Don & Lisa Ch. 02

Seventy Five! I think 75 is a milestone, don't you? Particularly when my final objective is only 100. I'm three quarters of the way there.

On the way to what, you ask? My 100th guy. I designed a stickpin just for the occasion. It's the symbols of the two sexes, interlocked and made out of platinum for, of course, 75. The center of it is a ruby for my red hair. I had two of them made. When I showed them to my husband Don he asked what I was planning on doing with them.

I told him my plans were to wear very sexy panties, and pin the first one right over my crotch, so that the guy would find it and I could explain the significance of that particular screw. Afterwards, I'd give him the other one, as a memento. Don thought I had it pretty well thought out.

For nearly a year, I've been looking for the perfect guy. He'd be tall, handsome, exciting, and suave. Those in are addition to my normal qualities of safe, clean, responsible, persistent and confidential. A man like this, of course, doesn't happen by every day. I've even let a couple of chances pass, waiting for just the right stud. (No big deal, those guys will be available, I think, for numbers 76 and 77.)

But things don't always go as planned, do they? Here's my quandary - Is the last guy my 75th? And, if so, what do I do with that jewelry? Let me tell you the whole story.

Doreen was a virgin. There is absolutely no doubt about that one. She was a virgin when we met as roommates that first day of college, and if she wasn't a virgin on her wedding day, it's only because she and Alan knew they'd be together, monogamously, for the rest of their lives.

Doreen was, and still is, my best friend. She knew all about me, particularly about how I wasn't a virgin. She found out that the hard way.

About six weeks after our freshman year started, I took a guy back to our dorm room. Of course it was illegal, and if I got caught, I'd get shipped back to Podunk. But I knew that if they sent back every girl who did it, the Senior Class would be all men. Except, of course, for Doreen.

So there I am, lying on my bunk with this guy. It's the middle of the afternoon, and I know we'll be okay because Doreen's got a math class. We've just finished a great screw, and he's laying on his side while I'm on my back, and I've got my hand down playing with his dick, hoping it'll come to life again. The door opens, and in walks Doreen. She looks at him, she looks at his thing, she looks at me, she looks at his thing again, gives a little shriek, and backs out of the room, closing the door behind her. Other than Alan, that may be the only real live cock she's ever seen.

Later on, we catch up with each other. She's a little peeved, not because she couldn't come into the room, but because she's worried I'm going to get pregnant. I explain the birds and bees and condoms and spermicides to her, and let her know that it can't happen. (It never did, either!) We make a pact - she won't judge me for what I am, and I won't try to force her into my lifestyle. I did promise her that I'd never take another guy into our dorm room again, and I kept that promise. Luckily, we only spent three semesters in there, and then we rented an apartment with separate bedrooms. After that, she just banged on the wall when we got too noisy.

Doreen was with me the night when I found out what I wanted to be when I grew up. A bunch of us were sitting around and a guy I was in the process of trying to gently dump figured out he wasn't welcome anymore, and called me a whore.

Vanessa looked at him, and in her best slave accent said, "Sheeeittt, that girl ain't no hoe. You have to have at least a hundred guys 'foe you a hoe. An' from what I seen, Tom-boy, you ain't worth no hundred, sweetcakes!"

We all laughed, but I took his crack personally. To get even with him, I went to another party where I knew his best friend was, pretended I was drunk, and got him to take me to their room. When we got there, I let him make out with me, and let him strip me down to my bra. I got his thing out, and gave him a handjob. My timing was perfect. Just as we were wiping it off Tom's sheets (I made sure we were on his bed!) Tom walks in and 'catches' us. Screaming and shouting ensue, I tell them they're both lousy lays, and I walk back to the party, laughing my ass off.

But the next day I start to feel a little guilty, and I get to thinking about what Tom and Vanessa said. Was I a whore? I was just starting to understand how much I like the varieties and vagaries of different men, and I decided that a objective of one-hundred men in my life was not only realistic, but would be one heck of a goal. I made up my mind right then and there that I would bag my limit.

