To Please Him - Cover

To Please Him

by Sindiseptember

Copyright© 2000 by Sindiseptember

Erotica Sex Story: The younger girl tries to please her boyfriend and gets more than she could ever imagine as fate might dictate.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Mult   Teenagers   Reluctant   Coercion   Blackmail   Drunk/Drugged   Heterosexual   Cheating   BDSM   DomSub   MaleDom   Rough   Gang Bang   Group Sex   First   Oral Sex   Anal Sex   Exhibitionism   Size   Slow   School   .

I had been dating my boyfriend for nearly a month. He had been my boss at a part-time job I took as a receptionist for a building firm (still was, only I seemed to be working less and less). We enjoyed a pretty casual, yet intense relationship. He was divorced and had loyalty issues. Plus, he was 19 years older than me, and my parents would not approve. I believe the forbidden nature of our age gap was something that enticed him, I know his age was in my mind a benefit. It made our relationship very exciting.

My folks knew him casually from church, ironically, though he had quit going nearly a year and a half ago when his wife filed for divorce. What they definitely didn't, and couldn't, know was that months earlier the clothes I wore to work and the way I looked at him had made his erections harder and harder to hide. He had been alone for so long. I was trying to seduce him, I think subconsciously.

I would sneak up on him, say flirty things, bend over when I shouldn't, etc... One night, when we were working late alone, I heard him filing and came around a corner. It was so typical, he spilled coffee on my top. The coffee was luke warm, but I let on that it was hot. His hands groped my chest and I quickly unbuttoned the top - revealing to his, and indeed my, surprise that I was wearing a black see-through bra (the only one I owned from prom).

The investment at Victoria's Secret was finally paying off. I acted unconcerned. I soaked my shirt in the company office's only sink. Because it was basically a trailer that they moved from site to site, quarters were tight. He came in, face flushed, apologizing profusely. He explained that he didn't know it was going to happen, that it was an accident. I said it was okay. I didn't think I was burnt, just hot. As my shirt soaked in the sink, he blabbed on, just inches away from me. His eyes darted about, trying not to stare at my breasts too long.

I could feel and see the tint and sticky feel of sweetened coffee. The smell lingered in the air, and I slowly patted paper towels on my chest and then-hardened nipples. Time and again I found myself, curious in my own rite, staring back at him. It seriously looked as though he was hiding some form of equipment behind the zipper of his faded jeans.

I said, hold that thought, and turned around, starting to unclasp the back of the bra. I started to complain, saying my bra was wet too. He said, oh that's a serious problem... and blabbered on, not leaving. The bra was unclasped when I turned around, loosely covering my young, firm breasts, their heavy bottoms exposed. He stayed, frozen, staring down at me. That was it, I knew he wanted me desperately. He couldn't avert his eyes and I could tell his breathing was heavy and deep. I knew I could take control. I could see the long bulge developing even more near his pocket as his eyes darted into my eyes then away, then scanning back over the nearly transparent bra.

He noticed my look and stopped. He knew I was staring at his bulging member, as it was independently trying to fire from its gate. I waited. I knew to let him stare, and let him feel like I was bothered by him, would give me complete control. What is it, he asked. I said, do you want to kiss me? That was it. It was frantic. I was, as usual, wearing a skirt. He literally tore the crotch off of my panties. Between the time he entered me and the time we climaxed together, only my bra, his fly, and my panties had been removed. It was fast and furious. It was intense. And though he lasted only moments, the build up, and the size of his manhood had produced the best sex I had ever had in my life.

Soon, we were having sex three or four times a day. Whenever and wherever. We destroyed furniture and made love atop blueprints on worktables. I would often not wear panties during our shifts, even though there would be others around. His hands would find from me from beneath my skirt with people just feet away. I would flash him and moon him. I would unbutton my shirt too far and lean over in front of him. His smell and taste were always on my mind.

I imagine that he had a very dull marriage, because he was hungry all of the time - more hungry than any man or woman I had ever met before. And though he was a considerably slight man in build and frame, he was driven by me and I by him. We weren't really in love, though, at the same time. It was fun and sex. We were cautious not to make it anything more. It was like finding something free, that two people can enjoy. We knew we weren't really going anywhere over the long term, but we were cautious not to ruin a good thing.

When we formally (though secretly to my parents) started to let people he knew know about our affair, and he brought on someone to do my job most of the time, things got more intense. I became a frequent visitor to his apartment. I even got a key. He taught me amazing things and showed me things I had never seen before. His budget for items of romance and sex was amazing, and to my surprise, he had replaced my entire lingerie wardrobe so I could have a complete collection of see through bras and panties in every color imaginable. It was another amazing gift in a long line of things he did to celebrate our encounters.

