Timmy Gets a GirlbyBakeboss©
The day my life changed was a day of infamy and one I shall never forget. Although it happened years ago, every detail was fresh in my memory as though it happened yesterday. Almost daily, it replayed in my head as if my mind enjoyed torturing me.
Freshman year of high school and although I'd discovered girls I was far too shy to do anything about it but dream. It was a Thursday and as with every Thursday it was co-ed gym day, when the boys and girls of the two classes were put together for some unknown reason, by the department of education. One of the students fell and scrapped his knee or something and as coach took him inside for treatment, the rest of us mingled around the track. As luck would have it, I was standing next to Darla Powers the hottest girl in our grade. Whereas most of the other girls were as yet to have the chest of a woman, Darla pushed out her gym top almost obscenely. I know a lot of the boys called her Darla Double D but never to her face. She also had long blond hair that she wore in a ponytail every day, and deep blue eyes that I swear could look into your soul.
Not that I knew Darla but I did have a class with her and using that as an opening I asked her about the test we'd had the previous day. She even smiled when I made joke about how hard it was and encouraged I blurted out an offer of a date. She said, I don't know Tim but then stopped talking so I braved a look into her eyes and saw that she was looking past me, was she looking to the future, wondering what our kids would look like just as I had many times? No, she was looking at Bobby Bragan who had snuck up behind me to pull the most humiliating of all schoolyard pranks, a pantsing. I was still lost in thought so my gym shorts and underwear were around my ankles before I could react. As I struggled to pull everything back up, I heard Darla laugh and then ask Judy Inglehart if she'd ever seen such a small thing. I tried to turn around to hide myself but in doing so I got twisted up in the clothes around my shoes and fell flat on my back. My underwear were now entwined in my shorts so bad I couldn't get them over my knees, so I had to stop and straighten them out before I could put them back. By now the whole class was standing around watching me as I flopped around on my butt like a flipped over turtle. Everywhere I looked people were laughing at me, red faced and totally humiliated I ran to the lockers where I changed back into my clothes.
From then on, every time someone wanted to be mean, they called me Tiny Tim. Every time I saw two people talking around me, I was sure they were joking about the size of my genitals. I guess, before that day I'd never considered the size of my penis, I knew I had one and if I had to guess I would have said average in size. I never looked at the other boys, not in the locker room or the shower or any other place, I mean that'd be gay wouldn't it? But after that day on the track, I began to compare sizes wherever I could sneak a peek and Darla had been right I was smaller than the rest of the boys. Because of that day, I never dated in high school, I was too afraid the girl would know about my curse.
As soon as I could, I moved from our small town to LA where even if I couldn't solve my size problem at least I could hide it from the world. I moved into a small apartment complex and was ready to remain alone for the rest of my days. With no life, my routine became the same week after week and so on my day off as always, I took my washing down to the laundry room. Imagine my shock as I walked in on a girl dressed in baby doll pajamas with her head in the dryer and her rear end pointed in my direction. The material of her nighty was so thin and gauzy I could see right through it and even saw the crack of her ass. When she heard me, she turned around and I saw a middle-aged lady of indeterminable years, but all I really noticed were her dark brown areolas showing through her nighty .
"Excuse me, I didn't think anyone would be here, I'll come back later."
"No, don't go, this is all so boring, I could use the company, why don't you stay."
She told me her name was Gina then asked my name, her open manner put me at ease and even though she was more than half undressed she was not shy at all. She reached into my basked and pulled a pair of my underwear out,
"My god Timmy, you're still wearing tidy whities? I like my men to wear boxers so I have easy access to them."
My faced burned red with embarrassment but somehow I managed to say that maybe I'd better buy some boxers then. I put my clothes into the machines and as I leaned back against the folding table she asked me to help her fold her laundry that was dumped into a heap on the table. She picked up a pair of panties and handed them to me, they felt as if they were satin, so soft, and tiny, I had no idea how to fold such a garment.
