The Women in My Life Cuck Me Ch. 02

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High school crush gets involved, they lock me up.
5k words
4.56
62.3k
85

Part 2 of the 2 part series

Updated 06/09/2023
Created 09/25/2019
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Philyssis
Philyssis
158 Followers

Continued from part 1, right in the middle of a sex club...

I was relieved when my wife grinned. Then I was a bit concerned as it turned into an evil grin.

"Wow Phil" my wife said to me. "I knew you had a dirty mind, but I didn't know you had THIS in you!"

Amy, my wife's little sister, leaned over and kissed me on the cheek, then looked at Tara, "I'm so glad he had this in him. I've never felt that full before. Or rather, I'm so glad he had that guy in him" both women started laughing.

Tara continued "I can't believe this got you off Phil. I don't even know what to do with you now."

"I can help you." I turned to see where that voice was coming from, and I couldn't believe it when I saw. There she was, with freckles and green eyes. It was Sarah, a girl I knew in high school and hadn't seen since then. I had such a crush on her. And here she was, walking up to me in nothing but a bra, with her perfectly round breasts spilling out, and her shaven pussy on display for all to see. And there I was, cum all over my face and leaking out of my ass. She looked at Tara and asked "Are you Phil's wife?"

"Yes, I am, do you know each other?" Tara asked.

"I'm Sarah, we went to high school together. I don't think I've seen him since then. But as I was getting fucked at the other end of the room, I recognized Phil when he came in, and I saw the whole thing."

OMG, I finally get reunited with my high school crush, and it's when my sister-in-law denies me sex, makes me take cock in the ass, and snowballs cum with me. I can't believe she was watching the whole time.

"Look," Sarah said. "I own an adult toy store downtown, and I also work as a part time sex therapist. Bring Phil down to the store this week and I'll teach you exactly what to do with him."

Amy asked "Can I come too? I'm curious."

Sarah smiled at her "Based on what I just saw, you should definitely come too. What's your relation?"

"We're sisters" the girls said in unison.

"Oh fuck, that's hot. Phil is lucky to be in this situation" Sarah said.

I had no idea what she had in mind, but I was excited for this.

"Wait a minute!" Tara said. Un oh, I thought she was going to put the brakes on all of this, but she went a different direction. "Is this the Sarah you told me about, the one that you had a major crush on in high school?"

Although I was already a bit embarrassed, I could feel myself turning red. "Yes, that's her" I said quietly.

They all giggled a bit and Amy said "Too bad you didn't find her instead of me, you could have lived out your high school dream."

This made Sarah laugh a bit harder. "No no" she said. "The purspose of this night is to get fucked by big cocks, and I can see that Phil's cock isn't big enough for me. I would have just made him watch. And based on how hard he came from tonight's events, that would have been the right thing to do. Some people are born to be cucks. I can't wait to see you all at my store. Make sure to call ahead and make an appointment." And with that, Sarah walked away. I just stared at her round ass as it moved with each step.

"I guess you still think she's hot, huh?" my wife asked. But before I could answer she said "I think she is too. We should get cleaned up and head home now."

*A couple days later

I pulled up to the adult store, just in time for our appointment. Me, my wife, and her sister all got out of the car and headed in.

Sarah was waiting with a big smile. She was just as beautiful as when we were in high school. She was wearing a tight shirt that showed off her midriff and her cleavage, as well as tight jeans that hugged her ass. I couldn't help but stare at her body.

She locked the door to the store and led us to a back room with comfortable seating. She sat us down and started telling my wife and her sister all about what it meant to be a hotwife with a cuckold husband. She explained how men can get off being submissive, and she even talked about what it meant to be a sissy, and why emasculation was so powerful.

"But there's something very important we should do as a next step" Sarah said. "If you really want to control him, I suggest you lock him up in chastity."

"Um, what?" I stammered.

"It's not up to you. You gave up your place on top when you submitted to a fat cock at your sister-in-law's request. And we all saw how hard you came from that, without even touching yourself. Tara, you should know that if you lock him up, you will have even more control over him. Not just sexually, you can even get him to do more around the house while you read a book and drink wine."

Tara's face lit up "Let's do it! Well, I should ask, how do we go about this?"

