PZA Boy Stories

J.O. Dickingson Donny's Conversion 2022 Boys Medical/Medicine Story

Edited by Boyman

Category & Story codes

Feminisation/Sissy Contemporary story
tt Mt – anal oral mast – femin first med
(Explanation)

Summary

Donny gets caught trying on his sister's underwear and it turns out to be a complete life changer

Characters

Donny (13yo) Dianna, his sister (17yo); High School Boys: Wally; Derek; George, College Student; Chrissie

Publ. 26 Feb 2022
Finished 7,000 words (14 pages)

Disclaimer

If you are under the legal age of majority in your area or have objections to this type of expression, please stop reading now.

If you don't enjoy reading erotic stories about boys, why are you here in the first place?

This story is the complete and total product of the author's imagination and a work of fantasy, thus it is completely fictitious, i.e. it never happened and it doesn't mean to condone or endorse any of the acts that take place in it. The author certainly does not want anyone to do the things described in this story in real life.

It is just a story, ok?

"Oh my God! Donny! What the friggin' hell!"

Oh shit, my big sister Dianna. This was Tuesday. She was supposed to be at cheerleading practice. She shouldn't be home for another hour.

"Dianna?"

"Take my panties off now! This friggin' instant!"

"Turn around. I have nothing on underneath."

"As if I'm supposed to care you little pervert!"

"Dianna. What is all the shouting abo – oh my goodness!"

Double shit. My mother wasn't supposed to be home yet either. Actually she was supposed to be picking up Dianna.

"George!"

Dad was home? He never comes home from work early. Never. Except today. Well might as well call him to come see too. Maybe we should call up Gram and Gramps on the computer and have a Goddamn video chat.

"Donald George, you take your sister's underwear off this instant!" Mom only used both my names if I was in serious trouble.

"What's going on here?" Dad appeared behind Mom.

They all stood there staring. I shut the door and stripped off Dianna's panties and bra and put on my boxers and jeans as fast as I could. It was her fault. If she had put her clothes in the hamper I wouldn't have seen them when I walked past her room, and if I hadn't seen them I wouldn't have been tempted to try them on. Anyway, what was the big deal? You'd think she was ten again and figuring she'd catch cooties or something from me. They were her dirty clothes. I should be the one worried about catching cooties, girl cooties. I was just curious was all. Everyone said how much alike we looked. I just wondered what I'd look like. 'Sides, I figured it would be sortta daring, sortta, well, sexy. Sexy was a totally new adventure for me.

I opened the door. They were still standing there. All three of them. Staring. Dianna pushed past me and demanded to know where I put her clothes and when I said I put them in the laundry hamper where they should have been in the first place she made a huge fuss like they were contaminated and had to be incinerated or something now.

"Donald, we need to talk."

I followed Dad to the workshop where he spent his evenings tinkering and repairing whatever needed repairing around the house. It smelled of leather and three-in-one oil and freshly cut wood, man smells. He sat in his swivel stool at the workbench. I stood.

"Boys don't wear panties and bras."

"I was just-."

"It isn't natural."

"I was-."

"Don't ever let me catch you doing that again."

"Yes, sir."

End of conversation. What Dad had meant was he needed to talk, I needed to listen. As usual, I never got the opportunity to talk, and even if I had, he wouldn't have listened. He never did. I went to my room. I still didn't see that it was any big deal. I was curious was all, and I liked nice things. Dianna had nice things. She always did. And I liked to look nice. I looked nice in her things, though they were a bit big. She was four years older than me. Three years and seven months actually. She'd turned seventeen just over a month ago. And it was sexy, I think. It gave my willy a strange feeling anyway.

I thought that was the end of the matter, but no, at supper the next evening Dad observed, "It's a crazy, mixed up world these days. Things were a lot simpler when I was a boy. You were either a male or a female. Well, there were a few hermaphrodites, but those were circus freaks and didn't live long. Lived in the tropics or someplace I think. There was none of this transgender and non-binary and cis this and cis that crap, whatever they all are. A boy was a he or a him, not an it or a they or a shim. A shim! A shim is a wooden wedge to make a window or door plumb for Christ sake! Can you imagine being called a shim? Oh sure, there were tomboys and girlyboys, but they grew out of it soon enough, even faster for some girlyboys after a few fistfights in the back alley. None of them went so far as to not know what their parts were for, not like what you read today."

