That Shirt

Story Info
Jake suddenly lusts after his engaged friend.
4.2k words
4.46
27.7k
15
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It all started when she wore that shirt. I had been spending almost 10 hours a week with Emily for over 2 months and never felt any attraction until she wore that shirt. Anyone would call her pretty: straight light brown hair a few inches past her shoulders, eyes that were some combination of blue and green, an average body with a slight hourglass figure. Because I knew her from her volunteering at the animal shelter where I work, I had only seen her in jeans and t-shirts, usually from the men's department because they were more comfortable and geeky. I stared right at her chest several times commenting on the 90's TV show characters on the front of those t-shirts, but never had a sexual inclination.

Ironically, when the weather got colder, I saw more skin. On that fateful day, she wore a black long-sleeve shirt with buttons from around the bottom to the top of her sternum. Of the 5 buttons, the top 3 were undone and I was treated to an amazing view of her cleavage when she bent down to clean one of the bottom cat cages. She was either oblivious or so used to men staring that she ignored my eyes lingering.

For the next two hours, I admired her body as discreetly as I could. Her breasts were my main focal point. I won't pretend to know anything about bra sizes, but they looked to be a little more than a handful and supported by a bra that left the smallest space between them. Just above them was a defined collarbone that was more appealing than I could have expected, leading up to a slender neck. When I stood behind her, it took all my willpower not to nibble at her neck and earlobes. Instead, I smelled the slight seemingly-impossible scent of apple and coconut of her hair. I pulled myself away and went to work in another room to try to control this sudden lust.

It wasn't long before she finished cleaning all the cages in the first room and joined me in the other room. As we worked, I admired her from a distance, realizing I almost lost control earlier. I was noticing the length of her legs when she bent over and gave me a wonderful view of her ass. It was round and firm, not in a going-to-the-gym-every-day kind of way, but in a not-afraid-of-manual-labor kind of way. It seemed like I had seen everything, then she turned to talk to me. In my awkward attempt to not get caught staring, I landed my eyes on her lips. They were forming words, but I didn't hear them. I was watching them move, noticing how naturally full and dark pink they were and considering how good they would feel on various parts of my body, when I realized she had stopped talking and was looking at me quizzically. I knew I couldn't just smile and nod my way out of this.

"Sorry, I...uh, zoned out there. What did you say?"

"Can I let Voldemort out, or is he terrorizing the other cats still?" She asked it so innocently that I hoped she couldn't tell where my mind had just gone.

"You might as well. He's never a problem when you're in here anyway. You're the cat whisperer." We both smiled at my horrible joke, knowing there was truth to it. She was asking about a fat black cat that hissed and scratched at everyone, but nuzzled up to her. She never really had problems with the animals and was even sympathetic towards those that scratched or nipped at her. An animal person myself, it was a quality I always found endearing.

I think I succeeded in acting normal, but it was a relief when she left. I buried myself in paperwork until 5pm and blared the radio on the drive home as a distraction. The second I stepped inside my house, my mind immediately turned back to Emily. I fell onto my bed, closed my eyes, and let my imagination take over, figuring I could get it out of my system. I remembered each bit of her I looked at earlier in order, letting my hand wander under my waistband. It only took a few stroked and the memory of the view down her shirt to finish. I drifted off to sleep satisfied that I had taken care of that problem.

She only volunteered three days a week, so I didn't see her the next day. My mind didn't wander to thoughts of Emily and I assumed I was cured of whatever had come over me. I realized how wrong I was when I saw her the next day. There was no cleavage, but she wore a long-sleeve shirt with a wide neck that fell off one shoulder. How can a shoulder be so attractive? I struggled through 15 minutes until by some stroke of luck, I had to go out on a lost dog call. I was gone long enough that she had already left by the time I got back. Thursday passed without her coming in, and I thought I was prepared to see her Friday.

On Friday, Emily was back to her boyish clothes, wearing a hooded sweatshirt, which helped me forget everything I had thought of her for the last few days. We were talking and joking as usual and I thought everything was normal again. Of course that didn't last long.

