There was no doubt that this was going to be my last baseball game in organized ball. I knew that after high school I would not get a chance to play anywhere else, save for the drunken beer league down the line. I was an average player who played for a small school. I played second base. We were losing badly and were about to be eliminated from the playoffs. We were down to our final out and I was up. My last at bat resulted in a hit to right field, but I wanted to leave the game with some drama, so I tried to turn a single into a double and ended up being thrown out. As we lined up for the handshakes against the opposing team, I started to think that I would not have to ever again feel uncomfortable in baseball pants. I did not like the way the pants accentuated the fact I had a bubble butt. And as for the shirts, I always felt my chest looked a little girly. I can't bring myself to use the words man boobs.
It was over for me. The seniors on the team just slumped away. We knew this was it. A few of us embraced and said goodbye. I drove straight to my girlfriend's house. She was expecting me to show up with a victorious grin on my face, but that was not going to happen. She lived with her sister, who was out of town at the moment. My girlfriend was also a senior, but she was 19 years old, to my 18. She was not the most ambitious person I knew. She sometimes had a strange sense of humor that tended to belittle instead of encourage. She was about 5'4" inches tall and was too thin for my taste. She had dirt blonde hair and a rather flat torso. She didn't mind having A cups, and always wore clothes that showed her breasts off as small. Her ass had no curves and was surprisingly a little broad. Amy seemed the wrong person for me to be dating. She was religiously into smoking weed and liked kinky sex. She enjoyed spanking me and liked anally inserting a dildo into me. The only reason we were together was because of happenstance.
Early in the school year, I, along with some other guys from the baseball team, had been given detention for causing a scene at a pep rally. It was my first time being disciplined for unruly behavior. Amy was a regular in detention. She was always late for school and late for her classes. She pretty much kept to her self in the back of the room. I ended up sitting next to her. I was embarrassed for being in detention and headed straight to the back of the room. She had always been in the background and I had never spoken to her. I think we once were in the same group for a project in chemistry. My friends from the baseball team took seats in front of Amy and started to give her some grief about being a stoner chick. She seemed to ignore them all too easily, but I really didn't like hearing anything they were saying to her. I told them too leave her alone, and they did. It could have been anyone, and I would have defended them against a couple of dumb jocks. Amy later told me that she was surprised at first, then felt a nice warm feeling that someone from another group, outside of her own stoner, slacker infested group that is, was defending her. A first for her. And pretty much, because of that day in detention, we started to exchange phone calls, emails, and text messages.
Amy took my virginity, and to be honest, I felt she could have made the moment seem special. I guess she figured a guy would get what he could. I enjoyed being with her. Sometimes she made me nervous when we would be out in public. I never knew what sort of comments she might elicit with her carefree attitude, or what kind of comments she might make to others.
When I arrived at her sister's place, I found Amy in the living room, reading a book on how to become a certified medicinal marijuana distributor. I saw her choosing that field to make a living. It seemed logical for Amy to pursue that.
"So, the San Francisco Giants won't be making you an offer?"
"No. Don't think so." I said.
I had to think about how sad I had felt a few days earlier, when a small division III School that had been looking at me, decided to pass. I was not even offered preferred walk-on status.
I should have changed out of my uniform because sometimes Amy teased me about the way my ass looks in it. She had told me that I have a soft body and still carry a small layer of baby fat. I can't argue with her. I should have remembered to change into something else.
I went into the kitchen and got a glass of water. Amy and I were not going to do anything as far as going out. We really could not afford to go anywhere. Our summer jobs were going to start soon enough. Mine was at least. Amy had not finalized a job yet. She wasn't planning on going to college. I had already been accepted into the local University, but not to play sports. I wondered if my mismatched girlfriend and I could continue.
"Hey princess, did you bring me some water. I'm thirsty." Amy said.
"Amy. Don't call me that, please." I said.
"I am sorry. You know I think you have a body like that pop princess, what's her name. Bubble butt and chubby thighs."
"I am a guy."
"Yes!" She said. "I know you are a guy. My guy!"
I wondered how true those words were. Did I even believe them? More importantly, did she believe them?
