Bugging Tiffany

Last summer, I was put in charge of investigating a local lawyer. We had heard through snitches that he was trying to bribe witnesses in a civil case that he had pending against a large insurance company. We got the clearance for a wiretap on his phone, and we also had him under partial surveillance.

I was working the wiretap one morning when his wife, Tiffany, got a call from her friend, Victoria. I knew I was supposed to stop listening, to stop the tape when the call turned personal, but I was never one to follow rules too slavishly. And I did want to get to know the guy’s wife a little better. She was a sexy brunette with sparkling green eyes and a body that, frankly, I found perfect.

She also had this sexy accent that I just couldn’t place, but enjoyed nevertheless. The main reason I kept listening, however, was the topic of conversation: the woman's annual trip to the doctor.

The transcript of the call:

Tiffany: "Hi Vic, I knew you'd call today."

Victoria: "Yeah, so tell me, how did your appointment go?"

Tiff: "You bad girl! You know a woman’s trip to her doctor is private."

Vic: "You know you're just dying to tell me. I still can‘t believe you go back to that guy, year after year."

Tiff: "He's a good doctor.... H-he's just...."

Vic: "A little perverted."

Tiff: "Shut up! Ok, maybe a little, but he's never touched me longer than he's supposed to."

Vic: "I know, but do his female patients really have to be nude for the entire exam?"

Tiff: "I think he’s just a little old fashioned. I guess that's how they did it back in his day. And he's kind of cute, for an old dude."

Vic: "You and your old man fetish."

Tiff: "Shut up! At least the doctor still notices me."

Vic: "Things still bad at home, huh?"

Tiff: "Yeah, give him his golf and his bourbon and he's a happy camper."

Vic: "You’re not thinking of cheating, are yah, Tiff?"

Tiff: "No, not really...,I just need to feel alive again.... I’m like starting to do stuff."

Vic: "Stuff...? Tell me."

Tiff: "Yeah, silly stuff, like dressing up really sexy and walking the mall, before school gets out."

Vic: "You’re such a little tease."

Tiff: "I know it’s wrong, but it’s innocent and kind of a cheap thrill, just turning heads."

Vic: "And with that body, I’m sure you sprained many an old dude's neck!"

Tiff: "Whatever! A couple of days ago I even wore my smallest bikini and went rollerblading around the neighborhood. Then, leaving my license at home, I went for a drive on the highway, really fast."

Vic: "ARE YOU CRAZY?"

Tiff: "What? I wore my seatbelt."

Vic: "No, not that. You know what they would've done to you if they'd pulled you over."

Tiff: "I know, it was silly, but all’s I got was a warning."

Vic: "A warning? Who pulled you over, a state trooper?"

Tiff: "Yeah, funny, he was really nice. I guess I talked my way out of it."

Vic: "And the bikini didn't hurt either, but you were still lucky, you know...."

Tiff: "I know, I know. It was stupid. I cringe thinking about what might have happened to me, had he brought me in to their station."

Vic: "You know EXACTLY what would have happened."

Tiff: "I know, I still remember what Mrs. Palmer told us about her search. I just wondered what it must feel like to have no choice, but to have to do what you're told."

Vic: "It sounds scary! But will you get back to the doctor, so I can get the picture of Mrs. Palmer, naked, out of my head, please?"

Tiff: (giggling) "Ok, ok."

Vic: "What did you finally decide on wearing?"

Tiff: "Now, who’s the bad girl?"

Vic: (giggles)

Tiff: "Well, I went with the business suit look. You know, sexy, but sophisticated."

Vic: "Was it that nice light blue one?"

Tiff: "No, it was black, and stop interrupting me. I will tell yah in full detail what happened, ‘cause I know that you get your kicks out of it."

Vic: "You know I do. I’ve been married for 20 years now, so If you hear a buzzing sound in the background...."

Tiff: "Oh brother! (giggling) Is that what I have to look forward to? Anyways, like I said, it was a black one to match my high heels. I went with a simple white bra and panties set underneath and some white mesh thigh high stockings."

Vic: "Blouse?"

Tiff: "Nah...it would have been just one more thing to take off."

Vic: "Lets go, get to the good stuff."

Tiff: "Alright, alright, so I get to his office, and I’m kind of nervous. Not so much from the nudity part, but you know, just nervous at what he might find."

Vic: "You’re as healthy as a horse!"

Tiff: "Geez Thanks. But you never know. Plus he didn’t do a rectal exam last time, so I knew...."

Vic: "Owww.... This is the year!"

Tiff: "Yeah, that was in my head too. I could already see myself on my hands and knees, on his exam table, naked as a jaybird, hearing him snap on that glove."

