A Phone Call to Judy Ch. 01

Judy and I went to work at our small company at about the same time. She as administrative assistant to the CEO and me as a marketing rep. We were about the same age—early twenties when we first started, but didn't work too closely together being in different branches of the company. Judy started out as administrative assistant in the executive offices, while I went on the road as a marketing rep.

Over the years, we both rose through the ranks. Judy finished her college degree and eventually became director of human resources, and I was promoted to vice president for marketing, after making my mark as one of our most productive reps.

During these ten years, Judy and I had an easy relationship. I thought she was really smart and funny. She had a wonderful and wicked sense of humor, and she told people exactly what she thought, whether they wanted to hear it or not. This made her a bit of a polarizing figure, but I was on the side that liked and enjoyed her.

Besides, she was very cute. She was about my height, around 5-3, but with a softer, more rounded figure. My breasts were a nice size, 34-C, especially when contrasted against my slender frame. But Judy was much curvier, with full-round hips and breasts that usually strained against the smart outfits she wore to work.

Her hair was dark brown like mine, and she often wore it curly as I did. But occasionally, she would let it grow into a long mane and let it fall in waves against her shoulders, giving her a decidedly sexy look. But the thing you noticed first, or at least right after her easy laugh, were her eyes. They were a remarkably clear blue and looked quite striking framed with her mane of dark brown hair.

Judy and I didn't "hang out" together, having lunches or anything like that. I was usually on the road and she was making her mark in administration. But we did have fairly frequent interaction on business matters, and we would often take the opportunity to gossip about what was going on in the company, talk a little about our own lives, and exchange a few off color jokes.

I could tell that Judy had "been around" quite a bit more than I had, and she didn't mind dropping a few comments to let you know it. She was one of those people who made her sexuality "available" more than most. She didn't seem at all embarrassed to talk about it if the occasion arose. And I found myself trying to think of ways to talk and joke about it more and more when we got together. There was something about Judy and her past experiences that fascinated me.

"Proper" women in the company were a bit put off by her bluntness and ability to curse like a sailor. And they certainly didn't like her sexual references. But I did. Perhaps it was because I saw her as the "bad girl" that I knew I had hiding inside me somewhere but had never let out.

Men, of course, liked Judy. She was cute and sexy and enjoyed teasing with them, even while talking behind their backs about what simpletons they were to let you lead them around by their cocks. My husband liked her, too, of course, calling her "eminently fuckable."

I knew I could always get my husband David in the mood by telling him my latest "Judy story." He loved it when I'd relate something she told me about her past, and I could almost see his cock spring to life at the mention of her name.

A few times, when we were making love, I would whisper to him about Judy, telling him how sexy all the guys thought she was; telling him how cute she thought he was; and asking what he'd like to do to her. When we played this game, I could feel his cock swell inside me with every word. I knew he was imagining that he was fucking Judy at that moment, even though he had his cock buried deep inside me.

But what David probably didn't know was that I was imagining it, too. I could picture the two of them together, rolling around bed, locked in each other's arms. My husband's eight inches buried to the hilt in her wet sex and Judy moaning and shouting at him.

"Fuck me you bastard," she would pant. "Shove that big cock in my cunt! I'm gonna cum all over you!" I just knew that's how Judy must be when she was really turned on.

And then, she'd roll David onto his back and begin to ride him, sliding her slick pussy up and down his thick shaft, her luscious round tits bouncing, her body coated with sweat from the exertion. I'd close my eyes tight, the way hers were in my fantasy, and grind myself as hard as possible onto David's cock until we both exploded into an amazing orgasm.

I didn't cry out as Judy did, it just wasn't how I acted, even during sex. But in my mind, I was screaming the words right along with Judy.

****

But despite my fantasies, as far as I knew, Judy never played around on her husband, at least not with anyone in the company. The gossip certainly would have made the rounds and I'd have known about it.

Over the ten years we worked together, there were a few times when we went to the same conferences or meetings out of town, although never just the two of us. There were other coworkers always along, too. But I looked forward to these trips and always made it a point to spend as much time with Judy as I could outside the meetings. She was just a hell of a lot of fun, and you never quite knew what might happen.

