Holly Day - Cover

Holly Day

by Thesandman

Copyright© 2008 by Thesandman

Erotica Sex Story: Two women whose paths are so different, come together in a special bonding and relationship.

Caution: This Erotica Sex Story contains strong sexual content, including ft/ft   Lesbian   BiSexual   First   Oral Sex   Masturbation   Petting   Sex Toys   Squirting   .

It was her father's idea to name her that, since his last name was Day. Back then, it was a cutesy thing to do, though in the beginning Holly wasn't too sure about that. Eventually, however, she liked it as it always reminded her of better days and a happier way of life.

Holly and I had been best friends ever since grade school. With reddish brown hair that fell way past her shoulders, green eyes and a picture perfect figure that had the boys drooling, it was in a way comical to know, a secret back then, she had no interest in them, none whatsoever, even though I wasn't to learn this for a while yet.

I was a little chubbier then too, though that was partially due to the fact that I developed fairly early on, so my breasts seemed to fill out overnight, and with the insecurity that went along with that, having "tits" when no one else really seemed to, caused me to eat a little more than I should have. I got a lot of teasing about my size, but realized a year or so later, it was more jealousy because I had boobs, and most of the other girls growing up with me didn't. The only one who never teased me, and who befriended me of course, was Holly.

The fact that she lived just a couple of doors down made it easy for us to spend a lot of time together as well. And being an only child, my mother all but adopted Holly and welcomed her at our home as much as Holly's mother welcomed me at theirs, especially that first year of High School when everything seemed to happen at once. When Holly's father left her mother for another woman, and when I first learned the truth about who my best friend in the world truly was.

By now of course I had shed all of those chubby little girl pounds and had filled out most of my five foot nine inch frame. One of the advantages of that of course at the time, was that I was taller than most of the boys in my class, and held it over them to some degree for the torturing teases a lot of them had forced me to endure growing up through grade-school. Not that I was a knock-out or anything like that, Holly was the real beauty, but cute enough to receive a great deal of attention, though I still attributed a lot of that to my larger than average sized breasts. I had grown out my dark auburn hair, trying to emulate Holly's I suppose, though it wasn't quite as long as hers, but we had spent many hours brushing one another's hair together, and which in a strange sort of way, is what brought me onto the path of sexual discovery and the long hidden secret about my friend.

The big thing was, we had finally graduated from high school and with summer vacation finally at hand, Holly and I looked forward to spending a lot more time together, especially the sleep-overs which both of our families welcomed, primarily because they knew where we always were for one thing, and for another, neither of us was involved with boys at the time, not that we didn't get a lot of attention from them, we both did. But with Holly shrugging them off like water on a duck's back, I tended to follow along doing the same.

We had spent a good part of the evening brushing one another's hair as we often did, having first slipped into our PJ's, which for me usually consisted of a short baby-doll nightie of one sort or another. Holly had always worn simpler things to bed, such as a loose fitting white tee shirt, and plain cotton white panties. And it was of course no big deal dressing, or undressing in front of one another either. After all, I had seen her naked in the showers at school for a couple of years now, just as she had seen me. We'd watched one another develop, change, even on occasion commenting on those changes, and several times doing laughable, childish comparisons of one another. I was in the process of slipping into one of my night gowns as Holly sat at her dressing table, already wearing her favorite nightly attire when she spoke, stopping me in stride.

"You really do have beautiful breasts," she told me. Like I said, she'd commented on them before, we both had. But I'd never heard her call them beautiful before.

"Thank you," I said feeling a little silly, then slipped into the top I had brought along preparing to button it up. "No don't, let me look at you for a moment," Holly said surprising me once again. I don't know why that flustered me, or why it suddenly felt different as she stood and walked over. But in the next instant she stood cupping my breasts in her hands, and then kissed me.

For a moment, I didn't know what the hell to do, so I simply stood there kissing her back, letting her feel up my boobs with my mind racing a hundred miles an hour. Seconds later she broke off the kiss and immediately apologized.

