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Intro: First I have to thank my dear friend AoE for encouraging me to write this story and for getting me started by writing the beginning of the story. I’m posting this in “first time” but in the unlikely event there is a part 2 it will be under erotic couplings.
You often hear someone say, “You will never forget your first love.” Well, I’m here to say that that statement is true. At least for me it was true.
When I was a young man, growing up in a relatively quiet neighborhood in Philadelphia, the girl next door was my fantasy girl for as long as I can remember. She was a year ahead of me in school, but that didn’t stop me from trying to hold her attention. Even when I was a freshman in high school, I lusted after her. Now, as a junior, I wanted to ask her out more than ever. She was a senior and that kind of made her ‘off limits’ for me. However, that didn’t change my opinion that she was the most beautiful girl in school.
It wasn’t the first time I had those kinds of thoughts about her. In fact, I’m fairly sure that I had similar thoughts from the time I entered puberty. My “girl next door” was my favorite fantasy when I first realized what it meant to “jack off.” In my youthful mind, she was a permanent resident. As I grew up, not much changed when it came to her residing in my thoughts. If an opportunity arose to make her notice me, I took it. If there was a chance to flirt with her I took it. If she even looked in my direction, I gave her a smile, a wink, a wave. I did anything and everything to get her attention.
The unfortunate thing, for me, was that I never got it in the way I so deeply wanted it. I wanted her to notice me as “a guy” and not “the boy next door” or “the friend.” At the least, I wanted her to notice me as “the cute boy next door.” That never really happened for me though, not in the real way I wanted at the time.
Yes, she was always nice to me. We were friends in more than a neighborly way, but only because our families spent a fair amount of social time together and we were often in each other’s company. When we were together, our conversation mostly centered on things that were happening at school, with friends, in music, or the current hot issue of the time. She was easy to talk to, easy to listen to, and even easier to look at.
We grew up in South Philly together. We were products of our environment and our family heritage. We lived in the area of South Philly that was made up of mostly Irish and Italian families. It’s an area where family names have been around for over a hundred years. No one ever sold their homes, they just left them to their children and the next generation of the neighborhood was formed.
My family is of Italian descent. My Dad’s family owned the trinity home we lived in for as long as anyone could remember. The wall, along the stairwell, leading to our second floor displays our family history and this house’s history in pictures.
There are pictures of my great grandparents holding my grandfather on the front stoop. A stoop, for those of you not from South Philly consists of one or two steps, usually not more than four that leads to a small platform too small to be called a porch. No one in this area has a porch; we all have stoops.
The photo of my great grandparents shows them arriving home from my grandfather’s christening at Saint Joe’s parish. Saint Joe’s is as much a part of this neighborhood as any of the families that live in it, if not more so. With a population of almost one hundred percent Irish and Italian families, Saint Joe’s gets a workout. If an event is occurring in a family, Saint Joe’s is involved. Christenings, Communions, Weddings, Births, Deaths, etc…all of the life events that occur in families, occur in one way or another, at Saint Joe’s.
A little further up our family photo gallery is the picture of my grandfather kissing my grandmother with three dark haired boys of varying heights standing at their legs. The tall one in the center is my dad. Next on the wall is the picture of my parents in their wedding outfits, with the traditional pose, outside our front stoop. Interspersed between and around those pictures are a variety of family photos, holiday dinners, graduation photos, you know all of the regular events that end up memorialized in photos.
Anyway, like I said, families don’t leave the area they just pass their homes and their history down to the next generation. It has its benefits and its drawbacks. The benefits are that everyone knows everyone and is very protective of each other. The drawbacks are that everyone knows everyone! If you grew up in this neighborhood, there wasn’t a thing you could do, that was even slightly out of line that your parents didn’t find out about one way or another. No matter how hard you tried to keep something secret, someone always saw it and told on you.
Given all of the pro’s and con’s of growing up in this neighborhood, there were more pro’s than con’s and I loved every minute of my years here. My favorites were the years between the ages of fourteen and twenty two Alanya Escort escort when the girl of my dreams lived right next door to me and I was more than aware of it.