"George, what are you going on about?"

"What Donald was doing yesterday. Guys at work say it's common these days."

"Donny? George! You didn't tell the guys at work what — ."

"Of course not. I don't want nobody to know our boy is confused if he is our son or our daughter."

"Confused? Dad, I-."

"You think I want the guys I work with every day knowing what sort of boy we have?"

Say what? What sort of boy did he think I was?

"Like I said, guys at work say its common these days. Boys not knowing if they're boys or girls I mean. Not a surprise. Look at all the women doing men's jobs these days, dressing and looking like men, thinking they can do what men can do. No wonder kids are confused. Well, there's one thing no woman can do that a man can. Let's see them stand up and take a – ."

"George!"

"And that comedian, what's her name, Ellen something, kissing another woman, on TV yet. There was a time you could never mention perversions like that on TV never mind show them. There's no sense of decency these days. Anyway, Joe, Joe Walaszczyk, said there's a cure. Conversion Therapy he called it. Sets things right in a boy's head. Gave me the name of a doctor that specializes in cases like Donald's."

"Dad-."

"Made an appointment for him Friday. You'll have to take him. Doctor Francis Stein is the name. He's supposed to be good. With a girly name like Francis maybe he understands boys like Donny."

Boys like me? What sort of boy was that?

Mom didn't argue. Mom never argues with Dad. Nobody does.

***

Doctor Frances Stein turned out to be a woman, chunky, jowls, fifty-something, looked a lot like Dad. In a dress. Conversed with you just like him too.

"So, Donald, how long have you wanted to be a girl?"

"Say what? I never wanted to be — ."

"That's okay. Nothing to be ashamed about."

"I'm not ash-."

"A lot of boys are confused these days. Well strip down to your underwear and we'll take some measurements." She measured my height and weight talking quietly to herself.

"Both average, chest, a bit flabby, but that's good, we can replace that baby fat with some tissue, firm those titties up real nice without needing to stretch the skin."

SAY WHAT?

"biceps won't have reduce those," she chuckled

well thanks a lot

"thighs mm, nice."

What does that mean?

"Butt very nice."

Blush!

"You have gorgeous hair. I'm glad you wear it long. Fewer and fewer boys do anymore, not like the sixties and seventies. Now lower your underwear and cough."

Lower – she was a woman! I was so concerned I forgot to turn my head away when I coughed. "Sorry!"

Thankfully she wasn't angry. If she had been she could have gotten even but good considering what she had in her hand!

"Should be no problem retracting the twins back into the abdominal cavity where they came from. Can use the skin to make a nice little pouch for you. Nice size willy. You're thirteen?"

"Yeah. Thirteen and six months."

She finally let go of the twins and her fingers moved up and wrapped around my thing! She was holding it! With her hand! My willy! And pulling back the skin … and pushing it back up … and pulling it back.

"NO!"

Didn't she know what that did? She was a doctor. She should.

"How often do you masturbate?"

"WHAT?"

"You know, jack off, wank, play with it." Stroke.

"I-I-."

"What do you think about when you do? Girls?" Stroke, stroke.

"Well, uh, yeah, sometimes."

"In their underwear? Naked? Their titties? Their pussies? Girls in your school?"

Stroke, stroke.

"Yeah, all those."

IT WAS SWELLING! What sort of doctor was she? I was ready to swear to thinking anything if she'd stop.

"Your sister?"

Stroke.

"NO!"

Almost anything. Stroke.

"Other boys?"

"Uh, well — ."

"When did you begin wearing girl's underwear?"

Thank God, she stopped wanking it.

"Begin? I just did it-."

"How long have you wished you had titties?"

"I, I, I never-."

"You wish you had a pussy too?"

"No!"

"When you play with yourself do you go all the way?"

"Uh-."

"You know, until you produce semen."

"Uh-."

