I am posting from a throwaway account despite this having happened approximately 17 years ago. The events are real but names and other identifying information have been changed. I recently posted this on /r/sexstories but just learned about this sub, so posting here too.
I [M] got my big break in my career around the age of 21, fresh out of college, taking a job in IT for a large company in the US Southeast. It was at this job that I met Julie[F]. She worked in a different department, but near enough to mine that we saw each other frequently. A day or two after my first day, she came up to me and introduced herself, which stood out as a little unusual; not everyone had been so outgoing or welcoming.
My first impression of Julie was that she was very physically attractive. I never learned her exact age but I would guess mid to late 30s. She was above-average height, maybe 5’10, and full-figured/voluptuous - large breasts, hips, and ass, but slender waist, flat tummy, and long legs. It was clear she took good care of her physical health despite her curves (or just really good genes). She had great skin and lovely dark brown, nearly black hair that was just passed her shoulders. Her make-up was tasteful and conservative, and she was a very classy dresser. She was less classically beautiful in the face but still quite pretty. Just more of a sort of “Country Girl Next Door” look.
When she came over to introduce herself, she extended her hand for a shake and locked eyes with me, giving a quick wink. After exchanging pleasantries, she joked that she was sure she would be seeing me around often. Fast forward a year or so and Julie was right. We became quite chummy with each other (we had our own little thing where I would sometimes refer to her as “Ms. Clarke” or she to me as “Mr. Fredrick”, the joke being that we were being overly formal in a not-so-formal office), and I learned that she had a great personality; very much a ‘Southern Belle with a fiery side’, if you know what I mean. She was assertive, intelligent, and professionally driven, but also quick with a joke and could give as well as she could take. Through being friends, I learned that she didn’t have children, had been divorced for a couple of years, and was “enjoying being single” to use her words. “Single and no kids?” I thought. “…nice!”
We occasionally ate lunch together and did other platonic work friend stuff. But, all the while, for me, the sexual tension was building. By now I was 22, single, and very attracted to her, which was out of the ordinary for me as I had never been with an older woman or even entertained the thought. Perhaps that was part of the attraction? But it is here that I should point out that I was clueless with women. I could never rely on my looks alone (I’m probably a 7 on a good day: tall and broad, but a little overweight. Brown hair and green eyes, light complexion and, at the time, I sported a short beard) and I could never trust if I was picking up signals or misinterpreting, so I would convince myself that women weren’t attracted to me, and I wouldn’t have the courage to capitalize on the signals if I knew they were true, anyway. Also, I considered Julie to be well out of my league. Having said that, she and I would routinely engage in what I though was harmless flirting. I never thought anything would come out of it, but always kind of hoped.
Then one day, it happened. It was a Friday and she emailed me around 2pm requesting that I come see her. When I got to her cubicle, she asked me if I ever did any computer work “on the side” and went on to explain that her home computer was having issues. “It’s being weird and I don’t want to lose all my photos!” I agreed to have a look and she asked if I could come by that evening. I was free, so I said, “Sure, no problem.” She gave me her address and said to come by around 6:30pm.
Of course, my mind went straight to, “Are we going to hook up?” But I convinced myself that she probably really does just need help with her computer. I got to her house about 5 minutes early and rang the doorbell. About 30 seconds later, the door swung open and there stood Julie, in a short silk black robe, tied closed at her waist, with her hair pulled back in a messy ponytail. I am positive that I was visibly stunned. I apologized for being early and offered to come back and she replied, “No, no it’s OK. I was just about to get changed. Come in.” So, I did.
I took my shoes off at the door and followed her through her foyer, between the living room and dining room, all while complimenting her on what a nice house she has. She blushed and deflected, saying it’s too big for just her but she got it in the divorce. Finally, she motioned towards an open laptop on the dining room table while turning to go towards her kitchen and said, “There’s my stupid computer. See if you can do anything with it. Want something to drink?” I replied, “I’ll have whatever you’re having.” while sitting down in front of the computer.
