Once I arrived home, my thoughts were racing over the encounter. I felt conflicted about my sexuality, and I needed to resolve that first. The fact remained that I was a cross-dresser, which I loved, and that would not change. Jack accepted that and expressed excitement. My secret for now would be safe. When I was dressed up, I knew I could please any man and give them a hard-on.

What I must settle on: how far I will go? Would I be comfortable sucking Jack’s beautiful dick and letting him cum in my mouth? His cum excited me when we kissed. The way he looked at me when I walked, I knew what was next. He told me I had a pretty ass. The thought of having his hard, pretty dick being pushed into my tight spot excited me.

I wanted to do what made me feel good with no regrets. Jack came across as a loving and gentle person. This could be an opportunity to explore my fantasies to bring them to reality. Until now, I’d been reading about others and wondering what it would feel like.

 The bold thing to do would be to call Jack and say, “I want you to fuck me.” I would not be so bold and follow his lead. I would make a short video and see if I could get a rise out of him.

I set up my video equipment. It was time for my transition and my clothing was on the bed. I stripped to get into something sexy. My favorite outfit included black panties, a garter belt with black stockings, and a bra. I took time getting ready. I looked in the mirror to admire myself and I was getting excited. The finishing touch was a mini red dress that hugged my body. I posed for a couple of still shots.

To tease Jack, I took a selfie and sent a brief text with the following, “Miss you.”

I pointed the video camera at the mirror to show a double. As I was walking, the bulge in my dress was showing as my member was growing. My hands went across the front of my dress.

“Hey, baby. Do you like what you see? I am horny after seeing your pretty dick shoot your sticky stuff. I wish you were here with me. This is to show you when I am comfortable.”

The more I was rubbing myself, the harder I was getting. I slipped out of my dress to show my dick stretching my panties. I removed my panties to free my dick. My coconut oil was close by. I squinted some drops in my hand and on my shaft.

Looking at the camera, I said, “Oh baby. It feels good having my hand sliding back and forth along my shaft. Agghh baby. I wish your hand was on my dick. Uuummm. It feels so good.”

I walked over to the doorway to hold my hand in place while I looked in the mirror. My hand was holding my dick, and I moved my hips like I was fucking my hand. I watched my dick slide back and forth.

“Agghh. Fuck. It feels so good. I can make myself cum from this. Where are you?”

I walked up closer to the camera to show the droplet of my clear lubricant.

“Do you see my lube? I am going to taste my sticky stuff.”

I squeezed my dick to force out more lube and took my finger to wipe it off. I brought my finger up to my lips to taste myself.

Looking into the camera, I said, “Honey, if you were here, we could share a sticky kiss.”

My balls were tight up against the base of my dick. The time for me to release my cum was close. I turned my back to the camera and leaned over. I spread my cheeks to show my tight anal opening.

“Do you see my virgin opening, baby? Do you think your dick can fit in there? If you are a good boy, I might let you fuck me. If it feels good you can cum in me. How do you think the head of your fat dick would feel being pushed into my tight anal opening?”

I turned back around to face the camera.

“Baby, it is time for me to cum. My favorite way to cum is to invert myself against the wall so that my dick points at my mouth. Yes, I want to taste my hot cum." I got in the position, so the camera was at good angle.

My oiled hand was sliding back and forth along my shaft. The head of my dick was inches from my mouth. My dick looked delicious.

“Oh, baby. Watch me shoot my cum in my mouth. Agghh. Oh. It feels so good. I want to cum, baby. Yes. Yes. I am cuummiinng.”

I tensed my legs, and my shaft pulled my balls tight against its base. There were three short squirts of my sticky cum that landed in my mouth, with some along the side of my face. Oh my. I tasted sweet as I swallowed all of it.

Looking back up at the camera, “Okay sweetie, the show is over, and I hope you liked it.”

I brought my legs down as I was flat on my back. I looked at the rest of my cum drip out from my dick. The sticky stuff felt warm as I rubbed it over my stomach. I felt nasty and horny.

Standing up, looking in the mirror, my dick was limp and covered with my cum. I was having mixed emotions about getting fucked. Using a dildo to play with my tight hole is one thing, but the unknown is having a pulsating real dick sliding in and out. The porn movies make it look so easy. I could feel myself getting aroused. The flashbacks from the gym pushed my emotions as the thought about holding Paul’s meaty dick in my hand and how beautiful it looked.

I haven’t made a final decision, and I will see how things develop. I got myself cleaned up and put on a matching bra and panty set with a red mini-dress. I sat at the computer and uploaded the video to prepare to send it to Paul. I was trying to imagine his reaction upon opening it.

To give Jack a heads-up, I sent a text to him before the video.

“Hey, this is your lovely boy. You will receive a video for your viewing pleasure. To get in the mood, you will need to get naked and a bottle of coconut oil. You can oil your dick and play with yourself while you watch the video. Cum hard baby.”

I sent a text message, and then I sent the video. It was a waiting game to get a response from Jack.

Two hours later, there was an alarm from my computer for an incoming message. The email was from Jack. The body of the email was empty and there was an attachment, which I clicked on, and it opened. I was unprepared for what I saw on my screen. There was an image of the head of a pretty dick that was coved with sticky cum. Down both sides of the penis, the semen was present. The image looked delicious. The longer I looked, I got horny and wished I had been there when Jack’s dick started pumping his cum. Oh my, I wanted to taste his cum.

