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The Convention Part 2 of 3

Posted by: Age: 28 then 65 now Posted on: 13 comments
20 likes 40 views Category: Masturbation Male-Male Tags: masturbation, jerk off, jack off, skinny dipping, massage, prostate massage, prostate orgasm

If you have not read Part 1, although it is not absolutely necessary, I would recommend you do so. As a reminder from Part 1:  Paul, a friend from college and grad school who was attending the same conference as I in Atlanta agreed to cut hotel costs by rooming together in a nice downtown hotel.  We returned to our room after eating dinner each of us took showers before bed.  Hoping Paul would join me, I made it clear to him I planned to masturbate myself sometime before going to sleep. I hope you enjoy Part 2.


While I was in the shower, Paul had changed the channel to a Pay-Per-View movie.  It was soft-core porn.  At the time, no hard-core porn was available on hotel TVs.  After turning down the covers on my bed, I sat naked on top of my covers with my back against the headboard, just as I had been before stripping and taking my shower.  I looked over at Paul.  He was watching the movie, still sitting naked up at his headboard and was randomly playing with his dick as we men sometimes do.  He wasn’t actively masturbating but playing enough so his dick remained at least partially hard.  Although I had been clear about my intentions to masturbate before going to sleep, I was still a bit surprised that Paul was being this open with me by playing with himself.  Although, at this point, I had never masturbated with another man, my curiosity had removed any opposition to the idea.  In fact, before our trip I had contiplated how I might be able get the ball rolling in that direction.  Since I was so sure Paul was totally straight and would never have masturbated in front of another guy, I certainly thought that if it were to happen I would need to be the one to push the idea.  But clearly, he had thought about this maybe as much as I had.   While contemplating all this, I suddenly remembered something from our past and realized I shouldn’t have been so surprised at Paul’s nonchalant attitude about nudity and masturbation.  During graduate school, we were each newly married.  After several months of getting to know each other, we began to be more open with about somewhat sensitive subjects.  We finally felt we knew each other well enough to talk openly about our sex lives.  Neither of us felt our wives had as strong a libido as we had.  We were both virgins when we married and partially because of that and the fact that school was so stressful, we both wanted sex most every night.  Neither of our wives was up for that.  We talked about the fact that to help deal with the discrepancies between our wive's sexual desire and our own, we needed to masturbate ourselves quite regularly.  These frank talks about our sexual appetites, what we enjoyed doing during sex and how often we desired sex with our wives caused us to become very close friends.  We also talked about other topics like nudity both in our homes and outside and the fact that we both really enjoyed skinny-dipping when the opportunity presented itself.  I told Paul that when I was young a friend and I used to skinny dip in his pool and how much I enjoyed being naked in and around the pool.  I told him about the day this friend introduced me to the pleasures of allowing the water from the return hole to flow over my cock head.  What wonderful hands-free orgasms I had that way.    After revealing to each other our love for skinny-dipping, Paul decided that we should take his small fishing boat out on the river near our school and go skinny-dipping together.  I thought it was a great idea so we planned a day when we were both free and off we went to the river.  We found a relatively private spot, anchored the boat and enjoyed the freedom of swimming together naked.  I had an erection almost from the moment of hitting the water.  I love the feeling of the water flowing around my low hanging balls and hard cock as I swim and can’t help but play with my engorged prick.  Of course, we also horsed around with each other and as we did, our hard dicks would occasionally touch each other’s bodies.  It was fun for us to jump on each other in an attempt to dunk the other.  When we did this, our dicks would rub against the others' butt or back.  When tumbling under the water, our dicks would sometimes touch each other or rub against some other body part.  This made for fantastic pleasure for the one whose cock was doing the rubbing, but we never really considered it a sexual act.  It was just two naked guys having fun in the water.    We went skinny-dipping together several times and once convinced our wives to go with us.  He and his wife, Sarah stayed on one side of the boat and my wife, Lisa and I stayed on the other.  We could still see each other’s heads and shoulders but we couldn’t see much else of each other.  Since skinny-dipping always makes me horny, after just a short time of swimming together, I pulled my wife close and started kissing her deeply.  I fingered her pussy and clit, making her moan quietly.  I saw that her breasts were floating beautifully high in the water, so I put my lips just under the water line and played with her very aroused, hard nipples with my lips and tongue.  My cock was about as hard as I could ever remember it and I was having the time of my life.  I loved making my wife gasp and moan.  I loved the way her pussy lips felt in the water and I adored making her shiver and quake as I played with her clit.    Not long after I started playing with Lisa, she became self-conscious and whispered, “You need to stop!  Paul and Sarah will see us.”  