I made the first time happen for me during my sophomore year in High School. Although I was sixteen, I stood only four foot ten and weighed ninety pounds. Most boys treated me like their little sisters, patting my on the top of my red head and cracking short jokes. Although I was short, I was well built. Some guys in computer class had gotten a hold of the band uniform list, and published the measurements of all the girls in school. In addition, they made a computer model of me at five foot two and one hundred ten pounds. I was 36-24-34, as compared with the average sophomore girl of 33-24-34. I took it as a joke, but even so, I could hear some of the guys commenting about my figure, even if I was small. Justin only smiled when the guys asked if Robin really was a handful.
Justin and I had worked together at a local amusement park during the past summer. I liked spending time with him because he accepted me as some one other than his little sister. We began dating a week or so before school started, and soon discovered that we had a good time together. Before long, I was the envy of every girl at Valley High School. Justin was a junior and already held three school records in track, was a starter on the Varsity basket ball team and a state recognized running back on the foot ball team. Any girl in school would have given her right arm to get him in the back seat of a car for an hour or two. If I believed the rumors, a few had already been there. It was probably true, but at this point, we hadn't done it yet.
Being so small, I hadn't had a boy friend for anything more than an occasional group movie date. Most boys didn't want to be seen with someone who looked like a grade school girl, but Justin seemed to accept me for just who I was, a sixteen-year-old sophomore girl who simply was smaller than average. I kind of wanted to do it with him, and sensed that all I had to do was let it happen. Being so small, I was afraid I couldn't handle a normal size boy so resisted going any further than a lot of groping in the car.
I wanted to try it out, but didn't want to risk a big scene with Justin. More than that, I didn't want to lose Justin because we couldn't do it together. As I pondered how to resolve the issue, the solution kind of fell into my lap. It was the Thanksgiving holiday, and all the relatives were at our house. My cousin Steve was there, and his college roommate, Kirk, came along. I had gotten fairly well acquainted with Kirk during Steve and his frequent visits. He was a nice guy, who also treated me like a person instead of a little girl. I especially liked the way he always referred to me as “Little Bit.” Kirk had just purchased a new van, and spent nearly every spare minute installing a new sound system.
After Thanksgiving dinner, we sat around talking until Kirk decided he had been polite long enough and wanted to get back to his van. I went along with Steve and Kirk, desiring some older companionship. Even though I was sixteen, the relatives still tended to treat me like a twelve-year-old. Before long, I was helping string wires, using my small size to get into places where the guys couldn't fit. After we got the sound system installed, we went for a drive to test it out. I showed them around town then drove up to the lake. It was a sunny warm afternoon, so we could sit outside the open doors of the van listening to the latest hits on the stereo CD system.
The next morning, Steve and Kirk decided to go their separate ways. Steve had a couple of errands to run and wanted to buy some clothes. Kirk said he wanted to putter around with his van. By mid morning, I was bored with the relatives so went outside to see how he was doing. He had the van pretty well organized as he wanted and pronounced it ready to roll, so he invited me to go for a ride with him. That suited me fine and in a moment I was in the right captain's seat cruising down the road listening to a CD.
After meandering around for about an hour, we ended up in a remote park off the river. We sat on the dock watching the river flow silently by, skipping rocks across the surface. It was a little chilly, and I began shivering. When Kirk noticed, he pulled me against his side, wrapping me inside his jacket. I snuggled close feeling the warmth of his body flowing into me. I sighed contentedly, enjoying the feeling of his strong warm body.
As I gradually warmed up, I became aware that Kirk was stroking my back, pulling me closer and closer. I responded by pressing against him and running my fingers in little circles on his arm. I could tell that Kirk was getting turned on, because I could feel his heart beating faster. I turned my face up looking into his eyes. Moments later, I felt Kirk's lips pressing gently in a tender kiss. I returned the kiss, hoping that I was doing it right. It must have been OK, because when we broke, Kirk hugged me tight and caressed my ears with his fingers.
I leaned against him feeling contented in his arms. A few seconds later, I turned my face up inviting another kiss. I was rewarded with a more intense kiss, and responded in the best way I knew. When we broke, Kirk pushed me away and said he was sorry, that he just got carried away. I looked him square in the eye.
“I'm not sorry!" I exclaimed and kissed him again, pressing my body as tightly against him as possible.
I hugged him as hard as my arms would allow, trying to transmit how much I was enjoying his attention and kisses. After kissing and cuddling for several minutes, Kirk kind of leaned back and looked at me.
"You sure don't act like a little girl," he chuckled.
"I'm not a little girl, and I'm kind of tired of people treating me as such! That's what always attracted me to you. You treated me like a real person."
