Stephanie Miller didn't expect her roommate for a week at a company retreat to end up being a younger man. Could she be faithful to her husband and resist him?
"Bye Sweetheart," she said as she kissed her husband one last time and got into her car. Waving goodbye to her two young kids and husband as she backed out of the driveway, Stephanie Miller was kind of excited about going away for a week.
Although she would miss her family greatly, she hadn't been away on her own in years and, at 40 years old, she felt like she could really use the break. She worked for a small advertising and marketing firm, who had just been acquired by a bigger company. Someone at the top had decided getting all the employees together for a week to do some team building would be good for morale.
There were a couple hundred employees, and it was decided that in order to get to know each other better, each person was assigned a roommate for the week, meaning two people would be sharing each hotel room.
Of course, it was going to be women with women and men with men, as would be appropriate for a professional setting. She knew her roommate was Terry Blanchard, but knew nothing about her. As a VP herself, she had some power and ability to do some digging. But all she could find out so far was Terry was new to the company, and worked in the kitchen in one of the cafeterias in one of the branches. Because she was so new, there wasn't any information on her yet. But Stephanie didn't care that much, she was happy to get away and hoped Terry was fun and they could enjoy each other's company for the week. After an hour or so she stopped for a quick bite to eat and checked the hotel amenities. She was happy to have learned they had a gym, as she liked to keep in shape, and although she was 40, she looked 30 and ate well and worked out hard. She wasn't against a little flirting from time to time if needed, and if it had played a small part in her getting to her VP role, she didn't mind. She'd never cheated on her husband, Dave, and never intended to. They were like most couples after a couple of kids and in their middle ages. Most days were routine and boring, and intimacy was pretty much a thing of the past. Sex once every week perhaps, maybe less, quick and unsatisfying most of the time. But Dave was a good man and treated her well and they were happy together. Finally, she arrived at the hotel and checked in. Minutes later she entered the room and saw that her roommate had not yet arrived. She settled in, called home, talked with the family, did a bit of work, then figured she'd go check out the gym and pool and get her bearings for the team events in the days to come.
Awhile later she returned to her room, and heard the shower on. A bag was sitting on the other bed and she was happy to finally be about to meet her roommate. She didn't want to freak her out, so she didn't call but just sat in a chair and waited a few minutes until she heard the shower stop. A couple minutes later the bathroom door opened and out walked her roommate, and Stephanie gasped out loud and waved a hand hello awkwardly.
Standing ten feet away was not the woman roommate she thought she was going to have, but a man! And a young man, he couldn't have been more than 25. And a naked man! She couldn't help but notice his cock was semi-hard, and large, and he was in great shape and gorgeous! He was over 6' tall, with a six pack abdomen, big green eyes, and wavy black hair that went to his shoulders.
"Oh hi!" he said enthusiastically as he dried his hair a bit with a towel, seemingly not the least bit concerned that he was naked in front of a strange woman. "I'm Terry," and he started to move forward to shake her hand. "Hi, um, Terry," Stephanie replied, not looking at him. "Um, can you put some clothes on please?
"Oh, yah, sure, sorry about that," he replied like he was surprised she would have a problem with it. He walked over to his suitcase and put on a thin pair of boxers and a tank top. "Ok, good now," he said and saw her still hiding her eyes. Stephanie slowly looked back at him and he walked right in front of her and held out his hand to shake hers. His manhood was still quite prominent through the thin material and she tried not to look again as she shook his hand, stood up, and moved away.
"Um, Terry, Hi, I'm Stephanie, but there must be a mistake. We're supposed to have same sex roommates. We have to correct this," she said, and did not like how cavalier he was being with exposing himself. "Oh, yah, sure, I mean, I don't care, if you don't. I heard the whole place is filled up. I mean, we have two beds," he answered, and really seemed to think this situation was totally fine.
"Terry, no offence, but I'm married," she replied and showed him her ring. "And common courtesy is not to expose yourself or walk around, um, half naked, in front of a woman who you just met." She was quite disturbed and angry that he didn't get that, and thought he just must be so immature still. "Sorry Stephanie, I'm just one of those people that's comfortable in my own skin. I don't mean to offend you. I'll put some shorts on," and he did.
They exchanged pleasantries briefly and he told her how this was only his first week on the job, and he was a cook in the kitchen at one of the office buildings. When she told him she was a VP, he replied,
"Wow, that's impressive. I'm flattered that I get to room with such a powerful woman. Maybe you can teach me a thing or two about business." She realized he had good intentions and was just young and naïve. "Well, Terry, that's flattering and thank you, but I cannot room with you, it's just wrong on many levels."
She proceeded for the next several minutes to call down to the manager, and other nearby places but there were no other rooms. She was getting more and more frustrated by the minute and her roommate saw her anxiety on her face and as she hung up the phone and gave up, sighing, he came over and stood in front of her and took her hands in his.
