Cuckholding Pt. 05

Oh the variety of Bulls I've been with has been incredible. Sometimes, though, I feel like I'm living a double life. I've never told any of my friends about my other side- my dominant cuckholding side. Keeping this whole other side of my life secret is enthralling sometimes, but at the same time, can be lonely. I decided that now was the time to open up to my best friend. She started to talk to me more and more about her sex life, so this seemed to be the best opportunity to let her into my world.

I've known my best friend, Abby for 8 years! Abby and I became friends during college. We shared some of the same business classes and quickly hit it off, spending many nights studying and many more partying. Abby was beautiful- 5'6", thin, medium length red hair, soft facial features, long muscular legs, and tits that were at least double the size of mine! There were a lot of drunken nights that we spent the night in the same bed, nothing occurred between us, but I always wondered.....

Abby was married to Zach for the last 3 years. In fact, I used to date Zach, several years before him and Abby got together. Actually, Cuck and Zach were pretty tight back in the day. Men are, well, let's just say that they didn't keep in touch during the years in between. But Abby and I stayed close despite our now-husbands. We would occasionally all hang out together, but not nearly as often as I would like.

I decided to send Abby a text, so we could get together for drinks. In fact, I had a proposal for her.

I miss you sweet friend! Let's get together this Thursday night for some drinks. Red Rooster, 7PM.

I waited for about 15 minutes before my phone vibrated that I had a response.

Oh, I miss you too!! Thursday sounds great!

I cannot wait to see you!

I was so excited! I called Cuck from across the house. "Cuck! Come here. Now."

Cuck meandered into the room and said, "Yes?"

"Are you kidding me?!" I shouted. "Do you not remember who you're talking to?"

Cuck looked down to the ground, then sheepishly answered, "Yes Madam. I am very sorry for that indiscretion. Please forgive me. What is all the excitement about?"

I sneered at him, but then answered. "I am going out with Abby on Thursday. I'm going to make a proposal to her."

"Madam, may I ask what that proposal is?" Cuck asked.

I pondered for a moment, then said, "You'll see!" as I grinned and walked out of the room.

On Thursday, I was so excited and started texting Abby first thing in the morning:

I cannot wait until tonight! The time is passing by so slowly and I am so ready to see you.

Abby replied:

Me too! How does time go so damn slowly

when I need it to move faster! Lol.

7PM!! Cannot wait! I want you to come with your mind open to adventure. 😊

Oooooh. Mysterious! I like this!!

As soon as work was over, I raced home to get ready. Before I went to the Red Rooster, I modelled my outfit for Cuck. "What do you think of it?" I asked him.

Cuck looked at me, a bit puzzled. "Madam, are you trying to pick her up? Because you look fucking hot." He continued, "If that's your intentions, then you are on fire!"

I smiled at him, "Then hot damn, I am ready!"

I wore skintight jeans with rips down the legs, snake skin boots, and a tight shirt that exposed my midriff and showed ample cleavage. I grabbed my wallet and headed out for the bar.

At 6:45PM I arrived at the Red Rooster, ready to "pick up" Abby. I sat at the bar, ordered a drink, and laughed at what I was about to propose to her. Never have I admitted my wild side before, so this was going to take a few drinks to get this going.

By 7PM, I was already 2 drinks in, when I got a text from Abby:

I'm running late. Promise I will be there in the next

15 minutes!

Abby- you may have to pick me up off the floor if you are any later than that! I'm already 2 drinks in! Lol.

Well, I guess I've got some catching up to do, don't I?

Hell yes you do!!

Finally, Abby arrived at 7:20PM. The poor bartender was tired of refilling my drinks, except that anytime he refilled them, I made sure to lean over the bar, showing as much of my cleavage as I could, to hand him a tip. He would just grin at me and wink. By the time Abby arrived, I had 4 drinks and was definitely buzzed.

"Oh my God!" Abby screamed as she ran over to hug me.

I wrapped my arms around her and squeezed her, like it had been years since I saw her. I let her go, but then took my hands, put one on her cheek and ran the other along her jawline. Looking deep into her eyes, softly I said to her, "You look stunning tonight."

Abby gave me a funny look, kissed me on the cheek and said, "Let's get some drinks!" She turned towards the bartender, waved him over, and told him, "I gotta play catch up. So, I'm gonna need 2 shots of fireball and then a drink- your choice." She winked at him and then sat down next to me. I don't think he knew what to do with the two of us. We just giggled.

