Friday, October 30, 2015

Prostate Milking

Isabel didn't call for three days after the night she put the face harness dildo on and I fucked her that way. I was going crazy. She doesn't like me to call, she wants to call me and I've been told off enough times I know better.

Valerie
Valerie has been strutting around the office and appears happy. Julie, the admin, told me she was seeing someone else now and it made me feel like shit. She's moved on. I love Valerie. Not the way I love Isabel. I love Valerie because she loves me, because she is sexy and nice and is kind and I like being with her and sex with her is always good. Just seeing her my cock begins to expand and then shrivels when the pressure of the cock sheath stops it.

Isabel confuses me. Valerie confuses me, but less. But I am with Isabel. At least I think I am. I know I am not with Valerie.

I love Isabel, but it is more of an obsession than real love. An addiction. Sort of like cigarettes. They make your throat sore and you smell, but you can't stop. I can't stop being with Isabel, and Isabel has me by the balls, literally.
Anyway, I called Isabel last night because I couldn't stand it any more. I left a message because she wasn't in. Today I tried to have lunch with Valerie, but she said no. She said she's had enough heartache and that she had just started seeing someone that made her very happy.

Isabel called at 5:00 and told me to take her out to dinner at Toca Madera. I picked her up at her place at 6:00.

"Where's your collar, Marc?"

"I, well, it's in the glove compartment."

"Put it on. I want you to have it on when we go out. I like to be seen with you, and I think you should be proud to show you are mine."

"Of course, Isabel." I reached in, got my dog collar, and put it on. She helped buckle it in place. She's nice like that.

This is typical of the way conversations go these days. She tells me what she wants, and I do it.

We drove over to Beverly Grove and went into the restaurant. She played with my hand on the gear shift on the way over.

It was a nice evening in it's own way. I told her about some of the nasty stresses I was under at work, and slipped in a little something about how I wasn't seeing Val and that I avoided her at work. I'm hoping the subliminal messaging might get through and she will let me out of my chastity.

Isabel also talked about her work and her mom; her mother is divorced and living with a woman. Apparently she realized she was lesbian after Isabel was born. I made a comment about the idea of women like, changing their minds about their sexuality, and wondering how that could happen. This rather set Isabel off.

"Marc, you have no idea the social pressure there is on a woman to conform and be straight. Many women live most of their lives without realizing they don't have to be with a man. I just happen to be lucky."

"What do you mean, lucky?" I asked curiously.

"Oh, I knew I liked girls since I was what, 14 years old? I've had a lot of men and men are nice playthings, but I've been aware I was lesbian and accepted it from an early age."

Uh.... wait. My girlfriend is a lesbian?

"Isabel, I uh... don't understand."

"What don't you understand, Marc?"

"Well, how can we be.. like, together, if you are lesbian?" I was dumb, asking this right out. There's a lot of things I am dumb about.

"Oh, well, I wouldn't say I am totally gay. I am more of... well, a bisexual lesbian. I like guys, but only in their place. I don't mind a fuck every once in a while, but when it comes to a real relationship, it has to be a woman." Isabel said this nonchalantly, almost dismissively.

God, I hurt, deep in my heart. I love this woman and here she was telling me... what? I still didn't understand. My relationship with her is more real than any I have ever had.

"What do you mean, in their place? We had a really good fuck that one time, I thought. We are good together, enjoy each other. Right?"

"Yes, Marc, it was fine. I was stressed and needed some relaxation and you helped out. But most of the time, well... I would rather just watch you humiliate yourself. Yes, we are a good fit, really. I have to agree on that."

My face was red hot by this time, with hurt and embarrassment and confusion. We were a good fit, but she was lesbian, but not completely lesbian, and we fucked once and she liked it but normally she likes to see me humiliated but we go well together and she likes being with me? What?

"Awww, Marc. Is this upsetting you? You did know I like girls, right? I mean, you saw me with Kim that first night you tried to hit on me and made a fool of yourself."

"Yes, I knew you liked girls. I know you still see them. But I thought you were bi, and really just doing it for fun, like on the side."

"Let's head back to my place," Isabel said.

I paid the bill (I always pay the bill) and we headed to my car. Driving back to Isabel's place I calmed down a bit. After all, regardless of what she said, I was with Isabel now driving back to her house. I spend several nights a week with her. I had just taken her out to a nice dinner. We get naked and have some sort of sex play frequently, even if it isn't exactly typical. If these aren't what a boyfriend does in a relationship, I don't know what else would qualify.