"Stephanie, I know you're frustrated, I can see that. Listen, it is what it is. You're a beautiful woman, and your husband's a lucky guy. You've got your bed, I've got mine. Let's just make it work. I'll be more careful about walking around naked, and you don't like fire me or anything, ok?" He laughed, but she thought maybe he actually believed she could fire him, which she couldn't. At least she didn't think she could.
She thought, and sighed. "Oh alright, fine. It's weird and probably will be awkward but I guess we can make the best of it. If you don't mind me asking, how old are you Terry?" "24," he replied. "Ten years younger than you," he said, smiling. "Thank you, you're sweet, but I'm older than that," she replied back and felt good that her hard work to stay healthy was at least noticed.
"Well you don't look it," the young man replied. "Well, it's getting late, I guess I'm going to go to bed, if you don't mind having the lights off."
"No, that's fine, I'm going to turn in too." And she went to the bathroom, he turned out the main room lights, took off his clothes so he was naked again, and got into his bed. She purposely waited until he was in bed to come out, shut off the bathroom light and made her way in the near total darkness to her bed. She had only planned on wearing a pair of panties and a tank top to bed, and changed in the dark into her sleeping attire so he wouldn't see. Then she crawled under the covers and went over in her head all the reasons this was inappropriate and wrong. He seemed harmless enough she told herself, and did seem respectful that she was married. She chalked up his thoughtlessness with being naked in front of her to youthful ignorance and boldness. Eventually she fell off to sleep.
In the morning she woke up, and heard him in the shower. Since she had to wait to use the bathroom, she decided to check in with Dave. As he answered the phone, she said hello and then asked him, "Well, guess who my roommate turned out to be?" And she went on to explain to her husband how she ended up with a male roommate nearly half her age. Of course, her husband was suspicious and livid, and wanted the situation corrected immediately.
Stephanie went on to explain that it couldn't really be fixed, and he was harmless and they talked about it and she set clear boundaries and believed it would be fine. She didn't want to keep secrets from Dave, so she did tell him how Terry had come out of the bathroom naked. Needless to say her husband almost jumped through the phone. After several minutes of talking, and her reassuring him many times it wouldn't happen again, and it was all a misunderstanding, he calmed down somewhat and reluctantly agreed to trust the situation. In his head, he wondered if she liked Terry's cock, and if it was bigger than his, but he didn't ask his wife, maybe he was afraid of the answer.
She reassured him several more times and told him he has nothing to worry about. Just then the water stopped and she told Dave she had to go into the shower shortly as Terry was done in the bathroom in a minute. They talked a little more and then Terry came out. As he rounded the corner and saw her up and on the phone, he figured he should be quiet so as not to interrupt her conversation so he just waved hello and smiled, holding his towel in his hand. Stephanie paused mid sentence talking to Dave, and gasped again. Her first feeling was anger that he didn't listen as there the young man was, fully naked again with that semi-erect cock and that beautiful body. She pointed at him and mouthed, "What the fuck?", annoyed that he did exactly what he said he wouldn't do. And then she felt mad at herself that she caught herself staring at his cock and quickly wrestled her gaze away. It had to be 6 inches semi-erect at least she thought, and actually had the thought of wondering how big it was fully erect. Immediately though she dismissed that thought, recovered, and continued talking to her husband, who didn't seem to notice her pause. She quickly ended the call.
"Terry, what the hell? What's with being naked again, I thought we agreed you wouldn't do that anymore?" He turned to face her, standing by his bed, only about five feet away. He made no effort to cover himself and his cock dangled in front of him. She tried to keep eye contact with him but her eyes wanted to lower and look somewhere else. "Oh crap, sorry Stephanie. I totally forgot. I was preoccupied thinking something else. Sorry," he sounded and looked genuine but made no effort to cover up.
"Um," she said annoyed and pointed at his towel on the bed. "Oh crap, sorry," he chuckled and sat down and covered himself as he reached for some boxers to put on. "Sorry, sometimes I'm so forgetful, makes me wonder how I get through the day." And he laughed again. She chuckled slightly awkwardly and shook her head, hoping this was just youthful ignorance and nothing more sinister.
The day passed and they had many team building exercises with their colleagues and had a big lunch together. There was some free time after lunch and Terry asked if she would talk with him. She learned he was really quite a nice young man, just very poor with personal boundaries. He was raised by a single mother, whom he was still very close to, and they never really had much money. He had moved out a couple of years ago and was trying to make it on his own. She felt sympathy for him, as he didn't have education past high school and had had a lot of struggles in his young life. She felt privileged with her upper-middle class lifestyle and after talking for over an hour, she really felt enamoured to this young man, but in a motherly or mentor type way, not romantically. After all, he was nearly half her age. "He just needs to learn to put clothes on!" she thought to herself and pictured his cock again, which she had seen twice already.
