Holly Day

I was tempted, really tempted. But I needed to go in a little earlier and talk to Jerry before she came in later. It was important to me that I do, as he needed to understand how close the two of us were, had always been, and always would be. Holly had changed enough to know, or that most would know by now, just what her true preferences were, and I didn't want there to be a scene if he didn't quite understand or be accepting of her.

"I'd like to, but I can't," shying away before my resolve melted. "But trust me, after work as soon as we get home, I want you to lick every square inch of this bare little pussy of mine," I quipped.

Holly was grinning broadly at hearing that. "I'm going to hold you to that!" She told me. "Now, get that sweet little ass of yours inside those shorts, this I gotta see!"

#

Jerry was a lot more understanding and accepting than I'd imagined he'd be. Which I was extremely grateful for, though I neglected to tell him of course that we'd been licking one another's pussies. Something I am sure he'd have been more than happy to watch on the one hand, but not too happy about in hearing on the other, when I hadn't so much as let him lay a hand on me beyond feeling up my bra covered boobs the few times we'd gone out together. And I had admittedly mixed emotions about that too. As fun and exciting as this had all been, and as much as I really did love and care about Holly, the fact was, I knew I wasn't a lesbian. I was attracted to men, Jerry in particular, and I had every intention about doing something about that shortly before Holly showed up.

Now, here I was enjoying a newfound sexuality with a friend, a girl friend at that, and enjoying every minute of it though I knew full well that one day I hoped to get married and have children.

I didn't even know or understand what the word "bi-sexual" was either, nor would that label be one I would necessarily consider myself being. It wasn't "women" in general I was sexually attracted to, just one in particular, Holly. And I knew that eventually I would have to come to terms with that, but for now, it was nice simply spending time with her, discovering myself, and enjoying my new-found sexual freedom.

#

I was standing behind the bar talking to Jerry when Holly arrived. For a few moments I didn't see her, which was probably due to the fact that my lips were mashed against Jerry's at that particular moment.

"Ah hem," we both suddenly heard a moment later. "Am I interrupting anything? Or can I just watch?"

"Wow, it's certainly been a while hasn't it?" Jerry said extending his hand in greeting. "How've you been Holly?" He asked.

"Yes, it has been, and I've been fine, especially lately," she said giving me a curious look.

I knew Holly and I were going to have a lot to talk about on the way home.

"I'm off tomorrow," I reminded Jerry.

"Yeah I know," he responded. "We still on for the weekend?" I merely nodded my head yes, and then slipped my hand into Holly's heading for the doorway.

"Plans?" Holly asked with a crooked smile on her face. Then, "So why didn't you tell me you two were dating?"

"We've just started dating," I explained as we reached the car. "Nothing serious, we've only gone out a few times."

"That kiss looked pretty serious," she added.

"Maybe, who knows, he's nothing like you remember back in school, he's changed."

"Haven't we all?" Holly said cryptically. "Especially you."

"Me?"

"Hell yes, in the last twenty four hours you've blossomed into a whole other woman!"

I had to laugh at that, she was right.

"You thinking on doing the nasty with him?" she asked.

Truth was, I had been. But I was nervous about that too. I knew Jerry certainly wasn't a virgin, which Darlene had seemed to feel was her duty in life to tell everyone about. And I hadn't told Jerry I still was one either.

"Thought about it," I admitted. "But the thought of it scares me a little too."

#

Things were abnormally quiet between us as we slipped into bed. For the first time in our friendship, it felt awkward.

"Listen, Mandy, I've known all along that you'd one day end of marrying some guy, settle down and have a bunch of kids."

"One kid, maybe two," I interrupted glad she'd at least spoken.

"Whatever, my point is, we're friends, perhaps very special friends considering the circumstances. And I know you like me, perhaps even love me in that same special way, but I've always known that you're not gay, and that a permanent relationship between us beyond this just wasn't in the cards."

What she said was true. There was something special between us that I really didn't want to end. And even though I now had certain other feelings towards Jerry, I didn't want him to come between us as much as I hadn't wanted Holly to come between Jerry and I either.

"So now what?" I said sadly, nervously.

"Well, I guess that's up to all of us now isn't it?" She said simply. "We either learn to deal with it and accept things, or we don't. It's really that simple."

Fact of the matter was, it was!

"So, you going to fuck him or what?" she said with a teasing tone of voice that immediately made me relax.

"I want to, but like I said, I'm afraid."

"Afraid? Because you think it will hurt?"

"Not so much that, no. More afraid because I don't want to disappoint him, or myself for that matter. And as silly as this may sound, I'd rather he not know I am a virgin. I don't want him thinking he as to do some big honor my virtue thing if I were to tell him I was before hand. I just want to make love with him without any of that other stuff getting in the way."

"Well, I don't know what to tell you about that," she mused "Glad I didn't really have that problem when I lost mine."

Her comment gave me the opening I needed as I'd been considering something else.

"Holly?"

