First Time Fist

First Time Fist

I.

I punched in the apartment number, and pressed the "call" button. Barely five seconds passed before the little speaker came to life. "Come on in," she flatly chimed. If she was a bit overeager answering the door, her voice betrayed none of her anticipation.

Cindy lives in a nice low-rise middle class apartment, built around the turn of the century. The walls are thick and sturdy, affording good privacy from the neighbors. It's an important feature if, like Cindy, you're a single lady in her mid-30s who has gentlemen visitors. Quite frequently, I would imagine.

As I pushed the half open door to apartment 3C, I was greeted by the lovely smile of... Emily, Cindy's roommate and friend from college. She was sitting on the armchair, her face resurfacing from the thriller book she had in her hands. Her long, brown hair nicely framing her mildly attractive face, accented with her thick rimmed glasses.

"Hey, how are you? Cindy's in the bedroom."

And for a millisecond, I swore her smile turned into a smirk. So much for privacy.

I found the door to Cindy's bedroom and knocked.

"One second," came her reply.

I dropped my backpack on the floor.

From the room came some rustling sound, then footsteps. Cindy opened the door and greeted me with a hug. She was wearing one of those oversized t-shirts that came down to her knees. Despite the baggy fabric's best efforts, the hug exposed her lovely curves to my touch. Ah, what have I done in a previous life to deserve her as my fuck buddy.

Time out, Dear Reader. I believe it is time to explain our relationship, because Cindy is not exactly my "fuck buddy." Because you see, we have never had intercourse.

By day, I am the stereotypical boring midlevel male manager, and Cindy is an attractive interior decorator. By night, I become an erotic writer, and she an avid reader of the same. We met in the comments section of our favorite erotic story forum, and one thing lead to another, as they say. We would meet and act out our kinky fantasies, but with one caveat: we would never have intercourse. She prefers sending me home to my wife, desperately horny.

We now return to the present, me closing the door to Cindy's bedroom behind me.

Cindy broke the hug, her hands still clasped behind my head, face SO close I could kiss her. But she would hate that. She loves reminding me that our relationship is based on sexual exploration, not intimacy.

"So, are we on? Like your last story?" her full dick-sucking lips asks, her deep dark eyes twinkling with anticipation.

"Yeah, I've had this fantasy forever. Let's see if the reality is as good as... I mean, as a writer, I have a responsibility to do research."

She laughed, and beckoned me to follow her into the ensuite bathroom. Another nice feature of these older buildings, which tend to be relatively roomier compared to new developments. In the middle of the room is a queen-sized bed. And a 90-degree turn to the left of the bedroom door, is the bathroom door.

As she made her way to the bathroom, her full hips swayed under the t-shirt. Like a teenager, I made an effort to grab the hem of her shirt, but she scooted away before I could reach her. Wasting no time, Cindy walked towards the bathroom counter.

"Come here, Butty Boy," she ordered.

II.

Cindy has been preparing for my arrival.

There is the familiar 1 liter enema bag on the counter. On the bottom end, a long silicon hose runs out of it for almost 2 meters. At the end of that hose, is a new nozzle I haven't seen before. It is shaped like a small metal butt plug, about 2cm across and 8cm long, with many small perforations on the surface of its head. The nozzle/plug tapers down to a short neck about 1cm in diameter. Instead of a flared circular base, this neck attaches directly to the hose. Securely, I hope. Instead of a valve, the water is held in the bag by clamping the hose with... a hair clip? I had a small chuckle out of that one.

While I was busy examining the nozzle, Cindy retrieved a bottle of lube from the drawer under the sink. She held the nozzle in her left hand, and applied lube from the bottle with her right. I dropped my shorts and duly bent over the bathroom counter. In the mirror, I saw her meticulously spread the lube over the nozzle with her fingers.

"Deep breaths, and push out."

I appreciate the cue, although having done this several times, I hardly needed instructions. The stainless steel nozzle felt cold to the touch, but the sensation quickly passed. Cindy let me adjust to having a foreign object in my rectum, before releasing the water.

"It's warm," I commented, feeling the water rushing into my gut.

"Hope you like it," she said. "Took me a couple of tries getting the correct temperature from the shower." She hung the bag by a hook she had put on the towel rack, above the toilet behind me.

Almost as soon as the water went in, I felt the familiar urge to push it out.

