I'd always spent my summers working in Daddy's insurance office, at least since I turned sixteen I did. I'd type and answer phones and run errands and clean up and generally make myself useful. That was in addition to taking care of everything at home. See, Mom died when I was thirteen, and, well, it's been just me and Daddy ever since, so I had to learn pretty quick how to take care of things. It was just him and me, and he did a pretty good job of being both a mom and a dad to me.
Well, I went away to college this year and things changed a little for me. I'd dated and everything in high school, but never let the boys I was with do much. Except for Bobby. We kind of grew up together, and, well, we kind of explored. You know, we played "doctor" when we were kids and we did a little more when we got older. Anyway, I turned eighteen my senior year and I'd decided that I wasn't going to go to college a virgin, and Bobby, well he was sweet and I always knew that he'd be the one.
It was all very traditional and kind of American Pie like. We went to prom, and after to a party. And then, well, we'd gotten a motel room and Bobby and I made love and it was wonderful and exciting and sweet and special. Daddy didn't want to talk much the next day and I guess he knew what had happened, but it didn't really change things between us.
At college things changed, at least when it came to me and sex. My roommate, Bethany, was a bit further along that road than I was. About two days after we got there she showed me her toy collection – she had a couple of dildos and one of those rabbit vibrators you hear about and a back massager and a little silver egg vibrator. And she insisted we share. And, well, let's just say I learned to enjoy sex and came to the decision that sex could just be sex, and even though it was better if you were in love, like I was kind of with Bobby, it was a whole lot of fun even if you weren't.
So I came back to Daddy's office that summer with a whole different attitude about some things. And all the innocent flirting and little jokes that Mr. Addemly, Daddy's partner, used to make made me think about things that I never had before. And there was a new person there, Mr. Kennest, and he was pretty good looking and a little younger than Daddy and Mr. Addemly, who both had just turned fifty that year.
One thing we had always done in Daddy's office, every couple of weeks when we had to stay late and finish up all the accounts, was to have a pizza or something together and then play poker. It was fun, and Mr. Addemly used to tease about playing strip poker someday, and I'd blush and Daddy would tease me a little and I'd blush some more.
But this summer when it happened about two weeks after I came home from school I felt a little different. I blushed, like always, but Mr. Kennest joined in a little and I was kind of squirming because, well, you know, because I kind of liked the idea, especially if he was going to be there.
I thought about it a little during the few days after it happened, but I was a little uncomfortable with the idea. I mean, I grew up with Mr. Addemly. And Daddy hadn't seen me naked since I was a little girl and he didn't know, at least I think he didn't, that I shaved my pubic hair now and only had a little triangular patch right above but kept my labia pretty much hairless all the time now.
Still, I'd thought to myself back then, it'd never really happen so what did I have to worry about? And Bobby and I were kind of fooling around a good bit, since he'd come home from school at the same time I did.
It all changed at the end of July. Daddy had gone out of town to meet with a big client who had moved away but still did business with Daddy. Bobby's parents had dragged him off to visit his grandmother at the same time. So I was by myself and, well, sometimes masturbating just isn't enough.
We all stayed late one night to work on the accounts so everything would be up-to-date when Daddy came back. Mrs. Lemington, Daddy's secretary, had to leave early, so it was just me and Mr. Addemly and Mr. Kennest After we finished the accounts we had a pizza, and then sat around the table and got out the cards.
We played a few hands, and then Mr. Addemly made a little joke about playing strip poker. But this time, instead of blushing, I said "Why not? It's hot in here and it would be nice to be wearing fewer clothes and I bet I can beat both your butts anyway."
I was kind of bluffing, but I was also half serious, which surprised me. But once I'd said it I wasn't going to back down.
"Are you sure, Maggie?" Mr. Addemly said. "I was just teasing, you know."
I was sure. I knew Mr. Addemly and his wife were swingers – I'd seen their pictures and ad on a web site my roommate had shown me one night. I was really surprised, but right then it kind of worked into what was going on since the ad had been pretty clear about the two of them playing together and apart.
Mr. Kennest spoke up, too. "Maggie, you have to be kidding." He was divorced so I figured he was available, and probably horny.
"No, I'm not. I bet I can beat both your butts. You'll be naked and I'll be dressed and you'll feel silly for having teased me all this time."
"But Maggie..." Mr. Addemly said.
"But nothing. Deal!" I demanded.
Mr. Addemly and Mr. Kennest looked at each other, and at me.
"Ok," Mr. Kennest said. "But no-one ever says anything about this, especially to your father."
