Two of Both Worlds
Thomas E. Scott
It’s weird how two unsuspecting people could meet and suddenly end up together in unexpected ways. It all started in high school with my long time and now ex boyfriend, Bill, and my long time and now ex girlfriend, Charlene, we called Charley for short. Charley and I have been best friends ever since middle school. We would talk about everything. The clothes we wear, the girls we thought was unpopular, the guys we screwed. We were like sisters. Well, sort of. I remember when I was having a sleep over at her house and we were watching porn. We used to talk about the guy’s dick and how it couldn’t be that big and the woman’s pussy couldn’t be that wide to take it all in. But it happened. And the things they say while they were fucking was hilarious. We would always feel sorry for the women because we knew they were faking it but we commended them on hiding it well. Then we came to a girl on girl scene which sparked our interests. We wondered if we could go as far as the girls in the video. Hell, even farther. Charley asked me if we could try it and I said sure. What can I say I was curious. Suddenly we kissed and something inside me sparked. We were so into it that we didn’t notice that we were kissing for a long time. Suddenly my hand was up her skirt and her hand was up mine. We were feeling each other’s tits, nipples, coochies the whole nine yards. The next day I wondered if that night brought me to the conclusion that I was gay. Either I was just curious or just bi? Or just that I know I can do it? After talking to Charley I came to find out that she too felt the same way. I guess it brought us closer together in some weird way?
In high school I couldn’t get my mind off of this jock named, Bill Holiday. The football quarterback and now praised as one of the popular crowd for scoring a touchdown. At first I didn’t think he noticed me until Charley hooked us up. After a couple of dates he took me too his place and we got down to it. After that night we were inseparable. But after high school graduation Bill told me about his fantasy of sharing me with another woman. Which is every guy’s fantasy of course. But I suddenly felt the curiosity popping its horny head up again. So I talked to Charley and she agreed.
It started out with Bill taking us out to eat. After nice meal and discussion Bill drove us too his home so all three of us can get better acquainted. I had to admit it was fun. Bill must’ve been watching more porn than we had because he knew how to do this better than me and Charley put together. First I got on top cowgirl style while Charley sat on his face. Both of us were riding him crazily until we both came. The next thing I knew I was on my back letting Charley lick away at my pussy. I looked up and saw Bill giving it to her from behind. I couldn’t believe we were doing this but I didn’t want it to stop either. All three of us laid in bed sweating and exhausted. That night we all got what we wanted. Or at least I thought we did.
Everything came crashing down when Bill and I began moving in with each other. We’ve been together so long that Bill finally asked me to marry him. So we were on our way to becoming Mr. and Mrs. Holiday. Or so I thought?
It all started when I was coming home from work exhausted but I heard something in the house. It sounded like a movement. But I wasn’t sure until I stopped and listened closely. I realized that it wasn’t movement at all. There were voices, but the slow moaning kind. I slowly creeped through the house hearing the moan getting stronger and louder until I came to my bedroom door. The door was opened just a crack for me to open it all the way without making a sound. And there I stood shocked at what I saw. Bill was in bed with another woman. Not just any woman. My back stabbing, so called best friend, Charley! That bitch was on top of him riding him crazily not knowing I was standing there watching the whole thing. It wasn’t until Bill caught me by the corner of his eye that the party suddenly stopped.
“Sarah oh shit!” He cried out as he pushed Charley off of him and covered himself with the covers. “When did you get home?” I looked at Bill and then took a quick look at Charley. Suddenly my face felt so hot I thought my head was going to explode. I clinched my fist so hard I didn’t care if my nails cut the palms of my hands. “Sarah baby,” Bill continued, “it’s not what you think.”
That only set me off even more. “Not what I think?” I shouted. “Not what I think?” I stumped over there and started hitting him as hard as I could hoping he would feel the pain. Bill guarded himself trying to block my hammer punches but it didn’t do any good. I still got a couple of licks on him.
“But baby you didn’t mind us doing it before?” Bill excused still guarding my punches.
