Raunchy, Romantic Escapades Ch. 01

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Chrissie takes a shy boy's virginity.
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It was my first year of uni. Completely new city, new people, new... Everything. I knew that the first year is not academically challenging, and with my straight A's earned in sixth form, by doing the bare minimum, I hadn't worried that much about the work load. First year was a time to make friends and memories, and to party my life away. This was of course balanced well with studies, just enough so that I pass - first year isn't counted toward the final degree anyway.

I had always been a shy a timid girl throughout my high school years and only started to open myself up to new experiences and new relationships at the end of my A levels. I had my first kiss halfway through year 13 with my best friend at the time. I had my first kiss with a boy a month after that. First dates, first boyfriends, first 'sleepovers'. I lost my virginity on a drunken, one-night-stand, mistake and regret filled night in the summer. With my plans of having the perfect and special first time ruined, I thought to myself, 'what the hell, might as well enjoy it'. So that's exactly what I did. Since starting university in September, and beginning the relationship with my current boyfriend in January, I has sex with 7 guys, oral sex with a further 3, as well as some girls, and got touchy-feely with more people than I care to count. My sexual escapades were always a good topic of discussion with my best uni friend Minnie. She was in a stable relationship, but she loved all hearing about the details of me getting raunchy with men, women, and everything in between.

To give you a little bit of context here's what I looked like: I was 5'4", petite, with a small frame. My breasts left much to be desired, no bigger than my own hand with small, bright pink nipples. But I made up for it with my ample bosom, hips a little too wide for my small waist and a round peachy ass. I had long red hair, unruly and wavy. I had large blue eyed, and small nose and small lips. Overall I never thought I was ugly, but possibly just below average, nothing to go crazy for. The guys that I met in pubs, clubs, and even libraries, seemed to disagree, as I was being asked out everywhere I went.

Anyway. This is a true story, of how the love of my life and I ended up together, but it starts very unexpectedly. In fact, the start is a cause for multitude of awkward moments, mishaps and bumps in our relationship. Let's start at the beginning.

October 27th

It was the Halloween social in my dance society. We all dressed up in matching zombie school girl outfits, and went to the student bar for pre-drinks. On most night outs I was one of the sluttiest-dressed girls there, but on Halloween I liked to go full on gore. While my 2 good friends showed a lot of skin and had minimal make up, with some fake blood splattered across their shirts tied up right underneath their boobs, I used PVA glue to give me an appearance of peeling skin, tissue and sculpting clay on the side of my forehead to look like my brains were actually falling out, and showed of my artistic skills using make up to make my skin rot. I looked pretty awesome.

In the bar I saw a guy who I knew from my classes and, being already intoxicated, I ran up to him to give him a hug.

"Leonard!" I shouted tapping his shoulder, and hugging him close as he turned around. No one else calls him my his full name, to most his name is Lenny, so he knew who I was, but when he saw me, shock and surprise painted his face.

"Woah, what the fuck?! Chrissie is that you?" He said hugging me back.

"Like my costume?" I twirled for him, laughing at his expression. I never believed in male/female friendships, until I met Leonard. Ours was the most platonic opposite sex friendship to have ever existed, and not once have I thought about his dick. And I like to think he's never thought of me in that way either.

"Love it! You actually look pretty fucking scary." He said, and I smiled and nodded, accepting his complement. He then introduced me to his friends. There was 4 of them, all standing around the pool table with pints in their hands, regular clothing. They all looked cute, fun, and rather dorky. I figured that they hadn't planned on going out. Kameron, Conrad, Luke and Andy. Not that I remembered their names after that night. I waved to each of them wishing them a good night before leaving to re-join my friends. I took 2 seconds longer to hang my eyes on Andy, as he was quite good looking, but then left, not thinking anything else of it.

I went out clubbing with my friends and came home alone after a good night out of dancing laughing and making out with strangers. Nothing else happened that night.

November 5th

I was at the student bar again, with my flatmates. It was karaoke night, and we had no intension of going out tonight, so I didn't really dress up. With simple black jeans and a frilly while crop top, I looked good, but not over-dressed. Plus, the tight jeans were doing my round ass justice while a year of vigorous squatting definitely paid off. Minnie, Mellissa and me sat on the sofa having some drinks and laughing. A few guys have already caught my eye, and the girls kept teasing.