She came back with two glasses of wine, which was kind of a surprise to me – I expected sweet tea or coke or something - sitting one down in front of me. She stood next to me, looking over my shoulder as I checked out her laptop. After a minute or two of not finding anything wrong, I explained to her that everything looked normal, but I could help her backup her photos if she wanted. She laughed and said, “Oh? Just like when you take your car into your mechanic and suddenly nothing’s wrong!” I laughed too and said, “Yeah, I guess, something like that.”
There was a loaded pause. I broke the silence by hinting that since nothing seemed wrong with her computer that I should probably go and let her get back to her evening. She responded, “You don’t have to rush off!” and clinked her wine glass against mine. We each took a generous swig and I agreed that I could stay a little while.
I followed her from the dining room into the living room, where I took a seat in the center of the couch. She sat next to me to my left, turned sideways to face me, with her right leg tucked under her left thigh. This made her silk robe taut, accentuating her curves and revealing the outline of her areolae and nipples. I pretended not to notice.
We made casual small talk for a few minutes, laughing about the idiots at work, etc. She was being very flirty but, again, I kept convincing myself that there was no way this could be happening. Julie must have found this frustrating because mid-conversation, in one fluid motion she leaned over toward the coffee table to set her wine glass down and, upon sitting back up, leaned right in and passionately kissed me on the lips. After my initial moment of shock, I reciprocated the kiss, which lasted about 10 seconds before she pulled away. I must have looked stunned. She feigned embarrassment and with a huge grin asked, “Oh my gosh. I’m sorry…Should I not have done that?” I blushed and mumbled something to the effect of, “No, it’s fine.”
She smiled wide and bit her bottom lip. Then I felt her hand sliding up my thigh. I looked down to see her hand continue over the crotch of my jeans and onto my belt buckle. “Guess I shouldn’t do this, either, huh?” she asked as she pulled the slack of my belt back through the buckle. I just smiled and relaxed, gazing back at her as she expertly unbuckled my belt. She then slid down off the couch onto her knees in front of me. “I have thought about this a lot…” she said coyly as she reached up to unbutton my jeans and began lowering my zipper. “…Have you?” I nodded, too happily perplexed by what was happening to make a coherent sound. She then grabbed the waistline of my jeans and boxers. I pressed my hips upwards off the couch while she pulled. I will never forget the way her eyes lit up when my cock flipped up and over across my lap like a sprung Jack-in-the-box as she pulled my jeans down to my ankles.
I will brag on myself in one aspect; as average as I think I am in looks; I think my cock is well above-average; 8.5 inches long and about 5 inches in girth. I keep everything nicely ‘manscaped’, too. It’s by far my defining physical feature, in my opinion.
Julie gripped my cock at its base, holding it up vertical as if she was examining it. She seemed astonished. She then laughed in a very sexy manner and said, “My goodness, Mr. Fredrick…” Then she leaned forward, opening her mouth wide and gently enveloping her lips around just the head, slowly sliding her tongue around in a circular motion while adding some suction. My eyes rolled to the back of my skull. Then, I exhaled and watched her as she began bobbing her head up and down slowly. I reached out to tuck the loose strands of her hair behind her ears so I could get a better view.
She looked up and locked eyes with me as she worked more and more of my now steel-hard dick into her mouth. She got about 2/3 of it in before struggling, pulling back sharply, and leaving long strands of saliva to stretch from her mouth. She laughed a sexy laugh again and seemed a little embarrassed. “It’s been a while. I am out of practice.” She used her hands to gather up the strands of spit and massaged it into the head of my cock. I moaned as her fingers worked corkscrews over the tip of my dick. Somehow I managed to offer the encouragement, “You’re doing great.” At this, she began again, more enthusiastically.
She gave the best blowjobs I have ever experienced to this day. Her technique was incredible and her enthusiasm was off the charts. It was evident she loved sucking cock and that she had plenty of experience doing it. I still don’t know how I didn’t cum after 30 seconds.