"Juice. Jizz. You can produce semen can't you? How old — ."

"THIRTEEN. AND SEX – I MEAN SIX — MONTHS! AND YES. I CAN."

"Do you like girls?"

"Well, yeah, sure."

"You have sex with them yet?"

"Sex? No! … Not yet."

"Do you like boys?"

"Well, sure, of course. I like — ."

"You have — ."

"NO! I don't mean like them THAT way!"

"That's okay. Nothing to be ashamed about."

"I'm not ash-."

"Nothing wrong with boys your age liking boys. Or having sex with them. Nothing wrong at all. Nothing wrong at any age. You can pull your underwear up and get dressed now."

Thank God! By the time I was dressed she had the needle prepared.

"We'll supplement the injections with estrogen pills."

"Injec-TIONS?"

"Once a week for now and we'll see how it goes. Take two pills daily." Fortunately you're not that far into puberty from the size of your willy."

HEY! If you'd kept stroking it, you'd have seen how big it can get!

"We can delay it with a shot of LHRH analog while your body adjusts to the treatments but once the twins retract it shouldn't be necessary. It would have been easier if you'd have come in earlier, before puberty, but I think we've begun intervention soon enough. Now this will pinch a bit."

Pinch? It hurt like hell.

"What was that?"

"Sugar and spice and everything nice, sweetie," she said with a smile.

The shot of LHRH hurt even more so. No idea what it was. Snips and snails I suppose. I didn't ask. I was too busy thinking of the pain to pay attention to what the bitch told Mom. They gave me something called a depilatory cream or something I had to rub into my skin on my legs and arms and chest every other day.

***

I began aversion therapy the following Monday, an hour a day, five days a week, right after school. I don't know the purpose or whatever but it was weird. I sat there and pictures of men and women flashed on a big screen, men and women kissing, hugging, doing more, doing stuff I never in my wildest dreams imagined them doing. The room must have been next to the bathroom cause after a bit it began to stink of piss and farts. Made me feel like puking. And then there were pictures of guys doing the same stuff together. Now that I definitely never ever imagined! There must have been a cafeteria on the other side of the room. I swear I could smell steaks, roasting turkey, even roses or lilacs or something sometimes. And something else that was familiar but I couldn't place. Mushrooms? The smells blocked out the bathroom smells and I inhaled deep. And I did chest exercises every day, push ups, dumbbells, something call chair dips.

***

Two months went by. Doctor Stein cut out the sugar and spice shots, started me on Apalutamide capsules (one a day), took some blood, felt me up again. I was really getting chest muscles. Even Dad noticed, which was unusual in that he seldom notices anything about me. He thought it great I was getting some muscle finally.

Saturday Doctor Stein took me shopping, for dresses, skirts, blouses, panties, and training bras, and for lipstick and makeup and stuff, and we stopped at a place called Mia Bella and the woman there showed me how to put on the makeup and a guy styled my hair. I didn't mind. I like to go shopping and often went with Mom, though not for that stuff of course, and the makeup smelled good and I looked beautiful. Really beautiful. I did have great hair, ginger blond, and thanks to Mom, Dad hadn't made me cut it. We celebrated my second month anniversary and end of the injections by going to A and W, me in my new clothes and with my makeup on. Doctor Stein told me she wanted me to get whatever I like, and gave me her purse, saying it was on her.

"So, what can I get you?" the guy behind the counter asked my breasts. He was a high-school student, seventeen, big ears, sort of geeky-looking. I ordered. He couldn't keep his eyes off my breasts, even while filling the mugs with root beer.

"There you go," he said, putting the order on the tray. "Enjoy your boober. I mean your bugger – BURGER! ENJOY YOUR BURGER!"

Poor guy was as red as a cherry. I had to try hard not to giggle. I wasn't used to a purse and when I opened it up it slipped out of my hands and the contents went flying everywhere. That was when I discovered you can't bend at the knees in a tight skirt, or spread your legs for balance when you bent at the waist. I turned around and held the counter for support as I leaned over. Several guys in the line behind and beside me leaped to my assistance. Several checked out my cleavage in case something had dropped there. When I straightened up and turned around the guy at the counter looked like a tromped on frog!

