2017 true gay stories: Highschool exploration – Chapter 2: The shopping trip with a surprise
True Story, Anal, Blowjob, Consensual Sex, Cum Swallowing, First Time, Humiliation, Transgendered, Transsexual, Virginity
Cindy helps me with some clothes and gets a surprise.
Thank you for reading my story. This is a true story as I remember it. This story may not be for Everyone.
Wednesday morning I started to think of a costume for the party. Jim is going to be Batman and his girlfriend will be there to. I needed to talk to her and find out what her costume will be I thought to myself.
I finally found her at lunch time in the school cafeteria. She was with Jim and a bunch of other students. Cindy Tompkins was just a regular girl. I mean nothing to special, average looks, small bee sting tits, shoulder length bleach blonde hair. She’s really got dark brown hair and has to die it often. She stands 5’3” tall about 100 pounds or so and is very shy. It’s amazing how she got the nerve up to even ask Jim out in the first place.
I figured I might as well just ask her so I walked up to their table and said.
Hey guys um I don’t know what kind of costume to wear to the party this weekend. Could you guys give me some ideas?
The look on some of their faces told me I probably made a mistake asking.
Embarrassed and quiet nervous I said um never mind. I turned and headed for the door. I could help you if you want that is Cindy says.
I stopped at the door and waited for someone to make fun of me. That’s a pretty good idea Cin. Maybe you and a few of your girlfriends could do something for this loser.
I smirked a bit. I’ll see you at the mall around 4 Cindy told me and with that I left and headed for my next class.
The last bell went off and I was on way to the mall. I ran into Jim just outside the school doors. Hey Todd. Don’t get any stupid ideas with my girlfriend got it. Ya no problem Jim. I just don’t know what kind of costume to get. Well you’re a fairy so I don’t know, there’s an idea he barks. Anger in his voice was very dominant suddenly. I was pushed from behind to the ground by some of his minions. Jim and his buddies left me there.
I got up and got my mountain bike and headed for the mall.
I found Cindy at the food court.
So what kind of costume do you want. I was thinking of something else, not paying attention to the conversation.
Earth to Todd.
What oh I don’t know I said. Jim suggested a fairy.
What you a fairy!! She laughed.
Why would he say that?
I don’t know, probably just to be mean I guess.
She was quiet for a moment. I looked at her as she said you know with a bit of help, you could pull this off.
I laughed and said you’ve got to be kidding right.
Not many people know I like guys and I wanted to keep it that way I thought to myself.
No really Todd! Not to be mean or anything but you got the perfect body for it. Your slim, your a bit short and you already have longer hair. If not a fairy then how about a… no you’d never go for it, nevermind.
Peaking my interest i look her in the eyes and say what. What are you thinking?
A whore. I’d help you with everything you’d need she said as she grabbed me by the hand and tugged me through the mall.
Are you nuts I said but she was on a mission and I really don’t think she heard me at all.
Cindy, I’m not going to…
She stopped at a girl’s clothing store and blurted out my friends told me about this place, come on let’s go. And she pulled me in with her.
The store was filled with all kinds of short and skinny clothes.
I found it odd that the attendant was an older lady of about 35 to 40 years old but she was dressed like a teen.
Hi I’m Tammy, can I help you with something she said. Ya um we need to make him into a hooker. Do you have any ideas Cindy says.
Excuse me but I’m not doing this I mean do I even have a say.
Tammy and Cindy look at me and then each other again and Tammy says of course I can help, come here boy she says to me.
I just looked at her, kinda dumbfounded. Really? You can do something for me? Um I’m a guy I said sarcastically. This isn’t a store for guys!
Cindy walks over to me calmly and whispers in my ear. Do you want me to tell Jim that you’re disrespecting me.
Um no. But.
She cut me off saying then you’ll do exactly what I tell you. Do you understand me.
I stood there silent for a moment.
Todd? Do you understand?
Yes. Yes I understand you.
Good. Now follow me. And she turned back towards Tammy with a smile.
So I was thinking of making him into a hooker. What can you do for him?
Well come here so I can get a look at you she said. I walked up to her embarrassed and she looked me up and down.
