Tw: sex work, depression, body image issues – are those triggers? I dunno
I mostly want to chronicle this for my own sake, but if other people find it interesting that’s cool too. Go to the ***** if you want to get to the interesting sexy part. This first part will just be me setting the table by talking about my past.
I recently turned forty, but I’ve had fewer sexual partners in my life than many teenagers. I spent many earlier years of my life lonely and depressed, suffering from body image issues related to being a lot smaller in stature than most males my age. My first sexual experience wasn’t until I was 25 and it was with a sex worker. I’m not ashamed of that, I’m glad I did it. I appreciate what sex workers do and thank them for making a guy like me feel good, even if it’s temporary and not necessarily “real”.
I was in a long-term relationship spanning most of my thirties. I was always monogamous in that relationship, but she was my first girlfriend and regular sexual partner. We had a pretty good sex life and she fulfilled a lot of my fantasies, but one thing I never got to do with her was oral sex. Giving it. There are reasons for that which I won’t get into, but I was resigned to the fact that I’d never get to eat pussy in my lifetime. However, that relationship ended, and I’ve made it my quest to eat some goddamn pussy. I’ve watched videos, taken meticulous notes, I just need a real-life vagina and clit to work with here. As I mentioned, I’m a smaller guy, so at the very least I want to know what I’m doing with my damn tongue.
I’ve never been one to get many dates. And you can’t walk around the grocery store asking cute girls if you could practice eating them out. At least around here that’s how you get arrested and cancelled. I tried dating apps and got nowhere. Truthfully, I don’t have time to get into a relationship and I’m only looking for something casual right now. So back to trusty sex workers I go! I hired an escort late last year and ate pussy for the first time. She seemed to enjoy it, and I fucking loved it more than I even imagined I would. Of course, with the pandemic still lurking around, I didn’t get a chance to go downtown again. Until tonight.
***** fun stuff starts here I guess
We’ll call the recipient of tonight’s fun Ashley, because I like that name. I saw Ashley back in October at an adult massage parlor. She came very well reviewed and our personalities instantly clicked. She’s 5’4” with long blonde hair, green eyes, D cup boobies, some tattoos, a wicked smile, and an infectious laugh. Extremely personable. So easy to talk to. Perfect for this line of work, really.
I told her straight up that I was longing and craving physical touch, which I hadn’t had in almost a year since my ex and I broke up. She made it a point to give me a very tight hug every time I said the word “touch” which became a running joke throughout the first session. We had a lot of laughs, she massaged the fuck outta me, I got a happy ending, and she made me feel great. That’s the point of this, after all. But this story isn’t about that first session, it’s about what happened tonight.
I prepped for tonight as if it was a date. Trimmed my nether regions. Washed and scrubbed all my crevices. Didn’t eat garlic today and did a deep clean of my mouth before I headed to the massage parlor.
I paid my money to the girl at the door and slipped into the shower, awaiting Ashley’s smiling face. She entered and recognized me right away, greeting me with a hug and a kiss! After some small talk, she got on the table and I began to massage her. As someone who has been quite touch-starved since the beginning of the pandemic, it was awesome to oil up her body and run my hands all over her. After some of that, I asked Ashley, “what’s on the menu?” We had a good rapport but I didn’t want to push anything that made anyone feel uncomfortable. Respecting boundaries is hot, y’all.
“*Are you up for some Australian kisses tonight?*”, I asked – she looked at me quizzically, and told me she didn’t know what that was. “*They’re like French kisses, but down undah!*” That made her laugh uncontrollably for a good minute, which I loved. There’s not much better as a guy than making an attractive woman genuinely laugh, y’know? I let her know straight up that I’d only done oral once in my entire life, but she said if I tipped a little more than she’d be up for it. I immediately put the money down on the table and I was so happy that it was time to get what I really came for!
