When Young Boy Met Sophia [MF] [Long]

First post here.

I’m almost 30 now, and this started nearly a decade ago so my memory may be a little hazy. But I’ll go off what I recall the best I can.

I was 20 or 21 years old at the time and in college. I was kind and not bad looking, but I didn’t have a lot of confidence. I had hooked up with a few girls I met at frat house parties but that was basically it. While things have drastically changed in the confidence and game department for me since then, back then I was anxious and shy.
The town I lived in wasn’t large enough to have many streetwalkers – though there were a few walking around – but they sure did corner the market on happy ending massage parlors. There was one that was very affordable and discreet. I had been maybe one or two times before but I had only gotten handjobs.

On this particular night, I pulled into the parking lot and took the back entrance. I had to get buzzed in because the door was locked. Once I got in, a hot, slender, light-skinned Latina who looked about late 20s was behind the plate-glass window. (A dead giveaway to what this place really was, but it was known that cops had allowed these places to remain open in exchange for free sex) The woman, we’ll call her “Sophia,” had blondish brown hair and a kind, pretty face. I paid the basic fee and I went into the room with her. She told me to get comfortable and she would be back. I stripped down to my birthday suit and laid down on my stomach on the table. She came back shortly after and gave me a rub down. These places are not known for their massage expertise, but it was relaxing, sensual and even comforting for this beautiful woman to run her hands all over my body.

I was visibly nervous. I wanted a blowjob, but was scared to do so with a woman I didn’t know. I’m not at all judging the people who work at those establishments, but I had been scared shitless by my high school health teacher about STDs and I had no idea how many times she did that sort of thing and if she was clean and disease free. She reassured me she was, but I was still very nervous. We talked tips and she was willing to go down on me for a relatively low price. Still, I must have almost been shaking at that point. She took pity on me and said that she didn’t usually do bareback blowjobs because – like me – she was concerned about STDs. However, she said that she could tell by my demeanor I hadn’t normally done this kind of thing. So, with not a whole lot of time left, she asked me if I could cum quickly. I was a young, inexperienced and very horny college kid. Of course I could cum quickly!

She had one rule: “not in my mouth.” I agreed of course. Here’s where it gets interesting. She took her top off as a way to justify the tip I gave her to the people she worked for. And she had me stand against the door to block the reverse peephole (love that Seinfeld episode lol). She crouched down and took me into her mouth. I’m not small, but I’m also not big. My “just right” Goldilocks dick was not difficult for her to handle. I asked if I could put my hand on the back of her head (I still do that with any new partner, actually, as I feel like that’s something that you should make clear she’s ok with before you do it) and she started to suck me. My goodness, did my dick feel good being slid between her lips and wet tongue. I guided her back and forth, and I held her head in place each time she deep throated me. I had probably seen it in a porno and thought it was hot. She had no problem with it, holding for a moment before sliding back out to continue her heavenly oral massage of my young member. It wasn’t long before I was going to cum, and I told her so. Then, she asked me something that blew my young, inexperienced mind.

“Wanna cum on my tits?”

Of course I did. She slid me out of her mouth and jerked me to completion, with my warm, sticky, pearly-white cum landing on her chest. I made that “oh-oh-ohhhh” sound when I came, and she chuckled. She was so very sweet, and after we cleaned up and got dressed she gave me a hug goodbye. I think she asked me to come see her again.

I did, and she began to affectionately call me “Young Boy,” because I was younger than most of her customers. I saw her a handful more times over the years, and over time my naïveté in regard to that first encounter revealed itself. She was so put together our first meeting, but as time went on her face aged somewhat and her teeth were missing. One of the other ladies who worked there would later tell me she was addicted to drugs and was dishonest and would sometimes have her own daughter steal from the wallets of customers’ pants pockets while she was in a hot tub or shower massage with them.

She was always very friendly to me, though, she never stole from me, and she gave great girl advice. I never got another blowjob from her, but I got more handjobs and fingered her. Twice, we fucked. Before the first time, I could hear her in the next room asking a client “you like that pussy?” That reminded me of my first meeting with her, and how she claimed she “didn’t normally do this.” I thought of her worry over being discovered by her coworkers. And I wondered…was that all an elaborate ruse to make me feel more comfortable with her, or was she still newer and the only one who was doing that sort of thing?

