Whole New World

This is the true story of my first real sexual experience. You see I am an unrepentant bisexual and I think part of me has always known this. I am not the sort of bisexual guy that insists that monogamy is desirable or even possible. I need to be with both men and women. That being said I do prefer to have a strong relationship with at least one person who shares my desires. It doesn't much matter to me if that person is male or female.

At the time all this happened I wasn't really a virgin or anything. I mean I had had some frankly quite awkward and uncomfortable encounters with both boys and girls in my home town. A few of those groping and ill-conceived encounters technically qualified as intercourse, so no I wasn't a virgin, but I always knew there must be more to sex, must be more to these driving needs my body felt.

It all happened a few years ago. I was 19 years old and on my own for the first time in my life. I had moved a couple states away to a city in the southwestern US that seemed pretty cool to me at the time. I moved there with no prospects and very little money. I got a crappy apartment and a crappy job doing catering. I went to my new home alone, no friends, no family, nothing but a sense of freedom that I could finally leave it all behind and just be me.

After a few months I had picked up a few friends from work and life was going OK, but I wasn't really doing the things I wanted to be doing. I was too young to go to clubs and didn't have the kind of money to buy the clothes I wanted or to go out very much. I was basically just existing and not much else. I had a small apartment and a reliable car and that's about it. Even this existence can be exciting if you open yourself up to possibilities you didn't see coming as I was about to find out.

"Shit!"

The exclamation was accompanied by a cacophony of cans and other things bouncing down the concrete stairs just below my second floor apartment. I poked my head out my door to see what was up.

"Hi Tommy" Ruth Mitcham said with an exasperated sigh.

"Hi Ms. Mitcham," I replied cheerfully, "Need some help?"

"Oh you're a godsend" my neighbor replied as I helped her gather up the things that had spilled from her broken grocery bag.

Ruth Mitcham lived in the apartment across from me. She was semi disabled, bad knees I think by the way she walked, and didn't work, she still got around OK though. She was a big woman with motherly features that came across as older than she actually was. She had rather lovely dark wavy hair with streaks of gray and if I had to guess was in her late forties. She was wide hipped and large breasted and very welcoming when I moved in. She often made me sandwiches or cookies.

I honestly didn't really see her as a sexual being, mostly because she was really nice to me, motherly in a way and very church going. That still didn't stop me from looking at her massive cleavage as we picked up the spilled groceries.

"Having a party?" I asked curiously as her haul contained a variety of snacks that seemed like they were for entertaining.

"Haha, yes Tommy," She replied with a big grin, "The Cowboys play tonight and I have a friend coming over to watch the game."

"I didn't know you liked football." I replied as she opened the door to her apartment and we went in to set things down on the counter.

"Oh Honey," she replied with a look of almost worship on her face, "you have no idea. I love my 'Boys' more than anything, they keep me feeling young."

"Wow you sound like a big fan." I replied as she put her groceries away.

"The biggest!" she replied laughing, "Are you going to watch the game?"

"I don't follow football I'm afraid." I replied. Being a skinny blond haired blue eyed kid with long hair, sport had never appealed much to me, mostly because the jocks in school had made fun of me for being a bit on the feminine side. I weighed in about 135 lbs. and had thick lips and long eyelashes that as a kid in school I felt were the worst kind of curse and the football loving kids always gave it to me the worst.

"Well we can't all be perfect now can we?" she replied laughing. She gave me a quick peck on the cheek and thanked me for helping her out.

I went back to my apartment and settled on the couch to read my latest science fiction novel.

I had fallen asleep reading, some party animal I was! I was woken by Ms. Mitcham and a masculine male voice screaming "Go, Go, Go!"

I roused myself from sleep, which was hard because the sun went down. I made myself some ramen noodles and curiously looked out the small window of my little kitchenette, which was directly across from Ms. Mitcham's living room window.

I was bemused by what I saw. Ms. Mitcham was wearing a tight Dallas Cowboys t-shirt that made her breasts seem massive and a pair of tight fitting yoga pants in the Cowboy's colors. The outfit really showed off some curves that I had no idea she had. Interestingly she also had on makeup, something I'd never seen her do before, her face looked younger and quite pretty.

With her was an overweight and rough looking fellow in a flannel shirt and cowboys ball cap. They were both jumping up and down screaming at the top of their lungs for their team. I had to admit that Ms. Mitcham's massive tits bouncing up and down were quite mesmerizing. Something exciting must have been happening in the game. They both had cans of beer in their hands and the coffee table was littered with empties among the trays of snacks Ms. Mitcham had laid out.

