My Dilemma

Info mikec1010
02 Aug. '18

I'm in my mid fifties, dark hair and eyes, mustache, nice looking six feet tall and one hundred ninety pounds.  My wife passed away two years ago and I was definitely in a blue funk.  It was difficult getting up and going to work, but I moved ahead knowing it was the right thing to do.  I didn't think I was ready to begin dating again but I did not need some way to relieve "stress."

Since I was a young man I had occasionally thought about being with a man.  In fact, I came close a couple of times but never followed through.  Mostly because I was married but also because society and culture said it was wrong for men to be together that way.  But now I was no longer married and I would think more and more about being with a man in an intimate way.  Yet I could not get the idea out of my mind that "it" was "wrong."

One afternoon I got on line and looked up bi and gay dating sites.  I found one that was dedicated to men over fifty.  I thought I would post an ad and then talk with someone about my feelings and get another opinion.  By the next morning I received a reply from a man, my age, named Greg.  He was bi and comfortable with his feelings.  I replied and after exchanging several emails we met for coffee.

He was a nice looking man, in his early sixties, grey hair, shorter than I.  We talked and I shared with him my feelings and my hesitations.  We talked more and he really listened to me.  Yes, I really wanted to explore sexual opportunities with a man but I didn't know if I should.  Was it right?  He finally said to me, "I think you'd like to be in a situation where you had no choice, where all the responsibility was taken away from you.  If you're a victim it would help you work through things."

He made sense and I asked how I could achieve something like that.  He said let me think and we parted.  Three days later he contacted me.  "It's not perfect he began, but if you are willing to play along it might help."  I was intrigued and he told that we could do a role-play in which I would be helpless.  He invited me over to his house and went into greater detail.  "What if I kidnapped you and forced you to have man to man sex."

I laughed but he was serious.  I said, "It might be fun and it might help me, but how do I know you are not some weirdo?"

"He handed me an i.d. This is my full name.  You know my address and you know my phone number and email."  He gave me the name of where he worked.  "You can have all this information, give it to someone you trust, and it will be my guarantee to you, that I won't hurt you."  Even though it was all pretend the idea struck me as a way to get around guilt.  I agreed.

I would come to his house pretending to sell insurance and then he would "kidnap" me.

I showed up at the right time and we began.  He excused himself for a moment and came back with a toy gun.  "Get up, do as I say, and you wont't get hurt."  I did what he said.  He directed me back to his darkened bedroom and ordered me to undress.  I did as I was told.  He then told me to get in the middle of the bed.  I did and then he proceeded to tie my hands and feet in a spread eagle position.   I was very nervous and he told me as long as I did what I was told all would be ok.

I nodded in agreement.  He took off his clothes.  He climbed in bed next to me and began to talk to me in a very low, sultry voice while at the same time lightly caressing my chest.

"I've been stalking you for two weeks.  I decided I wanted you as my sex toy."

I told him to let me go or I would start yelling.  He told me to go ahead as the room was sound proofed.   I told him I wouldn't cooperate and he laughed.  "It's going to happen whether you like it or not.  Easy or difficult it is going to happen."  I was actually a bit nervous and then he leaned down and tried to kiss me.

I turned my head and he laughed.  He kept caressing my chest and gliding his fingers down my body to my thighs.  This went on for a while and then he circled my nipples.  That did it.  My cock began to rise.

"Well, well, what do you have hear.  It looks like our little friend here is starting to take an interest."  He tried to kiss me again and again I turned away.  He then leaned down and licked my nipples.  That was it, I was now fully erect.  He laughed again, "Your mouth says 'No' but your cock says, 'Yes.'"

He begin to kiss my upper body all over, even my armpits.  He smiled and said, "That has to go."  He got up and left the room.  I had no idea what he meant until a few moments later when he returned with a pan of water, a towel, shaving cream and a razor.

I tried to get free as he lathered up my armpits.  He simply said, "Move all you want I just hope you don't get cut."  I settled down and in a few quick strokes I was shaved clean.  He stroked them and then licked them.  In an odd way I felt more aroused.

He smiled and said, "As long as I am here we might as well clean you up."  He lathered up my pubic hair and shaved me clean.  I felt so naked, so vulnerable, and so very turned on.

He climbed back in bed and tried to kiss me again and once again I turned from him.  "It's ok we will get there."

