Cum Drops Keep Falling on My Head

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Darren meets the wildest roommate.
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Many Feathers
Many Feathers
10,444 Followers

During my junior year at college, I'd transferred to a smaller State University. The one nice thing about living in a small town, attending a smaller school, it seems that everyone is far friendlier. The only problem I had was in locating a place to live for one, and for another, being able to afford it.

After spending several days hunting for a place, I finally found one. But again, the price was just a little beyond my means in being affordable. Solution: "Advertise for a roommate!"

I had enough to cover the first months rent by myself, so I moved in with the hopes that I'd be able to quickly locate a roommate to split expenses with. Placing an add in the local newspaper, I wasn't surprised when I got knock on my door the very next day. Not having a phone yet, I'd indicated that prospects would have to apply in person. I was surprised however when the very first person to knock on my door inquiring about the apartment was a rather attractive looking female. I hadn't indicated I was looking for a male roommate, truth was, I hadn't given it any thought. I'd simply assumed from anyone reading the add, they'd realize I was a 'guy', especially with a name like Darren Somers.

"Are you the one looking for a roommate?" she asked.

I couldn't believe my eyes. I mean she wasn't model material or anything like that, but she really was attractive. Her hair was reddish brown, long and fell perfectly over the slopes of two very prominently displayed breasts, both of which at the moment anyway, were accentuating two very erect nipples.

"Ah yeah, I am," I said stunned, still looking at her expecting to wake up from some wet dream I was seriously hoping I was really having. Her eyes were even more alluring, the most unusual color I had ever seen before. Almost violet in color it was hard not to drown in them as I stood there stupidly staring at her.

"You're surprised?"

"Ah, what? Excuse me?" I said, my thoughts finally gathering together. "Surprised?"

"Yes, that a woman would answer your add," she said smiling at me.

Oh, that smile, it was enough to make any man...or woman for that matter melt just standing there. It wasn't overly sexy, or even provocative. It was just pure unadulterated sensuality in its simplest form. "Yeah, guess I am a little," I responded, suddenly feeling a lot less sure of myself than I normally was. "I just didn't expect to see a woman actually answering the add. Truth is, I never even considered it as a possibility."

"So does that mean you aren't interested?"

Once again, I was hearing what I wanted to hear, and not what she was saying. "Wow...am I interested!" I thought. But we were obviously discussing two different topics here. "Ah, sure. You want to come in and see the place before you decide?" I offered.

She laughed. "Before I decide?" she said giggling as she brushed past me into the room.

I was still stunned, not even bothering to step out of the way as she let herself in. I felt the briefest, slightest contact with her breasts as she did. Whether she had done that knowingly or not, it didn't matter. At the moment, I was praying I'd picked up my underwear and hadn't left my latest copy of Hustler lying on the bed in my room.

"This is nice," I heard her say from just off the living room. She had stepped out onto the balcony. I had the top floor of a six-floor apartment.

"This isn't even the best one," I said grinning. "You should see the one off my bedroom..."

Realizing what I'd just said, or perhaps intimated to her, I stopped mid-sentence. She was looking at me with that same hypnotic smile again.

"Oh? Which one is your room?" she asked.

"Ah, down the hall, past the bathroom. There's only one of those," I added lamely. "Your room is across the hall from mine."

"My room?" she said smiling again. "Does it have a balcony too?"

"Sorry, no. But I guess we could switch..."

She grinned, "No, I wouldn't expect or want you to do that. Besides, we'll be roomies," she added. "And as roomies, I imagine I could share your balcony with you couldn't I?"

And just like that...I had a roommate.

"Ah, by the way. What's your name anyway?" I finally asked.

"Tanya, Tanya Hide."

"Excuse me?" There I was again, hearing what I wanted to hear, and not what I was supposed to.

She was laughing again. "I get that a lot. My last name really is Hide. I think my father thought it was funny when he named me. He was a 'good old boy' for one thing, grew up on a ranch, one of the old 'cowboy' types. Though mom always said he was born in the wrong century. To see him, you'd expect to have him drawing a pair of six-guns and wearing a Sheriffs badge on his vest to go along with the real-live handle-bar mustache he wears."

I wasn't having, or expecting to wake up from a wet dream anymore, this was now turning into a nightmare. The image of her father suddenly showing up at my door, a pair of pearl handled colts in each hand pointed directly at my crotch had deflated the erection I'd been trying to hide.

