It’s the story of my first anal intercourse expertise that occurred once I was 19, about 5-6 years in the past. It occurred with the primary woman I’d truly take into account a “girlfriend”, although we had been solely collectively about 6 months. First, somewhat about me. I’m a taller man, round 6’1. Pretty skinny construct, although I work out I’m positively not ripped, simply what I like to contemplate in form. I’ve darkish hair and hazel eyes. The half persons are most likely questioning about, my cock, is what I consider to be a great measurement, measuring just below 9 inches lengthy. You’ll be able to see an image in my profile. I’m very intercourse crazed, like most guys, and am always fascinated about it and women (therefore my lengthy membership to this web site!). I misplaced my virginity to a woman who was a buddy of mine once I was 17. She was very fairly, had nice tits, a shaved tight pussy that blew my thoughts once I slid in for the primary time, and I take into account myself very fortunate for having her. I’ve a deep obsession with the feminine backside. I’m a straight up ass man, and I like every part about them. The totally different shapes each woman has, the way in which they sway when a woman walks, every part! Anal porn is my favorite to observe, and it dominates most of my sexual ideas since I used to be most likely 18 years outdated.
Now on to the story. On the time, like most 19 yr olds, I used to be hitting night time golf equipment actually onerous with my finest buddy just about each weekend. Being the place I’m in Canada, you’ll be able to drink/smoke/gamble/something you need if you flip 18 years outdated. One night time at a rustic membership downtown in October we had been tearing it up like we often did. My finest buddy had more cash then most 19 yr olds, on account of him working for his filthy wealthy dad and mom. So we might usually get some consideration from women on the golf equipment by shopping for extreme quantities of pictures and drinks and handing them out to any women round (mainly one thing now that I’m somewhat older would take into account an enormous douche bag factor to do). We had been with just a few different buddies that night time as properly. Normally we might exit simply the 2 of us, however being within the membership scene as a lot as we had been we knew folks at mainly each membership each night time of the week, whether or not they had been folks we went to high school with or I labored with. Presently I don’t bear in mind the event of this night time, however we had been going actually onerous, dancing and ingesting like loopy. Ultimately we break up up as we typically did on our quest to satisfy women and hopefully hook up. I discovered myself on the dance ground exchanging eyes with this borderline petite blonde woman. Very cute face, shoulder size vivid blonde hair, brown eyes, decked out in a costume. Upon nearer inspection, she had smaller, most likely a-cup breasts, very skinny construct all the way down to her hips which expanded fairly a bit. I knew immediately what was behind her… a booty that you wouldn’t usually discover on a woman of this measurement. We moved in somewhat bit nearer to begin dancing. Because the songs bought extra intense, so did our strikes, with grinding and feeling eachother up. The dance flooring packed, so it’s not such as you ever get seen what you’re doing. We chatted briefly with some small speak because it’s clearly very loud, and I moved in with the basic transfer “lets go get a drink!”. We moved to a bar, I purchased us some fruity shot that we had been into on the time, in addition to a hi-ball of our selecting. We talked a bit extra, exchanged names, what are you doing right here, and so forth. Her identify was Kim, and she or he stated she was right here together with her older sister and some buddies whom she was separated from after we started our little dance on the ground. I stated I’d assist her discover them, and she or he stated her sister could be onerous to overlook as she was sporting a vivid yellow costume.
After a couple of minutes of us two strolling across the bar, holding palms after all, a buddy of mine walked as much as me and stated “Hey man, Derek (my buddy) is on the dance ground with some chick in a yellow costume!”. Kim and I instantly went over and noticed the 2 of them grinding and dancing in the same means we had been. “Mission achieved!” and we had a fast snort and determined to get one other drink. We had been within the nook chatting and sipping away at our drinks, and after some time the booze actually began to settle in. I had my palms on her hips and she or he was positively giving me the look, and I made a decision to maneuver in. We began to kiss gently, which rapidly escalated right into a hardcore make out session. I moved my palms up and down her, feeling her small boobs, then all the way down to her plump spherical ass. This lasted some time, until finally out of the nook of my eye I noticed her sister approaching with no Derek in sight. I used to be rapidly launched to her gorgeous sister, who was taller then Kim, bigger C-cup sized tits, and in superb form. I might later discover out she’s a private coach. She stated they had been leaving quickly, and insisted Kim go together with her. I later came upon that nothing occurred with the sister, Ashley, and Derek. We rapidly exchanged telephone numbers, and she or he was gone. I rapidly linked up once more with Derek, and we had been on our means again to his duplex the place he lived alone, and was our central hub to celebration at mainly.
