She Set Her Sights on Derek

It wasn’t that I had the hots for him. Well, maybe it was that, but it wasn’t one of those passing crushes. He made me weak when he was in the room. He made my chest hurt and sometimes it was hard to breath. I even got shy around him. It’s not that I was all flustered and out of control. I didn’t start doing dumb things or stumble all over myself; I just got shy sometimes. I got shy and wished things could be different; things that couldn’t be changed. I wished for that a lot.

Really though, I was never a shy type person. I was a girl pretty much without inhibitions and I think I was mature for my age. I was a model, after all. And there are things about modeling that force a girl to grow up in some ways faster than others. At first it’s mostly fun and glitter, but a girl will find herself in a life style she might not have been prepared for. To survive it, you grow up faster than you’re supposed to. You experience things that aren’t supposed to blemish youth. But, I only say all this so people will know, I wasn’t just a little school girl. I wasn’t a tramp either. Actually, for the life I led, I think I was more conservative than most.

Well, I started to do things to catch his eye; not really thinking anything would come of it, but I ached for his attention. I needed to feel he noticed me. Models get tons of clothes so I could find things that I thought would be subtly sexy. I didn’t flaunt it or anything. I’m just not that way. But I could wear things that flattered me without making a spectacle of myself. I wore my blonde hair fairly short. I had a really nice figure for my age, but not a knockout figure. I was pretty small really. I stood about 5’ 3” and my weight was right on for my size. If we talk about sex, well, my sex features were 32 B’s; so like I say, I wasn’t a knockout, but I had no trouble turning heads. A lot of my modeling was bathing suits and underwear, so at least I knew I wasn’t unattractive to look at.

One of the photographers I worked with tried really hard to get me to pose naked. He promised it was completely confidential and that I’d be totally safe with him. He said the photos wouldn’t be used for anything without my permission and that doing the shoot, would truly liberate me. He said it would make me more confident and capable for regular shoots. I wanted to do it, but for the wrong reason, I think. For me, it felt deliciously naughty. I even had images of really porn looking poses. But, in the end it was just fantasy and I didn’t do it, so I remained unseen in the buff by the opposite sex.

Well, I said I did things to catch Derek’s eyes. He was so hot. Derek stood 6’ even. He was thin but his muscles were well toned. I used to love to see him with his shirt off and I still remember the first time I brushed against his gorgeous body. Usually, I would do things like bend over where he would see my ass or a little bit of tit, or in pants and shorts I’d set with my knees apart so he’d see the shape between my legs. But, one day he was showing me how to do some of my work and I just did it. I moved close and pressed against his hand with my breast as I watched what he was doing. I can’t begin to explain what a rush it felt like to do that. I mean, girls do that to guys all the time, I know. But that was the boldest thing I had ever done with sex, and I assure you it was about sex. Wow, I had the most sudden fever I have ever experienced and I’m sure I blushed because my nipple totally betrayed me.

He paused briefly. It was almost imperceptible but he did pause. I know I got his attention and I think he liked it, but he did get quiet for a moment. For me though, the rush I got from that feeling stuck with me for days. You have no idea how much I wished for him to just walk up to me and touch my breasts. I’d have let him have them as long as he wanted.

He seemed cautious around me for a little while after that. It wasn’t like he was standoffish or anything. It was just more like he measured how he talked to me and how he treated me. But, I also found that he paid me more attention even if it did feel more distant. And I caught him looking at me more. Quietly, he was paying attention. I think he got cautious because I turned him on and he wasn’t sure how to deal with it. And that was one of those things I wrote about that I said I wished I could change certain things. See, Derek was 28. Derek was 28 and I was 15.

Well, it came to a head one day when I won employee of the quarter. I was surprised because I wasn’t an employee really. I mean, I got paid but I was there because of school. I was in this entrepreneur program at school, and I was a straight “A” student so I got to work and get credit. I was a hostess at Derek’s restaurant. With the award was a dinner for two at a really nice place on the waterfront and I was scheming not long after I won.

The next evening when we were sort of alone for a few minutes I thanked him for the gift certificate. He was so damn humble. He said it was from my team, not from him. It just made me like him more. Well, whatever…my plan was underway.

“Derek?” I started out. “Would you take me to use this?”

He looked at me with sort of a combination of shock and puzzlement, and suspicion. “Oh, come on, Dori. You must have a few boyfriends that would want to go with you?”

I couldn’t tell if he was fishing to find out if I had a boyfriend or if he was avoiding answering the question, so I pressed on.

“There isn’t anybody I want to ask. But it’s a big deal. I’d like to go with you sort of to say thanks for giving me this opportunity for school.”

