Jack & Walt

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Two good friends have a bisexual awakening.
2.4k words
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143.4k
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Part 1 of the 3 part series

Updated 09/22/2022
Created 06/16/2003
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I lay on the bed naked. The window was cracked and a cool summer breeze circulated over my freshly shaved and squeaky clean body. I arrived back at the apartment early this Friday and took advantage of the extra time to prepare myself for the sexual adventure that hopefully was ahead this evening.

My roommate and I had been friends since high school, and grew even closer during college – all the buddy things two guys can do – sports, gambling, drinking, and, of course, talking about girls and sex. However, it was not until we took an apartment together and began sharing living space that our sexuality took a dramatic turn.

I lay there pondering the events leading up to this day. Living in close quarters, it was inevitable that close friends would learn intimate things about the other – their bodies, their quirks, their sexuality, - sometimes with surprising details. Walt and I had shared stories of every sexual conquest that each of us had had; laughing and joking about the girls we had been with. On occasion we would watch x-rated videos and slip off to our separate rooms to relieve the resulting sexual tension in private…each knowing what the other was doing. One night during a particularly hot video we each pulled out our hard cocks and jerked off; watching each other the entire time. Nothing was said, but over a period of months there developed a sexual tension between us that further stirred each one’s curiosity. A crotch stare that lasted a little too long, a comment here or there that left one wondering of the meaning, certain internet sites that we would catch the other in, always bringing more questions than answers. Finally a month ago on a boring Saturday night, a dirty movie and a lot of beer, then a joke and a dare, and we crossed that fateful line…since that evening we had completely opened up to each other, sharing both our minds and bodies, exploring our mutual bisexuality, and bringing each other pleasures previously unknown.

Lying there, my body tingled with increasing anticipation. My penis was now completely erect, so hard that I could see my pulse thumping in its veins.

“Please get here soon, damn it!” I muttered to myself.

I had shaved my balls, anal area and the base of my cock totally smooth, and was deliciously clean both inside and out. I had prepared myself for anal intercourse. Before my shower I took two warm and soapy enemas on the bathroom rug, readying my back passage for the hot and slick visitor it now needed so badly . Over the past few weeks we had explored the oral part of man-to-man sex, and tonight we would begin to explore anal sex together. My best friend was going to fuck my virgin ass.

I faintly heard his key unlock the door, and shortly he peeked around the edge of the door and smiled.

“All the way home I was thinking that you would be lying there like that. I have been half-hard all day thinking about tonight; I even jacked off in the car this afternoon…I couldn’t stand it!” Walt’s voice was actually quivering. “ Give me a few minutes to shave and shower, and I will be ready to join you.” He paused, “are you sure you are ready for this?”

“I have never been more ready for anything in my life” I answered. “Get in there and get clean for me so we can do this, or I am going to cum all over this room!”

The next fifteen minutes seemed like three hours. Finally I saw Walt’s shadow in the doorway. He turned at an angle and I could see the outline of his cock standing at attention. He approached the bed and I could smell the residue of soap and shampoo, and the sexy fragrance of Paul Sebastian aftershave.

“I see you used your new enema bag and nozzle…how was it”?, he asked.

“Fantastic,” I responded. “Just like I remembered from all those years ago. “I always enjoyed them, but especially today knowing why I was doing it… it was really hot!”

By now he was standing next to the bed…I turned toward him and my lips were only a few inches from his gorgeous dick. It was longer and a bit thinner than mine, circumsized with a slight upcurve when hard. Over the past three weeks I had studied it in detail and decided that it was a perfect fit for my mouth, and hopefully now my asshole. We would soon find out.

He leaned forward. I licked my lips and took the head of this sweet cock into my warm and wet mouth. He exhaled a low moan, and gently began a slow rocking motion as I gradually took in more and more of him. Copious precum leaked into my mouth, tasting sweet as honey. The sensation of sucking a cock, completely foreign only a few weeks ago, now seemed to be the most natural thing in the world for me. I loved knowing the pleasure that I was giving my friend.

“ God that feels good, Jack, but I need to taste you too”.

We separated momentarily while Walt crawled on the bed and we got into a side by side 69 position crossways on the bed. I reached behind him and, grabbing his ass cheeks, pulled him again into my mouth. He copied this motion and my penis was quickly immersed in his mouth, his tongue swirling over the head and shaft, his fingers tickling my smooth balls.

I released his cock and moved lower so that I could lick and suck his balls. I knew he loved that. I pulled his thighs to me and spread them, allowing me access to his most private areas, and I stretched my tongue out to caress the rosebud of his hole. He gasped with pleasure and ground his backside back into my face. The next several moments were encased in a sexual fog: touching, licking, caressing, probing…incredible new sights, smells, tastes, and feelings that neither of us had heretofore experienced. It was way too much…we each sensed the other’s boiling need for completion and in a frenzy of sucking and stroking, brought each other to a tremendous climax. Streams of hot man juice shot in each other’s throats and we eagerly slurped it down. The spasms finally began to subside, our muscles started to relax, and we were able to catch our breath.

“Buddy, that was incredible! No chick has ever been able to make me feel the way you just did” he whispered.

“I feel the same way…I can’t believe we discovered this in each other after all these years as friends. I have been bi-curious for a while now but never acted on it…I’m just glad it was you, someone I can trust”, I responded.

We continued to cuddle for several minutes, resting, talking about what has happened with us, and recharging for what was to come. Neither of us were to the point where we could include kissing in our play, but we were very comfortable cuddling. Walt lay behind me, spooning against my backside, and I could feel his flaccid cock begin to stir as it rested in the crack of my rear. His breath was hot on my neck as he reached for my nipples and began fondling them. Soft pinches caused me to shiver, and I began to feel stirrings of my own. He slowly moved his hand down over my belly and softly took my penis into his hand.