"If I have another sleepless night because of you Chris," started Minnie "I'm gonna ram my foot so far up your ass, no guy will ever enter it again."

"Min, I'd probably enjoy that, and you know it." I laughed and winked at her. "Also, I've never done anal, so what you mean again?"

"Girl, you're missing out" Minnie stated. "And back on topic, either get me some earmuffs, or a gag for yourself."

"I'm not on the prowl today, quiet night for me. I do have an assignment due in on Monday, which I barely even started."

"Oh God please, don't talk about uni work," Melissa begged "we had a deal."

"Sorry, sorry." I said quickly and downed my half full drink. We agreed that every time someone mentions work today, she will have to finish her drink. As I got up to buy another one, I saw Leonard again with his friends. The good looking one from Halloween night was missing, but there was someone new. I brought my drink, went past my friends and told them I'd be right back, as I headed in Leonards direction. They just rolled their eyes, and Minnie made a blow job imitation with her hand and tongue.

"Hi Leonard, and hi Leonard's friends, whose names I don't remember!" I greeted them all squeezing in between him and Kameron. Leonard introduced them all again, and the new guy, Jake. Jake was very cute, very awkward. He had a baby face, and a gentle stubble that needed to be trimmed, and long dark hair, which didn't really suit him. Nevertheless, he looked cute, dorky and geeky, and just adorably endearing.

I waved my two friends over to come and sit with us, and we all had fun and drank together. Jake never initiated a conversation with anyone but Luke and Conrad. I tried my best to ask him questions and draw him in, but to no use, he just did not engage. I gave up for a bit and went to play foosball with Luke and Conrad, throwing my arms up in the air every time I scored, causing my little crop top to lift up a tad, just enough to show the bottom of my pink lace bra. I could feel myself pushing my hips out, to accentuate my shapely posterior, not necessarily on purpose, but definitely not accidentally. When we finished playing, I quickly took Luke's place next to Jake.

"Hey, that's my seat." He challenged. He had sandy hair, green eyes. He was the tallest out of the bunch standing just under 6 foot. Again, quite a cute boy with a baby face and soft dimples forming in his cheeks whenever he smiled. He was a lot more confident than Jake and enjoyed having the attention on him, which, I think, is why I gravitated towards Jake that night. I wanted a bit of a challenge.

"Well, looks like you need to find a new one." I replied, not planning to move.

"Why don't I sit back in my seat, and you can sit on my lap?" He offered with a cheeky grin. Ah. Like I thought, confident and enjoyed the attention.

"Why don't you sit back in your seat, and I can sit on Jake's lap?" I threw back at Luke, and looked at Jake with a soft smile. Jake was ready to protest, when I stood up and positioned myself on his lap, facing Luke. I was a small girl, only 5'4", so Jake, being a lot taller than me, and a lot broader could comfortably handle me on his lap if he just relaxed. However he was very tense and his hands were on either side of him, unwilling to move. I wanted to tell him to put his arms around me and to relax, but Luke beat me to it.

"That's perfectly fine with me, as long as that virgin relaxes a little bit." He grinned even wider than before, elbowing Jake in the side. I felt his body release a little bit, but his hands were still firmly pressed against the sofa.

"Hey, it's not nice to tease!" I reprimanded Luke.

"Damn, you should hear how he speaks to me when no one is around, the little Cunt McCunty." - Luke rolled his eyes. I laughed. I realised by now, 2 months into uni that in this area of England 'Cunt' isn't the most god dammed awful work you could say, like it would be in other places. Everyone uses that word, to describe people they don't like, people they do like and people who they are indifferent to.

After only a couple of minutes, when I realised that Jake wasn't relaxing at all, I got up and sat across from him on the table; despite everything, I actually didn't want to make him any more uncomfortable. The tables were low, the same height at the sofas so I was still on eye level with everyone, Minnie made eye contact with me. I knew what she was thinking; just an hour back, I told my friends that I will have a break today, but now, all I could think about is how can I get this shy and socially awkward guy to come home with me. I usually found that I can just flutter my eyes at someone, bend over to pick something up off the floor, and any guy I wanted was mine. But this was different, using sex appeal wouldn't work, and I needed to gain his trust, somehow. I rolled my eyes at her, and she did the same, and I shifted my focus back to Jake.

I noticed that his drink was empty, and I only had a couple of sips left of mine, which I poured down my throat in half a second. I stood, and grabbed his hand. It was sweaty and clammy, but I didn't care.

