Masturbating shemale jerking off and gaping

Masturbating shemale jerking off and gaping
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Phil, A 45 year old male virgin. Probably Biu-sexual, if you paid attention to his habits. He likes Internet porn, with some various fetishes.

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He liked to look at diaper porn, enjoyed wearing adult diapers, more for convenience than erotica. He also occasionally looked at male on male, more than anything else. So, I decided there may be some interesting possibilities. Phil and I used to be roomates. He had the upstairs, and wife and I had the lower, Then the WIfe moved, and it was just me and Phil.

We sometimes talked about our porn likes and dislikes, and it turned out we both had a similar habit. That habit would lead us to some interesting adventures. Self cleansing, and insertion. Yup, a nice warm enema to clean out the waste treatment facility, then insertion that would make some vaginas jealous. My play consisted of taking an anti-emetic/anti-diarheal about two to three hours ahead, to make everything more solid, and reduce the potential for surprises later.

Then when it was time, I would take over the bathing room, fill the tub with a nice warm bath, and also set aside a large pitcher of water about 115 degrees, from which I would fill my douche bottle. Insert water, hit the toilet, let it escape. Repeat til all remains clear. Once the water in the toilet remained clear, I would then take up my book and sit for a little while in the tub, allowing my abdominal muscles to relax prior to making them stretch in ways nature had not intended.

Then, the beginning. Starting small, a slender black penis shaped dildo, roughly 5 inches of insertable length, a little bigger round than my thumb.


Insert, leave in, and settle back in the warm water. SIt straight down on the toy, allowing it's small suction to stick to the bottom of the tub. Then I would start gently rocking, stretching the sphincter muscles at the beginning of the canal.

After about ten minutes, I would refresh the water, heating it up a bit, while I selected the next adventure. My Thudder, a thicker dildo, with a heavy vibe motor locater near the top.

Waterproof, and powerfull.

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Insert the thudder, and start the motor, allowing it to rumble around inside me, while due to the heavy vibes, my dick would get harder and harder. (More on THAT later) After my cock reached fully hard, I would switch back to the slender toy, and sit back again in the water, relaxing those muscles.

The Dick would go most of the way back, but didn't take long after ward to get fully hard. 15- 20 minutes later, Soaking done, I would stand up, plant my Adam dildo on the wall, and start washing my hair, while grinding my ass back against Adam.

Wash and condition the hair, wash the body, rinse down, all with Adam buried balls deep in my ass. 8 solid inches of fleshlike pressure on or near my Prostate. After stepping out of the bath, I would dry off, then I would play a bit with my erection. Squeexing gently from base to ti;p, repeatedly, I could get nearly a teaspoon of Precum, which I licked clean. One of my favorite snacks is the fluids that are presented by the excited and aroused Human.

Perhaps we'll discuss other snacks at another time. Then I'd head to my sitting room, and proceed with the big guns. Again with the toys already played with, and leading up to various household bottles, all shapes and sizes, cleaned and prepped. I would go from insertable to insertable, slowly working my way to larger toys. One of my favorite insertions is the aluminum Baseball Bat.


The kind used for second graders, Same thickness as a large bat, but short enough for excellent control. I would fuck my ass with anything I could fit, until I finally would jack my cock, and when cumming, find novel ways to get it in my mouth. And back to Phil. He was not nearly as large as some of my toys, But here's a secret. I have always preferred living cock to toys. Different feel entirely, and the thrusting of the hips on the partner of the moment, forcing your ass checks and hips that bit by bit further stretched open, plunging in, fucking, the gasping of air byt he person fucking me.

And then feeling his cock jerk as the cum made it's was into me. And then after my human toy left, sliding my Adam into my ass, coating it in mylover's cum, and licking that sweet toy clean.

Wow, I get distracted easily, hmmm? Phil was a hard working man, a bit nerdy, and always making remarks about sex, half joking, but I figured he may be wishing, so I decided to start granting wishes. I started letting him know a litle more about my insertion habits, until aswe started talking about dildos, and how they felt, a couple times a week.

I felt were getting closer to his giving in to me, when suddenly, I had to move north to where my wife was, due to some medical issues she had. Yes, we were still married, Just working in different states. SO my possibly getting a taste (and feel) of Phil's cock had to wait a while. But I didn't surrender. That cock was to be mine. And who knows. Maybe his ass too. Finally, I decided to go back down and stay a couple days, and knowing when he would be working, I made sure to arrive early, and took over the bath, cleansing myself, preparing for the potential of a good night.

I avoided the heavy stretching, keeping to the tiny toy, so as to not overstretch. Fully cleaned, I made a nice dinner, which was ready as he arrived, I prepared a nice steak dinner, potatoes, greens, full of energy. As a rule, Phil had been drinking citrus juices, a habit I go thim into. Little did he know it made cum almost always taste nice and sweet.

