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First Time On-Line Hook

Posted by: Age: 25 at time Posted on: 28 comments
15 likes 39 views Category: Masturbation Male-Male Tags: edging, older men/younger men
When my girlfriend was away, I found an older man with whom I could play.

All right, so when I was in my mid-twenties my girlfriend was overseas for a semester for her degree, which left me alone for about 6 months.  About 3 months in I really was starting to crave some human touch.  So I joined one of those adult hook-up sites and posted that I was looking to masturbate with, or be masturbated by, other men.  

     Now, I put my posting for men for two reasons.  One, in my mind it would be less like cheating on my girlfriend because it was a site designed for one-time discreet hook ups and because I was advertising for men with whom I was not interested in forming long-time relationships with.  The second reason was that I had had a male-male experience in college and liked it.  One night, my friend and roommate, Tim and I came home to our apartment after a night of partying.  I went to take a shower before bed and then he came in all laughing a couple minutes later in the shower with me.  We were both naked and pretty drunk and then he slurs, "Hey--jack me off."  And then I laugh and grunt back, "OK.  You jack me off too."  But then he actually grabs my dick and I start getting hard.  So I grab Tim's dick and he gets instantly hard.  And we just start jacking each other.  No more laughing, we just stroke each other's hard dick.  Well, Tim came and I watched agog as his semen burst from his cock head and dove to the shower floor and flowed to the drain in a couple of thick globs.  That kinda broke the spell for a bit, because Tim let go of my dick and looked at me all sober and mumbled, "Uh, that was intense..." and got out of the shower.  

      At the time, I didn't know what to feel.  I was aroused, but in a weird way, and my penis was seriously swollen from the jacking but also still ram-rod hard.  I finished showering and went to my room and got in bed.  Well, after lying there still a minute, I flung my covers down and my hand gravitated to my still erect penis.  I began stroking it, softly at first.  I reached over to my nightstand where I kept some petroleum jelly and lubed my fingers and then lubed my erection.  After a couple minutes of private stroking, Tim just comes in and flicks on the light.  Now you need to understand, usually I would be discreet and never let Tim know when I was bating.  We hardly ever talked about our masturbating habits or anything.  But the shower incident had changed everything, at least for this night.  So, when he came in, I made no move to hide what I was doing to myself. 

     "What?" I remember saying.  

     "Uh, sorry for leaving you hanging in the shower," Tim said.  "It's just uh... I don't know what etiquette is here."

     I stopped my stroking for a second.  "Who cares?" I said.  "It's no big deal.  But now I'm turned on and I gotta take care of it.  You can go to bed.  Now we've got a crazy college memory."

     Tim took a step closer to my bed.  "Do you want me to help?"

     I think I audibly gulped.  It registered to me in that moment, that I became even harder when Tim came in and turned on the light even though I stopped stroking.  It was because he was looking at me naked, I realized.

     My hand took up my dick again.  "OK," I said, stroking.  "Just keep watching me like that."  

     Tim stood there, his eyes glued to my glistening penis, while I masturbated.  After a few minutes, Tim took another step closer.  "Do you want me to touch you, cause I will."

     I was getting light-headed with pleasure.  "OK," I consented. 

     As I kept stroking, Tim came up and cupped his hand around my balls.  He pulled gently on my sac, then messaged my testicles and then traced his fingers on that tender space between my sac and my anus--and then I lost it.  I ejaculated massively, Tim sheepishly giggled, and once I regained my wits I mocked him with, "Duh... that was intense."  We both laughed and went to bed and barely ever talked about it again.  

     So, like I said, I knew I was open with being with another man in a masturbatory way.  

     Well, a few days after I made my posting, I got a lot of men that were interested.  Most of the responses were pretty intense and most were interested in going way further than just masturbating.  Except one.  Some guy, calling himself John, seemed pretty chill and said he would be interesting in just having a good jack off session.  The only kicker for me was that John was like 60 years old according to his profile.  I mulled it over and John and I messaged back and forth.  And even though John was older than my own father, I realized I just wanted a human touch upon my penis, and John's overall vibe was chill which was what I wanted.  I realized it was a win-win for both of us.  I would get a steady hand on my penis and John would get to play with some young cock.  

     So, we made arrangements and I drove about 50 miles to the address he gave me.  I was nervous as hell.  I had never done anything like this in my life.  He gave me the address to, what looked like on the outside, a small warehouse.  It kinda gave me Texas Chainsaw vibes and I almost drove off right then.  But I steeled myself and got out and knocked on the door.  And sure enough, this gray-haired, sixty-something year-old dude opened up.  Well, we greeted each other, shook hands and he let me in.  He seemed pretty fit for sixty, and just like our correspondence the guy seemed very friendly and chill.  The warehouse was filled with electrical supplies, which John said he owned and that no one would bother us here.  He led me back to pretty nice looking office, with carpeting, nice lamps, a desk and a couple chairs and a small sofa.  

     We sat down in the chairs, and he offered me a cool drink from a little dorm refrigerator.  He offered beer, water or Snapple lemonade.  God help me, for some reason I took the Snapple lemonade.  I was so nervous I had trouble unscrewing the bottle's lid.  I am sure John noticed my trembling hands.  

