Ali Ooops

Literotic asexstories – Ali Ooops by bobhardcastle,bobhardcastle
I live in a group house that’s in a really nice part of town; walking distance to the coop for food shopping, with a nice high end theater complex a little walk further away.

For some reason, even though the houses around us had been “upgraded” over the years and remodeled to be more upscale, ours has been a group house for decades. We were not ‘easily kicked out’ by the landlords, due to one of the former roomies having gone and gotten their law degree. He made sure that we — The House — stayed ‘unmolested’ by the gentrification going on around us. He still liked to come back ‘home’ every once in a while, and we in turn still liked to have some rather wild parties (considering the neighborhood).

But the rent kept on getting higher and higher. So much so to the point where our rooms had to be shared in order for us to stay there., usually two to a room. Which was where I was waking up this morning…

We were an eclectic mix of folks. Some of us are still hippies, some of us are edging towards moving out and moving up. I was on the borderline of both, but I was still here.

I also have to tell you, that I’m still here mainly because I hate the idea of full time work. I work part time down at that previously mentioned theater, and make just enough to satisfy my need to eat and pay rent, as well as having the perks to go to any movie that I wanted to. (The perk that keeps me working there.)

This morning, my roommate Randy had already gotten up and gone to work. From the sound of the house, most everyone else had left too. So I got my seldom granted, blissful grace of silence to sleep in. Not something that often happens here.

I was about to go back to sleep in order to wake up later in the day before I had to go to work. Also, since Randy was no longer here and the house sounded empty, I decided to indulge in another favorite past time if I was alone; wanking off. Without interruption (or so I thought). This would help me drift back off.

Another thing I should tell you. That eclectic mix I mentioned earlier? There were several of my housemates that were Gay or Lesbian. One of them was Allison, a rather larger and formidable woman of ‘interesting hair’ and ‘larger proportions’ (shall we say). Allison was kind of what was described in the song Lola, by The Kinks. Although she didn’t need to shave, she was, well…

Her name was Allison Gertner, but because of her bigger size than most of the other girls around, our secret house nickname for her was Ali Ooop. Like the cartoon character of the same name back in the day who was a neanderthal.

She wasn’t as ugly as the cartoon showed and she was not a man, but she was not what you’d call, a petite woman. Because of her size and the kind of women she normally went with, she was what you might call a “bull dyke.” And yes, I thought she was Lesbian, through and through.

She seemed like a Big Woman, although I couldn’t really tell. She was on the larger size alright, although I couldn’t tell you what her body actually looked like, because she always wore what the other roommates called ‘dyky kinds of clothes.’ Sack-clothe-like dresses, kinda like what my mother’s generation called muumuus (although here’s weren’t colorful floral patterned dresses). Oh, and clunky Doc Martins too. You know. Dyke fashion. (I know. Call me prejudiced if you want…)

And she had her Icelandic blonde hair cut in a bowl shape up around her ears, along with it chopped off as high bangs (almost like a fringe) in front.

She was rather quiet around the rest of us. In some ways she didn’t fit in… But Hey, when you’re living in a group of “misfits,” what’s fitting in?

Randy, my shared roommate, had apparently left the door to our room ajar when he left. I had begun ‘yanking my chain’ (so to speak) and was getting into it rather wildly, when I heard one of the boards in the hallway outside our door squeak.

“Shit!” I said, trying to cover myself and my activity. That’s when I saw the eye in the crack of the doorway, looking in on me.

“Ali,” I said, jumping when I saw Ali Ooop push the door open.

“Sorry, Rick,” she said softly from where she had moved into my room. She reached behind her, and while her eyes kept on me in the bed, she softly closed it. “I saw… what you were doing, and I… well… I couldn’t help myself.”

“I didn’t think you liked men?” I asked her, not realizing that I was still only half-way covered.

“Well,” she started to day, “I don’t,” she said, and then she paused, adding,. And I… do.”

Ok, I thought. What does that have to do with me? I took a deep breathe, and waited for her to explain more.

“Do you mind if I come in?” she asked me. Even though she was technically already in my room.

“Ummm,” I fumbled. “What would you–”

“I’d like to watch you. Beating off, I mean.” Ok. I gulped. Where was this leading to?

I should probably say here, that although I was thirty-two, it had been a while since I’d had a girlfriend. Which was why I was beating off, instead of ‘beating’ into a ‘her.’ So, why was she interested in me? And why would I be interested in her?

“But I thought that you–”

“Only liked girls?” She said softly with a grin forming on her lips. “Well… Yeah. That’s what I thought, too.”

I relaxed some, but my thoughts started to go all chaotic on me. Used to like only girls, I thought. Now, for some reason, you’re interested in watching me jerk off. Something didn’t…

I watched rather dumbstruck, as she quietly closed the distance between the door and the edge of my bed, very slowly bending to sit down there. Like… a foot away from my hand still unconsciously on my crotch. Like… almost as if she was going to touch me.

