I had known Jenny for about three years during high school when she was still living life as a boy. That's' right; Jenny is a girl, but she was not always a girl. She was a transsexual and had decided to become so just after we graduated high school together. Things had been rough for her but I had stood by her side and so had a few of our other close friends.
We lived in an apartment together; two best friends, two roommates and it worked quite well really. The only complaint I had was having to keep my real feelings hidden,
Jenny and me, we had always had a lot in common. We loved video games, Japanese Anime, Taco Bell, porn, beer and more video games. I guess part of her male brain could still' remain even though she had grown up feeling like' she should have been a woman. Whatever the case we were best friends and out of fear that it may ruin that, I didn't' want to tell her I wanted more.
The truth was though that I had always liked Jenny as more than just a' friend. She was beautiful; short neck length blonde hair, green eyes and an amazing body. There was also her personality; she was funny, and very easy to get along with and no matter what she could always cheer me up.
She had no clue how I really felt about her though and sometimes I wondered if she would even be okay with it if she did know. Or' would she try and' convince me I did not want to be with her; that everyone would call me gay. These thoughts had crossed my mind' own their own, but truth be told it did not bother me. I didn't' care if it meant I was gay or not.
I didn't' care what anybody thought about me for being in love with her, and I liked that she trusted me so much; so much so that I had been the one she told in high school first that she wanted to be a woman.
I remember it clearly, we were sitting in lunch alone at our usual table together just talking about random bullshit like we always did. When Mike told me' he had something important to say I hadn't' really thought it would turn out to be some huge thing like it was, but it was much bigger than just some big thing. I was surprised at first but how could I not be? I had known Mike since our freshmen' year, he had been my best friend and though I often wondered about him...I had never suspected he was a cross-dresser.
Yet here he was spilling his guts to me telling me that he had been dressing in his sister's clothes since sophomore year and that at first it was just for fun but over time he started to feel weird about it, he started to feel like it all just came so natural.
Like dressing as a woman felt right.
Mike said that as far back as six years old he could remember not feeling comfortable in his own skin. He buried those emotions around 8th grade but it did not last long obviously since he started cross-dressing two years later. Now he wanted my support; he wanted to come out to his family and start dressing full-time as a woman after we left high school.
He even planned on going as far as as changing his name and I wanted to support him through it all but really I just didn't' know how to feel about any of it...I was shocked.
Then on graduation day it happened; some girl named Tracey decided she wanted to completely' ruin the day for Mike. They use to date and Mike broke up' with her and apparently he had confided in her that he liked to dress as a woman...big mistake on his part.
He had even allowed her to see him dressed up once and that' was how she got a hold of the pictures that she somehow managed to display on the overhead projector during the ceremony.
Of course everyone recognized him and everyone laughed and teased him' humiliating him and when it was over with I watched as he broke into an argument with his family members before running off to the bathroom.
When I met up with him later' he did not seem happy to see me; or maybe he was just worried about what I was going to have to say to him now.
"Go on," he spat. "Just say it; you hate me right?
Just like everyone else, you think I'm a fucking faggot, some sort of fucking freak...right?"
I thought about it for a moment and realized that was far from the truth. I did not hate him at all; he was still my best friend as he always had and probably always would be.
"Dude...its' okay," I said. He seemed surprised and I had to repeat myself a few times before he got it through his head that my opinion was not the same as everybody else's.
After that day, Mike and I agreed to remain friend's' and when his parents tossed him out of the house he moved in with a close relative and started transitioning. Life had been much better for Jenny since she started living as the person she had always' been meant to become.
I was coming home from class on a Tuesday in March of 2013 and was feeling really excited for tonight; the Flyers were playing the New Jersey Devils and I was actually more than excited. I was' pumped; but I got that way with every game, especially when playing the Devils since Philly and Jersey were pretty much rivals when it came to hockey.
There were many things that Jenny and I both loved' but most of all we both loved one thing more than anything...Hockey, But' the one thing we did not have in common was that I was true to my hometown team, a hardcore Flyers fan but she had always preferred the New Jersey devils.