Later on, they were together again for a short while after a group assignment. "Stephanie, can I ask you something more personal? Well, it's not really personal but generally about women?" he asked. She was flattered that he thought of her as an authority on women, which she clearly felt she was not. "Sure Terry, I'll try my best to answer, but I'm no authority on women. What is it?"
"Well," he said. "I've been with a few women," he hesitated, like he was afraid of embarrassing himself, or her. "You know, sexually. But I'm wondering, do women really care about penis size? Is bigger really better?"
Her face went beat red and she struggled for an answer. Normally maybe she wouldn't have felt so bad, but having seen his naked cock, and how big it was not fully erect, and how it kind of turned her on, she felt very inadequate and quite inappropriate to answer that.
"Um, well, Terry. I mean I'm no expert, but, I think it matters more how you use it then its size." And she blushed again and couldn't believe she was talking about penis size with her new young colleague. "Oh, ok. Because, well, the girls I've been with, they were, well, they said they loved how big my penis is and when I was inside them, you know, having sex, they came really hard because of how deep I was in their vaginas."
The candor of this young man knew no boundaries at all. She couldn't believe he was being so open and blunt with her. Part of her was flattered, part of her was terribly uncomfortable and embarrassed. "Well, I don't know what to say to that Terry. I guess for some women it's a turn on. I'm not sure if it is for all women," was all she could think to say. She really wanted to end this conversation.
"Thank you for your honesty. Well, you've seen it twice Stephanie, although I guess by accident both times," and he chuckled awkwardly. "Do you think it's big enough to satisfy a woman as smart and successful and sexy as you?" He saw her gasp and quickly added, "Oh, I don't mean you, like YOU personally. I meant like a woman like you, beautiful, successful, powerful. I was just wondering if more mature women like the same as young ones my age?" She smiled and was happy that he didn't call her an older woman, at least that he had enough tact to choose those words carefully. But Stephanie was thoroughly embarrassed, and at the same time, deeply flattered.
She touched his hand. "Terry, you are an attractive, kind and nice young man." She paused and tried to sound professional and with no emotion in her voice as she said the next part. "And well, I shouldn't say this at all Terry. But because you want to know, I will say, yes, you appear to be very well endowed. I don't think you'll have any problem attracting nice young women your age." She added that at the end to make it very clear she was not interested in anything sexual with him, in case he was thinking that.
"Thank you," he said and was sincere. "I didn't mean to make you uncomfortable in any way, I just really think you're really smart and wise and I wanted your opinion. Thank you," he said again and kissed her hand like he was a knight, and she was a princess. Then he stood, still holding her hand and helped her up. "We'd better get back," and she agreed and was thankful that awkward conversation was over. She decided she would not tell David about this conversation with Terry about his penis size. On the way back she realized that David was not totally ok with this arrangement, and especially that she had seen Terry naked. She really believed he was innocent and sweet, and didn't mean to upset or offend her in any way. She reminded herself how immature men at that age are and knew he was harmless. She would just remind him not to come out of the shower naked anymore. Later on, they were back in the room and had some free time before a team dinner. He decided to go to the gym and she sat down to get some work done. She envied his free time and that his job required nothing extra of him, while she had reports to prepare and decisions to make even after hours. She was settled down at the desk working away and getting a lot done when he came back from the gym. He had on a pair of shorts, and a tank top, and was quite sweaty.
"Hi, how's your work going?" he asked. "Good, thanks. How was your workout?" she replied. "Great. I'm going to go shower now," he said, and headed to the bathroom. She started to speak to remind him not to come out naked, but he had closed the door already and she didn't want to embarrass him and trusted he would this time. A couple of minutes later he came out, naked again, but this time had a towel around his waist.
"Oh, um, Stephanie?" he said as he came around the corner. She turned from the desk to look at him and smiled a little. "See?" he said pointing to the towel. "I remembered this time," and smiled back. She could still see the outline of his cock through the towel, but was glad at least he covered up this time. But she saw a look of awkwardness on his face. "What is it Terry? What's up?"
"Well, I wanted to, um, ask you a question, but this time it is personal. Is that ok?" She wondered what it could be and was afraid to find out. She thought about saying no, as she did not want to open up another inappropriate topic with this young man. But he seemed genuinely concerned and she felt some type of responsibility towards him to give him life advice and wisdom for some reason. "Ok, what is it?" she asked and braced for whatever it was.
