Clothing Challenged

This is based on a true story from my life. The characters are of course changed in case any of them might still recognize themselves and object. It's true... up until it isn't. (My roommates actually challenged me to this, but I didn't 'accept the challenge. And that's where my fantasy kicks in. It could have been a true tale through The End, except that I chickened out.)

[As with all my works on here, The Authror Reserves All Rights excerpt those loimited rights give to Literotica.]

Once upon a time, I lived in a Castle. A fairytale castle (with sometimes more 'fairies' than not). Well, a hip, alternative castle that had been nicknamed The Castle. Except I only ended up living there for three months, before the wicked Landlord of the East evicted us.

The 'point of interest' (focal point) in The Castle was once Keith Hardwicke, and he had long considered himself the "agent provocateur" for this whole 'alternative operation.' Or as other people called him, The Ringleader. (And God knows, The Castle had become quite the 'circus' at various times.)

But all of a sudden, Keith had decided to move on. And since his was the only name left on the still existent lease, the rest of us had to find some new 'castle' to call our own.

Up until a certain point, I had pretty much lived in group houses for most of my adult years. Small 'communities' of anywhere from 3-5 people, sometimes out of being friends, and sometimes out of necessity. Because when I lived by myself, I had this tendency to cocoon off by myself in my lonely living space, and tend not to go out unless I needed to, for a particular event or work. I'm that way up until even today.

Now, living with others in a close in living situation can have its problems; Personal and Interpersonal. I had been in a number of roommate situations in the past that came with the territory of being a survival level hippie.

Sometimes my roommates were actively sleeping with other roommates, and at other times were sneaking around about it. It was a temptation, but I'd also known of situations where it had gone bad; really bad. So I decided to not make that same mistake and vowed to leave the idea of fucking my other roommates alone. This could have ended up being a big mistake.

———————————

When it came time for us to move, there was only two other roommates who were going to 'move on' to live in another house with me; Katie and Caroline (both of whom of course I was attracted to).

We had been living in our new house for about six months at this point, and we had gotten along fairly well by this point, having some good times and a few meals together. Where we lived now was quite diffrernt from The Castle. It was a traditional suburban home, the proverbial split level rambler, with enough rooms for all three of us (although I lived in the basement to accomodate that).

They were both quite socially gregarious, Katie being a yoga teacher and a former elementary school teacher, and Caroline was... Well, Caroline was a female Jock. She taught PE in the elementary school where she and Katie had originally met in.

Katie was a fierce (but cute) woman with tight, long, curly black, shoulder length hair, and a perfectly formed set of b-cup tits topping a body that had been sculpted by years of doing and teaching yoga.

God, did I have the hots for Katie. I was truly, madly, deeply in love with Katie. She had the almost perfect body that fit my dreams of what a perfect woman would look like, to... Well, perfection. and it was a good thing we weren't alone in the same room all that often, as I found myself walking around with a rise in my pants whenever we were.

Caroline on the other hand, was the somewhat more quiet sort (at least comp-ared to Katie). She was also on the cute side with tightly curled reddish orange hair, and body very similar to Katie's. But whenever I could, I would try to make her laugh, to bring her out of her shyness. I never really considered that Caroline had any interest in me, and she was also so into sports that I wasn't even sure that she was even interested in men anyway.

Now me at that point, I was still the shy and not very outgoing type. In contrast to them, at least. Oh, I had my friends all right, but not like the two party girls that I lived with. Katie was the really outgoing one, and Caroline sort of followed in her footsteps. For a while, I even thought that Katie and Caroline were secretly lovers, even though Katie had had a series of (apparently abusive) alcoholic boyfriends.

Katie had grabbed my attention from almost the very first time that I met her. But since she was in one relationship after another, not long being out of one because of her severely cute looks, I figured that I didn't stand a chance with her. And I never considered Caroline as someone I was all that interested in, us being so different seeming.

With Katie and her raging mane of black Italian hair, I found myself staring at her a little too often, very definitely interested but unable to say anything to her about it. Sometimes she would catch me staring and smile a little teasing smile and then turn away. I could feel the pull between us, but she had boyfriend after boyfriend, so I didn't see much opportunity there.