Doctor Stein thought it hilarious. "He couldn't stop staring at your breasts. And when you turned around and bent over …."

She was laughing so hard she couldn't finish.

"I thought his eyes were going to pop out of his head."

"That's not the only thing that I thought was going to pop out," she giggled. I had noticed that too.

"Well, you passed that test with flying colours," she observed.

I didn't even know I was being tested.

***

The next Saturday I dressed up while the family was out and went shopping on my own, and stopped in at the A and W. The same guy was there. There were three tills. I stood in the line for his. He flashed me a wide smile. The third Saturday he stopped by my table and asked my boobs how my burger was, and if they'd like to go out some time.

"Maybe a show or something. Spiderman is on now – though I don't suppose that's a show you'd like."

"I love Spiderman," I replied in surprise, forgetting I was a girl and that wasn't a girl show.

"Great. I'll pick you up at seven. What is your address?"

Uh-oh!

"I, uh, got some stuff I need to do first. I'll meet you at the theatre."

I'm sure not many girls take a backpack on their first date, especially to the theatre. But not many have to change into a skirt and blouse in the mall first, and carry a set of guy's clothes with them either. I changed back in the bushes after he dropped me off at home and drove off.

On our second date he must have found it strange I had something to do first again and brought my backpack but he didn't say anything. He stretched and dropped his left arm on the back of my seat. I rested my head on his shoulder like I'd seen couples do. It was awkward and gave me a stiff neck.

On our third date we held hands and when he dropped me off at home we kissed goodnight. Several times. I had to wait for him to head down the street before I took out the hoodie I had hidden in the bushes when he came to pick me up and to wear when I dashed to my room when we returned.

On our fourth date, two weeks before school resumed, he got bolder. He squeezed my knee and began to slip his hand up my thigh. I started to straighten up and was about to push his hand away but decided what the hell, enjoy it. I innocently snuggled up to him and let my hand drop in his lap instead as his hand stroked my thigh. That really sent a quiver up you know where. He snuggled into a more comfortable position, I thought, but realized later it was to get his crotch under my hand. I wasn't the only one hard. He squirmed again and I had another handful of popcorn and let my hand drop again. His fly was open. He had pulled down his zipper! When I did nothing he squirmed again so my hand slipped into his fly. He was good. He drew his ass back before I could do anything and my hand went in further.

Well, what the hell. He'd paid for my ticket and the popcorn and soda, and was taking me for a treat at A and W afterward, and it was our fourth date. His hand slipped up my dress and began rubbing what he thought was my pussy through my panties. Well two could play his game. I found the opening to his underwear and slipped my fingers inside. His was huge. Much larger than mine. It had to be hurting pinned in his boxers. I wrapped my fingers about it and squeezed. It was really hard and I could feel it throbbing. He suddenly stopped rubbing me and sat up and I figured he'd had enough. I gave it a few final strokes and it suddenly throbbed really hard. Before I realized what was happening I had a handful of hot, sticky jizz. I flooded my panties. I felt it trickling down my thigh. He didn't move his hand. He had to have felt me throbbing and the wetness through the thin cotton of my panties. I don't imagine he had any experience with a girl having an orgasm. Not under his hand surely.

When we left the theatre I could see a dark splotch in his jeans and he walked bowlegged. I held my purse in front of me and said I wasn't really hungry and he should just take me home. He didn't disagree. He gave me a kiss when he dropped me off. A quick peck. Almost missed my lips.

Tuesday while Dianna and Mom were out and Dad at work I tried on one of Dianna's bras and panties again. I really filled out her bra now. Totally. I put on her newest blouse. I looked better in it than she did, in my opinion. Definitely sexy. Willy stood up to look in the mirror with me. Totally sexy.

Wally was real nervous when he asked to take me to the show the next Saturday. I declined and we went rollerblading in the park on Friday instead, in public and daylight. Several of his friends came by and he strutted, wrapped his arm about me, squeezed my tit, stuff like that, showing off he had a hot date like me. Saturday I bought a larger bra and some new blouses for myself. If Mom was to check my dresser drawers or the garment bag in the closet she'd have a fit!

