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A Banker's Special Deposit Box

Story Info
Cheating girlfriend has rough sex with her boyfriend's boss.
6.7k words
4.21
114.5k
133

Part 1 of the 2 part series

Updated 06/09/2023
Created 07/18/2019
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Jordan45
Jordan45
263 Followers

My girlfriend Jessica and I have been dating for six years and sharing an apartment for two. We plan to get married, but first we are putting away money for a down payment on a house. Jessica is a petite, mousy brunette. Her face is cute, although not really beautiful, but she has a smoking hot body. We started dating in college. Back then, Jessica she was shy and extremely self-conscious about the size of her breasts, which are firm but incredibly large for a woman so small. On her slender frame they are impossible to ignore. Her nipples are small, perfectly round nubs, and they are seemingly always hard, making them completely obvious through any kind of light clothing. For years, Jessica wore baggy, loose-fitting tops and was always complaining that they didn't do enough to hide her enormous chest. It didn't help that her bras were always too small. It is nearly impossible to shop for bras in size 32EE, so Jessica was often forced to wear a DD, which would struggle to contain her huge jugs. Of course, I've always loved her tits. The great thing about them is that, in addition to their size, they are incredibly sensitive. When I play with her nipples, her legs start to tremble and she whimpers with lust. It's like her nipples are directly connected to her pussy. Jessica can have an orgasm just from having her tits played with—especially if I am a little rough with her nipples. That makes her crazy.

These days, however, that has been happening less and less frequently. Jessica has grown restless and unsatisfied with our small apartment. She wants to buy a house. I mean, we both do, but Jessica is especially determined that we move into a house of our own as soon as we possibly can. Her mind is so preoccupied with thoughts of getting out of our apartment that she seldom seems relaxed and in the mood for sex. In order to save for a down payment, I've taken on as many overtime shifts as I can get. By the time I get home from my job as a security guard at a mid-sized, family-owned bank, I'm usually too tired to woo her into a more receptive mood. Besides, I have never felt completely adequate in bed with Jessica. She never complains, but she never really compliments my performance either. My penis is average or maybe even a bit smaller and, on the rare occasions when Jessica wants to have sex, I don't last too long.

I've known for a few years that Jessica has unfulfilled sexual fantasies, but she doesn't share them with me. I only found out by mistake. Two summers ago, she happened to leave her cell phone lying around on the table when a text popped up from her best friend, Lauren. Lauren is a sultry-looking redhead whose breasts, while not as large as Jessica's, were plump and enticing in their own right. Jessica had gone out with Lauren the night before, telling me they were going to have a low-key evening, staying in to drink wine and maybe watch a movie together. Well, apparently the movie they chose was a porn film because Lauren's text was very dirty. She texted my girlfriend to say that she couldn't stop thinking about that one guy with the huge cock. Her use of the word "cock" is what caught my eye. Picking up Jessica's phone, I quickly read the exchange that led up to this. I was shocked by what I saw. It seems Lauren wasn't the only one who was transfixed with this big dick. My little Jessica's texts weren't as explicit, but what they implied left me reeling. She wrote two words that I'll never forget: "I wish."

I asked Jessica about her night with Lauren, but she never gave me any hint that it involved watching porn and fantasizing about some well-hung stud. We did have some hot sex after that—but I knew from then on that my cock would never satisfy her. She wanted more.

Jessica, now in her late twenties, has become more confident. She's stopped hiding her figure and has started wearing clothing that actually shows off her big breasts. Jessica works out a lot, so she's always prancing around in a pair of yoga pants that makes her tiny ass look amazing, with a tank top stretched to the limit by her amazing rack. She is so short that the deep cleavage bursting out of her tank tops is on display to nearly everyone who sees her. I find this exciting, but it also worries me because of all the male attention she now gets.

It all came to a head at a large pool party my boss Jeff recently threw at his house for our entire company. Jeff is divorced, about forty-six years old, and lives in an imposing mansion on several expertly landscaped acres. He has an Olympic-sized pool, a hot tub, and a patio with an outdoor bar. Jeff's house sits up on a big hill, with a three-hundred-yard driveway leading to it that keeps the place secluded. Jeff inherited the house, and the bank, from his father, and he really loves to throw his money around. Jeff played lacrosse in college and is still in peak shape, standing about six and a half feet tall and carrying about two hundred pounds of solid muscle.

