Chelseas First Love

Chelsea was an eighteen year old senior in high school that lived with her mother in a small suburb just outside of Philadelphia. She could never see herself dating or being with a boy her own age. The boys in school were like kids or brothers to her, definitely not boyfriend material.

As beautiful as Chelsea was, she never had a boyfriend in high school and didn't even go to her senior class prom. Chelsea wanted a man and not a young boy from school that had just finished puberty. Chelsea wanted someone experienced, wise, knowledgeable. She wanted someone that knew a little something about life already. She did not want an eighteen year old boy that had just gotten his drivers license and couldn't wait to make out with a girl from school in his parents car on a school night.

Needless to say, Chelsea knew absolutely nothing about courting, dating, or how to have a physical or sexual relationship with someone. Chelsea refused to get into a boyfriend girlfriend relationship merely for the experience. She knew it wouldn't feel right at all so Chelsea came to terms with being single all throughout high school. It never bothered her much being alone like that because she had plenty to keep herself busy with. The closer it got to graduation however, the more she desired having a boyfriend. And the last thing Chelsea wanted was to still be a virgin when she entered into college.

Gaining this sexual experience before college in the fall seemed important to Chelsea. She couldn't explain it, but something inside of her was constantly saying, "you need to experience love, before you go to college." That phrase was always at the front of every thought and action Chelsea had made during her senior year in high school. She didn't know why it was so important, but if her brain was telling her something over and over and over and over again, then it must be important in some way.

Graduation was only four weeks away and after that she knew that having any time for a boyfriend would not come easy. Chelsea was already registered as a counselor for the all girls summer camp that would exhaust all of her free time for having any sort of fun. And directly after summer camp, she would be moving into a Drexel college coed dormitory. So the four weeks before graduation was her only chance to get some sort of sexual experience under her belt.

Desperate times meant taking desperate measures. Four weeks before graduation, Chelsea posted a personal ad on Craigslist. She didn't have the time to sift through endless amounts of pictures on dating websites. Chelsea needed some fast action and Craigslist was her best bet. She wasn't completely naive though, she knew that 80% or more of the replies she would get wouldn't be serious inquiries. And a small fraction would probably also be down right scary.

However, even if she only got two or three potential suitors, that was a good enough start to get the ball rolling. Something inside her always told her that she would meet her future husband and soulmate while attending college. She couldn't explain it, but that constant feeling surrounding college, was always nagging at her from somewhere deep inside her mind. It was as if a spell had been cast on her, and now she had a constant reminder of her fate, once in college.

Having that strong of a notion, that no matter what you do, this thing was eventually going to happen, truly scared Chelsea. She didn't like the feeling of not being in control of her future. And she REALLY didn't like being forced to discredit anything she would normally label as a coincidence. She didn't necessarily believe in God or that the world was going to end any time soon. The only singular for certain, that Chelsea believed in 100%, was that she would meet her soulmate while at college.

Chelsea couldn't explain it, and she tried, multiple times. It was more than just a feeling or a strong possibility. To Chelsea, knowing she would meet the one person meant for her for the rest of her life, was more like an absolute truth. She just knew that it was/is/going to happen, period. Like the universe had already predestined it to become. There was no sense in fighting it or trying to change the outcome, because in Chelsea's mind, this "event" has already happened...the universe was just waiting for Chelsea to catch up with it.

Pretty deep thought for an eighteen year old, but Chelsea always felt that she was an old soul, passed down through generations.

Making the ad was really easy and kind of fun as well. Her ad read, "young, eighteen year old straight white girl seeks thirty to forty five year old man for first time physical relationship before going to college. Must be willing to meet in designated public place of my choosing for initial meeting. Only considers man after strict screening process. Must provide full name, picture ID or drivers license and be willing to have background check done, before any fun can begin."

