My adventure to getting laid by my best friends crush [MF] [Cheating]

Hello, I have never written anything quite this R rated that wasn’t for a college course. Here’s a strange set of events that I sure enjoyed many moons ago. Feedback is always welcome and I hope you enjoy. It may not be the most exciting story written, but I feel zero need to embellish or lie. There is some build-up, but I will make a line when the sexual stuff starts.

So it is winter break after my second year of college. I decided to stay home for school, while a good portion of my friends went off to venture the world for college. My friends are coming home for Christmas Break and lots are drinks are consumed as is usual. This particular incident is about a girl named Alex.

My best friend (Greg) since kindergarten had a family friend a year younger than us named Alex. Their relationship was a “destined in the stars” type. Their grandparents knew each other, parents went to school together, and they’ve been friends since they were toddlers. Both always played on the lines of indecent flirtation back and forth, but neither ever succeeded in making the move. To my friends, we all knew she was off limits, and once my best friend Greg pulled his head out of his ass, he would finally get together with her and the world would rejoice. Unfortunately, young people are stupid and do stupid shit. Greg dated a girl for a few years, and then started slowly cheating on his girlfriend with Alex, but only on an emotional level. Both have told me they never became physical, but Greg strung Alex along stating he would be dumping his girlfriend soon so they could finally be together. Unlike Hollywood, Greg kept dating that girlfriend and discredited Alex when she finally came out after getting pissed off. This is where I come in.

I’ve known Alex almost as long as I’ve known Greg, just due to the fact she was always around. They were neighbors, so I’ve hung out with her, but we never got too close out of respect to Greg I guess. Alex comes to all our friends about what Greg was doing, and Greg’s girlfriend dismisses it all and Alex goes off the deep end. She stops eating, starts hurting herself, suicidal thoughts, the whole 17-year-old girl love breakdown. Her parents are worried, but she can’t say anything since her family is is still close with everyone. I become the shoulder to talk to and cry on. I cared for her in the sense that no one should collapse after a breakup, and I believe most people don’t like watching an acquaintance wither away. I talk her off the ledge and she tells me all of the details of their inter-workings and discretion, and this leads to a strange but relaxing relationship. For the next few years we would chat more and more, sparing no details about our escapades and boy/girl drama. I was her magnifying glass into the male mind, and she was my magnifying glass into the female mind. Out of a bad situation we both gained a really good friend who wouldn’t pass judgement for making bad decisions.

Back to college break. Alex comes home from her first semester of college. I have heard a bit about her drama, but pulled back a bit so she could enjoy her college experience without being pestered. From what I understood she had a boyfriend at her school and things were going well. I invited her over to my house to come catch up on life, and this is when it starts getting weird.

I still live at home with my parents and siblings. My brother and I have converted our garage into a full-out man cave, with couches, tables, fridge, TV, etc. where our parents would let us do as we wished. She comes over and we are watching TV, and I break out the Crown Royal to bump up the fun a little bit. We talk about failed hookups, strange interactions, all the bullshit you go through the first bit of college with making new friends and trying to find your place in the world.

**Description time:**
**Alex:** If it isn’t abundantly clear she’s in her first year of college so ~18/19. A hair above 5 feet tall, and while her eating disorder that formed from Greg is not still prevalent, she couldn’t have weighed more than 100 pounds. Large A Cup/ small B cup boobs, with nickel sized areolas. Nice and a perky handful, without much excess. She was a volleyball player, so she had the volleyball ass which was just magnificent, and she knew how to utilize it. Forest brown eyes large almost animated eyes, dirty blonde hair just past her tits, perfect teeth, and skin so clear that she makeup only hindered her natural beauty. Oblivious me was not so observant to her all fancied up to sit and drink Crown Royal in a garage. Her pussy was just an ever so small bald slit, with a clit the size of a pin head.