"Well, I was about to get in the shower. I mean, I'm about to get in the shower. And, well, I, well I was going to masturbate in the shower Stephanie. And, well, I wanted to know, if it's ok if I think of you while I do?" Again, beat red. Of all the things running through her mind, she was not prepared for this one. Again, she felt so awkward, yet very flattered that this young, attractive man found her so desirable, and wanted to masturbate thinking of her. She wondered if Doug did that ever?
"Um, Terry. I'm flattered that you want that, I think. I mean I'm married as you know, so you shouldn't be thinking that way about me at all. I can't stop you from thinking whatever you think while you're in the shower," was the best answer she could think of, and it felt strange saying it. "Ok, I know. I just didn't want to disrespect you again, that's all. I wanted to know if it was ok?" He really sought her approval on this and she felt very flattered, as inappropriate as it was.
"It's fine Terry," she laughed awkwardly, and forced a smile. "Great, thanks," he said and turned and went into the bathroom.
She shook her head and chuckled, still amazed at how he had no filter for inappropriate talk or questions. She hoped he didn't offend some young woman sometime in the future with an inappropriate comment and get himself into trouble. But she went back to her work. Minutes later she heard his voice in the shower. It was too muffled with the water to hear what he was saying, but it seemed odd he'd be talking so loud to himself. As she worked she tried to ignore it but it continued. Something in her was curious and she got up and quietly walked to the bathroom door. She knew this was totally inappropriate and invasive, but she opened the doo r a crack to hear better, as she was pretty sure she heard him utter her name. Even with the door open so slightly, she could see him in the mirror in the shower, as the shower curtain was clear. He was stroking his cock hard, and it was huge. Her mouth fell open, realizing it must've been at least 8 inches long, maybe longer and very thick fully erect. "Oh, Stephanie, you are so beautiful and sexy. Oh, God you feel good. I'm going to cum," she heard and shut the door quickly and more loudly than she wanted to. "Oh God," she muttered to herself.
"Your pussy is so tight, I'm going to cum so hard," she heard clearly behind the door and she clasped her hands over her mouth in disbelief. He was practically yelling, groaning, and then she heard him cum, groaning loudly for nearly a minute and she could tell he was cumming. Stephanie was frozen in place, unable to believe that this young man was thinking about fucking her and just had an orgasm at that thought. Suddenly the water stopped and startled her back to reality and she quickly ran over and sat back down at the desk, resuming her work. She shifted her legs uncomfortably as she realized she was very wet from hearing Terry cum imagining he was fucking her.
"Stop it Steph," she said quietly to herself and tried to focus on her work. Soon he came out of the bathroom and did have a towel wrapped around his waist this time as well. She awkwardly said Hi again and pretty much ignored him, feeling embarrassed that she had listened, and quite mad at herself for how turned on it made her. There was an awkward silence for some time. She worked away and kept glancing over her shoulder to see what he was doing. He was mainly doing stuff on his phone, and at least had put on some shorts, though he was shirtless still. Stephanie had trouble concentrating on what she had to do, but managed to get it done before they had to leave to go down to dinner again.
She talked to Doug on the phone again briefly, and reassured him nothing inappropriate had happened again. She felt bad lying, but could hardly tell her husband that her young man roommate had masturbated in the shower thinking of fucking her. No, that would not go over well and she convinced herself she had really crossed any lines as nothing had happened between them.
Later on at dinner and after at team events, she found herself flirting with Terry. It was rather subtle, a touch on the arm here, a touch on the shoulder there. She sat closer to him than she should've and really had to catch herself several times. She knew she had to stop this before leading him on, but she found herself surprisingly attracted to this young man, which was highly inappropriate. She reminded herself she would be fired if she had sexual relations with a colleague on this trip. They had kept it quiet that they were roommates, as they didn't want to draw unnecessary attention and make the whole situation a huge company embarrassment. They talked more and he asked her questions about money management, life insurance, wills, and other topics that a young man would need to know. Stephanie was really caught up in his desire for her wisdom and smarts, and he hung on every word she said. It was a situation where she hadn't been in before, and to have a nice, attractive young man so interested in her w as quite intoxicating. Several times she had to remind herself she was happily married and he was a young man, and to behave and be professional. But Terry was not blind, and he picked up on her flirtatious manner. Although she had told him she's married several times and was not interested, he was getting the feeling she changed her mind. Several times while they were together in a group he would tell others how smart and wise she was, and how she had given him so much good life advice. She liked it. She really did.
Towards the end of the night, she was coming down a hall back from the bathroom, heading to the main area where all her colleague were, and there came Terry around the corner towards her. He stopped in front of her and she stopped. "Um, hi," she smiled awkwardly and wondered why he was blocking her. He quickly looked behind him and to each side. Seeing no one was around, he reached up and put both of his hands on the sides of her face, leaned down, and kissed Stephanie on the lips.