“I love it when you are freshly shaved…so smooth…thanks for showing me how to do it”, he said softly. “I think I will keep mine shaved all the time, too…it feels great!”

Walt released my now hard dick and moved his hand back over my hip and ass cheek, softly caressing the skin. He tentatively dragged a finger the length of my crack. I held my breath as he explored this new territory.

“You are so smooth and clean, I want to lick you back here”, he moaned. Blood was flowing to this area so fast that I felt lightheaded.

“Yes, please lick and kiss and tongue my ass, and then when you are ready, I want you to give me your cock…I want you to fuck me long and slow…” I was talking out of my head, no longer in control of the events surrounding me.

“Lay on your back so that I can see all of you” Walt requested. “I want to see your face”.

I rolled onto my back. My cock, full of blood again, waved sexily in the air. Walt moved down the bed and took a position between my legs. Acting like a total slut, I grabbed behind my knees and pulled my legs apart and toward my chest, vulgarly exposing my ass to my best friend and now lover.

“Do me now, damn it! I need it!” I blurted out. “Please fuck me!”

He was at once between my legs, sensuously licking my crack, kissing my asscheeks, and gently massaging the rubbery skin of my anal opening. He then focused his tongue directly on this rosebud. I gasped at the wonder of this new sensation – the feelings were like nothing I had ever experienced. I had rimmed a few girls before and knew that it drove them crazy, and now I knew why.

Walt reached for the nightstand drawer and retrieved the KY Jelly that he knew I kept there. He squeezed out a glob onto his finger and slowly began massaging the lubricant into my waiting hole. I had masturbated anally at times, but nothing I had ever done to myself compared to this. First one finger slipped past my sphincter, and then a second. He added more lube and was now finger fucking my ass. I never wanted this to end.

“My God, you are so hot and tight in there” Walt panted, gasping for air. “Do you think you can handle my cock okay? I know I’m not huge or anything, but I don’t want to hurt you”.

I somehow knew that my ass was ready for his penetration. Some primitive sexual instinct, perhaps derived and passed on from earlier gender-indifferent species, told me that I was ready to be taken.

“Lube yourself up really good, and go slowly”, I hoarsely responded, “but don’t worry, I can take it all. I want it all. I didn’t realize it but I have been waiting for this all my life”.

Walt grabbed a fluffy pillow and as I lifted up, positioned it beneath my lower back, providing a better angle for the coming assault. I again pulled my knees to my chest and waited. Precum dripped continuously down my shaft, glistening in the fading sunlight. Walt knelt directly below me now, his lovely cock bobbing invitingly in front of me. He squeezed a generous portion of the KY onto it, and carefully coated it’s entire surface with the slippery gel. Another squirt was applied to my anus, and his fingers went to work to lubricate and further stretch me open.

At this point I could wait no longer. I had to be penetrated and filled with this sexy piece of flesh between my friend’s legs.

“It’s time, buddy; let’s do it”, I said.

“ OK, here we go”.

I felt Walt’s cock in position directly against my hole. He applied a little pressure and the bulbous purple head popped inside me. A very brief and mild burning sensation dissipated quickly as my opening adjusted to the intruder. Walt was sweating profusely as he pressed his body onto mine. I gave him a reassuring smile and encouraged him to enter me further.

One, two and then three short in-and-out thrusts, and half of his seven inches were inside me. I was delirious with a wonderfully full feeling…no dildo or other toy had ever felt like this…it was hard, yet soft, and oh, oh, so hot!

Walt paused once again, but I could wait no longer. I suddenly thrust my hips forward, completely impaling myself on his dick. He gasped when he realized that he was now completely inside me – we could be no closer than we were at that moment.

”Oh my God, Jack, I can’t believe this! You are so hot in there. You are so tight and slick…it feels incredible!”

“Don’t move, Walt. Let me get completely adjusted to you”. I asked.

The early burning sensations had all but vanished, to be replaced by a wonderful fullness and pressure on my prostate that had my cock on the verge of exploding. Every slight move was a great new sensation for each of us as Walt’s cock settled into its new environment.

“How are you doing? You know, are you going to cum real fast or can you last a while”, I asked my new lover.

“I’m okay, I think”, he responded. “I’ve cum twice already today, but man, this feels really good!”

In my sluttiest voice I told him, “Please fuck me now”.

Leaning backward so that he could see the action, Walt slowly withdrew his cock from my rear, and again pushed it deep inside me. The feelings were indescribable…nothing had prepared me for this pleasure… Walt moaned and babbled obscenely about fucking his buddy’s bottom…we quickly developed a comfortable fucking rhythm and he pumped his beautiful cock into my waiting ass over and over…and then he groaned,

“I’m cumming”

“Cum in my ass…I want all of your juice inside me”

He then grabbed my cock and with a stroke or two brought us to a mutual climax… he shot thick ropes of cum deep into my bowels…I could feel the spurts against my inner walls…my own cum sprayed onto my chest and face in huge globs…

Walt scooped it up and licked his fingers, and then shared with me…

As the last spasms of our mutual orgasms faded, he collapsed on top of me, a tangled mass of skin and sweat. His cock was quickly returning to normal size, and slipped out with a plop. I could feel his semen inside me, and with a couple of squeezes I was able to expel much of his load onto the sheets.

“Holy shit, I’ve never seen so much cum in my life”, he said.

We both started laughing as we gradually came down from the sexual high.

“Hey Jack, next time can we switch? I think I want to try being on the bottom”, Walt asked as he drifted toward sleep.

“Sure thing, friend, sure thing”, I answered.

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