I ate, then got on some comfy shorts and settled in to get back into my book. It was a hot night so the windows were all open and I went shirtless. Ms. Mitcham had left her door and windows open too, so I could hear every time something went good or bad with the game. Eventually though I drifted off to sleep again.

I was woken suddenly be the loud sound of a hard slap on skin followed by a scream. As I struggled to make sense of the noise it happened again followed by a hearty male laugh and what sounded like loud whimpering coming from Ms. Mitcham's apartment.

I sprang to my feet and ran to the door without even thinking. I mean I am no a big or strong person, but if Ms. Mitcham was being assaulted I had to do something. I ran across the short landing and burst through her door into her small apartment.

What I saw in that instant baffled my mind and my assumptions about people. Sweet old Ms. Mitcham was bent over her couch, yoga pants bunched around her ankles, huge tits hanging down and swinging with the motion as she was fucked from behind by the big gruff looking guy whose pants were around his ankles and was grunting away as he fucked her.

"Oh my god Tommy!" Ms. Mitcham cried out and flipped over onto her back, arm flying to cover her enormous breasts and exposed pussy.

This move had caused the big guy's cock to slide free of her pussy with a squelching sound. He stood there looking at me dumbfounded, his big seven inch cock dripping with Ms. Mitcham's pussy juices. It's knobby head gleamed in the light of the little lamp in the corner of the room. We all froze, a tableau of shock as if frozen in time. My cock on the other hand was much quicker to realize what was going on and grew an obvious tent in the front of my shorts as I stared at this big man's hard, slippery cock.

"Don't just stand there boy, close the door and come in." the big man said gruffly as if nothing unusual were happening.

I instinctively obeyed, shutting the door behind me and taking a tentative step into the room.

"Roy no," Ms. Mitcham said with hesitation, "he's just a boy."

"Quiet now Ruth," Roy said putting a finger gently but firmly under my chin and tilting my head to look him in the eye, "boy or no, I think little Tommy here sees something he likes, isn't that right Tommy?"

I licked my lips, swallowed nervously and nodded my head. He was right, I was taken in by the scene, I couldn't stop my gaze from jumping back and forth between Ms. Mitcham's exposed flesh and the throbbing hard, pussy slick cock Roy had proudly on display.

"I thought so." Roy said stepping closer, so close in fact that the head of his massive cock touched the soft exposed skin of my flat tummy.

"Go on Boy" Roy said as he loomed over me, "give 'er a tug."

I tentatively reached out and took his big cock in my hand and stroked it up and down. My hand slid easily along its throbbing length as it was covered in Ms. Mitcham's juices. Roy tilted his head back and sighed deeply. It felt so heavy and warm in my hand that it made my mouth water.

Roy then reached up with big thick fingers and pinched and rolled my nipple. His fingers were hard and calloused; he definitely worked with his hands for a living. Pinching a bit harder on my aching nipple he pulled me in and kissed me deeply while I stroked his throbbing cock. I completely lost in this man's embrace, over on the couch I heard some soft mewing sounds and a wet rhythmic sound that indicated Ms. Mitcham was enjoying the show while touching herself.

"Mmm nice," he said breaking the kiss, "you know what happens next now don't ya Boy?"

Roy's hand moved to my shoulder and slowly but firmly started pushing me downward. Nodding that I understood I slowly sunk to my knees under the steady pressure, my hand still stroking his big fat cock, until I was stroking him at eye level. He was so, so big.

"Roy," Ms. Mitcham implored her voice tinged with concern, "what are you doing?"

"Don't you worry none Ruth" Roy replied grunting as I took the head of his cock between my lips, "just enjoy the show, I'll make sure you get taken care of."

I let his big gorgeous cock invade my mouth as he slowly thrust it in and out between my soft lips. I could taste Ms. Mitcham's pussy on his cock as he thrust it in and out of my mouth.

"Boy let me see them baby blues." Roy said as he lifted my chin slightly. I looked over his big belly up at him as his cock drove deeper into my mouth and started invading my throat.

"That's it Boy take it all" Roy grunted, "you like this don'tcha Boy?"

I nodded in response with his cock in my mouth. He took a handful of my long blonde hair and started thrusting deeper into my throat until his cock was all the way in, my nose buried in his pubes, his balls hitting my chin. This caused me to cough so he let me up to breathe a second.