Aileen Katherine O’Reilly was close to perfect in my eyes. She was everything her name makes you think she would be. She was tall, standing about five foot, eight inches tall. She had an athletic body, not too thin and not too muscular. Her hair was a beautiful shade of strawberry blonde; more strawberry in the winter months and more blonde in the summer. Her skin color was what my mother referred to as “peaches and cream” and oh god, how I loved peaches and cream.
Aileen had clear blue eyes that were almost always smiling. A straight Anglican nose, covered with just the perfect amount of Irish freckles and a smile that always made you think she was happy to see you.
Ok, ok, I’d be remiss if I didn’t also say she had a really great breasts. I don’t know for sure, but I always guessed that they were the perfect size C cup. Perky and soft, but firm enough to stay up on their own. More than a mouthful, but just enough to keep a man’s hands occupied. Christ, just thinking about them now gives me a hard on.
The rest of her body was pretty perfect too. She wasn’t one of those petite Barbie doll girls. Aileen had a curved waistline and flared hips. Wide “birthing” hips they’re called. Her ass was a little more than most, but it was faultless on her frame and I would know because I spent hours thinking about it. That is when I wasn’t actually trying to get a glimpse of it.
Aileen was popular in school and every guy I knew would have been more than happy to have been able to call her his girl. She, however, had a different plan; her goal was to get an academic scholarship. She knew after raising five children her parents weren’t going to be able to help too much with her college expenses and she had every intention of going to college.
Her dad and her three older brothers also had opinions on the subject of Aileen. The theme of their opinion was that Aileen was off limits. The word overprotective does not even come close to what the men in her family were like. No one wanted to mess with the O’Reilly brothers. They weren’t big guys in a sense, but all three of them boxed and they never went anywhere without at least one other brother. That rule was extended to Aileen.
Her younger brother, Brian was in my class. We were friends and we both played on the basketball team together, but I never once mentioned to him how I felt about his sister. I surely did not mention any of the thoughts that frequently ran through my mind whenever I was in visual distance of her. Hell, I didn’t even need to be in visual distance; I just needed to be able to picture her in my head.
The closest I ever came to carrying out even a small part of one of my fantasies was the night of her high school graduation. We were having a get together to celebrate her milestone and toward the end of the evening, she and I were the last two sitting in the backyard. The yards were narrow and the only way we could fit everyone comfortably was to open the gates between our two fenced yards.
Our parents had decided to go in and play some table games, her brothers had left a while ago to hang out with some friends, and she and I were sitting, in the backyard, on the glider swing talking. We started talking about going to college and what her plans were. The more we talked about her leaving for college, the more nervous and antsy she seemed to become.
She started to nervously shuffle around in her seat and twist her hair around her fingers. I noticed in the past that whenever she became nervous, she would do this hair twisting thing to calm herself down. Then, out of nowhere, she asked me if I would help her out with something.
“Sure I will. What do you need?” I thought she was going to ask me if I would help her move some of her stuff when she moved onto the Rutgers Campus or something like that. I was surprisingly wrong.
“Chris, you know how overprotective my family has been, especially my brothers.” She looked at me like she was expecting some sort of response.
“Yeah.” What could I say; everyone knew about that.
“Well, I have a small problem I would like your help with if you’re willing.” Her voice was a little hesitant and even a little shaky as she said it.
“Whatever you need.” Still expecting her to ask to help with something physical, but wondering why her four brothers wouldn’t be enough help.
“Are you sure. Because if you’re sure, I’d really like to take care of it as soon as possible.” She smiled shyly.
“Aileen, I told you, I’ll help with whatever you need.” I was happy she was asking me for help of any kind. It kind of made me feel special that she thought she could count on me and that she trusted me to help her when she needed it. “What is it you need?” I said as I took a drink of my Pepsi.
“I was hoping you would be willing to sleep with me so that I don’t have to go to college as a virgin.” She said it as Alanya Escort bayan if she was asking me to drive her to the store.
I couldn’t believe what I was hearing. In fact, for a few seconds, I was absolutely positive that I had imagined the words coming out of her mouth. I coughed and almost spit my mouthful of Pepsi all over her. It took everything I had to swallow without aspirating the soda into my lungs.
