night, and he knew that pulling the proverbially rug, or "cock" out from under her would make her want it even more. What did he mean by "his rules" though?

Right then she heard the toilet flush in the bathroom. I washed my hands and came into the living room.

She felt her heart thumping as she was still looking at the screen on her phone. "There's coffee in the kitchen if you want some." She managed to say. She quickly put her phone down as I went to the cabinet and got a mug to pour some coffee.

It felt like déjà vu. The same awkwardness as the morning before, but the tension was even more palpable. Abby finally decided that humor might be the best way to clear the air.

"So how's your butthole this morning?" She quipped, smiling at me.

"What the fuck, Abby?????" I snapped back.

"I'm sorry! I literally have no idea how to break the ice this morning. I'm just trying to add some humor to the situation." She replied

I sat back on the couch, sulking slightly, but about what, I wasn't exactly sure. Not even 8 hours ago, I had experienced the most intense orgasm of my life in this exact spot. Was I scared because I might have to admit that in the ensuing conversation?

"My butthole is fine. Thank you for asking." I finally replied

They sat in silence for another minute or so.

"I couldn't sleep last night Abby. I would like to have an open conversation about the actual encounter last night, but my main question is why did Reggie set me up like that? It's just fucked up."

Abby just nodded in agreement, not quite sure how to respond. As she was about to speak, she was hit with another twinge of guilt. Earlier this morning she felt guilt about being so honest about how good the sex was with Reggie. Now she felt guilt for the lie she was about to tell her husband.

"I don't know why Reggie would do that." She said as she looked me directly in the eyes.

Abby had never been a selfish person. But just now she had lied directly to me in hopes that it would mean she could keep getting fucked by Reggie. She didn't know how that made her feel in that moment, but she had done it anyway.

"I need you to be 100% honest with me Abby. Did he tell you what he had planned?" Anthony asked

"I promise you, he did not. He really seemed sincere in his text yesterday." Abby replied

"Last night was interesting though. Did you want to talk about that at all? I promise I'm not judging you about anything that happened. I want to let you know also that I'm sorry that I've never pinched your nipples or rubbed your taint before." Abby continued. She didn't want to mention the dildo unless I brought it up first.

"It's fine." I replied. "Don't get me wrong, it was fun, but it's not like our normal sex isn't intense too."

I always prided myself on being an honest person, but I too had just lied to my spouse. I was going to need more time before I could admit to anyone else the amount of pleasure I had experienced the night before.

"Ok, well just know that we can always talk about it if you want. I don't want to pressure you at all though. I'm going to get cleaned up and make the grocery run. Maybe we can relax and watch a movie this afternoon?" Abby asked

"Sure, that sounds like a good plan after the last few days" I replied

Once Abby left for the store, I flipped on the TV to watch some football and hopefully distract my mind for a bit. It didn't really help though. I just couldn't get over how intense the feeling was with the dildo inside me last night. I vaguely knew what my prostate was, but only in the joking manner that it was mentioned when one of our buddies turned 40 and had to go see the doctor for his annual checkup. The fact that it provided such pleasure was totally new to me.

I grabbed my phone and did a Google search. I quickly found quite a few medical based articles that lended credibility to the fact that the prostate can provide pleasure to all men. Why I felt the need to validate that, I wasn't sure. About halfway down the page he came across an article from Men's Health titled "The Male G Spot is Real". I clicked on the article and found that my experience definitely wasn't unique. Men across the world seemed to be exploring their prostates regularly. Again, this made me feel more comfortable for some reason. I had never questioned my sexuality, but the thought of getting off with something in my butt just didn't sit right until now.

As I continued to read, the article listed off a ton of toys that men used to explore this sensation. The article also alluded to the fact that some men came from prostate pressure alone. Last night was such a blur that I didn't know exactly what made me cum. Was it the dildo, Sam's rubbing, or her gorgeous rack? I couldn't really be sure. Curiosity had the best of me now though. I hopped on XHamster, to do a search.

Not quite sure what the best term was, I typed in "Dildo Prostate Orgasm". When the search fully loaded, I couldn't believe it. 1500 videos matched that search. Obviously the rest of the world knew more about this than I did. I began clicking on videos to see what I could learn, and I quickly found out that men were indeed having massive orgasms from anal penetration alone.

The more I watched, the more I became turned on. I could tell this was pretty close to what I experienced last night, and that made my dick hard. I also couldn't help but notice that the men in the videos cumming the most were using very sizable dildos. The one that Sam used on him really seemed to be the minimum size. Also, like last night, most of the men seemed to be using black dildos.