At first she was shocked and her instinct was to pull away. She grabbed his forearms with her hands just as he pressed hard with his tongue and she instinctively opened her mouth. Their tongues met in a hot, heated embrace, and he held her face tight. She shuddered and put her hands on his shoulders. Her brain was screaming at her to stop this immediately, but her lips didn't listen.
A few moments later he broke the kiss, and said, "Sorry Stephanie, I had to know. I had to know what it was like to kiss you. I just had to know. Sorry." And he let her go and walked away past her down the hall to the bathroom himself. Stephanie stood there stunned. That did not just happen. It didn't. She didn't just kiss this young man. She touched her lips with her fingers, as if trying to feel if it was true.
"Stephanie Miller, stop right now!" she whispered to herself. "Do not fool around with this man." She thought of Doug, and how this was technically cheating. She had just kissed another man and let him put his tongue in her mouth. And worst of all, she liked it. She shuddered. She knew she had to tell Doug, but more importantly, she knew she couldn't let anything else happen. She decided when they were back in the room, she would make it clear nothing else could happen. Period.
The team events continued, and she avoided him for the rest of the evening, afraid of what might happen. He eventually went outside with some other colleagues, and she was tired and needed some alone time so she went back to the room. Stephanie sat on the bed with her phone in her hand. She stared at her husband's name on the screen but her finger would not press the call button. She knew she had to tell him, but couldn't bring herself to do it.
She looked up and saw the bathroom, and decided a long, hot shower would help her feel better, and she would call Doug first thing in the morning. Minutes later she was in the shower and made sure the bathroom door was locked, in case Terry came in and had any ideas. Although she felt disgusted with herself because she knew she had led him on and shouldn't have been flirting. Finally she was done and turned off the water. She stood silently and listened, and didn't hear anything in the other room so figured he was still out. She wrapped a towel around herself and opened the door slightly. She didn't see him or hear him so she came out and walked toward her suitcase to get her panties and tank top for sleeping.
As she rounded the corner, she jumped. "Sorry, I didn't mean to scare you," Terry said, standing there, naked, with his fully erect cock. He grabbed her hands and started leading her towards the bed. "Terry, stop, what are you doing? You can't. Why are you naked? And, erect?" she couldn't believe she had just said that word to him. She pulled lightly against him and did not want to go, but he pulled a little harder and she reluctantly took the last few steps towards the bed. "Terry we can't. I can't. I know I led you on and I'm sorry, but this can't happen..." she was about to continue when he put a finger to her lips. "Shhhh," he said, rather sternly actually. Which surprised her. And he turned her around so her back was to the bed, and made her sit down on the end. He knelt in front of her, and said,
"I have to know Stephanie. I have to know." And he put two strong hands on her knees and pulled her legs apart. "No Terry, stop, you can't. I can't," she protested but not as hard as she should have. The towel fell open as he spread her legs and she grabbed it so it would not fall off of her firm breasts.
"No, stop," she said and place a hand on his head, pushing back as he opened her legs wide and lowered his head towards her vagina. With one strong hand he grabbed hers off of his head and put it at her side. She put her other hand on his head and tried to push him away. She knew she couldn't let him do this. There were so many reasons it was wrong. And she hated herself because her vagina was soaked with desire. Disturbingly wet. He pushed her other hand away and assertively bent forward, opened her legs wide, and as she put both hands on his head, he spread her clit open with his fingers and licked it quickly with his tongue. "Aaoohhh!" she cried out and shuddered. Her grip on his head loosened as he licked her clit again. "Nooo, Terry, noooo," she cried out and fell backwards onto the bed. His tongue found her clit a third time and licked hard. She moaned and he kept going, licking her clit over and over. Stephanie bit her lip as she felt his tongue. She knew this was wrong. He was nearly half her age. She was happily married. She had kids. She was a VP and should be setting an example. She shook her head from side to side, and moaned loudly as his tongue was driving her wild. She grabbed the sheets in fists and curled her toes, feeling an orgasm building as he masterfully licked her clit over and over. "oooohhh Goddd," she cried out as she felt one finger enter her soaked vagina. Terry slid his finger in a few inches and gently rubbed her sensitive area as his tongue licked hard on her clit.
"Oooohhhh Nooooo!" Stephanie cried out and tried with all her might to resist and fight her orgasm. She had not been this turned on by a man in a long time, maybe ever. To have this young, beautiful man so attracted to her was intoxicating, and she couldn't resist. "OOOOohhhh, Terry, I'm going to cum!" she cried out and gritted her teeth. A few more licks on her clit and she exploded, shaking and shuddering and cumming on his face as the young man did not let up with his masterful work on her clit.