"You were so mysterious the other day!" Abby said, just jumping right in.

I laughed. "Abby! You are just so ready to find out what my cryptic message was about, aren't you?"

Abby smiled and said, "Well, can you blame me??!!"

"Let's drink to it!" I said to Abby. Then, "Bartender! We need another round please!"

The bartender came over, placed our drinks down in front of us, winked, and said, "These are on the house, ladies."

I leaned into him, grabbed his tie, pulled him so close that our lips were almost touching. "Thank you, Sir. I promise that will be worth it." I released his tie, smiled at him, and after his initial shock, he had a naughty grin on his face.

Abby sat there, her jaw almost hitting the floor, "Girl! Oh. My. God!" She shouted. "You are fucking naughty!"

I said to her, "Oh Abby, you have no idea!" She glanced at me with a quizzical look.

I laid out my secret life to her and Abby sat there very intently listening. But never did she seem to think that I was crazy. In fact, it was just the opposite. It was as if she was taking it all in, and maybe understood more than I even realized.

"That's fucking hot!" Abby said, sounding elated. She hesitated, and then said, "But where do I come into play?"

I looked down at my drink, into her eyes, and then took her hands in mine. "As you well know, Zach and I fucked in the past, so let's just say......." I hesitated, "I know his package very well." She grinned.

"Yes." She laughed. "And?"

"Well, let's say that Cuck is not so...... endowed as Zach." I winked at her. "I want you both to join us. I want Zach to be the Bull for comparison. I want to bring y'all into our home for an intense sexual encounter." I paused, letting her process the proposal.

I had barely paused when she said, "Absolutely we are in!"

My jaw hit the floor, and I barely could get words out of my mouth. "Wait.... You.... Seriously? I..."

Abby had a naughty smile on her face, "You aren't the only one with secrets, you know."

Abby and I stayed out very late and had way too much to drink. The bartender was humored by the two of us, and I had a feeling he was listening to us talk about the sexual encounter proposal. When we went to pay our bill, he said, "I will cover all your drinks tonight if you girls make out right here, right now."

I didn't really give Abby any time to think about it. I mean, I was already over 6 drinks in at that point, so I took her hands and placed them on my breasts, pulled her face where her lips met mine, and damn did I kiss her. She picked up on my sexual prowess and decided to take it to the next level. She moved her hands from outside my shirt, to underneath- massaging them and pinched my nipples. The bartender stood there, his jaw practically on the floor, with an ever-growing hard on in his pants. "Hot damn!" he finally managed to get out.

And just like that, we broke it up, made plans for the weekend, and grabbed an Uber home.

Saturday was playing out just like any other weekend that I would be having a bull come over. This day was different though. I told Cuck that he was in for a surprise this evening, but I didn't let him in on the secret. "I need my outfit for tonight." I told Cuck. "It needs to be extra hot this evening. You are in for a surprise." I winked at him.

"Yes, Madam." Cuck replied. As he normally does, he immediately went into the closet and retuned with a dress, bra, and boots.

"You forgot the panties!" I said to him.

He grinned. "Madam, I didn't forget them." He continued, "It will be sexier for you to go without them." I beamed.

I slipped on the skintight red dress, that rested just below my ass, and made my small tits look like they were amazing. I spun around a few times, admiring myself in the mirror. Fuck I look hot, I thought. Zach is gonna love the looks of me tonight.

I had left Cuck uncaged all week, which was a rarity when I had a Bull coming over. I strutted over to him, and whispered to him, "Cuck." He gasped when he felt my warm breath against his ear. I smiled. "Tonight, is going to be different. I want you in a cage. I want you turned on. Same rules apply tonight as normal though, except for one. You will have 2 dommes. You will follow OUR instructions."

When I turned my gaze down, I saw Cuck's tiny cock growing before my eyes. "Two?" he asked hesitantly.

"You are getting turned on already?" I giggled. "I need that cage on you before you get hard on me."

Cuck looked down at his ever-growing mini cock. "Madam, the thought is exciting and terrifying all at the same time."

I put my finger under his chin, lifting his gaze up to meet mine, and commanded, "Cage. Now." His eyes widened, so I softened my voice, "You will love it."

As I commanded, he obtained the cage from inside our closet, but he was too erect to fit in, even as small as he was. "You know what to do." I said to him.

"Yes Madam," Cuck replied. He turned on the shower- ice cold, shivered, and stepped in. "Madam- it's so cold!"