"It's a lot warmer than I expected today," Emily commented. I didn't even have a chance to respond before she was pulling her sweatshirt over her head, exposing a little sliver of her stomach. As if that wasn't bad enough, instead of one of her usual t-shirts underneath, she had on a tank top that revealed more than I had ever seen. All I could think of to do was mumble something about paperwork and retreat to the office. This continued for weeks.

I'm not a coward. Under normal circumstances, I would have made a move or at least flirted a little. But, Emily unfortunately had a fiance. There was no reason for him to think I was a threat since she had plenty of guy friends, and he figured I was just one of them. I had a guilty mind, but I would never interfere in a happy relationship. I knew it was happy because half of the stories Emily told me were about him and what the two of them had been doing. She rarely complained and she couldn't hold back a smile when she talked about him. I regretted ruining our friendship, but I avoided her to keep my urges under control.

I had barely seen her or talked to her for well over a month, partly because I stayed away and partly because she was away for Thanksgiving and then sick for a week. Apparently absence does make the heart grow fonder, because she was out of sight but not out of mind.

It was the second Saturday in December, and I dragged myself out of the house to go to a coworker's holiday party. I figured any distraction was good for me, plus I was hoping to find a woman wanting to help me with my recent sexual frustration. Luckily, my coworker has good-looking friends and there was plenty of eye candy at the party. I was admiring the sights when someone tapped me on the shoulder.

"Like what you see?" Emily stood next to me giggling that she caught me checking out all the women I saw. When I looked at her, I completely forgot about every other person in the room. It was the first time I had seen her in makeup or a dress. The makeup was subtle, but noticeable. Even though she didn't need any, it accentuated her features. The dress was stunning. Or rather, the dress made her look stunning. It was dark grey with cap sleeves and a wide neck that showed off her lovely collarbone, but no cleavage. The bottom of it barely reached the middle of her thighs and I imagined that the back showed even more of her long legs. She had on purplish tights and black ankle boots with a heel that made her maybe an inch taller than me. She didn't need heels; she was already the same height as most guys.

I ignored her question only managing to openly stare and say, "Wow..." which made her blush.

"I feel so silly getting all dressed up, but Beth convinced me to," she explained, talking about the host of the party.

"I'm glad she did. I mean, you look great. Like, it's cool to see you not in jeans and a t-shirt." I played that off horribly, but it elicited another giggle and a deeper blush from Emily.

"You're looking pretty handsome yourself. I've always wondered what you look like out of your work clothes." I couldn't tell if she intended or even realized the innuendo as she said it, but I felt my own face go red and she immediately got embarrassed. "I mean, I've never seen you without your work shirt on...ummm...I've never seen you in different clothes."

There was an awkward silence between us where we avoided eye contact and I took the opportunity to look at her again. That's when I realized that the diamond ring that was always on her left hand was gone. She must have noticed me looking because she covered her hand.

"I don't want to be rude, but," I started before she interrupted.

"Shawn and I had...a falling out. Things weren't great for a while, but we had a big fight when he wouldn't join my family for Thanksgiving and he sort of kicked me out right before the holiday...I've been staying with Beth because I wanted to stay in town and can't afford my own place right now."

"I had no idea. That's horrible. I didn't mean to bring up a sore subject."

"No, that's okay," she shook her head for emphasis. "You've been so busy at work that I barely even see you anymore and the couple of times I did, I didn't know what to say. Plus, you've seemed really stressed so I didn't know if you were dealing with your own stuff and I didn't want to give you my problems to worry about," she was speaking quickly to hold back a tear. I acted on instinct and hugged her protectively. She let my arms wrap around her and buried her face in my chest. Before she could cry, I led her away from the crowd and into the closest room.

In the room, I spotted an unmade bed with a familiar nerdy t-shirt thrown on in and realized this must be the guest room where Emily was staying. I looked back at her expecting to see mascara running, but her eyes were dry. Suddenly, I felt awkward, realizing the conversation hadn't brought her to tears. And I had taken her away from the party into an empty bedroom. I hoped she understood and didn't think I was a complete pig, but she quickly eased my worries.

"You always make me feel better Jake. I definitely needed a hug and a break from all those people."

