A Man and a Trans Woman Make Love

If sex between a man and transwoman isn't your cup of tea, this is fair warning that this story is not for you.

This is a different sort of writing for me, in more than one way.

It's written from the first-person perspective with a male narrator, which is a first for me. It also includes a lot of build up before the sex as these two characters get to know each other.

Aaron is a thirty-nine-year-old divorced man, exploring a long-held desire to get outside of his comfort zone.

Paige is a thirty-year-old transexual woman. She is friend of Aaron's sister, eager to help him explore this new facet of his sex life.

I've written in this genre before (the My New Girlfriend Has a Penis series), but this story is based on a real encounter that happened to the real life Paige who is a dear friend of mine.

Paige helped me with the words I used for genitals in this, because I wanted it to be as erotic as possible, without being disrespectful. We had several conversations both in person and through text as I worked through several drafts of this story.

As with most things I write, this takes place in a fictional universe where people don't worry about birth control or STI's. Both Aaron and Paige are grown adults.

~~

For the real-life Paige who not only told me this true story, but encouraged me to write it, and then sat with me and offered invaluable suggestions, tips, and insight into what words I should use while I put it together.

Thank you.

~~

I pulled the door open and stood there trying to look confident, while completely certain that I was failing miserably.

"Hi!" I blurted, happy that at least my voice didn't seem to be shaking.

"Good morning," said the beautiful woman standing there. "Are you Aaron?"

"Yes I am," I smiled. "You must be Paige. Emily spoke very highly of you. Please come in."

"Thank you," she smiled. "I'd love to. And I think the world of Emily. She's always been very special to me."

I stood to one side while she stepped past me into the hotel room.

She was dressed in a conservative dark blue skirt that hung past her knees, and a red blouse. She was carrying a laptop bag and pulling a tiny suitcase on rollers.

"This is a nice room," she said, going to the window and looking out at the rainy view.

I went and stood beside her, wondering what to do next.

Twenty-two stories below us traffic was clogging the streets surrounding the hotel, and pedestrians were hurrying along the sidewalks.

It was early March, and a cold rain had arrived with a forceful wind overnight, and the air outside had a definite bite, which matched the gray skies.

But somehow this room high above the chaos of traffic and the people dealing with the lousy weather seemed separate and safe from those concerns, as if we were in a bubble.

"It is," I agreed. "I thought about asking for a view of the lake, but those rooms are harder to get reservations for, and I thought that...well I thought...well..."

I was suddenly nervous, aware that I was now alone in a room with someone who knew something very personal about me. Even if I changed my mind about the physical encounter, it was too late to back out. For better or worse I was committed to some sort of face-to-face conversation.

"You thought you weren't booking the room for the view anyway," she said with a grin.

She'd been smiling when she came in. But now she was grinning at me, and the grin implied some sort of shared confidence, and even a hint that the two of us alone knew something naughty and wicked that the rest of the world did not.

"You're right," I agreed. "I don't need to spend time looking out the window."

"So what do you need Aaron?" she asked, turning to look directly at me.

I took a deep breath and gathered my thoughts, hoping she couldn't hear my heart pounding.

"That's a good question," I said. "And the easy answer is that I don't know what exactly I need. But truth be told I know what I want, and I've wanted it for so long that denying it is just making it harder and harder to deal with."

"And what you want is an experience with a transwoman?" Paige asked gently.

"Yes," I nodded. "I've always been sexually adventurous, and for a long time I assumed that I had already tried everything that I'd ever want to try."

I took another deep breath and turned to look at her.

"But over the past few years I've been fantasizing about more," I said. "And once I admitted to myself that I wanted to take this step, I couldn't stop thinking about it. It's something that I need to try."

"Are you trying it to get it over and done with?" she asked. "Or are you wanting more?"

"I don't know exactly what I want," I admitted. "But I don't think this is a one-time thing for me. I think that today needs to be a beginning, instead of just an experience."

"That makes perfect sense Aaron," she said. "It's something that I understand more than you can know."

"Emily said you would understand," I said softly. "And that you would be a perfect beginning."

"I don't know about perfect," she smiled. "But years ago, someone took time to make things easy for me when I was unsure of myself, and I feel a definite desire to pass that kindness on."