“I was there the last time,” I yelled hammering away at his face, “besides we are getting married you short dick bastard!” I could see Charley trying to sneak out by the corner of my eye and I changed my course of action. “Where you going bitch?!” I yelled running after her. I grabbed her hair and pulled not caring if she was screaming in agony or not. I tried my best to rip the root right out of her head. Bill came up behind me pulling me off the back stabbing bitch so she could make her getaway out the door. After Charley got away from my grasp Bill finally let me go but that didn’t mean I couldn’t get him one more time. I turned and smacked him so hard across the face, the impact echoed through the house. “Cheating bastard!” I said before I went to my room and slammed the door.
After that moment me and Bill separated and as for Charley. I never spoke to her again. It was a harsh breakup between the three of us. I lost my best friend and my boyfriend in one fell swoop. I know half of it was my fault for getting involved in that threesome. Bill and I argued constantly until he stopped coming around the house period. Later on he told me that he was not in love with me anymore but with Charley and he was moving in with her. So the slimy bastard stuck me with not only the house but the bills too. It broke my heart that they both went behind my back the way they did but deep inside I was happy they left me. At least I knew who my true friends were.
I decided to go out to this gay club to clear my head. I didn’t feel like getting hit on by guys or women for that matter. I was too pissed off to even think about a guy right now. I headed to the bar where this tall woman was stirring up some drinks in a canister.
“What will it be?” She asked
“Apple martini please?” I answered still focused on her.
While she was fixing up my drink I couldn’t help but be mesmerized by her beauty. She had long dark hair tied up in a ponytail. Crystal blue eyes that looked like they were shining from the florescent light in the club. Strawberry red perky lips that I wondered what it would feel like to kiss. Her big rack that looked like they were going to pop right out of her black top. Her slender frame made me think she must work out regularly and took good care of herself. Suddenly I thought I felt this warm feeling I usually feel when I’m attracted to someone.
“Bad breakup?” The bartender asked.
I looked at her like she just read my mind or something. “Yeah, how can you tell?”
The bartender leaned over the counter facing me. “A lot of women like you come by here from time to time having that type of look.”
“And what look do I have?”
“The look that says you’re not ready to be fucked with right now.” The bar tendered smiled looking seductively into my eyes. Though I might’ve been wrong? “The look that every woman has when they don’t feel like dealing with a man’s bullshit.”
“You’re right on the money.” I said taking a sip of my apple martini.
“So what’s your name?” The bartender asked while she was wiping down the table in front of me.
I paused for a second. I didn’t think she would be that interested in me. But I figured she was just being friendly. “Sarah.”
The bartender reached out her hand for mine. “Dawn.”
“Dawn?” I repeated thinking how unique the name sounded. “I like that name.”
“Well thank you.” She said cleaning out a glass. “So Sarah are you doing anything else tonight than just sitting her feeling down about yourself?”
I took a deep sigh. “Well there isn’t much here to do unless one of these guys are interested in showing me a good time. Either that or they’re bi?”
Dawn chuckled. “There are some in here who are that type. But we all know what they’re really in here for, so good luck with that.”
“Thanks.” I said sarcastically. Though I didn’t think she caught it.
Dawn leaned forward over the counter again closing in on my face. “How long are you thinking of staying?”
I thought about it for a minute. To tell you the truth I didn’t know. “I don’t know why?”
“I get off at one. You think you’ll be interested in coming over my place and chill?”
Again, a minute pause. “I don’t know.”
“We can talk more about your boyfriend.”
“You mean my ex?” I corrected.
“Yeah, him. So are you game?”
I looked at my drink and then back at her. I didn’t know what was happening or how to respond. I just met this hot ass bartender and already she was asking me out. At a gay club of all places. “Sure.”
“Here,” She took out a bottle and poured more martini in my glass, “on me.”
“Just try not to get too sloshed while you’re here alright?”
I thankfully nodded and took a sip of my martini wondering how this night was going to end.