Waking up the subsequent morning to our ordinary cling over (which was nothing if you’re 19… these had been the times!). I had my automotive parked at his place as I usually did, so we stated our good byes and I used to be on my means again to my place. Once I parked at house, I checked my outdated iPhone 3g, and had a message from Kim. “Hey” is all it stated. I responded with a smug “Hey”. We rapidly bought to chatting about final night time, quickly responding to eachothers textual content messages. I’d exchanged a number of numbers with women at bars, however would not often pursue the subsequent day. Kim was enjoyable to speak with nevertheless, as we appeared to get alongside rather well. We agreed to satisfy for a date, and met for espresso by her place. I picked her up, and we chatted about life. I used to be in my final semester of faculty, and she or he was taking a yr off between graduating highschool and going to school. I additionally wished to notice that she had been a dancer her complete life. I graduated younger, which was why I used to be in my ultimate semester of my two yr program earlier than I used to be 20. Once I dropped her off again at her home, we had a fast little make out session, and referred to as it an evening. I watched her stroll again to her place to verify she bought inside, the entire time gazing her lovely backside she little question earned from the years of dancing.
The next week I moved into my brothers home for two weeks so I may home sit for him and his spouse. He had an important new place that I knew was going to be a blast to dwell at. After texting a bit with Kim, I satisfied her to come back over late one night time and hang around. It was a college night time, however I used to be getting the vibe that tonight might be the night time I hook up together with her! She lastly agreed to come back over after her dance apply, and I despatched her the handle. I let Derek realize it was lastly happening. I had an empty home, and I knew I may get this completed! He requested if I had a condom… and fuck! I didn’t! It wasn’t tremendous essential to me to get one (being younger and silly) however he had a great level that a number of women could use that as an excuse to not have intercourse. We rapidly hatched a scheme the place he was going to pop by, and if Kim had crushed him to my place, then we might declare that every one liquor shops round right here had been closed so Derek was choosing up a 40 of vodka I had as he was on his option to a celebration. Then, throughout the alternate of vodka, he would slip me a condom.
Kim arrived, we caught up on our days occasions. I discussed that Derek was coming by fast and the explanation why, who she knew so she wasn’t actually involved or something like that. We had been simply watching TV when he confirmed up. We rapidly made the alternate and Kim and had no thought as she wasn’t actually watching. Derek was on his means, and I acquired the ol “Good luck buddy” textual content. We had been watching TV spooning on the sofa. It rapidly escalated into one other make out session. We lastly had the place/time/privateness to get to the subsequent degree. I pulled up her prime and started fondling her tits, whereas she unzipped my denims and pulled my stiff cock out. She started gently stroking it, then I stated “let’s go to the bed room”. She stated she wasn’t positive, as our relationship was nonetheless very new. I attempted onerous to dodge her objections, and finally she began to come back round. Then it got here… “properly… do you might have a condom?” “Completely!” I snapped again nearly immediately. We had been then on our option to the bed room. A fast look on the clock and I noticed it was 2:00 am. I had class at 7:15… “Fuck!” I stated in my head. However I knew it could be value it. We rapidly undressed one another. She had fully shaved easy pussy, which I liked. I gently fingered her for a couple of minutes whereas making out. I then moved all the way down to suck on her small tits, and bought them good and onerous. Then I knew she was prepared. She put the condom on, and I started to maneuver into place. I pushed in slowly, as being a bit larger in that division I didn’t need to harm her (although its not like she didn’t have the hips to accommodate). She was very tight, as anticipated, and it was nice. We bought into a great rhythm of fucking. We moved right into a spooning place, and I bought an important prime view of her ass. It was as excellent bare as I had ever imagined. I gently unfold her cheeks open whereas my cock pumped out and in of her heat pussy, so I may see it in all its glory. We graduated to full on doggy fashion a lot to my pleasure, as she seemed wonderful from behind. I used to be pounding away, and glanced over on the clock. 3:00 AM… fuck fuck fuck. I knew I needed to wrap this up quickly. “Child, I’m getting shut. Can we take the condom off and have you ever end me?” “Fuck sure!” she rapidly rotated, pulled it off and devoured my cock in her mouth for the primary time. Arising and down for a couple of minutes, I knew it was coming, and she or he pulled it out of her mouth and started pumping furiously. Then it occurred, and I erupted an enormous load throughout her tits and abdomen. Mid means by means of she proclaimed “Wow!” as my load was positively enormous. However hey, fucking for an hour and 19 years outdated? In fact it was enormous!
