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Just when I (almost) stopped trying

Over the past decade I have become obsessed with experimenting with my bi side. I have no interest in a relationship with a man, or for that much no interest in a make out session- my focus is on the region (front and back) below the belly button.

Over the years I have tried to get picked up for some bi or gay action. For some reason, the idea of being picked up vs. approach someone seemed to make it more acceptable to me. I've tried standing at the urinal with my cock exposed vs. with my hand on it as usual. Tried on silky PJ shorts and stoked myself to get a little hard, then asked the attendant for help. Caught the eye of another single man at a restaurant, hoping for a note with a room number- still nothing. I have also frequented nude beaches/pool areas- but with my clothed wife alongside. Still with the hopes, some man would notice my extended stare- and approach me somehow. I have even arranged getting "caught" nude in my secluded hot tub by repairmen- only to have macho/butch men appear and show zero interest. I think it's worth noting here- I would be generally considered handsome and in good shape for my age. Not just a vain look in the mirror, but contrary to my lack of drawing men, women have responded regular enough to reassure my confidence.

I have always hated the idea of being one of the creepy old men, so until my recent event- I had largely given up and resolved myself to a fantasy life of gay masturbation.

Once I gave up looking, opportunity struck (and I responded).

I was on a business trip that would be several hours away. I was towing a trailer with some inventory items, to driving was the only means of transportation. My client asked me if I could pick up another consultant that lived near me as well. I quickly agreed as having someone in the car to talk with would make the drive go quicker.

We drove late into the night and eventually stopped to get a room. We knew we would be sharing a room for the trip, so no big deal. I slipped on a t-shirt and some silky bottoms that remind me of what Tarzan would wear. Covers little, and hides nothing- that was the plan. A few times I got up at night to pee with a raging hard-on, easily viewed. I was hopeful he saw this and would begin to ponder.

As we both answered the alarm, this would likely be the moment of truth. I got up and walked to the bathroom with a full erection, I made sure to speak with him so he would look at me and no doubt see my erection. Mind you, I am not one that is hung like so many profess. I am admitted on the smaller side of average, but a hard-on is still a hard-on!

My current room mate made no mention, but it was obvious he got a solid look. I was assured the bait was set, now to simply find out if he would bite. As we continued our road trip to our final destination, conversation covered the gambit. Only vague references to sex at this point however. We did speak of some sexy women in our industry and I interjected a score of sexy men as well. He seemed to take it at this as simply a compliment to them being handsome. I used this as a transition to focus more on a sexual nature. We discussed who would be our fantasy person to sleep with (women being the assumed). We named names and compared notes. We then talked about what we'd like to do, and/or have done. Both included getting a blow job, but I included my passion to rim a person. He found that intriguing, but didn't offer up much more. I forced the point a little more about getting a blow job- how often he's getting one from his wife and if she swallows. His answer was rarely and no.

Trap was set! He followed by asking me the same. I responded, "The same from my wife, but otherwise yes" (True on my wife, but not true as I was not getting anything from anyone on the side...yet). He replied "What do you mean, do you have a women on the side?". I replied, "No, not a women".

I believe we must have had about 5 minutes of total silence before he said "What do you mean, 'not a women'"? I went onto share the following (the part about sex with my wife is true, but the part about being with a man was still at this moment my fantasy). I shared my wife and I have a solid sexual life together. She is pretty vanilla, but lets me do things that help satisfy myself it if doesn't affect her much. Examples- she watches me use toys on myself. Let's me rim her, but won't reciprocate and on occasion lets me eat her after I've cum in her. She claims it is gross, but doesn't stop me. Each of these activities help me confirm I enjoy a bisexual side when it comes to sex.

Another 5 minutes of total silence. He finally asked if I then had sex with a man and I confirmed yes. I enjoy giving head, swallowing, rimming and giving and or receiving anal sex if the sizes align (we both laughed).

I asked in return- have you ever been with a man? He promptly responded NO!. I asked if he ever had anal sex? Again, a quick NO. Ever asked your wife if you could, and he said yes, often in the early years but gave up. Finally I asked him if we ever tasted his own cum? He said not on purpose, but some trace from time to time.

About this time we arrived at our destination hotel, unpacked and went out to dinner. No mention of our prior conversation, it was as if it never happened. Once we returned to our hotel, we both said we would take showers and relax in bed. I went first and put on my Tarzan bottoms. While he was showering, I opened my laptop to one of my favorite bisexual web sites, not wanting to freak him out over full blown gay.

