Chapter 44: Getting your holes raped by two men…

I wake up. It is 5AM in the morning. The first thing I do is check Skype if Eric is online. He is. I feel lustful already. We video chat and fantasize about our real future meeting. No kissing until we are somewhere private… It gives me butterflies when I think about Eric’s lips touching mine. My mood is set and I am ready for our session.

Sir wants me to put my hair up and get rid of my clothes. I put my hair in two pigtails, playfully strip and set myself in position one. I feel good about myself. I lost around 10 pounds since March. Sitting still in this position is not easy. My legs are cramping at some point.

“Look forward, mouth closed.

Hold yourself steady.

Remember, you are proud to be my Sub.

Shoulders back, chest forward.”

Damn. Not so perfect. I correct myself. Sir seems pleased now and instructs me to get my play things. Today I need the plug, both dildos, lube and two pillows.

“First step will involve you on your knees on the floor.

Bend over the bed, ass facing the camera.”

OK, I can handle that. I use the kitchen steps for my laptop and rearrange it until Sir is content. My ass is pointing to the camera.

“Damn that looks so good!” Sir says.

Sir confesses he almost wants to change his plans after seeing me in this bending position. Sir is not wasting any time and orders me to spank myself with my hand, medium intensity. After a few hits I get a reward. I can lightly touch my pussy.

“I love rewarding you after I spank you.

Does my little one like that?”

“Yes Sir.”

“Resume spanking.”

I hit my ass cheeks and hope it pleases Sir. Though I can’t wait for my reward again.

“Stop.

Back to teasing…”

Sir really has a thing for my ass, calling it a cute little bottom. Sir is imagining how it feels, how I will recoil with each spank and how he will push my ass back for the next hit.

“Baby, I would kneel behind you now.

Take my cock, slide it up and down that slit.

I know you are a good girl.

Arching your hips like the little slut you are.

Reach back with both hands…

Spread your cheeks for me.

Show me where you want me to fuck you.”

I don’t mind where Sir fucks me. As long as Sir rewards me… I will be a very happy girl. I show Sir him that my ass and pussy are his to be used.

“Mmm. Such nice holes.

Begging to be fucked.”

It makes me shiver that Sir is not going to fuck me yet and keeps me waiting and play some more. One of Sir’s dream is to bend me over his knee. Sir tells me to lay over the pillows with the camera pointed at my side. This way I can turn my head to look towards my laptop.

“Spank that naughty little ass again.

You deserve to see what you would be feeling over my lap.”

“Thank you Sir.”

I spank myself for ten seconds or so, but Sir seems greedy and instructs me to get the lube and the plug.

“While you put it in, I want you looking at me.”

How humiliating. I feel embarrassed, but continue anyway. I do want to feel my ass filled and satisfy my Sir.

“That’s a good girl…

Get that cute little ass nice and ready.

Now, that naughty ass needs more spankings.

A little harder…

I want to see you wiggling for me.”

This is hard. Reaching back and spank myself is difficult to do. I try my best and it actually hurts a bit.

“Stop.

Rub your ass for me.

Gently. Lightly.

I would slide my fingers over your red cheeks.

Sooth my poor little one.”

Sir commands me to tug on the plug a little and practice relaxing. This is his way to prepare me… To take his cock in my ass in that position. Fuck… That is so hot. Sir can’t wait to enter me and hear me whimper and feel my ass surrendering to him.

“I need my little slut to do something for me now…”

Wait what? Sir wants me to crawl down the hallway with the plug shining in my ass. My mind is resisting, but I do it anyway. Normally I would feel submissive when I get instructions, but this time I feel my dominant side rising. My little Bobby crawls down this hallway and Sir’s task starts an inner conflict inside of me. How could Bobby’s queen walk on hands and knees on this path? Bobby’s path. I am thinking. That is just not right.

I am back in the sex room again, on my hands and knees.

“Take the small dildo in your mouth.

Oh baby girl, I am going to have to hold you by the pigtails.

Train that slutty little mouth.”

This I can do! Mmm, sucking Sir’s cock would be such a treat now. I lick the dildo up and down and suck it off, thinking about his warm hard-on. Sir stops me.

“Lay on your back.

Spread your legs.

Put the dildo down for a second.

I want you to spread that pussy for me again.

Fuck… You look so good.

Run your finger up and down.

I will warn you, this gentleness won’t go for long…”

I don’t care if Sir is going to be gentle or not. I am enjoying his reward.

“Take the dildo in your mouth again.

Get it nice and wet.

Keep stroking your pussy.

Good.

Baby girl. I want you to take the dildo…

And in one slow but steady motion, force it into that sweet little pussy.”

Yes please, is all I am thinking. I want my pussy filled. Sir enjoys seeing me fucking my pussy with the dildo, nice and hard.

“Now, open your mouth wide, stick your tongue out…

I want you to take that dildo and slap it on your tongue.

Then push it back in your pussy.”

Mmm tasting my own juices, fuck it turns me on.

“I want you to hold the dildo steady and lift your hips up to fuck yourself.

Work your hips.

Show me you need this.

You need my cock filling you.”

Sir is asking so many things and here I am doing it for him… Pleasing Sir the best way I can. My body and mind are his to command. Sir is always good to me and lets me rest for a few seconds. After that it is back to fucking my pussy hard again.

“Such a good girl for me.”

It seems I am far from done. Sir thinks my ass needs a little more. I have to keep the dildo all the way in my pussy and rub my clit. Next step is removing the plug and to add lube. The dildo goes slowly into my little ass now. It hurts a bit, but I want to be Sir’s good little girl. Is this the first time I am doing anal in front of Sir? I can’t recall.

“Rub your clit as it goes in.

I want you to push a couple fingers inside your pussy.

Keep the dildo in your ass.

Can you handle the big dildo in that pussy baby?”

“I can try Sir.”

The big dildo is finally in the game. Sir needs me to lube both dildos. I slowly pull the small dildo almost out of my ass and relube it as instructed. I lube the big one and slowly let it slide into my pussy. It is a bit hard to push it in, because I can feel both dildos blocking each other a bit.

“Oh my God!” Sir loves what he sees.

Sir commands me to hold one still and fuck myself with one and then switch again. I don’t know what is happening. My mind is not here, is this really me doing this? It is intense.

“Yes baby, that’s it.

Getting your holes raped by two men…

Used despite her pleas and cries.

Fuck both, alternating.

Keep going.”

I am losing it. I feel everything turning black. I don’t know where I am anymore. Sir noticed I can’t cum this way and shows mercy. I can remove the small dildo from my ass. I turn back to my sexual self again and fuck my pussy nice and hard.

“Do you think you can cum for me or has it been too much?”

I nod that I can cum. Sir tells me to move to the floor. I fuck and I fuck, legs wide open for Sir to watch my pussy getting pounced. It doesn’t take long for me to cum, especially after seeing Sir’s delicious cock. A long squirt ejects from my body. Thick cum coming out of Sir’s cock. Mmm… So good…

“Such a good girl for me today.

You dripping wet is how I always want you.”

I smile. We both clean up. Eric is curious what I think about the session. He wonders if it was too challenging. I found it challenging indeed, but believe it or not… The hardest part for me was crawling in the hallway. I explain that it is the territory of my little Bobby. It is his beg place for food. I am OK with crawling, but just not in the hallway. Eric understands and it makes sense to him. He just wanted to see the cute sparkly plug rotating in my ass while I crawled.

But damn, that double penetration… It was hot. I wonder if I can handle it better in the future… Or if I can handle it with real men… I don’t know about that.

To be continued. Follow me to get a notification.

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