"Cold is better to shrink that already miniscule cock of yours." I sneered.

I looked at his trivial shrinking cock. It's ready, I thought. Damn it looks smaller than usual. I smiled and thought, how perfect! While he was still in the shower, I grabbed the cage and quickly clasped it on him.

"Oh!" he shouted, as the metal clanked together. "Madam, that is always a startling sound." I smiled at him, turned off the water, and handed him a towel. When he stepped out of the shower, I leaned down, massaged his balls, then ran my tongue up his cage-covered shaft. I looked up at him, and his eyes looked like they were rolling back in his head. I beamed and teased the tip of his tiny cock with my tongue. He started moaning, his mini cock hardening under the spell of my tongue. But it couldn't do much except push out against the cage that held it captive.

"Oh, God yes!" he moaned. "It.... that's so tight...ohhhhhh."

I teased him, edging him a bit longer, but knew if I pushed it too far, he may cum, and I couldn't allow that to happen. I withdrew my tongue, smacked his balls, and walked out of the room. I left him standing there naked, full of pleasure and pain, wanting desperately to cum.

Abby and Zachwere due to arrive at 7pm, and it was now only a short 10 minutes before they would get here. It was time to get Cuck ready for the exciting encounter we were about to have. "Cuck," I said to him, "You may wear boxers and a t-shirt." He looked at me puzzled but dared not to argue.

When the doorbell rang, I motioned to him to sit on the far couch. I strutted over to the door, opening it wide for Abby and Zach to come in. As Zach walked in, his eyes never left my body. He scanned every inch of my body, and then winked at me. I blew a kiss with just my lips and winked back. Abby was too busy looking around the room and trying to find where Cuck was waiting, to even notice the sexual tension between Zach and I. I knew this dress was going to be a home run tonight, I thought to myself.

"Abby!" I shouted, breaking the spell between Zach and I. She turned to look at me and I could almost feel the desire she had for me at that moment. I gave her a long tight hug, ending with her pinching my ass. I just smiled at her. "I'm so glad that the both of you came over tonight. It's exciting to have ya'll here!"

Abby was dressed in tight jeans and a loose tank top but didn't appear to be wearing anything under that. Zach was wearing an athletic cut t-shirt and tight jeans- which didn't hide the large size of his cock. Being turned on as he was already, you could see it trying to push out of the zipper of his jeans.

I nodded my head at Abby, and she gave me a signal back, to say that all was a-go in her book. Since I knew that Zach and I already had chemistry, I let her take the reins on this one. Abby walked over to Cuck, who was quietly sitting on the couch. She rested her hands on either side of him and leaned in so that her lips were next to his ear. Abby licked the length of his ear, then sucked on his earlobe. He was melting under her lips, and gave a small moan, but knew not to move. She then whispered to him, "I hear that you have a tiny cock. I want to see it. I want to know how it feels to have one in all my holes." Cuck looked at her with his eyes wide open, looked at me for approval and then back to Abby. She continued, "I am stretched out from years of fucking an enormous cock, so I need to know what a miniature dick feels like inside of me."

Abby spread her legs, and sat on Cuck's lap facing him, leaving her tits in full view.

Zach was just standing there, not believing what he just witnessed- his wife's promiscuity directly in front of him. That was my cue, and I turned to Zach, ran my hand along his chest and down to his waist while I walked around him, making sure to take in every bit of him. He just followed me with his eyes. I let my hand slide down his chest and land directly on his gigantic hard cock. I squeezed it, and he just moaned.

I took a step in, so my tits were pressed against his chest, and his line of view would be directly on my cleavage. "Do you like what you see?" I playfully asked him, still not removing my hand from his cock.

"Yes. As a matter of fact I do," Zach said confidently.

"Confident, I see." I smirked at him. I squeezed his cock harder and he moaned, leaning into me more. "Remember, I'm in charge." I whispered.

"Oh, fuck yes!" he replied.

I undid the button on his jeans, and then the zipper. "Take them off. I need to see your hard cock. Right. Now." Zach started to remove his jeans and boxers.

Abby stood up and demanded "Stand. Now, Cuck." He immediately stood. "Drop 'em," she motioned to his boxers.

"Yes. My Lady?" Cuck said, but in a questioning tone.

Abby looked at me, not sure how to respond, and I said, "Yes. Abby is 'My Lady' for the night."

Within a minute's time, both men were only wearing shirts. Well, and Cuck had a cage on too. "What is this?" Abby asked Cuck.