Sarah said "I have an assortment of sizes in stock, we just need to measure him. Phil, stand up and pull your pants down."

The women all giggled at the suggestion. I hesitated, but I found something inside of me compelling me to listen. I stood up, unbuckled my pants, and dropped them to the floor.

"It looks like we have a problem" Sarah said. "He needs to be soft for me to measure him."

Sure enough, I was raging hard. Standing there with my dick out in front of the three hottest women I knew all staring at it made the blood rush to my cock.

"We're going to have to take care of that" Sarah said. "Do you girls mind if I try something?"

"Please do" my wife said.

Sarah knelt down in front of me, and took my cock in her hands. I could see right down her shirt, and I could see the curve of her ass behind her. She started lightly touching my cock with both hands, and then she started moving her mouth closer to my cock. Her lips were so close, so I moved my hips forward.

She slapped my cock "You don't get to move unless I tell you to move, understand?"

"Yes" I said, surprised that that had happened.

"Say 'Yes Mistress.'"

"Yes Mistress."

She started stroking me now, but slowly. She stuck her tongue out but didn't quite touch my cock with it, then she pulled her head back and began to speak. "You want me to lick it don't you? You want your high school crush to lick the precum off the tip of your cock so that I can taste you? Or how about I take the head of your cock in my mouth. Would you like that?"

"Yes Mistress" I whimpered.

"Well that's never going to happen, ever" she said. That made Tara and Amy chuckle a bit. "The only time in your life that I will ever come in contact with your cock, is this handjob that you're getting right now. So you'd better enjoy it."

Denied, right in front of my wife and her sister. That blowjob I longed for was just out of reach. But something about it was so hot that I could feel my orgasm start to build, and Sarah could tell.

She pulled her top down a bit to show more cleavage, but not her nipples, and then she pointed my cock at her tits and said "I want you to cum all over my tits. Do it! Show me how much this is turning you on!"

I grunted as I started to cum, but she took that as a queue to stop stroking me. Her hand was motionless, completely ruining the orgasm. I spurted streams of cum onto her cleavage, but without the feeling of a full orgasm.

She stood up and pulled my head towards her chest. "You made a mess; you have to clean it. Start licking!"

I stuck my tongue out and started licking the breasts of the girl I secretly loved in high school. I scooped all of the cum off as she instructed, and swallowed it all.

"Well that did the trick. I can measure him now." she said while looking down at my now flaccid penis.

While taking measurements she talked to Tara and Amy about ruining an orgasm, tease and denial, and CFNM (clothed female, naked male). There were so many new ideas put in my wife's brain today, I didn't know what the future held for me.

Sarah said she needed to grab some things and left. She came back with a pink silicone chastity cage. She got on her knees in front of me again, and slid the ring around my cock and balls. Then she slid the cage over my penis. The lock was built in, and she used a key to lock it so it wouldn't come off. There were two keys, and she handed one to Tara and one to Amy.

Sarah started to instruct them. "You should wear the key in a place where he can see it, like around your neck. It will be humiliating for him if he realizes that anyone in public catches on to what the key is for." The women giggled at this. "And you don't need to take it off, ever. This has enough space in it that it can be thoroughly cleaned in the shower without taking it off. After showering, you can get a bit of baby oil gel in there to prevent the skin from getting irritated."

"Oh, I almost forgot!" Sarah exclaimed. "The theme next Friday is femdom, which means all women can come, and submissive males can come. Alpha males are asked to sit this one out. I have something that I think you two ladies should buy."

Sarah led us over to some strap-ons. "These" she said, "are going to be just perfect. They're a new model with a vibrator that touches your clit. They're made so that the faster you pump the cock, the more intense the vibration is. This means that if you are fucking someone, it will feel better for you to pump faster and harder."

"I've never really thought about fucking a woman with a strap-on" Tara said.

Sarah smiled. "You don't have to fuck a woman; you can fuck your husband." The women all giggled, and I noticed that my cock started to twitch in its new prison. "The great thing about being a woman on femdom night is that you can go back and forth from being dominant over a man or woman, to being submissive to a woman. Whatever fits your mood in that moment, you can just roll with it. Men, on the other hand, can only be submissive that night."

