Discovering I'm a bottom

Jim and I had been friends in high school and had just become roommates after graduating.  My only sexual experience, to that point, had been with girls.  Jim had admitted to having a drunken fling with a guy before, but he too had otherwise only been with girls.

We were in a cheap 2-bedroom apartment, and between us, we shared a TV and VCR in the living room.  When I entered the apartment one evening, I had obviously caught Jim getting off to a porno tape he had rented.  He was embarrassed, but I shook it off.  I added that I wouldn’t mind seeing the video with him.

I sat down on the other end of the couch, and Jim took the tape off pause.  The couple on the screen went through all the usual porno positions until the “script” had the woman’s husband walk in on them.  After a minute of terrible acting, the three of them were naked, and the husband made it a 3-way.

At first, all physical contact was limited to guy/girl.  I have to admit that as bad as the acting was, the “actors” were gorgeous.  Then it happened.  The husband mounted his wife, and the other guy positioned himself so that he could lick the length of the husband’s shaft as he slowly slipped in and out of his wife.  I was shocked as I had not witnessed a gay sex act live or on video before.

I couldn’t believe that I got hard as a rock watching the video, and it became apparent that Jim was studying me for my reaction.  He was encouraged that I had an erection instead of running from the room, so he decided to take things a step further.  He pulled his cock out of his pants and started stroking himself.

At that same time, the husband withdrew his hard-on from his wife and repositioned himself to fuck the other guy’s throat.  I couldn’t believe I was watching two guys going at it with the woman wondering what was going on below out of her sight.  My mind was racing with thoughts I’d never had before.  The biggest revelation was, “Of course, a guy can suck cock better than a girl.  He knows exactly what to do.”

No sooner had I opened my mind to gay sex, Jim said, “Look at that!  The guy knows how to suck a cock!”  And so I freed my erection from my pants, and we both took in the gay scene stroking our dicks in rhythm with each other’s movements.

I couldn’t hold back, and I shot cum everywhere.  Some of it spurted to the side and landed on Jim’s arm.  He stopped stroking himself to wipe it off with his finger.  And then my view of gay sex changed again.  He began sucking on his finger while he looked at me with a wicked smile.  I immediately went from “I am really not sure about this” to “I want to suck this guy’s cock and see what it’s like when he cums in my mouth.”

It was as if Jim could read my mind.  He didn’t say a word, but he started removing the clothes he still had on.  I followed his lead.  There was Jim with a magnificent hard-on waving like a flagpole, his legs spread apart and signaling for me to kneel in front of him.  He didn’t need to ask twice.

When I got positioned in front of him, I started doing all the things I had wished girls would have done when giving me head.  I cupped and caressed his balls with my left hand while grabbing his manhood with my right.  My mouth stroked his dick, matching my hand movements as my tongue went crazy over the head of his cock.  I worked his manhood with a pent-up fury I didn’t know was inside of me.  His involuntary moans turned quickly to gasps, and then all he could say was, “oh God, oh God, oh God” until he gave me his load.  He yelled and grunted as his cock erupted down my throat.  I was doing my best to keep working him for all I was worth while trying to swallow.  The torrent of his cum escaped my lips and spilled down my hands and his shaft.  I’d never felt so sexy in my whole life.  I was in heaven.

I kept slowly kneading his genitals as he basked in the afterglow of his delicious orgasm.  As he recovered, he said, “I was hoping you’d be into this.  I was also sure you’d be good at it.”

“How did you know?” I asked.

“I just had a feeling,” he said, “but you know there’s effeminate side to you when it comes to sex.  You once told me your favorite sexual position was to be on the bottom and let the girl do all the work.”

“What are you driving at?” I asked.

“I’m what’s called a top.  I think deep inside, no pun intended, you are a bottom,” Jim said, donning his wicked smile again.  “You want to be the girl when it comes to actual intercourse.”

“You mean like I want the girl to put a dildo up me?” I exclaimed.

Jim laughed and said, “Girls have nothing to do with it.  I think you want me to fuck you with the real thing.”

I wiped his cum off my mouth as I thought about what he had just said.  Having never had gay sex, I couldn’t imagine how two guys could actually have sex.  As I continued to think about it, Jim started to get hard again.

“Don’t worry,” he began, “I’ll be gentle, and you’ll only enjoy it.  I can’t tell you how much I want to feel my cock sliding inside you.  Get comfortable on the couch while I get some lube.”

He walked out of the living room, and I sat back on the couch.  He returned with a jar of Vaseline and told me to slide my ass just past the end of the cushions.  As soon as I did, Jim slathered the Vaseline on my anus and then on his erect cock.

He took his index finger and slid it inside me.  I gasped, feeling his intimate touch and venturing where no one had gone before.  Soon he had a second finger inside me, and he slowly worked them back and forth.  I was glad he was gentle because I could tell what he was doing could hurt a lot.  I also started to feel so sexy.  I could tell that Jim liked making me feel like I’d never felt before.  Here we were, doing what most straight people would find abhorrent, but I had never felt better.

Jim finally positioned himself with his pelvis directly in front of my crotch.  We locked eyes as I felt his manhood searching for the bullseye.  He used his hand to work his cock inside me.  I couldn’t believe this was happening.  What a fantastic feeling it was to have this gorgeous man’s rock-hard shaft seeking relief in such an intimate way.  He got the head of his penis inserted and then slowly pushed and pulled, but not going more than an inch inside of me.  I wanted him to penetrate me more than anything in the world at that moment.

“Push against my cock like you’re trying to take a shit,” Jim whispered.  “That will open you up to let me in all the way.”

He was right.  As I did what he said, I felt his shaft move farther inside me.  I thought it might be painful, but it wasn’t.  Jim continued to push ahead as I welcomed him into me.  I can’t say how long this went on, but eventually, I felt his balls press up against me.  I had my eyes shut, but they flew wide open when he was in all the way.

Our eyes stayed on each other as he started to withdraw and then thrust himself into me.  He asked me to hold my legs up, hooking my arms under my knees.  I felt so exposed and so sexy as he started pumping himself into me faster.  I understood the appeal that women found in sex.  I wasn’t worried about if I would cum.  I was more concerned with making sure Jim came inside me with an orgasm he would never forget.  I imagined myself as a female and luxuriated in my feminine mystic as Jim continued to pound his hips into my crotch.

It really didn’t hurt.  I started feeling the beginnings of an orgasm, but coming from a place inside of me I had not known existed.  My new sexual identity as a bottom was about to be born.  I was fulfilling fantasies I never knew I had, letting Jim have his way with me.  I was already thinking ahead to just how much we would do this together in the days to come.

And then the feeling intensified as Jim’s grunting grew louder.  I couldn’t help but gasp with each pounding thrust of his cock.  I was cumming as I’d never cum before.  A flood of cum spurted out of my cock and landed all over me.  Jim let loose as well, and I could feel his sperm spilling out of me as it trickled down my ass.  God, this was sexy!  This was how sex was meant to be!