Not What We Planned Ch. 04

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A couple finds a new life as a cuckoldress and sissy.
3.5k words
4.34
31k
56

Part 4 of the 4 part series

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

Hello everyone, I just wanted to take a few lines here to thank everyone for the feedback on the stories so far. It's been interesting trying to put this all together. I also apologize for chapter 3's issues as I copy/pasted in the incorrect version. I resubmitted the correct version, so hopefully you're able to read that soon. Keep the feedback coming though! Even the haters, I can handle it!

* * * * *

"Good Girl." Reggie's reply read when Abby woke up the next morning.

We both had to rush around that morning, and I knew my next couple of days were going to very busy at work. That didn't change the fact that the previous night with Abby had been really hot and I couldn't stop thinking about the video we watched. I wanted to see more, especially before we went to the local sex shop. I was never one for shopping, but this trip would be quite a bit different than heading to the mall to find socks it seemed.

Abby was excited by Reggie's reply, but that still left her lingering question of what exactly "his rules" were going to be. For some reason though, she was afraid to ask. Luckily she didn't have to think about it too long, as Reggie sent her a message just as she was getting to work on Monday morning.

"Here's the deal. I don't share my girls. Any time that you and I play from here on out, I'm the only cock that you'll have. The hierarchy goes Me---->My Girls---->husbands. Anthony will have to make a decision. He is free to sit and watch us together. If he wants to play though, he's going to have to go in a totally different direction. Neither Eden nor Sam are going to allow him to fuck them. There is nothing in it for them. They are strong, dominate women. They will make sure that he has nights he will remember forever, but as I mentioned before, most husband's egos get in the way. You've been given an idea of what Sam enjoys. I'll be back in 10 days from my trip and would love to tap your ass again, so you need to get to work on Anthony ASAP."

Abby read the message at least 10 times before noon. She knew for certain that there was no way in hell she was going to convince me to just sit in a chair and watch her get the fucking of her life. Based on last nights new developments though, she felt confident that she had the opening she needed to make the second option happen. Much like my search the other morning, Abby started searching online for more information as well.

Little did either of us know, but we were both highly distracted at work that morning. We both snuck away for a quick break and watched the same husband/wife strapon video. Watching it alone without each other this time was eye opening as it was easier to concentrate, and we both noticed more details. We both clicked on the couple's profile after we watched the video, and this is where Abby and I's path went in very different directions.

That day at lunch I decided to take my food outside for a bit of privacy. I wasn't sure why, but I was quickly becoming fascinated with the idea of strapons, and pegging, which was a new term I had learned. Sitting outside afforded me the opportunity to be alone and do a bit more digging.

The couple had at least 50 videos under their profile grouped in different playlists. They had been posting the pegging videos for the last 5 years. The general theme of their channel seemed consistent but diving deeper into each video provided a lot more nuance though. The first playlist was simply titled "Strapon". I clicked on the playlist that had about 20 videos. The one Abby and I had watched together was the 6th video in the group. I only had about 30 mins for lunch, so I decided to watch the first three on the list. You could tell from the first video that it was probably the very first video they ever filmed to post online. The realness of it was actually kind of endearing. They didn't have a good light turned on, and the wife's harness wasn't tightened properly on one side, so it was sliding down a bit. The video ended with the wife stroking her husband with her hand until he came. They obviously had not perfected the penetration only orgasm at that point. It was still a hot video, and the wife was sexy as hell.

After watching the first video with Abby on Sunday night, I wasn't sure that I was open to the idea of being pegged, but after watching these videos, and knowing that I could watch her amazing tits bounce about, I was definitely opening up to the idea a lot more. We hadn't actually discussed the fact that Abby would do me with a strapon yet, but I assumed that the fact we were going to the sex store on Wednesday implied that. This certainly wasn't what I was expecting to come from the overall first swinging experience, but it was a nice surprise.