I suppose it all began with the bathing suit Jessica bought for the party. It was a tiny bikini that barely hid anything. Her tits are so big and full that the bikini top only covered about half of each breast. From the side, in fact, you could see nearly her entire breast. The bikini bottom left most her little ass exposed too—it wasn't quite a thong, but it didn't leave much to the imagination. I told her that there would be over fifty people that I work with at this party and that she would probably be more comfortable in a modest bathing suit or a cover-all. The truth was that I would feel more comfortable if she wore something less revealing, but I wanted Jessica to think it was her idea to leave the string bikini at home. It didn't work. Jessica just laughed a little and told me that her new suit was in style this summer and that I was being ridiculous, whereas I should've been proud to be with such a confident woman.

When we arrived, Jessica had on a short terry-cloth robe that she wore over her skimpy suit. Looking around, I realized to my dismay that most of the other bank employees hadn't brought their wives or girlfriends. They were scurrying around the party, tending bar, keeping the food stocked and so on. Jessica sauntered over to the hot tub and slipped off her robe, putting her deep creamy cleavage on display in the process. She looked stunning. She began rubbing tanning oil on her body, and those huge, firm tits of hers were just jiggling and bouncing around. In a matter of minutes a small crowd of guys had silently taken up strategic positions around her just to leer at her body.

Just then, I got pulled aside by a co-worker who wanted to talk about last night's Orioles game. As he chatted my ear off about double plays and innings in relief, Jessica wandered in the direction of some chaise lounge chairs arranged between the hot tub and the pool.

Jessica was sprawled out, drink in hand, with her knees slightly up, when I walked over and realized that, in this position, her fetching little bikini bottom was completely inadequate: there were small tufts of pubic hair visible for everyone to see. Jessica keeps her pussy neatly trimmed, but with a suit this size, there just wasn't enough coverage. So imagine me standing there, asking her if she'd like me to get her a drink, knowing that about ten guys I work with were staring at her nearly naked body all afternoon long, and I couldn't do a thing about it. I just tried to enjoy the party, but it was tough.

After we'd all been drinking and catching rays for about two hours, my boss Jeff came up to me and told me it was my turn to be bartender—he needed me for a two hour shift. As I moped off to my bar tending duties, Jeff put his arm around Jessica's waist and said, "Don't worry. I'll keep your girlfriend entertained." She'd already had a few drinks, and I could see by the glazed look in her eyes that she thought Jeff was hot.

I manned the bar, about thirty feet from the hot tub, and did my best to keep the guests supplied with drinks. I could see Jessica moving through the party on Jeff's arm, laughing and whispering to each other and schmoozing as if they were a couple. All I could think is that her bathing suit was way too small. Her breasts and ass were only minimally covered by a bikini whose strings danced seductively as she let Jeff lead her around the party.

While I was bartending, someone turned up the music playing on the outdoor speakers so people could dance on the patio. Only a handful of ladies joined in because so few of my colleagues had brought a date, but as I scanned the swaying couples, I spied Jeff and Jessica in a dark corner beyond the hot tub, locked in a slow dance. Instead of keeping a polite distance, that asshole Jeff pressed her so close that her breasts were flattened against his stomach. I could tell from the way that she danced that she'd had too much to drink, which always makes her horny. As they danced in small circles in the far corner, Jessica kicked off her shoes and stood with her bare feet on top of Jeff's expensive-looking leather shoes. Jeff took her small hands in his giant mitts and slow danced her around the patio, periodically leaning in to whisper in her ear. I couldn't bear to watch.

About that time, we ran out of white wine at the bar. Someone directed me to the basement, where there was supposedly a large supply of wine and liquor. I went downstairs and gazed in awe at Jeff's expansive wine cellar. It had elegant built in bottle holders that put each bottle on exquisite display. I was rummaging lazily in the back, half staring at my rich surroundings and half looking for white wine, when I heard my girlfriend's voice. "Jeff, where are you taking me?" Jessica giggled.

Jeff told her he wanted them to cool off for a minute out of the hot sun, and thought she might enjoy seeing his wine collection. I crouched down behind the farthest wine rack—I was only about fifteen feet away from them.