"No reason for you to do that Holly!" I told her, a strange sort of excitement pulsating through my entire body. I certainly wasn't shocked by it either, not really. I knew a few of the other girls in school had kissed other girls, and many of them having done so long before we just had. A natural normal things for many women to do growing up, expressing curiosity, and romancing, or fantasizing about those first grown up kisses that would come later on, though most girls were using one another to practice on prior to that happening.

"Yes there is," she told me sitting back down in her seat. "There's something you need to know Mandy, something I've never told you about."

I knew she was being serious, she was wearing that serious expression on her face she always wore when it really was serious, like the time she had told me about her father's leaving, and then a year later when she informed me how her mother was dating another man, and how much she hated the guy already, primarily because of the way he looked at Holly whenever her mother wasn't around.

"So what? Tell me," I urged her now sitting down on the corner of the bed across from her. I didn't even realize, nor consider it really, that I still hadn't finished doing up the top of my nightgown. My full breasts continued to sit there in full view, my nipples actually hardened by the quick gentle caress of Holly's hands.

She spoke, though still gazing towards me, her eyes obviously locked onto my breasts though for a moment longer, the reason behind that still hadn't struck home, until she looked up into my eyes and then told me.

I was at first shocked. Back then, gays and lesbians really were in the closet, I mean you never really heard anything about them, and you certainly didn't openly see anything. The fact that Holly had come straight out and told me that she found girls/women attractive, and that she wasn't attracted at all towards men, still had me struggling to accept it. As I sat there listening to her, listening to all the years of pain she had struggled with her feelings, her hidden secrets, I began to see a side of Holly I had never known before, and finally, clearly had come to understand. Even having said that, I still wasn't sure how I felt about it personally. I knew that I was indeed attracted to men, a few of them anyway, but more importantly, had never really entertained thoughts or fantasies towards women. Until now.


As it turned out however, Holly's revelation to me came during the worst week of my entire life. Less than a few days later, she and I both learned that her mother had agreed to marry the guy that Holly absolutely despised, and worse, that her mother was pregnant. In addition to that, her soon to be stepfather had taken a new job in California, and had announced to Holly that they would soon be moving. Holly begged, even pleaded with her mother to at least spend some additional time with me. My parents had even agreed to let her do that, as there was plenty of room. All to no avail however, as both Holly's mother and soon to be stepfather were adamant about her moving with them. Holly's only consolation being that she had always wanted to see California.

We spent that last night together at my place. A night I wouldn't soon forget, and would spend the next year alone thinking about many a time.


A year later I had taken on a job at a local bar, and though we had continued to correspond, even talk on the phone several times, it just wasn't the same. We missed one another certainly, but I could tell that Holly was becoming withdrawn and even more depressed. Then one evening I received a phone call from her.

"Holly!" I said with delight when I realized it was her. "What's up, how've you been?" She was half laughing, half crying.

"I'm coming home Mandy," she told me. "I'm finally coming home!"

"What? What happened? What do you mean? What are you talking about?" I stammered into the phone. She laughed again trying to get me to shut up.

"If you'd quit talking for a moment, I'll tell you." Then she did.

