My first real job had me working in a cubicle in an office when I was just out of school and in my early 20’s. I’m a pretty average guy, 6 feet tall, sandy brown hair. Natalie worked in the cube next to mine and we hit it off right from the start. She was in her late 20s at the time, about 5 feet tall, curly black hair, curvy with big tits. She was friendly, but also sarcastic as hell. The age difference was not that significant, but she had been working for years, was married, owned a house, etc. so had had a lot more life experiences than me. Or so it seemed.
I learned that she actually lived out-of-state and her actual work assignment was at our company’s office near her home. She was only filling in at our office on a temporary basis and would be returning to her permanent office once the company had hired and trained some people to fill the role here. So, she typically stayed in a hotel near the office (paid for by the company) M-F and drove home to spend the weekend with her husband.
In addition to spending a lot of time talking and joking at the office, we also were spending time together after work, getting dinner and / or drinks together. She didn’t really know anyone else in town and had nothing better to do. She began to confide in me that her marriage was not great and her husband was an asshole. However, they had been together since high school, he was the only man she had been with and she was afraid to leave him. While I was always super attracted to her, it was pretty clear that I was just a good friend in her eyes and the fact that she was married made me think that nothing would ever happen between us. However, with the newfound knowledge about her marriage, and several drinks, I summoned up the courage to kiss her one night. She kissed me back and her tongue made its way into my mouth for several glorious seconds before she broke it off and gently pushed me away. She apologized and told me that it would be wrong to go further, etc. We talked about it again the next day at the office and agreed that it was no big deal and would not make things weird between us. She explained that she was attracted to me, but could not get involved in a relationship with someone who lived so far away from where her home, family, friends, etc were. With a deadpanned expression, I told her that a relationship was not really what I had in mind if we had gone up to her hotel room that night. She blushed a bit, but smiled and punched me in arm, with a joking “fuck off”.
Several weeks later, Natalie returned from a weekend home and was particularly giddy on Monday at the office. She dragged me outside to tell me that she had left her husband that weekend and told him she wanted a divorce. Over drinks that night, she told me more details about leaving him and about what a controlling asshole he was. She also told me that the company had told her that she would only have 2 more weeks of work at our office before returning to her home location. She explained that this is what actually prompted her to leave her husband – she realized that there was no way she could deal with him 7 days a week after having experienced what it was like to have a break.
While I was bummed that she would be leaving in a couple of weeks, I always knew it would happen and I was genuinely happy that she was happy and moving on with her life. We went out for drinks after work a couple of nights later and she dropped the bomb on me – she asked if I would please come back to her hotel to help her live out a fantasy. I told her to be careful about using the word “fantasy” as that almost always meant something sexual in my mind. She nodded her head and said (and I remember these were the exact words that she used) “your fucking right it does”. I nearly spit out my drink from a combination of surprise, excitement and just the fact that I thought it sounded funny. “Well, I’m not exactly sure what that means, but I’m pretty sure that my answer is yes”, was my reply.
She went on to explain that she had been having this fantasy almost since we first met. Now that she was free of her husband and she knew that we would not be seeing each other much longer, she felt like she had to make it happen now or never. The fantasy involved some role playing which I had never really done before, but I was certainly up for trying. As she leaned across the table explaining the fantasy to me, I could feel my suddenly hard cock straining against my pants.
As we started to put the fantasy into motion, she got up to leave while I ordered another drink. I grabbed her coat and helped her on with it, simply to have an excuse to rub against her and make sure she felt my hard cock. “Ooh, did I do that?”, she asked, seeming genuinely flattered.
The plan was for me to nurse my drink for 30 minutes before going to her hotel. I think I made it about 20 minutes before I couldn’t stand it anymore and headed over.
Her hotel was an Embassy Suites and that actually played a part in the fantasy. It was the typical design with a big, open atrium in the center with the rooms around the perimeter with doors and windows that faced out into the 5 or 6 story atrium. Natalie’s room was on the top floor, located in the corner, completely opposite of the elevators. Other guests would have no reason to walk past her room on the way to or from the elevators and she had requested this specific room for that very reason. Also, by this time, it was well after midnight on a weekday and there weren’t any people moving around in the hotel anyway.
As I approached her room, I could see light coming from the window that faced the atrium and my heart started thumping as I knew that fantasy was underway. It wasn’t a faint light as I had expected. It was actually really bright and there was about a 1 foot opening in the drapes. I looked around to make sure that nobody else was in the hallway and then looked in the window.
Natalie was lying on the couch with her head propped up on the side of the room, facing the window.
Her eyes were closed and she was wearing just a bra, her legs spread and her right hand lazily stroking her clit. I knew that this was part of the fantasy, but I still was shocked to actually see it. Because she was in a bright room and I was in a dark hallway, it seemed even more vivid.
At one point, I noticed that she opened her eye for a second, then quickly closed it. Checking to make sure that I was there, but also pretending that she didn’t know, as was part of her fantasy. Now that she knew I had arrived, she ramped up the intensity, stroking her clit much faster, while taking a break to occasionally finger her pussy or lick her lips, her eyes closed the whole time.