"Would you like to sit down?" I asked. "Do you want a bottle of water or anything?"

"I'm fine for now," Paige answered. "But I'd love to sit with you for a few minutes."

I sat on the edge of the bed, and to my surprise she sat on the bed next to me instead of in the chair. She pushed her suitcase under the chair and set her case carefully on the chair cushion.

"Are you nervous Aaron?" she asked gently.

"Yes," I replied. "I am. I guess it's pretty obvious."

"Why don't you tell me a little about how you got here this morning?" she asked with a smile. "Let me get to know you a little bit."

"I can do that," I told her. "Although when I'm nervous I tend to ramble. Feel free to cut me off if I talk too much."

"No worries," she smiled. "I like a good story."

"Well," I began, "I'm divorced. I have been for several years. We got married too young and weren't ready, but we're pretty good friends today. We didn't have any kids so that made it easier to go our separate ways."

She nodded as if I was fascinating to listen to, and I started to relax.

"I have some good friends and I like my work," I continued, "so all in all I guess I'm pretty normal. And for a long time most of my sexual encounters were too. I liked sex of course, and I always enjoyed spending time with women socially, so I think that helped."

"Do you masturbate much Aaron?" she asked me, flashing that devilish grin at me again.

"All the time," I laughed. "In fact, masturbation is one of the things that brought me here."

"How's that?" she asked.

"Well, I enjoy porn," I said. "And I like a lot of variety."

"The spice of life," she said. "I assume you would masturbate while watching porn?"

"Oh yeah," I admitted. "Not just masturbation though. I'd make sure to turn off my phone and block out plenty of time to indulge. I'm a big believer in taking my time and letting the pressure build."

"Emily was right," she laughed. "I do like you, Aaron. An awful lot."

"So I'd sort of collect videos," I went on. "I'd make sure to always have some that I knew would turn me on."

"What kinds are your favorites?" she asked softly, turning towards me, and bringing her knees up on the bed.

"All kinds," I said. "But I love facials, handjobs, and creampies the most. And of course, I like watching two women together."

"Every man's fantasy," she giggled. "But I love that too. If you like facials, you must like blowjobs too right?"

"A lot!" I said with a laugh. "Both in person and on video. But it was a blowjob video that first got me outside of my narrow focus."

"How?" she asked, leaning forward.

"I found a video with one of the prettiest women I'd ever seen," I started. "She made lots of eye contact and really looked like she was enjoying what she was doing."

"Maybe she was," Paige said. "Giving someone pleasure with your mouth is one of the purest forms of ecstasy that there is."

"I agree," I said softly, looking into her eyes.

There was a moment of silence right then, and I suddenly realized that I was no longer nervous. Paige was a good listener and I felt totally at ease.

"So you're watching this beautiful woman enjoy the cock in her mouth," she prompted.

"Yes," I continued. "And it was so good, nice and slow and sexy, so I saved it and kept browsing."

"By browsing, you mean you had your cock out?" she asked.

"Yes," I laughed. "Out and hard. And eventually I was touching myself, and getting to the point where I couldn't wait much longer."

"By wait, you mean you were close to cumming right?" she said.

"Exactly," I grinned. "And getting closer with each second."

"Oh I love this!" she said with a giggle. "Keep going!"

"So I went back to that video and restarted it," I said. "This time with a handful of lube and steady stroke. The video was a half an hour long, and I got pretty close to the end when I realized that I wasn't going to be able to last all the way through."

"So the choice was between satisfaction denied or immediate fulfillment?" she said, her eyes bright.

"I was alone so I opted for immediate," I laughed. "I decided to jump towards the end, hoping to see her swallow his cum. And to my surprise I landed at just the right spot, with her begging for his cum and tugging his cock as fast as she could while massaging his balls."

I swallowed, realizing that I had become fairly aroused. Partly from remembering the video, but mostly from having a beautiful woman hanging on my every word as I talked about jerking off to a blowjob video.

"So I was trying to time my own orgasm with the cumshot on the video," I continued. "I knew the guy was close because he told her he was. But then she stopped and stood up."

"And what happened then?" Paige asked.

"She started stroking herself," I said. "She had a cock, and it was rock hard. I had no idea she was a transexual until that moment."

