Feels Like the First Time - Cover

Feels Like the First Time

by Melanieatplay

Copyright© 2020 by Melanieatplay

True Sex Story: Simply put... My first time.

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   Teenagers   True Story   Cream Pie   First   Oral Sex   .

“You’re such a priss, Erica,” Jenna said snidely.

“Oh, my God, no, I’m not,” she squealed while giving everyone at our lunchroom table an appalled look. “I’m not a priss just because I don’t like the taste of it,” she said defensively.

“You’ve been with how many guys and you still won’t swallow it? That makes you a priss in my book,” Jenna shot back.

“I take care of my boyfriend, and, trust me, he has no complaints,” Erica retorted.

“You’re lucky he goes to San Dimas and not here, otherwise he’d be mine by now,” Jenna said, a sly smile crossing her lips while she gauged Erica’s reaction to her thinly-veiled threat.

I listened intently and wisely kept my mouth shut while pretending to pick at my disgusting cafeteria chef salad. When the two biggest sows in the pigpen decide to fight, the smartest move is to stay out of their way to avoid getting caught in the ensuing collateral damage. Just the threat of stealing your best friend’s man was shocking to me. However, everyone seated at the table knew Jenna was just vile enough to do it.

“What do you think, Danielle?” Erica said in an attempt to deflect some of the flak away from herself and possibly redirect it elsewhere.

I watched as Danielle looked at Jenna apprehensively. I could tell she didn’t appreciate being dragged into the middle of this seminal squabble.

“Well ... it’s not something I particularly enjoy. However, I don’t despise the taste enough not to do it,” Danielle said diplomatically.

“See, I told you...”

BZZZZ. The bell rang, which cut Jenna off and announced that lunchtime was over and we needed to begin making our way to fifth period.

“Tomorrow we’ll have to get Mel’s opinion on this subject,” Jenna smirkingly said.

I looked down, blushing, while Erica gave me a condescending sneer.

Danielle shot both of them a ‘back off’ look that immediately shut them up and ended their little joke at my expense.

“Don’t listen to them, Melanie. C’mon, let’s get to class,” Danielle said as she took the lunch tray out of my hand and dumped its remaining contents into the garbage can.

I watched as Jenna and Erica whispered and giggled under their breath while walking away from us and towards their next class. I was so fed up with their snide little comments. Two weeks earlier I had made the mistake of admitting to them that I was still a virgin, and since that fateful day they talked about nothing but boys and sex during our entire lunch break.

Danielle and I silently walked out of the lunchroom and down the hall towards our fifth period math class. I was still fuming and I knew I was going to be in a foul mood for the rest of the day.

“Don’t let what they said bother you, okay?” Danielle said as we walked towards our class.

“That’s easy for you to say, you’ve done all the things they’re talking about.”

“You’re not as old as we are, Mel, and you have plenty of time to do that when you’re ready.”

“They talk to me as if I was a child though and you don’t know what that feels like.”

“They’re bitches and you can’t let what they say affect you like this.”

“Yeah, right, you’re the most popular girl in school who’s dating the star quarterback; you have it made.”

She shook her head and gave me an exasperated look. “You’re lucky I like you and you help me with math, otherwise I’d be kicking your stubborn little ass,” she said while giving me a big smile and a little hug. Danielle was my best friend and she looked out for me like the big sister I never had.

This was the counselor’s fault anyway, I reasoned. At the beginning of the year I was told that I had really high test scores in math and our counselor wanted to place me in a math class with the older students. Unfortunately, that also meant that I had to eat lunch with them, which subjected me to this daily torment of cafeteria sex talk. Unlike math, sex was a subject that I knew very little about.

Even though they were raging bitches, Jenna and Erica were two of the most popular girls in school. Jenna was captain of the cheerleaders and Erica was her nasty little minion. Even though I despised them for the way they treated me, I also envied them because they were just so damned refined and sophisticated. They only wore the best clothes, went to the best parties, and dated the most popular guys. They were ten rungs ahead of me on the social ladder and it felt like I’d need a decade to catch up with them.

