She makes me nervous.  It’s not necessarily her naked body, with those full, voluptuous tits and wide hips that hold her delicious ass that I want to feel what it’s like to wear as a mask, but I feel nervous talking to her.  I don’t feel like I can be natural and relaxed.  All of my answers are stale, quick responses that mostly consist of a snorting agreement with whatever she suggests.  I’m sure she feels the awkwardness in me too.

I shouldn’t really start this off by saying that she is the one making me nervous because if you replaced her with any other girl I would be nearly the exact same way, so more accurately I’m making myself nervous because she’s a girl standing in front of me and I’m paying her for sex.  You would think that the sex being a forgone conclusion would make me feel more relaxed but it really doesn’t.

Her demeanor is amazing though.  She’s friendly and welcoming.  When she asked me to sit on the couch to talk I was thrilled with the way she practically sat in my lap and leaned into me so our bodies were touching.  That’s what I wanted.  It’s what I needed and why I ended up going to see her to pay someone for sex in the first place.  I wanted to be touched.

Sometimes you want something but are afraid to ask for it though.  What I wanted, deeply, was to suck at her breasts as she jerked me off slowly and lazily while talking to me in a soft and comforting voice.  

“There you go.  There you go.  You’re doing so well,” she would say in more than a whisper but less than her full unimpeded voice.

One hand would cradle my face to her breast and run her fingers along my cheek and jaw, with the occasional trickle down my neck and back up again.  The other hand would run down along my stomach and hip.  It would drift over my penis and just graze it before skipping along my testicles or inner thigh.  She would then fly her hand back around and her fingers would tap, tap, tap gently along my penis causing it to grow and twitch.

I would moan against her breast and maybe break the suckling of her nipple to whimper out.

“Shh, shh, shh,” she would respond and guide my mouth back to her breast and I would continue suckling and trying my best to latch onto her breast as if I were a newborn feeding at his mother’s breast instead of a man paying a woman to infantilize him for his own erotic pleasures.

How do you tell someone that you just met that you want that?  Or that you want her to continue doing this and saying almost pre rehearsed lines as she did it until she brought you to orgasm and it spilled all over your stomach?

“Do you like that, baby?  Do you like when I do that?”

“Oh there you go.  Keep on nursing.  Just like that.”

“Oh wow, look at you.  You’re so excited.”

“Are you close?  Do you want me to keep going?”

“There you go.  Almost.  Almost.  Almost.  Almost.”

“It’s okay, you can make your penis make cummies.  I don’t mind.”

“There.  There you go.  Let it all out.”

“You made a little mess on yourself.  Here, let me clean you up.”

“Aw, your penis is so cute when it’s finished making cummies.  It looks tired.”

Even with these phrases I’m holding back, although I don’t know why.  To think what I really want is for her to refer to herself as Mommy in the third person and occasionally call me baby, or some other term of endearment that is sweet and motherly sounding.  I can’t ask her to do that.  Not at first, not the first meeting, even if I am paying her to make me cum.

So we fuck instead, although I can’t cum with a condom on.  Even when I was married it was really difficult to cum wearing a condom, it always felt so tight and restricting.  I’m by no means well endowed, but I’ve been told my cock is kind of thick, at least for its length.  I don’t think that means I need any kind of magnum or extra large sized condom, but I wish there was a small, medium, large selection so I could go up a size and see how it fits.  I’m sure I’m just being fucking ridiculous though.

I can’t cum with the condom, even after trying various ways.  The last time I orgasmed while having sex it was with a random hook-up and I, stupidly, wasn’t wearing a condom.  The time before that?  Over six years ago when I was still married and we didn’t want to risk getting pregnant.  I would have to find just the right angle and just the right pace and make sure it continued just like that until I felt something akin to a tickle in the base of my cock.  If I could keep going just like that until it ran all the way through me I could fill the condom with sperm and finish, although that was a rarity.

Despite my effort of trying to cum inside another condom with a sex worker I failed.  She rode on top of me and I would slip out.  My dick felt rubbery and I almost knew it was the end and I wouldn’t cum, but I tried anyway.  I climbed on top of her and slipped my mostly stiff dick inside her and fucked her for another few minutes before giving up.  She sucked my condom-covered dick to finish me off the first time and I erupted in it.  It felt incredible.