I’m gonna need some measurements. Please take your shirt off.
What? Here in the open.
Cindy cleared her throat.
I pulled my t shirt over my head and through it to the waiting chair.
Tammy started to take the measurements needed and then said to step into the dressing room and get undressed. Cindy told me not to lock the door.
I did as I was told without question this time thinking at least I was out of sight.
A short while later Cindy opened the door to see me sitting there in my boxers.
I thought Tammy told you to strip she said.
I did suddenly realizing as i had my boxers on. You mean naked? I asked.
She just looked at me. I looked down and slowly slid my boxers to the floor. She giggled out loud and said well we won’t have to worry about that little thing now will we. My heart sank down into my stomach.
I took the clothing she had and looked at them. There was a bright pink bra and panty set along with a matching garter belt.
Well? Whatcha waiting for. Put them on she said.
Again I did as I was told and waited for her to return but she didn’t for a bit. Are you done in there Cindy calls. I mumble ya.
Well I’m waiting. Get out here. But Cindy I cried.
I’m going to count to three.
This is ridiculous I thought to myself.
Seriously I said.
I open the door and slowly exit the booth.
At first there’s silence as Tammy and Cindy are standing there looking at me.
Then Tammy says the bra doesn’t fit right. You’ll need this one instead as she handed me another bright pink one. I turned to go back into the booth. Tammy graded my arm and said let me help you. I stood still as she unhooked the one I had on and pulled it from my almost hairless chest.
Cindy, he’s got some hair in his arms, legs and chest. You’ll have to get rid of it.
Oh ok. I’ll make a note of that. Thanks Tammy.
She helped me with the second bra. This one fit much tighter and squeezed my scrawny chest together giving me the appearance of a cleavage. That’s when I sprang a boner. A micro boner as I’m only about 2” hard. Cindy noticed it first and grabbed a wooden measuring stick and whacked my dick with it hard causing me to yelp in pain. What the fuck? I yelled.
Cindy just glared at me which told me exactly what to do next.
Holding my quickly shrinking dick in my panties I say. I’m sorry. I’ll try not to do that again.
You fuckin better not you little weasel she says as she stands no three feet in front of me. Now put your hands down beside your body.
I did as I was told and Cindy told me that I looked great in pink.
Stand right there she told me and she disappeared into the store.
Thank God there was no one else in the store I was thinking when a group of people entered the store. I ran back to the booth and closed the door. I could hear people outside. They sounded like they were right outside the door. I reached out and locked the door. A short while later there was a tug on the door followed by a fuck my nail. Unlock this door right now Todd. I did as I was told again. But she didn’t come in.
I called out to Cindy but got no response. I could still hear other people outside.
Get your worthless little ass out here right now a very angry Cindy yelled.
I quickly got my sweatpants and t shirt on over the under garments and opened the door. Looking out first to see I was partially clear. I walked up to Cindy. She looked at me. She was more than just mad at me. Holding up her middle finger she screamed at me. Look what you fuckin did to my nail.
I’m sorry, please I’ll pay for it.
Your fuckin right you will. Why was that fuckin door locked. I told you to leave it open.
Now there was a bit of a crowd watching us.
I..I.. I thought.
No. You don’t think Todd. You do. Got it.
Looking down feeling very embarrassed I quietly say yes.
This seemed to anger her more. She screamed DO YOU GOT IT?
Yes I said loud enough for everyone to hear.
Now get those boy clothes off right there and right now she demanded.
Without hesitation I did as she demanded.
The whole store seemed to go silent as I stood there in the bright pink bra, garter belt and panties. I could feel people’s eyes all over my body. I was so embarrassed I wanted to cry right there and then but somehow I held it together.
Cindy handed me a bright green garment and told me to put it on. I slipped it over my head but it would not pull down over my shoulders. Tammy told me not to squirm so I stood still as she helped me. The minidress fit very tight but as small as my dick is it still showed through the dress.
We simply can’t have that Todd. You’ll have to pull it down and tuck it between your legs.
I attempted to do just that but with no success.
Tammy whispers something into Cindy’s ear. Cindy steps back looking at Tammy and says really. No way. I mean your a…
She stops talking and just stares at her.