Oh, and did I mention that I don't like to wear clothing?Any clothing? Did I mention that I was a hhippie? and Also a Naturist (that's Nudist for those of you who don't know better). My usual clothing around the house was just a pair of shorts and a tee shirt, and more often than not, just the shorts. I never knew that this was any problem with either Katie or Caroline. It's just who I was.

It wasn't normally a problem, unless either one of them came out of their bedrooms dressed in either a swimsuit or with Caroline, a tee shirt and tight gym shorts. Then I had a hard time... Well... not getting hard. It was hard to hide an erection in baggy shorts.

Until one day...

I came upstairs to fix something in the kitchen, and apparently someone else heard me. "Oh Roger!" I heard Katie shout out to me.

Walking into the living room, I found both Katie and Caroline standing there, wearing only camisoles and tight panties, and... nothing else.

Oh-kay

, I thought. Not was I was expecting. With my eyes going quickly from one to the other, I was stuck on which of their bodies I liked the most, standing there in their barely-dressed splendor.

"So," Katie started as she grinned widely. "We figured if you were going to run around the house in next to nothing all the time, then we'd do it too."

"Hope you don't mind," said Caroline, also grinning.

At this, I could feel my erection spring into action. Not good. "Uh. Uh." My mouth tried to from an answer, trying to

not

stare at the nubile, young barely covered (and quite desirable) female flesh in front of me. I was not doing a very good job of

not

looking.

Both sets of camisoles were covering the "essential elements" as it were, but was not really hiding the bumps of elevated nipples poking out on each of their nicely perfect b-cup chests. And the panties of course, were not covering the 'female equipment' that resided just under their fabric as well.

I could see their "camel toes" distinctly and their even more enlarging nipples as they tittered in front of me.

"So," Caroline said now, "We decided if you're not going to wear much of anything around the house, then neither would we."

"Ok," I said again, rather dumbly.

"So here's the thing," Katie continued. "Caroline and I decided that we would join you and not wear anything."

"But you first," Caroline said as she snickered.

I hadn't considered Caroline sexy before now, but there she was, standing next to Katie with her curly red hairs peeking out of her panties, and also her perky little tits doing just fine beneath the light cotton bra.

I stood there for a moment, tying to do my best to not have a raging erection at this turn of events, and wasn't having much luck. It had been a long time since I had had two women almost naked in this close a proximity. I was torn between not concentrating too much on either of them, and trying to pretend that I wasn't as interested as my now bulging shorts indicated.

Staring at both of them in turn, my eyes fell to the chests in front of me, and I saw that each of them now had their small erect nipples pushing out of the top of their camisoles and the fabric made both sets of tits perky as hell.

Now, remember that I had had a fairly big erection going into all of this. And in the last few minutes, that hadn't found its way into relaxing from its full 'standing at attention.' I was like a deer caught at night in headlights. And of course, by their looking down at my shorts, they obviously realized my predicament.

Was I going to take off my shorts and present my, what was then, engorged erection to them? And what would they do? Quickly run back into their bedrooms, laughing hysterically without complying with their 'part' of this bargain?

I watched as they both took in the rather large bulge growing in my shorts. They didn't run away, but then they also didn't look like they were prepared to 'pare down' even if I did.

So we three stood there for another few very hard minutes, waiting to see who would call whom's bluff first.

I was prepared to run out of the living room and down the stairs, slamming the door to the basement and throwing myself down on my bed and beating my prick senseless to compensate for what I was seeing now.

"Well," I said, still trying to be cool. "What if I decided to run around the house buck naked?" I asked, playfully challenging them, thinking that they would back down at this.

"Ok," Caroline said, just as nonchalant as could be.

"Sure," Katie said after her, "Why not?" They didn't think that I'd do it, I guessed.

"Ok," I said, accepting the challenge, and reaching down, pushed my shorts off, letting them drop to the floor. As soon as the fabric cleared my crotch, my half staff prick found itself springing up and standing more and more at full attention.

