Boy Meets Dildo: A Love Story
Warnings: Slash, dildoes (dildi? What is the plural?), bad porno movie titles. Also this is unbetaed but I checked it over pretty good. Let me know if I missed something. Disclaimer: I don't own 'em, but the so-called "real" owners knew what the hell they were doing, I wouldn't have to step in like this.
Feedback is better than chocolate!
I just had to know. Even though one fumbling encounter with Angie had supposedly taken care of my virginity, there was still another virginity to go. My ass.I've never been butt fucked. No one has even stuck a finger up my ass. Not even me, and I jerk off at least three times a day.
Not that I haven't thought about it. A lot.
Two of the guys I admired the most had crossed that divide. Buck I knew, never met a kink he didn't like, and had a wide assortment of devices, plugs and novelty gear, for fun and games with all the ladies he could convince to experiment. Buck had just grinned boldly when I go up the courage to ask if he was ever on the receiving end of these novelty items. All he said was "Don't knock it, kid."
Buck had also been the one to discover that Vin had been breached. On his last birthday, Buck had bought Vin a quart size bottle of WET brand Wild Strawberry flavored lubricant. Everyone had had a good laugh when Vin had placed the bottle of slick front and center on his desk, but the humor seemed to drain away in direct proportion to the lube inside the bottle. Almost everyday the level of strawberry flavored fluid inside the bottle seemed to get lower and lower. When Buck asked him right out if he was pouring the slick out as a joke, Vin confessed that he was gay and a active social life was causing the drain on the bottle. Buck laughed even more uproariously, and the rest of the guys seemed OK with it, although Chris got very quiet. He had a look on his face that was...well.... I don't know what it was. Chris can be real hard to read.
I told Buck that so-called gag gift was a bad idea. Just a week later, as the level in Vin's lube bottle got steadily lower, Chris evidently was fed up with it. Just yesterday, about an hour before we were all supposed to leave for the weekend, he yanked open his office door and yelled, 'Vin! Get in here! And bring that DAMN bottle with you!' Vin was in Chris's office for a long time, 'til after everyone else had left. I guess Chris was real mad. I had hoped Vin hadn't been in too much trouble, and Chris didn't lay into him too hard. Chris can have quite a temper. Although.... they both sure seemed happy when I had seen them later at Inez's, so I guess they made up.
Anyway, this was the perfect time to 'borrow' one of my roomie's playthings and breech my final frontier. Buck wasn't going to be back all night, as he was spending the night with Svetlana and Bebe, two SwissAir stewardesses that were keeping him busy all night every third Saturday when they would have their layover. I really don't think that Buck would mind.
I enter Buck's room and just in case, lock the door behind me. You can't be too careful. I look around for a second at all the dark green in Buck's room, everything seems to be in that color except for the track lighting over the bed. I headed for the old fashioned steamer trunk with the wood slats and the leather straps. Buck calls it his "Pleasure Chest." I took a deep breath and flung open the lid.
Holy cow! I couldn't believe my eyes. Pink ones, purple ones, jelly ones! One of them had two ends! What the heck was that for? Just looking at the array of sex toys was shooting signals straight to my cock. My jeans got real confining.
The collection of videos was daunting, too. "Driving Ms.Daisy into the Headboard." "In the Heat of the Nightie." "The Magnificent Seven Inches." "Sperms of Enrearment." "Genital Ben." "As Big as it Gets." "The Wadfather." "Ordinary Peepholes." "Young Buns." "Shaving Ryan's Privates." Hey, look at this one! "Journey to Uranus - an anal self love guide." Gosh! Just what I need!
I selected a smallish pink dildo, without all the bumps and everything. No sense trying to bite off more than I can chew. I pulled the green velvet coverlet from Buck's bed and threw the old blue sheet I had brought with me from my room over the bed to protect his sheets. No need to advertise to Buck that I had been in his room, borrowing his things. I put the condoms and lube I brought with me on it next to my dildo selection. Then I put the video into the TV/VCR combo that Buck had set up across from the bed in his room and brought the remote back with me to the bed.
Even though I was by myself, I started to feel self-conscious as I stripped. I thought about what Buck would say - "Kid, everyone has to decide what feels good for them. How do you know unless you try?" Of course Buck probably didn't mean for me to come into his room while he was gone and borrow his dildo, but it's the spirit of what he said.
