My first girlfriend (and eventually her friends): Part 1 [MF, oral, mast)

Edit: Part 2

Warning: This might get kind of long. This is the first in a series of true stories about how in my senior year of high school I went from an introverted virgin to fucking my innocent girlfriend, three of her friends and her coworker. Yes, I know, I was a piece of shit but my ego and my other head were definitely in control during this exciting time. This can get kind of long so this first part will set things up and include the first blowjob she ever gave me. If there’s interest, Part 2 will detail one of the best fucks we ever had. Parts 3, 4, 5, and 6 will be about fucking her best friend, a petite little Latina with a super-tight body, finding out the teammate on her high school soccer team is a kinky little slut, learning the truth about her foul-mouthed friend with the enormous breasts, and finally, being seduced by her beautiful mixed-race coworker.

Let me set the stage. This was around the very early nineties. I was a semi-jock in high school, playing baseball but not much else. I was on the taller side, 6’4”, and athletic but definitely more skinny than muscular. Most would probably say I had a swimmer’s body and that wouldn’t be far off considering I was in the pool all the time at home. All in all, I would say I was pretty average looking. More than anything, I was socially awkward and only had a couple friends. You would think that being on the baseball team that I would at least be in with that crowd. But that was far from the case. I was extremely introverted, and looking back on it, I’m sure I had/have Asperger’s. It wasn’t until my senior year that things got very interesting. School had just started and it was a warm fall day when I saw her walking across the courtyard. I couldn’t keep my eyes off her. She had beautiful curly reddish/blonde hair that went half-way down her back, green eyes, creamy white skin, and she was somewhat petite, but she had a wonderfully curvy ass, shown off by a cute little pair of jean shorts. I would later find out she was 5’3” and about 125 lbs. One of my only friends couldn’t help but notice that something had severely distracted me. I was usually easily transfixed on things but this was different. He looked over and saw what had caught my eye. “Oh, you know her?,” he asked. “No, but wow, she’s gorgeous,” was all I could mutter. He replied that he knew her from Spanish class and that her name was Rebecca. That’s all it took. She was all I could think about. I’m going to speed through the next bit here, slowing down for some of juicy bits. At a school basketball game the following week, my friend makes the introduction and we nervously chat. The nerves quickly dissipated between the two of us and shortly after, we were dating. From this point, things progressed fairly slowly. She was very naïve and completely inexperienced and although I had never done anything with a girl, my only knowledge about sex was from my Dad’s porn stash. All she knew was what her friends told her. This will actually play a big role in future dealings with her friends. It took several weeks to work up to our first kiss, which was a sloppy, tongue-bitten, breath taking (literally) exchange between two young teenagers figuring things for the first time. Things started progressing from there and soon our hands were wandering every chance they got and our kissing improved ten-fold. Soon, we were looking for opportunities to do some more private exploring, which proved very challenging considering at least one of our parents were always home.

The first opportunity turned out to be one of the more memorable times we had together. Her parents were fairly strict and at times, it seemed they would go out of their way just to make sure we were never alone together. I guess they finally started to trust me and one night, it finally happened. Her family was going to a party at their neighbor’s house and Rebecca and I had convinced them to let us stay home, watching movies and eating popcorn. Reluctance was in the air but her parents were probably figuring they were just next door and knew they could come home at any minute. I’m sure they thought we would be too scared to do anything foolish with them so close. Boy, how they were wrong. We waited a few minutes after hearing them leave before completely jumping each other. Our tongues immediately found each other’s mouths, jumping right in to their familiar dance of swirling and exploring. My hands immediately went to my favorite part, her ass. Squeezing and kneading her through her shorts, pulling her closer to me as our bodies pressed together, I could feel my heart was racing. Blood was certainly flowing south. I increased my grasp of her ass, firmly grabbing both cheeks as I pulled her on top of me. Straddling my crotch, she immediately started grinding down on me, fully aware of the effect it was having. I let out little moans in her mouth and she did the same as our pelvises mashed into each other. My hands continued to wander from her ass, up her back, under her shirt, and back down to her ass while she grasped the back of my head, pulling our mouths tighter.