“I just can’t imagine you wouldn’t want to share it with one of your friends. What about a girlfriend? It would be a fun night out for a couple crazy girls your age.”

That one bothered me and I think he saw my disappointment. I didn’t want it to be about age. I know I had no business trying to connect with a guy so much older, but I felt old enough to go out with him. I wanted to go out with him. I wanted to spend some time with him outside the atmosphere of his restaurant. OK, who am I kidding? I did have the hots for him and I was scheming – so what? I was crushed that he wasn’t jumping on it. And I was crushed that he brought up age.

I think he could see my disappointment because of the way he gave in. He acted like had hurt me and wanted to make it right. “Ok, Dori, tell you what. I’ll take you on one condition. I buy dinner and you keep the certificate and take a friend another time. But, Dori, this wouldn’t look good. You can’t go telling everybody or all the employees will wonder why I don’t take them all out when they win.”

That was good enough for me. I had a date with Derek and I felt higher than a kite. Everybody kept asking all night what was up with me. I guess my giddiness showed, but I didn’t let on to anybody. I think Derek would have been pretty pissed if I told someone we were going out.

At my age, I didn’t know anything about the subtleties of seduction but I had learned some about being sexy. Modeling underwear and bikinis might have been geared toward shoppers, but most girls buying that stuff want to look sexy wearing them. It’s a model’s job to convince them they will. Well, I wanted to look sexy. At the same time, I wanted to be a bit conservative, and I didn’t want to overdo it. Mostly, I wanted to look more grown up. I wore a moderately short black skirt that with the right moves could show more leg if I needed to. I wore red boy shorts. I thought about pink but red seemed a little older. I also wore just a little bit of heel to get myself looking taller. I wore a white silk top with spaghetti straps and I wore it braless. My breasts were small enough that it had somewhat of a modest look but I was determined. The next time I pressed a breast against Derek, I wanted him to have no doubt that there was fresh, young meat under my top.

That takes me to the other part of my determination. I fully intended to fuck Derek. I was tired of turning down opportunities because the guy just wasn’t someone I want to give my virginity to. I was also tired of the dildo my mom had gotten me. That would be the one she was so proud of telling me was just like hers. She said I needed it because it would help me avoid sex in the industry I was working in. She never said why she needed one; she had boyfriends around all the time. In fact, the Friday Derek and I were going out, she was headed across the state to spend the weekend with a guy.

Anyway, I wanted sex. I wanted it so bad that if I could just get Derek to do me, then I’d let him do just about anything else he wanted – anything.

Sliding into his car was one of those times I let my skirt ride up to show him my legs. As I climbed into the driver’s seat I properly pulled it down to where it belonged. Being sexy is not being a trollop. Derek was watching, but like before, he seemed cautious. I liked that. I liked thinking he might be nervous about being out with me. I liked that he might be nervous about what I had in mind, but outwardly, I behaved myself.

I behaved myself all through dinner, actually and had a great time being all lady-like and everything. I could tell Derek enjoyed the evening too and we turned out to be pretty good company for two people so far separated in years. After dinner, though, we strolled in the park a little and that’s when I started trying to do some of those subtle things. He got a few bumps and brushes and I wasn’t shy about touching. The big one, though, was once when he was standing with his arms at his side. I wrapped both of mine around one of his and pulled it between my breasts. Yeah, if he didn’t know I was braless before he sure knew by then. He lingered there. I know he liked it and I felt all tingly.

On the way home I had to find a way to make the night last. I started off sounding like it was a question.

“Derek?”

“Yeah,” he said, glancing over at me. He couldn’t avoid taking a quick peek at my legs.

“I want some wine. Can we get some? It would have been nice to be able to have wine with a dinner like that.”

“Oh, yeah, that’s a grand idea.” He laughed a little. “I need to get myself arrested for giving booze to a 15 year old.

Where exactly would I take you for wine anyway?”

I got just a little bit coy. I did know how to put on expressions, by the way. “Oh, someplace not so public. Everybody says you have a really cool condo. Can I see it?”

“Holy shit, Dori. What are you trying to do to me? I’m going to take you to my condo and get you drunk? No, I don’t think that sounds like a good plan.”

We batted it back and forth for a little while, but you know I won, right? How much argument can a guy put on with a girl that’s coming on to him? Yes, he gave in and before long he was pouring wine while I stared out the bay window at his view of the water. The condo was so cool. I felt like I was having sex already.