Over and over and over Stephanie came, more orgasms than she ever thought possible. She felt lightheaded and her back was arched, and her body was shaking and cum flowed out of her vagina in waves. Finally, she could take no more and pushed his head back and he understood and stopped. Terry stood up, leaned down and kissed her lips, as she was still shaking and shuddering through orgasms on the bed.
"Thank you Stephanie. I had to know what you tasted like. I just had to know. Thank you," he said calmly and walked into the bathroom. "What?" she asked, only half taking in what he said. Her body shuddered for some time, as multiple mini orgasms took her over and over. Soon, the young man came out of the bathroom and just went to bed, without a word. She was certain he wanted to fuck her, and was half ready for his huge cock. She knew she would've welcome it into her vagina if he had tried. As she finally calmed down and her heart beat slowed, she looked over at him. Her towel had fallen open long ago and he had seen her fully naked body when he stood up. He was lying on his side with his back to her.
She laid there, naked, staring at him. The sheets and her towel were soaked with her cum. Her thighs were soaked with her cum. She couldn't believe this young man had just given her oral sex. Incredible, mind blowing oral sex. She thought of Dave and tears ran down her face. How could she have let this happen. And why had Terry not tried to have sex with her. She was actually a little disappointed that he hadn't tried to fuck her. She felt anger towards him as well that he had seduced her. That he had eaten her out and that he was so godamn good at it. And that he made her cum so many times. She felt anger at him that his cock was so big, so thick, so veiny and that she couldn't get it out of her head. She shuddered. At that moment she almost got up, walked over and sat on his cock. She almost felt cheated that he hadn't fucked her, because she was expecting it. She desperately wanted his huge cock impaled inside her. But she knew she couldn't have it.
She had to get out of here. Quickly went to the bathroom, cleaned herself up, came out, put on a pair of jogging pants and a shirt and left the room quietly. She walked down the hall to where there was a small lounge area.
"Steph, what the fuck are you doing?" she said to herself, tears in her eyes. "Stop! He's 24 years old." She was disgusted with herself and blamed herself for this happening. She called Doug crying and sobbing. The words were there in her head, the confession was on her lips, but she couldn't say it. She said it was very stressful, and although Terry was a very nice young man, maybe he had poor judgment. She told her husband he had come out of the shower naked again, only this time he had a full erection. Doug was furious, mostly because of his own insecurity with a young, attractive man spending a week in a hotel room with his wife. He wanted to come down and strangle Terry, and it was all she could to talk him down. "I promise you honey, he's a good young man. He is lost in some ways, but he means well and I want to help him on the right path." She just couldn't bring herself to confess that Terry had eaten her out and given her the best orgasms of her life. Doug was furious but wanted to trust her and knew she always had a kind heart to those in need. But Doug's ego got the best of him and he insisted on knowing how big Terry's cock was fully erect. Stephanie would not answer and made excuses like she only glanced at it or turned her head and on and on. But he would not relent, and she sighed. She was lying to him enough already, and figured she'd be honest about this at least.
"Well, Honey, I didn't measure it, but if I had to guess, I would say maybe 9" approximately. " Doug felt ashamed that he was only 5 inches fully erect, and wondered if his wife secretly longed or thought about Terry's huge cock. He felt even more threatened now, but she continued to assure him it was no big deal. She reassured him of her love and fidelity and that she had no intention of having sex with him. And she meant it. Somehow she felt better about what did happen by assuring her husband there would be no sex.
They talked on further, and she felt somewhat better, but still like a lying whore for not confessing what actually happened. But she knew he would feel so threatened as a man, and had no reason to, as she was not going to let anything else happen. She sighed, scolded herself again and went back to the room. The next morning she woke up to hear Terry in the shower. As soon as he came out, thankfully wearing a towel, she said,
"Good morning. I need to talk to you as soon as I'm done." He agreed and she took her turn in the bathroom. Soon they were both out and dressed. She sat him down in a chair and sat across from him. "Terry, listen to me. What you did last night, you never should've done. It was inappropriate. Not just because I'm a married woman, but because I'm a VP at this company and I need to set an example. I'm ashamed that I let you do that, and I'm sorry for leading you on yesterday. I guess I got caught up in a young, attractive man being so enamored with me. But, it CAN'T happen again, do you understand?" She tried to sound kind but assertive at the same time.
"I do," he nodded. "I'm sorry if I offended you Stephanie. I'm very attracted to you, I'm not going to lie. You are a beautiful, sexy woman, and, well, I just wanted to pay you back for all the advice and kindness you've shown me, and I thought giving you some orgasms by oral sex would be the best way. I knew you didn't want to have sex, so I didn't try, but I wanted to thank you, that's all it was." He genuinely looked dejected and like he had failed her. She put her hand on his cheek.
"It's ok, I understand. And, thank you. It was wonderful in itself. You're quite skilled with your tongue young man," she said and tried to make him feel a little better.
