What is dating like for a young trans, femboy?

One word: Difficult.

It is tough to meet people in real life. Firstly, the internet is not real life. I learned that the hard way with trolls and online bullying. Now, I found some great people on the internet; Max, James, Brian, Jasmine, Trixie, Tasha, Reese. I have only met a few actually in person, and they all went very well, but again, not real life.

Dating apps go like this: You chat. They seem interested. You meet up. You hook up. Both, male and female dates want to see one thing, the novelty of my cock under my dress. They both want to touch my cock. Then the guys want a blowjob, and the girls want pussy licking or tribbing.  Then, if I am lucky, they might watch me jerk off. They are usually surprised that I can get a hard-on and that I cum so much! I have yet to have a second date.

When I meet someone in real life, I have a choice: whether to tell them that I am a trans right away, or don't for a few dates.

I tried not telling the truth, but then after a few dates, it was very awkward, especially when he is reaching between my legs and wondering why I am pushing his hand away. I decided it is always better, to be honest.

So, honesty, most dates end, directly after I tell them. Some wait until after the drinks or dinner to be finished if I am lucky.

I was just about to turn eighteen, and I thought I was destined to be alone forever.

Then, I went to a university party with my best friend, Greg. He was on a football scholarship but, I was in the last year of high school and couldn't afford university anyway. It was the first party of the year, and the party was raging when we arrived. Greg introduced me to some of his teammates, and they were very hot! We decided that I wouldn't say anything to anyone at this time and just have fun!

I was having a great time when Luke approached me as I was getting a drink.

"Hi, I've been watching you?" Luke said, smiling.

"Creepy," I answered, jokingly.

"No, not like that," Luke fumbled, "I think you... are beautiful."

"Well, then I forgive you. Watch away," I teased.

"I'm Luke." He introduced himself.

"Samantha," I said, extending my hand.

"Nice to meet you," Luke said with more confidence.

"You too," I answered back.

"Do you want to go someplace quieter to talk? Luke asked.

"Sure," I said, as we left with our drinks.

We went to his room upstairs, which was small but mostly clean, and sat on his bed.

Luke was a lineman on the football team. He was six-foot-five inches and over two-hundred pounds of muscle. Luke had beautiful, smooth black-brown skin and dreamy brown eyes.  He was a very handsome black man! When I stood beside him, my slight frame only went up to his chest.

Luke grabbed my hand, and we walked up to a room upstairs.

We talked for a couple of hours, and the conversation was exciting and enlightening, not what I expected actually.

I liked Luke, and I think he wanted me, which was proven when he leaned in to kiss me. It was a deep passionate kiss that made my entire body tingle. After that kiss, we looked at each other. I liked this guy, and I knew I needed to tell him about me before things got any further.

"Luke, I really like you," I started, "but I need to tell you something important."

"I like you too, go ahead." Luke listened.

I had rehearsed this speech, but it still stumbled out of my mouth.

"I was born a boy," I started.

Luke listened and didn't make a run for it. Good so far.

"I dress and live as a girl," I continued.

Luke looked at me for what seemed like forever before he spoke.

"Like a transsexual?" Luke asked.

"I don't know what to call myself, but yes," I answered.

Luke paused again, and I thought it was my time to run to the door.

"I have a secret too," Luke began.

"Okay," I said, with slight hesitation.

"I am bisexual," Luke told me.

"That's cool," I said, relieved. "Thanks for sharing that with me."

I then took the initiative and leaned forward and kissed him. Luke kissed me passionately back. His hands moved across my body. I was filled with nervous energy when his hand moved across my thigh toward my cock—the moment of truth. Luke lifted my skirt and found my hard cock under my pink panties. He rubbed it and smiled at me. I kissed him back, harder.

Luke then moved back, hooked his fingers inside the waistband of my panties, and pulled them smoothly off. My hard seven-and-a-half-inch shaved cock bounced out in front of him. He looked down and smiled lustfully, kneeling between my legs and grabbing my cock. He jerked it up and down, looking at me seductively and then took it into his mouth.

Luke was a fantastic cock sucker. He said my cock was the first one he had sucked, but he had watched a lot of porn. It must have been a master class. Luke pushed his finger, then two into my tight asshole, moving it in and out. It wasn't too long before I needed to tell him that I was coming. I expected him to jerk me off to orgasm, but he sucked on me even more diligently.

I was moaning hard and then started to cum in his mouth. He let some of the cum drip out of his mouth down my cock, but he swallowed most of it. He still had some of my cum in his mouth as he moved up and kissed me on the lips. It was the most erotic kiss I have ever had and my very first cum-kiss.

"Your turn," I told him seductively.

"You don't need to," Luke smiled. "I have always wanted to suck on a cock for as long as I can remember."

"And you are very good at it," I told him truthfully, "but I really want to pleasure you."

"You have an amazingly beautiful cock," Luke complimented.

"Thank you," I blushed. "Now, let me see yours."

Luke smiled and opened his jeans and pulled down his pants. I was shocked when he revealed his cock to me. It was a monster! Luke's cock was at least ten inches long, and he was not even fully erect yet. Large pulsing veins came from the base of his shaft to the large purple cock head. It was scary and beautiful.

"A lot of girls are intimidated by my cock," Luke confessed.

"I can understand that," I admitted.

Luke disappointedly started to pull his pants back up.

"No!" I said, stopping him, "Your cock is amazing, and I am not intimidated at all."

Moving forward, I pulled Luke's jeans back onto the floor. Kneeling before him, I took his massive cock with both my hands and took him into my mouth. My lips were stretched, but I managed to get almost half of his enormous member into my lipsticked mouth. While I couldn't get him entirely in, I did lick and tongue his cock head until he was rock hard. Luke's balls were heavy and round, and he moaned as I cradled them on my tongue.