"Yeah?"

"Would you?"

"Would I what?" she said turning over in bed to face me directly. Though by the look on her face, she knew exactly what it was I was about to ask her.

"Would you be willing to take my virginity?"

She lay there looking at me for several long moments. "Are you sure about this?" she asked.

"Very sure. I'm more sure about this than I've ever been about anything."

"Will you be able to live with the thought that it was another woman who deflowered you, and not some guy?" she questioned me seriously once again.

"The only thing I've ever been sure of, is I wanted my first time to be with someone I truly cared about, and who truly cared about me. And I can't think of a better person, including Jerry, than you."

I rolled over on top of her then, and began kissing her passionately. "Whoa sport. If you're really serious about this, then we're going to do it my way, and it won't be tonight, not like this anyway."

"When then?" I asked anxiously.

"Well, you said you were off tomorrow right?"

"Right."

"Then tomorrow, you leave things up to me. I'll make sure it's the kind of evening and night then that you've dreamed about."

I laughed when she said that.

"What's so funny?"

"How'd you know what I've been dreaming about all these years?" I said teasing her back.

She slapped my ass then, hard! "Because I know you Sleeping Beauty, I've always known you."

"Speaking of which, how about you come here and give me another one of those enchanted kisses again then?"

"How about I lick your pussy?"

"That's what I meant," I said giggling.

#

In a way, I was that nervous bride on her wedding night. Holly had gotten up early, long before I had leaving me a simple note saying she had a lot of things to do, and that I was to simply try and relax and let her take care of things. The only thing I knew for sure was that I was to meet her at the one really nice restaurant in town around 7:00. She had made reservations, and when I arrived, the hostess on duty escorted me to our table with a very curious look. When I arrived, I could see why. Holly was wearing what amounted to a men's white dinner jacket, tie and all. Black slacks, shoes, with her short hair slicked back in a very mannish style. She even stood, taking the back of my seat for me as I prepared to sit down.

"Thank you," I said demurely as the hostess continued staring at the two of us before finally announcing our waiter would be with us shortly.

"You look terrific!" I said laughing.

"So do you," she told me, and then kissed me full on the lips as several surprised customers seated around us watched.

Holly ordered an expensive bottle of wine, which was comical as the steward confusedly presented it, uncorking the wine as Holly took a sip and approved of the taste before he poured me a glass and finished refilling her own.

"This will be the talk of the town, and possibly the main subject at the hairdressers tomorrow," she warned me.

"I don't care Holly," I said honestly meaning that. "This is my life, and I intend on living it the way I want to now."

She smiled at that and began looking over the menu. "Just don't eat too much," she warned me with a wink. "We can always order room service afterwards."

#

Holly had booked one of the hotel's more expensive suites. I hadn't intended for her to do all this, but obviously she meant to make this night memorable for me, as if it already wasn't. We first sat in the enormous sunken tub that was in the same room as our bed, gently washing one another, caressing and playing around until we were prunes.

"Relaxed?" she asked.

"Relaxed AND excited, all at the same time!" I giggled feeling shy for the first time, knowing full well what would be happening tonight.

We stepped out of the tub shortly after that as Holly dried me, then herself off before leading me towards the bed.

"I promise, we're going to take things very slowly," she assured me.

"I'm not worried about it," I told her, which I wasn't really. I knew she would be gentle, but we were indeed about to banish my virginity forever.

Holly began by kissing me from head to toe and back again. She lavished every square inch of my body with soul penetrating kisses, especially my more than aroused breasts, before finally settling down between my legs and gently tickling my clit until I thought it was going to come off.

I was certainly more than wet, but even then I felt Holly apply a liberal amount of some really slippery lubrication that she'd purchased especially for our purposes.

"This will help a lot, even as wet as you already are," she said grinning down at me.

It was then that she reached beneath the pillow where she had hidden the naughty wicked looking toy she now held in her hand.

"Where the hell did you get that?" I asked staring at the life-sized phallus she then began waving at me so wickedly.

"I brought this with me, among other things," she said. "We used to sell these in that boutique I told you about."

"No wonder you guys were always so damn horny!" I told her. "I would be too if I had to be around this kind of stuff all day long!"

"You might be right about that," Holly said in reflection. "We did tend to try anything new that came into the store before selling them. Jocelyn thought it would be a good idea that we should know what we were talking about should anyone ask us, or have any questions about the merchandise."

Holly took her time, which I truly appreciated, and which truly aroused me even more than I already was. Touching the head of the life-sized, real flesh feeling prick to my pussy, she gently teased the inside of my opening, rubbing it up and then down my super-slick lips. Periodically, she would press it even more firmly just inside until I could feel the pressure of it trying to enter me. Always she would stop whenever the sensation started to become uncomfortable, and would either then tickle my clit with her tongue, or her fingers for several moments before continuing. I know she was taking an inordinate amount of time doing this, but I appreciated it.

"Fuck I'm horny!" I finally told her, "You're driving me nuts!"