The only bright spot in my miserable existence was Danielle. Because she was the star point guard on our school’s basketball team, she was incredibly popular. Yet she didn’t use her popularity to hurt people like Jenna and Erica did, and I admired her so much for that.

On the first day of math class we sat together, and she secretly confided in me that she struggled in math and asked for my help. I guess she thought she owed me because she constantly looked out for me whenever we were together, like today when Jenna and Erica were picking on me.

I knew that if I was going to be accepted into their little social group, and be popular like they were, I had to lose my virginity. Unfortunately, that presented me with another problem. Even though they were popular; Jenna, Erica, and even Danielle had reputations of being very, ummm ... slutty. The guys at school had really big mouths, and the minute they got a girl into bed they bragged about it to all their friends, and within hours everyone knew.

There had to be a way to have sex and get the experience I wanted without everyone knowing about it. This was just like one of those complicated math problems I had to solve every day. I just had to think about it for a while and then come up with the solution.


“How was your day today, honey?” my Mom said as I walked through the door.

These bitches at school were ridiculing me, Mom. How was yours?

“It was okay, I guess.”

“How did you do on that big math test you told me about?”

I rolled my eyes. “I did fine Mom.”

She gave me a stern look. “You know I hate it when you do that.”

“Sorry.”

Just then we heard a loud crash that came from the back yard. “Darn those boys, I’ve already told them twice to be careful out there.”

They’re assholes, Mom, what do you expect? “You know how they are when their friends come over and they’re playing basketball.”

“Would you go out there and tell them to come inside?.”

It took everything in my power to keep from rolling my eyes again.

“Okay.” I got up and walked through the living room towards the door to our backyard. Three years ago my Dad made the mistake of pouring a concrete slab next to the pool and putting up a basketball net. Since then our back yard has been the official ‘hardwood’ of Glendale. opened up the door and stepped outside.

“What do you want, runt?” my oldest brother, Todd, said, which elicited chuckles from my two other brothers and their friend.

“I want you to stop acting like an asshole for a couple of minutes,” I said saucily.

That elicited even bigger laughs and a couple of high-fives from the other onlookers. My other older brothers, Scott and Jim, really looked up to Todd, so when I got in a good zinger like that it felt especially good.

“Mom’s pissed because you’re banging into the garage again and she wants all three of you to go inside so she can chastise you.”

“Well, I know she didn’t say pissed; she probably said something like darn it or dang it,” Jim said, smiling.

“Trust me, she was thinking assholes, she just didn’t say it.”

That got all three of my brothers smiling. My Mom was very religious and never used profanity, no matter how mad she got. The rest of us swore enough to make up for her, though.

“Don’t touch the ball while we’re gone, runt, or I’m throwing you into the pool when we get back.”

“Whatever, Todd, just get inside and take your admonishment, and since your retarded ass probably doesn’t know what that word means, I’ll explain it to you when you get back out here.”

“You’re getting thrown into the pool as soon as I’m done talking to Mom,” he said before shutting the door.

I rolled my eyes. Yeah, right.

“How are you doing today, Melanie?” Todd’s friend Anthony said softly.

I shot him a dirty look. “Isn’t there another house around here you could be terrorizing?”

“Hey, take it easy. I was only asking you how your day was.”

I looked into his soft, gentle eyes and realized I was acting like a bitch for no reason. He wasn’t one of my smart-ass brothers and he always treated me really well.

“I’m sorry, Anthony; I had a good day, how was yours?”

We made small talk for a few minutes, which gave me an opportunity to sneak some glances. It was a hot day and he had taken off his shirt to combat the searing Southern California heat. He stood in front of me wearing only gym shorts and high-top sneakers. It was the first time I really noticed his long, lanky, tanned body, which was covered in sweat from the strenuous physical activity. He was actually kinda ... sexy. He had short, wavy brown hair and he was sorta handsome in his own way. He was way older than me, but maybe ... just maybe...

I heard the guys open the door and they joined us on the court.

“Who let you out of the kitchen, runt? Why don’t you get your ass back inside and help Mom finish cooking my dinner.”

“Do you want one turd in your soup tonight, Todd, or two?”

The boys busted up laughing again as I opened the door. I turned and snuck one more look at Anthony before going back inside to help Mom.


