Diary of a Loose Girl - Cover

Diary of a Loose Girl

Copyright© 2015 by Chase Shivers

Chapter 29: Jayna

Fiction Sex Story: Chapter 29: Jayna - Diary of a Loose Girl follows a woman named Carrie. From her earliest sexual experiences through her adult life, her first time, her kinks, the men and women she fucked and loved, she recorded it all in her Diary. Follow Carrie's retelling of those personal notes as she details what she tried and liked, what she tried and hated, the people she loved and lost, and what turns her on beyond imagination. Note - This story is open-ended with 28 chapters so far.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Fa/Fa   ft/ft   Mult   Consensual   Lesbian   BiSexual   Heterosexual   Fiction   School   Tear Jerker   Interracial   Black Male   White Male   White Female   Oriental Female   Anal Sex   Cream Pie   First   Masturbation   Oral Sex   Safe Sex   Sex Toys   Teacher/Student  

I woke the day after my meeting with Elise feeling fresh and alive like I hadn’t in a long time. Even with Lacy and Donnie and Andre, when days with them felt wonderful, I’d never come close to the deep emotional happiness I felt in earlier moments with Elise. Just knowing I could talk to the woman again, to know I could share my emotions, lifted a heavy weight from my thoughts. I knew I could never fully absolve myself of my mistakes, but I was determined to set things right as best I could. As friends, if that’s how it had to be, though I hoped that Elise and I might once more share our love as we had before. It was impossible not to fantasize about what was to come for us as I lay in bed that morning and tried to ready myself for a long day at work.

Thoughts of Elise made me step lightly and smile all day. Lacy had noted my improved morning mood before I left and I shared a long, lovely hug with her as I gushed about feeling so relived to know that I hadn’t completely lost Elise from my life. Lacy cautioned me about getting myself too deep in fantasyland, too caught up in rosy scenarios and dreams, but she was happy to see me not drag myself down for coffee looking morose and lost as I had been so often over those weeks.

That night, Elise called me and for an hour or more, I lay on my bed and lost myself in our conversation. We talked of school and work and old classmates and fun times we’d had together. She was having lunch with Julens the next day and I asked Elise to send her my love and thanks. Julens had been a fierce friend, a one-time lover, when I’d needed help during those dark days after Elise had discovered my affair with Drew.

All-too-soon, we were both yawning and Elise told me, “Wish you were here, Carrie ... I’d sure love to snuggle up with you right now. It’s really cold tonight ... and I always did love when we did nothing more than keep each other warm through the night...”

I told her, “I’d love that...”

I almost suggested I was already considering moving back to the East Coast but held off. It was true. The fantasies in my head involved me being close enough to Elise to restart our relationship, but as Lacy had cautioned, I couldn’t just jump in like that and expect everything to just work out. Whatever Elise and I might have together in the future, it couldn’t start with a spontaneous move back into her life. We needed to move more slowly, I knew, though it was painfully difficult to draw to a close the call, Elise telling me, “Love you, Carrie...”

“Love you, too...”

I lay awake a long time that night, fantasizing about doing nothing more than holding Elise in my arms and kissing her like the relatively-innocent girls we’d been back at Bitterwood where we’d first discovered our love together. It was bittersweet, admittedly, to feel the difference between where we were that night and what I’d destroyed in our past. At least we were talking again, I accepted as the huge step forward that it was. I wanted nothing else in life than to spend every day making up for my betrayal by showing Elise how much I loved her.


October turned into November. I continued to work and fantasize about Elise and what might be. We talked several nights each week, though Elise was quite busy with coursework and her own job as a teaching aide on campus. Mostly, it just involved her handling the set up for evening classes in Literature, ensuring copies were ready for students, and that any presentation materials were prepared ahead of time. As dry as that all might have been to anyone else, I loved hearing Elise describe every detail of her day.

I first broached the subject of me visiting during the first week of November. “Hey, uh ... I have a week of vacation to take before the end of the year ... uh ... Any chance you might like some company for Thanksgiving?”

Elise replied with light disappointment, “I’d love that, but ... I’m going to be visiting my parents in Switzerland, unfortunately...”

“Oh...”

“But,” Elise added, “I’m free for Christmas break ... could you come then?”

“Yes!” I exclaimed, “God, yes, Elise! Even if I have to quit my job, I’ll come to you.”

I heard the smile in her voice, “Good ... I really miss you, Carrie ... I love talking on the phone, but ... I just want to see you, in person, real soon...”

I told her I felt the same and our conversation soon turned back to more mundane activities, like work or school associates who we thought were a little odd.

