The Bet

Info hondolane1949
07 Oct. '20

Richard and I had been friends for several years.  We worked together and spent Saturdays watching college football.  Richard was 64, five ft 9 and 185 lbs, with grey hair, a goatee and mustache.  I am Michael, 62, five ft 11, 195, with dark hair and a mustache.  To make the game interesting we would always have a minor bet.  Like a beer the next time we are out.  Nothing major.  One Saturday Richard said, "Ive got some things around the house that I need to do and I am sure you are in the same situation so let's bet, the loser has to do what the winner says."  We shook hands and settled down to watch the game.  

There was two minutes left in the game and I was down by two points.  A field goal would do it and I was thinking ahead to what I would have Richard help me with at my house.  With ten seconds left my team ran one more play and then a chip shot field goal.  

The hand off was made and as the running back was hit, he fumbled the ball.  There was s huge scramble and the other team recovered as time ran out.  I laughed and just wondered what Richard would have me do.  Clean gutters, clean the garage, rake leaves.  

"All right Richard," I said, "what do you want me to do?"  Richard said, "Remember we said do what the winner says."  I nodded.  

Richard began to speak.  "Mike there is something that you don't know about me and that is that I am bi."  I froze when he said, "bi."  

I looked at him and started to speak but he cut me off.  "We agree to do anything."

"But I didn't agree to anything that had moral ramifications."  

"Look," he continued, "I am between girl friends and you are divorced.  Neither one of us is dating right now and it would sure help ease the tension to have some intimate fun with someone I liked and respected."

"Richard, look, I'm not that way.  I just don't think...

"How do you know until you have tried."

"Well, I have never tried, but I don't think I want to.  I mean it's not normal."

"What's normal?" he asked.

"A man and a woman is normal," I replied.  

"There are a lot of people who would disagree with you.  Many men like to explore as do women with other women.  Exploring, trying new things is normal," he replied.

I shook my head not really knowing what to say next.  

"You could try it and if you didn't like it, it would be one time thing between you and me and it would never go any further.  Our secret."

I started to object when he said,"But on the other hand, you might enjoy it.  And if you do, think about all the fun  you could be missing."

"I just don't know.  It's a big step."

"One small step for man..."

"One giant leap for mankind," I finished the statement.  "But this is not walking on the moon. It's two men being intimate."  

"And it might very well be two men enjoying their intimacy."

I shook my head.  "Damn I don't know what to do."

"See," said Richard, "you've gone from absolutely not, to 'I don't know what to do.'  Let's give it a whirl.  Besides a bet is a bet."

"I think I am going to regret his, but what the hell."  

Richard sat down next to me on the couch.  He put his arm around me and said, "Anything you don't like, just say the word."  With that he kissed me.  As we kissed he put his other arm around me.  I was surprised to find that it was quite pleasant.  After a brief period Richard withdrew.  

"Well, what did  you think?"

"Well, I was surprised because it was nicer than I thought."  I turned red as I talked.  "It was actually pleasant."

Richard smiled and kissed me again.  The kiss was long and lingering in.  It really felt nice and I really started to get into it, when he broke off the kiss once again.  

I sat back, took a breath and said, "That was really nice."  

Richard smiled and siad, "It only gets better," as he kissed me again.  Our arms wrapped around each other and our kiss was much more intense.  I felt his lips part and his tongue brush across my lips.  He pulled me close and I opened my mouth.  Our tongues met and as the toyed with each other I felt a stirring in my pants.  AS we kissed I never would have guessed that I would get an erection while kissing a man.  But happen it did.

When Richard broke the kiss i sat back a bit breathless.  I was flabbergasted and did not expect such a positive reaction.  He reached over and slowly unbuttoned my shirt.  Once open he kissed me again and this time his hand ran lightly across my chest.  I feelt a tingling all up and down my body and a little moan escaped my lips into his open mouth.  As we kissed I caressed his back and he began to lightly circle my nipples.  The little moan became much more pronounced.  And we kissed longer, harder, and deeper.  

I was panting this time when Richard leaned back and he even had red cheeks.  I looked at him and he said, "Time to go to my bedroom and get comfy."  He rose to his feet and I stood up.  We walked back to his bedroom.  We turned down the bed and quietly began to undress.  We stood naked at the foot of bed both us with erections and both of us wanting to explore more.  He walked over to me and we kissed.  

Our arms wrapped around each and our erections pressed into each other. It felt good.  It felt right.  It felt natural and even normal.  He reached down and caressed by ass and I copied hims.  We were breathing hard through out noses and we broke the kiss to walk to the bed.  We got in on opposite sides and move together.  

He pulled me close and we kissed our naked bodies caressing each other.  His hands moved down to my ass and I felt his finger tips gold gently down the valley between my cheeks.  I moaned once again into his mouth and as I felt his finger circle my anus I knew this was going to be wonderful.  

