The Tomboy and Randy


I had been riding for about two and a half hours and my stop was about three or so miles ahead. Since there was no major highway or paved road up to the lake, I’d have to walk the mile or so in. I didn’t really mind, I enjoy the woods that surround the lake and it was early enough in the morning so it wouldn’t be too hot.

I had packed light. A sort of backpack held everything I had brought and it really wasn’t too heavy. Finally I yanked the cord and the driver pulled over to the cut off. I nodded “Yes” when he asked if this was my stop, and then stepped off the bus.

Actually this was a surprise visit. I mean I hadn’t seen Randy in about two years and he had no idea I was coming up to the cabin. Well it wasn’t exactly a cabin, it was an “A frame,” and Randy was up fixing the roof for aunt Bertha.

When I received the email saying that Randy was working on the place, I thought it would be a great surprise. Sort of a reunion if that’s the right word for it.

Randy and I had been inseparable right up to graduation. I mean I was a tomboy and he always treated me as his best friend. We always had contests going on between us, or we had some sort of dare between us. If he won, he would strut around like a rooster. That’s why his nickname was “Rooster.” If he lost, he was a chicken. And I suppose that was sort of appropriate in a childish sort of way.

Two years ago, my mother remarried and we moved away, but the best parts of my life were when I was with Randy. We were inseparable. He was maybe a year younger than I was, but age never figured into our closeness. As children we used to make little forts together, or make a tent in the woods behind the house and camp out and share thoughts or scary stories with each other.

Then as we grew older we promised that we would always stay in touch. He had been awarded a scholarship at a University and I was off to college.

Actually I had a crush on him ever since grade school, but I could never let on. I guess girls mature earlier than boys because he never seemed to be really interested in me as a girl but rather as his buddy.

Well I finally broke down when mom told me that we were moving away and I was frantic to stay. I even begged her to let me stay in town until I had to leave for college, but that wasn’t practical. I even asked if I could stay at Randy’s house but she sort of frowned on that. I was getting too well developed as a woman for that sort of thing.

Randy and I had always been daring. I mean we would challenge each other to do things and that’s probably how I learned a lot about guys. I would listen to the stories the girls would tell each other at parties and sort of envy them in a way. Oh most of their supposed experiences were probably fantasies but still I was curious. You know to be getting ready to leave home and go to college and have no experiences of my own is sort of a downer.

Well to be honest the only times I got intimate with Randy was when we would wrestle. We did that quite a bit. I mean if he had something I wanted I’d wrestle him for it and he did the same with me.

I guess as young adults that was acceptable and we would do that right up until we were separated.

There were so many times that I would have him pinned down and his lips were close to mine and my small breasts were pressed against him, that I wanted to kiss him. Then I would hesitate for fear that our relationship would change. So the most I would do would be to grab his crotch and squeeze.

He would always give in and laugh or something. It was rare that he would do anything like that to me though. Hell I’m not sensitive down there, not in that way.

It was probably just a few days before we moved away that we were arguing over the last bottle of beer and he had me pinned under him. I grabbed for his crotch and he grabbed back.

I wiggled around as he held his hand tightly clamped to my jeans, squeezing my pussy, while I tried to get away, when suddenly I got this tremendous thrill.

Oh I had been masturbating occasionally for almost three or four years and I knew what it felt like to have an orgasm, but never anything like this.

It was so intense that I let out a squeal and began to moan. He thought he had hurt me and quickly let go. Naturally I kept up the pretense that he had hurt me and I got the beer, but I never told him what had really happened.

I went home that afternoon with the most intense need for him that I spent the next hour in the shower with my little lotion bottle. It was empty. It had been for probably a year, but it was plastic and the bottle was rather ornately decorated with swirls all around the outside. I would fill it with warm water and after screwing on the cap, I’d put the domed lid over it. It made the perfect dildo to use in the shower and no one ever suspected.

I must have cum three or four times, but never as intensely as when he had grabbed me down there. I wanted desperately to have him do that to me again but I never had the chance. We left two days later.

To this day I don’t think Randy knows that he gave me my first real orgasm or that from that time on I began to masturbate every day while looking at his picture.

