First Time 97

As always, thanks to my editors, LadyCibelle, and Techsan, for making my stories a much better read.

Boy, first time sure implies a lot. I was reading some first-time stories and it made me start thinking about my first-time everything. Some were really good memories and others not so memorable.

I have a hard time believing that everything goes right the first time for anyone. Even first kisses and trying to be a sexual lover would have to be a funny sight to anyone if they were able to see it happening the first time. Stupid, clumsy and a lot of other adjectives and verbs come to mind in my case.

I'll begin with my first kiss as a kid. Little Sharon and I were neighbors. We walked to school together and she was my pal. We were five years old and in kindergarten and were talking about her parents. She said she saw them kiss and they got all excited. I asked her, "About what?"

She said, "I don't know. Daddy kissed mommy and they told me to go play with you and they went into the bedroom as I was walking out the door."

"Geez! I wonder what it did to them? You want to kiss me and see if anything happens?"

She leaned over and we bumped lips.

"It didn't do nothing for me," I said.

"Me neither," replied Sharon. "I guess it's something that happens when you get old, is all I can say."

"Uh, oh, here comes Mrs. Braxton. Do you think she saw us?"

"Yep, we're in trouble again," I said.

Since Sharon and I were pals we always got in trouble together. This time the teacher put us both in the corner and made us sit there. Later when she saw our parents, she told them what we did. Our parents just told us that we were too young to be kissing, especially in school and we told them we wouldn't ever do it again. We told them we didn't like it anyway. They just laughed at us.

Sharon and her family moved away when we were about nine. I started hanging around with a couple of guy friends. We were all similar in age, pre-teen but I was kind of the leader if there was such a thing. We started messing around with girls. I don't mean sex, just kidding and pulling their hair, things like that.

Things started to happen after that. The girls started wearing bras and we would snap them, you know. Pull the back and let it go. One gal, Sara, was over visiting my sister. I have three sisters, two older and one younger. Anyway I snapped her bra and she yelled, "Ouch," and said that it hurt. My sister told my mom and I got a lecture out of it.

Mom said I was to treat all girls and women with respect and that she better not hear of me doing it again.

Sara was my friend too and apologized for getting me in trouble. I told her, "I'm sorry and didn't mean anything by it. I was just playing with you."

"Do you want to kiss and make up?" Sara asked me.

Now I'll admit I'm not the brightest crayon in the box but I was dumbfounded. I didn't really kiss girls but this was my first as an almost teenager. We kissed, kind of a peck, and Sara said, "Mark, surely you can do better than that," as she kissed me hard and long.

I felt her tongue touch my lips but kept my mouth closed. I opened my eyes and her eyes were closed, so I quickly closed mine again. When she pulled away she smiled and said, "That was better, but you could have opened your mouth a little. Also you're allowed to breathe when you kiss." She smiled as she walked away.

I yelled at her, "I'll do better next time."

I went home and talked to my oldest sister Kelly. She was like five years older than me and teased me all the time, but she would explain anything to me when I asked her. My next sister was only a year older and was part of the geek family. She didn't know any more than me and I knew better than to ask her anything. She would just tell Mom on me. My youngest sister was ten years younger than me, so she won't be mentioned much in my first time story.

Back to Kelly, she explained about French kissing and said that's why Sara was trying to put her tongue in my mouth.

I made a face and Kelly said, "It's not that bad as long as you brush your teeth and use mouth wash."

She told me to go brush my teeth and I could practice with her. I couldn't believe it. I hurried and brushed my teeth and used mouth wash. I came back and Kelly said, "Let me smell your breath."

"Now open your mouth just a little bit. That's too much, close it a little, that's better." She pressed her lips against mine and started applying pressure.

"Okay, Mark, keep your eyes closed. This time I'm going to just push the tip of my tongue in your mouth. Don't get nervous and don't bite down or I'll beat the shit out of you."

I got on her bed and lay down and she lay next to me. She lowered her head and started applying pressure. Did it ever feel good! She backed up and moistened her lips and pressed gently against my lips again. I felt her tongue enter my mouth. She felt so good that I applied pressure back. We did this over and over for what seemed like a half hour but when I check the clock it was less than ten minutes.