My young inexperienced cock was soon about to explode from all the rubbing, although we were still fully clothed. I decided to slow things down a bit, wanting to save my load for something other than my underwear. I slowly pulled away and saw the confused look on her face. Without hesitating, I started lifting her shirt. She got the hint and removed it the rest of the way for me. I now had this beautiful young girl in only her little black bra, straddling me, giving me a shy smile that still makes my heart melt to this day when I remember it. She placed her hands on my shoulders, pressing her small breasts together and leaned them forward, giving me a perfect view of her little cleavage. She leaned in and whispered in my ear that if I’d like to see more, I’d have to remove her bra. She stayed close, our bodies pressed together as I could tell she was quite nervous. I whispered back that she’d make my fantasy come true if she let me do that. With that, she slowly sat back up, giving me access to her bra. I reached around the back and she giggled. “No, silly,” she laughed. “It’s in the front.” Of course, I was confused as fuck. What the hell did I know? She pointed to the clasp between the cups and smiled. I reached for it and fumbled with it before finally figuring it out and soon enough, her bra was loose. I reached for both straps and pull them off her shoulders and slide them down her arms, revealing the most beautiful, perky breasts. I sat there in awe for a moment, taking in this beautiful sight. Her areolas were a perfect shade of pink and about the size of a quarter. Her nipples were slightly darker and hardening by the second, constricting right in front of my eyes. I watched as goose bumps formed on her areolas, all of this completely foreign to me yet so arousing. My cock started twitching and she giggled, now fully aware of the effect this was having on me, especially given I was speechless. I finally came to my senses and without taking my eyes off them, my hands reached for them and I took one in each hand. Not knowing what the fuck I was doing, I just held onto them, feeling their softness with my fingers, and enjoying her hard nipples pressed into my palms. Like I said before, she was fairly small chested, a B cup as it turns out, but god damn were they beautiful and perky. I continued holding them as she leaned in for more kissing. I was soon kneading them and playing with them, seeing what elected a response. She had fairly sensitive nipples and didn’t exactly enjoying direct stimulation but she loved when my whole hand grasped and rubbed them. At one point, I removed one hand and licked it, coating it in my saliva before returning it to her breast, using the new lubrication to continue rubbing. She seemed to really like that so I did the same with the other one. We continued making out while I fondled her, both of us taking in this new sensation. Not long, she stopped and asked if I’d like to kiss them. I was giddy with excitement as this prospect and dove right in. I returned my hands to both ass cheeks as I lowered my mouth to her left breast. Sucking it into my mouth, I started swirling my tongue round and round her nipple, stopping occasionally to switch to the other breast. I varied my routine between long swirls with a soft, flat tongue, and flicking her nipple with a harder tongue, gauging her reactions. She seemed to respond positively to both, given her heaver breathing and increased grinding.