Part of the chaos inside my head had me asking, If she’s actually interested in me, what does that make me? Does that mean that I’m less of a man, and more like a woman? I hesitated to even ask her. Did I even want to find out? How hard did I want to find out?

But there she was. Sitting on the edge of my bed, staring hard at my half mast prick still somewhat standing at attention through the covers, kind of like Shroedinger’s cat. Half up, and half down. Did I want my prick to rise to the occasion and come alive? Or did I want it to deflate and show no interest? Well, not dead. But dead to her. What would it mean if I found myself attracted to… her?

“Why me?”

“Am I that ugly?” she asked me rather plaintively. She looked like she was at the point of crying, which seemed so out of place for her.

“I, ummm… well… I just… I’m not…”

“You don’t find me the least bit attractive?” she asked, holding back a sniff, and looking like tears were going to stream down her face any moment. I felt really bad for how I reacted, and I reached over to touch her shoulder. I felt almost as if I wanted to take her into a hug.

She began huffing and puffing, and hyperventilating around her choked off tears. That did it for me. I reached over and grabbed her, and pulled her into me. This only succeeded in setting her off even more, and she began sobbing hard in my arms.

God, this was awkward. I had just had more conversation with Ali in the last several minutes than I had had since she had moved into the house about eight months ago. And here I was also, sitting up in my bed, nude, after having been caught masturbating. But with this woman who I had thought had no interest in me at all. As a man, or even as a person.

And here I was, comforting her. Patting her on the back sympathetically. And once again, completely nude only a thin sheet away from her.

After a few minutes of her crying, she began slowly stopping. Taking deep sighs in. And now she was whispering softly on my shoulder. Wow, this was a wild morning.

She sat up, still sniffling, and began wiping her face with her (somewhat) hairy arms. She didn’t look at me for another couple of minutes, but when she did, there was a look there that I hadn’t seen before. Hadn’t expected that I would ever see.

She was looking at me with a look of… attraction? Lust? At that point, my whole perception of her changed. She was looking not only attractive, but…

“Can I crawl into bed with you?” she asked in a whisper I could barely hear.

“Ummm. Sure,” I told her. It had been so long since my last girlfriend. Was this woman that I thought wasn’t even interested in men, going to end up being my next girlfriend? The look in her eyes told me that might be a possibility.

I fully pulled back the covers, and she surprised me once again. She stood, right next to my bed, and pulled her sack of a dress off. Pulled it over her head without hesitation. And then she let it drop to the floor and just stood there.

I had to admit, now that she was standing there naked, she didn’t look half bad. Oh, she was still a Big Girl all right. She was like a size eighteen, but her two breasts looked on the nice and voluptuous side, hanging down in nicely globe-like shapes with nice big areolae and thumb-sized nipples atop of them.

She did not have rolls of fat like waves all down her torso, like I would have thought that she did. That those waves of fat might be the cause for wearing those big dresses (if you could call them that). But she did have soft blonde down-like hair all over her body. But instead of looking gross, it made her look like she was a big sensual cat. It even glimmered in the hazy half-light coming in through the blinds at the windows, a soft sheen on her arms and belly and legs.

She had nice wide (grab-able) hips, with pillows of muscles both above and below her navel. Her size was spread out nicely, and although big, she seemed nicely proportioned (unlike some of the other Big Girls I’d seen lately).

But looking further down her body, I came to the big furry patch of blonde pubes that were just below her moderately curvaceous belly. And there was my next big surprise.

Because out of her blonde pubes, was sticking a… large clit? Vestigial prick? It was large enough that it was poking out from her furry There. It didn’t look like it was a male organ, but it was most definitely There.

She lowered her eyes to where mine were glued, and her whole demeanor began slumping forward. “Yeah. That.”

“Ummmm,” I tried to get out the next question, but couldn’t.

“Yes, it gets a little bit bigger when I’m… you know… but not by much. Is that gonna kill… I mean, you and…”

“It’s just… that I’ve never seen one that…”

“Big? Well now you know why I’m mostly with women. Most Lezzies kinda like it.” she said as she began swaying back and forth, like a little pre-teen girl. Half shy, and half embarrassed, starting to chew on her lower lip.

I couldn’t take my eyes off of It. I mean, it was almost bigger than some of the fat shorties in the locker room I’d seen at school. Except that it didn’t have a ‘helmet’ on it.

I licked my lips. I was hesitant to ask what I wanted to, but– “Can I touch it?”

She put her knees on the mattress, and kneeled right in front of me. She smiled a shy half-smile and moved forward towards me on the bed. The look in her eyes changed from hesitation to expectancy, and she licked her lips and then erotically bit her lower lip, looking at me seductively through half lidded eyes.

