MILF Costume Party

One summer I was working for an Italian restaurant called Caesar's. They were an old fashioned kind of Italian, with genuinely Italian chefs, a preference for hiring pretty young waitresses, and a lack of familiarity or desire to use social media in advertising. This led to them hiring me to stand outside and give out fliers, dressed as a Roman soldier! It was a good costume to be fair to them, leather armor that looked (to my uneducated eye) to be pretty authentic in design. But standing on the high street, dressed as a Roman soldier gets you a lot of attention. I'm pretty shy normally and suddenly all kinds of people would give me weird looks as they passed by, make comments, or even stop to chat and take pictures. That was, of course, the whole point of the costume, but it wasn't my most comfortable job ever. Guys were usually ok about it, I think the costume appealed to the inherent manly spirit. Older teenage girls were the worst. They would giggle and laugh or come and tease me mercilessly.

There was one particular group that came back again and again. There were four girls, not much younger than me, maybe just at the end of high school. The blonde was the largest and the loudest: big boobs, big ass, and carrying a few extra pounds. There were two brunettes, both skinny with pretty faces. One was more shy and had the flattest chest of the bunch, the other wore plenty of make up and dressed sluttiest with a decent rack, often showing plenty of cleavage. The final girl was a beautiful small redhead who could have been a model, with a tiny waist, maybe 5' tall and not much more than 100lbs, sexy green eyes, and nice boobs. I fancied the pants off her but she was the meanest of the bunch.

"Hey loser, how much do they pay you to stand there? Is it enough to make up for the fact you'll be a dorky virgin for the rest of your life?"

I tried not to listen to the girls when I could, but they were pretty damn sexy as a group and I couldn't help looking at them. They knew what effect they had on me and that I was effectively trapped and helpless before their teasing. Sometimes they would fake showing interest in the restaurant, coming and crowding round me and cooing over the flyers. The slutty brunette would drop a flier and turn round to bend over and pick it up, letting her short skirt ride up her smooth thighs. The blonde girl would often push her boobs together right under my face or press them against my arm. It was like she was trying to absorb my arm into her but I can't lie, it definitely got me hard. Often the teasing would end with my crush suddenly "noticing" that I was perving at them.

"Ew, gross, he's totally looking at your tits! What a perv."

Loser, freak, pervert, and virgin were their favorite insults to throw. I wasn't mature enough to be immune from their mockery but I also wasn't in a place to do anything about it.

One day they stole my plastic sword. I think they dared the shy one to do it. I tried to make a grab for it but she threw it to the blonde who put it down her cleavage.

"Ooh," she moaned, "that's big and hard."

"Not like this loser's tiny dick!"

At that moment, a bunch of women came round the corner, heading towards the restaurant. There were 3 of them and they were pretty hot, clearly ready for an early start to a night out, definitely Milfs. One of them was blonde with big boobs, a shy smile, and a summer dress with tights and heels. The second had long brown hair, brown eyes, a cheeky smile, black pearl necklace and a purple dress which hugged tight to a very voluptuous figure with absolutely massive breasts. The dress wasn't cut to be hugely revealing but she still showed off a large cleavage. The third was a latina in a grey figure hugging jumper dress. She was the most toned of the three with a nice pert ass and boobs, still on the busty side, much to my pleasure.

Just as they rounded the corner they took in the scene with the girls playing keep away with my sword. The redhead got in between me and the blonde who had my sword and "accidentally" tipped her frozen yogurt down my costume.

"Oops. It looks like he jizzed on himself!" All three of them laughed.

The milfs bore down on them, faces growing stern.

"What are you doing to this poor young man?"

"Give him his sword back this instant!" The latina grabbed it and pulled it roughly out of the blonde's cleavage.

"Get out of here you nasty girls!"

"You ought to be ashamed of yourselves, what would your mothers' say?"

The sheer force of personality of these sexy milfs completely overwhelmed the girls to the same extent as they had been overwhelming me just moments before. They beat a hasty retreat under the disapproval of these mature women.

All three of the milfs gathered around me, checking if I was ok.

"Here's your sword back."

"Those girls are such bitches."

"Just ignore them, they're bullies."

"Oh no, look, you've got yogurt down you."

The chesty brunette pulled some tissues out of her handbag and began to wipe off the yogurt vigorously, causing her chest to shake and wobble.