One of the related videos from the search caught my eye. The thumbnail was nothing but a great set of tits. The title read "Strapon Wife Pounds Hubby to Orgasm". Just like the prostate exams, I had been aware of strapons obviously, but always from a joking manner. I had never put much thought in to their use until seeing Eden come out of the bathroom with it on Friday night.

The video began with the wife walking up to her husband who was lying on his back naked.

"Are you ready?" The wife asked.

"Yes ma'am" the husband replied. My thoughts immediately shot back to the previous evening when Sam made me call her Ma'am in order to continue.

As the wife approached the husband, her body came in to view. She was amazingly curvy. Her large breasts had the perfect tear drop shape and her waist tapered in perfectly. She spread her husband's legs apart and you could see her hips perfectly outlined by her harness. As Anthony gazed up and down her body in the video, she reached down and lifted up her strapon cock. It was massive. It was well over 8 inches long, and so thick that her entire hand wasn't able to wrap around it. And of course, like most other dildos in the videos, this one was black. She pushed her husband's left knee further to the side while she plopped the cock down next to his semi rigid dick.

"MMMMM" she said she watched her husband's dick jump a bit as her cock rubbed across his crotch. "You've been needing this, haven't you baby?" she asked

"Yes ma'am, I've been thinking about this all week. I need it so bad."

"I can tell. Your little dick is jumping with excitement! I bet he's going to cum so hard tonight!" She exclaimed

She began lubing up her cock with copious amounts of anal lube. She used both hands, and as she spread the lube up and down the shaft, her arms gently pushed her breasts together. With her left hand she pushed her husband's knees back towards his chest. There was something so hot about that exact moment. I had done that numerous times in my life with Abby, but seeing the wife do it to the man was a totally different experience. She aimed her cock directly at his ass and applied pressure. As the big cock began sliding in, the husband moaned in pleasure.

"Hey Honey, I'm back!" Shouted Abby. "Can you come help carry in these groceries?"

My heart shot through my throat. I was so wrapped up in all the videos I had been watching that I didn't hear the garage door open. I quickly turned off his phone and jumped up, trying to conceal his hard on in the waist of his boxer shorts. I walked out to the garage and smiled at Abby as she walked in with a couple of bags of groceries. Luckily she didn't notice how flustered I was. I stood next to the car for a few seconds to let my nerves calm down. I grabbed the remaining bags of food and took them to the kitchen. We put the food away in silence.

"I'm going to take a shower" I announced. I needed more time to himself to cool off. I flipped on the shower and spent the next twenty minutes trying to wrap my head around what I had just watched, and why exactly I was so embarrassed I felt the need to hide it from Abby. The men using dildos on themselves were one thing. They were hot in the fact that these videos confirmed that men of all types were enjoying prostate play. The strapon video was something different though. The beautiful wife being fully in charge of her husband's pleasure, and most importantly that pleasure coming through his submissiveness was something that I had never really considered. My world view of sex had always been more rooted in societal norms.

I was still horny when I hopped out of the shower, but I was definitely calmed down now. I went back to the kitchen and helped Abby make lunch. Once everything was prepared, they sat down on the couch to watch a movie. After then ate, Abby snuggled up against him and they finished their movie. After that they watched a few episodes of their favorite shows. It was a perfectly peaceful afternoon. I was feeling much better about everything at that point. Little did I know that the tumult of the weekend wasn't over.

"Let me sneak out from under you, I'm going to take a leak real quick." I said, as I grabbed a pillow to put under Abby's head. She looked so innocent laying there all balled up I thought to himself. Nothing like the woman from Friday night that seemed to be hypnotically controlled by her sexual lusts.

After I took a piss and washed my hands, I walked back toward the living room.

"I love your black cock!" I heard as I turned out of the hallway.

"I love your black cock, what?" The wife from the video I was watching earlier said firmly

"I love your black cock, ma'am." the husband said

I froze, staring at Abby, with her staring back at me in total shock

"I'm so sorry!" Abby exclaimed, quickly shutting the phone off and tossing it back on the coffee table.

"Ray called, and I went to pick it up but didn't catch it in time and your screen just opened."

We both just stood there, unsure what to say next. After 17 years of my life spent with my wife, I never thought I could feel so awkward or embarrassed around her. After about 30 seconds of silence, Abby couldn't stand it anymore.

"I think his butthole is probably feeling pretty good." She said, hoping to break the tension.

I still didn't know how to respond, but after a few seconds, I began to chuckle. Abby did always have a wit about her.

"Yeah, it definitely sounds like it." I replied.

"So I guess we can talk about this now? Abby asked

I squirmed a bit. It wasn't that I minded having a general conversation, but at that point I knew I still didn't have exact answers to the questions that would likely be asked.

Abby patted the couch cushion. "Come sit next to me."

I walked over and sat down again. Abby was definitely going to have to lead this conversation.

