First Time Fist

She found Mr Reamer on the bed, and the bottle of lube on the floor, and before I knew it, offered the freshly lubed Reamer with a smile. I took the glass butt plug out, put it on the bed, and held my knees back to my chest, offering her my butthole. And waited in vain for another visit from Mr Reamer.

"You're SO open..." she said, marveling at my gape. That made me feel VERY self-conscious. And the next thing she did, made my heart do a backflip.

"Does it hurt?" Cindy asked, putting a finger in me. Or maybe three fingers. Fuck, how could I tell, being stretched this wide. I could only manage to respond with a moan and a mumble.

"Mmm... a bit sore. But that feels good!"

Almost before it started, it ended, and Cindy took her fingers out of me. The warmth of skin gave way to cold silicon, and Mr Reamer made his way back into me, but only to the 4cm width of the glass butt plug. Cindy was a woman on a mission though, and would not give up pushing, twisting, cajoling my butthole into accepting a new invader.

She took Mr Reamer out, and directly squirted lube into my rectum. I was so relaxed, I felt it splash all the way in. Before the lube had any time to ooze out, in came Mr Reamer, Cindy twisting and pushing the fourth bead in.

"Aaoooaaaahhhh..." was the sound I made, halfway between a scream and a moan.

"You made it to number four, Butty Boy. You should see your clitty crying now. Crying for more." She's right, it IS intensely pleasurable.

Here I am, lying on my back, holding my knees to my chest. Ahead of me, a topless angel with perfect C-cup breasts reaming a big toy into my ass. I was in heaven. My balls felt like they were going to explode. Sadly, it won't happen. Not here.

"Push out, Butty Boy." Cindy commands as she continues pushing and twisting.

I focused all my remaining consciousness into relaxing my sphincter. That fifth bead is still not coming in.

"Breathe in. Yeah, that's it babe. Come on, try to relax," Cindy speaks words of encouragement, while her hand encourages Mr Reamer to go all in. The stretching of my asshole felt good, but at the same time it was beginning to hurt. My pain, my pleasure, my entire consicousness was now focused on what's happening between my butt cheeks. It was crazy.

Cindy took the whole butt plug out, and with her other hand ran her fingertips along the rim of my dilated sphincter. Satisfied with the amount of lubrication, she pushed Mr Reamer back into service, and pushed gently but insistently.

I was lost in this daydream between pain and pleasure, when I heard her make the announcement:

"You did it. Hah, you took it all the way in." I looked down, and she was no longer pushing in. The huge pressure that was on my anal opening, is now on my prostate.

Cindy ran circles with her finger around my butthole where it meets the intruder. Despite the recent rough action, I was surprised that I was really sensitive there. It felt good. Real good.

Suddenly, Cindy left the bed to put on her oversized T-shirt.

"What are you doing?" I asked, still holding my knees up.

"Come on, let's drink to celebrate," she said, throwing my shirt and shorts at me.

VII.

We made our way to the fridge, me being very conscious of the large butt plug inside me, and of any lube that might be leaking out. I was wary of Emily and her smartass comments, but thankfully she wasn't there.

Cindy took a bottle of vodka cooler from the fridge, and handed it to me.

"Thank you," I said. A phrase with more than one meanings right now.

"Come sit at the table," Cindy said, motioning me towards the kitchen table. She even helpfully pulled a chair out for me.

"Sit?" Did she forget what she just did to me? "Right now?"

She gave a stern look, motioned again towards the chair, and said,

"Sit, BUTTY BOY."

I had to shush her. She made her point. Obey, or Emily knows everything. Stepping in front of the chair, I gently pivoted my butt down, my left hand setting the bottle down on the table. My right hand holding up the butt plug, as if it were going to fall out. Of course it wouldn't.

Cindy giggled and took the chair across me. We sat and chatted surprisingly normally. About life, work, everything but sex. Normal, except for the fact that I'm not exactly sitting down, but resting my body weight on my feet, and the front of my thighs. To help me balance, I'm leaning on my elbows on the table. It was all very amusing to Cindy, who had a laugh at my contortions. It was also the moment that Emily chose to make her reappearance, right next to me.

"Well?" Cindy asked me, "Are you going to be a gentleman and get Emily a drink?"

"Umm..." was all I managed to say, leaning forward on my elbows. "Not with this plug the size of a baseball bat in my ass," was what I wish I could say.

Cindy let me simmer for a few seconds in awkward silence, before getting up. Walking to the fridge, she took two bottles for me and Emily.

"So I was thinking, this Saturday..." Emily went on about her plans, but I didn't hear the rest of it, because Cindy reached down and lifted both my feet onto her lap. Ostensibly to give me a foot massage, but we all know what she's going for.

