My Very First Time

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An eighteen year old guy finally gets it on.
4.8k words
4.41
130.2k
11

Part 1 of the 2 part series

Updated 10/22/2022
Created 06/26/2008
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So, I'm lying in bed looking at my Hooter's posters. I have six of them on the wall. It took me six months for my Mom to let me put them up and every now and then my little sister Dody comes in, looks at them and whispers "Pervert!" shakes her head and leaves the room.

But tonight, I'm looking at them and playing with myself. Okay, so I'm eighteen. But just eighteen, okay? The first time I jacked off was when I was twelve and I thought I'd found paradise. Since then about every two or three days I'll look at those posters, especially the one of Tiffany and I get a hard on and then, well, you know. I do sleep better after, that is for sure.

But right now, I'm not thinking of Tiffany or any of the other posters. No. Tonight I am thinking of Angelica. Man, she is built! Her tits are like a thirty-four and she wears these real tight sweaters and tight jeans to school. I met her at this teen age club called Dukes a couple of months ago and we really hit it off and I danced with her and now we eat lunch together like four times a week at school and we had our first real date last week.

My Dad loaned me his Toyota and we went to Dukes and we made out in the car afterward and I got to touch her tits but just a little and I am really hot for her and I think she is for me, too.

Yeah, we got some girls at Lower Wellington High School who "go all the way" but it's not cool to date them. The football guys like fuck them all the time I guess, but I'm still a virgin except for my right hand, of course. Okay, so maybe I'm not cool because I'm still a virgin at eighteen. But that's the way it is.

Well, my last girlfriend was Becky Bernstein and she was really cute and I've known her since Junior High.. So one day last year we were at her house and up in her room doing some research on her computer and sitting really close and she suddenly leaned over and kissed me and put her hand on my leg.

I got like this incredible hard on and I reached over and kissed her and she tongued me and I tongued her back but that was it for that time. And after that, whenever we were alone up in her room we would kiss and one time we actually got on the bed when her folks weren't home. And she had this blouse on and she unbuttoned it and she was wearing a bra and she had these tiny tits. She was fifteen and I was too, but the truth is she is about the same now that she's seventeen.

But that time she took my hand and put it on one and I kind of stroked it and I felt her nipple get hard and then my dick got hard and I don't know what would have happened next but I almost came in my pants. But then we heard the door slam downstairs and we got up really quick and she straightened out the bed and I sat down in a chair and she sat at the computer and she was all flushed.

But then abut a week later some guy she used to know came back to school and that was the end of things for Becky Bernstein and me. Oh well.

Anyway, I'm thinking of Angelica whose last name is Sanchez and I'm stroking my dick which is plenty hard by now. Angelica is Puerto Rican. Well, yeah, on her father's side and Venezuelan on her mother's side. So she is a really dark brown with huge brown eyes and like I said, this great build.

And I'm thinking about her long brown hair and how it would feel if she gave me a blow job which I have never had but the guys tell me that it just this side of heaven. And I'm pounding away and then I cum and I'm shuddering and I grab the towel I took a shower with and wipe myself and now I think I can get to sleep. And I do.

Well, it is coming up on Friday and I have nothing planned for the weekend. I'm not sure what Angelica has in mind and I have about a half day's chores at home that I could do on Saturday if I don't sleep in which is my regular routine.

So at school I miss Angelica at lunch but I see her as school is letting out and she gives me this big smile.

"Hello, JeromeWoodley!" She always says my first and last name together, but it sounds really neat.

Now, she and I are both seniors and school has about three weeks left, so it is warm outside and we both have what we

call "Senioritis" which is an I-don't-give-a-shit attitude about school. I mean we are still wading through the last of finals, but most of us have sent away our stuff for college and now comes the waiting period which sucks, but what can you do?

Angelica is wearing a regular sweater with a V neck and I know she is wearing nothing but her bra underneath and the V is kind of deep and I can see some cleavage. Not too much, because Lower Wellington High School would never stand for that.

"Hey, Angelica! Wha's happening?"

"Nothing too much Jerome Woodley. What do you have planned for the weekend?"

"Dirty work, I'm afraid. Like I have a garage to clean out and the lawn to rake. Big deal, huh? What about you?"

"Well, I have to house sit the two dogs and our cat. Mother and Dad went to a lawyer's conference together."

