Recently, I was asked in a private DM about my first time with a guy after my purely and solely heterosexual upbringing and childhood.
I decided to share my first experience story with you all, as it may be meaningful to someone who is struggling and confused with their sexuality out there...
I had been hit on and propositioned by many hot guys in College and during the first year of my career after school, but did not act on my mutual attraction, because I was ignoring my natural instinct and instant excited hard on. I had a beautiful girlfriend throughout College and believed she was enough for me. We planned to get married after College, have kids and I would live a “normal” life.
I thought I was hetero and was taught to be a strong masculine man so I could not understand my strong attraction to boys, as well as girls, starting from early in my childhood. Additionally, there was no family or friends to talk to about my sexual cravings and no internet to learn I was “normal” and not alone in my duel attraction.
Then... in the second year of my career, I was invited to attend the annual sales conference held in South Beach Miami. As a rookie, I was rooming with a more senior associate. He was very friendly and took me under his guidance and mentorship to show me the “ropes”.
One night, after our scheduled dinner and social party at a night club in Miami, he suggested we take a cab back to the hotel together, so I went along with him. While in the cab we talked about past girlfriends and the difficulty with women in general. He acted very hetero straight with me at this point. I felt very comfortable confiding my history to him.
When we arrived at the hotel on the beach, he said he did not want to go up to our room yet... he wanted a late night swim in the ocean! It was about 1 am, but I agreed to go with him to watch. When he got on the beach, he immediately stripped down naked and ran into the water. I watched him get naked in front of me and popped a raging excited boner the whole time... I was nervous and could feel the sexual tension and expectation in the air.
He then yelled out from the water for me to come swim with him. I agreed and stripped down on the beach as well, desperately trying to hide my rock hard cock from view. I quickly ran into the water with my raging cock bouncing up and down and started to swim. It was completely dark out in the water, except for the colourful neon lights from the hotels along Ocean Drive. So I did not think that he saw my hard cock as I was running into the water. I was so naive at age 22... but he knew exactly what he wanted at the age of 35.
Once both in the water, he swam up to me and I could feel his hot breath on my face as he grabbed my hard cock, looked directly into my eyes and asked, “Do you like this?”
I timidly and uncomfortably said “yes.” He then started to stroke my cock, under the water, while he leaned in to kiss me. I kissed him back and enjoyed the feeling of the rough stubble on his face, that was a totally new sensation for me, having only kissed the soft and tender lips of my past girlfriends.
We frenched kissed for awhile, getting more and more passionate and he continued to stroke and jerk my hard cock, while the crashing waves rolling past us. Soon, I felt like my cock was going to burst from the pressure and excitement. Our passionate kissing was driving me crazy with anticipation. I had not felt like this with any past girlfriend?
He then asked me to return with him to the beach, and I followed, where he found a picnic table. He laid me down on the table and immediately started to aggressively suck the head of my hard cock. He licked at the tip and swirled his tongue around my rock hard smooth helmet. He then slowly sucked all the way down my shaft, taking in my whole cock, and tongued at my exposed tight balls. I did not even have to ask him, he wanted to suck my cock. He acted like he actually needed my cock. I did not understand his passionate necessity?
He knew how to suck cock so well, like nothing I had felt with my young inexperienced girlfriends. He sucked me so well, I unloaded in under 5 mins and he swallowed it all. Past girlfriends took 20-30 mins to get me off and always spit afterward making a nasty face. He licked it all up and moaned with enjoyment...
I said sorry that I could not return the favour. He replied that it was all ok; that he was not expecting me to and that we should probably get dressed and return to our room now.
I was silent with guilt and the discomfort of what just happened, yet strangely relaxed and completely satisfied. As we walked off the beach together toward the hotel, I was silently trapped in my head, reflecting on my family and stern religious upbringing. Thinking that now I was definitely going to hell...
Once in our room, I realized I was much more relaxed than stressed, after my amazing cum from his blow job, giving me an orgasm like none I had experienced before. I had shot hard, fast and pumped my cum with great force into his mouth. With that image in my head, I quietly undressed and put on clean underwear then went to my bed, saying nothing to him. He undressed and remained naked as he slid into his separate bed. We both stayed silent, but after about 10 mins, he broke the eerie uncomfortable silence and asked if he could join me in my bed?
I surprisingly agreed... without hesitation.
He jumped into my bed and slowly started to fondle and stroke my cock through my underwear. I was relaxed and getting hard again with excitement and anticipation, but then started to realize where this scenario may lead and was not sure if I wanted to cross that line, just yet...
