The Mole                    by: Alyssa Davis & Caitlin Rose

 

Police work is a paramilitary occupation. Uniforms, rank, weapons, discipline…It can be exciting and interesting for some and boring for others. Some officers seem to find lots of action during their career (or maybe it finds them) while others never use their sidearm except for target practice and hardly do much more than help children cross streets. This seems to describe my position. I have become completely unimpressed with my job and hardly felt cut out for this line of work. I’m a very peaceable person.

My name is Tim delGado. I’ve been in public safety for seven years…too long…and feel locked in since this is the only job I’ve had since finishing college. And I now question my career selection. Trouble is, I am good at this job. I am good with people, and I excelled in the department’s expectations such as marksmanship, physical endurance, police tactics, and many others. On the record, I am considered a good cop with potential. So why do I feel I want to give it all up?

It was the beginning of my next shift, this time working days. I had just finished the graveyard shift and was coming off a three day rest. I was in the squad room changing into my uniform, followed by the routine inspection of my personal equipment. My badge, name tag, service pin, a utility belt loaded with all the required police paraphernalia…baton, handcuffs, keys, pepper spray, flashlight, rubber glove case, radio clip, spare magazine case, and sidearm. Nine pounds of junk around my waist. All in order…Well, it helped keep me slender hauling it around everyday. But it did little to enhance my arms or shoulder muscles.

I had safety checked my 9mm automatic for proper operation and was loading a full ammo clip into it when I heard my name being called on the paging system.

"Tim delGado…Officer Timothy delGado…please report to Captain Tom Cook’s office."

Captain Cook was the officer in charge of the Patrol Division’s day watch. My first day shift and already I’m being paged. I wondered what he wanted.

I knocked twice, and entered the captain’s office to observe two men sitting there chatting like old friends. They halted their conversation and shifted their attention to me.

Upon greeting the Captain, I was introduced to Captain Bruce Person of the Criminal Division. There followed the usual round of handshakes, wisecracks, and male cordiality after which we settled down to business. Already I sensed an air of intrigue. Why was Captain Person here…and why did they want to see me?

"Tim, Bruce has requested your assignment, on a temporary basis, to his division for a special detail. It may last several months. It’s strictly voluntary on your part, so you aren’t being pressured into the transfer. But it might be a good opportunity for you to cross train in another area. Are you interested?" asked the Captain.

Sure I was interested. Interested in anything that was a change from this boring, dead-ended street patrol duty. Many times, I wondered why I ever chose police work as a career. High risk, low pay, unappreciated work…dealing with the public in less than favorable situations. Sometimes being spat upon. Very few times being complimented. Well, lets see what they have in mind.

"May I ask for more specifics of what the detail entails, sir?" I responded.

Lt. Person replied, "Confidentially, it’s a sting we’re setting up to shut down a major fencing operation. Their whole thing is rather unusual so it calls for unusual methods. I can’t go into more detail at this time unless and until you accept and are reassigned. But, after reviewing the entire department personnel files, we really think you’re the best man for this."

"And may I add, Tim, that this would look very good for you in your file and could lead to a commendation and promotion," the Captain interjected to further enhance the offer.

I had been in the department long enough to know that you don’t do well by declining such requests, voluntary or otherwise. Whatever it entails had to be better than mundane street patrol duty, but I wished I knew more about what I was being asked to accept , and my Captain was of little help here, too. I was entering a fog bank and flying blind. Oh well…

"Okay, sir…I accept the assignment and I’ll give it my best," I responded to Lt. Person. Well, I had to say something, and judging from the looks I was getting, this is the response they expected to hear.

Handshakes finalized the offer and arrangements for the transfer were started.

I proceeded back to my routine duties and finished an uneventful day. I had a feeling the boredom was to end.

The following day, Lt. Person and I met for a briefing of the new assignment in a very secure office in the street crimes and narcotics section of the Criminal Division. We quickly dispensed with formalities of rank and titles so it was just Bruce and Tim thereafter, a liberty not usually allowed during working hours according to department policy but this was a special operations group and they were allowed a wide latitude. After a commitment of total confidentially, Bruce began the briefing.

"Tim, what we’re going to do is shut down a large upscale fencing operation dealing in stolen art objects. We know where it is occurring and what they’re doing, but we don’t know is exactly how and by whom. We need to put someone on the inside, a Mole. What’s unique here is that they’re running it from a nightclub. We need someone to work there."

"So why don’t you use a female officer to work as a barmaid or waitress? She could cozy up to everyone and become privy to all kinds of information. Sounds simple." That was my contribution to solve all their problems. Like I was an instant expert without any background information.

"Ah well, you see, it’s not your typical club. Actually, it’s a gay and transgender bar. *Straight* females aren’t exactly favored there. So it’s not that simple."

I saw it coming and interrupted, "Hey Bruce! Wait a minute…I’m not gay nor transgendered. Why was I selected for this assignment?"

"Oh, I’m not saying you are, but that wouldn’t matter anyway.

You’re an experienced police officer. You’re young and unattached so there’s no wife or significant other to distract you, you’re not very tall, yet you are very slender and well proportioned, and forgive me, but you don’t appear overly *macho* so we feel you’d make a plausible and attractive transvestite, one who wouldn’t appear out of place in such an establishment.

Bottom line, you fit the profile of what we’re looking for. Working there, you’d be able to glean lots of information as would any waitress in a more traditional establishment as you mentioned earlier. Even a female officer posing as a lesbian wouldn’t get the reaction we need. You see, it seems that the owner of this place has a thing for transvestites…pretty ones. We want to attract who we think is the leader of the operation and we’re reasonably sure he’s the owner. Now, unless you know of any genuine transvestites in the department, someone we may have missed, we’re asking you to perform the task."

