Big Bad Cowboy: A Billionaire and a Virgin Romance

by Tia Siren

  “Okay, I’m going to consider this outfit a good jumping off point,” she said.

  She poured me into more outfits over the course of the next hour. Every one of them was more revealing than the last. I didn’t mind in the least, as I found more confidence in myself with each change.

  “Okay, I think we got it, now let’s get you something to wear underneath,” she said with a smile.

  I spent more money in the first store than I should have, but change is never cheap.

  We entered an expensive lingerie store, and I felt very out of place. Bras were hung prominently from the walls, as did the lacy underwear.

  We paraded through an assortment of tops where Jennie plucked out a few things that I would never have purchased alone. Then, just as before, she crammed us into a fitting room.

  “I think I can change by myself, Jennie,” I said.

  “Oh don’t be so lame, it’s not like I haven’t seen you naked before,” she said.

  I giggled.

  “That was 8th grade, Jennie,”

  “Do you really think you’ve changed much since then,” she asked.

  I shrugged, I couldn’t see any difference. I breathed deep, letting go of whatever embarrassment I might feel soon as I slid out of all my undergarments.

  Jennie began laughing, hard.

  “Okay, what now,” I said with a sigh.

  “You need to shave, Hun,” she said.

  “I’ll do that later, just give me those panties,” I slid on the laciest pair she found. They were more comfortable than I thought. They rid up my backside a bit, but it wasn’t so bad.

  For another hour, I tried on half the store. Jennie continued to make jokes about my unshaven womanhood, so much so that she called up and made an appointment for a Brazilian wax, which I’d heard of but had no idea. I just went along with it.

  “You’re in for a treat,” she said in a somewhat ironic tone.

  The day lingered on, purchasing new makeup, new shoes, and things I didn’t know I needed. Jennie had it all planned out, as though she’d been thinking about this for a while. Her madness continued until we stood in front of a boutique, my heart was beating hard, and I felt like I should run away; I probably should have.

  I’m going to spare the details, in fact, I really don’t want to think about it in the slightest, or go back for another wax. It was torture for a first timer and had a feeling Jennie was laughing the whole time in the waiting room. I wondered, in jest, what the coach would think if he saw me in the lacy underwear, and my clean shaven privates. It made me giggle as I thought about it.

  She drove me home, and I was grateful for the ride. I had too many things to take on the bus and was still a bit embarrassed after my first Brazilian.

  “I’ll pick you up in a few hours for tonight,” she said before she sped off.

  I wondered what Mr. Reynolds was up to.

  4.

  “Girl, Mike is going to love you,” was all Jennie said to me as I tucked myself into the front seat of her car. Brad was already waiting for her at the party with his friend Mike. I couldn’t get Mr. Reynolds out of my head.

  I was feeling nervous again but pushed it to the back of my mind. I had prepared and was ready for this, and I had never felt sexier.

  “Do I have to spend the whole night with Mike? If I’m not having fun, I might sneak back home before he notices,” I said.

  “You can do whatever you want, but give it a shot and see if you like the new you,” she said.

  I felt anxious, both wanting to see what people thought of my change in appearance and wanting to curl up under my blanket at home. I didn’t say anything else in the car until we arrived at the party.

  There were already people standing outside, drinking casually and talking. Some were even spilling into the lawns of the neighboring houses. The house behind them was large and old, made of red brick with ivy crawling up the sides; columns supported a balcony on the second floor with some old Greek letters displayed prominently on the railing.

  I could feel their eyes as I stepped from the small car, and a measure of silence fell over the crowd. I felt immeasurably embarrassed being the center of attention. My heart raced as though it would shoot from my chest any moment.

  “Come on, Sandy,” Jennie said, grabbing my arm to lead me inside.

  The talking started again as I strolled past, and I could make out my name being uttered by several of the partygoers; my name was now followed by the word ‘sexy.'

