tagFirst TimeThe Small And Large Of It

The Small And Large Of It


I do not mean to say that the penises in this story are the largest or smallest ever. I simply mean they are the extremes of the few that I have actually experienced. All of the people in the story are at least 18 years of age.

The first penis I ever saw was when I lost my virginity. That was on Prom night. Though it may sound like a cliche, that was when it happened. It was not a great experience. Actually there was nothing even good about it.

After our Prom, my date Kyle and his friend Tom took us to a motel across town. Mindy and I (my name is Hannah) and our dates were in separate cars, but for a moment I was afraid all four of us were going to share a room. That would never do, but thankfully we weren't asked to do that. That was about the only thing that went right. I sat in the car while Kyle and Tom went into the office to get our rooms. They had taken off the coats and ties of their tuxes and replaced them with normal jackets. This way they thought they would not stand out. I thought they looked silly, like someone trying to hide the fact that they were bringing their Prom dates to a cheap motel.

All the while I sat by myself in the car, dressed up and made up, feeling very embarrassed to be there. I tried not to look at Mindy in the next car, who looked as out of place as I felt. After what seemed like hours of waiting, it got only worse as Kyle opened the door for me and led me to the room. I nearly cried as I stepped in to the low rated motel room in my beautiful Prom gown where I was to lose my virginity to a boy I didn't like that much.

I suppose at this point the reader may wonder why I was doing this. The short answer is that it felt like it was time to give up my virginity, before high school was over. And why Kyle? Well, because he was there.

It wasn't always like that. I used to be a very popular girl. I think I peaked in my Sophomore year. I was a cheerleader, and that seemed to make me the object of desire for most of the jocks in school. It worked out well because that was who I wanted to date. I didn't seem to care too much about what they were like. Just what their status in high school was. That meant basically how good at sports they were and how good looking they were.

As for me, I was your stereotypical cheerleader. Tall, thin, athletic, cute, long legs, perky breasts, and a flirty personality. In my Sophomore year I attracted mostly Junior boys, and a few Seniors as well. I suppose I attracted a lot of Sophomores, too, but I didn't bother much with them. I liked the older guys, and they liked me. Well, I suppose they like nailing a cheerleader most of all.

But that was the problem. I wasn't ready to have sex yet. I was young, wanted to be popular, and wanted to get some experience with boys, but I didn't want to "go all the way." Most of the guys didn't seem to mind too much. Probably because my body was pretty much open to them in most other ways. Usually by the second date they were free to feel me up as much as they wanted. And I mean completely. My clothes would disappear and their hands would freely roam.

I even learned how to masturbate from a couple of those Junior boys. I didn't masturbate much before this, but their hands made me feel so good rubbing my clit, that I found I needed that same feeling more often, so I would do the same things that they did to myself. Most of the boys were just clumsy, though. Too rough on my breasts and little clue even as to how to undress me. We all have funny stories about the mysteries of unhooking bras, right?

But for some reason I drew the line when it came to the guys' bodies. Of course I could feel their erections in their pants, but I did not touch them. If they started to unzip while we were making out I put a stop to it immediately. No stroking, no blow jobs, nothing from me. I suppose some thought I was a real cock tease, but I let them feel my body so much that most of them forgave me. And I never had a steady boy friend. Two dates in a row was the most that I got. Or wanted. More than two dates was okay, but not in a row. That might send the wrong message.

Clumsy guys were especially common when I was a Junior and Senior. You see, I gave up cheerleading then - it just seemed like so much time and work - but then the best athletes seemed to have much less interest in me. So the boys asking me out were generally less experienced, and I kind of missed that. By the time I was ready to give up my cherry I was still looking for a special guy, which I never seemed to find.

That brings us back to the Prom. I went with Kyle because he asked me. He asked me early, but he was the first and I said yes. We had never even really dated. We were friends, and had gone out many times in a group of friends. The first time we kissed was the time he asked me to the Prom, and we didn't even have a real date after that. The Prom was our first, real, alone date. And I had decided that I did not want to leave high school a virgin, so when he said that Tom and Mindy were going to a motel afterwards and asked if I wanted to go also, I said yes. I knew what I was getting into.

