Like Showering With A Raincoat

A few weeks ago I got a text message from MG, saying he was free the following week and he wondered if I would like to hook up with him again. I hadn't heard from him since last August, when he expressed an interest in becoming more than just a fuck buddy. I was unsure about seeing him, but the throbbing monster between my legs had come alive, the memory of my tongue rimming MG's ass had got it's attention and it demanded satisfaction. I was instantly hard and feeling horny, so I replied that I could meet up on my day off.

A week rolls by and I find myself outside MG's building. It's freezing cold with heavy snow forecast. The doorbell to his apartment is broken, so I have to call him to let him know I've arrived. After two rings my call is answered, but before I can say anything he hangs up.

WTF!

I had texted him earlier to let him know I was on my way, so he couldn't have forgotten we had planned to hook up. I try to dial his number again, but the cold saps away my dwindling phone battery and I'm unable to make the call. I switch the cell off then on again, hoping that there's enough charge left to call MG again.

By now I'm not a happy chap. Its cold, I'm standing outside MG's place with a busted doorbell and if my phone craps out on me I have no way of contacting MG until I go home to charge my phone. I decide to wait for a few minutes before leaving, in case he's on his way down to open the door.

That's exactly what happens. He''s down a minute later to let me in. Memory is a funny thing, and I guess mine was clouded with lust for MG's ass (by far his best feature), because he didn't look like I remembered. It's bad to say, but he looked kinda ordinary, and I hoped that he couldn't read the disappointment on my face. Still I was there, I was horny and he was available, so I step into his foyer. As we walk up the stairs to his apartment, he explains that he pressed the wrong button on his phone when I called earlier, and cut me off.

We enter his place. Like the last two times I was there, he has all his curtains drawn, and no lights on. There is just enough light coming through the curtains to make out his apartment, and my eyes quickly adjust to the gloom. I remove my coat, dumping it on his sofa as he moves in for a kiss. We kiss for less than a minute before he suggests we go to the bedroom. He seems very eager.

We sit on his bed and kiss, but soon we're naked and I'm licking his nipples. We shift position so I'm on my back, my head resting on a pillow. After another kissing session MG turns around, gets on all fours and offers me his ass. I push the cheeks apart and dive in with my tongue. I'm in heaven as I rim him. My tongue soon snakes into his hole, and he lets out a moan of pure delight.

I begin to finger his hole. I start slowly, working one finger inside him, feeling for his prostate. I have a plan. I want to make MG so horny that he'll let me fuck him. The last time we hooked up I made him cum too soon, and after that he said that was too sensitive for me to keep fingering him, so fucking him was of the cards (although I did work the load he shot onto my fingers into his hole, and had a quick taste of his cum in his hole, so the encounter had a plus side). This time I planned to go slower, to open him up with my fingers, but not allow him to climax.

I sucked on his balls as I fingered him, but I was careful not to overstimulate him. I tried to push in another finger into his hole to join the first, but it was hard to get the second one in there. I asked if he had any lube. He got up and fished around his bedside drawer before tossing me a tube of KY. I lubed up my fingers as he returned to his previous position on the bed. My fingers slipped into his ass easily.

As I worked his ass, he took the tube of KY and squeezed some lube into his hand. I figured he was gonna wank himself off, but instead he wrapped his hand around my cock (which was hard and leaking precum onto my belly the entire time I was rimming and fingering his ass) and he began to jerk me off.

Whenever MG had tried to masturbate me in the past, he had always been too heavy handed, and choked the life out of my member. This time the lube gave enough slipperiness that his attempt was pleasurable. So much so that I wondered how I could maneuver his ass down to my groin and accept my raw cock. I could have nailed him right there. I stretched his hole with a third finger, while rubbing his perineum with my thumb.

He stopped jerking me and asked if I wanted to fuck him. My plan had worked, and I said if he wanted me to fuck him, I would. He got up again and went back to the drawer, this time to get a condom. I would have preferred to fuck raw, but it was his ass, so his rules. I roll the condom down onto my cock, lube up, and jerk some life back into me cock before he lowers himself onto my cock.

