Written by Bigbadwolf_PTA
01 Aug 2017
First time anal
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6 minute read
This story came about a long, long time ago in a galaxy far, far away… or, more accurately, nearly three years ago when I had had first started seeing Alyssa. Things were casual; it was a time prior to us becoming a couple, when everything about the other was new and exciting. (Not to say that new and exciting encounters don’t occur still.) Her body, kinks and uncovering her level of deviancy were an endless expedition that my 27 year old self was all too willing to undertake. I approached this new challenge with all of the excitement of a child on Christmas morning. This is the tale of the first time I was granted access to her ass.
Before we begin lets cover the obligatory descriptions of us. Alyssa was 22 at the time, 5’ 2”, and 120 lbs, with extremely wavy to almost curly dirty blonde hair that runs half way down her back. She has piercing green eyes, a flat stomach and a full round ass that complements her perky 34B breasts. Her breasts are adorned with a stainless barbell through each nipple. Moving on to the lesser of the characters, me: I’m 5’ 8”, at this point I was 165 lbs, average build with dark brown hair and roughly trimmed beard. I am pretty much the definition of average with a circumcised member that can only boast a 6.75 inch length and 5.5 inch circumference. Now, onto the stuff readers’ care about.
Alyssa lived a mere three minutes from my work, making it opportune to swing by for some entertainment during my lunch break. I quickly drove over, with one thing on my mind. She greeted me in at the door in a pair of faded jeans tightly hugged her toned ass and a washed-out red t-shirt that clung tightly to her tits. As soon as the door opened we began to make out and grope each other as we stumbled towards the bedroom. Once through the doorway, I pushed her onto the pink comforter that covered her bed.
As we made out on the bed I slowly slid her shirt up and over her head, tossing it amongst the scattered laundry on the floor. Looking to advance our tryst, I moved down her body kissing and biting lightly on her neck. This, I quickly discovered was a major turn on for her as she began to buck her hips and a quiet moan sensually escaped her lips. I continued to work my way down squeezing one breast while sucking on the other. The moans and bucking grew as I alternated sucking on and biting her perky nipples. I ventured farther south, slowly kissing my way from her breasts down her stomach and using one hand to unbutton her jeans.
I figured as it was lunch time I should allow myself to indulge in a banquet of her pussy and sweet juices, although I had the same thing a few days prior when I stopped over after work. (What can I say, when I find a meal I enjoy I stick with it.) As I started to unzip her pants she uttered the words a hungry man dreads, “I’m on my period.” I temporarily froze, unsure of how to proceed. “Want to fuck my ass?” she swiftly asked with a pleading expression on her face. “I could do that,” was my oh so witty retort. Despite my lackadaisical response, I was excited. Around half of the women I have been with have been receptive to anal but, I always had to initiate. Here was a girl practically begging to have her ass fucked, I was instantly harder than a steel beam. The instant I endorsed the idea she sprang off the bed, kicked her pants off her ankles, and headed into her walk in closet with a grin on her face. She quickly returned with a bottle of lube, small vibrator and a condom. “I like to be on my back, so I can play with my vibe”, she stated while sitting on the side of the bed. (I prefer to bend a woman over while fucking her ass but, figured it wasn’t the time to argue semantics.) “Fine by me,” I replied with a smirk.
Alyssa sprawled back resting her head in a throw pillow in the middle of the bed with her legs hanging off the side and began to slowly slide the vibrator back and forth over her clit. It was all the invitation I needed as I rolled the condom on and poured a generous amount of lube onto my erect cock and her puckered little hole. You could see her hole throb and relax as she continued to become more aroused while the toy grazed her swollen clit atop her already drenched slit. I hoisted her legs, which were already beginning to twitch in pleasure, over my shoulder and began to press my cock against her waiting asshole. As I began to apply pressure she turned up the speed on the vibrator.
This added level of stimulation was all it took as her hole yielded to the pressure and my head popped into Alyssa’s ass. She grimaced slightly at the intrusion and continued to play with her pussy as I slowly began to push farther into her. It was slow going; as her ass was so tight. It took a solid three minutes applying slow steady pressure, watching my dick creep deeper into her while minimizing her discomfort. Finally, I bottomed out in her. Once I was balls deep in her ass, I began to build a steady rhythm, pulling out to the tip before pushing all the way in causing my balls to slap against her. As my rhythm and pace continued to build, so did her orgasm. After only a handful of thrusts, she released a loud moan and began to shake as her orgasm was unleashed.
As her orgasm diminished, I continued to slide my well-oiled cock in and out as her ass pulsed around it. Like a metronome, I maintained my thrusting, while the juices from her glistening pussy dripped down her swollen lips. The strands dripped down mixing with the astro-glide already on my cock, providing addition lubrication for her pink asshole. The instant her orgasm abated Alyssa was right back at her clit with the vibrator, eager to coax out a second one. I began to pound harder, truly giving her ass everything it could take. I pulled completely out and rammed it back in to her yielding butt. The sudden emptiness followed promptly by being jam-packed elicited a gasp as she ground the vibrator determinedly into her clit. I alternated giving a few hard thrusts with repeating this maneuver as she started to twitch and moan, approaching another orgasm.
Those heavenly sounds were my cue and I began to thrust as hard as I could, pulling out to the very tip and slamming into her ass with a thwack as my hips slammed into the firm muscle of her buttocks. The combination of the tingling of the vibrator on her clit and my cock ravaging her ass triggered her next orgasm as she quivered and screamed in ecstasy. As I thrust into her ass the orgasm caused her ass to pulse again and clamp down firmly on my cock. The sensation was too much; I gave one last plunge into her eagerly awaiting ass and filled the condom with my hot jizz. Sweaty and tired I collapsed on top of her on the bed, using her breast as a pillow. With my dick slowly softening, still in her ass, all I wanted was some water and a nap. However, it was time to clean myself up and get back to work. Lunch was over.