It's kinda weird, but her Dad is a Judge and my Dad is a lawyer and they know each other. That really doesn't have an impact on Angelica and me. At least not yet.

"Shame!" I say. "I thought maybe we could get together at the Mall tonight."

"No way, Jerome Woodley. I have to get home." She looks at me with those huge brown eyes. She has this way of staring right at you when she talks. It's like almost hypnosis, I guess. "Could you come over?"

"You mean like now?"

"Unless you have to get right to the garage and the lawn."

"Umm...no! I mean, shit, that will wait until tomorrow morning. Of course."

So we get on the same school bus and we're chatting up a storm about my loser friends and how I did at wrestling this year, which was better than last year when I broke my arm and missed the last three matches of the year, including the State Championships.

"You look a lot bigger than last year, Jerome Woodley. Are you working out?"

"Oh, yeah. Weights and running and push ups and stuff. I get in the weight room with the weight lifting team. Coach Dumtree wants me to wrestle in college."

We are sitting together towards the back of the bus and the bus is not crowded at all. She reaches over and grabs my arm at the bicep. Now, biceps are still a pretty new thing for me.

Until I started wrestling four years ago, I was a skinny twerp. But now I'm all the way up to 125 pounds. I know, that's no Incredible Hulk, but hey, for me that is really cool.

"Jerome!" She says and her voice gets really breathy. "You have such muscles! Why did I not notice before?"

"Umm...I dunno. Umm...do you like muscles?" What a stupid question.

She breaks into a laugh. Her laugh is like bells tinkling and her teeth are so white against her dark skin. Man it is a turn on!

"Jerome Woodley! Of course I do. She leans over to me and almost whispers in my ear. "I love strong bodies. I love to feel strong muscles." With that she just sits back and stares out the window. I'm glad because I got a boner that I'm afraid is showing through my jeans.

We get to her stop and my hard on has subsided a bit, thank God. We walk about a block to her house which is really cool. I have been there a couple of times and met her Mom and Dad who are really nice. But we have never been there alone. I really don't know what to expect.

We go in the front door, which of course I cannot do at my house. It is back door, shoes off. That is the rule and don't you forget it. So, she drops her back pack on a bench in the front hall and I do the same.

"Whoops!" I say. "Better call my Mom to tell her I won't be home on the bus."

"You can tell her where you are, Jerome Woodley. She's picked you up here before, yes?"

"Yeah, right!"

Angelica comes up really close to me then and puts her hand on my arm and squeezes my bicep again. "But not too soon, okay?"

There goes my willie again! "Umm...sure!" I don't get Mom but I get her answering message which is just as well because I don't need to get into a big thing about why I'm at Angelica's now.

"Mom?" I say into the phone. "Umm...I'm with some kids at Angelica's," I wink at her and she winks back. "And, umm...could you pick me up about five? Thanks Mom" I hang up and I'm grinning big time and so is Angelica.

"Something to drink, Jerome Woodley?"

"Yeah, sure, Angelica."

She takes my hand and leads me into their kitchen. The kitchen is really cool with a big cooking island in the middle with all kinds of pots and pans hanging down. She goes in the refrigerator and takes out two Coke cans. She hands me both of them and I flip the tops and hand one back to her.

She goes to the radio and turns on a Spanish station of which we have like eight in our town now. "So, Jerome Woodley, you want to dance?"

Now understand I don't dance. I mean not normally. Yeah, the night I met Angelica at Dukes, I danced with her, but that is because she asked me to and I wanted to get to know her and stuff. But man, this is in her kitchen and just the two of us and I don't want to look like a dork. But I shrug and we start to do this reggeton.

I'm moving as best I can and she is wiggling all over the kitchen and her boobs are bobbing up and down and her ass is moving like a cement mixer and man am I turned on.

She slides right up to me and is up against me and I like stumble a little and end up backed up to that island I told you about. She stops right there and her eyes look all smokey and she puts her tongue on her lips. She has these lips. Man. I mean the lower one sticks out a little and is really sexy. She leans in closer. We are like crotch to crotch.

"Jerome Woodley," she almost whispers. "You remember how we kissed in the car?"

I can hardly breathe. "Oh man, yeah. I sure do!"

"And do you remember what it felt like when you touched me?"

"Of course I do!"

"Well?"