The next day was Saturday, and like usual I was procrastinating. I had some homework that I should be doing, but instead I was watching TV and enjoying the peace and quiet of having the house to myself. My brothers were outside in the pool, my Mom had gone to the market, and my Dad was at work. That was probably the best thing about having a pool in our backyard. If my brothers were outside splashing around and dunking each other, they weren’t inside picking on me.

I was flipping through the channels trying to find something to watch when I was interrupted by a knock at the front door.

Probably another of my brothers’ mongoloid friends who had come over to foul our pool.

I opened the front door.

“Hi, Melanie,” Anthony said in a gentle voice.

“Hi Anthony, it’s great to see you again,” I said sweetly, “come in.”

He gave me a quizzical look. “It’s ... ummm ... nice to see you too, Melanie.”

“All my friends call me Mel.”

“Okay,” he said as we exchanged nervous smiles in the doorway.

I studied his face; he looked so anxious and apprehensive.

This might be tougher than I thought.

“Your brothers ... ummm ... invited me over to swim; are they around?”

“Yeah, they’re out back in the pool. But you look really hot; would you like some iced tea?”

He gave me another confused look and then quickly scanned the perimeter, no doubt looking for my brothers. Thankfully, it was impossible to see into the backyard from the foyer.

“Ummm ... yeah, I guess so.”

He followed me into the kitchen. “Have a seat at the table while I get the tea.”

I could feel his eyes on me as I filled two glasses with ice from the door of the refrigerator and then poured tea from the large pitcher. I handed him a glass and then sat down beside him.

“So, how are your classes going?”

“Okay, stop. You’re freaking me out.”

“How am I freaking you out?

“You know... this ... this whole thing.”

“I can’t get one of my brother’s friends a glass of iced tea and ask him how he’s doing?”

“You’ve never said more than two nice words to me since I’ve known you ... and...”

“And what?”

“And just being in a room alone with you, that’s enough to get my ass kicked if your brothers knew, so you had better start telling me what this is about.”

I looked down sheepishly. “I want to learn about sex.”

“And you want me to teach you? Are you fuckin’ kidding me?”

“What’s so wrong with you teaching me?”

“This whole thing is wrong on so many levels.”

I gave him a few moments to calm down; agitating him like this wasn’t going to get me what I wanted.

“First off, I have a girlfriend, did you know that?” he asked.

“No, I didn’t.”

“Well, I can assure you she wouldn’t think much of this conversation.”

That brought a little smile to our faces, so I knew I still had a chance.

“The next problem is the three guys who are swimming in the pool back there, who just happen to be my best friends.”

“We could be careful, and they’d never find out.”

He gave me an exasperated look. “Even if they weren’t my best friends, Melanie, you don’t mess around with the little sister of the three nastiest rats in the shithouse.” That brought a big smile to my face, because that’s exactly what they were.

We silently sipped our tea for a few moments. I was losing the battle, and I desperately needed to turn this around.

“Okay, Anthony ... you don’t think I’ve noticed the way you look at me when you’re here?”

He looked down self-consciously. “You’re beautiful, and I’m a guy; of course I’ve noticed you.”

I could feel myself blushing. It was the first time that anyone called me beautiful.

We looked into each other’s eyes.

“Fortune favors the bold, Anthony, and sometimes you just have to take what you want.”

He gave me a disconcerted look. “You’re making it really difficult for me to do the right thing here, I hope you know that.”

I gave him a self-assured look that I very clearly wasn’t feeling inside. “I’ll put my cards on the table, Anthony. It’s either going to be you or my second choice, but one way or another this is gonna happen.” I hadn’t thought this through enough for there to even be a second choice, but he didn’t know that and I hoped he wouldn’t call my bluff.

He paused for a few moments as he thought. Then, “I’m taking my life into my own hands here, but okay.”

I gave him a big flirty smile. Victory! It also taught me a valuable lesson that I’ve used many times thereafter. If you appeal to a man’s base instincts, more often than not you’ll get what you want.

Day One

It was Monday and I agreed to meet Anthony after school at his house. It really was the perfect location, because he was an only child and his parents both worked.