“What did you just ask?” I still couldn’t believe what she said and I had to make sure I wasn’t dreaming. The last thing I wanted to do was answer her, thinking one thing, and having her think another.
“Christopher, please don’t make me repeat it. It took every bit of courage I had to ask you the first time.”
I could tell she was nervous and somewhat embarrassed by what she just asked. Also, she wasn’t sure about how I would handle what she had requested of me and that kept her from looking into my eyes as she spoke.
“Aileen, you could have any guy in school. Why me? I’m not even in your class or in your social group from school. Why not ask one of those guys?”
I wanted to cut my tongue out as I kept asking these inane questions. My heart wanted to take care of her and make sure she was making the right choices, the right decisions. I wanted to know why she was having this conversation with me. At the same time, my brain was saying, “Shut the fuck up and just say yes!”
Ok, maybe it wasn’t my brain saying that; at least not the brain in my head. Maybe it was my “southern brain,” the one below the belt. Either way, my mouth kept moving and the words weren’t much different when they came out.
“Chris, I don’t want to be with one of my friends. I know if I asked one of them they would be more than happy to, let’s say, ‘take care of the situation’. The problem is that I want someone I know well. Someone who I know cares about me, likes me, umm…maybe even more than likes me a little.” She smiled at me and looked right into my eyes.
Now she was looking at me and I’m sure, I was turning red. All of this time, I thought she didn’t have any idea that I was interested in her and attracted to her. Apparently, I was very wrong. My heart took over again and was out ruling my “below the belt brain” as I continued to ask stupid self-defeating questions.
“Aileen, why do you feel the need to do this? What difference does it make if you go to college as a virgin? Besides, who would know if you don’t tell them?” Again, I could hear the words ringing in my head to “shut the fuck up!” Yet I simply couldn’t stop myself. I really liked this girl and it was as simple as that. I wasn’t going to hurt her or let her make this decision without at least knowing that she was sure about it and that it was what she really wanted.
“I just do. I don’t want the pressure of having to date and be a virgin in college. I don’t want to pick some stranger who barely knows me as my first. Mostly, I want my first time to be with someone I know. Someone who knows me, likes me, and well, cares for me. Most importantly, I want it to be with someone who respects me.”
I didn’t know exactly how to respond to all of that. Everything she said, I felt for her. I definitely cared, liked, and respected her. I didn’t have any issues with what she said and she presented a pretty solid case for why she wanted it and why she chose me. I really didn’t see an argument to present to her. That is with the exception of her father and her four brothers. But hey, risk not, want not or something like that right?
I quietly looked at her in the dim light of the citronella candles that were still burning all around the tables. I didn’t want to argue with her or to try to make her change her mind. I knew I wanted her. If she wanted me to be her first, who was I to say, “no?” Not that “no” ever entered my mind, but I did want to make sure she was certain about what she wanted.
I nodded. “If you’re sure it’s what you want; I’d be happy to be your first.” I said it as if it was the furthest thing from my mind, and I was only thinking of it and agreeing because she brought it up.
“I’m sure Chris. I’m definitely sure.” She smiled and pulled me close to her as she held my face to her and gave me a big kiss. “When?”
“I’m not sure. Why don’t we hang out a few times together and see how things go?” I never had a girl proposition me before. I was no longer a virgin, but I surely was no Don Juan. I thought it would be better for both of us and a little more comfortable for her if we took it slow.
“No. I don’t want to wait too long. If we like it, I want to be able to practice and do more with you.” Then she bit her lip as if she wanted to suck the words back into her mouth. “God, that sounded awful didn’t it?”
I couldn’t help myself, I burst out laughing and took her hand in mine.
“Actually, it sounded kind of hot to me.” I brought her hand to my mouth, opened her palm, and kissed it lightly. “It didn’t sound awful at all.”
“Are you just saying that to make me feel better?”
“No. I mean Escort alanya it. It sounded fine. I know exactly what you meant.” I held her hand in mine for a few minutes as we talked more about her “favor.” We decided we would meet Friday evening and go from there.