We ate that dinner, and then I suggested we may do something later, without saying particularly what. Phil remarked that he should go get a shower first. He went in, and as always, left the door ajar. I stood in the hallway, and waited to hear him open and close his shampoo bottle.

After about three minutes, I udressed out in the hallway, and walked straight into the bath, climbed into the shower, with my back to him. I turned around, grabbed the liquid soap from him, and proceeded to wash his chest, worked my hands around his neck, over his shoulders, and down his sides. I turned him round, facing away from me, and worked the lather down his back, then ran my hands around the curve of his rear, making sure to grip firmly.

Then I ran my hands around him and cupped his balls with my left, while slowly gathering his cock with my right. My own cock was alread raging hard, But remembering what I was after, I made sure to turn enough to avoid pushing that angle. for now. I allowed the water to rinse hic cock and balls clean, and then knelt down and started washing his legs, thighs first, then calvs, feet, then I reached up, tucked his cock down between his legs a bit, and took it in my mouth.

Not knowing what to do, He bent at the waist, allowing me to get more than just the head. I started slowly sucking that sweet cock, while I massaged his balls gently at the same time. I felt his balls start to contract, pulling up closer to his pelvis, a sure sign he was ready to rumble, so I released his cock, and started to stand.

He made a wisecrack, asking if that was all.

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I simply said "no", and turned him around, then myself. I held his cock in my hand, and backed myself right onto it, It went into me, and so I bent a little, and started grinding it into me.

He got the idea, and started thrusting that happy little cock into me.He was a little excited, and sloppy, this being his first actual fuck, but I stayed patient, and allowed him to thrust away, until I feel him start to shake a little bit. I pulled away, and quickly wrapped my mouth around the head of his sweet cock, fresh from my slippery ass, and simply held it in my mouth til he subsided, not quite cumming yet.

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I stepped out of the bath, leading him, and stopped long enough to dry us both a little. I then led him to his living room, where there is a large ottoman, which I pushed him down on. WIth him on his back, I walked around the ottoman, and standing above his head, slowly rubbed my cock on his lips, until they opened, and took me in. My Cock?

Roughly the girth and length of a standard longneck beer bottle. Not the thickness of the neck, but the lower bottle. His hand came up and started stroking my shaft. I could tell he had done some oral before, so I let him explore. I ran my hands down his chest, slowly along his pelvis, and down around hios balls, then as one hand started stroking his cock back to stiffness, my other hand started rubbing around his anus.

As expected, this got him rock hard fast, and larger than the last play in the bath. I strolled back around the ottoman, and lowered my hungry ass onto his cock yet again, and started riding reverse cowgirl. Hell yes we'll call it cowgirl, I was certainly a slut tonight.

WIth my back to him, I started grinding that meat deeped and harder into me, He was starting to thrust hard back at me, and I pulled up enough to let himn pound that beast into me. Believe it or not, He was still getting bigger in side me, and I was really starting to feel it hitting around my prostate. I slowed him and turned around, so my knees were either side of his hips, and I again started the action, fucking myself slowly down onto his cock.

Up down repeat. repeatrepeatrepeatrepeatrepeatrepeatrepeatrepeatrepeat. I started cumming, with hot cum trickling down over my hand, as I tried co catch it.

I brought the cum up to my very hungry mouth, and licked it all in. But I didn't swallow it.

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Instead, I pressed my lips to his, as he fucked me harder, and trickled the cum from my mouth to his. As I did this, He started kissing like a pro, his hot lips grinding against mine, awith my cum sliding between our mouths, and I felt him again start rapidly slaming that cock into me. Realizing from his moans that he was reaching the point of no return, I released his mouth, and raised myself up a tine bit.

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Until I felt that last huge thrust, and then felt that cock shooting superheated cum, in insanely huge amounts, into me. I held that position, until I felt his throbbing subside a bit, then I started contracting my ass around his still mostly hard cock, and heard him gasp as my squeeze set off another burst of cumming.

Feeling that it was enough, and wanting him to recover for morning, I pulled up slowly, easing his cock out. As it slid slowly loose, I felt that spasming start a little more, and as I finnly came off him a trickle of cum escaped my well fucked ass, dribbling like icing onto his delectable cock.

I like icing. Trying really hard to squeeze my ass shut, I lowered my mough to his belly, where a little more of his cum had escaped his cock, licking it up, then moving my lips onto his cock.

I sucked it into my mouth, and the icing of his own cum came with it. Then I made a ring of my thumb and forefinger, and slowly squeezed from top to bottom, draining another good mouthful of cum from his cock, and into ME.

After cleaning him up, and making that sweet cock presentable, after swallowing the cum I took into my mouth, He lay there breathing hard for a bit, still recovering from the first fuck of his life.

I lay there with my ass full of his cum, almost wishing I was a woman, with the possibility of fertilization. I lay down next to him, cuddled into his chest like any freshly fucked woman would, ran my hand across his chest, and simply said "You are No longer a virgin".

He just said; "Wow"