"Good, now relax, lay back and let's see if we can't pop your cherry now shall we?"

It really was time, and I wanted it more than I had ever wanted anything in my entire life. Once again she began to insert the hard stiff prick inside my virginal opening. I felt the slight discomfort as my hymen began to stretch though she pressed slowly at first, cautiously.

"We're almost there baby," she soothed. "You ready?"

I hissed, "yes" then, that I was.

There was a slightly harder press then, a slightly stronger sensation of discomfort, a wince of pain, and suddenly I felt the entire length of the phallus slip deeply inside me.

"Ohhhh Holly!" I wailed out in a mixture of surprise and delight as she penetrated me fully. I felt the rubber cock completely filling my passage, where she left it unmoving, though she now lowered herself, once again lightly licking and sucking my clit, then moving upwards against me, placing her lips against mine as we kissed in a gloriously long embrace, the sensation of prick so deeply embedded, now suddenly moving in and out with a slow dream-like sensation that sent shivers of delight and excitement coursing throughout every nerve ending in my entire body.

After a time, she removed the toy, slipped back off the bed and retrieved something else from out of a near by overnight bag.

Enthralled, I watched as she then slipped a set of straps around her waste, a second later easing the prick that had so recently deflowered me through a specially designed hole in front, and stood there before me, a woman with a hard-on!

"Now we're truly going to fuck!" she announced wickedly.

We did in fact do just that. I lost count of the number of orgasms we shared or gave one another. At one point I even dawned the strap-on dildo myself, fucking Holly from behind doggy style just as she'd once shared with me that Jocelyn had done with her, her first time.

When the morning sun finally came up, we were still wrapped within one another's arms, satiated beyond reason, and committed to a bonding between us that would never be broken.

#

Holly stayed in town for a while. She was there for me, and with me in spirit at least, when Jerry and I finally made love for the first time. As I'd hoped, the evening was far more beautiful and romantic than it might have been otherwise had it been all about his taking my virginity.

When Holly finally announced she was going back to California, I wasn't at all surprised. She had friends there, other friends besides myself that she needed to be with, in ways that I always couldn't be. And I understood that, just as she had. And she came back for my wedding, just as a few month's later I went for the first time to California for hers, though sadly of course, hers wasn't legal, though they went through with it anyway.

And I liked her life-partner too. Janice was very much like Holly was in nature as well as looks, and we got along famously during the week I had spent there with them after the wedding.

On the last night there before I was to leave and head back to my own life and husband, Janice knowingly gave us time alone without reservation, jealousy or fear.

"How's Jerry?" she asked.

"He's doing fine, though we're selling the bar and opening a much nicer place in town."

She laughed, "No more peasant blouses and tight fitting shorts?" she asked.

"Only at home now," I giggled back. "He still likes the way I look in my outfit," I told her. "Never fails to get a rise out of him."

"I'll bet," she paused then, that half-serious expression she sometimes wore showing on her face. "He still ok about us?" she asked worriedly.

On the day that Jerry proposed to me, I decided to tell him everything before I said yes. But it was a lot more than that too. Holly and I had of course talked long into the night, the night she had taken my virginity. I had told her then, making a promise, a vow that I swore I would always keep no matter what, as she then did for me.

I had told Jerry about us, about our very special relationship, and how we had come to care about one another. I explained to him that though I certainly wasn't a lesbian, or even bi-sexual in nature, that Holly was someone I could and would be with again. He had to know this before I said yes. I wanted to give him the chance to know all the facts and think about it before giving me his ring, or in my accepting it. I honestly thought it could very well be the end of our relationship, and had prepared myself for it. But I told him pointedly, that Holly and I had sworn and vowed to one another that we'd at least see and be with one another at least once a year until and unless we decided otherwise. If he could accept that, and understand it, then I would indeed marry him.

It was the same understanding that Holly had presented to Janice prior to their own marriage.

"Yes, he's still ok with it," I told her. "Though he keeps hinting at the fact he'd enjoy seeing us together the next time you come out to visit me," I added.

"I'll bet," Holly snickered. "And I bet that's not all he'd like to do or see either," she added.

I laughed at that too, she was right of course. Jerry was a lot more open-minded than I'd ever considered him to be of course, obviously. But he was also like any other typical male in that regard too.

"Who knows? It might be interesting to see what a guys dick really feels like," she told me suddenly.

"Holly? You, with a man?"

"Hell you never know kiddo, it could happen! Look at what happened to you!"

And I smiled at that, a lot had indeed happened, and I owed her for much of that.

#

It's been several years now, Holly is still with Janice, as I am with Jerry. We have a little girl, who I named Holly after my dearest friend. And as we once vowed, we still see one another at least once a year and spend some very special time together whenever we do. Jerry's turned it into a sort of secret joke with our other friends and family whenever I go off to visit her. He like's telling everyone that I'm off on a Holly-Day.

Oh yes, and he finally got his wish too.