There was a letter on my desk when I arrived at work. It was addressed to “Lovely Roger.” I glanced around and saw no one. Sitting down, I opened the letter and read it.
“My dearest Roger. You need not try to figure out who I am. You will know at the right time. A mutual friend passed your name along. She figured that you and I would be a good match for some office sex. I hope I am not shocking you since you have engaged in an act already. Yes, Marsha shared the intimate details, and your fondness for wearing women’s clothing.”
Placing the letter on my desk, I was trying to determine whether I should continue reading. In the privacy of my home, I cross-dressed. It was more than an obsession, but a desire for soft, feminine lingerie. After the military, the opportunity to explore more of my desires increased. The only thing I could do in the military was to wear cotton panties that resemble male’s briefs. I had a few pairs of silk panties that I kept hidden. The feeling of soft material against my skin was amazing. Most of the day my dick would drip clear sticky fluid. There was a sense of sexiness.
After I started at the agency, my wardrobe expanded. My collection included mini-dresses, skirts, blouses, assorted lingerie, bras, garter belts, stockings, and thigh-highs. I had not gotten the nerve to shop in stores, but I shopped online at Victoria’s Secret and Shein.
The letter was on the desk, and my thoughts were causing me to get an erection, and I could feel the stickiness in my panties.
Picking the letter up, I resumed reading.
“The thought of you wearing panties excites me because I love guys with feminine tendencies. I know you would look beautiful fully dressed, and I imagine your cute ass walking around the office, unaware that silk panties cover your cheeks. I am getting wet as I write this. We have the possibility to share our intimate desires. I would love to see you in a matching black set wearing panties, bra, garter belt, and stockings. The vision of your dick sticking out from your panties is juicy. I hope this letter has you feeling like you want to pull your dick out and cream over this letter. You are such a horny girl, are you not?”
This mystery person was pushing all the right buttons. So much for Marsha keeping my secret. She told me there were horny girls in the office, but nothing like this.
There was a 9 AM meeting I had to attend, and I would see Marsha. As I entered the room, Marsha had already seated herself at the far end. Sitting down, her hand rested in my lap. She smiled and gave me a wink.
“Did you get your letter?”
“Yes. I know you had something to do with it.”
“I cannot keep you all to myself. We girls here like to share the finer things in the office. We need another girl like you. I know you will love it.”
“I was not expecting any of this. This is moving too fast for me, but it is exciting. I had a hard-on reading the letter.”
“You should have called me. I could have rubbed your dick while you were reading it. Did you read it all?”
“No. There are a couple of pages remaining.”
“Let me know what you think after you finish.”
The door opened, and Olivia walked in. She was the vice-president of our department. She was beautiful, standing almost six feet tall. Her legs were long and slender, covered in stockings. Her dress was tight-fitting and hugged her waistline, which made her breasts stand out. She wore a light shade of red lipstick, and her facial features were amazing. My eyes moved up and down her body. She did not notice I was checking her out. As she spoke, I was clinging to every word.
At the end of the meeting, Olivia walked around the room and gave each of us a folder of the main points discussed. She placed her hand on my shoulder as she passed. I thought that was strange. Prior to today, we had no interaction.
There was a note inside my folder: “Lovely Roger.” I pushed the note back in and looked at Olivia as we were walking out. She gave me a smile and a wink. I wondered if anyone saw that. I rushed back to my desk to finish the letter.
At my desk, I read the note given to me by Olivia.
“You know who I am now, and I hope you are not disappointed. Marsha told me some things about you that turned me on. I love seeing men wearing women’s clothing. Let me know your thoughts after you finish my letter.”
The letter had a lavender scent. I started reading and Olivia was expressing in detail her sexual fantasies and what she had in mind if I agreed. There was a strong attraction for office sex. She admitted to loving eating pussy and sucking dicks. She had a desire to have her virgin tight anal opening penetrated and had been waiting for the right person. She wanted me to text her the following number 73239 (“READY”) after I finished. I sent the text.
Later in the day, I received a text to meet at her office at 4 pm. There were thoughts about whether I was making the right decision. What would happen if we got caught? My desire to see this through was overwhelming.
At 4 pm I was at her door and she waved me in. She wanted the door left open while we talked. She came from behind her desk and sat in an opposite chair with her back to the door. Sitting in the chair, she did not cross her stocking-covered legs. I watched as she parted her legs and realized she was not wearing any panties.
“Roger. Do you have a good view of my pussy? I can change positions if you like.”
“Uh. Yes. The view is delicious. I mean it is good.”
“It would be nice if we chatted first to determine if we want to explore each other. Do you enjoy wearing women’s clothing?”
