My First Time in Panties Pt. 02

Note: All characters are over the age of 18.

I could see my mom pull into the driveway as I eagerly awaited on the couch. I tried to pretend to watch the tv, but I watched every movement. I could feel my erection stretching the seem of my pants when I saw her pull out a large pink bag from Victoria's Secret as she exited the car.

When she entered the kitchen, she called, "James, come see all the pretty panties I got for you!"

I turned red in embarrassment, but at least remembered that Rachel was still over at her friend's house. I made my way into the kitchen and saw my mom in a pale blue sundress with her blonde hair in a ponytail. She waved me closer with her hands and handed me the bag. I was shaking from all the emotions-excitement, nervousness, and a large amount of embarrassment.

My mom snapped me out of my trance saying, "Go ahead, and look inside."

I reached my hand into the bag and through the pink tissue paper, feeling an assortment of different textures underneath. I pulled out the contents of the bag and felt the same excitement I had when I first opened my mom's underwear drawer.

I placed the pile of panties on the kitchen table and held up the one on top - a red cotton thong with "Victoria's Secret" printed across the waistband.

As I looked at them, my mom said, "I made sure to get mostly panties that won't show under your clothes. That way, you can wear them out without worrying about panty lines."

I dug through the rest of the pile of panties, holding each up. There were five in all: a hot pink lace thong, a black lace cheeky, a nylon floral pattern bikini, a pale pink Brazilian style made of satin, and the red thong I already admired.

My mom remarked, "Now that you have your own, no touching your sister's or my lingerie. If you'd like anything else, please just ask. As long as you do that, your panty collection will be our little secret."

With that, she threw the bag into the trash and I brought my new panty collection into my room. I put my panties in the far back of my underwear drawer, only able to be viewed by pulling the drawer all the way to the rear.

For the next week, I wore my panties every night. I loved all the different textures and sensations I felt from each different one. I thought about what outfits I'd wear each with and which set a girl would wear for different occasions. I felt the need to try on other girl's clothes but didn't want to break my mom's one rule.

By the time Friday afternoon rolled around, I got home from school and my mom let Rachel and me know that she'd be going out for her book club that evening. Rachel let her know that her friend Kristin was going to spend the night because of the football game at 1 the next morning.

Kristin is Rachel's best friend and fellow cheerleader. Like my sister, she's a petite five-foot-five. She's of Asian descent and reminds me of the actress Brenda Song. She's been good friends with Rachel since middle school and I've had a crush on her since around then. I was pretty excited to hear she'd be spending the night.

After my mom headed to her book club, I went back into my room to put on some panties. I was so turned on about Kristin coming over that I had to distract myself. I put on the pink lace thong because it gives me serious girly sleepover vibes and I wouldn't worry about them showing through my black sweatpants.

I did some homework in my room and then made my way downstairs for dinner. When I entered the kitchen, I saw Kristin and Rachel chatting and eating pizza. I walked past them and opened the fridge to pour myself some lemonade. As I took out a glass, Kristin asked for one as well.

While I was pouring, I heard my sister say, "...Brad has been so horny lately, I literally can't handle his libido sometimes."

I was so distracted by what she was saying that I overfilled my glass, spilling lemonade down the kitchen counter and onto the floor.  Trying to hide my eavesdropping, I quickly grabbed a paper towel and bent over to clean the spill from the ground.

When I touched the lemonade, my sister let out a shriek and shouted, "Oh my god. Are you wearing one of my thongs James?"

I snapped back to attention and realized that my shirt must've flown up when I bent to clean the mess, revealing the pink waistband of my thong.

Once turned around, I shook my head and stuttered, "I promise I'm not wearing your thong Rachel, it's mine."

"What are you talking about?" she asked.

I explained to her and Kristin how I wanted to try some new underwear and that mom bought me some from Victoria's Secret to see if I liked them. In the back of my mind, I prayed that they wouldn't probe as to why.

Kristin asked, "And how do you like wearing those pink panties, James?"

"I like them," I muttered.

"Did she get you anything besides panties?" asked Rachel.

I shook my head no and Kristin let out, "Let's dress your brother up, Rachel. It'll be fun!"

Rachel nodded in agreement and ordered me to go upstairs.

