Shemale

Troy, New York in 1975, where Jimmy, the nerd captain of the school’s chess team, discovers women at the ripe old age of 18.

***

“Come on in Jimmy,” Mrs. Biondi said, stepping aside after I had knocked on the door, and as soon as I walked in the modest rural home I knew that this was going to be a great day.

Mrs. Biondi was Becky’s mother, and while Becky was supposed to be the reason I kept showing up at 2:45 every afternoon, the only reason I was there was to spend time with Mrs. Biondi, who was a goddess in my eyes.

Becky was Mrs. Biondi’s youngest child, and although she was only 14 she had shown an incredible talent for chess. She was in 9th grade and wasn’t even in high school yet, but was so good that the school let her play with the high school team.

Since I was the captain of the team I had taken an interest in young Becky, because not only was she an asset to our team but she would be a major contributor to our school’s team in the future.

Bullshit aside, while I did enjoy playing chess, and did want our school to do well then and in the future, my interests were not about Becky or chess but in her mother.

Even today, I would find it hard to explain to someone why I became infatuated by the twice divorced mother of four, the youngest of which was Becky, a very timid kid who seemed to be good at nothing except chess.

Mrs. Biondi wasn’t beautiful, although to me she was. She was an amazon of sorts, standing about 5’9″ or so, and while she wasn’t lean and trim by any standards, she was in good shape for a woman around 50.

Mrs. Biondi had a body that was peculiar, to say the least. She was built almost like a caricature, with a small butt – certainly compared to the rest of her – and legs that weren’t bad at all.

Above the waist was a whole different story. Her arms were a little plump but solid, and I could never really tell if she had a thick waist or not, but there was a good reason for that, and it wasn’t all because she wore loose fitting tops.

Her breasts. You couldn’t help but notice them, because they were huge. Even though she did everything possible to camouflage them you couldn’t help but see that those boobs were gigantic, and all fall and winter I had made a point of staring at them every chance I got.

I had gotten an inkling of how big they were one day when I had used the bathroom, and there hanging on the curtain rod of the shower was Mrs. Biondi’s bra. It didn’t have her name on it but it sure wasn’t Becky’s. I locked the door and took it off of the rod where it was drying and examined it like it was some sort of national treasure.

It was a long-line bra with five hooks, more on the side that the middle of the back, and after I played with the cavernous cups I checked the back for the size tag. Unfortunately, the tag was unreadable because the harness was old, so I was left to use my imagination.

Becky must have thought I got lost, because I was in the bathroom for a long time. I did everything possible to the bra, even hanging it on a hook and pretending I was standing in front of Mrs. Biondi and squeezing the empty cups.

In the end, I had an erection that wouldn’t go away, and so I dropped my pants and jerked off, pulling on my long, skinny prong for about ten seconds before popping a load into the toilet and the surrounding area. I felt like a pervert while cleaning up the mess of course, but it was worth it.

On that day in spring, I knew it was going to be a special one after Mrs. Biondi had let me in. I was in heaven because she was wearing a blouse that, while not revealing, was certainly more form fitting than the usual flannel tops and sweatshirts she had worn during the colder months.

Just another reason to be happy that the weather was getting warmer, I thought as I engaged in idle chit-chat with Becky’s mother, all the while trying not to stare at those incredible breasts that stuck out so far.

Additionally, the white and pink blouse had short sleeves that were a little baggy, so I kept hoping for a chance to peek into the armhole and see her breasts from the side encased in that magnificent harness. That’s how desperate I was to get a glimpse of any part of Mrs. Biondi.

She had gotten used to me being underfoot for the hour or so until Becky’s bus dropped her off every weekday, and she probably thought I was harmless because I was such a nerd. I hoped she didn’t think I was interested in Becky because I surely wasn’t. 18 year old guys dating 14 year old girls would get you laughed out of school, and I was already the butt of too many jokes because I was the classic skinny nerd.

I could see the outline of the straps of Mrs. Biondi’s bra through the fabric of the blouse, and when she started to take things out of the cupboard to get dinner ready I casually slid over to watch.

She had nice arms, I noticed, a little plump but nicely shaped, and when she reached up to get something I walked over to offer my assistance.