When my breathing and groaning would indicate that I was getting close, she would back off and kiss gently down the length of my shaft while a loose grip of her fingertips held my cock up alongside her face. Occasionally her tongue would slide over my balls. After a few moments reprieve, she would get back to it, even more vigorously than before.
After maybe 10 minutes, she sat back on her legs and gave my cock a few slow strokes. She asked me, “You OK?” I teased her by answering, “You tell me.” She stood up and pulled the drawstring of her robe, causing the bow knot to fall apart gracefully. “Yeah, I think you’re alright” she replied with a sarcastic nod. Untying her robe caused it to part slightly and I caught a glimpse of her well-manicured bush. She bent straight over at her waist and pulled my jeans and boxers completely off. Her large, impressively perky for her age, breasts hung and swayed. When she stood back upright, her robe had parted completely, revealing her nearly nude body to me for the first time. She stood for a moment or two, completely confident in herself and her body. She had every right to be. She had the body typical of a much younger woman, not a significant wrinkle or stretch mark in sight.
By now, her mood had changed from being coy and flirtatious to more serious and determined. She took a small step forward then straddled down on top of me. She used one hand to guide my cock between her legs, the other to brace herself on the back of the couch. I could feel the tail of her robe drape across the head of my dick as it poked out past her ample ass. I slid my hands over her thighs and onto her waist. She leaned forward slightly and I instinctively took the nipple of her left breast in my mouth, sucking hard and biting gently. I could feel it become erect in my mouth and I flicked my tongue back and forth across it.
Julie exhaled with a moan and reached behind her to stroke my cock. She leaned forward and arched her back, sitting her ass down onto my cock and started rocking her hips which made her pussy glide across the top of my cock’s shaft. It drove me wild to feel how wet she was. This went on for several moments, me occasionally swapping between sucking on her left and right breast. Then, I sat upright and wrapped my arm around her waist, turning and dumping her over gently onto the couch. Julie squealed and giggled and I slid down onto my knees in front of her. She obviously knew what was happening next because without hesitation she propped her feet up on the edge of the couch and spread her knees wide, using the middle and index fingers of her right hand to spread her glistening labia apart. I wasted no time, immediately planting my face between her luxurious thighs. She smelled and tasted wonderful. I reached my arms up and caressed her breast and she ran her fingers through my hair. After a few moments, she arched her back and exclaimed, “Oh fuck! You’re going to make me cum!” I pulled away just enough to clarify, “I want you to.” and went right back to flicking the tip of my tongue around her clit. She gently pushed my face away and said, “No, I want to cum on your cock.”
She began standing up and then walked away from me. She got across the room before motioning for me to follow her. I stood up and did as I was told but I lost sight of her as she disappeared through a dim hallway. I walked into the first open door I came to. The room was pitch black for a moment before two beside lamps, one on either side of the bed, flicked on. Julie was standing beside a very regal looking bed, made up with lots of little pillows and nice bedding. I walked up, removing my shirt in transit, and stood right behind her, intentionally pressing my still hard cock into her backside. She reached back with her right arm and dragged her fingers through my hair. My left hand cupped her left breast, my thumb and pointer fingers pinched her nipple.
Julie bent over at her waist and laid her torso down on the soft bed, reaching behind with one hand to pull her hair out of its ponytail. Simultaneously, I slid my right hand between the bottom of her ass cheeks and onto her pussy. I used the fingertip of my index finger to massage her clit. This elicited a huge moan of pleasure from Julie. Her hands gripped tightly at the top cover of the bed. I continued to massage her pussy as my left hand glided over her round ass cheeks. Julie looked back and whispered, “Give it to me.” I heard her clearly but I asked, “Hmm?” “Fuck me” she demanded.
I pulled my right hand away and gave my cock a few encouraging strokes, using Julie’s wetness for lubrication. Then I guided the head of my cock towards her receptive pussy. I rubbed my dick head up and down across it, spreading her labia and getting everything properly moist. Finally, I began to shove myself inside. Julie recoiled sharply and commanded, “Be gentle! You’re really big.” I pulled back and apologized but she reassured me. “It’s ok. Just go slowly.” So, I reapproached more gently this time. I shoved myself in slowly, pulling back out some as I went. Her moans had an almost musical quality. Once I reach maximum depth, I pulled nearly completely out and with one slow but steady motion shoved my cock back deep inside her. She released a long and loud, “Ooooh fuuucccck!” and pushed her ass back against me. That was my cue.
