Hope you enjoy Chapter 3 of Beach Weekend! Comments are greatly appreciated to ashram65@gmail.com. Flames will be ignored. This story is entirely fictitious. Feel free to share it, but please give appropriate credit to the author. Please remember to donate to nifty...it is a wonderful site.
BEACH WEEKEND – 3
I climbed off the bed, walked around and picked up the condom. I took it and the wrapper and went into the bathroom. I carefully wrapped it in toilet paper and set it on the sink to discard in the downstairs trash. Wouldn't want the other guys to see it and start grilling us over who got laid and wanting all the dirty details. Tom started the shower and stepped in. I sat on the toilet and we talked as he showered.
"You are still sure you are ok with this?" He asked.
I was more than ok, I felt great and wanted to do it again, but it was already well after midnight and I was a little tired from all the fun we had, and I told him everything was great and that I needed to sleep to regain my strength. Tom told me that if I was so tired, why don't I join him in the shower and we can get done faster and both get some sleep. I stepped in with him and we both washed ourselves without any playing around, got out and dried off. We said our good nights to each other and went into our own rooms.
I was exhausted, but the images of my cock going in and out of Tom's ass kept playing over and over in my head, and I found myself wondering how it would feel to be on the receiving end of a cock in my ass. My ass involuntarily twitched at the thought, and I reached my hand back and fingered my ass some to see how it felt. It was quite pleasurable, and I made a mental note just before drifting off to sleep to ask Tom to play with my ass some the next time we messed around...if there was a next time. The other guys were arriving tomorrow afternoon and who knows what time we would be able to find alone together.
I slept well considering all the exercise I had had the previous evening, and when I woke up, I threw on a pair of shorts and went down to the kitchen to make some coffee. The smell must have awakened Tom, and several minutes later he walked into the kitchen wearing a pair of running shorts. He looked so sexy in them, and I found myself wanting to drop to my knees, pull them off and suck that wonderful cock right there in the kitchen. He could see the look on my face.
"Like what you see?" He asked.
"You know where that led the last time one of us said that," I replied.
"I know," he said with a grin.
I poured two cups of coffee, handed him one, and we walked out onto the deck. We sat on the lounge chairs looking out at the ocean sipping our coffee. There was no question that there was a little sexual tension in the air.
"How long have you been taking it up the ass?" I finally asked.
"My first time I was about 19," he replied.
"What is it like?"
"It hurt at first, but with the right preparation and if your partner goes slowly and listens to you, it can be amazing. My first time hurt like hell, but he just wanted to get off, no prep, no nothing, just a quick fuck. I thought I would never try it again."
"So what made you try again?" I pressed.
"Another guy I met who was patient and listened to me. He never forced anything, he took his time opening me up and getting me ready, just like you did last night. Even last night, it hurt for a moment when you first entered me, but then that pain slowly flows away and a feeling of intense pleasure replaces it. Quite honestly, I love getting fucked and fucking too. I have topped other guys before as well, so I guess you would call me versatile."
I continued to sip my coffee and looked out over the waves as my brain tried to form my next question.
"How long would it take you to prepare me for it do you think?" I asked.
Tom sat bolt upright in the chair, leaned towards me and stared at me.
"Are you serious? You really want to try something like that? Christ, Jim, I'd love to have a go at your ass, and I would have tried last night, but I didn't think you were into trying it."
"I've got to tell you Tom, when I saw the look of pure pleasure on your face last night, something came over me and made me wonder what it would be like to be on the receiving end."
"It will hurt at first, I can tell you that, but if we go slowly, it will be ok after you get used to it."
I looked over at Tom. He looked back at me, sipped his coffee and leaned back in his chair.
"I would be honored to help you see what it is like, if you'll let me."
The tent in the front of his shorts was rather pronounced as his mind, I was sure, formed images of us naked again. My own cock had started to harden as well and there was really no way to hide my own tent either. I had already gone this far with my old friend; I might as well throw caution to the wind at this point.
"Then let's go inside." I said.
No words were spoken; we simply stood up, carried our cups into the kitchen, put them in the sink and wordlessly went upstairs again. I will admit I was a little nervous, wondering what I had just signed on for, but slightly excited at the same time. We again went to Tom's room. There was no pretense about getting undressed this time, we just stripped off. Tom took my hand and led me to the bathroom and started the shower.
"There is no easy way to put this," he said, "we need to clean you out inside first."
He went back to his room and came back with a hot water bottle with a long hose attached to it and the bottle of lube. He got the water nice and warm and filled the bottle up. I will spare you the details of all of this, but suffice it to say that 30 minutes later, I was as clean as I was ever going to be. We got out of the shower, dried off and headed back to the bedroom. Both of us were sporting the starting of some decent erections. After climbing onto the bed, Tom kissed me as he gently massaged my cock and balls. His hands danced over my body and it was like little electric charges going off everywhere he touched me. My penis has risen to its full size now and stuck off my tummy slightly. Tom continued his ministrations on my body, kissing me everywhere and saying soft words to me to relax me. He had told me in the shower that if anything didn't feel right or hurt, to tell him right away and he would stop. I didn't want any of this to stop right now. Tom moved over me and rolled my legs back up towards my head. I grabbed behind my knees to help him. My brain was thinking "here it comes", but it was wrong. Tom swallowed my cock to the hilt and started to give me another amazing blow job. His hands played with my balls and down over my ass and up and down my ass crack. He gently rubbed my virgin pucker, and I gasped slightly at the pleasurable sensation.