So I put my arms around her and lay one on her really good. It is a wet kiss like I never had before even with Becky Bernstein. And then her tongue! She is in my mouth and I'm in hers and I have a hard on like I never had and I don't know what comes next. Really.

She backs off just a little and keeps grinding her hips into my crotch. I swear I'm going to cum.

"You have muscles besides your biceps, don't you, Jerome Woodley?"

"Umm...yeah, I guess." What the fuck am I supposed to say?

She has a hold of both my arms and then she drops her arms and one hand reaches down and strokes my jeans right on top of my dick. I'm beginning to sweat.

"Yes, Jerome Woodley, you have other muscles, do you not?"

Suddenly she backs off and grabs her coke. She takes a big swig and smiles at me. What is she, big cock tease? Then she takes my hand and leads me out of the kitchen, into the front hall and up this winding staircase. I'm stumbling behind her. I've never been upstairs at the Sanchez house. At the top of the stairs she leads me into the second door just to the right of the stairs.

"This, Jerome Woodley, is my bedroom." It is painted a light blue and the bed is about the same size as mine. There is a desk with a computer and a big chair in the corner and posters of these Latin singers on the walls. She sits down on the bed and I'm

standing there like a dork not knowing what to do except I'm more excited than I have ever been in my life.

Angelica reaches up and takes off her sweater. Oh my God! Her boobs are gorgeous. I mean she has this flimsy bra on so I can see a lot more than I would in a bikini top.

"And can I see your chest, Jerome Woodley?"

Now, I'm not really buffed, but I have been in the weight room. So, I pull my tee shirt out of my jeans and pull it off.

She gets off the bed and comes real close to me and starts to rub my chest. She rubs my nipples for God sake! Now I never gave much thought to my nipples , but man they get hard too! And I get a sensation all way down to my nuts.

"Kiss me again, Jerome Woodley," she whispers.

So I put my arm around her and we go at it again, tongues and all. Then she takes her arms out from around me and reaches in back of her and undoes her bra. She shakes a little and it falls to the floor and there she is, half naked!

I remember the one time I felt Becky Bernstein's boob through her bra, but this is way different.

She takes my hand and lifts it to her right boob. "How does it feel, Jerome Woodley?"

I can't talk. I'm leaning down and I'm stroking and kissing this incredible breast on the hottest girl I've ever met and I think I'm going to faint, or at least shoot my load in my jeans.

"Are you wet, Jerome Woodley" she like whispers in my ear. At first I don't know what she means and then I realize that Angelica Sanchez is no innocent little girl. Not that I shouldn't have figured that out when she stroked my dick through my jeans or at least when she took her bra off, but she is talking about what the guys call pre-cum, that little wet stuff that comes out of your cock when you get really excited but haven't cum yet.

"I, I think I must be." I have trouble breathing, never mind talking.

"And I am too, Jerome Woodley. Feel." And with that she unzips her jeans, takes my hand and puts it down on her crotch. Oh my God! I feel her pussy through her panties! And Damn! It is wet as hell!

"You see?" She whispers holding my hand against her pussy. I just leave it there, I don't reach in or anything. I mean this is new territory for Jerome.

"I see, Angelica, and I feel it too!" God I finally managed to say something.

"And you?" She asks, still holding my hand there.

"What?" It's not the brightest answer, but what the hell...

She takes her hand away from mine, but I don't move mine – not a quarter of an inch. She takes that hand, her other arm still around my back and pulls down the zipper on my jeans. She reaches in and actually touches my prick through my jockeys.

Now I am going to cum, I know it. She takes her hand and reaches for my belt and undoes it and the top button on my jeans. Then she takes both her hands and pulls them down to my hips. She squats and my hand comes out of her jeans. She wiggles my jeans down to my ankles, reaches up and pulls down my jockeys.

And there I am. Pants and jockeys down around my ankles so I can't move, my dick standing at absolute attention. Now, I gotta tell you. I don't have a twelve inch dick like those guys in the porno sites on the Internet. More like five, maybe six when it's hard. And it has this little crooked bend in the middle when it's hard. And it is hard now, very, very hard.

Angelica is looking at it like it is some freaking artifact and I am just standing there hoping I don't shoot jiz all over her face. She smiles up at me and God! Her hair is around her face like in my fantasies. She reaches one hand out and grabs my dick. Not hard, but really gentle. She smiles up at me.