Derek sat on the floor with his back against the couch. I liked that. I stood close by; just close enough in fact, that he could see just a little bit up my skirt. Then I sat myself down right between his legs with my back against his chest. We sipped our wine and talked while his music played in the background. I’ve had wine, plenty of times. My mom always has it in the house and she doesn’t care. I don’t think we really needed the wine but it was nice to have. I couldn’t imagine Derek wasn’t already seeing this night was going further than he had anticipated and he was actually starting to loosen up a little. He didn’t seem so cautious. Then, to coolest thing happened.

I had my knees drawn back toward my chest and my skirt had fallen almost to my lap. Behind me he couldn’t see anything but leg, but it felt bold to me. I had my wrists draped over my knees when Derek set his glass down and reached up to rest his hands on my arms. He bent and smelled my hair. Holy cow, my whole body went into a hot flash. It was the first thing he had really done to connect with me. After a few minutes, I let my hands drop to the floor and Derek stroked my bare arms for a while. Then, he did it. He reached around to the front of me and molded his palms to my little breasts. I felt like I couldn’t fill his hands but my nipples went berserk. I leaned backwards and lay my head against his chest and let him have his way.

Pretty soon, his way was to slide his hands to the bottom of my shirt and slide them back up inside it. The heat of his hands against my bare skin was like nothing I had ever felt and I know I held my breath until he got back to my breasts. He cupped them and massaged them and he caught my hard nipples between his fingers. I was lost. I thought I had this whole thing under control; like I was in charge. Suddenly, I wasn’t. I was scared, actually, but at that moment Derek could have done anything he wanted to me. But then, that’s what I was there for wasn’t it?

The next thing I knew, Derek was sliding my top up over my head. He caressed and stroked my shoulders and arms and back and played more with my tits. It hadn’t taken any time at all for me to figure out this had been a really good idea and I let his hands wander all they wanted. I was definitely learning there was better technique to breast cuddling and nipple twisting than any of my friends had enough experience to understand. I decided it was time to turn up the heat and assumed I would be getting laid within minutes.

I excused myself, leaning over to give him a peck on the forehead before I went to the bathroom. I was grinning inside – my tits waving around in front of him. I loved it. It felt so natural to be half naked and I had just flashed myself to the first guy to see me without at least some of my clothes. I couldn’t wait to lose the rest.

I freshened up a bit, lost my skirt and came back to him wearing just my lacy red boy shorts and carrying my wine. Damn, being sexy at a guy is hot. I was loving this. This time, I didn’t sit between his legs. I pushed them together and straddled them on my knees. Spreading my legs to do that, I gave him a nice view of the shape of my mound and now I had my tits right in front of his face. I was dying to feel his lips and see if he’d bit my nipples. Well, he did. And he sucked them so sweetly. I was already clenching the muscles of my pussy, when I reached down and started to undo his pants. Yes, I was about to grab my first cock and if he complied, I was going to find out what one tastes like. I pulled his belt loose, unfastened the snap and eased down his zipper while he watched my hands. He was wearing gray stretch boxers and I was looking him right in the eyes when I pulled the waistband to get room to slide my other hand in. In seconds, I had my fingers wrapped around skin that felt just as silky as my pussy. I had no idea a hard cock could be so soft – and wet. The tip was sticky.

I grinned at him. “Is that cum?”

“Um, not exactly. You don’t know about precum?” he asked suspiciously.

“I’ve heard of it, but no, I don’t really know anything about it.” I was giggling.

Derek looked concerned. “Dori, is this new to you?”

I didn’t answer. I bent down and pulled his cock from his pants and touched the tip of my tongue to the tip of his head. I wanted to taste it. I can say now that I am more experienced, Derek wasn’t exceptionally large, but he was bigger than I ever expected a cock to be. It was bigger than my dildo anyway. After licking his tip for a while, I plunged, and my antics turned into a blow job. I was ecstatic. I was sucking a cock and Derek’s hips were writhing under my face as he ran his fingers into my hair.

My big problem was, I didn’t really know what to do, so for a while I just kept bobbing up and down. Then I got an urge to see how far I could push him in. I gagged myself a couple of times before I got the hang of it, but it was kind of exciting to figure out how to get so much of him in and to push him so deep. I experimented a little and judging by his reactions, I was at least doing a couple of things right. When my mouth got tired once, I pursed my lips round the rim of his head and I just licked his tip. He liked that, I’m sure of it.

Eventually, though, I felt his hands trying to pull me off. I was still holding his shaft when I looked up at him. I was afraid I had hurt him or something and it took a couple minutes for him to make me understand he was about ready to cum. So, let me tell you guys something. If you are with a young lady having her first playtime with a guy’s manhood, do not deny her the experience of getting you off – never.