  Brad took up a place in the backyard over a large stainless steel grill, being crowded by a group of football players looking for conversation and food.

  Jennie waved at Brad, who smiled at her briefly before his mouth dropped slightly at the sight of her new friend.

  “Who is that,” Brad asked in an astonished tone.

  “Brad, it’s me, Sandy,” I said proudly.

  One of the football players jutted his arm around my waist.

  “Hi, I’m Mike,” he said with a smiling and drunken expression on his face.

  He was cute, but not in the way I liked. His round and dimpled face made him look as though he were several years younger than he was.

  “Hi, Mike,” I replied.

  “I think Jen said I might just be your type,” he said.

  I nodded as he shoved a red plastic cup, full of beer, into my empty hand.

  “I’m already four drinks in; you have some catching up to do,” he said.

  I fought the urge to roll my eyes, so I looked over at Jennie with a sort of surprised and disgusted look on my face as I took a sip of the frothy liquid.

  “Do you wanna go somewhere and talk,” he added.

  I sighed.

  “Sure, let’s talk,” I said.

  He grabbed me by the hand and pushed his way into the house, shooing a couple from the ruffled and musty old couch in the living room.

  “Have a seat,” he said, playful pushing me down.

  I wasn’t used to being pushed around by men, and I hadn’t any interest in starting now, but I wanted to see what the ‘new me’ would do.

  I cozied up with the armrest and hid my face behind the plastic cup.

  “I’ll get you another beer,” he said, sprinting off to the backyard.

  Some cheering came from the front yard, and I was curious to see what was going on. I sat on my knees and peered over the back of the couch toward the front door. Coach Reynolds was making his way inside, a cheerleader or two in tow.

  I quickly ducked behind the tall back of the couch, hoping that he hadn’t seen me. Then a shadow cast itself over me and looking up revealed that he had indeed noticed me.

  “There’s no way that’s you,” he said.

  “Who do you think it is,” I asked.

  “Only one person I know has cheekbones like that,” he added as he paced around the couch. He plopped down by the other armrest and waved away his followers who looked at me with envious gazes.

  “You made me want to try something new,” I said.

  He laughed and crossed his legs.

  “I’m surprised you came,” he said.

  “Likewise,” I added.

  “This is a good look for you. If only I were ten years younger, I might have tried harder to muster the courage to ask you out,” he said.

  Ten years younger, I thought, he was still gorgeous now. I wanted to continue chatting, but Mike returned from the backyard.

  “Hey, Coach,” he said while handing me the beer, “wasn’t expecting you to come.”

  “Someone had to make sure you guys don’t drink yourselves stupid, just consider me more of a chaperone than a drinking buddy,” replied Coach Reynolds.

  I took a long sip from the glass and felt out of sorts with the two of them here. I would have much preferred just to talk to the coach.

  Mike plopped down in the center of the couch and threw his arm around me. I wanted to shove his arm off, but couldn’t muster the assertiveness to do so.

  “So
, Coach. How do you think we’ll do at the game?” Mike asked nonchalantly.

  “I think you know where I stand on that,” he replied.

  “You guys will do great,” I said, not adding much to the conversation.

  The two guys looked at me, and I regretted saying anything at all.

  “What makes you say that Sandy,” started Mr. Reynolds.

  “Well, I’ve watched you guys practice a lot, and you guys always look good when running plays and stuff,” I said.

  “If anything, they look good,” laughed Mr. Reynolds.

  “Hey, you want a beer,” Mike asked.

  “Sure, Mike,” the coach replied. Mike shot up, running to the backyard again.

  “So, Mr. Reynolds, do you like the new look,” I asked, straightening out my top.

  “Call me Jeff, Sandy,” he said.

  “Okay, Jeff,” I replied uncomfortably.

  “To answer your question; yes, you look fantastic.”

  “Would you have talked to me ten years ago if I looked like this,” I asked.

  “I’m not sure, I was pretty shy when I was younger,” he said.