"Thank you," he replied shyly. "And I hope you don't mind me saying Stephanie, but now that I've seen you naked, Wow. You have an incredible body. And I was so hard from hearing you orgasm like that, and so many times. I wanted to fuck you so bad, but I didn't because I wanted to be respectful of your boundaries, being married and all." She blushed again as he talked about her naked body, and was kind of disturbed that he didn't feel eating her out was crossing a line with her being married. "Well, if you change your mind, I'd love to eat you out again. Anytime," he smiled. She chuckled but it was a very awkward chuckle. "Let's get going," was all she replied with, and really hoped he got the message.
Later that evening there was a party for the whole company. Stephanie felt such anxiety and anger at herself for cheating on Dave, she had a glass of wine to take the edge of. Then, she had another. Someone in her group bought some shots and she couldn't say no when everyone else was taking them, so she had a couple of those as well. By now she was feeling her alcohol, wasn't drunk but a little tipsy. Terry found her sitting at a table with some colleagues. He came and joined them and sat beside her. For the next ten minutes or so, he raved to the group about how amazing Stephanie was. He shared how he was not sure about this company, just got hired, and she made him feel welcomed, and shared great life advice, and on and on. She felt he was sincere, and she was really flattered. One of the colleagues was someone higher up than her, and although she didn't directly report to this person, it was great for them to hear that feedback.
A few minutes later, some dance music came on and many people hit the dance floor. Terry stood up and took her hand. "C'mon, time to dance," he said enthusiastically, and she felt obliged since he had been so complimentary. On the dance floor where they had some relative privacy, she leaned into him and said,
"Thank you Terry, really, thank you for what you said back there. I really appreciate it." He smiled and replied, "You're welcome, I meant every word. I know I've been a little, well, naïve maybe. I don't know, I'm very carefree in my life generally. But you really have helped me a lot to have a better perspective on things. She hugged him and resumed dancing. A short while later he leaned in and asked, "Can I ask you another question?"
"Oh gosh, another one. I'm afraid of that question now," she laughed, but nodded. "I don't want to make you uncomfortable, but I was wondering, that kiss I gave you yesterday. Well, did you like it? I'm not sure if I'm a good kisser or not," he said. She blushed, wasn't sure how to answer and thought about it hard. She didn't want to hurt his feelings by reminding him how inappropriate that question was, nevermind kissing her itself, but she did feel he was trying to improve and do better. She sighed, and nodded. "Yes, Terry, it was a good kiss. It was a very good kiss." "Great, thank you. So you enjoyed it then?" he asked for clarification. St
"Yes, I enjoyed it, but I shouldn't tell you that. But I did," was all she felt she would say. "I'm glad. Well then, could I kiss you again? I mean, not here, not now. I know that wouldn't be appropriate. I mean back in the room. One more time? Could I kiss you there?" His boldness never ceased to surprise her. Apparently, he believed the only thing off limits was actually fucking her, when she clearly meant anything physical. Part of her wanted to, but she knew she could not take feeling like such a whore again, and already felt so terrible for what she had let him do last night. Shaking her head, she replied, "No, Terry. I'm married. I can't be kissing you, that's cheating. Don't you understand?" She really looked frustrated with him. "Yah, I do, I think. I'm not married so I guess I don't really get it but maybe someday when I am I would understand better. But, when you say kiss, Stephanie, what do you mean? Do you mean like I can't use my tongue like I did yesterday, or can't press against your lips for a long time? What about a quick peck, just like a thank you kiss. Nothing more to it than that. Is that ok?" He smiled, and there was that boyish, innocent, naïve young man she saw and was so fond of. He just had no idea how real relationships worked. She figured if it would placate him then it would be ok. One quick peck. Stephanie sighed and smiled back. "Ok Terry, one quick peck, when we're back in our room. Ok? But nothing more, understand?"
"Yes Ma'am," he said and took her hand and kissed it. He could be quite charming when he wanted to be. She hugged him briefly and they continued dancing. Time passed and they spent more time talking with colleagues and every chance he got he put his arm around her, or gently fondled her butt subtly when no one was looking. At first, he got an angry stare from her, and smiled and shrugged. After a few minutes she just gave in, and didn't react when he did those things. She really did like this young man, his company and his conversation. He was so real, so raw, so unafraid and it was nice to talk to a genuine person for a change. And it really felt good to be so lusted after by him, she had to admit that. Part of her wished she wasn't married because she wanted to see what he was like in bed. But she knew she couldn't go there, she felt bad enough already. Stephanie was starting to second guess giving in to his kiss request, but reminded herself if she stayed true to her convictions and didn't let him do anything more than a peck, it would be fine.