“It all started with wearing panties and how they made me feel. I do not identify as a transgender or gay. The attraction progressed to skirts, dresses, bras, and nylons. I wear my clothing only at home. I have not been in public.”
“You would look lovely dressed in makeup and a wig. If we proceed, I do want to show you off in public.”
“We can move slow on this.”
“I want to send you to see a friend, Isabelle, at her business, Totally Smooth. She does electrolysis. I love a smooth body free of all hair. I hope you have no objection. She can set up several sessions. This is my expense. I want to pamper you darling.”
“Alright. I will go along with all that you have in mind.”
This was all moving too fast for me to soak up. I glanced between her legs and noticed her wet lips.
“Come closer and stick your finger in my wet pussy so you taste my sweetness.”
Moving towards Olivia, I extended my fingers inside her moist love canal. Her lips were tight around my fingers. I pushed slightly and she moaned.
“Agghh. That feels so good. Can you push your fingers deeper? Please. Please. I want to cream on them.”
“You are nasty. I love the softness of your pussy. I want you to cum for me. Let Roger see you cum. Yes, baby. You feel so good. Your pussy is dripping. Your pussy is beautiful. Cum for me.”
“Oh. Oh. I am cuummiinngg. Do not stop. Push your fingers deeper. Move them around. Agghh. Agghh. Yes!”
Her long slender legs were stretched out in front of her. She had opened her blouse and was squeezing her breast. She was moaning.
“Oh fuck. Yes. Fuck. I needed this, Roger. Let me see you suck my pussy juice off your fingers.”
Withdrawing my fingers, I placed them in my mouth. Her juices were sweet. I wanted to get on my knees and place my mouth on her pussy and suck her juices.
“You taste sweet.”
“Well. Do you think we can enjoy each other?”
There was a leaky substance in my panties. My dick was pushing against my pants.
“Based on what I see, we have a yes. Let me give you my address and you can come over after work tomorrow.”
Olivia rose and walked over to close the door. She turned and looked at me and reached for the hem of her dress and pulled it to her waist. She was standing in front of me.
“Now, put your tongue in my pussy and lick me to a proper orgasm. I want to see my juices all over your face. Eat my pussy.”
Olivia had placed her hands on my head and pulled me tight. I had to adjust my head so I could breathe. Her lips were soft and wet. I pushed my tongue in as deep as I could while she was moving her hips.
“Yes, Baby. Suck my pussy juice. Make me cum. Please. Please. Deeper with your tongue. Move it around. Yes. Yes. Agghh. So good. Agghh. Agghh. I am so horny. Lick me. Almost there. Yes. Fuck yes. I am cuummiinng. I am cuummiinngg. Agghh. Oh fuck.”
Her hips were moving faster, and I was trying to keep up. I could feel her muscles tighten around my tongue. She continued to moan. I was pulled up from the chair; Olivia’s tongue was licking my lips as we kissed.
“I love the taste of my pussy juice on your face.”
After leaving Olivia’s office I went back to my desk and sat down. There was a lot to process. Marsha came to my cubicle.
“Hi Roger. It sounded like you and Olivia got to know each other.”
“How do you know?”
“Olivia had her phone on speaker. I was at my desk with my fingers in my pussy enjoying it all. My orgasm was intense. I had to change my panties because they were soaked. You two will have an enjoyable time. I want to see pictures when you are transformed.”
“I am not sure what I am getting into, but I am going to go along with Olivia.”
“You need to remember that you are mine. I will tell you that Olivia is obsessed with a man who dresses as a female. You are what she needs. If you get stares in the office do not be concerned because we girls, we talk among ourselves and we know who is sucking and licking who. You will make new friends.”
After Marsha left, I came to the realization that I was going to enjoy the female role. This would give me the opportunity to share my enjoyment of wearing feminine clothing without the guilt feelings. There were years I denied my feelings. I had an appointment to get my pubic area waxed before meeting up with Olivia.
Two days had passed since I heard from Olivia. I returned to my desk after lunch and there was a package with a note, “Meet me at the executive suite after work.” The note was not signed but I knew who it was from.
After work I used the pass key to get to the executive suite and I carried the package. Olivia was there to greet me.
“You can go to the bathroom to shower, and I will meet you in there.”
Following the instructions, I stripped and enjoyed the warm water flowing over my body. I was feeling nervous and excited over what was going to take place. When I stepped out of the shower, Olivia was waiting for me with a large towel as she started to dry me off.
“You can have a seat in front of the mirror. It is time to transform you into a beautiful woman. Your wax job looks lovely.”
