A series of encounters with a coworker. Part 2. (m/f)

This is a continuation of a story that started here.

The following day Jen and I texted about the events of the preceding night. We both agreed that it had been more than we were planning and we lost control of ourselves when it got down to it. Moreover we decided we had to do it again, but go further. Fortunately our work colleagues were still unaware and we restrained ourselves from texting too much. Jen did make a point to come to my cube twice during the day, which made me uneasy. I had a feeling that people just had to know just by looking at us. I hoped that I was wrong.

Over the next few days we compared schedules to figure out when we could meet again. Her evenings were filled with dance classes and book clubs and mine was complicated with after work beer with colleagues, games and league bowling. Our next rendezvous was further hindered by the proximity of our places to coworkers. Since everyone knew what everyone else drove at work, it was easy to see who was where by the cars in parking lots and driveways. So, things were not as simple as meeting up after work at home. We had gotten lucky with the first encounter and I wasn’t willing to be as risky a second time around.

Finally, I arrived at a simple solution. A hotel. It was simple, anonymous and cheap. Money wasn’t a problem for us so the plan was to meet, fuck and go our separate ways. It was a perfect plan.

We decided on a nearby (but not too nearby) hotel on a Thursday after work. We excitedly texted about the things that we wanted to do and that’s where I think that I began my entrancement with Jen. For me, while growing up in the conservative south, I was faced with a lot of things that were completely off limits sexually. I became conditioned to expect only a very limited repertoire of things during sex. Once I left graduate school, I unfortunately hooked up with a few women who perpetuated many of these taboos while we were dating. In my limited experience, swallowing was unheard of. Cum in general was something to be avoided like the plague. Hell, for a guy where I came from, touching the stuff, even your own pretty much made you gay. Going down on a woman after you had put your cock in her meant you were gay. Doggie style was borderline gay activity and if you liked it too much, you could be held in suspicion. So, for me there was lots of sequencing in order to stay within the rules. Kissing to start. Maybe some tit action would follow and then some oral if I was lucky. Kissing a girl after I had gone down on her was decidedly not cool. Once we started fucking, oral was over with until maybe after a shower. The list went on and on.

Edit: I should be very clear here. All this taboo stuff was a reflection of what I experienced as I grew up. back then in the repressed south, homophobia was rampant and much of our way of dealing with things was ridiculous. Saying something was gay was a way of expressing uncomfortable-ness and it applied to almost everything. Please don't think that I still have any of those feelings. In fact the stories that I am telling are my stories of slaying all those taboos and freeing myself from all of that stupid baggage. I've enjoyed doing every single 'gay' thing I can think of and frankly, it's pretty awesome. So, let's get back to it…

So much was my shitty sex life that Jen blew me away with the things that she wanted to do which, to her, were perfectly normal. Her willingness to blow me after I had fucked her was something so simple yet it would make me hard thinking about it for hours after we texted about it. Looking back on it now, my complicated, frustrating, abysmal sex for the first 30 years of my life perfectly primed me for a thrill ride of outrageous sex with Jen.

The anticipated Thursday arrived cold and dark at the end of January. We cut out of work a little early and drove our separate ways to the hotel. I checked in and texted her the room number. A few minutes later a soft knock at the door and we were together again. She came in carrying a large bag that was filled with some outfits and some liquor. Neither of us was very hungry so we sat down to have an icebreaker drink. We talked for a few minutes and then Jen made the first move and came over to sit on my lap. I was already rock hard and straining against my jeans. She noticed and with a sly smile reached down to stroke my cock through my jeans. We kissed, as it grew even larger. Jen moved off of me to position herself on her knees in front of me. My anticipation was off the charts and I could barely contain myself as she began to bite me lightly through my jeans.

“You are very hard already. Are you excited about something?” she teased.

I groaned and let my head drop back as I felt her fingers pulling at my belt. Next I felt the cool air on my cock as it leapt out of my jeans. Her hot breath followed and her tongue slowly licked up the underside. My cock stood straight upright bouncing off her nose, which made her laugh.

“My you are really excited aren’t you?” She whispered.

My cock throbbed upward in time with my heartbeat. With her left hand she reached out and pulled it toward her. As hard as it was, the downward tension as she pulled made it grow even longer and harder which always happens with me. She aimed it straight at her and moved forward taking it in. Her hot mouth enveloped me and I very nearly came. A few quick breaths calmed me down and the corners of her mouth curled into a semi-smile as she continued to swallow my cock. Again she stroked my shaft up the sides and down to underneath my balls. She then moved off my cock to run her tongue down and under my balls, which made me rise up in reaction. Her fingers stroked all over my legs and cock. This was something that I had never felt before and I loved every second of it. She continued for a few minutes and then moved up my body toward my face to kiss me. The old taboos ran through my mind and I could hear the thoughts of my high school and college friends.

“Man, she just had your cock in her mouth and now you are going to kiss her?”

