What If

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Many Feathers
Many Feathers
10,503 Followers

I don't think I'd ever been so fucking hard in my entire life! And then as I made my final trip...knowing it would be, I looked, and holy shit...it was suddenly there. This big, beautiful, totally naked hard nipple just waiting for me to kiss it, to suck it, to fondle it. And then I was. I remember reaching it, first kissing it of course, repeatedly, her hand suddenly on the back of my head holding it against her, as though nursing me in a way, which I began doing of course. Now sucking it, gently, almost afraid she'd wake up and find out what I was doing here. Until maybe I'd spent too much time doing that perhaps, which is when she then said, "Baby...suck the other one too."

I'd almost forgotten she had two. Like maybe she was saving one for another occasion or something. But now it was awkward. It meant putting one back, and then what...me pulling down on the other side in order to reach it? (What did I know?) But then she of course made it easy for me. She just reached down, and pulled her sweater up and over her breasts, now both of them exposed. And me, sitting there staring at them for the first time, both of them, in their absofuckinglutely beautiful glory.

I think time stood still. I know the stars eventually came out, but I sat until the kink in my side turned numb. Hell, I wasn't about to change positions, even if I left paralyzed after this. I took delight, and time...going back and forth between the two, never getting my fill of doing this. Of seeing her, seeing her breasts, hell...sucking and playing with her very bare breasts. Are you kidding me? Her mother would have had to come home and forcibly remove me herself at the rate I was going. I was in seventh heaven, and so was Teresa by the sounds of it.

The nice thing about that night was, we never went backwards from there. After that, every chance we had, every moment we could take, she wanted me to play with her tits, suck them, nurse them, and fondle them. I honestly believe to this very day, Teresa was one of those women who could actually have an orgasm just by my doing that. There were times after we'd been doing this for a while, she would shudder, and then shortly after...was when she'd almost have to forcibly make me give them up. Not that I minded, especially knowing, we'd be doing it all, all over again, the following day.

My problem was...I was beginning to think that I would forever have a persistent case of perpetual "blue-balls". I'd pretty much decided that was just the way it was, and that I'd have to learn to get used to it. Sure...after I got home, I'd furiously jerk off until the flames had momentarily been extinguished, but it was still a bit frustrating. I was now playing the same old "two second" hold game on her pussy that had taken me several years to get past and make it even this far with her breasts. At that rate, I'd be well into my late twenties before I even got to see her pussy, let alone anything else. I wasn't sure I could be that patient. But once more, Teresa was way ahead of me.

*My first triple*

It was another one of those rare precious times we could actually go out on a real date. Dinner and a movie...and not just a drive in. And though that certainly didn't allow for us doing anything inside a sit down theatre, even the drive home back to her place always held the promise of something more. She'd very often tease me, excite and arouse me by removing her bra in that almost magical fashion women can. Without taking anything else off. Suddenly, pulling it through the sleeves of a blouse or sweater, tossing it behind into the back seat. (I even think I had two or three others at this point I hadn't as yet gotten around to bringing back to her). But that was always a good sign that we'd still have some mess around time even if her mother happened to be home that evening, which she was in this case. Which made this particular night even more memorable, exciting...and to some degree, wickedly dangerous.

We were still a bit early yet from the time we said we probably would be back when I pulled onto her street.

"Cut your lights," she told me as we slowly approached. "And then cut the engine too," she added. I did both, silently letting the car drift up in front of her place. The lights were still on of course, including the porch light, though it was just dim enough not to shine down on us as we pulled over against the curb. Though her mom was home, and no doubt still up, she wouldn't be expecting us yet for one thing, but even if she did see us, and come out the front door, we'd have plenty of time to make ourselves presentable before getting out. Or so I hoped anyway. But I was again just expecting some more titty play before we called it a night again. So imagine my surprise when she turned towards me and said, "Baby...take it out, I want to please you."