I was very involved in my new found toys when my cock decided it seriously wanted some kind of release. I had to stop what I was doing for a moment or else I was definitely going to have that mess in shorts that I alluded to earlier. I explained the situation to her and that only made her want to grind me harder. I firmly grasped her hips and told her to stop. I didn’t want to come this way. She had a look of confusion on her face but she quickly understood what I was getting at. I could tell that she instantly got nervous and I quickly jumped to quell her reaction. I comforted her and let her know that we didn’t need to go any further if she didn’t want to and that I’d be happy no matter what. She took a minute to contemplate the matter at hand and asked what I had in mind. I could feel a lump in my throat and my heart pounding as I didn’t think she’d put the ball in my court. I quickly gathered the courage and managed to ask her if she’d like to see my penis. Holy shit, was all I could think. I said it, now what? It seemed like an eternity but she finally responded. “If you think it’s okay, but I’m very nervous.” I took her hand and reassured her that everything would be okay. She slid off to the side of me and watched as I unzipped and unbuttoned my shorts. I slid my fingers under the waistband of my shorts and underwear, lifted my hips and slid both down to my ankles, my cock springing free. I looked over to Rebecca and say the astonishment on her face. This was her first time seeing a penis, ever. Now, she was speechless. I leaned forward for a second and pulled one leg out of my clothes, leaving the other one just in case we get any unexpected visitors, then leaned back again. I looked back to Rebecca’s and asked her what she was thinking. She said she didn’t know what to think but was surprised by its size. I don’t consider myself large, but I’ve only got porn to compare myself to at this time so I just figured I was average. She’s certainly given me an ego boost but I also know she’s got nothing to compare it to. She continues to stare and then asks me to touch myself. She says that she wants to touch it but she has no idea what to do so she wants to watch me for a minute. I happily oblige and lightly stroke my shaft, coming up to head occasionally to get some precum on my hand. She asks about it and at this point in my life, I had no idea why I leaked precum but I knew it made one hell of a lubricant. Little did I know I was on the right track. I asked if she’d like to get a closer look and suggested she get down on her knees between my legs. She said okay and got in position while I still held my rock hard cock. As I slouched down on the sofa and slip hips down, I continued stroking it, intermittently running my fingers over the head and sometimes switching things up and caressing my balls. I watched her eyes as she continued to watch in amazement, the sight making me perhaps the hardest I’ve ever been. After what seemed like an eternity but was probably only a minute, I removed my hand and asked if she’d like to touch it. She giggled with nervousness but didn’t hesitate to answer yes. With my hard cock twitching as it lay flat on my body, she placed her palm flat on my shaft. She let out a little moan from her closed mouth. She started to move her hand up the shaft toward the head, still with her hand just open. I watched as she processed what was happening and I could see the inquisitive look in her eyes. Her hand made its way to my tip and then slowly wrapped around it, lifting my hardness from my body. With my cock now standing straight up, the tip firmly in her hand, I watch her examine every inch, checking all around the shaft then gazing down at my balls. She slowly stops and looks me in the eyes, that gorgeous smile again adorning her beautiful face and says she can’t believe how something so hard can feel so soft and hot. Looking at her, on her knees between my legs as she says this, I nearly bust a nut watching her touch it and examining it, with her beautiful bare breasts in the background. I keep watching as she continues her examination. She leaves no part of my cock untouched and even gently caresses my balls. She knows enough to not be rough with them. I then giggle as I see her wrap both hands around my cock, checking to see if she can fully close her hands around it. Seeing her petite little hands both wrapped around my cock nearly sends me over the edge again.

I’m getting anxious now, sensing that our time might be cut short. I quickly get the nerve to ask if she’d like to kiss it, the nerves much more in check this time probably because I’ve never wanted to bust a nut so bad in my life. Now this is completely foreign to her. She’s heard from her friends that this what girls do for their boyfriends but she’s never gotten much details. I bust out as much reassurance as I can give and let her know that we can get through this together and teach other what we like. She agrees and asks how she should start. I suggest she run her tongue along my shaft, starting from the bottom and move towards the tops. She leans down and her warm wet tongue makes contact with my shaft and electricity shoots through my body. She starts kissing it, like we do when we make out, swirling her tongue around and around as she inches towards the tip. She moves her hands down to the bottom of my shaft and grips tightly as her tongues moves higher and higher. I suggest she spit in her hand and use it to stroke the bottom half of my shaft. She does as I suggest and then goes right back to licking me. She gets right to bottom of my head and stops moving any higher, sensing this is doing something to me. I sense it too and I can tell this is going to be it for me. The muscles in my legs start to tighten and my hips rise slightly from the sofa. Rebecca senses something is about to happen but has no idea what’s going. Naively, she moves her swirling tongue over the head of my trembling cock and I quickly manage to tell her that I’m about to cum. Not knowing what to do, she lifts her mouth from my cock. I tell her to stroke my cock with her hand, like I was doing earlier. As she does this, in no time at all, I start spurting thick ropes of cum up in the air, some if coming straight back down on to her hand and the rest landing in my pubic hair. Rebecca has a look of absolute astonishment on her face as she continues to stroke my cock with her cum covered hand. She’s speechless, I’m speechless. My head is spinning. Having nothing to compare it to, it was the best damn blowjob I’ve ever had. I would have never guessed it would only get better from there.

We do end up talking about it later but our immediate concern is getting cleaned up before anyone comes home. She goes to the bathroom and washes off and put her clothes back on, returning with paper towels for me to get cleaned up. Everything worked out and nobody suspected anything but things changed dramatically for the two of us. From this point on, we were sex crazed teenagers, looking for every opportunity to get our clothes off. There’s a ton of stories about my first time going down on her, her first time coming, our first time fucking, etc. But, if there’s interest, the next story will be about one of our most memorable fucks.

Source: reddit.com/r/gonewildstories/comments/384aew/my_first_girlfriend_and_eventually_her_friends