I collapsed onto his chest, and felt my cock going flaccid inside him; his anal sphincter pulsating and tightening its grip around me, while my breathing slowly returned to normal.
I rolled over to my side, and beside, Simon; still holding him close to me. My cock slipped out along with a dollop of cum, and I used it to massage into his semi-hard dick.
"I think you're going to need some more treatment for that tight ass of yours, Simon," I said, continuing to fondle his cock to life with my spent seed that continued to leak from from his pulsating hole.
We decided we needed a bit of a break, so hit the shower and cleaned up before returning to the scene of the crime.
I laid on my back on the bed in a sitting position and instructed him to straddle me, but facing the opposite direction, toward my feet. His ass was up in the air and his hard cock was rubbing against mine; I now had full access to his hole and my whole jar of coconut oil with which to ply my new trade.
I assembled my tools so that they'd be easily accessible as I began Simon's treatment regimen.
He was still pretty slick in there, what with all of the previous activities of the evening, and me dumping my load into him. I started by having him back up into me and licking his asshole, just as I had earlier, while using my hands to fondle his cock and balls. He was still leaking a bit of my cum, which I could taste coming out of him.
I pulled his cheeks apart and drove my tongue in, flicking it this way and that to loosen him up. He pushed against me, opening his outer sphincter and allowing me to go deeper as I pushed back into him with my face. I never thought ass could taste so good.
"Tool time," I said, smacking his ass, signaling that it was time to move to the next level.
I pushed him back down into his original position, our cocks once again mashing together, so that I would have the leverage required to do my dastardly deeds.
"Stick out your ass and spread those cheeks for me, bitch! Time for some fun."
Simon willingly complied, and I started applying the oil and probing him with my fingers - first one, then two, then three.
It did not take long at all before I had four fingers buried inside him almost to the last knuckles. I thought that now was a good a time as any to bring out the horse cock.
"Bitch, meet Mr. Ed," I said in jest, showing it to Simon in mock intimidation.
"Why don't you suck it for me first, to get it wet?" I asked, my hand still half-way inside him and pushing further.
My horny bitch complied, but was unable to get past the massive head - it was just too damn large.
"Let's see if Mr. Ed is a good fuck, shall we?" I asked, pulling it away from him and lubing it up with coconut oil.
I placed the head of Mr. Ed right at his rosebud, and pushed gently as I coaxed Simon onward.
"Take it, Simon. Take the big cock for Master Dan. Show me what a cock-slut you can be for me."
I was surprised with the ease that it slid past his outer sphincter - I must have had him pretty well dilated with my hand, I thought. He'd taken the head of it and another inch or two; we just had to get it down the rest of the way.
WELL, didn't he start moaning NOW. Sounded like a bloody COW!
But they were moans of pure bliss, judging from all of the signals I was getting. I just kept applying more oil, and pushing that horse cock slowly in and out; in and out. With each stroke, it became easier, and a bit faster than the one previous. I got to the point where I was going in about ten inches - that seemed to 'bottom out' inside him - the limit of what he could comfortably accommodate, length-wise.
I glanced down beside me and noticed that Simon had also gotten out the red flogger - the one with the soft rope lashes. So I surprised him with it, and gave him a firm lash across the ass cheek.
"Bitch!" I shouted, as the red rope tails cracked across his flesh, glistening from the oil in the candlelight of my bedroom.
"Oh fuck, you can do THAT all night long . ." he replied.
He was taking Mr. Ed with ease now. I wondered if it was time to graduate to the next level.
I pulled it all the way out of him - and oh, what a gaping hole was displayed in living color for me - and shoved it back in a couple more times; adding a few more lashes of the flogger for good measure.
"Now we're gonna go bigger," I told him; setting Mr. Ed off to the side.
I poured more oil in the gaping hole where the fake cock had just been, and placed my hand there, poised to plunge home if I could get it there. I was good and slick and he was ready and willing.
This time, I went in with all fingers AND thumb, rounding my hand to lessen its diameter. I got in easily just to the last knuckles and - ah, THAT would be the challenge, I realized.
Simon pushed against me - he wanted this bad.
I pushed against him, and twisted and turned my hand, trying to find just the right spot - as if my hand were a key and fit only a certain way in the lock.