Tanya recognized the expression on my face. "Don't worry, Daddy wouldn't dare say or do anything. He's been fucking so much strange pussy, that should he ever try to make life tough on me, he'd find he'd finally bitten off more than he can chew."

Hearing Tanya's obvious relaxed vocabulary was refreshing. Already she was acting like my best buddy. And once again, I was thinking she'd be just that. A buddy...not a 'fuck' buddy as the earlier wet dream I'd been having had suggested. Maybe it was no longer a nightmare I was having, but now it was one of those dreams you wake up in the middle of just when things start to get good.

"Ah, before you make your decision, there's a few things you should probably know about me," I told her. Hell, in my mind, I was taking a major risk here. I could be fucking up the best situation any guy could find himself in. But it was that, laying my cards out on the table, or shocking the shit out of her once she'd moved in, only to watch her packing up the next day, or worse...having to act like I was living at home again.

I took a deep breath screwing up my courage, when I spoke however, I sounded a bit like 'Donald Duck' just having inhaled half a balloon full of helium.

"I like to lay around the apartment nude!" I exclaimed in my best Donald Duck imitation, which frankly, I'd never managed to do before.

"Oh? Good! Me too!" was all she said, sounding a little like Daisy, to which I of course, briefly wondered if she was making fun of me. "So, I can have the room then?" she asked seriously, sounding like herself.

I coughed, cleared my throat to speak, and nodded my head instead. "Better to be safe than sorry," I thought, though I'd managed to think that speaking like a duck too.

But, just like that, I had a roommie AND a wet dream all rolled up into one.

#

As it was the weekend, Tanya began moving in the following morning. As she had a truck, it took very little time to move everything into the apartment. Having a service elevator certainly helped, but the fact that she had very little furniture made it even easier. Her bed consisted of a giant blow-up mattress, which she preferred sleeping on anyway, and one or two pieces of bedroom furniture, the largest of which was a dresser drawer. By noon, we'd moved everything she owned into the apartment.

"Well, that was certainly a lot easier than I'd anticipated," I told her.

"I've learned, especially as I've moved around a lot these past couple of years. It's a lot easier not to have a lot of furniture to have to worry about. Especially the bed," she giggled.

Her statement made me curious. "Why have you moved around so much?" I had to ask.

For the first time since we'd met, I actually saw her blush. "I like to party, but I tend to get a little crazy when I do," she confided. "A few people haven't appreciated that, I think, seeing a side of me they didn't know existed when I have let my hair down. Does that worry you?" she asked concernedly.

"Who? Me? Not hardly," I replied, suddenly worried. "What had I gotten myself into?" I wondered. She really was too good to be true. And maybe that was the problem. I'd learned a long time ago that if something seemed better than it should be, usually there was an underlying reason behind that. And I found myself thinking along those very lines as Tanya made herself to home inside our apartment.

I had very little in the refrigerator aside from a loaf of bread, baloney, and a carton of milk that I wasn't any too sure of. Having gone into my room to change out of my semi-sweaty clothes, I'd decided it might be a good idea to make a trip to the store for a few groceries. I'd changed into one of my favorite football jerseys, cut-off Levis and sandals. I was a little surprised to see her comfortably sitting in my favorite armchair, one leg thrown over one of the arms. Though she was wearing a pair of shorts, sitting there spread eagled as she was, as I stood in front of her momentarily, it was obvious that was all she was wearing. Only then did I glance away from her nearly exposed crotch to discover she was leafing through my Hustler magazine.

"Hope you don't mind," she began. "I love looking at these. It's kind of nice seeing real people posing in these for a change."

"Oh, not at all. Help yourself, anytime," I replied a bit embarrassed that she was actually looking at my magazine, though why I felt that way I had no idea, especially as it certainly didn't appear to bother her.

Glancing up finally, she nearly caught me as I continued staring at her crotch. I'd already caught a hint of what appeared to be long thing wisps of her pubic hair that appeared almost as though she'd combed it.

"Hey! I love football jerseys!" she said out of nowhere. "I used to have one, but my ex-boyfriend stole it from me."

"Well, anytime you want to wear it, just ask," I said feeling friendly, if not somewhat guilty at having stood there trying to sneak as much of a peek as it was possible for me to get away with.

"Really?"