  “Well, if you had asked, I probably would have said yes,” I said.

  He crossed his legs the other way, and I felt a little nervous baring myself like that. I hoped I hadn’t said anything inappropriate.

  “You’re making me regret growing up,” he said.

  “The car you drive makes me wonder if you ever did,” I replied.

  He guffawed loudly, making a few people turn and wonder what we were talking about.

  “I’ve had that car for far too long, I should probably buy something newer,” he said, “and more responsible.”

  “I had fun on the last ride,” I said, “and hopefully it won’t be the last.”

  Mike returned with Jeff’s drink and handed it down to him before plopping back into the center seat of the couch. Jeff stood up, drink in hand.

  “I should probably check the rest of the party. I don’t want to see any drugs being passed around,” he said before walking away.

  I wanted to get up and walk around with him, holding his arm the entire time, but I was Mike’s date for the night, and I was nothing if not honorable.

  “So, where did we leave off at, cutie,” he said, starting to lean over for a kiss.

  I pushed him off, trying to keep his face away from my own.

  “Mike, I’m not making out with you,” I stated.

  “Oh, come on. Why else did you work so hard to look good for tonight,” he asked.

  A hand shot out from behind the couch, grabbing Mike by the shoulder and dragging him away. Jeff had returned and looked upset.

  Mike did his best to fend him off, but Jeff was the stronger man, and he effortlessly pinned Mike to the wall.

  “I want you to get everyone together and line them up out back. We’re having an impromptu lesson for all the players,” Jeff said authoritatively before releasing Mike.

  Mike scampered from the wall and started running around the house, gathering just about every guy there. It only took about five minutes before they were all crowded around in the backyard, and the other partygoers were pushed inside. Out of curiosity, I decided to listen in and hear what they were talking about.

  “Are you boys kidding me?!” he shouted to the gathered players, “You force yourself on girls and think that’s right?”

  The guys looked a little sheepish.

  “A good man doesn’t force anything; he waits to be received and is grateful when he is.”

  “Coach, since when have you had a girlfriend, though,” replied Mike, “girls are different today than when you were in college.”

  “Style’s change, Mike. Girls don’t.”

  “Yeah, but we’ve never seen you with anyone, why don’t we ever see you with a woman,” Brad asked.

  “I’m not here to get mocked by a bunch of college kids that think they’re big time stars and are owed sex,” Jeff started. “Next time you get that feeling that she owes you a kiss or anything else, if I hear about it or see it at all, you won’t be playing,”

  The guys looked around at each other.

  “Sorry, Coach. I think I speak for everyone when I say this is the last you’ll hear of it,” Brad said.

  “Good. And, when you meet the right girl, you’ll know,” Jeff went on to say. He saw me watching from behind the crowd and met my gaze, continuing to speak.

  “Sometimes you meet the right girl at the wrong times,” he said, “and you want to do nothing more than spend time with them. But, you know you shouldn’t.

  “You can’t take your eyes off them, and there’s nothing you can do.”

  “Umm, coach, what are you going on about,” asked Mike.

  Jeff shook his gaze from me and focused back to the crowd of players.

  “It’s nothing, Mike. I gotta get out of here. Don’t drink too much, we have a game in a couple of days,” he said.

  Jeff pushed his way through the group and walked towards the entrance to the house.

  I followed along, desperately trying to keep up. He walked fast; faster than I’d seen him move before. I pushed through the crowd that filled in the space behind him and realized I had lost more ground.

  Before I could even exit the house, he was already in his car and driving off down the road. I couldn’t let it end like this; I needed answers from him.

  I sprinted through the house again, towards the backyard. Then, once in the backyard I ran and hopped over the fence. It connected to a similar house, as well as the only road out of the area.

  I heard his car rounding the corner just as I made it to the road. I stood prominently in front of his path, and his car screeched to a halt.

  “Sandy, what are you doing, get out of the road or someone is going to hit you,” he said.