"Oh god Tommy are you OK?" Ms. Mitcham asked with concern in her voice.

I looked over at her trying to catch my breath. Her concern apparently didn't stop her from pinching her nipple and rubbing her sloppy wet cunt. I couldn't believe this was all happening, she looked so amazing.

Turning to her I said with tears in my eyes "Yes Ma'am, I'm fine." Saying this was made a bit awkward because Roy was slapping his cock against the side of my cheek. Then he shoved it back deep into my throat and started fucking my mouth in earnest.

He had a good rhythm going and I was taking him all the way down my throat as he grunted and fucked my mouth. His grunts were building in intensity and I thought I was going to make him cum. I wanted him to cum in my mouth so badly I couldn't believe it, but he had other plans.

He pulled his cock from my mouth with a loud grunt and slapped my face with it a few more times and started laughing, but not in a mean way.

"Wholio fuck Boy," Roy exclaimed heartily, "You almost made me pop all over that pretty face of yours."

I was on my knees and he still had a fist full of my long hair. I couldn't help but look over at Ms. Mitcham who was rubbing herself into a frenzy on the couch next to me.

"Haha, Ruthie girl," Roy bellowed, "looks like this Boy wants some of that fine cunt of yours."

"Jesus Roy," Ms. Mitcham complained, "the nasty things you say."

Again her protests we given the lie as she spread her legs wider to give me view of the first pussy I had really seen up close and personal. She was a big lady, but she was shaved smooth, with big puffy lips. With his fist full of my hair he dragged me over between her thick thighs and shoved my face into her snatch.

At first I was just licking about as Ms. Mitcham gyrated her hips trying to get my tongue to go where she wanted. I had no idea how to go down on a woman, whereas sucking cock seemed pretty obvious to me, home field advantage I guess.

So I licked her juicy cunt all over which she seemed to like at first but quickly became frustrated with. Then I stuck my tongue inside her and tried to kind of fuck her with it. My tongue was way too short to get anything like that done in any serious way I could tell as soon as I tried. I wandered lost in her fat wet pussy for a bit before Roy helped me out.

"Boy, suck on that little nubbin there." Roy said chuckling as he moved my head by my hair.

"That's it Boy" he exclaimed as Ms. Mitcham moaned deeply "suck that clit good."

I had apparently hit on the right thing to do as I sucked the hard little button of her clit between my soft lips and sucked gently while rubbing my tongue across the tip of it. Ms. Mitcham started moaning and grinding her hips into my face. I was fascinated and my throbbing cock was loving how her body moved. Roy eventually let go of my hair, but Ms. Mitcham grabbed a double handful herself as she ground away against my lips and tongue.

"Oh lordy, oh God Tommy" She moaned in a deep gravelly voice, "such a good Boy, so sweet, making me feel so good."

I was pretty proud of myself pleasing her so well. My cock was aching for some attention, so I reached back and gave it a squeeze as I wondered if I would get to fuck Ms. Mitcham. Roy then decided to make his presence obvious again.

"Jeeeezuz H Christ Boy" he exclaimed, "from back here you two look like a couple a hot lesbos goin at it."

He smacked my ass hard, making me cry out, the sound muffled into Ms. Mitcham's pussy and drowned out by her moans. Then he grabbed my shorts and pulled them down over my hips, leaving my underwear clad ass exposed.

"Ohhh fucking hell Boy," he chortled slapping my ass even harder "what the fuck are you wearing? Those panties you got on there Boy?"

I wanted to cry out that no, they were most certainly were not panties; they were men's bikini briefs. I liked to wear them because I liked the way my body looked in them. None of that was possible to say because Ms. Mitcham was building in intensity and my face was full of her plump wet pussy and she had fists full of my hair as she ground away moaning.

"Move aside boy," Roy said, yanking my head out from between Ms. Mitcham's legs, "I'm gonna get my dick wet!"

Roy moved up and knelt between Ms. Mitcham's thighs, his massive cock sticking out lewdly from below his hairy belly. He grabbed his fuck stick and slapped her sopping wet cunt a couple of times, making her cry out. Then he plunged in balls deep and started pounding away in a fashion that would have been comical if it wasn't so savage on hot.

