I was a young and fresh high school graduate living on my own for the first time in my life. I didn’t have much family support growing up to teach me about basic adult knowledge: owning a home, banking, taxes, or even a simple bird’s and bee’s talk. I wasn’t gaining anything by staying, so I had moved out as quickly as I could before starting a trade job my friend’s father hooked me up with.

I was a small, naive kid, still learning how the world worked and gaining contacts to further me along. I wasn’t the best student, so college wasn’t for me. I worked every weekend throughout my senior year, saving up to move out as soon as possible, so I never really got out and partied or went out with any girls. Basically, I kept to myself. I’m fairly short as well, and my body is proportionate. I was nervous about my size down there as well, so needless to say…I was a virgin.

Anyway, I was starting this new job, and a month or so into it, the benefits kicked in – 401k, health insurance, life insurance, etc. To be accepted to the company’s life insurance plan, I had to complete a medical screening. I assumed it was just a regular physical like when I was younger. I hadn’t been to the doctor’s for a check-up in a few years due to money problems, nor had ever had life insurance, so what did I know?

Covid lockdowns were kicking in at this point, so the examining agency was doing at-home screenings, meaning they would come to me. Not sure how this kept the nurses safe, but I guess it kept patients out of their facility. I scheduled an appointment and was told a nurse would give me a call when they were on their way.

I scheduled the appointment for one evening after work. The nurse gave me the call, and I just waited, not assuming anything unusual was to happen. Then, I heard her pull up, and she walked in with a small rolling suitcase full of her supplies. I’d guess she was about 50-55 years old but was in decent shape and wearing a knee-length skirt with what looked like a beautiful pair of tits beneath her blouse. She was built a little bigger like she worked out a bit, but she wasn’t wearing anything extremely tight and had a mask on, as did I, for Covid reasons. I noticed her voice was slightly deeper than most women’s, but I just figured it was due to her being old or maybe a smoker.

She set things up in my living room and started the exam with the basic background questions. I just sat, answering from the chair next to her on the couch. The questions got a little more in-depth, and she scooted closer to start the general exam process. Per her request, I took off my long-sleeve shirt to check my blood pressure and heart rate. Eyes, ears, and nose were next. All basic stuff. Then it got interesting.

She asked me to remove all of my clothes to examine my full body. I thought it was a little odd. I’d never been naked in front of anyone before, let alone a grown woman. I was hesitant, but she gave me that hurry-it-up look. I stood, removed my socks, shorts, then briefs. I looked down, and my nervousness clearly showed. I must have been 1.5″ soft at best. She took a peak and gave me a small smile and a thank you. Then, she had me do all sorts of stretches (hopping, that sort of thing), all while nude in front of her. She asked questions, asking if I had aches or pains anywhere, poking and prodding around my body in different positions. I caught her taking peaks at my manhood – or lack thereof – but she was professional and did not say anything about it.

She did a full-body skin exam next, checking for moles and that sort of thing. Then, she stood directly in front of me, staring at my upper body, working down to my legs but skipping the groin area. The same thing on the back, sitting down as she skipped my ass down to my feet and working back up.

“Okay, I’m going in,” she said and immediately spread my cheeks, doing her visual inspection. I gasped at her touch, which she noticed, and let out a small laugh while saying, “it’s alright, I’m not going to hurt you. I’m just looking.”

“I know. I’ve never had anyone have that close of a view of my butt hole before.”

“Well, in the medical field, we call that an anus and the good news is yours looks great!”

She slapped my bum and squeezed my cheek before spinning me around, now at eye level with my soft penis. She glanced up at me and smiled at me as she caught me blushing before going back to business. She touched around my groin area and moved my dick and balls around to inspect better. She told me I looked good and shouldn’t be worried about anything related to skin problems.

Next, she wanted a urine sample and asked if I could produce one. I told her I think I so and I would give it a try. I was clean, so I had no worries but assumed she would give me a cup and let me go into the bathroom. Not the case. She took the cup out of her case and shimmied her ass to the edge of the couch. After removing the lid, she reached her hand out and held my penis in one hand, and aimed it at the cup in her other. She waited patiently for me to begin, which felt like an eternity with my stage fright. Any growth I had gained from her fondling had disappeared due to my uneasiness at this point. Finally, after what felt like forever, probably only about 60 seconds of her holding my small flaccid cock in her small hands, I began.