I knew from previous conversations with her over the phone that she truly hated her new stepfather, and with good reason, which she now had confirmed with me as she spoke. She had told me before that whenever she had found herself alone with him, how he was always leering at her, making suggestive or totally inappropriate comments about her body, how she dressed, and that she was nothing but a slutty little cock-teaser. She had laughed at that, for little did he ever really know. But then one night less than a month ago, he had come home late from work, actually late from the bar as Holly new the truth of it to be. Her mother now admitting to having reservations about marrying him, though doing so because of the pregnancy and feeling like Holly's little sister had needed a father. A decision she would come to regret. Holly had heard her stepfather come home, pretending sleep of course as she heard him climb the stairs towards their rooms. Most often, he would simply turn and head down the hall in the opposite direction, but every once in a while, he would stop, quietly open her door and peek in towards her. Holly had once asked for a lock to be placed on her bedroom door to ensure her privacy, but he had forbidden it, using some flimsy excuse of needing to get into her room in the event of some stupid emergency. She hated that, hated when he would stand there in the doorway looking towards her in the darkness for several long moments before finally closing the door, leaving. Holly would be holding her breath, fearful of what she thought him capable of doing. This night, he had come up the stairs, and as Holly had feared, stopped, opening her door. But this time, he came into her room, closing the door behind him. He had walked over towards her bed, though Holly had tucked herself deeply beneath the covers. And though she couldn't see him, she could hear him. She heard as he unzipped his fly, heard as he began masturbating himself while standing over her, mumbling to himself about her constantly teasing him with her supple little body, her cute perky tits, and her near perfect ass that she was always showing off beneath her too short, short-shorts. Had it not been for the light in her bedroom suddenly coming on, the shriek of her mother's own voice yelling at him to get out of her daughter's bedroom, Holly wasn't sure what just might have happened otherwise. To her immediate relief of course, they had kicked him out and were coming home again. Holly's mother had already arranged to get her old job back as a hairdresser, and her Uncle had already managed to find them a new place to stay. They wouldn't exactly be living a few doors down as they once had of course, but they would only be living a few miles away.

"Oh Holly! I mean I'm sorry that all that happened!" I told her, meaning it. But I was also elated that I would soon be seeing my very best friend in the whole wide world once again. "When? How soon will you be here?" I asked. "Well, mom did say I could come earlier and stay with you for a few days, provided it was alright with your folks," she said hopefully. "Hell, I don't even need to ask!" I told her excitedly. "Just tell me what flight you'll be on, and I'll meet you at the airport!"

I had a hard time trying to get to sleep that night, just thinking about her. I had missed her horribly, more than I even realized, and more than I would eventually come to understand.


As I've already mentioned, that last night with Holly had been one I had never forgotten. We had spent the night sleeping in the same bed together, or rather trying to sleep which it seemed neither one of us really could, though at some point, we had both pretended to, not wanting to face the coming day. With mere inches separating us there in the darkness, I soon felt a subtle movement, wondering, and then realizing what it was she was doing. I mean after all, I did it myself then, frequently. But even more surprising, as I lay there, sensing, hearing and even feeling her movements, I became aroused, excited, and began doing the same.

She never spoke, but after a time I felt the touch of her hand upon me there beneath the covers, tentatively at first, and I'm sure worried. In an effort to ease her mind, as well as my own perhaps, I then reached over towards her, finding the touch of her, the surprising softness, and then the wetness to be mind numbing, thrilling, and exciting beyond imagination. Before long, we were openly finger-fucking one another with wild abandon, then Holly rolled over on top of me and began kissing me, all the while pressing herself against me as we humped like we were fucking one another, caressing one another's breasts, kissing some more, and finally fingering one another off towards two very intense, very heartfelt "this is good-bye" orgasms.


I picked Holly up at the airport late that afternoon. I was excited to see her of course, but almost missed seeing her even when I did. In the time she had been away, Holly had changed her overall appearance. I mean, she still looked like the Holly I once knew, but she was far more mature looking now than I remembered, and she had shortened her hair, considerably.

We had rushed home after that, settled her into my room, had eaten dinner with my folks and spent some time catching up with them before racing back upstairs in preparation for bed, though neither one of us had any intentions of sleeping. It was just like old times, with one little exception. I think we were both remembering that last night we had spent together, and it was something that was nervously on our minds.

"So I know about all the bad parts, tell me about some of the good ones," I prompted. "Surely there were some!"

"There were, but not sure you'd really care to hear about them," she told me truthfully. "I've gone through a lot of changes," she said wearing that serious look.

"That's obvious," I retorted, "But tell me anyway."

"It's pretty heavy stuff," she said warning me off once again. "And I'd hate to think I was corrupting you," she said with a bit of a devilish grin.

