I still do on occasion, but, years ago, I used to love escort encounters. I lived on one side of a big city, and my family on the other, and so I would have occasion to drive through the city for visits. Anyone who enjoys escorts knows that a big city presents a larger catalogue of choices; plus, there’s just something exciting about knowing that you’re going to enjoy some play time on that exact night of the drive.
One of the more memorable women I met was an asian MILF. Chinese/Japanese to be exact, as she eventually shared this with me. I happen to love mature women..in fact, I have a fixation upon them. I could get into why, but that’s best saved for another story. The short version is that they tend to be comfortable thanks to their experience; they don’t tend to give or tolerate bullshit that can be more common with younger girls; and they often can sense my desire for some nurturing and care-taking toward me when intimate.
This woman is a complete angel, and I think it goes beyond her “act” to some extent. She can speak a functional amount of English, but just the basics. While this isn’t usually helpful, in our sexual situation I have found it to be an advantage – it can be such a cute experience when language is limited. Body language, emotion, and simple kindness become the tools of communication, and this is how I feel able to conclude that she is a truly kind-hearted caretaker of an escort.
When I first met her (and every subsequent time – I think I’ve visited her maybe 7 times), she opens the door slowly, and stays behind it as it opens. This threw me off at first, because no one was there and it seemed like it was some sort of automatic door. Anyway, I hesitantly walk in and look for her, and she’s modestly smiling behind the door, and closes the door gently, as if she’s trying to please me in her gentle demeanor. I’m instantly charmed by this.
Then, she gives me a nice, warm hug, and says “thank you for visiting me”. Yes, she is an escort – I’m not delusional to think that this is anything but service. That said, I could tell then and know now that her heart is something she shares, and that it truly makes her happy to make others happy, too.
The details of what was said in the pleasantries to follow are a bit foggy, as this was about 10+ years ago. But everything was going well and we were going to start having fun, when she got a phone call. She spoke in her mother tongue and so I couldn’t possibly know what was being discussed. After the call, she asks if I can wait a bit; she has to see someone, but she promises that he is quick. Now, I would normally be more skeptical, but she had a good reputation, and, furthermore, I’m a pretty patient and understanding guy. This appears like the usual escort run-around bullshit, and so I could see many clients either getting upset, leaving, asking for a discount, whatever. I don’t do that, and never have wherever possible, and here’s why: if the goal is to have fun and achieve some intimacy, I can’t think of a tackier thing to do than harp away at the “transactional” aspects of the encounter. Again, not deluding myself, but paying for this encounter doesn’t mean we can’t have a mutually enjoyable experience within its boundaries. If I’m patient and understanding with her, she’ll do the same for me, we’ll establish a level of trust, we’ll be able to then look eachother in the eye, allowing the experience to be as inhibition free and sexually connected as you could ask for.
So yeah, I told her that it was ok, but I gently ask for one condition: “sure, but here’s the deal: If I can cum twice within the session, will you allow that?”. This was not difficult; she didn’t mind at all and said “I will ALWAYS make that deal!”. Fucking hot, as this shows how much she enjoys making her clients feel good.
And this is where one of my favourite little sexual moments of my life happens. She shows me into a second bedroom, and I sit on the edge of the bed, and there’s a computer monitor on where I think a baseketball game was on. But I didn’t realize that she was still there, standing and smiling in the doorway, until I looked up to notice. She then slowly walks to sit in the computer chair, between me and the monitor. She’s no longer wearing her shirt, only in her bra from the top up. I’d seen pictures, but nothing can replace real life: this woman was so slim and skinny like many asian women tend to be, but my god was she busty. That bra was the perfect fit, and those tits were hugged together in a way that makes my mouth water at the memory of them. She notices my fixation and finally reveals her intentions in a single sentence I will never forget:
“Do you want to see?”
In those 5 words, she beckoned all of my pre-pubescent fantasies to come forth into my consciousness. Oh, how I fantasized about this in my sexual coming of age: a woman older than me offering to show me her breasts, knowing how much they would mesmerize me.
With a beaming grin, I looked her right in the eye, and simply said “yes please!” It was hooked in the front, and so her hands slowly reached between those beautiful curves. She was smiling at me the whole time, and I think I’ve mentioned that smile enough times that you might be starting to realize: that smile is a HUGE part of this woman’s sensuality. She was with me in that moment, genuinely. She genuinely enjoyed that this would make me feel good, that I would look back on it with happiness.
And so she unhooked that latch. And so it happened: one of those rare moments where my consciousness was able to fixate on something entirely. 100%. As powerful as that smile was, I was now lost in her beautiful, naked chest. It was like time stood still. Like I could see her curves ripple in slow motion as she ran her hands over them, squeezed them, shook them. She pulled on her nipples, turning them up like teapots before letting them drop back down with all of their weight. She cutely giggles at the little-boy state of mind that’s written all over my face.
