It had been a stressful day at work, and I needed to relax. Olivia had mentioned that she had something special for tomorrow. She had a look in her eyes that stirred my emotions. She had placed her hand softly on my cheek and came in to kiss me. She walked away, and I watched her beautiful stocking-covered legs in her tight dress that hugged her ass. She was stunning, and my manhood was stirred.

Olivia had a strange effect on me. She has been the only person who has accepted me for who I am. For years, I had repressed my desire for cross-dressing and expressing my feminine desires. I am not gay, but see myself as bisexual. After a week of working as Ramona, I loved the looks that men gave me and the comments. Strangers in the elevator commented on how beautiful I looked. Hearing those words, I would blush. I knew some men knew I was male, but they did not judge. I could feel my panties getting wet.

Walking into my bedroom, I removed my clothes and went into the bathroom. Looking in the mirror, I saw my naked body. I had all my hair removed, and my skin looked smooth. My manhood was limp. After filling the tub with warm water, I added some lavender bath oil. I dimmed the lights and lit a few candles. I relaxed in the tub for thirty minutes.

Stepping out of the tub, I reached for a large cotton towel to dry off. Facing the mirror, I reached for a bottle of coconut oil and poured some into my hand. Wrapping my hand around my limp manhood, the feeling was exciting. I massaged until I came alive. It took a few minutes to reach an erect state. My hand was sliding back and forth. The swelling of the head of my dick made it look beautiful. My breathing had increased, and my legs were tense. I had to stop myself before I was ready to release my saved-up cum. I wanted to cum badly. Releasing my dick, a drop of fluid was at my tip. Taking my finger, I removed it to taste myself. I was feeling sexy.

I applied skin moisturizer to my body and put on a silk gown. The fabric felt soft against my skin. It took a few minutes for my manhood to return to its normal state.

My thoughts went back to Olivia and her comment. I walked to my closet to select my clothes for tomorrow. I had a new black skirt and a red silk blouse. It looked semi-business but sexy and knee-length. The skirt would show off my slim waist and tight ass. I was debating between garters with stockings or thigh-highs. I love both, but went with the thigh-highs. They would be easy in case Olivia and I wanted to get intimate. I found a matching red thong and bra. The blouse would fit tightly to draw attention to my breasts. A pair of low heels was selected. My outfit would turn heads for sure. Feeling satisfied, I went to bed to dream about Olivia.

The next morning, I woke up early. Pulling the covers back, my manhood was fully erect. My excitement was growing about seeing Olvia. Sitting at the vanity, I took time with my makeup. I applied red lipstick when I saw a transformed Roger into Ramona.

Walking over to the bed, I looked over the clothes, and calm came over me. Stepping into the thong, I had to arrange my manhood to keep it contained. Sitting on the bed, I gently pulled up the thigh-highs over my long, slender legs. The matching padded bra was next. I walked over to check myself in the mirror. There was a warm feeling that came over me, and I saw Ramona. I took a deep breath. Holding the skirt felt soft in my hands as I pulled it up over my hips. My blouse was last, and I left the top buttons undone to give a view of my bra as a tease. Taking another look in the mirror was a person whom I knew, and my feelings were mixed. I sprayed some perfume behind my ears. What I saw was a dream come true, and I felt like a woman. Finally, my feminine desires found satisfaction. I walked back and forth in front of the mirror, admiring my slender legs and how tight the dress was across my cheeks. I wore a pair of low heels. At that moment, I wanted someone there to hold me and to give me a soft kiss. It was time to face the world.

The parking lot at work was empty. I parked close to the building, and as I arrived at the door, Ian came up behind me.

“Wait, let me get that for you.”

“Thank you.”

“Roger, you look pretty, and I miss seeing you walking around the office. I need time to get to know Ramona. If you ever want to go out for drinks, I would love to take you out.”

“Ian, your words mean so much and accepting me for who I am.”

My heart was beating faster as I watched Ian walk off. I took each step with determination. As I walked to the elevator, I noticed the looks from the men passing by. On the elevator, I could feel eyes on me. Maria walked into the elevator.

“Hey Ramona. You look beautiful this morning. We must get together for lunch. I will call you to confirm.”

Maria stepped off to the next floor. I rode up three more floors to get to my office. Walking down the aisles, the other girls spoke as I passed. Arriving at my desk, the phone rang.

“Hello, this is Ramona.”