I watched as first as looks of shock crossed both their faces as they looked at each other. With Caroline mouth open and nodding and with Katie shrugging, they had both of their camisoles off in the blink of an eye, with their panties soon joining my shorts on the floor.

Now I'm not generously endowed, like many guys claim to be, but I'm not small and insignificant either. But it was now their turn to become like that deer, both staring down at my newly revealed manhood. They both gulped at they saw there, and then looked at each other like they were going to turn and run.

Except they didn't. They looked back at me, and then loking at each other, both slowly began pulling their camisoles up and over their now quite visible and still very perky tits, up and over their heads. Their panties soon joined their tops (like a strip show) on the carpet. Katie had a black bush down below, which I never doubted I would find. But Caroline... She had a bush that was as bright and orange (even though a little less bushy than Katies), probing her red hair was natural.

I stared in shock myself now, taking in both of them in all their naked glory in front of me. I never thought that something like this would happen, and I was now both standing straight at attention and pulsing a little in the rush of blood from my balls to the tip of my prick.

If I hadn't been rock hard before I took my shorts down, I was now. And their nipples didn't relax either, but only stood up more and more straight and mountainous. Their nipples and aureoles stood up at attention almost as much as my manhood did. (Not quite, but you know my eyes were seeing them that way.)

Katie had a wild raging black bush (as I should have guessed) down below spilling out all over now that it was free of its previous panty constraints. And Caroline's shining goldish red hair was almost as full, that was now glistening even though there wasn't any direct light to speak of coming into the room. I found myself growing thicker and throbbing more and more the more I stared at both of them.

Looking up to their two sets of chests, I was surprised to see that Caroline had those large wide nipples that I thought I would find on Katie. Instead, Katie had the small but mountainous red thumbs rising out off of hers.

We all stood there for a long seeming minute, all three of us not sure what each of us wanted to do next. This was a moment I had been waiting for (at least with Katie), and here we were, but I was more stuck as to what to do than I thought I'd be. They both looked at each other again and nervously laughed to the other.

I took a deep shuddering breath, and walked up between the two of them and proceeded to carefully put one arm around each of their waists at crotch level, pulling them both to each others hips.

I looked at each of them between me, still with their shocked expressions, and leaned in and kissed Katie first on her mouth, and then turned and kissed Caroline. Not little pecks either, but deep searching kisses.

I heard their twin sighs as they carefully each grabbed a side of my raging prick and held it in their hands. "I've been wanting this ever since I moved in here," I told them, reveling that my now visible instrument was between their hips and bringing them together with my arms even tighter.

"Wow," Caroline said breathlessly. "I didn't think that you were going to do it."

When I did this, I felt Caroline start to back away, and then Katie's left arm reached out to Caroline's waist and grabbed it. "Oh, no you're not. We agreed to do this. Together."

"Yeah, but—" Caroline started to object. Katie turned to her co-conspirator and wrapped both of her arms around her friends waist encircling Caroline so she couldn't jackrabbit away.

Since I was more interested in Katie than I was Caroline, I told Katie, "That's ok. Let her leave if she wants too."

"No," Katie said forcefully. "We agreed to do this, even if it didn't mean we were going to follow through with seducing him."

Seducing

? I thought. So that was this game was about all along? They didn't really believe that I'd follow through and go full nude on them, and Caroline obviously wasn't all that interested in the aftershocks that my doing that would do.

But this time it was Katie that became the dominant one. She grabbed my left hand, and then Caroline's right, and began pulling us into her bedroom. To Caroline, she said, "You wanted to do this almost as much as I did. So now, no chickenshit."

As I looked down the length of my body, I could see them hesitate, hovering on either side of my now glistening member. Katie moved in and began half encircling my prick, and Caroline sighed and did the same on the other.

I hadn't thought that either one of them might be more than friends before now, but now that they were both giving me a blow job together, their lips met and after a few seconds of hesitancy, they joined them together and began moving up and down switching sides with who would lick the tip.