It took about five or ten minutes of pushing and wiggling - that's all.
Simon was pushing back against me, my elbow braced against my chest; and I was pulling him by the thigh back towards me with my free hand. And all of a sudden, 'POP' my last knuckles broke past his outer sphincter and I entered his anal canal.
"OOOOOooooooohhhhhhhh FUCK!!!" Simon literally hollered out in ecstasy, as I sat as still as I could for a moment, waiting for him to adjust to my whole hand being in there.
"Congratulations Simon. I've really got to hand it to you . . you've accomplished your goal on the first go-around!"
I don't think he heard me, nor did he catch my play on words. But it didn't matter. This was turning me on, almost as much as it was him. Our cocks were rubbing together, and we were both hard - especially him. I could feel his prostatic fluids leaking onto me, and we were just sliding together as I penetrated him like I had never done to anyone before.
I cautiously started moving my hand inside him; in a bit further and out; then slowly in half-circles, watching closely for any positive or negative reactions.
Simon was having difficulty putting much more than two or three words together between moans and groans; so I just kept talking to him, telling him what a good anal bitch he was for me.
After about five minutes of experimenting with hand and fist positions, I attempted to pull all the way back out, and noticed that his outer ring had closed off a bit. He got a bit panicky, thinking I might get stuck inside him, but I assured him no worries, and gently worked my way back out of him again.
Once out, I thought he might have had enough; but oh no. Not the case.
"Please, put your fucking fist back in me. Fuck me some more."
Back in I went - and easier this time. Best not leave my hand in there TOO long at a time, I thought. Lesson learned.
In and out, THAT seemed to be the best way to do this. And once he was fully dilated to the right size, it was the most pleasurable for Simon as well. I was able to go harder, deeper, and really feel around in there too.
Making a tighter fist while inside him increased the diameter and gave him even more stimulation. And once fully dilated, it was much easier to find and milk his prostate; twisting and rubbing my knuckles over the left and right lobes of the organ and driving him insane with pleasure.
Simon's hard cock appeared to be in desperate need of attention.
"Do you want to flip around and have me suck you off while I fist-fuck you?" I asked. All that pre-cum was going to waste, and I was craving the taste of him again.
"That would be the cherry on top," he replied, as I pulled my hand out of him.
He turned himself around and straddled me, sitting on and impaling himself on my fist with the greatest of ease; before aiming his dribbling dick for my waiting mouth.
He had softened just a bit allowing me to take all of him into my mouth with the greatest of ease, balls deep. I sucked loudly, and he fucked me like that, with spit flying everywhere.
We both know there's nothing like a sloppy, wet, noisy, throat fucking blowjob to conjure up a nice load of man-cream; and that is what we both wanted to manifest at that moment.
I concentrated on his prostate and he held and stroked his cock - at least what wasn't buried in my throat - until he delivered what I so craved.
My cries of pleasure were muted by his spurting cock, flooding my mouth with his delicious warm cum; and I eagerly took all of his offering into me, swallowing until there was nothing left but his wilting dick-meat.
My fist slipped from his ass and he handed me a damp hand-towel; my work there being done for now.
"Holy shit. That was a fucking religious experience," he muttered, and embraced me as if to say thanks.
"You did well, my bitch. That was fun."
We got cleaned up and just ended up going to sleep that night, exhausted from our night of activities. Simon wanted to get off early the next morning and tie up some loose ends back home. We vowed that we would get together again soon - made a date for three weeks later for a whole weekend of just being together - and slept like logs.
The crack of dawn brought its usual morning wood to both of us; so we enjoyed a leisurely sixty-nine for a good thirty minutes prior to rising for coffee, breathing in each other's scents; licking and bathing each other's balls with our tongues; and finally engulfing our cocks and coaxing out their prize fluids into our hungry mouths.
There wasn't a lot left to milk in either of us - we had both shared much over the last couple of days and cum multiple times - but we cherished what was there and swallowed each other's depleted loads with glee, and finished by licking each other clean.
Eventually we dragged ourselves out of bed, showered and made coffee and breakfast.
We'd had the time of our lives, we agreed, and would save ourselves for our next meeting.