"Reggie feelings aside, tell me about last night from your perspective." Abby said

"I don't know yet." I replied. "I mean, you were there. I'm not sure what all there is to say."

"I'm not sure either. I already mentioned this, but I felt like pretty silly last night having a 26 year old girl teaching me about my husband's body. That should have never been the case. I should have been correcting her on her technique when she pinched your nipples. I should have been telling her you like your taint rubbed in a clockwise motion, not counterclockwise. 17 years and all I know is to give a generic blow job and let you bang me." Abby said, shifting her gaze down to her lap.

"Don't say that Abby. If you remember, that's the whole reason we are here right now. We were stuck in a bit of a rut. On both sides. Granted, I didn't expect to be having this conversation after such wild events, but at least we are opening up." I replied.

Abby looked up at me and smiled. "Yeah, it was a wild weekend. I'm glad we are talking though."

"So about that video...." Abby said quizzically

"Well, that's a bit of a story." I said, laughing a bit.

I told her about my curiosity about my prostate, and how that kept leading me down new paths until eventually she startled me when she came home. She seemed fascinated the whole time I was explaining the scenes in the videos. I also admitted that the main reason I clicked on the husband-and-wife video was the thumbnail of the wife's great rack.

"I noticed those too!" She said, smiling.

We got through the entire discussion and luckily we both seemed to feel relieved.

"So I have to ask. Does it really feel that good? You know, in your butt like that?" Abby asked

I swallowed nervously before I answered. "Yes. It really does." Admitting it out loud made my stomach flutter a bit, but it also felt good to be honest about it.

"That's the total mind fuck here Abby. Reggie didn't send Sam over here to have sex with me. But what the hell does I care about my prostate? It's all just weird." I said.

After the great conversation they just had, she didn't want to get off track with Reggie. Both because she didn't want to have to lie again, but also because she was genuinely curious about all she was learning.

"Yeah, it's definitely strange." She replied. "So does the husband actually get off in that video?" Abby asked, quickly changing the subject.

Anthony laughed "I really have no idea. I only made it a couple of minutes into the video."

"Maybe we should find out!" She said, rubbing her hand firmly across my lap.

I was already half hard just from the discussion.

"Mmmm, someone is turned on." Abby quipped.

She reached out to the coffee table to grab my phone and handed it to me.

"Here, you hold this. I'm going to need both my hands for a bit!" She said, smiling coyly

She began rubbing her hands all over my crotch, putting down extra pressure when she touched my dick. She then snaked her hand up my shirt, pressing firmly across my chest. Her fingers teased my nipples. Everything happened so quickly, that I was struggling to keep up. I finally got my pass code inputted on my phone and the screen came back up.

"That's a good boy. Look how deep this cock is in you. I know you love it when I bottom out." The wife from the video said

"I love that full 8 inches of cock in me ma'am. I can tell already I'm not going to last long. I need to cum so bad." The husband replied. With that, the wife started to really work her husband's ass.

"OMG! That is so dirty!" Abby exclaimed. She pinched my nipple firmly. A jolt shot through my entire body and I moaned.

"Are you moaning from pinching your nipple, or from the thought of a big dildo up your butt???" Abby asked sternly.

"I'm not sure, maybe both." I replied.

"Maybe both, what, Anthony?" She again asked sternly. She never called me Anthony, but in this context, it was kind of hot.

"Maybe both, ma'am." I said, moaning again.

"Ohhhh, I could get used to that Anthony." Abby said. "Now let's get those pants off."

I struggled watching the video and pulling my pants off. I wanted Abby to touch my dick so bad, but I couldn't take my eyes off the video either. The entire scene was mesmerizing. The husband's eyes were practically in the back of his head, and he didn't seem to even be able to speak at this point. That was a total shame though, because every time she thrust into him, her boobs swung perfectly.

As soon as my pants were down, Abby started her next newly learned technique. Laying across my body, she wrapped her hand underneath my balls and started applying pressure with her middle fingers. It felt amazing. With her other hand, she grabbed hold of my dick and started stroking it. I wasn't going to be able to hold out for very long.

Judging on the video, the husband wasn't going to last much longer either. His wife was relentlessly pounding him. He had gone from moaning to a much deeper, more guttural sound. I couldn't help but notice the similarity in the husband and how Abby looked on Friday night. Just fully present in the moment, and all the sensations created by it. Out of nowhere, his dick started spasming and his load shot all across his mid-section. As soon as I saw it happen, my own orgasm erupted, only not on my stomach, but mostly across Abby's face. It had been so quick I didn't have a chance to warn her.

She was obviously startled, but being a trooper, she didn't stop until I was fully spent.

KinkyDirty
KinkyDirty
206 Followers
12