Making Derek cum hadn’t even crossed my mind until he said that. Do you have any idea how cool it is when a girl finds out she was doing something good enough to get her guy off? This was about to be an adventure I hadn’t even thought of. I went right back to work and no matter how hard Derek tried to stop me, I kept working on him until it happened. I felt Derek tense up and I felt his cock sort of twitch or buck a few times and then his warm jizz shot into my mouth. This was so hot. He shot again and again and again and my tongue was swimming in it. I could feel his juice all over the inside of my mouth and my swallow reflex took over. Yep, I sucked Derek’s cum and I swallowed it. I kept swallowing until I couldn’t find any more to swallow. I was giggling and bouncing around like a kid with a new toy, and I was darned proud of myself. Pretty silly I guess, but this was an exciting moment for me.

I tried for a long time to figure out how to describe the taste. Wasn’t like anything I had ever tasted. And, like most say, it was a little salty but I still can’t describe the taste. I can say it was just a little slimy feeling, but that was ok. I liked how the taste lingered but what really made me hot was the smell. Oh, it smelled so much like sex. It smelled feral and musky.

Well, I fiddled with him for a while and he softened up some and that’s when it struck me. I’m here, almost naked and I just sucked him until he had an orgasm. He came in my mouth and I swallowed it, and we haven’t kissed. I felt such a sudden connection with that I really wanted to kiss him, and I’m not even that big on kissing. I rose up so our faces were close. I didn’t even know if he’d want to kiss a mouth that just took his cum. It was cool; just like in the movies. I just held my face real close to his where he could feel my breath and I watched his eyes. And then we did it. Derek kissed me. He didn’t just give me a peck; he really kissed me. He felt my lips and my teeth with his tongue and we kissed for a long time and he was holding me. I melted. This was feeling so wonderful.

Then I felt Derek’s hands. He reached around and cupped my ass. He kissed me some more and then he stood up, lifting me with him. He whispered in my ear. “Hold my pants up.” I laughed so hard. He had said it so seriously but when I grabbed his belt loops he started walking. Derek carried me to the bedroom and I am thinking to myself – “Oh. Oh, this it. This is really about to happen.”

But, Derek put me on the bed and while he was taking his pants and jockeys off he told me to lie on my stomach. I didn’t understand, but I did watch him toss his pants aside. Then he came to the bed and straddled my legs. I didn’t know what was going on and I was ready to be naked and feeling him push into me. I never gave a thought to the possibility that he might not be ready to go again for a little bit, nor to the possibility that he might be going to treat me to more than a fuck.

Derek started massaging my back and shoulders and sides. He scratched my skin and he kissed it and I could feel my whole body just sort of relaxing. I never expected to get treated like this. He kissed all the way down my back and down my legs too. It seemed like it went on forever and then he slipped his fingers into my panties at the hips, and started to push them down over my ass. As he pushed them down my legs as he was kissing my ass. Can you believe that? He was kissing my ass and dragging his tongue down between my cheeks. Oh, man, my pussy muscles were clenching so tight and I was wet and ready to get on with it.

Well, when Derek had been just about everyplace he could go on my backside he eased me over. It was just one more exciting moment for me. I was naked and he could see all of me. I never realized how cool it could feel to be looked at. His eyes sparkled. I know he liked what he saw. I do think he was a little surprised to see I didn’t have any pussy hair though. I guess you don’t expect that at my age, but when you model underwear and bikinis, you have to make sure there’s no hint. Well, I got tired of this bitch that comes around and trims you all up before a shoot. I didn’t like her messing around down there all the time so I showed her. I went and got waxed, and I liked it. I found out real quick that masturbating was a lot more enjoyable with no hair too.

Well, Derek treated my front just like he did my back. He hardly paid any attention to my breasts and pussy for quite a while but when he finally kissed my tits and went to work on my nipples it shook my whole body. It was really starting to feel like sex by then and he eased an arm between my thighs. Then he turned and put the other between my legs so he was resting on his elbows and pushing my legs apart. I could feel his hot breath on the skin of my pussy when it struck me that he was going down. I reached up and grabbed the rails of his headboard just as he slid his tongue into my crack.

I don’t know if youth has anything to do with the sensitivity of nerves or if it might have just been the excitement of the first time, but the feel of his tongue sliding down over my clit and into the slit of my lips was almost more than I could handle. I know I cried out but I have no idea what I said, and the feeling of his tongue in my flesh resounded over my entire body. I was suddenly on fire. I was gasping and couldn’t get my breath. I couldn’t hold still and I couldn’t move. I couldn’t do anything except completely surrender. I tried to push my hips up at him when he slid his tongue around my opening but that was hopeless. Then he slid a finger into my opening. He was focusing his tongue on my clit then and when he rubbed my front wall, I swear it sent sparks between the two places he was touching. Then he really surprised me. Derek slid a finger in my butt too. I knew I would like that, my Mom’s gift had been there a few times but it still surprised me. It also surprised me how good it felt to have something in both places while he sucked on my clit. I had to just let him have his way, but I’m sorry to say it didn’t last long. I felt my orgasm coming within minutes of the first lick, and I knew it was going to be huge.