You don't really plan these things. I know I certainly didn't, hadn't...though maybe she did. Maybe she had been thinking about it all day, all evening. But she certainly didn't let me in on it until the very last moment. So it's not like you actually come prepared for this. Especially when it's the very first time. I'm not even sure I had heard her correctly when she said that, I was still trying to comprehend the words she'd just spoken, which weren't made any easier to understand either as she once again lifted that still favorite sweater of mine up again over her breasts. (Maybe I should have taken a clue in the sweater...I think it too was magical in a way). But there I was looking at her gorgeous bare breasts as she leaned up against the passenger door and window, looking at me.

"Unless of course you don't want to," came the famous last words.

I don't think I've ever unzipped my fly that fast before, realizing she was actually serious. Though even then I hesitated, reaching in myself, taking it out. But then she started playing with her own breasts, and that's all it took. A moment later, I was sitting there with my cock (at least it was nice and hard already) sticking up and out as she sat there staring at it. Finally, she moved over, placing her hand on it, and then as though she'd been doing this for a number of years, began jerking me off. I knew the moment she began doing that, there was only two ways this was going to go. Thank god it didn't go the way I was fearing the most, though it almost went too far the other way.

I was nervous as hell. Sure...excited beyond belief. After all, Teresa actually had my cock in her hand and was playing with it! But I was still nervous, now fearful of her mom suddenly stepping outside. Or worse, perhaps even sneaking out the backdoor, seeing us parked there out in front, wanting to surprise us...catch us. And oh yeah...would she ever if she were to do that. Especially now. So maybe that helped a little, took the edge off the excitement, adding a pinch of fear into the mix. Which was just enough to keep me from losing it all too soon. The pleasure of my girlfriend's hand, hell...a different hand other than my own, now working my dick was far more than I could have ever imagined happening at this point. And yet...here she was.

It felt so fucking good that I finally started to realize that I was going to be shooting off in my girlfriend's stroking hand before too much longer here. And that now raised another concern. Once more, way ahead of me Teresa smiled looking down at my rock hard cock and tightening balls, and said. "Rick? Do you have anything?"

Had I known, had a clue that this was even remotely on the agenda for this evening, I'd have brought something with me. Ironically, having cleaned out the car earlier in preparation for a real date, I'd discarded the few paper napkins I'd tossed over into the back seat from one too many fast food stop offs. As it was, I couldn't think of a single fucking thing we could use.

Hell, I even had a first aid kit in the trunk in the event of a real emergency. Little help here for that. This was a different kind of an emergency. I swear, someone should invent an emergency first sex kit or something. They'd make a fortune on it. Have it handy in the trunk of the car for whenever it was needed, right next to the first aid kit perhaps. I was even trying to imagine all the things you could put inside it, beyond the obvious of course, for situations just like this one when she spoke again.

"I take it you don't have anything."

"Shit!" Was all I said still trying to come up with something we could use, though now worried that because I didn't, she'd stop...once more leaving me high and dry, only this time far fucking worse than a simple case of blue balls. Which is what I thought was happening as she suddenly let go of my cock, once more leaning back against the passenger door.

"Hold that thought," she grinned wickedly, suddenly raising her ass right there in front of me as I watched her suddenly lift the short skirt she was wearing, grabbing the hem of her white bikini panties, struggling out of them as she lowered them down her legs. "Grab them and pull," she announced, which I happily did of course, though now wondering where any of this was going. Was she actually considering fucking me?

Not possible, no fucking way. Not here, not now...not like this.

I was right about that, she wasn't. But what she now offered was almost as good. (I said almost). It wasn't something I had actually done before, (though I certainly have since). But then taking the panties back away from me as I sat there holding them in my hand, she placed them over the head of my cock, effectively covering it completely, though her hand still felt damn fucking good. But then again, so did her silky like feeling panties as she picked up where she'd left off.

"There, now you can squirt whenever you're ready," she informed me.

(Note to whoever decides to make a "first aid sex kit" to include a silk or satin pair of sexy panties...trust me. Oh, and maybe a short length of soft nylon rope too. I'll explain later.)

The thing was, I'd actually seen my girlfriends pussy for the first time too, albeit very briefly, too briefly...but I had, and was now sitting there realizing that as the tickling sensation deep within my balls was alerting me to the fact I was going to be shooting off here in a second or two. And I also knew, just by that preliminary sensation, this was going to be the mother-fucking best orgasm of my entire life. (Sorry about that mom, it's just an expression). But the truth was...it was going to be.