We held a fire and burnt all my other underwear, and made passionate love that winter night by the raging fireplace in his large apartment. Thankfully, my parents believed my new budget was due to the fact that I had been promoted. Had they only known I was the boss' mistress, they would not have been so impressed. My mom commented on the bras, but, she said, it's probably time you outgrew such things.

In many ways, his budget for all things was amazing. He took care of me, and I took care of him, though we had only really been in a relationship (err, having sex) for a couple of weeks. I called him my boyfriend, almost on a lark. In some ways it was a complete falsehood, and in others it was more real than anything. I would do anything sexually for him. The day after our first romp, I even gave him a blowjob from under his desk while he was on the phone working out a business deal. He put the client on hold to cum in my mouth, then went right back to work. We later joked that it was the most presidential thing he had ever done. I was his toy. I was his Barbie Doll. He would dress me up, and I would play the part.

At any rate, back to the story.

One night, he, his older brother/roommate/bitter-pain-in-the-ass, and four of his friends were over watching college football on a Saturday night. I had never met the friends before.

His brother I had met. From the first day I was hired by my now-boyfriend, his brother kind of creeped me out. There were always weird looks. Though they sounded amazingly alike, and looked alike - nearly identical besides the color of their hair and eyes - his brother was definitely not my type. His brother was more serious, more withdrawn, moody, mischievous, and calculating.

Though they looked alike and were very close to each other, their personalities made them opposites. They had been married at close to the same time, had owned the business together, and had gotten through terrible divorces together.

His friends seemed nice. Though, it was tough trying to track down their names and harder for me to remember. They had a definite edge to them. They could be crude, and seemed to have violent tendencies - probably in their younger years they would really raise hell.

They were all "guy guys," who had played football together in college. My boyfriend's brother was a quarterback, I think. He was supposedly very good at playing football, though that wasn't something that typically impressed me. He was still an asshole in my book.

When the football game got over, the guys started to play cards. I was debating calling a girlfriend and going out, but my boyfriend had gotten trashed, and I knew he needed me. Plus, we had just started dating and I wanted desperately to spend the night with him. The longer the game went, the more drunk they got.

I found myself getting a little tipsy as the night wore on. My boyfriend encouraged me to sit down with the guys. Have a drink, he said, play some cards. He told me they were great guys and had all been through a lot together. I sat down, somewhat disinterested. They changed the game into some weird drinking game. I didn't understand the rules all the way, but it was better than poker. My boyfriend joined us.

Before long, my drink was gone. One of the guys got up and mixed me a new one. It was devilishly strong. It seemed, by some strange alliance, that my boyfriend and I kept getting the worse of the game. The previous round's winner frequently changed the game's rules. The guys, and whichever jackass happened to be the last winner, started to make some weird suggestions that seemed somewhat intriguing, somewhat dangerous.

Though my boyfriend was rather small (he met the stereotype of the "thinking" philosophy major, despite his construction career), I guess he was a kicker or something because they used to tease him, they were all big. I imagined they could overpower me and the more they drank the more hungry their eyes seemed to get. Always looking to obey the rules of the game, my sweet boyfriend was nearly out of commission. He eventually passed out. We played several hands afterwards, this time, with me turning the tide, but getting sloshed in the process.

The men had given up all context of propriety. Though, with my boyfriend out, the suggestions stopped, the electricity of the room was at a feverish pitch. They were staring at my blouse, and I suddenly wished I hadn't worn something so revealing. You could definitely see my bra through the silk shirt, but on closer inspection, you could, with little imagination see through to my sheer white bra underneath.

Mind you, I had worn this quite on purpose. There was going to be a football game, and I didn't want to lose all attention from my boyfriend just because they guys were over. Plus, I wanted them to think I was hot, because I knew it would make my boyfriend proud to have me.

At the same time, I knew that these guys probably knew what was going on. His brother definitely did. They had to have questioned the legitimacy of our relationship. Most of them probably had daughters may age. But, by the looks of them, they weren't thinking about their little girls.

It seemed like my wardrobe selection had backfired. Especially when a light breeze trickled through the room when one of the guys opened the door of the porch. My nipples, though not extremely large or sensitive, suddenly came to life. Glancing down, it was unmistakable. I suddenly felt naked, and crossed my arms - rousing the fixated eyes of one of the men. But to use my hand of cards, I had to move my arms, and to move my arms was to elicit the same glares.

I felt like I was in a grab bag. I imagined that in their minds, the men were all contemplating how easy I must be. How the little slut just started working with the guy. I'm sure they had heard rumors about what was going on. My boyfriend wasn't the kind of guy not to brag about the blowjob in the office during the Clinton trial.

What's even more odd was that the guys kept dropping things on the other side of the table. They would take turns picking whatever it was up. I could have sworn they were cheating. So I would pear across the table. I would look around the table and see looks being passed among them. My boyfriend's brother had a smirk on his face like a fox that had just left the hen house.