Chelsea also posted a photo of herself with the ad hoping no one she knew would happen to see it. She posted a picture of herself wearing light blue yoga pants, a tight white tank top, and standing barefoot in the grass. Chelsea was an absolute vision of vibrance, beauty, and innocence. She was five foot five inches tall, thin, sleek, with long auburn hair that she normally had in one long French braid. Her skin was very fair with a slightly pale complexion. She had perfect eyes, a perfect smile and average womanly features for her young age. The only thing Chelsea didn't like about herself was that she had tiny moles all over her body. None of them were really big or unattractive, she would have just preferred to not have so many of them.

Upon request, she was willing to send some more revealing pics, but nothing that showed her completely naked. The pics were all pretty tasteful, but at the same time, very sexy. She had closeups of her petite, white nail polished, bare feet and one close-up of her face including her sensual neckline. Chelsea was about as close to looking like an angel as you would ever find on earth.

Chelsea loved to show off her petite sporty body by wearing much skimpier clothes than her mother would have liked her to wear. Chelsea had played field hockey for her high school during her junior and senior years of school and liked to run often to keep her body thin and sleek. Three times a week she would get up at 5am to do a one or two mile run before going back home to shower and get dressed for school.

Given Chelsea's extremely tight schedule during her average week, it was a surprise that she found time to even post an ad on Craigslist. With the added extra stuff that went along with graduating in four weeks, Chelsea slept maybe six hours every night. On the weekends she would try to catch up on lost sleep whenever she could, just like her mother would do frequently.

Chelsea's mother was a registered nurse at Mercy Hospital in Philadelphia. Her parents divorced when Chelsea was still very young, before her teenage years. Her father had been in and out of jail a good bit from the time Chelsea started going to kindergarten to when she turned twelve, when he abandoned her and her mother. Neither ever found out why exactly he had left them both, but more than likely it was because of his escalating drug addiction to pain killers.

Not having her dad around while Chelsea was growing up was never that big an issue for her. She was so young when he abandoned her and her mother, Chelsea only had one or two clear memories about him. On top of being in jail all the time, it was almost like she had never had a dad at all. Her clearest memory of him was the day he came home with a puppy for Chelsea's twelfth birthday. Chelsea was having a stage where she was constantly watching snoopy cartoons. With that in mind, her dad got her a beagle that she named peppermint patty.

Almost exactly one year from the day she got a pet beagle, her dad left and never came back. As if that wasn't traumatic enough for a thirteen year old girl, when her dad left, he took her beagle with him. Chelsea was devastated, mad, depressed, and cried for weeks over her two losses. The worst part was that Chelsea never found out why he took her dog with him. Her mom couldn't even make an educated guess as to why he took the dog.

Chelsea's mother never had anymore kids after Chelsea so she was an only child that learned at a young age how to take care of herself. Chelsea's mother worked constantly and would frequently just sleep at the hospital in order to pull double shifts for extra money. Chelsea's childhood wasn't all that terrible though, her mother provided her with pretty much anything she would ask for in exchange for Chelsea doing most of the housework during the week.

Chelsea often cooked meals, did laundry, took out the trash, cleaned, vacuumed, and anything else that her mother wouldn't have time to do. Because of all this, it was no surprise that Chelsea matured at a much younger age than most girls. By the time she turned eighteen, she was fully capable of running a house on her own AND still make time for field hockey, morning runs, and school. Chelsea had grown into an independent, hard working, mature woman before ever even having the experience of love or infatuation that most girls her age were experiencing right now.

Technically, Chelsea was still a virgin, but would occasionally pleasure herself when she had the house to herself and a spare fifteen minutes. Sometimes after school, and before she started her daily chores, she would watch one of her mothers porno movies that were tucked away under her bed. It wasn't very often, but like any newly developed young girl, she was curious with her body and with sex in general. If some of the girls in her high school were having sex with boys, then she should in the least be learning how to love herself. Besides she thought, how would she ever be comfortable with being with a guy if she didn't even know how to give herself a decent orgasm?