Unbeknownst to me, Abby had also gone back to the same couple we watched Sunday night on her lunch break. She asked for a booth in the back corner at her local diner to provide a bit of privacy. Clicking on the couple's profile, she came to the same set of playlists. The first was labeled "Strapon Play." The second was named "Toy Collection", and the third just had the initials FLR. Her curiosity got the better of her as she had never heard the term FLR before. She clicked on the playlist to check it out.

All the videos listed in here were from the last 18 months. There were a total of 12 videos, with the first one titled "BBC Bull Creampies Wife While Sissy Cuck Watches." There was a lot going on in the title alone that she didn't understand. She clicked on the thumbnail and the video started to load. The downside to the corner booth here was that phone signal was slow.

"More water?"

Abby jumped, startled by the waitress making her rounds.

"Oh, no. Thank you though." She replied

Looking down at her phone, the video was starting to play. There was a lot to take in with the scene. The first thing she noticed was the wife had on an incredible set of red lingerie. Bra, panties, garter, stockings. She looked fucking amazing. Her boobs seemed to be similar in size to Abby's and she wondered if hers would look that good in an expensive bra. She thought to her comfortable, but boring underwear drawer and realized she hadn't worn anything sexy in years.

Coming back to the video, the wife was making her way across what seemed to be a massive hotel room. Way more posh than the room she and I were in Friday night. The husband was sitting in a chair in the corner naked, and on the bed was a total hunk of a black man. Even watching on the small screen on her phone, it was easy to tell that the "bull" was a total stud.

The wife crossed the room and picked something up off of the nightstand and took it over to her husband. She stood in front of him speaking for about 30 seconds. Abby was really pissed she forgot to bring her ear buds, so she was watching the video with no volume. The wife then laid down on the bed with the Bull and began rubbing her hands across his body. He had a tight pair of boxer briefs on that showed off his very muscular thighs and a very pronounced bulge. He reached down to fondle her perfectly pushed up breasts. The wife sat up momentarily and pulled down her Bull's boxers. Out popped a beautiful specimen of a black cock. It had to be as thick around as her wrist. She laid back down next to him and immediately took it in her hand. She laid her head on his chiseled stomach and seemed to just be admiring it as she stroked it. This went on for a couple of minutes at least, until she finally took the head in her mouth.

Abby's thoughts rocketed back to Friday night. She knew that feeling of an unbelievably full mouth and the salty taste of precum. After stroking and sucking for at least 5 minutes, the wife started speaking to her husband again. Abby couldn't take not knowing what the discussion was. She took her last bite of sandwich, grabbed the check and went to the register to pay. As she moved, she became aware of how hard her nipples were.

Once in the car she fired the video back up and turned up the volume.

"Put the camera on the dresser and come lick my pussy." The wife instructed the husband.

"Yes ma'am" replied the husband

When the husband stood up, it was apparent that he wasn't actually naked. He definitely wasn't wearing what would be classified as men's underwear either. It was hard to see on the small screen, but it really seemed as though he was wearing women's panties.

He came to the end of the bed, and attempted to lay down as best he could, but half of his body was hanging off of the edge. It looked to be pretty uncomfortable, but he didn't seem to mind. His wife spread her legs, and he pushed his face in between her thighs. He pushed her red lace panties to the side and began to lick.

The wife took the massive cock out of her mouth and moaned.

"Oh baby. That feels good. I need you to make me cum. You got 2 nights a big black cock in your ass this week, it's time to return the favor."

Her husband was obviously skilled in this department because it didn't take long for her to climax. It was a thing of beauty, watching her sexy curvy body, perfectly accentuated by the lingerie, writh around in pleasure. Her orgasm seemed to continue for a couple of minutes. All the while, she never took the cock out of her mouth.

"MMMM, thank you so much sissy! You're soooo good at that!" The wife exclaimed.

Just then a text popped up on her phone.

"Meeting is in 10 mins girl, whereyat?"

