Ladies’ Night

Donna and I have been dating for six months now. We quickly discovered our shared love of kink. She had me wearing a chastity cage two months after we met and held the only keys. At first it was just to keep me from touching myself when we were apart and once together I was free. While she’d tease me and have me serve her, each session would end with me having an orgasm. Which is why a month after we started the chastity play and she locked me back up without letting me cum it was such a shock. She let me cum the following morning, but over the next month the time between my orgasms grew greater.

Fast forward to today. It’s Friday night and been over three weeks since Donna last allowed me an orgasm. I learned quickly never to beg for release, that just added days. I was permitted to politely ask once a day and her decision was final. So when she told me her plans for the evening I was both excited and apprehensive. Three of her closest friends were coming over. It was going to be a simple night of hanging out together and enjoying some wine and conversation. I was to be both servant and entertainment, and if I pleased everyone I’d finally earn my orgasm. At first I was shocked she’d even suggest this, assuming her friends would want nothing to do with our private kinky fun. Then I found out they already knew all about it! I had met each of them at one time or another and had secretly been in chastity each time, or so I thought. Donna told me they play like we do, more or less. In fact that’s how they met when they took the same class about chastity play and orgasm control at a local sex shop. It was taught by Rachel, who I was surprised to learn was a professional dominatrix. I knew she had a private practice, but I thought she was a mental health therapist. Her personality was very cheery and bubbly, and she was a petite woman, 5’2″ tops. I couldn’t picture her ordering anyone around or whipping a man. Her other friend from the class is Nicole. She is a little heavier than the others and also comes across as a bit reserved and shy, so it was also a surprise to find out she would be into this. Her last friend, Amy, was less surprising. She was a type-A personality. Knew what she wanted and wasn’t afraid to go get it. If she was a guy she’d be admired and considered an alpha, but instead is probably called a heartless bitch, but only behind her back. She’s a senior VP at a large advertising firm and the one I have no trouble picturing putting a guy on his knees and ordering him to submit.

At first I thought no problem. I pour the ladies drinks, get them some food, easy and I’ll finally get to cum! Then came the catch, “And you’ll be doing this naked the entire night, except for your cage, of course. You will not speak unless spoken to, and even then will just say ‘Yes Ma’am.’ Except for me you will say ‘Yes Mistress.’ Understood?”

I gulped, “Yes Mistress.”

She smiled, “Good! When you’re not of use, you’ll kneel in the center of the room with your hands behind your back. In fact, I want you on your hands and knees all night unless you need to do something that prevents it, like pouring a drink. I really want to impress my friends with how quickly you’ve come under my control, especially Rachel. She has her clients, but no personal slaves at the moment, and Nicole and Amy are between men too, so I mainly just want to show you off! Make me happy, and not only will you finally get to cum, but we’ll spend most the weekend in bed and really make sure your balls are empty, sound good?”

This was all a bit much, especially so last minute. Her friends were due in the next half hour! I know if I can get over my initial nerves and embarrassment I’ll be fine. Doing something like this has been a fantasy of mine for a long time. That and the promise of an all-weekend sex marathon with no restrictions really helped me get past any trepidations I may have had. “Yes Mistress, sounds good.” I immediately started taking my clothes off and putting them in her bedroom. She smiled wide as I did. Once I was properly dressed I helped her put out some snacks and get the place ready. She gave me some more last minute instructions when the doorbell rang. I’m not sure if I went pale with fear or flush with embarrassment, either way I was a little light headed as I went to the door and opened it. Donna lives in a nice, smaller house and the front door opens into the living room. As I opened the door I was a little relieved that it was Rachel. I figure she’s used to seeing stuff like this in her line of work. It’s summertime, so she is dressed casually in a tank top, tight short-shorts, and sandals. I greeted her the way Donna instructed me, “Good evening Ma’am,” and got down on all fours to kiss each foot, then stood back up, “Please come in.”

Rachel chuckled as she walked in, “Hello Victor, or is it slave tonight?”

As I was about to respond Donna answered for me as she came over to greet Rachel herself, “I think slave should do nicely.” They hugged hello and went to the couch. Donna offered her some wine, which I poured.

As I was about to kneel on the floor the doorbell sounded again. I opened the door, but before I could repeat my routine Nicole screamed in surprise and backed up. I froze as the ladies in the room burst out into laughter. Nicole yelled into the house, “Goddammit Donna! You could have warned me!”