"Come on, let's get a drink," I said, pulling him up. Luke helped, by pushing him off the sofa. "On me."

I made my way to the bar, continuously holding his hand, scared that he would somehow escape and run away. I lead the way, and he followed behind me. The queue was massive so I knew we would stand there waiting for at least 15 minutes, which gave me some time to talk to him and get to know him a little. Show him that I'm not that scary. I saw back at our tables that Kameron and Conrad were starting to get up, but Luke sat them down. They showed him their empty glasses, and pointed to the bar. Luke said something to them which made them sulk and remain seated and then he winked at me, nodding his head at Jake. From that, I understood that Luke just wanted his friend to finally get laid, and I made it my mission for tonight. Looking at Jake's expression, he appeared lost and vulnerable, not knowing what to do.

"Hi Jake." I turned to him with a smile. Start slow.

"Helloo." He said, lengthening the 'oo' at the end, smiled awkwardly and waved at me with his free hand. The other hand was still holding mine. He then instantly went back to looking lost and scared. I found him so adorable, I struggled to stop myself from giggling.

"How has your evening been so far?" I asked.

"It's been quite good. What about you?" He still had the same awkward, forced smile on his face.

"It's been lovely." I gave his hand a gentle reassuring squeeze, which made him flinch a little. "Am I making you uncomfortable? Be honest. "

"Noo." There it was, that lengthened 'oo' again.

"Are you sure?"

"I... Yeah, a little bit" he looked down at his feet. I let go of his hand, and he quickly put both his arms behind his back.

"I'm sorry, I didn't want to do that." I said truthfully, and sent him a warm, soft smile. The kind of smile I give to my grandma, not the kind that I usually give to guys. That smile would probably send him running. "What do you study?" I asked, starting a conversation.

"Oh... Nothing," he hesitated. "I mean, I'm not at uni here yet."

"Oh right," I said surprised, and genuinely curious I asked further "so what do you do then, do you work? "

"Noo." He said slowly, with the cute 'oo'.

"Oh, are you still in school?" I started to wonder how old he actually was. I assumed that he is over 18 since he's in the uni bar. I assumed he's in the uni, since he's in the uni bar. He did have a very youthful looking face, and if he is underage, I'm gonna feel like a complete and utter asshole. I need to stop assuming things.

"Well, kind of" he said, really not giving anything away.

"What does that mean?" I asked, still smiling, still a little concerned. He took a deep breath.

"I'm resitting my A levels, and didn't go to uni with the guys because I wanted better grades." He finally explained. This had been the longest sentence he had spoken to me since we met, I felt relieved, as that meant that he is at least the same age as me, 18.

"Ohh, okay, that makes a lot of sense. So how did you meet them lot?" I threw my head briefly at the crowd.

"In school."

"Oh right," I wondered for a bit. Did he come from a different city, to visit Luke? He seemed the closest with Luke. Or did he and Luke went to the same school in this city?

"Yeah, me, Luke, Kameron and Conrad went to school together." He said before I could ask.

"All of you guys? That's so sweet! Are you from here, or did you come to visit?"

"No, we're all from here."

"That's nice." I smiled at him again. I felt like he was opening up a little bit, and feeling a bit more comfortable in my presence. I also noticed that I was asking all the questions and we hadn't talked about me, so I told him "I moved like 200 miles away from home to go to uni. Didn't know anyone when I first started, not even one person from my city that I know of, came here."

"That sounds... Scary." He stated after a little hesitation

"It was," I admitted "but I felt like I could completely reinvent myself, and be the person I always wanted to be. It was kind of like starting fresh, with a clean slate." - He didn't say anything, so I prompted him "wouldn't you ever want to do that? Start over, in a new place, where no one knows who you were before?"

"I... Well, I think..." He went quiet for a moment. "Yeah. That's why I needed to resit my A levels. I wanted to go to Birmingham, but I needed top grades."

"Birmingham? That is a very big city, very busy." I said. I wanted to add that he might not cope, but I thought that would sound condescending, so instead I asked "why not somewhere smaller?"

"Birmingham has the best accounting school which he close to here," he explained, took a short break and then continued "I don't want to move too far."

