This is a true story about me having sex with my best friend after many years of friendship. I changed her name in the story, just in case. This recently happened about a week ago, but I will give a bit of a back story as well. Jessica has been my best friend since 7th grade. At first I felt intimidated because she was very good looking. She was an early bloomer, having a really nice set of tits so early into puberty.
In middle school, she was head over heels for my guy best friend Andrew. Andrew, I won't lie, was one of the more good looking guys in my school. We always hung out together and he would tell me how he wanted to fuck Jessica. Andrew had a girlfriend though, and he wouldn't cheat on her for Jessica.
Being my best friend, Jessica would complain about Andrew and his girlfriend to me all the time- which was annoying after a while. This actually lasted until senior year of high school, but that's not important. Anyways, in our first semester of freshman year of high school, Jessica was very lonely I assume, and always depressed.
She would come over to my house all the time and cry and talk about her problems. She didn't have many friends besides me, which kind of shocked me because she was VERY attractive. Many of the other girls didn't like her because of her clothing. She dressed in mini skirts and low cut shirts and tank tops. Overall she looked pretty skanky, I won't lie. But that wasn't really a problem for the guys, who always used cat calls and such. She hated that, she was not a slut or anything.
She was very normal, but many didn't see her that way. One day when she was at my house, she was sitting on my brothers bed and I was on mine. Nobody was home except the two of us. We were facing eachother an just talking about something, I can't remember. I just remember for some reason, she stood up and grabbed my hands and way swaying them back and forth asking me to stand up. I got up and I remember we were laughing and I fell back and landed on my bed, me now laying down.
She suddenly leaned forward and placed her lips against mine. She hadn't fallen, she climbed on top of me. She had both her hands on my neck, and we were instantly making out very intimately. She bit my lips gently and licked the roof of my mouth. I can still vividly remember this scene, as it was my first kiss.
I placed my hands on her ass, slowly lifting her mini skirt (which didn't need to be lifted that far), and grabbed her small, but tight ass.
I squeezed harder than I should have, but she seemed ok with it. This was very intense for me, especially since neither of us had been with anyone before. I tried to take off her shirt, but she stopped me and immediately got off of me. She just walked out and we never talked about it again. She got a boyfriend soon after, but we still remained best friends. I got with my girlfriend in my junior year (I have a story about her as well).
We still hung out every day, never experiencing any awkwardness or regret from our little make out session. However, in our last semester of high school, I began noticing that she would flirt with me a bit. She would call me stud and sexy, ect. Sometimes she'd sit in my lap and even pretend that she was a stripper at my "future bachelor party" and give me a little lap dance. I never objected to this, since we hadn't shown any signs of affection or sexual interest for over 3 and a half years.
We graduated high school and nothing changed, since we both went to very close schools. I saw her a little less, but enough to remain close friends. One day, she sends me a text, which I will copy and paste.
This is the actual text conversation : Jessica: omg man, like we seriously need to get drunk together one of these days!
Me: lol, you're suddenly an alcoholic now? Jessica: no haha, but I have drunken before with my bf at parties! It's totes fun :) Me: well get a bottle and we'll see what happens then lol Jessica: really???
Yay! You have to see me drunk! I get really friendly :))) Me: lol friendly? Like how? Jessica: you'll have to wait and see ;) After this we changed the topic. After re reading that little mini conversation, I thought only dirty thoughts.
I was actually getting turned on by the idea of us drinking together alone, imagining why might happen. I didn't go crazy thinking about it, but I kept the idea of us possibly hooking up in the back of my mind. A few weeks passed and she sends me a text, this time a picture of her in a thong. Jessica: what do you think of these panties? Me: wow what the hell lol.
All of a sudden your asking me to check you out? Haha but yea, you look sexy as hell in those. Jessica: omg it doesn't even matter lol, it's not like anything would ever come of it anyways :P Me: true, but still- imagine if kellie saw them?
That would suck lol Jessica: well then just don't tell her lol Kellie and Jessica became best friends after i started dating kellie, which actually began to worry me now. Brianna kept sending me pictures of herself in very provocative clothing and asking when we would get drunk together, until we finally decided to schedule our little drinking date. I live at home right now and commute to my school. So as of right now, it's really hard to get any alone time from a house of 4. Eventually, the perfect day came where my parents where going to visit some old friends and my brother was going to go out drinking with friends.
I tagged along with my brother do he could bye me a bottle, since I'm still only 19.
He got me Jack Daniels, which I didn't object to. He dropped me back off at home, and I got in my car and headed off to pick up Jessica. She told me to park outside and wait until she was ready, when finally she walked out wearing another mini skirt that was barely covering anything. When she walked pass the front of my car, I could see that she was wearing the thong that she had sent me a pic of her wearing.
She also had on a red tube top that showed off her almost D cup sized tits. I seriously had never looked at her the way I was right then. I had a boner so intense, it was clearly visible through my pants. When she got into the car, I tried to hide it, but she quickly glanced at it. She didn't say a word, she didn't even look at me. She just gave a small smile, and looked down.