Vic: "God!"

Tiff: "I know, so I’m sitting in his office, flipping through a mag, when his old nurse comes over, and she sits down next to me. It was weird."

Vic: "What'd she say?"

Tiff: "Well, she tells me that Doctor Adams had a car accident, and he’d be laid up for a little while, nothing major, and that they had another doctor covering his patients. She also asked if I wanted to leave and reschedule."

Vic: "You left, right? I mean they should have called you."

Tiff: "I was going to. I wasn’t happy, but he came out front a couple of seconds later, talking with a kind of heavy woman. And then he looked at me."

Vic: "What he do, faint?"

"Tiff: "Shut up! No, he just looked real nervous as he came over. We talked, and I found out that this was his very first day on his own. I don’t know who was more nervous, me or him, as we walked into the exam-room."

Vic: "You stayed?"

Tiff: "Yeah, he told me a lot of patients had cancelled on him. I kind of felt bad for him, and he was sort of puppy dog cute."

Vic: "'Puppy dog cute'?"

Tiff: "Yeah, it wasn’t like he was that attractive looking. He wore these thick glasses that seemed to always slide down his nose, and his hair was really messy. But his skin was clear, and he smelled good. It was just the way he seemed so shy and uneasy. It was...cute."

Vic: "So...."

Tiff: "Well, he left me with the nurse, who did her stuff. I’m starting to get nervous, but she said everything was fine. She took some blood and then went out to get the doc."

Vic: "Where you naked?"

Tiff: "Not yet, you ninny! That’s saved for the doctor, of course."

Vic: "But she’s still there, too?"

Tiff: "Yeah, she gets to watch, too. I kept thinking, why couldn’t the little blonde nurse be working today! Whoever came up with that rule, anyways? Did they think it was easier on us that way? Like I wanted to be naked in front of that old hag, too!"

Vic: (giggles)

Tiff: So, anyways, they both come back in, and now I’m really nervous. It feels like I’m 18 again. It also feels like the first time I went to Doctor Adams, like what, I’m thirty two, so some twelve years ago. But I know he’s nervous too, and I don't want to be catty, but I did see his last patient, and I certainly knew...."

Vic: "That you had a better body."

Tiff: "Well, yeah. That doesn't make me stuck up, you know. I didn't mean it like that."

Vic: "I know."

Tiff: "I also wondered how many naked women he’d seen. I mean this was his first day on his own. Although he did say that he'd assisted Doctor Adams for a couple of weeks, before the accident, so I knew he’d seen some. But anyways, the first thing he does is apologize."

Vic: "Apologize?"

Tiff: Yeah, for everything, and then he says he still has to follow Doctor Adams’s rules, ‘causes it’s his office. I knew what he meant. It was kind of sweet, actually. He sat on his stool and took some time to look over my medical records. He assured me that everything was fine so far, and then he asked me if I was ready to begin."

Vic: "Here it comes."

Tiff: "Yep, that’s what I was thinking. He stands and picks up a tongue depressor, and it’s time to say ahhh.... I know it’s weird, but I always think about what the doctor must be thinking, as he checks my mouth with that thing.... Anyways, he checks my eyes and ears next. He feels around my throat for a couple of seconds, and then he picks up that thingy that he sticks in his ears."

Vic: "Stethoscope."

Tiff: "Yeah, that thingy, but I knew what that also meant."

Vic: "Time to get naked!"

Tiff: "Yeah, he told me to take off my outerwear. I stood up and took off my jacket and skirt and hung them up on the clothes tree. When I turned around I was a little surprised that he told me to take a seat, ‘cause Doctor Adams usually has me naked by now. This one starts on my back with his scope and then goes around front. He’s also not watching my chest rise and fall, as I breath in and out, like I'm used to. He lets me know that everything sounds fine, so someone taught him well. He puts his 'scope back on the tray. I take a deep breath, this time without instruction, ‘cause...."

Vic: "It’s breast exam time."

Tiff: "Yep.... Again, I don't know who was more nervous. He even seemed to have trouble saying 'bra.' I think he even called it a 'thing.' Well, I handed my 'thing' to the nurse, who hung it with my other clothes, while I covered my breasts with my hands. And then, with her on one side, and the young doc on the other, he guides my right hand off my breast and behind my head and I let my left hand fall. My breasts are all his now. His hand didn’t go right for my breast, though. Instead he started under my arm, slowly working his way there. Finally, he starts pushing down on my right breast. His hands are much softer than Doctor Adams's are, but he's kind of shaky, too. He took his time...."

