First Night as a Topless Server

Fran is so brazen. I wish I wasn't shy and could be more like her. She is so at ease with her body and sexuality. The stories she tells in our dorm room are so naughty plus she thinks nothing about walking around completely naked. It's not that I'm a virgin or anything. I had a boyfriend in high school and we did it after the prom as well as in his father's car over the summer before coming here to this big university.

We both play varsity volleyball and she thinks nothing about showering with the girls and walking boldly nude around the locker room. It took me weeks of her shaming me for not showering after games before I finally did it with her and my teammates. She complimented me on my fit body. It's true it has matured over the last year. My breasts are smaller than Fran's, a 34B cup with a slim waist and small bum. I blushed a hot blush on my face when she checked out my body before complementing me. She joked about my full pubic bush. I shaved it off that same night to look like the other girls.

One night after our studies, I told her how I admired her natural way around sex and wished I could be like her. She had an idea to help me. As a part-time job, she was a topless server at men's bachelor parties and get-togethers. She urged me to do it too. It paid great and was completely anonymous. My hometown is a thousand miles away and nobody at one of these events would ever know me. It took me two days of mental and moral turmoil to decide and tell her that I would do it. She was overjoyed and the agency agreed to interview me for the job.

That was another story. Oh my god, the man who owned the agency needed to meet me to see if I was appropriate. Fran told me I would have to bare my breasts for him. I begged her to go with me for support. Thankfully, she agreed. I was told to wear a skirt with bikini panties. Fran lent me a pair of hers. I'll never forget the queasy feeling in my stomach when we went into the owner's office. He was a big, tall man about my father's age. He rose from behind his desk and walked around to great us with a big smile on his face. Fortunately, he was a handsome man which made it less creepy.

He said to my friend, "Fran, how the hell are you. You look great." They gave each other a brief hug and a New York air kiss. He turned to me looking me up and down with a hungry look in his eyes. "And this must be Alicia, your friend." He stepped to me and hugged me. I could smell alcohol on his breath. "Great to meet you, Alicia." He stepped back.

All I could say was, "Thank you, sir." As soon as it came out of my mouth, I realized how lame that sounded.

In a booming voice, he said, "That's what I like, a polite, refined girl." He leaned back on edge of his desk. His eyes drilled into my body. I felt naked even though I was still fully clothed. He continued in a firm voice, "Very nice. Come a bit closer. Good. Turn around Alicia. Yes, just like that. Very good." I gave a sigh of surprise when his hand cupped my bum-cheek. "Nice, firm ass. You must work out."

I bit my lip as he groped my bottom and said meekly, "Yes sir. We play volleyball."

He boomed out, "I love volleyball. Beach volleyball is my favorite Olympic sport. I'm an ass-man and those babes have perfect asses. Lift up your skirt, Alicia."

I looked over at Fran and she nodded yes. Blushing a thousand shades of red, I lifted my skirt to show him my bottom with the small panties that left my bum-cheeks naked.

"Sweet, I love the panties. I bet sexy Fran lent you a pair of hers. Let me feel your ass. Nice and firm. Very good. Okay, turn back around." I turned and his eyes were drilled into my chest. He is a very good-looking man and that somehow made it less tacky for what I had been warned would be coming next. "Okay, sweetheart, you want to be a topless server. Let's get topless."

I started unbuttoning my blouse and when I looked down I could see a big tent rising in his pants. I had mixed feeling of panic and some pride in turning on this alpha man. I finished the buttons and took off the blouse. He held out his hand and I gave it to him to hold. Now, the big leap, I undid the clasp between the bra cups and spread them to show my breasts. I just wanted to give him a quick look and cover back up but he held out his hand again. I knew he wanted my bra. I bit my lip and obeyed. Then, a big shit-ass grin came onto his handsome face.

"Nice, very nice. I like small, perky titties. Let me check if they are natural." He cups my breasts in his hands and massages them expertly. My nipples became diamond hard as he groped them. I think I sighed at his erotic touch but I'm not sure. My brain was in a lust fog. "Our clients are going to love these." He dropped his hands and continued, "Alicia, you are hired. Welcome to my company. Fran will let you know when you will be working. Right, Fran?"

She said, "Right boss."