Cuck seemed a bit demeaned when she grabbed his caged cock and was waving it around when she asked the question. He said, "My Lady, it is a cage. To prevent me from pleasuring myself out of turn." Abby grinned.

"Oh, I really like this!" Abby said to Cuck in a high-pitched voice. "And how cute is your tiny cock?!"

I was able to get a good long look at Zach's cock, and hot damn it still looked as good as I remembered it. "Damn you have an enormous cock!" I said to him. "How long would you say it is?" I inquired.

Zach looked at me and said, "I don't know. Been a real long time since it got measured. Didn't you measure it years ago?"

That instantly made me wet: Zach, talking about us fucking when we dated. "I probably did." I pondered. "But since we don't know for sure, we will be making that a priority tonight." I looked at Abby and asked, "What do you think Abby?"

"Oh yes. Zach's cock is so much longer and wider than Cuck's!" She turned to Cuck and asked, "I mean, what do you measure, 4 inches? Maximum?"

Cuck, feeling humiliated at the size Abby thought he was, said, "No, My Lady. Fully erect, I am 6" long, and 5" in girth."

Abby laughed. "Seriously? No way!"

"Cuck, come here. I will unlock you so that Abby can measure you I want you in line with Zach- for best comparison, of course." I said to him.

I directed my attention towards Abby, and while winking said, "You may want to facilitate the process."

Cuck walked over and stood next to Zach. Damn Cuck's cock looks miniscule comparatively, I thought. Zach was beaming, realizing the dominance he had in this scenario. I ran into my bedroom and grabbed the key to the cage and measuring tape.

When I walked back into the room, Abby was on her knees, massaging Cuck's balls and licking his cock with her tongue through the cage. I could hear him moaning in pleasure. I had a wicked smile on my face. "Looks like Abby is getting that mini cock to try and push its way out of that cage!" I said. Cuck didn't even recognize that I was talking to him, as he was so focused on Abby's attention to his caged cock.

"Ohhhhh, Abby! Fuck!!" Cuck cried out as she tugged on his balls. "Oh my God! Shit that feels soooooo..... oh God." His cock was turning a purplish color from being compressed and trapped in that cage, and now it was dripping pre-cum. I handed the key to Abby, who proceeded to release the wee little beast from its cage. His cock sprung out, standing straight up, the pink color returning, as blood flow ran through it. "Fuck yes!" Cuck cried out.

That's when Abby took it to the next level. Without hesitation, she engulfed his entire cock in her mouth, sucking hard upwards and pulling down on his balls. "Ohhhhhhhhh!" Cuck screamed out. He was moaning from all the attention.

Abby released his cock and asked for the measuring tape. "Let's see how big this miniscule cock actually is. I mean, I was able to get it all into my mouth without much effort. And then we can find out if it can even be felt inside of me." Abby teased.

As she grabbed the tape from me, I turned my attention to Zach. "I guess you've gotta get the blood flowing real good for us to measure you, huh?" I teased, batting my eyes at him.

He took this as a sign of dominance, putting his hands on my shoulders, pushing me down onto my knees. "Oooooh," I said. "A man who can show me his strength." Quickly turning my head towards Cuck, I said, "This is a man who knows how to dominate a woman. Watch as I take his entire cock into my mouth, then measure how enormous he is." I guided Zach's cock into my mouth, opening my throat as wide as I could. I realized, that try as I may, that cock was not going all the way in. Wow, he really is fucking huge, I thought to myself. I continued to suck on his cock, teasing it with my tongue. Zach groaned in pleasure.

"Suck it harder! Fuck that's so good!" He was crying out. That's when he wrapped my hair around his hand, put it on the back of my head and face fucked me. My eyes teared, but damn I sucked that cock like it was nobody's business. He kept moaning as he was sliding in and out of my wet mouth. He released me, and I grinned up at him.

"My turn for the measuring tape." I said, looking deep into Zach's eyes.

Abby had measured Cuck at 6.15". Cuck stood proud of the fact that he was slightly longer than he anticipated. But his pride didn't last too long.

I took the tape, starting at the bottom of Zach's cock, measuring to the tip. "Ten point five inches! Holy fuck!" Sneering, I said to Cuck, "Can you compare to 10.5 inches?"

Cuck looked at Zach's cock, then his own, and said, "No, Madam. At 6.15 inches, I cannot compare to his 10.5 inch cock."

Abby said to him, "Come on Cuck. Let's see what I can feel with you in my wet pussy."