Trouble is, my cock begins to deflate. I try holding the base, trying to keep enough blood in there for me to penetrate him, but its no use. I can't keep myself hard. I try jerking my cock while wearing the condom, but the sensation feels strange, and I can't stimulate myself properly. We try a few positions, but it doesn't work. I have to take the condom off.

I jerk myself off again and, condom free, get the life back into my cock. He wants to try again, so rolls another condom onto my dick, but even he can feel my cock start to deflate again. He leans over and starts to suck my cock through its latex sheath.

I never really understood the phrase "Showering with a raincoat on" when it came to condoms. I mean, I had always used rubbers when having anal sex and found it OK (that was until I tried raw sex with Momma's Boy, and discovered what I was missing with skin on skin sex), but this was the first time a guy had given me a blowjob with a rubber on my cock. I experienced the blowjob as though the rest of my body was detached from my penis, and the resulting sensation was dull and not very enjoyable. I also thought it was a little hypocritical of MG. The first time we hooked up he was more than happy to push his unsheathed cock into my mouth, and enjoy my oral talents.

His blowjob had little effect, but I tried jerking my cock in the condom again, with more success this time. I maneuvered him so he lay on the bed on his stomach, and the combination of the view and my digital manipulation got me hard again. I got on top of him, and was able to push into his ass.

I moved inside him slowly, letting him get used to my length and thickness. I was just getting into my stride, and even starting to enjoy fucking him with a condom, when he said he wanted to change position. Crap, I pulled out and promptly lost my erection, so couldn't enter him again in the new position.

We gave up fucking him. He asked if I ever got fucked, and I said no. Instead I jerked him off until he came. He cleaned himself up and I was all set to get dressed and leave, but he wanted to see me cum. I lay back on the bed, closed my eyes and wanked until I reached my own sticky climax, the fat gobs of white cum spraying my chest and his duvet.

I washed up, and dressed as he had a quick shower. He walked me down to his front door and said I could text him if I wanted to hook up again. I said sure, though I had no intention in doing so. Outside, fat snowflakes fell from the sky to join those deposited on the ground while MG and I attempted to satisfy our selfish desires.

Sexually, I don't think we're compatible. What started out as a curiosity about rimming had morphed into something more, but we're both in different places on our respective sexual journeys. He's at the "experimental, but safe only" stage that I was at a few years ago, and I'm...

I guess I'm at a crossroads. I know the risks of hooking up with random guys, and of having raw sex with them. But there's also a part of me that wants to feel the man I'm fucking, to enjoy the sensation with nothing between us. Ideally it would be as part of a relationship, monogamous with maybe a playmate or two on the side.

Though my life at the moment is hardly conducive to such a relationship.

Taken In Hand - Part 2

Part 1 can be found here.

The smell of fresh cum is unmistakable, and as MG's hole was only a few inches from my nose, I could easily detect the load I had worked inside with my digits. I removed my fingers and leaned my face in, my tongue probed his ass crack, and I could taste his cum as I rimmed his hole. I almost shot my load right there.

MG pulled himself off my body. He reached over to the nightstand and grabbed a couple of tissues, which he handed to me. I wiped up the splatters of his cum which had hit my chest during his ejaculation, while he used another wad to clean up his cock.

Having just cum, MG felt tried, so we held each other. Weirdly, it was the most intimate act we had performed. His naked skin felt soft and warm against mine. I slowly ran my hand up and down his arm. I'm ashamed to say that I closed my eyes and imagined he was someone else. The arrangement was for me to introduce MG to the joys of rimming, not to act like we were lovers, so I was unsure just how to react. He seemed to like being held, and from my point of view it wasn't the most unpleasant sensation, so we continued to hold each other for a while.

Soon, however, my libido got the better of me and I began kissing him again. I hadn't cum yet and was pretty horny. I ended up between his legs, licking and sucking on his balls, my fingers playing with the entrance to his ass. I wanted to fuck him.

MG had expressed a desire to try bottoming, and I thought that if I could get him worked up enough, he would want to ride my cock. I spat onto my palm and let the saliva run down towards my fingers. I began to rub my spit soaked digits against his hole. The drying cum became wet again and my fingers slid in easily. His hole was tight and he moaned as my fingers moved slowly in and out. I could feel his prostate press up against his rectal wall and I focused my efforts there.