***

The end of that summer Donald George Allen transferred out of Garnier Junior High and Dawn Georgette Alden registered in Grade Nine in Saint Mary's. Doctor Stein helped with the paperwork and forging signatures and official letterheads. The other paperwork got lost in the system.

I began a new life and a new routine. I began wearing bulky sweaters and loose shirts to hide my boobs at home. Arrive early at school in hoodie and baggy jeans and change in the girls can. After school change back in the girls can. When I went out whenever possible I left the house while the family was away, and returned when they were in bed or downstairs watching TV.

In September, Wally, who was now in Grade 12, and I went to the high school basketball game with a couple of other high school guys and their girlfriends and then out for pizza. Some of his buddies checked me out. None of them had a clue. They asked what school I went to and I almost said Saint Mary's Junior High! I said I was being home schooled.

Wally began seeing some of the high school girls more. Some of his buddies hit on me. Everyone was free and easy. I went out with a few of the high school girls I'd met after that, shopping, chick-flicks at the theatre, girl's night out stuff, even had a sleepover with a couple of them mid-October and talked about boys and kissing and who was hot. That was really wicked! All was going well.

At my next appointment with Doctor Stein she cut out the LHRH injections and the pills. My boobs had really filled out. She began laser treatments on my legs and one weekend she tucked away the twins, easing them back into the body cavity they retreated to whenever it got cold and stitching the opening closed. Showed me a nerve along my inner thigh to activate a muscle, the cremaster, that drew the twins back if they tried escaping. She folded the loose skin they had been in to "form a muff for your willy" and she showed me how to tuck him inside. I had to take a week off and rest. Doctor Stein told the folks I'd pulled a groin muscle. Dad thought that was a real man thing and he told the guys at work.

One night early December after the high school basketball game our little gang was joined by Dianna and her newest date, a first year college guy, Derek, muscular as hell and wickedly handsome. Dianna was the envy of every girl in our group. Well, almost every girl. She had no idea who I was! Derek kept checking me out, which was a real hoot! Dianna noticed and flirted with him even more. That was an even greater hoot.

The next Friday four of us and Dianna and her date went to a college basketball game and Saturday ten of us, me and Wally, Dianna and Derek, two of the high school girls with two guys from the high school, and a guy and his date from the college, went to Club Med to dance, those who were eighteen drinking liquor and the rest of us sodas.

The next Saturday one of the college basketball players, Greg, a third-year engineering student, took me to my first college dance. When they played the slow tunes he held me close and pressed his body against mine. He had a boner. So did I.

The next month when we went to Club Med Greg slipped me a liquor drink, a gin drink called a Tom Collins. I flirted with him. And with Dianna's date. She was not amused. The other girls in our group were envious. Greg was a real catch. When we got together on our girls' night out those who had been with me told the other girls and they all wanted to know all about him, and just how far we went. I wondered what it might be like, the two of us. He was a good kisser, and a lot more sophisticated than Wally.

February we girls took in a College game. When it was over Greg came over to say hello, said they were going for burgers after they showered and changed, and invited me. I told him I would love to but that would be too late as I had school the next day. He pouted and said he had really been hoping he could spend some time with me and tried to coax me to go. I made eyes at him and said I'd really like to and how sexy he was when he was hot and sweaty after a game but my parents would ground me. Then he got this look in his eyes and took my hand and said he had a better idea and to follow him.

He took me behind the barricade in the hallway to keep out the public who had come to see the game and down the darkened corridor and past the weight room to the handball courts. Slipping inside one he wrapped his arms about me and began kissing and caressing me and pressing his body up against mine. He soon had my blouse and bra off and I pulled off his damp basketball jersey and I pressed my tits against his hairy chest. His body was hot and sweaty and he began to bone up. So did I. We kissed, he squeezed and played with my boobs and when he pushed my skirt down I slipped my hands inside his basketball shorts and pushed them and his underwear down. They hung up on his boner and I had to struggle with them. He had his hand in my panties and was stroking my muff. My willy was swollen and throbbing inside and as he began pushing my panties down I told him we had to stop. Of course he said not now and I said I'd never done it, and that I wasn't on the pill, and I wouldn't do it bareback. I actually said that, bareback.