Behind me I could hear Rachel ask, “You didn’t tell her?” Donna could only shake her head no as she couldn’t control her laughter.

I still stood frozen and Nicole was beet red, either embarrassed or pissed, maybe both. She composed herself and apologized to me. That snapped me out of my freeze, “No Ni-, I mean no ma’am, I’m sorry.” I dropped to my knees and kissed her feet. “Please come in.” Nicole was always more modest in her attire, and tonight was no exception. Despite the warm weather she wore jeans and sneakers with a simple, loose top. Since I’ve known her she’s been self-conscious about her weight, but I always thought she was cute and also very kind and sweet. Another reason her being in that class surprised me.

Once past her initial shock, she calmed a bit and walked inside. She joined the others and playfully smacked Donna on the arm, calling her a bitch. After pouring her a drink, I kneeled on the floor and waited, listening to the three of them chat and catch up. They pretty much ignored me until Nicole asked, “So what’s the deal with Victor? It’s kinda creepy having him just sit there like that.”

Donna replied, “Well first, for tonight his name is just slave, and I wanted to wait for Amy to get here. She texted she’s stuck at work and running a little late. For now, don’t worry about him.” About fifteen minutes later the doorbell rang. As I was getting up to answer it, Donna corrected me, so instead I crawled to the door and only stood to open it. While the others were dressed for a casual night in, Amy came straight from her office in high heels, stockings, a tight pencil skirt and blouse. It didn’t look very comfortable, but she looked damn good! She stands around 5’11” barefoot and keeps her body in great shape. Very toned without being overly muscular. She’s almost like an amazon, especially when she towers over you in heels, which she was doing to my 5′ 9″ barefoot self right now.

After greeting her like the others she offered me a smile through her tired face, “Well aren’t you adorable? Thanks, I needed that.” As she passed me and went inside, Donna offered her some wine. “Ugh, do you have anything stronger?”

Donna laughed, “Pretty sure I have some whisky in the kitchen. Slave, would you be a dear and go check?”

“Yes, Mistress.” I drop to all fours again and crawl into the kitchen. After searching a few cabinets I find the bottle and a glass and bring them out. I pour Amy her drink and resume my position kneeling in the center of the room.

Nicole spoke up again, “Well, we’re all here. So now will you tell us why your boyfriend is naked and just sitting there?”

Donna laughed again, “I just thought it would be nice for us to spend the night in relaxing and having a handsome slave boy serving us. I promised him an orgasm if he behaves, so make sure he earns it.”

Amy wasted no time, “Don’t have to tell me twice. I had a long, rough day. I love my Louboutins, but they’re killing my feet. Slave, come massage them.” I crawled to her, removed each shoe, and start rubbing her right, stocking clad foot while I knelt on the floor in front of her. She ordered me to spread my knees wider apart then took her free foot and began lighting tapping it against my balls. Each tap isn’t too painful by itself, but she’s constantly swinging her foot back and forth so she’s hitting them every few seconds. They’re quickly adding up and taking their toll on me. It’s becoming a struggle to stay in place and keep up the massage. Amy is telling the others about her day and the misogynistic “boy’s club” she has to deal with at work, but I’m not paying full attention to what she’s saying, just focusing on the foot in my hands. To top it all off, the tapping and staring at her long, sexy legs is making me strain against my cage. That did not go unnoticed from Amy, “Hey Donna, I think your boy is about to break his cage. When was the last time she let you cum, slave?”

“Twenty-five days, ma’am.”

“Oh you poor thing. Knowing her, I’ll bet she teases you every chance she gets, too. Is that why you’re straining or do you have a thing for feet?”

Her constant tapping and my focus on not stopping her foot rub causes me to respond honestly and without thought, “No ma’am, not feet. I like stockings and you have very sexy legs. I like having my balls hit, too.”

Though she was tired, that seemed to perk her up a bit. “Oh really?” Her taps slowed their pace, but increased in intensity, causing me to grunt a bit with each kick. Somehow I still managed to keep still and continue massaging. She turned to Donna, “You didn’t tell us he was a pain slut!”

“Oh you know that’s not my thing. But don’t get any ideas. I don’t want you breaking him!”