"Well, size aside, right now you look pretty big to me."
We made small talk for a few minutes, continuing to cuddle and caress. After a moment of silence, I looked steadily at Kirk for several seconds.
"Teach me how to do it."
Kirk's mouth fell open as he took a sharp breath.
"You got to be kidding!" he stammered with a stunned look.
I shook my head, looking at him with a steady gaze.
"Why do you want to do this?" asked Kirk with an intense look.
“Well, I have a steady boy friend, and I knew that sooner or later, probably sooner, we will make love. I’ve heard so many horror stories about clumsy attempts at doing it for the first time, and just don’t want to go through that kind of experience. I know you and I will never be a steady number, so this will be a no-risk situation.
“Well, -- well, I guess I’m willing to start showing you what to do, but you have to promise me you will stop if you start getting scared or just don’t want to go through with it. Do you absolutely promise that you will do that, and I won’t end up getting charged with rape of a minor?”
I nodded silently, then took a deep breath and stood up. Kirk followed suit, leading the way back to the van. The dark color of the van had soaked up the heat of the sun, turning it into a comfortably warm enclosure. Kirk led me to the rear portion of the van where we sank down on the soft seats. After a few awkward seconds, Kirk took me in his arms and began cuddling and kissing. He became more passionate, holding me close and firm. He began running his hands up and down my back, then slowly unbuttoned my shirt. I moved back giving him space to get to the buttons. After opening all the buttons, he slid his hands up my back and began to fumble with my bra clasp. Obviously, he knew what he was doing, because in just a second or two, he had it unfastened. Without hesitation, he ran his hands around the band, then pushed the cups up and began caressing my breasts. I leaned back, marveling at how gentle his big hands were. I was also somewhat self conscious that his hands were able to completely cover my little breasts.
“I’ve wanted to feel those beautiful little tits ever since the very first time I saw you,” whispered Kirk in my ear as he nibbled it.
I responded by arching my back thrusting them into his hands. His hands felt fantastic, so I lay back enjoying the feeling. After playing with my breasts for several minutes, Kirk gently slid my blouse over my shoulders, and tugged it off. Seconds later, my bra was lying on the seat on top of my blouse, and Kirk was staring at my topless little body.
"You are absolutely gorgeous," he said with a smile.
"What should I do next?" I asked.
"Are you sure you want to go on?" he asked.
I didn't answer, just moved close to him and began unbuttoning his shirt. When it had joined my blouse and bra, I began to stroke his chest, and play with his jutting nipples. When I started to giggle, Kirk asked me what was so funny.
"I just noticed that if your nipples get any harder, your breasts will be as big as mine!"
Kirk roared with laughter then kissed me gently.
"I love your sense of humor, Little Bit," he said with a big smile.
We cuddled for a few more minutes, until I began to wonder if he was going to do anything else. Just about the time I was going to ask him what was next, I felt his fingers fumbling with the button of my jeans. It wasn't long before he had it open, and had slid the zipper down. I lay back, expecting him to slide my jeans off. Instead, he hooked his fingers under the band of both my jeans and panties, and before I realized what had happened, he had slid them off.
I was lying on the deep soft carpet totally naked. Kirk was kneeling at my feet, staring at my body with a kind of look of anticipation. He reached his hands out to me, and pulled me up to a sitting position.
"You are about the most beautiful little thing I have ever seen," he said with awe in his voice.
I smiled at him, gazing at his bulging pants. Kirk studied my face carefully before quietly asking if I wanted to go on. I took quick little breath, then nodded. Slowly, he unbuckled his belt and slid the zipper down.
"Have you ever seen a naked boy before?"
“I’ve seen lots of pictures, so I have a pretty good idea what to expect, but I’ve never seen a naked man before,” I replied with a shaky voice. Moments later, I was looking at a naked man with a jutting erection sticking out at me. I stared at it for several seconds, trying to imagine what it was going to feel like inside my virgin little pussy. More of a concern to me was if it would even fit inside me. I reached out and began fondling his cock. Kirk tensed up as I touched him, then leaned back and relaxed. I played with his cock, running my fingers up and down, finally playing with his balls, feeling the wrinkled bag and silky smooth balls inside. After several minutes, Kirk told me to wait for a minute. He reached over and pulled open one of the little drawers under the seats. He pulled it all the way out then reached inside and to one side. He withdrew a box of condoms, and a tube spermicidal jelly.
