From proud virgin to his Big Butt Ashley ** PM interest **

[ForeverIllinois]

From proud virgin to his Big Butt Ashley ** CLOSED **

It took him only five days - five days to turn me from a proud conservative virgin girl to a sex crazed submissive fucktoy. To make matters even worse, I met him less than a week ago. Now that I think about it, it seems that from every single one of those five days, he managed to manipulate and seduce me, taking things a bit further and further; before I was any the wiser, I was screaming and moaning my lungs out, taking in his huge fat cock inside of me, hearing him laugh as he kept fucking my brains out and doing the most degrading things imaginable to my young body. Truth be told, I had no idea about how badly I wanted to be used, degraded and objectified until he started doing things to me that I never dreamed of. I mean, for all my life I thought that sex was supposed to be soft and lovely and this experience has taught me that I can't get enough of this rough, porn star worthy sex that he was giving me.

But before I get to that, I should probably start from the top. Hi, my name is Ashley Rodriguez and I'm a high school senior at North Bay High.

...


http://i.imgur.com/SkjqVqS.jpg
Name: Ashley Rodriguez
Age: 18
Height: 5'9"
Cup: 38DD

...
​

As I've mentioned, I'm starting this story at about five days ago when I was still together with my boyfriend, Phil. Phil and I were pretty much your typical high school couple; we had a cute story about how we got together, how there was talk about how we'd get married and well, you know, how we were unseperatable. Phil was the team leader of the soccer team at school and kinda represented the ideal physique and social standing of an eighteen year old. He was pretty much the sweetest guy that I've ever met, even if he did lie to some of his friends about how we've done it.

That's right, up until yesterday, I was a virgin.

I mean, despite what you may think right now, my parents did a great job raising me into a conservative Catholic like most people from their generation. I went to Sunday school, I volunteered at my church, so it goes without saying that I absorbed and held some of the church's fundamental beliefs when it comes to sex and marriage. Even if everyone at school was practically chasing after me.

I'm a bit of a sex-bomb. I'm not a particularly arrogant person and I'm not some fashion model, but I'm pretty confident about my appearance. I'm 5"9', naturally brunette, constantly wearing a tight fitting DD cup bra and have a slimmer body type with curves in all the right places. I've really developed, but what really seems to attract guys are my wide hips and my big, round butt. Fortunately for me, the man that I'm about to tell you about is a notorious ass man.

...

Day one:

I was pretty upset that my mother needed me to pick up my four year old nephew at his day care. At eighteen years old, you'd think that my mother would know by now that I had a life beyond home and school! After all, it was summer and Phil and I had planned earlier to go to the park and spend some time together now that school was over and our summer break began. We had a couple months before college and I wanted to make the most out of it. While I was a bit annoyed over having to cancel at last minute, I was still pretty thankful that it wouldn't take too long; all I needed to do was pick him up and bring him over to my place and babysit him for an hour or two.

Unfortunately, the little brat was being a pain to pick up from the daycare. It didn't help that they installed some inflatable jungle today and I had to do my best to drag him out of here.

I was so caught up on this that I didn't even notice the older, mature man staring and recording my ass from behind - contemplating on how he'd approach me...

http://i.imgur.com/e5gK8HM.gif​

..

 

[Bevatoria]

And what a five days it had been...

One of the benefits of being divorced was that I didn't have much of a life outside of working, sleeping, and picking up younger women. Repetitive, but in the right way, at least outside of my job. It was a simple one working at the daycare, and since we were a smaller organization it meant that our jobs weren't really set a lot of days. We just did whatever needed doing, whether that meant making food for the kids, reading them stories, or just watching over them during naptime. Not the best career in terms of advancement, but in this economy you took whatever you could get. Which wasn't the way I thought about women; while I was careful during the job, outside of work I, Alan Smits was known as a bit of a ladies' man.

But at the job, I was just the helpful do-everything guy who used to sell cars.

Today, I'd been tasked with taking pictures of the kids on the inflatable jungle, which they let me do on my phone. I could always clean them up later and in any case I had a newer Sony phone which had a better camera on it then most phones. I was going around catching the kids in action on the gym, and then I saw one of them apparently trying to get away from someone...

...and then I saw something I enjoyed seeing. A round, barely clad female booty sticking out almost right at my face. Thinking quickly, I swapped from pictures to video, ostensibly moving around her to get a shot of the kid even as I was just trying to get another moment or two of her cheeks before I finally maneuvered around her to get the picture I 'wanted'.

That, and being too obvious was the wrong way to go about it. Even here, where I could explain almost anything away, I knew not to push it. I sidled up besides the woman who's ass I'd just gotten a great photo of. "Excuse me, but is that your child?"

