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My Very Special First Time

"I was going to watch a movie with my crush, but things got out of hand"

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Competition Entry: LGBT Sex Stories
There’s this girl called Jenny. She works at the local supermarket just like I do. She’s the most beautiful girl I know. She’s got a petite figure with a great pair of boobs, not too big, not too small. I’m too shy to talk to her though. I’m pretty sure she’s got a boyfriend. I mean, she must have one, right? All the beautiful girls do.

“Rick?” I heard a voice ask.

I snapped out of my thoughts and looked up to see Jenny.

“Are you free tonight?” she asked, looking nervous.

“I, uhm, what?” is all I managed to get out.

“Are you doing anything tonight? I’m all alone and I wanted to know if you would like to watch a movie with me?”

“No,” I say. “I mean yes, of course!”

I then realised how stupid I sounded.

“I mean that I’m not doing anything tonight and that I’d love to watch a movie with you,” I added.

“Great!” Jenny said.

She handed me a piece of paper as she smiled like a little schoolgirl and turned around. I looked on the paper and saw that she had written down her address and a time. I was nervous for tonight, but I also couldn’t believe what was happening. Was I finally going to get together with my crush?

The workday seemed to go on and on. Jenny went home early, but I had to stay until closing time. When I finally left I got home as quick as I could to take a shower and shave. I’m a virgin, but I have been shaving for years, hoping for an unexpected ending of my virginity.

When I got to Jenny’s house I rang the doorbell which was quickly answered by Jenny. She was wearing a tank top and a pair of very short shorts. I could see her nipples through her top, indicating that she wasn’t wearing a bra.

“Hi Rick!” she said as she hugged me. “Come on in.”

I walked into the house and into the living room.

“So, what movie do you want to watch?” I asked.

“You didn’t seriously think I wanted to watch a movie, did you?” Jenny laughed.

Before I could react she jumped against me and kissed me passionately.

“You’re a sweet guy,” she says as she broke the kiss. “The type of guy I need.”

“Don’t you have a boyfriend?” I asked.

Jenny didn’t answer; she just took off her tank top and gestured for me to follow her as she went up the stairs. It took a while for me to react, so when I finally walked up the stairs, Jenny was already out of her shorts. I could just see her moving into a room. I followed and when I entered the room I was hit by her panties, which she had taken off and thrown into my face.

“Come on, Rick,” she teased in a soft voice. “Gotta give a girl what she wants.”

She crawled to me and I could see her tits moving slightly. My cock was rock hard. I pulled off my shirt and Jenny unzipped my pants. She took my cock out and immediately put it in her mouth.

“Oh that’s good,” I moaned as she sucked on my cock.

“This is your first time, isn’t it?” Jenny smiled.

“Yes,” I moaned.

“Well, you’re not my first…” Jenny said. “But you could be the first to do something.”

“What is it?” I asked.

“I’ve never had a guy make me cum,” she said as she lay down on the bed and spread her legs. “Lick me.”

I wasn’t going to refuse to lick my crush’s pussy. I moved down so my head was between her legs and started to lick her. She started to moan loud right from the start, so I thought I was doing a good job. After a couple of minutes we heard a male voice scream.

“What the fuck?”

We looked up to see Steve, a very muscular guy I knew from school.

“Oh my god, Steve!” Jenny screamed as she tried to cover her tits with her arm.

“You hide those from your boyfriend, but not from this pathetic little boy?” he asked.

“Boyfriend?” I asked.

“Shut up you little shithead!” he yelled.

“Steve, I’m sorry,” Jenny started. “I thought you’d be gone for another two weeks.”

“Oh, well, that makes it all okay, doesn’t it?” he yelled.

“I think I should go,” I said.

“No, you’re going to stay. I’ll punish you both.”

I looked at Jenny and she seemed as worried as I was.

“I’ll punish you for cheating on me, you slut,” he told Jenny as he took off his shirt. “And you for fucking my girlfriend.”