"Not bad, little brother. If you need to practice again, let me know. By the way, you must have liked it because your dick was starting to get hard."

I looked down and she was right. My dick was hard inside my jeans. Kelly laughed as she left the room. The first thing that entered my mind was Sharon's parents. They told Sharon to come to my house so they could have sex.

A week later I asked Kelly if we could practice again. We did the same thing. I told her I wanted to be on top kissing her. She laughed and lay on the bed. We began kissing, just the way she had told me and I felt my dick start to get hard. I reached down and grabbed my sister's tit. She knocked me clean of the bed.

"You stupid pervert! I'm your sister, not your girlfriend. What the hell is the matter with you?"

I was dumbfounded. I didn't know why I did it, it just happened. After about a minute, Kelly was back to normal and explained that brothers and sister don't do that sort of thing. Besides I was five years younger than her.

"Mark, I still want to help you out, but you can't just do things like that. You need to ask me first. I am your big sister and I will look after you."

She helped me off the floor and gave me a gentle closed mouth kiss. "There, Mark, see? All's forgiven."

I practiced on my pillow every night. I probably had the wettest pillow in the county. I do have to say it worked and in the years that followed I was known as a stud for my kissing. Throughout my teenage years I kissed so many girls that I lost count. Now having sex was a whole other story.

My first masturbation came the same year Kelly taught me how to kiss. Like most inquisitive kids, my favorite magazine was National Geographic Explorer. It had all the tribal women in it with their tits hanging out. Even though it wasn't the most pleasing to the eye, it was a turn on for a young kid. Every time I went to the library, I looked for that magazine, hoping the latest issue showed some jungle tribe. My second favorite was medical books. They showed all these female parts only they had diseases and stuff. Most pictures weren't that appealing but you had to settle for what you could get.

I masturbated pretty regularly in my room at night. It never took me long. I found out later that most guys I knew did the same thing. Some bragged about getting laid but I didn't believe most of them. I took out a lot of the same girls and I didn't get any.

Here I was a teenager, Mr. Stud, but never got laid until I was eighteen. I had plenty of dates but there were a number of reasons I think I didn't have sex with them. One was I didn't know how to go about it. Then, as I got older I was happy with taking one base at a time while I learned about the next base.

In the back of my mind there was always my mom saying, "Treat girls and women with respect."

For some reason whenever I was making out with a girl, that thought always entered my mind. Finally I did try a few times but without success. I'll tell you about those in a few minutes.

I mentioned that I became a good kisser. Girls didn't mind kissing me. I thought I'd start trying for second base - that's feeling some titties. I don't know why it's always been a turn-on to touch a tit, I really don't. Must be the idea that a woman let me touch her.

After getting knocked down by my sister for touching her breast, I decided to at least get my sister to explain to me how to go about it. I was hoping she would let me touch the real thing but she told me, "In your dreams!"

She went and got one of her big teddy bears and told me to practice on it. Me and her bear became pretty good friends. Kelly told me never to grab a woman's breast. Touch it gently, always starting with the outer round part and work my way to the nipple.

Kelly told me, "When a girl says 'No,' she usually means it. To grab at her breasts after that usually pisses the girl off. Just take your time and go with the kissing and then gently try touching her breasts, first on the outside of her clothes."

I didn't listen to Kelly the first time and squeezed my date's breast. She said, "Ouch" and then slapped me. After that I listened to my older sister. Most girls that let me kiss them let me gently massage their breasts on the outside of their clothes. If I told them I loved them then for some reason they let me under their blouse.

Let's be honest here, we were all teenagers. They didn't love me and I didn't love them. I did like some of them an awful lot and touching their breasts gave me a hard-on. I have to say that there is a correlation between squeezing a breast and getting a hard-on. When I was finally able to get inside a bra and felt the bare breast, I noticed that every time I squeezed a breast my dick got harder. It was like pumping up my dick, I swear! I would squeeze a tit and my dick got harder with every squeeze. It's funny but it still happens the same way to me today. God, I love feeling a nice breast.