Amy laughed and stopped kicking, “Fine, but I think he really likes it! Why don’t you switch feet?” I gladly take her left foot in my hand and start rubbing, happy for my balls to get a break. “You know, slave, I had to spend all day with a bunch of sexist assholes. All I want to do is give them each a kick in the balls. Pretty sure HR would frown upon that, but you don’t seem to mind, do you? Think you could handle a few strong kicks for me? It would make me feel so much better.”

Everyone’s attention was now focused on us. I wasn’t lying when I said I liked having my balls hit, but up until now it’s only been light slapping and mostly fantasy. I’ve seen plenty of ball busting videos, and while it turns me on, the reality of it scares the hell out of me! I’m not sure if I can handle someone really kicking me, but I also really, really want to cum this weekend, so I take a deep breath, “Yes ma’am, I can handle it for you.”

Amy smiles wide and without a word swiftly brings her free foot into my groin. It was harder than before, but manageable. I could tell she was still holding back, thankfully. “That was for the jerk on the street cat calling me.” Another, slightly harder, “That’s for Mike in accounting and his sexist jokes.” She continued, each kick getting slightly harder. I’m amazed at how many guys treat her like crap in just one day. It’s getting more and more difficult for me to keep my position and continue massaging her foot. Somehow through all of this, my cock is still trying to break through the cage. Finally she says, “And this one is just for me,” and delivers the hardest kick yet that finally causes me to fall over and clutch my sore balls.

This irritates Donna, “Dammit, I told you don’t break him!”

Amy could only laugh, “Oh relax, he’s fine. I was going easy on him. Trust me, a guy’s balls can take a lot more than those little love taps.”

Rachel chimed in, “She’s right, Don. You’d be surprised how much punishment they can take and be fine. I have this one client who comes in once a month and all he wants is for me to tie him up and punch his balls the entire time. Gives me a great workout cause I really go to town on him. Not once has he used his safeword. So yeah, he’ll be fine.”

Donna doesn’t seem convinced, “That’s great for you guys, but not for me. Come here, slave.” I was able to recover while they were talking so am able to crawl over to her. “Stand up.” I get to my feet so my cage is right in front of her face. She gently grabs my sore balls and inspects them to make sure they’re fine. My attempted erection never went away and her fondling me isn’t helping that any, so I’m ecstatic when she pulls the key out from under her shirt. “Would you like to be unlocked, slave?”

Quickly I nod, “Yes, Mistress!”

“Okay, but only under one condition. You need to stay hard the entire night. If any of us see you tonight with a soft cock, no orgasm for you. Do you still want out?”

This sounds like a bad idea, but the cage is really starting to hurt, and if that little session with Amy was any indication, staying hard shouldn’t be a problem. “Yes, Mistress, I understand. Please unlock me?”

Donna shakes her head, “Horny boy, you’re probably going to regret this.” She unlocks and removes the cage and my cock wastes no time springing up fully. “Here, I’ll help you out a little.” I gasp as she slowly takes me fully into her mouth. She sucks me down to the base and then back to the tip and releases me. “There, now go kneel and…”

Before she could finish, Rachel interrupted her, “Hey, can I get one of those foot massages? I had a few clients today and they all wanted me in some ridiculous boots or heels.”

Donna smiled, “Of course, that’s why he’s here.” So I got on my knees and crawled over to Rachel.

After removing her sandals I started rubbing one of her feet, “Don’t worry, I just want the massage. But to show my appreciation, I’ll help you out a little.” While I massaged one foot, the other gently rubbed the underside of my cock. It was lazily slow and barely touching, so I was in no danger of cumming, but it was driving me crazy! After several minutes she was ready to switch feet, but noticed something, “Looks like you made a mess. Better clean that up before you start.”

I was confused for a moment until I looked down and saw my pre-cum coating the top of the foot that was rubbing me. Embarrassed, I say, “Yes ma’am,” and start looking around for a tissue.

“What are you looking for? It’s right here.” She raises her foot towards my face, “Start cleaning!” It finally dawns on me what she’s expecting and I freeze. I’ve never done that and the thought repulses me. I look over to Donna, hoping for a respite, but she’s just smiling at me and slightly nods. Realizing I’m trapped, I gulp, take her foot in hand, close my eyes and lower my mouth. The taste is about as bad as I imagined, but I persevere and lick clean the entire top of her foot. Once it’s “clean” she switches feet and we go back to rubbing one another. She then has me clean her other foot, which is even more covered than the first.