After my fast start as a Sophomore, I felt that I was inexperienced now as a Senior. I still had never even seen a penis, except for pictures and on the internet. That made me pretty nervous as I walked through that motel room door. A little like the sacrificial virgin.

"What should we do?" asked Kyle after he shut the door to the room.

I think that sounded more naive than he meant it to. At least I hoped so. I really didn't know how experienced Kyle was. I never asked if he was a virgin, though he didn't talk as if he was. But what guy did? As i said, we had never been on a real date before. Plus I did not know of any girls claiming to have slept with him. So I was figuring he was pretty inexperienced, and he sounded like it at the moment. At least he could have kissed me!

"Why don't you get - in bed - and I will go into the bathroom and get ready," I suggested.

Once in the bathroom I looked in the mirror at my makeup and my gown, and very nearly burst into tears again. This is not how I wanted to do this, and not who I wanted to do it with. Not that it was bad - Kyle was a nice guy and had an attractive body. It just seemed like I had painted myself into a corner without choosing a guy I really wanted.

Putting all that aside, I gingerly removed my gown and tried to place it where it wouldn't get soiled. I removed most of my underwear also, leaving only my bra and panties on. I peed and dabbed at my eyes. I couldn't wash my face like I wanted because I didn't want to ruin my makeup. When I was ready I took a deep breath and opened the door.

I was hoping for some complimentary words from Kyle when he saw me, looking my sexiest, but all I heard was a sound more like a giggle from him. He was indeed in bed, naked at least from the waist up with a sheet pulled over his lower half.

"Not bad looking at all!" I thought to myself as I eyed his chest for the first time. I walked over, as sexily as I dared, and pulled down the sheet on my side of the bed and slowly got in.

I laid down beside Kyle, almost on top of him, and gave him a slow and sexy kiss. He was slow on the uptake, but soon we were kissing passionately and our hands started to roam. I felt his chest and liked what I felt. I was starting to get into this! His hands were all over my breasts, but couldn't quite get inside the bra. He changed tactics and reached around behind me to unclasp it, but I ended up having to help him a bit. He made up for lost time by nearly ripping the bra off me as soon as it was open and attacking my bared breasts as if they were his first. He was definitely over eager, and seemed reluctant even to move on from my breasts to explore the rest of my body.

My hand eventually moved down his body to his erection. The first one I had actually felt with my hand on purpose, even though it was over the sheet. I still didn't squeeze, just pressed down on it, but this gave him the courage to explore my panty-covered area. Still hesitant, I finally removed my panties myself to give him unobstructed access to my entire body. He felt my ass up a lot, and a little of my legs, but stayed away from my pussy, much to my chagrin. I spread my legs, placing one over top of him, pushing my knee into his hardened dick, playing with it. Then I guided his hand between my legs, slowly, until he came into contact with my slit. He seemed to stiffen at that point. (No, I mean the rest of his body. His dick was already as stiff as it could be, I assumed.)

While he began to explore my pussy I pulled the sheet down off him to get my first view of a real live penis. I must say I was disappointed. It seemed like it was little more than four inches, I guessed, much smaller than the ones I had seen in pictures. But I realized that those pictures were probably doctored up to make theirs look so much bigger than they actually were. Kyle's penis, I assumed, must be the actual size. At least this is what I told myself at the time. What did I know?

I was not disappointed when I touched him. It was a shock to feel something so hard and yet so soft at the same time. The skin on his erection moved easily up and down, and Kyle moaned when I did this. I wanted to explore further but Kyle rolled on top of me, trying to find the place to get his penis inside of me. He didn't seem to know just where the entrance was, and it was a turn off for me to feel him prodding my crotch with his erection.

I had to help him, taking his penis and guiding it into my slit. I was hoping to rub it around a bit until I got wet enough to make his entry easier, but once he felt the hole he wasted no time in taking over and pushing it in. It did not go too far until I was moaning in pain. He at least understood this, and stopped pushing.

"Are you okay?" he asked.

"Yes. I will be," I told him. "It hurts. Just go slow."