He then began to slowly make love to me.  Caressing, licking, kissing, and sucking on my body from head to toe.  I was melting any resistance real or pretend was quickly fading away.  He began to focus on my cock and balls.  It was amazing.  The pleasure was simply overwhelming.  He giggled when the first drop of pre-cum appeared at the tip of my cock.  He swiped it up with his finger and raised it to my mouth.  "Open wide," he said.  I refused.  He laughed.

"Easy or hard, it is going to happen."  He pinched off my nose and when I opened by mouth to breathe he slipped his finger in my mouth.  It was slaty but otherwise unflavorful.   "See, that wasn't hard."

He kissed his way down my body and then began to orally please me.  The pleasure was overwhelming.  While he sucked me his finger tips played with the area between my balls and asshole.  It felt simply wonderful.  I had never experienced anything like it.  I was getting ready to cum when he stopped sucking.  "Not yet, we have a long way to go."  I gasped in frustration.

He went back to playing with my cock and sucking on it and as I got close to cuming he stopped once again.  "Do you want to cum?"  I nodded.  He moved up my body, "If you want to cum, all you have to do is kiss me.  Otherwise I can do this all day long.

"Fine!  Kiss me."  He smiled and he kissed me.  I felt his tongue move across my lips and figured I better open my mouth if I wanted to cum.  I did and as we kissed I soon began to enjoy it.  I wanted more of it.  We kissed and kissed.  I really got into it and I loved it.

He broke the kiss and smiled.  "I told you it would happen."  Now let's get you off.  He went back to sucking my cock.  I totally relaxed knowing that soon I would be cuming.  And the suddenly he stopped.  "Dman it," I said, "I was getting ready."

He said, "Well, I noticed and then i thought what has he done for me.  So, you wan to cum?" I nodded.

He got up and straddled my chest.  He placed his half erect cock at my mouth and said, "Open wide."  I turned my head.

He laughed, "Well, I can keep you at the point of cuming for hours or you can open your mouth and suck me."

"Fuck you," I said and then opened my mouth.

He slid it in.  He was fresh and clean and I licked it, sucked it, and did every thing I could to make him feel good.  He moaned in pleasure.  It felt good to feel him grow in my mouth.  To know I was making that happen.  As I sucked on him he reached back and gently stroked my cock.  I could taste his pre-cum as it oozed out of his cock and into my mouth.  He ran his fingers through my hair, "You are doing a great job."

He climbed off and began sucking my cock again.  But then I felt a new experience he slipped his lubed up finger in my asshole.  I moaned and as he fingered me he soon entered a second finger.  He moved i in and out in and out.  It was amazing.  I never knew such pleasure could be experienced.

I was moaning and getting close to cuming when he stopped.  "Do you want to cum?" he asked and I said, "Please."

He smiled, "Just one more thing and then you can cum."

He got up and moved on leg strap to my knee and did the same with the other leg.  I wasn't sure what he was doing until he then attached the straps to hooks in the ceiling.  My legs were up and spread open.

It suddenly hit me.  I began to struggle.  "I'm not ready for this."

"Yes you are."

He lubed up his finger and loaded up my asshole.  "Look, I can't do this."

He reached up and stroked my cock, "You are ready, so just enjoy it."

He put lube on his cock and knelt between my legs.  He took hold of his cock and I felt it press into my asshole.  He pushed slowly, very slowly allowing me to get used to this friendly invader.  Soon he was all the way in.  He smiled and blew me a kiss.  "Just enjoy the ride."

He began to move in and out, in and out.  I was surprised that it did not take long for it to become a pleasurable experience for me too.  I moaned and he said, "Glad you like it."  He then closed his eyes and picked up the speed of his thrusting.  I knew he was moving to completion.  All I could was enjoy the ride, and I did.  His breathing quickened and he moved faster and faster until he cried out, "Fuck!'  He came spurting his cum in my ass.  His strokes in and out slowed down and finally he pulled out.

He smiled and then lowered his head.  He began to suck on my cock and as he did he buried his finger deep inside me.  The feeling of pleasure was overwhelming and soon I said, "I'm cuming."  I hit that wonderful peak moment when the pleasure takes your breath away and then I began to spurt.  He sucked and sucked until I was dry.

He smiled and untied my feet and my hands.  He lay down next to me and I rolled over and kissed him.  "Thank you," I said, and I kissed him again.  It was a beautifully exciting afternoon, one I will never forget.  The first of many more to come.