When I walked away from her building my limbs felt like jelly.  They were extraordinarily loose and it was as if they flopped at the joints when I stepped or hung my arms down.  If it were windy I’d have been afraid of being knocked over by a sudden gust.  The feeling was unsettling, but nice.  I figured the orgasm was pretty powerful and it was the first I had in years that I got to enjoy because the encounter I had months ago with the random woman I had tried to hold back my orgasm because it was coming way too soon without the condom and despite my efforts it happened and was a muted, unsatisfactory feeling.

After a few days I had told myself I wanted to see the sex worker again.  At first I thought it was a one time thing, or maybe in a few months I would hit her up again, but the further I moved away from the experience the more I thought about wanting to have another go at it, at her.  Although it wasn’t just because I wanted to fuck her again, or even just because I wanted to be close to an attractive woman again.  A good portion of my wanting to see her again was that I wasn’t happy that I wasn’t able to cum inside of her while wearing the condom and I thought maybe she felt bad she couldn’t make me cum.  

Yes, you read that right.  I was concerned for a sex worker's self evaluation in her profession and that it might have hurt her feelings. 

The next time went even worse though.  I couldn’t cum and my dick felt flaccid as if it were a wet noodle.  It flopped around and I couldn’t get hard.  She tried to put a condom on it and it slipped off.  I wanted to crawl into a ball under her blankets and not come out.

“Do you want me to run my nails over you for a bit?”  She was trying to salvage the time I had left with her and give me something she knew I enjoyed.

I nodded.

I did want that, but I wanted more.  I wanted to cum.  I didn’t want to pay for sex and leave without having emptied my balls.  I would have been so frustrated and pent up that I probably would have jerked off in the bathroom at work as soon as I got back there.

“Uh, can you, can, would you jerk me off?”

I managed to stumble the words out in a meek, timid voice.

“Yeah, sure, absolutely,” she returned in a sweet and understanding voice.

I loved that about her.  There was no judgement and no hesitation.  The only thing she wanted to happen was for me to feel good.  She was such a professional at a job where she could do a lot less and still be considered good at what she’s doing.  I decided to ask for more of what I want.

“Can you do it while we’re standing up?  Your body pressed against mine and you reached around stroking me?”

She nodded, “yeah, anything you want you.”

I nodded and crawled out of the bed and stood at the foot of it.  She followed me and I watched her naked body.  Her full, luscious breasts hung from her chest and I ached to suckle them.  

Her body pressed up against my back, her nipples into me, and she reached down my front and cupped my balls.  I reached back and grabbed her hips, pulling her even tighter to me and moaned.

“I, I don’t want to cum like this,” I muttered nervously.

“That’s okay.  You tell me when you want me to stop,” then she began stroking my cock and getting it hard again almost instantly.

I wanted her to ask her to talk while she did it.  My cock was already hard and I wanted her to say what a good job I did getting my penis hard again, but I was still too nervous to be that vulnerable.  I should have just asked because I know she would have done it, but I can’t break free of this shameful shell I’m stuck in.

After a couple of minutes of her slowly stroking my now fully erect cock I put my hand on hers and pulled it off.  If she had continued for even 30 more seconds I would have orgasmed and my cum would have shot all over the floor.

I turned around and she kissed me and I kissed her.  I love kissing her, but I wanted more.  I wanted to drive my tongue wildly in her mouth in an insane kiss that had no boundaries, but I knew this entire experience does have boundaries and I couldn’t let loose like that.  I kissed her back and grabbed her bare ass and squeezed her delicious cheeks.

A thought entered my mind and I don’t know why but I suddenly was overcome with the urge to cum on her face and tits.  I didn’t know if that was allowed though, seeing as how it's bodily fluid on her and I wasn’t sure what the rules were for that kind of thing.  I had never done it though and I wanted to look down at a girl’s face covered in my cum.  I’m not sure why I wanted to but the feeling was there and it was strong, as if it were pounding in my chest to be heard.  

I don’t know if afterwards I wanted to kiss her and it was the cuckold, sissy, beta part of me speaking up or if it was just an alpha male speck somewhere inside of me that wanted to have a woman degrade herself with my cum on her.  I was hoping it was the former.  I was too nervous and shy to ask.  I didn’t want her to think I was disgusting and I didn’t want her to have to tell me no to something as everything else had been so agreeable and easy.

Even with a sex worker I’m a people pleaser.  

A flood of things ran through my head about what I wanted to do with her, but I couldn’t decide on one.

Suck on her toes.

Tongue fuck her ass.

Fuck her tightly closed thighs.

Fuck her tits.

Dry hump her ass.

Get a footjob.

Kneel at her feet and cum on her toes.

