The wind blew heavily in the opposite direction of Issei, as he for his bike down the dark deserted street.

He felt miserable; Rias had been counting on him to bring in this contract. Not only was he eager to please her, but she had even promised him the executive right to grope her tits if had gotten this right.

The prospect had driven Issei go do his best, but the guy had just sent him away for not being a chick. That ass hat thought that it was some kind of demonic prostitution service!

Issei sighed as he peddled through the windy dusk of his home town. He had no idea how he was going to tell Rias in the morning.

He didn't even bother to put anything on to sleep in as he stripped down to his underwear. He was miserable enough to sleep in his clothes but it was hot, and he intended to get at least some sleep.

But such a prospect did not seem possible, given the puddle of boiling anger and guilt that sat in Issei's stomach, refusing to leave him at peace.

He had been within groping distance of Rias' rack and he had fucked it up again. He felt so worthless that he couldn't even bring himself to jump when he began to roll over and touched something warm in his bed. Not the first time anyway.

When he felt it move and noticed that it was breathing that he began to tense up. Slowly, he began to roll over the rest of the way on to his other side so as to see what was in his bed. What he saw made his stomach turn to ice. Rias Gremory was sleeping naked next to him.

Issei was at a loss for what this meant or what to do. She initially appeared to still be sleeping, but just as Issei contemplated maybe leaving, her eyes fluttered open and she smiled warmly at him.

"Hello, you feeling ok"? Rias wrapped her arms around Issei's neck and drew him in closer. "You sounded angry."

Issei found his words to be eluding him, just below her piercing blue eyes and her pillowy lips; he caught sight of his lost reward.

Rias breasts were pressed up against his chest, soft, squishy and emitting a paralyzing warmth that was starting to make the room seem a whole lot hotter.

He knew he had to say something, but he was slightly scared of what her reaction would be. He decided to avoid the subject of his anger.

"No...Not at all, why are you in my bed"?

"I came here to wait for you and see how it went"

"Why are you naked"?

"I told you, I can't sleep unless I'm naked."

Issei was aware that something else was touching him as well. A soft twitchy something was rubbing against him in a lower place. He was even further baffled as he felt it start to get wet.

"I love it when you're embarrassed" Rias smiled as she whispered in Issei's ear. "I know that you didn't get the contract."

"You do"?!

"Mhm" Rias muttered as she began to rub her body against Issei's. Her boobs and pussy started to rub Issei down and he could swear there was a hot, wet sensation moving up and down with her pussy.

Issei winced slightly when Rias slipped her hand down the front of his comfortable underwear and began to grope his dick. Her smooth feminine fingers pulled the foreskin back and played with the head. It was rock hard in seconds.

Breathing hard, Issei tried to say something, but his words didn't come quickly enough. Rias had mounted him, and had pulled Issei's black underwear away. His cock sprung up, eager to serve.

Rias stuck out her tongue and ran it along the entire length of his dick. Rias then took the whole thing in her mouth and proceeded to milk it.

Issei had so much he wanted to ask: Why was she doing this? Was she happy or angry? What was she going to do next?

But all of these questions were rendered irrelevant as Rias brought her ass to rest on Issei's face, pressing her clit up against his panting mouth. Letting his instincts take over, Issei gave into pleasure and began to suck.

Issei was feeling it the most of all, the lips and tongue wrapping around his head gland giving her mouth good firm suction as Rias bobbed up and down on Issei's dick.

Her own pussy was soaking wet now, Issei had to gulp it down so fast he could barely breathe. The weight of her tits on his belly combined with the weight of her pelvis was making him feel trapped, Imprisoned by her sweet horny flesh.

Neither one could last long, Issei stuck his tongue further inside the twitching, squeezing folds of Rias' pussy as she sucked harder. She began using her free hands to play with Issei's balls and ass.

Rias began to make choking noises as she pushed Issei's dick to the back of her throat and ran her around in a circle inside the entrance of his butt. Issei stuck his full tongue inside Rias and began waggling is as fast as he could, rubbing her breasts with his hands.

Issei convulsed as cum shot into Rias' mouth. Rias' ass shuddered as she came in Issei's mouth. Rias continued to suck as she drank down Issue's orgasm.

Only after she drank everything did she allow the penis out of her mouth and contentedly licked it. Issei swallowed Rias' nectar and dropped his head back, panting with satisfied fatigue.

With his eyes closed, he didn't know what she was doing, but Issei heard shuffling above him and he felt two soft thighs pressing against him.

Opening his eyes, he saw Rias sitting on top of him, smiling excitedly and jerking his dick while it throbbed still erect just below her dripping wet pussy.

"This shouldn't be too complicated right? All I have to do is put yours in mine"?

Without giving herself time to think, she forced her body down and swallowed the entire phallus inside her at once.

It was a marvellous blend of pain and pleasure, as the dick stretched and filled up Rias' insides, she felt something tear within her as a fine little stream of blood escaped her.

Issei looked at it and realised that they had just given their first times to each other, and Rias was so warm and slick he could barely resist moving. Rias looked down at Issei, panting.

"Are you alright"?

"Yes...yes I'm amazing...move, please move."

Issei did as he was told and began to move. It was pure ecstasy, their genitals began to clash and divide like the tide and the shore. His dick and her pussy both were milking each other lovingly, passionately.

Issei sat up in order to embrace Rias with his arms, but she pushed his face into her breasts to turn him on even more. She knew it was what he wanted, and she wanted it too.

Issei came inside of her. He came hard and shaking, not having much air with his face in Rias' cleavage. The two held on tighter at the climax before flopping down on the bed.

Issei and Rias held each other as they caught their breaths. Rias took Issei's hand and guided it to her right breast. She allowed him to feel it while they made out.

"Why did you do that" Issei asked as he embraced Rias under his bed sheets as they smiled at each other.

"I had to punish you, you're cute when you're angry." She moved in and kissed him on the forehead."But it made me sad...I needed to cheer you up somehow."