"Did you like her cock?" Paige asked.

"At the time I was pretty shocked," I said. "Both by the cock and by how fucking horny seeing it made me. She jerked off and came all over the guy's cock, and then she went back down on him and licked all her cum off."

"There's nothing like the flavor of one's own cum," Paige said. "Have you ever tasted your own?"

She reached over and put her hand on my thigh, and I felt my cock throb at the heat of her hand through my pants, so close to my cock.

"Yes," I whispered. "My wife used to love it when I went down on her after cumming inside her. And she used to kiss me with my cum in her mouth after going down on me."

"That's so fucking hot," she said, squeezing my thigh. "I love a man who isn't afraid of his own taste."

"Sometimes I lick it off my fingers after masturbating," I admitted. "I think the taste is sexy."

"So did the guy in the video get to cum?" Paige asked.

"Yes," I answered. "All over her face while she jerked him and licked all of her own cum off of him. It was the hottest thing I'd ever seen."

"And you?" she whispered, leaning close enough that I could feel her hot breath on my ear. "Did you get to cum?"

"All over the place," I said. "I came so much that I soaked through the towel I had."

"That's so fucking hot," she whispered, pushing against my hard cock with her fingertip. "I love when someone's arousal is so intense that they cum an extra heavy load."

"It was," I agreed.

"Have you been hooked on girldick ever since?" she asked me.

"At first I pretended that I just enjoyed it because I thought she was a natural woman," I whispered. "But after jerking off to that same video over and over that week I knew that wasn't it. Especially when I couldn't stop fast forwarding to the part where she stands up and I could see how hard she was."

"They say that girldick is mesmerizing," Paige whispered. "Lots of guys start seeking them out after seeing their first one. It becomes an addiction."

"That's what happened to me," I agreed. "The sight of a beautiful woman with a hard cock started to drive me wild. Oh fuck."

I moaned and pushed up against her finger as it traced the pattern of my cock through my jeans.

"What about seeing a girldick all hard made you wild?" she asked, adding another finger to her rubbing motion.

"Just knowing what she was feeling," I groaned. "I know what an erection feels like. I know what it feels like to cum. It's so fucking hot to know that a woman is feeling exactly how I feel."

"And you reached the point where you had to do something about it?" she asked, licking my ear.

"Yeah," I answered. "I kept watching videos and fantasizing, and eventually I knew it wasn't just a jerk off fantasy. I knew it was something I wanted to try."

"And once you knew you wanted to try it, what did you do?" she asked. "Did you look for someone to try it with online?"

"I did," I admitted. "But I didn't know where to look so I could never really feel like I would find a real person. And eventually I confided in Emily."

"Most people wouldn't tell their sister that they wanted to try something that so many still see as unconventional," she said. "You must have really been driven."

"I was," I said. "And we talked about that. About it being unconventional to some people. I really wanted to try it. But I didn't want to make anyone feel like I was just some sort of sexual tourist. That's why I wanted a real person. Not someone who would feel like I was just using them to try something exotic."

"I'm a real person," she whispered. "And I don't feel any disrespect or sense any desire to treat me poorly."

"I wouldn't," I said. "I want you to enjoy anything we try. You're a friend of my sisters and I wouldn't ever do anything to hurt her. And if I treated one of her friends poorly, she'd be hurt."

"She told me that," Paige said with a smile. "I figured if she could vouch for you, I could at least meet you and listen to you."

"You're a good listener," I whispered.

"You're just saying that," she replied, "because I'm enjoying feeling your stiff prick."

She pressed her whole hand against the front of my pants, and I took in a deep breath at the pleasant feeling of pressure.

"Are you still nervous Aaron?" she asked.

"I was when you agreed to meet me," I said. "Eventually though, lust took over and I was just horny thinking about it. But when I got checked into the room this morning, I got nervous again, but I felt really excited too."

"The excitement is obvious," she giggled, wiggling her fingers against me.

"I'm not nervous," I said. "At this point I just don't want to say or do the wrong thing."

"It's perfectly normal to say the wrong thing when you're new to this," she said. "You should know that you can say anything to me, and you can ask me any question that you'd like."

"I appreciate that," I said. "And please tell me if there's anything that I should be asking but aren't."

