This is a true story of the most painful yet triumphant few months of my young adult life. This is not a story that dives right into the romping, but takes its time to explore character development and an intense yet short lived passion. While it may be slower to develop than other stories, the meaty content of this story is exceptionally explicit and provides intense imagery. I think many readers on this platform will relate. Enjoy..
Chapter Two
The next morning came quickly. I had very vivid dreams of Allie last night. They weren't exactly sexual in nature which surprised me. The dream started with us meeting by chance at a party. Both of us being rather unamused with the current social scene decided to go for a midnight walk through campus. During this walk our conversation took a very intimate turn. We discussed secrets and fears. We discussed our triumphs as well as our own short-comings. Although this was merely a dream, I couldn't help but think the conversation was real, perhaps a foreshadow of things to come.
I decided I needed to be proactive. I quickly rose from bed and headed down the hall for a shower. Standing in front of the mirror I swiftly undressed to get a good long look at my body. I absolutely despise my body. I thought I was pretty good looking, facially speaking. I had pretty much lost my gut but a bit remained. That didn't bother me. What bothered me the most was my penis. It certainly was not the envy of most men. When I was erect I was usually satisfied with its appearance. Fully hard I am about five inches long and fairy thick. When flaccid I thought it was pitiful. Only about two inches and barely exposing the head, it has always been a major source of insecurity for me. No doubt this was the biggest obstacle I faced trying to bed a girl. Resigned to the fact that I am what I am and there isn't a whole lot I can do to change that, I knew it was time for me to fire my shot.
After Getting cleaned up and dressed I headed down the hall to Nick's room to see what he was up to. Obviously I was trying to finagle my way into a social situation that featured Shannon and Allie. I knocked on his door and was immediately granted access.
"Come on in buddy" Nick called out. I threw open the door to find Nick laying in bed with Shannon. The blankets were pulled up over them but I could tell they wear both naked.
"What's up man" Nick said, not at all concerned that I was gracing their presence while they were nude.
"Sorry dude, I can come back later."
"Nonsense" he crowed, obviously hung over from the night before. "Shannon was just heading out." Taking her cue, Shannon motioned for me to turn around which I did. When I turned back around I saw that she had slipped on a black bra and matching thong. Shannon was a knockout. I tried not to stare but her large caramel breasts were staring me right in the face. The panties hugged the slight protrusion of her mound very tightly. I think I even briefly caught a glimpse of razor bumps around her inner thighs.
"If you're going to drool, do it over the trash can" Nick playfully joked. He pulled Shannon in close for a hug. While she leaned in giving him a full embrace he squeezed her ass and parted her cheeks. Knowing Nick very well, he was doing this all for my benefit. I flushed red but couldn't take my eyes off of her ass cheeks. Behind her thong I could definitely make out the dark ring right where I expected her asshole to be. The sight of this did nothing but increase my already maxed out level of arousal.
Shannon finished dressing and turned her attention to me.
"You know, Allie really enjoyed the time she spent with you yesterday."
"Oh cool" I responded meekly, doing my best to hide my jubilation. "I had fun with her too"
Shannon smiled at me.
"She's a really great person and she really deserves a great person to be with. I think you two could make a good match. I know everyone is going to the beta house tonight but I was thinking maybe the four of us could just hang at our house." Shannon was referring to the Sigma house where she lived.
"Yeah, sounds good," I said. "Does Allie live at the Sigma house too?"
"No she lives over on Winter street in an apartment by herself" Shannon replied.
"Ok cool, I'll be by around 9:00" I said as I opened the door to Nick's bedroom. I practically floated to my room feeling more elated than I had in quite some time. I decided I would take the rest of the day to prepare for my night out.
I decided that I needed to "empty my gun" as a preemption against a potential misfire. I settled into my bed and pulled the laptop toward me simultaneously dropping my boxers around my ankles. Immediately heading toward Riley Reid's videos, I settled on one where she was actually getting fucked this time. Maybe this was indicative of my state of mind going into the night, or perhaps I was just extra horny. The entire time I watched Riley getting plowed I was ferociously imagining Allie bouncing her perfect ass up and down on me. This fantasy did not provide for a long jerk off session as it took only 10 minutes before I came very hard.
Satisfied that I was empty I decided a nap was in order. The nap lasted longer than anticipated and took me right to dinner where I made a quick meal. Going over the meticulous details of my preparation brought me to another crossroads. "What if I do manage to get her in bed tonight" I thought to myself. I pulled out my gym shorts and looked at my package. I needed to trim desperately. Despite the fact that no girl had ever seen me naked, I generally kept up with my manscaping, but I had definitely let it go lately. So I headed to the shower and gave myself a full trim. Feeling pretty good about myself right now, I decided the finishing touches to my preparation would be a little liquid luck. Careful not to over do it, I poured out four fingers of Jim Beam.