It was her office mate Melissa. Abby had completely lost track of time. Luckily the diner was close to work. She was normally a very careful driver and only used the hands-free controls for her phone, but after what she just witnessed, Abby had to find out what FLR meant. When she came to the stop light, she typed FLR in the search bar. As the results loaded, she was pulling back into the parking lot. As she walked into the office, she clicked on the first article that came up titled "A Cuckoldress Guide to Life". She knew she was running out of time, so she quickly scanned the text. Female Led Relationship.

"Interesting." She thought to herself before she joined the meeting.

Abby and I got home pretty close to the same time that evening. We both seemed distracted, but we helped each other with dinner, and then sat down on the couch to watch some TV before bed. Neither of us mentioned anything about the previous night. After we watched a few episodes, Abby told me she was going to shower and read before bed. We kissed goodnight and she headed to our bedroom.

As soon as I heard the shower, I grabbed my phone. I immediately went back to the couple's videos. I just had to see more of what they were up to. I watched the next couple of videos, getting more and more turned on. The quality of the videos and thought put into them was getting better and better. The wife's fucking of her husband had gotten noticeable better as well. She teased him relentlessly, driving him crazy. She also seemed to be becoming more domineering in her language. It was weird to me at first when Sam made me call her ma'am, but there was also something strangely hot about it.

The last video on the third page of the playlist was titled "Husband cums on BBC." That title seemed a bit ambiguous. From the title alone it wasn't clear that the wife was using a strapon. BBC in my mind usually meant a black man. I clicked on the video though and was relieved to see that it was another hot strapon clip. The last 5 videos all ended with the husband cumming hands free just from the prostate pleasure. At this point I was also able to see just when he was about to get off and timed my own huge orgasm with his. As the sensations subsided in me, I continued watching the end of the clip.

"Oh baby, that was so hot. Look how hard you cum now just from getting fucked. James and I are so proud of you. You're becoming such a good little sissy!" The wife said, as the screen went dark right after.

"Whoa...." I thought to myself. So she had referred to him as a sissy at the end of the very first video I watched. That was kind of a mind fuck. The cock in the ass was one thing. At least there was a physical reason to gain pleasure from that. The demeaning/controlling talk was kind of hot in it's own strange way, but calling her husband a sissy? That didn't seem to make any sense in my head. Why would a woman want to be married to a sissy? What's in that for her I wondered. I had literally spent 90 minutes watching their videos though, and had an early morning the next day, so I had to get to sleep.

After Abby had showered and jumped into bed, she immediately got back on her phone. She read the entire article she had found earlier in the day, and then 5 other articles after that. Female Led Relationships seemed to encompass a lot of territory. It seemed as though many women in the cuckolding world that also played in the FLR world seemed to partake in the "sissification" of their husbands. Abby had to really stop and ponder for a moment all that she had learned just in the last 4 days. There was a huge world out there for the sexually curious. She had never been a prude by any means, but she had also never really attempted to explore anything either.

It did all seem to make sense. There were so many dynamics going on in these relationships that there did seem to be some logic to it. The Bull obviously knows what he brings to the table. What's in it for him to have to deal with any type of external relationship drama? He just wants to fuck. Really the same for the wife. She just wants to be fucked. But proper fucked. The way that only a man with a huge cock and expert skills can fuck. That word had really taken on a whole new meaning after Friday night to Abby. That leaves the husband on the outs it would seem, and as Reggie mentioned in his text, their egos get in the way a lot. Sissifying them really seemed to be the only answer. They are getting their rocks off, just not in a conventional way. That might be ok for some men in the beginning, but after a while, the novelty could wear off. By making it clear who is in control, and really embedding their submission in their brains, the Bull and the Wife free to enjoy their fun drama free. The husband gets his fun as well as long as he knows where he belongs in the hierarchy. It's a win/win/win, as long as the lines are clearly defined.

