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Disclaimer: I am over 18 if you are under 18 and/or offended by teenage male and a transgendered adult having sex. Any connection between the characters in this story and those in real life is pure coincidence.
This is a work of fiction.
Miss Richards: The Earnings
"Mom, hey mom, hey guess what?"
"What sweetie?"
"You're supposed to guess, but I found a car!"
"Really? What'd you find honey?"
"There was a car across from the school up for sale, and it's only $3000!"
"That's great sweetie, but what is it? Do you know how it runs or if there are any problems with it?"
"It's a 2003 Chevy Prizm, with about 60,000 miles on it. Tony's grandfather is selling it because he's too old to drive and they said it runs great with no problems."
"Well give dad the info and he'll go check it out. Since you found one so cheap me and your father will pay for half and you can keep your extra $500."
"You are the best parents ever. I love you mom."
Things were relatively quiet around school the next few weeks. My parents were finishing up the car and getting the title switched over. Meanwhile Sandy and I decided to take things slow, she was still uncomfortable with people watching her and for good reason. Sandy truly was packing two apples in the front of her pants, and I don't know how I didn't notice the ever so slight bulge she had until I saw them for myself exposed on my bed. After our afternoon in my bedroom she got dressed and told me her story. She told me that her Mom hated her new lifestyle but being the "good Christian" she was she wouldn't stop her. Her dad hated it so much that he left and her mom had to re-marry and the new husband wanted nothing to do with her. She also told me her testicles weren't always that large, that they only started to grow when she started hormone therapy about 2 and a half years ago. Her doctor told her that her body was trying to fight the influx of estrogen by generating more testosterone. Her growth became painful when her skin wouldn't stretch fast enough and so she stopped taking her pills. She told me that she was still getting used to her new self and just needed time to think about what it meant between the two of us.
"Hey Alex, what's up?"
"Morning Sandy, it's good to see you. I haven't been up to much except baseball, oh, and I just got my new car. Just drove it to school today actually."
"Oh my god, no way, you totally have to give me a ride to school and back like every day now!"
"No doubt, where do you live now?"
"Not far, just about 10 minutes from here off of Flewellen in Hawk's Point."
"Oh I know where that is, after class just meet me in the parking lot."
Just looking at Sandy, I could imagine spending the rest of my life with her. There was something in her eyes, in her smile. She was different from anyone I've met in my life. It's that thought alone that scared me though. What did this mean for me? Does this make me gay; would I tell my parents about her if we got together? These thoughts scared me, I had never thought of myself as gay. The thought of doing anything with a man, an actual man, disgusted me. With Sandy and Miss Richards it was different though. At least that is what I told myself. I keep telling myself it's different, but is it really? All this time I was waiting for Sandy to know whether she was comfortable or not, but I didn't take the time to ask whether I was. So I decided to pass notes to Sandy during our lesson with Miss Richards.
"Hey, do you like me?"
She took the note and tried to stifle a laugh when she opened it and wrote back giggling.
"Yes, why?"
"Do you wanna be my girlfriend?"
"Maybe, why? Do you wanna be my boyfriend?"
"I would love to be your boyfriend."
I meant it too. I don't know what that meant for my future, but with her it all didn't seem to matter. She was more of a woman than any of these girls around me, and more of a man in her pants than even me.
"And what would you do for me if I let you be my boyfriend?"
"I'd love you, make love to you, and let you make love to me."
"Really, well there are people together that aren't boyfriend and girlfriend that already do that, what else?"
"I'd make all your problems go away."
She stopped and wrote something on the note and slipped it into her pocket. She sat there and stared at the board for the rest of the class. Which actually wasn't that much longer, just about 2 minutes later and the bell rang. Sandy simply gathered her stuff and took my hand in a suggested "follow" manner. She moved with a purpose seeming to know exactly where she was going and what she wanted. I began to speak but was met instantly with a quick but polite "Shhh." We were in an old auditorium that I didn't even know the school had. The surfaces were covered in dust and cobwebs had accumulated in the corners of almost every place in the room.
"This is the school's original auditorium, they stopped using it in the 70's when a series of bad events happened."
"What..."
"In 68 they were preparing for a play and a boy fell down that elevator shaft and broke his back, he died, three days later. In 69 in that same elevator three members of the tech crew were on the elevator from the rafters heading to the sub-stage, and the cord snapped and it fell to the bottom. One kid died and two of them had their legs snapped directly in half and one broke their hip as well. In 70 the theater had a cursed atmosphere and the elevator wasn't used anymore they had ladders placed everywhere. One day a homeless man snuck in and raped a freshman stage hand on the top rafter of the entire stage. When they noticed it happening they rushed to save her but every time they tried climbing up he would kick the ladder down. She was raped for over an hour until police arrived. After that this place was shut down. The only reason it wasn't torn down was that it holds critical support beams to this wing of the school."
"Why..."