He said I needed to pay careful attention, because it was really important that I never did it with anybody without a condom. To be on the safe side, I should always use a spermicidal jelly just in case the condom broke. He opened the foil package, then placed the rolled device on the tip of his cock, and then began rolling it down. When he had it rolled all the way down, he kissed me passionately, then pressed me down on the soft carpet. We kissed and cuddled for several minutes as he began stroking my dripping wet little pussy. I shuddered with delight as he slid his finger into the depths of my hot cunt. By now, I could hardly keep from screaming out. Kirk continued to stroke me until I thought I couldn't stand it another second. Abruptly, he pulled back and looked deeply into my eyes.
"If you want to stop, this is about your last chance."
I didn't answer, just lay back and opened my legs. Kirk took the tube of jelly and spread a generous blob on the tip of his cock, then laid it aside. Carefully, he positioned himself between my legs and began moving his cock toward my quivering pussy. He guided it toward the target with accuracy that could only have been learned through practice.
"Do you think it will fit?" I asked.
“It will probably feel really tight to you, but the only way to be sure is to give it a try,” he said with a smile. In a second, I felt the tip touch my opening. I tensed up, pulling back without really meaning to. Kirk was careful, just moving forward very slowly with gentle pressure. I was thoroughly wet, which combined with the jelly allowed him to slide in a little way. I could feel the stretching as he moved in and in. I had expected some pain, although I knew I had long since lost my hymen to tampons. Kirk stopped for a few seconds, looking into my eyes with a silent question mark on his face. I smiled and hugged him close.
Again, I felt him inch forward, invading my very being. His persistence but gentle pressure kept his cock moving steadily inward. The stretching had reached the point where it was just on the edge of pain.
"Is it all the way in?" I asked.
“It’s about half way in, Little Bit, but you’re doing fine for the first time. Let’s just rest and let you get used to being stretched out a bit,” Kirk replied as he kissed me on the forehead. I didn't respond, I was just trying to get used to the presence of his cock inside me.
“Just relax, Little Bit, just relax,” he kept whispering as he kissed my eyes, my nose and my lips.
I took a deep breath and concentrated on relaxing my bottom. All at once, I felt him slide right on in until he bumped something deep inside my belly. I let out a little gasp, kind of a mixture of pleasure, pain and surprise. Kirk stopped his forward movement and held me tight as he continued kissing me all over.
“Hey, Little Bit, you doing OK?” he whispered as he nibbled on my ear.
“It feels really full and I can feel you hitting something deep inside, so don’t try to go any deeper,” I whispered, aware that my heart was pounding.
We lay still for a few seconds then Kirk began to move in and out carefully. I lay still, getting used to the feeling. Presently, the feeling of fullness gave way to a very pleasant feeling, and I began meeting his forward movements with my own thrusts. After several awkward moves, I became aware that his cock was going deeper and deeper, until I felt his balls bumping my quivering little ass. He kept thrusting for a few more seconds, then suddenly pushed in deeper and held me tight. I could feel his cock jerking and pulsing inside my bottom then he collapsed on top of me.
In spite of the pleasant feeling, the difference between our sizes was a bit over whelming, so I pushed him off to one side. He held me close, and rolled me over with him. After several minutes, he slid out of me and sat up. Carefully, he removed the condom, and wrapped it in a piece of newspaper.
"Did you like it?" he asked.
“I think so,” I nodded, “I’m glad we did it, but I’m not real sure what I think about it just yet.”
“Hey, Little Bit, you did great for the first time ever, just don’t gauge making love with just the first time, it takes some practice to learn to enjoy it."
We lay in the warmth of the van for about half an hour talking and cuddling. As I moved, I felt his cock pressing against my leg, and realized that once again he was fully erect and ready for action.
"Would you like to do it again?" he asked.
I nodded then asked if I could put the condom on him. He tossed me one of the foil packages, and gave me directions. Shortly, he was appropriately dressed for action. He spread some jelly on his cock and got between my legs again. He pressed forward, and in a single slow careful motion, slid right in! This time I moved with him. Since he had come only thirty minutes before, he didn't come so quick this time. We pumped into each other for several minutes when once again he collapsed on me breathing hard.
We did it one more time before we decided that we would be missed if we didn't get back home soon. In order to be more discreet, Kirk dropped me at the shopping center before going home. I spent a few minutes wandering around, bought a new scarf and a few other odds and ends, and then called home asking if someone could come pick me up. Kirk had told them that we took the van for a test drive and dropped me off to go shopping with friends. Everyone seemed to buy the story, so no questions were asked.
Just as the guys were leaving on Sunday afternoon, I engaged Kirk in a conversation, asking about his education plans. No one seemed to notice the implications when I asked if he had considered going on for a master’s degree. He glanced at me with a funny little look. I didn't let on like there was any thing but simple curiosity when I suggested that he really should consider advancing his educational opportunities.
The following week, Justin and I made love. It was perfect!