I had two apple martinis and already I was absorbing the night like it was a part of me. I started dancing for no reason. It didn’t matter if it was with a man or a woman. Hell, I was even dancing by myself. Suddenly this woman appeared out of the crowd and began dancing with me. I didn’t mind at first but as I took a closer look at her I found out it was Dawn. It was one already? We danced for a few minutes and the next thing I knew we were out the door the next. I still felt a little tipsy from the martinis but not too drunk to make me feel too hazy I couldn’t walk.
I was in Dawn’s car driving down the road. Though I didn’t pay much attention since the martinis had me relaxed. I felt the car slow down to a stop and I woke up. “Where are we?”
“Home dear.” Dawn said with a strange smirk on her lips.
I got out of the car and looked around. I was surrounded by brick made apartment buildings. Nicely done I might add. I could tell very wealthy people must live in a place like this? I followed Dawn up the stone white steps until we stopped at her door. Once she opened it, she stepped aside and let me in first. When I first stepped into the place I stopped at the welcoming aroma of some lavender scent that blew my mind. As Dawn was turning on the lights I looked around to see that the place was no different from mine.
“Outside makes it bigger than it looks.” Dawn mentioned. I could tell she felt a little discouraged about bringing a stranger she was attracted to into her home.
“No it’s alright,” I said trying to make her feel comfortable, “it’s better than my place.”
“Sit down make yourself comfortable.” Dawn said as she disappeared into the kitchen.
I looked around and I saw a red silky couch I sat on. It felt so comfortable that I thought about falling asleep right there, but I snapped out of it remembering Dawn in the kitchen. She came back with two glasses of red wine, just what I needed. More drinks to get me drop dead drunk.
“One for you,” Dawn said handing me the clear glass of wine, “and one for me.”
I took a sip and felt the cold cherry flavor rush its way down my throat. “Delicious.”
“I thought you may like it.” Dawn said sitting right beside me. We both placed our glasses on the clear glass table. “So I see you had a good time?” Dawn asked taking off the tie that binded her hair. She looked even more glamorous with her hair down.
“Yeah, sorry about that. I guess I got caught up in the mood.”
“No need to apologize. That’s what you were there for right?”
I couldn’t help but stare into those clear crystal blue eyes of hers. It was like I was being hypnotized but instead of fighting it I welcomed it. I was hoping she would make the next move because I was too shy to do it. Which was weird because I’ve done this plenty of times after Charley and never felt this way before.
“So what now?” I asked feeling embarrassed because I didn’t really know what else to say at that moment.
But all that changed when Dawn closed in and her soft red lips pressed up to mine. That’s when I felt the spark ignite inside me. The spark I used to feel with Charley but much stronger. She kissed me hard, harder than Charley. Then I felt her hand tightening on my breast and squeezed with strength I never felt before not even from Bill. Her tongue broke through my lips and played with mine fluently. Her tongue was longer than both my lovers. It was able to nearly reach down my throat licking away at the inside of my mouth. I felt her strong hand slowly make its way between my thighs and rubbed up against my panties. Her fingers slipped through rubbing my pubics and finding my clit. I moaned as she rubbed in circles around my wet stub and then went deep inside my gash rubbing my inner walls slowly. It was like a spark of electricity igniting throughout my body waking me up to her will. I wanted to return the favor. Though I wasn’t sure that I would do as fine of a job like Dawn. I first laid my hand on her tit squeezing as hard as I could but didn’t think I was doing a fair job like she did. But I heard her moan while she was still kissing me so I must’ve been doing something right? My hand slowly made its way under her dress and between her soft but strong thighs. As I touched her panties I noticed something bulging inside. I broke away from her kiss to face hers.
“What’s wrong Sarah?” Dawn asked with a look of concern.
“I don’t know,” I said trying to figure out a good way to break it to her, “I felt something different under there.”
Dawn looked down and then at me like she didn‘t have any other way to say it. “I have something to tell you.”
“What?” I said looking at her suspiciously.
“I’m not who you think I am.”
“What do you mean?” I sort of figured where this was going. A beautiful woman working at a gay bar must be too good to be true?
“You ever heard of the word, “Transgendered?”
My eyes opened wide. I didn’t know if I was cut off guard or just surprised. “Really?”
