An interesting turn of events [M22, F22]

In 2014, I graduated college with honors and a double major, but did not have any job offers yet. This forced me to move back with my parents after graduation. While back at home, I quickly found a job using my degree, but unfortunately it was only part time. In an attempt to move out, and with the knowledge that I would soon be paying back my student loans, I picked up two other part time jobs although they were just in retail. This was my situation for nearly a year, and while I did not overtly enjoy these obvious limitations in my life, I was able to start saving a decent amount, and began to look for full time employment. I finally got a job offer halfway across the country, and this is where my story officially begins.

Now I had just moved 1500 miles from anyone that I knew, and while I am fairly social, I am not great about making actual friends that I can spend significant time with. Luckily for me, my coworker Haley had pity on me. She had lived in this city her entire life, for the most part, and thus had a pretty set group of friends. Haley was 5’7”, a bit portly, but she had massive tits. I was not attracted to her, but she was also a pretty blatant lesbian. On top of this, I had no desire to date anyone that I worked with. I had been down that road in the past, and I knew that it never ended well. Not wanting the invitation to be strange, Haley not only invited me to hang out with her and her friends, but also invited one of our other coworkers named Jessica. Jessica was about 5’6”, in decent shape, had shoulder length light brown hair, and a pretty cute face. She had a bit of the girl next door look to her. She had fairly small breasts, 34 B’s most likely, but a nice looking ass. Even though I had only worked at my new job for a couple of weeks, I noticed the stark contrast in personality between the two girls. Haley was 28, raunchy and inappropriate in the best way, a perfectionist in her work, and she swore like a sailor. Jessica was my age (22) and had the personality of sort of your typical sorority girl but in a strange reserved way. If she heard me and Haley making an inappropriate comment, she would become mildly uncomfortable and turn away, or when we talked about plans for the week/weekend, she would rarely contribute to the conversation. My early read on her was that she was shy around new people, but I did not think more of it than that.

When Haley invited both me and Jessica to hang out with her and her friends at a local bar and grab a drink, I immediately answered in the affirmative, glad that I would be able to hang out with someone that I knew instead of trying to cultivate something from nothing at a bar by myself. To my surprise Jessica laughed and declined the invitation. Playfully asking around and giving her a bit of a hard time, Haley asked her what she was doing that could be more fun than getting a drink with the “two coolest people in the office”. Jessica laughed and said that she was having dinner with her family. Haley and I accepted her out, and after a bit more banter Jessica went home and Haley and I went to the bar where I met her friends. We had a great time, I probably drank a few too many beers, but so did everyone else. We closed down the bar, and with everyone laughing, Haley told me that I should come out with her more often. I smile and agree.

Haley was tons of fun to hang out with, and her friends all seemed pretty cool as well. The next few months saw me and Haley become better and better friends, and we hung out with each other on a semi-regular basis. We began to tell each other hilarious stories from our past, resulting in numerous inside jokes that we would try and use in the workplace as often as possible. As Haley and I became friends, Jessica and I also started to become friends, but in a vastly different way than Haley and me.

Like I said before, Jessica was much more reserved than Haley, but she also had some major issues in her home life. She began to confide in me about how she felt like she had to be there for her younger siblings because her mother was more concerned with her social life than with her kids. She told me about her time at college as well. She was in a sorority as I had guessed, but she told me that she was the black sheep of her sisterhood. She drank and partied similarly to everyone else, but she also did not sleep around. I told her that not sleeping around wasn’t a bad thing, but I could tell she was holding something back. I decided not press the issue, as I figured if she wanted to tell me she would.

Our conversation died down a bit, but then suddenly she stopped typing and said to me “I mean, just because I haven’t done that doesn’t mean I’m not fun.” The outburst surprised me.

I turned to her and I ask “Wait, are you a virgin?”

She blushes and dips her head while sheepishly saying “Yes”.

The conversation suddenly turned serious, but not in a bad way. “How far have you gone before, if you don’t mind my asking?” I asked.