We got to my house and small talked for a bit. We eventual began talking about high school and how we hated it, ect. She finally brought up what we hadn't talked about for 4 years now. We talked about that make out session we had and how we were both surprised at how it was never awkward after.
I poured us both some drinks and we continued to talk on the couch. She started asking me about kellie and how she can't believe we are still together, and that she is really happy for us. That was a little weird, especially since she had asked me to lie to kellie about us drinking together, which I obviously agreed to.
She talked about her boyfriend and how she hated him now, and that she's only with him because she doesn't like being alone. She puts down her drink and lays her head on my shoulder, telling me how I'm the only guy that ever treated her right, and never tried to make a move We sensed it was getting a little too romantic, so we both quickly changed the subject Eventually, we both started to get buzzed, especially after we both decided to take shots.
After about 4 shots of jack and 2 drinks, it was safe to say that we were both pretty drunk. She's very active when drunk, she gets hyper and likes to move a lot. She got off the couch and was just slowly bobbing her head and dancing in a goofy way while holding her drink that still seemed extremely sexy because of her outfit.
I could see her ass bounce everytime she turned around and her tits seemed to almost be popping out of her top. Eventually, and it must have been the drunk me talking, I laughed and said how cute her small ass was.
She got jokingly mad and objected, saying that she had a great ass. She stood in front of me and bent over, grabbed my hand, and placed it on her left ass cheek. I heart froze. She looked at me and asked "You can't tell me that THAT is not a nice ass!" I pulled my hand away and laughed "ok, yea that ass is pretty damn hot" We both laughed, and she took a seat on my lap.
Her ass felt so soft on my leg, I really wanted to keep squeezing it, but I was afraid she might get bothered. She quickly got up and was suddenly all excited "oh my gosh! I totally made up a dance I'm gonna do at your bachelor party when you get married!" I laughed at her and said that she couldn't dance right now since she was drunk. "please, I am NOT that drunk" she said, laughing at herself because she knew that wasn't true.
She stopped laughing and turned away from me, slowly lowing her ass onto my groin. I couldn't move, I wanted to stop her but I felt like my body was totally against me at this point.
I knew if this continued, we might end up doing something we would both regret. She lifted her skirt so her small but firm ass was in clear view. She placed it on my boner, slowly moving it in a circular motion. She turned around and began taking off her top. "what are you doing?" I asked her calmly, as I was beginning to feel the drinks hitting me a lot harder now She whispered to me while now taking off her bra, "You can't have a stripper who doesn't show off her boobs." She now sat on my lap facing me, her legs wide open on each side of me.
Her tits kept rubbing up against my chest. I really wanted to fuck her, but I knew it was wrong. Too bad the liquor wasn't going to let either of us stop.
She continued grinding my dick and wrapped her arm around my neck while leaning back and putting her other arm behind her head.
My hands were to my sides, not touching her at all. She finally leaned forward and told me that it was ok to touch, but I was really nervous about cheating on my girlfriend. She put her chin on my shoulder, right next to my ear and whispered to me in a very sad and gentle voice- almost as if she was begging and about to cry, "You can touch me anyway you want to." I tried to move her back, but she was still wrapped around me tightly, still grinding her hot body against mine.
I was totally against it at this point, I KNEW that what we were doing was wrong and that I shouldn't have ever aloud this to happen, but my body was not letting me do what I wanted to. She began kissing my neck and gently nibbling my ear lobe.
She was still grinding me. I finally got overwhelmed and placed my hands on her ass, just like I did my freshman year of high school. I squeezed her ass and moved her thong over so I could have full access. I reached down and found her asshole, slowly prodding it with my middle finger. I don't know if she felt it or not, she was going crazy on my neck and ear. She kissed me like as if she hadn't had sex in years, which I know was not true.
I stuck my finger into her ass, slowly moving it in out repeatedly. Finally, she gave off a small moan, her head still buried in my neck. Her asshole was so tight and warm, I had never done any anal play with my girlfriend before.
This was incredible. She began to take off my shirt and I took my finger out of her ass so I could pull it off.
She threw the shirt to the side and started liking my chest and nipples, which again, I had not ever had done to me before. My dick began to throb and and couldn't stop myself from letting out a small grunt of pleasure.
She reached down and started to massage my cock over my jeans, which felt amazing. She came up and starts kissing me wildly, with intense amounts of tongue. I clearly remembered the taste of her lips- and I felt like I had died and went to heaven. Her lips were so sweet and juicy, if it weren't for the taste of the Jack Daniels, they would have been perfect. She got off me and got on her knees, unbuckling my belt and lowering my pants to my ankles.
She grabbed my cock and looked at for a few seconds, slowly jerking it up and down. She pulled my foreskin, revealing the head of my cock which was very swollen. She placed her glossy lips onto the head of my cock and I could feel her tongue wrap around it. She gently sucked and licked my head, then she reached down and grabbed my balls, slowly massaging them.
She grabbed the shaft of my cock and prepared to insert my entire cock down her throat. She took my entire cock in, following right behind her hand. She came back up slowly, her hand now following her lips. She jerked and sucked me off very slowly and intimately. She never sped up too much, she seemed to just want to enjoy my cock in her mouth.