The picture got me excited. I stood up and stripped and wrapped my hand around my dick and jacked off. It took a few minutes for my dick to leak lubricant. The intensity was building up in my shaft and the release of my cum started squirting from the tip of my dick. The feeling was electric, and I wished it could last longer. My cum covered my balls and dripped down my legs. I had a sticky mess to clean up.

My phone was ringing, and I saw it was Jack.

“Hello, baby.”

“I do not know where to start after watching the video. I have watched it three times. I am horny and need to feel you close to me. There is something that I want to give to you.”

“Let me guess. Is it hard and long with a pretty head?”

“You must be psychic.”

“No. I am horny and want your dick. I am ready to let myself go so we can enjoy ourselves."

“I realized how beautiful you looked dressed up. When I come over, can you dress up for me?”

“Yes. I can do that if you promise to give me a good fuck.”

“That will not be a problem, as we can get nasty. I will see you later.”

I wanted to look sexy for Jack and get his dick hard as soon as he steps in the door. I had a new bra, panty, and garter set. I went all the way to do whatever Jack wanted.

Later that evening, Jack arrived, and I greeted him at the door with only my set on.

“Damn. You look beautiful, and you must be happy to see me. Your dick is sticking out. I hope it is for me.”

“This is all for your pleasure and get out of those clothes.”

Jack had stripped in no time and when he pulled his panties down, his dick sprang free and pointed out.

“I see I am not the only one that is excited.”

“It has been hard on the trip here in anticipation.”

“Is there anything special that you have in mind?”

Jack had pulled me close as our dicks rubbed against each other as our fluids leaked out. We embraced and started to French kiss. We were doing some tongue play. I was hot, horny, and ready to fuck.

We walked back to the bedroom. Jack sat me down on the edge of bed, and knelt between my legs.

“Your pretty dick needs to be sucked, and I want to feel your head in my mouth.”

I felt his hand wrap around the base of my dick. A few seconds later, his tongue was going back and forth along my shaft. His tongue played with the head of my dick as he tasted my lubricant. The feeling was wonderful and all I could do was moan.

“Be careful and do not suck me until I cum. I am so close.”

My dick slipped out of his mouth.

“I want to suck you until you cum in my mouth. I want to feel you pumping your hot cum. I want to feel your dick throbbing. I was thinking about this on the way over. You must cum in my mouth.”

Jack held my dick, and I watched as his lips circled the head of my dick.

“Oh. Baby. It feels wonderful. Suck me until I cum. Oh yes. Make me cum.”

I felt his finger putting pressure on my tight opening. I wanted to scream and tell him to push it into me. I wanted to feel his dick. Jack’s head was going up and down on my dick. I could barely make out what he was saying.

“Ummm. Your dick feels good in my mouth. I love sucking your pretty head. Your pre-cum tasted sweet and I want it all. Agghh.”

I looked down, and my dick was completely in Jack’s mouth.

“Oh, damn Jack. Suck me, good baby. Yes. Yes. I want to cum so bad. I can feel it building up. Please do not stop. Make me cum. Eat my cum.”

My dick slipped out of his mouth. I looked down at Jack and our eyes met.

“Your dick feels right in my mouth. I love the taste of your lubricant as it is seeping out. Your beautiful head is driving me crazy. I can suck you for hours. I want you to squirt all your cum, baby. Agghh. This is fantastic. I love your dick.”

I watched as his soft lips covered my head. I felt his tongue sliding across the tip of my dick.

“Keep sucking me. Agghh. Yes. Suck me.”

All I was hearing was moaning and the sucking sound.

“Please make me cum. I am ready to squirt. Yes. Yes.”

My dick was twitching, and I was close. I was unable to remain on the bed. I stood up and Jack kept my dick in his mouth. I had my hands on the top of his head while moving my hips.

As I was closer to cumming, I felt Jack place a finger over my tight anal opening. His other hand was on my shaft, going back and forth. His lips still covered the tip of my dick. He looked sexy.

“Oh fuck. Suck me, baby. I want to cum. I cannot wait any longer. Agghh. Please.”

Jack applied pressure on my anal opening, and it was like a trigger being pulled. My first release of cum squirted from the tip of my dick.

“Oh yes. Suck my cum. Eat all my cum. Agghh. Yes. Yes. Play with my ass, baby.”

The more pressure that was applied, the harder I came. I looked down and saw my cum seeping out the sides of Jack’s mouth. I never came so hard. My cum dripped down and landed on his dick.

“I want to suck your last drop of cum. You taste so sweet.”

Jack stood up, and I was licking the cum off the side of his face. We kissed, and I was tasting my sweet cum on his lips. I felt his hard dick against my stomach with lubricant at the tip.

“Poor baby. Your dick is hard, and you did not cum. We need to do something about that.”

“I am not worried about that because I wanted to please you. I hoped you loved having your dick sucked. It was amazing feeling you cum in my mouth.”

“When you had the pressure on my anal opening, I was thinking about something better. I want your hard dick in my tight anal opening. I want you to fuck me. You can fill me with your sticky cum. I want to feel your pretty head being pushed into my tight hole.”

“Oh, honey. Yes, I want to fuck you so bad. Your ass is pretty, and I cannot wait to feel my dick being pushed into your tight hole.”

We embraced again and kissed. I had my hand on his dick and was squeezing it.

“We can set up a time for you to fuck me.”

To be continued….