After a bit more chit chat, Tara and Amy each bought a strap-on. They made sure they got big ones, about 9 or 10 inches long, and thick. Looking at the strap-ons started turning me on even more, as I realized that I longed to have these women strap them on and fuck my ass with them.

As the week went on, my wife started getting into the keyholder role. She ordered me to do chores, lots of chores, and taunted me with the key. We had to be a discreet because we have kids, but she always got what she wanted without any complaints from me. Most nights, as we lay in bed, she'd tell me I did a good job that day, and let me lick her pussy till she came 2 or 3 times. My locked-up cock ached for release, but I was enjoying the constant sexual high.

One night, after three orgasms courtesy of my mouth, my wife flopped down in the bed next to me. She looked at me with a big loving smile and said "You've done so much for me this week; all the chores you do, and then at the end of the day it's me that gets off, usually 3 or 4 times. You deserve a reward. On femdom night, you should know that I plan on fucking you so hard that you cum in your cock cage. I'm really going to work your ass with my strap-on. Would you like that?"

"Yes mistress, I would love that reward from you."

"Good, because I'm looking forward to giving it to you. Oh, and by the way, I need you to go to my sister's house tomorrow. She has a few chores for you to do."

The next day I was over at Amy's house. She put me right to work. After about an hour of hard labor, I was tired.

"Do you need some motivation to keep going?" she asked, as she could see I was slowing down. "Here, come have a drink of milk."

She pulled her shirt down, exposing her bra-less breasts to me. She gave them a gentle squeeze which made a drop of milk appear on each nipple.

I knelt in front of her and took one of her nipples into my mouth. Once I started sucking and swallowing her milk, I got a huge sexual rush. This was exactly the kind of motivation that I needed. After I had sucked on her breasts for a few minutes she pulled away, "Good boy, now go finish your chores."

After I had finished the list of chores, she smiled at me. She held up a chain with the key to my chastity cage. "Do you want your reward now?" She asked.

"Yes mistress!" Holy fuck! What was she going to do? Was I finally going to get to fuck my sexy little sister-in-law?

"Well too bad, you'll have to wait for it. Tara told me that we were going to reward you by fucking your ass on femdom night. But right now, you just have to go home."

As I left the house and headed home, I could help but think how good it felt to be denied and frustrated.

**********

It was femdom night. As I entered the club with my wife and her sister, my heart was racing. We met Sarah at the entrance, she had been waiting for us, wearing only her bra. I realized that I had still not seen her tits. Maybe tonight...

"I've got a spot picked out, come with me before someone else gets it" she said to us as we stripped our clothes off.

We followed Sarah past a few rooms where the action had already started. There were so many things to see. One woman was dressed in tight leather whipping a man who was in chastity. Another woman was dressed as a slutty teacher spanking a school girl. (That school girl was hot, I would have tapped that, but I couldn't.) There was even a couple on their hands and knees, with a dominatrix behind them with one fist up each of their asses. The couple just kept saying "I love you" to each other. I guess they found what they were missing in their marriage.

Sarah led us to a room with a chair, it looked like a gynecologists' chair, where you would sit on it and have your legs in holsters, spreading them apart.

She looked at me and ordered "Phil, get in that chair and put your legs up."

I did as I was told.

My wife smiled at me as she tightened her strap-on, "Alright Phil, it's time for your reward for all the hard work you've done this week." Amy was also tightening her strap-on. The sight made my cock strain to get hard in its cage.

Sarah had opened a bottle of lube and dumped a bunch into her own hand. She put her hand on my hairless asshole and started rubbing it around. She said to my wife "Let's get him ready for that cock of yours." And with that, Sarah started pushing one of her fingers against my asshole. My heart started to race faster as she got it in up to the first knuckle, then the second knuckle, then pulled it back out. Then she thrust the whole finger into me. Now, it's just a finger, and she wasn't aiming at my prostate, so while it felt good, it wasn't the most stimulated I've ever been. However, the situation was extremely arousing. My high school crush, standing there in just a bra with her shaven pussy exposed, was fingering my asshole right in front of my wife and sister-in-law. They were both watching while spreading lube on their cocks, making it look like they were masturbating at the site. It was incredible.

Then Sarah slid in a second finger. I could feel that more. Then a third finger, and then a fourth, but only so far. Sarah sounded disappointed as she said "Aw, looks like you're not loose enough to fist. I guess we'll have to work towards that."

