The Very First Time [ The Lollipop Experience ]

T h e   V e r y   F i r s t   T i m e ( 2004 ) — I really hate that Rogene was the first person I experienced fellatio with. Because for the longest, it used to really disgust me. You wouldn’t believe that statement now, since I’m such a professional at it. But then again, I’m the type of person who wants to be great at everything I do.

As mentioned, the very first time I ever performed fellatio was with my first boyfriend, Rogene. We were both still teenagers. I was sixteen and he was nineteen. And Rogene had been begging me to try it for the longest. Not only because I had never done it, but because I told him it just sounded like a disgusting act. If you think about it, the urethra is where a man urinates and ejaculates through. And because I’m a hygiene freak, that alone turned me completely off about giving head.

Rogene begged me every single day. I mean he whined and cried about it. He would deliberately fetishize my lips touching his penis. He’d force me to watch porn and learn, but I was not turned on back then. It literally was an absolute turn off!

One day, his begging literally turned me completely off. I mean, I didn’t even want to have sex with him. I had initially went over to his house to just watch movies and play video games and he was begging for sex. He even got to the point where he said, “I’m not gonna eat your pussy any more.” and I was completely fine with that, because it wasn’t like he was ever really good at it. At least back then, I never really got much pleasure from it. I generally thought he was doing it wrong.

Anyways, I just wanted him to understand that we didn’t have to have sex on a daily basis. We should be able to just kick it and if it led to sex, great. But Rogene was always a fucking horn dog. I was just trying to play video games, and Rogene was being petty, trying to make me lose and distract me by grabbing on my chest and trying to kiss me on my neck. At that point, I got up and left his house. I walked home. He was so mad. He was harassing me on my cell phone, but if you remember how cell phone plans were back in the early 2000s my minutes were precious. Lol. Luckily, I was still in high school, and I had my own phone line in my bedroom. And of course, Rogene began to call my landline once he assumed I was home.

After over an hour of dodging his phone calls, Rogene came over to my house. Back then, my family was not happy that I was with Rogene, as this was our second time dating. Because previously, Rogene was very impatient throughout our dating and was always trying to force me into doing things I had no interest in doing (ie. sex). Therefore we broke up. And when we began dating the second time around, my family was adamant about making sure Rogene was not around the house. If I was going to be in a relationship with him, it was to stay out of our home. Well obviously, not much had changed this second time around, because once we did start having sex, he could not stop. Probably one of the reasons I’m an addict now. As mentioned, Rogene came to my house, and he was knocking at my bedroom window. I was pissed, but I was not surprised either. Rogene was very controlling and did not like not getting his way. He climbed through my bedroom window, and he got comfortable in my bed. After closing my window, I got in the bed with him, and we began talking, did some arguing, but we concluded with some compromising.

Rogene was very jealous that I hadn’t lost my virginity to him. It bothered him. And what bothered him, was that he knew who I did have sex with first, and he absolutely hated that I was still friends with that person. And this was why Rogene was pressuring oral sex so badly. He had to be first for something, as odd as it sounds. But we had made an agreement. He was going to be more attentive to what I wanted as far as our relationship went, and he was going to be less whiny. As long as he acted right, he’d possibly get more sexual favors.

A few weeks had passed. Things were getting a little better between Rogene and I. I had been going to the dentist about getting my wisdom teeth pulled, and I was nervous about the procedure. After a session with my dentist and getting my teeth cleaned, I went over to Rogene’s house to spend some quality time with him. Rogene had been making me laugh and playing around while we were in his bed laying down. He kept complimenting my new smile and telling me how beautiful I was, which he always did. Of course, when he complimented my beauty, he never could steer away from my lips. So we were laying in bed, cuddling and he just would not stop kissing me and looking me in my eyes.

“Dyana, you are so fucking beautiful.” He complimented, kissing my lips. “And your lips are so luscious.”

“Thank you, babe.” I responded, kissing him back.

“I swear to God, I bet if you gave me head, it would be so addictive.” He stated. “I just know it would be.”

“Here you go again with that shit.” I giggled. “If I did it one time, would you leave it alone afterwards?”

“Wait, so now you’re saying you would try it?” He asked, shocked.

I laughed. “Yes, if it meant that you could never ask me to do it ever again!”

“I’ll take that bet!” He exclaimed.

We both sat up in the bed and I looked him in the eyes.

“Let’s get this straight…” I began. “If I give you head, and it’s good, you can never ask me again. You can never beg me whatsoever?”

“Yes, I will never ask again!” Rogene smiled. “I just want you to try one time!”

“Alright, let’s put it in writing.” I said.

I got up off his bed, and I grabbed a notebook from his dresser and I began writing up a contract, which entailed:

Dyana will give Rogene head.
And whether it is good or not, Rogene will never ask for head again.

It was dated and then signed by the both of us. Rogene was excited. But I was scared because what if I kept thinking about the “urethra”. EWWW!!!!! I mean, that was literally my only turn off. As mentioned Rogene was so excited, but I had to turn him down.

“Babe, you’re going to have to give me 24 hours!” I told him.

“What do you mean?” He asked, annoyed. “We just signed a contract and everything.”

“Really, are you whining?” I asked him. “I need you to wash your dick before I even do this.”

“Shit, say less, I will get in the shower right now.” He responded.

“NOPE!” I said. “Tomorrow this will all happen, I promise.”