"Can I... I know sometimes we don't seem compatible, but I do care about you. You will go off to college and forget about me. That's just the way it will be."
"I don't know what will happen." I said.
I felt sad that she was already predicting that we did not have a future together. She was probably right.
"Can I ask a big favor? I just need it for me."
"What is it?" I said suspiciously.
Amy got up and stood in the center of the room. She looked as though whatever she was going to say was something she had rehearsed over time. I felt as though she was going to convince me of something that might not be all that great for me.
"I really do like when we are in bed together. Your body is so soft. It really isn't like the couple other guys I have been with. And I don't say that as a bad thing."
"I don't think any guy would like the sound of that." I said.
"Would you let me dress you up like a girl? Just once. Please, Eric."
My first thought was to just get up and leave, but her face was so sincere. She was not laughing or smiling. I was thinking about how she always liked running her hands across my body, just feeling my soft skin. What sort of fetish did she want to involve me in, I thought.
"No." I said. My answer lacked emphasis. I realized that I had left a small window for her to try again.
"It will be just for a minute. Please. I never dress girly. I kind of have something I might need resolving."
It was true. She always wore jeans and pullovers. There was nothing girly about her manner of dress.
"What do I have to put on?" I asked.
"I will be right back." She said.
Amy went into her sister's bedroom. Her sister was on a business trip. Her sister was a more serious person. Jill worked as a salesperson for some company that was always sending her to seminars. Amy was left alone. I guess her sister didn't mind Amy smoking pot, because the air always smelled of it. As far as I knew, the sister did not have that habit. Jill was more of a wine drinker.
Amy came out of the bedroom with a bundle of pink, with some white mixed in. Her face was eager. She was going to control this just like she controlled the bedroom. I figured it was innocent, and would be a nice memory to remember our days together. I knew she would probably start living a life that would punctuate or differences even more. The end of high school I was sure was going to be the end of any thing between us, and that saddened me some.
"Pink?" I said. "Don't you have, wait, you don't even wear pink."
"My sister keeps these around." Amy said.
Amy held up a short white skirt with ruffles and a rather small looking pink blouse. There was white thong and pink stockings. I just stared at the clothes and saw my masculinity swept to the side as if it could offer no resistance. I had visions of playing baseball in such an outfit, and of receiving congratulatory ass-smacks from my fellow players. I always hated the butt slaps. I felt one guy in particular, Tom, did it too often. I was sure he was feeling my bubble butt for his enjoyment.
"I will help you get dressed. Take off that dusty uniform." She commanded.
"This is just between us." I said.
I looked around the room to see if we would have privacy from the outside world. There was only one window I needed to concern myself with, and the shades were drawn. The shades were always drawn when Amy was alone. Using a bong might cause the nosier neighbors to either investigate themselves or have others more qualified to snoop around do it.
I had already removed my shoes, and now started to take off my uniform. I took off my shirt first. It was my team-shirt that said Warriors. I was some Warrior, I thought. I took off the t-shirt I wore underneath. I was thinking my chest was going to jiggle too much. I actually felt a little bloated from having drunk so much water during the game. I started to take off the pants, with dirt stains on both sides and on my bottom. I was standing there in my underwear with built in cup holder. I had forgotten to remove the cup. My white socks were also stained.
"Everything, Eric." She said.
"I see you have nice pink stockings for me to wear." I said.
I had passed the point of no return. She had me.
I removed what was left, and stood there naked for her. Even though she had seen me naked so many times, it still felt awkward for me, and I didn't think my manly member lived up my expectations of how big a man should be. While flaccid, the state it was in at that moment, it looked tiny. It was just a measure over two inches. I had resigned myself that the five inches it grew to would be sufficient to satisfy a girl. I had a grower, although not of any exceptional measurement. Amy never complained or made fun of my size, but she treated it dismissively on occasion. She seemed to grab it as though it were insignificant and would swallow me whole and sucked it like a pacifier. My little man worked and that was all that mattered. Well, mostly. Size was always going to be an issue.