“Well I have done other stuff” she plainly stated.

The answer hung in the air for a second, neither one of us aware of where the conversation was going to go. We were the only two people in our offices at the moment, and we could both feel the tide of the conversation turning. “How many people have you slept with?” She followed up her answer with a question of her own.

“11” I responded with little hesitation. “But most of them I was dating at the time.”

She seemed surprised that I had dated that many people, but kept her shocked expression to a minimum. “How do you get comfortable enough to date that many people?”

Not the question I was expecting at all. “Well I suppose,” I begin “I suppose it usually starts with a conversation, where we begin to talk about things that we normally wouldn’t talk about.”

Even though it was vague, she seemed satisfied with the answer. I could tell what we were both thinking: this might be one of those conversations. The dialogue did not go much further than that, but I noticed that Jessica started to say something a few times, but quickly thought better of it and swallowed her words. By the time we left, it was as if we had leapt a barrier, and if I was not mistaken, some very strange sexual tension.

Over the next few weeks, Haley and I continued to invite Jessica out, and every time she had some reason to not join us. Things between Jessica and me had gone from being more comfortable with each other to a palpable tension in the air whenever we were alone in the same room together. I was curious about what she thought about our conversation, but I chickened out every time I had the opportunity to talk to her.

It was around this time that I decided to have a bad movie night at my apartment. I invited Haley, as well as Finn and Pam, two of my friends that were engaged, and Jessica. Jessica knew Pam from work, but had not met Finn yet. When I told Jessica who all was going, she told me that she would think about it. At lunch, Jessica came and found me and told me that she was willing to come to the movie night.

“Great! I think we are planning to start around 8.” I said.

“Cool. See you then.”

She lingered for an awkward second before she left. I found myself staring at her sun dress clad figure as she walked away. It was a loose fitting dress that flowed off of her, adding to her girl next door vibe. I was suddenly acutely aware of the growing bulge in my pants. “Had Jessica just given me a semi?” I thought to myself. I attempted to push the thought of her in that dress out of my mind and finish the day of work, but I was less than successful. I had to clean my apartment and pick up snacks for tonight anyways, so I told my boss that I was planning on leaving a bit early. He was completely fine with that because I stayed late on a regular basis to finish up work.
I quickly left the building, ran to the liquor store to pick up a case of beer, then ran by the store to grab some chips and popcorn for snacks. When I got home I vacuumed my apartment, took out the trash, and did the few dishes that were left in the sink. As I finished up, I looked at the clock. 7:25. I still had half an hour before anyone would be arriving. My mind drifted back to Jessica in her sun dress. Her small perky tits were covered by that thin fabric, and nothing else. I began to speculate on whether or not she was wearing underwear under her dress. I came to the conclusion that she probably was, but for the sake of my fantasy she would not be. I went to the bathroom to take care of myself before my company arrived. After thinking about Jessica all day, it was not surprising that I did not last long, nor the incredible amount of cum that came out when I finished.

I cleaned up, and not a second after I sat on my couch there was a knock on the door. It was Finn and Pam. I was far from surprised that they were the first to show up, as Pam was always punctual. Jessica was the next to arrive, although not in her sundress to my disappointment. She was wearing a simple light blue v-neck shirt with a sweater and skinny jeans. I thank her for coming, and tell her that we have beer in the fridge as well as a myriad of other hard alcohol if she prefered that. She grabbed a beer out of the fridge and took a seat on the couch. We waited about 15 more minutes for Haley to show up. Again, not really surprised as she had a tendency to be about 10 – 15 minutes late regardless of the situation. We all started to talk and have a good time, and eventually we started the movie. I started in a chair on the side of the couch, and the other four were on it, quite nice and cozy. After the movie Finn and Pam left because they had to wake up early the next morning. Haley, Jessica, and I put in another movie, but we were not really watching it. We decided to get out a deck of cards as we continued to drink. We started playing rummy, but eventually we stopped that as well, and we began to just talk.