He knew I was a virgin, but evidently he was as well and didn't understand how things worked as well as I would have liked. Hell, I didn't know as much as I would have liked, either. I knew that the first time hurt, sometimes a lot. Most of my friends had talked about their first times, and I don't think even one of them started out without pain. As I thought about this I felt my tummy tensing up and my vagina tightening in response to the pain I knew was coming. I know now that this is worst thing I could have done, but it was a natural response. As Kyle began pushing in again I tightened up even more in an attempt to keep him out. I didn't want to, but I couldn't help it.

Kyle was not to be denied. Once he started he kept up the pressure. The word "banging" was in my head, as I thought this was what he was doing. Not actually fucking me, but banging on my door trying to get in. It wasn't pleasant for me, though, as I was not lubricated enough to allow him in. He not only had to open me up enough to admit his dick, but his dry dick was pushing into my dry vagina, rubbing us both raw. He did manage to get in most of the way before he let loose with a load of cum. Most of it went inside me, but he slipped out before he was done and spurted a bit onto me. Never having seen that before, I didn't know if it was a lot or not, and I didn't really know if it mattered. I was just happy that the experience was over. From now on it be much better.

Kyle rolled off me and muttered, "Oh, Hannah, that was good."

He smiled and laid back very satisfied. I wondered if he even thought about me. I started to get up for the bathroom, as I could feel quite the mess between my legs.

"Are you okay?" he asked, mostly because I was getting up.

"Yes," I said quietly, as if someone else might hear. "Just have to clean up."

He mumbled something as I rose from the bed. In the bathroom I used a lot of toilet paper to wipe up the mess. I inspected for blood but did not find any. That was no surprise. I was told there might not be, that my hymen may have been broken with all of my cheerleading, horse riding, and other activities that I had done. I was grateful for that, but wondered how my legs had gotten so much of his spunk on them. What a mess! I washed my legs off with a washcloth before they felt clean, and used another to clean the makeup off my face, trying not to think a lot about the experience. I was just happy that it was over.

When I got back to the bed Kyle was sound asleep. I searched for my panties and slipped them on. I kept my bra off, snuggling up to the sleeping Kyle and enjoying the feel off my breasts and nipples on his naked chest. So many thoughts were swirling around in my head that I took a long time to fall asleep, but I finally did.

I woke up a few hours later, feeling Kyle's hands stroking my breast. Not a bad feeling, even if he wasn't very gentle. I felt his erection pressing against my thigh, and as soon as he knew I was awake he rolled on top of me, kissing me and pushing his dick against my crotch, looking for that elusive entrance again. I told myself that this time it would be better, but he was in such a hurry to get in me that I was far from ready. Once again it was a dry hump - except that he managed to get his dick inside me. A dry fuck I suppose.

He took a little longer this time before he came. I could feel him get a little deeper than he had before, and I was starting to get a little lubricated. But just as I felt that, I felt him swell inside me and blast my insides with another load of sperm. I panicked a little while he was still spurting inside of me, as I suddenly thought of birth control.

Strange as it sounds, I didn't think I knew him well enough to tell him to get a condom. I know, I knew him well enough to fuck him, but not ask for protection. Such was my mind as a young girl. I couldn't wait until he was done so that he could pull out of me. I nearly ran to the bathroom to clean up. I had thought to bring a douche with me, but had not used it the night before. I did not know how long I had to use it, or if it would even work. But that was what I had so I used it. I told myself that I had to find a way to get on birth control pills.

When I came out of the bathroom, Kyle was dressed and pushed past me, saying that he had to pee bad! How romantic! I dressed in the other clothes I had brought, telling Mom it was for the party at Becky's house. (Thanks, Beck!) We loaded my dress in the car as carefully as Kyle would let me and drove home.

Kyle and I dated for a few weeks after that, having sex at least one time each week. The sex got better, but not good enough to give me an orgasm. After school was out we didn't see each other as much, just for our dates, and he seemed to lose interest in me except for the screwing. He didn't seem to mind that much when I broke up with him.


At my summer job there was a guy, even better looking than Kyle was. Nate was three years older than me, so he not only looked better, he also looked more masculine. I was in lust.

