Trans Fantasy

My co-worker and I are in long-term committed relationships with partners who do not provide us with enough attention from a sexual fulfillment standpoint. We both love our partners and do not have intentions to leave existing relationships. Despite loving our partners, we have both found comfort and interest in one another from a strictly sexual standpoint; neither of us feel emotional connection or desire towards one another.

While most would say that the first time, we shared intimate desires and encounters was the moment it became not okay, in effort to remove the guilty feeling (there's plenty) we have agreed that performing sexual acts would be considered "crossing the line".

Consequently, over the course of months, we have enjoyed exchanging our fantasies with each other and as a result we have accumulated these short stories.

We are not sure what the future holds, but for now we will enjoy the ride until one of us puts this to a stop. Yes, we know it is not okay, but we are not asking for unsolicited therapy advice.

Hi. My name is Danielle. I identify as a transgendered woman. As you could have guessed, I started out life as a man. I grew up in a mid-sized Midwestern town deep in the land of corn fields, soy beans and religious repression. As far back as I can remember, I always felt uncomfortable in my own skin as a man. Gender dysphoria was a very real thing for me, and I really would have preferred to see a woman in the mirror rather than seeing the person who I woke up as every day. I liked participating in some sports, but I really wasn't that great at them. I was more interested in music, going to concerts, and doing stupid shit with my friends. I always identified as bisexual in that I found women and men to be attractive in their own specific ways.

I grew up in a very religious house where gender and relationships were binary. You were born either a man or a woman, and you only dated the opposite sex. If you were anything other than straight, you needed to pray on it and to participate in conversion therapy to help repress those feelings. The plan for my life was supposed to be: go to college, find a woman to marry, get a good paying job, have kid(s), and settle down in a house in the suburbs, and have an unremarkable life, just like nearly everyone else. If I were a weaker person, I would have just let it all happen, as I was expected to do, and regretted that decision later.

When I turned 18, I was quick to leave that life, and that town, and struck out on my own. My parents may have wanted me to go to college, but I took the money my grandfather left me in the college fund and used it to get the body I wanted. I grew my hair out, got my Adam's apple removed, got a wonderful set of D cup tits, and added some silicone to my hips and ass. I couldn't do anything about being tall, I am around 6'5", so I was commonly mistaken for a basketball player. The next step for someone who really wanted to embrace being transgendered would be hormone treatments. At that point in my life, I wasn't ready to take that step yet. Additionally, I enjoyed having a functional dick.

After working some shitty low paying jobs, and my parents cutting me off financially (because extortion always works), I finally decided to use what was left in my college fund as it was originally intended. I went to a state school because that was what I could afford, and I was never ivy league material in the first place. I majored in some boring-ass business related field that no one wanted to do, just to make sure that I did something that was in demand and made paid well. In college, I dated some women and I dated some men. The relationships with the women I dated were wonderful. I really felt connected to many of them, and they accepted me for who I was.

The sex was also really awesome. Some of my partners were a bit apprehensive at first with being trans, but eventually they saw the benefit of having a girlfriend with a dick. Some would throw on a strap on and fuck me in the ass with I was fucking them in the pussy. Unfortunately, the conversation normally went to long term commitment, which I wasn't ready to do at that time. This is what typically ended those relationships. So, like a fucking moron, but I found myself turning to relationships with men. The problem was, most of the dates and I went on with straight men ended up being extremely painful. Some men would be caring and affectionate with me in private, but were embarrassed to be seen with me in public. Some men had a perverse interest in trans women, and saw me as some sort of unicorn and failed to observe respectful boundaries.

Most of their questions focused on my genitals and what sort of sex we would have. Not that I really cared, because I was horny as hell and needed to get fucked. Guys just had a tendency to be either too clingy or too aloof for my taste. That said, when I got super fucking horny I would get past all of this and try to have sex with one of them. I really liked the feeling of a dick in my ass and I liked taking my long cock, lubing it up, and shoving it into their tight little asses. However, what ended up happening over and over again was unfortunate. Some would let me fuck them in the ass, tell me how good it was for them, then never call me back. Some would call back, but just want to be friends. Perhaps I was being a bit too aggressive with these guys. Again, I wasn't really looking for a long-term relationship, so I guess I really was treating the guys I dated as a means to an end. That end being by sexual satisfaction.

Eventually, I graduated from college and moved on to my first job. After getting used to my new look and body, I ended up being very passable as a woman, except for the whole height and broad shoulder thing. Since I went to a college known for their basketball program, I just would imply that I played college ball, which was a complete lie. The company I ended up going with was a small company and was still a bit old-fashioned. When I was filling out the new-hire paperwork, there was only two boxes to check for gender. I, of course, checked that I was a female. The work wasn't difficult, there was just a lot of it. It kept me occupied late into the night and sometimes on the weekends. Not being in a relationship, I really didn't mind working the long hours.

Over time, I got lonely, and horny, and started looking someone to fuck. Dating apps are fun to use, but you never know what you are actually going to get when the person finally shows up. Is he really as engaging in real-life as he is on the app or texting? Does she really want a relationship with a trans woman, or is this just a phase for her in her transition to being a lesbian? These are all concerns that I had which didn't do anything for me dealing with the fact that I needed to get fucked. Given that I spend a shit ton of time at work, I started to look there instead of dealing with randos online. There were some prospects there, both male and female, but the good ones were in relationships. One woman who worked as an admin was particularly attractive, specifically nice tits and a great ass, and had a really fun personality.

