I was excited about the idea of going out on a real date with her despite all she had done to me. I have already explained that I was in love with her as only a 14 year old boy could be in love.
She was giving me the details of when and where we would meet, I would come to her house and her Mom would drop us off. It wasn't a formal dance, just a local band playing the hits of the day so I should dress casual but neat. The tickets were three dollars and I would buy our tickets at the door.
I eagerly agreed to all of this then just before she hung up she dropped the bomb on me.
"Make sure you're wearing that pretty bra and panty set you stole from me under your clothes", I heard her laugh, "I'll be checking when you get to my house."
"Aw c'mon Gail please", I pleaded, "don't make me wear that stuff. I told you I was sorry, you already um...you know...punished me".
"Just do it, sissy", she said crisply, "or Mom and Dad get the picture of you wearing my bra with your little bitty peepee sticking out."
I wsa trapped and felt tears welling up, "Please...OK...I'll do it....just don't show that picture to anyone."
"I bet you're crying again", she laughed, "god what a sissy you are! Be here at 6:45 on Saturday. Don't be late. Goodbye"
Before I could even say goodbye I heard her hanging up.
Instead of excitement about the dance I now dreaded what she might do, but I dreaded it all the way to the bathroom where I locked myself in and stroked my little dick until the first spurt hit the opposite wall, it took all of about 15 seconds to cum.
On Saturday I carefully picked out heavier clothes that I thought would conceal what I was wearing. I got instantly hard as I slipped on the panties and then clipped the bra around my belly before pulling it up and slipping my arms through the straps. Using a handful of toilet paper I jerked off for the second or third time that day, I was 14, remember, I could do that then.
I put on a pair of loose jeans and a dark colored collared shirt, I added a sweater over the top of that, feeling confident all was concealed.
I arrived at Gail's house at 6:40 making sure to give myself some extra time so as not to annoy her. She met me at the door with a beautiful smile and a short kiss on the lips.She slipped her arms around me and I felt her trace the bra straps with her fingers.
"Good boy",she said, taking my hand and pulling me into the house.
Her outfit was typical for her, a short gray skirt with a pretty print blouse. She looked incredible.
Her Mom was always nice to me and told us we made a nice couple, I thanked her as behind her back Gail was rolling her eyes. She bundled us into the car, Gail sat in front as I sat alone in the back, for the short drive to her school.
When we arrived Gail assured her mother that we would be fine walking home later and we would be home no later than 11 o'clock. Her mother reluctantly agreed and wishing us a good time drove off down the road.
I had passed by Gail's school a few times but I really didn't know anyone who went there other than her.
We walked to the entrance and I bought our tickets while Gail stepped away to see some of her school friends.
When I turned to look for her I saw her talking to a couple of girls who were looking my way and laughing. I hesitantly made my way toward them.
Slipping her arm around my back and laying her hand directly on the bra band she said, " Oh here he is, I'd like you to meet my friends Lee and Laura".
The girls said "Nice to meet you." before dissolving into giggles.
Gail just smiled, took my hand and led me to another group of girls.
"Hi ladies," she said, "this is the boy I told you about." turning to me she said "This is Christine, Ronnie and Kerri."
They all laughed as they said how nice it was to finally meet me.
Gail took my hand and lead me away after telling the girls we'd see them later. I said something unintelligible provoking further giggles from the girls.
"Why are they all laughing at me Gail? You didn't tell them about my wearing...you know..this stuff did you?"
"You mean that you're a sissy wearing a bra and panty set that you stole from me? Why would I do something like that?" she leaned over and kissed me hard on the lips and slipped her tongue into my mouth as her hand rubbed over the bra outlines through my sweater.
"C'mon," she said, "let's go on in. I want something to drink and I feel like dancing"
We entered the dance as the band started playing some rock song I don't remember. Gail started swinging her hips in time to the music and asked if I would dance with her. I told her I really didn't know how and she shrugged and pulled me onto the dance floor anyway.
I tried to follow her moves as she danced nut I was so nervous that I just made a fool of myself and embarrassed her.
"Fine," she said, "you go stand over there and wait for me and I'll dance with my girlfriends"
I stood near the refreshments as I watched her and her friends dance. I was painfully aware of how tight the panties were as they were holding my little hard-on tight against me thankfully not exposing my arousal to all around me.
As I stood alone I observed that most of the girls were dancing but most of the boys were not. The boys were clustered in groups laughing and yelling and making lewd comments about some of the girls, you know, being teenaged boys.
I didn't know any of them and none looked interested in meeting me so I stood apart and alone watching the girls move so smoothly on the dance floor.
After about a half hour Gail waved to me to come to her. She told me she and her friends were thirsty and would I be a sweetie and bring the three of them some drinks.
Blushing furiously I rushed away to the refreshment table and poured several glasses of punch and carefully carried them back. The other two girls took theirs but Gail told me to take hers back and put more ice in it and I of course hurried to do that.
When I returned with her glass she smiled at the, now laughing, girls and simply said "See, just like I told you".
Turning back to me she said "OK, that's all, I'll call you if I need you"
I heard the laughter as I walked back to where I had been.
After about 10 minutes the girl she had introduced to me as Kerri walked up to me.
Having a good time?" she asked "It looks like Gail's been ignoring you."
"No I'm fine....um it's just that I ....um...don't dance very well"
Before I knew what she was doing she had slipped her arm around me and said, "That's OK, I'm sure you excel in other areas"
I felt her hand slip over the bra and hoped she hadn't felt it. I almost jumped out of my skin as her hand slipped back up and stopped, her finger tracing the bra strap.