I started to get ready by uncapping the lube and pouring some onto the fingers of my right hand and rubbing over my dick and balls, all the while with one eye to the video. The cool lube gave me a little shiver. The Journey to Uranus video started out with a look at some dildos and a narrator talking about getting prepared for the experience of your life. The narrator introduces Dallas, a young guy with long light brown hair; he actually could have been Vin's younger brother.
The cassette had looked like it was a brand new video, but it must have been old. Just as Dallas enters his bedroom, the camera lingering on his jean clad ass, the tape would shift and make a weird whirring sound, as if that part of the video had been seen over and over again. There it goes again, the little whirring sound, as he gives this sly wink to the camera, just as he slides off his undone jeans. That wink, it made him seem even more like Vin's younger brother. I wondered if Buck had ever thought the same thing. Probably not.
The narrator was saying how you should go slow and have lots of lube your first time. Dallas however was ahead of the class and after a few circles around the outside, already had one lubed finger slipping inside. I hit pause so I had time to catch up. With the remote in my left had, the index finger of my right did slow circles just outside my pucker. That felt pretty cool! I pushed my first finger in and stopped with a small gasp. That kinda burned a little! I hit play again to make sure I wasn't missing something important. That always happens with stereo instructions.
The narrator says that I may feel a burning sensation the first time. Duh!! Now he tells me. I certainly wasn't feeling anything like the guy onscreen was, who had his head thrown back and was giving out little moans. The narrator was describing that as a prostatic response. I think Dallas must have longer fingers than me. I just had this weird sensation of fullness, like I had to go but it could wait. It was nice though and I missed it as I pulled my finger out again.
Vin's onscreen younger brother was already grabbing the bottle of lube again and rolling a condom down the rather sizable dildo that would be the first demonstration. I though about changing to a larger one, but this wasn't a competition right? The narrator was saying that the condom kept the dildo clean, and if I didn't use a condom I would have to wash the dildo thoroughly with soap and water. Duh again! In my haste to catch up with my video demonstrator, I almost didn't get the condom rolled down the shaft because I had tried to put it on upside down.
Still, with lots more lube applied, my carefully wrapped dildo was ready to go where no man had gone before. I snorted at my own joke. Nobody gets my jokes but me.
I tried to imitate the angle and movements I was seeing in the vid. That guy was sure having a good time, his head rolling back and forth as he started with short, shallow pumps as the narrator recommended. Now things were really starting to get good, a strange new warmth starting in my ass and spreading little tingles to my belly and cock. Following Dallas's lead I proceeded to push in the full length. Wow!! What was that!?! I hit, I don't know, a bump or something and my cock got a big jolt of electricity and started drooling. I could see now what my video playmate was enjoying, as I probed for that spot again.
Why had I waited so long to try this? I pulled almost all the way out and pressed right back in again, mirroring the action on the video, though he was obviously a little more experienced and was wailing away.
"Yeah man, fuck it. Fuck that cock deep!" even though I knew he couldn't hear me. My cock was drooling like a tapped maple now, and I just had to stroke it. I gasped again at the electricity that seemed to have built up in my cock. It was like I had never stroked it before, instead of just a few hours ago.
It was awkward to reach behind me with one hand on the dildo and try to use the other hand to stroke my cock, so I rolled back and sat up with just an inch or so sticking out of my ass and kinda wiggled around on the bed. My right hand became a blur on my cock as the wild new sensations went through me, the dildo rubbed my prostate on every wiggle. Almost before I knew it, my ass had clenched hard around the rubber intruder and I was having one of the most incredible orgasms of my life! I almost blacked out and I could swear there were little stars at the edge of my vision. My chest and belly was a sloppy mess of spunk. There was even some in my hair, I had come so hard!
I ran out to get a towel from the bathroom and clean up. Just to be sure I checked the headboard of the bed and sure enough I had to clean that too. I could have entered a 'shoot for distance' contest. The video had continued while I cleaned up and at this point Dallas had evidently moved on to the advanced class. He was on the balls of his feet, bending his knees and about to sit down on a huge black dildo, maybe 10 or 11 inches long in what the narrator was describing as the 'cowboy position.' Gosh, his eyes even look like Vin's. I figured I had learned enough for tonight though, so I stopped the tape and made sure I pressed rewind so I could put everything back in the "Pleasure Chest" the way it was.
Something that good though I would have to try again, that's for sure. Maybe try one that's a little bigger. Maybe I would start a "Pleasure Chest" of my own.
Heck, maybe someday I would even try the real thing.
The End
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