We cleaned up and she or he left. I went proper to mattress. It felt like I hit the pillow and my alarm went off at 5:30 AM. “God dammit…” I believed, and set off for college. We despatched just a few informal texts forwards and backwards all through the day, nothing awkward, simply “Final night time was enjoyable” “Can’t wait to do this once more” and so forth and so forth. I had some drinks with Derek the day after and we exchanged excessive fives. He talked about the weekend prior to those occasions, he attached with this woman that we went to highschool with (who I truly had intercourse with a couple of yr previous to this story). We had amusing about it, after which he talked about one thing that I couldn’t get out of my head. He fucked her within the ass. I used to be dumb-founded, and intensely jealous he bought to expertise that! After that, I knew I needed to fuck Kim within the ass, it doesn’t matter what it took. I had by no means had clearly by no means had anal earlier than, however had watched it many occasions in porn. I by no means thought, nevertheless, that standard women could be keen to do this type of factor, and that it solely actually occurred in porn!
Kim and I continued to see eachother over the subsequent few months. It was a normal routine, we might both go to a film or for espresso, again to her place, fuck, then I might be on my means. Our intercourse was bettering with every session. She didn’t care about condoms anymore as she was on the tablet, although I by no means did find yourself cumming within her as she felt it was nonetheless to dangerous. Tremendous with me! She did nevertheless let me cum often the place I wished, both on her ass, her tits, and finally she let me cum in her mouth. I’ll always remember that, because it was valentines day, and I had informed her about how good it feels to have your cum sucked out of your cock (I had solely skilled that one time earlier than this). She rapidly complied, and swallowed an enormous load after an evening of intercourse. Then she swatted me on the arm “OMG! that was like a liter! what the hell!” she stated. “Sorry babe! it simply felt so good!” I replied. We had a great snort then off to sleep.
I finally labored up the braveness to say anal intercourse to her. She wasn’t as repulsed as I believed she could also be. Seems, she had tried it earlier than with some man, however they may by no means get it in. She stated she was extra frightened as a result of my dick was thicker and longer then the final man she tried it with. I pleaded together with her that we might take it sluggish, use plenty of lube, and if she wished me to cease we might. She stated she would give it some thought. In my head all I may suppose was “so she’s saying there’s likelihood!”.
The subsequent couple occasions we had intercourse I might work my means all the way down to her attractive little butthole. I might gently probe it with my finger, rim it round and see how a lot of it I may get into her earlier than she would cease me. I might use among the residual wetness from her pussy as lube, and gently work her asshole as if to mentally and bodily put together her. I finally bought my complete thumb in her ass throughout a doggy fashion session, which was nice, as she was bucking onerous and cumming her brains out on my dick. I rapidly pulled out and exploded over her ass, together with her small gap barely agape from my thumb. I knew the time was coming quickly she would agree.
Then in the future at school I bought a textual content. “I bought lube”. We had by no means used lube earlier than, because it rapidly grew to become our ritual for her to suck my cock earlier than intercourse, and I might finger her to get her juices flowing. I knew why she bought the lube. The top of sophistication couldn’t come quick sufficient. I bolted house, showered up and bought prepared, then headed to Kims place proper after dinner. I picked her up, and she or he insisted we see a film. I don’t even bear in mind what film it was, as all I may take into consideration was penetrating her deepest, darkest gap with my metal onerous cock. We began making out within the theatre, and I moved my hand down into her denims. I slipped my hand inside and gently began to rub her clit. Her pussy was already soaked, so it’s apparent the anticipation of tonights occasions was on her thoughts as a lot because it was mine. We left the film the second the credit started to roll, and we had been off again to her place. Her dad and mom had been house, and Kim stated she’d want it in the event that they weren’t there for this. I stated “Effectively clearly I don’t need your dad and mom within the subsequent room whereas now we have anal intercourse… however what will we do?”. She thought for a second then had an thought. “hey mother, we’re fascinated about going to the on line casino, need to include?” “Certain! when?” her mother responded. “Proper now! Why don’t you guys go forward and we’ll meet you there!” “Sounds nice!” and so they had been gone. I couldn’t consider it! They fell for that?!! Unreal! I informed her this most likely wasn’t going to be over rapidly, and she or he stated her dad and mom liked the on line casino and received’t even care if we didn’t present up. “Alright then… totally different form of folks” I believed to myself.