Dawn looked down and licked her lips but not in a seductive way. It was more like she wondered what to do now since the truth was out. I was a little taken aback myself but then something deep inside me sparked my curiosity. “Can I see it?”
Dawn looked at me and smiled at the curiosity in my face. “I can do more than that.”
Dawn held both my hands and stood up in front of me. Then she pulled me up close to her kissing me again. I can tell by the strength of her kiss, I was feeling the manly side of her. At least that’s how it felt. I could feel the presence of her clothes slipping off and dropping to the floor. I broke away from her kiss to see the dark bra and panties she had on. Then I spotted a green dragon tattoo on the side of her hip. I could tell that Dawn was a force to reckon with. She unsnapped her bra and threw it to the side showing me her perky round breasts. I stared at them hard thinking how bigger they were than Charley’s. The next thing I knew I was burying my face in them like I was Bill gripping both boobs with my hands, sucking on the nipples between my lips and hardening them with the softness of my tongue. While I was busy up top, Dawn took off her panties and I felt the hardness of her member rubbing up against me. I broke away from her breasts and looked down. My eyes shot up and my mouth hung open as I stared down at her girth hanging between her legs. It was bigger than Bill’s! I took a step back to take a better look at her magnificence. Dawn was all woman and only had one part that was a man. A very big part. I touched it with my hand making Dawn moan.
“Does that feel good?” I don’t know what made me say that? Dawn nodded giving me the okay to continue stroking the thing. With each stroke I could feel it hardening. I went back to her breast sucking on them and pulling on her cock in unison showing my affections strongly. I sat back down on the couch with her cock in my hand gulping and wondering if I can really pull this off? I opened my mouth as wide as I could letting her dick slip inside. Slowly I began sucking and licking around the head first, then I pulled the whole body inside.
“You like that don’t you Sarah?” I heard Dawn spoke in a creepy tone that brought flashbacks when I watched that porn back in high school. “You like this beautiful cock don’t you?” I felt my hair held in her hand and my shoulder gripped by the other as she pulled my head into her privates forcing me to take all of her cock in one gulp. I was literately choking. Dawn pulled my head backwards releasing me from her dick so I could breathe. Then she pulled me back in sucking on it hungrily. I didn’t know if she was in enjoying this because of the feel of my mouth around her cock or she enjoyed punishing me. But in a good way. Finally she pulled my mouth away from it and forced my head up to look at her. “Are you alright dear?” I nodded trying to get the feel of my throat again. She kneeled down to my level facing me. “Sorry about that, sometimes I get carried away.”
I gave her a weak smile letting her know it was okay. She helped me with my clothes and stared at my body.
“You have a wonderful body.” Dawn said feeling her strong hands around it as if mesmerized.
“Oh please stop,” I chuckled, “it’s nothing much really. Not like yours.”
Dawn lips curved into a smirk looking at me as if I should know better. “I’ll show you then.” And she leaned closer to french me like before.
But this time she kissed and licked her way down to my breasts sucking on them with her lips and trapping them between her teeth so her tongue could have its way with them. Her hand made it between my thighs massaging my wet pussy with her fingers. Her orally and physically taking control of my body was more intense than any man or woman put together. I started moaning and moving about unable to control the vivaciousness that took hold of my body. Then Dawn traced her tongue down my belly leading it towards the middle of my thighs. I opened them with a warm welcome of her tongue. Her lips sucking on my clit hard and her tongue entering between my pussy lips had me pressed against the couch.
“I-I’m cumming.” I warned but Dawn continued letting the waves of my juices free from my body and splash on her tongue still licking it up.
Dawn rose up looking at me with her face wet from my pussy juices. She let her tongue lick around her lips to wipe away my mess before she jumped on me to kiss me again.
“That was good.” Dawn said still kissing me.
“I’m glad you enjoyed it.” I said kissing her back.
Dawn looked at me pushing my legs apart. I allowed her to spread my thighs knowing, waiting, ready to accept what was coming next. Taking a deep breath I felt the head of her cock rubbing up against my clit and popping inside. Then I moaned feeling the rest of the body make its way in. At first I thought she was in already. Then I felt her cock move deeper and I gasped. I totally forgot how big it was after giving her head.