The first time a gal let me suck her tit I was like in heaven. To suck a breast, any size, was a total turn-on for me. I especially liked it when the gal got into it and got hard nipples from my sucking. I could get myself off just by a girl reacting to my playing with her breasts.

I have two more first-time items I'd like to cover in this story that come to mind. First, touching and feeling a vagina - a pussy, for those who prefer the sound of the word. The other thing I'd like to cover is my first insertion into the valley of the deep. Hey, that sounded kind of cool.

The first time I was with a gal and she let me put my hand into her underwear, I shot off in my pants; I swear it's the truth. It was then that I realized I would have to learn to pace myself.

I learned another valuable lesson about a woman's vagina. Ladies, please don't get mad at me or send me hate mail for what I'm about to say. "Pussies stink," I wasn't expecting it and the smell got to me and not in a good way. Let me explain.

I wanted to get to third base and insert my digits – fingers - into a moist warm pussy. I looked for a date who might go along with me and play around a little. Rita and I were seniors together and dated a few times. She let me kiss her exposed nipples and was a fun loving girl. We liked each other but we both knew we were still kids and were experimenting.

I was on a date with Rita who was eighteen at the time. We went to the drive-in; for those who remember them, they were outdoor theaters where you sit in your car. In fact we still have a few around where I live. She was a great kisser and even asked me to suck on her tits. As I was doing so, I unbuttoned her jeans and pulled down her zipper. I started to slide my hand down into her panties and onto her mound. She was so wet, I thought she pissed herself.

"Mark, I can't have sex with you. Please understand, I'm not ready to make love yet."

"Rita, I'm not having sex with you. I just want to rub your pussy and make you feel good. I promise not to try and have intercourse with you, I promise. Just let me rub you."

"Okay, but remember you promised. Oh, that feels so good - you rubbing me. Keep doing that, Mark. It feels so good."

My cock was hard as a rock. I opened up my jeans and took it out.

"What are you doing, Mark? I said no sex."

"It was so hard in my pants it hurt. I just needed to take it out. Since I'm rubbing you, can you jack-me-off? It only seems fair."

She wrapped her fingers around my cock and it felt so different having someone else stroke me. While she was doing me, I slipped two fingers into her moist, make that wet cunt and started pumping them in and out.

"Oh, God, Mark it feels so good. Don't stop, I feel like I'm going to explode. Keep finger fucking me, Mark, please, oh, so good."

She was jacking my cock with one hand and pushing her pelvis up and down with my fingers buried deep within her. Our car windows were completely steamed up and I bet anyone seeing the car would probably figure we were fucking, but we weren't. We started coming damn near the same time.

"Push harder, Mark. I'm coming," she squealed."

At the same time my cock erupted and shot cum all over the dashboard. We both started laughing and she had my cum juices running down her hand. My hand was soaking wet with her juices and my fingers were still buried in her pussy. I pulled my hand out and reached for some napkins that I always had left over from the fast food chains.

I handed a few to Rita so she could clean up and took a few and wiped off my fingers. I couldn't get over the smell. I swear it smelled like fish. I didn't understand. My cum didn't smell anything like that. After wiping the juices off my hand the smell stayed. I didn't want to say anything but I was hoping Rita didn't have a disease or something.

I excused myself and told her I had to use the restroom. I went out and used a lot of soap trying to get the smell off of my hands. I got rid of most of it but it still lingered some. When I got back to the car, Rita was all back to normal and even had the cum cleaned off the dashboard. I just put my arm around her and we finished watching the movie. We did kiss a few times and then I took her home.

Kelly, my sister, was married then. I knew she stayed up late so I stopped by to see her.

"Well, little brother, to what do I owe the visit? Girl trouble?" she asked.

"Not exactly, but I do have a question."

She invited me in and I explained the evening to her and then told her about Rita smelling like dead fish.

"You didn't say anything to her, did you?" asked Kelly.

"No, I wanted to ask you if I should mention it to her. Does she have a disease or something? She's such a nice person but I was glad I didn't have sex with her. She told me maybe next time, but I don't think I want to with her. You know, the smell and all."