  “Jeff, we need to talk,” I said, making my way to the passenger seat.

  5.

  He didn’t seem to object to me getting into his car.

  “Drive,” I said.

  He put the car back in gear and started on the way again.

  “If anyone sees us in the same car, I’m in trouble,” he said.

  “I don’t care,” I replied sternly.

  We drove in silence for a few blocks while I thought about what to say. I honestly didn’t think I’d make it this far.

  “Were you talking about me?” I asked.

  He let out a drawn out sigh.

  “Yes,” he replied.

  “You couldn’t take your eyes off me?”

  “Yes, and I felt bad every time,” he said.

  “Why is that,” I asked.

  “I’m a teacher; I’m not supposed to get involved with students.”

  “How involved were you trying to get,” I wondered.

  He pulled the car over; we found ourselves on an empty street, not a house in sight. He clicked the car off and leaned back in his seat.

  “I wanted to ask you out,” he said, “I just want to-”

  I kissed him mid-sentence. At first, I thought he would try to fight me off, but he leaned into it and accepted my advances passionately.

  “We shouldn’t,” he said lightly pushing me away.

  “You’re right, it’s a good thing we aren’t,” I said while I rubbed his inner thigh.

  He squirmed in his seat, but not in a discomforted way. I was surprised at the new me that was taking over. My head was screaming for me to stop, but every other part of my body yearned for me to continue. My body needed this.

  I massaged his member outside his pants; he was getting harder with each rub. He pulled me in closer for a kiss which I cherished. The tenderness of his lips and the eagerness of which he gave them to me was turning me on more.

  His arms wrapped around my skinny torso and he ran his hand along the small of my back. I leaned down and unzipped his zipper to free his throbbing member. With a light tug, it revealed itself to me.

  I ran my hand up and down his shaft, a
nd he leaned his body back, letting out light moans of pleasure with each stroke. I took his free hand and moved it between my legs. He did as I wanted and rubbed his hand up and along my freshly shaven slit.

  Then I took him inside my mouth, as much of it as I could. His salty juices were already starting to flow from the tip, and I lapped them up.

  He undid my tight jeans and forced his hand down inside. His fingers made round motions around my clit, and I could feel my panties starting to soak.

  I bobbed on his rock hard manhood for a few more strokes before I leaned back and shoved off my bottoms. He did the same.

  He looked at my bare womanhood, licking his lips. In a quick motion he bore down on my dripping wet sex; playing excitedly with every part of me.

  His tongue flicked over my clit in wonderful circles that shot waves of pleasure through my head. I thought I might burst from the sensation alone, but it seemed he had other plans.

  He tugged at the bottom of my shirt and lifted it over my head, exposing my tiny breasts and nipples for his enjoyment. I felt a little shy, but wanted him to see, so I opened my legs a little wider and arched my back.

  He crawled along the seat, stealing another kiss from my lips. I could feel him rubbing his beast along my wetness. He wasted no time and pushed himself into me with a forceful lunge. It had been a long time since I had felt the sensation of another person entering me, and I was glad it was him doing it.

  His member pulled me apart, and I relished every inch. I moaned loudly, and this just turned him on more. I could feel him throb from inside.

  Then he began to pump, exiting, and entering me. He began to get rough, and I liked it. With every thrust, he came in a little harder. I wrapped my hands around his neck so that I wouldn’t fly away. He grabbed me by the waist and pulled himself into me as far as he could.

  My body ached with passion, and sensations I’d never felt before were flooding me from my head to my fingertips. I started feeling all tingly while he continued his onslaught of passionate thrusting.

  I felt it small at first, and then it became a cascading wave of sensation. My body tensed and my toes curled. He wasn’t far behind; I could feel his body tighten, pulling me in for one final thrust before releasing himself inside.

  When my orgasm finally stopped, I realized I hadn’t taken a breath in more than a minute and felt incredibly winded. He pulled himself out, slowly.