"Oh God, that is nice," I moaned.
"It is going to get a lot nicer," Tom said, pulling off my now wet cock.
Tom's tongue washed my balls, and proceeded south over my perineum to my ass crack. He nibbled and kissed and licked at my crack, deliberately avoiding my rosebud. I kept my eyes closed, reveling in the sensations my friend was giving me. When I finally felt his tongue touch my pucker, I again let out an audible gasp of pleasure. Tom knew what he was doing, and pressed on pleasuring me and my hole. He gently lapped at my hole, the feeling was like none I had ever experienced before, and I knew right then and there that this was what I wanted. He continued to rim me, eliciting moans and groans from me as I fought to stay focused on what he was doing down there. Tom must have rimmed me for several minutes, then he removed his tongue from my ass and went back to sucking my cock. Somewhere along the way, he had opened the bottle of lube, and I felt his lubricated fingers massaging my hole as he continued to bob up and down on my cock. I felt a finger slip into me, and while I expected pain, there was none. I was so totally relaxed that I barely even felt it until his finger probed and rubbed my prostate. My body twitched from the jolt of electricity that shot through it, and I leaned my head back.
"More," was all I could muster.
Tom put another finger into me, and while I felt it enter, again there wasn't really any pain. He continued to stroke his fingers in and out of me, while still paying careful attention to my cock, but pulling off now and then so as not to bring me to orgasm. When his third finger worked its way into my hole, I felt it. Not a great pain, but I could feel it. Tom asked if I was still ok, and I nodded. I think he might have suspected something from the slight wince on my face, but he took his time and continued on. As he stroked his fingers in and out of me, he would open them slightly, gently stretching my hole so as to accommodate what would come next. Finally after what seemed like hours, Tom asked me if I felt ready. I told him let's give it a try and see what happens. He sat up between my legs, fingers still buried in my butt, and reached over for a condom. He tore it open with his teeth and deftly rolled it on with one hand...a trick I think I have to learn. He squirted some lube on his cock and over his fingers that were still in my ass, then rubbed it all over his 7" and scooted closer to my ass.
"I want you to breathe and to try to relax," he said.
Tom slipped his fingers out and slowly pushed his cock into my ass. It hurt. I sucked in air hard.
"Breathe, try to push out like you are taking a shit," he said.
I concentrated with all I had on my breathing and relaxing and pushing out some. Tom's cock popped through my ring. He stopped pushing. I willed my body to relax more, and slowly the pain subsided.
"It's better now," I said, "doesn't hurt as much."
"Good, keep trying to relax."
Slowly Tom pushed more of himself into me. It was a most unusual feeling. I felt sort of full in a way. There was still some pain, but it was bearable. Not like the initial penetration, but sort of a dull ache. My cock had gone completely limp at this point, and Tom began to stroke it as he ever so slowly pressed into me. Finally I felt Tom's hips hit my ass cheeks and I knew I had all 7" in me. The pain was gone now, and Tom held tight in place without moving and asked how I felt. I told him it was alright, and he could pull back a little and push back in. He slowly withdrew a couple of inches then pushed back in. I felt his cock hit my prostate and a jolt of pleasure shot through me. I told Tom what I felt and he just smiled and nodded. My cock was starting to harden as Tom slowly started to fuck my now de-flowered ass. He was gently and kind and loving as he stroked in and out of me. He leaned in and kissed me and our tongues dueled with each other.
"Faster," I managed to pant.
Tom picked up the pace and on each down stroke, his cock slid over my hot button driving me into a frenzy. I grabbed at his back and pulled him into me harder and harder. I held my legs back so he could push deeper into me, so he could continue to stoke into me and give us both pleasure. It was a crazy jumble of legs and pumping asses and cocks...it was fantastic. I never wanted it to end. Tom held my ankles as he continued his now relentless assault on my ass. I had my hands around my legs and my cock slapped my belly each time he thrust into me. I didn't even feel it coming. All of a sudden, huge gobs of cum shot out of the end of my cock splashing everywhere. It hit me in my face, it hit Tom. I wasn't even touching my cock, and I had managed to cum hands free! What an amazing feeling. My cock continued to spew my baby makers all over both of us, the sheets, the headboard, everywhere. I was cumming like I had never cum before. With one final grunt, Tom pushed as deep as he could into my ass and orgasmed himself. He let out a howl as he filled the condom with his love offering. His body twitched and pumped and wave after wave of his orgasm crashed into him. He finally stopped cumming and collapsed onto me. Our bodies mashed together, smearing my cum over both of us. He kissed me deeply and licked some of my cum off my face. After several minutes of this embrace, he reached down, and holding onto the condom, slowly withdrew from my ass. He slipped off the condom and held it up. It looked to be almost full, and he tipped it out onto my chest and rubbed it into my skin slowly, while simultaneously feeding some to me.
"How do you feel?" He asked after a few more minutes.
"Folded, spindled and mutilated...and great" I answered.
"So you liked your first time?" He asked.
"Unquestionably, and I hope it isn't my last," I said.
"Maybe it won't be!" He grinned.
We both fell asleep in each other's arms, our shared cum drying on our skin.
Wow this has been a hell of a vacation so far.