I wanted to play out every kinky scenario that I had jerked off to in my entire life but I couldn’t tell which one I wanted most and it left my paralyzed to ask for any of it.  

“What do you want now, what would you like me to do?”

I smiled at her, that same shy smile I couldn’t shake, and asked her to jerk me off again.  It was safe and I knew she already liked that I asked for it and it was always a top five favorite of mine to be jerked off by a pretty girl.

“Okay, let's do that,” she said with a smile and crawled back onto the bed.

“I really like it when you tell me what you like,” she added as she lay stretched out and naked on the bed.  Her body was a temple to real, sexually empowered women.  There was nothing fake about her and she looked like the kind of woman you’d see on the street and admire her curves.  You’d think how you’d love to see her naked.  You’d think how you’d love to fuck her.  You’d never know you could for the right price.

She jerked me off again.  I had thoughts of telling her what I wanted, that I wanted her to tell me that I wasn’t allowed to fuck her anymore and that I was only a little jerk off boy.  The thought had me so excited but my shyness held me back.

I wanted to hear her say, “you’re paying me to jerk you off and you’re going to cum all over your stomach.  You’re not going to fuck me anymore, no matter how many times you come see me I’m going to jerk you off and you’re going to cum on your stomach.  You’re going to be my cuckold.  You’re not allowed to fuck me anymore.”

I couldn’t tell her that though.  My shameful thoughts were for me in private.  My weird kinks and fetishes couldn’t possibly be shared with another person that wasn’t a man I was being disgusting with on the internet.  She would think I was a freak and it would change her opinion of me, the man who is paying her to have sex.  The man who she doesn’t know if he’s married or not and could be cheating on his wife and this is why he’s so cagey and shy.  She might think I’m a freak or a loser, this woman who will only allow me to come near her if I pay her.

I liked her too much though.  I liked kissing her and laying naked in her bed.  I wanted to feel her sit in my lap and run her fingers through my hair and if I told her all of the fetish, weird stuff I like she would hesitate and it wouldn’t be easy like it is now.  Like the slow and sweet way she’s jerking me off because I can’t stay hard enough to have her ride my cock and how I can’t cum while fucking her with a condom on.  

“Can you say, over and over again, do you want to fuck me?” 

I asked her this while she was stroking me and she nodded and began immediately while her hand ran up and down the shaft of my cock.

“Do you want to fuck me?”

“Do you want to?  You want to fuck me?”

“Yeah, you want to fuck me.  Yeah you do.”

“Do you want it?  You want my pussy?”

“You want to fuck my pussy?”

“Yeah, yeah you want to fuck me.  You want it.  Yeah, yeah, yeah.”

She only had to say it a few times because with each time I got closer and closer to orgasming.  I pumped my hips and whimpered loudly.  I moaned even louder.  She could feel it getting closer and she got louder, right in my ear.  She said it faster and then my body shuddered and my cum shot out on my stomach.  She lowered her tone and continued saying it for another few moments after I finished while her hand continued to work out the cum from my cock.  It was so sensitive that it hurt and I had to move her hand away.  

She got up and went to get a hand towel and cleaned me up while I laid there and basked in the post orgasm reverie.  As she climbed off the bed to throw the hand towel in the laundry she saw that our time was over.

“Looks like you’ve got a great internal clock,” she smiled at me and handed me my clothes that were strewn across her floor.

I merely chuckled and agreed, back to the shy and nervous person I was before asking her to jerk me off and coax me into an orgasm.

We said our goodbyes and I went to my car and drove away, thinking I was going to see her again.  I wanted to do this again, almost exactly the same way.  I wanted to fuck her with the condom and not be able to cum and have to resort to her giving me a handjob and cumming all over myself.  But maybe the next time I’d ask her to say something different.  I don’t know if I could get her to let me nurse at her breasts while she jerked me off and mothered me, but I might be able to open up a bit at a time as if she were some kind of therapist and sexual entity.

I’d ask her to jerk me off and instead of asking if I wanted to fuck her I’d ask her to beg me to fuck her.  I’d ask her to say, “why won’t you fuck me, please I need your cock.”

Or not.  I don’t know.  I just know I want to do this again.  I want to keep doing it and spending money on a woman to have sex with.  Maybe it will help me open up sexually and try out my fantasies.  Maybe I’ll just end up having her jerk me off everytime and we’ll get into a nice routine.  Maybe I’ll be able to ask her for everything and I’ll be comfortable enough with a woman that I can be vulnerable.  Maybe I can just be me.