At age 28, I’m only 5’8" tall, I keep trim and am slender at 137 lb., my hair is jet black, straight, and very long. It’s worn in a bun as regulations permit, which these days of EEO rules, is allowable for minorities. I’m of Hispanic heritage and have always have long hair. It is my culture, my parents said. And I’ve been told by many that my facial features and hands appear soft and almost feminine. That comes from my mother’s side, I guess. Often, my effeminate features are an asset to help defuse a situation. I don’t give the illusion of a macho hard-ass looking to kick butt. For that same reason, female cops have an advantage. At times, I’ve even been mistaken for a lady cop.

Honey is always more effective than vinegar in catching flies, my Grandma said.

I learned that Bruce had searched the entire department’s files for a suitable candidate and he felt I was the best choice to pose as an attractive transvestite, one who could function in the position they hoped would extract the information they sought yet be able to take care of himself in case of problems. It only remained to convince me to attempt the gender bending role.

"But why must I appear as a woman? Why couldn’t I just portray a gay man working as a waiter?" I was still trying to evade what I felt was a socially revolting task, dressing as a woman. Somehow, it violated everything in my upbringing.

"Because they will have an opening to hire a bar waitress, and we know they will specifically look to hire a very pretty transvestite for the position. We’re already working on it. And believe me, you’d be much safer as a woman there rather than a gay guy. Trust me on this. Most of their clientele aren’t attracted to women."

All I could say was, "WOW!" as I shook my head in futility.

Now I wondered what I’d volunteered for.

"So I’m to become a woman and work the lounge in a gay and lesbian bar, right?"

Bruce nodded. "And transgender. There will likely be other crossdressers there as well. No…Appearing as a guy wearing women’s clothes and ENJOYING it. You don’t need to be a totally passable woman, in fact, we don’t want you to be too good. You’re just a guy who enjoys crossdressing. The owner prefers that kind…guys in drag…Shemales"

"And exactly how do I accomplish this bit of magic? I’ve never done anything even close to this before. How do I start?"

"Not a problem, Tim…remember, you don’t have to be a perfect female impersonator. You’re still a guy, but a guy in a dress, a cross dresser. They accept cross dressers there. Your goal is to convincingly enjoy yourself in that persona, get to know people, and get them to take you into their confidence…That’s where the police work comes in. Work it like you need money to support your expensive *hobby* of cross dressing and are looking for some easy cash. Do whatever it takes to win them over. Hopefully they’ll draw you into their operation. Somehow, they’re buying and selling stolen property, specifically art work That we know. We must find their sources of goods and their buyers. I’m sure we can manage to get you employed there. Still interested?"

Yeah interested…that was a rhetorical question. I knew I had little choice, now.

"Well, when do I get started?" I said, sounding dejected.

Bruce picked up the phone on his desk and called someone, speaking in hushed tones. Almost immediately, a gorgeous, young lady burst into the room. She appeared to be a college girl of about 20 years of age, perhaps an intern working over the summer. Petite in stature, perky in nature, wearing jeans and T-shirt, straight, long blond hair, shapely well developed figure. Eyes like pools of blue that I could swim in. I noticed all this with a trained eye and was instantly attracted to her. Attracted? I was in love!

"Debbie Blake, This is Tim delGado. Tim, she’s on our street crimes team. Deb’s been assigned as your partner and will help you and work with you on your transformation," Bruce said, introducing us.

Debbie smiled at me and I started to melt. I was floored! This *child* was a cop!

"As you can see, we’re a bit unorthodox here. Debbie is dressed to fit in with the younger crowd. Makes things much easier to blend in instead of wearing an intimidating uniform. And, by the way, she’s older than she looks," Bruce added with a smile and wink. Was my thinking that obvious?

"Hi Tim…what division are you from?" she asked in a perky voice.

"Hello Debbie…nice to meet you. I’ve been assigned here from the patrol division for temporary duty," I said after I recovered.

"Well, I already know the details of your new duty, so we might as well get started. Yes, I think he’ll do just fine!" she commented to Bruce, as she looked me over from head to toe. I felt as though she was undressing me with her eyes!

Bruce explained that they have budgeted for the necessary female attire and accessories to accomplish the "disguise." It remained for Debbie and me to go shopping, which we did for the remainder of the day. With her direction, we purchased a basic wardrobe and cosmetics while having a very enjoyable time in the process. The shopping spree gave us the opportunity to get better acquainted since we would be working together as a team. Deb was to be my official "girlfriend" as well as my mentor in the coming charade. She tried to make light of everything to help relieve my tension of being transformed into a woman.

We were to have three days to rehearse my female role before I was to apply for the bar waitress position which I learned had been created by some nefarious police work. During that time, Deb proposed that I spend the time fully crossdressed and practice some skills in feminine demeanor and application of cosmetics. She reasoned that most crossdressers have been doing so for a long time and many have gotten very well accomplished. I was to portray a very experienced transvestite to convince the club owner to hire me.

We set up a dressing room in my apartment. My first "official" act was to take a hot, soaking bubble bath, remove any extraneous body hair, and relax to get into the "mood" before my transition begins. While doing that, Debbie arranged my daily wardrobe for the three days, and created a makeup station in my bedroom.

I actually had very little body hair to shave off…mainly my underarms arms and legs. The luxuriating soak in the delightfully fragrant bath did it’s intended purpose and I emerged feeling relaxed and smelling as effeminate as ever due to the perfumed bath oils…Lavender, I think it was. Especially after covering my skin with an after-bath lotion, applied with Deb’s delightful assist. I stepped into a panty girdle, arranging and tucking myself in for concealment, followed by a half slip she had previously readied for me. Trying to be cool, as much as possible in this attire, I shyly walked out of the bathroom into my bedroom where she was waiting. I didn’t dare let my mind wander at this point. I kept reminding myself to remain professional. Over and over again. My thoughts turned to police tactics, city ordinances ...anything to prevent getting aroused in the presence of this beautiful young lady while I’m wearing nothing but lace trimmed, female’s undies. I was more than a little embarrassed, I was totally uncomfortable with the process but not with the garments.

