Diary of a Loose Girl MF anal creampie

From the imagination of Chase Shivers

May 30, 2014

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Chapter 10: The First Fork in the Road

Chapter Cast:

Carrie Minberg, Female, 18-19
- Narrator, high school graduate
- Beige, freckled skin, 5'6, 145lbs, curly back-length dark-red hair
Lawton, Male, 18-19
- High school graduate
- Beige skin, 5'11, 225lbs, unkempt neck-length brown hair


Lawton had chosen to attend Texas Tech, and I was convinced I was going with him. I'd even signed the documents and had them in an envelope to mail back. We'd talked about how we would get into the same coed dorm in order to be close to each other, the classes we'd take. I was undecided on a major, though I leaned toward Literature after my extensive recording of my life in my journal. I didn't have to choose for another year or two. Lawton was going into Chemistry, a subject he'd enjoyed greatly in high school.

The day I set to confirm my place at Texas Tech, another envelope arrived, and it impacted my world in many ways. The single page document inside started with the word 'Congratulations' and ended with a signature from a name I knew. Pascal Rajamanan was a world-famous editor of various literary journals. I'd seen his name during the many nights I'd spent reading some of those journals, and the letter's body spelled out why he was writing to me.

Mom had sent off a few 'special assignment' sort of applications. College education in unique environments, opportunities that most people never got to see, if they knew about them at all. I found that out later. The program offered by Rajamanan was based in Amsterdam and featured two years of pre-major education, effectively an Associate's level of work. But it was specialized, the professors were active in the subject, held impromptu lectures for milling crowds, encouraged students to explore their literary boundaries, and the location was the far-away, magical place called Amsterdam.

I knew nothing about The Netherlands, but it was a name that immediately got me excited. I let the fantasy of attending play out for a few minutes, feeling really happy, before the crashing reality of accepting the offer hit me like a stone.

I sat quietly a long time in my room, nauseous. I felt so torn. At first, I easily decided to go to Texas Tech and be with my love. But the tug of the unknown caught me. It was a unique opportunity.

When Mom came home, I told her what I faced.

She had no easy answers. Mom became a much better counselor to me after my high school years, and the advice she gave me then was excellent. “Lot to consider, Sweetie. You've got a great boyfriend who you love and who loves you... you never know when or if that might come again.” She'd recently begun dating again, and I think she was surprised to find how easily she was able to explore relationships again. I assumed she had sex, at least some times, but I never asked her, and she never brought it up.

“On the other hand... The Bitterwood Curriculum is one of the best in the world. You can get into the best universities in the world with that pedigree, you know that.” I guess I did. “It isn't going to be easy, but Sweetie, if you finish that you'll have proved a lot to yourself. It isn't that hard to attract partners, you know that... not always the right ones, but at least you have options.” I knew I did. “You won't get another opportunity like Bitterwood, not likely, but lovers... with patience you'll find them.”

It sorta sealed it for me though I didn't acknowledge it for a few days.

I didn't tell Lawton about Bitterwood, and when he asked me if I'd sent off the documents to Tech, I lied and said I thought I had. It hurt a bit to lie to Lawton, but I was stuck in the pull of two really good options, and it burned me inside to know I'd not chosen Lawton.

Telling him took a swig of vodka that Mom kept in the kitchen. The second swig didn't hurt my courage.

I felt I needed something first, though. I'd been there several times when a relationship cut off quickly, and I hated that feeling, that lack of 'one last time' before you lose the right to touch that person. I fucked him in my bedroom while Mom was out on a date. He came in my pussy and was on his way to another before I wanted to give him a very special treat that I'd never given anyone. Somehow, the logic consisting of 'if I'm going to break his heart, at least I should give him anal first' seems rather silly looking back.

But I meant well, and I was buzzed on the liquor. I'd never had anal sex, and only rarely had Lawton played with my ass at all. I never particularly asked for it because I was just that satisfied by everything else we did.

I pulled him out of my pussy from where I rode him and stroked him slowly while I looked him the eye. “Sweetie... do you want something special? Somewhere I've never had you before?”

Lawton wasn't stupid, and he wasn't opposed either. His smile spread wide as I used my juices to lube up my asshole. I moved forward a bit more, tilted my hips forward at a longer angle. His penis nestled first against my labia then I slid him back to rest against my tight backdoor.

I slowly sank, my anus not yielding at first. I rose, wet my fingers, and covered the head of Lawton's cock. Back down, he slipped inside, and I sucked in my breath as Lawton's penis became the first to sodomize me.