Growing up we always fought over it when the two teams would clash and it always led to us making some sort of stupid bet. If the Flyers lost' I'd' have to give her one of my favorite games or if I had money I'd have to cough it over to her and it was usually the same thing if the Devils lost only in reverse. So' I was sure that tonight's game would definitely be no different.
I walked into the apartment to find her in the kitchen prepping the snacks we would devour during the game.
"Hey...half an hour till it starts," I said coming out behind her.
"Yeah I know," she replied. "I just ordered the pizza and we're stocked up on beer. Should be good to go soon as the food gets here,"
I pulled out one of the chairs at the table and sat down running a hand through my hair and smiling as I lit up a cigarette.
"So...what's the deal huh?"
"C'mon you know what I mean. Flyers win you do what, Devils win I do what?"
She laughed shaking her head and lighting up a cigarette of her own.
"I don't know," she replied taking a drag. "I'm not really thinking about that. I just hope the Devils win that's all."
"Right...the devils win my ass,"
She looked insulted as she pulled out another chair and nudged my arm before sitting down across from me. We talked for a while and I continued to bust her balls about how the Flyers were going to kick the Devils asses and she leaned into me as well reminding me how 9 times out of 10 when the Flyers went up against the Devils, Jersey almost always won.
"Alright, well it's starting in five minutes," I said standing up and heading to the fridge to grab a beer.
The food still had not arrived yet and I was starving but excited for the' game to get started.
The doorbell rang and she went to answer it thinking it was the food but it turned out to be our friend Jimmy who was coming over to watch the game with us. Eventually, Jenny and I settled on a bet; if the Devils won' I had to do dishes for a week and if the Flyers won Jenny would be cleaning the entire apartment from top to bottom tomorrow. Jimmy wanted in on the bet though too apparently; he was on my side and happened to be a huge Flyers fan so this meant one thing.
The only one he could place a bet with was Jenny,
"Flyers call it five to three, $100," he said outright and I could hardly help but bust' out laughing at how straight' forward he was being.
"$100, are you shitting me? That's all I have," she said angrily.
"Hey, if you're so sure the devils will win why worry about it?"
I shot her a glance and she looked me' in the eye and I laughed out' loud at her.
"Yeah Jenny, what're you afraid of? Losing?"
She shot me a dirty look and Jimmy and I both laughed as she sighed and cracked open her beer. "
Fine," she said. "If the Devils lose I give you $100 and the same goes in reverse if the Flyers choke."
"Deal," Jimmy said as they shook on it and a few minutes later the game had started.
At first it seemed like neither side was winning, halfway through the first period and not a single goal had been' scored. Of course' out of nowhere the Devils landed on ten minutes left on the clock and only a few minutes later they landed another and one more in just the last few seconds of the period.
Jenny of course' was celebrating already so positive she had this that she was rubbing it in our faces.
"Relax," I said taking a swig of my beer. "We can still turn this around Jenny; get ready to lose that $100,"
"I'd like to see those fucking assholes turn it around now!"
"I guarantee you they will," I said taking in the beauty of her angry face.
Sure, she was a transsexual, also had been my best friend for quite a long time. But' I always loved it when she got mad; it made her look like such a bad girl when she was pissed off.
"In fact," I said. "I'm so sure that we can turn it around that if we don't and the Flyers lose not only will I do the dishes for a week but I'll clean the bathroom tomorrow bare ass naked and you can watch me."
Her eyes seemed to light up and I laughed as I stood up to retrieve another beer from the fridge and a slice of pizza as well.
"I think I like that idea," I heard her mutter as I walked past her and I looked back at her to see a very seductive smile on her face.
I always knew she would check me out from time to time I had caught her in the process on numerous occasions. I was really only fucking with her when I offered to clean the bathroom naked but somehow I wondered if she'd taken' me seriously.
The game started up again and only three minutes into the second period, the Flyers scored a goal, followed by another and then another tying them up three to three. It was starting to look like Jimmy's prediction just might come true, even more so when we scored another goal five minutes left on the clock, putting us one point ahead of the devils. Second period ended and Jenny was starting to get nervous, she was sweating and not looking to happy at all.