I started fucking harder, using long and deliberate strokes. My hands slid to her waist where I held onto her tightly as my hips moved in and out. By now Julie was up on her tiptoes and filling the room with the sounds of pleasure. After a couple of minutes, she pushed herself up off the bed, her arms locked out straight. She shoved her body backwards to meet my forward thrusts. Her big tits swayed rhythmically. I slapped her ass with my right hand and she cooed, “Mmm, I like that.” So, I slapped the opposite cheek a little harder and she nearly screamed. “Fuck yes!”
I started getting close, so I pulled completely out and took a step back. Julie turned around and dropped to her knees, resting her back against the edge of the bed. I stepped forward towards her, my cock hung heavy in front of her face. She batted her big eyes up at me and gobbled my cock into her mouth without using her hands. I laid my head back as she sucked.
As good as her head was, I wanted more of her pussy. After several moments, I reached down and grabbed her by the arms to help her stand and coaxed her up onto the bed. Then I crawled up over her and between her legs, kissing her tummy and breasts and finally her lips as I got into position. I then got up on my knees and brought her legs up to either side of me. She reached down and expertly guided my cock to her pussy where it plunged in effortlessly. I was hypnotized by the way her tits bounced in circles as we fucked. Julie arched her back and pressed the back of her head back into the pillows. She seemed nearly delirious as she came. “Yes! Oh fuck oh fuck oh fuck ohfuckohfuckohfuuuuUUUCCCKKKKKK!”
Another moment or two of pure pleasure passed before she looked up at me and said, “Let me ride you.” Without much hesitation, I pulled out of her and laid on my back. With the grace of a gymnast, Julie swung her long leg over me and climbed on top. Her eyes rolled back as she eased down on my cock. “Oh my gooooood” she moaned. I slid my hands up onto her breasts and held them as she began bouncing. The way her messy hair fell around her face was beautiful. She leaned over and kissed me passionately as her hips alone moved up and down. I reach back and held onto her ass cheeks and whispered, “Don’t fucking stop.” She laid on top of me and bounced her ass on my cock like a basketball. I groaned loudly and said, “I’m going to cum!” “Yeah?” she replied with a whisper. “Yeeaaahhh” I groaned louder. She bounced harder and faster, “Give me that fucking cum. I want it deep inside me.” I was not in the habit of cumming inside my partners without a condom on. The idea was off-putting to me at the time. But, I was in no position to do otherwise. I pushed my hips up, burying my cock as deep as I possibly could and released myself inside her.
We both reached crescendos of screams and moans of passion that subsided into heaving breathing. We laid in each other’s arms for several minutes as we caught our breath before Julie broke the silence. “You can stay over if you want…” I nodded and said, “Ok. Thanks.” We laid quietly for a few more minutes before stirring to get up. We ended up showering together and ordering a pizza.
We carried on with a FWB type arrangement for the next 9 months or so, but this first time as told here is probably the most memorable for me. Later on, we talked about her side of how that night came to be and she confided that she finds, “the ‘lumberjack’ look really sexy”. She said she had been attracted to me for a while and her girlfriends convinced her to attempt a hook-up. Things did get a little weird between us, though. She and I both ended up catching feelings but, between the age difference and being coworkers, et al, we both knew it wouldn’t have worked out. We each eventually got into relationships with people more appropriate for each other. Then, she left the business and I moved, so we lost touch. About 3 years ago, she added me as a friend on Facebook and we had a short friendly chat. She’s remarried and seems happy.
We had some fun together, though. I could share a few more if you enjoyed this story. If you read the whole thing, thank you. I have been carrying this memory around for almost 18 years, having never told anyone before. It feels kind of good to get it out.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/pdkkn2/my_coworkerf_and_im/
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