I spent the next few days trying to get anything at all out of Melissa. I had so many questions about what she and Diana had discussed in private, but it didn’t take long before I realized that I was pushing my luck. Melissa was was losing patience with me so I backed off.
Instead I moved on to trying to find out more about this party that we’d be going to on the weekend. I didn’t want to anger her after pressing her about the other things, so I made it sound like I was trying to prepare myself for it. I told her that I had to know what I should wear, hoping that might tip me off to what kind of party this was going to be and what I could expect from it, but her only reply was “everything is being taken care of, all we have to do is show up.”
As frustrating as not knowing was, I was frustrated for another reason too. I hadn’t been let out of chastity the whole week, despite servicing Melissa orally twice. After the second time, I had a bit of a break down.
“Melissa, please! Please!”
“I said no.”
“Please, I need to cum. I can’t take it anymore.”
“Aww, do you miss the taste of your cum so badly that you’re willing to throw this little hissy fit just to get that salty goo on your lips?”
“Yes! I mean, no… I mean I just need to cum!”
“Well, that’s too bad. I said no, and no means no.”
Melissa wasn’t making it any easier on me. I’d just eaten her out to a series of orgasms and she was still laying in bed naked with her legs spread. I couldn’t look away, but it hurt to keep looking.
“Can you please cover up at least? You’re teasing me.”
“I’m not teasing you. I’m just laying here minding my own business being annoyed by your begging.”
“Didn’t I do a good job?”
“You did a great job.”
“Don’t I deserve some relief then?”
“Is that why you service me? Do you do this to make me happy or because you think that you’ll be rewarded? You’re sounding selfish Grey.”
“No, I do it to make you happy. I just thought that….” I wasn’t sure if there was a way of finishing that sentence that wouldn’t risk angering Melissa so I let it tail off.
“You’re not the only one who’s gone without. I haven’t gotten any cock this week either, you know.”
“Yeah, but I’ve gone down on you twice! I haven’t gotten anything at all!”
“All I hear from you is ‘me, me, me’. You don’t seemed to be concerned at all that my little pussy hasn’t been filled and stretched out in over a week.”
Being as horny as I was, I couldn’t look at Melissa’s pussy while I listened to her talk about getting fucked – especially with the taste of her cunt fresh in my mouth. I got up to avert my eyes and Melissa reacted.
“Where are you going?” It sounded like a command more than a question.
“My balls are aching Melissa. I can’t stare at your pussy and listen to you talk about getting fucked. I don’t know if you’re trying to tease me or not, but it’s doing my head in and I can’t take it anymore.”
“A few things,” she began sternly. “Lay the fuck back down.”
I did.
“First, understand that it’s my job to set and push your limits so I’ll decide what you can and can’t take, not you. Next, use your dumbass brain. If I’m denying myself cock – when I definitely don’t have to – maybe there’s a reason that you’re being denied too. I want the party this weekend to be special for both of us. Stop thinking about yourself all the time. Lastly, if I was trying to tease you, trust me – you’d know it.”
Melissa had a way of twisting things around on me. She did it all the time. I went from feeling angry and frustrated to feeling selfish and guilty all in a matter of seconds.
“Now, instead of pouting about what you think that you’re owed I think that you should get what you deserve, and that’s a little punishment. What do you think?”
I knew it didn’t matter what I thought. I knew that I could take what was coming to me, or argue with her and get something much worse. “You’re right, I’m sorry.”
Melissa crawled down the bed, placing her head eye level with my caged penis. She cupped my balls in her hand and kneaded them gently. I’d never struggled so hard to get erect in my life, by dick was desperately trying to burst out of chastity to no avail.
“I wonder why they call them blue balls? Yours are red. A shocking shade of red, but still red. Maybe they’ll turn purple, and then blue?”
“Melissa please…”
“You thought you knew what teasing was. You don’t, but your little guy is going to get a little lesson.” Melissa brought her head down lower, stuck her tongue out and licked my balls with a single lick. What should have been pleasurable was one of the most intense pains that I’d ever felt in my life. It was also the first time I’d been touched there by anything other than my hand or Melissa’s. Feeling the softness of her tongue let me imagine what a blow-job might feel like and I was lost in thoughts of ultimate pleasure while dealing with the reality of incredible pain caused by the chastity cage.