“I thought I had more İstanbul Escort bread crumbs up there,” Mrs. Biondi said as she moved things around on the top shelf, and even though at best we were the same height I offered to help look, my eyes fixed on the hanging sleeve and her upraised arm.

I never got to see her breasts from the side that day although I got to see plenty, because when I looked down her sleeve I learned that Mrs. Biondi didn’t shave her armpits. This was 1975, and there were a couple of girls who thought they were hippies and had hair under their arms, but nothing like this.

I don’t know how long I stood there staring down Mrs. Biondi’s sleeve while I was supposed to be looking for bread crumbs, but it was long enough for her to clear her throat, the sound of which broke me out of my trance.

I was busted, and the only saving grace was that I did find a container of bread crumbs hidden in the back of the top shelf. I suspect that my face was every bit as red as it felt, although Mrs. Biondi seemed more amused than upset.

Becky finally showed up and that got me away from Mrs. Biondi but it didn’t get that image out of my mind, because Becky kicked my ass every game until her dinner time. Mrs. Biondi asked me if I wanted to stay for dinner, like she often did, but I declined because I had other issues.

I took off through the little patch of woods that separated our neighborhoods, and after I made sure no one was aroused I took out my best friend. That was no easy task because not only was I hard, my drooling had fused me to the cotton.

Once free, I closed my eyes and replayed that image in my head; that nicely shaped arm, the deep hollow of her underarm, and the jungle of black hair that filled it. Not just a little wisp like I had, but a thick tuft that seemed to overflow the crater it grew in.

I managed to last about 30 seconds this time, which was good for me, and the best thing was that I didn’t have to clean up the mess like I would have had to at home. Having gotten masturbation down to an art form was yet another one of my dubious skills, and had been the extent of my sex life at that point.

In fact, the only sexual experience I had with anyone was a hand job. It was a birthday present from the sister of a friend of mine. Karen was a chubby girl who was a year older than me, and my friend had let it out that it was my birthday.

When I left his house Karen was following me, and while we got along okay it wasn’t like we were friends or anything. In that very same patch of woods she caught up with me and told me she wanted to give me a birthday kiss. I had necked with girls a couple of times before, so the kiss was nothing new.

“Are your parents home,” Karen asked, and I nodded.

She made a face and asked me if I wanted another kiss, and I said sure, and this time along with the kiss came a grab of my crotch, which got my attention.

March 16 at 3 in the afternoon. It was a cloudy day and the temperature was barely above freezing. There was still some snow on the ground, and where there wasn’t snow there was mud so after Karen looked around and said there wasn’t any place better, asked me if I wanted her to jerk me off.

I think the hand would have been her mouth if the ground was dry, and if my mother wasn’t home, who knows? Anyway, I said yes and there I was standing in the woods, my teeth chattering and my pants down around my knees, and Karen’s chubby hand was cold.

“Sorry,” Karen said as she began to pull on my limp dick, and as her hand warmed my cock started to get hard. “Hey, you got a pretty big dick for a little guy.”

“I do?” I asked.

“It’s not very thick but it’s pretty long. Bigger than Brian’s,” Karen said, and then told me that she had caught him jerking off once, which was how she knew.

Her pudgy fist kept pumping hard and because of the combination of the cold, my nerves and an unfamiliar hand my usual rapid fire was delayed.

“Sorry,” I apologized when Karen changed her grip and moved a little behind me, because I thought she was getting annoyed with how long it was taking. “Usually a lot faster.”

“It’s okay Jimmy,” Karen said. “I like doing this. You even been laid?”

“Me – uh…”

“I guess that means no,” Karen said. “That’s okay though. Would you want to fuck me sometime?”

“Uh – yeah, I guess,” I mumbled, and soon I was on the brink.

“Oh!” I groaned and then I was spurting all over the winter wonderland while Karen milked every drop out of me. After I was limp she let go of my dick, calmly licked the rope of cum off of the back of her hand, and told me to give her a call sometime when my folks were out of the house.

Just like that, Karen left, and I pulled up my pants and went to the corner store to buy a quart of Genesee beer to celebrate. I went right back to the place I had just lost my sort-of virginity and drank the beer in the freezing cold.

That was a month ago, and I didn’t call Karen. Not Kadıköy Escort because she was unattractive because I was no prize myself, but because I wanted my first time to be special, and in my mind there was only one woman that would qualify. Mrs. Biondi.

