I celebrated my 40th birthday with friends and family in one of the best restaurants in town. The head of our law firm congratulated me for 12 successful years as a member of the company and 7 as an associate. My secretary, Jean, followed, complaining jokingly that I made her work too much. Then my wife, Sam, chuckled and agreed with Jean, saying the money was good, but I worked too many hours, so she hardly saw me at home. It was fun: The food was delicious, a lot of alcohol, and everybody had a good time.

I felt I reached the pinnacle of my life. I achieved everything I strived for. A beautiful wife with 2 well-behaved children, Amy, 8, and Michael, 5. Professionally, I was doing exceptionally well, and my success record was more than 90%. I was on our 5 members' board. I liked our team and socialized with most of them frequently. The only one I disliked was Logan. He was a 28 year old, junior lawyer who joined us at the special request of his uncle. The uncle was the CEO of the company who sent us more cases than others combined. Logan was a 6'1", 185 pound, handsome guy who thought he was a god gift to mankind. He had no respect for anybody in our firm but the boss. He was rude and inconsiderate to everybody on the team, including his own secretary. His success rate in the 6 cases he handled was a poor 50%. As I said, except for Logan, who I tried to avoid at all costs, my relations with the others were excellent.

What nobody knew was that I harbored a secret. I was a closeted crossdresser. In my office, I had a closet that nobody else could open because I installed a sophisticated coded locker. Twice a week, when everybody else left their offices, I'd dress like a lady, add makeup, mascara, and lipstick, and walk on high heels on downtown streets. Frequently I went to the movies and even to bars, where men danced with me and even suggested to take me to a hotel for sex.

I still recall the first time I did it: I checked myself in the mirror and liked the way I looked, but I was still scared to death that somebody would recognize me. To my utter joy, nobody on the streets suspected me. Slowly, I became bolder and wore sexier and more revealing clothes. Men ogled me and occasionally tried to talk to me about going on a date with them. I may have looked like a woman, but I doubted anybody had thought I was a very young one, yet some of the offers came from guys in their 20s! I was happy my secret was safe and continued enjoying the habit for almost 5 years.

One day, after lunch, Logan approached me and asked if he could talk to me. I tried to dismiss him, but he didn't budge and said it was confidential. I sighed, "I am very busy. Come to my office in half an hour. You'll have 10 minutes."

He showed up right on time and closed the door behind him.

He sat down and asked, "Can anybody else hear what we are going to discuss? Does your secretary have an option to listen to your discussions?"

"She never does without my permission; why?"

"I recommend that you disconnect anything that may be heard outside."

I disconnected the line phone and turned to him, "Young man, you better have a good reason for all of that."

Logan had a smug smile on his face. He pointed to my secret closet and said nonchalantly, "Joel, I know what you have there."

"Excuse me?"

"I know everything you hide in that closet."

"Whatever I have in my office is none of your business."

The mocking grin did not leave his face, "I agree. And usually, I wouldn't even care, but I know everything you use it for on Tuesdays and Thursdays."

I started feeling nauseous, "Logan, you better explain what you mean."

He giggled, "OK, but it will take longer than the time you allotted for me."

"Talk."

"Three weeks ago, on a Tuesday, I didn't have hot water at home. I decided to stay in my office, take a hot shower in our large bathroom, and later sleep on the couch. I was tired after work, so I turned the lights off and dozed for 40 minutes. Then I opened my door and saw a pretty woman leaving your office and locking the door behind her. Since you didn't accompany her, I got suspicious. I followed the lady outside. When she started strolling, I crossed the street and rushed forward. At the intersection, I made sure she didn't see me and stared at her up close. Your disguise was fantastic, but knowing who I suspected, the role play became clear. I continued following you, and saw you enter a bar, talk to a tall, dark man, and then dance with him as a woman. I sat just behind you and used my phone to video-record you two.

By the way, the high-pitched tone you talked to the guy was really impressive. I liked what I saw, and since my girlfriend moved to Arizona and these days my evenings are free, I chose to entertain myself being an evening detective. For a week, after usual working hours, I turned my lights off and waited for you to leave. I noticed you worked long hours in your office on Mondays and Wednesdays. However, each Tuesday and Thursday, you were prowling the streets, pretending to be a woman. I captured this on my phone, including your smiling at men who asked you for a date, your sashaying on your high heels, and flirting with guys. I wondered where you kept your different clothes and shoes, so one morning when you were in court, I told Jean I wanted to change my office and wished to check the view from your office. She let me inside but knew how much you hated me, so she stayed inside, too, the whole time. I pretended to look out but noticed only one large closet with a highly secured locker. It was obvious this was where the stuff was kept."

"Logan, what do you want?"

"First, you better be nicer to me."

"OK, I will."

He chuckled, "That's only the beginning, my friend."

"Logan, I am not your friend, and if you try to create trouble, I'll notify the police. What you were doing is illegal and harassment."

He continued smiling wickedly, "Did I forget to mention my uncle suggested I move to California? He said that after 3 years with you guys, I probably learned everything I needed to be a successful lawyer. If I moved there, he planned to send 50% of his business my way. So, if you decide to sue me, I'll move to California. Now, I am not sure what the law there says about a case like that occurring in another state, but I doubt my uncle will like it, and you'll lose all his business. What will be the implications on your career and family life?"

I was speechless. After a long pause, I asked in a low tone, "Logan, why are you doing it to me, and what is your ultimate goal?"

His face looked like that of the cat that ate the canary, "As I said before, first, you'll be extremely nice to me at all times, but you'll get further instructions in the upcoming days. In the meantime, continue doing what you did before, including dressing up like a pretty lady roaming the streets."