One thing was true, though I was almost twenty one, I was still a virgin and pretty naive about a lot of things. I'd only kissed a couple of guys, and only one of which I'd allowed to even feel me up, and that was through my blouse and not under it. But beyond that, not much else. And though I still masturbated nearly every day, that had remained my private little secret which I hadn't shared with anybody, including Holly.

"Well, don't say I didn't warn you," she told me once again very seriously as she settled down in the bed lying next to me. We hadn't changed our clothes or anything, no-where's near ready for bed as yet, just lying on the bed, side by side. In some ways I was nervously wondering about that, as perhaps maybe Holly had been, which is why we hadn't even made any pretense at taking our clothes off. It must have been a thought running around inside her head, it certainly was in mine.

"I met someone after we moved to California," she began.

I didn't ask who, or interrupt, I figured the unspoken question would quickly be answered, and it was a moment later.

"For something to do to occupy my time, and get me away and out of the house as often as I could, I went to work at one of those specialized boutiques they have there. Nothing like that here of course, and probably won't be for several years yet, but there ... they were all over the place."

I still wasn't sure what kind of 'boutique' she was referring to, but I remained silent letting her continue.

"There were only three of us that worked there at night, me, another girl and the night manager who was also a woman. About the same age as my mother I guess," she added in reflection. "Anyway, I'd been there about three weeks, it was nearing closing time and I had just finished doing my cash drawer. Usually I just left after making sure I balanced as Jocelyn always closed up the shop. Anyway, I was over for some reason and kept counting and recounting and coming up with the same number over and over again. I mean it was better than being short of cash, but still, even being twenty dollars over was frustrating, as I couldn't figure out where the extra money had come from. I looked around for Jocelyn but didn't see her, and I also realized that Suzy, the other girl who usually worked with us in the evenings wasn't around either, though I figured she'd probably already gone home. I decided to find Jocelyn, tell her about the discrepancy, and then head on home."

In had been interesting to note that Holly had closed her eyes as she recalled the story, as though seeing it all so very clearly in her minds eye. I decided to do the same, closing mine as she continued.

"Anyway, so I checked the back storage area where Jocelyn usually went at night to check on any restocks we hadn't done, or that she could put out to have done in the morning with the day Manager and the one other girl that worked with her. But she wasn't back there. Which left only the one other place that she could be, down the hall past the dressing room area in the small little room she sort of claimed as an office, though it was so crowed inside there, it was hard to even find a place to sit. And it was even rarer that she went there, as it had become more of an additional storage room than office. As I started down the hallway and began walking past the three dressing rooms, I heard what was obviously some kind of moan coming from the third one. I slowed, stopped, and listened, hearing it again. About that time it dawned on me as to what was actually going on in there."

"What?" I asked stupidly, but Holly continued without answering me directly.

"I pushed on the door just a fraction and peeked inside. There sat Jocelyn on the small bench seat facing the mirror, Suzy was kneeling down on the floor in front of her, tits out as Jocelyn sat playing with them, but what immediately caught my attention, was that she was eating Jocelyn out!"

"She was doing what?" I then said sitting up eyes wide open, which caused Holly's to do the same, though she merely continued to lie there.

"You heard me," she said. "She was licking her cunt!"

I really was naive. I'd never heard of such a thing before. I had heard about some girls, though I'd honestly never met one personally who had given a guy what many had called a "blow-job" so the visual workings of that had managed to stick inside my head though I'd never seen it. But I for some reason had never really considered the other side of that coin at all.

And though I had certainly heard the word before, it was one that was always used as a major derogatory vulgarity when referring to one of those women who gave those boys I just mentioned a blow-job.

"Oh my god!" Was all I said. "Why would she do that?" Which is when Holly burst out laughing.

"Oh you poor innocent sweet young thing you," she said easily. "Anyway, there I stood watching the two of them for a moment when Jocelyn looks up in the mirror and sees me peeking at them through the crack in the door. All she says is, "Either come in and join us, or close the door and give us some privacy."

"What did you do?" I had to ask. Holly grinned.

"I joined them of course!"

