Once upon a time

As a married man I had always thought that the “ball and chain” reference was regarding the lack of enjoyment I would have after being married. Simple stuff like hanging out with friends and watching sports, but now I am likening it to that of an anchor; holding me down from experiences. Specifically, and something I hadn’t thought of in years, having sex with another man. Obvioulsy having sex with anyone else would be something I would be unable to do after marraige, however the experience of having a homo-erotic encounter would never come to fulfillment.
I had never strongly sought to fulfill this curiousity in the past, even completely forgetting about it until I ran into the person who I had explored it with in the first place.  Unlike the feelings she had introduced me to, she wasn’t forgotten.  I never thought I was in love with Rachel, just obsessed with what might have been. My wife, before she was my wife, didn’t like her and the feeling was mutual. It came down to one or the other and I chose my wife, cutting off all contact with Rachel from then on. But she still lived on in my fantasies. They were mainly sexual, as thats what our relationship mostly consisted. Not that we had sex, just talked about it to endless limits. I don’t even remember how the homo-erotic ideas first started, although I’m sure it had something to do with her saying how hot it would be to see my lips wrapped around a thick cock. It was either that or me telling her about a time when I was a few years younger with an older friend.  Actually I’m pretty sure it was the latter.

I have no idea how it would have ever come up but I’m sure once she heard about it she would have demanded I tell her.  Some pouts.  Some whines.  Some refusing to discuss anything further.  Her mind was stuck on that idea and nothing was going to get her off of it.  So I’m sure I just gave up and told her.  I warned her that it was nothing special and I was sure she would be disappointed but she pressed on with her demands.  I told her he was a friend, kind of anyways.  He was a mutual friend between my older brother and I that lived a few minutes away.  He was 18 and I was 16 and, late bloomer that I am, just started getting interested in girls.  More specifically, their breasts.  The friend, Jamaal, would bring over some dirty magazines.  My older brother didn’t show any interest when Jamaal would show them to him so, I guess, he brought them to me.  He asked me which girls I liked, what I thought of them.  I was shy about it but I answered each question.  That opened up the dialogue.  It also opened up the start of masturbating.  Embracing the sexual images and thoughts full on.

One evening he had come over when my brother wasn’t home.  We went up to my room and played some video games, watched some tv and he asked me if I had liked the magazines he gave me recently.  I nodded and dismissed the comment with a grunting yes.  He didnt let up that easily.  He asked “Did you jack off a lot to them?”  I must have blushed because he didnt wait for an answer.  “How long does it take you anyways?”  I always thought this was a bizarre question, and still do.  How long?  Who cares.  “I don’t know, not very long.”  He didn’t let up on it so easily.  “Well, how long, like 30 minutes?”  “No, a minute or two maybe.”  He seemed surprised by the answer.  Either that or it was a ploy leading into his next request.  “No way.  I don’t believe it.  Come on, let me see.”  Dumb and innocent I had no idea what he meant.  “See what?”  “You jack off.  I want to see how long it takes you.”  “What?  No.”  I was confused by his request.  Why the hell would he want to watch me jack off?  I would have to pull my dick out in front of him.  Let him see it.  No way, I thought.  “Come on, if its so quick it won’t be that long.  Let me just see.  Come on.”  He continued pursuing it.  He wouldn’t let up.  I continued to tell him no, even getting up and walking away from the tv, but he followed.  He pursued me to the other end of the room and asked again.  This time, instead of continuing my onslaught of no’s I asked why.  “I just want to see how long it takes.  Thats it.  Come on.”  I knew he wasn’t going to stop but I still was very uncomfortable taking out my cock in front of him.  He took advantage of my long pause as I thought what to do next and he reached over and grabbed my crotch and squeezed.  Not to cause too much pain but to kind of have me at his mercy.  He told me to let him see.  I told him to let go.  “I’ll let go when you jack off for me.”  I almost shouted in return “Fine okay just let go.”  I was afraid he was going to squeeze really hard if I continued to say no.  He smiled instantly and released his grip.

I went over to the door to make sure it was locked.  What a mortifying experience to have someone walk in while my pants were down and I was jerking off.  He got out one of the magazines and laid it in front of me.  I hesitated and he prodded.  “Come on.”  Almost as if he was getting a high off of it, nearing orgasm himself.  I knelt on the floor and undid my pants, quickly pulling them down along with my underwear, to my knees.  My shirt was long and hung to my waist.  He complained that he couldnt see anything.  “Take it off” he said.  I nearly yelled back. “No!”  It was in a voice trying to defend myself against his aggressiveness.  He finally laid off one of his advances and simply said “okay, go ahead, start.”  I looked at the magazine.  A blonde woman, cowboy hat and cut off jeans with nothing on her average sized chest.  It was only about a minute in when I felt myself starting to come close to finishing.  My grip tightened, my breathing became quicker and I groaned as my cock began to spasm and I shot cum on the floor.  He quickly reacted with surprised and amazement.  Instantly saying “do it again!”  I lazily said no.  He shot back with “here let me do it for you then.”  Again I protested with a loud no.  “It doesnt matter anyways, I can’t.”  He smiled and laughed.  “Oh, I see.  You’re quick but can only go once.  That’s alright.”  And that was pretty much the end of that night.  Or it wasn’t, I dont really remember.  Thats all I can recall.  Rachel loved it.  She wanted me to go on but there wasnt anything else, ever.  We never did it again, like that night.  We didnt even really talk much after, just a few times.  But she wanted more, she thought I was holding back.  I told her that was it, however I admitted that I thought about it every once in a while.  A few moments if things had gone differently how it might have been more.  How we might have gone further.  She looked at me with wide eyes and demanded I keep going.

How do you put an advertisement out asking to be fucked without sounding like someone eager to be fucked immediately? I’m still not quite sure as I don’t think I succeeded but I guess it doesn’t really matter anyway.

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