***

The next day that I stopped at Mrs. Biondi’s house she didn’t answer the door when I knocked. I assumed she must have gone to the store or something so I sat on the porch for a minute and waited. The day was even warmer than the day before so I took my jacket off and tied it around my waist.

I heard a squeaking sound from the back yard, so I walked along the side of the house to the back. The squeaking sound continued, and when I got around to the back I saw clothes dancing along the clothesline, making the trip from the back porch where Mrs. Biondi was clipping the clothes on the line and pushing to line along.

There was one of her bras already on the line, but I had something much better to look at, and I savored the seconds before she saw me. Mrs. Biondi was wearing a pink sleeveless blouse, and it made her breasts seem ever larger because it was snug. I could see the outline of the bra cups as I approached, which every step getting me a better angle.

Mrs. Biondi was startled to see me and I mumbled something about knocking, but I was too busy staring under her upraised arm to pay attention to what she was saying. She was standing on the back porch about a foot above me, giving me a prime view up the underside of her massive breasts, but when I looked over I was shocked.

Shaved. Gone was the wild jungle of hair, and now the large craters were barren, although I could see a dense five o’clock shadow that covered the entire hollow and up the inside of her arm a bit.

When I glanced over, Mrs. Biondi was staring at me again like she did yesterday only even more so, and then she glanced over to her underarm since it must have been clear where I was staring.

“You okay, Jimmy?” she asked as she went back to putting the clothes on the line. “Something wrong?”

“No – uh – you shaved,” I mumbled for some reason.

“What? Oh yeah, although you’d never know it now,” Mrs. Biondi said. “Why do you – oh! I get it. I was wondering what you were staring at yesterday in the kitchen. I thought you were looking somewhere else. Didn’t mean to scare you.”

“I wasn’t scared,” I said.

“Warm weather is coming up and I don’t think people are ready for what I look like during the winter.”

“I liked it. I thought it was sexy,” I heard myself saying.

“Is that so? Boy, I guess my daughter has a crush on a kinky guy,” Mrs. Biondi said with a grin.

“A crush?” I said.

“Haven’t you noticed?” Mrs. Biondi asked. “I thought you two were sweet on each other but you were too shy to make a move.”

“Becky?” I said. “I’m not interested in Becky – I mean she’s a nice enough kid and all, but she’s a kid. I’m 18.”

“You are?” Mrs. Biondi said. “I – I’m sorry, I didn’t realize.”

“No, I just come over here to help her prepare for the chess tournaments,” I said.

“Better not tell Becky that,” Mrs. Biondi quipped. “She’ll stop letting you win sometimes if she heard that.”

“Letting me win?”

“That’s what she told me,” Mrs. Biondi said. “I don’t know the game, but she says she doesn’t try hard sometimes so you keep coming back. Please don’t tell her I said this.”

“I won’t,” I said, starting to feel like an idiot.

“I shouldn’t have presumed anything,” Mrs. Biondi said. “I couldn’t think of any other reason why you would come over here every day like that.”

“If chess was the only reason, I would be here an hour later,” I told her, and then waited for Mrs. Biondi to figure it out, but she was way ahead of me.

“I know,” she said softly. “I mean, I suspected as much and I guess I should have said something. Guess I liked being looked at for a change, but I didn’t really mean to lead you on. I remember having crushes on guys.”

“I don’t think it’s a crush,” I mumbled.

“Is it because of these?” Mrs. Biondi asked, pointing at her breasts and in embarassment I looked away and pawed at the ground. “If that’s what it is, let me tell you something. I think you look at Playboy pictures too much. Mine don’t look like that, believe me.”

“Maybe at first, but it’s more than that now,” I said, struggling to keep from getting emotional. “I love the way you kid around, and the way your eyes sparkle when you laugh. I love when I get to talk to you every day before Becky gets here. You treat me like a adult instead of a kid.”

“You’re a very mature young man,” Mrs. Biondi said. “Very intelligent and polite, although your taste in women is a bit screwy.”

“Don’t say that – please,” I said, because while I knew she was just trying to be funny, I didn’t think being her love with her was weird, or a joke.

I had taken the two steps up to the porch, so I could avoid having her looking down at me, and as we stared at Ataşehir Escort each other the sound of the front door closing broke the tension.