Finally, the end of the night came. Everyone said their goodbyes and headed for their respective rooms. Terry and Stephanie were in the elevator with a few others, and they stood at the back against the wall, and he had his hand on her butt the whole time. Moments later, they got off and headed to their room. As soon as they entered, he shut the door, grabbed her, and put her back against the wall. "Oh Terry, what are you doing? At least let me change first and get ready for bed," she said, startled. "No, Stephanie, this can't wait." He looked into her big blue eyes and was right in front of her. "I want that peck kiss now," and he smiled. "Fine," she said and smiled back. She puckered her lips and he leaned down and kissed her. It was quick, and she pulled away, and for a moment he paused. Then, surprising her again, he kissed her again. Another peck. And another. "Terry, I said ONE only, remember?" she protested as his lips touched hers again. This time he lingered and didn't pull away. He pressed his body closer to hers and put one hand on the back of her head and kissed her hard. Immediately Stephanie put a hand on his chest to push him away, but he held firm. With his other hand he took her hand in his and lowered it to his crotch, where he pressed her open hand firm against his cock in his pants. It was hard. Rock hard. She gasped as he kissed her and tried to pull her hand away. He held it there firm, making her feel his erection pressing against his pants.
She pulled his hand off of her head with her other hand and finally broke the kiss. "Terry, you have to stop. I said no, we can't do this. Oh My God!" she exclaimed at the end as he pressed her hand hard into his crotch. He slide the zipper of his pants down, and replied, "Ok, Stephanie, I will stop kissing you." And he was true to his word, and let go of her hand on his crotch, put two strong hands on her shoulders and pressed down. At first, she kept her hand where it was, excited at the huge erection she felt. She was overcome with this young man's seductive ways. She shook her head and said, "No, Terry, No," but lowered herself to her knees despite her protesting. There was part of her that had to see it. That had to have it in her mouth. With shaking fingers she reached into his fly and fumbled for what seemed like forever. Her pussy flooded with anticipation as she finally got it free and out sprang his huge, erect cock, inches from her mouth. She looked up at him, this 40 year old, successful career woman, a mother, a wife, and as her hand slowly closed around his thick shaft, she felt horrible, but couldn't resist. She opened her mouth and leaned forward, and took the head of the most massive cock she had ever encountered into her mouth. She couldn't look up at him and closed her eyes in shame as she sucked it.
He guided her mouth forward with his hand, and the thick shaft of his monster cock slid into her mouth, over and over. She sucked on his cock as best as she could, so turned on right now she couldn't think straight. Up and down his shaft her mouth stretched, and she had a mini orgasm she was so turned on.
A couple of minutes later and he pulled her off and back up. He didn't say a word and just took her clothes off and she let him. His pants fell to the floor and he picked Stephanie up, she wrapped her arms around his neck, and right there against the wall of the hotel room his cock entered her soaked pussy. And he fucked her standing there, her back banging against the wall, and she moaned loudly.
"Oh God Terry, Oh God! Yes.. " she couldn't believe she gave in, but right now didn't care. She just wanted this monster cock to fuck her as deep as it could. Over and over the young man thrust up into her married pussy. A few minutes later he stopped, pulled out, moved her a few feet to the desk, bent her over forward and shoved his cock back in. She grabbed the desk and cried out as he took her from behind.
"Ooohh God.. Terry.. uhh. Deeper.. please.. deeper," she cried out and wanted his entire cock. He grabbed her hips and thrust hard, over and over, lifting the heels of her feet off of the floor with each thrust. It seemed impossible but he was determined, and despite it being on the verge of pain, she cried for it deeper, over and over. Her pussy was so tight, but eventually she gasped out loud, as she felt his balls slap her skin, and his entire manhood was inside her hungry, aching pussy.
Terry fucked her long and hard like that, enjoying slow but hard thrusts. Stephanie came over and over on his cock, gasping and panting and loving every minute.
They fucked on into the night, in many positions, many times. Stephanie must have had at least a dozen orgasms, she'd lost count. Terry came in her pussy several times as well, and they ended up in bed, exhausted.
The morning came and they woke up together, Stephanie lying on his chest with her hand on his cock. Immediately she smiled at started stroking him. Soon after she lowered her head and sucked him again. Then she got on his cock and rode him until she came several times again.
They showered, went about their day, came back at night and fucked like rabbits again. Stephanie was lost in her lust for his cock. As they readied to sleep, she realized they would be leaving in a few days and going their separate ways. Suddenly she had an idea.
"Terry, I actually need a personal assistant, as mine is going on maternity leave in a few weeks. Interested?" he smiled, and immediately accepted the job as he lowered himself to eat her out again.
She opened her legs and accepted his familiar tongue, and for a moment she wondered about going off of the pill and what it would be like to get pregnant again. Only this time, by Terry's huge cock.
THE END..
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