“Holy fuck Melissa, please… please…”
“Please what? Please stop? Please continue?”
I didn’t know how to answer her. My brain could hardly process the extremes was feeling. As usual, Melissa decided for me. She lifted my chastity cage up, tilting it towards my bellybutton which pushed my balls outward giving her greater access to them. She gave them three long licks, each began with flat of her tongue and transitioned to a twirl with the tip before finishing with what felt like a sloppy kiss as she pushed her lips against me, marking me with her lipstick.
“I’m going to cum.” Despite being locked up, my penis was twitching and convulsing, I was ready to explode.
“No, you’re not.” Melissa stopped what she’d been doing and wasn’t touching me at all. If I came, it would be a ruined orgasm. I didn’t care.
My entire body began to spasm. My penis throbbed and pulsated, with each jump of blood being sent to my dick restricted by the cage causing immense pain. Instinctively, I reached for my penis. I thought that maybe if I could shake or tug it even a little bit it would be enough to put me over the edge, but as I went for myself Melissa’s hands intercepted mine. “No.”
I began to cry. Tears welled up in my eyes and streaked down the sides of my face. At the same time, my penis was leaking fluid like crazy, releasing what Melissa called ‘chastity tears’. I’d never been more frustrated in my life.
“You know, when guys get like this a Mistress can relieve the pressure by sticking something up a little subby’s ass. Kassandra told me that. There’s a spot you can hit where you message the prostate and all of that pent up goo will come leaking out. It’s a way of draining your balls without enjoying the pleasure of an orgasm. Would you like that?”
“Yes! Please anything!”
"You thought you couldn’t take any more before and here you are begging me to shove something up your ass! Well, you’re out of luck because all of my toys are too big for your virgin ass so you’re just going to have to ride this one out. Maybe next time though.”
I was in agony for several minutes, but the pleasure that I felt from her tongue was still sharp in my mind. It caused a euphoric feeling, the mixture of such pain and such pleasure was too much to process and it left me feeling stoned. In time I regained my senses. I could feel a steady stream of pre-cum flowing from my penis, leaking down the inside of my leg, surely forming a puddle on our bed sheets. Melissa was silent the whole time, I think trying to gauge where I was both mentally and physically. I broke the silence, wiping my tears away before engaging her.
“Melissa, that hurt so much.”
“I know, right? But it felt good too, didn’t it?”
“Incredible.”
She began to move and repositioned herself to where she was sitting on my lap. Once again, she took hold of my chastity cage placing it a fraction of an inch away from her still naked pussy. She wiggled my cage, like a cat playing with a toy.
“Just imagine Grey. Just image how it would feel to slide your dick into my pussy….my warm, wet pussy. Imagine if you weren’t locked up and I sucked your dick like you were a real man, got it nice and hard, and then I laid down on the bed and said ‘Fuck me Grey! Fuck me! My cunt needs your cock Grey, please give it to me, please!’” she said it with a panting moan, words I’d heard her say before when she was having sex – but this time hearing her say my name, with my penis close enough to her pussy that I could feel the warmth emanating from it, even though the plastic cage that confined me. The pain that it took me minutes to recover from returned in an instant. It felt like I was going to have a mental break down, but before it got any further Melissa climbed off of me.
“That’s teasing Grey. Don’t you forget it.”
She stood beside the bed, looking down at me – in more ways than one. “Don’t touch it. Keep your hands away. It will go down on its own.”
Melissa watched over me for a few more minutes until she was satisfied that I wouldn’t touch myself. After what I just went through, I wouldn’t dare disobeying her.
“It’s a pool party.”
“What?”
“This weekend, Diana invited us to a pool party.”
--------------------------------
It was a couple of days before the party on Saturday, and I made sure to stay on Melissa’s good side the whole time. The aching in my balls never really went away, or if it did the memory of it was so present in my mind that it felt like they were still aching. I never wanted to experience that again. Her tongue though, that was a different matter. I needed to feel that again, but even thinking about it brought back the aching and I had to force myself to stop.