Considering what she had just done to me and how good it felt, I was overpowered by lust and I threw the nonsensical taboo aside. She climbed on top of me and kissed me deeply. I could feel her saliva all around her mouth and now all around mine. The fact that she had just been blowing me didn’t bother me and was actually intensely erotic because of that stupid taboo.
I picked up Jen and together we fell toward the bed. I laid her in front of me and she spread her legs under her skirt. I moved up her inner thigh toward her pussy and I could feel her beginning to breathe a little faster. At first I ran my tongue over her underwear, which was already wet. Together we made it wetter which allowed me to see her lips through the translucent fabric. I ran my hands up her body under her sweater and bra to grab her tits. She moaned when I pinched her nipples and arched her pussy up toward my face. I tongue fucked her through her wet panties for a few seconds which frustrated her. She reached down and pulled them aside saying, “Eat my pussy dammit. I can’t wait any longer” I obliged her willingly and I dove in with my tongue. Her pussy was sweet to the taste. I couldn’t get enough. I licked her from bottom to top. When I got to her clit I sucked on it, which made her thrash about wildly.
After a few minutes I found a rhythm that had her orgasm building slowly. She was so wet that I had no problem sliding first one finger, then two into her pussy. When I did she moaned audibly. I ‘shhhhhsh’d’ her because I didn’t know what people could hear outside our room or through the walls. Much like our first encounter, she bucked up into my mouth as I finger fucked her and sucked on her clit. Together we brought her closer and I could feel her pussy clinching around my fingers.

“Faster…harder…” she whispered and I willingly followed her lead.
“Faster… faster… fas… oh….oh…. oh god… I’m cumming….I’m cumming…. I’m cumming.”

She convulsed and her cum ran down my fingers and onto the bed as I blindly finger fucked her. After a few minutes her breathing slowed just a bit and she hissed at me, “Get up here and fuck me.” I kicked off my pants and shorts and climbed up over her. As my cock approached her pussy she reached down to grab it. She squeezed and jerked it as I moved up inch by inch. In a moment, I felt the warmth of her pussy as my head made contact with her. Unlike our first encounter, the thought of a condom never entered my mind as I pushed my cock head into her. Although I had just finger-fucked the hell out of her, her pussy was very tight. Her cum worked to lubricate my cock as I pushed deeper and deeper into her. Several times, her lips would grab my cock and stretch the skin. Although it hurt, it was a good pain and I delighted in the warmth of her pussy as it swallowed me. I bottomed out into her and she squirmed up the bed away from me.

“easy…. That’s too much… give me a second to.. uh. Work up to it ok?” she whispered.

I withdrew my cock and then pushed into her again. This time her cum completely coated me and it was a hot wet plunge into her. Within a few seconds we developed a rhythm and she went completely nuts as I fucked her. For me, it was a struggle because I was so amped up by the days of texting and the fact that she was here fucking me and it felt so good, that I nearly blew on every stroke. It was frustrating to her because she was asking for it.. begging for it yet I couldn’t give it to her the way she wanted out of fear that I would cum. I had never felt anything like it. It was a tug of war between something that felt so good yet I desperately didn’t want it to be over. I knew that if I blew, I’d be done and she’d be disappointed and everything would be at risk. Thrust after thrust brought her closer to orgasm and somehow I managed to overpower my own. There was a lot of thought about anything other than the incredibly tight, hot wet pussy that I was plowing.
After several minutes of intermittent, start-stop-start-slow-start fucking, Jen started cumming. She grabbed me and clawed at my back, which actually helped stave off my own orgasm. She grabbed and pulled at my ass to try to get met to fuck her harder. I complied as much as I could yet I was still struggling to not blow. Even though she was cumming, I was nowhere near ready for this night to end.
Her orgasm lasted a few minutes and eventually reduced to fitful shudders as the last waves passed. My cock was still rock hard and I was happy that I had gotten her off. I felt relieved that I had accomplished that. I rolled off her to let her breathe a few minutes but as soon as I was on my back, she was up on her side moving down my body. Before I knew it she had my cock in her mouth and I was totally blown away. As hard as it is to believe, this was the first time in my life a woman had gone down on me after I had been fucking her. I watched in amazement as she not only licked her cum from my cock, but she got off on it. She became like an animal hungrily licking my cock and then sucking it deep down her throat. Seeing that taboo literally go down her throat was more than I could take and I very nearly started to cum. I pushed her off of me for a minute, which made her laugh.

“What’s wrong? Did I almost make you cum? Mmmmm I would hate to do that because I have so much more in store for us.” She whispered.

