It all started very innocently. The kids were in school, so I took a waitress job at night to help make ends meet. Bob, who my husband, Jim, knew very well, and used to bar tend for, needed a waitress.
The nights were fairly short as the restaurant closed at 8 p.m.
One night, the evening bartender never showed up. Bob asked me if I would like to learn the trade. I jumped at the chance. I was always fascinated by watching them work.
The bartender never returned, and I ended up working the bar at night. My husband suggested I wear sexy attire to enhance my tips, as the clients were mostly older men. He was right. I would wear a semi-sheer top with a sexy bra. The men stayed longer and tipped better. Good for me, and Bob.
Bob and his friends, his lawyer, Pete, two other bar owners, Steve and Lou, and a retired man Bill, would play cards once a month. Rotating the three bars on Mondays when they were closed.
Bob and Steve were younger, in their 40s, and quite nice-looking. Lou and Bill were older but kept themselves well. Pete was nice-looking but had a bad reputation for getting aggressive with women.
One day after everybody left, we were closing and Bob asked, "Would you consider working when we have our monthly card game?"
I said, "Sure." His friends were good tippers.
He left and returned with an outfit. "This is what we'd like you to wear."
It was a French maid's outfit, with high-cut legs, and only a built-in half bra with no blouse. My jaw dropped.
Bob said, "The guys and I love looking at you, wearing see-through tops with sexy bras. But we want to see those nipples that were hidden beneath the fabric."
He said, "They promise they won't touch, just look." I'd get two hundred a month, plus tips, for the next four months. If at any time I didn't want to do it again, he would understand. "Here would be first, then Lou's, then Steve's, and last would be back here."
I had been very sexually active before but was very nervous. We could use the extra money. I wasn't working so I could stay home during the day with our kids until they were both in school. It would be another four months, then I had a job in purchasing at a company waiting for me.
I said, "Maybe, but I have to ask Jim if he minded me being topless. I also want to make sure they know there's to be no groping of any kind."
I had been groped many times before when I was a stripper. I showed my tits and nipples often, usually shooting pool with a low-cut top and no bra, or listening to a band at a bar, with my tits popping out now and then as we danced. My husband liked it, and so did I. But that was with strangers who we wouldn't see again.
Bob said, "I wouldn't have asked you if I hadn't already talked to Jim about what we wanted, and showed him what you'd be wearing." Jim had told me what Bob had said he'd like to do to me.
I said, "If Jim said okay, then I'd love to."
I talked to Jim, and he was thrilled that I would consider working topless for Bob and the others, and that he loved the choice of outfit.
Monday came, and Bob handed me the outfit and two hundred dollars. I went to the ladies' room to change.
I couldn't wear my panties with the outfit the way it fit. I stood there nude, in front of the mirror admiring my naked tits, and my ever-hardening exposed nipples in the cool air. I massaged lotion on my breasts to keep from getting a rash from rubbing on the outfit. I wondered if the guys would have enjoyed doing it for me. I slid into the outfit, adjusting it so it held my tits in place but still showed my nipples.
With a deep breath and a wet pussy, I opened the door and went to the bar. They all looked at me with big smiles and gave me their orders, which, of course, I already knew.
Things went well. I became much more relaxed while they were enjoying me serving them drinks. I was having a few myself to help my nervousness. They enjoyed me taking away the empty glasses, and serving their drinks, with my tits hanging out, as much as they were enjoying their game. We were all getting more tipsy as the night wore on.
While serving and clearing, I had to bend in. I knew I was brushing my tits against them as they sat very close to each other. They made no effort to bend away, but they never reached up to touch me. Getting tipsy myself, I wanted them to.
When the game broke up and they were leaving, I told them, "As you followed the rules, and being as I am more than a little intoxicated, I will allow you to cup my tits and kiss them." Everyone thanked me but refused, citing my state of intoxication, and their promise not to touch me.
As Bob and I finished up cleaning, with me still in the outfit before changing, he got behind me, put his hands on my hips, and whispered in my ear," Jim told me it would be alright if I played with your tits, as long as you don't mind."
I said, "I wondered why you hadn't hit on me before now. You know, I couldn't wear panties with this outfit."
As soon as I said that, one hand was on my tit, and the other was unzipping the outfit. He pushed it down and started fingering my swollen, wet pussy. Paying a lot of attention to my clit, he was very good at it, and I was soon shuddering with a massive orgasm. I felt his erect cock pushing against my ass, wanting to penetrate me.