I felt bad lying to my mother, but under the circumstances I really didn’t have much of a choice. I told her there was a new tutoring program after school in the library and I could get the service hours I needed for the National Honor Society by assisting other students. She loved that I was ‘helping’ my peers and agreed to let me do it as long as I was home for dinner. It was perfect, because it gave me a solid two-and-a-half hours when no one would question my whereabouts.

The only problem with my perfectly-devised plan was my very nauseous stomach that was in no way cooperating. I was so nervous and apprehensive; I knew if I didn’t settle myself down I was going to vomit. Needless to say, it was very difficult to get through the day. I found it nearly impossible to concentrate in my classes, and even Jenna and Erica’s sex talk and snide comments didn’t seem to bother me.

“Mel, are you sure you don’t want to go to the nurse?” Danielle said with a concerned look in her eyes during our math class.

“No, I’ll be fine. I think I just ate something bad for breakfast.”

“Your face actually has a green tint to it.”

“Just get your math problems done, miss nosey,” I said while gently rubbing her thigh.

She gave me a soft smile, shook her head, and got back to work. She was right, though; I probably should have been in the nurse’s office. I was just hoping I had the guts to go through with this.


I very hesitantly knocked on Anthony’s back door. Even though he lived a block over, we thought it would be wiser for me to use the back door instead of the front, just in case somebody we knew walked by.

I watched as the door opened.

“Hi, Melanie, come on in.”

I stepped inside and we walked through a small hallway, past the washer and dryer and into the kitchen.

“Do you want something to eat or drink?”

Eat? Do you want me to vomit all over you? “No, thank you, I’m fine.”

A few moments of very awkward silence passed. Thern, “Would you like to ... ummm ... watch TV?”

Oh, my God, Anthony, are you trying to kill me? “No, let’s just ... you know ... ummm...”

“Okay, Melanie, I’ve got to be honest with you, it normally doesn’t happen like this. I’ve never had a girl just show up at my back door and then want to get laid, you know?”

I looked down, feeling deeply embarrassed. Maybe this was a bad idea.

“I’m sorry, Anthony, I ... you know ... this is my first time, and I ... I ... have no idea how this is supposed to work ... and I’m incredibly nervous, but I didn’t mean to weird you out or make you feel uncomfortable ... it’s just that...”

I was seconds from breaking into tears.

He took my hand and looked into my eyes. “Melanie, stop. It’s okay, and I’m sorry. C’mon, follow me.”

He continued to hold my hand as he led me out of the kitchen and into the living room. I would love to describe their furnishings, decorations, and wall colors, but honestly I didn’t even look. I felt nauseous and dizzy, and I was hoping I wouldn’t pass out as we walked up the stairs and into his bedroom.

We faced each other and looked into the other’s eyes for several seconds.

“I’m going to get undressed in the bathroom,” he said. “Why don’t you get undressed and then get under the covers, okay?”

“Okay.”

I watched as he walked out of the bedroom, closing the door behind him. Then I very quickly removed my clothes, slid under the covers, and pulled the blankets up to my neck, making sure none of my naked body was exposed.

And I waited ... and waited ... and waited ... and waited ... and waited...

It was probably only about a minute, but it felt like hours.

Finally, the door opened, and Anthony walked into the room naked, carrying a towel. I questioningly looked at the towel in his hand, and then back up at him.

“It’s for if you ... you know...”

“I understand,” I said softly.

I also looked at his penis. It seemed kind of long, and sorta thick, but I didn’t really have a base of reference to judge it by. I then remembered Jenna and Erica very shamelessly discussing the size of their boyfriends’ cocks at lunch and I recalled them saying they had even measured them.

I tried to make an educated guess. Did Anthony look like he was five inches, or six inches, or...

Anthony’s voice broke me out of my deep reflection. “Can you slide over, Melanie?”

I very quickly slid to the far edge, and he pulled the covers back while still ensuring that my naked body was still covered. He then laid the towel down in the middle of the bed. He slid in beside me and I hesitantly slid towards him, ensuring that my bottom was on the towel.