“Saturday – Becky’s father has her for the day,” Mrs. Biondi said as she grabbed her empty laundry basket. “If you want to come over we can talk some more.”

***

How do you prepare for a day when you aren’t really sure what it entailed? Part of me thought that she wanted me – wanted me like I wanted her – yet when I looked in the mirror, I thought the idea was absurd. Mrs. Biondi was a woman, and an amazon to boot.

She outweighed me and was a little taller than me to boot, and if we ever wrestled she would probably kill me. Ever hear the saying ‘I’m a lover, not fighter’? I was neither. I was a man only technically. Physically, except for having a pretty long dick, I was pathetic.

So I concluded that Mrs. Biondi just wanted to talk. Maybe she wanted me to teach her how to play chess, because she had mentioned that once, so with that in mind I went over around 11, which was a little after Becky’s father picked her up for the weekend.

I was dressed as neatly as possible, even shaving, which was silly since nothing was happening to get rid of. I knocked on the door like always, but the door had already started to open when my knuckles hit the wood.

“Oh – sorry,” I said as the door opened and Mrs. Biondi motioned me to come in, looking around outside to make sure nobody was around.

My apology was for the fact that I must have screwed up the time I was supposed to be there because Mrs. Biondi was wearing a bathrobe. It was like she had just woken up, although I noticed that her long wavy hair was brushed and she had on a little make-up, which she rarely wore.

I followed her to the kitchen, which was not unusual, but Mrs. Biondi didn’t stop there but kept going. I stopped at the end of the kitchen and looked down the hall.

“Are you trying to give me a chance to change my mind?” she asked after turning around and facing me while standing next to the open door of her bedroom for a second before going in.

On legs that felt as if they were made of rubber I staggered down the hall with the realization that this was really happening. This wasn’t one of my fantasies because in those dreams I was a suave and cool ladies man who was in control, not a sweaty and frantic kid who suddenly figured out that this wasn’t going to be an afternoon of playing spin the bottle.

I got to the open doorway and looked in to the bedroom where Mrs. Biondi was standing at the side of her bed waiting nervously, although not nearly as much as I was.

“Coming in?”

“Uh, yeah,” I mumbled. “Should I close the door?”

“Doesn’t matter,” she said, and then as she probably wondered what the hell was wrong with me she added, “Look Jimmy, if you don’t want to…”

“I do!” I almost shouted and then lowered my voice. “I just – I mean I’m just nervous.”

“Me too. You don’t think I do this every day do you?”

“No,” I said, and it was then that Mrs. Biondi shrugged the bathrobe off of her rounded shoulders, and there was nothing underneath except Mrs. Biondi, a whole lot of Mr. Biondi.

“Oh man,” I mumbled to myself as I looked at the first live naked woman I had ever seen in real life, and while she was right that she didn’t look like any of the women in Playboy, there weren’t any of them that were going to stand naked in front of me now or anytime soon.

She got tired of me standing there staring at her after about a minute, at which point she sort of wrapped her arms in front of her and started shifting her weight from foot to foot.

“Should I?” I asked as I tried to indicate that I was asking whether I should take my clothes off with some primitive hand gesturing, because my voice failed me.

“That would help,” she said.

“I’m not good at this girl stuff, and you’re so pretty – even better than I dreamed,” I managed while fumbling for my top shirt button while staring at her voluptuous form.

Those breasts – and there was no way to avoid them because they commanded your attention – hung down to her waist. I tried to think of something to compare them with but came up blank because they were bigger than footballs but smaller than watermelons and she had crimson nipples that looked as big as bullets centered on auroelas that were the diameter of baseballs.

Below that, unlike most of the girls in Playboy Mrs. Biondi had pubic hair, and even the ones that did had nothing to compare with the very wide triangle of dark brown hair that blocked any view of what was under the jungle.

Then below that, the woman had legs that were almost like a ballet dancer, slender and so out of place with the upper part of her, and her butt was small as well. It was as if she had been assembled in the dark with parts of two bodies, but while it wasn’t symmetrical it was as erotic a sight as I could imagine.

And then she was in front of me. Tired of watching me drool and fumble in an attempt to unbutton my shirt, she had come over to me and was doing it for me, and while her fingers were trembling a little too they were nothing like mine. The fact that she was looking down at me – physically because she was a couple inches taller – was no help to me.

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