I sat on my bed waiting with excitement. I could feel my boner pop out of the thong despite trying to tuck it in when I pulled it on. I could see the tent formed in my pants. When Kristin came in, she did too. Kristin told Rachel to pick out a dress and shoes while she helps me pick out the underwear.

She turned to me and said, "Now Jamie, if we're going to get you all dolled up for prom, we can't have your dick poking out of your dress now can we?"

"Pull your pants down so that I can see how big our problem is going to be."

I obliged, revealing my lacy pink thong and fully erect cock.

"Cute panties, Jamie, not a bad cock cock, either."

Kristin made her way to me. She was wearing black capris leggings with a matching black tank top. The leggings really accentuated her butt and I couldn't help but stare. When she got to me, she ran her hands down my chest and along the waistband of my thong.

She whispered in my ear, "When you go to prom, your date is going to expect you to put out. At the very least, you have to give him a blow job."

My eyes widened at the thought, and I felt my penis twinge. Kristin started to lightly rub her hand up and down my shaft I could feel my cock stretch as she brushed against the lace waistband with the other one.

She continued, "At last year's prom, I was such a slut. I took two guys on the football team at the same time."

She started to quicken her motion along my shaft.

"Jamie, it felt so hot. One guy was pounding me from behind while the other was thrusting into my face. I could literally feel the balls of each of them crashing against my cheeks on either end."

With that, she got onto her knees and licked from the base of my shaft to the tip After another small luck at the tip, she impressively took my whole cock into her mouth. She slowly pulled her head back while she ran her tongue underneath.

She looked up at me, and slowly rubbed her hand up and down the shaft saying, "I'll show you how to give a good blow job Jamie. The last thing I want is for you to be a knockout-looking date, but not be able to please your man."

She led my straining cock back into her mouth and this time she kept the hand on, circling around while she bobbed in and out. It felt unlike any sensation I've ever had. My eyes shot from the perfect view of her ass to her sucking on my dick. Occasionally, she'd look up at me and I could see how much she loved sucking cock from her eyes.

When I felt like I was going to burst, she stopped and said, "Usually before I make a guy cum, I'll tease him for longer, but we have things to do after this. Now, when you make a guy cum, it's important to think about what you want to do with it. If I'm feeling like a total slut, I like to have him cum all over my face. Now, if you're trying to maintain some level of class, or have to return to a party, just let him cum into the back of your throat. Either way, it's the best feeling. It's like winning a prize for giving your man the best feelings of his day."

With that, she resumed her blowjob, this time pulling me in with her other behind my butt. I could feel my lacy thong digging into my butt and felt the tiny brush of lace every time her hand came across it. Pretty soon, I gave into the incredible sensations and actually came harder than when I jerked off wearing my sister's thong the first time. As I burst into Kristin's mouth, she dutifully continued to suck, swallowing the immense load without stopping any motion. After a few more licks, she got off her knees and said, "Practice makes perfect."

"How about we pick out what you're going to wear underneath your pretty prom dress? Lay out your choices on the bed."

I moved to where I stored the panties, pulled them out, and delicately laid each on the bed so that Kristin could get a good look at each.

"I like this thong, Jamie, so cute," said Kristin as she held my red thong to my groin.

She continued, "I think you need something a little classier though."

Kristin held up the black lace cheekies and said, "These will be perfect. Don't you just love how sexy black lace makes you look?"

I nodded and Kristin threw the panties in my direction, landing on the floor. I took off my thong and ran the cheekies up my legs, ensuring that I tucked my flaccid dick between my legs. I loved the way the lace cupped my butt. I couldn't help but feel the material with my hands, which made Kristin giggle.

"What's so funny?" Asked Rachel as she burst through my bedroom door, prom dress in hand.

"Oh Jamie is just admiring herself in her sexy black panties," Kristin responded teasingly.

I got a closer look at the dress and saw it was a red sequin dress that looked a little short for prom. Before I knew it, I was in the dress getting zipped in by Kristin. I could feel my chest supported by a soft built-in bra and looked to see that the dress went over a foot above my knees.

"Damn, Jamie, you'd turn some heads at prom," said Kristin.

"Now we have to pick out some shoes," declared Rachel as she pulled me along into her room.