Saying nothing to further my embarrassment, Deb proceeded to wipe my hairless chest with alcohol soaked pads in preparation for the next step. She pressed a pair of very real looking silicon breast forms into their respective positions over my nipples. They conformed to my chest perfectly. She held them there for several minutes until their adhesive set. Of course, at that time, I didn’t know they had adhesive on them on nor how long they were to remain and she remained silent as she went about the business of my transformation. She then placed a 36C brassiere around me, hooked the back, and adjusted the straps. I hesitated to look down at this newly acquired form in more fear of arousal. But they did feel strangely very nice. There was a noticeable weight pulling on my chest and a fluid motion as I moved and they jiggled. And the bra was actually comfortable. It made me feel more "dressed."

Deb had me sit at a small table which she had improvised into a makeup station and began the process of metamorphosis from male to female. She plucked and trimmed my eyebrows to thin and arch them, she worked a foundation cream into my facial skin followed by various colored compounds explaining her technique as she progressed. I watched in fascination, refraining from stealing a kiss as she placed her face in close proximity to mine while detailing. I didn’t want to break her concentration, but I sure wanted to taste her lovely lips.

Beard concealer, eye shadow, eyeliner, blush, lip liner, and finally a bright red lip color to fill, completed the operation.

The last items were earrings. She pierced my ears with a needle and ice cube and installed a pair of gold rings, one in each ear. This I didn’t mind since I’d often thought of wearing an earring but that was against regulations.

When finished, admittedly, I was strikingly…well… beautiful! All her effort with the cosmetics had enhanced my facial features…like colorizing a monochrome photograph to bring it to life! I couldn’t believe what I was seeing…what she had done to me. Amazing!

She brushed out my long hair to it’s fullness. I had forgotten how much hair I actually had! She parted it in the center to clear my face and clipped it back over my ears. All very casual yet feminine. No more tight bun.

Debbie had me finish dressing with a pair of tan thigh-high hose under a form fitting, medium length green knit dress which she assisted me in zipping up in the back. My shoes were inch and a half high wide-heeled pumps. She added a necklace and stood back to admire her work.

"Tammy, you are stunning!" Deb exclaimed.

"Thank you, Deb…So now its Tammy, huh?"

"Well you’re certainly no longer a Tim! Look at you! What do you think?"

"Hmmm…It’s different!" I understated as I viewed myself from different angles in a full length door mirror. Yes, I guess I was indeed attractive! Definitely dating material, I figured. This was an entirely new experience for me and not altogether a bad one, I was thinking. Never having dressed like this before, I was focusing on the tactile sensations of all these new garments while trying to get familiar with movement in the confines of a dress and slip and bra. Yes, different was the best description. But different in a nice way. I knew I had some slightly feminine features, but they had never been exploited to this extreme. I was getting aroused at my image!

"You know, a person could get used to this," I half whispered as I continued to admire myself.

"Okay, so now you must constantly remain in this mode for the next few days. I’ll coach you as much as possible. This will be a crash coarse in femininity," Deb added. "You’ve got to give the illusion that you’ve done this many times and enjoy it very much. That’s what they’re looking for."

"But only as much as a transvestite needs to know, remember. I’m not going for a sex change."

"Oh sure, but you must remember, tv’s enjoy what they’re doing. They derive great pleasure in presenting as women. So you gotta start to enjoy this. And I mean, openly. So far, you’ve been very reserved. Like it’s an obligation."

"Well, you know, it is an obligation! This isn’t my choice of lifestyle. It’s only a job, even if it is rather interesting.

So now tell me, Deb, what’s your impression in seeing a guy like this? You’ve been quiet too."

"Since you asked, frankly, some guys look absolutely pathetic in drag…they’re a parody of women and a disgrace. But in your case, I must say, you are extremely passable and very pretty as a woman. No, I’m not offended, in fact, I’m flattered that you look so good and are actually willing to do this."

"So, does this make me less of a man to you?"

"Oh, so that’s what you’re worried about? Well, I obviously don’t see a man here now. But remember, I do know what’s under that dress. Manly? no….sexy? You bet!

Looking beyond all this, I see you as a gentle person, and a darn good sport. Even if you really enjoy this, I see a man in tune with his feminine side. That makes him a better person in my mind. Is that what you wanted to know?"

I was relieved with that disclosure and indicated as much. I may resemble a female at this point, but I still have my male ego, and it is fragile. And I wanted to be attractive to Deb as much as that would be possible in this role. I want her to like me more than just in a professional way.

Debbie and I began the training session in womanly mannerisms which continued into the evening, breaking only for a Pizza dinner, which was delivered. She taught me to sit in a skirt, stand, walk, all under various conditions. She coached me in speech…patterns, vocabulary, gestures, and eye movements while talking, female body language, all very subtle, avoiding showing too much exaggeration like a theatrical drag queen. All the while, she had me practice feminine vocal intonations…trying to cram a lifetime of a girl’s training into a few short days…an impossible feat. We worked till it grew late and we were fatigued. She then left for the night. That night, at her insistence, I slept in a frilly nightgown which subsequently became my regular sleep wear of choice. Normally I slept in my underwear anyway, but I obviously never knew how comfortable a ladies nightgown was.

The next day, Deb returned to again instruct me in re-application of makeup, this time allowing me do it. She helped me dress, and casually drilled me in what I’d learned. Being a quick study, I was now even more motivated by a new found pleasure of this strangely different wardrobe and Deb’s revelation that I was still sexy, but in a special way. I had also discovered that my new breasts were not removable without a special solvent which I didn’t have. Deb informed me that they would stay attached for at least a month, when they needed to be removed with solvent for cleaning and fresh adhesive. So I was destined to remain appearing as a woman full time for a while since I couldn’t easily conceal C cup breasts. She showed me how to blend in the edges with cosmetics to make them invisible in the event of my wearing revealing tops or even open collars. With that technique, you couldn’t tell they were fake.