“This is Ian. I am going to step over the line. You’ve been on my mind ever since I saw you earlier. I know you are a guy, but seeing you as Ramona is astonishing. You are beautiful, and I cannot concentrate. You have stirred a sexual fire in me, and I need to ask you for something. Can you come to my office? I need one hour of your time. You can leave a note for Olivia that I need you to help me on a special project.”

“Alright. I will be there in 10 minutes.”

My thoughts were trying to figure out what Ian could want. Ian has a reputation in the office as being a ladies’ man, and all the girls talked about him. He is handsome with broad shoulders and soft spoken, and always a gentleman. In my time here, he seldom spoke to me as Roger, and now I am getting attention.

Arriving at his office, I knocked on the door and twisted the doorknob. He was finishing a phone conversation and motioned for me to have a seat on the sofa. Placing the phone down, he gave me a smile with a strange look on his face.

“Ramona, if anything upsets you, please feel free to leave. By the time I got to my office this morning, I was sexually aroused after seeing you. When I got here in the office, I closed my door, unzipped my pants, and started fantasizing about you and almost came in my pants. I had you over my desk with my dick buried deep in your tight hole. I have never been so horny over another man who cross-dresses. I am not gay, but you have stirred my emotions.”

“I am flattered by your words, but I have not done anything to make you feel this way. I am just expressing my true self, and cross-dressing makes me feel free. I am not saying it is all sexual. I have repressed my emotions for years. Olivia has helped to free me. Why am I here?”

“As much as I would love to bury my manhood deep within your tightness place. I will settle for the opportunity to have you watch me masturbate. I want to jack off and have you watch me cum. I know I sound silly, but please say okay.”

“This is a strange request, and I never thought you saw me this way. This is intriguing, and I want to do it.”

“You do not have to do anything, just watch.”

“Can you unbutton your blouse so I can see your bra, and part your slender legs slightly. I want to see your creamy thighs and panties.”

I could sense excitement in his voice as he whispered. I watched as he performed a striptease act for me. As he pulled his pants down, I saw an opaque pair of pantyhose. He removed his shoes and his hosiery and the thong that barely held his tool.

“You look shocked. Why should you be the only one to wear soft things?”

“They do look lovely on your masculine, slender legs.”

Ian continued until he was standing in front of me naked. He walked closer with his manhood inches from me.

“Please wrap your hand around my dick until I get hard.”

Holding his limp dick for a couple of minutes, it started to swell within my grip. His dick was getting hard, and I saw his balls slowly move up to his base. Ian had his eyes closed as he was in another place. I heard a soft moan escape.

“Oh, Ramona. Ugghh. Your touch feels electric.”

Ian pulled back and walked over to his desk, pulled open a drawer, and reached for some oil. He returned in front of me and gave it to me.

“Can you put some oil on my dick. I like it when I am slick.”

Slowly, I held the bottle over his shaft and let the oil drip on his tool. Once it was covered, Ian wrapped his hand around his hard tool. The head of his dick was beautiful. I was fighting an urge to wrap my lips around his hard dick.

“Ramona. I feel like I want to explode looking at your beautiful legs. Your stockings are fantastic over your long, slender legs. I feel like an animal in heat.”

I had a close look as Ian’s hand was going back and forth over his hard tool. I saw a drop of clear liquid at the tip of his dick.

“Wow, Ian. You have a lovely dick, and it looks delicious. I hope you are going to reward me with your hot sticky cum. I know you have a lot of cum. Oh, baby, are you going to share your cum with Ramona?”

“Fuck Ramona. You are bad. I love this. Your talking will push me over the top. Ugghh. Agghh.”

“Come on, baby. Fuck your hand like you want to cum. Yes, nice, and slow. Keep moving your hips. Look at your dick, how it is throbbing. Do it, baby. Ramona wants to see your cum.”

Ian was in another world as he got quiet. His hips were gyrating. I watched as Ian turned around and leaned over his desk. I could see his puckered, tight hole. He kept pumping his dick in his hand.

“Ian, will you do something for me. Can you lie on the floor and put your feet up on the chair? I want you to shoot your cum on your face. When you start to cum raise your hips to get your dick closer.”

Ian got on the floor on his back with his legs extended onto the chair. I saw his hard dick pointing towards his face. He looked sexy.

“Fuck. This is going to be great. I am so close to cumming. Look at my dick, please. What do you see?”

“I see a horny guy with his hand sliding back and forth along his hard dick. A slippery hand around a rigid dick. I see a thick throbbing dick wanting to release a sticky substance. I see a dick that will be sending jets of cum into a waiting mouth. I see a guy ready to eat his cum.”