By the week of Thanksgiving, I had generally come to think of Elise as my girlfriend, to the exclusion of anyone else. A couple of guys at work had asked me out, but I declined, not offering my reasons, but I tried to be polite about it. Sure, it was nice to know I could still attract the interest of reasonable and decent looking guys, but my heart had settled on my favorite person in the world, and no one could ever make me feel what I felt for Elise. I knew I was treading on waters a little turbulent, that with the distance and only our phone conversations to maintain our foundation, I was creating a house of cards in my head about our relationship which might, one day, prove too unstable to match reality. I couldn’t help it, though. Elise had never been far from my thoughts even in the darkest of times, and hearing her laugh made me warm and find my love for her all over again.

That fantasy took a hit during Thanksgiving break. I was home alone, Lacy and Harrison had gone to a cabin by a lake somewhere near San Diego for the holiday, and I had a few days off work. They’d invited me to join them, but I knew that Lacy and her boyfriend were starting to grow closer, more serious than they’d been in the months before, and I didn’t want to go along and be a third wheel while they worked out where they might go next as a couple. Lacy even wondered if Harrison might propose on the trip. She was excited and told me she would accept, if he did.

Elise called me from Berne where she was staying with her parents and a couple of other family members. We talked briefly about her flight and the cold weather in Switzerland, as well as the slopes she was going to ski in the spare days before flying back to Boston. Then she hit me with something I had known deep down might come up, but which I really hoped would not hurt so much. “I, uh ... I need to ask, Carrie ... Do you ... Do you think of us ... like ... we’re exclusive?”

My throat constricted, “Uh ... I ... I dunno...”

“I know we’ve been getting closer, and you know I love you so much, Carrie, but ... you’re way out there, and ... I’m ... I get lonely, you know? I think you know what that’s like...”

Of course I did. It was part of why I’d failed so badly at being faithful to Elise in the past. “Yeah...” I offered, tentative and dreading what she might say next. “I ... I dunno ... I ... I’ve not been seeing anyone, Elise...”

“I haven’t, either ... But ... There’s a guy here, a guy I knew from my life before Bitterwood ... and...” Elise trailed off. She was trying to gently ask my permission to take a lover.

It wasn’t my place to give permission, I knew that, but I couldn’t help but feel the sting of what was going to happen. I hesitated, pausing, silent. Elise breathed, “Carrie?”

“I’m here...”

“I won’t see him ... don’t worry about it.”

“No,” I said more firmly than I felt, “no ... that’s not fair ... we’re not ... we’re not dating, really ... I know that ... Go have fun, Elise...”

“Carrie...”

“Seriously,” I told her, masking the hurt as best I could, “go have fun. If we’re going to get past ... what I did ... we can’t keep pretending that things ... are always going to be exclusive with us, right?”

Elise was silent a moment, “I think that’s true...” she said quietly.

I knew we were both thinking about my affairs and how I’d been completely unable to stop myself from cheating despite how wonderful and loving Elise had been to me. Part of me wanted to promise fidelity, monogamy, faithful exclusion, but deep down, and despite the rosy love which had been growing for Elise over the weeks since our reunion, there was an admission of weakness still clinging, still simmering, that I would always desire other relationships. I swallowed hard, almost bawling to think that Elise could never be enough for me, or that I wouldn’t fulfill every desire for her. It hit harder than it should have, but I kept back the tears and assured Elise that she was free to pursue anyone of interest. “Just be sure you think of me when he’s going down on you,” I forced a chuckle, hoping Elise wouldn’t notice the strained tone in my voice.

“Yeah ... yeah, I will ... You sure, Carrie? I ... I don’t want to ruin things...”

“Not at all ... remember when, before we were ... exclusive? Those were fun times, right? Just us having fun and not worrying about all this?”

“Yeah, I remember...”

I swallowed the lump forming, “Then let’s do this the same way, right? This should be fun, not painful ... Go have fun, Elise...” I paused, then steeled myself, “Hell, maybe I’ll go find some fun myself this week...”

“Yeah,” she replied, “that would be nice. Nice for both of us, huh?”

“Uh-huh.”

We were both faking being all right, but neither of us could say so right then. I sent Elise my love and she did the same for me. When we hung up, I burst into tears, feeling more down than any time since Elise had come back in my life. I was desperately jealous of some anonymous guy in Switzerland who would get to hold and kiss Elise that week, horribly angry that such an asshole would be in a position to do what I wanted to do. To taste her, to make Elise cum. I cried myself to sleep that night and didn’t know how the rest of my lonely Thanksgiving break could possibly improve.


My mom called the morning of Thanksgiving. She was vacationing in Thailand with her husband, Harry and wanted to let me know she was thinking about me. We’d stayed in contact over my months in California, but I’d never let on the struggles I’d had nor mentioned lovers over that time. I had, though, told her about seeing Elise again and she was happy to know that my dear friend was part of my life again, even if from a distance.

She’d sent some money to help me afford the trip to Boston. I did okay at my job, but it was far from lucrative, and even with the decent rent I paid to live with Lacy, it was still expensive to live in Boulder Creek and I often had little spare money for such things as travel and fun. The funds Mom sent were more than enough to cover the trip planned for December, and I had sat on the extra a couple of weeks without any impulse to spend it.