I smiled and said rather sarcastically, “I don’t think they are going to care all that much,” as I rolled my eyes toward them and pointed my head in their direction.  You see, Paul and Sarah were passionately making love to each other on the other side of the boat.  Lisa smiled coyly, giggled and said, “No, I guess they won’t.”  She giggled again and said, “In that case, get busy babes.  I need you.”  She didn’t need to tell me twice.  I immediately got back to work on her beautiful breasts and returned to playing with her pussy.  Lisa and I had wonderful orgasms that day and it was clear from their smiles that Paul and Sarah did too.  Other than burning our faces and shoulders a little, it was a fabulous experience for all of us.   Once I remembered these fun times on the river, Paul’s nonchalant attitude about nudity and penis play finally made complete sense to me.  I was sure that back during graduate school neither Paul nor I would have masturbated together.  We might have talk about it once.  We would get hard in our pants as we talked about sex in general but actually take our clothes off and masturbate together?  Never!  That would have been gay.  We couldn’t act gay.   It had been at least three years since we had been in graduate school together.  Over that period of time, our attitudes about such things had changed.  We no longer felt that simply masturbating in front of each other to deal with our sexual need for pleasure and release should be considered gay.  It was just a physical need and our wives were not here to satisfy those needs so it only made sence to take care of ourselves.  Paul looked over at me and said, “It looks like you have the same idea I have about masturbating tonight.  I thought I would have to wait 'til you went to sleep to jerk but how about we just be grown men about this and not hide what we’re doing.  Let’s just jerk together?”  I said, “Sounds good to me my friend.”    “Hey, I need lube to be able to jack off right and I forgot to bring any with me.  Obviously, you were a better boy scout than I and came prepared.  May I borrow some of yours?” he asked.  “Sure,” I said, “but I don’t plan to hurry through this.  I want to edge a while.  Is that ok with you?”  “Absolutely.  I haven’t had sex or masturbated for over two weeks and I’m about to burst.  Edging sound good to me too,” Paul admitted.  “Since we’re going to edge,' I replied, 'I’ll probably need to reapply lube every now and then, so why don’t you move over here on my bed with me so we don’t have to keep tossing the bottle back and forth.  After all, remember. . .I’m not a very good pitcher and I’d hate to toss it and hit you squarely in your balls.”  “Ohhhh, noooo!  That doesn’t sound good,” Paul said as he smirked at me.  He popped off his bed, walked to the other side of mine and jumped on it with me.    By now, I was fully hard again so I squirted some lube on my hand and began to lube up my cock and gave the bottle to Paul.  He did the same and we started masturbating ourselves with our bodies close together on my bed.  We were so close our hips and thighs were touching.  It felt good to be this close to him again.  I hadn't been since we skinny dipped and played in the river together.  Paul’s erect cock is 7.5” and very thick.  So thick, in fact he can’t get his hand all the way around his shaft.  Mine is a very average 6” and not as fat but still thick enough that in the beginnng of our marriage, it was sometimes difficult for me to push my dick into Lisa's very tight pussy.  Each of us got comfortable on my bed but we both were still sitting upright, our backs against the headboard.    Clearly, we both wanted to enjoy this and make ourselves feel as much ecstasy as possible.  I stroked my shaft slowly and every few strokes pulled my hand up over the head of my dick with a twisting motion.  I spent much more time watching Paul jerk himself than I did watching the soft-core movie.  I had my own hard-core video playing right next to me so why should I need the movie?   After having watched Paul for a while and after gently playing with myself for the same period, I got brave enough to attempt something new.  I worried it might mess things up between us but I decided to go ahead and give it a try.  I added some lube to my left hand and reached over toward Paul’s scrotum.  I didn’t actually touch it yet but with my hand ever so close to it, I looked into his eyes and raised my eyebrows in essence asking his permission to play with his balls and scrotum.  He hesitated just long enough for me to get a sinking feeling in my gut that I had made a huge mistake.  But then he nodded his head slightly giving me his permission. I felt so much better because I never wanted to do anything to ruin our freindship.   I swirled my hand over and around his balls and he softly moaned.  I continued playing with his sac, massaged each of his balls individually and tickled them gently.  Paul threw his head back and bellowed, “Ahhh, that feels great.”  As I continued to tenderly play with his balls, I rolled slightly toward Paul and began to lick and suck his left nipple.  I knew I was again taking a chance but thought his nipple was surely less intimate than his scrotum so he would probably be ok with me playing with it.  Thankfully, after giving his nipple some attention Paul groaned, “I’ve never had anybody do that to my nipples.  Shit, it feels better than I ever would have imagined.”  After a little while, I let go of his balls and nipples and began to stroke myself again but Paul said, “You seem to be ok with us touching each other, right?”  “Yeah, I am,” I said.  “Then let’s do this right.  Let me work on you for a while and then when you get close to cumming we’ll switch and go back and forth like that.  