"What's your name, soldier?" the blonde asked.

"John."

"I'm Charlie, and this is Eva and Arianna, and we all think you look very fine in that uniform. Don't we ladies?" They all chorus their approval together. The wiping of the yogurt descended to the leather skirt of the costume and I could feel her pressing the leather against my crotch.

"It's ok," I protested, "I'll get it cleaned up later."

"Oh honey, I don't think they pay you enough for being out here."

"Doesn't he look like such a stud in that armor though!" Eva stepped back, observing me, her eyes traveling up and down my body. Somehow I didn't mind their attention like I minded the girls. They seemed genuinely interested in me.

"Do you get to wear underwear under that skirt?" Arinna's hand, which had been cleaning me up, toyed with the edge of the skirt.

"Arianna!"

"What? I'm just curious what Romans used to wear and whether it's like Scottish men and their kilts. Do you mind if I check?"

I gulped. The idea of a sexy busty milf sticking her hand up under my leather skirt was making me hard very quickly. "Um, sure." She ran her hand up my thigh until she met the edge of my boxers. I expected her to stop there but she went up a little further and let her hand brush against my low hanging balls.

"Apparently Romans wear boxers," she declared.

Charlie giggled. "I'm not wearing any underwear!" she whispered. The women had all gotten closer to me as they were talking. Arianna's boobs were now touching my arm. Eva stepped closer.

"Do you have a big weapon, John?" she asked softly. I held up my plastic sword. "That's not the weapon I mean." She practically purred. "Can I touch your weapon?" She was now pressed up close to me, almost whispering in my ear. I looked around at the others and they looked eager, encouraging me.

"Go ahead." I reply with an effort at a confidence I didn't feel. This was not the sort of thing that normally happened to me and I was going to enjoy it as much as possible.

Eva reached down and Arianna lifted the skirt a little, her hand still on it, to allow Eva's hand access. She reached straight up for my crotch and her questing fingers soon found my hard cock. She wrapped her hand around it, making me breathe hard.

"Oh John, you have a big weapon! It's very hard John. Is that because of those girls?"

"Not really."

"Are you attracted to older women, John?" Charlie asked.

"Well definitely you three, you are stunning."

"Oh, you're such a charmer. I love it."

The milfs withdrew a little.

"I think we've used up enough of your time and we don't want to get you in trouble."

"Keep up the good work soldier!"

"Give us a couple of your fliers and we'll be back sometime." I hand them three fliers.

Arianna pauses as the other two turn to leave. "You don't do bachelorette type things dressed like that do you?"

"Oh, um, no."

"Would you ever consider it? I think you'd be a big hit as a stripper wearing that."

"Maybe," I give her what I hope is a cheeky smile.

"Write your number down for me on the flier. I could definitely find you some work that pays more than this if you're interested."

I hesitate for a second, then scribble my number for her. I wave the three of them off on their night out, adjusting my uniform over my still erect cock.

As I popped into the restaurant later for a break, one of the waitresses asked me what all that was about. I told her the older women had rescued me from my tormentors and were interested in the restaurant. I said she should look after them well if they come in.

****

That evening I got a call from an unknown number. Arianna's voice comes on the other end when I answer it.

"I've got a proposition for you John. How would you like to earn a few hundred instead of your usual wage?"

"Wow, that's a lot. Is this for a bachelorette party?"

"That kind of thing. It would definitely involve stripping. Would you be up for being touched as well?"

"What do you mean?"

"Well, it's for me and my friends. We have a tendency to get very handsy and we thought you looked very attractive. We're all adults and we'd love it if you'd be up for coming over in costume for some adult play. You know, us playing with your sword." My sword starts to rise as I imagine having it played with by those three sexy milfs. "Does that sound like something you might be up for?"

"I'm definitely getting up for it!" I replied without thinking, the innuendo just slipping out.

"Oh really, John? You might just be a lot of fun. How's Saturday night?"

"Saturday night is fine."

"Great, come to 24 Greenoaks for 8pm in your costume. And this time, don't wear any underwear."

"Yes miss."

"And John, I really like a big load, so don't jerk off between now and then."