After I got a better look at her, I could obviously tell that she was too young to be the child's mother... "Oh, sorry. I'm Alan, by the way. Not sure I've seen you here before." I had on a nametag which indicated I worked at the daycare, but the uniforms were all pretty casual most days; we knew who was supposed to be here and not.

 

[ForeverIllinois]

"Excuse me, but is that your child?"

I quickly turned around to see an older looking man staring right at me, focusing his phone on my nephew. It wasn't until I noticed his colorful name tag that I realized that he probably worked here, and that I obviously needed to speak to someone before getting James (my nephew) out of here. Wait a moment...

Did he ask me if this was my child? I mean, I know that I didn't wear as much make-up as I would have liked but I couldn't look much older than my age, right? Well, moving that out of the way, I think the day-care employee felt bad. Bad enough to give me a quick apology:

"Oh, sorry. I'm Alan, by the way. Not sure I've seen you here before."

I squinted at the name-tag (I was horrible at remembering names) before answering back "Nice to meet you Alan. Yeah, it's usually my sister who picks James up but she's on a conference or something. But you probably need proof right? Hang on..." I mumbled, before reaching into my thin leather jacket and pulling out a piece of ID with my name and age on it. My sister kept her last name, so I figured that this was good enough.

 

[Bevatoria]

"Nice to meet you Alan. Yeah, it's usually my sister who picks James up but she's on a conference or something. But you probably need proof right? Hang on..."

That we did, as child safety was the one part of this job we all had to take seriously. More than the standard background check was done on everyone who worked here, and we had to make sure that each child was let out to someone who was authorized to take them. Luckily, Ashley was on the list, and I almost let out a whistle as I looked her over. Yep, definitely not that old.

"That'll do." I nodded. "Looks like he's gotten pretty interested in this thing, so..." I stepped by her, reaching out my hand towards her nephew. "C'mon, bud. Time to go!" I clapped my hand a couple of times, and he bounded off of the gym to join us, and I gave Ashley a winning smile.

"Just gotta know the code, I guess." I gave another look around; I was pretty much done my picture taking for the day and the boss had said I could go when the guardians for the kids started showing up, so.... "Do you need any help with him? I know that people who don't take care of kids can be a bit overwhelmed, so I'd be willing to stick with you a bit if you need a hand." I tried to put on my nice guy look, just a guy who didn't expect anything.

Although what I really wanted was more time with her, and not the kid.

 

[ForeverIllinois]

"That'll do." he said with a quick nod "Looks like he's gotten pretty interested in this thing, so..."

With a quick movement, he stepped by me and reached out for James. If I knew my nephew, which I thought I did, I knew that he'd struggle getting out. But, as if this Alan guy knew magic or something, my nephew willingly bounced out of the inflatable gym and came towards us. I was surprised to say the least. I turn to face Alan and he gave me this triumphant smile; I couldn't help but do the same!

"Just gotta know the code, I guess." Alan said, seeing my surprise.
"Well I need that code, because he's not always this nice." I answered with a laugh.

"Do you need any help with him? I know that people who don't take care of kids can be a bit overwhelmed, so I'd be willing to stick with you a bit if you need a hand."

I paused for a second because I didn't know if it was the best idea to have a stranger over to my place. I mean, I was sure that Alan was harmless, it's just that technically it wasn't my place; it was my parent's. They weren't home and wouldn't be until late, much after my sister would come up and pick up James (which was in about two hours from now). Alan seemed good with kids and well, I wasn't - if he were around then I wouldn't have to deal with James if he'd throw a tantrum or a hissy fit later.

"Sure, I'd love some help!" I answered with another smile "I live just three blocks away from here. But are you sure?"

 

[Bevatoria]

The pause in her voice didn't make me nervous. It was only kids who needed to look out for strangers, right? Surely she could make her own decisions at 18, and I just wanted to look after the kid, and not that fine body of hers hiding under those less then flattering clothes...well, less flattering then I wanted. There probably wasn't any fabric that existed that wouldn't flatter her in some way.

"Sure, I'd love some help! I live just three blocks away from here. But are you sure?"

I shrugged, as if I was fighting my own indecision. "Eh, sure. I don't have much on the go for the rest of the day and I enjoy being around kids." A half lie. I didn't hate kids, exactly, but to say I enjoyed it was an exaggeration. The rest of my day, though, was as clear as the sky above us. "We can walk there together, if you didn't drive." I left my car here once in a while and the boss didn't mind."