"Yeah, really."

"Ok, I'm asking now then. Let me wear it?"

I really did need to schedule an appointment to have my ears checked. I could have sworn she was asking me to take it off so she could wear it now.

"Well?" Tanya suddenly reached down, pulling the tank top she'd been wearing up and over her head. Seconds later she was sitting there, her luscious breasts that I'd already secretly masturbated while fantasizing about, were sitting there staring at me. All she needed was an oversized pair of glasses with eyebrows and a funny looking nose to sit over the top of them to complete the picture I had suddenly formed inside my head as I gazed in a stupor at her exposed breasts.

"Well? You gonna let me or not?"

I wanted to. But now I had a new problem to deal with. My jersey was currently covering the erection I'd allowed myself to have while standing there staring at that soft patch of pussy hair I'd been admiring. And now, she'd gone and upped the 'ante' by exposing a pair that beat my "one of a kind", I thought abstractly.

"Ok, sure," I said, turning slightly as though struggling with the jersey in taking it off, slamming one hand down in front of my Levi's in a last-ditch effort to attempt to readjust myself so that the 'obvious', wouldn't be.

"Hey! You've got a woody!" she exclaimed happily. "I give that to you?" she asked.

"Fuck me!" I said silently. "Ah yeah, guess you did. You really do have nice tits," I said. "Shit!" I thought a millisecond later. "You could have said breasts, even boobs would have sounded better. But no numb-nuts...you had to say tits didn't you?" I asked myself.

Tanya laughed. "I like you. Not many guys I know call em 'tits' anymore, not to a woman's face anyway. Always behind our backs usually. And thank you. I'm rather proud of them myself."

"I can see that," I said silently, still carrying on a one-sided conversation with myself. "Well, they are...pretty." I finished.

Tanya frowned. "Don't go backwards on me Darren. Pretty tits don't fit together as well. Sexy tits, hot tits, even fucking nice tits are good. But if you insist on calling them pretty, then go back to calling them breasts, or boobs. But personally, I like the word tits, its cute. Just don't call them pretty at the same time."

I threw her my shirt.

"Ah, listen...I'm going to the store to pick up a few things. You need anything?" I asked.

"Matter of fact, I just started my 'monthlies' this morning. Would you mind picking me up some 'Tampax'?"

I heard her perfectly this time. I just didn't know what to say, or how to say it even if I did. I know my mouth was open, though nothing was coming out of it. Tanya burst out laughing.

"I'm just kidding silly. But the look on your face was priceless, not to mention the fact you no longer have a hard-on any more either," she added.

Only then did I realize, I didn't.

"You like Italian?" she asked, changing the subject.

"Ah yes, sure."

"Then pick us up some spaghetti, some sauce...." Tanya looked up towards me, "you want me to write this all down for you? I really do make a killer pasta."

"Maybe you'd better," I said sitting down, suddenly feeling rather exhausted. Tanya was certainly one thing, and that was totally unpredictable. Having her for a roommate was going to be an interesting experience.

"You know what I'd like to do later? After dinner?" she asked.

"No? What?" Images of being tied to a bed, handcuffed, blindfolded suddenly came to mind.

"Sit outside on your balcony," she emphasized saying, "after its dark, share some wine, and let the cool night air wash over our nude bodies," she added. "Doesn't that sound like fun?"

"How much wine?" I asked, "And what kind do you prefer?" I smiled asking. "And what about the handcuffs?" I silently asked myself while looking at her, looking at the larger than life '69' on the jersey she was wearing as her tits sat there pressing against it.

#

Dinner was even better than I had imagined. Tanya had insisted we dress formally for our first nights dinner together. She wore pearls. I wore a tie. That was all we wore however.

I'd splurged, purchasing a couple of bottles of a nice 'earthy' Merlot. We'd polished the first off during dinner, which we'd eaten by candlelight, the only source of lighting in the entire apartment. I stood uncorking the second bottle of wine when Tanya took our now empty glasses outside to the porch. Obviously, she hadn't been kidding about that either.

"You coming?" she inquired.

I had a come back for that, but I let it pass. "On my way," I said instead.

Tanya was sitting in the only lounge chair I had. Which was fine, except it placed my 'dangling' participle about eye level with her as she held up our two empty wine glasses for me to refill.