Chelsea's mother had a pretty varied and large selection of pornographic movies. She had everything from romantic sex on the beach movies to a thirty guy anal gangbang video. Chelsea's favorite video was one in which a young teenage girl would role play as a babysitter. The "dad's" would then seduce the babysitter and have wild crazy sex with them. Occasionally, the "mother" would also join in and it would become a threesome type sexual situation. Chelsea liked the idea of a much older man taking control and using her as his own personal sex toy. It seemed...delightfully naughty to her.

Even though she was a virgin, Chelsea knew her body very well and could control almost everything about it. She was so in tune with herself that she could dial up an orgasm rated from one to ten. A one, was a light, feathery, whisper of an orgasm, and a ten was Niagara Falls. Chelsea never had the Niagara Falls orgasm, but she was fairly certain that it was possible. She compared a ten to Niagara Falls because even though she had never seen it, she knew that she could, with a little help.

She would often wonder if all girls/women were capable of such an intense orgasm. Not all of her mothers movies had females that would squirt when they get off. Chelsea's curiosity about the subject became a little bit of an obsession at one point. Chelsea did a little research on it, but nothing was ever direct or consistent on the internet. Chelsea couldn't get a definitive answer about it so she decided to do something that no teenage girl does; she was going to ask her mother.

A day or so after Chelsea posted her ad on Craigslist, Chelsea sat down with her mom at breakfast. She spent a full day psyching herself up and then decided to just go at it like ripping off a band aid; the quicker the better. Chelsea's mom was reading the morning paper while sipping her second cup of coffee for that morning. Chelsea got a bowl of cheerios and took a seat across from her mother at the small dining room table.

Chelsea inhaled deep, sighed, then let it rip, "mom, we've been discussing the female body in health class and specifically about how a girl can orgasm. So, when a man has an orgasm, they obviously ejaculate and fluids...spurt...everywhere." Chelsea made an explosion motion with her hands as she said the last few words of the sentence to her mom.

Chelsea's mom gave her a look of sheer terror and at first couldn't speak. After a few seconds of processing the words she just heard come from her daughters mouth, her mom said, "we don't even say good morning to each other now? We just go straight into discussions on bodily fluids spurting during sexual intercourse? You're lucky this is my second cup of coffee."

"I'm sorry, good morning. How was your shift yesterday?"

"It's a little late for that. Now I'm thinking about things spurting. What's your question exactly?"

Chelsea laughed and remembered her favorite quality in her mother; her sense of humor. But it wasn't just that, it was their sense of humor towards each other and the ability for either one of them to ask absolutely anything to one another without judgement. Not all mother/daughter relationships were like that, and Chelsea knew it. Every now and again, Chelsea would be sure to tell her mom just how grateful she was for having her as her mother.

"So I've tried researching it and getting my own answer, but I can't seem to get a clear straightforward answer. Females, but not all, can have orgasms where they emit a fluid sometimes, but it's not like a guys. I can, but other girls can't. Why?"

"First off, going to the internet for information first is never a good idea buggy. So if you ever have a question concerning your young woman's body, come to me first, please. Second, not all women can have that kind of orgasm. Since we're being open about this, I'll tell you that I don't have those kinds of orgasms. I've seen videos too on it, but it's not something that just happens out of nowhere. A woman needs to know her body and kind of figure out how to do that on her own. Every woman is different, and not all have the same kind of orgasms from the same kinds of sex. There's more than one way for a woman to achieve an orgasm."

"Yeah, I already know that, but let's say, for example, if I were having sex with a boy, and I have a squirting orgasm, will he know that it's normal?"

"Ummmmm, I have no clue what they teach boys in sex ed. buggy, my advice is to not worry about it. Trust me, if a boy thinks that he just caused you to have a squirting orgasm, he's not going to think something is wrong with you."

"Ok mom, thanks. I'm not worried about it really. Just mildly curious that's all. I don't want a boy to think that I just peed all over him, even though I know it's not pee."

"Is there some boy in particular that you're thinking about having sex with? I know I can't stop you, but there's lots of things to consider before taking a big step like that with someone."

"Oh God no. I mean, maybe eventually, but not like today or something like that. Sorry if I scared you."