She kept shooting me dirty looks and I laughed silently. I knew she hated to lose, she always had; whenever I beat her in video games she would always get mad at me but it was never hard for me to cheer her up.
Usually, it ended with her pretending to be mad at me but then cracking some stupid joke.
Third period kicked off and for the most part no one seemed to be close to scoring any time soon until the last ten minutes when the Flyers kicked it in the net and scored their fifth point landing on Jimmy's prediction, 5-3.
By this point Jenny was screaming at the TV set like' she always did when the' Devils would lose while Jimmy and me sat back and laughed.
"I wouldn't laugh Tom," she said. "If the Devils lose you're the one who's gonna pay for it."
"Ohhh, you hear that Tommy?" Jimmy laughed.
"Oh and how am I going to pay?" I asked.
An evil grin crept over her face and she continued watching the game whispering under her breath,
The last minute of the game everyone in the room held their breath, there' was so much tension and when the buzzer went off signaling the end of the game Jimmy and I both jumped up and shouted cheering that we had won. Jenny just sat there with that evil smile the whole time that Jimmy and I continued celebrating for an hour or so.
Finally, when it came time for Jimmy to head home Jenny walked him to the door while I started straightening up the living room a bit.
"Here," she said handing him the $100.
"Thanks Jen," he said slipping it into his wallet. "Better luck next time huh?"
He walked out and she slammed the door behind him locking it before turning to face me. "You happy,"
"Oh me," I replied. "Yeah of course; and it looks like you'll be doing some cleaning tomorrow. You didn't just lose your bet with Jimmy remember, we had a deal as well."
"Oh don't worry I plan to uphold my end of the bargain. But' I also told you if the Devils lose you're the one who's going to pay; and I plan to stay true to that as well."
I suddenly felt a little uneasy with the way she smiled at me and simply nodded my head throwing out the last empty beer bottle and standing still for a few moments. We sized each other up from across the room and I laughed nervously as I brushed past her.
"I have to piss,"
I walked into the bathroom, emptied my bladder and wondered as I stood over the toilet what exactly it was that Jenny might be planning. I flushed the toilet, turned around and opened the door jumping in surprise to find Jenny standing right in my path. She had both hands placed above me on each side of the doorframe and was smiling at me as she blocked my path.
"Jen...what are you-"
"You know when you offered to clean the bathroom naked for me you got a nice mental image going there. And' I got real excited and was looking forward to that happening; but since the devils lost that means you're not going to do that and that disappoints me."
"Sorry about that," I said in a very easy tone of voice. She reached in and touched my right cheek running her hand down my shoulder all the while still smiling at me.
"But' I pictured it," she whined. "And' now I'm horny."
She leaned in and kissed me on the lips forcing her tongue into my mouth and I was surprised but offered no protest. Hey, this was something I had wanted for a very long time now so why would I bother to resist. She broke the kiss and shoved me into the bathroom, before she put the lid on the toilet down and sat there, sliding her panties off from underneath of her skirt and tossing them to the floor.
She lifted her skirt and for the first time ever I found myself staring at my best friends cock; it was definitely bigger than mine,
"The Devils lost," she said. "So now I'm going to take out on your mouth and asshole. Deal,"
My own cock was straining in my pants just looking down at her like this and I agreed before getting right down on my knees and leaning in to wrap my lips around her rock solid erection. She grabbed my hair and shoved her dick down my throat causing me to choke and gag as she began mouth fucking me. God she was being so forceful about it and while it was slightly uncomfortable, I also' found myself strangely aroused by her aggressiveness.
"I hate losing," she said while she throat fucked me.
"You of all people know that I cannot stand when I lose. But' it's' okay because we all know who the better team really is. There's' still two more games and the next time, the devils are going to fuck the shit out of the Flyers like I'm doing to you."
I gagged and slurped as I did the best I could to accommodate my mouth for the size of her dick. I noticed the taste; it wasn't' as bad as I figured it might have been. There was a faint hint of urine but I didn't' have time to register the taste as she was still so busy ramming it down my throat.