Day two, I was wearing a long full skirt and knit top which exaggerated my newly acquired bosom. I had to constantly adjust to these new appendages which I quickly grew very fond of. I always had been a breast man and now they were on me! But these kept getting in my way, another learning experience. Whatever I did, I seemed to brush against them which was a constant reminder of their presence…delightful! They felt so wonderfully real!

Deb took the dominant male position in role playing. I had to learn to handle myself in a bar-lounge environment. I had been in bars, but never as a woman. I never had to confront aggressive or unruly men while in a short skirt and mesh pantyhose. I had never been a sex object!

The training went well. We broke for dinner and actually went out in public to a restaurant to help develop my confidence. Deb even forced me to order my own meal. Scary at first, but I noticed nobody seemed to care about this lady with the low pitched voice. Of course, I was speaking softly and smiling a lot with lots of eye contact. Deb complimented me on my feminine mannerisms. I was trying hard.

Day three, I wore a short skirt and a blouse with a low, revealing neckline and a lace trimmed bra which showed. Again, the playacting centered around the gay bar scenario. Deb did whatever she could to tease and harass me as a drunken patron might do. She also tried to portray a "hands -all-over" manager. I did well to thwart the advances in a non-hostile manner, but I also really enjoyed the physical interaction with Debbie with whom I had become deeply attracted. We engaged in a lot of horseplay and I stole more than a few kisses which forced me to refresh my lipstick frequently. By this short time, I had adjusted to applying and wearing makeup and rather enjoyed the appearance of it on me.

It was a real challenge to maneuver in the short skirt yet maintain feminine modesty but I quickly learned. By the end of this last session, I was exhausted and Deb was convinced I’d do well in my new identity. She contacted Bruce and was given the okay to proceed with the plan for me to seek employment. Deb was to be the liaison for Bruce and I and cover me in case of trouble. I would be unable to carry a weapon, for obvious reasons, but she was armed. She was to pose as my "roommate and best friend. But while I was at work, I was on my own."

I was still very apprehensive about this whole matter, but then, I was only pretending to be a transvestite, not a real woman. So why worry? I figured I might as well enjoy the experience.

I entered the sleazy looking lounge, oddly named "The 19^th Hole," and asked to see the manager. These places all appear dank and sleazy in the daylight, smelling of stale beer, I noticed. It’s like opening a dark basement.

A man approached me and I introduced myself, speaking in a slightly effeminate but unmistakably male voice, as a "special girl" in need of a job. I was to find out he was Jerry Johnson, the owner-manager. He escorted me to his office.

I wore a form fitting but short green knit dress, dark hose, and three inch heels. My makeup was perfect and I had dangling earrings under my black hair. I knew I looked sexy. That was the intent. I sat with my skirt hitched up a bit, showing lots of leg and a bit of lace slip.

He paused, looked me over, literally undressing me with his eyes. Then, with an impressed and pleased expression on his face, he offered me a job application. Of course, he read me immediately as I had intended that he would.

Jerry was a tall, handsome guy, attractive to any lady, but from my briefings, I knew he preferred males…perhaps shemales. I know I appeared as a small person compared to him, almost petite, but very attractive as a woman, and he was obviously taken with me immediately.

"Just a formality," he said, handing me the paperwork. "I doubt if much of the information you’ll give me will be truthful. Do you have any experience?"

"Very little, but I learn fast." I winked seductively.

"As it so happens, we do have an opening for a server in the piano lounge and I think you’ll do nicely, pretty lady. When can you start?" His eyes said it all as he practically drooled over this vision of femininity. It was working!

"Thank you sir. I can start immediately. I live this way full time, and I need full time employment. This is a very expensive lifestyle for a *gender bender*...very high maintenance."

"Excellent," Jerry replied. "We can use you right away to start training, and you can work flexible time and get extra hours doing other things besides serving drinks. Seems our other girl had a brush with the law…traffic tickets or something… and left suddenly so we’re short a server."

So that’s how they knew this place was hiring. I completed the application form, we settled the salary arrangements, and Jerry proceeded to show me around the establishment, with introductions to the day staff. I was pleasant to all, being careful not to ask many questions. I overheard one person comment to Jerry that they had assumed he wanted to hire a transvestite for the job, not a real female to which Jerry laughed. He could hardly contain his excitement.

My first day, before business hours, I was shown how to serve drinks and keep orders straight, how to handle the money and make change without getting confused, how to keep track of the tables. All this in a semi-darkened lounge! Also, I was advised how to handle unruly patrons. I was reminded that being somewhat permissive would impact my tips favorably. (All the things Debbie had mentioned. Made me wonder how she knew so much!)

I awaited the regular bar opening with mixed emotions. I had the feeling that this was going to be a very long assignment. Especially wearing the short skirted, low-cut V-neck uniform, fishnet pantyhose, and high heels they provided to the servers. That, itself, would be a major adjustment.

Time passed quickly and I was learning the tricks of the trade. Both as a lounge waitress and as a woman! Debbie was there for me to dump on after hours. We chatted like two women as I debriefed her of the daily activities. And at the end of each shift, I was beat! But she kept up the encouragement and positive reinforcement.

We were now roommates and were sharing a bed. Without her, I don’t know what I would’ve done. With this total immersion of full time living as a woman, it was all becoming second nature to me to dress, "do" my hair, apply makeup, and conduct myself as a lady. It was like I always had been a woman…and it got to where I actually didn’t mind it at all, except for the daily very close shaving and beard cover application. I quickly learned that it’s a lot of work to be beautiful. I had always taken it for granted when seeing pretty girls.

After the fourth week, some lounge "lizards" were getting to know me and taking some liberties. Jerry was at my side a lot, perhaps a bit too much, being protective. At first as a concerned advisor, but later he was just being friendly, in fact he was obviously attracted to me. It was my duty to encourage him, to be friendly to him, and I was doing exactly that. He seemed to be a genuinely nice guy.

Time passed quickly and I was learning the tricks of the trade. Both as a lounge waitress and as a woman! Debbie was there for me to dump on after hours. We chatted like two women as I debriefed her of the daily activities. And at the end of each shift, I was beat!