At quarter of nine I grabbed my box of beer and headed out to make the trek across campus to the Sigma house. I am incredibly nervous but so excited. In the past I've only felt nerves before a date. Never excitement. Again, this was another indicator that Allie had a different effect on me. When I reached the door to the Sigma house I rang the doorbell and took a step back and a deep breath. Expecting Allie to answer the door I was slightly disappointed when Shannon answered it.
"Hey Jason." Shannon greeted me. "Nick isn't here yet. Have you seen him?"
"Nope" I replied hoping to not come across short.
"Of course" Shannon muttered. "I'll go get Allie , but first I have to warn you." My heart instantly dropped. "She's kind of a light weight. I mean she's already pretty tipsy."
"Oh, haha, that's cool I'm not much of a drinker anyway" I stammered, overcome with relief. Shannon left the room and quickly returned with Allie .
"Jason!" Allie exclaimed. Her voice is so sexy. It's not high pitched or girly girly. It's not deep or manly. It has a smooth inflection with just a touch of a Boston accent.
"Hey, how's it going?" I said, trying not to appear nervous. She gave me a big beautiful smile and wrapped her long arms around me. Trying to inconspicuously hide my immediate erection I held her as close as possible. I savored her natural scent. She didn't wear perfume but smelled intoxicating. I savored the feeling of her firm breast pushed against my chests. The hug probably only lasted three or four seconds but it felt like someone just threw a 200 volt switch into my body. We chatted for a few minutes while Shannon tried to get a hold of Nick. We covered some new ground and a bit we had already covered. Either Shannon was mistaken about Allie being a lite weight or she hid it very well. She showed no signs of impairment other than being a bit giggly. I was drinking Rolling Rock and she Bud Light. I got through three beers to her one when Shannon came storming through the door.
"Fuck him" she hollered. "I'm going to the Beta house. You guys wanna come with?
"No no no no no" I thought to myself, but instead glanced at Allie and said "I don't care. Do you want to?"
"Not really" Allie replied timidly looking toward Shannon then to me as if she were concerned about offending either one of us.
"No worries, but I'm still going anyway. So not to be a dick but I'm going to have to lock up" said Shannon.
"That's ok, Jason and I can go for a walk" said Allie, looking toward me for validation. I nodded my head which prompted another one of her beautiful smiles. I was in heaven. I had her alone. And it was early. And we had no plans for the night. The stars were aligning, and my nerves were mounting. Feeling the need to counteract those nerves I pounded another beer.
We started out toward the downtown area. There isn't a whole lot downtown but it's nicely lit and there are some cool storefronts. We walked for about half an hour until we reached the strip. Allie, leading the way, turned down a side road that was hardly lit. I looked up at the street sign. Winter Street. As the darkness increased she drew herself closer. I decided tonight I was going to be bold. I reached my hand down and gently fit it over hers. Again the electricity jolted through me. She didn't rebuke me but instead held my hand tightly. She even caressed my palm with her index finger. Her hands are soft and smooth. A model of femininity.
She stopped in front of a large three story house. By the faint light of the closest street light I could tell she was nervous. She was biting her lip.
"This is my house" Allie plainly stated.
"Nice place" I replied. You've got to be kidding me. This was the best I could come up with.
She smiled and laughed a little laugh. She knew how painfully awkward I was. And she didn't seem the least bit perturbed.
"It's early, let's watch a movie," said Allie .
Trying to quickly gain my composure and come up with something a little more substantial I smiled wide at her and said "I'd love to."
We climbed up the two flights of stairs to her one bedroom apartment. The place was very small featuring a kitchenette and an almost non existent living room.
"Umm Allie , where is the furniture and the tv?" I chuckled knowing the answer and growing more excited by the minute.
"Tv is in my bedroom but I don't have any furniture so we can just sit on the bed." She led the way into her large bedroom. Two things I noticed right away that surprised me. Allie was far from a neat freak. The second thing was a real curveball to my psyche. Allie was most definitely having sex. And judging by the 500 count box of condoms peeking out of her closet she was having plenty of it. I didn't know what to make of this. I guess I didn't expect her to be a virgin but I certainly didn't expect her to have a wealth of experience. I decided to shake it off and roll with it. I liked this girl a lot and I was ready to leave my insecurities behind in pursuit of her.