I was pleased when he returned from the shower in simply boxers and a t-shirt- not in full armor wear! It was obvious again I was sporting a mild hard-on and my viewing of porn was also not unnoticed. I asked him if used to get blow jobs before he was married and if the girls would swallow. He said yes, and knowing they were swallowing simply made it more erotic. I asked him a few more follow-up questions to have him fully engaged and finally asked him if he would like for me to give him a blow job like he used to get? He objected saying he was not gay, and I provided the typical answer that his cock won't know the gender of the mouth that is engulfing it. After a little more coaxing and my cock now exposed beyond my shorts, he semi-agreed. I moved over and sat beside him. I turned my laptop in his direction and he began to glance at a threesome where one guy was getting sucked by another while he was going down on a women. I said, "Doesn't seem that bad after all, does it?". With that I slowly began to move my hand up his thigh until I reached his nearly erect cock. I fondled it for a little while, but didn't want him to back out- so I moved my hand inside his shorts that touched his bare cock. Little did he realize, this was actually my first time touching another cock as well- a secret I would not let onto.

Without much resistance, I pulled down his shorts and removed them. I took a hard look at his erect cock with cum bubbled at the end and took the plunge. I have thought about this moment for nearly 20 years and obsessed about it for 10. The experience did not let me down. I worshiped his cock in my mouth like I do not believe he has ever experienced. It was beyond what I have experienced as well, but was fully what I had been dreaming of. I could tell he was close to cumming and I didn't want to time to pass, but neither of us could back off. He exploded into my mouth and having the taste of someone else's cum in my mouth beyond my own was mind blowing. Not because it tasted good (I'll give it a neutral at best), but because of the raw sex it represented. What could be a more fulfilling end to a blow job?

Knowing most of us lose a lot of our sexual nerve after climax, and the fact I didn't want to spoil either of our memories- we just backed up, cleaned up and watched TV until eventually going to bed. At the time, not speaking of the incredible cock sucking experience we just enjoyed on either side of the suckee or suckor!

We went about business as usual the following day and repeated the start of the evening the same. My taking a shower first and getting myself ready (hard) for him to return from his shower. This time it did not take as much coaxing to get things started. I began sucking him like the night before. A good while into this, I told him to roll over, I wanted to give him a butt massage before we continued. He didn't see any harm in this, so complied. I began to rub his cheeks, he obviously enjoys this. I allowed my fingers to slide closer and closer into his crack, knowing I was also glancing his hole from time to time. Given the stroke started on his cheek, I don't think we realized my purposeful efforts. I moved in closer, made my fingers linger longer and eventually just laid one finger across his opening. He seemed to struggle both with enjoyment and hesitation. I encouraged him to relax and simply enjoy. I focused more and more on his crack and hole to the point he no longer squirmed and then spread his cheeks and buried my face and tongue into his unaware ass. This was much more of a jolt to him than my taking his cock into my mouth. He jumped and objected. We returned to the argument- do you think you're ass knows the gender of the tongue that is licking it? I eventually got him to agree to relax and let me continue with the understanding if he wanted me to stop at any point, I would. He never called for stop. I sucked and tongue fucked his pucker with more zeal than I have ever provided to a pussy. Not because I like an ass more, but because I had such a long build up period of fantasy, and now a willing ass was being taken by my tongue, lips and mouth. When I didn't think either of us could take it much more, I rolled him over and in what seemed like seconds after having his cock back in my mouth, I had my second load of cum.

Work day about the same, but I knew this would be our last evening together as he was going to a different city after this event closed. I told him I had one more surprise to offer, by now he was comfortably skeptical. I had prepared myself for the balance of the evening as you'll read. I started the evening as we had started the prior. I began to give me yet another blow job. As I was sucking on him, I was also inserting a small butt plug in my ass to prepare me for what I hoped would follow. Eventually I rolled him over to rim his ass again. As he was readjusting, I moved to a larger plug and knew I would now be ready.

I returned him to his back and took him in my mouth for just a moment. Then I took the bottle of lube and began to ready his cock. I let him know it was time for him to fuck me in the ass. knowing both of us have only been with our wives for over 20 years- I believed it was safe to go bareback, and best of all, eventually feel his warm cum explose into my virgin ass. I knew he would come with his standard objection, so I just went to the answer before he could offer such. "An ass is an ass". You said you asked your wife to try anal sex and she said no. Now get behind me and slowly press your cock against my ass. Guessing his resistance on the other actions didn't last long he didn't even try. As requested, he began to press his cock into me. Once in I asked him to wait a minute, but after having the butt plugs in it turns out I was ready. I gave him to go ahead to fuck away...and fuck away he did! It was everything I had dreamed of over the years until he stiffed up and announced he was about the cum. What happened next was beyond what I had ever fantasied about- just as he began to unleash his cum in my ass, I too blew the largest amount of cum into the air since I was a teenager. I don't even remember touching myself (though sure I did), I was just focused on being fucked and realized I was about to cum.

These few days delivered everything I had been dreaming of. I asked my travel mate if he wanted to reciprocate anything we had done and he respectfully denied. I was cool with that, my fantasy that became reality just happened.

Here's to hoping I don't have to wait 20 more years! Cheers.