"Ok," I said.
Mr. Addemly dealt the cards for Blackjack. I got a queen and an eight. Mr. K got a seven and a five, and Mr. Addemly a ten and a four. I was feeling pretty good, so I stood on my eighteen. Mr. K took a hit, and busted with a jack. He took off his shoes and socks.
On the next hand I got a blackjack, and Mr. K got a nine and an eight. Mr. A. got a four and seven, and then a three. He took one more card and it was a nine, and he lost his shoes and socks.
We went on like that for a while, and I was pretty lucky. I lost my pumps on the fifth hand, and my hose on the sixth (Daddy ran a very formal office and Mrs. Lemington and I had to wear hose and dresses or suits and the men all had to wear coats and ties.) But I was still basically dressed, although I had teased the two men by turning around and pulling my skirt up a little and letting them see my panties before I tugged off my pantyhose.
We kept playing, and both Mr. Kennest and Mr. Addemly were in only their shirts and boxers when things started going bad for me. I'd only lost the jacket to my suit, so I was feeling pretty good about things. Boy, was I about to find out how wrong I was.
First I lost when Mr. A. drew a seven to get 21 and Mr. K had nineteen to my eighteen. I slipped off my skirt and was sitting there in my slip and blouse. Then I lost again when I bust after drawing a six and a seven. I slipped off my blouse. I was still pretty modest, since I had a full slip on, but things weren't going the way I thought they would – at least sort of.
Well, Mr. Kennest lost next, and he took off his shirt and he has a really nice chest and a nice flat stomach, at least for a man in his forties. But then I lost, and took off my slip and was just in my bra and panties. Thank god I was wearing matching ones that day – nice ones I'd just got – pale yellow with lace on the bra and lace panels on the hips of my bikini panties. Both of the men got kind of pale, but they both kept looking at me. Or at least at my breasts in my lacy yellow bra. I felt my nipples get hard. They do that all the time. It can be embarrassing. But it was a little exciting that night.
Mr. A. lost his shirt on the next hand. I was still pretty nervous. I was going to have reveal something pretty serious if I didn't keep winning.
I didn't.
When I lost the next hand I stood up slowly, took a deep breath, and reached behind me to unfasten my bra.
"Maggie, you don't have to, you know. This is far enough," Mr. Addemly said.
"No," I said. "It's all right. I lost fair and square and now you get to see my breasts. I hope you like them."
I unhooked my bra and shrugged it off. Actually, I think I have pretty nice breasts, but since the only people who had ever seen them were me, my roommate, my doctors, and a few boys, I was a little worried what two older men would think. I'm a 36B if you're really interested, and my nipples are smallish and light brown and kind of perched up high on my breasts. I wear my hair kind of long, and the tips of it just brushed over my nipples. They got even harder.
"Oh my god!" Mr. Kennest sighed.
"Goodness!" said Mr. Addemly. "You certainly have grown up, Maggie."
They were both staring pretty hard at me, and Mr. Kennest had one hand in his lap.
Now I finally blushed and quickly sat down at the table, crossing my arms in front of me. It was pretty clear that they both were getting hard, and I think Mr. Kennest was playing with himself.
The next hand was nerve racking. Mr. K. dealt. I got a nine. Mr. A got an ace. Mr. K. got a ten. He went around again. I got a three. Mr. A got a king – 21! Now it was between Mr. K and me. He turned over his card. Another ten!
"Oh, geez," I though. "This isn't good." I needed a nine. Mr. K turned over the card – another three. Fifteen! I had to take another card. An ace! Sixteen! This was getting to be too much. One more – seven, bust!
"Well gentlemen," I said, getting up slowly. "I guess I should have kept my mouth shut." I turned around and looked over my shoulder. Both men had pushed back a little from the table, and it was clear they were both erect now. Mr. Kennest's penis was even poking up a little over the waistband of his boxers. I hooked my hands in the waistband of my panties and slowly slipped them down over my butt, then down my legs to the floor. I stepped out of them, and then turned around.
"Maggie, you're gorgeous," said Mr. Kennest. Mr. Addemly's eyes were fixed on my shaved pubis. I felt myself begin to get a little excited.
"Thank you," I said. "But it's only 8:30. How are we going to play now?" I had a pretty good idea, but though I'd tease them a little.
"Well, I think that's up to you," Mr. Kennest said.
"Ok," I said. "I'll tell you what. Bobby's been out of town for a few days just like Daddy, and I'm horny. So, if I win you keep stripping. If you win I'll do something nice for you. And when we're all naked, well..."