How the Coronavirus Jump-Started my Sex Life - 10. Chapter 10

“What we’re going to do a few minutes from now will not only change your life, it will change who you are. It will put you in touch with the core of what makes you a unique and special person. It will allow you – no, require you – to experience feelings you’ve not even been able to imagine before. At first it may be very strange and uncomfortable. It might hurt a little, too.”

That made me a bit nervous. I know I can handle a little pain, but how much it would be was hard to guess.

Alan continued, “I’ll be patient and I will help you, but you need to be prepared for some pain for just a few seconds. If you feel pain, you need to concentrate on relaxing your ass, on not trying to close it to keep the dildo out.”

How do I relax my ass? I wondered.

“How do you relax your ass? You might ask.”

Damn, he was perceptive. For the first time I realized he had a good amount of experience with man-to-man sex. He must. In answer to his question, I nodded.

“Yes, I’m wondering that, Sir.”

“Push. Push out like you’re trying to take a shit.”

He paused while I thought of the movement.

“The sooner you can relax your ass, the quicker the pain will stop. But, rest assured, it will stop. When the pain goes away, it’ll be replaced by feelings you’ll find pleasant and soon you’ll begin to feel pleasure. You’re going to enjoy this, Cal.”

He smiled at me for the first time since dinner. That smile was as comforting as it was breath-taking. “Bottoms up!” he called as he upended his glass to drain the last of the liquid from it. I finished my drink and set our glasses on the sink.

When I turned around, he was standing beside the bed, startling me a bit with his movement.

He was holding up the pale pink rubber dick like a sort of club. Looking me directly in the eye, he nodded his head slightly, gently and said, “Open wide.”

Startled by his request, I slowly complied. He pointed the dildo at my tonsils and began coming forward. When the head of the dildo touched my lips, I opened just as I would if it was his dick heading my way. The feel and taste of this fake dick was a little different from his cock and I could tell immediately that it was noticeably thinner, too. He pushed the dildo all the way into my face until my nose was against the rubber balls. The tip was just entering my throat when he stopped moving. He ginned and said, “Now you can understand how much smaller it is than my Big Al.” He slowly withdrew the dildo from my mouth. When it was gone, I felt the empty feeling I always got when he would pull his cock out.

He slid the dildo back into my mouth before turning to the side to reach his desk where he activated a Pandora station on his laptop. Within a few seconds some of the most beautiful classical cello music I’d ever heard filled the room.

He stepped back in front of me, smiled, and reached up to grab the rubber scrotum attached to the pink dong. “I hope you like Hauser,” he said quietly as he pulled it out of my mouth.

“Uhm,” I nodded, “it’s exquisite.”

“Romantic and sexy,” he said, “which seems perfect for what we’re going to be doing.”

I nodded as the music crescendoed.

“Okay,” he continued, “I think the best position to try with the dildo will be on your hands and knees on the bed. I’ll get behind you and control the penetration. I’ll go as slow as you need and will pull out if you can’t take it. But you’ll be able to take it.”

I nodded.

“Any questions?”

I couldn’t think of any, so I shook my head.

“Good,” he smiled. “Okay. Face the headboard and get on your knees.”

I felt light-headed as I turned my back to Alan and leaned down across the bed. I drew my knees up and imagined the sight of my rump pushed out there where it was very visible and, oh god, very vulnerable.

Alan stepped up beside me, opened his nightstand drawer, and extracted a small bottle of lubricant. He walked the couple of steps needed to get back to my backside, popping the tab on the squeeze bottle of lube at the same time. My heart rate increased as we moved steadily towards the penetration moment. I heard the splop sound of the lube coming out of the bottle and everything seemed to be suspended in time for a few seconds.

Gently, Alan tapped the dildo on the topside of my butt, just above the top of my ass-crack. It felt totally weird. Soon he pulled it down so the head of the dildo dropped into my crack and began moving up and down in the slot between my cheeks. I could feel that it was leaving a trail of slime not unlike a real dick that was leaking pre-cum.

When the dildo met the opening to my innards, I felt a mild shock almost electrical in nature. “Oh, fu-u-uck,” I cried without thinking. My heart was pounding like a bass drum as I anticipated the pain of having something shoved inside me in opposition to the normal path of nature. Alan rubbed my hole for half a minute or so, then he pulled away for a moment and I heard the splop of lube again.

“Now,” he said gently as he touched my hole with a drippier dildo, “you might want to try relaxing your sphincter like we discussed.”

“Oh, okay,” I mumbled.

He repositioned the dildo against my hole and began to push forward. For a moment it seemed the irresistible force was bested by the immovable object.

“Push!” he ordered.

I pushed and instantly the dildo popped in through my sphincter. I had about a second of modest pain (maybe a 3 on a scale of 10). The dildo remained just breaking through for several seconds as my breathing began to calm and any memory of pain dissipated.

“Are you okay, Cal?”

“Uh, yeah,” I muttered as I asked myself the same question. “Yes,” I answered more forcefully. I was surprised at my physical feelings. I did feel stretched, I guess, like I was taking a shit but it wouldn’t go on out. Like it was stuck there. I felt a little cold from the dildo. Frankly, I felt just a bit disappointed because it didn’t feel particularly good. Not bad, but not great either.

“Okay. I’m going to push it in further.”

“Yeah.”