We broke the kiss and I said "I'm not sure what to do, but if I do something you don't like let me know."  He kissed my neck and gently rolled me to my back.  He kissed by neck and shoulders as I caressed his back.  The feeling was our pleasure and I totally gave into it.  

The pleasure was so sweet that I let my eyes close and just focused on the pleasure.  He kissed his way down to my nipples.  He kissed each one and then took turns licking and sucking on them.  It felt amazing.  My whole body melted as he loved me.  As he licked his hand ran up and down my body from upper thighs to chest.  Each time his hands glided up or down he purposely avoided touching my erection.  

He kept it up until I finally said, "Please touch my cock."  

He lifted his head and kissed me again.  As  he did his hand moved down and he gently took my cock in his hand.  It felt wonderful  He stroked it gently a few times as we kissed.  His had dropped and he lightly began to caress my balls.  His touch was just perfect.  Light and wonderful.  He found that little patch between my balls and anus and he lightly caressed it.  I thought I died and went to heaven.

He went back to gently stroking my cock kissed his way back up and whispered in my ear.  "How are you doing?"  

"Wonderful," was all I could breathlessly say.  We kissed and he kept gently stroking.  He alternated between stroking and caressing my balls.  UP and back.  I felt the tip of his penis against the back of my hand.  I turned my hand over and wrapped it mourned his cock and stroked gently.  Now it was his turn to moan into my mouth.  

We kissed and gently stroked each other for quite a while.  Then he told me to roll over.  I did without hesitation.  He kissed he back of  neck and shoulders.  He kissed his way down my back until he got to my ass.  He caressed it as he gently kissed the small of my back.  

As I lay I felt no embarrassment or awkwardness.  It all felt just tine.  I was enjoying his kisses and caresses until he move around between my legs.  He began to kiss my ass and then said, "Your ass is so sexy."  

Before I could say anything he parted the cheeks of my ass and said, "Your asshole is just so cute.  So pink and tight.  I thing it needs some loving."

He ran his fingertip around my anus and I moaned.  Even that, which to this point would have been taboo seemed right.  His finger probed me gently and I let him in.  He kissed my ass as he let his finger just inserted in an inch or two.  I was just getting use to it when he pulled it out.  He moved for a moment fumbled with something and then inserted a well lubed finger into my anus.  I gasped.  It was cold, it stung, but in moment is felt good.  

As he kissed my ass he gently pushed his finger in farther and then withdrew it.  Soon he was moving his finger in and out.  Fucking my puckered anus.  I just let it happen.  So he introduced a second finger.  The pain subsided quickly and it felt even better.  He kept this up quite a while fucking, probing,  It was amazing.  He withdrew his fingers and then fumbled for a moment.  He got in between my legs and told me spread my cheeks.  I knew what was coming and I did as he asked.  

I felt the head of his erection at my opening.  He pushed gently.  He kept up steady pressure until his stomach was pressed up against the cheeks of my ass.  He lowered the rest of himself on me and kissed my neck.  

"How are you doing?" he whispered.

"I'm good," I said and the he withdrew a bit only to push back in.  Then out.  Then in.  The stinging was soon replaced with pleasure and I hope he would be there for a long time.  He moved gently and steadily in me.  Many thoughts were running through my mind.  I couldn't believe this was happening.  I could not believe I was being fucked by a good friend.  I could not believe how good it felt.  I could not believe that I wanted more and more of this.  As I lay there lost in pleasure and thought I noticed he was picking up the pace.  

He was breathing faster and heavier.  His hips moved quickly.  His moans of pleasure were getting louder and his tempo was increasing.  I knew he was nearing the end and then he erupted in my ass.  Shooting his creamy cum into my waring ass.  He mumbled and told he how tight I was.  How good it felt and then he began slow down and then stopped.  He lay there until his penis went placid and he removed himself from me.  He flopped down on his back and we both just lay there.  

He put his arm across my back and said, "I hope it was as good for  you as it was for me."  

"It was wonderful ," I said.  "I could get addicted to this."  We both laughed.  He both relaxed and then caressed my back and told me to roll over.  I did and my cock was sticking straight up.  

He rolled over toward me, kissed me and then went down  on me.  He place a small kiss on the tip of my penis.  Then several long licks from balls to the tip.  I closed my eyes and brought my hands up to my nipples.  I lightly caressed them as his mouth closed around my erection.  His mouth was warm, wet, and welcoming. 

As his head moved up and down he slid a finger back in my anus.  I moaned at the pleasure.  All I could feel was the pleasure of his finger, his mouth and my own fingers.  I could feel the orgasm building and said, "I'm gonna' cum."  

This only increased his sucking and fucking.  I held off as long as I could and then i let go.  My hips rose up off the bed and i spurted into his waiting mouth.  He drained me totally and it felt wonderful.  He just held my softening penis in his mouth until it was totally limp.  He moved up my body and we kissed and then just held each other.  

After a lengthy quiet he said, "Well what did you think?"

I pulled him close and said, "Can I come over for Monday night Football?"  We both laughed and knew this was the beginning of a new direction in our friendship.