She confirmed me the lube. It was some “yours and mine” stuff that I had by no means seen earlier than. No matter, I didn’t actually care. We began undressing and kissing, and began with our ordinary rhythm. I started to softly finger her asshole whereas fucking her from behind once more, and she or he reached over and grabbed the lube. We moved into the spooning place. She slipped my cock out of her pussy, and lubed me up. I took the opposite bottle, and put some on my finger. I gently rimmed it round her asshole and started massaging it inside. I used to be so bloody excited that I felt nearly drunk with lust. Her ass was excellent. Her ASSHOLE was excellent! I needed to have it. I took my lubed up cock and place it on the entrance. “SLOW!” she snapped. “In fact after all… loosen up or this received’t work in any respect!”. And so I started to push in. The opening was very tight at first, nearly as if I hadn’t been fingering it in any respect. I pulled again my foreskin to make it a bit simpler. I had about half the pinnacle in, and Kim was taking it nice. She wasn’t doing something besides laying there, together with her one hand pulling open her butt cheek to permit me to enter. Ultimately, somewhat “pop” occurred, and her gap sucked in the entire head of my cock. “Unbelievable!” I believed, as her asshole was now co-operating to take my cock inside. I slowly pushed inside till I had about 2/3s of my cock in. I began to really feel somewhat resistance, so I didn’t need to push my luck and stopped there. I gently withdrew as much as the pinnacle, then thrust again in that very same depth. It was wonderful. I had by no means felt one thing so heat, easy and tight round my cock. To not point out the considered being inside this excellent ass. I glanced over and seen she was taking part in together with her pussy whereas I fucked her rear entrance. She was moaning barely, and I moved in and began kissing her neck, and clutched her boobs with my free hand. “Child your ass is probably the most wonderful factor I’ve ever felt in my life”. She had no response simply moaning somewhat louder. “The place’s my cock, child?” I whispered. She was completely infatuated with what was occurring, and I may really feel her butt gripping me even tighter. “My ass”. I figured she was near cumming as I may see her aggressively rubbing her clit. Then it occurred. She moaned deeply, and I may really feel her ass squeeze and suck me somewhat deeper inside. Her ass was cumming on my cock. I couldn’t consider it. It was all I may do to maintain from exploding myself! We lay nonetheless for a minute after, and she or he stored rubbing her pussy. She then whispered “I feel someones getting somewhat jealous”. I had no thought what she meant. She reached behind and slipped my cock out of her bum, and moved it to her pussy. I simply let it occur, perhaps her bum was sore and she or he didn’t need to admit it. I fucked her pussy for about 5 minutes, then pulled out and got here on her decrease abdomen and pussy. We handed out for a couple of half hour then I awakened, we stated good night time and I went house.
I slept like a child. She texted me the subsequent day expressing somewhat regret we had vaginal AFTER anal. I agreed, however she by no means bought an an infection or something, so it labored out. I had lunch with Derek the subsequent day and some different buddies. I texted Derek whereas we had been on the desk so it was simply between us two. I wrote “I fucked Kim within the ass final night time”. And he spat his drink out whereas studying it and laughed. We excessive fived in personal after lunch.
Kim and I ended seeing eachother just a few weeks later. I wouldn’t actually take into account it a break up since we had been by no means actually official. She began to get actually bizarre and clingy. It grew to become evident that there wasn’t a future there. We had a clear break and by no means noticed eachother once more. I used to be rapidly deleted off fb and that was that. I had since graduated faculty and started working full time in a brand new place at my identical place of business, which had ample quantities of girls working there of their youthful 20s who liked to celebration. I knew this was the start of my subsequent chapter, and would finally result in what is going to hopefully grow to be Half 2 of this story.
Nonetheless I by no means forgot Kim as the primary woman I ever had anal with.