If you are under age, or live in an area where reading stories that include sex between males is illegal, or if you're not into this type of story, please leave. This story is a work of fiction written for my amusement and yours. I have added a lot of fantasy to the very little I know about hypnosis. As they say on television, do not try this at home. Please leave hypnosis to the professionals.
The author retains all rights. No reproductions are allowed without the author's consent. Comments are appreciated at NJMcMick@yahoo.com.
Chapter Four
Josh
I got up Friday morning and checked my email as usual before leaving for work. There was one with a return address that looked familiar but I couldn't place it. I opened it and saw that it was Jake.
"Congratulations, kid! I would call that a successful test run. I have a suggestion, though. Sometime before our session next Tuesday, stop by one of the adult bookstores in the area and pick up a larger toy. You handled that small one nicely but you'll probably run into a larger guy now and then and we should make sure you're able to accommodate something a bit bigger. It doesn't have to be huge, just bigger than you think you can handle. Have a great weekend, Josh! Ya done good. Jake"
A bigger one? How big? He didn't say. I guess that was up to me. I really didn't think I could take anything bigger than I already had but I got his point. If I learned how to handle one of the larger ones I wouldn't have any problem with whatever came up, so to speak.
After work I went to Cupid's Toy Box out on the highway. I'd only been there once with a female coworker when we were buying gag gifts for a party. There was a back room with lots of video booths and a few guys lurking around but I didn't pay any attention to them. I went over to the wall of dildos and vibrators. They had every size from much smaller than mine to massive. There were too many choices and I had a hard time deciding. I finally settled on a nine-incher with a mushroom head. I couldn't imagine ever being able to get that up my ass but I knew if I did I was set. I'd never even seen a real cock that big so I knew I could take anything if I could take that.
Saturday I went out to Connexions with a couple of friends, Tom and Mike. They danced, I watched. I was always too shy to get out on the dance floor. Maybe Jake could work on that next.
"You should really start dancing, you know, Josh. What happens if you meet a guy who likes to dance?"
"We'll just double-date with you guys and the three of you can dance together, Tom. But I don't think I have to worry about that. There are no guys on the horizon for me."
"You ought to be dating more, not hanging out with old married couples like us."
"Well, if you guys were really my friends you'd be fixing me up with guys. You're falling down on the job here."
"All of our other friends are couples like us but we'll ask around. A cute sweet guy like you shouldn't be hard to fix up."
"That's what people keep telling me, Mike, but no one ever does. I think I'm resigned to being an old maid."
Maybe it was a good thing I got that new dildo. Chances were it would be my only boyfriend.
Jake
If I hadn't thought it was over with Teri before there was no doubt after the weekend. Things hadn't been good for a while but Saturday night was a disaster. We went out for pasta at the Reservoir Tavern and had to wait forever for a table. The food was great as usual but we were both in a bad mood by the time we got it. The real trouble began after we got back to her place. We sat in the living room, had some wine and intermittently talked and kissed for a while. I was usually in a rush to move on to the bedroom but I just wasn't feeling it that night. Finally, she started taking off our clothes and we went into the bedroom. We'd been making out forever, which didn't bother her because she really got into foreplay. But the reason I was drawing out the foreplay was that I just wasn't getting hard. Yeah, Big Jake was swollen quite a bit but not hard enough to fuck with. This had never happened to me before except a few times when I'd had way too much to drink. Usually he was up and at 'em at the first suggestion of sex.
"C'mon, baby, I'm ready. Make love to me."
Maybe she was ready but I wasn't. I kissed her again, closed my eyes and thought of Josh's ass, that cute little bubble butt, that hot pink hole, that dildo sliding in and out of it the other night. That did it. Big Jake was rarin' to go. I broke the kiss and positioned myself between her legs. I reached around under her and grabbed one ass cheek in each hand and pulled her up toward me. I closed my eyes and imagined I was squeezing Josh's cheeks and groaned.
"Oh God, I really want to get into that ass."
Teri tensed up and then pushed me away-hard. I tumbled to the side and rolled off the bed, landing on the floor with a thump.
"What the fuck is wrong with you, pervert? How many times do I have to say no to that?"
"I'm sorry, baby, I didn't mean it. It just slipped out."
"Well, you can just slip right out of here, mister. You're lucky I don't report you to the medical board. A man in your profession with such a kinky obsession. You could lose your license. Now get your sorry ass out of here. I'm sick of your shit."
I grabbed my clothes off the floor and hurriedly threw them on as I made my way to her front door. I got in the car and started home thinking, 'Damn, what is wrong with me? It's just a hole.'
I noticed Connexions was still open as I drove past. I was tempted to stop in but I didn't trust myself running into Josh in the mood I was in. Instead, I went home, stripped off my clothes, turned on the computer and watched Josh's performance from the other night, pounding myself and Big Jake into a frenzy. I tried calling Teri a couple of times on Sunday but she just hung up as soon as she heard my voice. Oh well, single again, I guess.
Josh
I was really looking forward to seeing Jake on Tuesday. Just being with him was always great but this was the first time since he'd seen me fuck myself. I was feeling a little like a guy who'd aced his first exam. I was a little uneasy though. He'd emailed me and asked if I got the new dildo. When I told him I had he asked me to bring it. I couldn't imagine why. It was one thing to do stuff over the web cam, but if we were going to do anything in person I wanted the real thing, not latex.