I was starting to feel very very guilty and ashamed that I was allowing him to stoke my cock again. What was I doing? Was I gay?
He noticed my building stress and relaxed me when he said, “to only do what I wanted and what felt good to me.” He assured me that it was totally normal to experiment with sexuality and that everyone experiments. He said he was not expecting anything back from me.
He slowly began to slide my underwear down over my now raging hard cock and then fully jerked my cock with his hand while kissing me. I was enjoying all his attention and desire for my cock. I was rock hard and excited but now knew that sex with women would never be the same again... first, because he was so much better than any girl I had encountered to date, and second, once I crossed that line I would have to be honest and confess this night to every girl I wanted to fuck in the future.
Regardless of my thoughts, I loved what he was doing. It felt so awesome, my entire body was quivering with excitement and I just wanted to surrender completely to him. I desperately wanted to cum again.
Once he removed my underwear completely, he started to massage and rub my virgin asshole gently with his thumb. Then he gently and very slowly stuck one finger in my tight hole and asked if I was ok. Amazingly, I was!!
I loved it... I never had a finger in my ass before. I had done anal play with my past girlfriend, but only with her ass. He continued with a second finger into my asshole and loosened up my hole. I laid back on the bed, grabbed at the soft hotel sheets, relaxed and enjoyed the sensation as he rubbed and massaged my prostate. That was fucking incredible! I could hardly breathe!
When he got the third finger in, I started to really feel it. I was in heaven!
He noticed that I was now relaxed and feeling amazing, so he asked if he could insert just the tip of his cock. For the first time that night, I looked more closely at his cock. It was shorter than mine but much much thicker, super pulsing hard and the head was glistening with pre cum. He had a smaller head by proportion and comparison to mine, but his shaft was so thick... beer can thick!
I felt so good that I decided I would try his tip, so I agreed. He pulled his fingers out of my ass and then rubbed his wet pre cumed tip against my hole and it felt so amazing...
We did not have condoms and I was slightly concerned; however, we were all tested for our career medicals, so I believed it would be ok. I trusted him and that he would be honest and tell me if he had a sexual issue.
He then spit on his cock, rubbed more spit on my asshole and gently pushed his hard tip into my relaxed and loosened hole from his fingering preparation. He moaned...
The tip felt awesome!! I was enjoying the slow expanding pressure as he entered into my aching hole. I moaned, with pleasure. My hole was accepting and slowly sucking in his whole head. He asked if I was ok?
I replied, “yes!” enthusiastically.
He asked if he could continue?
I said “yes!” again enthusiastically.
He pushed his hard cock a little further into my ass. I was still feeling awesome until the full thickness of his shaft started to really stretch my hole open. Then I felt some sharp pain and not pleasure. I was not sure if I could handle any more of his thick raging cock?
He noticed and stopped immediately and then pulled back asking if I was ok?
I replied, “oh no!” but, at the same time, I felt bad for him and me, that he could not complete his mission to fully take my anal virginity.
He was completely understanding, knowing how thick his cock was, he probably had difficulty with other partners before me.
He pulled out completely, still rock hard and jerked his cock over my young chest.
He jerked himself for about 5 mins and unloaded all over my abs and chest with his thick, hot, creamy cum.
Some shot up on to my face and a little into my eye, which started to sting. I also got a little on my lips as well, but was not brave enough to taste it. I had only ever tasted my own cum before and was not sure I wanted to eat or swallow another man’s cum.
He quickly got up to clean my face and chest with a soft fresh towel from the bathroom. He was really so sweet and caring about it all.
I still felt bad and so sorry that he had to jerk himself off to finish and that I could not or did not know how to reciprocate with at least a hand job or blow job.
However, he never made me feel bad about it. He was so generous with his affection and concern for my well being and satisfaction. He guided me very gently and expertly into the world of bisexuality.
All in all, it was a great first time with a man!
Since that first experience, I have had many male and female partners. Some accepting of my sexuality and others not, but what I have learned is that you must live your truth to be fully happy. When I hid my sexuality, I was miserable and negative to all around me. Life is way too short to be miserable and you should not deprive yourself of full pleasure.
You must live your truth... Be who you want to be. Do not suppress your sexuality. Explore and discover all that you are. Enjoy yourself and find peace, joy and love in your full self acceptance.
Below is a photo of me at 22, when I had my first experience with a man... and loved it!
Just asked again about my first time with a man... so here is my full story for all to read, learn and share. Thank you! Love to you all...!