That day, I started keeping a list of the different men I'd been with. It wasn't much of a chore then - it was just springtime in our freshman year, and Tom was only my fifth conquest. Since then, I've been very meticulous, and kept a detailed list of every guy I've been with, along with dates, ratings and degrees of kinkiness. Here's the summary:

High School - 2

College - 11 (I don't count Tom's roommate, I never fucked him.)

After college - 7

My first husband, Ray - 1

During my first marriage - 8

During my divorce - 35 (helped by a couple of very good orgies! )

[for more details, see the footnote at the end of the story]

My second husband, Don - 1

During my second marriage - 9

That's a total of 74 guys I've been with. I only count guys that come in one of my three holes, although I've never had a guy in the back door that didn't come in the front, too. I do count a couple of guys who only got a blowjob; that's almost as personal as being in my cunt, and both of them would have been invited to head on down below if they'd wanted to. Now the question is, does my latest guy count as my 75th, or am I still searching?

Oh, what's this about all the screwing during my marriages? Well, during the first one, I was young, and didn't have it figured out how jealous a man could be. Or maybe I just didn't care. It doesn't matter, either way it's my fault.

Doreen tried to warn me. She told me I wasn't ready for a wedding, even though she'd been married over a year, and was pregnant with her first daughter. She told me I wasn't stable enough, that I'd hurt Ray, and then, when I did go through with it, she told me to my face on my wedding day not to screw around.

Of course I didn't listen to her! In the two years Ray stuck around, I had round heels, as my record shows. And I wasn't very smart about it. When Ray found out, it was pretty much over. And then Doreen held my hands, and let me cry on her shoulder, and didn't even tell me she told me so.

Doreen was aware of my prodigious record between my marriages, and again, just tried to make sure I didn't get hurt. Which I didn't. At all. Then, when I found Don, and just stopped fooling around because I was happy with what I'd found, Doreen was ecstatic, and again stood as my bridesmaid. This time, she didn't give me a lecture, but she did tell me she didn't have to!

A few years later, Don began an affair, with my support and blessing. A few months later, I reciprocated with his assistance. Since then, we've had an open relationship. We both have affairs, and tell each other about them. For the last three years, we've even had another couple, Dave and Judy, who are sort of like our mutual fuck buddies. It's nice - I get to scratch my itch two or three times a year, and nobody gets hurt.

Both of us are very circumspect. We watch out who we have fun with, and try to make sure that no one gets hurt. So far, I don't think anyone has. And no one, I think, other than the people we have fun with, knows about our secret lives.

No one, that is, except Doreen.

After my first conquest broke up (he was a guy in our hometown who I was on a committee with,) I was looking around for someone else to do it with. Luckily, our college reunion was coming around. I go to it every year, as do about 60 or 70 others, including Doreen. Rich was a semi-regular, hitting it every few years.

I met Rich in college when I was dating one of his best friends during our junior year. I'd learned my lesson from Tom, and didn't take Rich to bed, even though both of us liked each other a lot. I figured I'd let the summer take its course, and then make a play for him in our senior year. But while he was doing an internship, Rich found himself a girl (who he eventually married,) and we never did get together.

Rich was still married, but when we got together, we always kidded each other and had a lot of fun. Once, during the years when I was being faithful to Don, we started to make out at the get-together, but I stopped it pretty quickly. It was clear, however, that if I ever had the inclination, Rich was willing to help me out.

So I called Rich up where he worked, and it didn't take him long to figure out why I was so interested in if he was going to go that year. We made plans to reach the campus a day before the official festivities began. (Yes, just to satisfy your prurient interests, Don didn't accompany me that year because he knew I was going to be otherwise occupied. Although I'm not absolutely positive, Rich's wife may have allowed him the same privilege.)