Eventually the weekend rolled around. I was still going the extra mile to keep Melissa happy and asked her if I could get anything that we could bring to the party – booze, food, anything at all but she assured me that everything was taken care of.
It occurred to me that I wasn’t sure if Melissa even had a swimsuit, I’d been through most of her clothes and never noticed one. With super pale skin, she wasn’t exactly a sun-hound.
“Stupid question, but do you even have a swimsuit?”
“I didn’t, but I picked one up the other day.”
“Nice, what does it look like?”
“Wait and see” she said with a wink and a smile.
“I doubt I’ll swim, but my blue shorts should be ok, eh?”
“Yeah, they’ll be fine.”
A few hours had gone by and Melissa was still in no hurry to leave, fashionably late I guess. It was really later in the afternoon before she said “let’s go”.
I’d been assuming all along that this party was at Diana’s house since the invitation came from her but it turns out the party was much further away. When we got into my car, Melissa gave me an address. I looked at it with confusion.
“This can’t be right, that’s like 2 hours away.”
“Yup. Better start driving.”
I thought it was crazy to go pool party and arrive after sundown, but at least it was hot out so the pool would still be nice to dip into even at night.
After our long drive, we eventually arrived at a house pretty much in the middle of nowhere. We were two hours North of the city, in cottage country but pretty isolated from the traditional weekend getaway spots. The house that we were visiting was definitely a house, and not a cottage. It looked like an old manor home that had been restored. It was a far cry from a mansion, but much bigger than any house that we’d ever see living downtown.
“Who’s place is this anyway?”
“I don’t know really, a woman named Rebecca. She’s a friend of Diana’s…and Kassandra’s. She’ll be here too.”
“Wonderful,” I thought but dared not say it.
There were quite a few cars out front, 15 or maybe even 20 in total. The driveway that connected the country road to the house was several hundred yards, leaving us plenty of space to park. By the time we’d got there and gathered our things, the sun had gone down. A strip of patio lights led the way to the back of the house, and we followed a path that led us there – hearing the noises and sounds of a party the whole time.
I wasn’t prepared for what I saw when we rounded the back corner of the house and stepped into the backyard. Taking just a quick glance, I reacted.
“Melissa, no…”
“Yes Grey,” she replied as she kept walking.
It was a pool party, but far from a conventional one. It took less than a second to realize that this was a ‘lifestyle’ pool party. There were about 10 women, on the back deck and in the pool combined. I recognized Diana and Kassandra - the others were unfamiliar to me. Mixed among them were a dozen or more well-built, very athletic looking black men, Phillip was the only one who I recognized and I was nervous to see him there. He knew all of our friends and I didn’t want any of them to know about this. I could see why he’d brag about being involved, but I didn’t need anyone to know that I was involved, especially being on the losing in of the stick. And speaking of losing, in an almost separate area of the party there was a group of sad-sack looking white guys, clearly the husbands and boyfriends of the women.
Diana saw us and came running to greet us. She’d clearly had a few drinks and I wasn’t sure if she’d make it to us without tripping over herself. Although she was much older than us, Diana looked shocking good in her bikini.
“OH MY GOD! You made it!”
“I told you we’d come!” Melissa enthused.
We started venturing deeper into the backyard and people had taken notice of our arrival, several heads turned to eye us up and down. I took a few steps alongside the ladies before Diana stopped us. She pointed to what looked like a utility shed.
“You guys can change in there, but hurry – I’m excited for you to meet everyone.”
The inside of the shed was much nicer than the outside. It had been done up to function as a mini pool house. There were two separate areas curtained off to function as change rooms, a couch, a couple of chairs and even a rack of brand new men’s and women’s swimsuits for guests who showed up without. Against the far wall there were storage bins where we could place our clothes and other belongings for safe keeping.
I changed into my shorts, relatively certain that my chastity device wasn’t too obvious. When I came out of my change area, Melissa was already out of hers standing with her back to me. The bottom of her swim suit was a thong that didn’t cover anything at all. Her entire ass was on display. She stood holding the strings of the top of her swimsuit behind her back.
