Category: first times

Freshmen Roommates Discover Each other

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After graduating high school and leaving my comfortable home in Florida, I found myself rooming with a wild child from southern California. Ella, was tall and slender with long flowing blonde hair and a deep tan. Her fit frame was ample for supporting her large B cupped breasts. Even at our first meeting, I wasn’t afraid to say how I thought she was attractive. Up to this point in my life, I had done quite a bit of sexual experimentation throughout high school with boyfriends and alone, however, I had not ventured into my bisexual side yet. Living in a fairly strict house, I hid my sexual activities and limited masturbation sessions to the shower or when I was home alone. Up to this point, my self exploration was pretty straight forward. Mostly with fingers, although I had found a hair brush handle that I became quite fond of. I knew of the world of sex toys, but wouldn’t dare to bring one into my home, for fear of being found out. My sex life was quite the norm for a high school student. Mostly consisting fooling around in the back seat, which led to many a blow jobs and eventually into some hot sweaty sex with the boyfriend of the moment. Toward the end of my senior year of high school, I had more often found myself fantasizing about being with another girl, but had not acted out on any of my torrid thoughts.

Ella and I hit it off right away. Becoming friends fast, we often found ourselves having late night erotic conversations about our previous sexual activity. It was obvious from the get go that she was far more experienced than I. Ella told stories of masturbation with vibrators and dildos and hot sex stories about being on the beaches and even on the school football field. She even spoke of an experience at a party where she found herself drunk in a bedroom with a cock in each hand. Ella never spoke of any experience with other girls so it left me to wonder if she was grossed out by the practice, or just shy about speaking of it in front of me. After ending each night and turning off the lights, I would find my hands sliding into my panties while lying in bed just feet from my roommate. As I would retell the story I had just heard to myself, as my fingers would slide up and down over my ever swelling moistening lips. Biting my lower lip to prevent the slippage of any moans, I would lye facing the wall, my back to Ella’s bed and gently moisten my pussy until access could be made to my sopping hole. Making sure to silence any noises, I would allow a finger to slip past and deliver an explosive amount of pleasure as it would plunge into me. While plunging my finger in and working in a second, I often found myself wondering if Ella was doing the same as she lay just feet away, thinking of one of my stories, or maybe me. Working my way to a silent orgasm, I would cum on my fingers and often bring them up to my lips for a gentle lick, to taste myself then doze off.

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Party Dare

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It was late at night at the residence of Maya Murdock. Her parents had left for a week-long conference across the country and it was the middle of summer. Maya, who was twenty-two, feeling ever so lonely, decided to call up some friends to hang out.

Maya invited Jenny, Lucy, Amber, Patricia, Christine, and Rebecca. As Maya waited for her friends to arrive, she kicked off her socks and began reading one of her dad’s golf magazine. Less than a minute after she began reading, she threw it away, quickly discovering her hatred of golf.

Amber and Rebecca arrived first in their blue convertible. Amber and Rebecca, both of whom were about eight months older than Maya, were known to, as Maya would say, steal the show, because of their incredibly revealing outfits. They were both wearing a black bra and a blue thong that lightly exposed their butts. Maya, on the other hand, was wearing an orange blouse and jeans above her underwear.

Jenny, who was a month younger than Maya, arrived just moments later, and like Maya, she was incredibly modest, with her red dress easily reaching down to her knees, not wanting to show too much to anybody. Jenny also brought with her two bottles of wine, which she stole from her father’s liquor cabinet.

Lucy, who was a year older than Maya, followed Jenny in, but her sense of style was in-between those of Jenny and Amber. She wore just a very small tank-top, one which didn’t reach down much farther than below her boobs. However, she was wearing a pair of jeans, and was also wearing underwear. Lucy brought three bottles of tequila, which she bought from the local liquor store.

Patricia, who was six and a half months older than Maya, came in just a moment later, and on her, she had a very long skirt that went to her crotch, and then just a pair of panties to cover her clit. Patricia brought to the party a bottle of scotch, which was part of her mother’s salary, since her mother works for a brewery.

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My Best Friend

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As I awoke it felt as if a freight train was actually traveling through my head. I immediately hugged the pillow again. ‘Too much wine last night’ was the main thought going through my mind. Of course, without all that wine, I probably would not have experienced one of the best nights of my life. Despite the freight train rattling around in my head, I smiled as I closed my eyes and relived what had happened just a few hours ago. The memory brought some relief.

When I came home from work yesterday, Josh, my boyfriend of 10 months, was sitting on my porch waiting for me. I ran up to him and tried to give him a kiss, but he pushed me away and told me we had to talk. Warning bells went off. Did he lose his job? Did someone die? Looking miserable, he sat back down on the porch swing. Giving him a moment to compose himself, I joined him on the swing.

“Baby, you know I love you. This is really hard for me to tell you this.”

He took my hand in his. He looked to be in agony. My thoughts went to his grandmother, who we both loved with all of our hearts. Did something happen to her?

“Is it Granny?”, I asked with rising panic in my voice.

“No..no..I …shit, hon. This isn’t working, me and you. I love you, I swear I do.. but…”

I went half numb with shock. I thought I would be spending the rest of my life with Josh. He tried to explain why he couldn’t be with me any longer. “. No matter what he said, the words “We are through” was all I could hear. He tried to ease my shock some, no doubt, but in the end, he simply walked off of my porch and out of my life.

I sat there staring into space for a while, the reality not really hitting home. As I stood up and walked into my now “empty” house, overwhelming pain seized me along with denial. I looked around and some of the memories of our relationship began to relive themselves in my imagination. I needed to blank this pain out.

I went inside and grabbed a bottle of wine from the fridge. I laughed ironically, remembering that we had bought this bottle together, planning on toasting mushy sentiments to each other in front of the fireplace one evening. Anger began to well up inside me now – “Well.. fuck.. I can’t let this go to waste now, can I?” I had started the fire and drank from the bottle as I stared into the flames. I must have sat there for hours, ignoring everything but the sweet warm liquid as it erased my pain and reduced the anger temporarily.

I felt a tap on my shoulder and dropped the bottle. For a split second I thought that maybe Josh had had second thoughts. Turning around, I saw my best friend Cheri close to me. She took one look at my face and dropped to her knees, pulling me close to her.

“What’s wrong, sweetie?”, she had asked so softly, her question tinged with fear.

I couldn’t talk; reality came swarming back. The tears that I had so successfully managed to hide for the past few hours suddenly surfaced again. I just curled into her, feeling so small as she wrapped her arms around me.

“Talk to me, hon. – I saw your lights on but you did not answer your phone. I was so worried.”

She told me that she had let herself in with the key I had given her because I had not answered her knocking at my door either.
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