Upon closer inspection, I realized that the guys were paying less and less attention to my chest and more attention to whatever it was they had dropped. Although I was drunk, I wasn't stupid. I realized that they weren't cheating, they were looking up my skirt from beneath the table. While sitting down, as drunk girls sometimes do, my skirt had become disheveled, exposing a large portion of one of my legs and riding my skirt a little too high.

My boyfriend's brother was somehow up to something bad. He was also divorced and said on more than one occasion that the word woman was synonymous with the word slut. I thought about how he had never really liked me. It occurred to me that he didn't want his kid brother to have a girlfriend so soon after his divorce. I decided to make a stand, if only for a moment. I stared at him, just as he had been staring at me all night.

My intoxication was taking over. The strong drinks effected me deeply, so much that at any point I questioned my ability to drive, I had decided I was invincible. I decided that I would show him. I am woman, hear me roar - only in my own way. The next time one of the guys "dropped" a card, I spread my legs under the table. I could feel the cooler air in the apartment sweep up between my thighs.

My matching white, sheer panties were exposed. They were cut high, and the white shade made my small patch of red hair pink. I took my hand, never leaving the eyes of my boyfriend's bastard brother, and ran it down beneath the table. The room froze. I locked eyes with the evil brother and without blinking deliberately slid the cards over my nipple with my free hand. We locked eyes.

I touched myself with my legs fully exposed to the peeping card player, running my middle finger lightly over the silky fabric, then quickly turned it around, flipping him off. With a thud, his head slammed into the bottom side, sending several beers pouring over the top of the table. I had to laugh, as did all the other guys.

It stilled the tension, and I accepted it as a minor victory in what was shaping up to be an entire campaign. The guys sort of took things a little less seriously after that. I wasn't scared of them for the moment. They seemed like big teddy bears. I quit shielding myself as we played cards and we all started to laugh and joke.

I didn't worry about my boyfriend. I knew it would get back to him, and I imagined it would likely arouse him before causing anger. We were fairly free in that way. But, too much was certainly too much. I knew I was fortunate to have such a good thing going.

I had somewhat become one of the guys, and I'm sure it infuriated my boyfriend's brother, who quit looking at me in defeat. After a while, I got up to go to the bathroom. While there, I went ahead and undid the top two buttons of my blouse and pulled up my skirt higher on my hips, exposing more of my white legs.

The attention was no longer frightening, it was sort of a turn on. I wanted to satiate my natural ability to tease, and I prefer to wear my sexuality more openly. As my boyfriend snored, we played several hands. The more I teased and got along with my boyfriend's friends, the more it seemed to anger his brother. The more I angered his brother, the more satisfaction I felt.

Talk of strip poker kept going around. Playful jokes were made. One of the guys told the peeping Tom fellow that he was so small, he'd better avoid taking off his pants unless he wanted to humor me. At ease, I seemed to be drinking more. And though we were kind of buddying-up, it was nearly eerie that whenever my drink was empty - even a quarter of the way - magically a full one would appear before me.

It reminded me that while it seemed like I had known guys like this all my life, I was among strangers, not "older brothers." They were tough guys, although I seemed to be in their circle. There was something rough about them. They laughed loudly and drank a lot. Most of them rode motorcycles and all had blue-collar management jobs, some working for my boyfriend. They were in charge of men. For some reason, the difference between all of these guys and my boyfriend seemed fascinating.

They all took care of him, though he was smaller than them. They teased him a lot, but not as hard as they were on each other. And while they fascinated me, there was really only one thing that I wanted tonight - my boyfriend's familiar sex. I imagined sobriety had taken its course on my boyfriend and began to wake him his favorite way. I quietly put my hand on his lap and felt around for his penis. Even flaccid, it was long enough to reach a considerable distance down his worn jeans.

As I ran circles over the fabric, it began to grow. The sensation brought my guy to life. He seemed startled, but like a boy waking up on Christmas morning, he was focused on the possibilities that lay ahead. Guys, he said, It's time for bed. I'm going to crash out. He looked at me and asked if I was getting tired, as if he needed the answer.

It seemed to upset the boys club - not to lose my boyfriend - but to lose me. I was flattered in ways I didn't want to fully contemplate. They told my boyfriend that before he went to bed, he had to complete what they called the "Endurohol," which was a college tradition for the first guy to crash out. It sounded more like alcohol poisoning to me - something guys my age would do to further intoxication as a sport. They lined up two plastic glasses of beer, two shots of tequila, a shot of nighttime cough syrup, a nodoze and a small glass of water.

 
There is more of this story...

To read this story you need a Registration + Premier Membership
If you have an account, then please Log In or Register (Why register?)

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.