**Myself:** Second year of college, short but messy brown hair, green eyes, 5’7 and thin. I have had multiple people tell me my smile is the first thing they notice. Once I learned how to get rejected at the start of college I had decent success with girls. In relation to reddits standards, I have an obnoxiously small penis and am built like a Wii Remote. I keep myself completely shaven, because the rest of my body hints that I am a hairy motherfucker otherwise. Plus it’s hard enough to get a 19 year old to go down on you as it is, I liked upping my chances as best I could.
Anywho, I’m a little drunk, Alex is a little drunk and I make the smart move cut her off. No need for anyone to get crazy, and I didn’t care to hold her hair as she puked if she wasn’t used to hard alcohol. She had a much more sheltered childhood than many, which comes into play a little later. We are bullshitting about our lives and I’m still drinking, but have regressed to just crown in a solo cup versus crown and coke earlier in the night. Alex still wants to drink so proceeds to take the initiative to sit in my lap so she could sip on my drink while not having a whole drink to herself. The logic made sense at the time, and my dumb ass didn’t register her sitting in my lap while she is grinding her ass into me as much as possible “trying to get comfy” as she told me later. She starts telling me about how she thinks her boyfriend might be gay, due to certain events that had happened and that he thinks going down on a girl was “yucky”.
We met up at 6 that night, by 7:30 we were both feeling it and by 8:30 we were starving and sobering up a bit. We decided on the ever-delicious Taco Bell and head through the drive through to pick up our sobering snack. In the drive through Alex is going on about her boyfriend and his troubles and proceeds to show me full-blown naked photos she has sent him, asking me why he apparently never would respond to messages like that. It completely caught me off guard, and for all of the shit we had talked about over the years, I had never registered her as a sexual being in my eyes. She was pretty, well borderline gorgeous, but I was just a friend and saw her more sisterly than sexually.
Now, I understand how oblivious I am in hindsight, but even then, seeing her northern and southern hemispheres completely bare, I was like “Yeah that’s pretty weird, I would love getting that from my girlfriend”, totally missing every glaring alarm that she is trying to seduce me. She even gives me the phone, still in the drive through at a Taco Bell and tells me I should scroll through the whole album. Through our chats over the years, I knew she had little experience but had a kinky mind. She had a gauntlet of pictures of with her ass spread, her fucking herself with a cucumber, bent over the counter, spread wide doing pretzel formations and the whole assortment of dream sexts. Every fiber in my being wishes I would have gotten copies of those, it was pure pornstar level stuff. For whatever reason, she is asking me to look through as she just looks at me and grins ear to ear, and I still miss the signs.

So we make it back to the house, I start drinking again, she’s sobering up while her hormones are heating up. The talking gets much more heated about how she is unsatisfied and at one point an awkward silence happens as I’m looking at her as she is full-out straddling me on the couch. Breaking the silence, I told her I could stare into her soul through her gorgeous pair of eyes, as she is just gazing upon me, waiting for me to make some sort of move. She proceeds to respond with “You can stare wherever you want as long as you’re fucking me tonight”.

____________________________________________________________________________________The sirens went off like a breakout at Jurassic Park. It was without a doubt the hottest thing I had ever heard in my life, and I about crumbled at the moment the words escaped her lips. I about ripped her dress off, spilt the cup of alcohol and pinned her down on the couch. It was the most raw and carnal attack I have ever had. Grabbing, biting, pulling, grinding, the whole 9 yards.
We made out and attacked each other for a solid half hour, before I realized my whole family was still inside my house, and I was dry-fucking a completely naked girl splayed out on my couch. I was still fully-clothed at this point, so we get her dressed and try to make our hair not look like hell as we walk across the house to my bedroom and innocently as possible with a full tent in my pants. If my parents know of any of that night’s adventure, they sure have been cool enough to never bring it up.

After what seems like a half mile walk, but in reality was maybe 50 feet, we make it to my bedroom. Christmas was just a few days away, and the following day I had family coming in, so my queen bed was moved to another room for them, and I had a super sexy twin mattress without even a box spring sitting on the floor to work with for the night. Luckily for me, and Alex would’ve fucked me in the drive through if it were up to her, so we made it work.

I’ve got my best friend’s childhood sweetheart, who at least at one point he was in love with, she was in love with, and he tried cheating with her for YEARS while she refused to get physical with him, naked, wet and ready for me on the bed. The endorphin’s, emotions, and the years of build-up that I was oblivious to were all cumulating right now. I got out of a friendzone that I didn’t even try to get out of. Or better she got herself out of a friendzone against a person who was a complete idiot.

I tell her I am going to make her world tonight. I’ve got a bit of a thing for oral, receiving and giving, and I went to town. Her pussy was just a sweet nectar that had begged to be tasted for years, and she was responsive. I dragged out reaching her clit with ever-small licks across the top of her pelvis and the outside of her mound for almost thirty minutes. I couldn’t dive in full force and had to spread out the enjoyment. By the time I stuck my tongue into her, my whole face was sitting in a puddle. Hands were only used to spread so I could play with different angles for my tongue. Nothing entered her for what felt like an eternity while she was in the palm of my hand begging for more. When I finally wrapped my lips around her clit, she was on the verge of crying and bucked her hips into my face with pure reflex, surprisingly not busting open my nose with the amount of force. The warmth of my mouth, and the tease from everything had her cum instantly and hard. She told me I could do anything to her in the world and she would do anything I told her, and I wasn’t done with my mouth. I slid one finger into her pussy, which thank god for being young, as it was endlessly wet and just soaking the bed. For the first time in her life, someone else was stimulating her G Spot, and I went back to give some love to her clit with my lips and tongue. She was incredibly easy to work with, and her tiny clit was a fireball of reactions being so small and so neglected. 1 orgasm came, then 2, then 3 and more. With using my just my lips, one finger and tongue, she told me I had made her cum more than any other person in her life. I felt like I conquered the world. I could have died in that moment and been stoked. In my eyes everything was all downhill from there in life. I had a woman with tears in her eyes just melted into me. I needed nothing, she didn’t even have to touch me and it was already the greatest night of my life.