One Thursday night, actually very early Friday morning, I got back to the apartment so tired and disgusted, that I was ready to go back to Bruce and chuck the whole assignment. I was considering resigning from the force if necessary. Deb was waiting up for me, reading in bed.

"Deb, it was horrible tonight."

"What happened?"

"There were four new guys in the club. I never saw them before. What a bunch of assholes. I think they were important to Jerry’s operation, but what sleaze!"

"Gave you a hard time, huh?"

"Yeah, it was like they were love starved puppies. You could almost see them drooling."

"Hey, that sounds like fun. Weren’t you flattered?"

"Deb, I know this sounds like a cliché, but I felt like a piece of meat."

"Come here sweetheart, sit next to me and let me tell you some of the secrets of womanhood."

I joined Deb on the bed. She began to massage my back, between the shoulder blades.

"Oh, that feels fantastic."

"You have to learn what it really means when guys look at you that way. It means that you are powerful."

"Powerful?"

"Sure, those jerks were ready to grovel at your feet. True, they didn’t care about your feelings, and that sucks. But they were under your power. You were the goddess. Let me show you to use it, how to control the power."

Deb got up and walked across the room. Her hips swung seductively. Even in her loose robe, she looked incredibly sexy. I could feel myself responding.

"That was the ‘high voltage’ walk. Now watch this."

Deb repeated the walk. This time she actually looked like a no-nonsense lady cop.

"Now you try it. Try it in three stages, cold, medium and hot.

I walked the room, trying to keep it "cold"

"That’s pretty good. Now try it on ‘medium.’ Think shy, demure, girl. Like walking to Mass."

I walked the length of the room again. I tried to imitate, even to feel like, a teenage girl on her best behavior.

"Oh, that was perfect. Ok, now turn up the heat."

I gave it my best shot.

"Wow, sexeee. Ooo, do that again, you’re getting me excited, and I usually go for guys!"

I strutted by once more. Deb grabbed me and pulled me back onto the bed.

"The next lesson will cover smiles and winks, but first…"

We spent an incredible hour, and then fell asleep in each other’s arms.

 

By the end of eight weeks, which seemed like eight months, Jerry asked me out to dinner…a date! Of course, I accepted. Debbie assisted me in dressing for the occasion. We were like two young girls getting ready for a date.

Something sexy, almost trashy, destined to turn Jerry on. A knee length full skirt over a lacy slip, thigh-high, lace topped hose, sheer panties with no girdle, a silk see-through blouse and a lacy bra. I wanted to give him easy access in case his hands started to wander. After all, it was what he desired. We did my makeup to perfection with a double coat of lipstick with a powder coat in between for permanence. We brushed and fluffed my hair to enhance it’s body. The final touch was a pair of dangling earrings. Deb gave me her approval at my ploy to seduce Jerry. All was fine but it made me wonder how I was to react alone with him. How far do I go? How far did I want to go?

Jerry arrived at our apartment, and after introductions to Deb, escorted me to his car, being the perfect gentleman. All the little courtesies women are shown were rather nice. I was very careful to maintain my ladylike mannerisms even though they had already become very natural to me. Off to a good start.

We had an enjoyable dinner and friendly conversation. Just get-acquainted small talk and lot’s of flirting. No need to conceal my true gender. Jerry knew I was a male under all this finery but he found that especially exotic and was very complimentary of my feminine presentation. I had to make up a story of my history of crossdressing…when I started, how it came about, and how much I enjoyed it. Well, I’ll admit, the last part wasn’t fiction. He asked many questions and I made up many lies from what I had been briefed about crossdressers.

I refrained from asking him anything detailed yet. Had to play it cool.

Jerry invited me back to his place for drinks. He lived in a very nice, upscale apartment. Expensively furnished, but obviously a bachelor pad. Everything in chrome, earth tones, and lots of leather. Certainly not a lady’s touch in decorating. Odd that I would think that.

While he poured drinks, I used his bathroom to freshen my makeup. Strange, I really felt the need to do that. Feminine vanity…me?

I checked my appearance…lips, eye shadow, blush, overall skin tone…all in order, I joined him on the huge, leather sofa where I gracefully sat down next to him while demurely crossing my legs, arranged my skirt, and kicked off my shoes. He leaned over, held me firmly and impulsively planted a passionate kiss on my lips. I had to submit to that. In fact, I returned his kiss to keep the momentum going.

It wasn’t like kissing Deb. It was inexplicably different. He had taken the initiative and I had submitted as expected. And that factor felt rather nice. Feeling like a woman, I didn’t mind the kiss as I thought I might. Kissed by a man? Tim would have been disgusted but Tim wasn’t here.

His hands gently roamed my body and slid inside my blouse cupping my breast outside the bra…I was enjoying this as much as he was.

"Oh…very nice…are they real?" he asked as he kneaded the lifelike plastic forms filling the nylon bra.

"Um…no….but I wish they were," I replied, softly.

"Be careful what you wish for, my dear lady," he whispered into my ear.

I let him fondle them for a while as our kissing continued. Why not….I felt nothing from the prosthetics but I liked the attention and I knew what it was doing to him. His next move was under my skirt where he went for my crotch as if he was investigating. I relaxed my legs and allowed him his pleasure. His fingers roamed up my nylons, past the lace covered tops supporting them and encased my genitals. He could feel my now erect male organ through the flimsy panties knowing it was for him. That really turned him on. His hand was soft and warm, his gentleness felt so nice. He began to moan a little as he stroked me to an even larger erection, all the while our lips remained engaged. I was having a problem remaining objective. After all, I was here to do a job…I was on a mission to gain this man’s confidence so I was duty bound to do what it takes, and yet I was enjoying this homosexual encounter! But was it homosexual? After all, am I not a woman now? 28 years of male socialization, everything I was taught and believed in was discarded in an instant and now, I suddenly felt like a genuine female about to have sex with a man and, in the heat of passion, I had no misgivings about it. He was bringing out the woman in me.