I’ve never felt my whole body react to an orgasm like this before or since. Literally, I felt like every nerve I have was going nuts. I tingled, I tickled, I burned, and I started trembling. Oh, I was trembling. It was my legs mostly; they were rattling like they were going to fall off and I was hearing noises come from my throat that I’ve never heard before. Wave after wave of the climax shot from the apex of my legs downward and upward at the same time. I felt like one of those sci-fi movies where the guy is strapped into a chair and you can see the electricity shooting through his body. It was absolutely amazing and after Derek moved off of me I had to just lay there staring at the ceiling, wondering what in the heck had just happened to my body. Yes, I decided I like sex a lot.

Then we cuddled. That felt so warm and so safe. I finally whispered in his ear. “Fuck me now,” I said. He said no. Derek said he was already probably going to jail. He laughed, but he did say it. He said all he needed for them to throw away the key was to fuck me on top of it all. I argued, of course. I pleaded. “Please,” I whispered. “I want this.” We kissed a while and I rolled up on top of Derek. I laid flat on top of him and spread my legs outside his. I loved that feeling of his cock being between my legs and it was so, so close. I could wiggle around and feel his tip rub my lips. I finally started to push to see if I could slide him in, but Derek stopped me.

He rolled me off onto my back and he turned to his nightstand. I was so happy to see him pull a condom out of the drawer. It meant I was about to lose my virginity but I didn’t want him to use the condom. Mom got me on the pill at the same time she got me a dildo. Funny how maybe she didn’t want me to totally ignore men after all. Derek wouldn’t do it. He talked about jail again, but mostly he talked about who might be showing up with a gun if he got me pregnant. This time, I gave in. I wanted this and if that’s what it took to get it, I wasn’t going to argue any more.

I watched him put it on. It was fun to see him handling himself and I watched every little turn as he rolled it down his length. I kept my eyes on his cock as he eased between my legs and began to lower himself. I kept watching down there until I felt his tip at my opening and then it happened. I could feel my opening stretch as he slid in. It didn’t hurt; I guess I can thank mom for the dildo after all. It felt exquisite, actually. It felt absolutely heavenly as he sank deeper into me and his size pressed outward against my walls. He lowered himself closer as he slid deeper and he was resting on his elbows as he started moving around inside me. I guess he was rolling his hips and I could feel him sliding in and out and sort of corkscrewing as his cock moved.

I wish I could think of some way describe the feeling of a guy filling a girl’s opening like that. I have no words for it but wonderful. It certainly felt better than my dildo, but that’s probably because I could just lay there and let it happen, plus, there was a cool guy on the other end of it. I know you guys like the feel of sticking that thing in a girl’s warm wet places, but I want to tell you, it feels every bit as good for us.

There was some virtue to those orgasms we both had before hand too. We got to do this for a really long time. I would have been happy to go even longer, but I wouldn’t trade my next orgasm for anything. It built up so slow; I got to enjoy waiting for it. It wasn’t so intense as the first one, though. It was more like warm and comfortable and exciting all at once; sort of like desert after the main course I think. What made it even better was that once it was obvious it was coming, Derek felt it. Whatever he felt made him cum too. We did it together this time. I felt that twitching inside me and I heard him groaning and that made mine just that much better. I was double satisfied. I felt good from the enjoyable experience and the fucking and I felt good that doing me got him off too.

Derek treated me special. I liked that a lot. And I liked that when he asked when I needed to be home I got to tell him my mom was out of town and if I could, I wanted to stay with him. He let me, and later that night I woke up when I felt him stirring. He was getting another condom out of his drawer. I was giggling again. I got up on my knees this time and waited for that wonderful feeling to start all over again. I felt bad for all my friends who had told me how bad their first experience was, but I didn’t feel bad for long.

It may sound odd; a 15 year old chasing a guy Derek’s age, but he treated me good. He treated me like a lady instead of a kid. We had sex several more times that weekend. He was patient with me when I didn’t know things and I learned a lot that weekend. He was in no hurry. He took me slow and we talked. He wanted to know what was feeling good and all that. I could not have found a better guy to share my first time with. I’m older now but I wouldn’t change my nights with Derek for anything in the world.

Still love ya, Derek.