However, she had the whole marriage and kids thing. That didn't stop me from lusting after her. I started off slowly with her, making sure I was on the same projects and committees as her, going to lunch with her, exchanging stories about our pasts, and finding that we had a great deal in common. We eventually became friends and started to spend time together outside of work. I also learned that she had a very high libido, just like me. She and I would have the most inappropriate conversations, which made me really fucking hard. I outed myself with regard to my bisexuality, but I wasn't ready to tell her about being transgender yet. I thought she may become uncomfortable with me given that we spend time alone together, or treat me like some sort of freak show science experiment. One day she started to see through the façade. She and I were sitting in my car after walking at the park. I was stretching my back and had my chest out.

"Your tits look really nice," she said. "They're real?"

"Oh, god no." I said with a smirk. "I've had work done."

"Oh. Good for you. That's cool," she said still staring at my tits. She was lingering there a bit longer than she should. I could also tell she wanted to ask more questions.

"You were wondering something else?" I asked as her eyes met mine.

"Oh. Just... wondering if you had anything else done?" She asked biting her lip.

"I had some work done on my hips and my ass too," I said smiling.

"Oh. That's awesome. You should do what makes you happy." She said breathing in deeply.

I could tell she was aroused, but trying very hard not to show it. I could tell she was still a bit uncomfortable. It wasn't the time just yet to make a move, but there was some promise in this situation.

After another month of equally interesting conversations, I remember the next time she really saw me for who I was. It was mostly my doing. Normally, I kept my dick tucked between my legs so that if I were to get aroused (which happened frequently around her) I wouldn't be showing a bulge in my crotch. That day, I didn't take the normal precautions, and I just had by dick sitting normally under my dress. We were playing a game of truth or dare we had picked up from the adult store on our lunch break and the topic was anal sex.

"Yeah," I said. "I like to have a dick up my ass. It feels great. But I also like to stick a dick up the guy's ass."

"How do you do that?" She asked raising her eyebrows. "Do you have a strap on that you use?"

"Sort of... " I trailed off.

"It's a yes or no question." She said sternly.

"I have a dick." I said nonchalantly.

"So, you are a..." She seemed to want me to finish the sentence.

"... Transgender female," I finished her thought.

We sat in awkward silence for a couple of seconds.

"I was wondering why I was so attracted to you," she said looking into my eyes.

"I am really attracted to you as well. I have been hoping you feel the same way," I said rubbing her arm.

She took a very deep breath. "You know this is really wrong," she said quietly.

I withdrew my hand from her arm.

"I didn't say stop," she said a bit louder.

I put my hand next to her head, and ran my fingers through her hair. She leaned towards my hand and licked my fingers. Then she started sucking on my middle finger. I was getting hot and my dick started to get harder. I could feel it straining against by panties. I uncrossed my legs to free my dick and my balls from any restraint. The bulge under my dress was quite noticeable now.

"Oh, is that for me?" she asked after she stopped sucking on my finger and noticing the tent pole under my dress.

"You are making me excited," I said with a smile.

"May I?" She asked.

"Of course," I said.

She put her hand under my dress and started rubbing my leg back and forth moving her way up to my crotch. She ran her finger the length of my cock which was pointing up towards my stomach. It had started to pop out over the top of my panties, which has not been designed for a hard cock.

"Very impressive," she said continuing to run her hand over my cock.

I had moved my hand from her hair to rubbing her leg. She turned more towards me, threw her purse which had been sitting on her lap to the floor, and opened up her legs. I moved my hand up her leg to between her legs.

"I am so wet," she said. "Let me get things more accessible to you." She unbuttoned her jeans and slid them down exposing her underwear.

I slid my hand over her underwear and felt her wet pussy through the material. She shuddered as I ran my hand across her pussy.

She then took my cock out of the panties and started rubbing it. Her hand felt so good on my cock. I was so fucking horny, I was about to burst. She slid her underwear down and took my hand and placed it on her pussy.

"Put your fingers in my pussy," she whispered.

I obliged and stuck two of my fingers deep in her pussy. She moaned softly as she continued to stroke my cock. She moved her other hand to my balls and started playing with them while she worked on my cock. Her pussy was extremely wet and her clit was erect. We continued to work on each other until I was getting really close to blowing my load.

"I'm going to cum," I told her taking my fingers out of her pussy and placing my hand on top of her and still stroking my cock.

"Stick your fingers back in my pussy," she said sternly.

I slid my fingers back into her dripping pussy and she bent down to put my cock in her mouth.

The orgasm ripped through me starting at my cock and flowing through the rest of my body. The tingling sensation was almost unbearable. I hadn't realized how long it had been since I had a proper orgasm. She felt me cum in her mouth and started sucking and swallowing. I felt her pussy tighten and start to throb on my fingers. Her body shuddered as she came as well. I was done, she let some of the cum spill out of her mouth onto her chin.

"I can't believe we just did that," she said cleaning up her mouth with a tissue.

"Maybe next time, you can get on my dick," I said putting everything back into my panties and straightening out my dress.

"That would be fun," she said. "Let's try that really soon."