I kissed her up and down, massaging her titties lightly and flicking her nipples with my tongue. Slowly from there I moved downwards, kissing a path down to her beautiful treasure between her legs. More gentle kisses around her inner thighs, then onto the main event. I took it slow, building the tension (but still keeping in mind that we were under the clock – she’s a professional!). I asked if I could use a finger, and she said please do! Her pussy was so fucking perfect and tasted amazing. Slow flicks with my tongue on her clit while giving some come hither motions with my finger. Slow flicks turned into long licks and if she was faking, she got wet as fuck while doing it.
I have no idea how long I was down there but I loved every fucking second of it. She was wrapping her legs around my head and I was eating the fuck out of that pussy like it was the end of the world. I would have stayed down there all god damn night if I could have. One important thing I’ve learned in my research: if a woman says “*Oh fuck yes, keep doing that*” or “*Mmmm I really like that*” or “*Yessss that feels really good*” **THEN YOU KEEP FUCKING DOING WHAT YOU’RE DOING AT THAT TIME AND DON’T EVEN THINK OF CHANGING IT**. The feeling of giving her that pleasure and her bucking her pelvis into my face while asking for more is something I want to repeat over and over and over again. Preferably without having to pay for it, but if I’m unable to find anyone in “real life” to give some head to, I’ll be going back to see Ashley again.
Again, if she was faking and being a professional, she did a great job of acting like I scrambled her brain with some pretty damn good oral. She admitted she was apprehensive when I originally mentioned that I’d only done it once before in my life. But in her words, “that’s a damn shame!” because I suppose I was pretty good for a beginner and I’ve wasted all these years not eating pussy? I asked her for some constructive feedback, and all I was told is to keep doing what I’m doing. So I guess the studying and note-taking paid off!
By now we were quickly running out of our allotted time and she flipped me over for the happy ending. At this point I should mention that I had been abstinent from pornography and masturbation for the past month, because I had been going a little overboard with it while locked down for Covid purposes in January. I was successful at a no-fap February, but I warned her that I might be like a fire hose going off after holding off so long.
Now just turning forty, my little guy sometimes doesn’t agree with how turned on I am anymore. The escort I saw back late last year was unable to get me to finish, despite her trying a lot of very sexy things including the greatest blowjob I’ve ever had in my life. And unfortunately, tonight my pecker didn’t seem to want to agree how hot it was that I just ate the fuck out of Ashley’s delicious pussy for god knows how long, as I now I have her soft D-cup boobies smothering my face while she jerks me off and I’m fingering her still-sopping-wet love canal.
Well, at least that was until she started talking dirty into my ear. “*I love how fucking great you ate my pussy. You made me cum so hard. Now I want you to cum. Do you wish your cock was in my dripping pussy right now? I bet you do…*” That did it. I fucking unloaded so god damn hard that my fire hose warning was certainly appropriate. I’m pretty sure I exploded **ropes** of jizz all over the place that would make Peter North proud. I’m not entirely sure, because Ashley was had situated herself between my penis and my face.
Now unfortunately for Ashley (or fortunately from some points of view, but I felt bad), being in the position she was in and the fact that she was not expecting that much cum, she got an unexpected facial. She was a good sport about it, even joking she should have known better because I had totally warned her beforehand! She also told me she’d never seen someone cum like that before, which I took as an incredible complement considering her line of work.
I laid there in ecstasy to recover while she showered, and I followed with a shower of my own. We had a ton of laughs and hugs before she sent me off feeling like a million bucks. As I mentioned, I’d love to be able to eat some free pussy at some point, but if that doesn’t happen for me, I’ll be very pleased to see Ashley again in the future. My lips and tongue still taste like her and I kind of don’t want to brush my teeth tonight! But I will. Begrudgingly. Ashley’s smell and taste won’t last on my face, but hopefully by writing this story out my memories of eating her out will last forever!
Source: reddit.com/r/gonewildstories/comments/t6bxhk/after_40_years_a_story_about_me_finally_getting
You sound like a nice guy. Maybe you just need to work on conversation on the dating apps or if the vibe feels right, go straight to “can I practice oral on you?”
I bet a lot of girls would be pleasantly surprised and up for oral 😉