He then said, "Fran, that reminds me, we have to discuss some marketing ideas. Right?" Fran had a quizzical look, then smiled and agreed. He continued, "Alicia, why don't you sit in the waiting room while Fran and I have a meeting."

I went out and sat on a chair in the waiting room. The receptionist kept a straight face as animal sounds, obviously of sex, came though the closed office door along with rhythmic pounding of the furniture. I'm embarrassed to say, the sex action turned me on so much that my vagina gushed with love juices. As soon as I got back to my dorm room and alone, I masturbated frantically to a huge orgasm thinking about my new boss. I might be shy, but I have the same natural instincts as other girls.

The first night as a topless sever.

Fran helped me get ready. She lent me a short shirt and the panties I wore at my hiring. The skirt was so short I could see the bottom of my bum cheeks in the mirror. I almost said I couldn't do it when I saw that, but Fran convinced me doing this could help me overcome my phobias. Plus, she kept emphasizing that I will be completely anonymous. "Give it a try", she kept saying. So off we went for our nine o'clock appointment at a big suite in the most expensive hotel in the city.

So, here we are. My heart is racing as Fran and I go up the elevator. I can hear the loud male party voices down the hall as soon as the elevator doors open. Fran takes out some lipstick, applies it and passes it to me. I do the same a bit clumsily since I rarely use lipstick. Fran knocks on the big double door and a blast of rock music and shouts of welcome hit us as they open. The executive-looking man who opened the door yells out, "The sexy babes are here, guys." There are shouts of joy and raising of glasses of alcohol all around. About forty men of all ages from mature older gentlemen to boys just out of high school fill the large room. A good-looking man, we later found out was the Best Man, leads us to a bedroom to get ready. Fran, bless her heart, can see I am very nervous.

She says, "You can do this girl. Just remember nobody will ever know. Just go around like I said getting drinks for the men. Watch what I do." I hang my blouse and bra in the closet. Fran looks over my naked chest and says, "You look great. The guys will love you." With butterflies in my stomach, I go back out to have all eyes in the room drilling into my chest. My cheeks are hot from the blush I know is there.

The Best Man shouts out, "Hey guys, let me introduce our two lovely ladies." He looks down at the note in his hand. "This is beautiful Fran." She smiles a big smile and lifts her hands high up in a cheery greeting that also lifts her breasts high up. "And this is totally cute, Alicia." I force a smile and lift my hands high like Fran. The cheers make me feel a bit more at ease as I display my nakedness. I can't look any of the men in their eyes. Fran takes my hand and leads me to the bar and the bartender behind it.

Chuck says, "Hi Fran. Great to see you." He looks at me. "I don't think we've met. My name in Chuck."

"Hi Chuck."

He says, "Here are your trays. Fran, you take the tequila shots and Alicia, you take the Corona beers. Go and make those guys happy and get lots of tips."

I go out amongst the men with my tray of beer. The bottles hide my bare breasts at first but as the men take them, I'm exposed to their hungry eyes. Some of the men are very brazen. They stare at my chest and even compliment me on my breasts. Several put five- and ten-dollar bills in the waistband of my skirt. I thank them graciously.

My goodness, many of the men are as old as my father and his friends. It feels surreal to expose myself to these similar mature men. It reminds me of pool parties my parents used to have. The older men would stare at my young chest and body but back then, I would have my bikini on. It did turn me on, but it seemed harmless. Here in the hotel suite, I could feel a strong, sexual energy around me and growing inside of me.

A man comes over to me and says, "Here's a twenty-dollar tip. I'd like you to come over and ask my son if he wants a drink. He's old enough to drink now but he is very shy around girls. Hell, I think he's a virgin. I'd like him to get a good look at your sexy charms." He leads me to a tall, thin young man with a nervous look on his face. "Richard, ask the girl for a drink."

He glances down briefly to my breasts and then back up with a guilty look on his face. He is so sweet. He says, "Could I have a rum and Coke?"

"Sure, I'll get you one right away."

At the bar, Fran says to me, "Girl, pull your shoulders back and show of your gorgeous tits. You are way too shy. Show those guys how proud you are to be a sexy, strong woman." She continues, "I try to think of holding an orange between my shoulder blades to lift and show off my boobies. Try it." I straighten up my spine and hold an imaginary orange between my shoulder blades. I instantly feel more confident and attractive. Wow, Fran is so great. I'm so lucky to know her.