"I had no idea where I was bringing you. Sorry about that."

"Well, it was this, the bathroom, or outside. There are people everywhere else. Everyone probably just thinks we're hooking up or something anyway." She said it so matter-of-factly and completely caught me off guard.

"Why would people think that?" I asked a little too defensively.

"Well, that's why people sneak off to bedrooms at parties, isn't it?" She laughed a little as she said that. "Besides, I heard there's a running bet about us."

"A running bet...?"

"I guess your coworkers took our friendship as more and figured we'd find each other irresistible or something silly. I only know because I finally got Beth to admit why she had an extra calendar with everyone's names in a different range of dates. It was to keep track of the bets." She laughed it off while I mentally cursed out Beth. She knew why I was doing paperwork to avoid Emily. I was sure that everyone else must know by now too.

"Something silly is right," I tried to laugh it off too.

"Yeah, you're right. Even that hug was totally platonic." Somehow that comment bruised my ego, even though she probably meant well by it.

"You have no idea how I could hug you." I knew it sounded ridiculous as I said it, but she got the message and played along.

"Oh yeah? How?"

Instead of responding, I pulled her toward me, one arm between her shoulder blades and the other on her lower back. Her face was less than an inch away from mine and I could tell I surprised her, but she didn't miss a beat.

"Is that all you've got?" she joked.

"You can't handle what I've got."

"Bet I can."

Her face was so close our noses were almost touching. She wore a smirk and dared me with her eyes. All the awkwardness and uncertainty vanished. I kissed her aggressively and she immediately responded with the same enthusiasm. She reached under my arms and up to grab my shoulders as I let my hand wander past the small of her back and over the curve of her ass. I could feel her smiling into the kiss and felt encouraged to do more. I pressed my body against hers and suddenly realized my cock was also pressing against her. I immediately pulled away afraid of pushing too far.

"What's wrong?" She looked confused.

"I don't want you regretting this."

"Do you not want to do this?" Her expression changed to concern.

"You have no idea how long I've wanted to do this," I admitted. "And you look so gorgeous tonight, it only makes me want you more."

She blushed again, then smiled. "You want me?" She took a step towards me. "How long have you wanted this?" She started unbuttoning my dress shirt. I didn't answer afraid to ruin the moment with words. She finished unbuttoning my shirt and I threw it on the ground. She kicked her boots in the corner and was suddenly and inch shorter than me again. I undid my belt buckle as she stealthily removed her tights. She bravely unzipped my jeans and I let them fall to the ground. I felt exposed standing in front of her in an undershirt and boxer briefs while she still had a dress on. It looked amazing on her, but I was dying to see what was underneath. She must have seen the longing on my face, because it was soon off her and thrown in a corner.

As much as I dreamed about what she might look like half-naked, nothing prepared me for this. She gave me a minute to take in her matching blue bra and panties. The cups barely covered her nipples and the panties were cut so they showed an arousing hint of cheek. I was still staring when she looked at my undershirt and cocked her head to the side. I needed no more encouragement and pulled it off over my head.

Thankfully, Emily smiled at my almost-naked body and approached me again. I was expecting more making out, so she really surprised me when she dropped to her knees in front of me. Emily looked up at me with a devilish trace behind the innocence of her blue-green biting her naturally pouty lips. My jaw must have been on the floor and I had no idea how to respond. Neither of us spoke. Instead, she pulled down my underwear revealing a fully erect cock.

Emily wasted no time in taking it in one of her hands and feeling along its seven inches. I barely even had time to moan before her mouth was covering the head and she began giving me an amazing blow job. I wanted to watch her so badly, but I was so overcome my the feeling of her warm, wet mouth, that my eyes closed. I'd pleasured myself plenty since lusting after Emily, but hadn't even flirted with anyone because it somehow felt like cheating. After months of celibacy, this girl was literally making my dreams come true.