"Ummhhhh..." something between a sigh and a moan escaped my lips, as the plug was driven deeper by her movement. I think my eyes rolled back in my skull. My erection returned, and with it a mighty tug on my balls. From Emily's point of view, I must have been getting the world's best foot massage. If she only knew...

After 30 minutes of listening to the girls' gym schedule, work gossip, the world's best foot massage, and two more bottles, I was grateful when Emily finally excused herself.

"Come on," Cindy winked. "We still have something to do," she said, gently lowering both my feet, then helped me up from the chair. I was too tipsy to object, when she led me back into her bathroom.

VIII.

In the bathroom, Cindy stripped me, and had me bend over the counter again.

"I'm going to pull it out, okay?"

She found it suprisingly hard to pull Mr Reamer out. There was so much lube on and around it, she couldn't get any grip. When she got the largest bead out, the rest flopped out without resistance. Cindy gasped.

"Wooow, look at that," she said, admiring my pulsing butthole, trying to regain its former pucker, and failing.

"Look how loose you are, Butty Boy," she said, pushing Mr Reamer back in. The first three beads went in without resistance, but with a little push, in went the two largest beads, also without much resistance. I moaned with pleasure, face buried in my arms, bent over the bathroom counter.

"You like that, hmm? It doesn't hurt?" Cindy asked while pulling it all the way out, and pushing all the way in again. My poor caged dick kept dripping precum on the floor. I answered her with a louder moan.

"Yesss I love it. Hell, Cindy, I love you. Fuck me. Fuck me till I pass out." Oh, that must be the booze talking.

"Don't pass out on me Butty Boy," She leans in and whispers in my ear, "You want me to fist you, don't you? You want my hand in your tush, don't you, Butty Boy? Yessss?" She said that last "yes" while biting my right ear, fingernails gently running down my back.

She pulled Mr Reamer fully out, then put it on the counter next to my face. I can smell my own ass on it, while my actual ass feels longingly empty. I heard the shower behind me. Cindy was refilling the enema bag.

"It's been two hours. Let's get you cleaned out again," she said, while removing her t-shirt. She had nothing on now, but the dark red lace panties. My cock responded enthusiastically to the sight, tugging my balls to the limit.

Cindy tried putting the enema nozzle in, but quickly realized,

"I don't think you can hold the water in. Can you get in the bathtub dear?"

I did as told, and she positioned me inside the bathtub, on all fours, my backside towards the faucet and drainage side. Cindy slid the nozzle in, and gave me a full liter bag of enema. As soon as she took the nozzle out, I started evacuating forcefully in the bathtub. Cindy hooted with delight at the sight, and even in my buzzed state, I felt complete humiliation.

After two more enemas, Cindy was satisfied that I was expelling clear water. She took me into the bedroom. Cindy quickly arranged two thick pillows into the middle of the bed. I got the idea, and got on the bed. My back on the mattress, and my ass elevated on the two pillows. Once again I pulled my knees back to my chest, and found myself face to face with my caged clit. No wait, cock. Damn it. My ass propped up high in the sky, blood rushing to my head.

Cindy, nude except for her panties, got on the bed as well. Bottle of lube in her left hand, fingers full of lube on her right. Sitting on her heels, astride the pillows, she faces my upturned crotch, now a convenient working height for her. She highlighted this fact by squeezing my balls with her right hand, slimy lube running all over the tortured sack.

"Ready, Butty Boy? Your clitty is so happy to see me, she's weeping with joy."

"Yes Cindy. Please fuck me with your hand... mmmhhh."

I moaned as she squirted lube directly into my gaping hole. Her right hand immediately found its target. Three fingers went in, knuckles facing down. She was massaging my prostate with the tips of her fingers. Felt even better than before, and I could feel more precum leaking out, and dripping on my balls.

"By the way," she said, after a few minutes of finger fucking, "this is four fingers. Can you feel it?"

"Give me five. I want to feel it all. I want to feel all of you." was my drunken response.

Cindy paused, pulled her entire hand out, then for theatrical effect, poured lube onto her palm and made a show of rubbing it all over her whole right hand. She makes the Silent Duck shape, beak pointing downwards this time, then puts the first four fingers at my anal opening.

"Look at my eyes," she said. "I want you to look at me this entire time. Do you understand?"

I nodded the affirmative.

Cindy began pushing in. The first four fingers went in all the way to the knuckles without resistance. She again hoots her approval. What, I thought, is she drunk too?

I could feel her twisting and pushing down there. The irregular shape of her hand making wet slurping noises. While I enjoyed the feeling of being stretched, this was becoming routine after a few minutes, and I thought that maybe... fisting is not all it's cracked up to be?