Rachel's room was the typical high school girl's room: pink, covered in posters, a walk-in closet, and a full-length mirror against the door. I caught a glimpse of myself in the mirror and could instantly feel my penis try to stretch against the lace holding it between my legs. I didn't look passable for a girl, but I certainly had some desirable features. The dress gave the illusion of small breasts, it hugged my butt nicely, and the blonde hair on my legs made it hard to tell I didn't shave them.

Before I could soak myself in more, Kristin and Rachel were holding up different pairs of shoes to the dress. They settled on a pair with a decently thick two-inch heel that was a sequin red and had a thin strap that went above the ankle. I was relieved they didn't choose what they described as "stripper heels" out of fear I wouldn't be able to walk in them.

I donned the shoes and instantly felt my butt raise. I felt so sexy in the ensemble and looked it too. Rachel and Kristin had me practice walking around in the heels and dress. After some stumbling, I finally got the hang of it.

Noticing that my mom would probably be home soon, the girls had me go back to my room and change back into my other clothes.

"How about you keep your black lacy panties on though," snickered Kristin as I exited the room.

When I met them downstairs after changing, the girls giggled and talked about how much fun they had dolling me up. They said they couldn't wait for more.

I couldn't either...

I awoke the next morning to Rachel shaking me awake. Startled, I looked down at my comforter to make sure it was covering me since all I was wearing was my mom's old black lace bikini panty. After a moment of relief that my secret wasn't revealed, I registered that Rachel already knew my secret. After raising my head, I saw that Kristin and Rachel were in the room wearing their cheerleading outfits.

Rachel quickly asked, "So, did you enjoy dressing as Jamie last night?"

My mind flashed through everything that happened over the past twenty-four hours - getting caught in my pink thong, getting my first and most incredible blow job, and getting dressed up by the two girls. I nodded my head, trying to contain my excitement.

Rachel responded, "Well, we have a favor to ask. We need you to fill in for one of the girls on the team. She's really sick and we can't do any of our routines without someone to fill in for her."

My eyes widened at what her question meant, which was dressing up in public for almost the entire school to see. I started to incoherently rant about how while I enjoyed myself last night, I wouldn't feel comfortable dressed up in front of everyone. As I continued, I saw Kristin give Rachel a look, causing Rachel to make her way out of the room and Kristin to move towards the bed.

She reached under the comforter and moved her hand down to the waistband of my panties. She snapped the elastic and whispered into my ear, "Those are some soft panties, Jamie. I know how much you much love wearing them." As she whispered, she ran her fingers along my lace encased shaft, causing it to stretch the fabric covering it.

As she continued to tease me, she whispered, "I think you'd really love being a cheerleader Jamie. We get to wear the cutest outfits and cheering the team on is so much fun. I'd be so thankful if you helped us. Think about how much fun we'd have!"

Fears be damned, I couldn't stop thinking about getting dressed in a cheerleader outfit by Kristin and Rachel. It definitely helped their cause that my cock was throbbing from the soft lace rubbing against my sensitive cock. A little too loudly, I told Kristin that I'd do it.

At that, she returned a smile and a quick peck on the cheek. Next, she quickly pulled down the comforter and revealed my strained black panties. She ran them down my legs, causing my cock to stand straight into the air. She nodded in approval and let me know that I'd have to shave my legs before the game. She hurried out of the room, quickly returning with a pink razor and shaving cream.

She said, "All you need to shave is your legs and pits. Since you have blonde hair, it won't be a big deal if you miss some spots. I'll inspect you after you get out of the shower. I'd hate for you to get embarrassed by having hairy legs!"

The irony was prevalent since hairy legs were the least of my worries. I made my way to the shower and did my best to shave my legs and underarms. While I struggled a bit with my knee area, I felt like I did a decent job and felt the smooth skin throughout most of my body. I hopped out of the shower and pulled open the door into my room. There on my bed was a red and black cheerleader's outfit and my red cotton thong.

If my cock wasn't fully erect before, it certainly was now. Before I could get closer, Kristin grabbed my erection and said, "We'll need to take care of this before we get you all dressed up. I think I know just the trick to make sure you don't have to worry about this little thing getting in the way for a few hours."