She backed off and my wife stepped up to me, slowly sliding the head of her fake cock inside of me. "Is this what you want baby? You want your wife's cock up your ass? Is this why you let me keep you locked away?"

"Yes mistress" was all I could say as her cock slid further and further inside me. She started thrusting slowly, then got a little bit faster. I could tell the vibrator was working as intended, it was getting more intense the faster she thrust, and the expression on her face showed it.

She worked up to a furious pace, and I could feel myself getting close to the edge. "I think I'm gonna cum!" she said. I really wanted to cum at the same time as she thrust faster and faster, pushing herself over the edge. "Oh fuuuuuuck" she moaned as her body started convulsing. I didn't get to cum with her, and I needed it so badly now.

She withdrew her cock and slid the strap-on off, leaving me feeling empty. I needed to cum. I needed to be filled. I looked at Amy, who was still standing there with her strap-on and asked "Are you going to give me my reward too?"

She smiled at me "I suppose you deserve it." And she got between my legs. With one motion she plunged her entire girl cock inside of me. It felt amazing, I needed it so badly. She started pumping, but not too fast. She would withdraw slowly, then thrust it in hard and fast, repeating this over and over again. I'm guessing the way the built-in vibrator worked, it was a tease for her too.

My wife came up beside me, smiling. "Did you like that honey; did you like when I fucked you? Do you like having my little sister fuck you in the ass? You must be so humiliated, having wanted to fuck her cute little ass for all these years, now here you are, getting fucked by her cock that's bigger than yours."

Just when I thought this couldn't get much hotter, something amazing happened. Amy stopped pumping, looking off to the side and said "What the fuck is that?"

Sarah had slipped on her own strap-on, but it wasn't like the one's the other girls had on. It was shaped like a horse cock and she was slathering lube all over it with both hands. My wife spun her head around to see. "Holy fuck" she said.

Amy started pumping my ass again, while Sarah moved up behind my wife. Sarah started talking to my wife "I know you like to be dominant over your husband, but you also like to be a little slut for big cock. Lean over your husband, I'm gonna fill you up till you scream."

She pushed Tara into me, our faces were close. My wife started moaning as her holes were being teased. "Oh no, not there. I've never taken it there before." she said. Sarah must have been teasing my wife's asshole.

"Too bad slut" Sarah barked at her. "I'm the domme here, and you're going to take it however I want you to."

My wife's breath got really short as Sarah pushed the head of the cock into her virgin asshole. I couldn't see how far into my wife's ass the horse cock had gotten, but I could see Sarah's hips moving more and more as my wife loosened up.

It was my turn to talk dirty, "You like getting your ass fucked? Do you like a big fat horse cock pounding into your most forbidden place? And while that's happening, your sister is having forbidden femdom sex with your husband."

She came back at me though "That's right, my hot little sister's tight body is fucking your ass, you're not fucking her. You'll never fuck her because you're all locked up. Now you're just an anal slut, no more straight sex for you."

"It looks like you're an anal slut now too, taking that big animal cock into your little rose bud. I bet it feels way better than you imagined."

She cut me off "That's right, it does feel better than I imagined. That's because it's filling me up more than you ever could. I could never have imagined feeling this way with you."

Someone might have thought that was mean, but I thought it was the hottest thing I've ever heard. Hearing my wife talk like this was amazing. I pulled her face into mine and our tongues became intertwined, as we had the most intense make out session ever, while we were both being fucked hard in the ass.

And as Sarah and Amy increased the pace, we could feel our orgasms coming on.

Amy had a pre-orgasm look on her face and said "Oh fuck, take my cock Phil. Fucking my sister's husband into submission...fuuuuuck" and she started to orgasm.

At the same time, Sarah was talking to Tara; "Your virgin asshole loves horse cock, doesn't it? Do you like being filled more than your husband could ever fill you?" And my wife started cumming too.

My wife and her sister were cumming at the same time. I was right on the edge, trying desperately to orgasm with them, but it just wasn't quite there.

Their orgasms subsided and everything slowed to a halt. Amy withdrew from me, and when Sarah took that huge cock out of my wife's ass you could hear an audible pop.

Philyssis
Philyssis
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