Vic: "You have a lot to examine."

Tiff: "They ain't that big."

Vic: "Really now, you're a D cup easy."

Tiff: "36C! Thank you very much."

Vic: "Uh huh."

Tiff: "Anyways, he asked me several times if I was okay, as he examined the other one."

Vic: "Were yah?"

Tiff: "Yeah, and he said everything was fine, thank God! But he still checked my breasts again, this time while I was on my back. One thing he did do now that startled me was check my nipples."

Vic: "Your nipples?"

Tiff: Yeah. Girl, was I embarrassed."

Vic: "They were hard, weren't they?"

Tiff: "Y-Yeah, yours get hard too, you know!"

Vic "Yeah, but they're not as long -- or as pink -- as yours are."

Tiff: "I know, all the women in my family have them, but sometimes I wish I didn't. And this was one of them times. I also wish I never showered with you at the gym. Anyways, I didn’t want him to think I was a pervert or something. It was just kind of cold in the room, and his hands were soft and whatever. I mean he was rolling them with his finger and thumb. I even let out a soft moan."

Vic: (giggles)

Tiff: "I couldn’t help it! Anyways, after he checks the other nipple, I had gotten through the breast exam for another year."

Vic: "What he do next, Tiff?"

Tiff: "Well, he surprised me by telling me to get up and walk back and forth a couple of times. He said it was to check my posture or something."

Vic: "Wait! Did you still have your heels on?"

Tiff: "Yeah, and just my panties and thigh high stockings. It felt strange."

Vic: "And don’t forget your erect nipples. He must have loved that!"

Tiff: "Maybe...but he was professional. Although, he was wearing a large white lab coat. So I don’t know, he could have been sportin' a woody."

Vic: (giggling) You’re so bad."

Tiff: "Oh, and then he checks my spine. I had to bend over and touch my toes...a couple of times...at least I had my panties on."

Vic: "Tell me you weren’t wearing a thong?"

Tiff: "Well, yeah. I only wear thongs, you know that."

Vic: "I also would kill for an ass like yours."

Tiff: "Owww...You’re such a sweet talker. So, I go to sit down, and the doctor clears his throat. The old nurse taps me on the shoulder and gives me that 'Well, while you're up' look."

Vic: "She wanted your panties, huh?"

Tiff: "Yeah, I think the doctor was too nervous to ask. I even had to slip them off right in front of her. I was back to being nervous, ‘cause, while I was doing this, the doctor had snapped out the stirrups."

Vic: "I hate them things."

Tiff: "Me too! And will you stop interrupting me! Ah, now where was I? Oh, he raised the back of the seat, too, before I sat down. I just sat there, almost afraid to move. He finally helped guide me into position. Left leg up and then the right, then slowly apart, before he sits down on his stool and swings the light over. Like it’s not bright enough in there. I never know what to do with my hands, so I just folded them over my stomach. I mean he’s seen and felt my breasts, anyways. Plus his eyes are focused elsewhere.

"Before he starts, he asks me if I want him to explain what he’s doing, or do I want him to just do it. I think for a sec, and settle for just doing it and getting me out the hell out of there. I mean, it’s not my first time, and being naked is one thing, but having things put into you, well, that’s another.

"He starts by rubbing some lubricant onto my pussy. I’m kind of thankful, because now at least I had an excuse why it was so shiny. Yet, I am a little embarrassed 'cause I'm waxed down there. I wondered if the heavy woman was? Anyways, he starts moving my pussy lips around with his fingers, doing an external exam. Wow, do I wish they weren't so prominent! He spreads them apart with his fingers, and I groan as I see that the lubrication keeps them there. I see him lubricate a finger, and I brace myself, ‘cause I know where that finger is going.

"He sticks it in me, quickly. I gasp. He apologizes, quickly taking it out. I see that his face is flushed. At least I wasn’t the only one, I thought. I took a deep breath and told him that I was ready now.

"This time he slides his finger in very slowly. I bite my lips. Was it more than one finger, or did he just have fat fingers? I wondered, as I had to do everything I could to suppress a moan. His other hand was pressing down on my stomach. At least he was working quickly, but still...."

"He grabbed a tool off the tray. I didn’t know what it was, but it looked like a shoe horn. He lubed it up and put it inside of me. He used it to pull me open. I guess he was doing an internal exam now. Maybe I should have asked! Doctor Adams usually just uses his fingers.

"With my p-pussy pulled open, he ran his fingers along my lips. My body shuddered when he hit my clit. He apologized again, but said he had to examine that, too. I had to grind my teeth as he pulled back on the hood. I closed my eyes tight, only after I got a glimpse of it. I didn’t want to cum in his face. If he had rubbed my clit one more time, I think I would have, but then he took the tool out of me. Like he knew!"