It eased my mind a little just to talk to Mom, but the conversation was rather mundane and soon I begged off our call, claiming that I had to be somewhere to meet up with friends for lunch. The reality was that I planned to stay home and drink myself silly that day and drown in jealousy and longing.

I had a desire to do something else, though, not really wanting to be alone and not wanting to sink further into my miserable thoughts. I had spent hours the night before and that morning dwelling on Elise and the casual lover she would take at some point that week. I really wanted to forget about those things a while. Drinking at home, alone, was not going to help.

I caught a bus and then another, and then more to get me to San Francisco. I figured I could use a diversion and headed for a district where bars were plentiful, many of them open on the holiday. I chose one at random and went inside. I’d worn a pair of tan corduroys and a beige blouse with a ruffled coverage of my cleavage, a warm, heavy jacket over top to protect me from cool late-fall wind blowing outside.

I felt a little sexy, had even put on a bit of lipstick and liner, but nothing like when I was actively seeking to attract an eye or two. The bar I’d chosen was half-filled with an assortment of ages, and predominantly by females. I saw only one or two men inside. It took little time to understand it was a queer bar catering to women. Never having been in such a place, I was intrigued and settled onto a seat at the bar along one side of the interior.

For an hour or so, I downed a couple of cosmopolitans and ordered a third, largely left alone by everyone except the pretty young tender whose name was Lisa. I couldn’t help eyeing her up. She was short and bubbly, dark hair, black shirt and tight black slacks. Quite a looker, really, and had I been seeking a partner that night, I might have tried to pick her up. Not that I thought she would go for it. I knew bartenders were regularly hit on and, justifiably, had strong reservations about such things.

Still, she was nice eye candy, and there were plenty of other beautiful women inside to distract me from my jealous thoughts.

Someone sat next to me as I was catching a solid buzz. I turned and nodded politely to the woman. She was clearly Asian and somewhere in her forties to my eye, black hair cut very short along the sides, left longer along the top and back of her head. She wore black or reddish-black lipstick, I couldn’t tell which in the bar lights, and dark liner around her eyes. The woman smiled at me and turned towards the tender to order a drink.

I returned to my own and sat quietly until the woman spoke to me, “You look like you’ve had a rough one.”

I shrugged, looking up a bit, “Had better. Could be worse.”

“Girl troubles?”

I smiled despite my down mood, “Yeah...”

“I can understand,” she said, “just broke up with my girlfriend a couple of weeks ago.”

“Sorry about that,” I sighed, “I’m in a different situation...”

“Ah, sounds like drama,” she grinned, “sorry for prying. I’m Jayna, by the way.”

“Carrie, and it’s fine. Decided to let the alcohol help me along today.”

She nodded, “Same. Maybe we can be miserable together awhile?”

There was just a sparkle of interest in her eyes, but nothing terribly forward. Maybe it was just wishful thinking. I agreed it would be good to chat, and I learned that Jayna worked for a bank in downtown San Francisco. She was divorced from a man many years. Jayna opened up to say she had always been bisexual, but tended to prefer women.

“I’m midway, myself,” I said, “no preference. I’ve dated both.”

“And the one now is... ?”

“A woman. A ... former girlfriend who I’ve been talking with again for a few weeks. She lives in Boston, so that’s tough,” I told Jayna, “but we talked about things last night, and we haven’t exactly decided we’re a couple, not formally, at least ... and ... and she’s visiting Switzerland ... see ... there’s this guy she might see...”

I had trailed off, my stomach already knotted to feel those emotions strongly again, despite the alcohol.

“Jealousy, then?” Jayna asked carefully. “Hating that she’s going to be with someone other than you?”

“Yeah ... It’s not fair. We never agreed we’d be exclusive, and ... we have a lot to figure out to even know if we can be together again ... I want it, and she does, too ... but until we have a chance to see each other again over Christmas ... It’s just unfair to her that I feel jealous. I told her to go for it, though it made for a rough night after she hung up ... Still rough,” I added, flourishing with a mock tip of my glass before swallowing the remainder.

Jayna leaned in, “That’s hard stuff to sort out, I know. I’ve been on both ends of that ... Never any good answers. I mean ... you get urges that just need tending, and waiting on someone else to get there with you ... That can be a very difficult thing to wait out ... I dunno about you, Carrie, but if you’re anything like me, there’s just a point where you need a physical connection in the world. I can only feel so good twisting my own bits. I just get where I need someone to hold for a while and let go.”

I looked at the woman, “That’s it, I know. I feel the same ... The truth is, if I couldn’t see Elise next month, if that got put off, I’d be right where she is ... needing someone to be with. That’s ... that’s the urge that sent me astray ... I cheated on Elise ... twice ... when we were dating in college.”

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