      We shot the shit for a little bit, before he asked me if I had ever done anything with another man before.  I told him about Tim in college.  I then asked him if he had a lot of experience with men and he laughed and said, "I've had a lifetime of cock."

      Jesus... I thought.    

     "Well--" John said and stood suddenly from his chair.  "Let's see about getting you off."  

     I stood up too--but had no clue how to start all of this.  John sat down on the sofa.  He was wearing dad jeans and a button-up shirt.  Some sort of brown loafers for shoes.  He looked at me standing before him and said, "Let's start off with you stripping down.  Are you OK with that?" 

     My heart pounded in my chest.  This was actually about to go down.  Now, at this point in my life I had had plenty of consensual sex with females--handjobs, blowjobs, intercourse.  But standing before John at this moment was completely nerve-wracking for me.  I nodded and took off my T-shirt.  I undid my belt, I took off my shoes and socks.  I pulled down my pants.  Now, I only stood before John in my bikini-style briefs.  

     "Hold on," John said.  He motioned me toward him.  I came close to where he sat.  He looked up and asked, "May I?"  I assumed he meant could he touch me and I said, "Yes."  He then grabbed my ass cheeks with both hands as if he was checking their firmness.  I nearly swooned at being handled like this.  He inspected my thighs and my calf muscles before gently nudging me away from him.  He said, "Now slowly take off your underwear."

 

      As I slid my underwear off, I saw John tug at his erection through his jeans.  I felt sweat in my armpits, I was still so nervous.  I was now completely naked in front of John and I was embarrassed because my penis was as deflated as a punctured football.  I started fondling myself frantically in hopes to initiate my erection, but John saw my terror and said, "Slow... down.  It's OK.  Take your hand off it."

      I took my hand away from my limp penis.  

      "You still want to do this?" He asked.

 

      I nodded.  "Yes.  Very much.  I think I'm just nervous."

     John nodded and said, "Take a breath.  It's OK.  Come here."

      I walked to where he sat again, and he scooted up to the edge of the sofa.  Slowly, gently, he put his whole hand and fingers upon my penis and balls.  He messaged my organ wholly, his fingers playing upon my penis like a piano, my head became like mist and I felt my firmness begin.  My most sensitive flesh stirred and lengthened and then stiffened until John's fingers made me as iron.

     "There now," John said, looking at my massive erection.  "Look at that cock."

     I looked down to my cock and John handling it and felt all the surreality of the moment.  Here I was, buck naked in front of a sixty year old man, whom I was allowing to fondle me to the utmost for both of our pleasures.  

      John stood up and went to his desk.  He took out a bottle of some kind of scented oil and sat back on the couch.  He then instructed me to lie across his lap on the couch.  I obeyed and proceeded to lie down with my back across his lap, while my erect penis jutted up to him.  He opened the bottle of oil and began applying it to his fingers and my penis.  It was heaven.  

      John proceeded to slowly message and oil the entirety of my dick and testicles.  At some point I began openly moaning.  John began a kind of rhythm where he would stroke me furiously and then down shift to mere massaging and tugging.  I would feel the semen of my orgasm rise within me, only to recede and further strengthen.  I realized that he was edging me.  Expertly edging me.  This  went on seemingly forever.  He played my penis in every way a penis can be played with in such a state.  My naked and moaning body writhed upon his clothed lap in endless waves and shudders of pleasure.  (As I write this I am married now, but even my own wife has never taken the time or patience to stroke my dick the way John did.)  Finally, John allowed me to cum.  He sped up his stroking, intending to bring about my final crescendo, and in a white flash my semen erupted from my slit eye and John continued to jack me till every drip of semen was ejaculated out of me--onto my limping penis, balls thighs and belly.  

      After I recovered and cleaned up a little, John stood up and stripped naked himself.  His pubic hair was gray, but his erect dick was enormous. My penis at its zenith had more girth, but John had me on length.  He laid down upon the carpeted floor and spread his legs wide.  "Here, come kneel down between my thighs and stroke me off.  Would you do that?" 

      "Certainly," I said.  I grabbed his oil, kneeled between his parted thighs and lubed my hands and his penis.  The second my hands touched him, John closed his eyes and started moaning and groaning.  It did not take long to get him off.  He growled and shuddered the whole time while I stroked him vigorously.  I had only previously stroked one other penis: Tim's, and I really had no lasting impressions of it.  But I loved stroking John's cock.  I was actually surprised how much I liked it.  He had a little weird growth on the tip of his dick I found fascinating.  And his face during the whole crisis was priceless--John almost looked in pain as I stroked him and he kept his eyes closed the whole time and veins were popping on his forehead.  When he finally came in thick ropey jumps of semen, John gripped my arms almost as if he were steading himself as I continued to jerk him dry.  

     I hooked up with John three more times, four in total in the months before my girlfriend returned.  The encounters were all the same.  I would come in, strip naked before him, I would lie on his lap and he would edge me for about an hour.  Then I would kneel between his thighs and stroke him off.  After the last session, I never saw John again.  But those were, undoubtedly, the hand jobs of my life.  

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