When I return with the young man's drink, his father is gone, and the boy has the courage to look more boldly at me. My chest is uplifted as Fran recommended to give him a good look. I wonder if mine are the first breasts he has seen. It makes me bolder to be with someone even shier than myself.

As the night progresses, the men get more generous with their tips. My nipples now stay erect and many men commented on that. At first, I blushed crimson but now I just smile. They also got freer with their hands on my bottom over my skirt. It didn't seem too out of line but some reached under the hem and give my naked bum-cheeks a squeeze. Fran told me how to tell those guys they had to pay an extra tip for that. Then, as other men see me accept the intimate touching, it happens more often. My crotch stays aroused as I serve the men. Fran was right. This is making me more at ease with my sexuality and I am seeing men's lusty nature exposed.

It is busy serving drinks but occasionally I meet Fran at the bar and she insists on me drinking a shot with her. I'm careful not to do that too often but it does make me feel very good and less inhibited.

I go into the bedroom with Fran to take the bills from our waistbands and fill our purses. Fran has some fifty-dollar bills. When I show surprise, she says she gave those men a feel of her breasts for the extra tip. I'm shocked but she says it is fun and super profitable. We go back out and I start thinking about whether I would let some man caress my breasts. I'm being bold now, holding my breasts up proudly as the men smile and check them out. The evening is going so much better than what I imagined. My god, what would my mom think of this?

At the bar, I have another shot with Fran. Was that my fourth? Then I serve a man over in a corner with my back to the crowd. He is a nice-looking man about forty with a wedding ring who obviously has had a few drinks. He says, "Why don't I give you a big tip and take a feel of your gorgeous, young tits." The devil makes me nod yes, and he puts a hundred-dollar bill in my waistband then cups both my breasts in his hands. My knees go weak with the pleasure of his touch. I just stand there like a tart as he massages them and rolls the nipples in his fingers. My god, he licks his lips as his eye hungrily drill into my breasts. My pussy starts to vibrate uncomfortably, and I get light-headed. I turn in a panic and walk quickly into the bedroom, close the door and sit on the bed to compose myself. My heart is racing and my body tingles all over.

Fran comes in to unload her cash. She looks down at me. "Are you okay?"

I confess, "Yes, but this is very overwhelming. I didn't expect exposing myself to these men would turn me on so much. I'm I a tart?"

"Hell no. It's all just natural, girl. Those are virile rich men, alpha types, and you are just a woman with natural feelings. It's all good, girlfriend. Just enjoy yourself and get some anonymous erotic experience. Come here girl and let me give you a big hug." I stand and melt into her embrace. She says into my ear, "Let's go back out there." We go back out and Fran leads me to the bar to have another shot. The alcohol and her pep talk have feeling good all over.

The man with the young son comes over and says, "I saw you offering that man over there a feel of your breasts. Please come over and do the same for my son." He takes my hand and leads me over. I follow obediently like I didn't have a will of my own. Truth be known, I want to be touched. The boy has had a few drinks in him by now and has a wry smile on his face as his father has me stand before him. "Here she is Richard, and she says she wants to do it." The boy's eyes opened wide as he looks at my breasts. The father continues, "Now first put the money in her skirt like I told you." He slips the bill in my waistband and then with a look of awe on his face, cups my breasts. His hands feel so naughty and blood rushes to my pussy. To my surprise, his father reaches his hand under the back of my skirt and runs his middle finger down the crack of my ass as the boy works my breasts. I grasp the boy's shoulders to steady myself. As my breasts are being pleasured the father's finger goes lower and lower below my panty-covered bottom to my vagina. Waves of erotic sensations shot up my body.

Fran's loud voice shouts close to me over the din of the music and male voices around us, "Hi guys. How is everyone doing?" The father and son freeze. She continues, "I need Alicia over at the bar." She pulls me by the hand away and whispers, "It looked like you needed a little rescue there, girl. Are you okay?"

"Yes, thanks. I was overwhelmed there for a moment. Whew."

"No problem. The party is over pretty soon."

I escape to the washroom and sit on the toilet to pee and compose myself. I can't believe how the juices from my vagina have soaked the crotch of my panties. Being so naked with all those horny, alpha men has really turned me on. This night has really opened my eyes to how my natural instincts are so strong.

