Gaining Confidence

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My first time isn’t a romantic story about two long young lovers who come together against the odds or an older woman showing me the ropes. I have a little different time; something a little more real and even better in my eyes. Probably because it’s how I lost my virginity.

My name is Jared. I’m a normal guy, by now a days standards. Overweight by at least 20 pounds, average looks, and I try to overcompensate with a humor that only my close friends get that leaves me no where with the ladies. But that doesn’t stop me, I still go out on the weekends talk up any girl that’ll play attention to me, but I could never seal the deal. Until this night…

Myself and a couple of my fraternity brothers went to a house party up the street from our apartment. Now this is nothing new, we walk in and take a seat amongst the best looking girls in the party, because even though I may not be the best looking dude around, my brothers would be in that category. We start drinking and doing our normal thing when all of a sudden there is a big scene by the doorway. I get up to check it out, it’s just some girl and her boyfriend or as it seems ex-boyfriend arguing. One of the girls we were with started saying how they were always fighting, it turns out that is her roommate.

She says her name is Erin and that she should go see how her friend is doing. Great that was the girl I was talking to tonight so I finish my beer and tell my brothers I’m going home.

I start to walk down the street and see a girl sitting in front of my apartment. Its the girl Erin.

Now normally I wouldn’t think twice about her because she is beautiful. A nice tan body, only 5′ 5″ but with 36,24,34 measurements. The most perfect brunette hair that came down to just below her shoulders. But the thing I’m most attracted to, is her eyes, they are a strange greyish blue. It didn’t help that her smile made her eyes glow.

Now I know what you think I invite her up and we end up in my room and we make passionate first time love. Nope, I’m a shy guy so the most I get out is

“Are you ok?”

She just looks up and almost gives me the look like ‘who the fuck are you’ until she recognizes me from the party; and says

“Yeah, I’m fine. My roommate, the one that I went after, is just a bitch. She said that I was trying to sleep with her boyfriend and that’s why they fight all the time.”

I started to laugh, just a little bit. I’m sorry but come on, girls fight over the craziest things.

So I say “Would like me to walk you home? Or you want to go and grab something to eat with me?”

She looks up and says “Yeah actually I could eat. But what’s open now?”

“Well there’s this little dive that’s open til 4, it’s not the best looking place but you can’t beat the food or the prices.”

“Cool, Etlik Escort lets go.”

We get to the restaurant and sit down in the first table we see, next to the jukebox. She didn’t notice but we were getting quite the stares, even I didn’t get how this girl was here in a back alley dive with me, of all people. We order our food and she really starts to look at me. It kind of creeps me out, no hot girls actually pay attention to me much less look me over. I’m wondering what to say until she speaks.

“So how do you know this place, I thought I’ve been everywhere in this town and I haven’t even heard of this?”

“My cousin used to go here a few years ago and told me about it and I decided to check it out and loved it. Now I only bring select people here.”

“Oh yeah, how did I become one of your select people”

“A moment of weakness”

She just looked at me and laughed. In the same moment turned around got up, I thought she was getting up to leave but actually was just going to play a song on the jukebox. As Elton John’s Tiny Dancer came on, I started to laugh and people began to groan but sure enough when the chorus came around, everyone sang along with the chorus. She is infectious, and no one can deny her.

As the next song came, thank goodness it wasn’t so cliche, our food came. And as I watched this beautiful woman scarf down her burger, cheese fries, and milk shake. I knew just from the look on her face, she had something in mind. I had no idea but she may be the greatest woman alive to this day.

By the time we got a little over half way done with eating, I had to ask.

“Why are you looking at me like that?” I laughed a little to try and hide my nervousness.

“Well I had a crazy idea and I was wondering if you wanted to go with it?”

“I’m not going to say yes, until I hear what you’re thinking?”

“Ok, well this is going to sound like it’s straight out of a movie but let me set you up with a girl.”

I almost choke on my fries. “What do you mean?”

“Well you’re obviously a good guy, I mean you don’t even know me and this is probably one of the best moments in my college history. Sooo why aren’t you out with more girls? I’ve seen you around and you only travel with your brothers and usually seem, umm not lonely but by yourself. You know what I mean.”

I can’t help but stare at her for a moment, am I that easy to get.

“Well I find it hard to talk to girls.”

“You’re talking to me right now…”

“Maybe you’re different.”

She just gave a slight smile and turned her head away, not wanting to look at me.

so I continued “I think I’m too nice.”

“Alright, alright so let me do this. I’ll get your confidence up. A little sex should Keçiören Escort help.”

I swear this woman is trying to get me to kill myself, because I almost choked again on my milkshake this time.

“You know I’m not a virgin.” Lying my ass off.

