Wedgie Relief

My sister Breanna and her friend Cindy walked through the front door and instantly took over the house. They were both on break from college and were working as lifeguards at a pool a couple of miles from my parent’s house. I didn’t mind that they took over, watching Cindy lounge around in her red, one-piece swimsuit was a thrill for me. She did have shorts on and a zip-up hoodie, but her legs would keep me occupied. However, my father was coming home early from work, and he didn’t like Cindy, thinking my sister’s friend was a bad influence on her.

Cindy had dirty-blonde hair, average-sized boobs that were prone to bouncing, and a shapely ass that was framed by curvy hips. Her most obvious flaw was her face because it was kind of long and she needed her hair to be just right to offset the asymmetry. The one feature of hers that got lost with so much going on was her blue eyes, which could alternate between bitchiness, secrecy, and passion. I had crushed on her for years, but she had just finished her sophomore year of college, while I had just graduated from high school. Cindy had never paid me any attention, occasionally she had waved to me when she saw me in the halls of our high school, but that was it.

“Hey, Cindy,” I said, ignoring my sister.

“Hi,” Cindy said, looking at her phone.

“Do you have something to do?” Breanna said, turning off the television I had been watching.

“No, but I wouldn’t get too comfortable if I were you,” I said, smirking.

“What are you talking about?” Breanna said, already annoyed with me.

“Dad is coming home early to pack for a last-minute trip for work,” I said, watching as she realized she had better get Cindy out of the house.

“I better go. I think he’s still mad at me after you came home late and drunk a couple of weeks ago,” Cindy said, looking nervous.

“Yeah, I’ll give you a ride,” Breanna said.

“It’s too late, he’s pulling into the driveway,” I said.

“Nick, can you take Cindy out the garage until dad leaves, please,” Breanna said, looking out the window and seeing our dad pulling behind her car in the driveway.

“Would he ground you at this age?” I said, jokingly.

“Don’t be a jerk,” Breanna said.

“Let’s go!” Cindy said, intervening.

There was no time to waste if we were going to avoid my father. Cindy led the way, moving quickly to get to the back door. My father usually came into the house through the front door, so we were safe, heading to the garage through the back door. Cindy’s flip-flops were making a smacking noise as she scurried to get out of the house. I watched her ass the whole time, mesmerized by its movement and surprised to see her acting anything other than cool.

Once outside, we made a straight line to the garage, entering through a side door. We could only hope that my father had not seen any of our mad dash. We were quiet, hoping things on the outside would also stay quiet. I was afraid to look through one of the windows, knowing my dad would probably see me. I knew that I could have gone back into the house as if nothing had happened, but I was excited to spend time with Cindy, especially since we were alone.

“I think we’re safe,” I said, getting two chairs for us to sit on.

“I doubt you’ll be in trouble,” she said, sitting down, crossing her legs, and unlocking her cell phone.

“You’re probably right,” I said, sitting down next to her, hoping she didn’t mind.

“You can go back inside your house.”

“I think my sister would want me to keep you company,” I said, watching as she dangled one of her flip-flops off her toes.

It was awkward at first; she was seemingly absorbed with her cell phone, and I was absorbed by staring at her. I knew that my gaze probably seemed intense, and I most likely looked like I was objectifying her, but I didn’t care. Her tanned legs were the most amazing thing I had seen all summer. I wondered if her torso was pale underneath her swimsuit, wishing I could see more of Cindy.

“Do you like working as a lifeguard?” I said, trying to get her to talk with me.

“Not as much as your sister does,” she said, shifting in her chair.

“You must get a lot of attention in that swimsuit,” I said, knowing she might not like the question.

Cindy finally looked away from her phone and stared at me for a few seconds before saying, “some, but I’ve got a constant wedgie in it, and my butt cheeks are on display if I take the shorts off.”

“Wow! Guys must go crazy seeing you like that,” I said, feeling very nervous.

“Your sister gets attention, too.”

“You seem so cool about it; it’s like you can take it or leave it.”

“Most guys look at all the girls around, so it’s really nothing special to get stared at.”

“I don’t know, I’d look at you instead of other girls.”

“Why are you talking to me like that?”

“Like what?”

“Like I wouldn’t know that you’re kissing my ass,” Cindy said, going back to her phone.

“I wouldn’t do that. I think I have a crush on you,” I said, unsure of everything.