I'd seen she was 18, which probably meant... "So, where are you going to school next year?" She could've just finished her freshman year although I doubted it.

 

[ForeverIllinois]

"Eh, sure. I don't have much on the go for the rest of the day and I enjoy being around kids."
"Great! Also, if my nephew is a pain, I'm so so sorry." I said with a light-hearted laugh before motioning James to come along. "Come on James."
"We can walk there together, if you didn't drive. I left my car here once in a while and the boss didn't mind."
"Oh sure, it's not much of a walk anyway."

And so, as we began walking towards my place, I began to wonder how much I stood out from all the people who were picking up their kids. I mean, I probably was the only one there who wasn't a parent and (not to seem really arrogant but...) was actually attractive. I suppose my clothes made me stand out even more; especially my white top and tights which showed off a lot of my um...assets. I just hoped that neither the cleavage that my top gave out, nor how my round ass was hugged by these tights made me seem slutty in front of those parents.

"So, where are you going to school next year?" Alan asked me, snapping me out of my thoughts.

"Oh um...I'm going to New York College." I replied simply "I'm looking forward to it!"

True to my word, it didn't take too long for us to reach the place; a modest five room apartment on the second floor. "Here we are." I said with a smile before heading up the stairs, keys in hand, before opening the door.

 

[Bevatoria]

"Oh um...I'm going to New York College. I'm looking forward to it!" She replied quickly to my question. I nodded, fully aware that I didn't want to sound like all of the other adults asking her what she wanted to do in life. That was for parents, folks who didn't have interest in her as an 'equal'. While what I had in mind was for us to be on anything other then an equal footing, I did want her to just think of me as a friend. An older guy who talked to her on the same level.

"That you should." I responded. "A good chance to broaden your horizons..." With the kid around, I needed to be careful about what I said, and eventually we got to her apartment. Nothing fancy, but functional, which is what I preferred.

"Here we are." She said, and I saw how a guy could get lost in that smile, even if a real man would just admire it for what it was while stealing a glance down her shirt. Keeping a mindful eye on her kid, I followed her into her small kitchen as I placed my thin jacket on a chair, walking to the counter where I couldn't help but think of how Ashley would look bent over it. "Nice place." I commented, getting out my phone discreetly as I looked to the fridge.

"I hate to impose, but do you have any orange juice? I could use a squirt or two."

Luckily, like most phones these days, mine could quickly switch to camera mode when I needed it...

 

[ForeverIllinois]

"Nice place." he said, walking to the counter and leaning on it. James was close by, so I wasn't worried about the little kid wandering too far off. I went to the kitchen to get myself a glass of water and I swear that I was right about to ask him if he wanted anything, just as he said:

"I hate to impose, but do you have any orange juice? I could use a squirt or two."

"Sure thing!" I answered eagerly, thankful that I didn't have to deal with James by myself - he is, after all, usually a huge pain to deal with. So, I opened the fridge and leaned in to pick up the carton of orange juice and filled a glass with it. I went over to Alan and gave him his glass of OJ. Of course, at the time I had no idea what he was doing. If I did know, maybe I would have paid more attention to my own mannerisms, especially how sometimes I wiggle my butt ever so slightly when I'm looking for something.

 

[Bevatoria]

"Sure thing!"

Her saying yes wasn't the surprising part; after all, if she'd done the same for me at my place I would've done the same thing. But being the practiced voyeur I was, the phone was out as she turned away, bending over and flashing me her tight clad ass. It was just a short, little moment but I couldn't help but admire how she wiggled her rear at me as she found my drink. Of course my mind went to naughty places as she did it. I could feel the urge in the back of my mind to reach in and give her a playful slap, but we had just met and I was going to be patient. Sure, it'd be fun to see and feel my strong hand slap her butt, but it'd be accompanied by being thrown out of her house and to never see her again, to say nothing of possibly being fired.

So instead I took the drink from her with a nod of thanks, sipping it as I ruffled James' hair; he was lurking around. "You're a good sister if you're willing to help out like this...it shows a level of responsibility that most 18 year olds don't have." A true compliment, even if I was just trying to get on her good side. "Some are just interested in partying mindlessly without caring about anyone but themselves. This will serve you well when you get into the working world - trust me on that." I gave a self deprecating smile as I continued. "I'm just glad you're willing to let an older guy hang out with you." An easy chuckle followed; she knew I was here to look after James, but I liked the idea of hinting that I wasn't.

 

[ForeverIllinois]

"You're a good sister if you're willing to help out like this...it shows a level of responsibility that most 18 year olds don't have." he said, after I handed him that glass of orange juice.