The cylinder began pushing in slowly but firmly as if it was not going to be stopped, even if I tried. Of course, I had no intention of stopping anything because I recognized this was a lot like taking a man’s cock and I wanted badly to learn this. I felt very tense as the rubber dick slid further in. I think I was tense because I wasn’t sure if it would begin hurting at some point. By this time, it was far deeper inside me than Alan’s fingers had gone. And I was starting to relax as I realized it was not only not painful but it was just starting to feel kind of good.

“How are you doing, Cal?”

“Uh, yeah, okay.”

“You’re taking it well.”

I couldn’t believe how long the fucker was. I had seen it, even sucked it, so I knew it was several inches shorter than Alan’s cock. Nevertheless, it seemed to go in for a long time. I was beginning to enjoy the fullness I felt. Although I had strained to push my asshole open for the dildo, I was feeling relaxed now. That seemed weird to me. A moment later I felt something against my buttocks and the dildo stopped moving.

“That’s it, dude. You’ve got it all.”

“Wow.” It felt good, but still wasn’t as wonderful as I had hoped it would be.

“Are you good?”

“Yes.”

“I’m going to start pulling back now.”

The dildo started back out. After about half of it was gone, I realized I didn’t like that empty feeling as well as I liked the full feeling.

Just when I thought he was going to pull it all the way out, it stopped moving with an inch or so still inside me. My sphincter didn’t get the chance to tighten back up. Alan just held it there immobile for a moment. Then he started back into me but much faster than that first time. Still, it was not too hard to adjust to its presence inside me this time. As the fake dick moved into me, I enjoyed the return of the fullness and more. It felt really good and I was glad to feel it coming back. The whole deep slide only took a second or two. When the dildo was again all the way inside, it seemed to sort of knock the air out of me, making me expel a sort of grunt.

After a moment’s rest, the dildo backed out again and then came in faster. I was starting to like this! Each withdrawal and each thrust seemed to come faster than the one before until I was moaning as it opened me again and again. The end of each stroke was a little like a punch and I would grunt. So there was a very distinct pattern of moans and grunts. And still Alan kept speeding up the tempo.

“Yeah,” Alan said excitedly, “take it, Calvin. Take this motherfucker.”

I moaned louder as he shoved it rapidly into my guts. “Ooooh! Fuck!”

I was practically overwhelmed by a buttload of feelings coming at me. I felt the fabulous fullness. I felt the magnificent rub of the dildo on my asswalls, giving me sensations I had never imagined as it created warmth and wetness in me. On most thrusts, I felt the burst of sexual excitement as the dildo passed over the bump of my prostate inside me. From my Anatomy class, I knew the purpose and job of a prostate, but I had not read or heard of the extreme levels of pleasure it gave me whenever it got thumped by the rubber dicky. I lost track of time as my brain focused so completely on the magnificent sensations in my ass that everything else ceased to gain my attention. I think my moans and grunts had gotten louder as Alan’s speed had increased. Oh, god!

Eventually, he stopped, leaving the dildo inserted to its maximum. He began gently pushing down on my back. “Lie flat on the bed,” he instructed.
I complied but Alan grabbed me on both sides just above my pelvis. Firmly, he pulled me lengthways down the bed until my legs went over the edge of the mattress. My legs dropped and my feet found the floor. Alan began to extract the dildo but reversed his movements to cause the dildo to rub every portion of my asswalls and slide across my prostate each time. Somehow he was moving with a little more force now and the sensations were almost more than I could bear.

“Oh, yeah, man,” Alan drawled in a sultry tone. “Oh, fuck, I knew you could take it.”

“Ohhhh!” I wailed.

“Fuck!” he cried out as he moved the dildo in ever faster plunges into my depths.

My mind was almost blown. I wasn’t really thinking, just feeling the immense sensations. Oh, god, it felt so good. Abruptly Alan stopped again with the dildo fully embedded in my rectum. My excited ass spasmed a few times as it alternated between squeezing the dildo and releasing it. As some coherence returned to my thinking, I realized I was hornier and needier than I had ever been before.

“Now rise up from the bed a little so you have room to take your dick in your hand.”

I complied with this latest request/command.

Behind me Alan moved around for a few seconds before I heard the click of the bottle-top and the splop of lube onto … ? What? I didn’t know where the lube was going until Alan’s hand slipped between my legs to grasp my dick and roll it in a glob of lube in the middle of his palm. The thought that he was touching my dick this way was the sexiest thing ever! For a few moments he lubed me up thoroughly until I thought I might be getting close to an orgasm. Before I came, he released my dick from his hand.

“Take your dick, man,” he said.

I complied again.

The dildo began moving again as I grabbed my throbbing dick.

He drove it into me harder and faster than ever before as I began tugging on my swollen dick. Oh, how I wanted to cum! I stroked my dick in time with the thrusts into me. In and pull. Out and relax. In and pull. Out and relax. It took only a few times before I felt the heat in my innards multiplying. In mere moments, the agitated feeling of desperately needing to release my wad grew and grew until it simply exploded. “Oh, fuck!” I screamed. “Fu-uck!”

White hot spunk raced through my urethra before flying forward over the mattress until it finally crashed onto the surface of the sheets. I screamed near the top of my lungs. “Oh, oh, god, oh, fuck!”

With each rhythmic blast of cum as my body shot it through the cannon between my legs, I felt the expulsion of the need, the excitement, and the evidence of my life-force in one giant explosion after another. When seven or eight great bursts had shot my wad, I collapsed onto the bed with the dildo still buried in my ass.

Behind and above me, I heard Alan chuckle. “Now, that was pretty spectacular, Calvin.” He said over the magnificent cello music. Then he slowly pulled the dildo out of my exhausted hole.