"Sometimes, really bad things happen to good people. Sometimes people have problems that aren't simple. My father left my mother because he was ashamed of what I had become. The man who loved having me as a son, took me to the park, nursed my bruises and scrapes, and told me stories when I went to bed, that same man cursed me and spat in my face when he left. My mother shut down when he left. I was alone in my own home. I was sent to live with my aunt who was also like me. She lives in your neighborhood, just a couple streets away. The time with my aunt was the best time of my life. She understood me and taught me all the things I would need to know about my new life. You see, I lied about my parents a bit, we didn't move because she married some guy. I had to move back because she married some guy and wanted to amend for her actions by taking me back. I was told by my aunt that I had a sister only slightly older than me. She left for college before I moved there. If you truly mean what you wrote then yes. Yes I will be your girlfriend. You have to promise to make sure that you fill my life with so much love that I will forget all my problems." That was a lot to take in. I Miss Richards made her life seem so easy. Her parents loved her for who she was. I always imagined that if I married someone that the entire family would get along, that we would be together on Christmas and Thanksgiving. Now I don't know. Wait, yes I do, I'm not getting with this one girl's family. I am becoming her boyfriend, not her families.
"Yes, I promise."
"Pinky swear on it?"
"Pinky swear?"
"It's something my aunt always did. Anytime she made a promise she made me pinky swear on it. If she were to break her promise, she had to break her pinky. She never broke her promises."
"I pinky swear." With that we locked pinkies and she looked into my eyes with those gorgeous gray eyes and she leaned in to kiss me.
"Well now what?"
"Well now you give me a ride home and we chill in my room."
"Sounds like a plan to me."
The ride back to her house was peaceful. She enjoyed playing with my iPod the entire way commenting every now and then on certain songs or bands I had. I was finding out that we both enjoyed much of the same music. It was only a ten minute drive as she said it would be and she wasn't lying about her family's wealth either. Her home was huge, the foyer alone was as almost as big as my entire house. The entire place dripped with elegance.
"So, this is your house?"
"Uhmm yeah, but don't worry, all this flare is my mom's choice. I like simpler thing. Here, let's go to my room."
"Speaking of your mom, is she gonna come home and have a problem with me being here."
"Probably, but don't worry she's too regal in her head to say anything to you about it. Come on, let's go."
With that she pulled me up their grand staircase. It alone was massive. It reminded me of something you'd see in an old movie. It must have been ten feet wide and I don't even know how many steps. We passed under a hallway that had "East Wing" hung over the entrance in grand elegant font. The concept that I was in a house with "Wings" seemed like an oddity to me, an unfathomable notion that I couldn't shake. Her room was at the end of a long branching hallway, and I couldn't help but think that a person could get lost for days in this labyrinth of a house. She opened her door and I think my heart stopped. Her room was a paradise. Instead of the usual pink or yellow walls of most girls the walls were a blacked out and filled with posters of various bands and singers ranging from Brad Paisley to Rise Against. A 60 inch TV sat in the far corner of the room. Underneath the TV sat a couple consoles and stacks of video games. In the middle of the room sat a couple of Sumo Beanbags which looked amazingly comfortable. Her bed was absolutely massive and sat in the closest corner on the right, and her desk sat in the corner to the left. The desk was strewn with drawings and books of art and music.
"Are these drawings yours?"
"Yeah, ever since staying with my aunt I started getting interested in art. They aren't much but it passes the time."
"No no, they're really good; I think you could sell a few of these."
"Well thanks, I've never really shown anybody them before, thank you again."
"You wanna play some video games?"
"Sure, but I'm kinda horny, wanna make it interesting?"
"I'm game, what'd you have in mind?"
"Well how bout whoever loses has to take off an article of clothing, and whoever loses all their clothes first has to give the other one a blowjob?"
"Hmmmmm, sounds like you're going down."
We decided to play a shooter and I had to admit she was good. She took an early lead and had me down to my pants in no time flat. She was predictable though and after two quick games I had her topless. Staring at her perfect breasts had me distracted the entire fourth and fifth game. I was left with just my pants and underwear. She stumbled on the next game and strategically decided to take her pants off before her sandals. The bulge of testicles inside her boyshorts was highly distracting. I couldn't get over how big they were and soon enough I was down to just my boxers which were trying their hardest to conceal an ever hardening erection. I couldn't help but notice that her dick started to bulge along the hip of her shorts and I capitalized by winning the next round. Continuing her earlier distraction strategy she took off her shorts before the sandals. As she did she hung her ass in front of my face and I couldn't help but take a bite before she moved it away.
"Hey, that's cheating, no distracting before the final round."
"Okay pot."
"Kettle."
The next round was for all the marbles and I put everything I had into it. I ended up winning by one kill and looked over to my not so upset opponent.
"Ha, off with the sandals Sandy."
"I could do that, or how about one final round with double the odds. The winner gets to fuck the other one in the ass."
"You're on, and just to let you know I'm gonna enjoy every minute of what lies in store."
"I bet you are."
With that we started the final round, she changed game strategies and went with being a sniper this round. She was playing with me the entire time for it wasn't even close. She won by a landslide and I knew what was about to happen and I had to admit I was scared.
"So what was that about enjoying every minute?"
"Actually I think it still holds true, just be gentle okay, I'm just a little nervous."