Rachel was all smiles and thanking me, but I felt disgusted. Donna must have had some pity as she told me to take the empty plates to the kitchen and bring out more snacks. Knowing this will take me a few minutes I’m happy for the break, plus a chance to swallow a gallon of water to get rid of the taste! After rinsing my mouth in the sink I take my time in the kitchen cleaning up and preparing some more food. It also gave my cock a chance to calm down for the first time tonight. But I don’t want to press my luck, so I quickly stroke myself back to full attention, grab the plates and head back to the living room. Donna playfully admonished me for taking so long, “It’s about time! We have some thirsty ladies here. Put the food down and refill their drinks, slave.” I do as I’m told and as I refill Donna’s she gives my cock a few strokes, “Glad to see you’re enjoying yourself.” Once the drinks are topped off I ask if anyone else needs anything, when no one does I kneel in the middle of the floor where Donna instructed me to go and wait as the ladies continue chatting. Every once in a while I have to stroke myself to keep my erection going. Each time one of the ladies would notice and giggle or make a comment about how men just can’t keep their hands off of themselves. Eventually, Donna “suggested” I just keep stroking to make it easier for myself and of course warned me not to have any accidents. So I found myself slowly teasing my cock in the middle of the living room while four beautiful women kept drinking and joking with each other. My only breaks were the occasional drink refill. I was pretty much being ignored until Donna asked, “What about you, Nicole? Don’t you want a foot rub or anything?”

Nicole started to look a little uncomfortable, “Oh I dunno. Just seems a little weird. He’s your boyfriend and all.”

Donna tried to reassure her, “We’re just having a little fun. He’s doing nice things for us, he just happens to be naked and hard when he does it! But I don’t want you to feel uncomfortable.”

“Well, I wouldn’t mind a neck rub. My neck and back get sore pretty often.”

Rachel cut in, “With those boobs, I’ll bet your back hurts.”

“Hey! Be nice!”

“Oh no, honey. I’m actually jealous. I wish I had half your boobs. Do you know how many more clients that would get me? What are they, D’s?”

Nicole blushed a little, “Double D.”

“Damn, I’m barely a B! You should be proud of those girls and show them off.”

When Nicole didn’t reply, Donna spoke up, “Slave, don’t just sit there jerking off, get behind her chair and give her a massage.” I jumped to my feet to comply. Nicole had a lot of tension in her neck and shoulders so I spent some time trying to rub it all out. Since both my hands were busy, I had to concentrate on keeping my erection. Nicole’s occasional moans from my massage helped, plus I kept sneaking peeks down her top at her double-D cleavage.

Rachel caught me, “See? Slave boy keeps looking at your chest. Guys are all the same. If you showed them off you’d have men falling at your feet.”

Nicole was getting a little more relaxed, a combination from my massage and the drinks I imagine. She sighed, “Oh, I like the sound of that.”

“Oh right, what was it you said in my class you like to do to boys?”

She was suddenly less shy, “After teasing them for a while I like making them kneel in front of me and tell me I’m beautiful while they jerk themselves off. It makes me feel so sexy and powerful, like they’re worshipping me.”

Wow, I didn’t expect any of that! I was even more surprised when Donna said, “Slave, do that.” I walked around to the front of the chair and went back to my knees, stroking myself and telling Nicole how beautiful she is. Occasionally she would question my sincerity or asked what I thought about specific attributes or if I thought she was fat. Each time I would double my efforts to convince her. The entire time I was stroking myself slowly and gently until Nicole surprised me yet again by telling me to get to the edge and stay there while I continue showering her with compliments. It didn’t take me long to get to the edge, but keeping myself there without going over was quickly becoming a struggle. The room went quiet as the other ladies’ eyes were riveted to my display. Nicole simply sat back and watched, looking very relaxed and happy.

I was afraid she’d have me do this all night until she said, “Donna, you better tell him to stop before I get down there and fuck his brains out.”

Amy laughed, “I love when you get drunk. The shy girl disappears and the horny, trucker-mouth bitch I love comes out to play.”

Everyone else laughed and Donna mercifully told me to stop and I moved back to my position in the middle of the room. Nicole rebutted, “I’m not drunk! Not really. C’mon, when you were kicking him you mean you weren’t thinking the same thing?”