"You are beautiful, Jerome Woodley." She begins to stroke me just a little and yeah, there is pre-cum on my dick and she is stroking it and getting it wet. I do not know what I am supposed to do.

I can't move because of my jeans down around my ankles with my jockeys. I can't reach her because she is squatted in front of me. So I stand with my hands at my sides and my knees are starting to tremble.

"For God sake, Angelica," I finally squeak. "I am going to freaking cum all over you hand if you keep that up."

She smiles up at me and stops stroking my dick. I don't know if happy about that or not.

She is standing beside me now, looking at my cock. Then she turns and climbs up on the bed/ lying on her back. She pats the bed next to her. Okay, what do I do? Do I pull up my jeans or at least my jockeys?

Well, she still has her panties on so I wiggle my feet on my jeans until I'm out of them, slip out of my socks, pull up my jockeys and step to the bed.

Okay, so we are lying next to each other, pretty close to naked. I'm still hard as hell and almost popping through my jockeys. She leans up on one elbow and looks at me in that way she has.

"Have you ever been this close to a girl before, Jerome Woodley?"

"No Angelica, I swear I haven't."

She laughs a little and puts her hand on my chest. "I'm just asking, Jerome, just asking. You seem so nervous."

"Well, yeah! I am. I mean you are the hottest girl I have ever known and here we are our first time really alone together and we are almost freaking naked and I am lying on your bed with you and God, Angelica! I am so horny right now!"

"Of course you are, my darling," she winks at me with those incredible eyes. With that she takes the hand that is on my chest and brings it down across my stomach and reaches inside my jockeys and grabs my dick again. She sits back on her haunches and pulls my jockeys down with both hands and throws them on the floor.

Then she leans down and begins to kiss the top of my dick. Oh my God! This is what I was jacking off to last night!

"Does that feel good Jerome?"

"Oh my God, Angelica, it feels, I mean, I mean..."

She giggles again a little and the next thing I know she is holding my cock and sucking on it. I mean really lathering it with her tongue moving all around it and then taking the whole thing in her mouth and it is warm and wet and I am stretched out with my legs spread and my muscles all tight. I see her head gong up and down faster and faster and her hair is flying around her head and this is a ton better than my fantasy and then....

Oh man, this is it! I am going to CUM!! And with that, I shoot this incredible amount of jiz and she just keeps sucking on my cock and it is so freaking sensitive I think I'm going to faint.

Finally she sits up and there is this little bit of my cum around her lips and her eyes are all smoky again. She licks her lips and then comes up and lies down beside me, with her head on my chest. I am still breathing like I just finished a marathon or something.

She looks up at me. I slowly put one arm around her naked back. I feel her boobs against my side and I am actually dizzy.

"Was that good, Jerome Woodley?" She almost whispers it.

"Oh my God, Angelica. I never, I mean this is the very first time I ever, I mean, well, I've never been with a girl before! Not naked, I mean and then I mean I never had anybody take my dick in their mouth and before this I only came on my own like, well you know..."

"I loved it too, Jerome Woodley. You are a beautiful man. Now, are you going to brag to all your friends that the Judge's daughter sucked you off?"

I sit up really fast and she has to roll off me and is sitting on the bed with nothing but her panties on and her boobs are incredible and the nipples are hard and damn! I'm getting hard again, already.

"No! Angelica! How could you even think such a thing! This is a well, a sacred moment for me. I don't want to share this with anyone. Honest!"

"I believe you Jerome Woodley". She smiles then and reaches for me. She puts her hand behind my neck and kisses me really softly. I mean, Angelica is my age, but damn! She is a woman and I know now man, I am just a boy. A horny boy, yeah, but just a boy.

As she sits back she looks down and sees my dick is hard again. She smiles at me. "Wow, Jerome Woodley, that did not take you long, did it?"

"Well, for God sake Angelica, you are sitting there with prettiest boobs, I mean breasts I have ever seen and wearing nothing but your panties and well, for God Sake!"

She puts her hand up to her mouth and giggles. "Well then come, Jerome Woodley, kiss them." With that she lies down on her back and stretches her arms behind her head and even spreads her legs out.

So I move over and I'm like lying beside her and I lean over and kiss the right breast really gently and I see the nipple begin to get even stiffer and she starts to breathe a little harder. I have seen enough porno movies to get the idea here so I take my tongue and softly lick at her nipple. She begins to moan a little and move her hips on the bed.

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