I've been thinking about writing a story based around a trans woman for a while now, so here it is. As it is based around a person transitioning to a woman, they will be referred to as she and her.
Back when I was in my late 20's, I worked as a certified masseuse, and the majority of the work that we did were full-on nude oil massages. We weren't a rub-and-tug or anything, but a legit massage parlor that specialized in this kind of stuff. If I had to guess, I would say it was about 80/20 in females to males that came through the door, and them having the option of having your midsection covered with a towel...I'd say it was around 50/50. Anyway, one particular day a new client came in and I noticed she was fairly tall; probably 5'10", maybe 5'11" and wearing a striped button-down shirt, flared jeans and worn Birkenstocks on her rather large feet. Why does this matter? We'll get to that.
So anyway, I take her back to the room and she sits on the table while I explained the processes, and eventually said I would give her a minute to undress and lie face down on the table. Like most of the others, she inquired about if she should cover up with a towel, and I said it was really up to her and what she preferred. I then stepped out for a couple minutes to wash my hands and collect my materials, and when I came back she was lying there bare naked with her legs closed tightly. I dimmed the lights and turned on some quiet, peaceful music, grabbed the bottle of warm oil and went to work. I drizzled some onto her upper back and started massaging it until her shoulders, and I commented that I'm glad she decided to come in...she was carrying a lot of tension that needed to be released. She said that things have actually been pretty stressful lately and that a friend recommended that she does it...although she was a little nervous about being exposed in front of me. I reassured her that there's nothing to be nervous about, and that the human body is a beautiful thing. I poured out some more oil and kneaded her back and arms, down her sides and to her butt and thighs. It was when I got to that point that the story turned interesting. Massaging her thighs, my hand slipped down between them to get to the insides, and it was then that I felt something...spreading them apart slightly revealed testicles and the head of a penis poking out from underneath.
Slightly startled, I moved my hands and said a quick, "Oh!" which, after a couple of seconds, she moved her head and looked back saying, "That's why I was nervous...I didn't tell you, but I'm trans. If it's an issue you can stop..." I snapped back into reality, telling her, "No, no, not a problem whatsoever. Just a little unexpected, that's all." "Are you sure? Most people think I'm a freak when they find out." "Not at all, sweetie. Just go ahead and relax." She smiled and put her face back in the hole.
Thinking about it, the height and big feet all made sense. Although if I wouldn't have made that discovery, I never would have known. She was that convincing! Back to the massage, I continued kneading into her thighs and calves, but all I could think about was that package between her legs. Moving down to her feet, I rubbed and stretched each of her toes and dug my thumbs down into her soles. While I was doing this, I noticed that she kept squirming and fidgeting around. After spending a couple minutes on her feet, I told her to go ahead and flip over onto her back, but what she said is still burned into my mind. "I'm not sure if I should..." "It's ok, most people are a little bashful showing themselves like this on their first visit. Nothing to be nervous about." "Well, it's just that I...I have an erection." Hearing that, I instantly felt butterflies in my tummy. "I'm not a pervert or anything, it's just with my meds, some days I get them really easily." I had to take a deep breath myself. "Don't worry, it happens. It won't be the first I've seen and I know it won't be the last. The best thing you can do is just not think about it and you'll be fine. She gave kind of an unsure smile for a second and then lifted herself up to turn over...and there it was. Her penis was stiff as a pole, looking a little over 5 inches long with a decent thickness, arrow-straight and leaning back towards her at about a 45 degree angle. Her balls, while on the smaller side were pulled up tight in their leathery sack.
I stepped back up to her head and started rubbing her temples and where her shoulders met her neck, trying to focus on the massage, but all I could think about was that hard penis right in front of me. I started to make a little small talk, asking about her meds and what it was like to transition, and she said she had started about three years prior, but also that she had lost some of her size in the process...about an inch overall. I told her it was still nice, and that a lot of guys wish they could have her girth. She giggled and thanked me, saying that while she always felt like she should have been a woman, she does still love having her penis and couldn't imagine not having it. By this point I had moved onto her arms again, and I noticed that a drop of precum had formed at the tip and was starting to hang down. This wasn't just a random erection...this girl was horny. I pushed the envelope a little further. "So, on days like this, when your hormones are running high, what do you you do? How do you control it?" "Well...there really isn't a whole lot I can do since I'm single. I just end up masturbating...quite a bit." Ok, at this point I could feel myself starting to get wet. "Oh? Well, how much is 'quite a bit' typically?" She giggled again and said, "It's too embarrassing." "How come? It's a normal thing and I think we can be open with each other about it. I'll start...I usually masturbate twice a day and I did it this morning in the shower. (Fact: I actually did.) Ok, your turn." "Well...um...a lot of days I'll do it...three or four times. Sometimes five if I'm really worked up." "Wow...I don't think I've even known any men that could go five times...that's pretty amazing." She smiled and glanced over towards me, saying, "Thanks...it would be nice to share it with someone, though." At this point her precum was making a small puddle on her belly. "It certainly looks like you're needing a little attention now!" I said that with a playful tone, and she looked down at it, saying "Oh, sorry...I was in a hurry this morning and didn't get a chance to...you know...so I'm a little backed up." I knew this was my only chance to get over that hump, so I just came out and said, "Why don't you go ahead and take care of that?" Her eyes opened kind of wide and just said, "What?" "It has to be uncomfortable for you to be like that. Let's go ahead and take a little break so you can masturbate and relax." "Are you sure...? I don't want you to get the wrong idea about me or anything." "No, no, it's ok. You definitely need it. Just act like I'm not here."