"Awwww, I'm sorry Alex, you don't have to if you're not ready."
"No, you won and fair is fair. Also, you wanna know a little secret?"
"What?"
"You're kinda cute, with your big balls and all."
We both giggled and snickered as she pounced on me and planted me to the floor. Her mouth was on mine in an instant and my senses were filled with the aura of cinnamon again. I could feel her erection grinding against my stomach. Her balls, heavy and full were resting against the fabric of my underwear. Her hands were resting against my chest feeling for the hard muscle underneath the surface.
"Hey Alex let's take this to the bed."
We returned to our embrace and I lifted her up by the bottom of her butt cheeks from the floor. She was light in my arms and with ease I used one arm to hold her while I hooked off my underwear. As soon as we landed on the bed she rolled me over onto the top of her. I could feel her hands freely exploring my ass now. It felt alien to me, but with every new touch I could feel every nerve tingle deep within me. Her fingers moved slowly but methodically, and gradually reached my twitching hole. When she started to push I broke our kiss with an audible gasp enthralled with a rush of new senses.
"Do I need to stop?"
"God no, keep going."
I continued our kiss as her finger pushed further inside of me. It wasn't entirely pleasant, but it wasn't entirely awful either. I couldn't get over the feeling as if whatever was inside of me needed to be out, but I wanted it so bad to be in me. My mind was a torrent of mixed feelings but I could do was push myself further onto her finger and when I reached the bottom she was the one who broke our kiss with a gasp.
"I think you're ready Alex, hold on one second."
"Where are you going?"
"Hold on, I need to grab a condom and some lube."
It had never crossed my mind to use protection, but the lube definitely sounded like a good idea. She walked over to the edge of the bed and I could see her balls, bulged with the skin horrifically tight. She rolled on a standard Trojan condom. I couldn't look anymore as she started to open the container of lubricant with an audible click. I got onto my hands and knees as I could feel the bed dip as she straddled in between my legs. Her cool fingers, slick and moist, ran along and inside my hole. I could feel the now all too familiar mixture of emotions return to the pit of my stomach.
"Hold on, I don't want to lose my virginity like this."
As I turned around I could see the hurt in her beautiful gray eyes, and I moved quickly to ease her troubles.
"Don't fret sweetie, I just wanted to look in those eyes as you enter me."
And as quickly as they turned dark, her eyes beamed to life with renewed excitement. I was filled again with the rush of cinnamon as her lips pressed into mine and I felt her hips surge forward and her modest girth pressed suddenly inside of me and with that we both gasped.
"Gentle sweetie, it still hurts."
"Okay baby, I will, just bare with me. This is a first for me as well."
I downplayed my pain to her. I knew it was just the tip of her, but it hurt more than most things I'd ever felt. The pressure against my hole felt a thousand times greater than when her finger was inside of me and I continued to wince with every new inch she pressed into me.
"Oh baby you're so tight, I love how this feels. Your ass is simply amazing!"
All I could do was return a chuckle as she pressed further until I felt her balls press against the bottom of my cheeks. I could feel her pull back as she readied herself to work her length into me once again.
"Keep going slow Sandy, I'm still getting used to you."
She slowly moved forward again and I could feel the pain start to ease away. Pain gave away to pleasure and every movement sent waves through my body. Her cock fit perfectly inside of me, every time she pushed all the way forward I felt a surge of pleasure shoot through my entire body.
"Okay sweetie, I think I'm ready."
"Are you sure Alex?"
Her voice was tinted with genuine concern as she continued to slowly grind in and out of me. I could see the sweat shimmer off of her body and her breasts bounce with every final shove.
"Yes."
She needed no further encouragement as she started to thrust harder and harder with every pass. Her hips pushed with more force and I could feel that special spot every time and I was driving me insane. I started to squirm wanting to feel her deeper inside of me.
"That's it baby, take my cock. Oh I love the way you look every time I push into you."
"Keep going Sandy I think I'm gonna cum!"
"Oh yes baby, god this feels so good!"
That's when I felt it, the first blast of cum erupted from somewhere deep inside of me.
"God Alex! Cum for me, I can feel your ass clenching me, Ugh! I'm cumming!"
I could feel an expansion deep inside me at that sweet spot. The condom was filling with all of her cum. She was buried as deep as her hips could push and the inflation never seemed to end causing me to only writhe in increased blissful agony. At the moment where I knew I would snap, I was filled with a rush of cinnamon as I felt those magnificent lips on mine. I felt her hips start to pull away from me and I broke our kiss to see the product of her work.
"Oh my god Sandy!"
It was monstrous. Her condom was misshapen from the utter engorgement. The reservoir tip was no more. There was only a ball the size of an orange stretched full with thick white liquid. It was scary to think that she could produce so much.
"That's kinda sexy, sexy. What do you wanna do now?"
"I don't know, but I really need to get this thing off of me."
That's when we heard it. There was a knock on the bedroom door.
Thanks for reading part 5. As always I welcome all comments, suggestions, or critiques. Also open to chat from fans. You can always reach me at das4200@yahoo and I will always respond to emails. There will be more to come. Love you all and thanks again for reading.