Olivias First Time

This is the second installment (on Lit) of Overlapping Circles. OC follows the lives of four fictional characters via their journal entries.

I write for fun. There are probably mistakes that make my English teachers wonder if I ever showed up for class but, whatever.

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Olivia: 28-October-1989

I met a guy at a frat party and had sex for the first time! It wasn't anything great. I think there's something wrong with me because I didn't have an orgasm.

Ade got invited to a frat party and asked if she could bring me. Even though it was Halloween weekend, this wasn't a costume party — this fraternity spent a lot of time mocking the other frat's who had costume parties. Rumor was the guys in this fraternity were cute, a lot of fun, liked to drink and were notorious for getting girls to sleep with them. Ade told me to wear a sexy bra and underwear because tonight could possibly be the night I got to do more than kiss a guy.

I wasn't convinced. I'm shy, skinny, and without a padded bra I look like a boy. Nobody is ever interested in me. But, I decided to wear black bikini's and a black bra with extra padding to make my small 32AA's look like actual A's and if I stood up straight they could almost look like small B's. Over that false advertising I wore a black dress that zipped in the back, had a high neckline, tight waist and went down to mid-thigh. I finished doing my hair and makeup, put on black pantyhose and black flats with little sparkles.

This party was pretty much like every other party had been. Ade flaunts her big boobs and blonde hair and gets lots of attention while I, the plain, boyish looking brunette stands by and watches while drinking punch from a red solo cup. She's such a flirt and guys always flock to her but after a while she makes her decision and sleeps with one.

Tonight one of the guys that was discarded pretty quickly started talking to me. Stephen was a good looking guy, short dark hair parted at the side, nice blue polo shirt, khakis and dress shoes. He was a few inches taller than me, probably 5'10 and had an easy smile. He lead the conversation, made me feel interesting and smart, and kept me laughing the entire time we talked.

I realized Ade had left, and was a little mad that she didn't tell me, but maybe she realized I was having fun with Stephen and just took off with her choice for the night. Slightly buzzed and a little upset that I was abandoned, I told Stephen I should probably go. He said it was still pretty early, maybe I just needed some fresh air and offered to go outside with me.

It had gotten pretty cold in the time that we were inside the frat house so we talked for a few minutes and I said again that I should probably go.

"Please don't, it's been fun talking to you and I'd miss you if you left," he said while looking deep into my eyes. I knew it was a line, but I didn't care. He was cute, sweet and funny. So I leaned in and kissed him. Softly at first, not sure he would be OK with it, but he kissed me back, held me close to him and let me wrap my arms around his neck as our lips pressed together.

Kissing is my thing. I hadn't kissed anyone before coming to college but I like it and I'm good at it. It hasn't progressed to anything beyond kissing because of the circumstances but I get very turned on by kissing and Stephen was good at it. Our tongues seemed to dance together just right and he wasn't over aggressive with it. My body just relaxed against him and whether it was the buzz or the kissing, I was enjoying it a lot.

Since it was cold Stephen suggested we go to his room inside so we could be alone and warm. He took my hand and brought me to the second floor where we could hear lots of laughter, music and other noise, but didn't see the cause of it. His room was down the hall past the closed doors his brothers rooms. I was floating, almost in a daze, being liked by a cute guy like this was something new for me.

Once in his room we settled onto the futon and continued fooling around. We kissed for what seemed like an hour, during which his hands made their way to my breasts. I felt a little guilty knowing he thought they were bigger than they are. I knew he was squeezing because I could feel the bra moving, but since my boobs don't even fill the cups of a AA bra, it didn't do much for me because all he was doing was squeezing the padded bra.

Stephen whispered in my ear that he was turned on by me and hoped we could go further but if I wanted to stop he would understand. I did want to do more, so I stood up and took off my shoes and my dress while he took off his shirt, shoes and pants. I'm sure I saw a flicker of disappointment when he realized all the curves he thought I had were the bra, but he recovered quickly and we continued kissing.

We stood there kissing and I was rubbing my hands all over his face, shoulders, back, arms and even squeezing his butt. He couldn't get my bra unhooked so I took a break from touching him and kissing and took it off.

"Sorry they're so small. I hope you're not disappointed," I whispered, looking down at the floor in embarrassment.

Grabbing my chin and turning my face up he smiled and said I was beautiful as he leaned in to kiss me. Our lips were mashed together and his hands found my little boobs. He was the first guy to see them, touch them and find out how sensitive my nipples are when I'm turned on. When he touched them I inhaled sharply which he correctly took as a good thing and continued kneading them and rolling them between his thumb and finger.

I wanted this so badly. I stopped kissing him and slid the stockings down along with my underwear making me naked in front of a guy for the very first time in my life. I wasn't sure what to do, and I told him so.

"It's your first time? It's OK, I'll do everything and be gentle. Come with me to my bed."

We laid side by side on his bed and kissed while he touched first my nipples, then my stomach, my thighs and finally, my pussy. I could feel the pressure through the course pubic hair and I wondered at what point it was going to hurt. At that moment it felt wonderful, feeling his finger slide up and down, rubbing my juices all around and finally finding my clit.

He was rubbing me erratically and it felt good but there was no way he was going to make me cum so I stopped him by saying, "I'm so turned on, get a condom and be my first."

I was laying on my back when he returned from the other side of the room with the condom. He took off his shorts and I was not expecting what I saw. His penis was hard but very small. Maybe 4 inches long and thin like a pencil. In my head I was thinking, "Well it least it won't hurt." He quickly put the condom on, came closer to me. I spread my legs for him and watched him clumsily poke his penis around my pussy.

I grabbed him with my fingers and lined it up then pulled his hip so he'd get the idea. It slid in easily and I made some loud moaning noises even though I couldn't really feel anything. There wasn't really any in and out motion like I was expecting, it was more just the pressure of his body increasing and decreasing against me. I had heard enough of Ade's stories to know guys like a girl who makes noise and moves so I made noises but didn't move because I was worried he would come out of me.

After a minute or two he said, "Liv, I'm gonna cum. Cum with me, cum with me!" Then he stopped humping me, and started grunting really loud. I started moaning, too. "I'm cumming with you, it feels so good!" although I had no idea if he was even still inside me.

He rolled off me, breathing heavy, and asked how it was my first time. He is so sweet and cute, the fact that it was so uneventful must have been my fault, so I said it was really great and thanked him for such a nice time.

We got dressed quietly, kissed a little, and agreed to see each other again. I reminded him of my dorm and we planned to meet tomorrow for lunch.

I can't believe that's how I lost it. I'm such a failure for not knowing what to do or how to make it amazing. I couldn't even cum until I got back and touched myself.

Ade is still out, I guess I'll tell her about the whole thing tomorrow.