And the winner is …

I had always been a strong supporter of the cheerleading squad at high school. My best friend, Sally, was a cheerleader. Sally and I had been best friends ever since we moved into the house next to hers when she and I were four years old.

I had encouraged her to be a cheerleader when she was getting cold feet before tryouts. I had been there to help the squad with many practical things and have always bought tickets for their fundraising lotteries. No, I had no wish to be a cheerleader myself but the girls were fun and good friends. All of them, not only Sally, by now.

So it was a no-brainer that I would buy a ticket for their latest lottery early in senior year. Only one this time. For some reason you were only allowed to buy one. On the other hand it was expensive. Sally wrote my name on a small card and put it in the bowl. Only then did I think about asking about the prize. Shows how strong and unthinking my support was.

- A date with Arnold Racioppi.

Oh, oh. Arnold Racioppi was not only the most valuable player on the football team (Quarter-back). He was also the most sought-after boyfriend in school. Apart from being a great athlete he was an all-round nice guy. No, he didn’t have a girlfriend at the time. That happened a lot. No one, not least himself could understand why. I actually knew him quite well since we both worked on the school newspaper. But back to the situation that quite obviously needed some rectification.

- Sally, take my name out of that bowl. You can keep the money but you must understand how ridiculous it would be.
- Why? You are not the only boy who has bought a ticket.

Despite our friendship Sally absolutely refused to do what I wanted and demanded. I finally gave up. The risk that I would “win” was miniscule so why bother?

I should have bothered. At the lottery draw:

- And the winner is ….. Peter Smith!!!

The reaction to that clearly shows that I go to a completely crazy school. Cheering and people congratulating me. I realized that I had gained a reputation for being girly and/or gay just because I hung out with the cheerleaders. Why can’t people see another reason for a boy to hang out with a bunch of beautiful girls? And the cheerleaders are not my only friends. I have many guy friends as well! All of them apparently happy for my sake. And I’m on the baseball team. So what if it’s the B-team. It’s still a school team. By the way, my teammates congratulated me as well.

Arnold came up to me and told me how glad he was that I had won. He also said that he was looking forward to the date and would plan something really special for me. Did I say that I go to a crazy school? I’m not small. I may not be a huge football player but I’m not small. However, standing next to the massive Arnold, who IS a huge football player, I was dwarfed.

Looking around, I realized that trying to back out was not a good idea.

That started two weeks of madness. First of all, I was named an Honorary Cheerleader and expected to train with them. Of course I had to be. I was going to a date with a footballer players and football players date cheerleaders. Q.E.D.! At least that gave me (and the Principal) an out. Cheerleading practice was counted as PE so at least I didn’t have to face the locker room - I thought. As it turned out I still had to change with the boys. Only this time at the same time as the football team. You know the one with my future date. Somewhat embarrassing, especially considering the tiny hotpants and crop top I was required to wear. Just to make a point clear. I did NOT wear skirts of dresses to school. NOR lingerie.

Of course, my embarrassment and humiliation didn’t end there. Last spring I had had a rather tempestuous disagreement with my parents. My father wanted me to go a manly man camp that he had gone to at my age. Apparently, that was the high point of his life (rather sad really). Me? I love baseball and had insisted on a baseball camp. So what if I’m not the greatest player? I still love the sport. I had won. The camp was great.

Still, that had left my parents a bit miffed with me. I had not realized how long they could hold a grudge. I was about to learn.

Normal parents would have been shocked about the date thing and stopped the thing there and then. My parents didn’t. Out of sheer spite they aided and abetted the other lunatics instead. Of course in the most humiliating way possible.

My mother took me lingerie shopping.

- Mom, I don’t need any lingerie!
- Stop being silly. There is no way I’ll let my son go on a first date with a boy without proper lingerie.
- Why? It’s not like Arnold is going to see it anyway.
- Well, you never know and just in case …
- Mom! I’m not that kind of a boy!
- Well, I should hope so. Not on a FIRST date. But just in case …

Somehow I found myself in the lingerie store with my mother.

- Hello. Can we get some help? My son is going on a date with Arnold Racioppi and he needs some really nice lingerie.
- Oh, he is the one that won the lottery. How excited he must be.
- White. The lingerie must be white. He is a virgin you know.
- Really, no girls either?
- No, he isn’t that kind of boy.

Actually I’m THAT kind of a boy but for some reason I never had a girlfriend that this had been an issue with. Sally? Don’t be silly! She is like a sister to me.

- Peter is a late bloomer and rather flat on top. Is there anything to help him “enhance” things?
- Of course. He is not the first one I have helped. Not even the first boy. But he is MUCH cuter than the other one.

Surprisingly we left the shop without buying any “chicken filets”. No, it was my victory. Between my mother the enthusiastic assistant, more than eager to help me, I was outgunned. The assistant had performed miracles with tucking and nipping and hooks and things like that so now I was the not so proud owner of a white see through underwired bra that with the right tricks gave me the appearance of small but enticing breasts (with nipples showing through the flimsy fabric. My only consolation was that Albert NEVER was going to see anything more than the upper edge (wort case). My wardrobe was also extended with some stockings (black) and a garter belt (white). And why did the panties (white) have to be thongs? Most uncomfortable. At least Mom paid for “my” lingerie.