She finally pulled me up for air before standing up and demanding that I get undressed. I obeyed, stripping down to absolutely nothing and she slid out of her skirt and Devils Jersey before instructing me to stand in the bathtub. I climbed into the tub and she got in with me, forcing me against the wall and rubbing her' huge cock against my asshole.
I could feel it probing my hole as she nibbled on my ear and ran her hands up and down my chest soothingly.
She grabbed hold of my cock and started stroking it nice and slow and I moaned while she slipped a finger into my ass and began massaging my prostate gland. It felt weird to have something up there; but it wasn't' a bad feeling just something I figured I would need to adjust to.
"I'm going to fuck you," she whispered before slapping me hard on the ass.
"Do you want me to fuck you baby?"
"Yes," I replied anxiously.
"I thought so," she slapped me again. "I've known for a long time now that you wanted to be with me Tom. I see the way you look at me...you've always wanted this cock,"
"You got me," I laughed. She gripped my ass giving it a nice squeeze before spreading my cheeks and probing me a little harder.
"You want this?"
I tensed up biting my lip as I felt her huge cock pushing into me and immediately I felt as though I were being' split in two. The searing pain shot up my spine and I gasped then yelled out in pain as she reached around and tweaked my nipples, kissing my neck, trying to comfort me.
"I'm sorry," she whispered pulling out. "Stupid me' forgot the lube; why don't we take this to my bedroom where things can be a little more comfortable."
I agreed and she carefully pulled out before leading me out of the bathroom and to her room. When we got there' the first thing she did was shove me onto the mattress, face planted in the pillow and ass sticking straight' up. She climbed onto the bed behind me and grabbed the lube pouring it all over my asshole. It felt good as she smeared the cold jelly over my hole and I turned around a bit to watch as she rubbed some onto her cock as well.
"Now, where were we?"
With that, she grabbed me by the hips and guided her cock right back into me. This time it was easy going and the only thing I noticed was a feeling of sudden fullness as she thrust her entire length into me right up to the hilt. I grunted and then moaned, gripping the bed sheets and then moving my hands up to her pillow to clutch the pillow tightly.
"Oh shit," she moaned. "You're so tight,"
"Uhmmf," I groaned, the sound muffled by the pillows.
She began thrusting in and out of me harder and harder with each thrust while running her fingernails down my back. "You like that baby?"
"Oh fuck yeah,"
"You like my big cock in that tight little asshole?"
"Good...now I'm going to punish you for the Flyers winning that game."
And' punish me she did; her thrusts suddenly became much harder and faster, now she was slamming her cock in and out of my ass with such ferocity that every time she slammed in my entire body would jolt and I would cry out in a mix of pain and pleasure.
"Devils are the best team in the NHL; say it!"
"Agh, the devils are the best team in the NHL,"
"The Flyers suck Jenny's dick."
"Oh, the Flyers suck Jenny's dick,"
I could hear the sound of flesh slapping against flesh and I could smell the musky aroma of sex filling the room as she pounded the hell out of me.
"Now tell me you love me and you want me to cum in your ass,"
That was a sudden change but I certainly had no problem at this point going along with it.
"I love you," I moaned. "I want you to cum in my ass."
"You got it baby," she whispered as she drove herself balls deep inside of me and then I felt the warmth of her cum filling me up.
As she pumped me full of her semen' my own cock jerked and twitched as I began to shoot my load all over the bed sheets underneath of me. When we had both finished, Jenny collapsed on top of me pushing me into the bed. I could feel the weight of her body pushing me further into the mattress.
We lay like that for a while with her dick still buried in my ass and both of us covered in sweat before I shifted a bit uncomfortably and she pulled out and rolled over lying next to me. We locked eyes and she smiled seductively at me; she was so fucking sexy.
"Say it again,"
I thought I knew what she meant so I said what I figured she wanted to hear.
"The devils rule, Flyers blow."
"No, no, no" she replied giggling and I was a bit confused now what she wanted if not to hear that the Devils were better than the Flyers.