She then leans in my direction, letting them hang and swing as she continues moving toward me. I don’t know about you, but with me, for some reason, when a woman leans forward and lets her tits hang freely, my cock just throbs on another level. My eyes fixate. She’s still smiling, which makes me feel all the more welcome to *stare*.
Eventually, that swaying femininity was hovering right in front of my eyes. That tan asian skin tone. Those dark, dimpled areolae. Thick and prominent pencil-eraser nipples that brushed over the palms of my hands as I had gently cupped them, letting them pendulate over my skin. I looked up and smiled back into her eyes as I had taken her in my hands and was made to feel like I was given toys to play with.
It’s that snowflake effect – I had handled many breasts before, and have many since, but in that moment there is no comparison. There is no one perfect pair, but only examples. Her womanhood in my hands were my favourite things in existence in that moment, and are example of perfection in my memory. I love all sizes, being totally honest, and can be equally turned on by A cups, B cups..size is no issue. But in this woman’s case, her genes made it such that body fat did not accumulate anywhere BUT her magnificent tits. Slim with big tits, for me, is certainly one of those irresistable body types!
I nuzzle in, burying my face in her warmth. What a place to be..if only she was there any time I felt anxious, alone, any type of distress..this is an instant cure of any such hang-up. You women out there, I’m happy to tell you that your breasts have power – a positive, alluring one, that makes a guy like me just wanna disappear in them forever.
Of course I’ll eventually suck her nipples, but I enjoy kissing and sucking the entire breast, too. Such softness. I love them entirely, and want to give them a complete shower of appreciation. Meanwhile, I’m tweaking her nipples with my thumbs and forefingers, really enjoying how perma-hard they are. I could feel them up all day.
I eventually realize that she had the back of my head in her hand for some time as this was all happening. She was also still kinda standing or hovering over me, letting those tits – more properly, those *breasts* in this moment – dangle in my face, and so looking up at her was incredibly angelic, that nurturing smile never wavering the whole time. That’s my last image of that moment before she slowly stood up, rubbed my cheek lovingly, and said, “I will be back. Wait here.”
She closed the door and I was so electrified that I came within 2 minutes of her exit. I had noticed a tissue box, and so I made a nice mound on the computer desk and shot a frenetic load onto it. Why would I do this, considering that I was going to fuck this woman within 15-20 minutes? Well, partly because I couldn’t contain myself, but I also needed to let it fly so that I wouldn’t cum within 10 seconds of penetration come that time.
From there, 15 minutes or so seemed to take forever as I waited for her to return. I couldn’t complain, though – those topless moments also seemed to last forever in a good way, too, and so all things must balance.
The eternity eventually passed, as I hear muffled voices in another language briefly, and the apartment door opens and closes. Footsteps approach my door, and the door opens and there she is, beckoning me to her. She invites me to shower with her, which I’m all too happy to do.
We washed each other’s bodies, which I found to be a tantilizing combination of sensual and cute, because of the way she smiled all the time, and took care of her “sweet boy”, her chosen pet name for me. Being called that name completely enchanted me. I wrapped my arms around her from behind, her tits covered in lather, as my forearm caressed them, shelved them under the stream of water, my hands exploring her flat stomach, and down her abdomen I went to feel her prominent mound of Venus.
Her pubic hair was not shaved but trimmed nice and tight, which gave a nice, gentle roughness to her pubic region. I let two of my fingers spread her cleft, and pulled slowly upward, my other arm tightly hugging her close across her breasts, my hand gripping her opposite shoulder. I firmly but sensually reached back with that hand and grabbed the hair at the back of her head, pulling it back so that I could nibble at her neck while my fingers continued to glide along her wishbone between her legs. I also playfully bit her earlobe, my steamy breath tickling her eardrum, whispering to her about her beauty. All the while, her soapy hand was stroking my turgidity as I heard light, breathy moans sneak past her lips.
After showering, we toweled eachother dry in a similar fashion, giving her another chance to show her love for pleasing her sweet boy by toweling me down. I did the same for her, and so it was time to get to the bedroom. It had nice dim lighting, a perfectly intimate setting. She lay me on my back, and sat at the side of the bed, as I looked up at this angel in a haze of sexual drunkeness. Smiling at me as she had been the whole evening, eyes locked, she said “let’s make love.”
From there, she shifted over to straddle my hips, her head above mine so that her perfectly straight black hair created a fortress around my face as our sexes made contact. I loved the intimacy of our faces being hidden together in this manner. She lowered her flowery lips onto the base of my shaft, and, slick with her nectar, began sliding up and down, as I thrust my hips along with her rhythm. If I hadn’t cum earlier in my waiting room, I certainly would have now. She slid up so that my cockhead could almost slip up to her entrance, but would then slide right back down my shaft as I thrust up against it. God, that felt so good, those labia hugging my girth the whole time. My hands were busy the whole time exploring her soft skin..brushing up and down the sides of her torso, the small of her back, that soft, supple ass of hers..I loved everything I touched.