"I cringed when he picked up the speculum. At least he gave me a couple of minutes to relax. I could smell my arousal. I knew from where he was sitting he definitely could, too. The old nurse flashed me a 'here-it-comes' look when she caught my eye. The young doctor was a little uneasy with the speculum, but he finally got it into place and opened it with a snap. After a quick look with a penlight, he took his samples and thankfully took the cruel device out. I took a deep breath, figuring the exam was over, but I forgot...."

Vic: (almost inaudible) "Rectal exam."

Tiff: "Uh huh. I climbed into the humiliating position. He apologized yet again, as he snapped on a rubber glove. Why do they always have to snap it on? With me in the doggie position, my heels dangling off the end of the table, I felt his hand on my ass. My body quivered as I felt my ass cheeks pulled aside. Of course, he told me to relax. What a joke! He was about stick his finger up my asshole.

"It was so strangely exciting, but also humiliating. I mean, here is this young guy I just met like twenty minutes ago, and now, just because he’s a doctor, he’s fingering my ass. Something I wouldn’t even dream of letting my husband do!

"A sudden jolt shoots through my body when I feel something bigger than a finger being pushed into my asshole. I snapped my head around. I saw the rectal thermometer, half in my asshole, half in his hand, and I sighed, because for one quick second I thought.... I mean, I should have known it wasn‘t.... Maybe I should have taken the explaining option after all. But why this way? Even Doctor Adams never took my temperature this way. I was too embarrassed to ask.

"The worst part of the whole thing might have been the clean up. The doctor took out the thermometer, and then the nurse helped me flip over onto my back. She was kind of rough, as she wiped in between my legs, with a damp cloth, never once asking for permission, before she brought my knees to my chest and wiped my asshole too. All while the young doctor watched. At least they left me alone to dress. Thankful that my yearly exam was finally over.

"After I dressed, I was walking out of the exam room and down the hall, when the nurse passed by with a pretty blonde teenaged girl. She was probably here for her first exam, judging from what the nurse was saying to her and by her petrified expression. I wondered if she knew just what was in store for her?"

Vic: "Or if she’d like it as much as you did!"

Tiff: "Did not."

Vic: "Did too."

Tiff: "Did not."

Vic. "Did too."

This is when Tiffany hung up on her friend, and I stopped the tape.

For the next two weeks I listened in on her conversations. I knew that a bored housewife was not a new phenomenon, but I really felt for this one. Her husband had a real jewel here, and he treated her miserably. It seems that they hadn’t had sex in months, and she was getting desperate. Her search for adventure was starting to go from silly to dangerous.

She had seemingly spent much of her time alone, watching TV and movies. She was talking to Victoria one night about a movie where a beautiful woman wondered into this run-down bar. She didn’t have any money. The manager offered her all the drinks she wanted for a dance. She found herself up on the bar dancing, as a crowd of men gathered round. What she didn’t know was that she would have to take it all off before they would let her down. In the movie, she ended up driving off into the sunset with some hunk. Tiffany gushed about how exciting it was to watch her strip, while Victoria just called her crazy.

It was like she was starting to cross the line between fantasy and reality. One night I followed her to this biker bar. She was by herself, dressed in next to nothing. I kept an eye on her just to make sure she was safe. She didn‘t stay long, as I think she knew she was in over her head with these guys. This wasn’t a movie. I had a feeling that, if she kept this up, something really bad was going to happen to her. Working undercover, it should have been none of my business. But after weeks of snooping, I was beginning to think of her as, well, someone I ought to be protecting.

I continued to listen in, even after we had officially called off the investigation, due to a lack of evidence. I was now on my own. She talked to Victoria every day. And one day it was different. I knew something was wrong; she was pissed. It seems she found out that a large sum of money was missing from their savings. And when she confronted her husband, he admitted to using the money for bribes. I banged my fist on the table -- we finally had the bastard. There are few things I love more than busting a crooked lawyer.

Yet, the more I thought about it, the more I hesitated. Once I'd calmed down, I knew I really had pretty much nothing. Since the investigation had been canceled, the tap was no longer legal. It was hearsay anyway, and she couldn't testify because of spousal privilege -- so it was inadmissible. (At least it would have been on "Law and Order.") It could maybe get the bastard disbarred, maybe, but it was sure to hurt Tiffany. She would be the innocent victim in a huge scandal. But I was the only one who had heard her conversation, and I had the only copy of the tape. So I had some thinking to do.