Now remember I’m a 18 year old boy. That means I jerk off every day. Every single day. I said I wasn’t a virgin. Well technically I wasn’t. But I’d only gone all the way once. Most of what I knew about sex was theoretical. Aileen was who I wanted and the subject of most of my masturbation fantasies.
To think that Aileen wanted to have sex with me was more than a dream come true. It was like parting the Red Sea and and winning the lottery on the same day. Of course I let my mind wander and pretend that she wanted to make love and not just have sex.
Then self doubt crept in. Please don’t let me screw this up. Don’t let me prematurely ejaculate. Or fail to get hard. Or say something stupid. Or bite too hard. Just don’t let me screw up.
Friday night was the Saint Joe’s annual carnival. Aileen and I used to go together when we were younger along with her parents. She and I hadn’t gone to the carnival together since she was 13 and became cool. But we decided to go this year. A chance to reconnect and be together without raising suspicion. It was a warm summer night and we walked down the street together. Everyone from the neighborhood was at the carnival and no one had a second thought of seeing us together. We were able to buy beer even though we were underage. It was sort of a carnival tradition.
At midnight we walked home together. I held her hand as we walked in silence. My heart was pounding. It wasn’t the beer. It was because I was holding hands with the most beautiful girl in the world. When we got home I started to give Aileen a hug. She grabbed me and kissed me. Full on open mouthed. She slipped her tongue into my mouth for a split second. Instant erection. “Good night Christopher”. And she was gone.
The next day was Saturday. My parents went to the shore and her parents went to the Poconos. Around noon she knocked on the front door and entered before I could answer the door. She was wearing a pale blue t-shirt and a pair of denim shorts. Her hair was long and flowing and she was gorgeous. I gave her a glass of iced tea and we made small talk. She smiled at me and said let’s go upstairs.
We sat on the bed and started to kiss. I was in heaven.
Aileen let me undress her. I lifted her t-shirt over her head. I reached behind and unhooked her bra. As her bra dropped forward and her breast came into view I thought I was going to have a heart attack. I kissed the top of her left breast. Then the right breast. I took a nipple in my mouth and sucked gently. My god I couldn’t believe how good this was. We started to french kiss. Aileen was so alive. So vibrant. So full of passion.
She lay down and let me unfasten her shorts. She lay on my bed in just a pair of pink cotton panties. Without hesitation, she raised her hips and I slipped the panties over bottom and she was naked. Beautiful and naked. Her body so ripe. So sexy. Her pubic hair was golden blond. I wanted her so bad. I quickly undressed and joined her on the bed. We held each other and kissed.
Aileen whispered in my ear, “I’m ready”. I reached for a condom and rolled it down my cock. My cock had never been harder. As she lay on her back I climbed on top of her. I looked down and admired every inch of her body. She was so sexy and alluring. My cock entered her pussy. Slowly at first. I didn’t want to go too fast. Once I was fully inside her, I paused to let her body relax.
I started to move a little at a time. Slowly at first and then a little faster. Aileen started to move her hips in time with me. For her first time and my second time we were moving together like a couple who’ve been married for 20 years. After five minutes Aileen’s body stiffened and she orgasmed. I came a split second later, holding Aileen, my cock exploding inside of her.
Aileen and I saw each other over the summer but we never had sex again. She always had a ready smile for me and treated me a little differently, a little sweeter. I know she didn’t regret what we shared together but at the same time she wasn’t looking for a repeat performance.
Aileen went off to college in September and I started my last year of high school. We saw each other on semester breaks and holidays. Aileen was always sweet to me but there was an invisible wall between us. I accepted what was and cherished my afternoon of pleasure with her. I started to date other girls. Nothing serious. I liked some more than others. Some of the relationships were sexual and some were not.
I started college in the fall. I went to Temple and lived at home to save money. I could take the Broad Street line and be on campus quickly. I was double majoring in engineering and business. On breaks Aileen and I would talk about our studies and college life. We both left out any mention of our love lives. Mine was taking a back seat to studies and working part-time. Aileen was still the high-water mark of my sexual adventures so far. I kept myself from falling in love with her because I knew nothing was going to happen and I did not want to get disappointed. I knew if I let myself, my heart would run astray. So I didn’t let myself.
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