“Please just let him go. It’s my fault, not his,” Jenny begged.

“No, I won’t,” he said. “Now suck my cock.”

Jenny started to move towards him, visibly scared.

“Not you, him!”

Now I was scared. Jenny looked at me as if trying to say she was sorry.

“Me? But I’m not gay,” I stammered.

“I don’t care. You fuck my girl, I fuck you, easy as can be.”

He walked over to me and grabbed me by my hair. I gasped in shock and he quickly shoved his half deflated cock into my mouth. I knew I wasn’t able to fight him and somehow I didn’t even want to. I don’t know why, but it felt great to suck his cock. It felt even better to know that he was in charge over both me and Jenny.

He noticed that I started to enjoy sucking his cock and let go of my hair. I didn’t stop sucking him and even started to moan a bit. Suddenly I heard Jenny move, followed by the feeling of her mouth on my cock.

“That’s it,” Steve moaned. “Look at these two bitches sucking cock.”

After a couple of minutes of cock-sucking Steve wanted more.

“Get on all fours,” he ordered.

I did as he said while Jenny pleaded for him to let me go.

“Please, just take my ass and let him leave,” she begged. “He has never had sex, please let his first time be better than this.”

Steve just continued doing what he was doing. Suddenly I felt cold liquid being applied to my ass and I knew what was going to happen. Shortly after I could feel the tip of his cock pressed against my virgin-asshole. Jenny was still begging for Steve to stop, tears running down her cheeks.

“Shut up, slut!” he yelled.

I started to push his cock into my ass and I started to moan. I had never experienced anything so painful yet so pleasurable. As Steve continued to push his rod in Jenny stopped talking and just watched.

“Put that thing on.” Steve ordered Jenny.

I had no idea what he meant.

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Jenny then walked away from us, took something out of a drawer and the returned. Steve had buried his complete cock inside my bowels and started to pull back slowly. I moaned loudly.

“I’m so sorry,” Jenny said.

As soon as I looked up she shoved a big strap-on dildo in my mouth and started to fuck my mouth. My moans were muffled by the fake cock, which Steve liked.

“Now that little bitch is finally quiet.”

They spit roasted me for a couple of minutes. Steve had started to pound my ass quite hard and my cock bounced in all possible directions. The feeling was amazing. I now understood why people could enjoy anal.

“Get on the bed, slut,” Steve moaned.

Jenny pulled the strap-on out of my mouth and took it off completely. She lay down on the bed and spread her legs. Steve then pulled out of my sore ass.

“You’re going to fuck this slut while I fuck you,” he explained.

I did as he ordered. For the first time in my life I was going to have sex with a woman. I walked over to the bed and leaned over Jenny. She still looked at me in a way as if feeling guilty. I just lined up my cock with her pussy and slowly pushed my cock in. As soon as I had buried my cock inside her completely, I felt Steve’s cock press against my ass. I moaned loudly as he entered my asshole for the second time. As soon as he had buried his cock completely in my ass he started to pound as hard as he could.

I didn’t have to move, the force of Steve’s thrusts was so big that my cock moved in and out of Jenny’s pussy at an amazing pace. I was in heaven. Never did I think that being fucked while fucking someone could be this good. I could feel my orgasm building up.

“I’m going to cum,” I managed to moan.

Steve pulled his cock out of my ass and pulled me out of Jenny by my hair. He threw me on the ground and then grabbed Jenny by her hair and pushed her on the ground on her knees. He held her head so she couldn’t move it.

“Cum on her face!” Steve ordered.

“No, that’s gross,” Jenny cried.

I didn’t want to cum on Jenny’s face like she was some kind of whore, but I was blinded by lust. I stood up and pointed my cock at her face. I started to jerk myself off and quickly reached the point of no return. I shot an enormous load and covered all of Jenny’s face in cum.