He leaned in and very cautiously kissed me. I loved kissing guys and normally I was really good at it, but this time I was so nervous and apprehensive we probably looked like two fish hitting glass.

I tensed up when I felt him touch my breasts.

“You need to relax a little, Melanie; this is supposed to be fun.”

“I’m having a really good time, Anthony.”

That was a lie, and we both knew it. But his hand traveled lower, and I shivered when he touched my stomach. Thankfully, I didn’t feel like I was going to throw up anymore, but I still felt sick from being so nervous.

His hand traveled further south and I could feel my pubic hair brush through his fingers. I had to fight the intense desire to close my legs and deny him access to the most private part of my body.

He continued to kiss me as his fingertips lingered over the lips of my vagina. His mouth retracted from mine and he whispered into my ear.

“God, you have such a sexy body, Melanie.”

“Thank you,” I said shyly.

I couldn’t help but think that his fingers and sensual words should be turning me on and getting me into this, but they weren’t and he knew it.

“You should be getting more ... never mind ... let’s try something different.”

“Okay,” I said hesitantly.

He rose and stood beside the bed; pulled open a drawer on his nightstand, and produced a big jar of Vaseline. Then he reached back into the drawer and pulled out a condom.

I look down at his very erect penis, and I was a bit taken aback. It looked a lot bigger compared to when it was flaccid when he walked into the room. There was also a clear liquid oozing out of the slit in the head. Even though what we were doing wasn’t working for me, it was obviously doing a lot for him.

I observed him tear open the little foil package and pull out the condom. He then rolled it down the length of his cock. I continued to watch as he opened the jar of Vaseline, scooped out a large dollop, and rubbed it over his condom-encased penis.

He got back into the bed and moved between my legs, which I hesitantly opened wide for him while ensuring that my bottom was still centered on the towel. He scooped out another large glob of Vaseline and rubbed it over my aperture.

“I’m going to go really slow, but it still might hurt. If there’s too much pain, just tell me and I’ll stop, okay?”

“Okay.”

He reached down and rubbed the head up and down my vulva before positioning himself at my opening. I felt him split my lips and then push forward slightly until his progress was halted. He took a deep breath and I felt a sharp surge of pain as he pushed forward again, and I could tell he had worked himself inside me. There was some discomfort as he continued to slowly push in, but nothing like the sharp pain I had felt a few seconds before. Moments later, I felt his balls resting against my bottom and I knew he was completely inside me. He lay on top of me, remaining motionless, letting me get used to this very new sensation.

“Are you okay, Melanie?”

“I’m all right.”

“I’m going to go really slow, and remember, if you want me to stop, just let me know.”

“Okay.”

I felt him begin to move backwards and then slowly push forward again. There was still a little bit of discomfort, but not really much pain, so I could handle it. Very gradually, I could feel him picking up the pace and moving in and out of me a little more rapidly. I looked up and watched his face intently. His eyes were tightly closed and it looked like he was in another world. He began to let out little moans and grunts, and I could tell he was really getting into it.

“God, you’re so fuckin’ tight,” he said, almost to no one in particular because he appeared to be off somewhere else.

He began to thrust into me harder, and I wasn’t entirely certain that he knew he was doing it because it seemed to be an almost unconscious act. As the hard thrusting continued, the discomfort increased, but I didn’t feel it was bad enough to make him stop and ruin this experience for him. He continued to slam into me, and his body began to stiffen and his breathing changed. His solid trusts turned into short little pumps and I thought he might be coming, but I couldn’t be sure. Then, without warning, he collapsed on top of me.

I could feel him soften inside me, and a few seconds later his breathing returned to normal; he slipped out of me and rolled over to my side.

“God, that was good.”

“Yeah ... it was, ummm ... really nice.”

“Did you come?”

“I ... I’m ... not sure. I don’t think so.”

“It’ll get better, I promise.”

“It was really nice, Anthony, and I enjoyed it.”

“Good. I’m going to go into the bathroom and get dressed, okay?”

“Okay, I had better get going too. I don’t want to be late for dinner or have your parents catch me here when they get off work.”

A slight smile split his lips. “Yeah, we don’t need that.” He turned and walked out the door into the bathroom.