To reciprocate, I deftly unzipped his slacks and reached for his massive organ and massaged him as he was doing to me. This was all new to me, yet not unpleasant. I had never touched another man’s genitals. But then, I had never felt so feminine before, either.

His hand, fully inside my panties now, and wet from my fluid, was stroking me gently while kissing my neck and chest, complimenting me on my beauty and how feminine I was. The words were a real turn-on for me. I actually enjoyed hearing those things. He whispered for me to finish him. Somehow, the idea of it appealed to me…Tammy… his woman. He was very handsome, very gentle, and I suddenly felt the desire to satisfy him…orally? Not yet, though it did occur to me. I would masturbate him for now.

What I was doing felt good. My objective was to satisfy my man. MY MAN! That sounded so strange yet not so distasteful anymore.

And he was groaning in pleasure along with me as his body undulated with my strokes. I had been ordered to do whatever it took to accomplish my mission, and that’s what I was doing. Just following orders, and enjoying doing so. Caught up in the moment, I suppose.

In the relatively short time I had transitioned to living as a woman, I had become permanently transformed psychologically. It all had become so natural for me. Could I ever go back to being a guy? Would I? I’m not so sure.

My gentle, pleasurable rubbing of his hot shaft continued until his body stiffened and he shot his seed into my hand in multiple spurts.

I carefully cleansed him with a tissue and acted grateful for the pleasure of satisfying him. We kissed again, a long, wet, emotional kiss, after which he slowly went down on me, lifting my skirt and slip and took me fully into his mouth and repaid the pleasure! With him on his knees in front of me, I placed my shapely, nylon clad legs on his shoulders and let him rub his face on the smooth, silky, lace tops of my hose. I had had the foresight to dab some perfume on my legs. This seemed to further enhance his desire. This is exactly what he desired.

I withheld my orgasm as long as I could but watching his head joyfully bobbing between my legs, hearing him suck and moan his pleasure, savoring every second, and the tactile sensation of what he was doing to me, I finally had to let go, with Jerry devouring all my love juice. My fantasies were of me being a real woman and him ravishing my clit, and how much we both enjoyed it. It was sheer heaven! Oh, at this moment, I truly enjoyed being the woman I had become!

We recovered and sat silently in each other’s embrace. Nothing needed to be said…we enjoyed the afterglow of our lovemaking.

I took my time repairing my makeup, viewing myself in a different light now, seeing the image of a genuine woman in the mirror. I did feel differently now. Jerry took me home where I found Debbie waiting up for me. She wanted all the details of our date. I didn’t want to tell her everything, but she sensed something different about me.

"Tammy….somehow you seem more feminine. I sense a change in you. You have a glow! Oh girl! Did you do IT?"

"What do you mean?"

"Did you have sex with him?"

"Well sort of…I didn’t do much to him, but he sure took me! I’m sure he’s bisexual."

I was ashamed to disclose all the details…my thoughts… so I was very evasive. I couldn’t make eye contact with Deb.

"You DID! Way to go, girl! Now you’re a real woman!"

"Oh Debbie…I don’t know what came over me! I’ve never touched a man before nor have I been touched like that!" I was almost in tears.

"Tammy, honey…this doesn’t change a thing between us. You just experienced the feeling of a woman with her man. All this feminine training and grooming has affected you. Relax and enjoy it. It’s wonderful!"

I finally did explain to her what we had done and not done, lest she get the wrong impression. But I kept my fantasies to myself.

We embraced, kissed, and went to bed, snuggling together beneath the blankets. I now felt different about everything as my thoughts reflected on what happened… and the future. I couldn’t see myself as a "normal" man anymore or even much of a man at all. If Jerry was considered bisexual, then what was I?

Two weeks passed when Jerry called me to his office as I arrived for work. He closed the door, deep kissed me, and fondled a bit. Again I responded warmly, this time with more feeling as we tongue wrestled while I touched him on his growing member. I knew this is what he wanted and it gave me power over him. We pulled apart and sat down as he began to discuss business before he lost control of his desires.. Ah, the power a woman has over a man.

"Tammy, I want you to be my administrative assistant. I don’t want to share you with the patrons. I want you near me. I’ll pay you your current salary plus whatever you made in tips. And you don’t have to wear those heels and silly outfits!"

"You need an assistant for this small place?" I had to ask.

"This isn’t my only business. I own others too, and I really could use your help. You’re an educated and intelligent woman."

I knew he wanted more than my help and I was ready to give it to him.

I accepted the offer, both for the reprieve from the high heels and the ability to worm into his business operations. I hadn’t minded the short skirts. It was a real challenge to wear them and keep my panties concealed, an almost impossible feat, but they were meant to be seen in that outfit. And an occasional pat on the behind under the skirt wasn’t that bad, either.

Debbie was excited about the turn of events too. Better than we had expected. That evening, we had dinner to celebrate my promotion and to plan more strategy. After dinner, we did a little shopping for more suitable business attire and returned to our apartment for some post-dinner lovemaking. Starting with a simple kiss, we both progressively stripped to our lingerie, kissing and fondling each other into our bed where we finally finished undressing each other layer by layer while kissing each body part as it was exposed. I especially loved to suckle her breasts and make her nipples erect. She was beautiful. Pity she couldn’t reciprocate the pleasure for me.

I eventually reached Deb’s love canal where I kissed and licked her sensitive spot to the first of many orgasms. She turned and took me into her mouth where she remained for a long time. This became our preferred method of lovemaking, satisfactory for both of us ladies with no worries of pregnancy.

It was a nice change of pace being a clerical worker rather than a waitress. It necessitated a whole new wardrobe of business attire. Jerry even purchased some items for me as he deemed appropriate. I became quite adept at selecting my own outfits and accessories. I knew how I wanted to look and how to get it. Always in dresses to show off my sensuous legs. Jerry liked that.