Then, that moment came..she reached down, grabbed my cock, and pointed it upward. She lifted her pelvis so that I pointed straight at the target. Then, she lowered herself onto it, and I began to penetrate herself with me, inch by inch. Complete ecstacy. I’m cupping her tits in my palms as this is all happening, and we’re making full, sensual eye contact as the ultimate connection is being established.
Her pussy is as warm as her smile. It hugs my penis as tight as she did went I first entered the apartment. As she finished her descent, I’m also slowly finishing a nice, slow thrust so that I’m deep to the hilt against her downward push. We now both push hard against each other, as she grinds downward into my upward pressure. I can’t go any deeper, but oh my what a sensation in us both wanting more..we push as though we want both of our bodies to fuse into one.
I reach back and grab her ass firmly, pulling it up and down as we begin to gently fuck. In a connected rhythm, she’s bouncing up as I pull out, and then slamming down to meet my strong thrusts into her. We both have *depth* on our minds..I want my entirety inside of her, as she hungrily tries to swallow me into her infinite female need for depth.
Her tits are bouncing in my face, slapping together rhythmically as she’s pounding her pelvis harder and harder onto my insatiable cock. We’re both moaning like animals, completely lost in our inner animal drives, her hair continuing to contain me in sexual force field.
We’re both fucking betond control now, going for broke, loud slapping noises happening all over the place as my balls are smacking her asshole with every thrust, and my hands violently slapping that ass to bring out even more energy into her riding. I start moaning on a deep level, as we’re locking eyes and sharing steaming breath in the column of intimacy that we’re sharing in her dangling hair.
She can tell that I’m about to flood that pussy, and so she meets my determined rhythm as though to milk it out of me. “Go, boy” she moans to me as she keeps this steady motion. I wrap my arms around her tightly and hug her close as I approach orgasm. She digs her arms under me, wrapping her arms around me too, and we embrace in the tightest hug we can possibly experience as I thrust into her with all my might.
Both of us are moaning at the top of our lungs as we cum together. My cock is pressed as deep as it can go, her lips pussy pressing back with all her might back at me. We’re grind-fucking as my cock begins to pulsate, and I’m sure her opening can feel the spasms at the base of my cock as shot after shot of my essence starts pumping into the deepest reaches of her pussy. We are one in this moment, our minds centrally focused on this togetherness, this pleasure, this warmth..the height of my manhood and her womanhood fulfilling each other on a profound level as a seemingly endless series of cumshots fills her abdomen, both of us riding the wave of pure bliss, squeezing each other with all of our strength out of pure sexual desire, her pillowy breasts firmly against my chest making the feeling all the more wonderful. Her hungry pussy wanting more and more as I continue grinding my cock to its absolute max, shooting, shooting, shooting the pure liquid desire that her body hungrily milks from my balls. What a moment, one that you feel will never end during the experience..
..but it always does. Our grips eased. In the fog of the aftergow, I realized how hard we must have been holding each other, as it felt impossible now that I could feel how slick we were with sweat. As we were catching our breath, she did something that no one else has ever done, I think to put her stamp of approval on it all: she tenderly took a moment to coyly bite my shoulder before lifting up, which made me feel special in a newfound way. Our stickiness was so apparent that you could almost hear it separating, similar to a sweaty leather seat. “Good boy,” she whispered as my cock started to soften; I trembled in aftershocks as I felt myself slipping out of her. “Now *that’s* how you make love,” I thought to myself.
Between now and my departure is again a bit of a blur as far as talking points went. I recall talking about music, ended up sharing that I play guitar, and she asked if I could bring it next time to show her. Then she sang “you are my sunshine” for a bit, the song she would want to be shown, which melted my heart all the more in it’s completely unironic cute-heartedness. Obviously I couldn’t stay forever, but how nice of her to enjoy some real moments afterward, which shows that we both really enjoyed the company beyond a a cold hard transaction. There truly is humanity to be found within the walls of an escort encounter sometimes if you look for it (and find one who sees it this way, too). And it’s very healthy as long as you understand proper limits.
She walked me back to the front door, and gave me another loving hug. I told her I would love to come back. “Anytime,” she replied with her smile. Then she opened the door the same way as before, waved and smiled as I walked by, and out of the fantasy I walked, back into real life.
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This was my first time sharing a journal entry like this. It the way I’ve found for myself to springboard into erotic writing. I have a list of minor details for every sexual encounter I’ve ever had, and time allowing, I’d love to make a long version like this for all of them. But I’ll have to start from the most meaningful ones and go from there. If you made it to the end, hope you enjoyed, and I’m flattered that you took the time. Feedback is fully welcome! If it’s negative, that’s totally fine, and in fact good for growth – all I ask, of course, is that it’s kept constructive.
Source: reddit.com/r/gonewildstories/comments/fiqqu4/an_entry_from_my_sex_journal_my_first_of_many
Beautifully written! How do you go about finding a reputable escort the first time? And did you get to skip the condom this session?