It’s been a distracting week.  It’s been a distracting two weeks actually, which is frustrating because it’s really pushed into my time to be able to be creative.  Well, my time to be creative and perverted.  It didn’t, however, have any interference with my new found extracurricular activity; meeting sex workers.

Well, it's a sex worker.  Singular.  I haven’t gone and dipped my toe in another woman’s business just yet.  I’m not sure if there are any others that are regular in my area so I’m fine partaking in the very wonderful company of the woman I’ve found.

Starting off with a positive, because the overall experience was a positive again and a majority of any negative experience is because of myself, so I don’t think it's fair to start off and seem overly negative.  She was great.  

• I fucked her, as in penis in vagina sex (condom on, of course).  
• She played to one of my favorite kinks.  
• She’s got an amazing ass which I got to tongue a little bit.  
• I got to have her sit on my face.
• We kissed wildly on the bed

I’m still nervous going to see her though.  Mostly, I think, it's because I’m going to get a text or a call as I’m going in, or already in, and I’ll have to ignore it and then there'll be more texts or calls and I won’t be able to concentrate on having a good time.  For someone who considers themselves pretty relaxed I can really get inside my head really bad sometimes.  It’s part of what negatively affected the experience.  My fault.  

It turns out it was kind of justified though as when I was leaving I ran into someone I knew.  

Oh-fucking-yay!  

Thankfully I was far enough away from my new friend’s door that it wasn’t obvious where I was coming from and I could tell this person I had a meeting to get to so I wouldn’t be stuck in an endless conversation and it didn’t seem like I was blowing them off.  But at the same time, what in the actual fuck are the chances of running into this particular person, at that spot, on that day.

It all worked out alright though, none of my fears that kept me distracted happened and I was able to enjoy the full experience with my SWer.  I got there and this time she sent me the pertinent information instead of coming down to meet me, and I went in.  Thankfully nobody was around because I’m dreading the time I’m coming or going and I have to see another live human in the building.  That wasn’t this time and I liked that when I got to her door she had left it open a crack as she texted me, “no need to knock.”

One of my favorite parts about her is that she’s very touchy, which seems like it would be something obvious with a sex worker, but she’s the only one I’ve dealt with so it’s my only frame of reference.  She hugged me as I came in and sat extremely close to me on the couch for a little chat.  

She had on thigh high socks.

I love thigh high socks.

We kissed on the couch and I squeezed her body.  I hugged her tight and pulled her as close to me as possible. 

One of my favorite things about her, and I might have mentioned this in my previous post about meeting her, is that I love that she’s not extremely fit.  She’s not fat or chubby or overweight in any way.  She’s got the perfect body for what turns me on.  I love to be able to grab a woman’s hip or back or ass and have it feel soft.  I want my partners to be a little bit, as I somewhat unflatteringly say, squishy.  When I squeeze her hip or side and I have her skin in my hands I feel so incredibly aroused from it that it makes me want her more.

After a short make-out session she asked if I wanted to go to the bedroom and this is where the first negative came in; I was expecting to shower.

In our previous meeting she had me go into the shower and wash up then come in and see her.  I had expected that to happen again where I could make sure I was fresh for her.  Of course I had showered that morning but it had been four hours later and my stomach had been bothering me slightly earlier which led to me using the bathroom.  I made sure everything was tidy but I had hoped for the chance to do a double take and my mind had been stuck on that so much that I felt too nervous to lay flat on my stomach at one point.

That was fine though, I tried to not let it get too far into me and I followed her into the bedroom and crawled on top of her as she threw herself onto the bed.  I was fully dressed and she was wearing a bra, panties and those wonderful thigh high socks.  I kissed her lips and dry humped between her legs, thrusting my hips into her and showing my need to fuck her.  

God, I just wanted to fuck her.

My hands would repeatedly venture to her ass and I think she got the hint.  At one point she was undressing me, removing my pants with her head down by my knees and I took that opportunity to kiss and bite her ass cheek.  

She mewled and I continued.

She told me to take off her panties and I obliged, then leaned awkwardly as far as I could to press my tongue against her anus.  I wanted to slide my tongue inside her tight little asshole but I couldn’t get the right leverage, and I didn’t want to assume it was allowed either.  I know butt stuff is considered extra and some girls don’t do it.  The ones that do refer to it was the Greek experience, or some version of the term Greek, which I find funny because it's referencing anal sex and all of the male on male fucking the greeks did.  I love those cute little sayings sex workers have.