On one of these trips, she told me about Mr. Big. Judy and I and another of our coworkers were having a few drinks after the conference had ended for the day. We had been in the lobby bar for a couple of hours and were feeling no pain.

The other woman with us, Jane, was much closer to Judy than I, and it was obvious that they had exchanged a lot more stories over the years. Finally, Jane mentioned something about Mr. Big and the name of course caught my attention.

I asked for an explanation. Jane looked at Judy smiling, waiting for her to tell the story, and with very little prodding she began.

"Well, he was this guy I dated my last year in college. He was on the wrestling team. Wrestled at heavyweight, must have weighed 260 or so. But he wasn't fat at all. He was about 6-5 and really cut."

"Thus the name, Mr. Big," I chimed in.

Jane was just grinning at the two of us as Judy went on with her story. "Well, not exactly," Judy corrected me. "I called him Mr. Big because he had the biggest cock I'd ever seen!"

She and Jane burst out laughing as my eyes widened a bit and I moved a little closer to Judy so she wouldn't have to talk so loud. Not that I thought she would quiet down much, especially after several drinks. But I was hoping not to create a scene there in the lobby bar of our very swanky hotel.

"Not only that," Judy continued, "but it's still the biggest cock I've ever seen even after all these years. And, god knows, I've seen more than my fair share."

"Don't waste our time telling us something we already know," Jane teased, as Judy stuck her tongue out at her.

"We actually measured the thing one night when we were playing around," she went on, "and it was a little over ten inches long. But the thing that I really loved about it was that it was six inches around. It was like wrapping your fingers around one of those cardboard cylinders in a roll of paper towel. Only it was so warm and . . . alive. I loved to feel it throb in my hand." Her voice trailed off and she closed her eyes for just a second.

"Come on," I chided, "you have to be exaggerating. The only guys hung like that are in pornos."

"Oh, really," Judy shot back with a big grin. "And how would you know about that Miss Goodie Two Shoes?"

I could feel my face turn crimson, partly because she had called me on my sexual naiveté and partly because I'd tacitly admitted that I'd watched pornos. Actually, David and I enjoyed them every now and then as one form of foreplay. But I didn't make a habit of advertising it.

Jane was enjoying our little back and forth, but she wanted Judy to get on with her story. "All right, you two, that's enough. Judy, quit screwing around and get to the good part."

"I thought screwing was the good part," Judy deadpanned. But then she went on with her story.

"So one night we were at my apartment, fooling around in the bedroom. Mr. Big was lying back on the bed, we were both naked, and I was pumping that big ole cock of his up and down with both hands." She put one fist on top of the other and lifted them up and down a couple of times just to make sure we got the picture.

"Finally, I could feel him beginning to swell, so I started using just one hand so I could jack it off as fast as I could. Then all of a sudden, that big purple head of his swelled up and he shot a load of cum sort of above and behind us. It splattered against the wall at least four feet above my headboard."

My mouth and eyes were both open by this time, and Jane just sat there smiling and nodding her head in approval. "My god, Judy, I've never seen a guy shoot it that far," I marveled.

"Oh, wait," Jane interrupted, "that's not the best part. Go ahead, Judy. Tell her the rest."

"Well, there wasn't much more that night," Judy said. "It's just that I decided to leave it there."

"On the wall?" I asked incredulously.

"Yeah and . . ."

"Where everyone could see it?" I still couldn't believe it.

"Sure, that was the point," Judy laughed. "What good is it to set some kind of record for sperm slinging if no one knows about it? I left it up for the rest of the semester. It was a great conversation starter. Besides, it gave other guys something to aspire to!"

Well, Judy never ceased to amaze me. But the story of Mr. Big was one for the books. I was both fascinated and turned on, and I filed it away in the back of my mind for future reference.

I also went back to my hotel room that night and masturbated while I played the scene over and over in my mind. I knew Judy had given us the shorthand version of the story, probably because servicing that huge cock with her mouth might not have fit her image of always having the upper hand on guys.