"Holy shit babe!" Was all I managed. And then I think my entire body somehow became weightless, or I found super human strength or something, lifting my ass completely off the seat, toes curling into the floorboard like a ballerina as I somehow arched my back, meeting that delicious stroke of my girlfriends hand as it came down, me coming up...and then just coming. Over, and over...and over again. Nonstop for what felt like a fucking eternity.

Her panties were soaked. But then again, they sorta had been before I soaked them myself, which was something else that added to all this wicked deliciousness too.

"Holy shit baby," she said as my semen literally soaked through her panties, enough that it bubbled up through the material and still managed to soak her hands and fingers. "Do you...always come like that?"

"Only when you do it," I informed her, seeing the smile on her face after saying that. She knew what I meant. The problem was, I was still pretty messy, even with the panties catching most of it, though she used those to finish wiping me off with the best that she could. And then she surprised me again, perhaps without thinking when she did it, actually licking some of the residue off her fingers. It was like watching her after she'd baked and frosted a cake. I don't think I'd ever be able to see her do that again without thinking about this very moment.

"Shit babe," I said looking at her as she just then realized what she'd done.

"What?"

Don't laugh...back then, I'm not even sure shit like that was legal. Or even if it was, I'd never heard of ANYONE, EVER doing that. I'd never even seen it, and it wasn't a subject that was even discussed amongst any of the guys...seriously.

"My stuff, you ah...shit babe...you ok?" I asked somewhat worriedly. I mean the last thing I wanted to see was Teresa suddenly gagging, puking on me after experiencing some horrible chemical reaction or something. I could almost see it happening. Talk about a major bummer after such a major orgasmic explosion, especially as it was my first one ever with her.

But what she said was, "Actually, it's not half bad...not like anything my girlfriends said it would be like."

"Jesus," I thought to myself. "You mean to tell me girls actually talk about shit like that when guys don't?" And then I said..."Yeah?"

"Yeah, haven't you ever tasted yourself?"

"Are you kidding? Why would I? Have you?"

Teresa's look gave me the answer. But what was even more interesting, was the fact we'd never really discussed it, never talked about it, it was a subject that just never came up, until now anyway. And then I suddenly knew, Teresa masturbated too, obviously...and now I had another interesting image, fantasy, to add to my stored collection.

"Of course I have silly," she responded back. "Kind of hard not to...you know?" As she now wiggled her fingers at me, laughing. Two fingers in fact, which again spoke volumes. "Well," she then said suddenly changing the subject on me here, leaving me with my mouth still hanging open, my somewhat flaccid dick still hanging out. "I'd best go inside before mom discovers we're out here," she said putting all my toys away, straightening her skirt once more, though tossing her cum filled panties into the back seat, along with the bra she'd discarded earlier. "Oh, and do me a favor though if you would please. When you wash those? And you WILL be bringing them back, along with ALL my other bras, make sure you wash them on the delicate cycle, otherwise you'll ruin everything."

"Ah...Teresa?" I began finally putting myself away. "Would you like it if I..." She actually blushed, giggled and then opened her car door stepping out before I could run around to do it for her. She stood waiting for me as I finally managed to get out myself, speaking at me over the roof of the car.

"Eventually...maybe. Let's not rush things ok?"

"Ok," I responded back a bit dejectedly, though I asked her something else. "Can I...at least see it again? This time a bit longer than a second or two? I mean after all, you've seen me...so I'd sort of really enjoy seeing you."

She turned walking up the steps towards the front door, but I heard her as she said, "Maybe...I'll think about it."

I kissed her goodnight at the door, thanked her for the lovely hand job, and floated home I think. It had been one of those incredibly memorable evenings. And yes...I washed her stuff on delicate the following day after mom and dad left for a while. With plans on seeing her again the following day, even though it was a Sunday, her mom had pulled a Sunday shift at the restaurant she was working at, so we had every intention of taking advantage of things again. Something we always did too of course.

And we would yet again accomplish another milestone when we did.