"Uhhh I gotta go..."

"Just go," she directed her gaze at the toilet.

I positioned myself over the toilet bowl, and pulled the hose out. Cindy used the hair clip to stop the water flow.

This is the first time I ever had to evacuate in her presence. She looked at me with an expression of... curiosity? No, more like a cat playing with her prey. Although she has told me on several occasions that she's usually submissive in her relationships, she's always keen to point out: "but I'm not YOUR sub." Ouch.

As I finished cleaning myself, she had the bag refilled to full capacity and ready to go. This time, more of the water went in. I voided again, and she gave me more enemas.

After the fifth time, I saw the bag going completely empty on the hook, without feeling the familiar cramps.

"Hold it in for me babe?" She asks, as she pulled the nozzle out.

I nodded.

"Did you bring the cage?" She asked.

"Yeah, but... now?" I pointed to my belly, holding a full liter of warm water.

She gave a mock pout. I started looking for my bag, only to remember that I dropped it outside the door. Putting my shorts on, and acutely aware of the water sloshing around my insides, I opened the bedroom door and walked outside.

"Oh, forgot your TOYS?" Emily asking, book still in hand, a firm emphasis in her query.

"Ha ha," I said, walking back into the bedroom with the backpack. Cindy was waiting, sitting at the foot of the bed. Reaching into the bag, I handed her the cock cage, dropped my shorts, then went and voided on the toilet. I cleaned myself, then went out to see Cindy on the bed, playfully inspecting the chastity cage.

III.

Made from clear plastic, it is part of our agreement. You see, Cindy would not be nude in my presence, unless I have the cage on. At the end of our fun and games, she would again be fully clothed, before releasing my cock from its confines, raging and desperate. This is the only condition, she says, that she would agree to our relationship.

In one practiced move, I laid on the bed next to her minus shorts, but with my shirt still on. I bent my knees and brought my feet close to my butt. My crotch is thusly exposed and presented upwards for her convenience.

Staring at the ceiling, I felt her move towards my crotch. I could feel her gaze, burning into my scrotum. Her soft breath on my inner thighs, driving me crazy.

But I kept my eyes on the ceiling. Looking down meant looking at her playful eyes, her beautiful dick-sucking lips so close to my dick, that I don't know if I could stop myself from jumping her. Best case, we end up with a full-blown affair, which is bad. Worst case, she would throw me out. She knows I won't look. Not YOUR sub, as she would remind me.

The chastity cage is divided into two parts. There is a ring that goes around the penis and scrotum, slightly warped to follow the curvature of the pubis. After this is put in place, the second part is a cock sleeve that covers the entire head and shaft, so that they cannot receive stimulation. There is a rather large slot in front of this sleeve part that allows piss and some air to go through.

The top part of the ring, and the top of the sleeve are made to come together and interlock. A small lock goes into this junction, and then the key can be turned and pulled out.

The scrotum hangs in a small gap between these two sections, effectively forming a fleshy padlock to secure the chastity cage in place. Any attempt to pull the cage off, will translate to pulling on the scrotum. Any erection, however, will also result in stretching the balls away from the body.

Cindy finished the process wordlessly. And with such efficiency that I couldn't help but wonder where and how much she has practiced.

"Babe, help me out and put the key in the kitchen," she said, dangling the key above my face. The key has a small padlock charm with the letter C on it.

"Left hand cupboard, behind the mugs," she continued, impatiently.

Mocking a pout, and a huff, I put on my shorts, and brave the path to the kitchen. Gingerly, because I'm still getting used to the alien device that has become a part of my crotch.

"Hi Em, Just getting a mug," I tried to explain. I put the key inside the cupboard, and took a mug.

"Mmm hmm," Emily said, without looking up. Am I looking like an idiot, carrying an empty mug? Am I walking funny, because my caged balls are rubbing the insides of my thighs? Did she notice?

None of those thoughts mattered, because as I walked into the bedroom, I was too busy picking my jaw off the floor.

In my absence, Cindy has removed her t-shirt, and is now wearing nothing but a see-through lace slip dress, with matching lace panties underneath. Casually standing in the doorway, just beyond Emily's line of sight, arms hanging by her side, lips closed and eyes piercing to the back of my skull, Cindy looked stunning with her C-cup breasts and curvy hips highlighted by her deep red lingerie.

IV.