Jessica replied with a exaggerated little girl voice, cooing that she didn't know anything about wine, except that she liked to drink it. She punctuated her innocent act with a giggle. Jeff responded to her playfulness by swooping behind her and grabbing her at the hips, where the strings of her bikini bottoms beckoned, and he began subtly grinding his crotch against her adorable little ass.

"You have a tight little body, don't you?" he said. "Do you know you've been driving all the men at this party crazy?"

My girlfriend giggled again, but quietly this time, her voice soft and feminine. She stood still and wide eyed while Jeff's grinding became more obvious. Instead of pushing him away, Jessica leaned back into him, fluttering her eyelids as she slurred, "My boyfriend is really mad at me. He thinks my bathing suit is too small."

From my hiding place behind the wine rack, I could see a look of smug satisfaction cross Jeff's face as he realized that Jessica was responding to his moves. I could detect a subtle shift in his tone, too. Although Jessica was surely too drunk to notice, there was a slight edge to Jeff's voice as he said, pointedly, "Your boyfriend should be proud of your body. You like men looking at you, don't you?" As he asked the question, Jeff slowly brought his hands up and took a breast in each one, squeezing them gently. I couldn't believe I was watching my boss put his hands all over my girlfriend's big tits, which looked like they could burst out of her bikini top at any moment. But I scarcely had time to process what was happening before Jeff repeated the question, this time more insistently. "You like men looking at your body, don't you, Jessica?"

As his question hung in the air, I slowly realized that this was my chance to intervene. But I felt frozen in place, overcome by the fear of being discovered and a powerful curiosity to see how far Jessica would let this go. Her eyes were closed and she was rocking slowly back and forth, rubbing her ass against his cock while he fondled her tits. But Jessica's eyes opened wide as Jeff pulled her around and smashed his lips into hers. She let the kiss linger for just a moment before pushing him back, saying, "My boyfriend is right upstairs—I shouldn't be doing this." But Jeff could hear the uncertainty in her voice and so could I. He took her hand and placed it on his cock, which was now pushing the front of his bathing suit out a couple of inches.

"We can leave right now if you can honestly tell me you don't want to see this," he said. He held her wrist while she rubbed his cock through his suit. Then he leaned forward and kissed her again, and this time she opened her mouth, sucked on his tongue and began making little moaning noises. Jeff let go of her wrist, but she kept rubbing his erection.

After a passionate make out session, Jessica pulled back to look at the obscene bulge protruding from the front of Jeff's bathing suit. "Oh my God, Jeff, it's so hard!"

I could see Jeff smiling. He told her to wait a minute, then walked over and locked the door. He said, "Don't worry about your boyfriend. He'll be busy bartending for at least another thirty minutes, and nobody would dare come down to the wine cellar without asking me."

Jessica looked dazed with lust as Jeff took her by the arm and led her to an oversized leather sofa about twenty feet away from where I was crouched. He slowly peeled off his suit. His cock was truly awesome—about nine or ten inches long and very thick, with a huge head. Jeff sat on the sofa and instructed Jessica to take off her bathing suit. She stood up in front of him and reached behind her back as if to release her bikini top, but she hesitated for just an instant. "Do it Jessica, right now," he commanded her. "You know you want me to see your body." I couldn't believe it—she reached up and untied her top, and there were her enormous breasts, in the flesh, dangling before Jeff's eyes, the perky nipples completely erect. Jessica then peeled off her bottom and stood there quietly. She must have expected Jeff to resume manhandling her chest, but he didn't. Remaining seated, and watching her intently, Jeff said, "Rub your tits for me. Play with your nipples." Jessica followed his orders obediently. She began to rub her breasts, which looked even more massive in her delicate little hands, then took her nipples between her thumb and forefinger and began pulling and twisting them. Jeff let her play with those spectacular tits for several minutes, a painfully long time for me as I remained rooted to the floor, kneeling to stay out of sight. The tit play got Jessica hot and as she continued tugging at her nipples, her moans became deep and rhythmic. Finally, Jeff said, "Get down on your knees and suck my cock."