"Shit Holly! Then what happened?" It was at that point that I noticed Holly had actually slipped one hand down the front of her jeans, there could be no other reason for her doing that, except to obviously be touching herself in some way, though she was very subtle about it. Laying back on the bed, I once again closed my eyes and listened as she continued on with the story.

"For a moment, I just stood there watching them. It was mesmerizing really, watching Suzy licking the woman we worked for's pussy, but rather than finding it vulgar or revolting, the longer I stood there watching the more aroused and excited I became."

"Would you like me to lick yours?" Suzy asked a few minutes later.

"I wouldn't mind doing that myself," Jocelyn added. "How about we all take turns lying down on the floor here, and then we can eventually switch places."

With my eyes closed, I suddenly had this very clear, very distinct vision of the three of them naked, lying on the floor in a connected circle licking one another. And as Holly had just stated, rather than finding it nasty, dirty or revolting, I found myself becoming fairly aroused by the thought of it.

"So what was it like?" I asked, hearing Holly's giggle once again though I kept my eyes firmly closed, not willing to look into her eyes and let her see the flush that had spread suddenly across my face, though if she was looking, she'd have seen it anyway, just not the curiously-lusty look I might have given her.

"It was heavenly," she sighed. "Especially when Jocelyn finally did it. I mean, Suzy enjoyed doing it, but Jocelyn was damn good at it! And it was the very first time for me too," she added with another long sigh. "And I knew there and then, there was no going back."

I opened my eyes once again at that one. Holly still had her hand down the front of her pants, and it was very obvious now what she was doing to herself.

"You ever think about that last night we spent together?" She asked suddenly.

I caught myself short, but there was no use denying it either. After a moments more pause, I admitted I had. "Several times."

"Did it freak you out? Bother you?"

"No, but you should know that. If it had, I would have told you," I told her.

She smiled at me. "Wish then I knew what I know about now," she added. "I wish I'd gone down on you rather than just finger you to climax."

I remembered the orgasm, several of them in fact.

"You can cum like that?" I questioned again stupidly.

Poor Holly just shook her head laughingly and smiled at me. "Even harder than what we experienced," she admitted to me. "I've never cum so hard before in my entire life!"

"Holy cow!" I retorted, "Who'd have thought?"

She giggled once again. "I did, several times. And several times, wondering what it would have felt like if you'd been there instead."

"You did?"

"Oh yeah, on more than one occasion too," she added with a little wink. "Oh and one more thing I need to tell you about," she said. "I'm no longer a virgin either!"

"Holly! No shit?"

"No shit Mandy, but this part might surprise you, it wasn't a guy who popped my cherry either, it was Jocelyn."

"Jocelyn?"

"Yeah, Jocelyn."

"Ok, now how is that possible? And how is it if you didn't do it with a guy that you're not still a virgin?"

"I see this is going to be a long night," Holly said slipping out of bed. "And if we're going to stay up all night, which it looks like we will be, then I'm at least going to get comfortable before I tell you the rest of it."

Holly immediately pulled the tight fitting tee shirt she was wearing up and over her head, quickly unclasping her bra, and throwing both items into the nearby chair. She then stooped, chucking off her jeans while I continued to lie there watching her. She wasn't wearing any panties, and as she turned to once again face me and slip back into bed, I saw the tiny little tattoo just above the neatly trimmed line of her pussy hair.

"Hold it!" I said flatly. "What the hells that? And what did you do to your pubic hair?"

She grinned kneeling down on the bed next to me. "Well, to answer your first question, it's a tattoo, and to answer your second, it just feels better this way, for a number of reasons."

"For real? You mean it's permanent and won't come off?"

"Nope!"

"Let me see!" I didn't really realize I was suddenly face to pussy, or nearly so with Holly's cunny mere inches away from my face. "It's a butterfly!" I stated as though she didn't already know that.

"You are correct," she said sarcastically, which is about the time I did realize I was hovering so close to her, and inched back a ways.

