Losing my virginity to my best friend’s girlfriend

So I will start with a little backstory at the time I was 19 (yes I know pretty lame for a guy to lose his virginity) but I was a late bloomer. I was always extremely shy in school and would really only talk to girls if we were put into group projects. Being the short chubby nerdy band geek I convinced myself no girls would ever be interested in me. Growth spurt hit and ultimately ended high school lettering 3 sports all 4 years.

At this time I did have a girlfriend that I was on and off with. One day in the summer after we graduated my older brother invited a few of his coworkers out with us to a kick back we were having at our house. One of these coworkers was a really short Latina girl with long black hair, really cute smile that made it hard not to notice her big full lips. There’s something about a girl with glasses. Despite her always being moderately dressed there was no denying that she must of had some really large breasts that complimented the rest of her body. We drank and talked like normal. But I could sense some chemistry with her that would lead to casually flirting. As a group we all pretty much had no filter and throw out random sexual jokes or conversations.

She began to hang out with all of us more frequently. Shortly after my best friend began to work with her and my brother. So ultimately she would become one of the group. Some nights we’d go out partying she’d spend the night at our house. Before long my best friend and her ended up hanging out more but would never make it official and would continue to joke with everyone. But we would always end up noticing each other staring at each other even without making Sexually charged comments. I even caught her staring at my crotch a few times.

Her and my best friend would always stay over at my house on weekends where the nights would almost always end in my best friend and brothers glued to the tv playing video games. I would usually be in the living room watching tv with my parents. I found that we began get close spending all that time together once my parents would go to sleep we’d sit there confiding in each other about everything. One night I was surprised when she ended up telling me that if it wasn’t for my gf that she would’ve pursued me instead of my friend. I didn’t believe her but joked about it. Our conversations would become more interesting and she would ask me personal questions about my girlfriend like “have we had sex or how many times has she sucked my dick?” I would reply completely honest and say “no we have not actually had sex because for one reason or another we’d have to stop” as I told her that she would smirk and be like “what I don’t believe you.” She would look down at my crotch and said “from what I’ve noticed, she’d be crazy to not want to be all over that”

I started to get hard and made my bulge way more noticeable. So I tried to shift and cover my self with a blanket. She kept smirking. Some time passed with us watching tv while everyone was still in the room playing games with no break insight. She then went to go check in and kiss my best friend. She came back into the living room and turned off the lights and laid on the couch with me and got under the blanket with me. We had our feet in the center but she would casually stare at me and slowly start moving her feet onto mine. Casually making comments saying she does not believe I’m still a virgin. And I told her I swear I was.

She continued to reach closer and closer up my shorts while my dick continued to get harder. As she finally felt my dick with her foot she said “your telling me your gf has never had this? Don’t lie I know she’s tasted it” and at that moment my dick pumped and twitched. She then sat closer and reached for my dick and asked if she could finally see what has been running thru her mind She reached into my shorts and grabbed my dick and pulled it out

She slowly stroked it up and down with one of the biggest smiles I’ve ever seen on her. Intensity filled her eyes and she kept just stroking my dick. Casually picking under the blanket and finally said your bigger then my bf. And she whispered she wanted to taste it. And at that moment I realized I’m all in. And finally going to lose my virginity.

So many thoughts were rushing through my head I began to over think and she was able to sense the nervousness and took charge. We moved to the floor in front of the couch. Laid next to each other under the blanket on the floor. We began to kiss while she was still rubbing my dick. I began by squeezing her huge breasts over her shirt and that just shot so much blood to even harder dick. I pulled up her shirt and was in awww they were way better then I could’ve ever imagined. She then spits on her hand and continues stroking my dick.

Our breaths continue to deepen as I then reach down and slid my hand into her shorts. I peeked down and looked back up at her and said in such a turned on tone “wow thong?!” As she guides my hand to her pussy causing her hips to jerk towards me. We continued to rub on each other for a little because my lack of experience didn’t help me in knowing how exactly to progress further. I ask her if she’d go down on me. But she panted and said “I would but if you are really a virgin like you say you are. You mite cum to fast”

She said “let’s just do it. I want to feel you in me. “ so I got on top and awkwardly started lining up our hips while she pulled one leg out of the shorts. And as I started moving my dick towards her pussy she took charge and pulled her thong to the side and grabbed my shaft and rubbed her clit up and down. And I just remember how wet and warm her lips felt against my tip of dick. She told me to use some saliva and wet the tip of my dick. I then began to slide into her pussy and she told me to go slow cuz of how big I am. But the lack of experience led me to just thrust my entire dick into her and all the while she gasped and grabbed me tight. And and I continued to slide in the tip of my dick slammed into her wall causing her to let out a moan and I had to quickly cover her mouth to not make any loud noises to not get caught by my best friend or family.

I continued to thrust into her slowly then faster following her lead. She continued to get wetter and wetter with every stroke. Her panting and whispered moans continued to just get my dick harder and harder. It all felt like slow motion. We continued for what felt like for ever but I’ve heard that most people don’t last too long even tho it feels like it

I start pounding my dick in and out of her pussy feeling her pelvic bone thump against my as our hips met. I began to feel my balls fill and at that moment I realized to my self “wait I didn’t put a condom on…..and we never talked about where I would cum” but at that moment I know she felt me holding back and said “just cum in me. I want your cum in me. “

With a long deep thrust my dick pulsated exploded so much cum into her. She pulled me in tighter to make sure I shot every last drop into her. She held me in her while my dick continued to pulse and squirt more. I then rolled off her and with a huge smile I tried to slow down my breathing. She pulled her shorts back on and then suddenly went down and licked and sucked both our juices off my dick.

As I was Laying there in complete bliss she looks over at me and looks at her phone and asked me “if I’m completely sure I’ve never done that before” and I said “yes I promise. Why?” She said “because you were actually really good” then I told her that “I’m sorry I didn’t last that long” she said “shut the fuck up, you gave it to me for almost 20 mins” and then said that’s way longer then my best friend.

Me and her are still as close as we can be while still respecting our own relationships. It’s been 15 years and I still think about that night from time to time.

Side note. Through your the multiple family gatherings and events she’s been invited to. I still catch my self subtlety undressing her with my eyes. And there has been multiple times that we lock eyes and can feel the intense connection we share and even sometime give each other looks as if to acknowledge that we would soo revisit that night again if the opportunity to arise