I had never been so fastidious as a man, but a woman has so much more to choose from…so many variations and I loved all of them.

In time, perhaps several months, I learned of Jerry’s other enterprise. The bar and lounge was indeed just a front. The fact that it catered to gays and transgendered made it even less obvious and provided deeper cover. Jerry actually was acting as a broker for hot merchandise. But I needed the identity of his sellers and buyers and who was bankrolling him. This was going to take time. The man was very crafty in his business dealings. And time meant many more love sessions. We became very intimate friends and he treated me like a princess. We spent so much time in bed together that he wanted me to live with him, but I told him I would not leave my roommate, a friend since childhood. He accepted that. I never denied him the pleasure of my body. He loved oral sex with me…it’s all he wanted… and I really enjoyed him doing it. He couldn’t seem to get enough of the penis of a shemale.

He was especially intrigued with my stick-on breasts. Their realism. But he preferred the real things. He was bisexual…he loved women, but preferred sex with males. With Shemales he had both. I was his personal shemale and I accepted that with pleasure. It almost seemed Debbie enjoyed me for the same reason. So what did that make me?

Jerry was called to make a trip to Las Vegas and invited me to go along. It was a business trip and I could not miss it. Maybe close to a source.

I packed, with Deb’s assist, and left on the trip. It was to be a two week event, I was told. I was on my own. My partner could not go with, nor could she be seen there anywhere near me. By this time, Jerry had met her many times and might recognize her. At Jerry’s insistence, we traveled as husband and wife ostensibly for his convenience, although I didn’t know why. Now I was a married woman! So I dressed and conducted myself as one as much as possible. I wanted to make him proud of his wife. He even gave me an appropriate ring to wear.

We checked into our hotel as Mr. and Mrs. J. Johnson. We freshened up and hit the casino’s for a few hours. Then we returned to our room and went to bed. By this time, I was content sleeping with him. And I wore my prettiest nightgown and undies to keep him interested. I had to maintain influence over him.

I learned that as his wife, his clients wouldn’t hit on me to sleep with them, hence the disguise.

I attended a few meetings with Jerry, where I met some of the clients. We met in various hotel rooms, very casual, very private. Of course, I played the role of the loving and attentive wife as well as his business assistant. I couldn’t associate anybody with anything suspicious, but I remembered names and faces for the future. They all seemed to come from South America. Although they’d often speak Spanish to each other, their conversations even in English with Jerry were very cryptic. I felt they didn’t trust me, but then, why should they?

I figured I’d get Jerry in a mellow mood, in private, and pump him for information. That night, in bed, I began the foreplay, leading to some heavy lovemaking (My male inhibitions totally gone, I had come to enjoy it as much as he did). During the course of our activity, while he was nibbling on my phony nipples, I casually threw out some random questions about this excursion to Vegas, and his clients. He disclosed that these were sellers of some merchandise he was acquiring. He told me he was a broker for imported artwork. A sideline he was into.

Okay….the first step. Now what was their source? We didn’t need the sellers as much as the origin of the goods. The Mother Lode, so to speak.

All in time.

Jerry scheduled me for a facial and makeover one morning while he was to be gambling with his friends. I graciously accepted and he drove me to a spa where it was to be performed. I was instructed to disrobe and given a white lab coat type gown to wear. It was to take a full day…a steam bath, massage, facial…the works. They tried to make me very comfortable. I was offered a reclining chair, told to relax and given a beverage to enjoy. I started to read a magazine. That’s the last thing I remember till I awoke the next morning in a what appeared to be a clinic of some sort. Certainly not the spa where I started. I was a little sore under my arms, and my face felt the effects of a bad sunburn. I was still very groggy from some type of medication or drug. A nurse entered to check on me. I asked her where I was and what happened. She gave me a vague answer, something about pain medicine, and left to summon a doctor.

"Hello Ms. Johnson. I’m Doctor "Bob." You’ve been given some special treatments. You’ll be fine. Your husband is coming to get you in an hour so you may get dressed whenever you feel ready."

"Doctor, what treatment? Why am I here? Did I have an accident? Where is this place? What happened?"

It appeared like a side street clinic where no one uses their last names nor asks many questions. Often times, abortions or other illegal procedures are conducted in these places

"Oh, your husband sent you here. A surprise gift to you, he said. You’ve had breast implants and laser treatment on your face. We also applied tattooed makeup on you for permanence. He said they were things you always wanted. What a thoughtful man you have," the doctor said, all smiles. "A bit unorthodox maybe, but thoughtful. You’ll be sore for a few days, but otherwise fine. Just don’t use your arms too much. We inserted saline implants through your underarms so you’ll find some dressings there but you’ll have minimal scarring. I suggest you wear the surgical bra we’ve provided day and night for a couple of weeks until your skin adjusts to the new dimensions. And I’ll give you some pain pills to take as needed."

"Doctor, what exactly is tattooed makeup?"

I’d never heard of that.

"Ah yes…Your lips are now dyed permanently red, your cheeks are tinted with a permanent blush, your eyelids are permanently lined, and your eyebrows are permanently contoured and darkened. You’ll save a lot of time and money not having to apply makeup each day. And in a short time, it will all look very natural. Of course, you may want to add a touch of lipstick to alter the color a bit. We’ve had a great deal of success with this treatment. Professional models do this."

I cringed every time he said the word *permanent.* Was I to be a *permanent* woman now? Yes, I guess so…that, or a very pretty guy from now on!

And the breasts…I was shocked! The weight I now felt on my chest was really me! And no more beard! No more shaving! Well, I could certainly live without the shaving, but these breasts and the makeup are PERMANENT! I was now truly a shemale!

I gently caressed them and felt the twinge of pain when the nipples were pinched. They were indeed my own flesh. I really had mixed emotions about this whole thing. Obviously, there was no turning back, but then, I don’t think I could’ve been much of a man anymore anyway. I had become too adjusted to living and behaving as a woman…too effeminate.