"Wow, you're brave," I stated. "What did your mother say?"

"She doesn't even know I have one," Holly told me. "And it's none of her business now anyway."

"So why'd you shave your pussy like that again?" I asked now actually looking at it, to which she laughed.

"Lets just say it's a lot nicer having it a little neater for whenever someone might decide to start licking it," she said almost in a way of challenge. "Now then, you going to continue to lay there with your clothes on and make me uncomfortable? Or you going to finally get undressed and get back into bed?"

I know she didn't mean for it to sound the way it might have, but the implication was there, and surprisingly, I think it had been all along. I wasn't one hundred percent sure of anything, nor was I expecting anything for that matter, after all, it had been a while, and we'd both gone down two separately total paths. I did slip out of the bed on my side at that point however and began to undress.

"You still wear those silly looking outfits?" she asked,

"Silly looking?" I shot back, "I thought you said they were cute!"

"Back then maybe, yes. But that was another time, another place," she told me.

Then it was my turn to surprise her. "Nope, now I just sleep naked!"


In seconds I was as naked as she was, flipping off the overhead light throwing the room into darkness. A moment or two after that, I had slipped back into bed beneath the sheets beside her.

"Why'd you turn off the lights?" she asked.

"In case mom or dad comes up to check on us," I lied. Truth was, they wouldn't do that. "If they come up and see the lights off beneath the door, then they won't even bother us," I said continuing the lie.

"Oh, ok," Holly responded.

The truth of the matter was, I felt a little embarrassed. Here Holly was, looking far more mature and grown up, a naughty little tattoo, much shorter hair, and a trimmed pussy. And here I was, still feeling like the same little girl I'd always been, even with big boobs.

"So, tell me how you lost your cherry," I reminded her.

"Ok, but if I do, then you have to let me tell it my way, and do it my way while I do," she said cryptically.

"What do you mean by that?" I asked. Then I felt her hand suddenly appear between my legs as she began slowly caressing me, just as she'd once done so long ago.

"That answer your question?" she asked.

I didn't answer her back, I was still trying to find my voice, but I did spread my legs a little, which was answer enough as she began speaking again.

"One night after we had closed the store, Jocelyn asked if I'd like to come over to her place and have a drink. So I did. We sat on the couch sipping our drinks for a while when she asked me if I'd like to go into her bedroom and fuck."

Though startled by the use of the word, the touch of Holly's fingers gently pressing against my lips as she related the story to me, kept me from responding to that.

"It was then I told her that I was a virgin, and had never been with anyone before. She seemed surprised by that, but then assured me if I was willing, that she would be lovingly gentle with me."

It was then that I felt Holly's other hand seeking mine, lifting it, and placing it upon her smoothly shaved mound.

"We got undressed, then I sat there watching her as she began to put on one of those strap-on dildo's we sold at the store."

"Strap on what?"

"You know, dildo's?"

"Dildos?"

"Yeah, fake cocks, women wear them to have sex with one another if they're lesbians, or in some cases, women use them on themselves to masturbate with when they can't find a decent man to do it for them."

"You're kidding me!" I stammered in disbelief.

"Oh Mandy, you really do have a lot to learn don't you?" she stated, giving my lips a little pinch before settling back into the bed and continuing.

"Anyway, she's really careful with me, takes a lot of time preparing me. She put a lot of baby-oil on the toy, which helped a lot, then had me kneel down on the bed "doggy-style".

I had heard that term before of course, but now it had a whole new meaning for me as I envisioned my very best friend kneeling on this woman's bed while she in turn had fastened some sort of fake prick and was about to shove it inside Holly's cunt.

"I don't know Holly, sounds kind of wickedly nasty to me," I told her.

"Oh yeah Mandy, it was, wonderfully wicked and nasty," she sighed remembering, and proceeded to give my hard little clit nub a nice stimulating twirl with her fingers. "Then she slowly eased it inside me, just a little at a time, and the next thing I knew, she was in, though she just stayed there for a while without moving until I got used to it."

 
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