She never fully positioned herself so I could tongue her asshole, but I got close enough to make it enjoyable.  I’m not sure if she didn’t fully bend over and let me lick her anus because it was extra though.  She does offer the Greek experience but its an extra charge (not much), although I assumed it would mean fucking her ass with my dick and not my tongue, but I’m still a novice so I don’t assume to know anything.

When she got a gauge on my eagerness she did throw a knee on the other side of my head and let me hungrily suck her clit, eventually asking if I wanted her to sit on my face.  I gave her an enthusiastic, “yes!”

I love licking a woman’s pussy.  I absolutely love it.  It’s always the first thing I want to do when I’m going to have sex with a woman.  My hands will pull off her panties and I push her thighs apart and dive in licking, sucking, using fingers and moaning hungrily.  The only downside of doing it with a sex worker?  I don’t know if she’s actually into it (spoiler alert, she’s probably not).

So, while she’s leaning back and wonderfully sitting on my face with her pussy pressed against my lips I’m thoroughly enjoying every second of it until I let that thought, is she enjoying this, creep into my head.  I wasn’t getting in my head in a negative way thinking I was doing a bad job, but I typically enjoy cunnilingus because I love hearing a woman moan and enjoy it.  If she’s doing the moaning for my benefit and not actually enjoying it then the entire process can be over much sooner.

And it didn’t last overly long.  I enjoyed feeling the weight of her body pressed down over my face.  Her pussy on my lips was perfect, and at one point she did press her weight down and practically smothered me with her cunt and I wish I had the conscious thought of wrapping my hands around her thighs and pulling down harder.  I wanted to be suffocated with her pussy until I needed to push her off to gasp for air.

At this point she began to run her fingers over my body and drag her nails delicately across my skin.  It was heaven.  She made my entire body tingle in pleasure.  This was the big thing that got into my head though, she asked if I wanted to lay on my stomach so she could run her fingers along my back and I desperately wanted that.  

I had thought of this exact scenario leading up to the day.  It was something I used to do to my ex-wife and she would then do it to me, albeit much shorter in duration.

I craved it.

I needed it.

She offered it and I had instantly said yes, but then I remembered that I didn’t get to shower first and felt a heat swim over my face.  I didn’t want to flip over onto my stomach and have her see something I might have missed.  That would have been embarrassing for me and awful for her.  So when she got up and I was supposed to flip over I had instead kissed her and sucked on her breasts.  I kept doing that and eventually we laid alongside each other and made out while I fingered her.  I kept thinking she must be confused and it took me out of the moment, and I think affected the rest of the session.

At this point she had also asked if I wanted her to use more coconut oil.  For the most part I didn’t care what she did as long as her naked body was within arms reach of me, but take it or leave it I could have left it.  Apparently I have very dry skin though and she kind of asked if she could rather than asked if I wanted her to so I assumed she wanted to.  Who am I to tell a woman I’m naked in bed with not to do something to my body?

She oiled me up.  She oiled herself up.  She slid up and down my body again.  I had been erect for a while and she put a condom on me.  I was finally going to fuck her.  A small part of me, the prejac, beta, cuckold part that jerks off to no pussy porn wanted me to go another session without having my dick go inside of her pussy just for the kink aspect of it, but a part of me that would not be denied had a louder voice and let it happen.  

My dick lined up with her pussy and she slipped in.  The problem with condoms is that it's really difficult to tell when I’m actually in and when I’ve slipped out or never actually made it in to begin with.  Thinking back now, a few days later, I think I actually tried to fuck her with rocking my hips up and down while my dick had slipped out of her and wasn’t even inside her pussy.  Nice.

She was a pro though and slipped me back in, muttering playfully that, “just have to get the right angle.”

Then I was in again and she was rolling her hips toward me.

Then I slipped out again and she slipped me back in.

This happened a few times, her riding me slowly and my cock slipping out of her pussy.  When she finally gave up and climbed off of me I could tell my cock had gone wobbly.  It wasn’t exactly soft but it wasn’t nearly hard enough to stay inside of her for long.  God-fucking-damnit.

It had been quite a long time since I had fucked a woman but I knew what was going on and I knew there was a very large chance that I wasn’t going to be able to cum with the condom.  That didn’t stop me though.  I wanted to fuck her and I held out a small hope that I could actually fill the condom while my dick was in her pussy, so I climbed on top of her and she spread her legs around me.