“Tie this up for me” she instructed. I did, and I was shocked when Melissa turned around. The top half of Melissa’s swimsuit was just as skimpy as the bottom. It was basically two very small triangular patches of material that barely covered her nipples. She might as well have been naked.
“You can’t go out there dressed like that!”
“Of course I can! You saw what Diana was wearing. I’m half her age. I need to be wearing half as much!”
I was still nervous about my chastity device being visible through my shorts and decided to press my luck. “Do you think you could let me out of my cage for today?”
Melissa laughed. “Yeah, right. You’re going to be out there with all of those women in bikinis and not be locked up? You’d have boner the whole time!”
She had a point. The one good thing was that all eyes would be on Melissa, which made me a little less self-conscious about hiding my chastity. Talking about it made me realize that she wasn’t wearing my key around her neck like she usually did. Sensing my panic, she pointed down to her foot where my key had been attached to an ankle bracelet. At least she wasn’t leaving it in the shed. Maybe that was a reason to be hopeful.
“Let’s go.”
We stepped out of the shed and Diana was still waiting for us. The shed wasn’t too far from the deck and pool area, maybe 30 feet or so and Diana led the way.
The deck was about 4 feet off the ground and circled most of the above-ground pool that was the centre of the party. The women and black men were either on the deck or in the pool. Those who I assumed were the husbands and boyfriends gathered together in an area on the far side of the pool, on ground level. Diana walked us to the stairs that led up to the deck, stopping before we went up and called everyone to our attention.
“Everyone! Everyone! We have a new addition to our circle of friends! I want you to meet Melissa and her cuck Grey!”
A smattering of welcoming comments came from both the deck and pool. Diana took Melissa by the hand and led her up to the deck, after taking a few steps up she turned to me.
“Grey, why don’t you go meet the others down the back?”
I watched Melissa’s exposed ass climb the stairs in front of me, then peeled my eyes away and headed over to the ‘B squad’.
I made a few awkward introductions to the husbands and boyfriend’s group and helped myself to a beer. Most of these guys seemed somewhat normal, but I had a hard time fitting in with them. All of this was new to me and I found it really hard to be openly called a cuckold in front of so many people – the fact that I was standing with a bunch of other cuckolds didn’t make it easier on me. It felt like it solidified my position as one of them.
I was trying to be polite and talk to the guys but I was focused on and distracted by what was happening up on the deck.
“First time, eh?” a guy who I hadn’t met yet spoke up.
“Yeah, and I think last.”
“Ha! I think everyone of us made that same joke, and yet here we all are. My name is Mikey btw.”
“Grey.”
“I know. I’m with Kassandra. Melissa has been over at our place a few times. I’ve heard a little bit about you.”
My mind flashed back to all of the crazy things that Melissa told me about Kassandra and her boyfriend. “Nice to meet you, I’ve heard a few things about you as well.”
“We have ways of doing things around here, and one of the big things is that we don’t stare at them up there from down here. You’re new so I’m sure you’ll get a pass for now, but its best if you let them have their fun up there and you just hang out here and get to know the guys. Not a lot of people know what you’re going through, but we’ve all been there before.”
I wanted to tell Mikey thanks but no thanks, I wasn’t one of them and I wasn’t ever going to fit in with this group of guys but the reality was that I was one of them. I didn’t have to accept it though, at least not then and there.
At this point Diana was still taking Melissa around, introducing her to the other guests. Another older woman, around Diana’s age, came outside from in the house. I assumed that was Rebecca. She was remarkably ordinary looking. Neither attractive or unattractive, more or less plain looking. She looked like a typical soccer mom and probably was. Melissa seemed focused on meeting everyone but it was impossible to not notice that the bulls had noticed her. At least 4 or 5 of them weren’t shy about looking her up and down and making comments about her appearance. Just about all of the women there were young and beautiful and yet Melissa stood out even among them. It made me proud to know that she was with me, but fearful that one of these bulls was going to try to take her away from me.