She had me take a seat on my bed and wrapped the black panties I was previously wearing around my throbbing erection. She started to slowly twist the panties up and down my shaft, making my cock tingle with excitement. It felt so good that I was on the verge of having to push her hands away because I almost couldn't handle it.

Kristin sped her motions and put me over the edge by whispering about how much I was going to love dressing up again and how excited she was to see me in my "cute little thong." With that, I felt a rush of ecstasy build through my legs and multiple seconds of pleasure as I burst cum into the awaiting panties. I felt my cock push out multiple streams of cum, and afterward a moment of tremendous relief and satisfaction. Kristin pulled the panties off my now flaccid dick and threw them towards my nearby hamper.

"Let's get you dressed, Jamie," giggled Kristin. She held the red thong on her finger and held it in front of my face and said, "Let's get your sexy thong on girlfriend. Prude girls wear spandex under their skirts, but I know you want to show off just like I do." With that, she lifted her skirt and showed off a black cotton g-string that really accentuated her tight core and visible hip bones.

I took my red thong out of her hands and pulled them up my legs. I made sure that the waistband laid flat and saw the "Victoria's Secret" laid across the front. I felt the back of the thong fitting nicely in my crack. Something about wearing thongs made me feel so sexy.

Kristin handed me the skirt, which I pulled up my legs and she helped to zip into place. It seemed to fit well around my waist, but the hem was over six inches above my knees. I did love the airflow I got underneath and the feeling of the fabric brushing against my bare butt cheeks. Kristin gave one a pinch before putting the outfit top on my chest. Like her, my belly button was left exposed.

"Damn you look hot! Love how smooth you got your legs, girl," Kristin teased.

She held my hand and led me to my sister's room down the hall. There, Rachel had her makeup collection set up on her vanity. They put me down in a seat in front and went to work. Rachel carefully applied blush, eye shadow, and mascara. Finally, she had me purse my lips to apply some pink lip gloss. Looking at the mirror, I hardly recognized myself. Somehow, Rachel managed to make my face look way more feminine. Finally, Rachel put a short amber wig on my head, which she wore the previous Halloween when she dressed as Velma from Scooby-Doo.

Kristin and Rachel couldn't contain their excitement. They giggled and chatted about how girly and passable I looked. They weren't wrong -- looking in the mirror, I was turned on by the girl they turned me into.

Snapping me out of my trance, Rachel said, "You need to do more than just look sexy today, Jamie. We need you to show you our routines!"

Over the next hour, Rachel and Kristin went over all their different routines. My biggest struggle was jumping enthusiastically without my skirt rising above my waist, revealing my red thong to the world. Once the two girls felt confident, we headed downstairs to head to the football game. Without even thinking, I walked into our living room and saw my mom with her keys in hand.

She gave a smile and remarked, "You've come a long way since trying on my panties, huh James."

The girls let out a fit of laughter and I could feel myself getting aroused through the sheer terror of embarrassment. The group of us made our way to the car. By the time I got in, I couldn't wait to get out. After pulling out of our driveway, my mom broke the silence.

"I think we're going to need to do some more shopping for you, James. Girls, do you want to come too?"

Kristin and Rachel enthusiastically nodded their heads.

Kristin said, "I think James definitely needs some more panties. Definitely needs some cute bras too."

After about ten minutes of teasing, the girls had a laundry list of shopping items and we finally arrived at my high school for the game.

When we got to the sideline to the rest of the team, I got the sense my sister gave them a heads up that I was coming. They greeted me with enthusiasm and pretended that I was a normal girl on the team.

The rest of the game was a blur. I did the cheers to the best of my abilities and even had a ton of fun. Like the practice before, my biggest struggle was not flashing my thong every time I leaped into the air.

After the game, my mom added to the anxiety by saying, "Interesting choice with the thong, honey. We're going to have to get you some bloopers if you're going to stay on the team."

When we got home, Rachel let me know that the football team was going to have an after-party to celebrate the win that evening. When we got home, I headed to my bathroom to take a shower. I couldn't believe what I saw in the mirror. I looked like a passable and hot high school cheerleader. I lifted my skirt to get a glimpse of my red VS thong and could see my cock throbbing. I turned around and saw the back and was instantly even more aroused. I loved the way the waistband made my cheeks pop and how the thin strip of fabric was nestled in between.