She eventually got promoted to manage the joint, and what was once simply a happy ending place turned into a glorified brothel. She eventually got new teeth. I, being young, sweet, and very naive, viewed this damsel in distress with genuine concern (which, I regrettably admit, did not keep me from paying her for sexual favors). I would ask if she was going to leave the parlor for something more legitimate. She kept saying “as soon as I get my back deck redone, I will.” Either that back deck resembled something out of a mansion, or she was bullshitting me.

As time went on and I had long since graduated college, I moved away. However, I still found time to see her when I returned to town. There was a period where I lived less than two hours away, and I would go see her on occasion. At this point, though, my cock played tug of war with my conscience. Sometimes I would call to see if she was there, but I wouldn’t show up. I sensed a little bit of irritation in her voice when she asked “are you going to come?”

I remember the last time I saw her. I was planning another move, and this time I didn’t think I’d be back to see her again. She would act real sultry when we played, but I was so comfortable with her I was more amused than anything. She got on the table on all fours, and I entered her from behind while admiring her smooth skin, hot body and tattoo on her lower back. I went slow. My stamina had increased like fivefold in the intervening years, but with her, I couldn’t last long. She began to moan in appreciation. It wasn’t long before I was cumming into the rubber. I asked her if she faked the moans and she said “no, I don’t have to do that.” A small, sad part of me wants to believe that. It really does.

After we cleaned up and got dressed, she said something that touched my heart. She told me I could still call and chat with her from my new town. Purely out of anxiety and awkwardness, I snorted out an “ok.” I think she was mildly hurt, and I still feel guilty about that to this day. Like I said, she had always been good with girl advice, and she told me she told me she hoped I found the one. We hugged, kissed on the lips and I told her to take care.

As stupid and silly as this sounds, when I got in my car and drove away, I felt weird. I think there was a tiny bit of sadness mingled with some calm reflection and a strange sense of closure. The thing is, though I had random hookups, I had always liked women who weren’t available to me. I was, you could say, king of the friend zone. It was what it was. But looking back on it, Sophia was the closest thing I’ve ever had to a romantic partner. (It’s not that no one was interested, but I was either hung up on someone else, afraid to take that step because of my illnesses, or feeling like I needed to be well before I jumped into a relationship.)

A year later, I went back to the parlor. I asked if Sophia still worked there. The woman told me that no, she didn’t. I think she had a boyfriend or something, and he didn’t want her working there. She moved away with him and her kids. I was happy for her, but a selfish part of me wished she was still there.

Apparently, the club (kind of) cleaned up after she left. A few girls were still willing to go below the belt with fingering and oral for the right price, but it wasn’t excessive and straight up penetration was no longer in practice.
It’s been about a year since I’ve been there. I came to find out last year that these habits of mine were a result of hypersexuality associated with borderline personality disorder. It was basically a way for me to feel validated and combat the never ending pit of self-worthlessness I was trapped in. As I worked to get better, I became ashamed that I used to go there. It was gross, sad and far beneath who I really am. I want to be clear that my intent was not to perpetuate the cycle of vulnerable women having sex for money. I was just trying to be good enough.
I am still a work in progress, but visiting those places is a thing of the past for me. I always used a condom for penetration, but not other things, and I’m lucky I didn’t end up contracting an STD. My anxiety over such (and wasting money) is far too much for me to go back there. I’ve also grown past it. I don’t have it in me anymore. I don’t allow myself to hope for much anymore, but it would be nice, if I ever get to a good place mentally, to have a girlfriend and even (gasp!) a wife. I’ve done random hookups with girls on dating apps a few times, and even that isn’t me anymore. Even though I’m not sure I deserve it, I want the real thing.

But I still, sometimes, think of Sophia. I know, you’re probably thinking I’m stupid, that I was just a way to finance her probable addiction to pills and who knows what else, and that I’m one in a long line of Johns who caught feelings for a sex worker. And maybe I was. But I didn’t really have romantic feelings for her. I just felt connected to her, I guess.

In any case, for some strange reason, I’m glad I met her. I hope that wherever she is, she’s doing well.

Source: reddit.com/r/gonewildstories/comments/ifa6zl/when_young_boy_met_sophia_mf_long