My college roommate and I used to do that and it felt great.  Does that sound good to you?”  It did, indeed because I was finding it hard to concentrate on Paul and myself at the same time.  I must admit though, I was very surprised at what he told me about he and his roommate masturbating each other.  I knew his roommate fairly well and couldn’t imagine he would let another guy touch his package.  I began to feel like I had really missed out on something fun.   Paul told me to lie flat on the bed and spread my legs.  When I did, he knelt between my legs and began to play with my balls.  He pulled on them with one hand and tickled them with the other.  It felt fantastic.  I loved it.  He added more lube directly to my cock head allowing it to drool down my shaft and then started gently stroking.  He used different hand configurations, sometimes underhanded, sometimes over.  Sometimes he used one hand, sometimes two.  He stroked fast for a while and then slowed way down.  He continued to jerk me while playing first with one nipple and then the other.  I was in 7th heaven but felt my balls pull up toward my body and my dick begin to thicken even more.  I was about to say we needed to switch places when Paul noticed these changes too and stopped jerking my dick.  He started to turn over so he could lie on his back when I said, “Hold up.  I want to try something different on you.”   “I want you to lie on your stomach and let me massage your back and butt some before I actually start masturbating you.”  Without complaint he changed positions and I used the silicone lube in place of oil for his massage.  My dick was still fully hard so right before I sat on his butt, I squirted some lube in his ass crack.  As I sat just below his butt, I pushed my dick into the cleft of his ass.  I moved forward and back in a fucking motion thereby stroking his asshole with my dick as I massaged his neck, shoulders, upper back and arms with my hands.  With each movement of my dick in his cleft, I could feel him push his butt up toward me a little more.  He clearly enjoyed the feel of my prick gliding over his asshole and so did I.  I had never done this before and I was quivering with delight.  Once I completed his upper back and arms, I put my knees between his legs and nudged them open more.  I moved back, now kneeling between his legs began to massage his ass cheeks.  Paul has a perfect ass; round, tight and dimpled.  I tried to think of as many wasy to stroke this region as I could so he had plenty of time to enjoy the massage.  After giving his ass lots of attention I started rubbing round and round his rosebud with my fingers.  I heard Paul say in a dreamy voice, “You can push your finger in there if you want.  I do it sometimes when I masturbate.”   I was surprised Paul gave me his permission to do it but I did want to try it on him so I gently began to apply more and more inward pressure to his hole and eventually it opened to me.  Almost as soon as my finger entered, I felt a swelling I knew had to be his prostate.  I stroked it gently as Paul began to howl louder than before.  I pulled out and added more lube to both his crack and my finger and pushed back in.  I massaged his prostate gently and then increased the pressure and massaged it a little harder.   I removed my finger from his prostate and finger fucked him a while.  He seemed to love both actions so I continued to alternate between them. His breathing became harder and harder and then, he almost screamed, “Ohhh man.  Ohhh fuck.  That feels so good I almost can’t take it anymore!”  Then, only about a minute later I felt him tense all his muscles as he franticly shouted, “Wait . . . wait, I think I’m gonna pee!!”  I knew from experience in having prostate massages myself that he wasn’t going pee.  He had urinated right before his shower so he couldn’t need to yet.  Instead, he was about to have the best orgasm of his life; a true prostate orgasm.    I kept massaging his prostate and said, “You’re not going to pee.  You’re about to have a prostate orgasm.  Just relax and let yourself enjoy the feeling.  Let your body move any way it wants to.  Just go with it.”  Thankfully he trusted me enough to allow himself to enjoy the feelings he was having and began to bounce on the bed and squirm all around.  I knew my only job now was to somehow keep my finger impaled in his asshole, massaging his prostate as his body bucked and moved all over the bed.  Paul was sweating from every part of his body.  He was breathing incredibly hard and his muscles began to spasm.  His asshole clamped down so hard on my finger it felt as if it would break and his toes were curled the most I had ever seen.  He was experiencing a huge, full body, prostate orgasm.  He leaked a massive amount of pre-cum but when his orgasm hit, he didn’t ejaculate.  Just a very small amount of pearly white cum rolled from his slit.  When it was over Paul told me he felt the orgasm from the top of his head, through his spine, down deep in his groin and down to his toes.  I told him to check out his cock.  He said, “What?  What are you wanting me to do?”  I said, “Look at your cock.”  He got on all fours and said, “What am I supposed to be looking at?”  I said, “Look at your cock.  You’re still hard as a rock.”  “Oh Shit.  Yeah I am.”  He exclaimed.  “That’s because you had a prostate orgasm, not a penile orgasm.  We can repeat what we just did and you can have as many full-body orgasms as you have the energy to enjoy,” I explained.  “That’s amazing!” he said.   This is the end of Part 2.  Part 3 will be added either just before or after Christmas. Feel free to leave comments.  They will help me become a better writer.

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