I smiled at that and nodded, replying "Thanks! I appreciate it." Of course, I didn't bother correcting him that the kid wasn't my brother, but I appreciated the compliment nonetheless! I mean, even if I was a bit lazy when it came to handling this by myself, at least I didn't try to weasel my way out of this chore. I guess at the end of the day, I was a sucker for compliments.

"Some are just interested in partying mindlessly without caring about anyone but themselves. This will serve you well when you get into the working world - trust me on that. I'm just glad you're willing to let an older guy hang out with you."

I chuckled a bit, brushing some hair off my face as I said "It's no problem, I don't mind hanging out with you."

I glanced at James and it seemed as if the little guy was falling asleep on the chair. I glanced at Alan and nodded towards my nephew. "Looks like somebody is sleepy. I'll just take him to bed and I'll be right back!"

 

[Bevatoria]

"All right." I idled around a bit, still picturing her brushing her hair back in my mind - it was a cute little gesture - as well as what she'd said earlier about not minding hanging out with me. I resisted the urge of thinking about how amazing it was that this sexy 18 year old soon to be college freshman wanted to hang around with a fortyish year old daycare worker. I was confident enough to know that things would end up this way; it was how I got the ladies I did. I took a few looks around before she came back down, my eyes latching back onto her the moment she returned.

"You must have had guys chasing you all over the place." I teased, taking a sip of my drink, needing to get a measure of how much she'd let me get away with. "Not to be too forward, but if I were still your age, I think I would." Another beat passed as I let her respond, liking how she seemed to be going with it. So innocent, so naive...she'd be fun to have, in more ways then one.

A plan was starting to form in my head, albeit one subject to revision at any time (especially if she stopped playing along). "So do you live with your parents, or on your own?"

 

[ForeverIllinois]

It didn't take too long to tuck James in. While he was one of those kids with a crazy amount of energy, he seem to have spent it all at that inflated playground. So, within five minutes, I went back downstairs and saw Alan in the same spot as earlier.

"You must have had guys chasing you all over the place." he teased when he saw me, sipping from that glass I gave him earlier. I chuckled at it; surprised that he said that. I mean, don't get me wrong, it wasn't as if I was offended or anything. Just that well...doesn't that mean that he's attracted? Maybe I'm just reading too much into this. "Not to be too forward, but if I were still your age, I think I would."

I giggled again "Well, thank you." I replied with a smile before I sat down near him.

"So do you live with your parents, or on your own?"

"Well..." I answered, almost ashamed of the fact that I lived here."I still live with my parents. I'm planning on moving out in a year though!"

 

[Bevatoria]

Her answer to my question wasn't that surprising, although it did give me a bit of needed information. "Well...I still live with my parents. I'm planning on moving out in a year though!" So taking advantage of their leniency while here yet still pushing for her own independence. I was begging to like this girl more and more for reasons other then her 'assets'. "That's good." I nodded in approval. "You're getting to that time of life where you need to be free, spread your wings and try some new and exciting things...college isn't just about getting your degree, after all."

I should know, since I spent more time partying then studying. C means degree, or so the saying went. Probably still did, if what I knew of college coeds was any indication...

Her parents living here, however, meant I didn't want to linger, lest I get caught. There was still some time, though. "I shouldn't stay too long, don't want to feel like I'm imposing on you now that your nephew is in bed...but I always like to test out friends of mine with a game or two." I paused, supposedly self conscious. "Assuming it's okay if I call you a friend..."

 

[ForeverIllinois]

"That's good." he said with a nod "You're getting to that time of life where you need to be free, spread your wings and try some new and exciting things...college isn't just about getting your degree, after all."

I knew what he meant; it wasn't worth going to college if all I was going to do was shove my face into books. I nodded in response before saying "Yep! That's the plan alright."

"I shouldn't stay too long, don't want to feel like I'm imposing on you now that your nephew is in bed...but I always like to test out friends of mine with a game or two." he then said with a pause "Assuming it's okay if I call you a friend..."

I felt bad - I mean, he's asking if it's okay to call me a friend. I protested quickly "Oh of course it's okay to call me a friend!" and then with a smile I said "And what game are we talking about here?"

 

[Bevatoria]

It probably wasn't hook, line, and sinker but her response was about as good as it could have gone without her offering me a blowjob. Eventually, but Rome wasn't built in a day...

"Oh of course it's okay to call me a friend!". Her smile warmed me despite myself as she continued "And what game are we talking about here?".

I shrugged. "Well, if you've got some cards, we can play blackjack for a bit. I like seeing how people compete, what can I say?" I shrugged, giving a guilty smile. "Or if you've got another game you'd prefer, but I want to keep it simple." And short, since I wanted no part of running into her parents. Best to keep her separate and unknowingly compromise her judgment with innocent statements.