Ian’s breathing was racing, and he was jacking off with determination. His hand was moving with precision. He was moving more slowly to enjoy each stroke.

“Oh, fuck Ramona, I can't hold back, I'm cuummiinngg!" Ian cried out.

The head of his dick was inches from his mouth. I saw his first load of cum from the tip of his dick. “Eat your cum, baby. Yes, I love seeing you eat your cum.”

“Fuck. I love this. Look at all my cum. It is so sweet. Yes.”

Ian relaxed as his last drop of cum shot from his dick. His face was covered with his sticky cum.

“Ian, can I take a picture of you naked with cum on your face. You can use it to jack off later when you get horny.”

After taking the picture, I knelt to the side of Ian, and I let my tongue go across his lips to taste his cum. “You taste sweet, honey.”  

Ian rose, and his cum slid over his chest and legs. I took another picture of his cum-covered body.

“I see that someone loved the session.”

Looking down, my manhood was pushing my skirt out. I felt dampness in my panties.

“Thank you, Ramona. This has been the best masturbation that I can remember.”

“If you need me again, give me a call. I will leave you alone to get cleaned up. This is our secret. I will let Olivia know that your project was a success. BTW, your dick looked pretty when you started cuming.”

I opened the door and returned to my desk. Since Olivia wasn't at work, my absence went unnoticed. Taking my phone out, I stared at the picture of Ian in his intimate moment. The taste of his cum was on my lips. I reached for my bag to get a thong to replace the wet pair I was wearing. The bathroom was empty, and I refreshed my makeup to wait for the arrival of Olivia.

Getting back to my desk, my phone was ringing. “Hello, this is Ramona.”

“Hi sweetheart, it’s me. How is the morning going?”

“Olivia. Everything is going well. What time will you be getting in?”

“I am one hour away. Can you clear my schedule for the rest of the day? There is something I need to take care of.”

“Is there anything that I can help with?”

“Yes, you can. It is you that I need. Since you have been in my life, I am a different woman. When I think about you, my heart races. Talking with you, I can feel the warmth between my legs.”

“I had no idea about what you were saying. I do not do anything special. I am just me. You are the one to help set me free.”

“You are a beautiful woman, and I love everything about you. The way you walk and dress affects me.”

“What can I do to help?”

“When I get in, I want you to fuck me. I am horny, and my pussy is wet. I need to feel your warm dick being pushed into my pussy. I do not know what has brought this on. You are amazing. I need you.”

“Olivia, are you alright?”

“No, I am not. I need your dick. The need to have you in me has been building up.”

“Is there something wrong?”

“No. I want you as badly. I did not know how to tell you that I wanted you as well. My heart beats fast when I see you coming into the office. Your beautiful stocking-covered legs stir me. I like looking at your ample breasts. I would love to have my dick between your tits.”

“If I did not have pantyhose on, I would finger myself while talking with you. I want to feel you shooting your warm cum deep in my pussy.”

“You are making it difficult for me to concentrate here at work. How am I supposed to work now? You have me thinking about fucking you. I want to suck your pussy first so I can taste your juices.”

“Now, I am getting wetter. I will try not to get a speeding ticket.”

“Calm down, Olivia. I do not want you to have an accident. I am here waiting for you.”

“Okay. I will see you shortly, darling.”

Placing the phone down, my thoughts were racing. My manhood was stretching my thong. I was trying to sort out how I got to where I am. A few months ago, I was a guy at his desk and cross-dressing in secret. Along came Olivia, who encouraged me to be by myself. I had been with other girls, but when I opened up about my feminine side, they would ridicule me. My heart was beating fast. My phone rang, which broke my concentration. “Hello, this is Ramona.”

“Just wanted to call you to say thank you so much for this morning. I can honestly say that was the best jack off that I have had in my life. I keep seeing my cum spurting from the tip of my dick. When my cum hit my lips, that was the first time I tasted my cum. It was fantastic, and I tasted something sweet. My dick is dripping now. I hope that we can have another meeting.”

“Ian, I am glad that I could help you. You do have a pretty dick. To be honest, I wanted to suck your tool to taste your cum as well. It was a rush being in the office.”

“Call me later when we can get together again. Bye.”

I was watching the hands on the clock as the minutes were ticking by. Olivia was closer, and soon we would be entangled in hot sex in her office.

Looking up from my desk was the object of my attraction. It was Olivia. With each step she took, her breasts bounced. Her skirt was above her knees, and the stocking-covered legs caused my heart to beat faster. She gave me a warm smile. I fought the urge to run to her and wrap my eager arms around her. She flashed a seductive smile.