I even gave a name to my little lotion bottle, my Randy bottle. I had discovered that simply by pumping it in and out while I played with my clit, my climaxes were a hundred times more intense, and I even began gasping his name out aloud each time I would cum.

By now I had finally reached the lake and the house. Looking across the opening I saw him carrying a bundle of shingles around to the shed in back, and quietly came up behind him.

“Hay. You a Rooster or a chicken today?”

He dropped the stack of shingles and turned. I gasped. My Randy was something dreams are made of. Good looking, broad shoulders and a narrow waist. I was speechless. And I just stood there staring at his bare chest.

“Elli? Oh my god have you ever changed. What happened to my little tom girl? You really filled out. I mean you have curves where there were none before. What are you doing up here?”

I explained about the email and how I wanted to surprise him and decided to come up for a few days.

He took my bag and holding my hand walked me into the house. Now an “A frame house” is generally one large room with a sort of loft up above. Everything is open except for the bathroom which is sort of partitioned off in one corner. He set my bag down and swung me into his arms. A bear hug sort of thing that took my breath away.

I couldn’t think of anything to say so I just blurted out. “Still think you can beat me in a wrestling contest?”

He seemed a little bashful and sort of gasped. “Nope Elli, you win hands down. So how long will you stay? What have you been doing, married or a boyfriend? Tell me everything that’s happened since they took you away from me.”

This wasn’t my Rooster. This was a young man I had always adored and I got that old feeling again. I was having flash backs of that day at Wills river where we had skinny dipped and touched each other, and my pussy began to do that crazy twitchy dance it does when I’m excited.

I wanted to relive that day again. I wanted to get him in the water again and this time let him see how well I had filled out. So I began to scheme.

He took my bag up to the loft and put it on to the only bed in the place. Then returning he sort of apologized for being so unprepared and sweaty. I just looked at him demurely and made a suggestion.

“You remember what we used to do at the cove in Wills River? Well, I’m pretty sticky too, so let’s go skinny dipping in the lake. You gonna be a rooster or a chicken today, Randy?”

He looked at me as if amazed. “Are you still into making dares Elli? You’re not the same girl I knew back then. You’re a young lady now. I think I’m going to be a chicken today.”

Awww don’t let me down. I’m the same tom girl you knew back then. Just a few more curves and what the hell Randy, I don’t want things to change between us, so loosen up and come on. Be my Rooster again.”

I guess that got to him because he nodded and took off his shoes and sox. Then stripped out of his shirt and took my hand and walked us down to the dock.

We stood there each waiting for the other to go first. Finally we both began to wiggle out of our clothes. I still had my blouse and bra on so I shrugged out of them first. Then we both took off our jeans. He wore no shorts so he stood with his back to me as I stripped my jeans and panties off. He wasn’t going to turn around and I sensed it. He just made a mad dash for the end of the dock and dove in.

I had wanted him to at least look at me. I guess I wanted to be admired. After all, I had just taken off a bra with a C cup and my nipples were now atop breasts that were perky and full.

Now, making the best of it, I dove in after him. Normally I would never feel shy around him, but now he wasn’t just my pal, he was someone I wanted to make love to and I didn’t know how he felt about me.

I surfaced next to him and my breasts rose to the surface of the water. “Great,” I thought, now my nipples were firm and quite sensitive as I deliberately brushed them against his chest. He seemed uncomfortable and began to swim away. I followed. Were we having a race, I wondered.

Twenty minutes in the water and I was beginning to get numb. It was cold as hell and I wanted to get out. I swam back to the dock and heaved myself up. Now I sat there, my feet dangling in the water and my legs invitingly apart so he couldn’t help but see my pussy.

He didn’t miss my little show but pretended not to notice, but when he heaved out of the water and sat next to me, he had already started to get a hard on. I sneaked peeks at it and so help me god it was massive. I smiled to myself and wondered, “How is he going to hide that?”

I sat there staring out at the lake and started a conversation. “Remember that time when you thought you had hurt me and I made you give me that last beer?” He nodded. “Well you didn’t know it but that day you made me cum right there on the living room floor.