He found it all too much and moved his hand down to stop the movement of mine. I slowly withdrew my fingers, so much for trying to get him to bottom for me. Instead I put my mouth back on his balls and licked them while I jerked him off, quickly bringing him to orgasm for the second time. I reached over and handed him some fresh tissue paper to mop up the cum which had landed on his abdomen. I moved back up the bed and again we kissed before we spent time holding each other again.

Whilst holding each other, MG began to rub my back, in between my shoulder blades. I had been working out with more intensity over the past few weeks and my muscles were sore. Who new that massaging my sore muscles would rev my engine, making me hornier than ever. I began to kiss him with more intensity, and started to rub my hardness into his hip. This had the added benefit of moving my hip over his cock, giving him some stimulation as well.

I ended up sitting on his crotch, rubbing his cock with my perineum as he jerked me off. I reached underneath myself and maneuvered his cock backwards so it slid in between my ass cheeks. I continued moving backwards and forwards, and his cock ran up and down my crack.

I wanted more. I held his cock and positioned it so it would rub against my hole with each movement of my hips. My mind was fogged with horniness, and I considered whether or not to take the next step. If I held his cock still, and pushed down, his raw cockhead could slip into my hole.

I did, and the head of his cock began to stretch my hole. I knew I could go no further. My hole was not prepped, and had no lubrication. There was no way I could take his cock, as small as it was. Instead I rubbed his cock between my ass cheeks again, then jerked him off in my hand until he came for the third time.

As before we held each other and talked. By now he was well and truly spent, so he couldn't have done much more. We chatted about his situation, that he was bi, but wanted to explore his gay side more, and that the few one night stands he had left him wanting more from the experience.

He said that he thought I was gorgeous, and I knew he was leading up to something. He wanted us to hang out again, I think as a prelude to us becoming boyfriends. It was moving a little to fast for me. Like I said, I was happy to help him explore his body, but I'm not looking to get into a relationship, which I let him know. I find it's best to tell it straight, instead of leading people on. I could see a look of disappointment cross his face, but he covered it with how he responded.

I cleaned up, dressed and we shared a final kiss before I left his place. I sent him a text later that day, saying what I said to him earlier, but he didn't reply. It seems unlikely that I'll see him again.

Having written about this encounter, I see that I'm falling back into old patterns again, like I did with Mr. Silver. Again, I denied myself gratification in favour of his (he came three times, I didn't cum once) and consequently I found myself in the situation where MG thought more could develop from our meetings than I wanted. The old adage is true: learn from your past mistakes or you are doomed to repeat them.

Taken In Hand - Part 1

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Third Time's The Charm

It started off a few weeks ago, with MG placing an ad on a Craiglist type site to which I responded. He's a top guy who wanted to get back into bottoming again and as such wanted to be rimmed, fingered and eventually fucked. How could I turn down an offer like that?

After two failed attempts, we finally got to meet up yesterday. Even though I only had a half hour to meet him, I wanted to taste his ass.

He was kind of nervous and wanted to keep things as discreet as possible, to the extent that when I entered his apartment the curtains were drawn and the rooms dimly illuminated. He said that he found first meetings awkward and asked what I wanted to do. I said as he was planning on being the bottom, it was up to him. I would go as far as he wanted.

His shyness meant that when we started kissing, it was tentative. My tongue probed his mouth, but his tongue did not reach out meet mine. I was a little disappointed, but instead used the tip of my tongue to lick his lips and the sensitive skin inside his mouth, which he liked.

He led me to the bedroom, and spent time fiddling with the lights, trying to get the right amount of dull light out of his bedside lamp. Then he mentally debated the bed coverings, before opting to remove the duvet all together. Eventually he came back to where I stood and we kissed again. He pawed at the bulge in my jeans, meanwhile I was trying to unbutton his pants.