When I finally came down from my orgasm I realised what I had just done to Jenny. I looked down at her and expected her to be looking at me angrily. Instead I found her licking my cum of her lips while smiling at me. As we exchanged smiles, Steve felt it was time to continue.

“Bend over, Rick.”

I did as he asked. I bent over at a desk and he quickly lined up his cock with my ass. I was starting to wonder why he hadn’t fucked Jenny and was so focused at me, but I have to say that I enjoyed every second of it.

He pushed his cock inside me again and I knew he wouldn’t last long, since he had fucked my tight asshole for quite some time now.

“I’m going to fill your ass with my cum!” Steve groaned.

He pushed into me further than before and moaned loudly as his cum filled my bowels. His orgasm didn’t last as long as mine did earlier, not even close, but as soon as he pulled his cock out of my ass, cum started to drip out of it.

“Lick my cum out of his asshole, you whore!” Steve yelled at Jenny.

Jenny did as Steve ordered and soon I could feel her breath against my cheeks and her tongue around my butthole. The thought of having Jenny lick my asshole got me hard again. As Steve was getting dressed, Jenny wrapped her fingers around my hard-on and softly jerked me off. Her other hand massaged my balls while her tongue still tried to catch as much cum as possible.

“Jenny, I’m leaving you,” Steve said, but Jenny didn’t react.

Steve just walked out of the room and we heard the front door close seconds later. Jenny stood up as I turned around.

“Are you alright?” she asked.

“Yes. Are you?”

“Sure. I’m so sorry your first time has been like this,” she said as tears filled her eyes.

“Sorry?” I asked. “Why? I just had the best night of my life!”

“Really?” Jenny asked, unable to believe that I enjoyed being fucked roughly.

“Yes, I really did. But are you sure you’re alright? Your boyfriend just left you,” I asked in a concerned voice.

“I don’t care. He was a bastard anyway.”

I smiled, knowing that this was my chance to get my crush.

“Maybe we could date for a bit, I’d love to take his place,” I joked.

“Date? We’re going to be together whether you want it or not!” Jenny smiled.

She then pulled me in for a kiss. As our bodies touched, she could feel my boner pressed against her belly.

“So, boyfriend,” Jenny started as she broke the kiss. “Shall we help each other out? I haven’t cum yet and you look like you need some help with that,” Jenny continued as she softly stroked my boner.

She then walked over to the desk and bent over, spreading her legs simultaneously. I walked up to her and pushed my cock into her pussy.

“By the way, I won’t cum on your face again. I’m sorry for doing that earlier,” I said as I started to move in and out of her.

“That’s right. This time you’ll cum in my mouth!” she moaned.

“What?” I asked.

“I loved your taste. I hate Steve’s taste, so now I need your cum to wash away his.”

“You really are a slut,” I said as I started to pound her roughly. “My slut.”

“Oohhhh, yes I am, I am yours.” Jenny moaned.

I moved my hand to her tits and squeezed them. Jenny moaned loudly and her body started to shake. Her orgasm took over and she was barely able to stand on her legs. Although I loved squeezing her tits, I needed to hold her by her hips to keep her from falling to the ground. As I did move my hands, Jenny’s upper body fell onto the desk as she was completely exhausted. I just kept pumping in and out of her and Jenny had several smaller orgasms.

“I can’t stand it much longer,” Jenny moaned.

I pulled out of her and helped her to get down on her knees. Jenny opened her mouth and I shoved my cock in. I started to fuck her face. Her slurping sound quickly became too much for me to handle and I started to fill her mouth with my hot seed.

“Hmmm, so good,” Jenny moaned as she licked up the last bit of cum.

“You fucked me so hard,” she added.

“Let’s get some rest,” I suggested.

We walked over to the bed and lay down together. Jenny rested her body against mine. We both fell asleep within minutes. It was a special night. It was my very special first time.

Published 
Written by ilp99
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