Late in the afternoon, I checked into the campus hotel, where all the alumni stay. The clerk said, "Oh, yes, Suite 209." When I took my luggage up there, a dozen roses awaited me, as well as a bottle of champagne on ice. The bedclothes were drawn down, and a beautifully wrapped package awaited me on the pillows. I opened it and found a midnight blue bra and panties set. Also enclosed were a dozen condoms and a note that read, "Slip these on, call me in room 211, and I'll slip one of these on. Love, Rich." Of course I realized that he was right next door, and so I took some time primping myself and getting myself into the getup. I banged around a bit, making sure that Rich knew I was in the room, and when I was ready, first I silently opened the interlocking door and then unwrapped a rubber. I called him, and when he answered, I told him to come on into my room. He came in, dressed in a matching pair of midnight blue french-cut briefs, and I let him chase me into the corner of the room. He grabbed for me, and I reached down, unleashed his tool, slid the condom onto it (he was as ready as I was,) and let him skewer me with my back to the wall. He had good control of himself and we bumped and grinded for three minutes or so. Three minutes is a long time in that position. Then we slid onto the couch and I climbed on top of him to finish both him and myself off. It was a great first fuck, spontaneous, quick and totally satisfying. When it's like that the first time, you can't wait for the second to find out if it'll still be as good.

We just sat there, sort of cuddling and sort of making out, and he stripped me of the lingerie. When we were both naked, Rich opened up the champagne and poured the wine directly out of the bottle into my mouth. When I began laughing and letting the beverage slip out of my mouth, Rich licked it up, and then began pouring it all over me, licking it up where it spilled. He had great tongue action, and after he got done with my nipples, he poured it lower and lower. Finally, he got to the good part, and I tilted myself up so that my pussy could hold quite a bit of the champagne without spilling it. He licked three or four helpings out, and then started on me proper. Rich knew just where my prominent button was, and what to do with it, and, like the good mistress I am, I came properly for him.

Then, of course, it was my turn. I got a glass, filled it, dunked his limp penis into it and licked it off. It wasn't long before it wouldn't go into the thin crystal (Rich turned out to be thicker than average,) and so I started sucking in earnest. Before he could come, he got me to sit back on the couch, fitted another rubber on, knelt between my legs and entered me again. It was even better than the first time, because Rich could really control his movements in that position. He pumped in, out and around inside of me, varying the rhythm and tempo until I was in full spend. Then he turned me over and did me from the rear, making me even more frantic. Finally, I couldn't stand it any longer, stripped the rubber off of him, and went down on him. I've been told by many guys, including Don, that I give the best blowjobs in town. In fact, in many towns. When Rich started moaning and pumping into my mouth, I knew I had another satisfied customer.

The rest of the night is sort of a blur, because of the champagne and all the sex. I seem to remember room service, and then finally we slept.

We sort of woke up mutually, sometime around eight. Rich went into the shower, and I just laid there, luxuriating in the feeling of being well fucked, and knew I wanted some more. I put on a green negligee I'd brought, hoping to get Rich ready again, and the phone rang, and it was Doreen. She was going to get in later that afternoon, and just wanted to check with me about a few details. We were chatting about our plans, when Rich came out of the bathroom, toweling off his hair, and yelled, "Lisa, you are one great lay!" When he looked at me and saw that I was on the phone, he ducked back into the bathroom.

Doreen stuttered a couple of times, finished the conversation quickly, and then told me she'd see me later. The idea that I'd been caught sort of excited me, and I was able to get Rich all sweaty again.

It didn't take long for Doreen to get me aside that evening. After a few false starts, she asked, point-blank, if I was having an affair. I admitted it, and then, before she could start in on me, I told her about my arrangement with Don. She plainly didn't believe it, and was clearly pissed with me for the rest of the reunion. Rich wasn't, though. He met me in my room every evening and to this day, we get together every once in awhile.

Doreen stayed upset with me until Don took her aside and talked to her, and let her know it was okay. Once she heard it from him, she turned into her old self. Later, she told me she doesn't understand the life I choose to live, but like always, she refuses to judge me. She just wants to make sure that I don't get hurt. Don's included in that, too. I don't tell her about every conquest I've made, like I used to in college, but she's been aware of a few of them. She's a pal. She'd do anything for me, and I know I'll do anything for her.

Alan and Don get along pretty good, too. Just before their last son graduated from high school, Alan bought a sailboat on a lake a couple of hours north of us, and asked Don if he'd help 'break it in.' They stayed up there the whole weekend going around in circles. I knew Don was as hooked as Alan was when he suggested we buy a boat, too. I got him to climb off that one by appealing to logic; if we were off on a boat in the middle of the water, how could we be golfing? Don realized the futility of trying to have too many playthings, and for the next couple of years he and Alan took day trips up to the lake, and sometimes Doreen and I had to go with them.