After pouring, I sat the bottle down on the little table next to the chair she was sitting in. With nowhere to go, I wandered over to the railing, trying to appear as nonchalant as possible. Which was hard to do with her sitting there all sexy and naked.

"Nice fucking tits," I thought as I walked over to the rail looking down.

Below, the rather large sized open aired hot tub sat looking lonely. Visions of Tanya and I soaking, playing in it together immediately came to mind. The soft blue lighting of the water looked inviting enough, but the fact there was no one else around at the moment was an opportunity that would rarely, if ever come again. I had learned from 'Jeff' our landlord, who was also a senior attending the same college that most everyone else who lived in the apartments where, was away for holiday. With the next semester starting in just over a week, most would soon be returning.

"What are you thinking about?"

I sensed rather than saw as Tanya stood, moving over to stand next to me looking down at the romantically lit hot-tub.

"Just wondering when we'll meet the rest of the tenants," I said truthfully.

Each floor was its own apartment. So there were six units, though all except for Jeff and some guy he had called "The Geek", there were a total of ten people actually living here. In the second floor apartment lived two women, one of which Jeff had said was "pretty wild". I smiled inwardly upon hearing that, wondering if she'd be any match for Tanya. The 'Geek' lived on the floor above them, with another pair of guys sharing the forth floor. A married couple, attending college together lived on the floor just below us, also home for a visit according to Jeff. As for Jeff himself, he'd landed this cozy little job watching over the place for the actual owner, which was nice as we could 'party' without getting into a whole lot of trouble.

"Yeah, I was wondering about that too," she said leaning over the rail. I watched as her breasts pressed against the railing, wishing it was me she was leaning against like that.

"How far away do you think the tub is from here?" she asked.

"Why? You're not thinking about jumping into it from here are you?" I asked incredulously.

"Of course not! Don't be silly!" she responded. "I was just wondering about something is all!"

"What?"

"You really want to know?"

I did, and I didn't. "Yes, I do."

"Be careful what you ask for," she said smiling in that way that could melt steel.

I was very aware of that fact, but I asked her again anyway. "Tell me, what is it you were thinking about?"

Tanya laughed, and I felt the hair on the back of my head stand on end as though I were about to be struck by lightening.

"You ever measure how far you shoot when you cum?"

The truth was, I had. But I wasn't about to tell her that! "No! Why would you even ask such a question anyway?"

"Just curious, I was wondering if you could reach the sidewalk at least," she said leaning over the railing again as though trying to imagine it.

Curious, I leaned over looking down, judging the distance in my mind. "I dunno, maybe," I said stupidly. "Why would you even wonder about something like that?" I asked.

She was grinning, wickedly.

"Ah oh, what are you up to Tanya?"

"Wanna play a game?"

"A game?"

"Yeah, it's called if you win, you can do anything you want to me. If I win, I get to do anything I want to you."

I didn't see a way to lose here actually. Which was what was wrong of course. "What kind of game are you thinking about?" I asked tentatively, already wishing I hadn't asked.

"A naughty game. You do like naughty don't you?"

Just the way she said the word made me feel that way. The fact I'd begun to get an erection standing there in front of her said that much. With no way to hide it, I let the 'naughty' feeling wash over me urging me on to accept whatever proposal she had in mind.

"Ok, why not?" I said giving in.

Tanya was beaming. Moving away from the railing to face me, her hand reached down clasping my rapidly hardening prick.

"How long do you think it will take you to jerk yourself off?" she asked.

"Not long," I said huskily.

Tanya winked. "Will this help things along?" Her hand on my cock, busily stroking it certainly was.

"Oh fuck yes!" I moaned. "What are you planning on doing anyway?" I asked through clenched teeth as her hand drew me towards greater pleasures than I'd known in quite a while.

Once again she smiled that devilish smile of hers. I wanted to smear my orgasm all over those sweet luscious looking lips, deciding as I considered the thought that if I won, that's exactly what I was going to do.

"Let me know when you're getting close," she warned me. "I want to have enough time to get downstairs."

"Down there?" I questioned incredulously. "You're gonna go down and stand on the sidewalk?"

"Yep! Then, when you're ready to shoot...it will be your part of the game to see if you can hit me with your cum!"

"You're serious!"

"Very. Just don't take too long though, I'll be standing there in my birthday suit waiting for you."

Many Feathers
Many Feathers
10,444 Followers
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