"I will," she murmured. "I promise."

She reached out and patted my arm, and to my shock that gesture suddenly filled me with confidence. I knew I was safe in her hands as we explored this together.

I looked up at her and felt myself flush.

"I don't even know what to say," I blurted.

"That's okay too," she said. "Do you want me to talk for a bit?"

I nodded my head, feeling foolish.

She reached out and patted my arm again and then reached over and pulled her laptop case from the chair and put it on the bed between us. She unzipped a side pocket and reached into it.

"I brought some lube," she said. "It's natural and safe, and it feels so good that it can help overcome even the most persistently shy or nervous person get hard. But I have a feeling that we won't need this. We still might enjoy it though."

She put the vial of lube on the bed and pulled out another little bottle.

"This is massage oil," she said. "If you'd like to relax first by having me give you a nice slow rub, this stuff smells amazing and it's very relaxing. Or you can use it to massage me if you'd like to do that."

She set that bottle next to the first, and pulled out a third bottle, this one red and a bit smaller.

"And this lube," she continued, "is flavored, in case you want to taste me. Maybe you won't want it, but if you're nervous about the taste this will help."

My face suddenly felt hot, and I was aware of the sudden thudding of my heart.

"But that's not an expectation I have," she told me. "And I'm not going to ask you to do that. However, if it's something you'd like to try this might make it easier. Just put it out of your mind but know that it's here if we get that far."

I realized I was blushing intensely, and I felt hot.

"Would you teach me how to do that?" I asked softly, unable to meet her eyes. "If I wanted to?"

"Of course I would!" she said. "You've never done that before have you?"

"No," I said softly, embarrassed again.

"Well we all have our first time," she said, patting my arm again. "You're in good hands and I can guide you through anything you want to try. That's one of the reasons I'm here."

"One?" I whispered.

"The other reason is to make you feel good," she said softly. "In any way you'd like to feel good."

I took a deep breath and looked up at her, this time holding her gaze.

"You're really pretty," I said. "I'm glad you're here. Even if all we do is talk about some of this."

"Thank you," she smiled. "I'm glad I'm here too. And I like talking. But sometimes doing things are way more fun than just talking about them."

"I agree," I whispered.

"May I kiss you, Aaron?" she asked softly.

I nodded.

Paige leaned over and brushed her lips against mine, lightly at first, and then with a bit more pressure, before pulling away.

I leaned forward to kiss her again, and she leaned towards me, this time putting her hand on my cheek. We kissed quickly, and then I pushed against her and kissed her again, this time feeling something deep inside me begin to grow.

I pulled away and felt a sudden pang of uncertainty.

"Are you okay Aaron?" she asked. "What's wrong?"

"Nothing," I said. "I'm just, I don't want to move too fast. I don't want you to feel pressured."

"Oh honey," she smiled. "I don't feel any pressure. I'm right where I want to be and I'm with someone I'm enjoying getting to know. I'll tell you if we go too far or too fast, so unless I speak up, don't worry."

"I appreciate that," I said. "Thanks for understanding."

"It's quite alright dear," she said. "We can take our time and do anything you want, and we don't have to do anything you don't want. I'm here to take care of you, and I promise I won't do anything to make this bad for you."

"I'm okay," I whispered. "I've just wanted this for so long, and now here I am and I'm happy and scared and nervous and afraid of fucking it all up."

"We won't fuck anything up today," she whispered back. "I promise."

She sat back and looked at me for another long moment.

"Would you like me to get naked Aaron?" she asked quietly. "Or maybe just take off some of my clothes?"

I nodded my head, my heart suddenly thudding.

"You can undress if you'd like to," I said. "I'd like that."

With a soft smile she stood and turned to face me.

"Would you like to watch me undress?" she asked.

I nodded again.

She undid her blouse first, undoing all the buttons and then taking it off and laying it on the dresser behind her. Next, she unzipped the skirt and held it as she stepped out of it, before putting it with the blouse.

My eyes were immediately drawn to the tell-tale bulge in her panties, and I felt my cock strain in anticipation.

She turned her back to me and undid her bra, and then turned around so that as it fell forward I could see her soft breasts and beautiful brown nipples revealed right in front of me.