My First Time With A Guy

In chat, I've had conversations about limited "gay" experiences I have had. Typing a private message on a smart phone can be a bit challenging. I can give context and detail better in this forum. 

My values regarding sex/sex acts: Honesty and respect among consenting adults. Regardless of the act, regardless of the gender(s) there should be NO deception. Lying/tricking to soothe a sexual itch is 100% wrong. Be honest with what you want and why you want it. Boundaries should be clear and respected. During the act, emphasis must be placed on the other's desires. 

I am not (fully gay). I have no desire for a romantic relationship with a man. I do not want to be kissed, hugged. I do not want to be orally satisfied by a man. However, pleasure comes in many forms.  Nerve endings around the anus, prostate, feet and inner thighs can blur the lines between gay and straight. Also, the ability to give sexual pleasure to another can be highly erotic and satisfying.  This story is about my first gay experience.

In the 90s there were many movie-video-tape rental stores. The store I frequented was small (not part of a chain). Joe owned the store as well as the house it was in. Similar age (late 20s), he looked a bit like the Happy Days character, Potsie (Anson Williams).  I was always renting R-rates T/A(tit/ass) movies like Porky's.  I was too shy to rent actual porn until Joe said something.

"Dude, I know you want jerk-off material, so just pick from the real stuff. I was embarrassed, but could not disagree. I started going 2-4 times/week. I would go after 11 pm. At that hour there was no chance of running into families or the elderly. Joe would watch porn behind the counter- usually gay porn. I had no taste for it, but was intrigued. Over the weeks, the conversations became personal and sexually charged. He spoke about gay romance and the like terms like twink, top and bottom. Joe liked to be a top, but enjoyed being a bottom sometimes. I could not imagine anything except pain regarding anal penetration. 

"Dude!" (his favorite word), "being a bottom is like wow because you gave satisfaction to someone. Anyway, lots of nerve ending there." Now I was more than interested. A few more weeks passed. I decided to try it. Joe knew the boundaries I mentioned in the back story.

The fateful night:

I arrived at the store at closing, 1 am. I had prepped myself, as instructed, to ensure I was exceptionally clean "back there".  We talked about various things as we drank Zima (remember those?). I would need to be semi-drunk before doing this to get over the mild repulsion I had (a repulsion that no longer exists in me).

Joe began with compliments. My looks, my shy/innocent nature and my legs/butt. He loved my butt (as many do still haha).

"Undress, Ray." I was a bit shy as I exposed myself to him. He undressed too. He was already erect. His cock was similar in size to mine- 6" and proportionately thick. He gave my butt a light tap and pointed to a slightly reclined Lazy Boy. There were pillows set up to position and support me. Effectively, I was on the chair facing backwards. Knees were bent under me, legs slightly apart. Pillows under my chest supported me and my penis dangled freely. I trusted Joe 100% and allowed him to bind my hands to prevent me from changing my mind. I am happy he did.

Joe brushed his fingers all over my lower back, butt, and inner thighs. I was resistant at first and did not like it. I would have stopped it but for my bound hands. Soon, it became pleasurable as he tickled my virgin backside. He applied lube to his finger and worked it partially inside me. With more lube and a breathing exercise, I was able to accept his finger. Joe was extremely patient. After an hour or so of working with his finger, he introduced me to his cock, pressing it to my anus. After another hour he was able to get his cockhead partially in without too much pain. We did another breathing exercise before he tried to enter me fully.

"This may hurt a bit, but give it a chance," said Joe.

He counted down from 5. At zero, I tensed, expecting his push inside me. Instead, at zero he tickled my feet. Distracted, I relaxed. That's when he pushed fully inside me. The pain was intense, but I gave it a chance. Once inside me, he thrusted very slowly and shallow. He rubbed and massaged my butt cheeks. Gradually the pain changed to mild pleasure. The pressure on my prostate caused a bit of cum to ooze out.

His pace gradually quickened, but not by much. His strokes became long and urgent.

No words were spoken. I felt his penis swell slightly as he grunted.  My insides felt a flood of warmth as his cock twitched and erupted. He then pulled out, causing his seed to leak from me. I felt a sense of accomplishment.  I had made another person feel the ultimate pleasure of orgasm.  He smiled widely.  

As per my desire, he did not touch me further and I did not cum that day.  I have no desire to do this again, but the memory is a positive one.

Hope all enjoyed

-Ray