When she was almost to my face, I reached up and used my finger to move it back and forth. And when I did, it began growing larger. It ended up about an inch and a half in length, poking out of her blonde furry thatch.

I sat there and stared. And then she did something that I did not in the least expect. She pushed me by the shoulders until I lay back in bed, and with her knees, walked herself up to where my face was and stuck her now dripping clit on to my face.

“Do more than just touch it,” she commanded. And I stuck out my tongue to taste it.

Putting it in my mouth, I began to suck on it, like I would a nipple or a whole tit. I lifted up my mouth to take it completely in, and sucked it in deep.

She spasmed and came shivering then like a quake above me. Her juices gushed out into my mouth, and onto my chin and dribbled down my chest.

She looked down at me lovingly, and gently grabbed me by the hair and ears and began massaging my head and neck. “Now that was more like it,” she said still breathing hard, her words dripping with contentment like her snatch had dripped out of ecstasy.

After several more moments of her caressing my head, she began knee walking in the opposite direction, down to where she was at my now fully erect and shaking prick. She lifted her hips up when she got there, and grabbed it by the head and pushed it in her soft and yielding pussy cat. She began pumping up and down on me, faster and faster, until I could once again feel her spasming and quaking over top of me. Needless to say, I came like a motherfucker, shooting into her, time after time after time, until I lay back exhausted.

As exhausted as I was, she gently laid herself down to lay on my stomach, and stretched her thick legs out on either side of mine. We were still breathing hard, when I asked her, “Was this your first time? With a man, I mean?”

I could feel her begin to sob, tears beginning to flood my chest and shoulders. I wrapped my arms around her, and moved my own legs out from under her, and then wrapped them around her legs holding her tight.

She sobbed for what must have been ten or fifteen minutes. When she slowed down her crying, she turned her head to lie in the cook of my neck.

“With a man my own age” she whispered. “My uncle… when I was a child…”

“Shhhhh,” I whispered into her ear. She didn’t need to tell me any more.

“That’s another reason why I’ve only been with women,” she whispered into my ear. She sighed, and I felt her arms strong on either side of me, holding herself up so as not to crush me.

“So… Why me?” I asked her once again.

“Cause you didn’t seem like a lot of the other guys I know. You’re more quiet. More respectful. More… laid back. You haven’t tried to hit on me, try to ‘turn’ me straight.”

“You mean, other guys here?”

“And where I work. That’s why I wear what I wear. Trying to discourage…”

“And don’t you think that I might make you–”

“Pregnant? I’m on the pill, just in case some guy tries to rape me.”

I was confused. “So are you straight? Or are you Gay?”

“Well… I guess I’m Bi-,” she said rearing up and laughing and smiling. “Aren’t I?”

“Yeah, but… Does this mean that you want to be with me? Or do you still want to be with other women?”

“I’m not gonna lie. I like fucking other women too. That’s probably not going to stop.”

“Can I–”

“You want to be on top now?”

“Yeah. I know you’re been holding yourself up, but…”

So, as strong as she is, she began turning us over. Pulling us to my right, her left, until I was, yes, on top. Of her and feeling on top of the world. “Has your hair always been this short?”

“Well,” she smiled at me, “Maybe that I have a man in my life, I’ll grow it out. Don’t have to make myself look more like a man if I don’t need to.” She smirked and rolled her head to look at me strangely, “If you really need me too, that is.”

What did I want? Did I want a relationship with her? Or just that we be fuckbuddies?

“So, what do you–” I began to ask her.

“I don’t know. You and me be together sometimes? Me and Sadie like to hook up every few days; I mean, since she’s right there as my roomie. Maybe we go find another Bi-honey that we both like and start our own polypod? Or maybe,” she pursed her lips and kissed my neck, “We just see where it takes us. I’m not ready to settle down and become Suzy Straight Homemaker.

“Ok?”

Going from being lonely to having even a semi-regular fuckbuddy would be nice, I thought. I didn’t need her to move in with me. Even fucking once or twice a week would be wonderful for me, and would suit my slacker lifestyle.

“Play it as we lay,” I finally decided on, “Take it from there.”

——————

We did find that “honey” we could both agree on — Rachel. We also moved out of the group, and found ourselves our own one bedroom apartment (with a nice comfy couch for the living room, in case one or the other of us wanted a night with Whoever alone… and a nice king sized bed for the be-room).

And eventually, both Ali and Rachel had my children. I’m hitting my forty-fifth birthday soon, having settled into our “alternative household nest, ” and looking forward to continuing that “happy ever after,” (albeit, not in the way that our parents wanted for that to happen). But we’re happy. All three of us.

God, I’m so glad that Randy had left that door open that crack!