Jerry arrived as I finished getting dressed, still a bit groggy. Somehow, my clothes had been transported with me. He sure had this all planned, the crafty fox!

He kissed me passionately before I could say anything and of course, I returned the kiss. He then went on to explain what he had done. He knew if he had told me in advance, I’d have refused, but having several times wished for my own breasts, he figured it’s what I really wanted, so he granted my wish adding a few bonuses. How could I hate him? I jokingly commented about hormones, but he said he didn’t want to lose my erections. How could I deny him? Good thing I hadn’t wished for a vagina!

I was sore for several days from the surgery and the facial treatments. I wore the sturdy surgical bra to support my new bosom, and moved very slowly. Also, looking like I lost a fight, I felt self-conscious about the swelling in my face, but it went down rapidly. During this time Jerry did some gambling at our hotel and left me to convalesce. I relied upon room service for meals and spent my time watching television. I also re-arranged my wardrobe for my new figure. I packed the breastforms away as well as most of my makeup. They were history.

This time alone gave me time to plan my strategy for gleaning more information. I needed to know when Jerry’s shipment would arrive and from where. How to get that info….???

Three days in a hotel room and I was going crazy. Television and room service….enough!

I felt much better and begged Jerry to take me somewhere, so he rented a car and we toured Hoover Dam. In the course of our conversations, he mentioned that we had to get home to receive his shipment. He wanted me to help with the inventory of it’s contents. This was my opportunity. I acted as though it was a routine request and let it pass.

We completed our tour, had a lovely day driving around the area of Las Vegas and nearby Henderson and returned to our hotel where Jerry arranged our return trip home. I have to admit, it was a nice vacation, my first, traveling as a woman. Being pampered and cared for is a nice change from the male role of being responsible for everything.

It was good to be home and to see Debbie again. I really missed her. She almost fainted when she saw the new ME! The real bosom with real cleavage, the colors on my face…so natural looking complementing my long black hair. I now had the appearance of a professional model. I filled her in on all the details, both of our meeting with Jerry’s clients and my personal experiences with the makeover and how it wasn’t my choice but one I’d have to live with. Deb was very understanding and, appeared to be delighted with my latest transformation. The whole thing further enhanced our lovemaking as we made up for lost time. There was a feeling of genuine passion between us…I truly loved this woman. If she once mentioned she didn’t see me as a man in a dress, what is she seeing now? I’m hardly even a male anymore!

Back at the club, everything seemed as though we had never left. The shipment of art arrived the day after we did. I carefully inventoried each item both for Jerry and, surreptitiously, for the police. The source was indeed South America. I gave Deb a list of the contents which she forwarded to Bruce.

From that information, and with international cooperation, they were able to trace the origin of the goods. It was artwork confiscated by the Nazis during WW2 and again, stolen by the Allies after the war and hidden in Argentina. With military efficiency, the stuff had been well documented, complete with the original sources and estimated value at the time they were acquired. This was all very useful in tracing the origin. Jerry was just a middle man to handle the transactions in the US and The 19^th Hole lounge was used to launder the money. He was bankrolled by the people in South America and was their pawn.

With the cooperation of Interpol, and US government agencies, the operation was terminated at the source and the majority of the artwork was recovered and returned to Europe. Working from that direction and from tips, the authorities ostensibly tracked down Jerry’s operation and arrested everyone involved, including me in a massive raid of the bar. With the other ladies, I was sent to a woman’s lockup and held until my *girlfriend* Debbie came to bail me out. It was made to look like I was just a bystander in the situation…a bar hostess who happened to be there at the time of the raid, along with the other low level employees, for the purpose of media coverage. All not uncommon. I was to silently fade into obscurity after the raid.

Jerry and his other more prominent helpers were initially charged with possession of stolen property and held for trial. More charges were to follow, I’m sure. There was no one left to bail him out. I felt bad, but I had to vanish.

After a short vacation, Debbie and I reported to Bruce in his office where she had to re-introduce me to Bruce in a different form. He obviously didn’t recognize me. In fact he’d never seen me crossdressed so he didn’t know what to expect. And now, I’d become a well dressed, well endowed, stunning woman in every aspect. This whole detail had taken over a year and a half and was a total success for him. Debbie explained in her report everything that had happened, especially to me, the sacrifices I’d made, the non-reversible bodily changes, the danger I had been placed into…not to mention the psychological transformation that had affected me, which Bruce then reported to his superiors with embellishment. I had undergone everything but a total sex change.

There was no doubt that I could no longer be a street cop….nor did I want to be one. I wasn’t sure I even wished to remain in police work of any nature.

Without the usual fanfare, I received a commendation for my successful effort and personal sacrifice, along with a promotion to Inspector, working in the sex crimes division. That’s an unusually big step for a patrolman, but it so "happened" that there was an opening for a female Inspector because it was felt that a woman could oversee the staff and victims better and I was qualified to fill the position both for my gender and background. Yes, I was considered a female employee now. And it satisfied the EEOC requirement.

Of course, I accepted the position with gratitude, along with the substantial salary increase. After all that I had been through, it was the least they could do and they knew it. (Actually, I now felt the gender bending was the best thing that ever happened to me, but I’d never admit it to my superiors.)

I was well received within the division where I was introduced as a transfer from another city. I think my physical appearance went a long way to assure my acceptance. The power of a pretty woman.

Deb was promoted to Sergeant within her own group. The department decided to keep the whole matter quiet, especially my gender swap, to avoid any embarrassment to all parties involved, namely me. In return, I signed a waiver of any litigation resulting from my involuntary gender transformation or physical alterations occurring in the line of duty.

Debbie and I were married by a judge shortly after our promotions. We had a simple wedding with two brides in attendance…of course, one was legally a male.

I was to spend the rest of my life in contentment as a woman living with my *girlfriend* and, secretly, my wife. And the job was a perfect fit for me since it indeed needed an experienced "woman’s touch." At last, I had found happiness. Oh, and I didn’t further pursue any male sexual attention.

 

 

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