A tiny sigh escaped her lips as my girlfriend fell to her knees in front of my boss and slowly licked his dick from his balls to the tip, rubbing her tits as she did so. While Jessica slurped on his mighty hog, her bare feet crossed at the ankle and swaying in time with her ministrations, Jeff began talking to her. At first, he was complimentary, telling her how beautiful she is and how much she excites him. But as Jessica worked his cock deeper into her throat, his words became more condescending — almost a taunt — as he patted her head like a child and repeated, "That's a good little cocksucker." I have no idea how long this went on, but it seemed like an eternity. Eventually, however, Jeff helped her to her feet and told her to sit on the sofa. He stood in front of her and slowly rubbed his big cock all over her face, saying to her, "Tell me you love it. Tell me you're my little suck slave and that you'll do anything I tell you to do. Tell me I can have you anytime I want. Tell me, Jessica."

Jessica sat there with her mouth wide open, moaning around Jeff's immense penis as he thrust it in and out of her mouth. My boss really knew how to work his dick. He teased her with it as she sucked, putting the giant spongy head between her lips, then pulling back and rubbing it all over her cute face, which was getting wet from her spit and red from the friction. Suddenly Jessica started pouting and begged, "Please don't tease me anymore. Just let me suck it. Let me feel it gush down my throat."

Jeff smiled down at her and said, "First tell me you'll do whatever I say. Tell me you love being my sex slave."

Jessica sighed and said, in her best little girl voice, "I'll do anything you want, just let me have that beautiful cock."

Jeff leaned forward, and I watched, slack jawed, as my girlfriend sucked and slobbered over his cock for another ten minutes. Every so often, Jeff would pull his tool out of her eager mouth to ask her, "Are you my little cockslut?"

Every time, Jessica said yes, and every time he rewarded her with more cock.

Finally, after my girlfriend had made a complete slut of herself on his dick, Jeff must have been close to an orgasm because he said, "I don't want to come in your mouth. I want to fuck you so you can spend the day feeling my hot load inside your pussy."

Jeff grabbed my girlfriend by her ankles and slid her body until her ass was all the way to the edge of the sofa, then knelt down and pushed her knees up to her chest so that her cunt was spread wide. He said, "Rub your pussy for me. Get yourself hot." I couldn't believe it—Jessica reached down and began to rapidly rub her clit.

"Fuck me, Jeff," she whimpered. "Give me that giant dick." Apparently that is what Jeff was waiting to hear because he began to rub his engorged cock up and down the sopping wet entrance to Jessica's pussy. He didn't put it in; he just rubbed that monster cock back and forth against her clit, as Jessica watched in wide-eyed awe. She began to moan and shake and plead with him to enter her. As she lay there splayed on the couch, her trimmed pussy damp with arousal and obscenely exposed, her enormous chest pressed down firmly by her knees, Jeff lazily pulled back and, with a single thrust, pushed his full ten inches into my little Jessica. He began to pound away, fucking her very hard. Jessica immediately had a violent orgasm, moaning and grunting as she climaxed, bucking her ass up to meet his cock.

My boss then began to tease her again, fucking her hard, then stopping suddenly. Jessica frantically reached up and began pulling his ass toward her, saying, "No, Jeff, please don't stop. Make me come again ... please!" Her voice was whiny with need as she shamelessly begged him for cock. Jeff resumed his assault on her pussy, playing very roughly with her breasts as he screwed her into submission. I couldn't believe his stamina—he must have fucked her hard for twenty-five minutes. Jessica had four wild orgasms in that time. She was so exhausted that she could hardly even make a sound and her moans were reduced to a hushed whimper. Finally she reached down and began milking his full balls. "Come for me, baby," she urged. "Come in my pussy."

I had never heard Jessica utter those words and they sent shockwaves through me. She had always made me wear a condom, even when she took the pill, just to be extra safe. Now here she was, begging my big-dicked boss to shoot his load deep inside her. Jeff grunted loudly and had a tremendous orgasm, driving his magnificent cock into her as deep as it would go and filling her little pussy with his semen.

He pulled his prick out of Jessica's vagina, slapped it hard against her face and said, "Clean it for me with your pretty mouth." Jessica didn't even hesitate—she began alternating between licking the come off his cock and swallowing it until she gagged, not stopping until it was soft again. Jeff tossed her bikini at her and told her to get dressed and go back to the party. "I'll be up there in a minute," he informed her. Jessica wriggled into her bathing suit and turned to go upstairs. But before she could leave, Jeff grabbed her and asked, "Are you my big titted slut?"

Jordan45
Jordan45
263 Followers
12


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