To bad that wasn’t the most embarrassing stop on our shopping spree. Mother dragged me in a drugstore.

- My son is going on his first date with a boy. I want to be sure that they have condoms if the football player my son is going to date has forgotten to bring any.
- MOM! I’m not THAT kind of boy!
How many times would I have to say that?
- What size?
- Peter, how big is Arnold?
As a matter of fact I had seen Arnold in a turgid state (once). That was another reason that THING never would come near a hole of mine (apart from me being decidedly heterosexual that his). That thing was huge!

My blush revealed the fact that I had had no intention of revealing.

- Extra large that is.

By that time I was wishing that I could turn back time and have gone to dad’s camp instead. At the time I didn’t reflect on why I didn’t wish I had checked what the lottery prize was before buying the ticket. Addled brain. Definitely addled brain.

This time I was expected to buy the offensive package myself.

At the beginning of the week, I wouldn’t have believed that going over to Sally and practice cheerleading with her, already changed into the tiny hotpants and crop top of course, would be a relief. Anything to get as far away from the risk of having to show off “my” new lingerire to dad. What I hadn’t realized was that that was only postponing things. Why did Dad keep repeating what a lucky guy Arnold was?

I was happy to learn that it was Dad that would take me shopping for a dress and shoes. How deluded of me!

- Peter, change into your new pretty lingerie.
- Why? I don’t need that to buy a dress.
- Don’t be silly. Have you never seen how girls are dressed? I had expected more of you.
-
OK. That could be interpreted in more than one way. I was not to ask for clarification. By now I had stopped to fight and just went and changed. The whole thing. Stockings, garter belt , panties and bra. I even did all the artful things to fill it out. Despite the hot day I chose to wear long trousers for some reason.

- Hello! My son has a hot date with a football player. He needs a sexy dress for the date.
- So this is Peter. I heard about it. Not many boys are as brave as he is. He will have a great date with Arnold. I had a date with him and he quite destroyed dating for me. No date after lived up to that one.

I recognized her. We had cooking class together. So what if I like to cook? Most great chefs are men. Manly men!

- His best feature is his legs. So something short would be best. And something that shows of the tops of his breasts. A little bit of tit-illation.
You could hear the pause. At the time I already had a very low opinion of Dad but that was a new low. I had not expected him to be that crude.

- Come here Peter. Get into the changing room. Get down to your undies while a get you a dress. I know just the right dress for you. It will knock the socks off Arnold. And perhaps something more as well.
Wink, wink. I felt nauseous. I did get undress while waiting for her.
- Oh my, what a pretty boy you are. The bra is to die for. How did you get those A+ breasts? Arnold will be drooling when he sees you in that lingerie.
- Arnold will never even see the edges of those things. I’m NOT that kind of boy.
How often would I have to repeat that?
- Sure you aren’t. That’s why you bought the ticket.
Wink wink. Please shoot me!

I have to give it to her though. The dress was just right. Just right if you wanted to seduce Arnold that is. I didn’t. Still I couldn’t deny that it looked good on me. Really good. Dad was right. I have great legs. And the way the top of “my tits” cleared the top of the dress was amazing. If anyone but me had been wearing this dress, I’d have asked her. Damn, I would have done it even if it had been a boy. That thought disturbed me given that I WAS going to wear it to a date with a boy.

- I knew this was the dress for you. Let’s show it to dad.
- Oh my Peter. This is so you. You are beautiful. Arnold is a lucky guy indeed.
I could see the glint in his eyes. He knew very well how much I hated this. Which of course only made him enjoy this even more.

- I’m sorry Sir. I will not allow Peter to buy this short dress if he insists on wearing garters and stockings. It’d be positively indecent.
I saw the disappointment in my dad’s face.
- Oh too bad. I’m sorry, Peter. I know how much you wanted to wear the stockings. But Betty is right. I can’t allow you out of the house dressed like that. Betty, do you have any long hold ups?
- We do. And, Peter, I saw you wore long trousers coming here. In this heat! Wouldn’t it be more comfortable with a short skirt instead?
-
At least I didn’t have to pay for the dress, skirt and stockings. I wore the skirt out of the shop. A strange feeling since I still wore the thong panties.

You know how people talk about male shoe salesmen? It’s true. At least in one case. He got his view up my skirt when trying on shoes. Only AFTER that did he suggest I put on the dress and everything to get the right feel (up). And did Dad give him a wink?

How can girls walk in shoes like that?

I had hoped for a tactical retreat home after that but we were ambushed. As we passed the salon the owner ran out at dragged us in. The owner gave an offer I couldn’t refuse. Well, an offer my father wouldn’t let me refuse. She offered a full makeover with all the trimmings as long as she was allowed to use before and after pictures in her advertising. The full work would be next Friday. The day of the date but I still left the salon with expertly applied but toned downed make-up. I was lucky in that this was the GOOD salon, the one Sally used. I could have done without the piercings and earrings though. And the necklace was totally not necessary. And I was getting a bit tired of hearing about how brave a boy I am. Not afraid to show the inner me. This is NOT the inner me! My “proud” father is lapping it up though. That malicious smile! I could kill him!