"Oh my,"she said with a big grin on her face, "what have we here?"
I tried to stammer something while trying to walk away but she wouldn't let me go.
"You know that Gail has told just about every girl here that she was bringing a sissy boy with her tonight, don't you?"
I couldn't answer as my face was pure red with embarrassment.
"Haven't you noticed all the girls pointing and laughing at you?"
"I um thought it was...something...um I wasn't sure...."
" I'll tell you what you seem nice and I don't think what Gail's doing to you is fair, come with me and we'll find a quiet place and talk, OK?
Not waiting for my answer she took my hand and pulled me behind her toward one of the exit doors. I turned and saw Gail watching us leave before turning back to her friends, dancing and laughing.
Instead of going outside Kerri led me upstairs into the school. It was a little eerie being in the empty hallways of a school. The band playing downstairs was reduced to a muffled echo.
She led me to a door marked teachers lounge and pushed me inside.
I was confused and didn't know what was going on.
"You know" Kerri said, "all the girls are laughing at the idea that you're wearing girl's undies. I know I felt a bra under that sweater are you wearing panties too? Gail said you would but I can't tell through those jeans".
I was panicked, oh my god I thought, she'd told them all!!! I was the reason they were all laughing....they all knew my shameful secret. I burst into tears and fell to my knees sobbing, I had been completely betrayed by the girl I loved. How could I even show my face to get through the crowd to the door.
Kerri knelt beside me, she was stroking my hair and pulling me toward her. She held my head against her chest as I cried and cried. She made some soothing noise telling me I'd be alright and that I'd done nothing wrong. She kissed my hair a few times slowly moving from my head to my forehead.
"It's alright baby" she cooed at me, "Its alright".
Slowly she slipped down and kissed me lightly on the lips. I was still crying lightly as she kissed me again, this time with a little more pressure and her tongue touched my lips.
Breaking the kiss she looked at me as she wiped the tears away. I was so confused that I didn't know which way was up.
"Better?" she said smiling.
"A little, I guess" I answered through sniffles.
She pulled me tight against her and kissed me with all she had, her body pressing against me as her tongue explored my mouth. Her hands slipped under my sweater and felt my chest through the bra before slipping down quickly under my pants and feeling the soft panties I was wearing.
"The others may laugh", she said looking at me with lust filled eyes "but I think this is just sexy as hell, Can I see what you look like in your undies, please, please."
She got up and moved to the door, realizing it had no lock she pulled me into the bathroom and locked the door.
"Now," she said, "we're alone and no one can see. Please can I see?"
My head was spinning and when I didn't answer she started pulling my sweater over my head.
What the hell I thought, might as well. She seems like the only nice girl here.
So I nodded my head as my face blushed crimson and started to unbutton my shirt slowly revealing the yellow lacy bra.She licked her lips as she reached out and ran her hand over the empty cup. She asked me to turn around so she could see and I slowly turned until I faced her again.
She looked into my eyes and said quietly, "Can I see the rest too? Please? Pretty please?".
Nervously with shaking hands I unbuttoned my jeans and pulled down the zipper, they fell halfway down my legs on their own as they were a little big on me. She took a deep breath and slipped her arms around my waist as she leaned forward and kissed me. I was rock-had in my panties as her hands roamed over my body.
She stepped back and looked me up and down before settling her gaze on the small bulge in the front of the panties,
"You look so pretty and sweet in those undies, I just have to get a closer look"
She dropped to her knees and pulled my panties down so that my little dick was sticking straight out at her. If I hadn't jerked off so many times today I'm sure I would have cum right there.
Reaching out she took my dick between her fingers sending electric shocks through my entire body, then she shocked me by taking my entire dick into her mouth,
It was bliss, hot, wet, her velvet soft tongue licking the underside of my dick and it took about 5 seconds before i moaned and warned her I was going to cum. She kept me in her mouth as I shot my load into her and she swallowed it all, sucking on me for another minute as I shuddered with the aftershock of what had just happened
As she leaned back she took my tiny soft cock between two fingers.
Smiling at me she said, "It's so cute and small, the last guy I did that with almost choked me to death but yours is so nice"
She got up and kissed me again and then I realized that I could taste myself on her lips. I didn't care. I had gotten a blowjob! An actual blowjob from a pretty girl! I was in heaven.
"We better get back to the dance", she said "Gail will probably be looking for you, why don't you give me your number and maybe we can get together sometime."
We stepped back out into the teachers lounge and she found a pen and paper and wrote down my number.
She helped me straighten my clothes and, taking me by the hand, we walked back to the dance. I saw Gail was still with her friends and I saw some girls notice me and whisper and laugh but I was above it all.
Kerri squeezed my hand and stepped away. She smiled and mouthed the words "I'll call you" before turning and joining the crowd.
I resumed my waiting position and before long Gail joined me and said she was tired and wanted to go home. She guided me through the crowd to the door with her hand on my back holding the bra band.
I heard the laughter fade as we walked outside.
She slipped her hand down the back of my pants and rubbed my ass through the panties as we walked home in silence. When we got to her door she kissed me and gave me a strange look, I just smiled back at her.
"Go home sissy, I'll call you soon".
As I was walking away she called out to me, "Make sure you hand wash your panties sissy, a girl should always have clean underwear."
Thankfully no one was out but I'm pretty sure she hadn't checked before she had said that, I don't think she would have cared.
When I got home I went straight to the bathroom to slip out of the bra and panties and to take care of another stiff little dick, by now I was bearly shooting anything at all.
I slept well that night.
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How very exciting!!!!!! I LOVE this!!!!
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