"I'll pull out, I promise…."

He had my panties pulled down mid-thigh. Doctor Stein said a boy wouldn't know the difference between my muff and the real thing, especially with my ginger blond hairs which she showed me how to curl over it, and it was dark. Before I lost my courage, I dropped to my knees and took his thing in my mouth. It didn't taste at all bad. The smell of ball sweat was delightful actually and I remembered when I used to play with the twins and then smell my fingers. Greg inhaled deeply and made no protest. I eased my lips up and down and sucked. Tube steak the guys called it. I was fourteen, fourteen and four months, Greg twenty-one and eleven. I inhaled through my nose again. It was the same fragrance I had smelled ten months ago in Doctor Stein's office and couldn't place. My willy began throbbing, flooding his muff, my stuff oozing out and dripping down my thigh. Greg began squirting too. He didn't pull out. I swallowed. It wasn't that bad actually. He took me home. It wasn't until I stripped for bed that I realized I'd given him my address. Damn!

Dianna turned eighteen the next month and celebrated by going to Club Med to drink legally with Derek and the high school group, including me. She got stupid drunk, and then puking drunk. Derek rolled his eyes at me.

The next week a group of us girls went to the College basketball game. At the end of the game Greg came over and said some of the guys were getting together to celebrate their win and asked if I'd like to come along.

It was a Friday night and I and one of the girls in our group, Melissa, had arranged for a sleep-over after the game. I glanced at her and she formed an O with her mouth and gave me the thumbs up.

The get together, seven of the team, each with a date, was at one of the player's homes. Everyone was high from the game, and there was no limit to the bowls of snacks, sodas, or beers. The smell of weed was thick. Greg tried to get me to try some but I refused. I did have a gin and tonic, one. Doctor Stein had warned me. My pills and booze were not compatible. Dianna had several and flirted with Greg, hoping to get Derek, and me, jealous. Couples were necking wherever you looked and I noticed a steady stream slipping away and returning. Dianna and Derek were one couple. They did not stay long. Then she and Greg disappeared, for a much longer time, but when they returned Greg didn't look that pleased, not as pleased as he would have looked if anything had happened.

Then Derek gave me a leer and nodded to the hallway when the next couple returned. Well Dianna had gone with Greg so why not? Going to one of the bedrooms, Derek closed the door and had his hands on my boobs immediately, and then up my dress. I told him up front I don't go all the way. We kissed and caressed and Derek had my sweater up and my bra off and was rubbing and squeezing my breasts. When he slipped his hands down and tried to remove my skirt I slapped his hands and reminded him what I had told him.

When we returned to the group I hung onto him and looked up at him and batted my eyes. Dianna was not happy. I phone Melissa and her brother came and picked me up. We got to Melissa's safe despite her brother's eyes being on my boobs more than the road.

***

Two weeks later I was feeling depressed and decided to get dressed up and go out. Phoned Melissa on the spur of the moment to meet up with me in the mall and go shopping. It was a Tuesday. Dianna was at cheerleading, Mom was out. I put on my favourite sweater and skirt and opened the door, and looked up at Derek as he was about to ring the doorbell.

"Uh. Oh. You surprised me. Ah, Dianna's not home."

"I know. Cheerleading practice."

"Ah, yeah."

"I came to see you."

"Me?"

"Yeah."

"How? How did you know to find me here?"

"Greg gave me your address."

"Oh."

"I didn't know you lived here with Dianna. I've never seen you here before."

"Ah, yeah, well, we're cousins. I spend as much time here as I do at home. My parents … travel a lot. They're away right now."

"Cousins huh? I should have known. Can see the resemblance now. You could be sisters you're so much alike."

I could not help smiling. If he only knew.

"We're not that much alike."

"I meant in appearance. You have very different personalities. And you wear much … ah … nicer … ah … you look much hotter," he said, gesturing at my outfit. "Of course I haven't seen as much of your body as I have of hers."

