So this is a story that happened last year, but I still look back at it fondly as a great night that helped develop my confidence in the dating world. I’m 24, 5’11 and have not had too many experiences with girls. However, for the last year and a half, I had been having a lot of close encounters with one of my really good friends Lupe, she was 22, Latina, and had a pair of C cups and an ass that was unlike any other (it was seriously distracting when she would walk past me).
We had gotten really close over the years and this year, in particular, we had been hanging out a lot and texting every week. We would go for drinks, hang out, and she would come over to my place for movie nights. Looking back at it now, I was very much being an idiot and not catching a lot of hints she was dropping. Both of us flirted with each other, and a lot of times we would get very comfortable with each other but we never crossed that line and always remained “Just really good friends”. It was nice having someone to always talk to and depend on and hang out but we never called it dates, and I honestly didn’t have the balls to ask her out at the time.
One Christmas break, however, we both left for about a month and didn’t see each other for a while. We kept in touch and texted and things got increasingly flirtier over texts, she would let me know how much she misses me and how she’s really excited to catch up with me and see me and I would do the same. I really liked this girl. Finally, Christmas break was over and we were both back and our friend group decided to hang out and have a night out in the town. We ended up in some dive bar that hosted karaoke nights and started drinking a lot and having a great time. A bunch of our friends were scattered throughout the bar but Lupe and me ended up talking and eventually, shots were had and we were both being quite handsy with each other and generally just having a good time.
Then pretty much all of our friend group goes out for a smoke and asks if we want to join, we politely turned them down and it was just us at the bar having a couple of shots. In our drunken states, she pulls me aside and asks to go somewhere more private and decides to make the first move and kiss me. The dive bar had a kinda backroom were the bathrooms were and we were both making out and getting quite into it and I guess kinda hoping that none of our friends would notice us all over each other. At that time I felt like a king, finally having this girl I was crushing on hard all over me and making the first move on me and clearly stating what she wanted.
After a couple of minutes of us making out she drags me into the washroom of this dive bar and we really get into it. I thought she wouldn’t object to me having my hands on her ass so I used this moment as free reign to explore and get to know this girl a lot better. My hands still on her ass we both stopped and made sure this was okay and what we wanted, and to this day it still remains one of my favorite moments when she just looked at me and said: “All I really want to do right now is to fuck you right now”. Needless to say, we got back into it and her shirt was off and I got to play with her amazing tits, hands caressing her, I decided I wanted to taste them and see what nipples felt like in my mouth.
I realized quickly that I didn’t want my first time with this crush of mine being in some gross dive bar’s bathroom so as much as I had to constrain myself, I stopped myself from escalating the situation and asked Lupe to put her shirt back on and to go back to my place. We left the bathroom, and all our friends were at the booth wondering what happened to both of us, at the time I didn’t really care what they thought and we both made some stupid excuse as to why we had to leave right now (we were obviously very horny and just wanted to fuck)… Not very slick… I know.
On the way back to my place we stopped, made out, my hands always grabbing her ass, and keeping the whole excitement of the situation we were both in alive. After a few blocks of walking, we got back into my apartment and then we both realized that we could do whatever we wanted and it was fair game. I started making out with her again and started taking off her shirt in my room, revealing her bra and not gonna lie, I honestly struggled taking it off.. It was an innocent funny moment both of us chuckled at. From then, I started to work my way down and I took off her pants, at this point I knew what I wanted. I told her to turn around and get on all fours as all I’ve been wanted to see is her incredible ass and it did not disappoint. I slowly took off her panties enjoying every minute of it and decided to lick her pussy and give her some attention. She was so wet, and I think us escalating quite quickly had her turned on and ready to go, after a while I took off my shirt and pants and we were finally both naked in front of each other. Its kind of a pseudo moment that is really hard to describe when you finally get to see someone you’ve been crushing on hard to be completely naked and vulnerable in front of you. But she was gorgeous, and in the moment, she was all I wanted.
I laid in the bed and she started to slowly ride me, giving me a great view of her tits while she bounced up and down and moaned in pleasure. My hands all over her body and then I told her to turn around. All I’ve been wanting to do is fuck this girl doggy style and get a great view of her ass. She turned around and I honestly could’ve cum right there, but I wanted to enjoy the night so I went at it and just kept going as best as I could. After a while, I knew what I wanted to happen next so I told her to get on her knees and give me head. The blowjob she gave me felt amazing, a little sloppy, but overall my drunk self was really enjoying the moment and the fact that I was lucky enough to essentially be able to fuck my friend whichever way I wanted. Some more highlights of the night, include: me telling Lupe to stand up against the wall and just railing her from behind, Lupe sitting on my face and me eating her out, me working up the courage to tell her I want to fuck her tits, and then when it was all said and done, she said probably one of the hottest things a woman can tell you while you’re having sex “you can cum anywhere you want”, I ended up cumming in her face, but that last feeling of realizing what had happened and crossing that line was a great feeling at the end because I realized had she not made the move I would’ve of still been wondering what if, and that feeling would’ve of sucked.
In the end, it didn’t work out between me and Lupe and we were ultimately not compatible, but one of the lessons she taught me was not to be afraid to go for it. Ever since that one night stand with her I’ve been more confident in the dating world and ask women out a lot more rather than just being afraid of what if, having that feeling on my mind and not knowing sucks and she honestly did help me build up my confidence. We don’t talk anymore and aren’t friends, but I remember this night very fondly and am extremely grateful for the experience. Sometimes, things don’t work out the way you want, but you are still grateful for the lessons learned.
Source: reddit.com/r/gonewildstories/comments/f0edq1/after_months_of_flirting_back_and_forth_i_finally
What happened to make you two not friends anymore?