****

I show up to the house pretty nervous in my uniform. Luckily the street is quiet so I don't get any weird looks before I reach the front door and knock. The door opens quickly and I am greeted by the sight of a massive cleavage. Arianna is also in costume, dressed as the sexiest barbarian warrior I've ever seen. Her massive breasts are squeezed together by a tan bra that is just visible inside a leopard print tunic cut low down the front. The outfit is completed with leather bracers, a leather headband, and fur boots. My jaw drops open.

"Come in quickly." She grabs my arm and pulls me inside, letting the door close behind me. "Do you like my costume?"

"It's, wow! It's amazing. You look amazing! I didn't know this was going to be a costume party."

"Aw thanks, we didn't want you to be the only one dressed up and we thought a little bit of costume roleplay might be fun. I'm a barbarian slave girl. Come on through and see the others."

She leads me through to the living room where Charlie and Eva are also dressed up. Eva is wearing what looks like a modified wonder woman outfit, leather armor over her big boobs, leather bracers, leather skirt and leather thigh high boot, a rope (or lasso?) at her waist. She waves at me as I come in and gives me a twirl. Charlie is sitting on a chair like it's a throne, her smooth bare legs nearly completely exposed under a white and gold dress. I've never been the biggest fan of sandals but her black leather ones, laced all the way up to the knee, are very sexy. She also wears a golden circlet on her head.

"I am Queen Cleopatra," she announces. "Welcome to my court. This is my loyal gladiator," she gestures to Eva, "and this is a rebellious barbarian slave," she points to Arianna. "I want you to arrest this slutty slave for me."

I turn towards Arianna who has put a sofa in between me and her. I move slowly towards her, not quite sure what to do. She circles around, keeping the sofa in between me and her. I realize that this is going to be a game they want me to play. I pretend to go one way before darting the other way and nearly catch her before she manages to get round the corner of the sofa and put it between me and her. Eva starts to cheer me on.

"Come on soldier. Take down that barbarian slut."

Arianna sticks her tongue out before giving me a dirty, sexy look, licking her lips and cupping her boobs. "You'll never catch me."

I dive over the sofa, catching her by surprise as the other women cheer. One hand catches her costume as she tries to spin away from me and suddenly her massive boob spills out. She gasps, catching it and covering her nipple with her hand, pulling herself out of my shocked grasp.

"Oh, naughty soldier!"

I'm about to apologize when the other two both cheer and whoop. Arianna tucks her tit away and I chase after her again. This time I'm too fast and catch her round the waist. Pulling her into a hug, her big ass pressing against my leather skirt. I can already feel my cock beginning to swell from the situation. I'd never really played around with this kind of game before but I liked it so far.

"Grab her wrists!" Charlie called.

"Subdue her!" Eva added, coming over and offering me her rope.

Arianna struggled, her ass rubbing delightfully against my hardening erection, as I pulled her hands behind her one at a time and tied her hands loosely behind her back.

"Oh no, you captured me," she lamented.

"Search her!" Charlie ordered. "She may have hidden weapons. You'd better search everywhere, who knows what she could be hiding under those clothes."

I turn her round and start to run my hands up her sides. She shivers as I brush the sides of her big breasts.

"Get her big tits out!" Eva encourages me and Arianna gives me an eager look, biting her lip. I put my hands on her massive tits and squeeze them together and she moans. I pull her costume to the side and pull her tits out of the costume. They are incredible. Massive soft mounds of flesh each nearly the size of her head. I have never played with tits this big before and I start to grope and squeeze them, which Arianna seems to enjoy greatly. My cock is at full mast and I have a moment where I can't believe that I'm being paid for this. Amazing!

"I'll take a closer look," I tell her, before burying my head in her massive cleavage. It would be easy to drown in them so it's not long before I have to come back up for air. I concentrate my attention on her nipples, licking them and sucking them into my mouth and she moans.

"Check up her skirt too!" Charlie calls, "maybe she has something dangerous underneath."

Arianna bends over the back of the sofa and lifts up her skirt revealing leopard print panties and her big ass cheeks. It's so hot to see her still half clothed but displaying her sexiest parts to me, letting me have complete control over her body. Her ass looks so good to touch. I reach out and touch it, then grab it and grope it. Then I spank her lightly and she yelps, biting her lip.