Before last summer rolled around, Alan started pushing a sailing trip around the Virgin Islands. Don thought it was a good idea, too, and Doreen seemed to be supportive. I wasn't sure about it. A week out on the water with nothing more to do than read and drink doesn't appeal to me that much; I'm more of a big city type. But I was outvoted, so one Friday night I'm aboard a flight to St. Thomas. The guys planned the whole thing - they got the charter, and 'laid in' all kinds of supplies, mostly liquor, so that all we had to do was sail from place to place and anchor in pristine bays off deserted islands. I'd done some research of my own, and discovered that the wardrobe de riguer for such a voyage is topless. And that's only if you get cold. But I was going with Doreen and Alan, so I packed as many one-piece suits as bikinis, and brought along a bunch of cover-ups.

The first couple of days went along pretty much as expected. Sail in the wild tropical winds from about ten o'clock in the morning until about three, then find someplace to anchor without another boat in sight. In the morning and then in the evening we'd all jump in for swim and play time. Maybe some volleyball or keep away or something like that. A little roughhousing went on, bodies crashing into bodies, but I never felt uncomfortable with it, and Doreen didn't seem to mind the incidental brushes.

On the third day there was almost no breeze at all, and the sea was as flat as a tabletop. While the guys were trying to figure out how to get the boat to go somewhere, anywhere, Doreen and I thought about what we would make for dinner, and the four of us came to the same conclusion - head for port! We turned the motor on and set course for the nearest village. When we finally got there, it was late afternoon, and we got off the boat in the metropolis, glad to be back in 'civilization.' There were only two establishments in the place that catered to tourists, and we hit both of them. First we had a long dinner of fresh vegetables and fish, and then we went over to the nightclub. It was long after dark when we arrived, and the place was, if not jumping, at least lively. A reggae band was playing loudly, and perhaps fifty people, mostly tourists but some natives, were imbibing and dancing. We gladly joined them in both of their pursuits, and until well after two in the morning we got wild and crazy.

Mostly, Alan danced with Doreen and Don pranced with me, but occasionally we would switch off. This wasn't odd; Alan and I often danced with each other at weddings or parties at our Club. After awhile, Doreen decided she wanted to get some air, but Alan wanted to have another Planter's Punch. I sent Don out to look after our friend; even if we were in the tropics, it was still a strange area, and women should be escorted. After they left, Alan and I started dancing again, and then they shifted to a couple of slow dances. Alan grabbed me, and we drifted around the dance floor. Soon, I was aware that he was pressing himself to me much closer than he'd ever done before, and he stole a little kiss. I let him, thinking it was just the romance of the setting, but when I felt his hand wandering toward my ass, I sat down! Half an hour later, we were back on board, bedded down on our proper side of the curtain.

The next day was much better. The breeze kicked up, we sailed along, and everyone was in much better spirits. As usual, we anchored in the late afternoon, and took a swim. When we frolicked, even though Alan and I made contact as usual, it didn't seem like any big deal.

After we climbed back on the boat, Doreen and I began to sun. The guys folded sails or something, and Doreen turned to me and said, "You know, to hell with this. There they are, with just their loose trunks on, and here we are, with these tight things on." She was wearing a bikini with some underwiring in the bra. "I'm going to do something about this!" And she whipped her top off! A few moments later, Don looked over and nearly twisted his neck. He didn't know whether to stare at her in amazement, or to ignore the whole thing. Alan caught his act, glanced at her, and said, "Hey, you're finally going to get comfortable, huh?"

Now I'm not a nudist, but I've never seen the use of clothes just for the sake of covering up something that doesn't really need it. (Fashion? But that's another subject, dear.) So I went below, took the one-piece off, and put just bottoms on. When I went back on deck, I could tell that Alan was trying not to gawk, but the longer we let it go on, the less uncomfortable the situation became. The night ended up with both of us girls eating dinner and cleaning up without changing our costume. Later, Don and I went to bed, and heard the sounds of the other couple making love up on the deck, so we did it too.