Sitting in the airport with time to kill reliving some of my better days. This story takes place with one of my ex-girlfriends, let’s call her Sarah. Let me know if these stories are too long. I am not a huge fan of the ‘parts I, II, etc.’ but I tend to get carried away as I relive these experiences…
Sarah and I were at a party her friends were throwing and it had been a week or so since we had seen each other. We met at the party and enthusiastically kissed and said hello as we grabbed drinks and started mingling with our friends. It was clear that the sexual tension between us would need to be settled ASAP.
We were out on the patio chatting it up with a group of her friends, and Sarah was standing in front of me as I leaned up against a railing. Sarah did this wonderful thing when she was drunk and horny…while engaged in a conversation with someone else, she would place her hand behind her on the front of my pants and stroke my growing bugle. Then, without warning, she would unzip my pants and slide her small hands through my pants to grip my cock.
She was engaged in a conversation with one of her friends about god knows what as she was slowly stroking my dick and bringing me to full attention. Knowing she could only have so much fun with me there, she would always try and help me conceal my boner by flipping it up into my waistband and zipping my pants back up (pro move that she seemed to have mastered).
After this, I knew it was time to go and I grabbed her hip and said we should probably get going before our big day (lies) tomorrow. We both had a pretty strong buzz going, and as we got in the cab home we were all over each other.
As we got home, our clothes were coming off as we furiously kissed and grabbed at each others bodies. I pulled off her top and started to kiss and suck her goldilocks tits (C’s – not too big, not to small, just right). Our pants and underwear came off and she immediately dropped to her knees.
Up to this point, she had never given me head while on her knees, only while I was lying or sitting down. As she sucked me and looked up I almost blew my load all over her right there. The liquid courage was doing its work on my stamina and she was pushing her gag reflex, leaving a string of spit hanging down her chin.
Nearing climax, I need to return the favor and build myself back up. I picked her up and brought her over to the bed and got between her legs. She put her feet on my shoulders as I started to lick her clit and slid fingers inside of her. We had previously fooled around with butt play and we had talked about taking it to the next level at some point, so I decided to see if tonight was the night.
While kissing and sucking on her clit, I pulled my index finger out of her pussy and pressed it softly against her virgin asshole. She was sopping wet and her juices formed a perfect lube as she moaned deeply and pushed her sex against my face. I took this as a sign to press forward, and I slowly worked my index finger in to her asshole. First the tip, then the knuckle, all of a sudden my finger was deeper inside her ass than it had ever been.
She continued to moan deeply, muttering ‘yessss fuckkk yessss’ as I ate her out and slowly fingered her asshole. She then grabbed my hair and pulled me up to her face and insisted that I fuck her immediately.
Not that I needed the encouragement, I slid my dick all the way into her, feeling her tighten around my shaft as I began to pump in and out of her in missionary. In this position, she grabbed my arm and started to move my hand back towards her asshole…I guess she liked what we started with. Fully inside of her, I pressed my middle finger against her hole as she gasped for air. I slowed my thrusts as I worked my finger past the knuckle and all the way inside of her ass.
I started to move my dick and finger simultaneously inside of her when she stopped me and said ‘no no…just your finger’. I buried my cock as deep inside her as I could and I proceeded to finger fuck Sarah into her first anal induced orgasm, as I felt her pussy squeeze my cock as she thrust her head back in bliss. As she started to come down to earth I began to slowly thrust into her again before she said ‘no, no I need more of you’.
It took me a second to realize that she wanted my cock inside of her ass. She pushed me off of her and got into doggy, pressing her ass in the air and begging me to fuck it. To this point, we hadn’t done more than a finger, so I was worried my cock might be too much at this time. She did not seem to share the same worry as she reached back and grabbed my dick, lining it up with her asshole.
She was soaking wet, so lube was plentiful. I slowly slipped the tip of my dick into her asshole, releasing a grunt of pleasure? pain? from Sarah. I asked her if she was ok to which she moaned ‘yes, but please go slow’. I took a solid 10 minutes (probably more) slowly pressing into her asshole and sliding my cock in and back out to the tip to slowly loosen her hole. Suddenly, I found myself balls deep in my first asshole.
I rested my cock fully inside her ass and let her know it was all the way in. She let out another grunt that could have been one of the sexiest sounds I have ever heard, followed by my favorite command – ‘fuck me’. Sarah was still super tight, so it was very slow thrusts, but I could tell she was starting to enjoy herself as she moved her hands to her clit, occasionally rubbing my balls as I bottomed out in her asshole.
Between the prep work of sliding into her asshole, and Sarah rubbing her clit, she seemed to be approaching another orgasm. Running near the edge myself, I felt her grab her own pussy and tighten up, as her asshole clenched on my dick. This was all that I needed to unload our first anal creampie, shooting several jets of cum deep inside of her. She fell forward and I fell on top of her, my cock still buried in her asshole. We each caught our breath as my shrinking dick came out with an audible ‘POP’ from her ass.
That night was the first of our many anal adventures and was one of the hottest things we did until she DP’d herself with a dildo while I fucked her ass.
Source: reddit.com/r/gonewildstories/comments/7798hb/first_anal_with_my_exgirlfriend
More to come I hope
Mmm Sarah was a very sexy gf