"Search between her legs," Eva adds and I run my hand up between her thighs until my hand touches her panties. They feel wet to the touch and I press against them, pushing them against her pussy and she moans. "I think you found something! Explore that more."

"Yeah, really get your fingers in there!" Charlie sounds like she's enjoying watching. I am just concentrating on the sexy woman in front of me and I can tell she is enjoying it, eyes closed and moaning. I pull her panties aside so that I can see her pussy and start to run my fingers up and down her wet slit. She moans even louder, her breathing getting harder and faster as I slide my finger inside her. I can't believe I'm finger fucking this sexy woman in front of her two friends and she is absolutely loving it. I slide a second finger inside her and keep thrusting them in and out of her, spanking her ass. The other two are cheering me on as I finger her. I start to explore the top of her pussy with my thumb, finding her clit and rubbing it back and forth.

"Oh fuck you're going to make me cum!" she moans loudly. "Oh yes!"

Suddenly her pussy clamps tight around my fingers and she collapses against the sofa, moaning and gasping. "Oh fuck, oh yes!"

Charlie and Eva applauds and Charlie beckons me over.

"Well done soldier! You have vanquished the barbarian. Now you may kneel at my feet."

I leave Arianna moaning and dripping and come to where Charlie still sits on her throne and kneel in front of her.

"Now, kiss the feet of your Empress." I feel less comfortable about this part. She reassures me in a whisper "my feet are really clean, just give it a try if you want, you might like it."

I bend my head to the floor and kiss her feet. They smell nice and are very smooth in her sandals, arched over the heels.

"Do you like my feet, soldier?"

"Yes, Empress," despite my early misgivings, I find myself continuing to be turned on by the scenario she is playing out. My cock is still hard and throbbing.

"Why don't you sit at my feet then, cross legged, just like that, and I'll use my feet to find out if you've done as we asked." She must have seen the worry cross my face. "Don't worry, I'll be gentle."

She slides her foot up under the leather skirt of the uniform. She finds the inside of my thigh bare and starts to slide her toes up towards my still hard cock. I gasp when her toes make contact with my balls. She gently rubs against them, making me moan. I wasn't really into feet before tonight, but with this sexy lady playing with my balls like this, I could definitely learn to get into it.

Ava came up behind me and her hands rested lightly on my shoulders as she watched. "I hope you don't mind," she murmured in my ear, "we've had quite a lot of experience and by the end of tonight, we plan for you to have experienced a lot of new things." Arianna had left the room by this point while my attention was elsewhere.

My eyes are drawn up Charlie's long smooth legs as she spreads her legs wider for me. Her white toga with its gold hem rides up until it only just covers her pussy. Her toes move up my balls and start to stroke their way up my erect shaft, making me moan again. Her toes are soft and gentle against my erection and I can just feel the leather sole of the sandals touch against my balls on each downstroke.

"Oh soldier, that is a massive weapon you have there. So straight and hard and long. You please your empress!" She pulls her dress up further and reveals her shaved pussy, right in front of my horny gaze. My cock twitches against her toes. "You may kiss my pussy soldier."

The whole scene is so sexy, and I find I am loving the fact that Ava is watching me being ordered around by this sexy milf. I lean in and press my lips against the lips of her pussy as she spreads her legs wider. I kiss her, her sexy aroma in my nostrils. I kiss her again and my tongue starts to explore, licking up and down against her pussy lips. She moans as I slowly part her lips and slip my tongue inside her and start to lick her out. She rests her hands against the back of my head and starts to rock her hips against my probing tongue.

"Mmmm, yes, keep doing that."

Ava leans in across the top of my head and starts to grope Charlie's big tits. She kisses her on the lips as Charlie moans more urgently. My tongue explores her clit and I take it into my mouth, sucking on it. I start to flick my tongue back and forth over her clit and she starts to shudder. Ava releases her mouth and she cries out "yes, yes, yes!" She holds my head tighter into her and I flick my tongue harder and faster. "Oh yes!" she calls, as I taste her juices flooding her pussy, climaxing hard. She slumps back in her chair, breathing hard.

I stand up, my cock still hard, enjoying this roleplay immensely. I wonder what she will get me to do next. As I wonder, Arianna comes back into the room dressed in a similar toga.

"Oh it looks like you had a lot of fun without me! He's good, isn't he? I'm so glad we ran into you and hired you."