My sister couldn't keep from laughing. "I'm sorry, little brother, but you better get used to that smell if you expect to get any. All girls and women have a similar smell. Some might not be quite as strong as others but every woman will have the smell of sex."

"Oh, Christ, I've heard jokes about fish markets and things like that. Now they make sense to me. I used to just laugh and act like I knew what they were talking about; didn't want to look stupid, you know. I'm glad I didn't say anything to her. Could you imagine what that would do to my 'He's a stud' standing, if that got around? Thanks again, sis, you helped me out again."

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Well, I figured it was time to hit a home run. Who should I choose to be the lucky girl? Shit, if any girl asked me, she could have me. I was eighteen and still technically a virgin. I was at a point that I thought about going to a prostitute but I wanted my first time to be with a woman I didn't have to pay. I thought about calling Rita but she started dating one of my friends and I didn't think it would be a good idea.

I stopped by my sister's place and she was on the phone. I heard my sister talking to one of her girlfriends telling her that Frances, another girlfriend, will fuck anyone when she gets drunk.

I knew Frances; she was the sister of one of the guys I knew. She was twenty-two and pretty decent looking. Frank, her brother, told me he knew his sister was wild. He saw her having sex with different guys after she came home drunk. He said he would hide and jack-off watching his sister have sex. Needless to say, I invited myself over to spend the night when his parents went on a trip.

When I got to Frank's house he told me Frances was staying home that night because she had a cold. I figured I had lost my chance but stayed at Frank's for awhile anyway. They had rented a couple of movies and were just going to rest. They invited me to hang around as long as I wanted and could still spend the night. Frances coughed a few times and I told her she needed to take something for it. I told her alcohol would be good for her cold and if she could get someone to deliver it, I'd pay for it. I couldn't believe she agreed to it. She called one of her friends and asked him to pick her up two bottles of rum and a twelve pack of coke.

When the guy came to the door, Frank invited him in for a minute. He told him that he couldn't stay since Frances was feeling so poorly. The guy looked pissed. I figure he expected to score that night and it wasn't going to happen for him. I paid him for the rum and coke and sent him on his way.

Frank, Frances and I decided to start watching one of the movies. It was a horror flick. Frances had on a nightgown and was sitting on one end of the couch. I was on the other end and Frank sat over in the chair. I made Frances and Frank a drink, but I just had coke over ice.

"Don't you want a drink?" asked Fran.

"Not right now, maybe later," I told her. I didn't want to drink much because I wasn't used to it and either get sick or fall asleep. I didn't want to take any chances, just in case. She looked awfully good for a sick woman, or maybe I was thinking with another part of my anatomy.

Frank was twenty and drank whenever he got the chance. He was downing the drinks pretty rapidly. Fran on the other hand was taking her time and sipping them.

"Thanks for the rum, Mark. I do believe it's helping. I haven't coughed since I've been drinking tonight. It's warming up my tummy a little too."

"Glad I could be of assistance to such a pretty lady. Maybe I should have a drink, I feel a bit chilled."

"Slide over here and I'll share my blanket with you," Fran smile.

Oh, shit, this is good, I thought. I slid over and sat next to her and covered under her blanket. My thighs were touching her thighs. I could feel the warmth radiate off of her. I put my hand on her thigh.

She whispered, "Naughty, naughty, my brother is sitting right there."

She didn't tell me to remove my hand or anything so I left it right there. I looked over at Frank and he was getting close to passing out. I slowly rubbed her thigh, "You are really soft and warm," I whispered.

"...and you're being bad. Taking advantage of a sick woman," she smiled. "Aren't you a little young for me?"

"I'm eighteen and you're twenty two. Eighteen goes into twenty-two pretty easy, I hope. I don't have a problem with it if you don't."

"What about Frank? I don't want to do anything in front of him. Look, I know he peeks at me but I can't do anything openly in front of him."

I walked over and told Frank he was drunk and needed to go to bed. I helped walk him to his room where he collapsed on the bed. I went back to the living room and Fran was lying on the couch and under the covers.

"How do you want to do this, Mark?" she asked.

I was dumbfounded and not even sure what she meant by that statement. I just wanted to take out my dick and put it into her. She must have seen the odd look on my face.