Before I start, just wanna say I’m not much of a writer, so any and all constructive criticism is appreciated! I should also mention that I sadly was only able to spend a few more days with Katie after the events in this story, since I was moving to another state to start my new job. Nevertheless, it was a week I’ll never forget. Ok, here we go.
“What would your roommates think if they knew what you were doing–uuuggghhhfff!”, moaned Katie as I once again thrust my throbbing dick into her beautiful wet pussy.
My roommates. Hm. My 3 roommates, Jim, Melvin, and Mike were more or less the only real friends I had at school. They knew I got nervous around others and that I didn’t really have much of a social life. They were often kind enough to invite me to social events involving their friend groups. Most of the events I went to with Jim and Melvin were church events, since they were both fiercely Catholic. Even though I was no longer religious, I still went because the people there were always so nice and friendly. However, if they knew that I was currently fucking someone senseless on my bed right now, they would likely express righteous disapproval. It was for this reason that I never talked to them about sex or intimacy in general, because they always related it back to Catholicism.
Mike, on the other hand, was just your average outgoing college guy. He would party and get wasted 3 or 4 nights a week. He would probably be beaming with pride if I told him.
I laughed imagining their reactions. Them knowing that their shy, anxious, polite, lamb of a roommate had taken a walk on the wild side.
But I’m getting ahead of myself. I got no sleep in the hours after that makeout session with Katie. My heart was still racing, and I had the bitter taste of adrenaline in my mouth. I was actually looking forward to seeing another human being again. Most of the time during social interactions, I would just be waiting for it to be over so I could relax again. But I didn’t want to relax. I wanted to feel the touch of Katie’s warm skin against mine again.
Many people who suffer from social anxiety also deal with inferiority complexes, including me. Inferiority complexes are a general unrealistic feeling of inadequacy caused by actual or supposed inferiority in some setting, which usually results in aggressive overcompensation. This basically means that when it comes to things of importance (or things that I believe are of importance) such as job interviews, studying, exercising, and now, sex, I overprepare.
For example, during one of my more recent internships, I was a professional ass-kisser and I performed like my very life depended on it. I of course want to do well at my work, but I overcompensate because I feel if I perform poorly I will be looked down upon by others.
For me, this also applied to sex. So, for the entire day leading up to my next encounter with Katie, I basically researched how to have sex. I learned where the erogenous zones were and in what order to touch them, I learned about the g-spot, and how to touch a woman in general. I even practiced putting on condoms. I also asked my closest friend, James, if he had any advice for me. I was determined to make this fun, not awkward. I was gonna know what I was doing and make my time with this girl worth it.
That night at about 11 PM, Katie texted me that she just got off work, so I went to go pick her up. She got into my car looking rather tired and exhausted. She had worked a double shift that day. I told her that if she was too tired to hang out, it was alright. She said no, she wanted go come back to my apartment. My dick was already starting to tingle. We got back, and I wasn’t sure what to do. I didn’t know if I should just start kissing her or if we should ease into it.
We both sat down on the couch, and I turned on Brooklyn 99. It was here that I pulled “the move”. I reached my arm over her shoulder, and she snuggled close to my chest, her arm drooped over my crotch area. I started kissing her. This time, I was on top of her.
I went from her lips to her ears and then to her neck and repeated this in various different patterns. I could hear her softly moaning.
I asked her if this was okay and if she really wanted to do this. “Mmmhhhmm”, she moaned. I slipped off her shirt and then my shirt. Then I came to the bra. She was wearing a sports bra, and I could not for the life of me figure out how take it off. As I was kissing her upper chest area, I said, “How do I get this thing off?” She giggled and slipped it over her head, revealing her scrumptious breasts.
She was French kissing me and digging her nails into my back. I never thought I would be the type to enjoy pain, but there’s just something really hot about having the claw marks of a beautiful woman on your back. Katie’s little pink nipples were already firm and erect, and I spent the next few minutes alternating between her neck, lips, ears, and tits as I had read online earlier that day. I then slipped off her jeans, revealing her amazing Star Wars panties.
How did I get this lucky? This girl was beautiful, athletic, and she was a complete nerd, like me. I couldn’t help myself from laughing when I saw them. I got her pants off and began kissing her toned and flawless tummy. I slowly moved down and breathed onto princess leia, who was on the area of her panties that covered her vagina.
“Mmmmmm…. Why don’t we go to your bedroom now?”
I agreed, but then I did something I didn’t expect I would do. I grabbed her back and legs, and lifted her clear off the couch and carried her to my bed and laid her down. “Okay, so you’re pretty strong,” she laughed while biting her lip. I continue kissing her torso region and she periodically pulled my head back up to kiss me and play with my hair ( I have long hair lol). I then pulled down her panties, and set my eyes on the first real-life vagina I had ever seen. It was shaven, pink, and (to my satisfaction) wet.
I started by kissing her inner thighs and around her lower tummy area, ocasionally flicking my tongue across her labia and clitoris. She was moaning a little more loudly now. I started to focus more on her pussy and stuck a finger in and stroked where I assumed her g-spot was. It was warm. I felt that firm, spongy tissue that I had read about and started making a “come hither” motion with my finger.
“Wow, you’re pretty good. I thought you said you were a virgin…”, moaned Katie as I continued to finger and eat her snatch. I smiled devilishly and continued.
This is when her breathing really started to pick up. However, I wasn’t able to make her orgasm. But it did get her moaning pretty loudly.
She ended up giving me a blowjob, which felt really good. Then at last, we did the deed. For the next 1.5 hours the only sounds in my apartment were my (protected, mind you) cock pounding away at Katie’s pussy, and our sweaty, writhing bodies moving around in my bed.
Now, you’re probably wondering how in the fuck a virgin was able to last that long. Well, I didn’t exactly “last”. I never came. That’s right, I had masturbated so much that I had developed the dreaded death grip syndrome. My dick was so used to my hand making it cum that pussy stimulation wasn’t enough.
It also wasn’t just masturbation. I mentioned in my last post that I have a rather high libido. Because of this, I developed some pretty interesting was of pleasuring myself growing up. One of these was teaching myself to suck my own cock. There were many times that I had sucked myself off until I came. Yep you heard it here first. I was better at giving myself blowjobs than Katie was at giving them to me.
Anyway, we only stopped after that long because we were both exhausted. We both enjoyed ourselves, but nevertheless, exhausted. She ended up spending the night and we got lunch the next day because we slept through breakfast.
We hung out and fucked several more times throughout the week and it was absolutely amazing. On the night I said goodbye to her, I assumed we would have sex again. But when she came over, we just laid down on my bed and kissed in complete silence for two hours and said goodbye.
“I’m gonna miss you.”
“I’ll miss you too.”
It was about 12:30 AM. I drove her home, we both got out of the car, and kissed in that empty, dimly lit parking lot for about 30 more seconds.
We both agreed that neither of us had the time nor the energy for a long distance relationship. She was a sophomore and I was a senior, and I didn’t want to put that pressure on her. But we have managed to say in touch and still text each other every now and then. I hope I’ll get to see her again when I come back to my college town.
Source: reddit.com/r/gonewildstories/comments/dsbjjp/mf_how_the_awkward_shy_kid_22_m_lost_his