You see, I have always been told I had a tight ass.. And it’s true really. My ass does look kind a nice and appealing even if I say so myself and as a teenager at school, I realized quickly the attention this tight was causing. Standing by my locker, I would often bend down, quite inadvertently and there are many occasions when I felt stiff cocks brushing against me, by accident of course, as boys would pass by. I admit it was a real turn on for me.
When I turned 19, I met a 44 year old man who was quite obviously “enamored” with me. I would “bump” into him often and on one of those occasions, I guess I mustered enough strength to ask me out.
And so a relationship that was quite platonic to begin with turned more physical even though I couldn’t believe I was fucking a man who was the same age as my dad. Talk about Daddy’s girl! At 19, a girl is supposed to be a young adult, but the teen in this woman is still there and I was flattered by the whole thing. He would shower me with compliments, help me with book purchases and a few bills and was quite charming as well as being an excellent lover.
As a lover and an older man showing the ropes to a teenager, he showed more than a fair interest in my butt and would often times pin me against my desk as I was getting ready to sit down. He would stand behind me, strip me naked any press his hard dick against my ass, letting it rest in between my butt cheeks whilst playing with my pussy at the same time, and taking me to quick and sudden orgasms. I was always surprised as to how fast I would come with him. After all, my school days teen boyfriends had never made me come before. As I would start to come, he would whisper in my ears that the next time he would do me, it would be with his cock deeply buried inside my ass.
I didn’t know how to respond, or if would even enjoy anal sex and so he continued with his games, bringing me to orgasm, and with each passing day, he would shift the position of his dick until yesterday when it was clearly pressing against my butt hole.
He had brought in some lube for the occasion and although feeling the head of his cock slightly pressed against my ass, ready to push right in, was exciting, I knew that it would be quite painful and told him so.
He obviously had done this before since he began to lubricate my butt hole with an ample supply of oil until a whole finger was fucking it slowly. The sensation was unnerving, painful and surprisingly satisfying and I could help thinking about all these adolescent males who as teenager had looked at my butt wishing they could make it theirs, somehow.
When he was done with his thorough lubrication, he replaced his hand with the head of his cock and began to push it inside my butt hole.
And so, at the age of nineteen, barely legal in terms of sex, my boyfriend gave me my first anal sex experience and whilst searingly painful to start with, the pain gradually subsided until it actually felt nice enough for me to enjoy it.
That very first anal sex did not give me an orgasm though. The second and many more after did!