Amy walked over to me and held out the thong. She lowered it so I could put my feet through it. This was to be my first ever thong. I had tried on my sister's panties a few years before. But this was my first thong. It went on like a comfortable wedgie. Next came the blouse top. She lowered it onto me. It fit an inch or so above my belly button. My stomach felt a little flabby. I tried to suck it in a little.
"You're fine baby." She whispered into my ear. "I was going to get you a sports bra, but this makes you look adorable."
As I said before, I hate the word man boobs, but that is what I looked to have. I now had little ones that disrupted the flow of the male chest.
Now came the skirt. This was the real closer on the matter. It was very short. I felt my bottom was not being covered.
"Now the stockings." I said, with a surprising hint of enthusiasm.
"These are going to feel so good." She said.
"You really look nice."
"Yes." She said.
"You really look girly." She said, as though she were proud of her work.
"Please don't call me that. I did this for you, Amy. Don't demean me." I said.
She was quiet, pensively calculating what my willingness to fulfill her wishes really meant.
I walked over to a mirror that hung by the front door. I brushed aside my blonde hair and before I knew it, Amy was there with more items to completely feminize me: a black wig, lipstick and some powder for my cheeks. The wig was shoulder length. My penis was getting hard, as I contemplated fucking Amy while I was wearing this outfit. That, I thought was her true motivation. Being fucked by her boyfriend who was dressed as a girl, as a very slutty girl.
"There, Eric." Amy said.
"Thanks for making me into your woman." I said, sarcastically.
"Thank you for doing this. Whatever else happens, just know it is all in fun."
"What?" I said.
There was suddenly a knock at the door. It seemed an insolent interruption. I was ready to flee with my discarded uniform into one of the rooms and dress myself back up into the man I was. Part of me wanted to play with Amy a little longer, but there was no way anyone else was going to see me dressed as a female.
"Who the fuck is that? What the fuck?" I said. Panic in my voice.
"Just relax, sweetie." Amy said.
She called me sweetie. I couldn't believe it.
She walked over to the door and greeted someone she obviously knew. I immediately bolted for the bathroom, grabbing what I could of my uniform. I locked the door and as I was getting ready to take off the pink blouse, I got a good look of myself in the larger bathroom mirror. The skirt looked good on my chubby thighs. Not really fat, just healthy. The dark hair made me look bitchy. I kind of wanted to continue the afternoon with her, but I felt things had been ended by an uninvited visitor.
"Eric...a?" Amy called from the other side of the door.
"You fucking called me Erica." I said.
"Open the door."
I paced the floor a few seconds trying to compose myself. I opened the door. I needed to know what was going on.
"Its just Rick. He's a friend Jill's. Will you come out and say hello?" Amy said.
"Let me get dressed."
"You are dressed, Eric."
"Why did you call me Erica before? Not fuckin' cool."
"Let's see if we can fool him."
"Are you crazy?" I said.
She acted as though it was no big deal for me to walk into a room dressed like a girl, and in that room would be a strange man.
"It'll be fun. I promise. I will owe you big time for this. You look really good." She said.
I caught my image in the mirror again, and was starting to turn myself on. I felt like a kid, when my mother would make me come out and say hello to her friends, when all I wanted to do was stay in my room and play video games.
"Just really quick." I said.
I walked behind Amy, wishing I could stay behind her the whole time, but she had other plans. She stepped to the side of me and gently pushed me into the center of the room.
"Rick, this is Erica. She is my best friend. We go to the same high school."
"Hello, Erica." He said.
I stood there silent. He looked to be in his early 20's. He sort of fit the mold of someone more inclined to be her friend than that of her sister. He had a couple of tattoos of mysterious symbols on his right arm He wore jeans and a loose fitting t-shirt. He wore a pair of unlaced work boots. His hair was uncombed. The only neat thing about his appearance was his trimmed mustache and goatee.
"Say hello." Amy prompted me.
"Hi, Rick." I said meekly.
"Hey, Girl." He said.
They started talking about some appointment he had missed that morning. They spoke as if I had disappeared. I was so nervous, felt so silly, and didn't know what to do. I felt trapped in a moment of indifference. That morning had ended so many dreams I had about playing baseball beyond the high school level. I actually felt divorced from the person I had been just the day before.