"I believe a girl should wear pretty panties, don't you?"
I could only nod as I stared at the all the undergarments on the table.
"As you can see I've gotten a little behind with my washing, maybe if you'd help me all the time I do it more often."
When we finished she invited me to her apartment for coffee and then once inside she said,
"I think I may have something for you."
She went to her bedroom and then returned with a pair of men's boxers covered in pink hearts with arrows trough them.
"I bought these for an old beau but he refused to wear them, you know how men are about pink. Let's see if they fit."
She dropped down to her knees in front of me and began to unfasten my trousers. I tried to stop her but she had my pants opened and half way down my legs before I could do anything. Well I decided it was too late now so I might as well face the music.
Gina almost squealed with delight when she saw my member all flaccid and tiny. I apologized for being so small but she stopped me before I could finish.
"I love little peckers, they're so much fun to play with," and she took me in her hand and kissed the tip. Now fully aroused I stood up almost twice the size of when I was flaccid.
"See honey you're a grower not a shower."
All I could think to say was I thought women liked a man with size.
"I'm not like other woman," she said and then put me in her mouth.
Gina looked into my eyes as she made love to me with her mouth; with a big slurp, she licked the ring around the head of my dick. Her mouth was so wet that her saliva trickled down my shaft and soaked my pubic hair. When she began to caress my balls, I came into her mouth and she swallowed every drop. Right then and there, it was the first time I had ever been touched by a girl, my first time of having oral sex and my first climax brought on by something other than my fist. After my climax, I had another first as I tried on my new boxer shorts. Maybe it wasn't love but it defiantly was lust and I wanted to reciprocate but she stopped me, telling me she just wanted to cuddle for a while. We lay together on her couch where we made out and then she lifted her nighty allowing me access to her tiny but perfectly shaped breasts. Those brown half dollar sized areolas I'd been starring at through her gown were now available for my lips to kiss.
I was so aroused; I became brave enough to beg her to let me please her, even if only with my mouth as she had done for me.
"Tim I told you I'm not like other girls..."
"I know I know I think that's why you turn me on so."
I reached between her legs to caress her sex only to discover what felt like a penis instead of a vagina. She smiled when I looked at her, "See I told you I was different."
"But but you've got a dick, I sputtered, how can a girl have a penis?"
"You wanna see it, go ahead pull my bottoms down and look for yourself."
Afraid of what I'd find I slowly lowered her nighty as she raised her butt up to help.
Let me say right here that I am not homophobic but then I'm not homoerotic either. It's not that I'm against men it's just they don't turn me on. All of my fantasies had involved women but here I was starring at Gina's penis and it was one of the sexiest moments of my life. It was even smaller than mine and with no hair around it, made her appear almost childlike. I didn't even ask her for permission and leaning down I put her soft little worm between my lips. The sensation of her growing, at first firm and then hard in my mouth sent shock-waves of passion straight to my groin.
"That's right Timmy, suck mummy's clitty, make her feel good. Do it good and mummy will give you a special tasty treat."
I knew she was talking about her sperm but I didn't care I wanted her special treat and I began to suck with abandon and I felt her grab my hair and hold me in place. At the time, I wasn't concerned about the taste and I never even thought about the consistency but the shock of her spurting on my tongue brought me back to earth. Although the taste was not vile, it was not pleasant in any way, but it was so thick it coated my tongue and so I couldn't get it down my throat. As Gina softened in my mouth, I began to concentrate on her penis rather that her issue and I relaxed a little. Now instead of holding on to my hair she was running her fingers through it and cooing about what a good boy I was being.
Gina and I have been together since that day and my life has never been so close to perfect. That horrific day no longer haunts me because my girlfriend calls my penis cute instead of tiny. Yes, my girlfriend has a dick but she also has nice perky tits and full red lips that kiss me all over. Her curves could never be on a man's body and to me she is all woman no matter what's between her legs. One more thing, she tells me she is going to bring home a harness and prong to take my virginity, I just hope she's gentle.