“Are you alright Sarah?” Dawn asked. Though I didn’t think she was really concerned.
I didn’t say anything. I just nodded and held on knowing this was going to be one rollercoaster of a fuck. Dawn pulled out and in slowly. She closed in on me wanting me to feel her breasts up against mine in virile embrace. She kissed me again pulling out halfway and pushing herself back in again. Dawn began to speed up moderately, then faster as I held onto her tight. The body of her cock rubbing in and out of my gash started to burn sending waves of heat through my body. Her mouth nipped at my ear making the side of my face tickle.
“Hold on tight.” Dawn said as she gripped my as cheeks real hard.
I didn’t know what to expect. Hell the way she was plowing me I couldn’t even think straight. But I listened wrapping my arms around her neck and my legs around her waist as tight as I could. Suddenly I felt my body being lifted off the couch and held in the air. At first I was surprised how strong she was but when she dropped me on her dick and picked me back up only to let me land on it again. The levitation was awesome. Bill never would’ve done something like this. I never thought he could. Dawn laid me down on the floor still plowing that monster inside me. Then she flipped me over grabbing my ass and began pumping that big bad boy inside me over and over. I felt and heard my as cheeks smacking up against her privates as she rammed her nine inch cock inside me. As she thrust herself into me I climaxed again. But I didn’t tell Dawn to stop. I let her go at me over and over until I felt her pull out.
“Aww shit!” Dawn cried as she her stream of cum erupted all over my ass.
I don’t know about Dawn but I was breathing deeply trying to gain back the air I lost from this extreme fucking.
“Are you okay Sarah?” Dawn asked.
“I think so?” I said still shaking from what just happened.
“Don’t move an inch,” Dawn said, “I’ll be right back.” She made me yelp by slapping my ass before heading to the bathroom to get a towel so she could clean up her own jizz.
The fucking didn’t end there. We continued our sexcapade in the bedroom where I was on top. I held onto her breasts squeezing them tightly as if I was going to fall off while I was riding her. Dawn helped by pushing herself upward while I was pushing down. Again I came. Then we switched positions with Dawn on top of me throwing my legs over her shoulders as she repeatedly pushed that dick inside my wet snatch.
“Here it comes.” Dawn warned as she pulled out and more of her warm, milky, wet cum erupted on my body.
We both laid in bed side by side spent and exhausted. I’ve never experienced anything so extreme in my entire life and that’s saying something. I looked at Dawn and she looked back at me, both of us bursting into laughter. After that night she drove me back to my place. I let her in letting her check out my residence which was nothing compared to hers but she said she liked it all the same.
“You want anything to drink?” I asked heading to the kitchen.
“No thank you,” Dawn said sitting on my boring, brown, raggedy couch, “I think I’ve had enough.”
I came back with a bottle of Aguafina water and sat next to her. After the wild fun we had last night she still looked radiant in the day.
“So I guess you had fun last night?” Dawn spoke.
“Fun is an understatement.” I said putting the cap back on the bottle.
“So what are you going to do now?”
“Good question,” I said feeling down now that I had no clue what to do today, “now that the fun is over I guess I’ll get some of that sleep I lost last night?”
Dawn laughed a little bit. But she straightened up her face and leaned closer to me. “I’m not doing anything today; you want some company while I’m here?”
I looked at her with brightened smile on my face. I didn’t know why I was happy to hear her say that. After the force she put me through last night I guess she would be off about her business. “Yeah,” I said getting closer, “I would very much like that.”
That was it. We went back to where we started amazingly kissing and fucking again like two crazed rabbits.
Bill finally proposed to my treacherous so called bestfriend, Charley, and they soon got married. I didn’t see nothing much of it. After all I figured they deserve each other more than anything. As for me I let Dawn move in as my roommate and fuck buddy at first. But then we became closer than I realized. My family and friends still think she is this hot roommate that I cross paths with having no idea what she really is. The secret was naughty but fun in my opinion. We became more than just lovers. We became bestfriends for life.