Being the ever-flexible volleyball player she was, I give her pussy a break and get to work on her ass. Later she told me this was brand new territory and started an addiction for her. I throw her legs behind her ears and start tongue-fucking her ass, with her cunt leaking down providing me extra lubrication into her. I do circles with my thumb around the edge, and as her ass relaxes I slowly enter a finger into her ass. Once I’m in, I move my thumb up to her clit and give it a massage for the first time as she comes again. After she settles from this orgasm, she finally snaps and pins me down. I try to fight her, as this night is about me, but she was adamant on giving my cock some love, and at a certain point I wasn’t going to bitch.

She was one who was fairly inexperienced sexually right up until college, but she boasted she knew how to handle a cock in her mouth. I had fucked and been sucked by women with years more of experiences and much older, but she knew what she was talking about. To this day, I have not gotten a blowjob with that much passion and veracity. Instantly she knew every spot that could make me squirm and played along every line of my body with her tongue. For her it was the cumulation that she was never going to fuck Greg and all of the raw emotions from that, plus the years of build-up to me that I was oblivious to. I had never had someone suck, bite and lick every inch of my body, and she was on it. My modest cock gave her just enough to hit her gag reflex, and she had her make and eyeliner all over her face. She played with my frenulum, gave my balls some love and even played with my ass a little to return the favor. I have to take a moment to thank Crown Royal, because without you I would have cum 2 seconds into the experience. Luckily my whiskey dick consists of myself getting hard, but having a difficult time coming. That, plus my head running a million miles a minute slowed down that process luckily. I did have to stop her a few times just to make sure I didn’t come, which was a real bitch because she was not letting up and begging for me to. I am a sucker 99/100 times the second a woman tells me to cum I lose all control and grant their wish. With the alcohol in my system, I didn’t want to have to gamble for round 2 and hope my small solider would be up for battle.

Alex blew me like a champ and it was one of the longest blowjobs I have ever experienced, and by far the best. Somehow, and we are a good couple hours into sexual activities, she has just soaked my legs sitting on my while blowing me, so it finally all comes to her end-goal.

This is where in the perfect world, I would have been a gentleman and gotten the condom. What really happened was Alex asked if I had a condom, and I said yeah, but it’s in my car. It was fucking cold outside, we had out rhythm going, and I already had proven to not be a great sense of judgement, along with the drinking and driving that night as well.
What we did instead was the “In for a penny, in for a pound”. We both had tasted every inch of each other’s bodies, and had been inside with our tongues. She was on birth control, we are passionate, she grabs my cock, slides up a little, winks at me and takes it all in in one fell swoop. I heard the angels playing trumpets, my long-gone dead dogs clapping, and God himself give me a thumbs up. Her perky ass nestled into my hips and our bodies were one. We switched off who was thrusting and both were drenched in sweat head to toe. She stayed on top for most of it because she wanted to be in control, and I loved watching her body react to mine. It wasn’t the first time I had sex without a condom, but there was a long drought prior, and she was experiencing it for the first time. I am 100% an advocate for safe sex, but that night we needed to be completely one entity. Her fluids mixed with mine, and we were one. She spun around, I got her face down ass up, legs over shoulders, behind her head. We tackled kama sutra with as much aggression as we could that night. Breaks happened with fondling, cuddling and some light oral to keep our hearts inside of our chest.

For a good 4 hours, all time was gone and it was just her and I. The only real break was to get water well after my family had gone to bed. The whiskey had taken a bad toll on my cock, and while the sensations were great, there was no chance at me coming that night. It was a blessing and a curse at the end of it all. We went for hours, but I believe she always felt bad that I never got off and she practically cried and pleaded for my cum at the end of the night. It is the only black mark on a perfect night.

The night ended covered in bite marks, backs clawed to all hell, hickies plastered across both our necks and collar bones for everyone to see at Christmas, and bruised pelvises for both of us. We were laying on top of each other lightly fondling back and forth when her phone went off, which I somehow missed was between my asscheeks and may have accidentally answered if I remember, since I don’t think Alex wanted to take the phone call from her mom. Her mom was wondering where she was, since she didn’t tell her where she was going and thought maybe she had left to go get breakfast early (it was 4:30 in the morning at this point). I drove her home, and we both agreed that we couldn’t tell anyone in our friends group about this.

We hooked up one more time, Christmas night, but it wasn’t the same as this. After that she went back to school.

**TL;DR: Hooked up with my best friends childhood sweetheart after years of teasing on her end. **

Source: reddit.com/r/gonewildstories/comments/6i2ilf/my_adventure_to_getting_laid_by_my_best_friends