I wanted you to do it again but I wanted you to think that you had hurt me so I couldn’t admit it. Actually I wanted to cum again so bad that I went home and did it to myself again in the shower. It wasn’t as good as when you did it, but it was something I wanted and needed.”

“I still dream about that a lot when I’m alone and need to finish. I guess the first time for anything is sort of the best.

You know I’m still a virgin. I haven’t found anyone I want to touch me like that again. Except you, I guess. Do you ever think about those times Randy? I mean the times we spent together?”

He turned and looked down at me and answered. “Sometimes I guess. I’ve sort of shied away from girls after you left, Mostly because all the girls I meet are sort of worldly. I mean it’s a guy thing to want sex all the time, but now days, by the second date; they want to suck you off or something to show you how good they are and expect a guy to do something in return. And I don’t know exactly how to please a girl and I don’t want to act inexperienced. “

My heart nearly beat out of my chest. If I could bring our intimacy back to where it had been, I could teach him. But I would have to handle this carefully; I didn’t want to be one of those girls that he was afraid of.

“Have you ever had a girl suck you off? I mean even if you never went all the way you must have let someone try it once.”

“No, not yet. I thought about it, but what if I couldn’t stop my self and something happened? I guess I’m a chicken. And then they would probably expect me to do things to them and I don’t know what to do. No I’ll have to learn more before I try something like that,” he mumbled.

At that moment, he sort of rolled away from me and stood up. Keeping his back towards me, he struggled to get back in his jeans but nothing could hide that hard-on he had, so he walked in front of me back up to the house.

I made sandwiches for a late lunch and we sat around drinking some dandelion wine that we found stashed in the shed. Someone must have laced it with some local white lightening because it was much too potent to be just wine. So that led to some more reminiscing and I kept the subject of sex in the conversation so he wouldn’t balk at what I had in mind.

So what do you think of me now, Rooster? Still think of me as a tom boy? Nice boobs and titties, my pussy isn’t a little cunnie any longer but a full fledged cunt and my little boyish tush is a well rounded butt. Like what you see?” He nodded before I went on.

“And I even keep my pussy shaved so it still looks the way it did when you first saw it.” I watched him and tried to read his body language. I guess he was either getting comfortable with me, or the wine was beginning to affect him. Maybe both, but I was getting bolder and I needed to take it further, so I actually offered to teach him a few things about making love to a girl, which actually would be like the blind leading the blind. I didn’t know a damn thing about things, except what I had read or tried on myself.

By now it was raining out and the sun had gone down. He got up and lit the kerosene lamps and turned on the gas to the water heater. At least we’d have hot water later. He started a fire in the fire place and returned to the couch.

I guess it was at that point that he realized that we might have a problem with our sleeping arrangements so he went and got his sleeping bag and put it next to the couch.

“Oh no you don’t Randy. Unh unh, we share. Just like in the tent. You on the right, me on the left. No arguments now, understand?”

He wanted to argue, but when I started chanting, chicken, chicken, he gave in and just sat back as I poured another wine for him.

A half hour later I had him in bed with me. He had insisted on wearing his shorts but he said nothing when I crawled in bed totally nude. For the better part of an hour we chatted about things we’d done together, about our pets and other cherished memories before he turned away and whispered, “good night, Elli.”

I had no time to waste. I was horny as hell and he was in bed next to me. I wanted him so fucking bad that my pussy was getting creamy just thinking about him. And to make matters worse, he was so damn innocent. Just like he had been so many years ago.

I began to wonder. Had I avoided having affairs so far because I wanted him to be the first? Sure we had bonded and really there wasn’t anything we wouldn’t do for each other back then, but had anything changed? I was going to find out.

I broke the pattern. I rolled over towards him and reached out and grabbed his shoulder. Tugging slightly so he rolled onto his back.

“Randy? Take your shorts off for me. Please? I want to teach you something. Do it for me, please? Be my Rooster tonight, do it for me.”

I guess the wine had worked, or perhaps it was our closeness, but I sat up and pulled the blanket off us and had him lift up enough so I could helped him wiggle out of his shorts.