Rogene was so upset, but I convinced him to be ready for me the next day, right after I got out of school. He was not excited, but it gave me time to prepare myself. I got to talk to my two homegirls, Victoria and Tiffany, who I already knew were doing it and knew how to do it. So I had asked for advice. They both gave me some pointers and how to not think about the “male anatomy” so much.

Well the day was FINALLY here! I was released from school at 2PM and was home by 2:20PM. I called Rogene, advised him I was getting in the shower and changing my clothes and that I would be at his house within the next hour. Well, of course, I took my time getting ready. Apparently, I was taking too much time to get ready, because Rogene’s impatient ass was calling me from his cell phone, to let me know he was near my house and wanted to walk with me to his house. I quickly finished getting ready, and met him the next block over. We hugged and kissed. He grabbed my hand and we headed towards his house.

Once we got to his house, we went straight to his bedroom. When he opened the door, I noticed that his bedroom was very clean and organized. He had a few candles lit and it smelled fresh. We sat on the bed and we removed our shoes, then we laid back.

“Thank you.” I said, placing a kiss on his lips.

“For what?” Rogene asked.

“For your patience, and cleaning your disgusting room for once.” I joked.

He laughed, as well. “I had to make my baby feel special, since you’re gonna do something special for me.” He kissed and sucked on my lips.

I kissed him back, as I grabbed at his shirt and pulled him closer to me in the bed. And he began running his hands under my shirt, grabbing at my breasts. We eventually released our lips from each other. Rogene took my shirt off and then took off his. I unzipped his jeans and he helped me pull them off his legs.

“I’m still a little nervous.” I confessed to him.

“I can help you, baby.” He said, sitting up in the bed. “I’ll let you know if you’re doing it wrong.”

“No, I’m gonna try to do this on my own.” I whispered.

I kissed his lips. And I placed my hand on his dick through his boxers, and he was already hard. I grabbed at his dick and massaged him in my hand slowly and gently. As we kissed, he grabbed at my face. I pinned him down on the bed, and I climbed on top of him, still massaging him. I began moving my lips from his lips, down to his cheek then to his neck. I began sucking on his neck. But Rogene was getting impatient.

“Baby, come on, I want to feel those lips!” He exclaimed.

“I bet you do.” I said, and then began moving my lips down to his chest.

I licked, sucked, and bit on his nipples. He screamed out a cry of joy. I kissed my way down towards his stomach. And as I approached his genital area, I pulled down his boxer shorts. I sat up and looked at him. Rogene had a smile on his face, while looking back at me. I had to take a big leap. This was going to change my life forever, and there was no turning back.

I kissed the head of his dick. I had lip gloss on my lips, so things got sticky very quickly. So I opened my mouth and licked it too. Rogene moaned. So I kissed it again, then licked again. Then I opened my mouth wider and I put a little bit more of him inside my mouth. He moaned again, and I looked up at him. He was biting down on his bottom lip to stop himself from moaning. His eyes were closed at first, but then he opened them back up and was looking directly at me. I felt his dick jump in my mouth and a little bit of my spit ran down from my mouth, spilling down on the rest of his dick.

I released him from my mouth, and I licked up the spit from the bottom, all the way back to the top, and I swallowed him into my mouth again.

“Ouuu baby, you swear you never did this before?” He asked and moaned.

I still had him inside my mouth and said, “No.”, and shook my head.

Things got slippery again… More spit slipped down from my mouth and down his dick again. So I put more of him into my mouth to capture the spit from sliding down further. Rogene heavily moaned and I finally felt the tip of his dick hit my throat. I figured that was the reason for the moan. So I began to bob my head up and down a few times to make him moan like that again. Every time the tip of his dick hit my throat he moaned and jumped up. I looked at him frequently and he was squirmish, but in a good way. He had to sit up in the bed, as if he was adjusting himself.

I released him from my mouth, and asked, “Why you keep moving around?”

“WHOOO!!!” He exclaimed. “Those lips and that mouth.”

“Am I doing okay?” I asked.

“Fuck yes.” He answered. “God damn, I knew those lips were luscious for a reason.”

“Then why do you keep running away?” I asked, giggling.

“Shit, the same reason you’re always backing away from me when I’m eating up that pretty kitty kat.” He said. “It feels too fucking good, baby.”

I laughed and giggled. I was so nervous before, and did not think I was going to be any good at it. Here I was a newbie and he was making me feel like I was an expert at it. But I also had to remind him…

“It’s that good, babe?” I asked him.

“Yes.” He answered. “You swear you never did it before?”

“I swear to God, I never did it before.” I confirmed.

“Then you’re gonna have to do that every day now, baby!” He joked.

“Nahhh baby.” I laughed. “You can’t ever ask me to do it again. A deal is a deal!”

“Damn, that fucking contract.” He whined.

I winked at him, and I felt so fucking confident. I went right back at it. Rogene moaned and ran his fingers through my hair. He complimented how good I was at sucking his dick.

“Yesss baby. Suck that thang just like a lollipop!” He moaned. “Yesss, just like that.”

I kept going. His leg shook a few times. He grabbed my head when he was about to cum, but nope I stopped right before he came. I sat up and watched him cum all over himself. His stomach. It was all over him!

Of course, after that day, Rogene never asked for head again, at least not directly. He would have to earn it. And yes, years later, Rogene and I would have broken up. I, of course, got even better at my craft. And have become a sexual addiction in other men’s life, all because of my lollipop suckers on my face.

XOXO,
D i r t y   D y a n a