Jessica had started out slow on the drinking, but she had really picked up her pace, and I could tell that she was quite tipsy, maybe even a solid drunk. I had not held back with the drinking because I did not have to drive home, and so by midnight I was pretty drunk. Not stupid, incoherent drunk, but drunk nonetheless. Haley had also drank quite a bit, but she noticed that it was starting to wind down, and she told me that she was going to meet some other friends at a bar. She left, and it was all of the sudden me and Jessica alone in my apartment with loads of alcohol and a penchant for bad decisions. Jessica was curled up on the couch and was looking pretty tired. Because I am not a complete asshole, and also aware that I would still have to work with her, I made no move on her. I told her that she was more than welcome to stay on my couch tonight if she wanted.

“Ok, that sounds nice” she purred. I got up to leave, but stopped when I heard her say “Are you going to bed already?”

“I just assumed you were tired and wanted to crash” I said, as I began to meander back to the couch.

“I’m not that tired. We should put in another movie and we can fall asleep to that” she stated.

I was ok with that, and I sat back down on the couch after I loaded up the third movie of the evening. She immediately took the blanket off the back of the couch and laid her head on my chest. I could smell the sweet scent of her shampoo in her hair, and almost unconsciously started to stroke her hair. She sighed and melted further into me.

“This is nice” she she said in a voice barely above a whisper.

“I agree” I breathed, as I leaned down to kiss her forehead.

She shifted so I had better access to her body. Without thinking, I gently kissed her cheek, her neck, and then finally her lips. Her lips were so soft, and while it was fairly obvious that she did not have a plethora of experience in this department, her innocence was incredibly attractive to me. My tongue parted her lips and I kissed her deeply. I broke my lips from hers as I again began to kiss down her neck to her shirt, each kiss being accompanied by a very light nibble. I slid her sweater off, and took off her shirt, but I stopped myself from taking off her bra. I did not want to move to fast or have her feel pressured to do anything that she was not comfortable with. Taking her shirt off, however, seemed to have emboldened Jessica. She pushed herself on top of me and began to make out with me furiously. My hands caressed her back and sides as she continued to kiss and nibble at my lips. At this point, I felt my raging erection trapped in my jeans, and it was everything that I could do to not take it out right then.

I sat up. My left hand grabbed her head as I kissed her, and slowly danced its way towards her breasts. I slid my hand under her bra, my fingers finding her nipples and gently playing with them. Jessica let out an audible gasp as this happened. She paused for a moment, and I told her that we could stop at any time. “I’m ok. It just surprised me is all.”

“Ok” I replied. “But tell me if you are uncomfortable at any time and I promise, I will stop.”

“Deal” she said as she leaned her head in to continue making out.

As I was playing with her soft, supple boobs with my left hand, my right snuck behind her back and undid the clasp on her bra. She shrugged the bra off, and as it fell to the floor, I got my first full look at her tits. She had tiny, light pink nipples, and right now they were as hard as rocks. She was noticeably turned on. I felt my dick strain further against the prison that was my pants, resulting in my adjusting myself. Jessica stared as I did this, but I could tell that she was not ready for me to pull it out. I pushed her back on the couch and I climbed on top of her. I began to kiss down her neck to her perky breasts. I take her nipples in my mouth, sucking on them, and then moving to the other. Jessica is enjoying herself, quietly moaning with each new sensation. I drag my tongue down, past her tits, across her stomach. When I reach her pants I feel her tense up for a second, but then she relaxes. I can feel the heat coming from between her thighs. I brush my hand across her crotch before I unbutton her pants and unzip the zipper, but i do not pull her jeans off. “Not yet” I think to myself. I see her pink cotton panties underneath her jeans, poking out of the newfound space.

I pull her panties down, making a V, allowing me to kiss her cleanly shaved mound. My tongue can just reach the top of her slit, and as it does, I hear her almost yelp. I immediately stop and ask her if she is alright. “I’m good” she said. “It’s just that nobody has ever done that before”.