I did what any man would. Slammed the door shut, and carried Cindy to the bed. She let out a squeal as her body made contact with the sheets. I climbed on top, knees on either side of her thighs, pinning her down. I took my shirt off, and fell on top of her, my hands pinning her hands down and spreading them wide. I overpowered her, and started kissing her forehead. She did not resist.

Taking her left hand close to my face, I started licking her fingers, her hands, all the way inside her elbow. I held her arms wide apart, and started licking her left armpit. Her breathing got heavy. I started kissing her right hand, and repeated the process. She started moaning, and threw her head back against the pillow.

I lifted my head, and looked into her face. Her lovely, beautiful features, now filled with passion. I started kissing her forehead, and she closed her eyes. I kissed her eyes, her cheeks, and down to her neck, carefully avoiding her lips. She doesn't like french kissing. Not with me, no.

Cindy got off the bed, and pushed me back. It's her turn to be on top. She took off my shorts and tossed them aside. She took her time rummaging through my backpack, looking for a specific item.

She found Mr Reamer. It is a 20cm long butt plug with five round beads, the next one larger than the other like a pagoda. The first one is around 2cm across. They get progressively larger, until the fifth is more than 6cm across. I know, because I measured. When I first showed it to her, I joked:

"Maybe, if I can take the whole thing, I can take your fist."

Tonight, we're planning to make the punchline a reality.

Taking the butt plug, she walked to the bathroom, her lovely ass, her dark tanned skin now very visible in the soft rays of the dying sunlight. When she returned, Mr Reamer was slathered in lube, in her right hand. In her left, the bottle of lube. She was an angelic vision of anal pleasure.

Still lying on my back, I put my hands behind my knees, and pulled them back towards my chest. I looked between my legs, and saw her face rising above my chastity cage. For the first time, I distinctly felt my cock, trying to get an erection, pulling on the cage, the cage pulling on my balls. Such delicious pain.

Cindy squirted a bit of lube on my butthole, and used the head of Mr Reamer to spread it around. Feeling the very pleasurable stimulation on my anal opening, I laid my head back on the pillow and closed my eyes. Cindy took this as her cue, and started to push. I took a deep breath and tried to relax my butthole. The sphincter gave way, and I felt the "pop" of the first bead in me. Then another pop.

"Babe, you're up to three," Cindy half whispered.

"What?"

"It's more than halfway in. Have you been stretching? You Butty Boy," she playfully slapped my ass.

She left some pressure on the base of the butt plug to hold it there for a while. Then, as swiftly as she pushed it in, she took the whole thing out. I felt a jolt from my prostate, and some precum made it out at the same time a moan escaped my lips.

Cindy added more lube to Mr Reamer's whole length, and pushed it in again. More precum leaked out. She repeated this several times, adding more lube each time, never going past the third bead. It was immensely pleasurable, having my prostate stimulated this way. I decided to be passive and enjoy the ride.

"Uhhh fuck Cindy, please don't stop. Oh fuck oh fuck."

After a few minutes, she decided that it's time to move on. She left the plug halfway in me and got off the bed. Despite my best effort to relax, because of the shape, I involuntarily pushed the plug all the way out. Mr Reamer landed with a soft thud on the bed.

I was still collecting my breath, when Cindy came back with another toy from my bag. It was a clear glass butt plug, more than 4cm across and quite short. The bulb tapers down into a 2.5cm neck, and ends in a wide flared base.

"Hold that position for me," she commanded.

Without lubing it, because of the smooth material, and because I was already well-lubricated, the tip went in very easily. It's still larger than the beads I had before though, and Cindy was patiently alternating between gently pushing and releasing pressure. Because it hasn't gone in, there is no stimulation on my prostate, and the pleasure is purely anal. After a few minutes, she started twisting the plug in my hole, and pushing harder. It went in, again with the "pop" I enjoy so much. The pressure on my prostate is greater than before, and my dick slowly deflated.

This time, there is no risk of this plug getting out. She reached for her bedside and took another object.

"Hold it..."

Flash! She took a photo with her phone. Not satisfied with the result, she took another one. This one she's happy with, and showed to me.

"I've always liked the way glass plugs expose the insides. Kinda erotic," she said, smiling.