"The only thing that would scare me is if you came to me and told me you were pregnant. Now that would definitely terrify the shit right out of me. I'll drive you to school buggy. Just give me a minute to compose myself after all this squirting and spurting talk going on this morning. They sure don't make coffee strong enough for talks like these, let me tell ya."

Chelsea never told her mother that she was aware of the secret stash of videos. Like any curious teenager, she was curious and turned on by some of the different videos. When her mom was either at the hospital or out doing errands, Chelsea would frequently watch a snippet of one of the videos while enjoying and discovering just what kind of things she liked and didn't like about sex. Her mother had a wide variety of videos that were all clearly categorized and labelled accordingly. Chelsea, being only eighteen, didn't know much of anything the first time she discovered the videos under her mothers bed. However, three or four months of viewing them daily, Chelsea was kind of a sex expert before she turned sixteen.

Her favorite one out of the entire collection was of a petite young girl, allowing more than ten different men to have vaginal sex with her, unprotected. The girl in the video would demand all of the men to cum inside of her vagina whenever it was their turn to have sex with her. The men in the video were all much older than the teen, surprisingly, the teen was more excited and aroused than the men. The girl in the video was laying on a big bed on her back and was sucking one guys penis while stroking two other guys while being fucked by a fourth guy. It was a total sausage party and Chelsea was really turned on by how aroused the young girl was with all the attention she was getting.

Chelsea surmised that the girl couldn't have been much older than what she was. The girls size alone suggested that she was under twenty one years old. But the way she handled herself was extremely impressive for her age. Obviously this wasn't this girls first porno shoot. She seemed very focused and not phased by any new circumstance she was presented with. Definitely not the kind of career Chelsea could see herself in.

Chelsea knew she could have just as theatrical an orgasm as any one of these pornstars. Maybe even better. Still, being a pornstar was not as glamorous a life as it seemed to be on these videos, Chelsea assumed. In one video, the 35+ year old woman had BOTH her vaginal hole and ass hole penetrated with sex toys that were insanely large at the same time. Chelsea thought, there was no way that woman would even be able to feel a penis penetrating either hole after using toys like those. Hell, it would probably take two or three dicks just to come close to getting off. No...Definitely no interest for that field of work.

Over the course of six months, Chelsea knew everything there was to know about sex. EVERYTHING. From gangbangs to all lesbian squirt orgies to bondage and watersports. Chelsea was a professional which would serve to purpose as to why she was only really interested in an older, experienced man. Chelsea laughed every time she would try to envision herself having sex with a particular boy from her high school. Her vision always ended up with her having to explain to the young boy that a vaginal penetration orgasm, an anal penetrating orgasm, and a clitoral stimulation orgasm were all three very different experiences for a woman.

Six months of hands-on sexual education did come with a price though. As smart and crafty as Chelsea was, she was eventually caught red handed, ironically, a few days after posting her ad on Craigslist. Chelsea was completely naked and sitting on the floor looking up at the video while she penetrated her young hairless pussy with the handle of a thick hairbrush. Chelsea was laying on her back with both legs in the air on the verge of having a really strong orgasm. Even though she wasn't having sex with anyone yet, Chelsea loved the clean feeling of her freshly shaven twat. Being so young, there wasn't all that much to shave, but when she did, it looked amazing. She had even taken several pictures of her clean shaven pussy and saved them on her phone. If she were to gain a boyfriend before graduation, she thought it might be fun to tease the poor man a little.

Chelsea was on the very edge of her orgasm when she heard the front door being unlocked. Unfortunately, the front door led straight into the living room so she had no time to do anything except put her legs down and sit up. Chelsea's mom walked into the living room to see Chelsea fail at her attempt to not just turn the TV off, but to try and attempt a jumping, one handed, pants AND underwear pull up while ALSO going for her bra and shirt. The bra and shirt shot across the room and landed on the couch at the same exact time Chelsea's ass landed flat on the floor in an enormous loud thud.