*Mirror Images*

The nice thing about Sundays was, even though Sunday's were a rarer day for us in being together, was if Teresa's mom had to work one. When she did, it meant we had all sorts of private time to be together. Being Catholic, Teresa's sister and brother had no choice but to go to church. Which usually meant, a minimum of two hours, if not usually three where we were totally alone. Sure, Teresa was expected to go too, but at eighteen now, that was one of the few things her mom allowed her to make her own decisions about. And since she did go most of the time even then, on the days when her mom worked and didn't go herself, neither did Teresa. Though her sister and brother weren't given the same options as she was. Which was fine by me. I pretty much had the same call myself needless to say. And so it was, that I rushed over to her place the minute she called me to inform me her siblings had just left. After what happened the night before, I was hopeful for just about anything, and rushed over (with her panties and bras all cleaned and folded for her too!)

She must have been thinking about the night before almost as much as I had been. Almost from the moment I walked in the door, taking my hand, leading me over to sit down on the couch, we got right to it. This time there were no preliminaries, no small talk, no easing into anything. I honestly believe this was the first time she was hornier than I was!

I swear, it was inside of two minutes that I was sitting next to her on the couch sucking on her tits. And it was two minutes after that, when she asked me. "So...you still want to see it?"

Do bears shit in the woods? Though I think all I managed to do was sit there shaking my head yes. And then she stood, telling me she'd be right back as I watched her walk around the hallway corner heading towards her bedroom. I had no idea why...but I was certainly content to wait. She came back moments later carrying a fairly large hand held mirror. Ok, don't laugh...but this is the way I first got a really good look at her pussy. No kidding.

Teresa came out sitting back down next to me there on the couch. Curious, I sat waiting...wondering. "Sit back, look...it's the only way you're going to see it," she told me. (No...I'm still not kidding here). So I did. She'd been wearing a skirt, and like the night before, she'd removed her panties, only this time, leaving them back in her bedroom perhaps. So there we are, sitting side by side on the couch, and she holds this enormous hand-held mirror down between her legs, and then says. "OK, go ahead and look."

Now...it wasn't the style back then to run around sporting a shaved, or even a trimmed pussy per say. And I'll be the first to admit, I'd caught a glimpse here and there of my own mother's on infrequent occasion. And she was Irish. So you can only imagine. But here...Teresa being Spanish and all, I was surprised at what I initially was looking at. She didn't have much pubic hair at all. And what she did have, was so fine...and thin, that it literally laid down straight, almost as though she'd combed it that way. Now it's not like I'd seen a lot of women's cunts before...not like this anyway, mostly in a few magazines (the really dirty kind) where about all you ever did see was a thick bush. (Much like mom's, only her's was bright fucking red in color!) Teresa's pussy hair was jet black, but like I said, not much of it, thin, and wispy, laying down flat just above this magnificent looking slit. It was the most erotic thing I had ever seen. But...I wasn't seeing much else, not certainly inside, not with her legs tightly closed, and me looking into a mirror at her, which we both were.

"Well? Satisfied?"

I think I remember saying "It's beautiful!" (Score points for me on this one, because it led to a hell of a lot more because of it, I think.)

"Yeah? Really? You think so? Really?"

"Yeah, really," and then I told her I'd seen mom's once or twice, ALL bush...and ALL red. She laughed at that, told me her mom was the same way, though dark black too...but yeah, real hairy and all bush. I then told her how I thought her slit looked really cute. (Well it did!) and then she said "Yeah? You like it then?" I told her I did of course, and said I'd like to see it again if she'd let me. But this time...without the mirror. She thought about it for a moment, and then stood up, reaching for my hand. I took hers...and felt my heart jump up somewhere inside my throat as she then led me down that hallway towards her bedroom.

"Don't go getting any ideas," she informed me. "We're not having sex. Well...not intercourse anyway," she then added. Which told me in an instant a number of things. We were about to do something...far more perhaps, or at the very least, as much as we had done. Only this time, once again in broad daylight. "No more than an hour though," she likewise stated. "I don't want to take any chances in getting caught." Once again telling me, we were definitely about to do something. And then Teresa took off every stitch of clothing she had on.

Many Feathers
Many Feathers
10,503 Followers