Harry Styles One Shots

Ready?

Anonymous asked:

Omg i love the idea of a "first time anal" one omg i love your writing, pleasd make this ask a piece omgg

A/N: This is installment 5 of A Series of Firsts!!! This one has been highly requested for some time now so I'm finally writing it. I decided to do a simple plot to this one so yeah...it's crazy filthy tho. Also, this one is pretty freehand for my writing. So I hope you guys like it...Enjoy🙃

Harry'd been training your second hole for the past couple of weeks. The two of you had been wanting to give anal, particularly on you, a shot for a good while now. After seeing how well Harry adjusted and responded to having his hole played with, you were really interested in trying it out and getting a taste of the pleasure that Harry felt. From the way his cock twitched between his legs as you pushed your fingers or toys into his puckered entrance and the way he'd let out the loudest whines and moans from the feeling, you could tell that it felt amazing. So the possibilities for pleasure with his fingers and cock were endless. And the same way you were excited to give anal a try, Harry matched that excitement plus some. When you told him that you wanted to give it a go, Harry lit up like a Christmas tree.

The last thing Harry ever wanted to do was pressure you into something that you were unsure of or weren't comfortable with. So despite the fact that he was being teased by your puckered entrance every time he took your from behind, and he that couldn't stop swirling his tongue around the area whenever he had his head between your legs, along with thumbing at your entrance and lightly nudging his cock at it, Harry made sure to never pressure you. That's why when you told him that you wanted to play around with your second hole, he was ready to make sure that you're pleasured to the fullest and comfortable in the process. Since you voiced your concern about his size being too big for your entrance, Harry went straight into buying and researching any and everything to gradually move you towards taking his entire cock.

Before he bought anything, Harry did a pretty good amount of research. He even cross referenced different pieces of information. He looked into the best lubes for extended use of anal plugs, he looked into the best ways to train your hole to take more and more over time, and he even went as far to see if it was safe for you to sleep with your plug inside of you. Luckily for him, he got all the answers he needed and was hoping for. Once he compiled all of his information, Hary then went on to purchase items. He bought two types of lube, an oil based lube for when you wore the plug throughout the day, and a water based one for when he was playing with you at night. He also bought an extensive array of toys. For starters, he purchased a set of four shiny steel anal plugs with a big jewel in your favorite color on top that gradually increased in width and length. These would beused for everyday wear. Along with these plugs, he bought a couple silicone dildos that varied in girth and length. These were for when he would be training your hole and helping you become accustomed to having a cock inside of your tightened hole. And none of them were the size of his cock. He did this simply because he wanted to give you a bit of a surprise once the time finally came. Harry also threw in a couple accessories that you'd enjoy. He bought a couple bunny tail plugs that he thought would look adorable on you, and he got a string of ben wa balls. Those were definitely for him; he found the picture of you struggling to maneuver and hold them inside pretty amusing to say the least. After he picked everything and put a rush on the shipping, Harry anxiously awaited his large package of toys that he was dying to break in.