I was 18, and in my first long term relationship. The sex was great, we were both adventurous and at it all the time - anywhere and everywhere! There was, however, a bridge we had not yet crossed...
I've had an anal fetish ever since I watched my first porno, an amateur video my mate had recorded off Television X... While I was turned on enough watching the guy pounding away at her pussy, when he pulled out and slowly eased it into her tight little arsehole, something stirred within me. Watching her eyes widen, before closing in ecstasy and hearing her moan as he pushed deeper and deeper, going harder and harder, I was infatuated, and fantasised about it constantly from that day on.
In my younger years, though, I was prone to shyness, and whenever I got lucky, I was reluctant to push it (literally and figuratively!) But having been with my then girlfriend for a while, we were getting more and more explorative, and one day I decided to stick my toe in the water... well when i say toe, I actually mean finger, and when i say water... well you get the picture.
We were out having few drinks one night, and as standard we were getting shamelessly frisky and boring our mates, so we decided to head home to carry things on. There was something in the air that night, maybe it was a full moon, and we were both a bit tipsy so we were going at it a bit harder than usual. At one point she even dragged me down an alley, dropped to her knees, pulled my cock out and took it so deep in her throat i nearly shot my load right there and then, but as she felt my knees start to shake she pulled back, grinning, and stood up, tucking my rock hard cock back into my pants and sauntered back onto the street. She could be such a bloody tease sometimes, but to be honest, I loved it.
Anyway, we finally made it home and as per usual tore each other's clothes off as soon as we'd shut the front door, eagerly making a beeline for the bedroom to carry things on. We loved all sorts of positions, and she loved starting things off with a 69 so I laid back on the bed as she mounted my face and took me deep in her throat again, while i flicked my tongue in and out of her hot, wet cunt. I felt her judder as she came, and she rose up and shuffled forward, mounting my cock in reverse cowgirl and bounced up and down feverishly. I love that position, seeing her long hair dance over her shoulders and her peachy ass bob up and down as she held her hands up behind her head, knowing how much I was enjoying the view.
After a while, I felt my excitement rise, and I was ready to cum. We always liked to finish in doggy style, with me pounding her hot pussy as deep as i could go, getting faster and faster until I exploded - she loved feeling me cum when i was at my deepest, so raised my self up, pushing her forward gently to signal i was ready. Eagerly, she climbed off and got on all fours sticking her beautiful behind up in the air, and gave it an excited little wiggle.
At this point, I have a confession to make - I loved fucking her pussy, but with my fascination with anal, sometimes I'd close my eyes when i was reaching my climax and imagine I was fucking her arse, and this was lining up to be one of those evenings, but that night, the way she wiggled her sweet, peachy bum at me awoke an extra sense of mischief in me....
I grabbed her hips firmly, pressing my fingers in, and began fucking her doggy style, teasing her a little by going slowly at first, but gradually ramping up the pressure and speed until I was thrusting hard and fast, as deep as i could go, getting off on hearing her high pitched moans. I was almost ready to cum, but this time, instead of closing my eyes to fantasise, I became transfixed by her neat little arsehole as i pounded into her repeatedly. I don't know what came over me, but feeling adventurous, I licked my finger, and pressed it gently on her arsehole, before easing the tip in...
She clenched, and froze solid... There was an awkward silence that felt like an eternity, but then without saying anything I felt her relax slightly, and she began to push back onto me again. Excited, I began fucking her again, but slower, as I eased my finger deeper. It was so hot and tight, and with only a little saliva as lube I had to go slowly, but I kept going until I was up to my knuckle. At this point we were both almost silent, but breathing heavily, and the atmosphere was so intense it felt like the air was electrified. I curled my finger slightly as I began to speed up my thrusting and she let out a soft, deep, long moan, pushing her arse up onto it. Every time I thrust into her I could feel her arsehole twitch tightly round my finger and it drove me wild. I began to moan too, and could feel the orgasm brewing, and with one last thrust I came deep in her cunt. Again, there was silence, but as i gently slid my finger out of her arse she let out a little giggle before curling up onto her side. I wrapped my arms around her and we spooned, as we always liked to do after sex, but this time she was quiet. After a few moments I broke the silence and began to ask "did you-"
"er..." she interrupted, "I don't want to talk about it right now."
"Oh..." I said, feeling awkward "I just-"
"It's ok," she said, "It's just, er... Not right now"
I was a worried I'd over stepped, and I think she sensed it, so she took my hand and pulled my arm around her, giving it a reassuring squeeze, and I felt better...
Surprisingly, she drifted off almost instantly. I didn't sleep so well though, part of me was excited, triumphant almost, but I was also worried I'd crossed a line. Maybe I should have asked? But would that have spoiled the moment? I was pretty sure she'd enjoyed it, although I was also concerned she'd just played along because she wanted to please me. After finally getting a couple of hours of restless sleep, morning rolled around and I got up quietly, and I made my way to the kitchen to make her a coffee. She stirred as I came back into the bedroom. I set the mug down onto her bedside table and gave her a soft kiss on the cheek.
"Morning" I said quietly, with a hint of trepidation in my voice.
"Hey," she said softly, then with a sleepy yawn she held out her hand, beckoning me back into bed. She wrapped her arms around me, laid her head on my chest and we cuddled for a while, as we liked to do in the mornings. She was still a bit quiet, but once she had woken up a bit she giggled and said in a slightly shy voice "so... that was new.."
We both began laughing, I was so relieved!
"Come on, let's get some breakfast. I'm starving for some reason" she said, looking at me coyly..
"Yeah me too" I laughed.
She bounced out of bed and padded to the door, where she paused, and gave her bum a little wiggle before heading to the kitchen....
TBC....