The men started leaving and Fran and I have a nightcap and go into the bedroom to get dressed. She says, "You know that young guy that was so mesmerized by feeling your breasts?" I nodded yes. "Well, his father rented a room in the hotel and has offered me a huge amount of money to have sex with the boy. He actually asked to do you first, but I knew you wouldn't want that. Right?"

I say, "No way." Then gasp and say, "You're not going to do that either, right?"

"I need the money badly, so I said yes. Alicia, my dear, I need a big favor from you. His father is going to be in the room with me and the boy. Please be there with me. I don't feel comfortable with two men and just me. You don't have to do anything. I told the father, you won't. These hotel suites have separate bedrooms like this one, and you can just wait outside in the living room with the father while I do the son." I hesitate. She goes on, "Please, please." How could I say no.

So, the four of us get on the elevator and go down a few floors to another hotel room. When we go in, I see that it isn't a suite with a separate bedroom. It's one large room with a bed and a sitting area with a sofa. My god, I think, I'll be in the same room as the lovers. The multiple tequila shots I've had plus the sexual buzz I have on, leads me to sit on the sofa, curious to see actual sex close up. Fran turns on the bedside lamps and turns off the overhead lights. The father and I sit in the dark as the two lovers embraced in the light, standing at this side of the bed. The young man is much taller than Fran and well built. She takes his hands and guides them to her bottom. It's so sexy watching him massage her ass as she slowly unbuttons his shirt while kissing him submissively on his neck under his jaw. She takes his hands to her blouse, and he unbuttons it, exposing her naked, full breasts. He groans and gropes them amateurishly. A small animal sound comes from the father's throat beside me as he is moved by his son's lust. I can feel his male presence close beside me on the sofa in the dark. The sexual energy in the room has my crotch awakening.

Fran pushes the boy to sit on the bed and he leans his face forward and he suckles her breasts as she stands before him moaning in pleasure. It's my turn to give a sigh as I imagine her pleasure. The man beside me shifts closer and cups my breast through my blouse. My nipples are rock hard and his hands feel great. I think, what the hell, he has seen my breasts naked and many men have felt them this night. I stare forward at the erotic actions of the couple on the bed as my breasts are being massaged expertly.

Fran's back is to us. She unzips the back of her skirt, and it falls to the floor, exposing her sexy bikini panties and perfect ass. I feel the father unbuttoning my blouse. Yes, I want his hands on my naked skin. I stare ahead. Oh great, he's undoing the clasp of my bra between the cups. My breasts have become extremely sensitive with all the men caressing them this night. His hands go to my bare breasts, and it takes my breath away. I close my eyes and enjoy the shear animal pleasure of his touch.

I hear a zipper being undone on the bed and it is Fran kneeling on the floor between the boy's legs undoing his pants and pulling them down and off. There is a big tent in his underwear. I can hardly breath as she strokes his erection through the cloth. My blouse and bra are off, and the father's head is now low and his lips are circling my hyper-sensitive nipple. An electric jolt shoots through my chest to my crotch. Sweet Mary, that's incredible. Fran pulls down the boy's underwear and my eyes are riveted on his big cock standing up proudly as his father's tongue swirls maddeningly around my nipple.

Holy shit, Fran is licking the shaft of his cock as he looks down at her face in boyish wonder. That is so fucking sexy. My god, I feel a hand on the inside of my thigh. Yes, yes, he's sucking my other nipple. It that my loud moan? Wow, Fran has wrapped her lips around the head of the boy's cock. I feel a man's hand sliding up the inside of my thigh to my crotch. My knees just instinctively spread. If he touches my pussy, I might die.

His fingers do find my pussy, I groan out, "AAAAHHH. Ohhhh." and clamp his hand between my legs. My brain is a fog of lust as my nipples are being pleasured and I watch Fran's head bobbing and the boy's cock sliding in and out of her mouth. I should keep my legs closed and save my modesty. Holy shit, Fran is licking the boy's ball-sack. That is so freaking erotic. My pussy is vibrating. Fuck it, I open my knees and a hand slips inside of my panties to my sex. My legs spread wide in obvious invitation and the father's fingers expertly slide up and down the folds of my very wet crotch. A blast of the odor of my love juices hits my nose. I hear an animal growl in the older man's throat as he also smells my lust.