“I never said you were one.”

“Ok then, I’ll try it out.”

We finished eating and paid and started to walk back. As we get to her apartment after little back and forth, she gives me her number and I call her so she has mine. She says that she’ll call me tomorrow so we can do something.


I had gone home and drank more later that night so I was fast asleep when I heard my phone going off. I picked it up, and heard “Hello, is this Jared? It’s Erin.”

“yeah, what’s up Erin?”

“Hey get up you’re going out with my friend Megan tonight and we got to get you ready.”

“Erin, what are you talking about? Who’s Megan and why do I need to get ready?”

“I know you remember what we talked about last night,” Damn straight I remembered because not only did I spend it with her hotness sitting across me the whole night but she said and that she would help get my confidence up with sex! “so I’m coming by to tell you what to wear and how to act with her.”

“Ok, I’ll be here.”

I almost fell back asleep and then I realized, ‘shit I have to clean up this fucking room’. I jumped up and did it in four minutes flat, basically because I just stuffed it in the closet in the hall way. Lucky it took four minutes because she was there in five; so with a minute to spare I washed up and was downstairs to answer the door before my idiot brothers could.

In my room she proceded to throw my clothes all over, finding nothing acceptable for this date with this mystery girl Megan. She found my one button up shirt and a decent pair of jeans, so this was decided. She looked at me and told me to cut my hair, short. I nod in response.

She then sits on my futon, and starts talking about this girl. She tells me to say the bare minimum, but respond to her with simple yet strong answers. Erin then goes on and on about Megan, it seems that she doesn’t really like her but whatever.

She tells me to hurry up and get ready, so I head into the bathroom; cut my hair, hop in the shower, shave and get out. She’s still sitting in my room and is kind of surprised when I come out with just a towel, I ask if she wants to stay and she gets up and stands in the hall way. I’m dressed in a flash and put a little cologne on. I open the door and she gives me the you’re ready look.

I walk Erin back and wait because this is where I’m suppose to meet Megan. I have to say I’m pretty nervous. Megan is here I stand up as Erin opens the door, I say “Hello”. Kızılay Escort Erin introduces us and we head out.

Megan is a beautiful girl. At least 5’8″, dirty blonde, grey eyes and a great smile. She starts talking about nothing and the truth is she’s really boring. But I don’t mind it because she’s nice to look at. I can’t tell if things have been going well until she asks me back to her apartment. ‘Damn it worked’


I walk into Megan’s apartment, she asks if I want a drink, and I never turn that down. She brings me a beer and we sit on her love seat. ‘What a corny name’ She says something else and I remember what Erin says “if you get back to the apartment, don’t just sit back and think it will happen. Take it if you want it.” So in the middle of Megan’s sentence I kiss her.

She starts to kiss me back and we both find the table, put our drinks down, while continuously making out. The only thing in my mind is take it if you want it. So I take her shirt off and as soon as it comes off, I can see the fire in her eyes. She rips off my shirt, buttons everywhere. ‘Damn my fucking shirt’.

I just pick her up straight off the couch and carry her to the bedroom. I throw her on the bed, she sits up and immediately she takes off my belt and pants. By now my dick is hard, come one I’m not exactly Don Juan, and she starts to give me the best blowjob I’ve recieved to this date. I’m going to blow this load, so I tell her to stop and start to eat her. I’ve never done this, but she seems to be enjoying it. I’m getting into it too; sucking on her clit and tasting her juices. She moans lightly and begins to move her hips.

I put a condom on and stand up. She says “lay down and I’ll show you how its done.” I give her a smile because of that horribly corny line and lay down. She gets on top and rides me. I can’t believe it seeing this girl naked, let alone on top of me practically bouncing on my dick; can it get any better than this and then I think of Erin and I get extra hard and Megan can tell my dick has grown. A new fire has come over those eyes and I have to take over I hold her while she’s still on me. I flip her around and start to fuck her from behind.

I think all would agree that doggy style is the best. I’m pounding Megan, she can hardly breathe in between her moans. She comes all over the bed and I’m still pumping she collapses and says her pussy can’t take it anymore. I ask so what do you want me to do about this, pointing to my dick.

She gives a little smile and starts to blow me again. I swear her mouth must have a motor because her tongue is BUILT FORD TOUGH. Never stops, I tell her I’m going to blow and she deep throats me for the first time and I can’t hold it back anymore and it feels like a weight comes off my balls. She’s surprised because she can’t handle the amount, it comes out her mouth and that is the best look possible for this girl.

We fall back in the bed and cuddle up and she falls asleep and then I get up and leave a note. I know I can’t be here when she wakes up, I’m not looking for anything more than what we just did.

I see my phone and there’s a text from Erin…

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