I pretended not to get the hint.

"You said you came to see me?"

"Ah, yeah. I came to apologize for the other night. At the party. I didn't mean to come on that strong."

"That's okay. I understand. The excitement and the booze and all."

"No. Wasn't the booze. I've been attracted to you ever since the first day I saw you."

I remembered that day well.

"Really?" I asked surprised.

"Yeah. You're fantastic looking. Really beautiful. And I've discovered you have a great personality."

"Well, thank you."

"I'd really like to get to know you better. More intimately."

I got the message. "What about Dianna?"

"She's okay. But, well, you're much more attractive. And well, when it comes to the intimate part, she's sortta stuck-up you know. Cold."

"And I'm not."

"Greg says you're very hot."

"Greg? What has he been saying about me!"

"Ah, nothing," he said quickly. Too quickly. "Just that he has a good time with you. Ah, when he's with you that is, you know."

I knew.

"He know you're here?"

"Of course he did, you idiot. He gave him your address didn't he?"

"Ah, yeah. He said you two weren't in a relationship or anything."

"What about you and Dianna?"

"Dianna and me? Oh no. Good friends, that's all. No, you know, attachment."

Dianna would be surprised by that. She'd be even more surprised to know her boyfriend had come hitting on me. She'd be even more surprised if he and I — .

"Why don't you come in?"

He hesitated.

"The folks – Dianna and her parents won't be back for an hour. We'll have the house to ourselves."

His face lit up like a kid invited into a candy store. I took him upstairs, almost to my room until I realized it was obviously a boy's room. I veered into Dianna's bedroom.

"Nice," he said, looking around.

"I didn't invite you in to admire the decor," I said.

We embraced, and kissed, and began to caress. Derek pulled my sweater up over my head and had no difficulty undoing the snaps on my bra and had my breasts cupped in his hands again. Lots of experience with Dianna I suspect. We were soon down to just his boxers and my panties. The way his boxers jutted out there was no question of his arousal. I was wearing one of Doctor Stein's pouches of course, my swollen dick encased in the folds of the pouch, my hairs curled around it like Doctor Stein had showed me. When he tried to slip my panties off I reminded him I don't go all the way and have never done it. He said he'd be gentle and had lube, and had brought protection.

"You brought bodyguards?" I joked, looking around as if surprised.

My joke didn't discourage him. I told him rubbers were not foolproof and I was not taking chances.

"Besides, I'm saving that for my future husband. But we can do something else," I suggested, and his face lit up.

"I've never seen a rubber before. How do you put it on?" I asked all innocent.

"It's simple, really." He looked at me and it took a moment for it to dawn on him what I'd suggested. He took out his wallet and a packet like a book of matches. He took out the rubber and then slid it down and over his dick. It was a nice size. Not as huge as Greg's.

"And lube?"

"Oh yeah. I came prep – you know, just in case."

He took a tube out of his jeans, squeezed some gel in his palm, and greased up his dick. Meanwhile I pulled back the sheets on Dianna's bed, tossed her pillow in the middle, pushed down my panties, and lay down with my crotch pressed against the pillow. Derek leaped up on the bed, tongue hanging out, and knelt between my legs. It was the first time for both of us. We had to try several times before he got it in, but it wasn't that wide and the lube helped.

It was weird feeling it pumping in and out of my ass, and his hot breath panting against my neck, but it was hot. That I was making out with Dianna's boyfriend was even hotter. And in her bed hotter yet. Suppose she caught us with him in me! And she thought me in her panties was perverted. I began squirting and I squirmed and grunted. Derek knew I'd climaxed and he came too, filling the condom. I was fourteen and a half, Derek five years older.

When we finished I noticed a damp spot on her pillow when I put it back and quickly turned it over. Derek took the rubber off and stood there sort of dumb like wondering what to do with it. He ended up wrapping it in his handkerchief and stuffing it in his pocket. When I pulled the sheets back in place I noticed he'd dribbled. When she went to bed tonight she'd be smelling my crotch, and laying on his wet spot. Wicked.