I didn't have anything to worry about though. He apparently just wanted to check it out. He looked it over, tossed it from one hand to the other, like he was gauging it's heft, even wrapped his hand around it and stroked it a few times. It was weird watching a straight guy playing with a dick, even though it was made of rubber.
"Not bad, Josh. I guess it's big enough."
"They had much bigger ones than that, Jake, but I can't even imagine there are guys that big. I'm sure I'll never run into a guy any bigger than this. Even so, I don't think I'll ever be able to take this."
"I've got confidence in you, Josh. With a little work I'm sure you can do it."
I put on the headphones and lay down on the couch for another forty-five minute session. I didn't know if he was putting me in a deeper state but I didn't seem as aware of everything this week and the time flew by. Maybe his voice was just so soothing that he was putting me to sleep. In any case, I felt great when he snapped his fingers and brought me out of it.
Once again I stayed and talked for a while before heading home to put on my show. When I got home I started the same way as I had the week before, using my fingers to loosen me up, then my small dildo. It went in with no problem this time and I moved it around, twisting and rotating it, trying to stretch my hole more than before with it. After a while I decided I was as ready as I was ever going to be. I took the new dildo and slathered a lot of lube on it, then pressed it to my stretched hole. Nothing happened at first so I pushed harder. All at once the mushroom head popped through my ring and I gasped at the pain. It was much worse than the week before and I was tempted to pull it out but I remembered that the head was bigger than the shaft; so taking it out would hurt more than leaving it in. I took some deep breaths and tried to relax, using some of the techniques that Jake used in our sessions. Finally the pain went away and I just had a very full feeling. I gave the base a push and started sliding the long thick shaft into me. When I got it all in I turned and looked over my shoulder at the camera and smiled to let him know I was okay.
Once I had it in there was no way I wasn't going to fuck myself with it but I wanted to try something different this time. I turned over and lay on my back with my legs spread apart. With my left hand I fucked the big dildo in and out of my ass while I pumped my dick with my right hand. In this position the dong kept hitting my prostate with each stroke. I didn't just feel full now; I felt great. I started thrusting it harder and harder into me, trying to get it further and further up inside me. I was really getting into it but I knew I couldn't last long. I felt my balls about to boil over and lifted my head up to look at my dick and the camera beyond it. I let out a loud groan with my first volley and it shot straight into my mouth. The rest coated my neck, chest and stomach. I slowly pulled the dildo out of me and set it aside.
I was feeling a little devilish so I half sat up, leaning back on my elbows and looked at the camera. With my right index finger I scooped up some of my cum from my stomach. I stuck my finger in my mouth and sucked it. I repeated that a few times, then smiled and winked at the camera. I got up and turned of the web cam. As I was cleaning myself up I stopped, looked in the mirror and said to myself, 'You're flirting with a straight guy. How pathetic is that?'
Jake
I was anxious to see what size dildo Josh had purchased. It would be hard to judge the size over the web cam so I asked him to bring it over. I thoroughly checked it out. It's not that I was interested in the dildo per se, but I was curious to see how it measured up to Big Jake. It seemed to be about an inch shorter and not quite as big around, although the head was just about the same size. I didn't want to admit it, even to myself, but I knew what I was thinking. If he could handle that dildo then he could handle Big Jake. Not that that was ever going to happen. It was just nice to think about.
When I put him under I took him deeper this time. I knew he was going to need help when he got home with that big toy and the deeper he went the more susceptible to suggestion he was, the more I could urge him to relax.
That was my altruistic reason. The more selfish reason was that these sessions with Josh had rekindled my interest in hypnosis. It had been a while since I'd tried it and I wanted to see how good I was. Josh was a good candidate and I was curious to see how far I could take him.
Afterwards we sat around and talked again. Our relationship was getting to be very strange and disjointed. First there were the hypnotherapy sessions to help him relax. Then our talks, just two buddies shootin' the shit. Then he'd go home and perform sexually for me over the web cam. It was like we had three different relationships going, therapist-patient, friends, exhibitionist-voyeur. I was enjoying all three and I think he was too.
At ten thirty I was sitting naked in front of the computer monitor, all boned up, waiting for the show to start. Josh didn't disappoint me. He put on a hell of a show, fucking himself like a madman on that big dick. I leaned back in the chair, watching Josh, stroking Big Jake with my right hand, my left hand wandering over my body, squeezing my pecs, pinching and twisting my nipples, caressing my smooth abs, tugging on my balls. Oh man, I couldn't remember ever being that turned on. I even got off on watching Josh stroking his own dick. And when he lapped up his cum at the end it just blew me away. I exploded and creamed all over my chest and abs, imagining him licking up my jiz like that.
Later, I was lying in bed, thinking about Thursday. What next? Josh had wanted to learn to relax so he could get fucked. In just a few sessions I'd relaxed him enough to handle a big dick. He'd need a little reinforcement and maybe a brush-up now and then, but we'd pretty much done what we set out to do. But that couldn't be the end of it. That boy and his hole were getting to me like no one I could remember. I wanted more of him, more of that hole. But how much more? How much did I want? How much would he give?
To be continued...