But I just knew that she had taken Mr. Big in her mouth, licked that big purple head with her tongue and made him all slick before she started using her hand to bring him home. I saw it all as I lay there in the hotel and fingered myself to a very satisfying orgasm.

****

I thought about Judy and Mr. Big from time to time over the next couple of years. The image provided a great masturbation fantasy, and I even replayed the scene in my mind occasionally when David and I were making love. But unlike other "Judy stories," I didn't tell David about Mr. Big. I don't know exactly why, because I'm confident he would have loved it. But there was just something about that one I wanted to keep all to myself.

Then came one of our annual planning retreats. It was a time when almost the entire company would shut down for a couple of days and go away to assess where we were for the current year and develop objectives for the next. The actual work sessions were usually pretty boring, but I enjoyed the retreats because they allowed for a lot of socializing in the evening, and with people that I didn't get to see in an informal setting very often. Judy, for example.

This particular year, the retreat was to be held in a small lodge about 75 miles away from our headquarters. It was out in the middle of nowhere, a picturesque little place nestled in the rolling hills of western Oklahoma. Everyone would certainly stay right there during the one night we stayed over, because there was simply nowhere else to go for any night life. Our company rented the entire lodge for two days, so we had the place all to ourselves.

About 70 of us attended the retreat. After the first day's meetings and a mandatory dinner, people began to drift to one part of the lodge or another for the evening. Some went straight to their rooms, others gathered in little groups to share stories and, believe it or not, some even talked about the next day's meetings.

But a good number of us, probably 25 or so, congregated in this recreation room that featured a bar, juke box, ping pong table, pool table and television. The group included Judy and me.

While some decided to get competitive at the various games that were available, probably 15 of us gathered around the bar and began mixing drinks from the liquor we had brought for the occasion. We had been warned in advance that the lodge didn't provide liquor for its guests, so several of us brought our own. And it was, shall we say, an eclectic assortment, everything from Jack Daniels to some god awful thing called Hot Damn.

But those of us gathered around the bar did our dead level best to make sure that none of it had to be toted home the next day. Of course, as the bottles were emptied one by one, the conversation got looser and bolder, until there was a lot of kidding about all things sexual. Not surprisingly, Judy was right in the middle of it all, giving just as good as she got. I, on the other hand, sort of sat back, got mellow and just took it all in.

Finally, we got around to sort of a PG-rated version of truth or dare. Most of us in the group were married, so we didn't dare get too risqué. Nonetheless, soon came the dare for Judy to flash us all. And wouldn't you know, she refused to back down and calmly raised her sweatshirt and showed us her tits.

Now, don't get me wrong, it was not a Mardi Gras flash. She was wearing a bra underneath. But we all still got a good look at her pretty lace bra and some wonderful cleavage. Not to mention the soft, milky skin that covered her belly.

I don't know if it was the flash per se, or the fact that the liquor was almost gone. But for whatever reason, our group began to break up soon after. I think most of us realized, at least subconsciously, that there was nowhere else we could go with our game without the potential for some major trouble. So people began to head back to their rooms.

However, there was a small group of us girls, Judy and I included, who were not quite ready to call it an evening. So we accepted an invitation from one to join her in her room to watch a little TV before bedtime.

It wasn't long before six of us were sprawled out on the two beds in the room, shoes off while our hostess began to flip through the channels to see what was on. As luck would have it, she came across a show on HBO called Real Sex, which is sort of an R-rated news magazine with stories about all kinds of sexual things. Of course, when we saw what it was, everyone yelled "stop," and we proceeded to watch.

I can still remember vividly how quiet the room got as six women, away from their husbands for the night and each in various states of drunkenness, watched the sexual images that flashed across that screen. Yes, at first there were some hoots and whistles during the segment about the male strippers with unusually large cocks. But as the segment went on, the only sound was some pretty heavy breathing.

