First Bi-Guy Experience

I am an older guy, but had a Bi experience in my early thirties. I had fantasized about is since puberty but it was such a taboo for men to discuss, let alone try, and still is verboten I guess. I was newly divorced and started an amazing affair with a woman 25 years older than me. She was attractive and a fairly well known public figure in Canada. It was quite a turn to have hot sex with a lady with a straight laced public, respected image.

One day in bed she shared a fantasy of having two men. As the conversation progressed she became really turned on, especially when I mentioned I knew a guy that was very much into this. Long story short, we ended up at my place twice a month with my friend and had a great threesome time. I loved to watch as she performed oral on him. She knew I liked watching, so she used to put on quite a show. What she did not know is that I was getting turned on because I was envious of her sucking on his sexy erection. It was the same when he mounted her in just about any position. I would fondle myself imagining what it would be like to have his cock inside me anally.

We arranged to meet at my place one afternoon for one of our great threesomes. He arrived first, and then my girlfriend called and bailed due to an emergency. We had already showered and were sitting around in housecoats and continued to chat about our crazy sex lives when I plucked up the courage to ask him how he got into Bi. He was open and easy to talk to about it (my heart was in my mouth!). He sensed my interest and came right out and asked me if I wanted to try it with him. At this point I was so turned on that I could hardly sit still, so murmured yes.

In the bedroom he slipped out of his robe and lay down and I nervously slid onto the bed and knelt next to him and took his cock into my hand and began to stroke and fondle it. It was electrifying as it became harder and harder until it was fully erect. I could hardly believe that this fantasy was finally happening and that the reality was better than the fantasy. When I could resist no more I lowered my head and began to lick up and down his shaft and from time to time and took his balls into my mouth and did my best to swirl my tongue around them. I spent quite a bit of time teasing like this before I finally took the head of his cock between my lips and then slowly swallowed almost the entire length. I started to apply different suction pressures and tongue swirling, occasionally nibbling with my teeth and I was surprised that he came very quickly (CIM). He told me later he was really turned on by a new "conquest". We had already assumed a male-male sex thing where he was dominant and in charge and I was sub which suited me just fine. That's probably why I dabble in BDSM from time to time.

He recovered in no time flat and pushed me onto my back and knelt over my face and had me suck him off. After a few minutes of this he got on top of me in a 69 and now I could hardly believe the sensations. He told me to perform oral on him exactly how I wanted it done for me, which he then began to mimic perfectly. It was almost like being in my own head and giving myself a blow job if that makes any sense. I came in no time flat and rolled over not believing what was going on. So much had happened in just thirty minutes.

We took a break, had a shower and back to the bed for another 69. When we showered together he had been behind me and fondled me to erection with a soapy hand and at the same time had begun to play with my anus. I am incredibly sensitive down there and in no time at all I had to lean forward on the shower wall to steady myself as waves of ecstasy ran through me as he gently worked his soapy finger inside me. He had already figured out that he was going to fuck me and I sure as hell knew that I wanted him to. Before we were too carried away with the 69 he rolled away, stacked a few pillows and told me to lay my hips over the top of them. I was laying there, my ass in the air feeling crazy vulnerable yet excited and nervous.

He took his time going to get the lube from the bathroom and when he returned he started off by massaging my buttocks, then gently biting and licking them until the electrifying sensation of his tongue in my anus shook me. He had me squirming at this point and after a while started to apply lube and slowly work my ass loose (well somewhat!!) as he probed me with one, then two fingers. The moment of truth arrived when he switched positions and I felt the head of his cock working against my opening. I was having a huge adrenaline rush from both fear and the thrill of it all. No question it was difficult and painful at the beginning. I can see how some men turn women off for life when they are not careful, but my friend knew what he was doing and really took his time. I could certainly tell he had a giant boner going! After a while everything relaxed and he was all the way in and I could feel him filling me up down there. We varied the pace, and I really enjoyed the sensation of him sliding nearly all the way out then slowly sliding all the way back in until he gave a hard push at the end. As he became more excited I managed to find his rhythm and he ended in quite the explosion.

The reality exceeded the fantasy and part of the thrill was the taboo and looking forward to those visits. We got together a couple of times a month for about a year. There was never any kissing of hugging, and I have never tried to label myself as gay, straight or Bi. It was a perfect storm of events in that I knew him before the MFM threesome, and I was already used to being around him sexually. I never did it again, but have often thought about those experiences and doing it one more time. BTW, true story.