Olivia reached my desk and came closer, and gave me a sensual wet kiss. Her tongue was in my mouth. I slipped my hand under her skirt to feel her wet panties. She pulled back.

“Sweetheart, you look beautiful sitting here. What an amazing sight.”

“You know how to make a girl feel pretty.”

“Did you cancel all of my appointments?”

“Yes, and I have a message on your phone that you will be out of the office the remainder of the day.”

“Good. Give me a few minutes, and then come into my office.”

The anticipation was unbelievable. My breathing increased, knowing what was behind the door. My hand reached for the door handle and pushed the door open. I saw Olivia standing in front of her desk.

“Come here, you beautiful girl.”

Olivia wrapped her arms around me, and we kissed. Her lips felt soft. Her hands gripped my ass to pull me in tighter. I let my hands move up and down her back. I walked Olivia back towards her desk. I knelt and reached under her skirt to pull her pantyhose down, and removed them. Her thong was soaked as I removed it. I moved my face closer. I licked and kissed all around her pussy lips before moving up to the hood over her clit and started massaging it with the soft underside of my tongue.

“Oh, sweetheart. Please suck my pussy. Agghh. Agghh. Your tongue is amazing.”

I was enjoying her sweetness. Her lips were moist as her juices were dripping. I slipped a couple of fingers to massage her inner walls.

“Make me cum. Oh fuck. Your tongue feels wonderful. I am so wet. Can you suck me until I cum?”

My mouth covered her warm pussy. I pushed my tongue deeper. Her walls were tight around my tongue. Olivia had her hands on my head as she was grinding her hips.

“Fuck. So good, Ramona. Push your tongue in deeper. Make me cum, make me cum, I'm cumming, I'm cumming, yes. Agghh. Agghh."

Olivia’s legs were tense as she held my head tight. I tasted her sweetness. My hands were holding her ass as my tongue was deep within the folds of her pussy. She relaxed.

“Come up here baby, so I can taste my juices on your lips.”

We shared a kiss, and Olivia was licking my lips to enjoy her sweetness. Olivia stepped back to remove her blouse and skirt. She was standing in her lingerie, and she looked beautiful. Her hands reached for my blouse to remove it, and she pushed my skirt to the floor. She looked at my thong as my dick was erect, pushing beyond the thong.

“You look pretty.”

Olivia’s hand reached out to hold my dick as she stroked me.

“I want your pretty dick deep in my pussy. I want you to fuck me good. I have been waiting to feel your cum in my pussy.

We walked over to the sofa, and Olivia was on her back. I knelt between her legs and looked at her waiting pussy. Olivia reached for my hard dick and held me tight, and took the head of my dick, held it to her opening. She rubbed my head up and down her opening.

“Darling, I want to enjoy this. I want you to fuck me slow and fill me with your hard dick.”

The head of my dick was pushed slowly into her pussy. I stopped to feel the tightness of her pussy.

“Push the rest of your dick in me. I want you all the way in. Fill my pussy. Please. Push all your dick in me.”

Once I was in, we started to get a slow rhythm. Our hips were moving in unison. The softness of her pussy was an electric feeling. I was fighting the urge to cum quickly, but I wanted to enjoy every minute.

“Agghh. Agghh. Fuck me good, Romana. I love you. Please make me cum.”

My urge to cum was building as our bodies rose and lowered as one. My dick was sliding back and forth in her wet pussy. It was a wonderful feeling. We both moaned as the sexual tension increased.

 "You feel so hot and big. Yes, baby, I want your dick. Fuck me, sweetheart! Make me cum, baby. Fill my pussy with that hot seed. Ohhhh fuck. I love your dick.”

We were both sweating as our bodies were deep in our lovemaking. The air smelled of sex.

“Ramona. Ramona. I am so close to cumming darling. Push your dick in deeper. Please. Agghh. Agghh. Fuck me. Please. I am cuummiinngg. I am cuummiinngg. Deeper baby. Oh, Ramona. Do not stop. I want all your cum.”

"Oh fuck, I can't hold back I'm cuummiinngg.” I cried out as the walls of Olivia’s contracting pussy milked every ounce of my cum.

"Oh, sweetheart, that was the most wonderful lovemaking I ever had. You were fantastic, and I just love the way your dick fits me. Thank you so much for making me feel so alive."

We kissed and embraced and drifted off for a nap in her office. The aroma of sex was in the air.