Friends to Romantic Benefits

We were friends since the beginning of high school and would tell each other EVERYTHING. Constantly gave each other relationship advice and support. We scheduled all our classes and lunch for the same period, went on food dates and would spend HOURS at each others houses just talking and laughing. I loved being around her and wanted to spend as much time with her as possible. There was a sense of comfort being around each other, we changed our clothes in front of each other (our underwear not naked) without giving it a second thought. Although I must admit, I would secretly peek over and be mesmerized by her perfect body in her hot lingerie. Oof. I still vividly remember her in a pair of scantly red laced lingerie that barley covered half her breasts and how the area below her belly button seemed so smooth and enticing.

Since I was a douche bag, I made make fun comments like "hey its really hot in here right, you should take your bra off! :)" or if I knew she was showering I would knock on the door asking her to unlock it so that I could shower with her, because water conservation is good for the environment. She knew I was goofing around (kinda true), we made playfully sexual jokes with each other all the time. There was just a strong and comfortable bond between us as close friends who wanted nothing but the best for each other.

Our relationship in high school was pretty tame though, there was some tension between us but we never really did anything intimate except hold hands and sometimes cuddle. There was a lot of playful complementing and jokingly flirting "...Wait. What did you say? I just got lost in your eyes" etc lol. Despite all of this, we both agreed that we were just having harmless fun and it wasn't really serious. I did not want a relationship with anyone and neither did she. Also, I considered her so much more than just another girl I could hook up with and never seriously considered being in a relationship with her. We were just both happy to be each others ride or die.

Both of us were very open about who we hooked up with/had feelings for etc. Never felt jealous, in fact I was very very happy for her every time she "scored" someone she found hot. She gave me advice about girls and I believe that talking to her really boosted my confidence early on approaching girls. People thought we liked each other, but that was just not true. Around this time, I was starting to get serious with this insane girl and she freaking FLIPPED OUT once she found out how close we really were, despite me ensuring her that it was nothing like that and that we were just good friends. She ultimately gave me an ultimatum. Easiest decision of my life. NEXT. I cared more about my friend than anyone and felt lucky that i could always be there for her...(obviously all that playful flirting/cuddling would've truly stopped w her had I dated the psyco girl).

We were lucky to get accepted to the same state college and got dorms on the same floor 3 doors down (sucks that co-ed dorms arent a thing). During college, we would often sleep together in the same dorm bed while watching Netflix or w.e but never did anything more than cuddling and me caressing her hair while her head lay on my chest. I love it when girls rest their head on my chest and I play with their hair. Some urges to kiss her or suck on her neck did come to my mind, but that was only because I was, and still am, a freaking horny dude.

We gave each other frequent non-sexual massages too. I was on the soccer team at school so I was always asking for one. The way she worked her hands and glided over my back was the best pain and stress reliever in the world. Pure euphoria. I loved, and still love, giving massages to girls there's just something about being able to relieve their stress that really entices me. I have probably watched every single massage instruction video on YouTube just so I could get better, and she was usually my unfortunate victim who I would practice on. She would lay in her bed facing down. Shirtless. Every time I looked at her oiled-up and glistering gold colored back I became lost for a few seconds and thought about how sexy her back is. Shortly afterwards those feelings would go away. The massages weren't sexual or anything, although I would often joke about letting me go lower to massage her butt or she would always make me look away when she took off her bra and I would playfully try to scare her to hopefully startle her to sit up so I could see her boobs lol. I would sometimes see her boobs pressed against my bed and seeing them pressed like that on the bed and knowing she wasn't wearing anything and it was such a turn on. Regardless, all of this was just normal for us, just messing around, being stupid college kids and having harmless fun. It never felt like a romantic or sexual thing it was so normalized and we generally didn't think much about it.

I guess our first kiss was fairly typical. We both got hammered at a frat party and when I dropped her off to her dorm, idk what happened, but as I was about to leave her dorm. We were just standing in the doorway of her room and I could feel myself reluctant to leave for some reason. We were standing in the dark, with faint white light coming in from the hall and made this deep and odd eye contact. None of us said it but I know we were thinking the same thing "fuck it"...and then we leaned forward, closed our eyes and made out for a good 3 minutes. I finally tasted her lips, it was amazing, DAMN this is what I was missing out on? It felt so blissful and I was just overwhelmed with emotions but at the same time I was terrified about what this would mean for our friendship or that I would regret it. I pulled away and didn't go further, especially since we were drunk. From there I helped her get into her PJs, tucked her in bed, got her some Gatorade and quickly left.

I never really made any moves in the past because I dont think I had feelings for her like that. Also I did not want to lose my FREAKING ride or die hommie, like seriously she could call me at 4 AM and if she needs help, I'd drop everything to help her. No matter what and vice-versa. We watched out for each other during parties but also gave each other space to talk to other people. I made sure she was staying safe and not being taken advantage of (plus she was an BOMB wing woman, we came up with this whole scheme to approach girls and practically had it down to an art form lolol). I just felt responsible for her well being. She would always text me the name/address of the guy every time she went to hookup w someone for safety.

The morning after the make out I was so nervous. But then I received a text that said "That was fun lol. Only took 5 years" to which I responded "Yeah lol"..."walk over to my suite, my roomates arent here ;))". She came over, still in her cozy pink PJs in which she looked so damn adorable like a bear...they were kinda tight and really brought out her whole sexy voluptuous figure. We gave each other a hug sat on the bed and talked about what next?