He definitely noticed me as well, and I did my best to make sure of it. You know, paying attention and giggling at his jokes, bending over - frontwards if I had something low cut on, backwards if I had tight slacks on. Or short skirts. I thought I might go broke buying new and more revealing outfits for work. But fortunately for my budget and my sex life, it didn't take him too long to ask me out.

My track record with guys is to let them have my body pretty easily, and Nate was going to be no exception. He took me out to a very nice restaurant, one that I had seen but never thought about going to. I dressed nicely and we had a great time. We talked. And he didn't get all handsy with me. This was something new for me. I guess I had to act classy with this guy.

After a long, relaxing dinner he asked if I wanted to stop somewhere for a drink. He laughed as soon as he said it, because we had already had this discussion at dinner - I wasn't old enough to drink. He said he forgot about that because I seemed so sophisticated. I thought that was a line, but it still made me feel hot!

"Okay, I have an idea," he said. "You're too young to go out for a drink, but I have some at my place, and you're allowed to drink it there."

Was I? I didn't know, but it sounded good. I agreed to go, then realized that it could be another line, just to get me to his place. But that was okay. I was not shy, or slow in that regard. I even thought I might like to screw him, even if it was our first date. That is what my dates with Kyle had mostly been anyhow. This date was just with a sexier man.

We went back to his place, which was impressive. It wasn't that great, actually, but it was much nicer than I was expecting. And to my surprise, he made me a drink and sat down to talk. He still did not try to get in my pants! Impressive! But at this point a little frustrating for me. If he only knew what I was expecting. And hoping for.

When I was halfway through my second drink he finally leaned over and kissed me. A beautiful, soft, romantic kiss. I responded well, and when we broke he took the drink from my hand and set both of them on the table. He situated himself again and kissed me again, this time a little stronger. More passionate. And he could hold me with both hands since he was holding no drink. We soon had our tongues battling and saliva was leaking onto our chins. Our lips were in danger of being bruised. He seemed to want this as much as I did.

I was so grateful when his hands began roaming. He had been stroking my neck and touching my ear while we kissed, which was driving me up the wall. I loved that! But now his hands moved lower, gently cupping my breast. Soon he was unbuttoning my dress and reaching inside, stroking the soft flesh of my upper breast, then easing into my bra cup to feel the nipple. I was responding with sharp intakes of breath and gentle moans to what he was doing. I loved it all.

I hadn't realized that his other hand had finished unbuttoning my dress until he began to ease it back over my shoulders. He let it fall behind me to my waist, leaving me sitting there in the sexy black bra that I was hoping he would see. He leaned back a bit and took me in with his eyes, gazing longingly at my breasts in their flimsy restraints. This was the sexiest thing he had done yet, and I tingled with excitement.

"You are beautiful," Nate said softly, looking into my eyes.

I was speechless, but looking for something to say. "Me? Or my breasts?" I said, trying to sound as if I was teasing.

"Oh, definitely both, Babe. I knew you were lovely, and I see your breasts are just as beautiful."

That was the first time I understood what the word swoon meant. My whole body went a little weak, and I could feel a twinge between my legs. My pussy felt a bit moist. I was searching for a response when I felt my bra release. It hadn't been difficult for him to master the clasp. His hands raised to my shoulders, slowly letting the straps edge over and down, letting my bra cups rest precariously over my breasts, held up by nothing. As he slid his hands slowly down my arms, I wanted to rip the bra from my body and press his hands into my breasts, but I didn't.

I was, however, nearly shivering with excitement as he gazed at my newly uncovered breasts. My nipples must have been the hardest they've ever been. I was tingling with anticipation as he gently cupped the curve under each of them, saying, "My God, you have beautiful breasts, You are a sexy lady." Then he leaned down slowly and kissed each nipple, gently but firmly. I could feel my panties getting damp. That never happened except when I was alone!

He began licking around the areola, then the nipple, and finally gently sucking each nipple into his mouth in turn. I heard a nearly constant moaning, not realizing it was coming from me. He was giving my breasts this treatment for many minutes. Who knows how long? When he was done he slid his hands underneath my ass, lifting up gently to get me to stand.

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