I pushed my cock into her cunt and it went in, thankfully.  It was hard enough that it didn’t slip out right away and I fucked her missionary style for a couple of minutes, but I couldn’t feel anything.  I knew my dick was inside of her but there was no arousal anywhere close, but I didn’t want to give up yet.  With her feet straight up in the air and her legs closed tight I pushed inside of her still.  I kissed her feet and she pressed them to my face.  Still nothing.  I gave up.

I think at this point she gave up too.  She took the condom off of me and continued rubbing and kissing me.  Her fingers ran along my skin and I loved it but I was upset with myself, with my pathetic dick.  I wanted to fuck her and cum while I was fucking her.  That wasn’t going to happen, but I didn’t want to leave her without cumming at all.  As much as it would have been a feather in the kink cap of my gooner, no cumming porn brain I really did want to cum.  

How could I still be nervous with her?  I knew what I wanted but I was too nervous to ask.  I’m paying her to fuck me and I couldn’t ask her to do something for me that would help me cum?  Jesus Christ.  She was grinding against me and it felt like she was getting ready to call it quits.  I could almost hear the words.

“Looks like it’s not going to happen, I’m so sorry.  I hope to see you again though.”

I couldn’t have that.  It was all still there, built up, and it wanted to come out.  The words just needed to sneak past my lips, and finally they did.  I was able to ask her to do the thing I wanted to happen the first time, before her blowjob did a better job than I thought it was going to.

I said, “could you jerk me off,” and then added in a meek and timid voice, “could you do it while saying do you want to fuck me?”

She enthusiastically agreed and began stroking my bare, condom free cock in a steady, rhythmic fashion.  It wasn’t 30 seconds before I felt myself close to cumming.  Her voice was just the right amount of sexy and whiny as she repeated herself over and over again while she jerked me off.

“Do you want to fuck me?”

“Do you want to fuck me?”

“You want to fuck me, huh?”

“Yeah, yeah you want to fuck me.”

“Do you want to fuck me?”

“Yeah, you want to fuck me.”

I held her close.  I didn’t even think that I wanted to be sucking her breasts while she did this.  My mind was nearly in a state of euphoria.  This was perfect.  Oh my god, how is this really happening?

The only thing I struggled with, and I’m mostly glad I didn’t ask, was that I wanted to tell her to switch between, do you want to fuck me and no, you’re not allowed to fuck me.

I wanted to cum when she was telling me that I wasn’t allowed to fuck her. 

I wanted to cum while she told me I had to fuck her hand pussy, or that I had to cum all over my stomach instead of inside of her.  

I’m glad I didn’t ask that though because the orgasm felt so fucking incredible with her just asking if I wanted to fuck her.  My cum shot out all over my stomach and the only way it would have felt better was if she stopped stroking sooner because my dick got really fucking sensitive immediately after and she continued stroking for a good fifteen to twenty seconds and it hurt.  Yes, I could have told her to stop but I just asked a sex worker to jerk me off instead of cumming while fucking her so it goes to show I’m not the most assertive type.

After cumming she wiped me up as if it were the world’s best maid service.  I had laid there nearly comatose when an alarm started blaring from the other room.  She must have lost track of time or something because she seemed startled by it as well.  It had reached the end of our session and I came just in time.  

When I was getting dressed she told me that she really liked that I told her what I wanted, that it makes the experience so much better.  Yeah, that makes complete sense but the people pleaser in me has a hard time asking for things that only benefit me.  That sounds like a really stupid thing to say for someone who has gone to a sex worker twice now, but I have to try to remember that for future sessions to get the most out of it.

To recap:  I worried about being properly cleaned, had my dick go soft and couldn’t cum inside of her while wearing a condom, and waited until the very last moment to tell her what I really wanted. Sometimes it's not surprising that I went over 6 years without having sex.

She’s incredible though.  I gave her a few extra dollars as a tip because I enjoy how easy going and comfortable she makes me feel.  I also like that she’s made me ejaculate twice since knowing her.  

I’m considering scheduling another session with her, but it’s at an awkward time of the month so I’m trying to wait to see if the timing will work out.  I hope it will because I really want to be naked with her again, and, funnily enough, all I can think about is her giving me another handjob.  I wonder if she’ll let me cum on her tits.