Her eyes were closed the entire time, she never opened them once. I laid my head back and shut my eyes. She continued to slowly Move up and down cock, occasionally taking it out in order to lick the head or suck my balls. She finally stopped and stood up. I opened my eyes to see her facing away bent over, taking off her panties.
She lifted her left leg, reaching down to pick them up. She then tossed them aside and turned to face me. She grabbed my hand and placed it on her shaved pussy. I looked at her eyes which seemed to be glistening. She opened her mouth to say something, but nothing came out.
I stood up and began to kiss her, my hand still placed on her pussy. She wrapped her arms around my neck and started to play with my tongue. I stuck both my index and middle finger into her and began to finger her. Her mouth opened wide and she began to moan. I wasn't being slow and gentle like she had been with me, I fingered her fast and hard, letting all her wet fluid soak my fingers and fall onto the floor.
I took my middle finger out and began to rub her clit. Her legs began to shake and her moans got louder- and she got harder to kiss because her mouth wouldn't stop opening wide. She finally stopped kissing me and put her face into my neck. She tugged on my hair as I spend up and her leg lifted and wrapped around me.
I pulled her off and bent her over the couch in doggy style position. I immediately went down and started licking her pussy from behind her. She forced her face into the cushions as a searched her juicy wet pussy with my tongue, tasting her sweetness. I stuck my middle finger into her asshole as I ate her pussy.
It was so tight, I couldn't imagine fucking it with my hard cock. I came up and started to prod my cock into her asshole. She didn't object, so I assumed she had done it before with her boyfriend enough that it wasn't painful to her.
I slid in slowly, causing her to take in and hold her breath for a few seconds before releasing it all in one huge sigh of pleasure. I grabbed her cheeks with both hands, spreading her small ass open. I started off slowly, watching as she turned her head to lay on the cushion. She had her eyes closed and her teethe were showing.
She was gritting her teeth, which made me think it might be hurting her. "should I stop?" "no, keep going" I took her word, and began to quickly pick up pace.
She gave out a huge cry as I suddenly sped up, fucking her tight asshole harder and harder each second. Her cry turned into moans. She squeezed the couch cushions as I ass fucked her. I began to go so hard, she began letting out small farts which were accompanied by loud moans.
Normally I would probably be turned off by this, but being drunk, I was totally fucking wild about it. Her ass clapped against my thighs as I pressed deep into her with no signs of slowing down.I continued to fuck her ass intensely, pulling her close to me with every thrust.
I was pretty drunk, so I could not feel an orgasm coming on at this point. I must have fucked her ass hard for about 15 minutes before finally stopping to rest.
I pulled my cock out and sat next to her, sweat dripping off me onto the couch. She got up and faced away from me. She bent down over my cock and grabbed it with her hand, slowly slipping it back into her ass. She sat down on my cock, being completely inside of her ass. She then started rotating her body in a circular motion, just like she had done in the lap dance. I wrapped my arm around her and grabbed her firm tits. I squeezed them as she began to bounce her ass on my cock.
She leaned forward and grabbed the coffee table. She began to heavily bounce up and down on my cock. Seeing it slide in and out of her little asshole was so fucking hot. I placed both my hands on her ass and brought it up and down faster and harder.
She began to moan harder. Sweat started dripping down her back and down the crack of her ass and onto my cock. I was so horny. I wrapped my hands around her stomach and squeezed her tight to me. She placed her hands on mine as I quickly brought her body down heavily onto my cock.
Her moans turned into squeals, a mixture of pain and pleasure. I could feel the orgasm finally building up. I quickly got up and placed her back into doggy style. I slipped my cock back in immediately.
I grabbed both her arms and pulled them back with every thrust of my cock. I started to feel my cum about to burst out of my cock. "I'm going to cum." Before I could cum inside her ass, she pulled herself off me and got on her knees. She quickly grabbed my cock and stuck it deep down her throat. She sucked it ferociously. She wrapped her hands around my ass to help me fuck her throat.
I grabbed the back of her head and shoved my cock deep into her throat and began to spray cum into her welcoming mouth. Her eyes closed tightly and tears began to shed as she gagged and swallowed all of my load. I pulled out and she gasped for air, her hands placed on her chest.
She looked at me and smiled, laughing a bit. "Damn that felt good." I said. She giggled and nodded her head. "you're fucking crazy you know that? " "why?" I said with a huge smirk on my face. "that shit was hurting at some point and you just kept going harder!" We both laughed and I apologized for being too rough. We both got dressed and just relaxed for a few hours. We eventually passed out, waking up mostly sobered up.
My brother was already asleep in his room. I decided that I would take her home in the morning, just in case I was still drunk. I didn't want to drive at this point. The next morning I took her home and we didn't really say much. It wasn't awkward, just quiet.
Yesterday she texted me, telling me she had fun and that she broke up with her boyfriend. She also told me that she's transferring to a private school, one which is far greater than the one she attends now.
This school is hours away, so I probably won't be seeing a lot of her until semester breaks. I doubt we will have any more encounters such as this one, but if we do- you can expect another story from me in the future.
Thanks for reading!