Hi! My name is Judy. I am a mid thirties woman who lives in the Midwest. I am not a particularly wild woman. Oh, I did the hook-up thing while I was going to college, just like most of the other girls. We'd go out in a pack to the bars with our fake ids, drink and dance and flirt with the guys.
If you found a fairly hot guy who was interested in you and you were horny enough or drunk enough you'd end up back at his place or your place and you might make out, or let him feel you, or maybe get naked and play together or maybe you would give him head. And then there were the times that you went all the way. Everyone, well almost everyone did it, both girls and guys. It is all part of exploring your sexuality in college.
But, after college, you got a job and started to think of a more permanent relationship. At least I did. So I did the dating thing, with the occasional hook-up but I never really found that one guy who I really wanted or he wanted me, enough to get that ring and start planning the wedding.
I had just broke up with my last fairly steady guy and was at loose ends
Now to tell you a little about my job. I work in a good sized office that employs a lot of people. A lot of women and a lot of guys. I'm probably in the mid range in age. Some older women, some about my age, younger women and the younger ones were not wild, but more open to things. There was an older girl named Amber who I was pretty good friends with and there were some younger ones that Amber hung out with. I really didn't hang out with people from work other than Amber.
So this day Amber comes to me.
"Judy, some of the girls and I are going to Florida for a week or so. Do you want to come along?"
I sort of looked at her. I had nothing to keep me here. It sounded like fun.
"Sure, when are you going?"
So she told me and I put in for vacation and got it approved. So it was going to be me, Amber, Michelle and Shelley. We all had the vacation approved and since it was sort of expensive to fly we figured we could pool our money and rent a van to drive down. Then we would have transportation while we were there to bum around. Amber got us some rooms at Key West and we figured it would take us two days to get there and two days back. We all had two weeks vacation so we could spend a week there and get home and have time to rest before work started for all of us.
So I packed my stuff. I had a nice bikini to take along. Not a string bikini or a thong. I was more modest than that. But it showed me off fairly nicely. I am not the big breasted woman but not bad either. The others were pretty much like me. Just your normal women, I guess.
So we all finished work on Friday and Saturday morning Amber picked me up with the rented van and then we got Michelle and Shelley and we are off for some time in Florida.
Now it just so happens that women are as bad as men when they are together. We talk about sex. We talk about guys we have been with before. Just like men do. We just don't talk about it like guys when we are with guys. Then we are all kind of reserved about sex. So it isn't long before the two younger ones are talking about finding some guys when we are down in Florida. Amber and I not so much. Finally the two younger girls asked us what we were going to do and we were pretty boring.
So the two younger ones started asking if we had any fantasies. Amber was non-committal but I was feeling sort of like I needed to do something different. So I opened up a little.
"Well, I have this fantasy of being caught naked."
Which got them all laughing. So I was asked what exactly I meant.
"Well, I used to have dreams of being locked out naked. Or having to show off to people. Stuff like that I guess."
So now that I admitted that my mind was a little kinky and they finished laughing at me Amber kind of looked at me.
"So, Judy, do you want to act out some of your fantasies>"
I was hesitant to say yes but the other two jumped in telling me that it would be good for me to get this stuff out of my system. They kept talking at me and finally the three of them made me a deal. They'd pay for my vacation, if, and this was a big if, I would do what they told me to do for the time we were gone. Now, I wasn't hurting for money, I could afford this vacation but the thought of getting it for free and maybe cutting loose a bit was tempting. So I said, that I would think about it.
So, we drive most of the morning, stop for gas once, stop for lunch and are back on the road when Shelley says to me:
"All right Judy. It's time to make a decision here. Do you want a free vacation and a little fun? Time to make up your mind. What's it going to be?"
So here it was. Was I going to be the settled mid-thirties woman or was I going to be a little bit out there? I was still pretty hesitant. Amber looks at me and then back to the road.
"Come on Judy! We promise that what happens stays with us. Think of the fun that you can have living out your fantasies."
So, being a little turned on by admitting to them what I fantasized about and listening to them gently push me, with the laughter at me when I admitted what I did fantasize about, well I decided, why not?
"OK, I'll do it, but what exactly do you mean by you tell me what to do?"
"Just that, Judy. You've told us some of your fantasies but there are probably more that you haven't admitted to having. So we pick one and you do it. It's that simple."
I thought about it. How bad could it be?
"OK. I'll do it. But if you guys get too wild, I reserve the right to say no."
"No way Judy, it's all or nothing. Have some guts, girl. You'll probably love every minute of it."
So that's how I ended up agreeing to do what they told me. So I was expecting them to immediately tell me but nothing. We drove down the road, heading Florida. And I was sitting in the front captain's chair kind of waiting for the other shoe to drop. Finally we come up to a rest area and Michelle tells Amber to pull in. She does and Michelle tells her to park down past the rest rooms so the side door is facing away from them. Amber pulls in maybe 75 feet past the rest rooms. All of them lean towards me and smile.
"Ok, Judy. Do you need to pee?
"No."
"I'd suggest you go and try. Because in a little bit you probably will need to."
So we all go the rest rooms and use them and I did have to pee. I was the first one done so I get back to the van and I am sitting in the front where I had been when the three of them walked up.
"No Judy, you are going to sit in the back."
So I was getting nervous and a little excited and got out and opened the side door to get in the van.
"No, Judy, just stand there for a minute." So I am standing like a dumb ass while they get in the van, Amber driving still, Michelle in the front and Shelley in the back. They all settle in and look at me. Shelley has this ear to ear grin on her face.
"OK, Judy, fantasy girl. Why don't you take off your clothes?"
My eyes must have almost popped out.
"I can't do that!"
"Ah, Judy, I'm sorry, but you agreed to this, didn't she girls? So, I guess you can take them off or we can take them off for you. Which do you prefer?"
I looked at Amber and Michelle and their grins were just as big as Shelley's. I looked around nervously and saw that although I was not in sight of any cars I was in plain sight of where the truckers parked.
"Judy, Judy, either get started or we will come out with you and do it for you."
Soooooo, I looked at the trucks parked to my right, closed my eyes and then I took off my top. I felt my face turn hot. I got my shoes off, cursing myself for not thinking and undid my jeans and pushed them down. I hurriedly pulled them off, turning them inside out to get them off faster. I reached behind my back and undid my bra, pulling it off and then pushed my panties down and off. Shelley had been taking each article of clothes from me. I started to get in the van.
"Uhuh, Judy, socks too."
So now I am leaning on the side of the van, pulling my socks off. Shelley takes them from me. I cover my boobs and crotch.
"No Judy, hands at your sides."
"For God's sake, let me in!"
"Turn around Judy."
Defeated, I turn around so they can see my bare ass. Then and only then does Shelley let me climb in the van. She shuts the door, smirking at me.
"There, that wasn't so bad, was it?"
I glared at her. They all started laughing. I was naked in a van, headed to Florida and I had just probably made the biggest bad decision of my life. Amber backed out of the parking spot and pulled back on the interstate. I was blushing and I was feeling, God damn it, I was feeling turned on! "Get your suitcase, Judy."
So I got up my knees and reached behind the bench seat to get my suitcase. When I pulled it over the seat, Shelley took it from me, opened it, folded up the clothes I had just taken off and put them inside it. Then she closed it and smirked at me.
"You can put it back now, Judy. Oh, and don't cross your legs, dear."
So, once again I am leaning over the bench seat, putting my suitcase with all my clothes in it in the back of the van.
"So, how are you feeling?"
"Embarrassed."
"Are you a little turned on, Judy?"
"Not exactly."
"Well, just give it some time."