She had a beautiful pussy, with big full lips and a neatly manicured little triangle of hair above her clit. Her big tits jiggled inside the black bra in rhythm to the motion of the hand between her legs. Her eyes remained closed and her mouth was tensed as she bit her lower lip. I had become mesmerized and lost track of time, but realized it was probably time for the next phase of her fantasy.
I took my keys from my jacket pocket and dropped them to the ground next to me. Natalie’s eyes flew open at the sound and she grabbed a throw pillow to cover herself. “Wh…..wh……wh……who are you?, she mouthed. I reached down and grabbed my keys then put my hands out in front of me and started to back away from the window, mouthing “I’m sorry.” After backing up several steps, I turned and started to slowly walk. Seconds later, the door snapped open loudly.
“Who the fuck are you?”
“Sorry”, I muttered. I thought this way my room. I guess I’m one floor down.
As I turned again to walk away, I heard “want to come in?”
I hesitated for a second, as though considering the offer, then turned and walked quickly to the door, Natalie returning to her couch. Once inside, I quickly shed my coat and shoes, then peeled off my shirt and socks. I went a little more slowly with my pants, hoping to add a bit of drama to the moment that my impossibly hard cock sprung free. She stared at it in a trancelike state as her hand returned to lazily touching her pussy, making me feel quite good about my average-sized dick.
I made sure to close the drapes all the way, then approached the couch, my precum-slick cock bouncing in front of me. I kneeled down to kiss her, out tongues intertwining immediately as my cock grazed the rough fabric on the front of the couch.
After several minutes, we broke off the kiss and Natalie rolled over onto her stomach, then pulled her knees up under her and leaned forward, her elbows resting on the arm of the couch, facing away from the window this time, but right at a full length mirror on the opposite wall. I took my spot behind her on the couch and lined up the slick head of my cock with her juicy hole. She pushed back forcefully and my full length was inside of her in an instant. She gasped a bit as I pushed back into her, grinding against her pussy and pushing her against the arm of the couch.
We started out with slow, short strokes even though she was wet enough to handle much more. I looked down at her ass jiggling slightly with each stroke, her perfect hips and cute little asshole. Then I looked at her bra strap and realized I had yet to see those big beauties. The fantasy that she had relayed to me at the bar did not really address this part, so I ad-libbed, using both hands to unclasp her bra. I watched them in the mirror for a moment, hanging beneath her, swaying with each thrust before leaning forward to rub each of them, giving her big, dark, pointy nipples a twist as I removed my hands, returning them to her hips. I started to slam into her much harder now, because it felt fantastic and because I loved watching those tits bounce in the mirror.
She had already gotten herself plenty worked up on the couch while I was watching outside and came loudly within a few minutes of starting to fuck. She let out a deep guttural groan as she pushed back against me as hard as she could. The room grew quiet for a minute or two as she came down from her orgasm and I felt my own building. I was now fucking her with long fast strokes, the sound of skin slapping echoing in the room and Natalie moaning softly each time my balls slapped against her clit. I let out a loud groan of my own as I pulled my hard, wet cock from her pussy and shooting my first spurts of cum on her back, with subsequent shots dribbling out and covering her asshole.
I stayed that way for a minute or two, panting in a post-nut haze, my cock nestled in the crack of her ass. I then remembered the fantasy and forced myself to pull away from her, silently and quickly putting on my shirt and pants and walking out of the room without a word, carrying my shoes and coat as I went.
Immediately after leaving, I realized that the fantasy part was over, but we had never discussed what was supposed to happen next. I went to the end of the hall and sat down to put on my socks and shoes, hoping that her door would open and I would be invited back in. But it didn’t happen and I made my way to the elevator. As I walked through the lobby toward the parking lot, my phone rang and my heart soared. Had to be her. “Where the fuck are you? You can’t just leave after that.”
“Sorry, I said. I didn’t know how far you wanted to play out the fantasy. I’ll be back up in a minute.”
She met me at the door, this time wearing panties and a t shirt and we hugged and kissed. “Holy shit, that was 10 times better than I even imagined it would be”, she said. “I think I’m still in a bit of a daze because I came so fucking hard”, I told her.
We returned to the couch, gently snuggling and talking. She shocked me by telling me that was the first time she had ever had an orgasm with a man. She had only ever been able to get there with her hand or a vibrator in the past. Apparently, her husband (soon to be ex) was not interested in foreplay and believed in just sticking it in until he was done and then moving on to something else. And she had never been with anyone else.
“Can you spend the night?”, she asked. Now that I know what that feels like, I’m gonna need more.
I wound up spending that night and just about every other night there for the remainder of her stay. We discussed (and did) all of the other things that she had missed out on as well. Some were pretty basic, but some were a little wild.
I hope that you enjoyed the story. It brought back some great memories for me. Thanks for reading!
Source: reddit.com/r/gonewildstories/comments/p3tsem/gave_a_28_year_old_woman_her_first_orgasm_from
This was very sweet and sexy.
Did you get to cum in her?