"Fair enough. Accounting... That sounds cool. Also a little boring, but I never saw the appeal of an office job, so what do I know." Finally the conversation started to flow a little better. We were also moving up in the queue, and I managed to put my hand on the bar to take the next spot.

"I'm good with numbers." Jake explained with a smile, which seemed a lot more natural than the ones he gave me previously.

"I think I'm equally as average with numbers and words. Never really excelled at either one in particular"

"I was okay at English, but I always just preferred numbers. They're a lot more predictable"

"True, but you can have more fun, and be more creative with words." I pointed out.

"My point exactly." Jake said and grinned. "I'm boring and unimaginative." He added, making me smile.

It was our turn to order, so I got us a pitcher of snakebite and 2 straws. I didn't ask for glasses, and when Jake pointed that out, I replied with a quick "I know" and winked at him, hoping that wouldn't scare him away. When we got back, Luke stood up, making space for me to sit next to Jake. I offered him a straw, took the other one myself, and we drank at the same time, which caused a loud "Ooooh" to come out of the guys voice boxes, which in turn, made Jake go the colour of a fresh, ripe tomato. I sent them a death stare, and they shut up.

The night carried on, with all of us getting more and more drunk. I was being responsible and not consuming too much alcohol, as I know I get very slutty and very forward when intoxicated, and that sort of behaviour would ruin my mission of getting Jake. I noticed that he was taking it slow as well, but he had loosened up a bit and I felt like he was enjoying my company, and I was really enjoying his. Once we felt at ease, he was funny and witty, and, truthfully to Luke's word, he was roasting the shit out of his friends.

Feeling a bit braver, Minnie and I joined in with the karaoke, singing a beautiful rendition of Frozen's "For the first time in forever". When we returned, Jake scooted along to make space for me, tapped the seat next to him. I gladly took it, revelling in the fact that he had become so much more confident.

"That was beautiful, Chrissie." he said theatrically, touching me on the shoulder. He hadn't initiated a touch before, so it kind of took me by surprise, but I smiled widely.

"Ahh, I could barely stop myself from choking up as I was singing." I played along, reaching for his hand on my shoulder and squeezing it tightly.

"I couldn't stop the tears from rolling down my face." He reciprocated the squeeze, and then pretended to wipe a tear from his eye. "No but seriously, you guys were crap." He started laughing.

"Oh fuck off, like you could have done a better job." I challenged and laughed with him.

"I'm actually an amazing singer."

"Prove it." I snorted.

"I don't sing in public."

"I live on campus, if you want to go somewhere more private." I said daringly, glaring into his eyes with a sultry look on my face. He held my gaze, visibly trying to figure out what to say, for no longer than 2 seconds, and then looked away. 'Too much, and too fast' I thought to myself. "Sorry, Jake," I said quickly "But you kind of led me into saying that." I joked and poked him in the side.

"I kind of did, didn't I?" He said and smiled at me again. We returned to our normal conversation with just subtle flirtatious undertones, which Jake was handling a lot better. It was nearing midnight, and the bar closes at 1am (seems early, but it is supposed to be for pre-drinks only), so I didn't have a lot of time to act.

As we were chatting, the bar photographer came and asked to take our picture for their social media, which we obviously all accepted graciously.

"Put your arm around me." I said to Jake. He hesitated for a spilt second, but then lifted his arm, as I snuggled into him. His hand was hovering by my waist, so without thinking I grabbed it to bring it down onto my skin, while I rested my other palm on his chest, and smiled for the camera.

When the photographer left, Jake attempted to lift his arm back up to let me go, but I didn't move, so he sighed and put his hand back down. This time he didn't need my prompt to touch my skin, and did it by himself. 'Victory!' I thought to myself.

We sat like this for the rest of the night, and suddenly I noticed that Jake was gently stroking my skin with the tips of his fingers. I felt that familiar squeeze in my navel and a pleasurable tingle in my pussy as, with each movement of his hand, I was becoming more and more wet. With my hand on his chest, I felt that his breathing had become faster, as I moved my hand down towards the hem of his trousers.

While I was still carelessly talking to everyone, not letting anything show, Jake stifled in his seat, as I noticed a small movement at his crotch. For a moment I thought he would remove his hand off of my body, but he continued to gently tease me. I didn't want him to get an erection right there and then, with everyone around us, so I rested my hand, on his hip, with my thumb gently tucked under his shirt, and millimetres from touching his bare skin, with no sudden movements.