Jen moved up toward my face and kissed me again. Simultaneously she straddled me and began taking off her skirt. She sat back and pulled her sweater and bra up over her head. Now completely naked she slid backward on me to position herself directly over my cock. With an evil smile she pointed it toward her pussy and sat down right on it. Her pussy had dried out a little and she had sucked all her cum off my cock so as she ground down on me the tension and pulling on my cock was intense. Fortunately, it was just painful enough to push my orgasm back a good bit. I remained rock hard and once she reached the bottom she wiggled her hips to fully impale herself. She then began to rock herself forward and back with my cock completely inside her. Fortunately, this felt pretty good to me and it didn’t do much to advance my orgasm. Jen on the other hand loved it and she worked herself to frenzy. Back and forth, back and forth. Little strokes and then long strokes. She would launch a burst of very quick strokes that seemed to drive her crazy. I could feel her pussy tightening around me yet with this position there was not much for me to do other than sit back and watch her ride me. I absolutely loved it because I was enjoying the show of the century with Jen’s tits bouncing while she squirmed, fucked and ground herself all over my cock. She let loose with a torrent of dirty talk which didn’t help me too much but I managed to contain myself.

“Ugh.. your cock feels so good… oh, it is so deep. I have never felt anything like this. I just can’t stop myself….”

Soon, she quieted down and I saw her get lost in the pleasure. Her thrusts on top of me grew even faster as her exposed clit looked like a blur of motion. Next came the moans that grew ever louder. I again tried to quiet her but eventually gave up and let her go.

Soon, she was whispering again, “oh god.. oh god… oh god… I’m going to cum.. I’m going to cum.. I…. I…..”

And then I felt it. Suddenly there was a warm feeling running down my balls and out onto my stomach and into my belly button. Her bucking pussy started to slap and slosh and I could hear something liquid splashing all over my legs. The main thing that I felt was the warmth. It was incredible.
Jen came and came and came. It seemed to go on for a long time and she was totally lost on a different planet. Soon, she regained sensibility as she came down from her orgasm. She looked down at me and splashed up some of the fluid that had gushed out onto me.

“what the hell is this? Did you cum THIS much? What the hell?” “I have no idea. It isn’t me because I haven’t cum yet” I answered.
“What? You didn’t cum? Then what is this? THIS has never happened before? What the hell is this?” “I don’t know. I guess it is your cum.” I chuckled. “MY cum? No way. I don’t do things like this? I’ve never seen anything like this?” “Well, it certainly has to be you because I know I didn’t cum, and my cock is still rock hard.. plus, who cares? That’s the most incredible thing I have ever seen!” “Well, like I said, this has never happened to me. That damn cock of yours must have done something to me because that was one hell of an orgasm.”

I laughed as she slid off of me. Her cum was everywhere. Underneath me was a huge wet spot on the bed.

She touched it and whispered incredulously, “this is everywhere… my god… how much did I cum? “I don’t know but that was pretty much the hottest thing I have ever seen.” “Are you sure? You aren’t put off by that are you? “No way. That’s incredible”, I answered.

I pushed her back on the bed and spread her legs. Jen seemed to be preoccupied with trying to process what happened. I moved up her inner thigh and started to kiss her skin. As I moved closer to her pussy I began to taste an intensely sweet flavor. Once I got to her pussy, it was covered by what I guessed was her cum. This time it tasted different and much more sweet. I licked every inch of her and when she had had enough, she pulled me up on top of her. Again I positioned my cock at the entrance to her pussy. Entering the third time was just as intense when I felt her warmth surround me.
I began to fuck her again with long, deep strokes. This time she had no problem with me bottoming out deep in her pussy. Apparently the cowgirl ride on top of me had made things a little easier for her. Together we fucked for what must have been 20 minutes. Again, I conjured all sorts of thoughts to delay my orgasm. I was so focused on maximizing this experience that I walked a tightrope between indulging in the sight of my cock pounding her pussy and her tits bouncing versus cliché’ thoughts of baseball.

The end came when Jen moved to position her legs up over my shoulders, which gave me complete, total access to her pussy. She encouraged me on and as I felt her cum and clamp down on me for the second or third time, I could stand it no more. I unloaded, or should I say unleashed a torrent of cum deep into her. The sensation was so intense that I couldn’t stand it and I had to hold still with my cock buried in her as it shot spurt after spurt. In a few seconds I was able to begin moving again as the intensity passed. I enjoyed a few more seconds of fucking before I collapsed off to her side.

“That was incredible” I croaked out. “Yes. That was pretty damn good. I still can’t believe that you made me cum like that” “well, I think I blew a similar sized load in you if that means anything.. ha ha.”

Together we laid on the bed off to the side of the huge wet spot. We talked a little and eventually we both decided that we were too spent to do anything else. As much as I wanted to fuck her again, my cock just wouldn’t have it.

Jen packed up ahead of me and headed out to catch up with some friends who were going to be having drinks later. We kissed goodbye at the door and she disappeared into the night. Shortly afterward the texts began to arrive and I spent the rest of the night consoling her that what had happened to her was not something to be ashamed of.

Source: reddit.com/r/gonewildstories/comments/36f505/a_series_of_encounters_with_a_coworker_part_2_mf