First Femboy

I'm an average divorced guy: middle aged, dad bod, decent looking, decent cock. I'm primarily straight in that I have only dated women and only find women attractive, yet find sex with someone with a penis incredibly erotic. I've experimented a little and had fun - those memories are often ones I relive in my fantasies.

One day while shopping at the local Trader Joe's, I encountered a being I had never really known about at the checkout. He was tall and thin with long hair and feminine features. He wore feminine clothes and even had a bit of makeup on, but otherwise spoke and acted like a boy. As he rang up my groceries, we interacted a bit and I felt like he was checking me out. I paid and left but was left with the impression that a bit of flirting had just happened with this young man. I was a little flattered and a little intrigued. What would it be like to hang out with such a human? A completely new experience. The thought stuck with me.

A few months went by and the relationship I had been in for a while ended. No good guy, no bad guy - she was just in a different place in her life and I didn't fit.

After being single for a while, the thought of the checker came back to my mind. I decide to go shopping and see what I could find. No luck. I bought a few things and could not find him. Perhaps I had waited too long and he had moved on. I let the idea go and got about my life. After a few more trips to TJs, I wasn't even thinking about it - when who should be there than my curiosity. I grabbed what I was there for and got into his line even though there were other shorter lines available. When he finally got to me, we chatted again but I lost my nerve. I had not been mentally prepared for him to be there, and then I thought why would someone so young want to have anything to do with me? I bought my stuff and left.

As I was getting to my car, my new friend - Jamie - came up to me, letting me know I had forgotten one of my bags. I thanked him for bringing it out and mustered up the courage to ask if he would like to hang out sometime. He gave me his number and told me to text him. Wow!

I texted him later that day letting him know it was nice to meet him, that I found him intriguing, and asked if he would like to meet for drinks at a local pub. We set something up and met at 8. We had a few beers and told each other the major facts about our lives. For me it was college, marriage, kids, divorce, single life. For him it was just school, lack of sports, a litlle college, etc. After a few more beers I inquired about his sexuality, apologizing in advance for any offensive I might give in my ignorance. He was very open about and let me know that he was primarily attracted to older men - me especially (that was a nice flirty way to clarify why he was here :) - and that he did not have much experience yet. When he inquired about me I let him know my history - primarily women - not attracted to men but that I had fooled around a bit. I also let him know that he was the first male I ever found attractive which is what has held my imagination for a few months. I then suggested that we call it a night so that we didn't make any foolish decisions. He told me that he had also been thinking about me for a few months and has fantasized about being with me many times. He added that he has been waiting to finally see my cock and did not want to wait any longer. So we headed to my place.

On the way, I thought back to my few experiences with guys. They were explorations into letting go. I have a stressful job where I manage people, lots of responsibilities. So in my explorations I mostly assumed the bottom role - no stress - no thinking - just taking and pleasing. It was clear that this was not one of those situations. I was the top - Jamie was the bottom. We did not have to discuss it, the vibe was there. So I thought through the things I had wanted and decided to give those things to Jamie.

When we got to the house I took control. The first thing I told him was that

"We should never do anything you are not comfortable doing. Use the safe word "detention" if you ever need to."

I then grabbed 2 beers, sat in my chair and told him

"Strip."

He complied - with a sexy little show - though unintentional - of disrobing. He quickly took off his shirt, then slowly lowered his pants, and took off his socks until all he had left were his Victoria's Secret lace panties. He turned a few times, and bent over to show me his tight ass, then slid them down, past his knees and around his ankles and off. I was not able to see his cock yet, and when he turned around his hand were covering himself. I commanded him to

"put your hands behind your head and show me everything."

He closed his eyes and did it. I told him to

"walk to me."

I lifted his cock and caressed his balls. They were nice - nothing huge but respectable and clean - totally clean. Jamie did not have a hair on his body.

Then I told him to

"turn around and grab your ankles."

I then grabbed his ass and spread his cheeks apart. Again - totally clean. I liked what I saw.

Now I commanded him to

"get on your knees and pull my cock out."

As expected, the power structure worked for both of us. He had clarity on what to do / what I wanted and I was in the dominant headspace. He knelt down, undid my belt and button and unzipped my pants. I lifted up and he slid them and my boxer briefs down to my ankles. I got back into command mode

"Hold my cock and stare at it."

He complied - mesmerized by the sight of the cock he had dreamed of in his hand.

"Smell it."

"Kiss the tip."

"Lick my balls."

He eagerly complied. I sipped my beer with one hand and grabbed my cock with the other. I rubbed my precum on his lips then slapped his face with my cock - everywhere: forehead, cheeks, nose, chin, eyes...

"Tell me what you want."

"May I please suck your cock?"

I put my beer down and grabbed his head with both hands. Then I slowly guided him down until the head of my cock pressed on his lips. Down further 'till he could feel my cock enter his mouth, past his lips, onto his tongue. I let it there for a second and he gently sucked. Then I pulled him up and entered again.

"Yes. Suck that cock honey."

More face fucking.

"Yes. Take it cocksucker."

Now pushing toward the back of his throat.

"Yes. Take it deep little girl."

Now into his throat.

"Yes. Choke on it bitch."

After a bit of throat fucking I pulled him off.

"Drink some beer. Let's go to the bedroom."

We headed to bed and I stripped off my clothes. I laid down.

"Get in bed and suck my cock some more honey."

Compliance.

I reached into the drawer and pulled out a towel and lube. I squirted some into my hand and began massaging it onto his rosebud. I took my time and rubbed the outside only for a few minutes. Jamie was so eager in anticipation that he kept pushing back on my hand as he sucked my cock. Finally I gave him what he wanted and put a finger in.

"You like that?"

"Um-Hmm (mouthful of cock)."

Now hitting the prostrate.

"Mphhh (mouthful of cock)!"

Another finger.

"Ohhh (mouthful of cock)!"

Another finger.

"You are about ready to take my cock in your ass. You want it honey?"

"Please fuck me!"

I pull my cock out of his mouth and slide it into his ass slowly from behind.

"Ohhh! (ass full of cock)."

I grab his hair hard and hold steady for 15 or 20 seconds. Then I start to slowly fuck him.

"You are my bitch now. I own your ass."

"Yes! Yes! Take me."

I push his head into the pillows as I fuck him harder. Pound. Pound. Pound.

Now I flip him over and put his ankles up to his ears. I slide back into him without even holding my dick. His asshole is so open now I slide in easily. I fuck him like a woman.

"Take that cock deep in your ass faggot. You are getting fucked. You are getting owned."

Then he cums all over our stomachs.

"Yes. You love getting fucked."

"I do."

Then I pull out of his ass and jump up to his face so I can cum all over him. He opens his mouth and closes his eyes and I blast him. Shot after shot of heavy hot cum hit his face, his tongue, nose, cheeks. I keep cumming hard - this is such an incredibly erotic experience for me. I love it. And I'm spent.

We clean up and have another beer. I explain that I will address him with respect everywhere except the bedroom. Jamie begs me to be even nastier next time. Of course there will be many more...