Ms. Mitcham for her part cried out loudly as he penetrated her. Her body became a moving mass as Roy's bounding set up a standing wave through her thick thighs that traveled up through her belly and rocking her massive tits back and forth. She was like art in motion and so beautiful as her face and upper chest began to flush red from his fucking. I pulled free my five inch rock hard prick and started pumping it as I watched.

"You enjoyin this boy?" Roy asked through his animalistic grunts as saw what I was doing.

I just nodded in response and kept rubbing myself. He laughed again, his voice deep and rich, which sent shivers down my spine.

They both seemed about ready to cum as Roy pounded away at Ms. Mitcham's massive flesh. Just when I thought he was gonna fill her cunt with jizz he pulled out with a loud "Arrrgh!" and grabbed his dick and squeezed so hard I thought he might break it. It was once again shiny and slick with her juices.

Ms. Mitcham whimpered and pleaded with him to put it back in.

"Nah Honey just be patient," Roy chided grabbing me by the hair once again, "the boy here's gonna finish you off with that pretty mouth."

With that I was back where I was a few minutes ago, on my knees with my face shoved into her sloppy wet pussy. I immediately went to work sucking and licking her clit. I wrapped my arms around her massive hips. She grabbed my head and pushed me in harder as she resumed fucking my face hard.

"Ohhh yeah, that's fucking hot." Roy exclaimed as he moved behind me and slapped my ass hard again.

Then he started yanking my underwear down over my hips. I started to get really scared once I realized what he had in mind. I'd always wanted to get fucked, but his cock was so big and I was afraid he would hurt me.

"Oh fuck yeah, that's a sweet little ass." He said spreading my cheeks. I braced myself for what I thought was coming. I was surprised by a warm wet sensation and it took me a moment to realize he was tonguing my ass. I moaned deeply as he worked me over with his thick wet tongue. Wow that felt so fucking good. I redoubled my efforts of eating Ms. Mitcham's pussy. Then he pushed his thumb inside me and I was surprised by how good that felt too, I pushed back against his hand as he worked it in and out of my ass.

"Hahah, yeah boy get it," Roy said laughing at my reaction, "knew you'd take to ass fucking like a fish to water, fuck your body is built for this."

Then I felt something long, hot and slippery, slap against my ass.

"Get ready for the real thing boy." Roy warned. I felt the slick knob of his huge cock press against my tight wet opening. I cried out into Ms. Mitcham's pussy as he slowly started to push into me.

"Go easy Roy!" Ms. Mitcham said with concern as he continued to stretch my ass wider than I ever thought possible, "he's just a boy".

I was nearly constantly whining and whimpering into her cunt now as he continued to press forward. It felt like my body was going to split in half.

"Grrraaaah," Roy grunted breathing heavy, "Don't worry none Ruth, I aint gonna hurt him, fuck you're fuckin tight boy."

Technically it was painful, but his cock also awoke in me an animal need that didn't care at all about the pain. My eyes filled with tears as I whimpered and moaned, but my ass was pushing back against the pressure, wanting more of him inside me.

Ms. Mitcham lifted my face from her pussy, in the intensity of it all I had gotten distracted from pleasing her for the time being anyway.

"Are you OK Tommy?" She asked, her expression full of motherly concern as she held my face in her soft caring hands and wiped the tears from my cheeks with her thumbs.

"Yes ma'am." I responded through my whimpers nodding.

"Good boy," she replied smiling with encouragement, "Tommy, such a good boy."

She patted my cheek with a final look of encouragement. Behind me I could feel Roy's hairy belly on my lower back and his thick thighs and hair hips pressed against my ass. He was finally all the way in and starting to pull back for another thrust. Ms. Mitcham's moment of empathy seemed to end as she watched him taking me. She pushed my face back to her wanton cunt, which I eagerly began sucking.

Roy started to slowly but powerfully piston his cock in and out of my ass. Each time it made me suck and even bite a little on Ms. Mitcham's clit. I was worried about this but that seemed unfounded as her moans became deeper and very wild, her hips rocking hard.

"Yes Tommy, yes!" she cried out, her body began shivering and convulsing as she rammed my face harder into her pussy making it hard to breathe, "you're making meeee cuuummmm!"

"That's it Ruthie, cum on his sweet face." Roy called out as he rammed his big dick into me harder, his hips slamming against my ass.

After that her voice was unintelligible as she held my face and ground her pussy against my lips and tongue. Her big body gyrated all over as she cried out over and over and it seemed to go on forever. Her juices flowed from her cover my face.