Simon DID get the job, just one hour from me, in a city of about 270,000 people; and was due to start one month from the date of our first meeting, that fateful night in room 1504, a number I shall not forget.
We had both refrained from ejaculating in the three weeks we were apart, saving our seed for our next weekend get-together, and in a series of e-mail exchanges had detailed more about how horny we were, and what we fantasized about doing to each other.
Three weeks is a long time to abstain from such an activity. Simon was apparently used to this; I was not. But apparently, there was method to his madness; and when he fully explained it to me, I thought it a worthwhile pursuit.
The question that had been dogging us, was: could a man experience an orgasm, just from being anally penetrated - just from the intensity of having one's prostate stimulated from anal intercourse. We had come close to experiencing this with each other on our first chance encounter, but had already spent our seed - and plenty - prior to bottoming for each other.
Our plan was thus set in place: we would devote the first night of our weekend together to explore this in more detail. Simon agreed that - since he was already more experienced at "abstention from ejaculation" - he would top for me first; then wait for me to recover and top for him.
The reader should keep in mind - we were rank amateurs. Until our meeting in Room 1504, neither of us had experienced any same-sex contact. Everything in this arena was new to us.
"Whatever you do," he wrote, "Do not ejaculate. Save your seed. It will be well worth your effort, I promise."
Of course, we discussed other things in our e-mail dialogues; like more fantasies, and our previous kinkiest experiences (the ones we were willing to admit to, anyway ...)
"I loved it when you talked dirty to me, and when you used the flogger on me. I loved the feeling of total surrender. I couldn't have done that with just anyone, but I trusted you, and that allowed me to experience what I did without any hesitation or embarrassment. I don't know if I can explain it any better than that."
I replied that I too felt the same way.
"You know that I'll be your bitch too, Simon, don't you? So do not be afraid to ask me anything. ANYTHING."
Our emails were getting pretty hot, and as you might imagine, it was getting pretty difficult to keep from cumming in my pants just reading his, even without touching myself. It seemed I would always have a giant wet spot on my crotch when I was through each night before bed.
"Just you wait until I get there," he answered; "And feel my hard cock buried inside you. I'm going to lash you down to that bed and have my way with you. So, Danny boy . . you would do ANYTHING Simon says?"
I had to think for a moment, but then relaxed and typed out my reply.
"Yes, I would Simon."
I knew he would never ask me to do anything I didn't want to do. The level of trust in our short relationship had already evolved that far. And I knew that he knew that too.
Another thing I had been practicing every night, unbeknownst to Simon, was the art of fellatio . . specifically, deep throating. I had a couple of realistic dildos, one of course being Mr. Ed - the size of a horse cock - but the other being a more modest six and a half inches in length, the one that came with the strap-on I bought years ago but of course never managed to talk my ex into using on me. That is the one I was practicing on.
Each night, I would take a few minutes and try and relax, and practice taking it just to the point of my gag reflex; then back out. I found take I could take it progressively deeper each night and, eventually, voila! After almost three weeks of consistent practice, and only two days before Simon was due to arrive, I got it ALL the way down!
I had trained my gag reflex to become more of a "voluntary" rather than "involuntary" reaction. Boy, did I have a surprise in store for Simon.
As the time drew nigh, I would lay awake at night, trying not to touch myself after almost three weeks of celibacy; thinking of how good his balls would smell, and how his cock would feel filling my mouth and throat. Fantasizing about tasting his cum again, sharing it with him, passing it back and forth between our mouths; about watching him shoot great volumes of it in all directions as I owned his ass with my cock; and about him taking me the same way and perhaps even bringing me to orgasm that way.
We also talked about 'cleansing' ourselves, and resolved to be as prepared for our rendezvous as practically possible.
Simon officially took possession of his apartment the same day he was coming for the weekend, and would stop there along the way to move a few things in before driving the last hour to my place. He would call right before leaving.
Friday finally arrived, and I was proud that I had succeeded in saving my seed so long. Simon was due around 2 PM. I had prepared well: I had his favorite beer all stocked up and chilled; a good assortment of nibbler-type finger foods and hors d'ouvres on trays and ready to pop into the oven; and a veggie and cheese tray with dip for grazing. So we could pretty much concentrate on just having fun.