She took a deep breath and closed her eyes, then wrapped her fingers around her shaft and slowly started to stroke. I couldn't believe it...this beautiful trans woman was masturbating right in front of me! She was quiet other than the sounds of her precum getting smooshed under her hand and her long, soft exhales. Watching her hand slide up and down her rigid penis, it took every once of restraint I had not to tear off my clothes and mount her, right there on the table. My pussy was itching like crazy, almost screaming out 'rub me...finger me...make me cum!' I held out, however, keeping myself as professional as I could be in this situation, simply watching as she quietly masturbated. Her fist quickly slid up and down her shaft and her toes flexed and spread before she bent her knees and pulled her feet up close, pressing her soles together. She must have laid there, eyes closed and softly breathing while quickly stroking herself for a couple of minutes before she quietly whimpered, "Could...could you please get me a towel...I'm almost there..." "It's ok, we'll clean you up after...just let it go on your tummy."
She kept stroking and her eyes clenched, letting out a soft, "Oh...oh...ooh...ungh...oooh..." as she shot a small, yet thick load of cum onto her belly. Her toes curled in as she stroked and squeezed her penis, milking her shaft of every creamy drop. When her orgasm finally finished, she took deep breaths, slowly straightening out her legs and wiggling her toes. "Do you feel better?" "Yes...much better...thank you..." Well...I wasn't. My pussy was so wet, my panties were absolutely soaked...thankfully I had on a skirt that day and told her, "Just keep your eyes closed; enjoy that after-orgasm relaxation." This gave me a few seconds to push down my panties and let them drop to my feet, step out, wipe myself with them and hide them in a drawer. As her penis deflated back to a soft, but still full state, I went back and began massaging the tops of her thighs, more feeling the cool air against my damp, bare vagina.
I probably spent another 10 minutes or so on the massage, working both legs and down to her feet, digging my thumbs into her soles and rubbing each of her toes. As I worked on her feet, her toes continued to bend back and spread as she laid there breathing deeply through her mouth. It wasn't too long after that I told her we were finished and asked how she felt, to which she giggled and said, "I feel like a wet noodle." I helped her sit up and spin around, and I told her I would help her into the other room to rinse off the oil (and cum). I went to one of the cabinets and pulled out a pair of simple flip-flops to wear in the shower, slipped them on her feet and helped her off the table, holding her hand as she walked to the shower. Stepping in, I pulled the shower head down and began rinsing her, using my other hand to help with the oil off of her shoulders and back, down to her ass. After a minute or two I had her turn around and face me, focusing first on the slimy cum stuck to her belly. My hand then slid down to her shaved pubic mound, and beyond that...I just couldn't help myself. Making it seem like part of the procedure, I took her penis by the head and lifted it up, directing the water onto her testicles. I then ran my hand back and forth against it, causing her to softly moan. By the time I made my way down her legs and washed her feet, she had another erection. Drying her off, she was still rock hard, with it bobbing up and down along with her pulse. She was breathing hard as I ran the towel over her thighs and back between her ass cheeks, and when I moved the towel around and caressed her balls, another glob of precum suddenly leaked from her piss slit. She softly said, "I'm sorry...I need to..." as she again grabbed a hold of her cock and began stroking for the second time in a half hour. I went to my knees and watched closely as her fist pumped her shaft, seemingly already on the edge of cumming. Her toes tapped and wiggled against the flip flops as she inched closer and closer to orgasm, her balls pulled tight and her cock head bright purple. It took no time before she groaned, "I'm gonna cum..." and I simply said, "Do it...cum." With a few more strokes and hard breathing, she stiffened as the first string of cum shot from her penis with the rest flowing onto her hand and the shower floor.
As she started coming down, I couldn't help myself, taking her hand and licking the seed from her fingers, then wrapping my fingers around her penis and squeezed, milking out the rest of the cum onto the towel and causing her toes to curl hard. I slowly ran my fingers from the base up to the head, wiping off any other drops that leaked out. She shivered, now covered in goosebumps.
Being dried off and drained of cum, I walked her back to the main room so she could get dressed, but while still naked she thanked me and hugged me. I asked her what for, and almost getting emotional, she said for just accepting her for who she was and not teasing her like some kind of freak, to which I wrapped my arms around her and said she was a beautiful person, inside and out, and not to change herself for anyone. For a solid minute after that, we just stood there in an emotional embrace...the only thing that would have made it better for me is if I were naked with her, just being skin to skin together. We eventually separated and she pulled her clothes back on, thanking me again for everything. I told her I'm glad she enjoyed everything and that I hoped she would come back again. She smiled and nodded, saying she would come back soon. As soon as the door closed, I was leaning against the table with my skirt hiked up, furiously rubbing my pussy. I don't think I had ever been that horny in my life, and it took maybe 15 seconds for me to cum.
Later on that night I masturbated twice more, both times thinking about her. Hopefully when she comes back she won't just have to pleasure herself.
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