She stopped suddenly and the air felt cold as it hit the spit she'd left on me. I opened my eyes, worried something was wrong, just in time to see her face move to my balls. She grabbed my thighs for support as she took one of my balls in her mouth and sucked it gently. Even though I'd been with a number of girls, this was a foreign experience. Most weren't opposed to oral, but Emily was the first who eagerly paid attention to every part of my penis. It could barely have been a minute before I let out a deep groan, feeling ready to explode. She understood the warning and moved her lips back around my shaft, letting her hand fondle my balls. I couldn't hold back and shot deep down her throat, forgetting for a moment that we were in a house full of people and screaming out her name.

As Emily sucked the last few drops from me, I realized our surroundings and my face gave away my fear of being caught.

"Don't worry," she smiled. "It's louder out there than you think. And I've screamed louder than that fantasizing about you the last few nights, with no complaint from Beth. This room seems pretty soundproof."

It was my turn to smirk. "Fantasizing about me? What else did you imagine?"

"You know...stuff..." She stood up as she answered, crossing her arms over her chest. Her nerve was fading and I was afraid I'd lose this sexy nymph too soon.

"So far reality's beaten my imagination, but I imagined me inside more than just your mouth. Of course, I didn't count on you being able to make me cum so easily. Or me being ready so soon after finishing." With that, I glanced down at my cock, which was amazingly completely hard again. I hoped admitting something slightly embarrassing would make her more comfortable, and luckily it worked.

Emily looked down as well saying, "Well, I guess since I've seen yours, it's only fair if you see mine." I thought I was in heaven already seeing her in lingerie, so when she reached behind her to unclasp her bra, she had my undivided attention. Once it was undone, she let the straps slide down her shoulders, then the whole bra fall to the floor. They lost a slight amount of lift, but the bra had hardly added any size. I was so mesmerized by her naked breasts that I didn't even notice her sliding her panties off until they hit the floor. Unlike most girls I had seen, she was not shaved bare. I always assumed I wanted no hair down there, but hers was clearly groomed, very short and neat. Somehow not being shaved like a porn star made her seem innocent and experienced all at once. And she wasn't afraid to be different, which I always loved about her.

"Please, turn around," I begged. Her face lit up realizing I wanted to admire every inch and she complied. I don't know what came over me, but I had to touch her. I came up behind her, first grabbing her round ass cheeks, then moving my hands along the side of her body, over her hip bones and along the side of her ribcage. When I got to her chest, I gently moved my hands over it, realizing I had been right. Her tits were a little more than a handful. I smiled to myself at this and pressed my body against hers. My lips kissed along her slender neck, just like I had wanted to do for so long. This elicited a soft moan from Emily and I knew she wanted more.

I moved my right hand off her breast and traced my fingers between them. My fingers traveled down her stomach, over her belly button, and stopped just above the top of her pubic hair, all while I continued kissing her neck and collarbone. My hand moved over her mound, with my middle finger resting over her clit. I could hear her breathing heavier as I applied a slight pressure with that finger and slowly moved it side to side. She stood still, letting me explore with my hands. My finger moved back and felt the heat coming from her slit. I gently slid the finger inside her, feeling how tight she was. I knew she couldn't be a virgin having shared a bed with a man she planned to marry for almost a year, but she could have easily fooled me.

I was enjoying the quiet moans I caused her to make and barely noticed her hand moving between us. She wrapped her fingers around my cock, which was pressed against her back, and repositioned it so it was between her ass cheeks and pointing at the entrance to her pussy. My brain told me to wait and enjoying teasing her a little longer, but my body took over. I bent her over the end of the bed that was in front of her and admired her glistening pussy lips for a second before I forced my entire length inside her.

Somehow, I regained my composure and stayed in that position for a minute instead of ravishing Emily completely. She took the pause to move my hand away from her mound and replace it with her own hand. I could tell she was playing with herself, which was fine with me. I wanted to bring her to an orgasm, even if she helped it along.

Slowly, I started pumping in and out, grabbing her hips as they matched my rhythm. We quickly gained speed and I was happy I had already cum once so I could enjoy this longer. She pushed back against me hard, wanting every inch inside her and this only made me fuck her harder. I couldn't see her face, but I did see her gripping the sheets tightly and heard her moans getting louder, encouraging me to go faster and harder.

12