As I was trying to follow things up on the deck, Mikey offered a little insight. “There are rules up there too. The bulls hang back when it comes to a new girl, they have to wait for a first timer to approach them. It avoids a feeding frenzy on the ‘fresh meat’. We’ve had fights here in the past, when two drunk alphas want the same thing it can get ugly in a hurry.”
While trying to follow what was happening with Melissa up on the deck, Mikey and I were interrupted by Kassandra. She’d swam over to the edge of the pool that was closest too us. Seconds later, a tall black guy popped out of the water behind her and began cupping her breasts while staring at Mikey and I.
“Mikey darling, Charles is going to take me upstairs for a while. Run ahead and make sure our room is ready, ok pet?”
“Yes Mistress.”
And with that, off went Mikey. Kassandra hadn’t moved and continued looking at me as the guy who I assumed was Charles kneaded her breasts as she spoke.
“Having fun Grey?” she asked with contempt. The wicked smile on her face left no doubt that she wanted to torment me. I didn’t answer her.
“Well, I hope you are because I know Melissa will be.”
Satisfied that she got her dig in at me, she turned to swim back towards the deck with Charles in tow. As the two climbed out of the pool and went inside, there was clear recognition of why they were headed inside and the group on the deck cheer and jeered them playfully.
Less than a few seconds later, an Asian girl grabbed one of the bulls and pulled him into the house. “I didn’t want to be first,” she said with a laugh “but now that dirty slut Kas is gone we’re going too!”
A shlubby looking guy from behind me yelled out, “do you need anything hun?” to which she replied “just a big black cock!” which caused the party to burst out laughing.
The shlub said to no one in particular, “I married a Korean girl because I thought she’d be submissive. Boy was I wrong.”
Soon after the first two pairings went inside, two more couples went into the house and upstairs. Knowing what they were all there to do, and knowing that it was all starting to kick off left those out on the deck and in the pool feeling more frisky and they began to get a little more forward with each other, lots of touching, holding and kissing.
Melissa was doing a lot of flirting, but hadn’t yet coupled off with anyone yet. She spent most of her time talking to a girl, who I later learned was named Jessica. The two talked for quite a while and then disappeared inside. I knew that had been with women before, but there was no way that she’d gone inside to fuck around with Jessica with so many black cocks on offer for her to choose from. I was curious though and as the time went on I really wondered what they were up to. A little over an hour later, I had my answer. stepped out into the backyard with an entirely new hairstyle. Jessica had braided ’s hair into cornrows. It’s not a look that I ever would have imagined for her, but she looked great and the guys on the deck really seemed to approve too.
Melissa’s new hair and the nice job that Jessica had done with it seemed to be a point of conversation and a group of three guys gathered around them. The flirting began pretty quickly and was very obvious, no one was trying to hide their intentions. Jessica was beautiful in her own right, and provided a pretty stark contrast to Melissa. Where Melissa was petite, blond and curvy Jessica was tall, rail thin, had smaller tits and black hair. The guys gathered around them towered over them, each of them well over 6 feet tall with muscular, athletic builds. I thought that I could see how this was going to play out, and tried to emotionally brace myself for it.
The three guys were definitely trying to get both Melissa and Jessica to go upstairs with them. I guess this was the work-around for the ‘not fighting over fresh-meat’ rule – they’d all fuck Melissa, and Jessica. At first it seemed like the girls were playfully doing a hard to get act, but Jessica gave in pretty quickly and it seemed like the inevitable was going to happen, but Melissa held out. I couldn’t hear their conversation from where I was but clearly Jessica and the 3 guys were attempting to get Melissa to follow them inside but she seemed content to stay where she was. Realizing that they weren’t going to convince her, Jessica went inside with all 3 guys to herself.
I thought maybe this might be a turning point in the night. Melissa had an incredible opportunity and passed on it. Maybe all of this was just to test me or something? It didn’t take long for that idea to get dashed when strolling in late, Tayshaun walked into the back yard. Melissa’s eyes lit up and she ran to greet him, jumping into his arms and giving him a long passionate kiss.