We reasoned that we aren't necessarily romantically boyfriend-girlfriend type attracted to each other but maybe sexually and physically yeah. She suggested if we should try out a FWB type scenario and to go from there. , I exclaimed that I wasn't sure but then I looked down and saw the outline of her breasts (typical me lol) and looked up and stared into her hazel colored eyes with a soft gaze. I slowly leaned in for a slow but passionate kiss, one hand gently grabbing on the back of her neck to pull her lips even closer to me. We quickly increased the intensity and pressure. I wanted needed her so fucking badly. I made out with her as if she was the last person in the world...it was... it was so mindblowing and insanely passionate. I pushed her backwards in the bed, grabbed both her hands and pinned them down above her head and started to suck and light bite the side of her neck; while my other hand unbuttoned her goddang cute af PJs.

I then unhooked her bra with my hand hand that was still free. I couldn't wait to finally see her boobs that I have secretly admired. I finally got to see her perky and most perfect breasts I've seen. I laid on top of her, my dick was rock hard and it was pushing down on her panties. I could feel her pussy lips engulf my penis through my boxers. I pushed my self deeper into her, I felt as if I was going to cum just by me pressing against her. We were just going insane with each other, our lips were just kissing so frequently. I hugged her with one hand on her bubblelicious ass and spun so that she would be on top of me. Her breasts were dangling right in front of me and I licked lightly on her nipple. The licked it again, and again. She closed her eyes and was like "suck it already. PLEASE". It felt nice hearing my homegirl, the person I care so much about, wanting me to please her so badly. I wanted to give her the most intense orgasms she has ever had.

As I sucked on her brown perked up nipples she told me to bite them hard. Feeling her nipples on my tongue was out of this world but her pussy would taste so much better. I went back on top of her kissed below her breast and slowly made my way towards her flanks and stomach taking my time to kiss each and every part of it. Once I arrived came close to her perfect pussy I stopped, Ignored it completely and kissed her inner thighs, working my way up to her pussy. She was soaked. I had never seen such a wet pussy before. I was still kissing her sides but then she just grabbed my hair and pulled me up to her pussy. "Please lick me I cant take this. I need you". I gave in because I couldn't wait either. I was excited to taste her vagina. Once I put my mouth on it I couldn't control my self and began eating her out as if I had never seen any food before...I felt her pussy clench as she moaned so loud in satisfaction. I felt proud, shocked and happy because I never had a girl orgasm just by oral alone.

I stuck my fingers inside of her, giving her another orgasm but she then said "fuck me right now, take it off". I went to grab a condom from the drawer next to the bed but she held my hand and stopped me. "Please no condom, just get inside me already". I was a little hesitant but she said just pull out. I couldn't wait either and placed my THROBBING dick inside her. (I later learned that I was the first person to enter her bareback) I was hugging her and pushing myself deeper and deeper inside her. We had been making out this whole time. I LOVE making out while having sex but had never kissed someone so much in a session. It was just something else, as if our lips never left each other the whole session. I would make eye contact with her and fucked her so fast and deep with all my energy. The workout felt more intense than my soccer practices lol. I told her I was about to cum and was about to take it out, but she just said "cum inside me please. Ill buy plan B". I really did not want to because I knew she was not on BC, but it was already too late and I exploded inside of her and felt a rush of endorphins flow throughout my body. I made out with her with so much force.

It was the most passionate and intense sex I've ever had. It was amazing and as if all the tension that had been building up for so long was finally released. It just felt so different compared to the other girls ive been with, I can't describe it. I held her in my arms afterwards, laying next to each other and were still making out. (My jaw really started hurt a lot after that session lol. I would get used to it tho :))

After the first week, it was obvious that nothing really changed b/w our friendship except amazing sex and make out sessions. This was a really good time period for me because a lot of things were going my way regarding school, career, sports and best of all being able to fuck my best friend. If I was ever randomly in the mood she would be the first person I would text. It was just so chill... We'd cook for each other more often and get each other food.

I would be playing video games and she'd randomly walk in my suite. She'd realize that I was too invested in playing and to get my attention would take her clothes off to show me that she was wearing my favorite or new lingerie. Which she knew would drive me crazy and make her irresistible. Freaking smooth and I fell for it every dang time. But whenever we were alone she was always naked or in her bra walking around the suite because I told her I liked it when she did that. (and I'd do the same whenever she asked me to lol) It just became a very natural thing and was awesome.

Both of us were still hooking up with other people at this time, but we didn't really care about that at all, in fact we were very open and told each other everything about our sexual prospects. She was still an amazing wing woman whenever I told her about finding a friend of hers or someone at the parties hot. I even asked her for a threesome once!! Which she denied after calling me an idiot. Bummer >:(.

I was still an amazing wingman if she needed me but made sure to give her some space as well at parties. I would sometimes even scope guys out for her that I knew she would like or were her type. We were just happy with our arrangement with no jealousy at all. She once knocked on my door in the middle of the night to ask if I had any condoms because the guy she had over didn't. I made some stupid joke that I only had Magnum XXL's (not a total lie) and that he wouldn't fit in it so she should come to me. She told me to shut the fuck up and get her one haha. And I was cool and chill with that, never really felt any type of jealousy or sadness as long as she stayed safe and happy. I made sure that she wasn't having any of those feelings either by frequently talking about us.

I started getting really serious with another amazing girl the last year of college so stopped the whole fwb and fucking around thing. We also drastically reduced the amount of times we spoke towards the end because of school but were still good friends. Then we graduated and started working in very demanding fields which reduced the talking even more.

I actually broke up with the new girl a few months ago for reasons unrelated to my best friend. Writing all of this out is actually making me realize how amazing she was and that I really fucking miss her. I've been thinking if I'm open to something more serious with her now. maybe I think I am. I should probably call her soon and hit her up to talk.