Allie fiddled around in a box sorting through dvds until she found what she was looking for. "I have just the movie for you" she gleefully announced. She held up a copy of "The Sandlot". Pleased at my reaction she popped it in and took a seat on the bed. Kicking off her shoes she motioned for me to do the same. I kicked off my shoes and sat down next to her.
An uneventful hour passed where I pretended to focus on the movie. I'd seen "The Sandlot" many times and was hardly interested. I decided to push the boundaries of physical contact. I swung my arm around her back and rested my hand on her shoulder. She accepted my advance and even dropped her head onto my arm. After a few minutes I dropped my hand lower and cradled her lower side. She responded by moving in closer. She was pressed right up against my body now. This is the most physical contact I've ever had with a girl at this point but I was remaining calm.
The movie ended and we snapped back to reality. Not knowing at all how to play this, I let Allie lead. I watched her as she yawned a big yawn. "It's already midnight, I guess the night got away from us," she said.
"I had lots of fun though," I added "I love that movie."
"Me too" she grinned. "Hey, I was wondering, would you want to spend the night here?"
An instant boner and a tsunami of butterflies ensued but I remained strong. "Yeah I would" I said as smoothly as I possibly could.
"Ok but I have a few things I want to cover first" Allie started. "First of all, we aren't having sex tonight. I'm sorry if that disappoints but I have had a string of bad relationships lately and I am just not ready right now." Instantly worried that she may have offended me she quickly carried on "not that I wouldn't have sex with you, but tonight isn't the night." She grabbed me by the waist and pulled me in hard to her warm embrace. "I need intimacy but not sex right now. I want you to hold me while we sleep. Is that something you are up for now or is that too weird?"
Truth be told I was very relieved at this revelation. This meant that I could work up to sex at a slower place while still enjoying my time with Allie .
"Yeah, I'm fine with it. Being with you is enough for me" I said. Where were these words coming from? A few days ago I never would have had the confidence to say that to a girl. Allie beamed at this.
"You are sweet Jason. I'm sure this is a little odd for you, I mean you're quite the charmer. Waiting for a girl probably isn't something you're too familiar with." Allie clearly was misreading me now. My false confidence was working and she had no clue that my virginity was firmly intact. How would I play this going forward? Obviously she's going to know when we have sex. Oh well, we will cross that bridge when we get to it.
"Im going to sleep in my underwear if that's ok" Allie said awaiting my reaction. "You can do the same if you want."
"Of course, that's how I sleep too," I replied. With that Allie pulled her shirt over her head. She unsnapped her jeans and dropped them around her ankles. She was wearing a white plain bra that concealed most of her breasts but from what I could see they were an A cup just as I suspected. Her stomach was smooth and creamy that featured the cutest outie belly button. She put on a baggy undershirt and unhooked her bra underneath her shirt, denying me a chance to see her in her glory. Her panties were red cotton surrounded by two very thick thighs. One of Allie 's best features were her legs; super creamy like the rest of her body and super smooth. She smiled at me as she peeled the blankets back and climbed into bed.
"Your turn" she flirted. I stripped of my shirt taking note of how Allie was studying my body. Then came the jeans and I realized I had a big problem. My penis was very erect. Perhaps more erect than it has ever been. Sensing my apprehension, she smiled ear to ear.
"You have a boner don't you Jason?"
"Um ye-yeah" I admitted.
"It's ok, as long as you don't try to stick it somewhere it shouldn't be" she laughed hard. That vote of confidence was all I needed. I dropped my jeans to the floor and let my erection pitch my boxers straight out at her. Allie, seeing all of this, bit her lip and clamped her legs shut. I could tell that turned her on but she really didn't want to act on it right now.
I climbed into bed and cuddled right up next to her. She reached up and flicked off the light switch. Then she grabbed my arm and pulled it across her waist to hold her close. My hand was directly on her bare stomach. Her skin is so amazingly soft and smooth. I lightly caressed her stomach with my index and middle finger. Then I moved my hands down to her thighs. I did the same down there, being careful not to push the boundaries. I was getting closer and closer to her butt when I noticed she was emitting faint little moans. I desperately wanted to know if her panties were wet but didn't want to push my luck. After a few more minutes of me teasing her thighs, she grew bolder. She slid her ass in as tight to my groin as possible. My erect cock was wedged right into her ass crack. She moved her ass around for a little while longer then suddenly it all stopped. The motions and the soft moans. Had she fallen asleep or had she actually gotten off by rubbing her ass against my cock? I didn't care. I was spending the night with the girl of my dreams and that was good enough for me. With that I drifted off to sleep with my cock still firmly pressed between Allie 's ass.