We stripped off our tops, and I gasped as his cold hands touched my exposed skin when he wrapped his arms around me to kiss me again. His hands went back to my bulge and tried to get into my pants, so I unbuckled my belt and lowered my jeans to the floor, all the while still wearing my boots. He pawed at my growing erection through the thin material of my boxers.

I knew I had to get things moving, time was ticking away and I had to get going soon. I whispered in his ear if he would like to be rimmed and he nodded. He slipped of his pants and boxers and got on all fours onto the bed.

There it was, his ass, presented to me like a feast waiting to be devoured. He was in shape and had quite a meaty ass on him. I said that if it was too much or he didn't like what was happening, he could say so and I would stop.

I pushed his cheeks apart, and by now my eyes had adjusted to the gloom and I could see his hole. I leaned in and licked with the flat of my tongue. He tasted clean. I licked again, this time up and down in a continuous motion, making his hole slick with my saliva. He gasped and moaned as I did this. I love eating out a nice clean ass.

I ran my index finger over the spit soaked sphincter, before slowly pushing in. I could feel the warmth of his insides. I pulled out my finger and replaced it with my tongue, this time darting it in and out of his hole.

I alternated between tongue and finger, and then wanted to open him up more. I slipped in my middle finger, withdrew it and immediately replaced it with my index finger, withdrew that and put my middle finger back inside him. By doing this in rapid succession, I was able to get both fingers inside him before long. Now the fun really began. I held my fingers still whilst I rubbed his perineum with my thumb.

I pushed my fingers in with a bit more force, pushing down onto his prostate as I did this. All the rimming has made his hole wet, but I added a bit of KY jelly into the mix to make it as comfortable for him as possible. I asked if he was okay, and he said he loved it. As I finger fucked him, his hole started making a squelching noise. I probed his ass with my fingers, eventually getting them in to the third knuckle.

He turned his body so that he was lying on his back, all the while with my fingers inside him. I fingered him with abandon, again pushing against his prostate. My dick was hard and leaking precum into my boxers. He was on the verge of shooting his load, but he asked me to stop, so I did, holding my fingers still inside him.

After he regained his composure I resumed finger fucking him. The air was filled with the sound of my fingers squelching in his ass, the creak of the bed, and his moans of delight. I leaned in and began licking his balls, staring up into his eyes as I did so. With my free hand I jerked him off, and again I had to stop when he was about to shoot again.

The need to shoot abated, and I resumed my oral and digital ministrations. I traced the infinity symbol over his balls with my tongue, while rubbing the sensitive underside of his cock head with my thumb of one hand and fingering his ass with the other. I licked at the shaft of his cock, and then back down to his balls as he took over jerking off his cock.

My fingering increased and he said he was going to cum. I kept on fingering him and could feel his ass start to clamp down on my fingers. His hole became tighter as he shot his load onto his abdomen.

After he came, I held my fingers still. I asked if he was ready for me to remove my fingers, and breathlessly he nodded. I ever so slowly pulled my fingers out of him. I slid my body next to his and kissed him. He was a little hesitant again, probably because of where my tongue had been, but we kissed anyway.

He tried to jerk me off, slipping my boxers down and handling my cock, but I wasn't feeling it. I need a specific touch to get me to cum, and he didn't have it. We chatted and I learned that he is bi, and in a relationship with a guy, who he tops, and that's why he had to keep things discreet. He asked if fingering and rimming was all I was willing to do, and I said I do like to fuck too, but I thought it best to take it slowly with him, which was partly true, I also didn't have the time to fuck him.

He said he was surprised that I was single, and said I was very good looking, which boosted my ego no end. I told him I thought he was cute too, and I would like to meet up with him again. As we talked, he maneuvered me onto my back, and straddled my cock, which was still hard, but back in my boxers.

I could have fucked him right there, but I knew I had to get going. We dressed, which for me was simply a matter of pulling my jeans up from my still booted ankles and putting my top back on. I used his bathroom to wash my hands and he walked me out.

I texted him later and asked if he enjoyed himself. He replied that he did and that he had never been fingered or rimmed like that before, and was still feeling the effects. He is definitely up for meeting again, on the sly, as he puts it. and I would like the opportunity to fuck his ass.