I was really starting to look forward to Friday. Don’t get me wrong. I was certainly not looking forward to the date. But the date meant that the whole thing would be over with. My parents would have got their revenge. I could stop practicing with the cheerleaders and things would get back to normal. Normal! What a lovely word. Come on Friday!

I owe it to Sally. She made sure she and not Mom taught me how to walk in those ridiculous shoes. She also assisted when learning to dance in those torture things. NO boy should have to learn how to dance with his father, at least not when HE leads. Not in a dress, stockings (long hold up) and in those menaces to public health laughingly called shoes but consisting of only a few tiny straps.

Friday night I was all ready for the big date. The one and only big lottery date. The date the whole school had been waiting for.

The salon had surpassed itself. I was cute. Really cute in a toned down way. The indecent dress was actually just on the decent side of the line after Sally’s help. My new earrings sparkled as did my necklace and anklet (While cheaper than diamonds Swarowski is damned expensive). Over my mother’s protests Sally had put in the finishing touches. This had really made us come closer. Maybe I’d be brave enough to ask her out? Yeah, ironic or what. The boy everyone lauded fore being so brave was too afraid to ask his best friend out. Sally even gave me a peck on the cheek after getting my breasts in order!

Sally and I were waiting in my room, giggling. Wait! Was I giggling? Anyway, I could hear Arnold ring the bell. I had been firmly told to wait in my room and give my parents time for the “meet the parents chat”. I finally was called down. I floated down the stairs in the most magnificent way. I damned well should, given the hours of practice. Arnold looked great. He met me and gave me a kiss on the cheek. Maybe this wouldn’t be so bad after all?

That was without taking my parents into consideration.

- Peter, I put the extra large condoms you bought in your clutch.
- Peter and Arnold, we understand that young people are young people and that hormones are raging. Still, we would prefer that if you have sex that you have it here at home where it is safe. Arnold, you are welcome to use Peter’s room whenever you want.
- DAD! I’m not THAT kind of a boy.

Hey, that is MY room they are offering. Why didn’t anyone ask ME? I wish I could have wiped that satisfied smirk off their faces. And I really hope that wasn’t a smother laugh from Sally that I heard from upstairs.

Exit one thoroughly humiliated, embarrassed and blushing (but very cute) boy.

Given the circumstances and especially what my parents had put me through, I had a great date. I remember thinking that apparently Arnold knows me better than I do myself (hm, that was an unsettling thought, if any).

I had not expected to enjoy a ballet, but Spartacus was not was I had expected. The force, the vitality, the virility … Hm. Yes ehm. I had never dined on such fine food. I had dismissed that as something for snobs with more money than sense. I was wrong about that. The dancing lessons had somehow stuck in my head. In short it was the greatest date I’d ever had. Let’s not get into such irritating details such as it was my first date. Let me rephrase it. It was a great date. We talked about many things and enjoyed all of them. Arnold was not stupid, so he had seen through my parents and their attempts to embarrass and humiliate me. I told him the background. We dissected them thoroughly. After that I relaxed and just enjoyed the evening. And it was some evening to enjoy. As promised he delivered me at my porch before midnight. Not much before midnight but still before.

- Peter, I had expected this date to be just for fun and for the cheerleading squad mone drive. I had not expected a boy to win. In hindsight I’m really happy you did. No girl could have been cuter. You are fun to be fun with. I knew that from the school paper but still… This was the first time I really enjoyed a date. Usually the girls are so focused to “land” me as their boyfriend that I lose interest halfway through even if I go throuth the motions, every time. This time was so relaxed. I was happy to discover that you like the same things I do. Who’d expected you to be a ballet fan. And you dance quite well. Sally?
- Sally.
- And you are just so cute.

At that point he gave me the goodnight kiss. On the lips. Intensely. I just let myself be swept off my feet. Quite literally as he lifted me up as he kissed me. I was still quite giddy when he put me down and asked

- Peter, I have never had such a great date as with you. Will you go on another date with me tomorrow?
- Eh, yes
Still giddy I hadn’t really heard what he’d said.
- Great! I’ll pick you up at ten tomorrow morning. Wear something informal. I thought we’d just spend time together doing things just the two of us, together. Still, if you have comfortable skirt please wear it. Don’t tell anyone I said this but you have the prettiest legs in school.
-
I finally got what I had agreed to then. Strangely enough, I didn’t regret it.

The door opened and revealed a couple of parents that judging from their smirks had seen the kiss even if they hadn’t heard the conversation.

- Mr and Mrs Smith, your have raised a son that is a delight to date. We had such a great date that I asked him out tomorrow again. He graciously accepted. For the whole day so I expect that we will be back earlier tomorrow evening. Perhaps even in time to have dinner with you. And regarding sex, is the offer about Peter’s room still open? I assume it’s OK if I stay the night?

I could have broken out in loud cheers when I saw my parents faces when they heard that last. Arnold really knew how to troll them.

For he WAS trolling them, wasn’t he?