The call came in at 1:25 PM - I pulled the shades and filled the jacuzzi, and set it to the ideal temperature of 102 Deg. F.; prepared the bed with towels and toys and such; then attended to some 'personal care' details that would enhance our coupling and that I was sure Simon would come to appreciate.
I'd told him to come in the back door (no pun intended), so felt comfortable being naked. My home backed onto wilderness. His car pulled into the driveway at 2:20.
We barely got the door closed before becoming locked in an embrace; we kissed like long-parted lovers, and both of us were obviously hard as a rock before our bodies even came together.
I managed to wrestle his coat off and drop to my knees; I wanted to taste him so bad.
"My cock has been hard for you all the way here, Danny boy. I want to fuck you SO bad!"
I pulled off his trousers and then his briefs, deliciously gooey where the end of his erection was nestled. His upturned cock sprang from its binds and hit me in the bottom of my chin, spraying me with its oozing juice before I even had a chance to bring it to my lips. I grabbed his shaft with my hand and squeezed the vein along the bottom, trying to milk out the rest into my hungry mouth while I sucked loudly on the engorged purple head.
"MMMmmmm... Fuck, I couldn't wait to taste your cock today, Simon!" I said, then took him in one motion deep into my throat, swallowing him while looking up into his eyes for a reaction.
"FUCK! I can't believe you just DID THAT!" he exclaimed, as I held him deep inside me as long as I thought I could.
I withdrew his cock and gave his balls a good suck - he smelled so good - before standing back up and sharing the taste with him in an open-mouth kiss.
"I've been practicing on one of my fake dicks. Wanted to surprise you!"
"Now I know what MY homework's going to be for the next week or so . ." he answered, smiling from ear to ear.
"Let's go to the playroom," I suggested, not wanting to waste another moment of our precious time.
Simon had brought two suitcases with him; I helped him in with them, and placed them in the bedroom. We immediately jumped each other's bones, rolling around on my California King and finished ripping away the rest of Simon's clothing while taking turns playing the dominant one.
Eventually, of course, he ended up on top - straddling me in a sixty-nine position with his balls planted firmly over my face and grinding his sex into my mouth, much to my delight. I licked him from stem to stern and wallowed in his manly scent, while he pulled my legs up and did the same.
He worked his way further down to fully access my ass, and planted his right over my mouth, so we both concentrated on each other there for a while enjoying the finer art of co-analingus. My arms were pinned beneath his body, so I just probed him with my tongue; but Simon was much more the aggressor, using both of his free hands to probe me and spread me in preparation for what would turn out to be a mind-bending experience for me.
Suddenly I felt the familiar slipperiness of the coconut oil - his fingers reaming me, getting me ready for penetration.
"You still have that P-spot vibrator, Danny boy?" he asked, as he continued finger-fucking me.
"On the bedside table," I mumbled, muffled by a mouthful of his beautiful ass.
God, I thought, that thing is probably enough to bring me over the edge right now . .
Simon must have heard my thoughts, for just as he was slipping it inside me, past my outer and tighter sphincter, he spun around off my face and gave me new instructions.
"Don't worry, Danny, this is only to wake up those nerve endings. I won't make you cum this way. I will only tease you for a few moments. Now, turn over, and stick your ass in the air for your Master. Show me your ass. Show me you want cock."
"Oh Fuck, I want YOUR cock, Simon!" I said, as I complied, sticking my ass out like any good bottom bitch would.
"That's right. Now, I am going to just wake up that prostate of yours before I fuck your asshole. Now, RELAX. Do NOT tighten your PC muscle. Do you hear me?"
"Yes SIR!"
He popped that thing in and turned it on, and HOLY FUCK. I just pushed out, to stop myself from tensing up, and the sensation was WILD. I moaned like a woman - I mean, high pitch. It felt THAT good.
He didn't keep it in there long, maybe ten or fifteen seconds, tops. Then, twisted it up, away from my prostate, and pulled it out.
"Well, fuck, THAT really woke things up in there!" I told him.
"Then THIS is gonna wake it up even more," Simon warned, as he started sliding his cock up and down the crack of my ass. "Beg for my cock, Danny boy. Tell me how much you want my cock inside you."
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