"Do I really have to wear this?"

"Come on, Miles, please? It would make me so happy. I ordered it just for you. And I probably won't see you again for a while..."

A night in an out-of-town motel was nothing new to Tails and Vanilla. As "friends with benefits", they were well used to each other's company, and took trips together away from everyone else for some private time. Sometimes Cream tagged along too, but it was just them this time.

The circumstances behind this meeting were a little different though. Tails was on another adventure with Sonic, and they happened to meet Vanilla nearby. They settled into a motel for the night, since the weather was going to be to wet for camping.

Vanilla knocked on Tails's door a short while ago, and brought something for him. It was a set of "specialist clothes" she had ordered online just for him. Obviously, it was for use when they were alone.

The outfit was a tight fitting top and thong, with white gloves that ended past his elbows, and thigh high boots that were a little difficult to walk in. Tails looked in the mirror with them on, and thought he looked ridiculous. But, Vanilla had gone through all this just for him, so he didn't really have much of a choice.

Stepping out into the main room, Tails displayed himself, his left hand shyly grasping his right arm.

"I feel stupid..." He muttered.

But he flinched slightly as he heard a shriek of delight from Vanilla, which almost threatened to pass through the room's walls, and alert their neighbors. The rabbit milf bounced towards him, taking in his new look.

"Oh, Miles! It fits you perfectly! And it's even better than I imagined! You look so cute and sexy! I could just eat you up right here!"

Tails just stared at the floor in shame. He couldn't think of what to say, until he saw a pair of shapely legs stepping in front of him, and he felt two hands embracing his shoulders. He looked up, and saw Vanilla's beautiful, caring face looking at him.

"I know you might find it a little... unorthodox. But I just want you to know, if you wore this for me, it would make me very, very happy..."

Tails felt himself getting hotter at Vanilla's close proximity. And it was only a couple of seconds before he felt his thong getting tighter and tighter. He looked down, and saw a telltale bulge forming between his legs. The thong was stretchy, and was able to contain his raging erection fairly easily.

"It seems you like this more than you thought." Vanilla cooed softly. "Now, how about I do something about that?"

Within the minute, Tails was lying on the bed, with Vanilla unsheathing his cock, and stroking it with a new passion, causing the young fox to moan in ecstasy.

Maybe he could get used to this after all...

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Tails and Vanilla models, along with Tails's outfit, by KabalMystic
Vannah hotel map by Ganonmaster