***

Dianna graduated that June and I went on to Saint Ignatius. That summer I and some of the girls discovered Jakes, a bistro/karaoke restaurant. I met Chrissie there. She was Catholic, from Bishop Grantam Junior High, and going to Saint Ignatius too. Long, gorgeous walnut brown hair, sensuous lips, a real knock-out. She sang some karaoke and she convinced me to join her in a duet. I found she had her own band, the Heaven's Angels, and played guitar and was the lead singer. A second girl played second guitar, another the drums, and a third the synthesizer. They convinced me to join them. I had a decent voice, soprano, higher than it had been before puberty, and I loved to sing. In September we discovered we were in the same math and science classes. The end of the month we played for the high school dance and were a huge hit. And we were hit on by half the high school boys. That was really hot.

That summer and fall I broke away from Wally and his gang and the high school girls from the public school, and their college crushes. Derek tried to hit on me several times but all he wanted was sex, and I'd had my revenge on Dianna, and Greg was already trying to get in the panties of another grade tenner. They were both predators with only one goal.

Doctor Stein gave Willy a checkup and gave me a supply of soft gel booster capsules to keep him in shape and she gave me my last laser treatment, declaring my armpits glabrescent and me glamorous.

Early October Chrissie and I were practicing in the sound booth after school. There was nobody else around. She suddenly turned and kissed me, on the lips. I was still in shock when she opened up my blouse and undid the straps of my bra.

"Your tits are fantastic."

"Ah, well, thanks." Hers were too but Christ, she was another girl.

"Gramma Stein does great work."

"Stein? Doctor Stein?" She nodded. "She told you about me?" I asked aghast.

And we had hit it off so great. She was my only close friend besides Melissa.

"She'd never do that. Classified doctor-patient information stuff you know. She'd never reveal that."

"Then how did — ."

"I'd recognize Gramma's work anywhere," Chrissie said with a smile. She threw back her shoulders and stuck out her chest.

"You mean … you …"

"Used to be Christopher."

We kissed.

Tuesday she … he … shim came over right after school to do math together. I didn't have to switch clothes – she knew. Ten minutes and Chrissie closed the door and we went at it. Stripping each other, lip kissing, stroking and kissing tits, sucking nipples until they were hard and burning. She had a muff too and we admired each other's and then let each other's willy out. We lay on my bed in opposite directions and sucked each other's willy. We were about the same size, a hand width plus two fingers long. It was awesome having someone sucking mine. Even more awesome sucking her willy at the same time. We swallowed each other's jizz, down to the last drop. Better than milkshakes. I was in love.

We were coming down the stairs when the front door opened. Shit!

"Ah. This Chrissie. We take classes together."

"Donald was helping me with my mathematics." As if she needed any help!

"Ah. Nice to meet you. Ah, Donald, you shouldn't really be entertaining up in your room when there's nobody around," Mom said.

"Nonsense," Dad intervened. "You heard the kids. They were doing homework. Glad Donald offered to help you. He is a real whiz when it comes to mathematics. I know math can be hard for girls."

He was talking but he was assessing Chrissie's boobs.

"Oh, yes, it was hard, very hard," Chrissie said.

I choked. I walked with her to the door. "Next time my place," she said.

"Sure," I croaked.

As she walked down the driveway I admired her butt. So did Dad. God, Willy ached to be up it. I could smell someone barbequing steaks. I wondered what gift I could get Doctor Stein to show my thanks. As I turned to shut the door Dad winked and gave me the thumbs up. I felt a bit guilty, but, well, we had been doing math. Sixty-nine is a number. And next time we planned on doing fractions. Improper fractions considering mine was bigger. I'd told her I'd never been a numerator and she said she preferred the denominator. I can't wait.

The End

© J.O. Dickingson

Did you enjoy this story/update?
Give it a thumbs up!
Click the icon.

Like!

Please send comments:
J.O. Dickingson would love to hear what you think of the story!

If you would like a response to your comment, you must provide an e-mail address in the box below.
Your message will remain fully anonymous if you leave it blank.
Your E-mail:
Your first name:
;