Abby began wondering if this would ever be possible with me. A week ago, if you would have asked her if I would allow another man to exclusively fuck her, and all the while I would be accepting of the fact that my sexual pleasure was going to be derived from being fucked in the ass with a large cock, she would have looked at you like you had 3 eyes. Today though, after witnessing how I reacted on Saturday and Sunday night, along with the incentive she had to get fucked by Reggie again as quickly as possible, she became determined to try her best. It would really be the maximum pleasure for everyone, she convinced herself.

Abby was never one to masturbate often, but she decided she should probably continue watching the couple's videos you know, for "research", and was feeling pretty horny at this point. Opening back up the video she started at lunch, she made herself comfortable and began rubbing herself.

The video continued, as the wife and her Bull were now heavily making out. The husband was back off the bed and filming with the second camera. After a nice session of foreplay, the real action was about to begin. The Bull was clearly in control. He flipped himself on top of the wife, slid his arms under her legs, and easily pulled her body in tight towards his. He put his hand over her mound and pressed his thumb firmly against her clit. Her back arched and she moaned loudly. From there, he pulled her red panties to the side, and aimed his cock directly at her pussy.

"Are you ready for this big black cock?" The Bull asked?

"Oh my god yes. I've needed to get fucked by your cock so bad!" The wife replied. "I can't stop thinking about it."

Abby thought to herself that while not identical to the first video she watched with me, the language the wife used now was really similar to the language the husband used before he got fucked by her strapon. Both yearned equally to get fucked by these huge cocks.

As the Bull pressed his cock into the wife, she let out an audible gasp. Abby knew that feeling. She hoped to have it again soon. She began to rub herself more vigorously. After a few minutes he wife and Bull were really getting into it. Unfortunately, the husband kept getting in the way of the other camera as he was trying to get in closer to the action. After he moved to the other side of the bed though, what a sight to behold. The wife's breasts moved in perfect rhythm with her Bull's strokes. She had a death grip on the sheets.

As Abby also neared orgasm, she started to wonder if the Bull was going to cum inside the wife. That was one thing that Abby was glad I had not brought up. When Reggie fucked her, he shot his thick load right in her, and she begged for him to do it. It was so primal. Abby was on birth control, so that wasn't really a concern, but begging for a strangers jizz was pretty unbelievable. I didn't bring it up for the same reason. It just seemed so crazy that I didn't even know how to process it.

That being said, the wife and the husband in the video both knew what they wanted.

"James is going to pump me full of his cum. Does that turn my little sissy on?" The wife asked her husband. It was the first thing she had been able to say in ten minutes.

"Yes it does ma'am. He's shooting deeper in you than I'll ever be able to." The husband replied.

With that encouragement, the Bull began pounding away at the wife's pussy. Again, similarly to the video of her husband being pegged, the wife's moans had turned guttural, and her eyes seemed to have rolled into the back of her head. She just laid there being pounded and wave after wave of her intense orgasm rushed over her.

Abby's orgasm began rushing over her as well. She wondered to herself why she didn't masturbate more often as her pleasure subsided. In an effort to not have a repeat of the previous night when my phone gave away my curiosity, she quickly closed out of the video and turned off her phone as to not get caught if I came in the room for bed. She laid there in silence though, pondering all that she had learned and seen recently. Her homework the following night would be watching the "Toy Collection" videos so she would know where to steer our evening of shopping. Little did I know, it was going to be more extensive than I thought. Abby's last thought before bed was counting down the days until the following Friday. She had 8 nights to sway me down a path that I had never considered, or even knew about just 5 days prior. The real work was just about to begin...

KinkyDirty
KinkyDirty
205 Followers
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22 Comments
bobbisworldbobbisworldabout 2 months ago

I love it when a Mistrss takes contol. He will be a great sissy.

AnonymousAnonymous4 months ago

Please. More

EhsheehsheEhsheehshe10 months ago

Would love to see the story progress to the husband becoming feminized with a loving wife

TrstxxxTrstxxx12 months ago

I love this story. PLEASE CONTINUE, PLEASE.

darthnader19darthnader19over 1 year ago

Please continue this. It's been amazing, really hope you eventually come back to continue the masterpiece!!!

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