While I was getting my clothes on, I looked down at the bed and noticed a spot of blood on the towel I had been lying on. I had just finished putting on my blouse when Anthony entered the room.

“Do you want me to, umm ... get rid of that?” I asked sheepishly while looking at the soiled towel.

“No, Melanie, I’ll take care of it.”

“Okay.”

He walked over to me and gave me a hug and a little kiss. “I know it wasn’t the greatest for you, and I promise it will be better next time.”

“It was nice, Anthony, I liked it.”

“Well ... jst let me know when you want to come over again.”

“It might be towards the end of the week, but I’ll let you know.”

I didn’t want to tell him, but I was sore already. I knew I’d need a couple days of respite before we tried this again.

I snuck out the back door, and made my way home.

Day Two

It was Thursday and I was finally starting to get back to normal. When I had awakened Tuesday morning, I was so sore I didn’t think I would be able to move. I told my Mom that I’d been up all night vomiting, and thankfully she took mercy on me and let me stay home from school. I spent most of the day in bed, but by the evening I was starting to feel better. The next day, Wednesday, I was still a little bit sore but I was able to go to school and function normally again.

I texted Anthony and told him I’d be over today after school. There had to be more to this sex business than I had experienced on Monday, and I was anxious to get back in the saddle and give it another go.

After school, I snuck around the back of Anthony’s house and knocked on the door.

“C’mon in, Mel, let’s sit down and talk, okay?”

We walked into the kitchen and I sat down at the table. Anthony got me a big glass of iced water and then sat next to me.

“I know what we did wasn’t that great for you,” he said hesitantly.

I looked down shyly. “It was okay.”

“Look, I was really nervous because of your brothers. I’m still terrified of them finding out about this, you know...” He paused for several moments. “I guess my point is, if I could do it again, there would be things I’d do differently.”

I took a deep breath and collected my thoughts before I spoke. “Anthony, listen to me. First, my brothers aren’t going to find out what we’re doing, so please stop worrying about that. We’re sneaky and being careful. Also, they aren’t that smart, okay?”

We smiled at each other, and for the first time I really felt comfortable around him.

“Second, that’s why I ... I came back. So we can hopefully make this better.”

“Your first time should have been good, and I made it shitty for you, and I’m sorry.”

“Let’s just put that behind us and figure out what we can do, going forward, to make it better.”

We sipped our water, and I watched as he thought for several moments.

“My girlfriend says it’s better without a condom, but she won’t let me do it with her without using one, and there’s no way in hell we’re risking that anyway.”

If this is going to work, I have to be honest with him.

“I’m on the pill, Anthony.”

His jaw dropped. “Why would a virgin be on the pill?” he asked incredulously.

I took a deep breath and tried to figure out how to proceed.

“I don’t want to gross you out, but my periods were really, really bad. My Mom took me to see my gynecologist and she put me on the pill to help regulate it and make it less severe.”

“So I ... I ... don’t have to use a condom?”

“Well, from what I hear, that’s the other thing the pill is supposed to do, keep you from getting pregnant.”

“Smart-ass.”

We smiled at each other.

“There are other things I know how to do that will make it better for you, if you’re willing to let me do them.”

“Anthony, I trust you, and I’m willing, okay?”

He took my hand and we proceeded to the living room. I took a few seconds to look around. Their house was a lot smaller than ours, but it felt really cozy. The living room was very tastefully decorated, with nice paintings and various pictures of Anthony’s parents and Anthony at different stages of his life.

“You were a cute baby,” I said softly.

“Of course I was, and I’m still cute,” he said, giving my hand a little squeeze.

This experience was nothing like Monday. I felt so calm and comfortable. Anthony was really nice and really sweet. I realized that, even though we hadn’t had many interactions, when we did he was always kind to me. I just had never given him a chance, probably because of my brothers.

We went up the stairs and into his bedroom. Again I took a second to look around. Like my brothers, he had a lot of posters on his walls of different NFL and NBA stars, as well as some posters of various rock bands. However, unlike my brothers, he had several posters of pretty girls in very small bikinis. That was something that my very religious mother didn’t allow.

 
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