She gets this smeek like grin on her face and says pérfict. This is going to work out even better then I thought. Go ahead.
Tammy turns to me and says step into the booth and pull up your dress and drop your panties.
I didn’t know what was going on but I did as I was told. Tammy got some masking tape and told me to pay attention as she was not going to explain this again.
Sit down honey, I’m going to show you how to tuck your junk properly.
What? I said.
Look maybe I should just show you. Would that be better.
I repeated my question. What? Show me what?
She pulled up her skirt and yanked her panties down to her ankles. When she stood up again, I thought I was looking at a nicely trimmed pussy. My little boner was back. But then something happened that would change my life forever.
She spread her legs and reached in with her index finger and pulled her cock out. As she did she said this is a properly tucked cock.
I was beyond stunned. I was mesmerized by what I was staring at. Tammy stood directly in front of me. I was turned on to the max. It just happened. I leaned forward and sucked her cock head into my mouth surprising her as she moaned rather loudly. She didn’t pull away so I continued sucking her off. Not using my hands at all. Tammy grew in my mouth as I sucked and swallowed.
Somewhere along this process the door was opened and Cindy was watching us but I didn’t know it.
Tammy says softly to take my panties off and turn around. Without missing a stroke of her cock with my mouth I pulled my panties off and let them fall to the floor.
Tammy was at least 7.5” long and slender. I could swallow her down with ease and did so many times until she grabbed my head and picked me up. I spun around and bent over expecting her hard cock to penetrate me but instead a felt her slobbering tongue push into my ass. She spent the next few minutes tonguing and probing my ass.
Just when I thought I was gonna cum she stands up behind me, lines up her cock, grabs my forearms and plows it balls deep causing me to stretch out in pain.
I didn’t care at that point who or what was watching, I was enjoying the first ass fucking of my life. Ya I did play with my mom’s dildos and vibrators and her double dong was a lot longer and thicker but this one was real and bareback. I swear I could feel each thick vein in her pulsing a throbbing cock. But alas nothing lasts forever and Tammy grunted and filled my ass with her hot gooey seed. I was even more amazed to see that I’d cumed without touching myself at all.
Tammy stepped back a little and I stood up and turned to face her. She was just outside the changing room booth. Cindy was just standing there with her jaw on the floor. Cindy spoke first.
Holy fuck Todd, I can’t believe you just did that. Like wow. You got fucked in the ass.
Boi pussy Tammy said.
Cindy looked confused but then I don’t think she cared.
We got shopping to do, can you show him that tuck thing Tammy. Cindy asked.
Sure. Ok look Todd. You wrap a piece of tape around the head of your penis like this. Then you pull it back like this and tuck the end of the tape in your ass like this. Now you try.
As I did what she showed me she kept saying. Ah hum yep that’s right you got it. But the tape kept falling out of my used ass so she said I needed something. She walked up to Cindy and whispered something in her ear. Cindy looked confused but said ya, right here reaching into her purse and grabbing a tampon.
She soaked it in some water from a bottle nearby then wrapped the tape around the string and I wrapped the tape around the head of my little dick and Tammy inserted the tampon into my ass.
There, you’ll never know this gurl has a dick.
Cindy told me to pay for the clothing I was wearing out of the store but Tammy wouldn’t have it. She slipped me her phone number and whispered in my ear that she really enjoyed herself, you really do have the tightest boi pussy I’ve ever fucked, and wanted to meet up with me again.
We kissed and I told her I would be calling. Then we left.
Cindy was in a hurry as it was already just after five and her parents were expecting her for supper at six so she told me to go home and she would get the remaining things herself.
I said ok and rode my bike home in my new clothes. It’s a good thing everyone was either at work or out when I got home.
If you want to know what else happened then please comment and vote. Positive or negative. It up to you.
And thank you in advance.
Other Chapters: Highschool exploration – by toddh1970
- Highschool exploration - Chapter 2: The shopping trip with a surprise
- Highschool exploration - Chapter 3: Todd gets feminized
- Highschool exploration - Chapter 4: Finally the party