“Is that a good thing?” I ask.

“Definitely.”

I pull her pants off with her help (they are skinny jeans after all) but I make sure to leave her underwear on. I can see a wet spot forming on the outside. I begin to gently rub her pussy over her panties. She begins to moan and squirm. I finally pull them aside and my tongue dives into her wet cavern. My tongue dances over her clit as she twitches and moans quietly.

“Would you like to move to my bedroom?” I ask. “It would probably be more comfortable in there.”

Jessica nods silently. I stand up, take her by the hand, and lead her to my bed. I let her get on the bed, when I realize that I am still fully clothed while she has nothing but her underwear on. I take my shirt off, followed quickly by my jeans. I leave my boxers on, but now Jessica can completely see the huge tent that I am pitching. She stands up and kisses me, then reaches down and grabs my rock hard cock. I can tell that she does not know exactly what to do with it, but just the feel of her hand on me cause my heart to skip a beat. I reach down and push her panties down; she wiggles her ass causing them to drop all the way to the floor. She pulls down my boxers leaving both of us naked in my room. I stare at her fit, nude body: my eyes traveling from her gorgeous, perky tits to her swollen pink pussy, and finally resting on her face. She has a faint smile about her and she seems very happy. It makes me think that only a few months ago, I had barely even spoken to her, and now she was naked right in front of me. “Jessica…” I began.

“I want to do this” she said. Before I could even get out my thought, she voiced what I wanted to know. “I’m ready.” She declared.

I went to my desk where I kept my condoms, tore one off from the pack, and put it on. Jessica giggled. “I didn’t know that was what condoms made penises look like.” I burst out laughing, not just at the random comment, but at the hilarity of the situation. Here she was, about to lose her virginity, and she makes a joke about what the condom makes my dick look like. We are both laughing, but the laughing turned into us making out fiercely. I begin to finger her wet cunt. She is so tight that when I put one finger in it feels as if there is not room for anything else, but she is also drenched. I put in a second finger so that she would be at least a little more stretched out when it came time for my cock. Initially the second finger was too much, but she got used to it and started to moan louder. “I want you!” She said in a combination between a yell and a gasp.

I said nothing, I just laid her on her back, spread her legs, and began to kiss her as I rubbed my dick against the soaking lips of her cunt. I opened her lips with my dick and pressed in gently. When the head of my cock entered her, Jessica moaned and yelped.

“Are you ok?” I inquire, not wanting it to stop.

“It’s just so big” is what I hear after a second of silence. This strokes my ego. I didn’t care if she had never been with anyone else, all guys love hearing shit like that. I slowly probe deeper and deeper into her as I feel the warmth of her pussy envelope my cock. She is so tight and so wet it feels amazing to me.

“Is it ok if I go faster?”

Jessica nods, in a state between intense pleasure and new sensations. I still thrust into her slowly, but I start working up a bit of a head of steam. Jessica begins to squeal and moan loudly as I thrust into her faster and faster. By now, the sensation is so intense that I am overcome with lust and desire. Jessica wraps her legs around my back, pulling me into her even deeper. I grab at her tits and pinch her nipples as I can feel myself getting closer to cumming. Jessica spasms, and I feel the familiar tightening of an orgasming pussy on my dick. That feeling was too much to overcome as I thrust deep into Jessica and expel my load into the condom inside of her. We stay in that position for what seemed like ages, but in reality was probably only 20 seconds. I dispose of the condom, and come back to the bed. I put on my boxers, and climb into bed next to Jessica who is still naked. She scoots close to me and falls asleep in my arms. I lie awake for a while longer, trying to imagine what this means now, but eventually giving up, and deciding that we would cross that bridge in the morning.

Source: reddit.com/r/gonewildstories/comments/4dhz1o/an_interesting_turn_of_events_m22_f22