"My bed's bigger," Katie said.

"Ok, that's fine" Caroline said, as if she was suggesting a nice tea that Katie was about to make.

Apparently it was more safer when we had only been standing in the living room. Now we were in Katie's room, it was suddenly not a playful challenge any more but had become throbbingly real.

Just inside her door, she turned around and kissed Caroline full on the lips, sticking her right fingers in between Caroline's legs and beginning to rub Caroline's vag and clit. Caroline moaned and succumbed to this 'attack,' and Katie used her left hand to grab and stroke my now throbbing member in that hand.

She let go of the kiss with Caroline and turned to face me, now kissing me. Full on the mouth and sticking her tongue in my throat. I was suddenly in heaven, and I sure didn't want to fall. Except for her, of course.

I had wondered sometimes whether Caroline was a lesbian or not. I hadn't known her to have many friends over, although some of them (both male and female) went into her room with the closing door behind them. Since I hadn't heard any noise when it happened, I just thought nothing of it before now.

Katie on the other hand, had had a series of lovers that I had been jealous of, but now finally found myself in their place. I had fantasized beating off many times to what I thought Katie was like under her sometimes form fitting clothes, but now I no longer had to fantasize. And this time, I had two women laying down on either side of me, not just the one I had dreamed about.

After a few minutes of her attention and a carefully placed set of my right hand fingers in Caroline's clit and labia, Katie pulled away. She pulled my still throbbing prick and guided me towards Caroline's waiting clit and lips and said to me, "Come inside of her. She's been wanting this for a while now, too." With a look of shock, I wasn't going to argue.

I grabbed Caroline's waist and drew her to me, sliding me right into her pleasant looking thigh gap, right below her flaming red pubes. Once I had plunged into her folds, I freed my hands from her waist and brought them up to her cute and perky (and standing at full attention) nipples and began rubbing and clenching them with my fingers. I began kissing her passionately as she began moaning louder and louder.

And then with one thrust, I went up and into her vag, raking her clit as I did and she threw her arms around my neck and squeezed me in close. Her left leg began rising and wrapping itself around my right hip, and I quickly grabbed her other leg and pulled it up around my waist as well. I was now fully inside of her and riding her to ecstasy. Standing up.

"Oh, God. Oh my God, Yes!" She began screaming. "Harder! Higher!"

So I began slamming into her even harder. My hips became like a locomotive as I pistoned in and out of her, driving her to the raging orgasm that she finally let happen. Crashing through her, from her head to her toes, she spasmed on my body like a jackknife thrusting herself as far onto me as she could with a shriek. "Yessss!"

After about a minute of this, she squirted her juices on to my belly and down our legs, hyperventilating. It took her minutes before she began breathing easier and easier, coming down.

"See," Katie told the exhausted Caroline. "I was sure that you'd like that." And turning towards me, "And isn't that a really good exhaustion?"

I turned in her direction, and found her kissing me deeply once again, her arms going around both of us and pulling us in tight.

"Now you're going to have to share," she said to Caroline — who just nodded lazily in her direction.

Turning to Katie, Caroline told us, "Whatever you say, hon." And then returning to me, "I don't know why I was so scared. I think I'm going to like wearing you out."

I gently let her legs release from my hips and slide slowly to the floor beneath us. "I think I need to go and take a shower and have a nap now." Caroline said as turned towards the door, opened it and left.

"Well. Speaking about a nap, I'm going to have to let you sleep and rest up for me next!"

I turned completely to her now, and asked her, "Can we take a nap before that? Together?" I really wanted her to say yes.

She just smiled and began dragging me towards her bed. "I think I can handle that!"

———————————

Katie and I made deliciously delirious love after that nap, fucking like bunnies and melting into each other. Round after round after round, all afternoon and into the evening.

At some point, Caroline returned to the room and snuggled into the two of us, which felt wonderful to me. No more lonely nights for the foreseeable future. My only regret is that I felt that I couldn't ask Katie to marry me, since Caroline and I were almost as much in love as Katie and I were.