Surprise… He was already semi-erect and my god he was big. I actually had to fight the urge to put my mouth over that beautiful cock. That would have been a first too. I had sort of sucked on my lotion bottle sometimes, imagining what it would be like to go down on him, but never actually done it with anyone yet.

You hear all sorts of storied that girls tell about how great it is to make some guy explode in your mouth and the feeling of power it gives you when he begs to fuck you, but sometimes it’s just talk and nothing more. But at that moment, it was my dream. I wanted my Randy to need me as much as I needed him. And I wanted him to go down on me and learn what needed to be done to satisfy me.

I whispered. “Just hold still. I want to try something with you. Let me do it my way and you tell me how you like it. Then I want to teach you what I want, OK?”

He took a deep breath, and answered, “Deal.”

Hell I was probably more inexperienced than he was. I watched the lantern flicker patterns of shadows across his tight abs as I held his shaft up and began to stroke it slowly. As he grew larger and larger I lost control and lowered my lips to his cock.

I heard him draw a quick breath as he slid into my mouth. My first taste of a man and it was my childhood buddy. He tasted good. Well, really not much of anything in the beginning, but then my mouth began to fill with my own saliva and I began to bob my head up and down.

I had one hand wrapped at the base of his cock while my other hand cupped and gently rolled his balls in my palm. He began to sort of push up. He wanted more and I began to get more excited knowing that.

Now he began to ooze slippery precum in my mouth and he grew even larger and more rigid. I couldn’t take him too deep without gagging but I began to take deep breaths just before I would try to get him down my throat.

Three or four tries and I had learned to resist gagging and I began to alternate quick thrusts in and out of my mouth with occasional deep swallows. He was beautiful. He began to moan but tried to hold still.

I was losing it quicker than he was. My jaw began to ache from holding him in my mouth so I began to take his cock out and lick it from its base to its head. Sometimes gently sucking on his balls before wiggling my tongue up along the bottom of his long cock, then slipping it back into my mouth.

When he began to groan and shake I knew I had him. Quickly I let him slide from my lips and I whispered, “don’t stop me Randy. I want it!” Then I returned his cock to my mouth and began to move as quickly as I could, bobbing my head up and down while swirling my tongue around the rim of its head.

His voice went up an octave as he gasped. “Elli? Elli, I’m gonna shoot. Oooh god here it comes.”

My heart pounded, my nipples seemed to tingle and my cunt began to seep. Just knowing that he was going to cum in my mouth, was erotic beyond belief.

I hadn’t even thought about what I would do when he began, but instinct took over. The first jet was weak. Mostly thin and tasteless, but after that my mouth began to fill with thick ropy jets of cum.

I held my tongue against the tiny slit and could actually feel each burst of the thick fluid as it continued to fill my mouth. I didn’t give it a thought, I began to swallow and as my throat worked to gulp the thick mass down, I came as close to an autoerotic orgasm as anyone can.

I sucked and swallowed, I bobbed my head trying to keep him cumming but it finally ended. Because he stayed firm and rigid, I began to bob my head again, hoping I could make it happen a second time, but now my jaws ached so much that I had to let him go.

He reached out to me and I put my mouth to his. His tongue slid between my lips and I know he could taste what I had just tasted, his cum. For perhaps minutes we clung to each other and I ground my erect nipples into his chest. Then we separated, gasping for air.

“Now you,” he began. “Teach me what you want, Elli. Tell me what to do and I’ll do it, I promise. I’ll be good for you.”

I was floating. I had made him cum for me and now he needed me. Or perhaps I needed him more. I just didn’t care, I wanted to cum and I needed him to make it happen.

“OK, I began, just do what ever you think I would like. Surprise me. My breasts are a good place to start. Suck on my nipples, but don’t bite them too hard until I tell you to, OK?”

I rolled off him and lay on my back. Then the world began to dance. He began by kissing my forehead, and then he moved to my eyelids and down to my lips. I was floating. As he nibbled at my lips his hand moved to my breasts and his palm slid back and forth across my nipples, bringing them to hard, hot points of sensation that seemed to be connected somehow to my pussy.