"Sit down." Amy was saying, as she patted the seat next to Rick on the sofa.
I sat down next to Rick, covering myself in an odd pose of arms and hunched shoulders. Amy went into the kitchen to get some drinks. Rick wanted a beer and I asked for the same.
"I can't believe Jill." He said to me. "She gets to vacation as part of her job. You'd think she was trained by now. Get to work bitch! Shit!"
I mumbled something as Amy handed me a beer.
"She jokes that she wants to quit this job and find another like it, and go though the whole process again." Amy said.
Before I even took a drink of my cold beer, Rick had brought out a bag of blunts. Amy's eyes widened.
"Erica doesn't indulge. Not first hand anyway." Amy said.
"Erica can do what she wants." Rick said, putting his hand on my thigh, just above the knee.
His hand felt very masculine. I was surprised this stoner had working, calloused hands. I felt so feminine with my soft body. I brushed aside the wig hair. I looked at him out of the corner of my eye. They continued talking about some appointment he was not able to make, as though his whole life was altered because he had missed it. The whole time they passed a blunt back and forth between each other. When they finally grew tired of dissecting his reasons for being late, and the implications of his mistake, Amy turned to me and smiled. A half, chiseled into her face smile that bespoke of an apology for what was to come. The air had filled with a smoke that was stronger than any Amy had ever produced.
"I think Erica has a surprise for you, Rick."
"I like surprises." Rick said.
"Close you eyes." Amy said.
I wanted to smack her. I wanted to leave, but was not able to think for myself.
Amy grabbed my hand and guided me up. Rick had his eyes closed. He looked less intimidating with his eyes shut. Amy took the bottle of beer from me. I had barely taken two sips. She positioned me in front of Rick and stepped behind me. She whispered into my ear that I looked fantastic and that this was all just fun. I nodded my head. She reached down under my skirt and felt for my dick. I was half way to a full erection. She started to tug on me, and when she was satisfied with the results, she let skirt fall back over me. My dick did not make a difference in the way the skirt fell over me.
"O.K., Rick. Open your eyes."
"He opened his eyes and smiled at me. I knew he was not expecting a pussy when Amy lifted the skirt.
"I'm surprised, Erica. Amy knows what I like though. Thank you for being here, Erica." Rick said.
I half nodded, without fully understanding what I was agreeing to.
His cold fingers took hold of me. They felt large, and I didn't think I could move away even if I had wanted to.
"Erica is adorable. Tell her that." Amy ordered.
"You are adorable, baby." Rick said.
He played with it a little. He looked at it from all angles, as if he were a doctor. One hand held my penis, while the other made for my balls. He tugged on the skin a little before grabbing hold of one ball. I was afraid he was going to squeeze too hard, but this grunge dude was actually gentle. His rough hands belied an inner softness. I stood there, my privates not so private. I was pink and I pulsated with a need, a desire, to be satisfied. Now he held both balls, and weighed them in his hand. I was staying hard. A strange hand felt good, and having my girlfriend behind me made it all seem so normal.
Rick opened his mouth, and I think my mouth opened a little. This was no longer fondling. I was going to be blown by a man, as Amy held me tightly and whispered how I was not like those other boy's in school. She praised that my mind was open to something so natural. She cursed those boys from school that made her feel like an outcast. His lips were strong. I was expecting to be ground up like a piece of candy, but he had obviously learned the art of oral sex from experience. The bristles on his mustache made contact with my soft skin, and after a minute or so they started to feel part of the stimulation. He made small noises, and I could hear that he was breathing through his nose some. He let me go and just looked at my penis. Was he admiring having made it stiffer than when he had begun? It was very rigid, and after what seemed like approval of his work, he began his sucking again.
"Does it feel good?" Amy said.
"Yes." I said.
I wanted to tell her, to tell Rick, that he was better than her. His lips were fuller and had seemingly logged in more time doing this. I was surprised I was lasting so long without cumming. I was taking the whole idea in, and finally, succumbing to an adept turn of tongue, I started my orgasm.