We got to her house, and went inside. I took off my pants almost automatically; she has asked that I remove them so she could check my chastity each time I've been over there. I fold them neatly on a chair near the front door when I enter. I'm getting used to the ritual, I guess.
I spoke with Isabel again as she inspected me.

"Isabel, I've been faithful to you and had this chastity thing on for three weeks now. Can we pleeease take it off? I can't even masturbate in it, and I haven't cum in ... well, three weeks."
"That must be hard, I know," Isabel said sympathetically. "I tell you what. I know just what you need. You've been trapped in there for a while and need to cum. Guys need to spurt their semen every once in a while or they go insane, I know."

She took my by the hand and we headed into the bedroom. My heart leaped. I was going to get the device off, and maybe, just maybe we might fuck. Or anything. 

"Kneel on the bed, all fours," she said. I took off my shirt so I was naked and climbed up onto the bed.

"Spread your legs a bit. Let me get in there."

I was so excited. She was actually going to take the fucking chastity thing off. I held still, making myself available to her.

She fumbled a bit, and then I felt the lock click. The sheath slid off... omg... the air hitting my cock felt sooooo good. It went erect, hard as a rock, instantly.  The ring around the base of my cock and balls was still on but my cock was free and clear!

"Now, let's see about helping you out a bit, shall we?" Isabel said kindly. She reached for a small plastic dish from her side table and put it on the sheets between my legs. Then she began stroking my cock.

I moaned. She stroked from the base to the top, paying attention to the best spots, which was electrifying. It felt like her hand was reaching inside my body and stroking the semen right out of me.

Then I felt something pressing against my ass, pushing into my anus. Wow, her finger. She was reaching into my asshole with her finger, penetrating me.

The experience was fucking amazing. She reached her finger in, hooked it a bit and pressed down hard. It felt so strange; not like, really sexually stimulating like she was doing to my cock, but wow it added so much sensation it made me grunt. It was overwhelming.

She just worked me like that, rubbing inside my ass with one finger, and stroking my cock with the other hand, and talking sort of quietly, urging me on.
"That's it, Marc. Let it come. Let it flow inside you. Let me help you get it out. Release your semen. Flush your system. Relax, concentrate and let it go now..."

And it did. The fluid began flowing out, I shuddered with pleasure as an orgasm rocked my body. She kept on working my cock and ass as the cum jerked out of my penis onto the sheets. The orgasm had built up for nearly three weeks and now she was doing me, it just went on and on.

It felt like I had cum a gallon, because it just kept flowing. Her finger in my ass pressing hard seemed to increase the flow as well. I didn't just moan, I grunted and cried out as she kept stroking and urging more and more out.

"That's it Marc! Give it to me! Push it all out, get all that stuff out of you. Pour it out. Let it flow."

Then it was over. Suddenly. There was no fluid left inside me, and after a few last strokes Isabel said, "Good boy," and stopped stroking. She withdrew her finger from my ass, and put the plastic dish with my cum on the side table. I looked at it; it had a lot of white stuff pooled on the bottom.

My cock wasn't completely limp, but it had lost a lot of its hardness. Isabel took the chastity sheath and slipped it back on. Some of the left over cum smeared my cock and helped lubricate it as it went on. It wasn't easy and she had to shove hard because of the remains of my erection, but she finally got it on and with a click it was locked back in place.

"There!" She smacked my ass with satisfaction. "You are all nice and emptied out."

I rolled over onto my back and looked at the chastity device trapping my cock.

"Isabel, can't we--"

"We just got you milked nicely, you should be good for another week or two. Let's discuss it then, shall we?"

We used the face cock again then. I fucked Isabel good, except I didn't actually touch her while doing it. I'm getting good at using it. It's a special skill and I think I did well. Isabel seemed happy afterward.

I'm back at home now, thinking about the day and evening. It's clear I am with Isabel, she is spending time with me and we go on dates, I am committed to her as she is with me. So her sexual approach is a little kinky? So what?

OK, her sexual approach is very kinky. Like, totally kinky. I'm adapting to it. In fact, it is weird but I am actually into it, more than just adapting to it. I am becoming completely involved with it. When she milked me tonight it was the best thing in the world. Yes, I would have loved to lay on top of her and thrust into her and fuck her until we both screamed and leave a huge load inside to come dripping out of her.

But, I like the way she handles me. Takes control. And the orgasm tonight? Was it worth three weeks wait? Well, not sure... but... maybe?

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