With a push, the knuckles on top of her hand finally made their way in, pressing against my prostate. Whoa now, this is different. Cindy continues to slightly twist her hand left and right. I can feel her thumb flailing, left behind just outside my anal gate.

"You want five, Butty Boy? Can you handle it?"

Cindy takes her knuckles out and reforms the silent duck. I close my eyes and try to relax.

"Look at me," she reminds me, roughly slapping my balls with her left hand. I let out an involuntary yelp. Slightly tearing up from the sharp pain, I opened my eyes to a blurry sight of short cropped hair, tan skin, and those lovely tits. Cindy plunged her right hand back into my butthole, determined this time to push it through.

Suddenly, I felt my anus contracting on her wrist. I had expected a "pop" like when a big butt plug goes in, but her hand goes in far smoother. I saw her eyes widen for a moment. The flesh of her thumb presses home into my prostate. I took a deep breath, and let it out slowly.

"We did it Butty Boy," she coos softly, satisfaction in her voice.

Gingerly, using her free left arm, she crawled up and went face to face with me.

"Tell me, is it all you imagined? Like in your stories?" She asked, right hand buried well inside me.

I couldn't answer. Honestly, it's a very pleasant stretch. But other than that... perhaps slightly painful?

"Hmm? Can't find the words now, Mr. Erotic Writer?" Cindy continued demanding. Meanwhile, her right hand starts twisting left, and then right, very slowly. After a while of this, I could feel it building up. It's a feeling that starts in the base of my dick, but instead of throbbing, it just kept building up slowly, and steadily. Sometimes it's a lot of pressure that feels right at the threshold of pain, but other times it's very very pleasurable. My eyes roll back in my skull, while I start losing control.

"Hey, Butty Boy, look at me!" She was barking orders now.

Nodding my obedience, I started moaning uncontrollably. I tried to think of something erotic to say back, but no coherent words came out. My dick felt strangely alien to me, feeling stimulated from the inside out. Cindy pulls her whole hand out, then plunged it back in, repeatedly fisting me. I was in nirvana.

Then suddenly, I came. Thick white fluid came spurting out, through the gap in front of the plastic chastity cage. I let go of my knees, and held Cindy's head to my right, close to mine. My face to her face. My nose to her nose. Sharing the air we breathe. But no kissing.

IX.

We took a shower together, Cindy and I. It was incredibly erotic, washing up her entirely nude body, against my nude... oh yeah, I have to get rid of my cock cage. I waited until Cindy finished drying her hair and got dressed, then I asked for her permission to unlock the cage. Emily has resumed her reading on the armchair.

I opened the kitchen cupboard looking for freedom, but the key was not there.

"Looking for something?" Emily helpfully asked.

I took out a glass and pretended to pour water from the faucet. What the hell, let's pretend to drink, while I'm at it. My mind was racing. Where could I possibly...

"Looking for your chastity key?" Emily finished my thought, nonchalantly.

I felt the blood drain from my face.

"Emily, if you think...," I started, but she cut me off.

"You had your fun with my roommate, and now you want to go home to your wife, is that right?"

Emily reached sideways with her slender arms into her conveniently located work bag, her long brown hair obscuring whatever she was looking for. As she turned back to face me, a mischievous smirk adorned her face, and she stood up holding her laptop.

"I've been reading your stories too," she said matter-of-factly, as she walked to close the distance between us, in that fluid, graceful way that dancers move.

Oh. I didn't expect this.

"Cindy has been borrowing THIS laptop to read. She didn't even clear her history," Emily shrugs.

"I'm sure she doesn't mind me knowing. In fact," Emily turned down to a half-whisper, mere centimeters from my face, "I know Cindy has a favorite story. One she's read several times."

I swallowed hard, as I watched Emily sit on top of the dining table, and set the laptop next to her right.

"You wrote a good story, the one about your wife and her part time job. SO realistic, I wondered if it was, maybe... not a fiction?"

A dramatic pause. I wonder where she's going with this.

"Tonight, you're going to write a nonfiction. For me."

Ah finally, there's the demand.

"Write down every little detail of what happened tonight. Every little detail, or you're going home with a locked cock. If you write a good one, we'll decide what to do with you later."

CINDY'S NOTE

Hi, I found this laptop open with this story on it.

Can't believe he actually wrote down what happened earlier, in detail lol.

Kinda embarrassing to read. I see he's changed our names.

Looks like those two are getting busy in "Emily's" room, from the sounds of it.

Well you know what, I'm going to click the Publish button, then go knock on her bedroom.

Hope you guys enjoy the story. C u!