"Assuming you think you can win, anyways."

Okay, maybe a prod or two would work, too, if she was competitive.

 

[ForeverIllinois]

He shrugged in response and gave me a guilty smile in response to my question. I looked at him, wonder what his idea was.

"Well, if you've got some cards, we can play blackjack for a bit. I like seeing how people compete, what can I say? Or if you've got another game you'd prefer, but I want to keep it simple."

A card game? Well, I suppose that it would be the fastest but...that sounded an awful like gambling; not something that I was too crazy about, anyway. But I gave it some thought and really, I was about to say no. Well, that is until:

"Assuming you think you can win, anyways."

Okay, so I am a bit of a hot head and an awfully competitive woman. So when he said that, I couldn't help but answer back:

"Oh, you're so on." before I went towards the fridge and picked up a deck of cards. "We're playing blackjack and I'm going to beat you."

 

[Bevatoria]

Whether she was playing it up or not, it seemed my minor jab had its intended effect. "Oh, you're so on. We're playing blackjack and I'm going to beat you."

Blackjack was a game of luck, but I'd made it a practice to count cards to get whatever tiny edge I could. Even if I could cheat, I wouldn't do that this early on; this was just setting the table for what I wanted to happen later. "If you say so..." I smirked back. "Usually, I play for a bit of money so I'll put up five bucks." I put the bill on the table as I looked at her. "You can do the same, or we just play for fun." I looked around deliberately. "Although then I'll assume you just think you can't win."

Unfair, sure, but I wanted her to get used to the idea of playing for something, even if it was just a bit of a risk. Tiny risks could lead to larger ones, and eventually I wanted to be playing for more then money.

 

[ForeverIllinois]

"If you say so..." he said with a cocky smirk "Usually, I play for a bit of money so I'll put up five bucks. You can do the same, or we just play for fun."

I was about to suggest that we play with no wager. As I might have mentioned earlier, I hate the idea of gambling; in my mind, it always felt as if 'losers' were the type to place bets. After all, my family raised me to be against certain things - like alcohol, drugs and of course gambling. But once more, Alan's cockiness stirred up my competitive side, especially as he added: "Although then I'll assume you just think you can't win." and placed a five dollar bill on the table.

I searched the thin pocket of my tight yoga pants and replied with:

"Oh yeah? Here's my five bucks!"

 

[Bevatoria]

She could have taken forever searching her yoga pants for her money and I wouldn't have minded, as long as the fabric kept rubbing all over her well defined curves, her young, flawless skin that was visible through the material....pulling out a bill to match it, I theatrically put it on the kitchen table nearby, inviting her to sit across from me. "I'll deal first." My hands shuffled the cards tentatively, not wanting her to know that I'd played a weekly game with several of my friends for years until too many of us had finally moved away...

"Best three out of five?" I tilted my head, dealing one card down and one up to both of us, as they were supposed to. "Tie goes to the dealer, so I'll let you deal the fourth and fifth times..." I saw that she had a jack showing (which meant ten), and I had an eight showing and four in the hole. After she decided how many cards to take, I played. "Dealer hits..."

Got a five, which put me at seventeen, although she would only see thirteen. "..guess that's good for me." I said, flipping over my card to show my final score. "How did you do?"

 

[ForeverIllinois]

Okay, so apparently blackjack was pretty damn fun! With each shuffle, I paid careful attention to the cards - or more specifically, the movement of the cards while Alan shuffled them and eventually when he passed them. I think I saw a...ten? I wasn't sure and the more I tried to guess the cards Alan got, the more anxious I got. It wasn't a good strategy for me...

"..guess that's good for me." he said, flipping his cards to show his final score. "How did you do?"

With a pout, I revealed my cards. "15. Well, there goes five bucks."

...That's when I realized it was blackjack - I had another shot! "I mean uh...can you draw another card for me?" I added with a grin on my face.

 

[Bevatoria]

"As the lady wishes." I grinned at her, knowing it was bending the rules a bit but what the hell...I flipped it over, and it turned out to be a five, which left her with twenty. "You win this one..." I teased, pulling the cards of the deck back together with a flourish and handing it to her. "Why don't you deal me some and see if you can repeat your lucky draw?"

I saw my cards first, and I there was a eight and a four. About as bad as it could get; although at least the four was the visible card. "Hit me." I said, asking for another card as I got the nine! That put me at twenty one, but I barely reacted as I looked at her. "Good now." I smirked, as I looked to see what she had.