It wasn't wholly pleasant, I admit. There were some movements that caused me to tense up, to clench him uncomfortably. I felt like I was about to take a huge shit on him, which I desperately hoped I wouldn't do. I'd already peed on one boy, I think this would have been immeasurably worse.

But I rode him as best I could, resting some moments before slowly moving again. I didn't take all of his cock in my ass. I couldn't, only able to stretch enough to have about three inches inside. He felt huge, and I couldn't imagine how in the hell porn actresses regularly took eight-inch dicks pounding in their butts.

Lawton groaned and rose up, his face one of concentration, of pleasure, focus. His cock stretched and I cried out in discomfort. It pulsed again, sending tiny spiders of pain from my ass down my legs and up to my stomach. He groaned loud, said, “Oh.. OH... CARRIE.. OOOOOOOOOHHHH” I felt his cock throbbing as it ejaculated in my bowels. It was all I could do to stay on him as he came, my sore butt trying to force him out.

I didn't feel the cum splashing in me, but I knew it was there, and I gritted my teeth and tried to record that moment as one of pleasure, not pain. I mostly succeeded, thinking back, but it would not be the last time I had uncomfortable anal.

I rose off Lawton soon after he'd drained his nuts in my ass. I kissed him and went to the bathroom, heard him rise and go to the one down the hall. I wiped away the mess, streaks of brown mixing with his cum which ran from my raw, slightly gaping anus. A few minutes of soap in the shower and I was clean again.

And almost ready to tell Lawton the truth. It was a big 'almost.' It was hard, possibly the hardest thing I'd ever done in my life. I loved him so much, and I tried to find ways for it to work. We could be in a long-distance relationship, we could stay celibate until I returned... if I returned. I knew each one would fail, and I accepted the reality that I just had to tell him.

And so I did. He cried, I cried more. He wasn't angry, just sad, and I knew exactly what he felt. He handled it much better than I thought, and he reminded me that we still had a couple of months of summer together before it became time to break up.

That summer was wonderful for me. I turned nineteen and I amazed myself at getting over the sadness, the anticipation of loss I dreaded to think on. It wasn't that I wasn't sad about it, just that... it didn't dominate my mood. My future path offered two choices, and perhaps, for the first time in my life, I decided with my head instead of my heart, instead of with my puss.

We spent a lot of time together. Mom's dad passed away and left her a nice amount of money, enough to pay off the house we lived in and put some money into the bank for my expenses. The two of us went to Seattle for his funeral, and Lawton was there with me.

Lawton and I fucked a lot, horny young rabbits, and I never had an experience with him that I'd take back. He gave himself to me freely, perhaps the first person that really had, and I'd felt the freedom to offer myself the same way. He came in my vagina. He came in my mouth. He came in my ass. He liked that, in case it wasn't made clear. And as I got used to it, learned how to stretch myself out first, learned how to pick a good lube, anal sex with Lawton was amazing, and I came hard riding his dick with my ass.

The last week together was hard. Every tick of the clock meant a measurable amount of time less to be together. He stayed with me the week before he left for Tech, and Mom was a great host, allowing us lots of privacy and an empty house. I really appreciated how she supported me then, and Lawton and I made the most of it.

I had a ten second fantasy at one point, as Lawton tensed, ready to fill my pussy, about having his child. I let the fantasy play as he came in me, imagined that he was fertilizing me, his seed soaking through to my womb to find my egg. It was the first real impulse I'd ever had to want pregnancy. It passed as he came and I sank into the way he held me tight as he ejaculated into my body.

Nothing serious, nothing I worried about, but that fantasy played out many more times in my future.

He left and was gone for an hour before I allowed myself to cry. I felt so hollow. All the joys I'd looked forward to no longer held a color without Lawton there to share them with me. I cried, and Mom cried, and she shared a bottle of wine with me for the first time.

Since Dad died, my mom had blossomed in more ways than just relationships. She spoke her mind more freely, she held opinions on politics, religions, and some of them surprised me. She was more willing to have a drink or two with dinner. Never more than two, but she enjoyed both wine and sherry with meals.

We drank a bottle of some red wine that I thought was a bit sour, but I didn't pass up a second glass when it was offered. We got a bit drunk and cried some more. And after that, I was ok. Really ok. I thought about Lawton daily for many months, but that was the point that it became ok to let him go. I cried sometimes in the days that followed, felt unbalanced for weeks, and the rare times I had a chance to talk to him on the phone, I felt the distance growing between us very quickly.

I still loved him, still considered him a friend, but he wasn't mine anymore. Perhaps more importantly, I wasn't his any longer, either, and that opened the world up to my eyes, and to my sex life, in ways that I could only begin to imagine.


End of Chapter 10

Read Chapter 11