Well, it's... artsy? The screen shows a picture of skin with sparse hair, dominated in the middle by a glass circle pressing on the skin. Inside the circle is another circle, this one a semi transparent window into a pink interior, glowing from the camera flash. Hell, if you don't know what you're looking at, it's almost not a dirty picture!

V.

Cindy decided it's her turn for some fun. She laid back on the pillow on my left, and looked at me. Tugging on her neckline, she exposed her right boob.

"Come here and kiss me again."

Declining her invitation, I went to the bag again, and retrieved a pair of suction cups. These are made from clear, rigid polycarbonate. On the top of these cups are thumbscrews, and as you turn them clockwise, the pistons inside move up, sucking on whatever part of the skin the cup is placed on. Twist = suck. You get the idea.

Moving on top of her again, I pulled the lace dress completely above her head. Her boobs naturally sag slightly to her sides. Grinning, I positioned one cup on her right nipple, and twisted the tumbscrew a bit. The piston moved 2cm, just enough to get her attention, and for the cup to not fall off. I repeated the same on her left nipple.

"How do you like them? Better than clamps?"

She took a deep breath and nodded.

"Yeah, clamps are painfuuuu.... OOWFUCK!" She couldn't finish the sentence as I flicked the suction cups, swinging madly on her jiggly flesh. Not MY sub? Hah.

Roughly, and swiftly, I pulled the cup off her left nipple. My right hand rakes my fingernails s l o w l y across her breast, top to bottom, intentionally missing the nipple. She struggles and gasps for breath, her eyes closed.

"Ughhhh... that's... aaahhhh..."

Ignoring her, I went for another pass. This time my middle finger nail hits right across her nipple. She gasps and moans loudly, this time staring into my eyes.

Gently caressing her left breast, I asked her,

"What do you want me to do?"

"Kiss me." was all she managed between gasps. I cradled her head with my right hand, and kissed her gently on the forehead.

"No, not there. Kiss me."

Finally understanding what she meant, I made my way down, and licked her left nipple. She moaned her agreement. I stopped licking to twist the screw on her forgotten right nipple. The piston moves another centimeter. She moaned her further agreement. I returned to the left nipple, this time taking it fully into my mouth. Cindy has lovely fat nipples, almost the width of my thumb, and sticking out proudly when engorged, just the perfect length to pinch between my fingers.

I licked, sucked and bit on her left nipple, while increasing the suction on her right nipple several more times.

After a few minutes of this, the screw came to a stop and the piston would not move any further. I took her phone, quickly swiped the camera shortcut, and took a picture of her right nipple under the cup. Without flash, of course. I'm all for natural skin tone.

Cindy looked at the phone screen, and could not recognize her own body. It's a close up picture of a long clear cylinder, filled with a distended nipple that's stretched to 5cm long. She laughed at her own picture.

"If you flip it, it looks like one of those cow milking machines, up close," she said.

I tugged on the cup roughly, trying to take it off her right nipple. She squealed in pain as the vacuum seal broke. On her nipple was a few drops of liquid. Milking machine, indeed. Fulfilling her wish, this I also kissed and gently sucked on, keeping in mind how sensitive the nipple must be, being this engorged. She caressed my head while encouraging me to suckle.

"Top drawer..." she said. I retrieved a small bullet vibrator from the drawer she indicated. Cindy puts it on high, and used her left hand to rub it on top of her panty-clad clit. I returned to orally pleasing her right nipple. Within a minute of using the bullet, she held my head even tighter against her breast, and her breathing became a lot heavier. After another minute, it was over... until the next orgasmic wave washes on top of her. I counted five waves, before she finally dropped the bullet, still buzzing, on the bed.

This is how she likes her orgasms, quietly, with me sucking and nibbling on her nipple.

VI.

"You're a naughty, Butty Boy." Cindy broke the silence, as she came down from her high. Me lying on my back, her head on my chest. Her whole body curling into my left hand side, her still-sensitive breasts poking into my ribs. Lazily, she propped herself up on the bed, the afterglow still weighing on her mind.

"Hold your knees up," she demanded, wanting to inspect my butt plug. I did as she asked.

"Ooh, your clitty is crying." I used to hate it when she feminized my dick as a clit. But somehow, it's now a turn on.

My prostate has been getting a good massage from all the thrashing about, and precum is now pooling on my scrotum, from the awkward position the cage puts my dick in. To my surprise, Cindy quickly licked the precum off my balls. She never did that.