And it truly was a sexy segment, showing those strippers performing for an enthusiastic group of women who were grabbing them, stroking them, rubbing their tits all over them, all while these amazing cocks swung lewdly as the guys danced.

As the show ended, everyone seemed a little unsure about what to say or do next. Did anyone dare speak about what we were obviously all feeling—this tremendous sense of arousal? The answer, as it turned out, was no. One of the girls mumbled something about needing to call her husband before it got too late, and that comment broke the spell.

We all said our goodnights and drifted back to our various rooms. I expected there would be some serious masturbation going on.

I went back to my room, extremely aroused by all that had gone on during the evening. Besides, I was still slightly drunk. I normally sleep in an oversized tee shirt and panties, but that night I quickly shed my clothes, went to the bathroom, then slid naked between the cool sheets.

My head had barely hit the pillow before I began running my hands over my breasts, letting my mind drift back over the night's events, especially the image of Judy flashing us. That glimpse of her body was sexy, all right. But it was her willingness to do it that really got to me. Her daring—that "bad girl" daring-- made me tingle all over. I knew right then that I was truly attracted to a woman sexually for the first time.

So on impulse, I reached over and picked up the phone from my bedside table and dialed Judy's room. She answered on the first ring, leading me to believe that she was in bed, too, and very close to the phone. Her voice sounded a little sleepy, even though neither of us had been in our rooms long enough to have dropped off.

I tried to make a little small talk about the day, but quickly came around to mentioning the show we had all watched just a few moments before. And I knew exactly where I wanted the conversation to go. I wanted to get Judy thinking . . . and talking . . . about her Mr. Big.

I wanted to hear the story again from her. But this time, I didn't want to hear her tell it in the kidding way she had done with Jane and me. I wanted her to focus on the sexuality of the experience. I wanted to know how it made her feel. I already knew how it made me feel.

So I tried a leading comment. "That one guy tonight must have reminded you of Mr. Big." I tried to keep a light tone in my voice, even though I was very serious, just in case she wasn't in the mood to talk about it. But, fortunately, she was in the mood to talk, or at least to answer my questions.

"Mmmmmmm. Yeah, he did," she responded, her voice sort of husky.

"That guy really got to you, didn't he? You still think about him after all these years."

"Um, yes. Sometimes."

As she answered my questions, I propped the phone against my ear and began to caress my breasts again. "I can't believe you left that 'trophy' on your wall all that time."

Giggling, "Well, it seemed like a good idea at the time."

I wanted her to volunteer more information, but it was clear that she wasn't going to. So I decided to see how long she'd answer my questions.

I began to ask her for details about him. How he looked. How he felt. What they did other times they were together. What it was about this guy that made her remember him so vividly after 15 years. And she answered all my questions.

As she told me details about Mr. Big, I allowed my hands to roam over my body. I pinched my nipples, ran my fingernails lightly over my belly, before finally sliding two fingers just inside my wet slit, dipping into the nectar that had been flowing ever since Judy flashed us earlier that evening. I used it to lubricate my clit, which by now was simply begging to be touched. I made slow circles, up, over, down and around, over and over, trying to match the rhythm of Judy's words on the other end of the line.

I was almost certain that Judy was doing the same thing as we talked. I could hear her breathing grow faster, movements on her bed. I'm sure she could hear the same thing on her end of the phone.

"What did he feel like, Judy?" My voice was barely above a whisper by this time.

"Oh my god, Sarah," she sighed. "It was like I was impaled . . . ummm . . . on this huge pole. The only way I could take it . . . mmmmm . . . was with me on top. I'd just slide down as far as I could . . . ohhh . . . and ride up and down real slow."

By this time I had buried three fingers inside me, trying to feel the fullness that Judy was describing, while the fingers of my other hand moved furiously over my clit. I was close and I knew my breathing must surely be giving me away. But I didn't care. I wanted to hear Judy's voice in my ear when I came.

"Then what?" I hissed through clenched teeth.

"He'd grab my tits . . . hard . . . ohhhh . . . and by then I'd just be bouncing up and down . . . mmmmm . . . on that big cock."