"Would you like to fuck me, Luke?" I asked.

"Do you think you can take me?" Luke questioned.

"I think I can," I told him honestly, "I have been practicing with a large dildo, not as big as you, but close," I added.

Luke moved to his dresser and pulled out a lubricated condom. It was an extra-large, but it still didn't roll all the way to the base of his cock. 'What had I gotten myself into,' I thought?

I moved onto the bed on my hands and knees, and Luke got behind me. He spit on my asshole and then pushed his cock to the opening of my tight pink hole. As Luke pushed in, I felt like he was splitting me open. I braced myself against the headboard as he pushed deeper. I was ready to cry out when he stopped thrusting.

"Just hold it there for a second, please," I begged.

I took a few short breaths and then said, "Okay."

Luke started to move out and then back into my asshole. He started slow and then built up in speed. After that initial pain had subsided, the feeling of his cock in my asshole was amazing. Each stroke was giving me more and more pleasure. I was begging him to fuck me!

Luke started to slap my ass as he fucked me, which added to the sensation.

"Fuck me with that big black cock!" I breathed.

My dirty talk seemed to encourage Luke. He pounded my asshole with even more speed and vigor.

Then he stopped and spun me around onto my back, and his cock never left my asshole. He never even missed a stroke. Luke grabbed my ankles and lifted my feet, and started to suck on my toes. He was pulling out all of the stops! I wasn't much of a foot-fetish girl before, but now I was all aboard on the foot train! My cock was rock-hard again as he fucked me. Luke saw this and smiled, grabbing my cock and stroked it in time with his cock going in and out of my hole. Luke was filling me up, and I was very close to cumming!

"Going to cum!" I announced.

"Cum for me, baby!" Luke responded.

That was it for me, and I started to cum, shooting my hot cream all over my stomach and chest. Luke pulled out his cock and quickly took off his condom as he was about to cum as well.

"Cum on my face," I begged.

Luke shimmied up the bed and put the tip of his cock in my mouth. He quickly stroked his cock until it exploded into my awaiting mouth and all over my face. It was like he was saving his cum for weeks; he came so much. His cum tasted surprisingly good, but a little saltier than I was used to. Luke scraped some of his cum off my face and playfully put his finger in my mouth for me to lick it off. He then kissed my cum-covered face and licked up his own cum as well, another surprise.

We fell asleep in each other's arms and in the morning, he drove me the two hours to my house. He kissed me good-bye and I went into the house, having had a wonderful time and expecting never to see him again.

To my pleasant surprise, Luke called me later that night, and we talked on the phone for hours.

For the next two months, we were dating like boyfriend and girlfriend. He would make the two-hour drive to see me. We would go out on dates, to dinner and movies.

The sex was outstanding as well. I was taking Luke's large cock in my asshole much easier now, and I could even take his entire length. Sixty-nine was also one of our favorite positions, and we would compete to get the other to cum first.

Things were wonderful, and I was falling head-over-heels in love with Luke.

I went to see Luke play football in October. He was a freshman but was starting that day, I was so excited for him, and he played great!

After the game, we went to the local bar for an after-game drink. I had never seen Luke so happy, and I was so delighted for him. The waitress, Kate, saw the game and said how great he did and what a cute couple we were. I couldn't be happier.

Luke and I were in a corner table holding hands and kissing when two of Luke's teammates came over. Luke introduced them.

"Samantha, this is Travis and Mike," Luke said.

"Nice to meet you, Samantha," Travis said.

"Nice to meet you," I answered back.

Travis turned to Mike, ignoring Luke.

"You know Mike, Samantha is cute and all, but he has a cock," Travis said mockingly.

Suddenly the air was completely sucked out of the room and I couldn't breathe.

"You're kidding?" Mike asked.

"Yep, it's true. Luke's girlfriend is a tranny and has a cock!" Travis explained.

"Wait a minute," Luke tried to intervene.

"That makes you a faggot cocksucker," Travis teased Luke.

"Do you suck her cock, Luke?" Mike taunted.

Luke didn't say anything, and he couldn't look at them or me.

Travis put his hand under my chin.

"I can see what you like, Luke. He's pretty," Travis taunted.

I looked toward Luke, but he was catatonic. I was starting to get scared.

"Leave us alone," I demanded.

"Or what?" Mike challenged.

"Please, just leave us alone," I pleaded.

Luke then stood up. I thought that he was going to confront the bullies, but he just pushed past them and left. I was in shock as Luke just abandoned me. I tried to get up, but Travis pushed me back onto my chair.

"Where are you going, fag?" Travis asked, "I think you need to give a couple of blowjobs."

I looked up to the huge men, terrified when a female voice from behind.

"That would make you fags, wouldn't it?" the waitress Kate said.

Travis and Mike turned to Kate, who had a baseball bat in her hands.

"Get the fuck out of here, or your playing days will be over," Kate warned.

Travis and Mike considered for a moment, but then reluctantly walked past Kate.

"Are you okay, sweetie?" Kate asked gently.

"Yes, I think so," I said, shaking.

"They are such jerks," Kate stated.

All I could do was nod.

"Was that your boyfriend that left?" Kate asked.

"I thought he was, but I don't think so anymore," I said, sadly.

"Do you live around here?" Kate asked.

"No, a couple of hours away, but I am okay, I just need to go," I said, trying to leave.

"Nonsense. I am off now, and I live around the corner, we can talk and have a drink," Kate offered.

As I considered this, I finally really looked at Kate. She was gorgeous and had very kind eyes. I agreed to go with her.

I didn't know it then, but Kate was the next chapter of my life.