“Oh! There we go! I wasn’t sure if he had gotten scared,” she said as she laughed.

I filled up the cup to the line and stopped myself. Never a comfortable feeling, but she added that it was a strong sign, being able to stop like that in the middle of a pee. She spun the lid back on and placed the tape seal over it.

As she sat in front of my nude body, looking up at me, she began the sexually related questions: how active I was and if everything was functioning normally. I answered honestly and told her I had yet to have any sexual experiences and was uncertain.

“That’s okay, we’ll take a look and feel to make sure everything is working properly,” she assured me.

“Thank you, I know I am a late bloomer, so I’m pretty nervous about putting myself into any sexual activities.”

She smiled and said not to worry as she worked her ungloved hands around my goods, asking me to turn and cough.

“Have you ever checked yourself for testicular cancer?”

“I have not, and I’m not sure I know exactly how,” I replied.

“It’s a good thing to know and learn. I will show you. First, you take one of your testicles in your hand like this,” as she pinched my left testicle between her thumb and index/middle fingers, “and roll it through your fingers to check for any bumps and lumps anywhere on the testicle itself.”

She did exactly that and told me to try the other one for her.

I noticed there was a bit more blood pumping to my organ as my shrinkage and embarrassment subsided. Finally, I did as she asked and said, “I don’t think I feel anything unusual, just something on the back?”

“That is the vas deferens. It carries semen from the testes up inside of you and back out through the penis when you have an orgasm and ejaculate. Have you masturbated and experienced this?”

“I have a few times, but not often. I usually have wet dreams every week or so.”

She smiled at my innocence and told me, “it is perfectly normal to masturbate regularly, and that will help you avoid any mess you make in the middle of the night. But based on this exam, it appears everything should be working normally there. Do you have any concerns about anything?”

Talking about my penis but not actually touching it, countered with a mature woman staring at it, had me shrinking a bit again. Finally, I wanted nothing more but to put my clothes back on. Still, I was curious about it and wanted to know for sure, so I asked, “I’ve never seen another penis before aside from some porn, so I’m just wondering if you think I’m growing and developing how I should be?”

“It is perfectly normal for a teenager to wonder about these things. You look fine, and your penis is normal. It does appear slightly below average at the moment, but it is in its flaccid state. I’m sure it grows quite a bit when you get an erection, correct?”

“A little bit, but not much. You don’t think it looks odd at all, with its size and scar there?” I asked.

“That is just your circumcision scar. The majority of American men are circumcised, so you have absolutely nothing to worry about.”

“Okay, that’s good to hear. I have heard of that but never seen one before, only in textbook drawings.”

I must have been visibly shaking in nervousness at this point because she told me to take a seat next to her, still naked, and said to me, “If you are really that concerned about this, I am uncut and am average size myself. I can show you we are the same to help ease your mind.”

My mind flipped upside down. What does she mean? She doesn’t have a dick. My face must have clearly shown my confusion as she said, “I am a trans woman. I was born with a penis. These are fake,” pointing to her own chest.

Wow, this blew me away quite a bit. Growing up, I had always thought it wasn’t an outrageous idea that a girl could have a penis. I had heard of trans people but had never seen or been in contact with anyone as far as I know. So this had caught me completely off guard. I sat there speechless and only came up with an “Okay.”

She stood up and pulled up her skirt above her waist, and I noticed a small bulge in her panties. Those went next, and my jaw must have dropped as she giggled. After that, I was eye level with the first penis I’d ever seen, other than my own. It was similar in size to my normal flaccid state (not at the moment, though, as I was still suffering a bit from my stage fright), but it looked different with the foreskin.

“See, it’s not much different, right? Just a little bigger and uncircumcised,” she said as she began to roll her foreskin back over the tip of her cock. “Underneath that, though, we are the same, see? So go ahead and feel it. You’ll notice it’s the same as yours.”