I returned home shaking. My life may be ruined. As Logan mentioned, if his uncle took his source of revenue from our firm, at least 70% of the staff would have to be let go, including lawyers. But more importantly, my family would be devastated. Sam, my wife, came from a conservative family who did not believe LGBTQ should have a place in society. Finding out I was a crossdresser would be a death sentence to our marriage.

I did not see any escape route and could not sleep the night. At 3 am, Sam turned to me, "Honey, you toss and turn all the time. Is everything all right?"

"I have a complicated case pending. Go to sleep, and I'll try to be quieter."

I didn't hear or see Logan in the following 3 days and hoped he would give up on pursuing the case. I was wrong.

On Thursday morning, he summoned me to his office and blurted, "After hours, you cross-dress as usual, but before you go outside, I want you to come to my office. I'll be waiting for you."

"Logan, look, I am sorry if I offended you before. I promise to respect you from now on and even recommend you to become a senior member early."

He stared sternly at me, "Joel, you'll do these things anyway. Now leave, and knock on my door dressed as a woman when everybody is gone."

I had a bad feeling about it but had no idea what I could do other than comply. The rest of the day I was distracted more than ever before.

At 5 pm, the last employee left the building. I dressed up with my preferred midi-style black dress and 3" heel shoes, applied makeup and lipstick, and knocked softly on Logan's door.

"Come in, Joel, the door is open." I entered slowly, blushing profusely.

He laughed, "You look really beautiful. If I had seen you like that on the street, I would have never recognized you. Except on times we work, and since you wish to be a lady, I decided to call you Sarah. Is it OK?"

"I don't think so. I prefer you do not not use any name."

"You don't get it, do you? It was a rhetorical question. As of now, you are Sarah."

I stayed quiet.

"Well, my dear Sarah, since you wanted to be a female, I think it's time for you to perform a lady's duties. As a young, highly sexual guy, I demanded my former girlfriends give me a blow job 3 times a week. So, be useful: Kneel before me, unzip my fly, pull it carefully, and suck me to a happy ending."

I stood still, shocked at his instruction. After a long moment, I tried to negotiate, "I'll make your coffee and arrange your desk 3 times a week instead."

"No way, Jose. It's been weeks since the last time my pecker felt hot lips around it. As far as I am concerned, it has been too long. So, Sarah, stop wasting my time and get going."

If a look could kill, Logan would have been dead by now, but it didn't work.

Slowly, I bent to my knees and began lowering his zipper. As the zipper started going down, it became clear he planned it in advance. He didn't have underwear on, and his penis created a significant tent in front.

As the zipper was lowered, a massive, erect cock jolted, hitting my chin. I retreated and gasped. He laughed, "A big one, isn't it? All my girlfriends said that it was my best attribute. So now, as my current bitch, it's your turn to admire my asset with YOUR mouth."

I looked at him pleadingly, "Logan, please, I'll do anything else you want but this."

"Sarah, I do not like arguments. You better start now, or I'll resort to punishment."

I grabbed his pole between 2 fingers and pulled it toward my lips.

Logan said, "Honey, just in case you have crazy ideas of injuring my buddy, I remind you that pictures and video clips of you in your beautiful attire are ready in envelopes with the right addresses in my lawyer's safe. If anything happens to me anytime in the future, my lawyer's first order of business is to send these by mail."

I smelled his member. The odor was a combination of musky and soapy. Logan had the decency to wash the organ before I entered his office.

I licked the tip and then kissed it. I had never done this before, but I recalled how Sam gave me orals. Then I engulfed his giant mushroomed head. I had to open my mouth as much as I could to accommodate its size. But at least the taste wasn't bad. I began moving on his shaft. Unlike the soft head, it was rock-hard and tougher to adjust my jaw around it. I started gagging when only 2" were lodging in my mouth and pulled it out.

He giggled, "That's OK, Sarah. First time is always a learning process. Now be a good girl and try again."

I pulled it one more time and, with much effort, was able to take in about 4" before feeling that I was about to choke and pulled it out again.

"Sarah, you are almost there. When you have 6" down your throat, and you bob it nicely, I'll be able to cum. Then you just have to swallow my little present, and everything will be over."

I gave it another try. This time, about 5" penetrated my mouth before I began gagging. He placed his hands on the back of my head and started to face fucking me. Kneeling down, having on a tight dress, I was in no position to resist him. I gagged, my eyes teared profusely, and my saliva was leaking all over the place, but Logan continued ravaging my mouth mercilessly.

As I was about to faint, I felt my mouth being filled with slimy liquid. It made me want to vomit, but I couldn't, and I had to choke or swallow it. Instinctively, I began to swallow his goo. Some of it entered my larynx, and I coughed between swallows.

Eventually, he slowed down and pulled his shriveling monster out. He looked at the leaky organ and commanded, "Now, complete the job. Clean it with your lips and tongue. I do not want my carpet stained."

It was another blow to my self-esteem and another nail to my humiliation.

When I was done, he smiled, "Sarah, I know your first time wasn't as pleasurable as you hoped, but trust me, once you get the hang of it, you'll love it."

I mumbled, "I doubt it very much."

He laughed loudly, "Honey, every woman should be an expert cocksucker. Otherwise, her man won't be happy."

I climbed on my high heels and asked, "Logan, may I leave now?"

"Yes, Sarah, you may. But there are 2 issues we need to discuss: A. Logan is a name I use in the office, just like your name is Joel. However, after hours, you are my bitch Sarah, and I am your Master, unless you prefer to call me Daddy. B. You have a break until Tuesday. I suggest you buy a large dildo or a wide cucumber to train your mouth on it because next time, I expect you to be a much better cocksucker. Capisce?"

I whispered, "Yes, Master."​