This was 10 years ago when I was in college, living in a college town, and I posted a CL classified ad offering to jack off in front of other people—which is still my fetish. At the time, I was imagining I might get a reply from a curious college girl... but instead, in my inbox I received an email saying: "I would love to watch you, but full disclosure I am a trans woman." Turns out she worked at a hair salon right down the street. At that time, I had never really thought before about how I felt about trans people, but right then I decided that I was totally fine with it.

So we made a plan for the next day or maybe the day after, we would meet in the parking lot of the hair salon after hours. No pictures were exchanged—aside from the dick pick in my classified ad—and my mind was imagining more or less an old man in drag like a Monty Python skit.

But much to my surprise, as I approached the sole compact car in the lot, I saw through the window a middle aged white woman probably in her 40s maybe 50s. No square jaw or stubble, but rather long blonde hair, age appropriate attire and makeup. Honestly, I bet the people she meets in life do not have any idea that she's trans, and if she hadn't told me I would have been none the wiser. For this reason, I wasn't sure if I had the right person! So I just dumbly stood and stared at her through the window like a weirdo until she eventually rolls it down and says something like "Hi... Are you meeting someone here?" I told her yes and she says to get in the car. Her voice isn't particularly deep or manly either.

The car is a mess! It's piled floor to ceiling with stuff... nothing gross like garbage, but rather boxes, shopping bags, hair curlers. Hey, my car was not so organized either, so who am I to judge. But hers was like totally packed! I squeeze into the front seat. I had sorta thought we could do this inside the salon, but she tells me that the salon is all closed up, we can just do it in the car. That's fine I guess, just not what I had expected. She tells me I'm handsome, and tells me I can take my pants off and get started. So I take a quick look around, the coast is clear, I undo my belt and take my jeans and boxers down.

I'm stroking for about a minute or two. She says to me, "Do you like breasts?" —of course I do! So she pops them out the top of her blouse. Maybe it's because it's dark, but I cannot see any scars at all, and her nipples are a nice light color. I'm rock hard, slowly stroking while I look at her surprisingly great boobs, probably at least a C cup. Can hormones grow them that big? If not, the cosmetic surgeon has got some next level technique.

I continue stroking for a few more minutes while she's got her eyes locked on my hard cock. I'm just shy of 7" and pretty thick. I know this was supposed to be looking only, but in the heat of the moment I decide to tell her, "You can touch it if you want to." She grabs it with a light grip and gives it a few strokes softly... But then she bites her lip and gives it a long, firm squeeze at the base.... Then finally settles on a more medium grip and a long, slow strokes.

I'm almost over the edge. I didn't bring anything to clean up with, and I'm a long distance shooter, so I don't want to blast cum all over this sweet lady's car. I tell her I'm close, ask if she's got some tissues or napkins. She lightens her grip and slows her stroke (thankfully) while she looks around the car. "No, sorry, I don't have anything..." What? With all the stuff in this car, there's not a tissue or napkin? "I'm gonna cum a lot!" I tell her...

"Well, there's this!" she says as with her free hand she pulls at a small, thin, see-through handkerchief that's loosely tied around the rearview mirror. She is still stroking me, and I'm doing everything I can to keep sperm from flying. I say hurriedly "yeah sure that will work!" and she unties this brightly colored, gossamer sheet with one hand while the other speeds up. She wraps it around the top of my cock and strokes me with this handkerchief while her other hand massages my balls, and I start cumming. The thing is like mesh, so it can't absorb any of my cum, and my jizz is flowing right through it all over her hand. However, it does accomplish the purpose of stopping my spurts from hitting the ceiling, and we make it through this monumental orgasm without getting too much cum on her interior. But like I said, this decorative pocket square can't really wipe anything up per se, so it just kinda spreads my cum all over my cock.

After I've finished cumming, she pulls the handkerchief away and is holding it while I pull up my boxers. We chit chat for a minute. She tells me "You're so cool" at least a couple times. I say I had a lot of fun, then hit the road! Never saw her again. But I'll always remember this experience. I wish I could live it again.