I sat in front of the mirror. Olivia started to apply my foundation, and concealer to create a smooth, even base. She added dimensions with bronzer, blush, and highlighter, then filled in my brows and applied eyeshadow, eyeliner, and mascara. The finish was a soft red lip gloss. Olivia was creating a masterpiece. At the end she selected a shoulder-length wig to complement my soft brown skin tone. She sprayed her favorite perfume, Nina Ricci.
“Darling, you look beautiful.”
Looking in the mirror, I did not recognize myself, and I was feeling like a woman. My feelings were hard to describe. I stood up and faced Olivia.
“Honey, you must like what you see. Look at your hard-on. Follow me.”
We went into the next room. Olivia had laid out a black matching lingerie set, bra, panties, garter belt, and stockings. Also, a red mini dress. I had a tingling feeling looking over the garments. I took care as I started to get dressed. Once completed, I looked in the mirror and froze.
“You look beautiful. I may have to make you my assistant, and I know heads will turn.”
I was speechless as my heart raced. I was an attractive woman and feeling delicious. This was a dream come true. Olivia was standing back and silent.
“Well, how do I look?”
“You are Romona now. You are beautiful and honestly you are sexually attractive. I am horny and I need to have you. I want to take you now.”
“I am here for you to make love to me. You do whatever will make you happy.”
My confidence was rising as I started to tease Olivia by walking around the office. Pulling up the hem of my dress, I showed off my panty-covered cheeks. “Do you want to fuck me?”
“Romona, your teasing is working. You are the girl I have been looking for. You look delicious and I have just what you need. Yes, I want to fuck you good.”
“I want to feel something nice and hard in my tight opening. Please, fuck me.”
Olivia had me get on the desk on my back. She pushed up my dress and pulled my panties off. She parted my legs and walked up closer. She pulled up her skirt and removed her thong to free the double-headed seven-inch dildo. I felt a warm liquid over my balls that dripped over my tight anal opening. Olivia used her thumb to massage my anus. I held my hole wide as she pushed the head against my tight hole. She slid it up and down against my awaiting ass. She slowly pushed her head into me. I gasped as my fingers let go and felt her dick slowly push into me. I looked down and saw my dick dripping a stream of clear liquid onto my belly.
“Oh Romona. I am going to fuck you good, baby. Your ass looks beautiful with my dick in you. Yes. I love this. My pussy is getting wetter as I am fucking you.”
“Fill me up. Give me all your dick. It feels so good. Agghh. Agghh. I need your dick. Keep moving your hips.”
“Ramona, you are going to make me cum. My dick feels good in you. Oh yes.”
The feeling was exciting as Olivia was fucking me. Her dick was moving slowly, going back and forth. My tight hole was tingling. I never thought it would feel so good. “Olivia, fuck me. Agghh. Yes, baby. Push your dick in deeper.”
“I am pushing my dick all the way up your tight love hole. You are my first that I have fucked. I love your beautiful ass. I am getting close to cumming. Do you love this, baby?”
My legs were over Olivia’s shoulders for better penetration.
“Give me all your dick. Fuck my ass, baby. Yes, yes. I want you to make me cum with you. Agghh. I need this.”
“Oh, Ramona! Yesss. I’m coming, darling! You’re making me come, lover! It feels so wonderful! Yes! Yesss! I’m coming! I’m cuummiinngg.”
I felt a warm fluid running between my legs. I realized that Olivia had squirted. Her orgasm was intense. Olivia relaxed and withdrew her dick. I had a feeling of being satisfied.
We walked over and sat down on the sofa. Olivia wrapped her arms around me and gave me a gentle kiss. I had a feeling of being a woman who was fulfilled by her lover. This was something for which I had longed. Olivia was gentle.
“Romona, that was the best fuck I have had in years. You are going to be my assistant. We are going shopping for some outfits. I want you to look delicious every day. It will be exciting having your pretty body outside my door.”
“Olivia, you make me feel complete by allowing me to fully express my feminine desires. It was exciting having you to fuck me. You were gentle, and feeling every inch of you in me, I will never forget it. I will be the best assistant you have ever had.”
“Leave it to me to prepare the office for the new girl who will be joining us. You will be welcomed with open arms.”
I was overcome with a feeling of excitement. The opportunity to be fully dressed outside of my apartment was scary. Being able to walk around the office wearing stockings and a short skirt to show off my shapely legs? My thongs would show off my soft cheeks when I bent over. Yes, I would be the office tease. My desires would come true.
“Roger, you are a handsome man, but your true self is a woman. I love seeing how you fill out a dress with your long slender legs and perfect hips. The way you walk around the office, I have seen the way the other girls look at you. You have the potential to be a beautiful girl here in the office. You make my panties wet. We are going to make each other feel good.”
Things were going to be different in the office.