I’ve always considered myself straight, never thought of the idea of doing anything with another man. But at this moment, everything was happening so fast, and my brain was frozen. I was following her orders. Finally, I reached and squeezed it in my hand. Wow, what a feeling! I gave it a few tugs and rubbed my thumb up and down it once. It was the same but different. Similar enough for me to agree with her and remove my hand, though.

“It looks like that woke someone up!” She laughed, looking down at my cock. I glanced down. I was growing and didn’t even realize it. She sat down next to me again. “That’s good, though. Now we know it works. If you can get it all the way hard, I can even measure it for you to comfort your insecurities.”

I didn’t move. I didn’t know what she meant. Did she want me to start stroking it in front of her? I guess so because she took her left hand and started doing it for me. “Does this feel good?” She asked. “I’d love to get a sperm sample from you too for more medical tests.”

Um, yes! It felt amazing! But I only managed to say, “Yes, it does, that’ll be fine.”

Within no time, I was hard. She had me stand up, grabbed a sewing measure, and measured. “You’re five inches, not even a half-inch under the American average. You should never worry about this at all, I’m about the same size, and I can say for certain it is still plenty big enough to satisfy any woman.”

Half thinking she was just nice, half wanting to see where this would go, I called her out for it. “That’s easy for you to say. You’re probably a lot bigger when you’re hard.”

“Why don’t we find out?” and she leaned back on the couch, exposing herself to me again. Did she want me to do it?

I sat down, and without thinking about it again, I listened to her and just went for it. I wrapped my right hand around her shaft and began stroking. After about one minute, she was hard enough to measure. We both stood up and measured it. She was telling the truth. It’s just five inches.

“See, we’re the same, and you’re normal and capable,” she said as she dropped the tape, took a step toward me, and placed both cocks next to each other in her hand, touching one another.

She was right. They did look very similar, apart from the foreskin. I reached down and pulled it back for her. I liked the way it felt, and it was easier to stroke.

“Now, how about that sperm sample?”

“Okay, but you may need a release now, too,” I replied, and we both laughed.

She reached into her bag, grabbed some lubricant, and dropped some onto both of our cocks in her other hand. We both just stood there next to each stroking each other, sometimes together. It was a brand new feeling I’d never known, and I didn’t want it to end. After about 5 minutes of that, she sat me down on the edge of the couch and leaned me back. She took off her blouse, revealing 2 large breasts behind her bra. It must have been at least Cs if not Ds.

“Have you ever felt fake boobs before?”

“I’ve never felt any boobs before,” I exclaimed while we both laughed as she took off her bra. What a sight! Perfect sized areolas and small hard nipples on the front of those big firm titties.

“Give me a feel,” she said as she straddled me, far enough back for her to reach down and play with my balls.

I reached up and squeezed them. I bounced them around and played with her nipples, giving some playful pinches. She went a little lower, tickling and massaging my anus. I leaned my head back and let out a moan.

“I see you’re enjoying this,” she said as she left one hand playing between my anus and my sagging balls and used her other to stroke my dick.

I reached down and was stroking hers. We started slow and got faster over about 5 more minutes. She noticed I was close and grabbed the sample cup. She was just in time as I exploded a healthy amount into it. She began humping my hand harder with her gorging cock and busted all over my sack and thigh in no time. We both sat there, out of breath and satisfied. She grabbed some tissues and cleaned up the mess as I laid back on the couch, thinking about what just happened. Was this a dream?

“I think we got a little distracted from the exam,” Sse said, snapping me out of my trance. I looked up in time to watch her putting her panties back on and pulling down her skirt before grabbing her bra and blouse. “That should do it for the physical part of the exam. After that, you can put your clothes back on, and I’ll have a few more questions for you.”

I did as she said, answered her final exam questions, and thanked her for such an experience. “I feel much more comfortable in my own body now.”

“If you ever want to meet again, outside of a work setting, you have my number,” she said as she walked out the door to her car.

I couldn’t believe what had just happened. It was an experience I’ll never forget, and it left me wondering if there would be more to come?

 

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.