There was silence, but I could tell that she had stopped looking at her phone and seemed pensive. I liked how her face looked with her hair up; it made her look bitchy and as though she didn’t care to hide her facial asymmetry. My sister once told me that Cindy was self-conscious about the shape of her face and would find the right hairstyle to compliment her features. I didn’t care; It looked normal to me, maybe just slightly long.

“What do you think having a crush on me gets you?” She said, smiling a little.

“I don’t know, maybe seeing you with your shorts off,” I said, desperately wanting her to play along with me.

“Really? Don’t you think that’s asking a lot?”

“I saved you earlier,” I said, pleading some.

” I really don’t think so,” she said, playing with the zipper on her hoodie.

“A bunch of guys at the pool you don’t even know get to see you without them on,” I said, sounding a little more desperate.

“Come by the pool if you want a show.”

“You’d probably leave your shorts and hoodie on, so I couldn’t see your body. Anyway, my sister would throw a fit if I did that.”

“Why should you get your way?” Cindy said, turning to look at me with an interested look on her face.

“Because it would mean so much to me,” I said, feeling out of options.

“Your sister just sent me a text saying your dad is packing and then he is eating dinner. She thinks it won’t be too much longer.”

“Oh,” I said, disappointed.

When she unzipped her hoodie, I knew there was a chance for something with her. I finally got a peak at her boobs, looking at the shape of them, and I was excited she had done that, giving me even the slightest amount of hope she was willing to indulge me. I could make out a nipple that was pressing bravely against the material of the swimsuit.

“If you promise to kiss my ass and whatever else I tell you to do, I will take off my shorts,” she said, teasing me.

“I will kiss both sides!” I said, ecstatically.

My crush stood up and took off her hoodie, giving it to me to hold. She then put her hands on her hips and looked down at me with a playful look on her face. I never expected a garage would be the place where Cindy and I would share a special moment but, to me, her beauty could only make any place that much better.

When she started to lower her shorts slowly, I felt invigorated with something beyond all of my fantasies. This was real, she was real, and she was willing to carry me along for a glimpse into something a virgin like me had only dreamed about. I could see her pale tan lines at the edges of her swimsuit, willing me to get an even clearer view of her white skin and fantastic body.

“Is my ass looking cheeky enough?” Cindy said, turning to let me see her behind and the wedgie the swimsuit had given her.

“Wow!” I said, dropping to my knees.

She must have suntanned with the wedgie in place because her butt was not so pale. I touched one ass-cheek, feeling how soft her skin was. I pulled out the wedgie, giving my crush some relief from any discomfort she may have felt. Cindy acted as though she liked what I had done; she let out a small moan that had the tone of approval. I just wanted to make Cindy happy.

“Your ass is so nice,” I said, squeezing both sides, finding it firm with just a little give.

“It’s time for you to kiss it,” she said, turning her head and looking down at me.

“I can do that,” I said, sensing she needed this as much as I did.

The ass staring at me looked so delectable, and I started to kiss it as if I were feasting on a meal. My tongue also wanted to play, prompting me to lick her booty, tasting a combination of sunscreen and salty sweat. Cindy moaned some more, and when I looked up, I could see that she had put a hand inside her swimsuit and was fingering her pussy.

“You’re so beautiful, Cindy,” I said, licking at the crease at the bottom of one cheek.

“Tell me that I’m the hottest lifeguard,” she said, working her pussy.

“You’re the hottest lifeguard in all the city. My sister, with her chubby thighs, can’t compete with you,” I said, caressing the front of her thighs while gently biting down on her butt.

“Tell me that I’m hotter than Olivia!”

“You’re way hotter than Olivia. She is so nasty with all her cellulite,” I said, remembering that Olivia was part of Cindy’s circle of friends.

“She’s so disgusting,” Cindy said, fully into our moment.

“You’re the queen of Turbine Park.”

My words must have helped because she worked herself more vigorously. Cindy finally turned around and presented me with the front of her body. She took her fingers out of her private area and offered them for me to taste. I gobbled up the wetness on them, savoring her juices. Cindy then reached for the top of her swimsuit and pulled it down, revealing her titties to me for the first time. I stared at them hungrily, thinking that they were smaller than I had imagined them being, but they were definitely round and firm. She stood proudly before me, letting me see them from below. The front of her torso looked pale from tanning with her one-piece covering most of it.

“You’re so wet,” I said, licking her swimsuit in front of her pussy.